Chapter 1
Jason was walking to the park. Things were too crazy at home and he was still afraid of being discovered by his parents. As he crossed the street to the park some highschool girls passed him in the other direction giggling.
"Probably laughing at me because I'm too short to get a date" he thought. "They can't possibly know my dick is the size of a thumb."
He shook his head. 25, still living with his parents and no job. None of which was as embarrassing as his 2" peen and tiny child-like nuts. What a looser. He deserved to be laughed at. He was destined to spend the rest of his (hopefully short) life alone.
Or at least that's what he used to think. That was until he found sissy porn. Sissies were weak, subservient men with tiny useless dicks who were dominated by their partners. Sissies were too weak and useless in bed to be real men. So their wives or girlfriends feminized them. Turning them into girls and using them accordingly. Jason took a look down at his groin where he knew his dick was but you couldn't tell. There was no tell-tale bulge in his pants. Jason was a sissy. He didn't deserve a normal relationship. He didn't deserve to fuck women, only to be fucked by them with huge strap-ons or by the boyfriends any of them would undoubtadly have to take in order to feel sexually satisfied. Jason had realized that he finally had a chance at a future. That future might make him a housewife but it was still a future. He just had to find a domme to take him as their sissy.
But he didn't know how. Where do you meet strong dominant women? And how could he possibly ever approach one if he did? So he'd settled for his imagination and Sissy hypno porn. Sissy hypno porn was hot. It showed sissies transformed into beautiful women being used by women with gigantic strap ons or hung, hot men. Jason wanted to be dominated by a woman. Even if she was going to fuck him with a strap on. After all, he was straight, right? He'd never felt attraction to a man. Though, he thought, he did have to admit that the huge cocks in the sissy hypnos were mesmerizing. That he chalked that up to jealousy.
Having never had gay sex he worried that it would be painful. So he began experimenting, first one then two fingers into his rectum. It was an interesting sensation having something going IN his ass instead of out of it but it wasn't a whole lot different from taking a shit. That was until he finally found his prostate. His p-spot, a little hard spot about the size of a cherry only truly detectable from within the rectum. But oh the sensation when he pressed it. A whole new world exploded through his body. Maybe getting pegged wasn't going to be so bad after all.
Then about four months ago he finally decided to search disboard for discord servers that might be sissy friendly. Where he might meet a domme. He found a bunch of servers full of sissy hypnos, and captioned pictures but he was too nervous to reach out to anyone. That was until he joined that unicorn server. He had read the server rules, chosen his roles. "Sissy" for gender, obviously, "straight" for sexuality and others, "looking for femme", "unlocked" and more. He thought back to the sissy hypnos and their insistence that sissys are for eating dick and getting fucked. So he'd changed sexuality to "Bi" and started looking at the server's channels.
Taking a seat on a table at the park his thoughts returned to the present. It wasn't the lack of a job or his micropenis he wanted to hide. It wasn't even his crazy porn addiction he wanted to hide, not today.
Today, Jason was expecting a message from his Daddy. Not his father, he was at home drinking beer and watching the game. Jason's new Daddy was from thousands of miles away, Seattle.
In discord he had posted his introduction and had scrolled up to read the introductions of some of the others. Directly above his, the intro from TERP, caught his eye. It was an older man in his late 40s. A computer programmer and nerd into D&D, star wars and anime. All things which Jason adored. He seemed so warm and safe. Jason's mind kept going back to the hypnos with their massive cocks. Yeah, "bi" had probably been a better choice. trembling he clicked on TERP's profile and there it was, exactly what he was hoping to see. "DM's open."
He'd opened a DM and typed "hi." Not expecting a quick reply he'd began to move the phone to his pocket but was surprised when it buzzed. It was a response.
"Hello."
"Excuse me for writing to you out of the blue but I saw your profile and I would like to know more about you."
He had held his phone in both hands waiting for the response. When it came Jason's heart sank.
"I'm not really looking to get together with anyone at this time."
"Oh, ok. Sorry for bothering you."
"No bother sweetie, anything else I can help you with."
In desperation he wrote "Do you know someone else, some dom or keyholder?"
"I'm sorry sweet pea. I wish I could help you get locked, spanked and used but I've been away from any kink community for more than 20 years. I'm kind of new here on this server myself."
"Sweet pea." He was so tender Jason's heart swelled. And "locked, spanked and used." TERP knew exactly what his sissy heart desired.
TERP had started giving him advice. First about the server, how to unlock secret channels, where to post that he was looking for a domme. Jason had been so comfortable that he'd forgotten himself and asked for any advice TERP might have on how to progress. There TERP had excelled. Oh boy did he have advice. He had advice on toys, on training your ass and throat for larger sizes. Recommendations on chastity cages, toy cleaners, positions and more. Jason was beginning to wonder how TERP knew so much about sissification. Had Jason misread his profile. Was he not a dom?
"That's because I'm a Daddy poppet."
"A Daddy?"
"Yes, I take sweet little sissies like you and teach them to be wonderful obedient little girls."
In his head something clicked. He'd never felt this way about anyone before. None of the high school girls before he graduated or the women at the jr. college (before he dropped out) had made him feel this way.
They continued to chat. Jason had plenty of questions about anal sex (which was terrifying) and cock cages. He wanted to be locked. To have someone else. No, not someone, to have TERP hold the key to his ability to feel sexual pleasure. And to have the chastity cage hide his embarrassing little dick. No, he corrected himself. Sissy's don't have dicks. They have little sissy clitties. But without a domme or dom and a chastity cage he wasn't even a sissy yet.
He'd forgotten his place and begged TERP to refer him to someone. If this wonderful man wouldn't take him, he must have friends just as wonderful."
"Sorry kitten, I still don't know anyone. If you were in Seattle I'd cage you and make you a little girl myself. The idea of having a sissy to train is pretty damned compelling. It's been a fun conversation."
"well i'm not a sissy yet"
"But you want to be?"
...
"Y-yes."
That was when TERP started giving him homework.
"Start brushing your tongue, not only does this help with your breath but you'll be doing it to learn to control your gag reflex."
"Buy yourself a dildo." TERP had given him a very detailed description of what sort of beginner toy he should start with.
"Head to the store and buy some panties. You'll start with just a couple of pairs and you'll wear them to sleep. When they no longer distract you, you'll start wearing them during the day."
When the weather had begun to cool off Jason had added a tshirt to the panties as his normal sleeping outfit. When TERP had discovered this Jason had learned what camisoles were. Basically they were tank tops but with thin little straps. He'd picked up a couple and begun sleeping in a cami and panties. By then he had to start taking his laundry to the laundromat to hide the women's clothes. This pleased Daddy, er... TERP, very much.
"Good girls do the laundry without complaint."
TERP began assigning porn to watch. Sissy porn, Cuck porn, ladyboy porn. Any porn where you were likely to find small dicks.
"You will masterbate from time to time." That order made his heart drop a bit. (He had hoped to be able to hold out until the day he was actually able to meet Ian.) "It’s important to empty that prostate and until there’s a CG around to milk you right you’ll have to do it the old fashioned way. Since I’m not around you’ll eat the cum afterwards. I don’t want my cum fountain going to waste and you'll get you used to drinking it. Learn to play with it. I love to watch little girls play with cum." A CG was a caregiver. Part of a CGL relationship: A caregiver, someone who acted like an adult, and a little, someone who acted like a child and needed to be cared for.
He started getting femboy/eboy clothes, and learned that pretty much all of his favorite anime had plushies which he began to decorate his room with.
On his own he found a sissy exercise regime. It was almost entirely squats. Designed to give women a big ass they work the same for men. He also knew TERP liked his sissies clean and smooth and began to shave.
The clothes he was starting to wear to bed were getting pinker and frillier. He dreaded the day TERP would ask him to wear something like that in public.
"We'll start getting you chokers to wear instead of collars in public. Initially you can choose manly ones but they will get girlier."
"Start looking up metrosexual/femboy/androgynous outfits and moving your clothing style in that direction. We don’t need you in dresses while you’re with your parents. Well do that later but you’ll totally feel like a girl wearing a bodysuit as a top.
"Start paying attention to women's fashions. What would you want to wear, what would you want to look like as a woman. The kawaii stuff will likely only be for private time."
By now TERP, who's real name was Ian, wasn't just helping. He'd become directly interested and they'd started roleplaying from time to time. Initially the play was a bit disappointing. Instead of the cruelty and degradation Jason had been expecting (and looking forward to) Ian was sweet, caring and understanding. Jason had expected a stronger hand. He was also thrown off by Ian's desires. Ian doesn't believe in "Sissy boys." To Ian they are all "Sissy Girls." And instead of being worthless scum whose only purpose is to be abused and used, Ian feels that sissies deserve to be loved and cared for (as long as they earn it.) But then Jason began to enjoy Ian's pet names. Being called "Princess" and "Kitten" made him feel girly and cute. And Ian's insistence that Jason didn't have a "worthless dick" but instead "A cute and lovely little sissy clitty" had begun to increase his confidence. Though they both agreed that it was too small to be considered a dick or a penis.
Jason had begun to buy more feminine clothing for daily wear. Not women's clothing just what Ian referred to as "metro sexual."
Ian lives on the other side of the country so the odds of them meeting in person had been low. During their play Ian had begun talking about "Finding Jason a local dom like his good little sissy deserved." It was filling Jason with feelz. He'd really begun to get attached to the idea of having a Daddy and of serving Ian specifically. He'd even changed his roles to "Not looking" and "Honorary chastity."
But today Jason was ecstatic. Today Ian was arriving in NY on a business trip. His plane should be landing right about now and they had dinner plans later that evening.
Jason had been preparing for this moment all day. He had shaved all over and moisturized his skin like Ian taught him. Then he'd gone to his closet and picked out 3 outfits, laid them out on the bed, taken a picture and sent it earlier that morning. But Ian had been in the air and wouldn't get it until he landed. Jason expected Ian probably wouldn't respond until he got settled in to his hotel which would probably be about an hour away. But Jason liked this park. For one thing it wasn't filled with the bickering of his parents. And he didn't mind the wait.
Jason was about to doze off when his phone dinged. "Just hit the tarmac and we're taxying to the gate. Such a good girl to get her picture out early." Jason's chest swelled with pride. "But none of those outfits. Dress like a man, no choker, no makeup, boxers. I want you out of subspace for dinner."
Out of subspace? Subspace is the place you go when you are being controlled by a capable dom or domme. Subspace is the place where all your desires flow through your owner. You want nothing but to please them and in turn you are only happy if they are happy. Sub space was where Jason lived whenever Ian talked, or texted, hell Jason was in subspace the moment he even thought of Ian. And "Dress like a man?" Ian had been very clear that he wasn't sexually aroused by men. What was going on? Jason had a terrifying thought, is this dinner a breakup dinner? He had so many questions.
"Why"
"Everything will be explained at dinner sweet pea. We're at the gate so I won't be able to respond until I get to the taxi."
"But you don't like masculine men and I want to be sexy for you."
The wait for a response was torture. Jason knew Ian would have his hands busy carrying luggage or whatever but he couldn't help feeling like he'd made a mistake. 20 minutes later his fears were confirmed.
"Good girls don't ask twice once they've been told no. You know this."
Daddy's Home: (M/TF)
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terpinderp
- Forum Contributer
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- Joined: 1 year ago
Daddy's Home: (M/TF)
Last edited by terpinderp 1 year ago, edited 2 times in total.
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terpinderp
- Forum Contributer
- Posts: 7
- Joined: 1 year ago
Chapter 2
Two hours later Jason's mind was still racing. He'd been so distracted that it had taken repeated tries to put together a "manly" outfit. It didn't help that he'd been in subspace when in front of the closet for long enough now that every time he started flipping through clothes he would slip back in and the new lace up arm sleeves he'd purchased just for the evening would start to call to him.
