Party Surprise - First sex as a Crossdresser

We sat back down on the couch and I
had a cigarette before re applying my lipstick at the mirror next to Paul’s bed. I adjusted my dress and he put his pants back on. I looked at him and jokingly said, “Thanks for the fuck”. We laughed and I re confirmed, “Our secret?” “Yes, for sure” he said.

We went back into the party and I quickly found Stephanie. She was alone outside on the balcony having a cigarette. I lit up as I joined her. I was waiting for the “where have you been?” and was trying to think of excuses when Stephanie turned to me and gently stroked my hair. She said, “Did you enjoy that my darling?” I was confused and said, “Wha, what are you talking about?” With that Paul joined us on the balcony, walked up to Stephanie and they shared and deep lounge kiss. My eyes were wide again. What was going on?

Stephanie, with one arm still around Paul, turned and looked at me but directed her question to Paul. “Was she good sweety?” I was agasp. “She was everything you promised babe”. They kissed again. I then saw Stephanie pull a $50 note from her pocket and hold it up as though she had lost a bet or was making payment. Still looking at me she asked Paul, “Did she let you bareback her?” “Sure did” he smugly replied. Another $50 was offered. Then she asked, “And did you cum inside her?” “My god, did I?” He replied. Yet another $50.

Stephanie then cupped her hand onto Paul crotch holding the cock that had just fucked me. She said, “Babe, this cock has been fucking me for several months now. It just seemed so wrong not to share such a gorgeous piece of meat with you. But you have disappointed me. Letting a man cum in your ass on the first date, I’ll have to teach you some etiquette.” They both laughed. I still couldn’t speak. I’d been set up. When I finally spoke, I asked about the money. “Well Paul bet me $50 he could fuck you, $50 that he could bareback you, and another $50 that he could get you to let him cum in your ass. So you cost me $150. But it was worth it knowing what he just did to you” and she laughed again.