One Time

I am married and have been for 15 years. I travel for work often but have always been faithful until this month. On my last trip I was eating dinner in the hotel bar when I saw a beautiful woman walk in. I suspected she was a professional but damn she has hot. Half Asian tall with an amazing body and smile. I was seated at the bar and she sat next to me and order a SavBlanc. She introduced herself as Jackie and we made small talk. She was really smart and funny and I was really enjoying myself. Before long we had finished several drinks and it was midnight. We just lost track of the time. I eventually said it was time to go to bed and she asked if it was an invitation. I should have said no but her smile was impossible to deny. I paid the bill and headed for the elevator. As the door closed she kissed me passionately and her lips were as soft as I had hoped. We made it to my room and she had my pants out and cock in her mouth in seconds. I couldn’t believe how good it felt. The best BJ I have ever had. I warned her that I was about to cum and she doubled her efforts. I released in her mouth and she swallowed it all. I was speechless. After recovering I told her it was my turn but that’s when it got a little crazy. She wouldn’t let me take her skirt off. Then she stood up and admitted that she was trans and had a penis. I was shocked. She started crying saying that she was having so much fun but didn’t know how to tell me. I comforted her telling her that she was the most beautiful woman I have ever been with. I promised that I didn’t hate her and while I had never done anything like this, I wanted to make her happy. She wiped her tears and got undressed. She had a small penis, only about 5 inches. I spent the rest of the night and next few nights learning to please her.

Comments

Anonymous

by Anonymous on Mar 8, 2025 at 7:54 AM

It's wonderful that you broadened your sexual horizon, especially when we hear so many anti-trans messages these days.

One thing I'm not clear about is whether she charged or not. You mention suspecting she was a professional, and then paying the bill before going to the elevator with her, so that's why I'm curious. Many trans people are ostracized, have trouble getting hired for regular work, and need additional income for hormones, makeup, clothing, and other expenses related to their transition. Still, this doesn't excuse the high prevalence of "spoil me" references in trans women's online profiles. (I have nothing against prostitution -- hell, marriage is the same thing, it's just that you pay by buying her a house -- but it should not occur on apps intended for dating.)

As far as your marriage, monogamy is unnatural and people have needs. Will you tell your wife? Will you step out again in future? Will you allow your wife to step out, as well? Open marriage is a wonderful thing!

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Anonymous

by Anonymous on Mar 8, 2025 at 8:25 AM

I am sorry I didn’t make it clear. Jackie did not charge me, I picked up the bill because I wanted to treat a lovely lady to drinks and a bite.

Jackie and I had several long talks, it wasn’t all sex, though there was a lot of that as well. She admitted to occasionally selling sex for extra money but said it was rare and she was very picky. She also admitted that she was in the hotel bar for that reason because she needed some extra cash but ended up having so much fun that she decided to forget it. I learned a great deal about her struggles in life and my heart went out to her. I actually offered to help her financially but she said that she would not charge me so I treated her like the princess she was for a few days and snuck 500.00 into her purse before saying goodbye. I didn’t see it as prostitution, I wanted to help her.

I have not told my wife and may not ever. It would be hypocritical of me to deny her sex outside of our marriage now if that ever came up. As for it happening again. I return to the same city in May and plan on seeing Jackie.

I admit the sexual experience was different and very enjoyable. I did things with her that I never thought I would do. I do not like the taste of cum but don’t hate it. The texture is the worst part. I will admit that I really enjoyed anal sex. I am little larger and kinda thick and my wife won’t let me have anal sex with her. I also enjoyed Jackie in my backside. It was fun and exciting.

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Anonymous

by Anonymous on Mar 8, 2025 at 10:51 AM

Well, you are now hooked on cock. Enjoy. Happens all the time. Nothing wrong with it either.

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Anonymous

by Anonymous on Mar 9, 2025 at 8:43 AM

Thank you for answering, Sam. What an exciting new connection for you! May you and Jackie enjoy a long, wonderful, mutual relationship!

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Anonymous

by Anonymous on Mar 11, 2025 at 8:38 AM

That is a spicy story Sam. I can relate. I had a similar one time deal happen with me when I went to a sex club once in San Francisco. An Asian Trans sucked me off. They looked really good and passable as a woman and they sucked me off so good with that eagerness to swallow it all.

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