Eventually Jason managed to put together a passable outfit. Loose fitting jeans, a t-shirt, and topped it off with a sports coat his mother had bought him for his great grandmother's funeral. Jason looked at the clock.
Shit, how did that take two hours?
Jason sprints out of the house. He had two buses to change. The restaurant, Le Bernardin, was in the middle of the island of Manhattan. Hell's kitchen or Midtown East, something in there. There was a bridge to cross which always adds at least 20 minutes. Making it in time was going to depend largely on the transfer between the buses.
According to his watch there were two minutes left when He reached the front door of LeBernardin. Cutting it kind of close. The greeter ran his eyes up and down Jason, when they stopped pointedly on his baseball cap he began to worry that they wouldn't let him in. He'd known the hat was a stupid choice but a lot of manly men wore caps so he'd given it a try. Jason snatched it off his head and held it in front of him and the greeter continued as if he'd been in a movie on pause.
"Do you have a reservation... Sir." He didn't even attempt to hide the disdain in his voice.
"I'm meeting someone."
"Ah yes, we have a gentleman guest expecting a young man. Right this way."
What kind of a restaurant was this? Jason was led to the dining room past a bunch of art he didn't understand to a table by the window.
And there was Ian, real and in the flesh. He was bigger than Jason had imagined. Jason had seen pictures but in person Ian's shoulders were bigger and his chest broader. Or maybe that was just the effect of his belly being smaller. It looked like Ian had lost some weight since those photos. Still a cuddly dad bod but at the same time, in Jason's eyes, Ian looked a bit like a dark haired Thor. Ian was looking at his watch with a scowl when they stepped up. Jason had no idea what the etiquette for the situation was. What he wanted to do was jump into Ian's lap and wrap his arms around his neck but his insecurity got the best of him and instead he just stood there staring like a weeb. When the greeter pulled the chair out for Jason Ian looked up. Instantly the scowl was gone and a huge warm smile split his face.
"Great, you made it. I was beginning to think you'd be late." Did Jason catch a slight look of disapproval at the end?
He didn't notice the greeter leave. He couldn't see anything except Ian's eyes. Ian stood and took a step towards him. He felt a tiny involuntary shudder go through his body. He was MUCh bigger than Jason had expected. Jason knew Ian was tall at 6'3" but everyone was tall to him so he didn't understand the scale. Ian extended a hand. Reflexively Jason took the hand and they... shook... hands? What? Where was the hug, where were the cuddles and the head pats he was expecting. Ian indicated the chair across from his own.
"Yes sir" Jason moved to the chair.
He felt a strong hand grab his arm and turn him.
"Look at me." Ian demanded.
Jason looked at Ian, and Ian's delicious mouth, Ian's graying beard, Ian's broad chest, Ian's OH MY GOD look at the SIZE of that bulge.
"My eyes. Look me in the eyes" Ian said patiently.
With some effort Jason looked Ian in the eyes.
"No subspace at dinner. Right now we are simply two men having dinner. We will enjoy good food and drink, nerd out about something and finally have a serious chat. Now sit down, at your leisure and decide on what you want to eat."
With that Jason was out of subspace. "Have a serious chat" could only mean one thing. they were done. Jason had slid directly from subspace to despair.
They order their meals. Jason doesn't understand anything on the menu but with some help from Ian they get through it. Ian even orders Jason a scotch but it simply sits there on the table while they eat and talk. It's far too strong for Jason to handle.
They chat briefly about the traffic and his flight. The entire time Jason's skin is crawling. And not just because cotton boxers aren't as comfy as satin panties. Maybe it was time to just get it over with. Rip off the band-aid.
"O.k. I'm ready."
"Ready for what?" Ian asked
"Ready for you to tell me I'm too worthless to even be your sissy. Ready for you to dump me." Their relationship had always been too good to be true anyway.
"Do you want me to dump you?"
"NO!" Jason cries out just a little too loud drawing eyes from other patrons.
"Then why would I dump you?"
Now Jason was completely confused.
"Then why..." he managed, indicating his clothes.
Surprising himself Jason raises his head and makes eye contact with Ian. Ian is smiling.
"I asked you to come as your old self. To wear clothes that you chose yourself, to be the old you. I asked you this because this is the first time we have met in person and both of us are going to have to make some decisions for ourselves."
"Wha..."
"We've discussed our kinks and done some roleplaying and it's been fun. It's been rea fun." Ian says seriously. "But if we're going to take this to the next level we need to start over a little and get to know one another in person. We have to LIKE one another if we're really going to get together." Ian took a sip of his scotch before continuing. "Beyond that we have to have a serious talk about safety, limits, safe words and everything."
Ian does have a strong DDLG/CGL bent but isn't into actual children. He's not going to call Jason his daughter but will call him his little girl, little princess, and more. Jason is already aware that Ian isn't interested in degrading, abusing or forcing Jason to do things (often) but instead taking care of him "like a beloved pet." Jason still wishes Ian would take a firmer hand when they talked but he did enjoy being a pet beneath Ian's feet. Ian doesn't seem to have many other limits. He likes spanking, rope, suspension and more. "I do draw the line at skat and anything that will cause permanent harm."
Jason is much more quiet. He's already spilled most of his desires to Ian on discord but Ian does manage to coax out of him that beyond just wanting to be owned Jason would love it if Ian found a beautiful trans femme woman and the two of them used him like the most popular girl at the party.
"I'll keep that in mind." Ian says smiling.
They spend the next hour talking about nerdy things like dungeons and dragons and anime. They discuss their favorite Netflix shows. It takes a minute for Jason to get over the fact that they aren't having sexy talk but once he relaxes he finds himself enjoying the evening. He even gets up the courage to try the scotch but that doesn't work out and ends with an embarrassing episode of coughing.
They finish their food and Ian pays the check without even looking at the bill.
"Normally I would insist that the first date be dutch and end with us going our separate ways. This would give you an evening to ruminate on the date and decide if you wanted another. Then if you did choose, the second date would be much closer to what you were probably expecting. You would be in subspace proving you can be obedient for at least the length of a meal. But we've known each other for long enough that I'll let you decide. We could meet tomorrow for breakfast, dinner or not at all."
"Or.." he added, pausing. "you could simply join me in my hotel room. No obligation, no pressu..."
"YES" Jason blurts out
"Good girls don't interrupt." Ian says clucking his tongue and wagging his finger like a schoolmarm in a children's cartoon.
Instantly Jason is back in subspace.
"I'm sorry daddy, I'll do better."
Ian patts Jason on his head and sticks out his elbow. Jason looks up in confusion.
"It's called offering you my arm." Ian says wagging the elbow. "You slip yours into mine."
Meekly Jason complies, looking around hoping no-one will stare. They walk somewhat uncomfortably at first. Then Jason discovers he can hold on to Daddy's strong bicep and lean against him. Arm in arm they walk to the car.
The drive to Ian's hotel is quiet and short. They leave the car with the valet and take the elevator up to his floor. By the time they get to the door Jason is perfectly comfortable and has forgotten to worry that he might be seen by someone he knows.
Two hours later Jason's mind was still racing. He'd been so distracted that it had taken repeated tries to put together a "manly" outfit. It didn't help that he'd been in subspace when in front of the closet for long enough now that every time he started flipping through clothes he would slip back in and the new lace up arm sleeves he'd purchased just for the evening would start to call to him.
Eventually Jason managed to put together a passable outfit. Loose fitting jeans, a t-shirt, and topped it off with a sports coat his mother had bought him for his great grandmother's funeral. Jason looked at the clock.
Shit, how did that take two hours?
Jason sprints out of the house. He had two buses to change. The restaurant, Le Bernardin, was in the middle of the island of Manhattan. Hell's kitchen or Midtown East, something in there. There was a bridge to cross which always adds at least 20 minutes. Making it in time was going to depend largely on the transfer between the buses.
According to his watch there were two minutes left when He reached the front door of LeBernardin. Cutting it kind of close. The greeter ran his eyes up and down Jason, when they stopped pointedly on his baseball cap he began to worry that they wouldn't let him in. He'd known the hat was a stupid choice but a lot of manly men wore caps so he'd given it a try. Jason snatched it off his head and held it in front of him and the greeter continued as if he'd been in a movie on pause.
"Do you have a reservation... Sir." He didn't even attempt to hide the disdain in his voice.
"I'm meeting someone."
"Ah yes, we have a gentleman guest expecting a young man. Right this way."
What kind of a restaurant was this? Jason was led to the dining room past a bunch of art he didn't understand to a table by the window.
And there was Ian, real and in the flesh. He was bigger than Jason had imagined. Jason had seen pictures but in person Ian's shoulders were bigger and his chest broader. Or maybe that was just the effect of his belly being smaller. It looked like Ian had lost some weight since those photos. Still a cuddly dad bod but at the same time, in Jason's eyes, Ian looked a bit like a dark haired Thor. Ian was looking at his watch with a scowl when they stepped up. Jason had no idea what the etiquette for the situation was. What he wanted to do was jump into Ian's lap and wrap his arms around his neck but his insecurity got the best of him and instead he just stood there staring like a weeb. When the greeter pulled the chair out for Jason Ian looked up. Instantly the scowl was gone and a huge warm smile split his face.
"Great, you made it. I was beginning to think you'd be late." Did Jason catch a slight look of disapproval at the end?
He didn't notice the greeter leave. He couldn't see anything except Ian's eyes. Ian stood and took a step towards him. He felt a tiny involuntary shudder go through his body. He was MUCh bigger than Jason had expected. Jason knew Ian was tall at 6'3" but everyone was tall to him so he didn't understand the scale. Ian extended a hand. Reflexively Jason took the hand and they... shook... hands? What? Where was the hug, where were the cuddles and the head pats he was expecting. Ian indicated the chair across from his own.
"Yes sir" Jason moved to the chair.
He felt a strong hand grab his arm and turn him.
"Look at me." Ian demanded.
Jason looked at Ian, and Ian's delicious mouth, Ian's graying beard, Ian's broad chest, Ian's OH MY GOD look at the SIZE of that bulge.
"My eyes. Look me in the eyes" Ian said patiently.
With some effort Jason looked Ian in the eyes.
"No subspace at dinner. Right now we are simply two men having dinner. We will enjoy good food and drink, nerd out about something and finally have a serious chat. Now sit down, at your leisure and decide on what you want to eat."
With that Jason was out of subspace. "Have a serious chat" could only mean one thing. they were done. Jason had slid directly from subspace to despair.
They order their meals. Jason doesn't understand anything on the menu but with some help from Ian they get through it. Ian even orders Jason a scotch but it simply sits there on the table while they eat and talk. It's far too strong for Jason to handle.
They chat briefly about the traffic and his flight. The entire time Jason's skin is crawling. And not just because cotton boxers aren't as comfy as satin panties. Maybe it was time to just get it over with. Rip off the band-aid.
"O.k. I'm ready."
"Ready for what?" Ian asked
"Ready for you to tell me I'm too worthless to even be your sissy. Ready for you to dump me." Their relationship had always been too good to be true anyway.
"Do you want me to dump you?"
"NO!" Jason cries out just a little too loud drawing eyes from other patrons.
"Then why would I dump you?"
Now Jason was completely confused.
"Then why..." he managed, indicating his clothes.
Surprising himself Jason raises his head and makes eye contact with Ian. Ian is smiling.
"I asked you to come as your old self. To wear clothes that you chose yourself, to be the old you. I asked you this because this is the first time we have met in person and both of us are going to have to make some decisions for ourselves."
"Wha..."
"We've discussed our kinks and done some roleplaying and it's been fun. It's been rea fun." Ian says seriously. "But if we're going to take this to the next level we need to start over a little and get to know one another in person. We have to LIKE one another if we're really going to get together." Ian took a sip of his scotch before continuing. "Beyond that we have to have a serious talk about safety, limits, safe words and everything."
