by Wedgieboy » Fri Jul 23, 2010 6:04 pm
I'm going to share some stories that happened to be when I was much younger, stories that got me into my various fetishes. See, I was an only child, and my mom had dated this guy for years. After a very long time he and his daughters moved in with me and my mom, and we became a family who all lived under the same roof. His two daughters, named Ashley and Cassie, were really nice and we all got along very well. Their bedroom was right next to my own, and our parents would usually leave for hours on end. I was 12, and they were both 14. This is this the story of the first time I ever got tied up.
Ashley was downstairs watching TV or something, and me and Cassie were talking together on the her bed. We soon started to wrestle abit like how we usually did, and since Cassie bigger and older than me she would usually win our tussles to my embarrassment. This time she pinned me in a way that made my shorts ride down, revealing my white briefs to her. She took great glee in my humiliation and helplessness, and pinned both my hands down with the power of just one of her hands, leaving her other hand free to pull down my shorts pass my knees. She curiously inspected my covered crotch area, and commented on how she thought my undies were cute. She said they kinda looked like panties, and my face was scarlet with shame. I begged her to get off of me and give me back my dignity, and she agreed in one condition.
She let me go and I went to pull up my shorts, but she grabbed my hand and told me not to. She said to take them off along with my shirt. I pleaded for her to leave me alone, but she said that if I didn't listen she would call up Ashley, who I knew would only make my case worse. Being seen in my underwear by one girl was awful, being seen like that by two girls I imagined, was a nightmare, so I did as I was told. I stripped off my shirt and pulled off my shorts completely, standing there infront of her in nothing but plain white briefs, which actually did look alot like panties I have to admit. I was mortified but at the same time I also kinda liked having her inspect my body like that, and I also liked being unable to handle the situation. She looked like she just received a brilliant idea and shot up, and told me to get on the bed facedown. I had no choice but to listen.
She then took out a very long scarf and tied my hands above my head to the post of the bed. She seemed like an expert with knots, and made quick work of tying my hands. I was totally subdued, and couldn't free myself no matter how much I tried, and she flipped me over onto my back, to my horror. See, inside of my underwear, my penis had betrayed me and turned into a boner, which my sister seemed delighted over seeing. I was humiliated even further, but I was loving this tie up adventure, and she was obviously enjoying it just as much. She locked the door of the room and then went back onto the bed next to me, tickling my sides and legs. She knew I was super ticklish, and I giggled and laughed at every touch she made to my body. After a few minutes of brutal tickle abuse, there were tears forming in my eyes and my sides were soar. But worse of all, I still had a small tent pitched in my underwear, so denying that I was having fun was pointless.
She made another comment concerning how my underwear looked like female underwear again, and she laughed at her own joke while I moaned in shame. She then said how she had gotten ANOTHER idea, and based on her last one, I wasn't looking forward to hearing what it was. Cassie flipped me again onto my stomach, and removed my underwear, leaving my totally naked, and tied up infront her. Luckily it didn't last long. My fiendish half-sister made another degrading comment, this time she was pleased that despite my underwear being white, there was no skid-marks. I said nothing to this, and she slapped my butt demanding my opinion. I shyly told her that I always made sure to keep my underwear clean, and she said that I was deserving of a reward. I signed at whatever she had inmind.
She skipped over to what I knew was her clothing drawer, and opened the first shelf. She pulled out, to my horror, a pair of pink silky panties! They were also very skimpy, almost like a thong. I knew what was coming next, and she slid them onto me, fixing them to they covered everything comfortably. Surprisingly, they fit perfectly and were quite comfortable, and then for the third time she flipped me onto my back to inspect her work. There I was tied with my hands over my head unable to prevent her torture, dressed in nothing but her pink silky panties, that blessingly covered my boy-parts and left alot to my imagination, atleast as far I as I knew. I did not however know that they mostly see-through, meaning she could see everything! The fabric was so soft and felt so good on my body that my boner swelled again, and she flipped me again. The back of the panties were basically a thong on me and covered nothing, leaving my cheeks on display to her joy, which she mockingly said were cute. Secrectly, I was loving every minute of my torture.
She went back to the tickle torture and which not after long made me cry with laughter, and then decided to give my behind a few smacks 'til it was reddish. We were enjoying ourselves so much that it was amazing, both us indulging in our young sadistic fantasies with great pleasure. Finally it got to the point where I could no longer hide how much I was liking everything she was doing to me, and I was unable to keep it a secret any further, so she got her third and most evil idea yet. She stripped off her jeans, and since we were half-siblings I had seen her in her underwear before, hell, I was even wearing her underwear. So it wasn't a massive deal I had to admit she was very attractive so seeing her like that turned me on even further. She was wearing a pair of blue silky boyshorts, which complimented her large bubble butt quite nicely. But that was just the beginning.
She sat her butt onto my face, and my face disappeared into her behind, which luckily was fully covered by the underwear or else it would have been disgusting. I loved it! The humiliation, the feel of her silky underwear and her butt, the helplessness, everything felt so good and I was so turned on. She kept her behind on my face for quite awhile, making sure I could breath. She sat ontop of my face, and she would occasionally wiggle her bum and shake it slightly over it, and everytime I enjoyed the feel. While she was doing this, she was looking at my barely-covered crotch which she said she loved watching. After what she told me was half an hour she got off of me, allowing me to breath easily again without her intimate scent permeating my lungs. She untied my hands and I got up, and we both gave eachother a little hug to show no hard feelings, and we both sat and talked with out silky underwear on display, having a good time.
After another hour Ashley was moving around downstairs so we had to call things to an end, and I admitted I loved wearing her feminine underwear. She reassured to me that anytime I felt like trying on her delicates that I was allowed to, and she showed me where she kept her undies. She opened the drawer so I could I get a good look inside, and saw dozens of very skimpy and sexy looking undies. Evidently Ashley had aton of panties of her own, but Cassie wasn't sure she would be cool with letting me wear her's, but she promised me I access to her own underwear, which seemed so kind to me. I put on my shorts and shirt and left on her silky pink undies on underneath my clothing, bringing my white briefs with me. I spent the rest of the day feeling so erotic and nice wearing her underwear, like an intimate secret that only we shared. We made sure to try that again, and of course, we did.
