Category: Cross-Dressing Stories

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

My wife knew that I was a bisexual crossdresser before we even got married. Well since was still glued down from last time I was dressed as Paula my wife decided we should go to a alternative club this way I can be Paula. We decided to get a motel room since it was 2+ hours away.

After we got out of the tube. I was going to put on my jeans and get dressed. She said to me please don’t put those clothes on. She said look your eyebrows are thin and arched feminine and nails done and painted and toes painted and your hair is cut and styled feminine and I want you to be Paula 24 7 for a few days maybe longer. Well okay then I said. Then she said something to blow my mind. She told me that the super glue that she gave to use to glue myself down to look like a woman’s virgia was industrial strength super glue and I will be like a woman’s virgia for real for at least 2 years or more.

The blue and white Bell Jet Ranger helicopter was closing on the oil rig, eighty miles into the green choppy sea off Port Fourcon, Louisiana. Jack told himself he wasn’t going back offshore again! Ever! Yet, here he finds himself, accepting another hitch — not on the platform he’s flying to, but on the one-hundred-forty foot supply boat tied up to it. Twenty-eight days of – fourteen days off.

Hello guys…

John was only 17, a slim but very feminine looking guy. Only 5ft tall and even talked very softly. He left home at 16, as life was unbearable at home. He got a job working in a office and now had a small 1 bedroom apartment. He had only one friend, a girl named Sofia (who worked in office with him). She was very close to him and challenged him to go to party dressed as a girl. She joked you act like a girl, you look very feminine so do it. After argument, he give in. In the next couple of weeks Sofia went about transformation of John. First she got him to learn to walk in higheels, then tight skirts. Next was to shave every hair off his body waxing him. She made him grow his hair longer (To his shoulders). There was only one other person knew about it, their boss. He had a wager with her she couldn’t pull this off. Then make walk very sexy. On the day she started by getting his feet nails painted and finger nails, a nice red. Next she done John’s hair to he looked really nice, followed by make up and eyelashes. Then lipstick. A bra with padding a nice blouse, a skimpy pair of pants (see through). Joking you may get pulled Sofia said. Then hold me up stockings and a body clinging skirt followed by higheels. Wow you look stunning Sofia said. Very proud of herself. John looked in mirror and felt great, even felt seductive. Sofia said we call you Clare. Sofia dressed she looked beautiful. And they got taxi to party. The first person they met was their boss. He looked stunned omg wow he said. Sofia said I win you owe me. He said you deserve the money. As the party was going Clare had to dance the night away. After a while sitting in a corner with some guy who kissing her and groping her. Sofia then moved in to save Clare before they went to far. As it was time to leave their boss (Mike) offered them lifts home. Sofia was very drunk and Clare wasn’t far behind her. They dropped Sofia home first then Mike drove Clare home. Sitting outside Mike leaned over and surprised Clare with a kiss, then a longer one. Clare (John) responded kissing back. Can I come in Mike said. Yes please do. They entered the small apartment and Clare got Mike a drink he sat on the settee. Well Clare what’s next he asked. There was a silence then Clare undone her skirt and let it fall to the ground. Mike looked at her sweet body and the small but sweet cock in the see through pants. Smiled then asked for more. Clare removed her pants and Mike’s eyes lit up at shaved body. Clare walked into her bedroom and waited, lying on the bed. When Mike walked in he was already naked. Clare was only 17 and was about to taste her first cock, slowly licking and sucking Mike’s cock. She was feeling so turned on as Mike caressed and groped Clare’s body then Mike got in 69 position and began sucking Clare’s small cock. Soon Mike made her cum and now positioned Clare so he could enter her virgin ass.. Lifting Clare’s legs in the air he eased his hard throbbing cock in side her. Clare moaned as inch by inch entered her. Soon Mike had a rhythm and fucking his boy pussy without mercy. Soon Clare cock was dribbling cum before Mike started to thrust his cum in her tight wee hole. Mike was to fuck her 2 further times that night. In the morning he didn’t go back to been John he dressed in tight leggings and girl top he bought. He phoned Sofia and told her everything.. That was the last time he was John and now has become Clare. And is going out with Mike. She has now started hormone treatment and has started growing small tits. The thing is Sofia has become part of the company and has had sex with both Clare and Mike. And has become pregnant to one of them. Clare and Sofia both moved in with Mike. People talk but they don’t care. Away with John and a new life as Clare a VERY sexy life.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

Hi you can call me Julissa.. I’m a crossdresser from Los Angeles CA. And here’s my story I first started crossdressing as far back as I could remember I do know I was young. Wearing my sisters clothes were Like a year apart so I would slip in her clothes fine.. I don’t know why but it gave me a rush. My heart will start beating fast I would enjoy the excitement of it.. So it escalated to me finding random things and putting them in my ass.. I guess training or just curious.. So now that I’m older I wear my wife’s clothes… I also bought her a 9 inch dildo.. Well its really mines.. Now. Lol well when she’s not home. Anyhow I found this website well app called grindr. I took sum sexy pics of me made a profile.. And posted it, it started going crazy I was surprised of how many guys wanted to fuck.. I’m not that fem but I do have an amazing ass so I hear lol its big.. Invade tour wondering.. So I started looking and found a sexy white boy with a huge cock.. I can tell from his pics… I answered him.. He would reply fast… Told me he wanted me I told him ok.. Finally.. Lost my fear and when I was alone at home I got dressed in some nice panties a bra short skirt and heels.. I was kind of scared so.. But here we go.. I told him come over I left door open as I wanted in my room feeling sexy lights off… He finally came walked in came in room I was shy at first but the dark room made it better.. He grabbed me started kissing me grabbing my ass gently pulling me closer I was so excited I went for it I grabbed his cock it felt huge and already hard.. I was shy no more I pulled it out quickly putting it in my mouth it felt so warm and good I sucked him Like 5 min he put me on the bed and ate my ass and kissed my ass cheeks and me till finally he started to go in me. I first felt alot of pressure when the head was going in he was huge….. To be continued.. Let me know if you want to hear part 2… I promise I wont let you down.. And I still have my grindr account till this day so let me know if you would Like to know more about me.This content appeared first on new sex story .com

It was my younger days. I was at a friend’s house only one that didn’t make fun of me for being being completely hairless an smooth except for my eyebrows and eyelashes and hair my long hair on my head and feminine.

***Disclaimer – this is a complete work of fantasy fiction, none of the characters are based on any real persons, living or dead.***