14 years ago I posted a couple of stories from my first sexual experience, which…
Just a quick recap of part one: Greg seduces Paul who was Greg’s former mentor. Together they watch adult movies, Paul then masturbates for Greg. Paul then gets on his knees and sucks Greg’s hard cock until Greg cums in Paul’s mouth.
Three days had passed since their get together and Paul was thinking about how Greg had used him just to get his cock sucked by someone. When the shift was almost over Greg popped his head in the door and asked if he could come in I motioned him to quickly get inside so I could shut the door. Greg said he liked what went on and would like it to continue. Greg then said he would like me to be his lady. I was shocked mainly because I thought I had buried my feminine side. In my late teens, early twenties, I had discovered a passion for cross dressing. Greg said he would like me to come over as soon as my replacement got here.
When I arrived at Greg’s I was greeted with a deep french kiss that made me shiver and made everything seem alright. After a shower Greg led me to the bedroom and there on the bed was everything a woman could ask for; from panties to lingerie, Greg had gotten it all. He said a woman friend owned a boutique and these items were just the start. Greg then said Ellen would be stopping by to take measurements and to make sure everything fits correctly.
In a second I had Greg naked and we proceeded to start giving each other a blow job. Then there was a knock on the door and it was Ellen. She smiled and said, “I hope I’m not interrupting anything.” Ellen proceeded to take the measurements needed so I would look sexy dressed as a woman. As soon as Ellen left, Greg said he wanted to make sweet love to his lady, and with that I was getting his cock hard again by giving him a super blow job.
Greg then lubed up my waiting ass; I wanted to be fucked so badly. We started with me on my back and my legs on Greg’s shoulders; this gave Greg the room he needed to get his big hard cock inside my tight male pussy. Once inside, his hard cock made me shudder and before I knew it I was having an orgasm like I never felt before. Greg then pulled out of me and got me on all fours, my ass in the air waiting to be fucked doggie style. Once inside me he was like a man possessed; it was not long before he started to shake then he shot his load deep into my male pussy. We both collapsed and drifted off to sleep.