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I didn't suck my first cock until I began going out as Melissa at the age of 49. I'd met Jimmy at a local bar and talked to him a few times before that night. The gurls I was with dared me to go for it and take him out to my Jeep to play a little. I was attracted to Jimmy and decided to invite him out to my Jeep. I was nervous but also very excited. He obviously knew what I had in mind because as soon as we got into my Jeep he unzipped his jeans and pulled out his semi erect 7" cock. I reached over and took it in my hands and began to stroke him. I thought "Wow! I can't believe I'm jerking off… Read more

Derrick dared me to walk down the hallway of our hotel wearing only a black corset, a black gaff, fishnets and 4" heels. I took him up on his dare and walked half naked down the hallway. The night concierge caught me right before I went back into the room. He stopped me in the hallway and said "Ma'am! you can't be out in the hallway like that! I'm going to call security!" he had a thick West Indian accent that really turned me on. I coyly said "Oh come on can't we make some other arrangements?" He looked up and down the hall and said "What do you have in mind? "I said "How about an incredible… Read more

This is Part 2 of "Monday Morning Fun" Kyle arrived at 7 p.m. sharp. It was summer out and very warm. He wore a really nice Hawaiian shirt, shorts and Chaco sports sandals. I invited him in and kissed him. I led him to the living room and suggested that he sit down on the couch and I'd get us a glass of wine. I was wearing a light blouse with a leopard skin pattern, a denim mini skirt, a pair of shear seemed thigh highs and my favorite black 4" pumps. Underneath I had on a beige strapless bra and a beige gaff that hides my cock and balls but shows off my cute derriere. I got us each a glass o… Read more

One night in 2009 while coming home from a night of clubbing I walked up the stairs to my apartment and encountered my neighbor Darren. I freaked a little because I was still "in the closet' and only going out in my Melissa mode on weekends or when I was on vacation. Darren is a handsome black man with a great build, sexy eyes and a wonderful smile. Up until that night I had seen him before but we never said more than "Hello!" to one another in the breezeway or parking lot. He said "Hey, I didn't recognize you at first. You look great!" I felt myself blushing but I was also excited and flatter… Read more

This happened me last night when I was meeting a friend at his hotel room. The night concierge approached me and said. "Did Ginger tell you about me?" I said "No, what should I know? Let me call her." Ginger is my CIS female friend. I text Ginger and she said "Oh yeah, that's Carlos. He's cool and very cute I suck his cock once in a while. Are you willing?" I was like "Fuck! Well I suppose so. He is very nice looking!" I got off the phone and text Jesse and told him I was running late. He's said "NP". I looked at Carlos and said "Okay, where shall we go?" He smiled and said "Follow me". He's a… Read more

About a month after we began dating Raphael took me to Las Vegas to meet two of his friends. I was in my early 20's and hadn't really begun exploring my feminine side. One of his friends was a very well hung black guy named Tommy and the other a guy named Juan. Juan was a hairstylist who owned his own salon near the Las Vegas strip. Raphael convinced me to get a girly make over. Actually, I didn't need much convincing. I shaved my legs and what little body hair I had and we went to Juan's salon. He had purchased a few slutty outfits for me from Frederick's of Hollywood; short cocktail dresses,… Read more

I met  Raphael hitchhiking when I was living in San Diego. I was very bi curious but never acted on my feelings  He picked me up and we went to where he was house sitting. I was a little scared but also aroused at the thought of him doing me.We smoked some weed and drank a few beers by the pool. Raphael suggested we go for a dip. We got on undressed and I dove in the water and swam a lap. When I swam back he was sitting on the side of the pool stroking his 8" uncircumcised cock. I thought to myself;  "Well I guess I know where this is going!"  I was 19 and Raphael was in hi… Read more

I came to terms with my gender identity about 12 years ago. I've identified with being female for as long as I can remember. I read Christine Jorgensen's autobiography when I was teen and readily identified with her and admired the courage that she had to transition in the 1950's. In my mind Miss Christine was a pioneer and in many respects a role model for all transgender people. However, in 1974 young men weren't supposed to want to become girls and I learned to repress my feelings quite well. I dated girls, drove fast cars, drank beer and enlisted in the Navy when I graduated from high scho… Read more

Last night I met with a Solider with a BBC stationed nearby that just returned from overseas. We met on xHamster and have been chatting for several months. He told me that he'd never been with a transsexual but was very curious and was jerking off to transsexual porn including my photos. As a veteran and I know how horny they can get. We planned a rendezvous when he got home. He was nervous as hell when he came to the hotel room. I got us a Heineken and suggested he sit on the couch. I took off my black satin robe. I was only wearing a black bra, garter belt, panties, fishnets and heels. I tur… Read more

I knew when my friend Sierra invited me to spend the weekend with her we wouldn't just being going to the mall and out for dinner and drinks. Sierra loves sex as least as much as I do and like me she has a penchant for BBC. She invited me up to Lexington for the weekend and said to bring a couple of slutty outfits because she had some friends that she'd like me to meet. She wouldn't provide any details other than I'd like her friends and have a wonderful weekend. I selected a sexy black bra, garter belt and panty set. Of course I added some sexy fishnets and fuck me pumps to my ensemble. I als… Read more

I began exploring my feminine side sexually about two years ago. I had been a crossdresser for years and definitely bi curious but was always too inhibited to live out my sexual fantasies. Until last year I rarely went out dressed up unless it was Halloween or Mardi Gras. I had been told I was very passable (nice legs and :lol: ) I met a t-girl named Celeste on line in a crossdressing/transgender forum. We chatted for hours over the course of several months and she finally convinced me to meet her in the city where she lives. Celeste does girly make overs for aspiring crossdressers and trannys… Read more

The fascinating part about exploring this phase of my life are some of the unexpected pleasures and surprises. I work as a consultant out of my home office. I send and receive a lot of things by express courier. I use the same company that shall remain nameless, but it suffices to say it's one of those overnight outfits that lets the driver's wear cute shorts when it's warm out. I generally have the same driver and his name is Kyle. This man is one of the kindest and sincere young men that I have ever met. Kyle is built like a football wide receiver or cornerback, slim with just the right amou… Read more

I wanted to share an encounter that I had year in New Orleans during Mardi Gras. My t-girl friend Deanna and I were hanging outside a GLBT friendly bar on Bourbon Street called Oz. It was about 8:00 p.m. and we were partying but pacing ourselves. A handsome young black college aged guy approached me and asked me which direction Canal Street was. He stated that he lost this friends in the crowd and was going back to their hotel. He was a little buzzed but not drunk. He looked Deanna and I over, up and down and stood back and said "Are you she-males?" At first I was annoyed as I find that term p… Read more

I'd been seeing Darren for the last couple of months. He's a nice looking guy in his early 30's with a physique like a running back and a magnificent Big Black Cock. The first time we made out and I reached down and unzipped his jeans and took his thick 9" cock in my hands. I tried to promise myself I would only give him a hand job and make him "earn" a blow job or a piece of my white booty. I stroked him for about five minutes and he seemed to enjoy my ability to give a hand job, but as soon as I saw this pre-cum emerge from his pee hole I leaned over and licked it off. That was the point of… Read more