Ian does have a strong DDLG/CGL bent but isn't into actual children. He's not going to call Jason his daughter but will call him his little girl, little princess, and more. Jason is already aware that Ian isn't interested in degrading, abusing or forcing Jason to do things (often) but instead taking care of him "like a beloved pet." Jason still wishes Ian would take a firmer hand when they talked but he did enjoy being a pet beneath Ian's feet. Ian doesn't seem to have many other limits. He likes spanking, rope, suspension and more. "I do draw the line at skat and anything that will cause permanent harm."
Jason is much more quiet. He's already spilled most of his desires to Ian on discord but Ian does manage to coax out of him that beyond just wanting to be owned Jason would love it if Ian found a beautiful trans femme woman and the two of them used him like the most popular girl at the party.
"I'll keep that in mind." Ian says smiling.
They spend the next hour talking about nerdy things like dungeons and dragons and anime. They discuss their favorite Netflix shows. It takes a minute for Jason to get over the fact that they aren't having sexy talk but once he relaxes he finds himself enjoying the evening. He even gets up the courage to try the scotch but that doesn't work out and ends with an embarrassing episode of coughing.
They finish their food and Ian pays the check without even looking at the bill.
"Normally I would insist that the first date be dutch and end with us going our separate ways. This would give you an evening to ruminate on the date and decide if you wanted another. Then if you did choose, the second date would be much closer to what you were probably expecting. You would be in subspace proving you can be obedient for at least the length of a meal. But we've known each other for long enough that I'll let you decide. We could meet tomorrow for breakfast, dinner or not at all."
"Or.." he added, pausing. "you could simply join me in my hotel room. No obligation, no pressu..."
"YES" Jason blurts out
"Good girls don't interrupt." Ian says clucking his tongue and wagging his finger like a schoolmarm in a children's cartoon.
Instantly Jason is back in subspace.
"I'm sorry daddy, I'll do better."
Ian patts Jason on his head and sticks out his elbow. Jason looks up in confusion.
"It's called offering you my arm." Ian says wagging the elbow. "You slip yours into mine."
Meekly Jason complies, looking around hoping no-one will stare. They walk somewhat uncomfortably at first. Then Jason discovers he can hold on to Daddy's strong bicep and lean against him. Arm in arm they walk to the car.
The drive to Ian's hotel is quiet and short. They leave the car with the valet and take the elevator up to his floor. By the time they get to the door Jason is perfectly comfortable and has forgotten to worry that he might be seen by someone he knows.
Last edited by terpinderp 1 year ago, edited 1 time in total.
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terpinderp
- Forum Contributer
- Posts: 7
- Joined: 1 year ago
Chapter 3
Not that there was much chance of that up on Ian's floor. The long hall that the elevators spilled out into held no more than three doors and Ian had needed to use his hotel key to simply press the floor number at all.
Ian unlocks the door with a swipe of the hotel key and opens it. Standing aside he indicates that Jason should precede him.
The suite is grand with a sofa and a television that Jason barely notices. On one side of the room a pair of double doors open into the bedroom. Jason's heart jumps at the site of the bed. He desperately wants to be cuddled, and more, by Ian in that bed.
Ian finds himself in front of the bed feeling the soft down comforter
Suddenly Jason's arms are pinned back and his head forced down. He recognizes being in a headlock, his childhood had been full of them. His face is forced down onto the bed before he can even gasp. On the bed he is released briefly before his wrists are grabbed and brought together. His arms are tied behind his back with his hands grabbing his elbows. Jason begins to wonder if he's made a mistake. Where is the love and care from texting? Ian reaches under him and unclasps Jason's belt. His pants and underwear are slid down to his ankles. One strong hand holding Jason down the other collides with his naked rear end. The pain is nothing like the experimentation Jason had done on himself with a hairbrush. In shock he cries out.
"Well that won't do." Says Ian.
And suddenly Jason's legs are being lifted, his back arching. His shoes, socks, pants and undies are removed.
"These should do."
Jason's legs are dropped and the underwear shoved into his mouth. This is followed by a ball gag.
Ian has frequently mentioned how he would keep his little girl's ass red but Jason has never been spanked before.
Then the spanking resumes. The pain is excruciating. Jason tries to keep quiet but with each slap it hurts more. Despite his efforts he screams and tries to roll away. But the gag and cotton boxers do an excellent job of quieting him and the hand holding him simply pressed down harder instantly preventing him from rolling away. A flurry of blows pushes all conscious thought from his mind, his ass and his brain are on fire.
As suddenly as it began the spanking stops. Jason is left with an aching rear end. He can feel tears beginning to dry on his cheeks and his nose has begun to run. Has he been crying? He blinks his eyes and tries to take a deep breath but the sniffling bad enough that he has trouble taking a deep enough breath. He's still terrified but also a little excited. As wonderful as being dominated via text has been he's never been so completely controlled before. In the quiet, broken only by the sound of Ian moving behind him, he begins to tremble. A heavy weight falls onto the bed next to him. Gravity rolls him in that direction and he stops against a warm, firm chest. Turning his head he find's Ian's face inches from his own and wearing that heart melting smile he'd seen at the restaurant.
"Are you scared?" Ian asks.
"Y-yes." He replies meekly.
Ian's face droops with concern.
"I'm sorry baby girl. I don't want to scare you. But Daddy needed to set the tone."
He begins gently stroking Jason's hair and face.
"You're mine now. And I get to do whatever I want to you whenever I want. I know we've talked about it before so you know it up here." He says gently tapping Jason on the forehead..
"But I need you to know it here." He lays a hand over Jason's heart which immediately begins beating faster as if it was trying to jump out of his chest and directly into his daddy's hand.
"I hope my little princess understands."
Ian was right. Through all the role-playing and e sex Jason had definitely felt subservient to Ian. But until that moment he hadn't truly felt like Ian's property.
"I do daddy." He says lowering his eyes.
Ian's arms slide around Jason.
"You did such a good job, baby girl."
He begins kissing Jason's cheeks.
"You have no idea how much I enjoy tears on a beautiful girl's face. Daddy is so proud."
Slowly the ball-gag and undies are removed. Somehow Ian doesn't even slow down kissing Jason's tears away.
"We'll do whatever you want next. A reward like this is usually saved for special occasions. But since it's our first time together and it's brief, it will be better for developing your attachment if we do something you really want to do."
His mouth freed, Jason desperately wishes Ian would move his mouth to his. Should he ask? Daddy had said he could ask for things but only once. He can't wait to feel it crushed by Ian's thick wonderful lips. To feel the beard that was currently scratching his cheek scratch against his lips.
Instead Ian's mouth moves away. Jason finds his mouth moving to a pout. Damn, what was happening. Now he was pouting like a little girl.
Ian's eyes move down Jason's body.
"But not yet." He says with finality, "I'm not done with that ass yet."
Jason shudders and waits expecting the gag to be returned. But it isn't. As Ian moves behind him something wet and warm lands on his ass and begins to slide down his ass-crack. Ian's hands spread Jason's cheeks apart and he begins rubbing the liquid around Jason's anus with his thumb. As the thumb's pressure increases and his anus, his boy pussy, begins to open. Jason realizes that's not Ian's thumb. It's been the head of his cock this whole time. Jason is terrified, daddy is not small. They've shared measurements and pictures. And Daddy was not only Far bigger than him but was significantly larger than his current toy with probably twice the girth. At the same time he was also elated. His greatest joy of the past three months has been imagining this moment. Now that it was here he hoped he could take it.
Ian began caressing his back gently.
"Shh... don't worry little lamb, I'll go real slow. Just relax. Now you should feel an ache as you are stretched but not a sharp pain. If you feel a sharp pain tell me and we'll stop and get you taken care of okay?"
"I'll try daddy."
"I need you to do better than try sweetheart. You know how I feel about my things. I don't like them being damaged. If you're going to be my little girl I'm going need you to take as good care of my things as I do." He said in a serious tone.
"And you're mine right?"
"Yes daddy."
"Then you need to help me take care of you. You need to tell me if you feel a sharp pain and let me take care of you."
"I will daddy"
"Good girl."
And then he was being stretched. The head of Ian's cock slowly spreads his anus wide. And it felt amazing. It certainly hurt but whenever he let out a small cry or started to tense up Ian would stop or even back out. When the latter happened Jason desperately wanted to grab daddy and pull him back into him. It hurt like hell but he couldn't wait to feel the whole length.
Before long daddy was slowly sliding in and out of him. The head of his cock bumping against Jason's prostrate was unbelievable. It was somewhat like using the toy but so much more. His vision blurred and he realized that he was being fucked cross eyed. Another promise from daddy had been kept. He'd promised to use Jason and fuck him cross eyed on this trip. As his brain began to turn to mush he felt the last vestiges of any resistance disappearing. He knew there was no going back. He belonged to Ian completely now, heart, soul, and certainly body.
Not that there was much chance of that up on Ian's floor. The long hall that the elevators spilled out into held no more than three doors and Ian had needed to use his hotel key to simply press the floor number at all.
Ian unlocks the door with a swipe of the hotel key and opens it. Standing aside he indicates that Jason should precede him.
The suite is grand with a sofa and a television that Jason barely notices. On one side of the room a pair of double doors open into the bedroom. Jason's heart jumps at the site of the bed. He desperately wants to be cuddled, and more, by Ian in that bed.
Ian finds himself in front of the bed feeling the soft down comforter
Suddenly Jason's arms are pinned back and his head forced down. He recognizes being in a headlock, his childhood had been full of them. His face is forced down onto the bed before he can even gasp. On the bed he is released briefly before his wrists are grabbed and brought together. His arms are tied behind his back with his hands grabbing his elbows. Jason begins to wonder if he's made a mistake. Where is the love and care from texting? Ian reaches under him and unclasps Jason's belt. His pants and underwear are slid down to his ankles. One strong hand holding Jason down the other collides with his naked rear end. The pain is nothing like the experimentation Jason had done on himself with a hairbrush. In shock he cries out.
"Well that won't do." Says Ian.
And suddenly Jason's legs are being lifted, his back arching. His shoes, socks, pants and undies are removed.
"These should do."
Jason's legs are dropped and the underwear shoved into his mouth. This is followed by a ball gag.
Ian has frequently mentioned how he would keep his little girl's ass red but Jason has never been spanked before.
Then the spanking resumes. The pain is excruciating. Jason tries to keep quiet but with each slap it hurts more. Despite his efforts he screams and tries to roll away. But the gag and cotton boxers do an excellent job of quieting him and the hand holding him simply pressed down harder instantly preventing him from rolling away. A flurry of blows pushes all conscious thought from his mind, his ass and his brain are on fire.
As suddenly as it began the spanking stops. Jason is left with an aching rear end. He can feel tears beginning to dry on his cheeks and his nose has begun to run. Has he been crying? He blinks his eyes and tries to take a deep breath but the sniffling bad enough that he has trouble taking a deep enough breath. He's still terrified but also a little excited. As wonderful as being dominated via text has been he's never been so completely controlled before. In the quiet, broken only by the sound of Ian moving behind him, he begins to tremble. A heavy weight falls onto the bed next to him. Gravity rolls him in that direction and he stops against a warm, firm chest. Turning his head he find's Ian's face inches from his own and wearing that heart melting smile he'd seen at the restaurant.
"Are you scared?" Ian asks.
"Y-yes." He replies meekly.
Ian's face droops with concern.
"I'm sorry baby girl. I don't want to scare you. But Daddy needed to set the tone."
He begins gently stroking Jason's hair and face.
"You're mine now. And I get to do whatever I want to you whenever I want. I know we've talked about it before so you know it up here." He says gently tapping Jason on the forehead..
"But I need you to know it here." He lays a hand over Jason's heart which immediately begins beating faster as if it was trying to jump out of his chest and directly into his daddy's hand.
"I hope my little princess understands."
