crossdressing first time

John can’t remember how young he was when he tried to dress as a girl maybe ten or twelve. But every chance he got he put his sister’s clothes on. John was slim about 5feet6 and even talked very feminine. He got bullied and harassed at school by most off the boys, but secretly one off the bullies had taken his virginity in the boys toilet one day. Pushing him in cubicle, pulling his trousers down and forcing his hard cock in John’s ass. John remembers the pain but also the ecstasy as his virgin hole got fucked. But our story starts when John was 17 and left home and moved to the nearby city. He found a job in a shop and shared a flat with a guy called Mike. He already explained to Mike he loved dressing up as a girl and to his joy Mike didn’t mind. Slowly John started wearing girls clothes round flat and even went to work dressed as a lady. No one seemed to mind. As his confidence grew he began crossdressing nearly all the time. His figure was slim and quite sexy and didn’t have a hair on his body except hair on his head, which was growing longer everyday. Mike would have poker night’s once a fortnight, so John would make sure he was out to late to keep out off the way. But one night Mike asked him to stay and could serve drinks and look sexy and bring him luck. John dressed up nice make up, painted his nails and toes, sexy blouse and short skirt, stockings and highheels. Wow you look stunning. Only thing he didn’t put on was pants. As mike’s friends arrived they all kissed John on the cheek but treated him well with the odd dirty remark. But all in fun and when the drink was in even groping John’s ass. One guy Phil said our you fucking Your bitch. Their was a silent pause, then Mike said I am tonight. John was shocked at first but walked over to Mike and planted a hot kiss on his lips and smiled. Everyone looked gob smacked and seemed to lose their concentration on the cards as Mike began winning alot. What coloured pants you wearing under that skirt one shouted. None, John said. An awkward silence fell over the room. When Mike said take your skirt off. John unbuttoned the back and let the skirt fall to the ground, exposing his shaved balls and small cock. Mmmmm lovely Phil shouted our we getting some off that later. Mike looked at John and said yes we all our. John’s heart was pumping like mad and his mind was going crazy at the thought off what was going to happen. Soon the cards where forgot about and John was on his knees sucking cock and getting groped. He then was carried into the bedroom and was on all fours as he sucked cock, a guy below him sucking his and another massaging his asshole with vaseline and slowing figuring him. Mike shouted I’m the first inside her she’s my bitch. It felt sore but nice as mike’s cock entered his bum. Soon he was fucking John’s ass hard and without mercy. Every thrust sent John crazy but kept sucking cock. He felt mike’s cum full his hole, as one by one they fucked the shit out off his ass. The night was long as these four guys abused his body. By morning John felt sore his mouth from sucking and cum inside it, his nipples where the guys bit them, his ass from the pounding it took and his cock from sucking and wanking it received. Everyone had gone except Mike. Morning baby and threw him a kiss. John fell asleep but when he woke up Mike was gone. When arrived back he had been shopping for clothes. Nice dresses, sexy pants and lingerie. And a butt plug and love balls. Which he inserted in John’s ass, making walk around flat in. Which caused a hot sensation in John’s body and even caused precum to drip from his cock. The next number off days Mike fucked the brains out John ( who he called Jessie now ). And every poker night Jessie would dress sexy and would have love balls or butt plug in her ass. And every poker night Jessie would get gangbanged and used like their bitch. Then one day Phil called and before he new it Phil was fucking her. Mike caught them but instead off screaming or going mad joined in. This happened over the next couple off years until Mike persuaded John ( Jessie ) to have hormone treatment and started to form nice tits. Now he has been converted from crossdressing slut to transgender slut. She’s looks beautiful, sexy and deeply in love with Mike, but still once a fortnight the boys bitch.This content appeared first on new sex story .com

Ricky was 18 and looked very feminine. He had been crossdresser since he was 12. He loved the way it made him feel. He awoke lieing naked except for a pair hold me up stockings in a stranger’s bed. His bum was on fire, sore from some serious pounding. He had a taste in his mouth off cum. He new he went to party and was very drunk, he remembered kissing a couple off guys. He looked round and beside him was the naked body off a black guy. Omg he thought as he noticed the size off his cock. Fuck no wonder his ass was sore and mouth. Was that fucking monster inside me. Ricky would call herself Rachael when dressed up. He grabbed his clothes quietly and tried to sneak out. It was the 3rd time this week he ended up in someone s bed. Fuck at 18 I’m a slut he thought. He lived with his mother who new off his fetish to crossdress and infact bye him woman’s clothes. As he tried to go the door creaked, the guy woke looked round, where you going baby he said. I have to go Rachael said. He was dressed everything except his knickers ( which where lost in the bed somewhere. ). At least give me kiss goodbye. He hesitated but moved  round to kiss him. But the black guy slipped his hand under the dress and started to caress Rachael’s cock and balls. Omg it felt good. He lifted his dress exposing his small white cock. Bending over the black guy so his now white cock was over his mouth. Soon Rachael was like ragged doll as his drained out off him as the guy sucked his cock. It felt so good, it felt great been a whore. Before he could cum he was pulled on the bed and legs parted. And this big black cock re entered his white ass. He felt every thrust and pounding as the guy fucked him deep and hard. He even moaned like a girl. The guy shouted what our you. I’m your white whore I’m your white whore. Then felt cum full his battered ass. After another hour he made his way home. It was ok he was able to get home without anyone recognising him. In the house he dressed like a lady all the time. His hair was long and he kept himself well shaved all over. A few days later he was invited to another party, and he always went as Rachael. He wore a pink blouse, a short skirt and tights. With no underwear. It wasn’t long before a couple off guys hit on him. Drink flowed and soon Rachael was tipsy. Both guys where taken turns to grope him. The three off them left the party and got taxi to this house. They hardly entered the door before he was pushed against the wall and a tongue pushed in his mouth. It was like whirlwind before he new it he was on a settee sucking cock as the other guy had lifted his skirt and was licking his cock through the tights. Suddenly he felt a rip as his tights where ripped open and the guy released Rachael’s cock and started jerking it as he rimmed his ass. Mmmmm Rachael moaned in between sucking cock. A finger replaced the tongue then 2 fingers. Fuck it felt good. The guy said to his mate we got ourselves o proper slut this time. And forced his cock inside Rachael’s ass. Now she was getting spitroasted. And not gently either. They fucked him good taken turns to empty their load in Rachael’s ass or mouth. After been fucked all night she lay asleep in between both guys. Well used. He showered and dressed, but didn’t leave. After a while one guy woke. What’s for breakfast he shouted. Rachael stood up lifted her skirt and pulled her cheeks apart, showing her asshole. This he laughed. The guy came up behind her, and Rachael stroked his cock to it was hard and guided inside her.. Your a proper slut as he fucked her. She went home full off fresh cum. Since then she is now taken pills to grow a pair off tits, she wants to be a proper transgender. She also caught up with the black guy who is her boyfriend and pimp. Infact also gets clients for his mum, so is making money from both off us. Signed a young crossdressing whore.This content appeared first on new sex story .com