Little Red Femboy Hood (CD/M)
Posted: Sat May 13, 2023 2:44 pm
Hiii! It's Alice again with a new fantasy I want to share with you all! This one is Halloween themed, despite the fact it's May at the time of writing this but I couldn't resist! Once again, everyone in it is fictional other than myself.
For those of you who don't know, I am a part time Femboy/Crossdresser that goes by the alias Alice. I am a Switch, with my Sub side coming out when I dress up.
So, with that out of the way: here is the first part of my story.
It was Halloween in the small New England town where I lived. Halloween is one of my favorite holidays of the year due to the fact I could dress up without anyone really batting an eye and the fact I was a lover of all things Horror as well as supernatural ranging from the occult to the mythical. So while I had decided that I wasn't going out to anyone parties or go Trick or Treating that day, I still wanted to dress up and hand out candy to anyone who was.
I stood in front of the full length mirror on the inside of my wardrobe door and checked out my reflection, turning this way and that to get a different angle on my costume when needed: I had chosen to dress up as a Character I saw as an archetypal damsel in distress: Red Riding Hood.
The outfit was nice: a white button down blouse with poofy shoulder sleeves under a black low-cut corset that gave me a bit of a curve and a red and white gingham pleated mini skirt that poofed out a little and made it more revealing than it already was and a white fluffy petticoat that just about hid the tops of my black sheer stockings which went up to just beneath my scantily clad buttocks and were held in place by garter belts. A pair of black over the knee boots and a red hooded shoulder cape completed my outfit but I was still missing two items which were close at hand
On my bed was the woven basket in which all of the candy was going to be stored in and on my desk was the dark brown curly wig I had decided was going to be worn with the outfit when I was certain everything was right.
I'd always been equal parts Perfectionist and Control Freak and as I stared at my reflection as I switched from pose to pose, wiggling my bottom to see if my skirt would reveal anything I didn't want some random person to see when I was handing out candy, I felt a sense of pride in how I looked.
My body was by no means feminine which I was more or less fine with: I was short and stocky, with a broad chest and untrained but very obvious muscle but I had still somehow managed to come across as a short boyish girl in her early twenties despite it all.
I grabbed the wig from my desk and placed it atop my head, making sure it was secure before grabbing my basket and departing my room.
I lived in a single floor bungalow in a Cul-de-sac with a river at the back, which I wasn't too pleased about as I really didn't like water but it was a nice place and had been relatively cheap.
I rushed into the kitchen, setting my basket down on the countertop as I did so beforeore opening the cupboard door and pulling out bags of wrapped candy and chocolate from within and tearing the bags open before pouring the contents into the basket, but not before making sure that none of these treats had nuts or gluten in them.
Not because I had any allergies but in case anyone else did, last thing I wanted was to end up hospitalizing another person because of a bout of carelessness on my part.
Anyway, with that done I closed the cupboard door and binned the empty packets before grabbing my basket and making my way to the living room where my front door was.
I was a relatively private person so all the windows had their curtains drawn to avoid any peeping toms. This had the added benefit of meaning I could practice self-bondage in my home whenever the mood grabbed me without anyone inadvertently looking in and seeing me bent over the arm of a sofa with my panties on display because my skirt had accidentally-on-purpose ridden up or writhing on the kitchen table and mewling into my red ball gag as I pretended to struggle to free myself.
I had actually gotten pretty good at self-bondage and always made sure I had a way to get myself free if I needed to.
And it tended to grab me quite a bit if I am being honest. But despite how much of a horny bondage-slut I WAS, I had made a promise to myself that I wouldn't be indulging in that particular past time tonight as that would mean me quite possibly missing out on handing out candy to anyone that knocked on my door or even worse despite how unlikely it was to happen: being found in a compromising position because someone had come in to see if I was alright.
So, despite how horny the thought of being tied up in this outfit was, I couldn't do that. Not when it meant accidentally ruining someone else's night because I wasn't able to hand out candy.
Instead I simply opted to take a seat on my sofa, which had it's back to the front door, and turn on the TV while I waited for someone to knock. I adjusted my skirt, pulling it a tad bit lower as it rode up in response to my movements as I grabbed the remote and began looking through Netflix and Amazon Prime for anything horro-based to watch while I waited. Eventually I decided on Paranormal Activity and let that play before sinking into my seat, trying my best to be as ladylike as I could.