Wedgieboy : Tortured by my sisters (ff/m)
Moderator: Archiver
So me and Cassie continued our kinky tie up games for about a month, every other day I would willingly come back into her room, and she would lock the door behind me, making sure we were alone. We were often alone, as Ashley had soccer promise. Afterwards she would have me strip off my shorts and shirt, which would always reveal to her a pair of her own underwear that I was wearing. She asked me why I enjoyed wearing women's underwear so much, and I honestly admitted that they just felt nice. She was very kind and accepting of me, and would always tie me up in a comfortable, safe way, and would always make sure to keep my penis covered with the panties as I never wanted to be fully naked and completely exposed. Apparently seeing my uncovered penis made her feel awkward anyway.
Even kinder of her, was her continued desire to shove my face into her behind, which was always covered with a frilly pair of underwear to be clean. I was always tied up during this, sometimes spread eagled. She would sit on my face about 20 minutes every day, and while she was doing this she would often play with my nipples, twisting them and feeling them up while I writhed behind the weight of her butt, but she was very light and never put much pressure on me. I had to promise her a few things, for example in return, I had to shave my body all over and make sure to be hairless at all times, other than the hair on my head, which she wanted me to grow out so I looked more feminine. She had bought a lot of new underwear, which she demanded I wear at all times and even went as far as to take away all my own underwear and throw it all away.
All these adventures with Cassie made us very close, and we eventually became like twins/best friends. She took several pictures of me dressed in her underwear, which she promised she would never show anyone and only had them for her own pleasure. It got to the point where we so comfortable being around eachother, that while I was tied up on her bed, she would strip down to her own underwear while she tortured me. I nearly always had a boner during these times because I could never seem to keep my boy at bay, as it seemed I got turned on easily, and the sight of my beautiful half-sister in her pretty delicates was a sight to behold. She was a pale, pretty, skinny girl, with long black hair and bangs that complimented her gorgeous lake-blue eyes. She had a nice bubble butt and firm breasts, which she allowed me to grope every once in a while if I was good and she was feeling loose. Cassie was a sweet, caring girl who always loved having fun.
During a particularly embarrassing tie up game, which involved me dressed in a blue cotton pair of boyshorts and nothing else, she made me hump a pillow for her amusement, while she swatted by bum with one of her belts. I got very tired very quickly, but she made me continue to thrust my crotch into the pillow while she swung the belt against my behind, causing a loud wack each time. My hands were tied above my head, and my legs were secured with a dog-leash that made sure I wasn't going anywhere. After about twenty minutes of this humiliating but enjoyable abuse, we were both tired and she flipped me back onto my back while we both caught our breath laying next to eachother on her bed. She rested her head on my chest as she relaxed, and I watched her chest go up and down with every breath, covered in sweat, and clad in only a skimpy white bra. She was so hot and I wanted her so badly, but she was always incontrol of these games and she showed no lust back towards me... or so I thought.
She confessed something to me; that she had been thinking about me in some strange ways. She said that she loved looking at the pictures of me that she had taken, and had been equally as turned on during our games. Since we weren't really related, she didn't fear incest, but didn't want to ruin our friendship and fun together by pursuing anything romantic, atleast for a while. I was so pleased and told her that whenever she was ready, that I would be, and we kissed while I was tied up, eventually making out. It was the most amazing feeling in the world and I cursed my binds for not allowing me to embrace her back, and then told me another little secret.
Then she sat up and very innocently, told me that she wanted Ashley to know about our games. I barked at her that there was no way that I would allow that, but, somehow, her cuteness made me change my mind. Her darling blue eyes and adorable bangs just always made me fold to her, and I agreed. She promised me that we could be a couple as soon as my hair got aslong as her's, (lol) and when Ashley was aware of what we doing and ok with it, which she assured me she would. Cassie then untied me and we hugged closely, both us dressed in only her underwear. She was wearing a white thong which matched her bra, because for some reason despite her shyness and meekness, her underwear selection was always less than conservative and quite skimpy, which she justified as having to do with how uncomfortable she felt normal underwear was. Plus I loved the extra skin it would show off.
She had me pose for a few more pictures, and told me to get dressed and she did aswell. The next day I came back, and she told me to get ready and clean myself in the bathroom. I asked her why, and she told me that mom and dad were going to be gone that night, and that it was the prime opportunity to reveal our secret to Ashley. I gulped and did as I was told, preparing for what was surely going to be the most humiliating night of my life.
Even kinder of her, was her continued desire to shove my face into her behind, which was always covered with a frilly pair of underwear to be clean. I was always tied up during this, sometimes spread eagled. She would sit on my face about 20 minutes every day, and while she was doing this she would often play with my nipples, twisting them and feeling them up while I writhed behind the weight of her butt, but she was very light and never put much pressure on me. I had to promise her a few things, for example in return, I had to shave my body all over and make sure to be hairless at all times, other than the hair on my head, which she wanted me to grow out so I looked more feminine. She had bought a lot of new underwear, which she demanded I wear at all times and even went as far as to take away all my own underwear and throw it all away.
All these adventures with Cassie made us very close, and we eventually became like twins/best friends. She took several pictures of me dressed in her underwear, which she promised she would never show anyone and only had them for her own pleasure. It got to the point where we so comfortable being around eachother, that while I was tied up on her bed, she would strip down to her own underwear while she tortured me. I nearly always had a boner during these times because I could never seem to keep my boy at bay, as it seemed I got turned on easily, and the sight of my beautiful half-sister in her pretty delicates was a sight to behold. She was a pale, pretty, skinny girl, with long black hair and bangs that complimented her gorgeous lake-blue eyes. She had a nice bubble butt and firm breasts, which she allowed me to grope every once in a while if I was good and she was feeling loose. Cassie was a sweet, caring girl who always loved having fun.
During a particularly embarrassing tie up game, which involved me dressed in a blue cotton pair of boyshorts and nothing else, she made me hump a pillow for her amusement, while she swatted by bum with one of her belts. I got very tired very quickly, but she made me continue to thrust my crotch into the pillow while she swung the belt against my behind, causing a loud wack each time. My hands were tied above my head, and my legs were secured with a dog-leash that made sure I wasn't going anywhere. After about twenty minutes of this humiliating but enjoyable abuse, we were both tired and she flipped me back onto my back while we both caught our breath laying next to eachother on her bed. She rested her head on my chest as she relaxed, and I watched her chest go up and down with every breath, covered in sweat, and clad in only a skimpy white bra. She was so hot and I wanted her so badly, but she was always incontrol of these games and she showed no lust back towards me... or so I thought.
