The Greatest Orgasm of My Life



What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Los Angeles
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Exhibitionist
How many sexual partners have you had in your life (including oral sex)? 30-40
How many hookup stories have you here posted before? 0

The Greatest Orgasm of My Life

How long ago did this hookup happen? 15 years

What was your relationship status at the time? In a relationship (open)

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

How long did you know the person before this hookup? For 1 to 3 years

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? E and I met through friends in college. We started making out and hooking up and fooling around after a few months of being just friends. We never had sex, because she thought I’d slept around too much. She didn’t feel safe in that way with me, so we kept it to heavy fooling around for months.
E was a short curvy girl, pretty. Cute. She had giant boobs and was proud of them.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I left town for a few months and we lost contact to some degree. I came back and hung out at her place with her. We talked about the fact that we’d both slept with other people. She’d slept with one of my friends, and since we were friends with benefits, I couldn’t really be mad. She told me they hadn’t even used condoms. Which was completely her M.O. (and a huge turn on for me)
Suddenly she turns and says that she’s sorry she never had sex with me. That she’s made a big deal out of nothing. And she wanted to make it right.

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? I was in town three days. This hookup lasted all three.
E grabbed a condom and we started fooling around in her bed Friday night. We started having sex, me on top. It was fun — until her roommate walked in. We stopped and pretended to be asleep. Friday was kinda ruined.
I came back to hang out with her Saturday night. We made out on the couch in her living room. The next thing I know she took off her underwear and straddled me. She rode me for two minutes until she looked me in the eyes and said “I. Am. Gonna. Cum.” And she had this earthquake of an orgasm. Her whole body shook and she collapsed over on the couch next to me trying to catch her breath. I told her that was awesome. She told me she had to stop… For the rest of the night. I was flattered that she came so hard she couldn’t continue. But my blue balls were swelling from two consecutive nights of sex without orgasm. With a new girl no less.
Sunday night, E brings me back to the same couch and tells me she’s sorry she made us use a condom and she doesn’t want to do that tonight.
I was cautiously optimistic about this. We made out and I went down on her for a good while. She always came easily from any fooling around. So by the time she told me to fuck her, she had the wettest vagina I had ever felt. It was the best vagina I ever felt. Before or since. And I had no condom on.
I started slowly moving in her for a whole thirty seconds. Then I had to stop. I was so close to cumming I couldn’t move. Couldn’t think. I sat still inside her for a few seconds and then got my control back. I started again, but thirty seconds later the same thing. I held back my orgasm no less than twelve times in about five or six minutes.
E asked me what was wrong, why I kept stopping. “I just can’t hold it back.”
She told me to just cum. I asked where and she asked me where I wanted to cum. I pushed into her as deep as I could and said “right here.” She smiled and said that sounded good.
Not having to hold back, I pounded her for about 15 seconds before my orgasm started.
At first I felt an amazing surge and I unloaded a gallon of pre cum into her. “Oh. My. God.” She said. I told her “not yet. That’s just pre cum”
And then I came. My pulses were coming three times faster than normal and the actual ejaculation must have last thirty seconds. Halfway through the orgasm, at least a whole load had run out of her and onto her couch.
It was the most intense, longest orgasm I ever had. Two days of blue balls were so worth it.

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? We had a friends with benefits/open relationship for a few years afterward. It turns out that bareback orgasms were a huge turn on for both of us. We had some rest sex for a few years until it started to get a little too long term.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

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? Told my friends as this was the greatest sexual exploit of my life. They were a bit jealous.

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

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? I felt so satisfied. It was so many months in the making and it was the best possible physical sensation imaginable.

What was the WORST thing about this hookup? I guess I’ve chased that feeling the rest of my sex life. It’s never been that good ever since. With her or anyone else.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. At first I thought sex should be a bit more private. If I was still hooking up with her, I’d try to get her to sleep with my friends. She was so amazing that I just wanted other people to understand. Kind of like eating at your favorite restaurant.

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

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I think more people should get tested more and and have more casual sex. I think we’re wired to want it more than we admit.

What do you think about the Casual Sex Project? So great. I love knowing other people are interested in the same experiences I am.

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