Bi-Sexual Male / 26
More Boys Who Dress Up As Girls
i told the story of the first time i dressed as a girl and had sex with a man. a few people wanted more about the sex and as it is all about the sex really, i'm happy to oblige.
after that first time as a teenager that i became cassie, and gave myself to a man for sex, i just couldn't get enough.
i didn't meet other 'girls' and i stuck with the same man. we had a little system. he would tell me a date and time to come to his house. he would usually give me up to a fortnight notice and i loved this because i had days of planning, fantasizing and masturbating in advance of the date.
pete would leave me a key and i would let myself into his house, going straight to the bedroom where i had clothes and make-up. i would make myself into cassie, wearing very sexy next to nothings and when i was ready (i would get so turned on doing this), i would let myself through to the living room. he would normally be sat in front of his huge screen watching transgender porn and stroking his big dick. we would watch this together, commenting on who the sexiest girls were and why, or he would suggest that i would look good in a certain dress or panties. he would also play what's now known as sissy hypno, though i'm not sure it had that name then and he would have me stand in front of the screen and dance along to the music, or he would rewind a bit and tell me to 'shake your little ass like she does' or 'bend over like that and spank your bum'.
i'd get even more hot doing this and drinking and smoking weed. weed just makes me think about hard dicks at the best of times. later i would kneel down between his legs and suck him while he sniffed poppers and watched the porn. then he would lube up my tight hole and give me some poppers to help get his big cock up me. he would do me nice and slow, building up speed until he was hammering my hole. my little dick would get hard and sometimes i'd manage to cum while he fucked me, which was amazing. sometimes he would cum in me and others he would lie me down on the floor standing over me and shooting his come onto my face and body. my hole would be pretty sore for days after and that little reminder would get me horny and i'd jerk off thinking about how good it was.
although we'd done the same thing about 7 or 8 times i wasn't slightly bored and it was becoming a real obsession for me. the next time i went over, i made myself up and as usual looked in wonder at myself, what a sexy, slutty looking teen girl i had become. i looked at the little bulge in my lacy panties and my slim, hairless legs with the stockings. i blew a kiss to myself and walked into the living room.
i was shocked and put off my stride to find 3 other men there as well as pete. for a second i thought i'd made a mistake on the day or something and i was humiliated. then pete just casually said 'oh this is cassie, the girl i was telling you about' there were a few 'hi cassie' responses and then pete said 'hey cass, the boys are out of drinks here, be a good girl and get a round of beers from the fridge.'
he turned right back to the tv and some comment about the girls on the screen. i was totally out of my comfort zone and had to have a word with myself in the kitchen and pull myself together. i got the beers and went straight back in trying to look as sexy and relaxed as possible while handing the beers round. it turned out the men were watching some video of a thailand holiday two of them had just returned from. they had spent a month with various ladyboy escorts and had managed to video a lot of it. to my annoyance they seemed more interested in looking at the (admittedly hot) girls than watching me as i gave out the drinks. the last beer i handed out was to a man about 40, sat on a sofa. before i could turn away he thanked me and then reached up with the palm of his hand and softly rubbed against the small bulge in my lacy panties. holding my eye he said 'hm there's something going on in here i think?'. 'yes. i have a little cock' i replied, turning myself on and blushing as i moved away, being careful to let my bum twitch a little as i walked.
a while later pete came over to me and leaned into my ear saying 'look, why don't you go through to the bedroom and get yourself ready. some of the boys want to fuck you and i think that would be the best place'
a few things struck me. how turned on i was that he was telling me instead of asking me. i loved that. he'd been no less casual when he'd told me to bring in the beers. i don't think it can get any better for a true submissive. secondly, hang on a minute 'some of the boys' want to fuck me. you mean they don't 'all' want to fuck me . i felt very disappointed.
i went through to the bedroom and arranged myself. it was light outside and with the curtains closed it had a nice half-light quality. i got on all fours and pulled my panties down enough so that my hole was accessible, then applied plenty of lubricant as i was thinking i might be in for a bit of a rough time. then i waited. they really know how to treat somebody like me as it was an age before they came through and i was almost frantic with longing.
they came through together and as i turned round i was told to 'look at the bedspread baby'.
