The night with Greg and Tim ended up being a one-time thing. Greg simply stopped returning my calls and Tim never called again. In the three years that followed, I only connected with two guys in person as Jenni. Both meetings resulted in quickie blowjobs that took far more work and risk compared to the amount of satisfaction that followed. I recognized that I wasn't the hot piece of twenty-something ass I used to be, but...

After watching Greg pull back onto the highway, I took the next fifteen minutes to reapply my makeup in the rearview mirror and gather my thoughts. I realized that the sun had gone down and the rest stop parking lot was not quite as inviting as it was when I pulled in. Two overhead street lights dimly lit the parking lot and the short sidewalk to the building in front of me. I decided that staying in the parking lot too l...

It was strange for Brad to not email me or connect online for more than a few days. It had now been a week since our last meeting, and I still hadn't heard from him. A week became two and two became a month. Five emails I wrote to him had gone unanswered. I was alone at home. I stood naked in front of a mirror. I rubbed my belly which had become very well pronounced to the point where I just looked fat. My breasts had bec...

It only took a month the see a subtle change. Two months in, I really started to feel it. It had been years since I didn't have a regular workout routine but in an effort to show Brad how committed I was to him, I was all in on role-playing my pregnancy. Not only was I feeling the additional weight I had put on, but it was noticeable to my family and friends. I blamed the lack of working out on a nagging back injury. I wr...

Brad and I had been seeing each other for over a year when he would come into town. Our meetings started in his hotel suite and progressed over the months to restaurants, walks around town, and trips out shopping. Brad was extremely well off, successful, and more than generous when it came to gifts. In bed, our relationship was fantastic. Brad was a marvelous kisser and loved foreplay. As many sexual experiences that he a...

I couldn't help but feel very self-conscious. It had been nearly two and a half years since I had been out in public dressed as Jenni. I walked through the lobby of the hotel with far less confidence than I had when I was out walking the streets looking for a trick. I tried to dress down but couldn't help but think all eyes were on me, thinking I was some cheap, ugly hooker going to meet up with her date. The hotel itself...

As far as motel rooms go, this looked like a very nice one. The mattress appeared to be new, the décor was very modern, and all the light bulbs worked, at least the ones that were turned on. I was making these observations while a truck driver named Jerry was fucking me doggie style, carrying on about how I was his “little princess slut” and “little baby fuck hole.” I could only imagine that where Jerry was from, both wer...

I met with Tabby on two other occasions after meeting her that night at the professor's. It was evident that after our third encounter that neither of us really knew where to take this relationship and mutually decided it was best to end our little fling. I was not heartbroken at all. I knew things would eventually run dry with her. As winter came along, most of my weekends were spent alone. Sal and Sophie were typically...

In hindsight, I should have expected that the Friday night date at Professor Lambert’s apartment might not be everything I was expecting. I had duped a college professor and made the assumption that just because I had sucked his cock in his office and swallowed all of his cum, that he wouldn’t be able to resist me again and was ready to fuck my brains out all night. I spent more time debating whether to wear a leather or...

The sexual high of Halloween weekend came crashing down three weeks later when Missy stopped by my house unexpectedly. She was in tears. I assumed the worst, thinking something had happened at school. It was far worse. Missy’s brother and I had grown apart. I was a jock by day, diva by night kind of guy. He was kind of a stoner who had abandoned our friend group. So while it wasn’t surprising he wasn’t the one delivering...

The days couldn’t go by fast enough as I patiently waited for the last weekend of October. While crossdressing on Halloween seemed all too cliché, Missy and I had collaborated on quite an outfit that undoubtedly would be my most outlandish and revealing look yet. Missy and her friend Laura had decided that a trio of slutty pirates would be the perfect opportunity for Jenni to make her college campus debut. Missy said she...

The hardest part of the school year and the winter was finding opportunities to explore my newfound feminine side. Often times I would sneak my bra and panties into the bathroom and masturbate while I replayed everything that happened in the back seat of Larry’s car in my mind. I would never forget touching his cock, feeling him get hard, the taste of his cum, and the satisfaction of knowing that I had the ability of maki...

Who was this girl? Just minutes ago, Missy was giving me an incredible blowjob. Now she was casually reminding me to make sure I turned over to balance out my tan lines as she sipped from her glass of water like nothing had happened. I was looking straight up at a nearly perfect sky for a September weekend day, feeling the warmth from the sun beating down on me. Three months ago, I was playing dress-up with this girl as a...

A day did not go by when I didn’t think about that night at Jimmy’s house. I would frequently wear the black bra and panties Missy gave me when I was alone at home or occasionally out with friends. My buddies and I were looking at girls in a completely different sense. I started looking at girls for what they were wearing and how they carried themselves. And my fellow sixteen-year-old friends, well they were looking at th...

Like many sixteen-year-old boys, I was at that age where I had moved on from department store magazine bra and panties pages to the pages of Playboy magazine. There was not much left to the imagination in these pictures, and I quickly became fascinated by the female form. As much as I admired the female body, I couldn't help but be drawn to their makeup, hair, and everything satin, lacy, and sexy that gave them that allur...