by Pseudonymous Miss

What’s your gender? Woman
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? New York metro
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Writer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Jewish
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? none

Lovely Frustration

How long ago did this hookup happen? 12 years

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than 6 months

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? I met U at a social gathering. Both of us had recently moved to town. He had curly brown hair and hazel eyes and was quite short and barrel chested. We were chatting and when I mentioned I liked to tango, he asked for my number. I was impressed with his wit and confidence–it takes a certain amount of attitude for a short man to ask out a tall woman with the intention of dancing (I am almost 6 feet tall.) Our first date was terrible though–he’s a doctor and was on call and spent half the time on the phone consulting about a patient with a terrible urinary tract infection. Despite that, we became friends and hung out regularly. We were emotionally close. He shared details of his life with me, including his estrangement with his father in the year or two before his father’s untimely death.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few months later, he dropped in at my place on his way to meet friends for dinner. We chatted for a bit and then he said he had to go. We hugged goodbye, and he asked for a kiss. He sometimes did that, and I sometimes obliged. He was a lovely kisser and we’d made out once but at this point we were strictly friends.

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? So I kissed him, a little impatiently. He laughed and kissed me again, and this time he reached down and tickled my clit through my jeans. This was impertinent so I took his hand and said, ‘you have to go!’ Good naturedly. He agreed, and walked into the hall toward the door but then stopped. I was like ‘what?’ for by this time I was a little annoyed.

He didn’t answer, just pushed me up against the wall and kissed me again, with passion. I was turned on in spite of myself and let him. He began to stroke the seam of my jeans, and instead of tickling it felt amazing. Warmth spread through my pussy and thighs, and I began thrusting against his hand. It felt good and I was just in the moment and moaning with pleasure.

He picked me up and carried me over to the door and set me against it, holding me up with one arm while he stroked me with the other. He was surprisingly strong. And his fingers were so delicate. He kept a light, rhythmic touch. I lost track of time and was on the verge of coming when he abruptly stopped and put me down.

I was completely taken aback, and so aroused.
‘Don’t stop!’
But he just smiled and said he had to go. Then I got kind of irritated. I walked into my bedroom and called to him to come in and sit, that I just wanted to talk, but he said he was going to be late and left quickly. It was weird.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, but I was close

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? I was rather annoyed about what had happened, maybe men are more familiar with this kind of scenario but I’d never had a man just walk away like that. U was more religious than me though, came from an orthodox family, and I suspected that had something to do with it,

We stayed friends, and some time later we were at his place and cuddling and ended up in his bed with me wet and aroused again and really wanting it, but as soon as I touched his cock he said ‘no.’ So I made him tell me what was up. Apparently he’d taken a one year vow of celibacy when his father died. He allowed himself to mess around but no penetration or orgasms allowed. That explained a lot.

He eventually moved away to pursue career opportunities and I got married and had kids, but we still talk occasionally. He never married but always has a tall, attractive girlfriend.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Emotional intimacy, closeness, connection

How intoxicated were you? Not at all (no alcohol or drugs)

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

How wanted was this hookup for you at the time? A little bit

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? No one. We traveled in the same circles, everyone was fairly religious and looking to marry…didn’t want to damage reputations, his or mine.

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 unexpected pleasure and delicacy of his touch.

What was the WORST thing about this hookup? Him not letting me come and leaving abruptly.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. It opened my eyes to how skilled a man can be with his hands.

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

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

What do you think about the Casual Sex Project? It’s good reading–other people’s experiences are quite diverse.

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

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