i did as i was told and so without knowing who was doing what started to hear belt buckles and shoes coming off. there were lots of nice comments coming over about my ass or my legs and i liked this. then i felt a hand on one of my hips and seconds later the head of a thick cock being forced into my tight little hole. 'wow, you're right it is sooo fucking tight....aww she lubed herself up for me already. come on baby, help me out here, loosen up...oh there it goes' as i gasped in pain and pleasure as he got right inside and without any concern for me just started to rut on me as hard as he could. i became aware that there were three other men i the room. i could smell cock and pre-cum and i was really getting off on having men watch me being a total sissy faggot, backing onto the lovely dick as much as i could. 'she's got a little hard on for you man, think she loves you' prompted some laughter from the others, but the humiliation was lovely and just made me gasp and buck and twitch all the more. after not very long he was cumming inside me with a twitch or spasm for each spurt. he pulled out of me and then grabbed my head and turned me round. ' come on sweetheart, clean it up for me' he said pushing his dick into my mouth. so he must have fucked me raw. what could i do? i put my mouth round it and even as i relished the smell and taste of cum and my own ass, i felt the next one slip into me and i started to move my hips with him like the slut that i so clearly am. as he was fucking me the guy leaned in and said 'you like your first gang-bang, baby?' and pushed some poppers onto my nose. as it hit me my head was swimming and i was almost incoherent just managing ' hmm, gang-bang. yes gang-bang '
i think the hottest thing that drove wild was just hearing them shout out stuff like 'fuck her harder, suck his dick bitch, you like that sissy bitch? sweet' while these men watched me totally submitting to all they did, all of them knowing i was a cock crazy sissy whore and i'd do anything they asked - all this just about made me crazy.
the other best thing was having a man come inside me and then instantly have another rock hard cock shoved in on top of the slippery load and thinking what a hot slut i was.
when the third guy fucked me he sat on the edge of the bed and had me back onto his cock and ride him. one of the others laughed at my little stiffy sticking out so useless, but then a few seconds later got on his knees and started to suck me while i was being fucked. i could tell this really turned him on so i kept my mouth shut right until i shot my red hot cum into his mouth.
the men left the room 1 by 1 and pete had last go, kneeling me down and fucking my mouth telling me how pleased with me he was.
the final humiliation was that afterwards back in the living room they drew lots on who i was going home with. the guy who had sucked me off won this and was gratifyingly triumphant. he told me i was his girlfriend tonight and would sleep with him in his bed. these men really know how our minds work as his last shot was to call a taxi to take me to his. although it was dark now, i was dressed like a total slut, the state of my make up told the story of the evening and i must have reeked of sex. remember i had never been out in public and just imagine the sickening excitement as i left the house and got in the taxi, even more so as i got out at the other end, where i had to walk past several staring people before we got to the house.
nice end to the evening. he was as good as his word and treated me like a girlfriend fucking me slowly and passionately in missionary position with lots of kissing before i fell into an exhausted sleep. good girl, whore, sissy-faggot or all of these? you tell me.
after that first time as a teenager that i became cassie, and gave myself to a man for sex, i just couldn't get enough.
i didn't meet other 'girls' and i stuck with the same man. we had a little system. he would tell me a date and time to come to his house. he would usually give me up to a fortnight notice and i loved this because i had days of planning, fantasizing and masturbating in advance of the date.
pete would leave me a key and i would let myself into his house, going straight to the bedroom where i had clothes and make-up. i would make myself into cassie, wearing very sexy next to nothings and when i was ready (i would get so turned on doing this), i would let myself through to the living room. he would normally be sat in front of his huge screen watching transgender porn and stroking his big dick. we would watch this together, commenting on who the sexiest girls were and why, or he would suggest that i would look good in a certain dress or panties. he would also play what's now known as sissy hypno, though i'm not sure it had that name then and he would have me stand in front of the screen and dance along to the music, or he would rewind a bit and tell me to 'shake your little ass like she does' or 'bend over like that and spank your bum'.
i'd get even more hot doing this and drinking and smoking weed. weed just makes me think about hard dicks at the best of times. later i would kneel down between his legs and suck him while he sniffed poppers and watched the porn. then he would lube up my tight hole and give me some poppers to help get his big cock up me. he would do me nice and slow, building up speed until he was hammering my hole. my little dick would get hard and sometimes i'd manage to cum while he fucked me, which was amazing. sometimes he would cum in me and others he would lie me down on the floor standing over me and shooting his come onto my face and body. my hole would be pretty sore for days after and that little reminder would get me horny and i'd jerk off thinking about how good it was.
although we'd done the same thing about 7 or 8 times i wasn't slightly bored and it was becoming a real obsession for me. the next time i went over, i made myself up and as usual looked in wonder at myself, what a sexy, slutty looking teen girl i had become. i looked at the little bulge in my lacy panties and my slim, hairless legs with the stockings. i blew a kiss to myself and walked into the living room.
i was shocked and put off my stride to find 3 other men there as well as pete. for a second i thought i'd made a mistake on the day or something and i was humiliated. then pete just casually said 'oh this is cassie, the girl i was telling you about' there were a few 'hi cassie' responses and then pete said 'hey cass, the boys are out of drinks here, be a good girl and get a round of beers from the fridge.'
