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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? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Server
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Generally repressed. My mind is still very free.
How many sexual partners have you had in your life (including oral sex)? 20+ (without doing the math)
How many hookup stories have you here posted before? 0

TEEN SEX COMEDY

How long ago did this hookup happen? Year 2001

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? 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? C was a ginger, about 5’5” and slender, had squinty eyes and wore glasses, flat booty, pretty nice tits. Super chill girl. Very smart. We were friends even though she was a grade behind me. She was 17, I was 18. We were in some classes together, and I used to check her out and fantasize about her, though I fantasized a lot about many men and women at that time. I lost my pussy virginity (I had been jerking and sucking off guys long before that) to her best friend, M, who wanted to be in a relationship with me. I was going to be off to college soon, and I was looking for something a little more casual so I broke it off with M, which was difficult because she was pretty emotionally attached to me. My home life was tumultuous and chaotic. I became an escape artist. And soon I found myself hanging out with C on a regular basis. She lived three blocks from me and loved to smoke weed which was pretty much all I ever wanted to do at that point in my life, aside from fuck. Eventually, we started to do both in combination. And she was cool to just be friends. Pretty ideal situation.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had been fucking for at least a few months. Instigated by me. She was betraying her best friend by fucking me and we both knew it. But we did it anyway. We had lots of fun, in an awkward teen way. We had pretty limited knowledge of sex at that point, so looking back the sex we had was pretty vanilla, and I kinda regret that I didn’t try more things with her. But it was just fun being naked with a girl and touching each other. I had had more than a few experiences with guys, and though I tried to keep it DL, eventually everyone knew and most people assumed I was gay. Which made experimenting with girls exceedingly difficult. I was bi-sexual, of course, and aware of it but back then people, especially kids, didn’t really buy into the notion of bi-sexuality. Everyone thought I was in denial: the men I jerked off, the women I tried to persuade to touch my cock, my friends, my parents, etc. Annoying to say the least. C never asked me about that. Maybe she didn’t know, maybe she didn’t care. Either way, I appreciated it. With her, I felt freed from other people’s perception of me, the rumors, the expectations, the reputation etc.

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? On one particular occasion, I went over to C’s apartment that she shared with her mom. It was a weeknight in the summer after we had both gotten off of work. Her mom was gonna be spending the night at her boyfriend’s place so we’d have the place to ourselves. C and I weren’t official, and as far as I knew, her mom had no idea we were fucking. I was just a friend who would come over to smoke pot. When I arrived we most likely smoked a blunt of the shwag her mom kept in the drawer of her nightstand. I can’t really remember what we did since it was like 18 years ago, but this being the Casual Sex Project, which leans toward the ultra-descriptive, I’ll invent for you a little play-by-play. C leads me to her bedroom, we strip along the way. I’m high and already hard. We make out a little standing up, she’s stroking my average-sized cock, I’m feeling her tits and reaching down to finger her clit. I throw her on the bed, she’s got her legs spread. I dive down and put my face in her pussy. I suck long and deep. I’m getting her hips bucking. She pulls me up and says “fuck me.” I slide my dick in her, missionary. She’s very wet. We thrust and pump building intensity. At some point, she wants it from behind. I tell her she has to suck me first. I’m on my knees on the bed with my cock pointed at her. She springs up on all fours and takes me in her mouth sucking. I love how this looks, but I have no intention of coming this way and it’s not long before I flip her around and enter her from behind. She’s on all fours, pussy in the air, she’s looking back at me smiling. I give her ass a smack and she pouts and writhes, waving her trimmed pussy at me. It’s pink and glistening. I’m on one knee with my other leg bent and foot on the bed, and we’re fucking. Her asshole is on display, an eye winking at me. I love this view of her asshole and her pussy right below and my cock going in and out and my pubic hair and stomach and her back stretched out before me and her red hair in my hand as I’m pulling her head toward me and her voice, the moans, the expletives, her tits swinging, my finger rubbing her clit back and forth and the sound of the front door slamming and keys jingling.

And now we’re both on our feet and she’s saying I have to hide. She runs down the hall to the bathroom and jumps in the shower. I’m naked and erect and her mom’s coming down the hall to the kitchen. She stops at the bathroom, knocks on the door and greets C. I’m throwing on my pants, can’t find my shirt or shoes, and throwing my back up against the wall out of view of Mom whose passing the bedroom down the hall to the kitchen. There’s no way out of here that I can see except the bedroom window. It’s three stories up, long way down, but there’s no other option. I’m sitting on the ledge with my feet out the window contemplating how to do this, and I hear them coming towards the bedroom. And now I’m hanging by my fingertips from the window ledge as C and her mom are arguing about something. They leave the room and now I’m swinging my leg toward a drainpipe next to me, reaching over to grab it, letting go of the window ledge and now I’m clinging to the drainpipe, which won’t take my weight very long. I slide slowly down the pipe to the floor below and reach over to the patio to my left. I let go of the pipe and my body slams up against the patio railing. It makes a deep loud thud and rattles the windows. I hoist myself up and over the railing and on to the patio. I very delicately open the door to the stairwell and descend to the back door and I’m out. I sneak through the back yard, around the house down the driveway and to the street, straight back to my house. No shirt, no shoes. I light a cigarette, inhale exhale, I’m electric.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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 call her later. Mom was clueless, hilariously. C came and picked me up later in her Oldsmobile, we parked on a chill street and fucked in the back seat. I’m pretty tall so it was awkward but still enjoyable.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To feel better about myself, To feel more desirable, To feel more confident, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Marijuana, hashish

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

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

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

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 some friends at the time. Generally, the reaction was positive. People found it to be amusing. But haven’t told it in years.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? the fun awkward sweaty young sex part. Two kids learning how to enjoy each other’s bodies.

What was the WORST thing about this hookup? I got a few scrapes and bruises climbing down that building.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This relationship showed me that I really enjoyed having sex with women. I hadn’t had much before her, and everyone thinking I was gay had me second-guessing myself. When you’re a teen you care very deeply what people think of you. Twenty years later, I’m much more comfortable with myself, I give less of a fuck. I’m married and my wife knows me and loves me. Times have changed a little bit as well.

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

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

Anything else you want to add about this hookup? I think about C a lot. She was a good sex partner. We stopped fucking after I left for college with one exception, in which she confessed that she missed me inside her. Other than that if she was ever emotional over our relationship she never let me see it, we remained friends for years.

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 interesting. I feel like casual sex for me is a weird concept. If I have sex with you and I don’t like it, I’ll stop having sex with you. If I like it, I’ll want more of it, and then boom you’re in a relationship. I don’t know. But in general I believe that more sex and honest communication about desire is a good thing.

What do you think about the Casual Sex Project? It’s fun and very arousing to read other people’s stories, though many of the stories here smack of fabrication. I wish more women would share.

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