A Night To Remember

by ChubbyChaser

What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Very
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

A Night To Remember

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 don’t actually remember her face that well. She was okay-looking, I guess. She wasn’t wearing any makeup and she was wearing glasses. She was white, thicker build (like I like it), brunette, and pale. I remember she had big tits, thick legs, and a big ass, and even though she was wearing kind of plain clothes (sweats and a sweatshirt), she was hot somehow. We met when I responded to her ad on Craigslist about looking for someone who liked BBWs, and I came right over from my dorm, so I didn’t know who she was. I met her at her place, where we snuck down to her room, fucked three times, then I left. I guess if I could find her again, I would love to meet up for another fuck session. I’m pretty sure her name is Michelle.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at her place late at night, when her family was asleep. A girl broke my heart that year, so I was just looking to feel anything I could, by which I mean anything that was sexual in nature, you know. And I posted a lot of ads on CL, looking for some fun…at that time in my life, and still to this day, I had a thing for BBWs. So I looked everywhere I could for one on Craigslist, but each time, they flaked, were fakes, or didn’t respond. Until I posted one ad, and then erased it a few weeks later. But some girl saw it and posted her own ad about it, looking for whoever posted it, and if they wanted to meet up. Naturally, I replied quick as lightning, told her it was me who posted that (I did), and that just like the ad said, I would love to give her a massage, with oils and all that hot stuff. I left my dorm late that night and headed out to meet her. As I was stopping by for condoms, I got a text from her: she said her family was asleep, so we’d have to be really quiet. I texted her back, telling her that was up to 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? So I get there to her place: a one-story near the interstate, late at night, nobody out, and I meet her on the porch. She’s wearing sweats and no makeup, and I’m wearing a pair of corduroys and a sweater. She leads me down to her place, tiptoe down the stairs as quiet as we can, and we’re in her area. It’s a basement/room, with a bunch of shelves, a ratty old rug, and a glowing aquarium. At first I think we’re sticking to the plan, and I’m massaging her, which to be honest, I really wanted to do. Call it foreplay, but it would have been fun to get her naked, oily, relaxed, and then to get to the good stuff…uh, better stuff. But nope, she had other plans. She leads me to a closed door in a soft, seductive voice, and of course I head over. From there, it’s a blur as to how it started: a steamy, dark blur, actually. What I do remember was that her bed was near the window, and we got naked: I’m pretty sure she unbuttoned my shirt and took off my sweater. I took my own pants off, I remember, slipped on a condom, and came down to her on the bed. We started making out at first, and then I slipped myself into her.
Now, before this, I didn’t have too much experience with girls and sex, so I stupidly asked her if it was in yet, but I could kind of tell it was. As we fucked, I kissed her vigorously, licked her tits, squeezed her ass and tits, and basically unleashed my repressed sexual energy. I then proceeded to do something I never had before, and that was to eat her out. I’d never eaten a pussy before, and didn’t know what to expect, so it was quite a surprise. First, I pulled myself out of her, then licked her tits, belly, waist, and then made my way down to her hairy little cunt. It was like I was programmed to know how to do it, because she was moaning in some kind of delight, and even though it smelled like weed down there somehow (and something overcooked, I guess), I couldn’t stop until she asked me to get back inside her. I tried getting anal, but she was firm about it: no. I asked her what if I tried it anyway, and she said she’d slap me. Now of course that kind of talk revs up some men, so I hit her with a one liner of my own: “go ahead”, in a seductive voice. Then she said if I tried it, she’d stop and call her landlord (her family)…that sent me on my best behavior. So we got back to vaginal, and it was hot and all, we then tried an ass job, a titty fuck, and some other fun things. I never cared much for blowjobs, so that wasn’t an issue. When she moaned/whispered that she was going to cum, I told her coolly “not yet”, which pleased her to hear and we went on, harder and rougher than before. At that point, we stopped for a breather, into which I slipped off the condom (since it was hot in that thing, and uncomfortably tight), and she was panting like she’d run a marathon. I asked her if she wanted to go again, and she asked me if I was clean.I told her “my thoughts aren’t”, and she laughed a bit, told me she was as well, and we went again, hard as the first time, with no condom, the way nature intended.
And I have to say, without a condom is the best kind…that is, of course, if you’re absolutely sure that your partner is clean. I was…or at least, I was too blinded by arousal to care. No, she was definitely clean. So we went at it again, groping, squeezing, twisting, like beasts in a passion. As time went on, we both got so tired, we just lay there, and I covered her a bit with the blanket (and myself, since I’ve always thought that was sexy), and we just played with each other there: sweaty and tired. She told me something I wasn’t expecting to hear, but was pleased to hear anyway. I was the best sex she’d had in years. She was divorced, I think. Not too long after, she asked me to leave since she had work soon (she worked in a convenience store, I think), but I asked her if she’d want to keep up the fun just a little longer (since I hadn’t cum yet), and five minutes later, that became a bit firmer as she said she’d call her landlord if I stayed and didn’t leave…not a threat, really, I could tell. But sex or not, I know when not to overstay my welcome. So that was that.
We got dressed, I rinsed my mouth, and told her I had a great time and that we might even make it a regular thing. She didn’t seem to think about that too much as I kissed her goodbye and went off into the night. That night, I went back to my dorm, locked the door, jerked off, and came, finally.
That was the best sex I’ve had in my life…thus far.

How sexually satisfying was this hookup? Very

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

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? After that night, I went to class the next day and got a message from another girl asking about the ad. I decided that enough premarital sex was enough, and that I had a change of heart and wouldn’t be meeting 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, Attraction to partner(s), Learning new things, experimenting

How intoxicated were you? Not at all (no alcohol or drugs)

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? 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 spoke to my church leaders, my sister, a few trusted friends, and I think that’s it.

Why do you regret this hookup? I don’t really mean to make casual sex a part of my life, but I lapsed. I mean, I don’t regret the pleasure, but I regret going against my faith for a bit of sex.

What was the BEST thing about this hookup? EVERYTHING. Sex is awesome. I mean, premarital is sinful, but it feels amazing.

What was the WORST thing about this hookup? No anal. I’ve never gotten to try anal on a girl before.

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

Anything else you want to add about this hookup? I can’t forget how wonderful it was.

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? I now think of casual sex as something really hard to come by, and I don’t really intend to try it. Now, I’m just gonna save what’s left of me for marriage.

What do you think about the Casual Sex Project? I’m just glad there’s someone who wanted to hear my story.

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