Note: I wrote this a couple weeks ago, looking for input before I write another.
How I became a Crossdressing Sissy Slut –
When I was 16, the summer before my Senior year in High School; I use to chat and cyber with men and women from around the US. I use roleplay/catfish as a teenage girl, most of the time if they asked, I would tell them the truth. I found a guy that lived near me and he convinced me to meet him. He knew I was a boy and enjoyed being a girl.
We talked about what we could do together. We concluded that I could probably fit in his daughter’s clothes, who’s a year older and just graduated. She was out of the house a lot and he found himself alone on his days off while his wife worked.
The day came and I showed up at his house. He was super nice and offered me a alcoholic drink that I took him up on, to calm the nerves. We both were nervous, neither of us had done this before. He showed me his daughter’s room and he had laid out an outfit he would like me to wear. Short while skirt with a lacy tank top. Matching bra and panties of course.
He closed the door and let me get dressed while he refilled his drink. I could barely contain my dick in the cute satin panties. After I was ready, I came out and sat on his lap in the living room area. I could tell he had a huge hard-on too. After a few minutes of playful banter, I slump down between his legs and he pulls out his cock. Without hesitation, I start sucking it and he starts moaning his daughters name. I’m completely turned on by this and work even harder to please him. After a few more minutes, he asks if I’m ready to be fucked. I nod my head while he drops his pants. He get into position behind me while I’m bent over the arm of the couch. He showing pulls my skirt up over my ass exposing my panties and gives it a firm slap. He then rubs is cock all over the panties. We talk dirty for a minute while he pulls the panties to the side and squirts some lube on my asshole. He rubs it in with his cock and gently applies pressure until the head popped in. I was totally turned on and in complete shock of what was about to happen.
He pushes himself firmly deeper into me. I playfully moan at first but he keeps going. He had to be 7 inches long and somewhat thick. I wasn’t quite ready for my first time. That didn’t stop him. He kept pushing and I started whimpering, asking him to go slower. He reached the end, he was fully inside me and I felt like I was impaled and bleeding. He starts thrusting and said I should just relax and not think about it. He calls me his daughter’s name again and remember what I’m here for. I was in pain but powered through it to let this man enjoy the fucking of his daughter. I gave him a great performance and it wasn’t long before came in me. It was best feeling I’d ever had.
Being able to give pleasure to that man, made me a Crossdressing Sissy Slut, that I think about all the time since.
Source: reddit.com/r/eroticliterature/comments/67u0sr/becoming_his_daughter_crossdressing_mm_olderyoung
10/10