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Accidentally in a trans bar in NOLA, I took home a CD

1177 words | 2 |4.67

I was working in New Orleans for a three month gig. After the first week I was bored of bourbon street and on one of the side streets in the corner just down from my hotel there was a little neighborhood bar. It was quite, soft music playing and not a lot of people. Just what I wanted. I went in and sat at the bar, ordered a drink. It took me a while, then I realized the two barmaids were men. They were men with tits and pretty damn nice looking bodies too, one was downright beautiful the other quite pretty. I didn’t give a shit and kept on. They struck up conversations with me, and telling me I need to meet the “girl” with their air quotes, sitting in the next room alone. That room had a dancefloor and there were 3 couples dancing, two were mm couples, the others once looking good were a man and a CD or trans. I saw her sitting at a table to the side, all alone. One of the barmaids, told me that she just ordered another drink and for me to take it over to her.

I did, and asked to sit down. She said it was ok with her, so I sat. I tried to get a conversation going, and she wouldn’t look me in the eye, and tried one word answers anytime she could. Not going over too well I was about to leave then Olivia one of the trans barmaids comes over with two more drinks on the house. To the seated girl “Sandy, this is Tommy, he’s from New York and her on business for 3 months, you need to stop moping around and talk to him, he’s fun, he’s interesting, and you’re being a pouty little bitch girl!” I was shocked by Sandy wasn’t. She looked up finally at me and apologized. She explained that she’s only been coming outside dressed for about 3 days and feels very self conscious. I told her she needn’t, she looked great. She was pretty, but not overly made up, just barely some make up, and light lipstick, no falsies, but wearing a green dress, a jumper type that hung straight down about 6 inches above her knees. She thanked me, and said that helped. I asked her to dance, not to worry about anything just dance. It was a slow one and she didn’t know, I stood up and took her hand and got her up. I took her on the floor and we started dancing, soon, I moved both arms around her waist, she had a little waist like a real girl. Soon she was leaning into me, her head on my shoulder. It was there I asked her for a date, a real date, dinner, movie, some drinks whatever she wanted to do. She hesitated and Olivia and the other yelled out “Fucking do it honey, he’s a catch”.
We both laughed and she accepted.

I picked her up at her apartment, she was very self conscious, and even asked me about wearing small liquid filled falsies she had. Inside her bra, and under her blouse she looked like a large A cup girl. I liked it. She was pretty good with her voice, she had small hands too, unlike most men. Back at the same bar, we had drinks the girls razzing us insufferably, She held my hand, looked me in the eye and asked if I’d like to go back to her place for “a drink”. I just laid it out there, “A drink? Not really, something else DEFINITELY”. She got out of her chair and stood up holding my hand and said “Lets go”. At her place she told me that she’d not done this before. I asked and yes she’d had sex with two boys (she was only 18) back when she was 15 and the second one at 16. The first one she only sucked and he did it to her also. The second one after a month of sucking made her take his cock inside her ass, unwillingly at first but she let it continue. He fucked her several times over a month or two. Then he left and never came back around. This was her first time as a transgirl. I told her we’d do whatever made her comfortable. She asked if I wanted her in lingerie or something she had a few things. Instead I sat with her on the edge of her bed, and kissed her. While we kissed I slowly took off her blouse, her skirt. Now in only panties, thigh highs, and bra with the falsies, we laid back. She was moving her hands on my cock, and I dipped into her panties and did the same. She had about 5 inches, not too thick. She said I didn’t have to do that, I asked if she minded, and she didn’t but didn’t want me to think I had to do anything for her, she was just wanted me to be happy with her. “I am” I said. With that she went down only and swallowed every drop when I came. I did her with my hand, and let her shoot on her belly. I scooped up some of her sperm and fed it to her, and the rest I purposely took into my mouth. After I told her that was the first I’d ever done that with.

After listening to some music, smoking some pot we started in again. This time she rolled over, handing me lube. I lubed her up, and myself then rolled her back over. “Don’t you want to do it in me?” she asked. “yes, I do, but this way” and I pulled up her legs, pulled her panties down just so she was covered in front, and I put my cock at her hole. “Do it” she whispered “Do it, do it now” and I sank into her pretty little butt. I went slow and fucked her for about 30 minutes and finally asked if I could cum inside her and she welcomed it. We fucked once more that night, and after I went down, pulling her panties totally off and sucked her cock, another first for me.

I had a gurlfriend for 3 month in NOLA, and I enjoyed it a lot. She was loving, cute, nice body, and yes I sucked her off, and twice let her fuck my ass. She didn’t like though and quite frankly neither did I. It was hot, it was a great memory, I often think back as i fuck my wife and think about how S’s life turned out. My wife is very pretty, even now after 2 kids, she does it in her butt too which is my fave, but I remember the first time I fucked my wifes ass, it was her first time doing it. I went nice and slow and she made me turn all the lights off. To tell the truth in the dark, in my mind I was back in NOLA fucking S

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2 Comments

  • Reply Ricky ID:1egzi95iptyi

    Learn how to write. Then read what you write. But otherwise decent story

  • Reply Emma ID:1edyitvw3d12

    I need to find a guy like you.