Ian was right. Through all the role-playing and e sex Jason had definitely felt subservient to Ian. But until that moment he hadn't truly felt like Ian's property.
"I do daddy." He says lowering his eyes.
Ian's arms slide around Jason.
"You did such a good job, baby girl."
He begins kissing Jason's cheeks.
"You have no idea how much I enjoy tears on a beautiful girl's face. Daddy is so proud."
Slowly the ball-gag and undies are removed. Somehow Ian doesn't even slow down kissing Jason's tears away.
"We'll do whatever you want next. A reward like this is usually saved for special occasions. But since it's our first time together and it's brief, it will be better for developing your attachment if we do something you really want to do."
His mouth freed, Jason desperately wishes Ian would move his mouth to his. Should he ask? Daddy had said he could ask for things but only once. He can't wait to feel it crushed by Ian's thick wonderful lips. To feel the beard that was currently scratching his cheek scratch against his lips.
Instead Ian's mouth moves away. Jason finds his mouth moving to a pout. Damn, what was happening. Now he was pouting like a little girl.
Ian's eyes move down Jason's body.
"But not yet." He says with finality, "I'm not done with that ass yet."
Jason shudders and waits expecting the gag to be returned. But it isn't. As Ian moves behind him something wet and warm lands on his ass and begins to slide down his ass-crack. Ian's hands spread Jason's cheeks apart and he begins rubbing the liquid around Jason's anus with his thumb. As the thumb's pressure increases and his anus, his boy pussy, begins to open. Jason realizes that's not Ian's thumb. It's been the head of his cock this whole time. Jason is terrified, daddy is not small. They've shared measurements and pictures. And Daddy was not only Far bigger than him but was significantly larger than his current toy with probably twice the girth. At the same time he was also elated. His greatest joy of the past three months has been imagining this moment. Now that it was here he hoped he could take it.
Ian began caressing his back gently.
"Shh... don't worry little lamb, I'll go real slow. Just relax. Now you should feel an ache as you are stretched but not a sharp pain. If you feel a sharp pain tell me and we'll stop and get you taken care of okay?"
"I'll try daddy."
"I need you to do better than try sweetheart. You know how I feel about my things. I don't like them being damaged. If you're going to be my little girl I'm going need you to take as good care of my things as I do." He said in a serious tone.
"And you're mine right?"
"Yes daddy."
"Then you need to help me take care of you. You need to tell me if you feel a sharp pain and let me take care of you."
"I will daddy"
"Good girl."
And then he was being stretched. The head of Ian's cock slowly spreads his anus wide. And it felt amazing. It certainly hurt but whenever he let out a small cry or started to tense up Ian would stop or even back out. When the latter happened Jason desperately wanted to grab daddy and pull him back into him. It hurt like hell but he couldn't wait to feel the whole length.
Before long daddy was slowly sliding in and out of him. The head of his cock bumping against Jason's prostrate was unbelievable. It was somewhat like using the toy but so much more. His vision blurred and he realized that he was being fucked cross eyed. Another promise from daddy had been kept. He'd promised to use Jason and fuck him cross eyed on this trip. As his brain began to turn to mush he felt the last vestiges of any resistance disappearing. He knew there was no going back. He belonged to Ian completely now, heart, soul, and certainly body.
-
terpinderp
- Forum Contributer
- Posts: 7
- Joined: 1 year ago
Chapter 4
Ian was really pumping him now. He wanted to grab Ian, grab the sheets, grab something but his arms were still tied. No, her arms were still tied. I'm daddy's good little girl. So she settled for biting the sheets. Which had the added benefit of muffling his moaning.
Pressure was building in his groin, her groin. Her prostate throbbing between every thrust. Jason cries out in ecstasy as her brain explodes. What's happening. Her eyes squeezed tightly shut he can't breathe, he can't think, all she can do is shudder as wave after wave of pleasure crashes through her body.
"Oh fuck" he hears behind him and Ian, daddy, thrusts deep inside of her pinning her to the bed and holding his cock deeper than it's been before.
Daddy's hands grab Jason's hips roughly and she feels daddy's seed filling her up. Then her little clitty is pulsing and her own is spilled onto the bed sheets. She hopes daddy won't be upset at her for not asking permission before everything slowly begins to fade. Was that a "Good girl" I just heard she wonders before succumbing to the black.
Jason wakes up in daddy's arms. Apparently he'd passed out for a minute. Lying on his chest he feels daddy untying the rope binding his arms. Once freed they both sit up and Jason finds himself in his daddy's lap.
"Let's get you cleaned up and treated." He rumbles
Jason is swept up in daddy's arms and carried to the bathroom where he is gently lowered. When his feet touch the floor Jason knows she won't be able to stand on her own. Fortunately Jason is bent over, her chest laid on the sink. Daddy picks up a jar of aloe from next to Jason's head and begins to spread it on Jason's ass. The touch stings slightly at first but then the aloe begins to work and the stinging subsides into a dull ache.
They move to the main room, Jason now on her feet able to stumble meekly behind Daddy. Daddy sits down in a large chair and draws Jason down into his lap. Carefully she sits down. It hurts like hell and takes a couple of tries. Each time she lets out a little yelp daddy smiles a little better. Once she's settled she looks up into his eyes and daddy begins caressing her cheek.
"Fuck that was hot. You were so beautiful with your red ass in the air and tears on your cheeks."
The pain from sitting on took Jason back to every slap. At least the ones he could remember before he lost himself completely. In fact sitting on it was making it hurt more. He'd been shifting around trying to find a more comfortable position. And now he felt something firming under him. Something that was beginning to poke into his ass cheek. Jason knew what it was and found himself blushing.
"You are such a good girl." Daddy said, still stroking his cheek. "Now it's your turn. What does my princess want to do on her first day in bed with daddy? Anything your little heart desires."
She couldn't believe it. She had been thinking of nothing but this evening for weeks now imagining all of the things daddy would do to her. Now she was in his daddy's arms and being told to choose anything to do. And her brain simply couldn't come up with any ideas.
Daddy brushed Jason's hair behind an ear. "It's ok. Whatever you want. What do you want from daddy?"
His dick. Came the thought un-biden into his brain.
"Well..." she stuttered, "I still haven't..."
"Yes?" Daddy's voice was filled with patience.
"I still haven't seen your cock in person."
Ian smiled.
"And you would like to poppet?"
"Very much daddy."
Ian unraveles himself from around Jason and indicates that she should move off daddy's lap. Jason complies, kneeling in front of him. Tick, a promise from Jason kept. Hesitantly she reaches for his belt.
"Eventually you'll learn to do this with your arms tied behind your back. But for this trip I want you to explore me, to learn my body. Go ahead and take it out and look at it. In fact you can do whatever you want with it once it's out."
Timidly Jason works daddy's belt and buttons fly open. Daddy kicks off his pants and Jason is presented with Daddy's enormous, perfect cock. He wants to touch it but he's afraid. It's so damned big. He can't believe that had recently been in his ass. Seeing her trepidation daddy takes her hand and gently places it on his cock repeating "Whatever you want to do with it."
Jason looked into those big brown eyes and he knew what he wanted to do. He'd been wanting to do it for over a month now. He wanted to show off his new skill to his daddy. He'd been working extra hard on controlling his gag reflex and four weeks ago had been able to get his dildo into his throat for the first time. He had kept it a secret until now.
Hoping the extra girth wouldn't derail his plans he dips his head and slides daddy's cock into his mouth. When it bumps against the back of his throat he hears his daddy moan low.
"Mmm... good girl." Daddy says quietly.
And then the moment Jason has been waiting for. She relaxes her throat and shoves harder.
"Jesus Christ!" Daddy gasps and Jason's heart skips a beat. Strong hands land on his head. Not shoving but caressing. Daddy holds still as Jason begins to bob up and down sliding the dick in and out of his throat. He's seen rough porn where a guy shoves his dick into a woman's mouth and pinches their nose closed so that they can't breathe. Secretly he wishes daddy would do this but doesn't want to ask. Daddy is probably too nice for that. Besides, it's hard to talk with an enormous dick in your mouth and Jason had no interest in slowing down. Her hands begin to caress his daddy's chest and thighs as her pace increases. She pulls back and begins to play with the head and frenulum. Daddy looks at him with a smirk of surprise.
"Someone has been practicing." He smiles.
Jason blushes and turns her eyes back to her work.
She cups, fondles and eventually sucks on daddy's balls enjoying the sight when daddy closes his eyes and leans his head back. Daddy's body begins to tense more and more. His breathing becomes labored and rapid. She works back to throating the meaty member and daddy's hips begin to move.
"Aah!" cries daddy and his hands return to Jason's head. This time those gentle hands are much firmer and daddy's cock is thrust further down Jason's throat than ever, her face bumping into daddy's stomach and held there.
It turns out that daddy doesn't need to hold Jason's nose. His dick is long enough to completely cut off Jason's air supply on its own. She finds herself completely unable to breathe when the meaty cock starts throbbing. Jason can feel the throbbing on her tongue, cheeks and throat. Then warm cum is spurting down her throat and into her stomach. Oh no, daddy has always said he wanted to cum in Jason's mouth and watch her play with it; she'll never be able to do that if it's already in her stomach. She tries to move out to catch the rest on her tongue but the hands press harder. By the time the cock stops pulsing she is beginning to get light headed from lack of air.
As suddenly the thrust begins her head is pulled off the cock and she gasps for breath. Light headed she begins to tip over but daddy leans down and his strong arms catch and hold her. When her head clears a bit she turns her eyes down in shame.
"What's the matter, poppet?" Daddy says with concern. "We didn't hurt that lovely throat did we?"
"No, I just know how much you wanted to cum on my tongue and I screwed it up."
Daddy gently takes her chin and turns her face to his. Yes, She was daddy's little girl now and forever.
"Daddy is going to cum wherever daddy wants to cum silly little princess. Don't worry, I plan to cum on that lovely little pink tongue many times before this trip is over.
They have sex four more times that night. Jason can't cum again but daddy makes up for it by showering her in cum. Tick, another daddy promise fulfilled. Until finally they fall asleep in each other's arms.
Jason wakes up a short time later, it's 1am. She's going to have to climb the tree next to the garage and sneak in his bedroom window. She hoped she'd left it unlatched.
Quietly he gets dressed and makes his way to the door.
He is startled by a voice behind him.
"Where are you going?"
"I'm sorry daddy I didn't mean to wake you." She says turning. "I thought you were done with me and would want me to go home."
Daddy was still stark naked (was his cock getting hard again?!?!) and what was that in his hand.
"I'm certainly not done with you yet." He says with a grin.
"Go if you need to. But I was hoping my kitten would stay the night."
He passes her the object in his hand and she realizes it's a key card just like the one daddy used to open the hotel suite door. He couldn't mean.
"For you, so that you can come back when you are free. I might be at work but you can watch TV, order room service, and escape your family."
Looking up into those inviting brown eyes Jason made his decision. He was going to have a hard conversation with his parents the next day when they ask where he'd been all night but there was no way he was leaving now. As she slipped past daddy on her way back into the suite she takes a chance and slips her hand into daddy's. She's pleased when the larger hand clasps her own and daddy lets her lead him back to the bed..
Despite the erection they don't have sex again. Jason offers his body to daddy to take care of the erection but daddy declines.
"There will be time for that in the morning."
She falls asleep curled against daddy's chest. Daddy's arms wrapped around him. His large, real man's cock pressing against Jason's backside.
Ian was really pumping him now. He wanted to grab Ian, grab the sheets, grab something but his arms were still tied. No, her arms were still tied. I'm daddy's good little girl. So she settled for biting the sheets. Which had the added benefit of muffling his moaning.
Pressure was building in his groin, her groin. Her prostate throbbing between every thrust. Jason cries out in ecstasy as her brain explodes. What's happening. Her eyes squeezed tightly shut he can't breathe, he can't think, all she can do is shudder as wave after wave of pleasure crashes through her body.