She confessed something to me; that she had been thinking about me in some strange ways. She said that she loved looking at the pictures of me that she had taken, and had been equally as turned on during our games. Since we weren't really related, she didn't fear incest, but didn't want to ruin our friendship and fun together by pursuing anything romantic, atleast for a while. I was so pleased and told her that whenever she was ready, that I would be, and we kissed while I was tied up, eventually making out. It was the most amazing feeling in the world and I cursed my binds for not allowing me to embrace her back, and then told me another little secret.
Then she sat up and very innocently, told me that she wanted Ashley to know about our games. I barked at her that there was no way that I would allow that, but, somehow, her cuteness made me change my mind. Her darling blue eyes and adorable bangs just always made me fold to her, and I agreed. She promised me that we could be a couple as soon as my hair got aslong as her's, (lol) and when Ashley was aware of what we doing and ok with it, which she assured me she would. Cassie then untied me and we hugged closely, both us dressed in only her underwear. She was wearing a white thong which matched her bra, because for some reason despite her shyness and meekness, her underwear selection was always less than conservative and quite skimpy, which she justified as having to do with how uncomfortable she felt normal underwear was. Plus I loved the extra skin it would show off.
She had me pose for a few more pictures, and told me to get dressed and she did aswell. The next day I came back, and she told me to get ready and clean myself in the bathroom. I asked her why, and she told me that mom and dad were going to be gone that night, and that it was the prime opportunity to reveal our secret to Ashley. I gulped and did as I was told, preparing for what was surely going to be the most humiliating night of my life.
Cassie demanded that I had to strip nude in her room and then go straight to shower and shave and get ready; she assured me that she would bring in what I was wearing and that Ashley would be back at 8 PM, and it was then 7:30. I got squeaky clean and made sure every inch of me was spotless and shaved, and she knocked on the door and told me that she had what I was supposed to wear picked out. I covered myself with a towel and let her in, and she had a black thong with her, a pair of her short-shorts, and a tank top. I was supposed to wear fully female clothing! Cassie seemed sorry and told me I had to, and allowed me to change in peace. I slipped on the black thong, which luckily covered my balls and penis quite well, but was so silky I instantly got turned on.
I slipped on the short-shorts which barely fit me and left very little to the imagination, and they also gave me a major wedgie. The tank-top slipped on quite well but it was so short it barely covered above my belly, leaving alot of skin on show. I heard a commotion begin downstairs, and heard Ashley's voice and alot of shifting about, meaning she was here and my moment of humiliation had come. I inspected myself in the mirror... my shoulder length hair and totally hairless body made me look like a girl, and if it wasn't for the undeniable bulge in my shorts and flat chest, I could have passed off as a lady. Cassie had seen me like this quite a few times and I was very open to her, but the idea of Ashley seeing me like this horrified and turned me on simultaneously.
Cassie came back in and said it was all ready, and tied my hands tightly behind my back, and then loosely tied my legs so I could walk, but running was totally out of the question. For some strange reason I also had to wear a blind-fold, but she promised me that she would guide be into her room safely, missing me on the lips gently. She grabbed the front of my shorts, giving me a slight frontal wedgie, and slowly directed me through the hallway. I couldn't see a thing and my heart was beating like a drum, and eventually we entered her room. I could sense a presence inside the room already, and was utterly mortified when I was instructed to lay on her bed, where my hands were then tied above my head and my legs were tied similarly to the bottom. I heard some subdued whispering and giggling, and I felt a pair of hands on my feet, which I could tell were Cassie's. But then!...
A pair of hands grabbed my hips, but.... another pair wrapped around my blindfold, removing it. Which reveled that there was Ashley, Cassie, another girl! It was Ayme, one of Cassie's best friends, who had her hands clutching my hips. I asked what the hell was going on, and then all three girls started tickling me relentlessly to avoid answering. Cassie made cruel work of my feet, Ayme had my hips, and Ashley had my armpits, all of them brutally invading my body with the feathery hands. I laughed hysterically and was quickly out of breath, which hurt badly since my lungs were without air. Tears filled my eyes, and I was in agony and utterly humiliated moreso than I had ever been in my life, dressed like that infront of three very attractive girls I knew very well. But still, my erection revealed otherwise to them.
Then they untied my hands and stripped off the shorts and tanktop, tying me again, in nothing but the skimpy black thong. They all sat around, staring at me, which made it very hard for me to think straight with their eyes invading my space. My face was bright red but I still managed to ask why Ayme was there, despite my condition. Cassie looked really sorry and said that Ashley had brought her, and that there was nothing she could do. Ashley and Ayme said the idea that I was a cross-dresser and bondage fanatic all sounded too good to pass up, and that they all jumped at the choice to join in with my torture. They promised to keep everything a secret. Furthermore, Ayme decided to place her hand over my covered cock, which I did not like. Cassie knew well enough not to do that, but Ayme didn't know better. Cassie swatted her hand away soon after, and they all got up and untied me again, deciding on a new technique of abuse.
Ashley got out a dress from her closet, a pink, mostly see-through one, which was actually a nightgown that she used to wear. I was forced to try it on, infront of all three of them. They hurled insults at me of course, and mocked me while I had no choice but to parade around infront of them in nothing but a pink night-gown and black thong. They laughed and were having a great time at my expense, and I would be lying if I said I wasn't enjoying it. They tied me down again, and got to my favorite part... the face-sitting part. Cassie explained that I loved it when girls sat on my face, and even though it was embarrassing to have my fetish revealed, I loved that I was going to have such a chance with three girls. Ashley and Ayme seemed really happy with indulging that whim, as I had been their play toy for the entire night already, it only seemed fair.
Cassie removed her pants first, revealing a white thong that she had on yesterday, and Ashley took off her pants next. Ashley was alot like Cassie, but had much bigger boobs and far nicer behind. Her hair was shorter and was a bob style, but it was black aswell, with similar blue eyes and sexy bangs. She was also a bit taller. Ayme was blonde, and very skinny, and had the best female parts of all of them, but was very short. All three girls quickly took off their pants, and Ashley's nice black thong and Ashley's blue bikini-cut briefs all looked so sexy to me. Here I was with three babes in their underwear surrounding me! Since Ayme was the only one not in a thong, she was supposed to sit on my face to be clean, while Cassie was to sit on my stomach, and Ashley was supposed to sit on my crotch! They all got into position and it was pure heaven.
