Valentine Day Cheaters



What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Finance
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Super charged sexually
How many sexual partners have you had in your life (including oral sex)? 100
How many hookup stories have you here posted before? 0

Valentine Day Cheaters

How long ago did this hookup happen? 6 years

What was your relationship status at the time? Engaged/Married (monogamous)

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? She was a guest at a hotel bar in a big US city. She traveled a lot for business and was married. She was the same age as me, 40ish, with fake breasts. She had a gymnast’s body.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I came into the city to have a discreet job interview when I was looking to change companies. Unfortunately, I had to stay overnight because of how late the interview was. It was also on Valentine’s Day. After the interview, I had no plans and didn’t want to be seen in the city in the event that I bumped into anyone I knew and had to explain why I was there. So, I went directly back to the hotel and wandered into the bar. She was at the bar alone, talking to the bartender. I sat close to her on one side and then casually struck up a conversation. We both talked about how it sucked being married and away on Valentine’s Day. I said we should make the best it, asking if she wanted to eat dinner with me at the bar. She accepted. Soon after, drinks started flowing and our open talk started to get more suggestive. We admitted that we were attracted to each other.

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? After dinner and a Valentines themed dessert, I jokingly said that, if I were home, I would probably be having sex now, but it won’t be happening tonight. She said, “not necessarily.” The ice was broken and it was on. I told her my room number and said that she could come by for some champagne if she liked. After fifteen minutes in my room, I heard a knock. When I opened the door, there stood this tiny married woman in a sexy pink sweatsuit. She bounced into my room and onto my bed. The clothes came flying off. She was very aggressive. She put my whole cock in her mouth. She also admitted that she was very aroused throughout our entire dinner. She wanted to fuck me the second I walked into the hotel bar. I had her on her back with her big fake tits in my face and we fucked for close to 30 minutes in missionary position. It was very loving for someone I had just met. I was inside her bare and asked where she would like me to cum. She said she wants it inside her so that she could remember me while leaking my cum all the way home to her husband.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? After spending most of the night with me, she did eventually go back to her room. I never saw here again but we texted for a bit. About a year ago, she said that we couldn’t text anymore because she was tired of hiding her phone from her husband.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? I was feeling lonely

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 your partner at the time? Very

To whom did you talk about the hookup? How did they react? I have a small group of trusted friends who know how a monogamous marriage can slowly kill a man. We share a desire to please more than one woman.

Did you get emotionally hurt as a result of this hookup? A little bit

Why do you regret this hookup? I regretted it immediately afterwards. But now that its long history, I look back at it as an amazing night with a great person.

What was the BEST thing about this hookup? Her tiny gorgeous body and the fact that she found me attractive.

What was the WORST thing about this hookup? nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve always been open to casual sex and think it’s great.

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

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