Hi Stephanie,
Thanks for starting this thread. I think that this is a good way for us to share our experiences and let some of our admirers understand that we are people and not just objects of their erotic desires. I'm nearly 53 and have only been in transtion for about four years. I was married for many years and repressed my feminine feelings. Prior to the I only ventured out "en femme' during Halloween or Mardi Gras when I resided in New Orleans. When I found myself 48 and divorced a lot of my feminine feelings emerged. I discovered sites like
www.crossdressers.com and
www.urnotalone.com and realized I wasn't a freak. One thing led to another and Melissa emerged from the shadows.
I began ordering clothes, lingerie, wigs, shoes, a set of breast forms. I learned to act more feminine, walk in heels, do my make up and eventually began going out. I made friends with other t-girls on line and enjoyed the new friends that I made. I decided that I should begin to venture out and explore the world as my new found self. First I attended house parties with girls I met on line. Eventually they convinced me to go to a T girl friendly club in Nashville. I realized hardly anyone really cares if you are tranny if you are a decent person and don't act like an idiot. Regardless, I am always careful when I go out.
I began meeting a lot of people and liked it when other t girls or men flirted with me. On New Years Eve 2007 I went out clubbing with some t girlfriends. About ten until Midnight I met a nice looking guy at the bar. He introduced himself and said his name was Ryan. He asked me to slow dance. I accepted his offer and he put his hands on my ass and something stirred inside me. We danced to a couple of more songs until Midnight. Everyone of the dance floor was kissing. I looked at him and kissed him passionately, long and slow and worked my tongue into his mouth. He reciprocated. I felt my cock swell and was thankful it was tucked away with a gaff. I could feel his cock through his trousers and the fabric of my dress.
I met my friends at the table and they were all going to Waffle House. I had driven my own car and said I would follow them. He looked around the parking lot outside and evidently his friends had ditched him. He said "I guess I'll take a cab!" I said "Bullshit!" "Jump into my Jeep!" "Come have breakfast with us and I'll take you home!" We had breakfast and I told the girls I was taking Ryan back to his apartment. He shared a little apartment in the near the university. His room mate was away for holiday break. He invited me in and I accepted and sat on his couch whille he got us a glass of wine.
When Ryan sat down next to me my urges took over and I reached over and unzipped his trousers. By now his young cock was rock hard. It felt good in my hands. It was similar to mine but about an inch longer. I told him to take his pants off and I pulled my cocktail dress over my head and put it on a chair. Now I was only clad in my bra, garter belt, a gaff too hide my goods, seamed hose and heels. I sat down next to him and leaned over and took his cock into my mouth. I was sooooooooooooooo fucking excited to be giving my first blow job I was beside myself. I got into a rythym and soon discovered I was about to take most of him in my mouth without gagging. I kissed the tip of his cock and licked the shaft and sucked on his balls. I muttered "When you are ready to cum just blow your load in my mouth!" "No need to pull out or warn me!" I know what a skank! I can't believe I said that! It must have been something I said because he shot a thick wad of semen in my mouth less than a minute later. At first I didn't realize he was cumming. I began to swallowing and didn't waste a drop. The sensation of him ejaculating into my mouth was something I will never forget.
I liked sucking cock from the very first time. My only regret was waiting until I was forty nine but everything happens for a reason. I went out with Ryan a few nights later and decided to let him buttfuck me. I had been diddling my ass with toys and dildoes and knew he would feel good inside me. Before our date I douched and I wore a medium sized butt plug to prepare myself for my first anal experience. I had Ryan lie on the bed and I sucked him off and put a Lifestyles condom on his cock and straddled his narrow waist. I eased down on his cock and he was soon balls deepside me. Ryan came in a few minutes and I continued to ride him until I felt his erection soften. It felt good but I didn't cum. I think I was too nervous. I was so fucking horny. I tugged the condom off his pecker and squirted the contents on his nipples and sucked it from them. A little while later we attempted it again. I was on all fours and Ryan was behind me thrusting his 8" cock deep and long into my ass. Something stirred inside me. My cock grew hard and a stream of cum erupted all over Ryan's bed sheets. I had a total body orgasm and nearly passed out with pleasure. That was over four years ago and my journey continues without regrets! Sex isn't the end all of my femininity. Psychologically, emotional and sexually and I a woman. The physical part is work in progress. Regardless sex is an aspect of my new life that I find exceptionally pleasurable!