I breathed in and was delighted to find that Ayme smelled much different from Cassie, and her massive butt nearly devoured my head. Cassie's little behind wiggled on my chest, and Ashley's delicate bottom encased my very erect cock. Ashley commented on how it felt weird, but my crotch was covered and flattened by the thong and gown, so it wasn't anything serious. Suddenly I felt Cassie starting to stroke my tummy, and Ashley followed suit, stroking my legs. Ayme then did the same to my arms, and having all three girls doing this sent shivers down my body and I was desperate to cum or release. Cassie never allowed me to but I thought that maybe these two girls would have more mercy, and I started to thrash my head around to tell Ayme to get off. I explained my embarrassing situation, and they said that they had to leave then! I begged for them to allow me to release myself and Cassie said she didn't want me to cum or anything, though I had no idea why.
I was going to ask why but I was soon gagged, and was kept there tied up while Ashley and Ayme got dressed and soon left. It was almost 11 by then and Cass and Ash got ready for bed; they had a bunk bed and both slept under eachother. Ashley slept in her bra and panties, and Cassie slept in only a thong, a cute red one. I wanted to shout at them to let me go, but Cassie got into bed with me and put the covers over us. She hugged and embraced me like a teddy bear, and quickly I relaxed and figured that I was probably going to have to sleep that way all night. And I did. Sleeping next to Cassie like that was the best part of the whole night. She teased me a few times by placing her hand near my crotch, but other than that, it was a great night's sleep, though my tied hands got tired.
I slipped on the short-shorts which barely fit me and left very little to the imagination, and they also gave me a major wedgie. The tank-top slipped on quite well but it was so short it barely covered above my belly, leaving alot of skin on show. I heard a commotion begin downstairs, and heard Ashley's voice and alot of shifting about, meaning she was here and my moment of humiliation had come. I inspected myself in the mirror... my shoulder length hair and totally hairless body made me look like a girl, and if it wasn't for the undeniable bulge in my shorts and flat chest, I could have passed off as a lady. Cassie had seen me like this quite a few times and I was very open to her, but the idea of Ashley seeing me like this horrified and turned me on simultaneously.
Cassie came back in and said it was all ready, and tied my hands tightly behind my back, and then loosely tied my legs so I could walk, but running was totally out of the question. For some strange reason I also had to wear a blind-fold, but she promised me that she would guide be into her room safely, missing me on the lips gently. She grabbed the front of my shorts, giving me a slight frontal wedgie, and slowly directed me through the hallway. I couldn't see a thing and my heart was beating like a drum, and eventually we entered her room. I could sense a presence inside the room already, and was utterly mortified when I was instructed to lay on her bed, where my hands were then tied above my head and my legs were tied similarly to the bottom. I heard some subdued whispering and giggling, and I felt a pair of hands on my feet, which I could tell were Cassie's. But then!...
A pair of hands grabbed my hips, but.... another pair wrapped around my blindfold, removing it. Which reveled that there was Ashley, Cassie, another girl! It was Ayme, one of Cassie's best friends, who had her hands clutching my hips. I asked what the hell was going on, and then all three girls started tickling me relentlessly to avoid answering. Cassie made cruel work of my feet, Ayme had my hips, and Ashley had my armpits, all of them brutally invading my body with the feathery hands. I laughed hysterically and was quickly out of breath, which hurt badly since my lungs were without air. Tears filled my eyes, and I was in agony and utterly humiliated moreso than I had ever been in my life, dressed like that infront of three very attractive girls I knew very well. But still, my erection revealed otherwise to them.
Then they untied my hands and stripped off the shorts and tanktop, tying me again, in nothing but the skimpy black thong. They all sat around, staring at me, which made it very hard for me to think straight with their eyes invading my space. My face was bright red but I still managed to ask why Ayme was there, despite my condition. Cassie looked really sorry and said that Ashley had brought her, and that there was nothing she could do. Ashley and Ayme said the idea that I was a cross-dresser and bondage fanatic all sounded too good to pass up, and that they all jumped at the choice to join in with my torture. They promised to keep everything a secret. Furthermore, Ayme decided to place her hand over my covered cock, which I did not like. Cassie knew well enough not to do that, but Ayme didn't know better. Cassie swatted her hand away soon after, and they all got up and untied me again, deciding on a new technique of abuse.
Ashley got out a dress from her closet, a pink, mostly see-through one, which was actually a nightgown that she used to wear. I was forced to try it on, infront of all three of them. They hurled insults at me of course, and mocked me while I had no choice but to parade around infront of them in nothing but a pink night-gown and black thong. They laughed and were having a great time at my expense, and I would be lying if I said I wasn't enjoying it. They tied me down again, and got to my favorite part... the face-sitting part. Cassie explained that I loved it when girls sat on my face, and even though it was embarrassing to have my fetish revealed, I loved that I was going to have such a chance with three girls. Ashley and Ayme seemed really happy with indulging that whim, as I had been their play toy for the entire night already, it only seemed fair.
Cassie removed her pants first, revealing a white thong that she had on yesterday, and Ashley took off her pants next. Ashley was alot like Cassie, but had much bigger boobs and far nicer behind. Her hair was shorter and was a bob style, but it was black aswell, with similar blue eyes and sexy bangs. She was also a bit taller. Ayme was blonde, and very skinny, and had the best female parts of all of them, but was very short. All three girls quickly took off their pants, and Ashley's nice black thong and Ashley's blue bikini-cut briefs all looked so sexy to me. Here I was with three babes in their underwear surrounding me! Since Ayme was the only one not in a thong, she was supposed to sit on my face to be clean, while Cassie was to sit on my stomach, and Ashley was supposed to sit on my crotch! They all got into position and it was pure heaven.
I breathed in and was delighted to find that Ayme smelled much different from Cassie, and her massive butt nearly devoured my head. Cassie's little behind wiggled on my chest, and Ashley's delicate bottom encased my very erect cock. Ashley commented on how it felt weird, but my crotch was covered and flattened by the thong and gown, so it wasn't anything serious. Suddenly I felt Cassie starting to stroke my tummy, and Ashley followed suit, stroking my legs. Ayme then did the same to my arms, and having all three girls doing this sent shivers down my body and I was desperate to cum or release. Cassie never allowed me to but I thought that maybe these two girls would have more mercy, and I started to thrash my head around to tell Ayme to get off. I explained my embarrassing situation, and they said that they had to leave then! I begged for them to allow me to release myself and Cassie said she didn't want me to cum or anything, though I had no idea why.
