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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? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Senior manager
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 36
How many hookup stories have you here posted before? 2

Thinking With The Wrong Organ

How long ago did this hookup happen? Last summer

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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? I met her at a singles event two years earlier. We went on a date thereafter. She was pretty, tall, and bigger boned, but with a fit build. I wasn’t interested in her romantically because her life wasn’t going anywhere. She was working at a dead end job and she didn’t seem to offer anything stimulating to a potential relationship plus any guy could tell that she just wanted to get married. Still, she was friendly and nice. We went out for lunch sometimes. I guess I kept in touch on the chance that it could lead to a hook up, however, I could also tell that she was the type that would get possessive and go “nuclear” if she was used for a one night stand. That was what held me back somewhat.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I’ve been offering to take her kayaking for some time. We eventually met up to do it on a Saturday afternoon. I picked her up at her condo. She was wearing a body-clinging tank top and very short athletic shorts. It showed off her legs and strong thighs. I could have fucked her right there.
She said she was tired from not sleeping the night before. She shared the condo unit with her younger brother and apparently he took his girlfriend home and they had sex all night. The girlfriend’s loud moans kept her awake. She was complaining that his brother’s girlfriend is a slut and I asked why. She said that she left her “cum-fuck-me-heels” on the shoe rack and was clearly looking to fuck last night. I was getting a hard-on from hearing all of this!

As we paddled around, she was telling me how she found a vibrator ring under her brother’s bed (there’s that red flag about stalking!). I teased her, asking why she was sneaking around in her brother’s bedroom. I teased and flirted with her by saying she’s jealous, because she wants to be fucked like that. Deep down, I think this was true! She had not eaten all day, so after our kayaking excursion, I suggested to take her for dinner which she gladly accepted. We had sushi at a restaurant near her condo. It was fun and we had a lot of wine. I walked her back to her condo and she invited me in. We were in the kitchen and she was pouring water for both of us. There was a slightly drunk, hot, sweaty body in front of me so I just reached out, pulled her in, and kissed her.

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? She did not pull away as I kissed her, she actually started getting into it. We went into her bedroom and continued to kiss and make out on her bed. I pulled off our clothes. I continued to kiss her and started sucking and biting her tits. I licked her pussy and then I started finger fucking her. I didn’t bring any condoms, but she knew where her brother kept a box and got some! I thought that was crazy that she was checking his things out!

We started sex in a slow, missionary position with me looking into her eyes. I figured she needed that kind of seduction to get into it. She was moaning quietly and then we switched to doggy style. She was moaning a lot louder as she got more uninhibited. Then we could hear her brother coming in the front door! She froze and stopped making any noises. I leaned in to her and whispered, now it’s our turn to keep him up at night. She said: “shit what are we going to do?” I said: “we’re going to keep fucking,” and started up thrusting into her again in doggy position. She remained quiet as I fucked her, but as I started to pound into her harder and faster, she started moaning again, and it got rather loud with time.

We switched between doggy, cowgirl, and missionary. I fucked as many times as I could that night, because I wasn’t sure if I could get this chance again with her. In between rounds, I kept her pleased by finger fucking her and with oral sex. I ejaculated into her three times that night. As anticipated, we made it a long, loud night.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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 slept over and let myself out early the next day. We continued “dating”, but all the next times, she stayed over at my place for the sex. After about a month, she asked about where the “relationship” was going. I told her it was good, but I’m not ready for serious long term. She was extremely upset. We broke up then, but she kept emailing me and texting me. She was also stalking me with “likes” on my Facebook. That’s when I started to lay low, and that was also when I pretty much stopped using Facebook.

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

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

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

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Told no one.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Very

Do you regret this hookup? A little bit

Why do you regret this hookup? I was not interested in her romantically, but I knew she was only interested in a long term relationship leading to marriage. Her reaction to the short fling was entirely predictable. I knew what I was signing up for, but I was horny at the time, and all that sex talk got the better of me. I was responding to my dick.

What was the BEST thing about this hookup? I had great sex and it led to a month of good sex.

What was the WORST thing about this hookup? She got hurt and she was very upset and angry with me.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I used to only be attracted to slim, attractive women. She was not heavy, but she was certainly not slim. More like average to athletic. Surprisingly, fucking that kind of body was great. In fact, sex with beautiful slim women has often not been as satisfying. I have since found that women with average builds and shorter women have more passionate sex with me than beautiful, slim women. I don’t mean to generalize, but that’s my latest experience.

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? I am happy to learn that she has since gotten engaged to some older finance guy. He’s not that attractive in my opinion and out of her league in terms of looks, but I can see he is also desperate to get married. I’m glad she found someone.

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