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What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? ABC
What continent do you live on? North America
What country and/or city do you live in? San Francisco
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Engineer
What’s your current relationship status? In a serious relationship (monogamous)
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)? 15
How many hookup stories have you here posted before? 0

Weekend Visit…

How long ago did this hookup happen? 2 years

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 less than a month

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 Annie through another friend of mine. She was 32 at the time and lived in the Pacific Northwest and I was in California. A mutual friend thought it would be nice if Annie and I chatted and get to know one another since we were both single at the time. So we exchanged numbers and texted each other as friends. I had seen a picture of her and she looked ‘ok’. She was not my type really. A lot of makeup and physically average. She was short, had thick legs and zero cleavage. She did have great lips though. But I figured why not – can’t have enough friends right?

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After texting for a month or so, Annie decided she wanted to pay me a visit and I offered to show her around. I booked us a hotel room and planned to take her wine tasting and sight seeing, etc. A week or two before she was due to arrive, we made it a point to chat on the phone in person. It was a bit awkward at first but she seemed nice. Mind you our conversations never had a ‘sexual’ tone to it whatsoever. It was mainly to get to know one another as friends.

The big weekend finally arrived and I picked her up from the airport.
She looked pretty much like her picture. Short (5ft at most), long brown hair, flat chested and somewhat thick legs. I’m a leg man so it was somewhat of a disappointment. But I was determined to make the most of it and have a fun weekend anyway. The first thing we did was go up to Napa and hit up some wineries. Already at the first winery we were getting buzzed. She was opening up to me about her last relationship – how many years she was in it and how her ex cheated on her. She started to cry while telling me this. In my mind, I was thinking ‘uh oh’ – but chalked it up to the wine talking. The rest of the wine tasting went fine. But I did not feel any connection or attraction to her. In fact I was getting a bit annoyed with her. I had planned where to eat, etc and she made some backhanded remark about she and friends go to places that aren’t expensive but the food is still good, etc etc. The places I took her to weren’t even fancy or nice or trendy! She just seemed ungrateful, etc. The other annoying thing was that she took forever to get ready – even though I told her what time we needed to be at the restaurant.

I wasn’t sure how I was going to make it through the rest of the weekend with just me and her.
Luckily – as kind of a backup I had told my good friend and some other friends to meet up with me for drinks later on. That took some of the pressure off. My good friend (girl) got along great with Annie and drinks were flowing at the bar we were at. I found myself having a good time.

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? A little after midnight, Annie told me she wanted to go back to the hotel as she was super tired from the long day we had. I agreed and we went back to the hotel. Both of us definitely buzzed from the drinks we had during the night. We walked into our room and I started emptying my pockets on the desk.
I turned around and Annie was right there – she walked into me and started giving me a hug – her hands were roaming around my back and she started slowly kissing my neck. She looked up at me and her eyes said it all – she looked like she was in heat – her eyes were half opened and she just had that look of pure lust. I was taken aback, but went with it. We started making out – tongues probing – then she bit hard on my bottom lip. I’m like wtf?! I could taste the blood in my mouth but we kept going. We started undressing each other and I moved her to the bed. Her top and bra come off first, then I slid her thong down off her legs. She was clean shaven and I proceeded to go down on her. Her breathing was heavy and moans were growing louder. She tasted wonderful. I licked her pussy and put my fingers in and started fingering her. She couldn’t take it any more and told me to fuck her. I slipped off my boxer briefs and without thinking just plunged into her. She completely lost it – she was literally screaming and moaning at the top of her lungs. No one I had been with previously was this loud – I was worried about the rooms next to us for I was certain they could hear. We started in missionary and then I put her legs on my shoulders. “Oooh fuck, oooh fuck!” was what I heard – I wasn’t sure I could last that much longer and I pulled out to rest a bit. But she was insatiable – I flipped her on all fours and did her doggy. Then she rode me cowgirl and proceeded to grind herself into ecstasy. She rolled onto her back and I entered her again. I was pounding away when she told me she wanted me to choke her. I was like huh? She said it would heighten her orgasm, etc etc. I told her I knew why – I just wasn’t sure I could do it. She begged me – hard to turn down a girl you’re balls deep into – so I tried it. I grabbed her throat with my right hand and used my left to prop me up as I was thrusting into her. I started squeezing her throat but apparently it wasn’t hard enough for her – she moaned ‘harder!’. I squeezed more and her back started arching upwards – she was cumming again. I let go of her throat and I just marveled at the sight. I realized then that I hadn’t cum at all – it was almost like I had passed that point. The night was about pleasing her. We did fuck a few more times during the night but I was getting tired. I felt like I couldn’t keep up! We finally went to bed for much needed sleep.