I was going to ask why but I was soon gagged, and was kept there tied up while Ashley and Ayme got dressed and soon left. It was almost 11 by then and Cass and Ash got ready for bed; they had a bunk bed and both slept under eachother. Ashley slept in her bra and panties, and Cassie slept in only a thong, a cute red one. I wanted to shout at them to let me go, but Cassie got into bed with me and put the covers over us. She hugged and embraced me like a teddy bear, and quickly I relaxed and figured that I was probably going to have to sleep that way all night. And I did. Sleeping next to Cassie like that was the best part of the whole night. She teased me a few times by placing her hand near my crotch, but other than that, it was a great night's sleep, though my tied hands got tired.
I woke up to a beautiful sight: Cassie changing infront of me. She was just removing her bra, and when it landed to the ground, she turned around and caught me. ''You're finally awake!'' she proclaims, apparently I had slept in. I tried to move but I was still tied the same way as the night before, still in Ashley's nightgown and Cassie's thong. But I wasn't the only one nearly naked, Cassie was standing in nothing but a red thong herself. My boner woke up aswell, giving me a bad case of morning wood. She smiles and made a comment concerning my erection. ''Boy, does that thing ever take a break'', she jokes, and she unties me finally. We have a good firm hug and I loved Cassie's sense of caring, as this entire experience was made so lovely because of her, and we kissed awhile. I take off the gown and she tells me to get dressed. ''In what?'', I queried.
She picks out a pink skirt and a frilly blue cotton shirt with a flower pattern. I recognized them as her own. ''Now that Ashley has seen you like that, you're free to dress in women's clothing all day long. We both know mom and dad are never around.'' There was much truth in her comments, as it was true that our parents were always working and very busy. She guaranteed me that the three of us were home alone, and I put on the shirt, and just as I was putting on the skirt, Cassie tells me to change my underwear. I guess she was right, and I pulled them down, going over to her underwear drawer. I picked out a cute pink pair of bikini-cut panties I always liked, and as she was changing on the other side of the room, she tells me that I'm now free to wear any of Ashley's pairs if I wanted. I jumped at the chance.
I had never seen Ashley's underwear drawer before, and as I opened it, I was amazed. Her choice of underwear was far more skimpy than Cassie's, with nearly every pair being a thong or g-string. The g-strings were far to skimpy for me, as my boy-parts would fall right out of them, but there was an adorable white thong that had alot of fabric on the front. It was satin, my favorite fabric. Nearly all of Cassie's underwear drawer consisted of cotton and silk, so a satin thong like that was to good a chance to turn down. I tried it on and was instantly turned on by the cool, sensual feel it had. Then I slipped on the skirt and Cassie was nearly done herself, putting on a pair of jeans and a shirt under her red bra and thong. She opened the second drawer and took our two pairs of pink socks, one pair for her, and one pair for me.
When we done we went to the bathroom and fixed our long hair. ''Your hair grows fast'', she praises, ''you should have hair as long as me in a week.'' I was glad I pleased her and when I fixed my hair to have bangs like her, I looked at myself in the mirror. If it wasn't for the flatness of my chest you would never have known I was a boy, infact I was surprised she didn't have me wear a stuffed bra or something. She then fixes some eye-liner on, and helps me put on some myself. We then rushed downstairs for breakfast. Ashley was down there already, and she seemed very amused at how I was dressed. ''Wearing any of my thongs?'' she asks as I sit down, and I nod yes. She demands me to show her, and I flipped up my skirt revealing what I was wearing, to both of their enjoyment. She smirks, and asks what we're doing for the day.
Cassie turns to me and says we're going shopping. I asked loudly ''what!'', and Cassie told me that nobody would recognize me dressed like that. ''But I have no boobs'', I argued, and she admits I have a good point. ''Stuff one of my bras, you'll look the part'' Ashley volunteers, and just as I was afraid as it was obvious that would happen. Cassie orders me kindly to go upstairs and get one of Ashley's bras, and I fetched a matching white one. Then I had to put it on under my shirt, which was filled with a bunch of toilet paper. As we were leaving I admitted I didn't want to go, and Cassie said that we would go underwear shopping as I needed some better fitting panties. The desire to pick out any pair of underwear I wanted made me say yes, and she said that we'd pick up some hand-cuffs to! Ashley tagged along.
The three of us called a cab and we eventually got to the mall. We went straight to the women's departments, and Cassie tells me to look around, as she needed to pick something up. I looked in the non-thong piles, and found a few pairs. Ashley comes up behind me and asks me how I'm doing, and I say fine. ''You know what would be embarrassing?'', she asks, and I say I have no idea. She continues ''you're skirt may get tucked into your thong by accident, or you may even get pantsed''. I got very worried and begged her not to do anything publicly, and she puts her hand down my skirt and gives me a strong wedgie. It was very painful (though I actually quite liked it) but I ignored her and picked out a total of 6 pairs, all of them very feminine and covering, and she laughs at my selection. ''Alright, now to the changing room'', she barks.
Luckily the skirt allowed me to try on the different pairs easily, not having to remove my skirt completely to change. Atleast so I thought; she says she wants to see the panties on me, so I have to remove my skirt. She watched intently as I removed each pair of panties, revealing my bare crotch to her each time. Eventually she tells me to stay right there for a moment, while I was wearing a pair of pink boy-shorts with a flowery pattern, with yellow lacing around the legholes. It felt so good on me, and I was very turned on. Then, to my horror, in comes in Ashley and a saleswomen, named Charlie! ''My brother is a huge pantyfreak'', she jokes, ''he wanted to get a fitting to see what kind of panties he needs to wear.'' Ashley later told me she knew Charlie very well as she always shopped there, and she was in on the joke.
The sales women is very humored by this, and I stood there humiliated, covering my very visible erection. ''I'll have to get Cindy'', she says, and I'm mortified! Another stranger is going to have to see me like this. Ashley is smiling all the while, loving every minute of my humiliation. She tells me that if I cover infront of the next girl, she'll pull down my panties, and I place my hands behind my back despite what my body is telling me. Cassie never actually was cruel and sadistic like this, and always did everything lovingly. A very young, pretty red-head walks in and laughs as soon as she sees me standing there, and Ashley joins in, while my face turns red. Secretly, I loved this and Ashley was doing me a major favor.
