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What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Insurance
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 3

Cheating During Work Training

How long ago did this hookup happen? Last week

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? J is a woman my age, I didn’t ask her age. She is average looking, not ugly in any way, but also not what people would call smoking hot. She is slim, ginger, green eyes. Her boobs are rather small. I have not asked her whether she is married as well. Neither has she asked me. I think she also wanted to get rid of some sexual energy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had to attend a work-related training in a different city. This time I would get the training and not be the trainer myself. Perfect opportunity to cheat.

I have a wife and a child but the sex in my marriage does not satisfy me entirely. I crave the thrill of conquest and the novelty of the skin of strangers. I have cheated on my wife in the past and gained confidence that I can find women who are willing to hook up with me. It is not that I don’t love my wife and want to have a different relationship, I just want to have one night stands that my wife cannot find out about.

So my mind was set that I would either pick up a woman during this training or if that failed, I would go to a brothel. I know that some people use those work training for hookups, so I should try my luck as well.

I was indeed lucky and J got flirty with me on the first day of the three-day training. On the second day, the whole group went for after-training drinks. J and I flirted heavily. She really made it easy for me, I was getting sure that she had the same thing in mind that I had. J gave me an easy cue when she mentioned later on in the evening that we were both in the same hotel. I got the hint and told her that maybe it was already time for us to go back. Even though people were still hanging out and would probably do so for at least another half an hour.

J smiled at me and agreed that we should leave. We walked the short way back to the hotel closely next to each other. J was bubbling with energy, laughing a lot and casually bumping into me. At one point I took her hand and she let me. J kissed me and whispered into my ear that we both want the same thing. So it was set, I got lucky.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We went into my room and got undressed quite quickly. There was no long fooling around. We didn’t even kiss a lot during intercourse. J was pretty much into business. She gave me a blowjob which I turned into a 69 session. She went on top and started riding. We changed position and in the end, I pumped my dick into her doggy-style. J seemed to enjoy this and moaned loudly.

After my first ejaculation, J asked me whether I thought I could muster the strength for a second round. I said yes and then we made out for a little while until J wrapped her lips around my penis to get it up for the second go. I got it hard, we fucked missionary until I had a second orgasm. This time it wasn’t as good but certainly worth the while.

J seemed to be happy with my efforts but left to go to her own room shortly after we were done.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? J was friendly but professional during the last day of the training. Our planes left in the evening, and we did’t even say goodbye to each other properly. It was just fire and forget, but that was what I had been aiming for anyway. I think the same applies to J. I wonder whether she has been cheating on a partner as well.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, To feel better about myself, To feel more desirable, To feel more confident

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one, this is my big secret

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? the ease of it. We both wanted the same and got it. Of course, I like it that there were no strings attached, no feelings hurt. If I meet that woman again I will probably try to get into her pants again. She seems to want it.

What was the WORST thing about this hookup? It was not very emotional, that has to be admitted. It still felt a lot better than going to a brothel. I really would not want to do that because I like the thrill of the chase and the pride of conquest.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It is almost getting a routine now! I want to hook up some more because I really enjoy it. It is a nice adventure and a huge ego boost. Too bad I can’t tell my wife about it.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? I good site to tell about my escapades.

You have a hookup story to share? Submit it here!