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What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Copywriter
What’s your current relationship status? In a serious relationship (monogamous)
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)? 16
How many hookup stories have you here posted before? 4

My Potential Roommate

How long ago did this hookup happen? 8 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

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? I’d never met Lisa (not her real name) in person, even though I’d been talking to her for months. Earlier that year, I was looking for a short-term roommate to fill in the gap between long-term ones. Just a way to avoid paying too much in rent. What a nightmare. I went through 3 people in as many weeks, all male. The 3rd guy ended working out, thank god. But, in all this time, I’d been talking to Lisa who was interested in moving in permanently. I had a friend moving from back home in a few months, so this wasn’t something I was interested in doing. She was persistent, but I just got a weird vibe for a roommate.

That all being said, I had no idea what she looked like. Age, race, height, weight… all a mystery.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few months after my permanent roommate moved in, I got a text out of the blue from Lisa on a Saturday night. I don’t remember what it said, or why she was texting, but the apartment conversation was long over. Not wanting to keep it up, I decided I’d try to cut off contact with this stranger there and then. She asked something in the area of what I was up to, and I wrote back something like, “Not much. Just horny lol.” We’d never had a conversation like that before, so I thought this would end this. To my surprise, it didn’t. She was into it.

Our conversation progressed. It became clear this was happening, and tonight. My friend/roommate went to bed and I was headed for her place, except… we had tandem parking. And he was parked behind me. And he’s nosey. I couldn’t wake him up and be like, “Hey, let’s move cars, I’m gonna go fuck a stranger” because there’d be a million questions and a lot of talk amongst mutual friends. So, I had her come to my place. This was before Uber, so I had to pay for her cab and I didn’t have a ton of cash on me. Oh well.

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? Lisa finally showed up at my place. The only thing she’d told me is that A) she was African-American and B) she wore glasses. She’d asked if I was okay with both. I told her of course I was, not including the subtext that my dick DID NOT CARE. She got out of the cab, I opened the door to the building, and there she was, as advertised. Average weight, average looks, not disappointed. We get in the elevator and she looks me up and down and seemed pleased as well. As I opened the door to my apartment, she seemed more interested in the space than me (remember, we’d had a few conversations about it before). It took a second to get her into my bedroom, but then we went in and got comfortable.

We started to kiss, but I was impatient. I tried to make it heavier, but nothing. No frenching. My hands roamed her body, finding she had much nicer tits than her baggy clothes had let on. Eventually she got on top of me and took her bra off, and I was right, they were great. I sucked on them for a little bit, and she grabbed my cock. No oral, but I don’t think I wanted it (more on that below). I would say this was turning out to be a disappointment, but an out-of-the-blue text had gotten me this far, so it was hard to characterize it as that.

Finally, I flipped her on her back and took her panties off. I grabbed a condom, and slid it on. She wanted the TV off, but I wanted some white noise so as not to wake my roommate. Plus, I wanted to at least see who I was fucking. I won out and slid into her. She felt good… a little too good. This was my first time since my New Year’s Eve experience I wrote about in another story, so it had been months. I finished way quicker than I’d wanted to. She seemed disappointed. I wanted to keep going, but also it was really late and I had zero affection for this stranger. She called a cab and went home.

How sexually satisfying was this hookup? A little

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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 never talked to Lisa again. I don’t blame her, it was hardly the experience she’d hoped for. In retrospect, I think I was a little afraid of doing anything more than protected intercourse, since a friend of mine had recently told me he contracted HIV and I was super paranoid about it. Hence, no oral.

I would have definitely seen Lisa again. I don’t remember if I texted her again or not, but either way, I never saw or heard from her.

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? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? A little bit

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

How wanted was this hookup for your partner at the time? Somewhat

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 a friend I’d hooked up with a black girl once. Didn’t go into detail past that.

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

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? A little bit

Why do you regret this hookup? I feel like I could’ve had a more fun experience if I didn’t have so many mental factors. She had originally wanted me to go to her place, but the car thing was an issue. If only Uber had been invented then. I feel like maybe we could’ve had more fun if I wasn’t as concerned with my roommate hearing.

What was the BEST thing about this hookup? Had sex.

What was the WORST thing about this hookup? All the neurosis

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? That was the last time I’d consented to sex with someone who I had no idea of who they were. I only had one other partner after that wasn’t my current, long-term partner, and we had a good idea of who the other was. But that’s another story for another day.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? A little negative

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

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