The main issue I soon found with this outfit though was the skirt: every slight movement made the tiny skirt that just about protected my modesty ride up to expose the curve of my ass and my stocking tops, forcing me to hurriedly pull it down and sending a little pulse of euphoria and excitement through me whenever I did so. It didn't help that I had something of an exhibitionist streak in me, albeit one that only extended to those who had consented.
Eventually the door bell ring, jolting me out of my euphoria filled thoughts in the process. I took a couple of moments to compose myself as I did so, standing up and tugging my skirt down to get some modesty before bending over to pick up the basket from where it sta on the sofa next to me.
And that was when I discovered another issue. Even when I bent slightly at the waist, the tiny thing rode up. I grabbed the basket handle and stood up straight, taking a moment to once again pull my skirt down to hide my underwear before sauntering over to the door and opening it to say hello to the Trick-or-Treaters, a collection of college students that were clearly looking for free food.
"TRICK OR TREAT, SMELL OUR FEET!" They cried out and I grinned sheepishly as I flipped up the lid of my basket. Some of them had actually put in effort into their costumes and were immediately identifiable to my nerdy eye: I could see a Captain America, Eren Jaeger (which made me snicker), Lucy Heartfilia and Luke Skywalker, while the others had seemingly haphazardly thrown their costumes together last minute.
"Looking for guys!" I chirped cheerfully in my best approximation of a female voice as I started handing out candy to them.
"Thanks, I love your Red Riding Hood outfit! Looks really cute!" The girl dressed as Lucy remarked, her eyes moving up and down my body as she did so.
That was when I noticed that some of the others in the group were also checking me out despite the fact I was guy. Maybe they didn't know, in that case my attempt at passing had worked, or if they just didn't care then that was also fine by me, just meant that I looked good in a miniskirt and stockings.
"Aw, thanks. I love your Lucy costume too, looks very cool." I responded, closing the lid of the basket as I did so "Fairy Tail's pretty fun."
"Thanks! Yeah I loved Lucy in it, she was soo cool!" I nodded in understanding and spent the next few moments chatting about nerdy things to the group, occasionally having to readjust my skirt as I did so before they left and I shut my door before returning to my seat.
The next few Trick-Or-Treaters would come and I would once again have to pull my skirt down and get leered at by the more grown-up ones as I handed out candy. This went on for a few hours until the door bell once again rung while I was watching Dracula and I went to open it.
Much to my surprise, instead of Trick-or-Treaters who were looking to score some candy, was instead a young man that was the same age as me.
He wore a simple letterman jacket over a pale pink button down shirt and denim jeans with baseball trainers. He had short, messy sandy blond hair and blue eyes and was looking down at me with a wolfish grin on his face.
"Trick-or-Treat!" Eric teased and my free hand immediately went to my skirt, trying to pull it down even further than I already had to no avail.
Eric. To describe Eric as a person would actually be pretty easy: he was a deviant with a bondage streak bigger than my own. We were Friends with Benefits and that was all either of us wanted from one another. But, that didn't mean I wasn't going to get immediately flustered at what I was wearing now that he was standing in front of me.
Other people, it was different. I hadn't dressed with any sexual thoughts in mind in regards to them so my attempts at modesty were entirely that.
But with Eric? I guess, it was also kind of part of our games. I would always play the part of the damsel-in-distress that he has come to kidnap and do sordid deeds to because he really liked it and I did too. So it was just as much "shit I don't want him to see anything under my skirt" as it was "let's remind him just how short this little thing is and hope he's here for some fun."
I know I had promised myself no self-bondage, I hadn't actually made that same promise in regards to regular bondage so if Eric decided he wanted to tie me up and put me somewhere out of sight for later, then who was I to stop him?
"Hey, Eric! Surprised to see you here." I remarked coyly before stepping aside to let him in "wanna come in?"
"Sure thing," he stepped inside and I closed the door behind him, pressing my back to it and turning the lock quietly.
"So, what brings you here?" I inquired, crossing my arms under my chest as I did so and making my pushup bra push my chest up somewhat. Eric turned to face me, that wolfish grin still plastered on his face.
