Jenna & Stephen Part 1

Here was her stunner. "Well, neither I suppose. In college, I dated a guy and we hooked up with a shemale. So I don't know how you'd classify that."

Wow, I thought my story was interesting! As she explained how they hooked up with a shemale, I sat there pondering the logistics of a guy, a girl and a shemale. Maybe it was the alcohol, but I found myself bewildered by the possibilities of who could have done what to whom. So I asked.

"I have always fantasized about shemales. Adam, my boyfriend at the time, was cool with my bringing one in, but refused to do anything with the shemale, even though I think it would've been so hot. Anyhow, she called herself 'Chrissie' and I had sex with each of them. While one was inside me, I was giving the other a blowjob."

Jenna volleyed the discussion back at me. "How did you come to experience taking it up the ass?" It was a very forward way of asking, but I have to admit, it turned me on to hear her talk that way.

I gave her as brief an explanation as I possibly could, but made sure to keep in the key details.

"One night Stacy and I were 69'ing," I told her. "I felt her finger poking around at my butt hole. While it wasn't an experience I was seeking, I decided not to stop her. I wanted to see where she was going with this, no pun intended. She probably just got past her finger-nail that first time, but still I was overwhelmed by the sensations racing through my body. It was almost too much, too pleasurable. I nearly told her to stop, but just then she started to move her finger back and forth, essentially fucking me with her digit. I couldn't protest because I couldn't even speak. All I could do was let out a loud moan. It was -- up until that point -- the best orgasm I ever experienced."

Jenna listened intently as I continued. "The fingering became a regular part of our foreplay," I continued. "Then one day Stacey came home and said she had a present for me. I opened the flowery gift bag she handed me and found a butt plug.