"Oh fuck" he hears behind him and Ian, daddy, thrusts deep inside of her pinning her to the bed and holding his cock deeper than it's been before.
Daddy's hands grab Jason's hips roughly and she feels daddy's seed filling her up. Then her little clitty is pulsing and her own is spilled onto the bed sheets. She hopes daddy won't be upset at her for not asking permission before everything slowly begins to fade. Was that a "Good girl" I just heard she wonders before succumbing to the black.
Jason wakes up in daddy's arms. Apparently he'd passed out for a minute. Lying on his chest he feels daddy untying the rope binding his arms. Once freed they both sit up and Jason finds himself in his daddy's lap.
"Let's get you cleaned up and treated." He rumbles
Jason is swept up in daddy's arms and carried to the bathroom where he is gently lowered. When his feet touch the floor Jason knows she won't be able to stand on her own. Fortunately Jason is bent over, her chest laid on the sink. Daddy picks up a jar of aloe from next to Jason's head and begins to spread it on Jason's ass. The touch stings slightly at first but then the aloe begins to work and the stinging subsides into a dull ache.
They move to the main room, Jason now on her feet able to stumble meekly behind Daddy. Daddy sits down in a large chair and draws Jason down into his lap. Carefully she sits down. It hurts like hell and takes a couple of tries. Each time she lets out a little yelp daddy smiles a little better. Once she's settled she looks up into his eyes and daddy begins caressing her cheek.
"Fuck that was hot. You were so beautiful with your red ass in the air and tears on your cheeks."
The pain from sitting on took Jason back to every slap. At least the ones he could remember before he lost himself completely. In fact sitting on it was making it hurt more. He'd been shifting around trying to find a more comfortable position. And now he felt something firming under him. Something that was beginning to poke into his ass cheek. Jason knew what it was and found himself blushing.
"You are such a good girl." Daddy said, still stroking his cheek. "Now it's your turn. What does my princess want to do on her first day in bed with daddy? Anything your little heart desires."
She couldn't believe it. She had been thinking of nothing but this evening for weeks now imagining all of the things daddy would do to her. Now she was in his daddy's arms and being told to choose anything to do. And her brain simply couldn't come up with any ideas.
Daddy brushed Jason's hair behind an ear. "It's ok. Whatever you want. What do you want from daddy?"
His dick. Came the thought un-biden into his brain.
"Well..." she stuttered, "I still haven't..."
"Yes?" Daddy's voice was filled with patience.
"I still haven't seen your cock in person."
Ian smiled.
"And you would like to poppet?"
"Very much daddy."
Ian unraveles himself from around Jason and indicates that she should move off daddy's lap. Jason complies, kneeling in front of him. Tick, a promise from Jason kept. Hesitantly she reaches for his belt.
"Eventually you'll learn to do this with your arms tied behind your back. But for this trip I want you to explore me, to learn my body. Go ahead and take it out and look at it. In fact you can do whatever you want with it once it's out."
Timidly Jason works daddy's belt and buttons fly open. Daddy kicks off his pants and Jason is presented with Daddy's enormous, perfect cock. He wants to touch it but he's afraid. It's so damned big. He can't believe that had recently been in his ass. Seeing her trepidation daddy takes her hand and gently places it on his cock repeating "Whatever you want to do with it."
Jason looked into those big brown eyes and he knew what he wanted to do. He'd been wanting to do it for over a month now. He wanted to show off his new skill to his daddy. He'd been working extra hard on controlling his gag reflex and four weeks ago had been able to get his dildo into his throat for the first time. He had kept it a secret until now.
Hoping the extra girth wouldn't derail his plans he dips his head and slides daddy's cock into his mouth. When it bumps against the back of his throat he hears his daddy moan low.
"Mmm... good girl." Daddy says quietly.
And then the moment Jason has been waiting for. She relaxes her throat and shoves harder.
"Jesus Christ!" Daddy gasps and Jason's heart skips a beat. Strong hands land on his head. Not shoving but caressing. Daddy holds still as Jason begins to bob up and down sliding the dick in and out of his throat. He's seen rough porn where a guy shoves his dick into a woman's mouth and pinches their nose closed so that they can't breathe. Secretly he wishes daddy would do this but doesn't want to ask. Daddy is probably too nice for that. Besides, it's hard to talk with an enormous dick in your mouth and Jason had no interest in slowing down. Her hands begin to caress his daddy's chest and thighs as her pace increases. She pulls back and begins to play with the head and frenulum. Daddy looks at him with a smirk of surprise.
"Someone has been practicing." He smiles.
Jason blushes and turns her eyes back to her work.
She cups, fondles and eventually sucks on daddy's balls enjoying the sight when daddy closes his eyes and leans his head back. Daddy's body begins to tense more and more. His breathing becomes labored and rapid. She works back to throating the meaty member and daddy's hips begin to move.
"Aah!" cries daddy and his hands return to Jason's head. This time those gentle hands are much firmer and daddy's cock is thrust further down Jason's throat than ever, her face bumping into daddy's stomach and held there.
It turns out that daddy doesn't need to hold Jason's nose. His dick is long enough to completely cut off Jason's air supply on its own. She finds herself completely unable to breathe when the meaty cock starts throbbing. Jason can feel the throbbing on her tongue, cheeks and throat. Then warm cum is spurting down her throat and into her stomach. Oh no, daddy has always said he wanted to cum in Jason's mouth and watch her play with it; she'll never be able to do that if it's already in her stomach. She tries to move out to catch the rest on her tongue but the hands press harder. By the time the cock stops pulsing she is beginning to get light headed from lack of air.
As suddenly the thrust begins her head is pulled off the cock and she gasps for breath. Light headed she begins to tip over but daddy leans down and his strong arms catch and hold her. When her head clears a bit she turns her eyes down in shame.
"What's the matter, poppet?" Daddy says with concern. "We didn't hurt that lovely throat did we?"
"No, I just know how much you wanted to cum on my tongue and I screwed it up."
Daddy gently takes her chin and turns her face to his. Yes, She was daddy's little girl now and forever.
"Daddy is going to cum wherever daddy wants to cum silly little princess. Don't worry, I plan to cum on that lovely little pink tongue many times before this trip is over.
They have sex four more times that night. Jason can't cum again but daddy makes up for it by showering her in cum. Tick, another daddy promise fulfilled. Until finally they fall asleep in each other's arms.
Jason wakes up a short time later, it's 1am. She's going to have to climb the tree next to the garage and sneak in his bedroom window. She hoped she'd left it unlatched.
Quietly he gets dressed and makes his way to the door.
He is startled by a voice behind him.
"Where are you going?"
"I'm sorry daddy I didn't mean to wake you." She says turning. "I thought you were done with me and would want me to go home."
Daddy was still stark naked (was his cock getting hard again?!?!) and what was that in his hand.
"I'm certainly not done with you yet." He says with a grin.
"Go if you need to. But I was hoping my kitten would stay the night."
He passes her the object in his hand and she realizes it's a key card just like the one daddy used to open the hotel suite door. He couldn't mean.
"For you, so that you can come back when you are free. I might be at work but you can watch TV, order room service, and escape your family."
Looking up into those inviting brown eyes Jason made his decision. He was going to have a hard conversation with his parents the next day when they ask where he'd been all night but there was no way he was leaving now. As she slipped past daddy on her way back into the suite she takes a chance and slips her hand into daddy's. She's pleased when the larger hand clasps her own and daddy lets her lead him back to the bed..
Despite the erection they don't have sex again. Jason offers his body to daddy to take care of the erection but daddy declines.
"There will be time for that in the morning."
She falls asleep curled against daddy's chest. Daddy's arms wrapped around him. His large, real man's cock pressing against Jason's backside.
-
terpinderp
- Forum Contributer
- Posts: 7
- Joined: 1 year ago
Chapter 5
When Jason wakes up she finds herself clasping the sheets tightly, her back arched and her daddy's cock sliding slowly in and out of her ass. Apparently they'd begun having sex while she was still asleep. The sex is tender and loving. Daddy's arms wrap around her chest toying her nipples and holding her close to him. Again she finds that unfamiliar warmth in her groin and ass. Before long she is cumming from daddy's cock. When daddy sprays her back with cum she wishes it had been her face but doesn't turn. She knows daddy is looking at her ass.
Afterwards they shower. Daddy washing her body carefully. Stepping from the shower they dry one another and daddy sends her to the bedroom while he shaves and gets dressed. Back in the living room Jason sees clothes laid out on the coffee table. She sits and examines them. There are three pairs of panties. Two in simple satin bordered in delicate lace and one crinkly, bright pink pair with gigantic frills. The last pair was for sleeping, daddy had sent her pictures before. Next to the panties were two camisoles. These were lounging and sleeping outfits for Jason. She chooses one of the simpler panties and a camisole both in blue.
Daddy steps out of the bathroom and stops smiling.
"Good, I see you found the lounge wear. We'll take you out and let you pick something special for tonight's dinner after work." Jason felt a warmth in her cheeks. What was that? Was she blushing? She'd never done that as a boy.
"But before I go I have a surprise for you.
Daddy opens his luggage and pulls out a small box wrapped with a big pink bow. Handing it to Jason he tells her to open it.
Jason's eyes widened. It's a chastity cage. Her heart skips a beat. She'd been waiting for months wishing daddy would lock her up. Tick, another daddy promise fulfilled. It's one of the smaller micro cages. Most chastity cages were designed so that the wearer could get partially, but not fully, hard. The sensation was supposed to be very frustrating. Jason had saved up and purchased one before he had met daddy and found that his worthless little clitty was so small she could get fully erect in the cage. Then Daddy showed her the micro cages. They were so small they would squish even Jason's insignificant member. Not only that but since they constantly squished the dick down supposedly it didn't even try and get hard. Jason couldn't wait to feel it on. Every erection he got felt like his clitty was betraying him. It was too small to be used hard. He wished it would shrink to the size of a real girl's clit. He couldn't get his hand on it, just a few fingers, and wished it would almost disappear so that it could be diddled like a real clit.
The cage has a ring that goes around her shaft and behind her tiny balls. Then the cage is slid over her clittly and a lock inserted where the two meet. There is a click when daddy turns the key and the lock engages. Jason's heart skips a beat. Tick... Another daddy promise delivered. The promise he'd been dreaming of for months. Daddy has taken complete possession of her and any chance she has of pleasure.
There is a knock at the door and daddy moves to answer it. He returns with a tray filled with plates and glasses wrapped in saran wrap to keep them from spilling. He sets it on the table in the middle of the main room.
"I took the liberty of ordering breakfast. You don't mind." It wasn't a question so Jason doesn't answer. Daddy lifts the lids off of their dishes and sets them aside. There are eggs sunny side up with toast and hash browns for daddy. Jason looks at her own plate and finds scrambled eggs and pancakes. The pancakes are decorated with a happy face made from whipped cream. Jason smiles and picks up her knife and forth. Before she takes a bite she hears a "tut, tut" from daddy. Looking up Jason sees that he is indicating her napkin. Waving his knife in the direction of her top Jason tucks the napkin in like a bib and digs into her pancakes.
The chastity cage is tighter than she expected. And having something wrapped around your boy clit is highly erotic. Before he'd always been ashamed of it and almost afraid to touch it. But now he wanted to.
Noticing Jason squirming daddy dips under the table and pulls down her shorts. He begins playing with jasons balls and the sensation is fantastic.
A soft "Thank you daddy." Slips from his lips.
Daddy puts his mouth on the cage and for the first time in years Jason wishes he had a big dick. One that would please daddy. Secretly he begins to dream of daddy letting him out of the cage and sucking his little clitty.
He doesn't of course. After a few minutes of teasing Jason's caged clit, balls and nipples he simply stops, slowly stands and watches Jason squirm.