"Nice outfit, love the little short skirt." He remarked and I hummed in agreement.
"Little bit TOO short though, don't you think?" I asked, lightly pinching the hem of the skirt's side and lifting it to reveal my garters. His eyes widened slightly before settling down as he stalked forwards.
"No, not really. Just short enough for what I have in mind." And just like that, I was aroused, my hardened cock pressing against the fabric of my panties as I pretended to sink away from him.
"O-Oh? And what's that, you naughty boy?" I asked with mocking concern as he pressed his body against mine, trapping me between himself and the door. I let out a not-so-pretend squeak of surprise as I felt a cold hand reach up under my skirt and pinch my buttock as he whispered into my ear as the heat rushed to my cheeks.
"Stay here like a good girl and you'll find out." With that he pulled away from me and walked off, making his way towards my bedroom.
Realizing I had mere seconds to avoid "punishment", I set the basket down onto the floor before hurrying over to the sofa, sitting down on it with my legs tucked into my body, causing my skirt to ride up further.
Eric returned shortly after that with a bundle of rope in his hands and I swallowed.
"Oh come on! Th-that's so not necessary, Eric." I moaned as he came over to me.
"Yes it is." He argued.
"But whyyyy! I just wanted to dress up for Halloween and hand out candy." I bemoaned through a pretend pout as he sat down behind me and forced my wrists behind my back.
"Cuz of that outfit" he admitted as he started tying my wrists together.
"You're just jealous that other people can look up my skirt. Perv."
"Yup! This ass is too cute to be viewed freely by the public" as he said this, a hand grabbed my ass and I squealed again, hips bucking slightly as he let go of my wrists. I rubbed them together to see if I could escape them to no avail while Eric proceeded to tie a chest harness on me, pinning my arms to my sides and then went about undoing the first few buttons of my blouse, allowing my lacy black push-up bra to spring free.
"H-hey! You don't have to do that! W-what if someone s-sees me!" I protested, squirming as I did so.
"Yes I do." Eric said before he forced me to bend over and he immediately wolf-whislted at the sight of my skimpy black panties which did nothing to cover my ass and my garters. I yelped as he gave me a quick smack before pulling my underwear down.
"Oh fuck. Really?! NOW you wanna stick it in?!" I asked "but I won't be able to walk for hours!"
"Shut up, I'm not sticking my dick in you." Eric chided before I felt something cold, hard and plastic be inserted into my bottom. I squirmed in pleasure and moaned abit, earning me some teasing from him as I unintentionally wiggled my ass.
"Naughty girl, aren't you? Like to act all coy but you love being treated roughly." I bit my lip and nodded as he pulled my panties back up and then threw me over his shoulder, a hand planted firmly on my ass and giving one cheek a tight squeeze.
My heart started to pound in my chest as he carried me out of my living room and into the hallway connecting every room in the bungalow together.
"H-hey, maybe this is a bad idea." I remarked "what if the door goes"
"I'll answer it."
"Whilst balls deep in my mouth?" I asked sarcastically, still squirming under his grip.
"Nope." I frowned at that but said nothing "so, what's made you decide on this outfit?"
"Well, Red Riding Hood's a damsel in distress isn't she? I mean yeah in most renditions of the story she isn't tied up but-"
"So you were hoping this would happen?"
"Hmm, maybe subconsciously yeah." He came to a stop in front of an empty cupboard and put me down. I looked at him in confusion and arousal as he opened it to reveal a pole running horizontally inside.
"Oh no, you're not sticking me in th-mmmphgrmph!" I squealed as he forced a large red ball-gag between my lips and secured it tightly behind my head.
"Yup, I am" Eric chortled before pushing me into the cupboard, making sure I was straddling the pole before using the remainder of my rope to secure my thighs, shins and ankles together before putting a crotch-rope between my legs while I mewled into the gag, squirming against my restraints and glaring at him as he stepped back to admire his depraved handiwork.
"That'll do for now, just need to keep you hidden away until later." I scowled, throwing my hair back as I did so.
"Mphmmphgrmrphm?!" I demanded before he just chuckled and closed the door in my face, leaving me trapped inside the cupboard with my skirt hitched and bunched up dangerously high and precum starting to soak my panties.
