Date: 10/10/2017, Categories: Fiction, Anal, Bisexual, Consensual Sex, Straight Sex, First Time, Gay, Hardcore, Oral Sex / Blowjob, Trans, Trans, Author: jen128, Source: sexstories.com
It is amazing how a decision or two can change your life completely. I guess I should give you a little background. Two years ago I was a computer technician for a small firm here in town. At 32, with no family and a small apartment it seemed like a dead end. I did not have a girlfriend and had been with a couple of guys over the years, mainly for a quick blow job or at a glory hole for some satisfaction. I have always been a little small for a guy at about 5'7 and fairly thin. I was told I was too thin at about 130 pounds so most women looked at me as their little brother so it seldom went any further than that. That fateful Friday night, I had been given a two week vacation. We had been extremely busy and with all of the overtime and accrued vacation the boss insisted that I take at least two weeks to rest up. I had heard of a gay bar on the near west side of town called Satan's Den so I thought why not check it out for some quick relief. Not wanting my car spotted there, I grabbed a bus for the half hour ride to a nearby bus stop and headed over to the lounge. It was a little different with the entrance down a couple of steps and then after through the door continuing down a flight of stairs to a basement. It was a little dark with a dance floor in the center and a U-shaped bar to the side. The music was captivating and the beat almost seemed hypnotic. I took a seat at the bar and the waitress, with a pretty deep voice for a woman, smiled at me and asked what I would ... like. With a wink she was off and came back a minute later setting the drink on the bar. When I asked how much, she just said, "Honey. As good as you look I am just going to run a tab for you. Play your cards right and they won't cost you anything." I know the waitress was a crossdresser but she was cute. I am usually rather shy so I just sat there and nursed my drink while watching many crossdressers both cute and otherwise with guys, some guys with guys and some crossdressers preferring to stay with each other. The music was great and it was fun to watch all of the patrons having a great time. I was in the middle of my second screwdriver when a nice looking older gentleman asked if he could sit down next to me. As he sat down, all he said for a few minutes was, "Pretty, very pretty." Looking around, I tried to find who he was talking about but he was staring at me. Smiling he said, "I was talking to you. You may not realize it but you would make a very beautiful girl." I sat there for a minute with my mouth open not sure what to say. "I have to say", I said nervously, "I have never heard that line before." "My name is Richard, but most of my friends call me Dick. I hope you will be one of my friends. I find you extremely attractive", he said very softly. I told him I had always been attracted to older gentlemen. We sat and talked for a while and he bought me a couple more drinks, also taking care of my tab. The more he talked the more I found myself hanging on his every word. ...