Awakening Hookup



What’s your gender? Man
How old are you? 44
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: Some college (not currently in college)
What’s your occupation? IT Professional
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
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)? 20+
How many hookup stories have you here posted before? none

Awakening hookup

How long ago did this hookup happen? 15 years ago

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? 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 my age (about 30 at the time), tall, slender, blonde, and a great smile. I met her through a mutual friend who, looking back at it, likely set us up. This girl was recently divorced, as was I. Immediately we clicked, and there was a mutual attraction.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met with the mutual friend at a bar for a drink. An hour later she and I were at a strip club, mutual friend long gone, many drinks flowing, lap dances, and last call. It was a blur. We stumbled out into the parking lot, realizing neither of us was in any condition to drive, and conveniently there was a motel a block away.

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? When we got in the motel room, I was half expecting to just pass out. Instead, her clothes were on the floor immediately and she grabbed my hand and led me to the shower. I was clumsily undressing on the way, asking a few times if it was OK as I kissed her in the shower, asked if she wanted to have sex, just wanting to make sure we were on the same page. “Yes, I want to fuck,” was her reply. Our wet bodies were on the bed moments later.

She was pretty aggressive in bed, shoving my head between her legs and loudly yelling to eat her pussy. I happily obliged and was amazed at how quickly she came. I spent maybe a minute, tops, giving her oral before orgasm. She returned the favor and unfortunately in my excitement I came quickly as well. Up to this point, this is all within 5 minutes of getting in the motel room and having met her only 6 hours earlier.

We rolled around in the bed for a bit, making out, hands going everywhere. Then it suddenly occurred to me: I didn’t have any condoms. My mind started racing, trying to think of where the nearest market was that’d be open at this hour. I stopped, told her the situation, to which she replied, “Get gatorade and lube, too!”

I sprinted to the market. I mean full on sprinted. Gatorade, two different multi-packs of condoms, two different lubes. SPRINTED back. As I came through the door, I was half expecting her to be asleep and considering the earlier events, it’d still have been an awesome night. Instead, she’s laying on the bed touching herself. OK, seriously great night.

Clothes back off, condoms dumped out on the bed, she selected one quickly and put it on me, and asks what I’m cool with. This was the first time a woman had ever put a condom on me, which turned out to be way more erotic than I’d have imagined… plus I wasn’t sure what exactly she had in mind, but I answered, “I’m cool with everything.” She pulled me down on top of her and we were fucking. After a couple minutes of grinding away, she pushed me back, got on her hands and knees and said something along the lines of, “Fuck me.” As I’m fucking her, she squeezes some lube on her ass. It was at this point that it sunk in; this is seriously the trippiest first experience I’ve ever had with a girl. She moved forward, guided my dick to her ass, and pushed hard against me. The excitement was too much, and I came within a minute of fucking her ass…to my surprise, she came when I started to. We collapsed on the bed and caught our breath. She took the condom off of me, and rubbed my dick. I was still pretty sensitive, but it felt good and the erection was back. Another condom on, and she got on top, slowly grinding on me. We were kissing, hands all over, grinding away, when she came again. Collapsed on the bed again, and passed out.

It continued when we woke up later that morning, with more oral, vaginal, and anal. We talked for what felt like hours after, where she told me her ex husband refused to do anal, and was upset that she was attracted to other women. My mind was blown.

We went to brunch, decided we should totally go camping and left for a camping trip that night.

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 hooked up somewhat regularly for the next couple years, as friends with benefits. I kinda started falling for her, but she wasn’t interested in a relationship… then some time later it was the other way around. I haven’t seen or heard from her since I met the woman who’s now my wife. She’s the one and only person from my past that I’d like to have sex with again (my wife is cool with it; she sleeps with an ex occasionally / we have an open relationship).

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Making new friends, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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? The mutual friend that introduced us, who thought it was great that we got along. I told my ex wife about it (we were good friends at the time), who was happy.

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? It happened at a time in my life where I was confused, unmotivated, lonely, and probably withdrawn from everything. Oh, and the sex was fucking awesome!

What was the WORST thing about this hookup? Having to interrupt it to get condoms.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It has, really for all the above. It wasn’t the first time I’d had casual sex, but it was the first time casual sex was something entirely more than just sex- it was freeing. It made me realize that casual sex can be more than just sex, without the extreme of being in a relationship. In other words, there was something between just a one night stand, and marriage. This hookup opened my eyes towards my own sexuality to the extent that I realized how sexually unhappy I’d been in previous relationships.

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? Casual sex doesn’t have to be something completely without feeling towards the partner. It can be an almost spiritual experience.

What do you think about the Casual Sex Project? I think it’s awesome!

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