Which was when the thing he had inserted into me started to vibrate and I moaned loudly into my gag.
What. An. Asshole!
For those of you who don't know, I am a part time Femboy/Crossdresser that goes by the alias Alice. I am a Switch, with my Sub side coming out when I dress up.
So, with that out of the way: here is the first part of my story.
It was Halloween in the small New England town where I lived. Halloween is one of my favorite holidays of the year due to the fact I could dress up without anyone really batting an eye and the fact I was a lover of all things Horror as well as supernatural ranging from the occult to the mythical. So while I had decided that I wasn't going out to anyone parties or go Trick or Treating that day, I still wanted to dress up and hand out candy to anyone who was.
I stood in front of the full length mirror on the inside of my wardrobe door and checked out my reflection, turning this way and that to get a different angle on my costume when needed: I had chosen to dress up as a Character I saw as an archetypal damsel in distress: Red Riding Hood.
The outfit was nice: a white button down blouse with poofy shoulder sleeves under a black low-cut corset that gave me a bit of a curve and a red and white gingham pleated mini skirt that poofed out a little and made it more revealing than it already was and a white fluffy petticoat that just about hid the tops of my black sheer stockings which went up to just beneath my scantily clad buttocks and were held in place by garter belts. A pair of black over the knee boots and a red hooded shoulder cape completed my outfit but I was still missing two items which were close at hand
On my bed was the woven basket in which all of the candy was going to be stored in and on my desk was the dark brown curly wig I had decided was going to be worn with the outfit when I was certain everything was right.
I'd always been equal parts Perfectionist and Control Freak and as I stared at my reflection as I switched from pose to pose, wiggling my bottom to see if my skirt would reveal anything I didn't want some random person to see when I was handing out candy, I felt a sense of pride in how I looked.
My body was by no means feminine which I was more or less fine with: I was short and stocky, with a broad chest and untrained but very obvious muscle but I had still somehow managed to come across as a short boyish girl in her early twenties despite it all.
I grabbed the wig from my desk and placed it atop my head, making sure it was secure before grabbing my basket and departing my room.
I lived in a single floor bungalow in a Cul-de-sac with a river at the back, which I wasn't too pleased about as I really didn't like water but it was a nice place and had been relatively cheap.
I rushed into the kitchen, setting my basket down on the countertop as I did so beforeore opening the cupboard door and pulling out bags of wrapped candy and chocolate from within and tearing the bags open before pouring the contents into the basket, but not before making sure that none of these treats had nuts or gluten in them.
Not because I had any allergies but in case anyone else did, last thing I wanted was to end up hospitalizing another person because of a bout of carelessness on my part.
Anyway, with that done I closed the cupboard door and binned the empty packets before grabbing my basket and making my way to the living room where my front door was.
I was a relatively private person so all the windows had their curtains drawn to avoid any peeping toms. This had the added benefit of meaning I could practice self-bondage in my home whenever the mood grabbed me without anyone inadvertently looking in and seeing me bent over the arm of a sofa with my panties on display because my skirt had accidentally-on-purpose ridden up or writhing on the kitchen table and mewling into my red ball gag as I pretended to struggle to free myself.
I had actually gotten pretty good at self-bondage and always made sure I had a way to get myself free if I needed to.
And it tended to grab me quite a bit if I am being honest. But despite how much of a horny bondage-slut I WAS, I had made a promise to myself that I wouldn't be indulging in that particular past time tonight as that would mean me quite possibly missing out on handing out candy to anyone that knocked on my door or even worse despite how unlikely it was to happen: being found in a compromising position because someone had come in to see if I was alright.
So, despite how horny the thought of being tied up in this outfit was, I couldn't do that. Not when it meant accidentally ruining someone else's night because I wasn't able to hand out candy.
Instead I simply opted to take a seat on my sofa, which had it's back to the front door, and turn on the TV while I waited for someone to knock. I adjusted my skirt, pulling it a tad bit lower as it rode up in response to my movements as I grabbed the remote and began looking through Netflix and Amazon Prime for anything horro-based to watch while I waited. Eventually I decided on Paranormal Activity and let that play before sinking into my seat, trying my best to be as ladylike as I could.
