A Glorious Mistake



What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: College degree (eg., BA, BS)
What’s your occupation? mgmt (not the band unfortunately)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

A Glorious Mistake

How long ago did this hookup happen? 4 months

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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? My physical ideal. Petite, Asian, and she was also sharp as tack and a bit of a humanitarian.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a cafe. Mind numbing small talk, broadened into something more interesting. When she got up to go to the washroom I noticed that she had a tight little ass, which was when the tug in my groin overrode the fidelity to my wife angle on life I’d been attempting to take. I didn’t mention the marriage to her, didn’t expressly state I was single, but she probably got that impression when I mentioned a great restaurant I knew in the area, and hey, why don’t we swing by. I’m a bit of a slow mover, so there was zero physical contact that evening. Frustrating, but I’ve always preferred long game, letting the excitement build up. My wife was out of town that week, so I imagine I debased the wifi quite a bit to get the brain down to the level. Via text, we flirted and I asked her if she wanted to meet at the beach, and we did. We kissed, it was great, but she confided that she was a virgin. I was shocked, I didn’t know that could happen anymore. She was also nineteen which surprised me, I had been thinking 23ish. I wasn’t too pleased. I knew there could be no future. She was religious, strict asian parents, but when we started making out. In the dark, in the park on a knoll. I was really thinking victimless crime. The wife wouldn’t know, we would have a short fling, then I could pretend that I had to go work overseas for a couple years. Cowardly I know. But more than the physical what I really craved was falling in love with someone and someone falling in love with me. What a fucking conflagration of intensity in life born in little sparks. Breathing life into a suffocated brain. Caution gave way to desire.

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 on a road trip. By this point we had progressed far beyond kissing. I had explored most of her body. She hadn’t taken her panties off, she said she could only do that when married. But I had been kissing her perfect little breasts, and damn since when did suckling such beautiful little nipples get me so high, She was cautious around the bulge in my pants, gently grazing it occasionally but hesitant, like it was a grenade that had the pin half pulled out, to throw in a crappy metaphor. When we got to the hotel she said she was in love with me. This was not testament so much to me, I don’t think, but more related to her inexperience. Oh man this might not end so well, I would think to myself, stroking my finger ever deeper into her jeans, under the band of her panties. Everything was a first for her, the first cock she’d ever seen. The first time she’d taken her panties off with someone, the first time she let someone lick her. We started very slowly, took a shower together, where she got on her knees and asked me how she was supposed to suck it. I got her to lick it just on the underside, then she took the whole thing, at first hesitant, but with progressive confidence, into her mouth, until, so close to cumming, I had to pull out. We went back to the bed and I fingered her for awhile. She asked if I wanted to fuck her, and I said god yes, maybe I shouldn’t have mentioned god. But I wasn’t going to. Already too much weight and deception on my shoulders.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? No

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? My wife found out and the world fell apart for awhile. I convinced her to stick it out, and we’re happy again, but damn as good as it was I’m never doing that again.

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel better about myself, To feel more desirable, To feel more confident

How intoxicated were you? A little tipsy/high

How intoxicated was your partner? Not at all (no alcohol or drugs)

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? Very much

Why do you regret this hookup? Because it’s pointless to make a commitment to monogamy if you’re not going to commit to monogamy. Whether I should have committed to monogamy is another question, one I consider daily.

What was the BEST thing about this hookup? The connection, rekindling of passion with real connection.

What was the WORST thing about this hookup? Psychological armageddon for a couple of months.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, that brief euphoria that comes from squirting white stuff from your cock is not worth ruining your life.

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