He looks at his watch. I'm going to have to leave in a hurry, you've distracted me more than I expected this morning. A familiar warmth spreads so Jason's cheeks and he ducks his head.
"Bye, kitten," he says, turning to the door. As he leaves he slips the do not disturb sign on the outer handle.
"Have a good day at work daddy."
Jason finishes her breakfast and then sets the tray on the floor in the hall like daddy told her to. She has to do this quickly since she is still wearing nothing but panties and a camisole. turning back inside the massive hotel room suddenly feels empty. The day won't be the same without daddy around. She makes the bed (daddy says good girls make their bed in the morning) checks her butt in the mirror and is disappointed with what she sees. It's still a little pink and a nice bruise has formed on each cheek. But unlike the night before she could no longer see daddy's hand print. Desperate to feel some connection to him she sits on the hard coffee table. The pain in her rear brings back memories of that first spanking. Of being taken so completely and utterly. But she finds the memory simply makes her miss her daddy more. With some trepidation she moves to daddy's luggage. In there is the bag he's put his dirty laundry in. From it she removes a pair of boxers. Butterflies float around her stomach as she moves them to her face. The scent of his sex is strong on them.
"Hrm... now I'm an underwear sniffer too. I don't know why I'm surprised."
She spends the morning lounging around the hotel room. Watching TV in the living room, watching tv in the bedroom. She even spends 1/2 an hour watching pay per view porn. This is "homework" given to her by daddy. He wants her horny when he sees her again that evening. But all she can find is straight porn. Cis men fucking Cis women. In none of them are they even tied up. So she tries slipping a finger into her bum and massaging her prostate. But none of it excites her as much as she hopes and she shuts off the TV after 1/2 an hour passes.
Bored, she puts on her old clothes. Well most of them. The boxers go in the trash. She'll never wear those again. She picks up the key card daddy gave her holding it close. Bringing it to her face she smells the plastic and rubs it gently on her face. He gave her a key. It's not a house key but it's still a key to his temporary home. She steps outside and lets the door close. With some fear she tries the key card. Instantly the light on the lock turns green. She turns the handle and steps into her daddy's temporary home. The feeling is so wonderful that she does it three more times before leaving the hotel. The key card, safe in her pocket.
Absently she takes the train to her parents house. Uh... Her house. It certainly doesn't feel like home anymore. Home is where daddy is. She exits the train and walks the four blocks to the house stopping at the corner. The house is only four driveways in but she can't bring herself to take another step. She pulls out her phone and texts her mother.
"I'm fine, I won't be coming home, spending the day with a friend." A friend, right.
Turning she returns to the train that will take her back into NYC. At the platform, on the train, on the streets of NYC she can't help but swing her head back and forth. Constantly afraid someone will notice her cage and call her out publicly as a sissy. Somewhere in the back of her brain a small part of her quietly hopes it will come true. She's been to the city many times before. It's just a train ride away. But today it seems different. Today daddy is in town and they have a date later that night.
For lunch she picks up a slice from bleecker street pizza, it's a big day so why not a treat. She only eats the one since she'll be with daddy soon and they'll probably have an early dinner like they did yesterday so that they can go home and play. An involuntary shudder passes through her. Around four she begins heading back to daddy's hotel. He should be leaving his client's office some time between 4:30 and 5. By 4:15 she's opening the hotel room door again. Unable to help herself she lets it close and opens it three more times before stepping in. Uncomfortable in boys clothes she slips them off and slips the second camisole on carefully folding her clothes and setting them on the counter.
Daddy arrives 1/2 an hour later. Unable to resist him, she throws herself into his arms.
"Wait, wait princess. Let me set down some things." He laughs.
She pulls away, her eyes at her toes.
She sees him set a bag and then his backpack on the floor then he steps close and wraps his arms around her. She looks up imagining her eyes glistening like an anime girl.
"Don't be sorry little princess, that was exactly the welcome home daddy was hoping for."
With a smile she loops her arms around his neck. He bends down and crushes her mouth with his. Then she feels herself lifted and held tight to his chest. Cradling her in his arms he begins walking towards the bedroom. Passing her neatly folded clothes he stops. He casts one tortured look at the bedroom then looks back down at her with a serious expression.
"No, not yet. First things first."
Gently he sets her down and turns to the bag, from it he pulls two things. An elegant black choker with a kitten head shaped ring in the front and the tiniest little bell. The second thing she recognizes as a prostate toy but it's not one she has seen before. Gently he bends her over the kitchen counter, lubes her ass and inserts it. It feels wonderful.
"Get dressed," he orders. Walking to her clothes the toy rubs against her prostate and feels quite nice. She slips one leg into her jeans and then as she lifts the other her prostate buzzes with a completely new sensation. Her eyes blur and she finds herself in daddy's arms again the sensation gone. It had been so intense she'd gotten dizzy, stumbled and he'd caught her. She finishes putting on her pants and as he stands she notices a small remote control in his hands. He presses a button and again her knees buckle. She leans against daddy's chest for support. As suddenly as it started it's over.
"Finish getting dressed." He says with a smirk placing the remote in his pocket. "We're going shopping."
Shopping is a nightmare. As they step into the new super fancy Nordstrom all eyes do turn on her and she begins to back away. A strong hand grips her arm and he leans down to whisper into her ear.
"They're looking at us because that's the sales staff hoping we will buy something from them. Nobody knows anything."
To Jason's surprise they head to the women's section. They're going to buy him a woman's clothes. In public? Again the strong hand on his arm but this time there are no comforting words. They both know what's about to happen. A wonderfully dressed saleswoman with a warm smile steps over to them.
"Can I help you?"
Daddy puts his hands on her shoulders and moves her to the forefront.
"This lovely young lady has just begun transitioning and is in need of something fashionable for dinner."
"Oh" she says as Jason prepares for ridicule. She looks Jason up and down as she pulls a measuring tape she'd had hidden somewhere. "Well congratulations, and good luck. Let's take some measurements and get you into something pretty why don't we."
Her measurements taken (and collected by daddy) the next hour is spent trying things on and showing them to daddy and Elisa the saleswoman. Eventually deciding upon a form fitting skirt (Jason has always had somewhat girlish hips) and a deep red blouse which goes perfectly with her new choker. Clothing selected and paid for they move to the makeup section. All sorts of new things are spread first on the back of her hands and eventually on her face. When Nithisha the makeup consultant finally turns her to the mirror Jason doesn't recognize what he sees. The girl in front of her is beautiful. With luscious ruby lips, pink cheeks and a dusting or rose across the tip of her nose. She had big beautiful eyes now that they were highlighted by eyeliner. Tentatively she turns. Biting her lip she raises her eyes.
"Do you like it daddy?" She asks. From the corner of her eye she catches the sales woman's face. There's the look of shock Jason had been expecting. But it only lasts for a moment before she busies herself tallying up their purchases at the register.
"You look lovely dear." She says turning to daddy. "Doesn't she."
"Yes she does." He affirms caressing her cheek.
Lastly comes her hair. They find a beauty salon with walk-in appointments and step inside. Her makeup and hair clothes complete, the beautician doesn't bat an eyelash and leads her directly to a chair.
The entire time in the store and at the beautician's daddy has been messing with the remote. Whenever the saleswoman or now the beautician would turn away he would turn on the toy buried deep in Jason's rectum and Jason's knees would get weak. He had begun to feel a wetness on his leg at the makeup counter.
The hair is an ordeal. It was his first cut since he'd begun growing it long for daddy. As a boy, haircuts had been over in minutes. Do womens haircuts always take this long?
Finally they head to a restaurant. This time is different. Stepping in front of the server, daddy pulls the chair out for her. As the bus boy fills their waters daddy takes her menu from her and begins perusing it, his still on the table before him. In the quiet she begins to look around. She'd forgotten briefly on the drive over but now she was super conscious of the satin blouse against her skin, the air flowing across her calves and if she wasn't careful her inner thighs. She was certain she could see a bulge in the tight skirt and that everyone would know she was an imposter, not a woman at all but a man in chastity.
Shopping had taken longer than she had expected, her stomach having long forgotten the single slice of pizza she'd eaten since breakfast. She eagerly digs into the salad that is set before her. They eat quietly. Daddy with his steak and scotch, her with her salad and soda. The action is so natural that she almost relaxes. Almost
Back at the hotel daddy looks down at her, eyes burning with desire. Gently he moves her to the bedroom and carefully strips her clothes. Naked, more rope is produced and she is tied to the bed, her chest on the comforter arms stretched out to the sides. Her feet on the floor, short ropes tying ankles to the beds, legs her ass out, her caged little clitty dangling. She hears a whooshing sound behind her before a thin bamboo rod about three feet long is set in front of her. Turning her head she sees daddy holding what appears to be a gag with a hand pump attached to it.
"As much as I would love to keep that mouth open and accessible we can't have you disturbing the neighbors."
The gag is placed in her mouth and slowly inflated. Her jaw is spread wide and her tongue pressed hard to the bottom of her mouth. And then he is gone. Soon she hears the shower. Daddy is showering without her. Wishing she could be in there with him she squirms trying to catch a glimpse of him. Shortly he steps from the shower glistening. His broad shoulders forming a nice manly V despite his "dad bod" cuddly midsection. Drying off Jason is mesmerized by his rock hard cock. She slides her tongue around on the bottom of the gag as much as she can wishing it were his dick.
By the time he gets back to the bed the comforter under her face is wet with drool. She turns her eyes down embarrassed.
"Good girl" daddy says, wiping some of the drool from her chin and then up on her face.
His big hand slides roughly across her backside and she is surprised that it doesn't hurt at all. Even with the slight bruising she must be healing fast.
"It is simply a shame that this isn't still red, black and blue after only 24 hours."
"Stronger measures will be taken." he adds, swishing the bamboo switch.
The moment the switch touches her flesh Jason is glad for the gag. Because the pain is unbearable. Screaming at the top of her lungs only a muffled keen makes it to her ears. Nothing loud enough to reach the hotel suite next door. The switch is brought to her ass repeatedly. From time to time she feels a hand smacking, grabbing, twisting her ass. At some point the toy still plugging her rectum turns on again and the sensations run together. The pain from the switch, the pleasure from the toy, her joy at being used by her daddy. Tears running freely down her face the flogging eventually stops. He is beside her on the bed when she opens her eyes.
"What a beauty." He says giving her a peck on the cheek. Then he is behind her. The toy is removed, she hears the click of the lube bottle opening and he is slipping into her. Unlike the night before she doesn't pull away but relaxes and pushes back onto his dick. It slides in easily; and quickly she is being thoroughly used for his pleasure. Her hips burn where he grabs the flesh like handles to slam into her harder. The ropes cut into her wrists and ankles and she wants nothing more than to see her daddy's face as he fucks her. Turning her head they lock eyes, hers glistening with joy, his burning with lust. He reaches forward and grabs her hair pulling her head back as he pumps into her even harder. She cries out (as much as the gag will let her) and something sticky and wet slides down her thigh. She has come from him again. She's never been able to cum twice in two days when masterbating. Daddy lets go of her hair and slows a bit. Turning she sees him looking down where the cum must have pooled on the carpet.
"Good girl," he says again. He resumes his brutal and wonderful thrusting, grabbing her hips, slapping her ass. Eventually she is lifted completely off the bed straining the ropes as he impales her, spilling his seed deep into her ass. The pain where he is holding her hips is excruciating but the sensation in her ass is overwhelming.
Gently she is laid back on the bed. The bonds and gag are removed and aloe is spread on her wrists, ankles and backside. One final trip to the bag he'd set by the door and daddy returns with a frilly yellow nightie and undies. She slips into them and looks at herself in the mirror. The nighty is lovely but her face is streaked with mascara. The lipstick smeared across her mouth, her hair a rats nest on top of her head. She looked well and thoroughly used.
