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What’s your gender? Man
How old are you? 20
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Chicago
Highest education received: Some college (currently in college)
What’s your occupation? Student
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
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? 2

18 Hour Sex Binge

How long ago did this hookup happen? A few weeks

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? Jennifer was 30 years old. So ten years older than me. Courtney was a year younger. I met Jennifer at a bar that recently opened in my neighborhood. I have a fake ID and have never once been questioned and sometimes am not carded since I look a little older. Jennifer was a brown-haired, freckled woman who was recently separated from her husband. Courtney, who’ll I’ll only talk about a little, was black, tall-ish, very into fashion and makeup, etc. She and I had nothing in common except the willingness to fuck each other. Jennifer was much cooler.

I had already been seeing both of them simultaneously. Jennifer I’d just met at the bar a week before. She had been seeing a movie with a (male) friend who I learned wasn’t her boyfriend from talking with her. So I made my move. We went back to her apartment, nearby and in the same neighborhood as me, had sex twice and spent the night. She learned that I was ten years younger and seemed to think it was kind of odd/funny but was okay with it. What she didn’t know, and wouldn’t, was that the previous night I’d banged Courtney at her dorm. Courtney I’d met online a week prior. I’ve had multiple girls at the same time before, but never with such an age discrepancy, which I thought was kind of awesome.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The second weekend of Jennifer: I’d made plans to hang out with her on Saturday and Courtney on Sunday. So Jennifer and I went to see a movie, came back to her place, listened to the Beatles on vinyl for a little while and talked for a bit. I’d already kissed her when I first saw her and held her hand throughout most of the movie so she knew what I wanted and I knew she wanted it too. At some point while listening to music on the couch I leaned in and we started making out. I felt her skin under her shirt and slid my hand up to her bra strap. Just FYI, I can unhook single-strap bras pretty quickly but it seems like most of you ladies are wearing double-straps with velcro these days and those are a little tricker. But I got it unfastened. She shook it off. I felt her tits and french kissed her. She led us to her bedroom.

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? We got each other’s clothes off and lay on her bed and I thought about what the most thrilling way would be to go down on her (which I’d already done once, the week prior). I told her I had an idea. She asked what and I told her to sit on my face. She thought it was a good idea. I lay on her pillows and she straddled my face and I swiped my tongue sideways across her vulva until it had blossomed open pretty good and then I moved my index finger inside her, below my chin, and rubbed while I licked. She moaned and grabbed the back of my head with her hand, pushing my face deeper in to her. My chin got damp and my index and middle finger got wet all the way down to the knuckles and she had this rapid series of spasms that made her thighs buck my forehead and her body to convulse upward. And once this happened I got a view of her messy wet vagina just hovering over me and thought for a moment of my ex girlfriend, who had sat on my face a year earlier and whose thighs did not feel as satisfying when they caved against my head.

I’ll be honest, my specific goal for this weekend was to bury my face in pussy as much as possible. So I’ll say that yeah, we had sex right after, but now I’ll skip to the early morning when we woke up and got busy again, and I ate her out again.

This second time I was under her sheets, my feet sticking out from the back of her sheets, the sunlight streaming in and illuminating her entire body and I was down there, my neck craned in a sort of uncomfortable position. But at least I was getting this older woman wet as fuck, so I wasn’t going to complain. I did the same thing as before, licking her side to side and fingering her, but this time with just one finger. She was doing the same thing, tugging on my head with her hand and making moans and gasps that were sort of muffled under her covers. It’s insane how expansive a vagina can get during cunnilingus; Jennifer was expanding on my mouth. My finger began to feel so wet I wondered if she was leaking on to her sheets. My tongue made squishy noises against her vulva. Then came her pleasure-seizure thing again. Thighs over my forehead, grazing my ears, body moves back, I stared at her eaten-out vagina for several seconds while wiping my finger on the sheets. I came up from the sheets and looked her in the eyes and told her I wanted really badly to do her without a condom. She looked uncomfortable and didn’t know what to say. I said that okay, I was getting a condom. She said, “Yeah…” and laughed.

When we fucked that time, I lay on top of her for a bit and told her to look straight into my eyes. She had these amazing bright blue eyes. We stared at each other, wide eyed, and she whispered, “Fuck me.” I was getting tired but I moved faster. She said, “Harder, harder…” I went harder.

We had breakfast at her place and I left. I’d hardly gotten any sleep.

Later that same day, I headed over to Courtney’s. I knew as soon as I walked in the door that this would be our last time. She was in a kind of sassy mood. I got my watch, which I’d left at her place last time. We left the building and had a picnic. We talked about this and that and she announced at one point that she’d already decided we weren’t going to have sex. I thought, bullshit. But I played along for a little bit. We went back to her apartment, watched some T.V, she loosened up a little and we joked around. I put my hand on her shoulder at one point and didn’t take it off. I moved down to her leg. She said after a moment, “Okay, you can touch my vagina if you want.”

The next image I have is of me moving in towards her vagina, which I’d already fingered for many minutes, and seeing this thin white streak of foam oozing out of her lips. Some guys would stop immediately but I was horny and did not have any common sense so I kept going. I ate her out for a few minutes at least. Courtney didn’t do the thigh-bucking thing, which was a shame. She made these light whimpers throughout. I pulled away from her, put on a condom–out of total hubris/confidence, I’d bought a huge box–and entered her. I was fucking her diagonally on her bed. I was going lightly for a bit and asked her on a scale of 1 to 5 how it felt. Still kind of sassy, she said 3. I pushed in further and lay right on top of her and started moving faster and she said 5. Despite feeling kind of exhausted already I kept going and when I came it was fucking amazing for some reason. More than a five. I shut my eyes and buried my face in her pillow. After, she remarked to me in teasing sort of way, “Aw, did you just have an orgasm?” I left shortly after.

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? I found out that having this much sex in a fairly short time frame is pretty exhausting. Also, it is technically possible to overdose on pussy. The next day I woke up and my neck felt stiff from so much cunnilingus. Not only that, but I had a sore throat for some reason. It was only later when I read that yeast infections can be transferred and turn into a new infection that I remembered the white stain on Courtney’s pussy and thought, “Oh…” She texted me saying she had a great time, but I’d already made up my mind not to contact her again.

Jennifer and I, on the other hand, continued to talk but she said that she was sick and couldn’t hang out the next weekend. The following week she texted me saying that she’d thought about it and realized she wasn’t ready to start dating. She’d ended a relationship earlier in the winter and it was hard for her. I told I didn’t think we had been dating. I tried to convince her otherwise, but eventually gave up. Haven’t gotten laid since.

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, Attraction to partner(s), Learning new things, experimenting, To feel better about myself, Power / Dominance

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A few friends. There wasn’t much of a reaction. I didn’t go in to the details I’ve gone into here. In any case, it isn’t a big deal.

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

Did you get emotionally hurt as a result of this hookup? A little bit

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Eating Jennifer out.

What was the WORST thing about this hookup? The possible yeast infection

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m in a phase where I just want to have as much casual sex as possible. That’s honestly how I feel. I know that I’m attractive to certain girls and I know what to do if the opportunity presents itself. At the same time, I think maybe both Jennifer and Courtney saw me as a casual fling only and realized that I wasn’t really looking for any kind of relationship, just sex. Maybe Jennifer at least was not okay with that.

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

All things considered, how NEGATIVE was this experience? A little 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? It’s fun. Everybody likes it. If you feel bad about it, it’s more because of some moral afterthought rather than anything that happened during the act.

What do you think about the Casual Sex Project? Right on.

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

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