he turned right back to the tv and some comment about the girls on the screen. i was totally out of my comfort zone and had to have a word with myself in the kitchen and pull myself together. i got the beers and went straight back in trying to look as sexy and relaxed as possible while handing the beers round. it turned out the men were watching some video of a thailand holiday two of them had just returned from. they had spent a month with various ladyboy escorts and had managed to video a lot of it. to my annoyance they seemed more interested in looking at the (admittedly hot) girls than watching me as i gave out the drinks. the last beer i handed out was to a man about 40, sat on a sofa. before i could turn away he thanked me and then reached up with the palm of his hand and softly rubbed against the small bulge in my lacy panties. holding my eye he said 'hm there's something going on in here i think?'. 'yes. i have a little cock' i replied, turning myself on and blushing as i moved away, being careful to let my bum twitch a little as i walked.
a while later pete came over to me and leaned into my ear saying 'look, why don't you go through to the bedroom and get yourself ready. some of the boys want to fuck you and i think that would be the best place'
a few things struck me. how turned on i was that he was telling me instead of asking me. i loved that. he'd been no less casual when he'd told me to bring in the beers. i don't think it can get any better for a true submissive. secondly, hang on a minute 'some of the boys' want to fuck me. you mean they don't 'all' want to fuck me . i felt very disappointed.
i went through to the bedroom and arranged myself. it was light outside and with the curtains closed it had a nice half-light quality. i got on all fours and pulled my panties down enough so that my hole was accessible, then applied plenty of lubricant as i was thinking i might be in for a bit of a rough time. then i waited. they really know how to treat somebody like me as it was an age before they came through and i was almost frantic with longing.
they came through together and as i turned round i was told to 'look at the bedspread baby'.
i did as i was told and so without knowing who was doing what started to hear belt buckles and shoes coming off. there were lots of nice comments coming over about my ass or my legs and i liked this. then i felt a hand on one of my hips and seconds later the head of a thick cock being forced into my tight little hole. 'wow, you're right it is sooo fucking tight....aww she lubed herself up for me already. come on baby, help me out here, loosen up...oh there it goes' as i gasped in pain and pleasure as he got right inside and without any concern for me just started to rut on me as hard as he could. i became aware that there were three other men i the room. i could smell cock and pre-cum and i was really getting off on having men watch me being a total sissy faggot, backing onto the lovely dick as much as i could. 'she's got a little hard on for you man, think she loves you' prompted some laughter from the others, but the humiliation was lovely and just made me gasp and buck and twitch all the more. after not very long he was cumming inside me with a twitch or spasm for each spurt. he pulled out of me and then grabbed my head and turned me round. ' come on sweetheart, clean it up for me' he said pushing his dick into my mouth. so he must have fucked me raw. what could i do? i put my mouth round it and even as i relished the smell and taste of cum and my own ass, i felt the next one slip into me and i started to move my hips with him like the slut that i so clearly am. as he was fucking me the guy leaned in and said 'you like your first gang-bang, baby?' and pushed some poppers onto my nose. as it hit me my head was swimming and i was almost incoherent just managing ' hmm, gang-bang. yes gang-bang '
i think the hottest thing that drove wild was just hearing them shout out stuff like 'fuck her harder, suck his dick bitch, you like that sissy bitch? sweet' while these men watched me totally submitting to all they did, all of them knowing i was a cock crazy sissy whore and i'd do anything they asked - all this just about made me crazy.
the other best thing was having a man come inside me and then instantly have another rock hard cock shoved in on top of the slippery load and thinking what a hot slut i was.
when the third guy fucked me he sat on the edge of the bed and had me back onto his cock and ride him. one of the others laughed at my little stiffy sticking out so useless, but then a few seconds later got on his knees and started to suck me while i was being fucked. i could tell this really turned him on so i kept my mouth shut right until i shot my red hot cum into his mouth.
the men left the room 1 by 1 and pete had last go, kneeling me down and fucking my mouth telling me how pleased with me he was.
the final humiliation was that afterwards back in the living room they drew lots on who i was going home with. the guy who had sucked me off won this and was gratifyingly triumphant. he told me i was his girlfriend tonight and would sleep with him in his bed. these men really know how our minds work as his last shot was to call a taxi to take me to his. although it was dark now, i was dressed like a total slut, the state of my make up told the story of the evening and i must have reeked of sex. remember i had never been out in public and just imagine the sickening excitement as i left the house and got in the taxi, even more so as i got out at the other end, where i had to walk past several staring people before we got to the house.
nice end to the evening. he was as good as his word and treated me like a girlfriend fucking me slowly and passionately in missionary position with lots of kissing before i fell into an exhausted sleep. good girl, whore, sissy-faggot or all of these? you tell me.
- That's Juicy! 14
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