Ashley fills ''Cindy'' in on the situation, and Cindy comes up to me a with a measuring tape, taking some basic fittings. ''Hm, it seems our friend here is already perfectly fit. However, it seems his little friend there needs a bit more room'', she jokes, and both her and Ashley have a large laugh while I shyly retreat into my own skin. ''I can bring out some pairs for men'', but Ashley tells her I only wear female underwear. She pondered for a moment and the says she has some pairs for transvestites that would support my boyparts. I was humiliated, knowing I had to try on underwear for women born with cocks. She leaves and quickly returns, with twenty pairs, all my size. ''Could I?...''' Cindy awkwardly asks, and Ashley understands she wants to see me change, and decided to ask me.
''Come on, you'd love for Cindy to stay and watch'', and I figure out she's going to make me ask to her stay. ''Cindy'', I force myself to say, ''I would love it if you stayed and watched''. They're both very delighted, and I'm agonizingly forced to pull down my panties. The large mirror made sure they saw every inch of me, and I picked up the first pair in the pile. They fit amazingly, they felt good and girly, but supported my boy parts and cradled them with the support I needed. I angrily repeated this process twenty times, and finally, I put on my original satin thong. They talked for a while and apparently, Ashley was going to but me every pair, as they were cheap and the lady was willing to give us a bargain. To my surprise, Ashley actually did me a very generous favor, and I thanked her. ''After all that, it was the least I could.''
Cindy happily puts every pair in a bag for us, and asks me if I want to wear one of the pairs right now out of the store, as they were all paid for. Ashley answers for me ''nah, I want to get the most out of the pair he's wearing right now'', and she thanks her and we leave. Evidently they had those panties there for ages, and nobody ever bought a single pair, meaning they were willing to give them away cheap. We waited for a while, and eventually came Cassie, and I thanked god for finally seeing her return. She looks very pleased and has a large bag, which she tells me I'm unable to see the content of 'til we get home. We bought a few more things and took a cab back home, and when we got back home, she anxiously showed me what she got.
''A ballgag, and two pairs of kinky fluffy hand-cuffs'', she shows me, and I asked how she was able to get them. Apparently Ayme's mom worked at the sex shop, and that was the real reason why Ayme came over, to grease the wheels so she could buy this legally. But that wasn't all, as she pulls out a pair of vibrating panties! She said she was penisaphobic (lol) and hated touching and seeing penises, so she was unable to help me cum, so the vibrating panties would solve all our problems. I looked at all the bondage gear, and was so excited for the most perfect night I could imagine. She asked Ashley to find something to do for the night as she wanted to have some alone time with me, and Ashley agreed. I was so happy I could have orgasmed right there.
Sorry for no actual bondage this time, I needed to set up the next part. Now that part is bondagetastic.
She picks out a pink skirt and a frilly blue cotton shirt with a flower pattern. I recognized them as her own. ''Now that Ashley has seen you like that, you're free to dress in women's clothing all day long. We both know mom and dad are never around.'' There was much truth in her comments, as it was true that our parents were always working and very busy. She guaranteed me that the three of us were home alone, and I put on the shirt, and just as I was putting on the skirt, Cassie tells me to change my underwear. I guess she was right, and I pulled them down, going over to her underwear drawer. I picked out a cute pink pair of bikini-cut panties I always liked, and as she was changing on the other side of the room, she tells me that I'm now free to wear any of Ashley's pairs if I wanted. I jumped at the chance.
I had never seen Ashley's underwear drawer before, and as I opened it, I was amazed. Her choice of underwear was far more skimpy than Cassie's, with nearly every pair being a thong or g-string. The g-strings were far to skimpy for me, as my boy-parts would fall right out of them, but there was an adorable white thong that had alot of fabric on the front. It was satin, my favorite fabric. Nearly all of Cassie's underwear drawer consisted of cotton and silk, so a satin thong like that was to good a chance to turn down. I tried it on and was instantly turned on by the cool, sensual feel it had. Then I slipped on the skirt and Cassie was nearly done herself, putting on a pair of jeans and a shirt under her red bra and thong. She opened the second drawer and took our two pairs of pink socks, one pair for her, and one pair for me.
When we done we went to the bathroom and fixed our long hair. ''Your hair grows fast'', she praises, ''you should have hair as long as me in a week.'' I was glad I pleased her and when I fixed my hair to have bangs like her, I looked at myself in the mirror. If it wasn't for the flatness of my chest you would never have known I was a boy, infact I was surprised she didn't have me wear a stuffed bra or something. She then fixes some eye-liner on, and helps me put on some myself. We then rushed downstairs for breakfast. Ashley was down there already, and she seemed very amused at how I was dressed. ''Wearing any of my thongs?'' she asks as I sit down, and I nod yes. She demands me to show her, and I flipped up my skirt revealing what I was wearing, to both of their enjoyment. She smirks, and asks what we're doing for the day.
Cassie turns to me and says we're going shopping. I asked loudly ''what!'', and Cassie told me that nobody would recognize me dressed like that. ''But I have no boobs'', I argued, and she admits I have a good point. ''Stuff one of my bras, you'll look the part'' Ashley volunteers, and just as I was afraid as it was obvious that would happen. Cassie orders me kindly to go upstairs and get one of Ashley's bras, and I fetched a matching white one. Then I had to put it on under my shirt, which was filled with a bunch of toilet paper. As we were leaving I admitted I didn't want to go, and Cassie said that we would go underwear shopping as I needed some better fitting panties. The desire to pick out any pair of underwear I wanted made me say yes, and she said that we'd pick up some hand-cuffs to! Ashley tagged along.
The three of us called a cab and we eventually got to the mall. We went straight to the women's departments, and Cassie tells me to look around, as she needed to pick something up. I looked in the non-thong piles, and found a few pairs. Ashley comes up behind me and asks me how I'm doing, and I say fine. ''You know what would be embarrassing?'', she asks, and I say I have no idea. She continues ''you're skirt may get tucked into your thong by accident, or you may even get pantsed''. I got very worried and begged her not to do anything publicly, and she puts her hand down my skirt and gives me a strong wedgie. It was very painful (though I actually quite liked it) but I ignored her and picked out a total of 6 pairs, all of them very feminine and covering, and she laughs at my selection. ''Alright, now to the changing room'', she barks.