The main issue I soon found with this outfit though was the skirt: every slight movement made the tiny skirt that just about protected my modesty ride up to expose the curve of my ass and my stocking tops, forcing me to hurriedly pull it down and sending a little pulse of euphoria and excitement through me whenever I did so. It didn't help that I had something of an exhibitionist streak in me, albeit one that only extended to those who had consented.
Eventually the door bell ring, jolting me out of my euphoria filled thoughts in the process. I took a couple of moments to compose myself as I did so, standing up and tugging my skirt down to get some modesty before bending over to pick up the basket from where it sta on the sofa next to me.
And that was when I discovered another issue. Even when I bent slightly at the waist, the tiny thing rode up. I grabbed the basket handle and stood up straight, taking a moment to once again pull my skirt down to hide my underwear before sauntering over to the door and opening it to say hello to the Trick-or-Treaters, a collection of college students that were clearly looking for free food.
"TRICK OR TREAT, SMELL OUR FEET!" They cried out and I grinned sheepishly as I flipped up the lid of my basket. Some of them had actually put in effort into their costumes and were immediately identifiable to my nerdy eye: I could see a Captain America, Eren Jaeger (which made me snicker), Lucy Heartfilia and Luke Skywalker, while the others had seemingly haphazardly thrown their costumes together last minute.
"Looking for guys!" I chirped cheerfully in my best approximation of a female voice as I started handing out candy to them.
"Thanks, I love your Red Riding Hood outfit! Looks really cute!" The girl dressed as Lucy remarked, her eyes moving up and down my body as she did so.
That was when I noticed that some of the others in the group were also checking me out despite the fact I was guy. Maybe they didn't know, in that case my attempt at passing had worked, or if they just didn't care then that was also fine by me, just meant that I looked good in a miniskirt and stockings.
"Aw, thanks. I love your Lucy costume too, looks very cool." I responded, closing the lid of the basket as I did so "Fairy Tail's pretty fun."
"Thanks! Yeah I loved Lucy in it, she was soo cool!" I nodded in understanding and spent the next few moments chatting about nerdy things to the group, occasionally having to readjust my skirt as I did so before they left and I shut my door before returning to my seat.
The next few Trick-Or-Treaters would come and I would once again have to pull my skirt down and get leered at by the more grown-up ones as I handed out candy. This went on for a few hours until the door bell once again rung while I was watching Dracula and I went to open it.
Much to my surprise, instead of Trick-or-Treaters who were looking to score some candy, was instead a young man that was the same age as me.
He wore a simple letterman jacket over a pale pink button down shirt and denim jeans with baseball trainers. He had short, messy sandy blond hair and blue eyes and was looking down at me with a wolfish grin on his face.
"Trick-or-Treat!" Eric teased and my free hand immediately went to my skirt, trying to pull it down even further than I already had to no avail.
Eric. To describe Eric as a person would actually be pretty easy: he was a deviant with a bondage streak bigger than my own. We were Friends with Benefits and that was all either of us wanted from one another. But, that didn't mean I wasn't going to get immediately flustered at what I was wearing now that he was standing in front of me.
Other people, it was different. I hadn't dressed with any sexual thoughts in mind in regards to them so my attempts at modesty were entirely that.
But with Eric? I guess, it was also kind of part of our games. I would always play the part of the damsel-in-distress that he has come to kidnap and do sordid deeds to because he really liked it and I did too. So it was just as much "shit I don't want him to see anything under my skirt" as it was "let's remind him just how short this little thing is and hope he's here for some fun."
I know I had promised myself no self-bondage, I hadn't actually made that same promise in regards to regular bondage so if Eric decided he wanted to tie me up and put me somewhere out of sight for later, then who was I to stop him?
"Hey, Eric! Surprised to see you here." I remarked coyly before stepping aside to let him in "wanna come in?"
"Sure thing," he stepped inside and I closed the door behind him, pressing my back to it and turning the lock quietly.
"So, what brings you here?" I inquired, crossing my arms under my chest as I did so and making my pushup bra push my chest up somewhat. Eric turned to face me, that wolfish grin still plastered on his face.
"Nice outfit, love the little short skirt." He remarked and I hummed in agreement.
