embarrassed naked babysitter stripped

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.

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