Luckily the skirt allowed me to try on the different pairs easily, not having to remove my skirt completely to change. Atleast so I thought; she says she wants to see the panties on me, so I have to remove my skirt. She watched intently as I removed each pair of panties, revealing my bare crotch to her each time. Eventually she tells me to stay right there for a moment, while I was wearing a pair of pink boy-shorts with a flowery pattern, with yellow lacing around the legholes. It felt so good on me, and I was very turned on. Then, to my horror, in comes in Ashley and a saleswomen, named Charlie! ''My brother is a huge pantyfreak'', she jokes, ''he wanted to get a fitting to see what kind of panties he needs to wear.'' Ashley later told me she knew Charlie very well as she always shopped there, and she was in on the joke.
The sales women is very humored by this, and I stood there humiliated, covering my very visible erection. ''I'll have to get Cindy'', she says, and I'm mortified! Another stranger is going to have to see me like this. Ashley is smiling all the while, loving every minute of my humiliation. She tells me that if I cover infront of the next girl, she'll pull down my panties, and I place my hands behind my back despite what my body is telling me. Cassie never actually was cruel and sadistic like this, and always did everything lovingly. A very young, pretty red-head walks in and laughs as soon as she sees me standing there, and Ashley joins in, while my face turns red. Secretly, I loved this and Ashley was doing me a major favor.
Ashley fills ''Cindy'' in on the situation, and Cindy comes up to me a with a measuring tape, taking some basic fittings. ''Hm, it seems our friend here is already perfectly fit. However, it seems his little friend there needs a bit more room'', she jokes, and both her and Ashley have a large laugh while I shyly retreat into my own skin. ''I can bring out some pairs for men'', but Ashley tells her I only wear female underwear. She pondered for a moment and the says she has some pairs for transvestites that would support my boyparts. I was humiliated, knowing I had to try on underwear for women born with cocks. She leaves and quickly returns, with twenty pairs, all my size. ''Could I?...''' Cindy awkwardly asks, and Ashley understands she wants to see me change, and decided to ask me.
''Come on, you'd love for Cindy to stay and watch'', and I figure out she's going to make me ask to her stay. ''Cindy'', I force myself to say, ''I would love it if you stayed and watched''. They're both very delighted, and I'm agonizingly forced to pull down my panties. The large mirror made sure they saw every inch of me, and I picked up the first pair in the pile. They fit amazingly, they felt good and girly, but supported my boy parts and cradled them with the support I needed. I angrily repeated this process twenty times, and finally, I put on my original satin thong. They talked for a while and apparently, Ashley was going to but me every pair, as they were cheap and the lady was willing to give us a bargain. To my surprise, Ashley actually did me a very generous favor, and I thanked her. ''After all that, it was the least I could.''
Cindy happily puts every pair in a bag for us, and asks me if I want to wear one of the pairs right now out of the store, as they were all paid for. Ashley answers for me ''nah, I want to get the most out of the pair he's wearing right now'', and she thanks her and we leave. Evidently they had those panties there for ages, and nobody ever bought a single pair, meaning they were willing to give them away cheap. We waited for a while, and eventually came Cassie, and I thanked god for finally seeing her return. She looks very pleased and has a large bag, which she tells me I'm unable to see the content of 'til we get home. We bought a few more things and took a cab back home, and when we got back home, she anxiously showed me what she got.
''A ballgag, and two pairs of kinky fluffy hand-cuffs'', she shows me, and I asked how she was able to get them. Apparently Ayme's mom worked at the sex shop, and that was the real reason why Ayme came over, to grease the wheels so she could buy this legally. But that wasn't all, as she pulls out a pair of vibrating panties! She said she was penisaphobic (lol) and hated touching and seeing penises, so she was unable to help me cum, so the vibrating panties would solve all our problems. I looked at all the bondage gear, and was so excited for the most perfect night I could imagine. She asked Ashley to find something to do for the night as she wanted to have some alone time with me, and Ashley agreed. I was so happy I could have orgasmed right there.
Sorry for no actual bondage this time, I needed to set up the next part. Now that part is bondagetastic.
I was ready for my intimate night alone with Cassie, and as I entered her room at 10 PM, the time she told me to, I was dressed in a sleek red sundress. Underneath were black frilly panties, and I had my hair the way she liked it, dressed exactly the way she told me to. Hidden behind the pretty dress was a large boner naturally, as I was so excited. I came into the room, and Cassie did not disappoint - when I entered I saw her standing there in a white strapless bra and a matching satin thong, revealing nearly all of her amazing body. ''Ready?'', she asks in a hushed sensual tone, and I nodded yes. She told me to remove the dress and I did, and then the thong, laying on my stomach on her bed totally nude. She then got out the new equipment!
She handcuffed my hands above my head once I got onto my back, and then she quickly covered my nakedness with a frilly, black pair of boyshorts, which were nearly like granny panties and covered me very well. My half-sister told me that they were the vibrating pair, and I got very excited and slightly nervous. She made quick work of securing my legs, cuffing my legs immediately. The handcuffs were amazing, being able to tie someone in mere seconds when the scarfs and ropes had taken minutes. I was so turned already, and Cassie increased it all when she got ontop of me. I felt her entire body press against my own intimately, and it took mere seconds for a tent to be pitched in my undwear. We made out for a few moments and she rubbed her hands on me making it even better.
She went through the motions and sat on my head as always, as she knew I loved it so much. I had never felt her bare cheeks on me as she usually had on bikini-cuts or boyshorts when she sat on my face, never wearing such a skimpy thong. I smelt her slightly sweaty skin which was heavenly, and my entire face was surrounded by her confident curves. She wiggled and thrusted her behind onto my head, and I savored every movement of it. She got off of me after a few minutes and I had never been so horny in my life, I was begging for her to turn on the vibrations, and she seemed to agree. She took out the remote and switched the panties on, starting on low.