The next morning, I felt her hand my cock and she was slowly trying to get it hard again.
We started making small talk about the previous night. I had never hooked up with anyone that quickly before really. She said the same – as her hand explored my rising cock. She said she wasn’t surprised we’d hook up – after all, we were sharing the same hotel room (2 beds mind you) so it was bound to happen. We got onto the subject of favorite things in bed and mine was blowjobs. I asked if she didn’t like giving BJs since she didn’t go down on me last night. She said she didn’t think about it and just wanted to fuck. As she was saying that, she slid down my body and rested her head on my belly and said “like this you mean?” then wrapped her lips around my cock and proceeded to start pumping with a quick pace with her hand and mouth moving up and down in unison. It felt good but her technique lacked sensuality. After a few minutes, she stopped and said let’s shower.

We jumped in the shower and started soaping each other up. Of course, since I was still hard we started fucking. I bent her over and started pounding her from behind. The echoes of her loud moans once again made me fearful of our neighbors! After a few minutes, she got up, turned around and knelt in front of me. She took my cock into her mouth, her little hand wrapped around my shaft trying to milk me. Seeing her gorgeous lips wrapped around my cock was such a turn on. I knew I wasn’t going to last very long. As her head bobbed up and down I could feel the cum amass – I told her I was about to cum. I expected her to just jack me off but she instead kept her mouth on it. The excitement was too much and I exploded into her mouth. She didn’t miss a beat and kept going. It was like something out of a porn movie. I could see cum slowly oozing out the side of her mouth, down her chin and onto the tub as she didn’t swallow all of it. It was amazing to watch….

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? The rest of the weekend was spent much the same. During the day we’d go sightseeing, then have dinner and at night finish with sex. When it was time to go home, she started crying. I wasn’t sure why. I began to wonder if she regretted sleeping with me. But she said she’s just emotional. We said our goodbyes at the airport. I really wasn’t sure if I was going to see her again. I didn’t have an overwhelming feeling of wanting to. I was going to chalk it up as a great weekend experience.

We continued texting here and there, but nothing sexual. Just your friendly hellos, how are things, etc.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? I told my brother and a few friends eventually.

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

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? Somewhat

Why do you regret this hookup? We didn’t use any protection during our sex sessions.
I usually finished in her mouth or on her.

What was the BEST thing about this hookup? Experiencing the kind of sex she liked. Loud and rough.

What was the WORST thing about this hookup? About a month later, Annie texted me saying she had missed her period.
I called her and she was in tears, saying she was scared. I told her to get a pregnancy test.
She also made an appointment with her doctor to confirm. My mind was racing. I did not want another child – let alone with her. I already had a son from a previous marriage and I was in the middle of planning his bday party. I was stressed. Annie called me and confirmed she was pregnant. After much back and forth and discussions she decided it was best that she abort the pregnancy. I was relieved but sad at the same time. Annie and I haven’t talked since she told she went through with the abortion…..

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. It made me realize I was missing out on ‘casual sex’.
That if two adults were willing, they could have sex without having to be committed to a relationship.
Because this was somewhat ingrained in my head, I felt I had bypassed some opportunities where I could’ve gotten laid when I was younger but was worried about falling into a relationship with the person.

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

All things considered, how NEGATIVE was this experience? Somewhat 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? Perhaps one day – casual sex among friends or people, in general, would be as common as going out to a movie.

What do you think about the Casual Sex Project? Glad I stumbled onto this site.
It’s opened my eyes more and made me realize there are women who just enjoy sex, no strings attached necessarily. I just need to find them! =)

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