"Little bit TOO short though, don't you think?" I asked, lightly pinching the hem of the skirt's side and lifting it to reveal my garters. His eyes widened slightly before settling down as he stalked forwards.
"No, not really. Just short enough for what I have in mind." And just like that, I was aroused, my hardened cock pressing against the fabric of my panties as I pretended to sink away from him.
"O-Oh? And what's that, you naughty boy?" I asked with mocking concern as he pressed his body against mine, trapping me between himself and the door. I let out a not-so-pretend squeak of surprise as I felt a cold hand reach up under my skirt and pinch my buttock as he whispered into my ear as the heat rushed to my cheeks.
"Stay here like a good girl and you'll find out." With that he pulled away from me and walked off, making his way towards my bedroom.
Realizing I had mere seconds to avoid "punishment", I set the basket down onto the floor before hurrying over to the sofa, sitting down on it with my legs tucked into my body, causing my skirt to ride up further.
Eric returned shortly after that with a bundle of rope in his hands and I swallowed.
"Oh come on! Th-that's so not necessary, Eric." I moaned as he came over to me.
"Yes it is." He argued.
"But whyyyy! I just wanted to dress up for Halloween and hand out candy." I bemoaned through a pretend pout as he sat down behind me and forced my wrists behind my back.
"Cuz of that outfit" he admitted as he started tying my wrists together.
"You're just jealous that other people can look up my skirt. Perv."
"Yup! This ass is too cute to be viewed freely by the public" as he said this, a hand grabbed my ass and I squealed again, hips bucking slightly as he let go of my wrists. I rubbed them together to see if I could escape them to no avail while Eric proceeded to tie a chest harness on me, pinning my arms to my sides and then went about undoing the first few buttons of my blouse, allowing my lacy black push-up bra to spring free.
"H-hey! You don't have to do that! W-what if someone s-sees me!" I protested, squirming as I did so.
"Yes I do." Eric said before he forced me to bend over and he immediately wolf-whislted at the sight of my skimpy black panties which did nothing to cover my ass and my garters. I yelped as he gave me a quick smack before pulling my underwear down.
"Oh fuck. Really?! NOW you wanna stick it in?!" I asked "but I won't be able to walk for hours!"
"Shut up, I'm not sticking my dick in you." Eric chided before I felt something cold, hard and plastic be inserted into my bottom. I squirmed in pleasure and moaned abit, earning me some teasing from him as I unintentionally wiggled my ass.
"Naughty girl, aren't you? Like to act all coy but you love being treated roughly." I bit my lip and nodded as he pulled my panties back up and then threw me over his shoulder, a hand planted firmly on my ass and giving one cheek a tight squeeze.
My heart started to pound in my chest as he carried me out of my living room and into the hallway connecting every room in the bungalow together.
"H-hey, maybe this is a bad idea." I remarked "what if the door goes"
"I'll answer it."
"Whilst balls deep in my mouth?" I asked sarcastically, still squirming under his grip.
"Nope." I frowned at that but said nothing "so, what's made you decide on this outfit?"
"Well, Red Riding Hood's a damsel in distress isn't she? I mean yeah in most renditions of the story she isn't tied up but-"
"So you were hoping this would happen?"
"Hmm, maybe subconsciously yeah." He came to a stop in front of an empty cupboard and put me down. I looked at him in confusion and arousal as he opened it to reveal a pole running horizontally inside.
"Oh no, you're not sticking me in th-mmmphgrmph!" I squealed as he forced a large red ball-gag between my lips and secured it tightly behind my head.
"Yup, I am" Eric chortled before pushing me into the cupboard, making sure I was straddling the pole before using the remainder of my rope to secure my thighs, shins and ankles together before putting a crotch-rope between my legs while I mewled into the gag, squirming against my restraints and glaring at him as he stepped back to admire his depraved handiwork.
"That'll do for now, just need to keep you hidden away until later." I scowled, throwing my hair back as I did so.
"Mphmmphgrmrphm?!" I demanded before he just chuckled and closed the door in my face, leaving me trapped inside the cupboard with my skirt hitched and bunched up dangerously high and precum starting to soak my panties.
Which was when the thing he had inserted into me started to vibrate and I moaned loudly into my gag.
What. An. Asshole!