My entire body shook and I started to pant and moan, and it became evident that she needed to uncuff me and flip me over onto my stomach, allowing me to hump the bed in pleasure, which my body forced me to do naturally. Like a bomb remover she worked expertly and undid my binds, flipped me over, and recuffed my hands, not bothering with my legs for some reason. She increased the panties and turned them onto medium, and I was thrusting my hips into her bed, feeling myself build up. Suddenly, she switched them off, and I whined for an explanation. She got beneath me, sliding her body underneath my own. Cassie positioned herself so we were facing eachother, her entire body beneath my own like a couple making love.
I demanded an explanation for this strange altercation, and she said that she wanted to climax aswell. This way my thrusting would please her aswell, and she could feel some of the vibrations. Since our sexual organs were secured by our underwear, it made sure we would just be humping, and since I was still somwhat tied, I had no choice, not that I was complaining. She reached her free hands around me, hugging me, and turned the panties onto maximum. The vibrations permeated my body to such a degree I started to dip my crotch against her own, and she gasped in pleasure each time I humped her, which just turned me on further.
I continued doing this, as the panties seemed to have taken over my body, and soon we both panting. She was begging for me to go harder and I tried my best to be as pleasing as I could, and not after long, I felt myself building up, and she started to clutch my back tighter as she was climaxing aswell. Eventually it came, and she begged for me to wait a few more seconds while she caught up, and I did, allowing us both to orgasm at the same time, with both our crotches slamming tightly into eachother's, separated only by the panties. The pleasure, after what felt like a beautiful eternity, stopped, and I could feel her tongue slip deep into my throat and I kissed her back. Not after long though, we were tired and sweaty, and had to stop.
We breathed heavily, both having our first orgasms with eachother. For the first time I felt her boobs press against my chest, and I could feel myself crushing them. She got herself from underneath my body, and freed me from my ties. She looked at eachother satisfied, and she was out of breath, but she pointed towards the bathroom and I figured out that she wanted me to clean myself up. I gladly did, and as I was leaving she got her voice back and asked me to leave the panties. She wanted to wash them so they were clean for tomorrow! She left to wash them while she waited for her turn in the bathroom. Evidently the mechanical parts of the panties could be removed when you washed them, meaning we could use them every day.
We both showered and changed into some new panties, and we both got into bed, snuggling eachother tightly. Ashley soon came home and we all got into bed, and I slept firmly next to Cassie. I was inlove.
She handcuffed my hands above my head once I got onto my back, and then she quickly covered my nakedness with a frilly, black pair of boyshorts, which were nearly like granny panties and covered me very well. My half-sister told me that they were the vibrating pair, and I got very excited and slightly nervous. She made quick work of securing my legs, cuffing my legs immediately. The handcuffs were amazing, being able to tie someone in mere seconds when the scarfs and ropes had taken minutes. I was so turned already, and Cassie increased it all when she got ontop of me. I felt her entire body press against my own intimately, and it took mere seconds for a tent to be pitched in my undwear. We made out for a few moments and she rubbed her hands on me making it even better.
She went through the motions and sat on my head as always, as she knew I loved it so much. I had never felt her bare cheeks on me as she usually had on bikini-cuts or boyshorts when she sat on my face, never wearing such a skimpy thong. I smelt her slightly sweaty skin which was heavenly, and my entire face was surrounded by her confident curves. She wiggled and thrusted her behind onto my head, and I savored every movement of it. She got off of me after a few minutes and I had never been so horny in my life, I was begging for her to turn on the vibrations, and she seemed to agree. She took out the remote and switched the panties on, starting on low.
My entire body shook and I started to pant and moan, and it became evident that she needed to uncuff me and flip me over onto my stomach, allowing me to hump the bed in pleasure, which my body forced me to do naturally. Like a bomb remover she worked expertly and undid my binds, flipped me over, and recuffed my hands, not bothering with my legs for some reason. She increased the panties and turned them onto medium, and I was thrusting my hips into her bed, feeling myself build up. Suddenly, she switched them off, and I whined for an explanation. She got beneath me, sliding her body underneath my own. Cassie positioned herself so we were facing eachother, her entire body beneath my own like a couple making love.
I demanded an explanation for this strange altercation, and she said that she wanted to climax aswell. This way my thrusting would please her aswell, and she could feel some of the vibrations. Since our sexual organs were secured by our underwear, it made sure we would just be humping, and since I was still somwhat tied, I had no choice, not that I was complaining. She reached her free hands around me, hugging me, and turned the panties onto maximum. The vibrations permeated my body to such a degree I started to dip my crotch against her own, and she gasped in pleasure each time I humped her, which just turned me on further.
I continued doing this, as the panties seemed to have taken over my body, and soon we both panting. She was begging for me to go harder and I tried my best to be as pleasing as I could, and not after long, I felt myself building up, and she started to clutch my back tighter as she was climaxing aswell. Eventually it came, and she begged for me to wait a few more seconds while she caught up, and I did, allowing us both to orgasm at the same time, with both our crotches slamming tightly into eachother's, separated only by the panties. The pleasure, after what felt like a beautiful eternity, stopped, and I could feel her tongue slip deep into my throat and I kissed her back. Not after long though, we were tired and sweaty, and had to stop.
We breathed heavily, both having our first orgasms with eachother. For the first time I felt her boobs press against my chest, and I could feel myself crushing them. She got herself from underneath my body, and freed me from my ties. She looked at eachother satisfied, and she was out of breath, but she pointed towards the bathroom and I figured out that she wanted me to clean myself up. I gladly did, and as I was leaving she got her voice back and asked me to leave the panties. She wanted to wash them so they were clean for tomorrow! She left to wash them while she waited for her turn in the bathroom. Evidently the mechanical parts of the panties could be removed when you washed them, meaning we could use them every day.
We both showered and changed into some new panties, and we both got into bed, snuggling eachother tightly. Ashley soon came home and we all got into bed, and I slept firmly next to Cassie. I was inlove.
-
Jason Toddman
- Honorary Member
- Posts: 609
- Joined: 6 years ago
- Location: Portland Maine USA
I was planning to post this set of stories myself eventually, but you beat me to it. Good work! Imo a definite classic. 
Only problem is... isn't it a tad much to post the same set of stories twice? Especially in the same forum?
Only problem is... isn't it a tad much to post the same set of stories twice? Especially in the same forum?
Woops, was doing some digging to get some stories back and came across this one, forgot to check if I already posted it. You can delete it xD
-
Jason Toddman
- Honorary Member
- Posts: 609
- Joined: 6 years ago
- Location: Portland Maine USA
but fortunately this version was recoverable.