Exactly like a sissy hypno.
With a smile she turns and throws her arms around his neck.
"Thank you daddy." She giggles.
She kneels on the floor in front of him and takes his cock in her hands. He reaches to the towel rack and drops a folded towel on the floor next to her. What a caring daddy she thinks placing it under her knees she sets to work. When he tenses she moves her hands to his shaft and balls. Finally able to catch some on her tongue she plays with it while he watches. Something she knows he's been waiting to see. Apparently she does a good job because he takes her head into his hands and proceeds to fuck the cum down her throat following it with a second load.
They make love three more times that night. She is unable to cum a second time but by the time the evening is over she feels completely filled. They fall asleep spooning, his dick still inside of her.
When Jason wakes up she finds herself clasping the sheets tightly, her back arched and her daddy's cock sliding slowly in and out of her ass. Apparently they'd begun having sex while she was still asleep. The sex is tender and loving. Daddy's arms wrap around her chest toying her nipples and holding her close to him. Again she finds that unfamiliar warmth in her groin and ass. Before long she is cumming from daddy's cock. When daddy sprays her back with cum she wishes it had been her face but doesn't turn. She knows daddy is looking at her ass.
Afterwards they shower. Daddy washing her body carefully. Stepping from the shower they dry one another and daddy sends her to the bedroom while he shaves and gets dressed. Back in the living room Jason sees clothes laid out on the coffee table. She sits and examines them. There are three pairs of panties. Two in simple satin bordered in delicate lace and one crinkly, bright pink pair with gigantic frills. The last pair was for sleeping, daddy had sent her pictures before. Next to the panties were two camisoles. These were lounging and sleeping outfits for Jason. She chooses one of the simpler panties and a camisole both in blue.
Daddy steps out of the bathroom and stops smiling.
"Good, I see you found the lounge wear. We'll take you out and let you pick something special for tonight's dinner after work." Jason felt a warmth in her cheeks. What was that? Was she blushing? She'd never done that as a boy.
"But before I go I have a surprise for you.
Daddy opens his luggage and pulls out a small box wrapped with a big pink bow. Handing it to Jason he tells her to open it.
Jason's eyes widened. It's a chastity cage. Her heart skips a beat. She'd been waiting for months wishing daddy would lock her up. Tick, another daddy promise fulfilled. It's one of the smaller micro cages. Most chastity cages were designed so that the wearer could get partially, but not fully, hard. The sensation was supposed to be very frustrating. Jason had saved up and purchased one before he had met daddy and found that his worthless little clitty was so small she could get fully erect in the cage. Then Daddy showed her the micro cages. They were so small they would squish even Jason's insignificant member. Not only that but since they constantly squished the dick down supposedly it didn't even try and get hard. Jason couldn't wait to feel it on. Every erection he got felt like his clitty was betraying him. It was too small to be used hard. He wished it would shrink to the size of a real girl's clit. He couldn't get his hand on it, just a few fingers, and wished it would almost disappear so that it could be diddled like a real clit.
The cage has a ring that goes around her shaft and behind her tiny balls. Then the cage is slid over her clittly and a lock inserted where the two meet. There is a click when daddy turns the key and the lock engages. Jason's heart skips a beat. Tick... Another daddy promise delivered. The promise he'd been dreaming of for months. Daddy has taken complete possession of her and any chance she has of pleasure.
There is a knock at the door and daddy moves to answer it. He returns with a tray filled with plates and glasses wrapped in saran wrap to keep them from spilling. He sets it on the table in the middle of the main room.
"I took the liberty of ordering breakfast. You don't mind." It wasn't a question so Jason doesn't answer. Daddy lifts the lids off of their dishes and sets them aside. There are eggs sunny side up with toast and hash browns for daddy. Jason looks at her own plate and finds scrambled eggs and pancakes. The pancakes are decorated with a happy face made from whipped cream. Jason smiles and picks up her knife and forth. Before she takes a bite she hears a "tut, tut" from daddy. Looking up Jason sees that he is indicating her napkin. Waving his knife in the direction of her top Jason tucks the napkin in like a bib and digs into her pancakes.
The chastity cage is tighter than she expected. And having something wrapped around your boy clit is highly erotic. Before he'd always been ashamed of it and almost afraid to touch it. But now he wanted to.
Noticing Jason squirming daddy dips under the table and pulls down her shorts. He begins playing with jasons balls and the sensation is fantastic.
A soft "Thank you daddy." Slips from his lips.
Daddy puts his mouth on the cage and for the first time in years Jason wishes he had a big dick. One that would please daddy. Secretly he begins to dream of daddy letting him out of the cage and sucking his little clitty.
He doesn't of course. After a few minutes of teasing Jason's caged clit, balls and nipples he simply stops, slowly stands and watches Jason squirm.
He looks at his watch. I'm going to have to leave in a hurry, you've distracted me more than I expected this morning. A familiar warmth spreads so Jason's cheeks and he ducks his head.
"Bye, kitten," he says, turning to the door. As he leaves he slips the do not disturb sign on the outer handle.
"Have a good day at work daddy."
Jason finishes her breakfast and then sets the tray on the floor in the hall like daddy told her to. She has to do this quickly since she is still wearing nothing but panties and a camisole. turning back inside the massive hotel room suddenly feels empty. The day won't be the same without daddy around. She makes the bed (daddy says good girls make their bed in the morning) checks her butt in the mirror and is disappointed with what she sees. It's still a little pink and a nice bruise has formed on each cheek. But unlike the night before she could no longer see daddy's hand print. Desperate to feel some connection to him she sits on the hard coffee table. The pain in her rear brings back memories of that first spanking. Of being taken so completely and utterly. But she finds the memory simply makes her miss her daddy more. With some trepidation she moves to daddy's luggage. In there is the bag he's put his dirty laundry in. From it she removes a pair of boxers. Butterflies float around her stomach as she moves them to her face. The scent of his sex is strong on them.
"Hrm... now I'm an underwear sniffer too. I don't know why I'm surprised."
She spends the morning lounging around the hotel room. Watching TV in the living room, watching tv in the bedroom. She even spends 1/2 an hour watching pay per view porn. This is "homework" given to her by daddy. He wants her horny when he sees her again that evening. But all she can find is straight porn. Cis men fucking Cis women. In none of them are they even tied up. So she tries slipping a finger into her bum and massaging her prostate. But none of it excites her as much as she hopes and she shuts off the TV after 1/2 an hour passes.
Bored, she puts on her old clothes. Well most of them. The boxers go in the trash. She'll never wear those again. She picks up the key card daddy gave her holding it close. Bringing it to her face she smells the plastic and rubs it gently on her face. He gave her a key. It's not a house key but it's still a key to his temporary home. She steps outside and lets the door close. With some fear she tries the key card. Instantly the light on the lock turns green. She turns the handle and steps into her daddy's temporary home. The feeling is so wonderful that she does it three more times before leaving the hotel. The key card, safe in her pocket.
Absently she takes the train to her parents house. Uh... Her house. It certainly doesn't feel like home anymore. Home is where daddy is. She exits the train and walks the four blocks to the house stopping at the corner. The house is only four driveways in but she can't bring herself to take another step. She pulls out her phone and texts her mother.
"I'm fine, I won't be coming home, spending the day with a friend." A friend, right.
Turning she returns to the train that will take her back into NYC. At the platform, on the train, on the streets of NYC she can't help but swing her head back and forth. Constantly afraid someone will notice her cage and call her out publicly as a sissy. Somewhere in the back of her brain a small part of her quietly hopes it will come true. She's been to the city many times before. It's just a train ride away. But today it seems different. Today daddy is in town and they have a date later that night.
For lunch she picks up a slice from bleecker street pizza, it's a big day so why not a treat. She only eats the one since she'll be with daddy soon and they'll probably have an early dinner like they did yesterday so that they can go home and play. An involuntary shudder passes through her. Around four she begins heading back to daddy's hotel. He should be leaving his client's office some time between 4:30 and 5. By 4:15 she's opening the hotel room door again. Unable to help herself she lets it close and opens it three more times before stepping in. Uncomfortable in boys clothes she slips them off and slips the second camisole on carefully folding her clothes and setting them on the counter.
Daddy arrives 1/2 an hour later. Unable to resist him, she throws herself into his arms.
"Wait, wait princess. Let me set down some things." He laughs.
She pulls away, her eyes at her toes.
She sees him set a bag and then his backpack on the floor then he steps close and wraps his arms around her. She looks up imagining her eyes glistening like an anime girl.
"Don't be sorry little princess, that was exactly the welcome home daddy was hoping for."
With a smile she loops her arms around his neck. He bends down and crushes her mouth with his. Then she feels herself lifted and held tight to his chest. Cradling her in his arms he begins walking towards the bedroom. Passing her neatly folded clothes he stops. He casts one tortured look at the bedroom then looks back down at her with a serious expression.
"No, not yet. First things first."
Gently he sets her down and turns to the bag, from it he pulls two things. An elegant black choker with a kitten head shaped ring in the front and the tiniest little bell. The second thing she recognizes as a prostate toy but it's not one she has seen before. Gently he bends her over the kitchen counter, lubes her ass and inserts it. It feels wonderful.
"Get dressed," he orders. Walking to her clothes the toy rubs against her prostate and feels quite nice. She slips one leg into her jeans and then as she lifts the other her prostate buzzes with a completely new sensation. Her eyes blur and she finds herself in daddy's arms again the sensation gone. It had been so intense she'd gotten dizzy, stumbled and he'd caught her. She finishes putting on her pants and as he stands she notices a small remote control in his hands. He presses a button and again her knees buckle. She leans against daddy's chest for support. As suddenly as it started it's over.
"Finish getting dressed." He says with a smirk placing the remote in his pocket. "We're going shopping."
Shopping is a nightmare. As they step into the new super fancy Nordstrom all eyes do turn on her and she begins to back away. A strong hand grips her arm and he leans down to whisper into her ear.
"They're looking at us because that's the sales staff hoping we will buy something from them. Nobody knows anything."
To Jason's surprise they head to the women's section. They're going to buy him a woman's clothes. In public? Again the strong hand on his arm but this time there are no comforting words. They both know what's about to happen. A wonderfully dressed saleswoman with a warm smile steps over to them.
"Can I help you?"
Daddy puts his hands on her shoulders and moves her to the forefront.
"This lovely young lady has just begun transitioning and is in need of something fashionable for dinner."
"Oh" she says as Jason prepares for ridicule. She looks Jason up and down as she pulls a measuring tape she'd had hidden somewhere. "Well congratulations, and good luck. Let's take some measurements and get you into something pretty why don't we."
Her measurements taken (and collected by daddy) the next hour is spent trying things on and showing them to daddy and Elisa the saleswoman. Eventually deciding upon a form fitting skirt (Jason has always had somewhat girlish hips) and a deep red blouse which goes perfectly with her new choker. Clothing selected and paid for they move to the makeup section. All sorts of new things are spread first on the back of her hands and eventually on her face. When Nithisha the makeup consultant finally turns her to the mirror Jason doesn't recognize what he sees. The girl in front of her is beautiful. With luscious ruby lips, pink cheeks and a dusting or rose across the tip of her nose. She had big beautiful eyes now that they were highlighted by eyeliner. Tentatively she turns. Biting her lip she raises her eyes.
"Do you like it daddy?" She asks. From the corner of her eye she catches the sales woman's face. There's the look of shock Jason had been expecting. But it only lasts for a moment before she busies herself tallying up their purchases at the register.
"You look lovely dear." She says turning to daddy. "Doesn't she."
"Yes she does." He affirms caressing her cheek.
Lastly comes her hair. They find a beauty salon with walk-in appointments and step inside. Her makeup and hair clothes complete, the beautician doesn't bat an eyelash and leads her directly to a chair.
