Last Hurrah to Casual Sex



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? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Education
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 1

Last Hurrah to Casual Sex

How long ago did this hookup happen? 9 years

What was your relationship status at the time? Single

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? Like my previous Ottawa hookup through Lavalife (“Lavalife, Intimate Section”), she was a French Quebecker. Something kind of wonderful about those women, a kind of mix of sweetness, straightforwardness and passion. She was somewhat older than me, past thirty and had a child, but was still keen for hookups it seems.

She had short raven hair and a plump, substantial body. Not fat, not flabby, just coated in softness and warmth. Dressed casually yet conservatively, she was matronly in a kind of erotic way, if you follow; I think in some way I was sort of getting off on the idea of her as a “permission giver.” She had big breasts, big brown eyes, yet there was one part of her that seemed to bely this matronly package hidden at the core of her. One almost would have expected (preferred?) it to be covered with thick black curls; instead it was completely bare. Bowing to social convention? Or the naughtiness of this waxed pussy concealed beneath that motherly exterior? It was exciting.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We communicated through Lavalife, met at a bar, got some alcohol and came back to my tiny basement apartment and its single bed, which, given as my prior fling detailed in my earlier post was just weeks earlier, was finally getting some action.

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 shared a bottle of something as we goofed off on my couch. I think she might have preferred a slower start but I was impatient and peeled off her shirt and bra, sucking at her womanly breasts and nipples as we watched TV. When we got naked, she was especially responsive to my attempts at oral sex; it was easy to keep up with since she was vocally responsive and tasted pretty nice. We fucked in different positions around the room; it was a distinct pleasure feeling her soft, lovely body against mine and burying myself deep in her wetness. It was a long, draining session and I think I made her orgasm several times with my mouth.

The downside was that I couldn’t come inside her. “What’s wrong baby, you can’t come?” I recall her asking. It was less than ideal, but I finished by jacking off into her mouth; she ate it, something that no woman had done in years. Not sure why it makes a difference; feels like acceptance I guess.

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? We cuddled a bit and she drove home, and I never saw her again (see below). My sole one night stand, probably ever. Good to have gotten that out of my system, I suppose, and there were some nice moments (you’ve probably noticed how much I focused on her body throughout — it was a nice change). But to quote Leonard Cohen, “I don’t think of you that often.”

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, I was feeling lonely

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? Very

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

To whom did you talk about the hookup? How did they react? Don’t recall telling anyone, except my now-wife much later.

How would you best summarize people’s reactions about this hookup? Neutral

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? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? She wanted it to go somewhere else and it didn’t. I ended up in a relationship right afterward, and I think I could have informed her of this more gracefully; she was obviously put out. I’m now married to a woman I started seeing right after, so I think I made the right call.

What was the BEST thing about this hookup? I remember fondly her stretched out naked on my floor while my face was buried in her pussy, listening to her moans as her smells filled the apartment. And her body — to harp on, I’ve been with more flabby women and that doesn’t even bother me especially, but she was more large-figured in a way that complimented her utterly.

What was the WORST thing about this hookup? Sort of a checkered postscript as detailed above.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It did make me a tad more aware of its potential emotional costs.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? This was sort of a last hurrah, though I didn’t know it at the time. I do sort of wish I had taken advantage more when I was a single,

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