The entire time in the store and at the beautician's daddy has been messing with the remote. Whenever the saleswoman or now the beautician would turn away he would turn on the toy buried deep in Jason's rectum and Jason's knees would get weak. He had begun to feel a wetness on his leg at the makeup counter.
The hair is an ordeal. It was his first cut since he'd begun growing it long for daddy. As a boy, haircuts had been over in minutes. Do womens haircuts always take this long?
Finally they head to a restaurant. This time is different. Stepping in front of the server, daddy pulls the chair out for her. As the bus boy fills their waters daddy takes her menu from her and begins perusing it, his still on the table before him. In the quiet she begins to look around. She'd forgotten briefly on the drive over but now she was super conscious of the satin blouse against her skin, the air flowing across her calves and if she wasn't careful her inner thighs. She was certain she could see a bulge in the tight skirt and that everyone would know she was an imposter, not a woman at all but a man in chastity.
Shopping had taken longer than she had expected, her stomach having long forgotten the single slice of pizza she'd eaten since breakfast. She eagerly digs into the salad that is set before her. They eat quietly. Daddy with his steak and scotch, her with her salad and soda. The action is so natural that she almost relaxes. Almost
Back at the hotel daddy looks down at her, eyes burning with desire. Gently he moves her to the bedroom and carefully strips her clothes. Naked, more rope is produced and she is tied to the bed, her chest on the comforter arms stretched out to the sides. Her feet on the floor, short ropes tying ankles to the beds, legs her ass out, her caged little clitty dangling. She hears a whooshing sound behind her before a thin bamboo rod about three feet long is set in front of her. Turning her head she sees daddy holding what appears to be a gag with a hand pump attached to it.
"As much as I would love to keep that mouth open and accessible we can't have you disturbing the neighbors."
The gag is placed in her mouth and slowly inflated. Her jaw is spread wide and her tongue pressed hard to the bottom of her mouth. And then he is gone. Soon she hears the shower. Daddy is showering without her. Wishing she could be in there with him she squirms trying to catch a glimpse of him. Shortly he steps from the shower glistening. His broad shoulders forming a nice manly V despite his "dad bod" cuddly midsection. Drying off Jason is mesmerized by his rock hard cock. She slides her tongue around on the bottom of the gag as much as she can wishing it were his dick.
By the time he gets back to the bed the comforter under her face is wet with drool. She turns her eyes down embarrassed.
"Good girl" daddy says, wiping some of the drool from her chin and then up on her face.
His big hand slides roughly across her backside and she is surprised that it doesn't hurt at all. Even with the slight bruising she must be healing fast.
"It is simply a shame that this isn't still red, black and blue after only 24 hours."
"Stronger measures will be taken." he adds, swishing the bamboo switch.
The moment the switch touches her flesh Jason is glad for the gag. Because the pain is unbearable. Screaming at the top of her lungs only a muffled keen makes it to her ears. Nothing loud enough to reach the hotel suite next door. The switch is brought to her ass repeatedly. From time to time she feels a hand smacking, grabbing, twisting her ass. At some point the toy still plugging her rectum turns on again and the sensations run together. The pain from the switch, the pleasure from the toy, her joy at being used by her daddy. Tears running freely down her face the flogging eventually stops. He is beside her on the bed when she opens her eyes.
"What a beauty." He says giving her a peck on the cheek. Then he is behind her. The toy is removed, she hears the click of the lube bottle opening and he is slipping into her. Unlike the night before she doesn't pull away but relaxes and pushes back onto his dick. It slides in easily; and quickly she is being thoroughly used for his pleasure. Her hips burn where he grabs the flesh like handles to slam into her harder. The ropes cut into her wrists and ankles and she wants nothing more than to see her daddy's face as he fucks her. Turning her head they lock eyes, hers glistening with joy, his burning with lust. He reaches forward and grabs her hair pulling her head back as he pumps into her even harder. She cries out (as much as the gag will let her) and something sticky and wet slides down her thigh. She has come from him again. She's never been able to cum twice in two days when masterbating. Daddy lets go of her hair and slows a bit. Turning she sees him looking down where the cum must have pooled on the carpet.
"Good girl," he says again. He resumes his brutal and wonderful thrusting, grabbing her hips, slapping her ass. Eventually she is lifted completely off the bed straining the ropes as he impales her, spilling his seed deep into her ass. The pain where he is holding her hips is excruciating but the sensation in her ass is overwhelming.
Gently she is laid back on the bed. The bonds and gag are removed and aloe is spread on her wrists, ankles and backside. One final trip to the bag he'd set by the door and daddy returns with a frilly yellow nightie and undies. She slips into them and looks at herself in the mirror. The nighty is lovely but her face is streaked with mascara. The lipstick smeared across her mouth, her hair a rats nest on top of her head. She looked well and thoroughly used.
Exactly like a sissy hypno.
With a smile she turns and throws her arms around his neck.
"Thank you daddy." She giggles.
She kneels on the floor in front of him and takes his cock in her hands. He reaches to the towel rack and drops a folded towel on the floor next to her. What a caring daddy she thinks placing it under her knees she sets to work. When he tenses she moves her hands to his shaft and balls. Finally able to catch some on her tongue she plays with it while he watches. Something she knows he's been waiting to see. Apparently she does a good job because he takes her head into his hands and proceeds to fuck the cum down her throat following it with a second load.
They make love three more times that night. She is unable to cum a second time but by the time the evening is over she feels completely filled. They fall asleep spooning, his dick still inside of her.
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terpinderp
- Forum Contributer
- Posts: 7
- Joined: 1 year ago
Chapter 6
They get up early. It's check out day. Daddy is going home that evening and she is sad. They pack his things into his suitcase and hers into the bag. She puts on the dress from the night before.
"Dressed as a woman, alone, during the day? Are you sure you're ready for that."
With a confidence she's never felt she gives him a smile and a quick nod. They leave the room each with a bag in one hand their free hands clasped the walk to the elevators.
The hotel keys returned and bill paid they head to the parking lot and daddy throws his suitcase in the trunk and then surprises her by following it with his bag.
"I have another surprise for you baby doll." He says taking her in his arms. This was a two day gig. I moved my flight home from last night to this morning so that we could have one more evening and morning together."
He takes her shopping again this time getting her a couple of outfits both of which are younger and more casual than last nights outfit. She leaves the store in a frilly pink blouse, shorts and white stockings with pink stripes. Pink Mary Janes, a pink kitten collar with a bell and a pair of kitten ears complete the outfit. She has never felt so beautiful, so girly, so... something snaps in her brain.
"Squeee....!" She wraps her arms around his waste and squeezes. He hugs her lightly and pats her head.
At breakfast he slides a piece of paper across the table to her. It's a list of girl names.
"These are some names that I like but you're under no obligation to choose one of them. You should make this decision yourself, later out of sub..."
"Jes..." She starts before realizing she's just interupted him.
"I'm sorry daddy." She says turning her eyes down.
"Out of sub space he finishes."
"Jessame." She blurts out when she decides he's finished. She's given it plenty of thought. Both in and out of sub space. She wants to be called Jessame.
After breakfast they spend the rest of the morning doing silly childish things. He takes her to mini golf, they get ice cream, they head to the mall to plan more outfits. All the while she becomes more talkative and bubbly until he grabs her and heads down a plain white hall. They step towards the men's bathroom. She makes an attempt to move towards the woman's but he has a strong hold on her arm and drags her into the mens. They press into an open stall and he lifts her up. Unbuckling his belt with one hand and holding her with the other she wraps her legs around his hips. Pushing her panties aside he enters her again. She is much more quiet this time but they get some funny looks when they leave and she blushes. This only makes daddy hold her tighter.
He brings her with him to the airport. Standing at the entrance to the security check point he crushes her mouth with his own. He stands looking serious and she knows it's time for him to catch his plane.
"Cab fair home." He says slipping some money into her new clutch.
"Your disguise." He hands her, her backpack with her boy clothes in it and she realizes it's true, boy clothes are now a costume. She's daddy's sweet little girl. "You can change in the bathroom."
"For later." He slips an envelope into her clutch
He gets in line for security.
"Jessame" he calls to her "Don't open that until I've left."
They lock eyes until he eventually dissapears. She realizes she has no key, no way to take the chastity cage off. Smiling she realizes she's happier that way. A new spring in her step when she turns and leaves.
They get up early. It's check out day. Daddy is going home that evening and she is sad. They pack his things into his suitcase and hers into the bag. She puts on the dress from the night before.
"Dressed as a woman, alone, during the day? Are you sure you're ready for that."
With a confidence she's never felt she gives him a smile and a quick nod. They leave the room each with a bag in one hand their free hands clasped the walk to the elevators.
The hotel keys returned and bill paid they head to the parking lot and daddy throws his suitcase in the trunk and then surprises her by following it with his bag.
"I have another surprise for you baby doll." He says taking her in his arms. This was a two day gig. I moved my flight home from last night to this morning so that we could have one more evening and morning together."
He takes her shopping again this time getting her a couple of outfits both of which are younger and more casual than last nights outfit. She leaves the store in a frilly pink blouse, shorts and white stockings with pink stripes. Pink Mary Janes, a pink kitten collar with a bell and a pair of kitten ears complete the outfit. She has never felt so beautiful, so girly, so... something snaps in her brain.
"Squeee....!" She wraps her arms around his waste and squeezes. He hugs her lightly and pats her head.
At breakfast he slides a piece of paper across the table to her. It's a list of girl names.
"These are some names that I like but you're under no obligation to choose one of them. You should make this decision yourself, later out of sub..."
"Jes..." She starts before realizing she's just interupted him.
"I'm sorry daddy." She says turning her eyes down.
"Out of sub space he finishes."
"Jessame." She blurts out when she decides he's finished. She's given it plenty of thought. Both in and out of sub space. She wants to be called Jessame.
After breakfast they spend the rest of the morning doing silly childish things. He takes her to mini golf, they get ice cream, they head to the mall to plan more outfits. All the while she becomes more talkative and bubbly until he grabs her and heads down a plain white hall. They step towards the men's bathroom. She makes an attempt to move towards the woman's but he has a strong hold on her arm and drags her into the mens. They press into an open stall and he lifts her up. Unbuckling his belt with one hand and holding her with the other she wraps her legs around his hips. Pushing her panties aside he enters her again. She is much more quiet this time but they get some funny looks when they leave and she blushes. This only makes daddy hold her tighter.
He brings her with him to the airport. Standing at the entrance to the security check point he crushes her mouth with his own. He stands looking serious and she knows it's time for him to catch his plane.
"Cab fair home." He says slipping some money into her new clutch.
"Your disguise." He hands her, her backpack with her boy clothes in it and she realizes it's true, boy clothes are now a costume. She's daddy's sweet little girl. "You can change in the bathroom."
"For later." He slips an envelope into her clutch
He gets in line for security.
"Jessame" he calls to her "Don't open that until I've left."
They lock eyes until he eventually dissapears. She realizes she has no key, no way to take the chastity cage off. Smiling she realizes she's happier that way. A new spring in her step when she turns and leaves.
-
terpinderp
- Forum Contributer
- Posts: 7
- Joined: 1 year ago
Chapter 7
Jason... no Jessame stands in front of the front door she's shared with her parents for her entire life. Taking a deep breath she steels herself. This is going to be even harder of a conversation than she expected and not just because she's been gone two nights instead of one.
She tucks her hair behind her ear, her clutch under her arm and straightens her skirt.
Taking a deep breath she steps inside. Yeah, this will be a much harder conversation.
Jason... no Jessame stands in front of the front door she's shared with her parents for her entire life. Taking a deep breath she steels herself. This is going to be even harder of a conversation than she expected and not just because she's been gone two nights instead of one.
She tucks her hair behind her ear, her clutch under her arm and straightens her skirt.
Taking a deep breath she steps inside. Yeah, this will be a much harder conversation.