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What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? South Florida, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
What’s your current relationship status? Engaged/Married (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)? 50 for sex, 55-60 counting oral
How many hookup stories have you here posted before? Quite a few now

3 Girls I’d Never Met Drove 8 Hours for Me

How long ago did this hookup happen? Spring College Semester of 2004

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

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? There’s quite a few people in this story, so I’ll give the basics and then provide some more details.

Firstly, there’s myself and my college roommate at the time. We’ll call him Jack. We were both 19 years old. Jack was about 6 feet tall, thin, had shaggy brown hair, and was in a band. He was pretty shy, but intelligent and funny if you got him to open up. I was 6’3″, about 200 lbs, blonde hair, blue eyes, and had a swimmer’s build.

Then, there’s three girls. Two of the girls (“Jenna” and “Jessica”) were sisters. Both of them were Hispanic (Cuban), had mocha colored skin, full lips, were around 5’2″, and had absolutely enormous breasts. Jenna’s boobs were nothing less than 34 DD and her sister Jessica’s were even bigger- I’d guess around 36 FF. Their family was absolutely blessed when it came to giant breasts; but, neither of them had much ass to speak off. Jenna was a surfer, so very toned and athletic. Her sister was a bit chubbier, but by no means was she fat. The third girl was their mutual family friend. I can’t remember her name, but I do recall that it was rather exotic sounding, so we’ll pretend it was Verita. This poor girl was slightly overweight, incredibly ugly, and not a major part of the story.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Before Facebook, and just before MySpace really took off, meeting strangers on the Internet was somewhat difficult unless you were willing to use a website that charged money. To circumvent cost issues, people would use the rating site, “Hot or Not,” to post their pictures and hide their contact information in the photo. This is how Jenna first got into contact with me.

I was a freshman at FSU and Jenna was 8 hours south near my hometown in southern Florida. She saw my hidden email address in my photo, we began exchanging messages, and within two weeks, she was agreeing to come visit me. My ego was feeling super inflated for convincing a girl I’d never met to drive 8 hours and stay with me in my dorm room. She told me she was going to bring two of her friends for safety’s sake (who wound up being her sister and the ugly friend).

My roommate was desperately hoping that either the sister or friend would be hot so that he’d have someone to hook up with while Jenna and I did our thing. “Our thing” wasn’t explicitly stated, but I was very confident that I was going to be having sex the coming weekend (as long as she looked like her pictures).

Anyway, they arrive on a Friday evening while I’m away at class, so I arrange for my roommate to meet them downstairs, get a feel for them, and sneak them up to our dorm (we’re not allowed to have visitors stay the night, let alone females). When I ask him (via text) about the girls’ appearances, I just keep getting vague responses like “dude…” “dude!” so I’m not really sure what to expect.

When I finally make it up to my room, I meet all three girls. The sheer, massive size of Jessica’s tits was impossible not to notice, but I was supremely happy with my pre-pairing with Jenna since I found her to be much prettier, have a better body overall, and an incredible smile. I’m a sucker for a nice smile.

The five of us got along cordially; we never had an awkward moment. There was no alcohol involved, but there was a lot of laughing, joking, and getting to know each other. At the end of the night, it was time to figure out the sleeping arrangements. Naturally, Jenna was welcome to share my bed (which she happily agreed to), while her massively chest-blessed sister was invited to sleep in my roommate’s bed with him. Keep in mind that our dorm, like most dorms, was a small, single room. There wasn’t a lot of space. The poor ugly friend was given a pillow and a blanket and had to sleep on the floor between us.

So everyone climbs into their respective sleeping arrangements, and within minutes, I’m putting the moves on Jenna.

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? I wasn’t sure what Jenna had told her sister or friend about me before driving up here, so we had kept our interactions platonic throughout the day. By the time we got into bed together, there was so much sexual tension that we immediately had our hands all over each other. We began by kissing, attempting to keep the smacking of our lips and tongue to a minimum. Both Jenna and I have pretty full lips, so those kisses were some of the softest I’ve ever had the pleasure of experiencing.

It wasn’t long before I was pulling her shirt (no bra) up over her breasts, and driving myself absolutely wild at the enormous size of them. They were, at the time, the largest breasts I had ever felt in my young life. I distinctly remember marveling at how I needed both hands to fully cup just one of them. It was right around this point in time where we were no longer able to be as quiet as we had hoped. I had begun to finger her and she started letting out these quiet little moans. I would put my finger over her lips or kiss her in an attempt to quiet her, but it just wasn’t working. The ugly friend was giggling on the floor. We ignored her and kept exploring each others bodies.

Finally, I climbed on top of Jenna. She was the first girl I fucked who kept some hair downstairs; so that was new for me. All of the usual sexual nuances took place: she gasped when I entered her, her flat stomach arched and bent in rhythm with my thrusts, her nails scratched my back and head, and she breathed deeply and moaned into my ear. My eyes had adjusted to the darkness by this point, so I remember spending a lot of time staring at her tits and watching them bounce up and down at the same time with each thrust.

My bed springs were now squeaking like crazy, but we didn’t care. It was obvious at this point that everyone in the room knew we were fucking and there was no longer any point trying to hide it. The only reason Jenna continued to try and muffle her moans was because her sister was laying down next to us just ten feet away.

I’m not sure how long we had sex for, but after some amount of time, Jenna began to have an orgasm. I wasn’t sure if it was her “style” or if it was because she was trying to stay quiet, but her orgasm’s moans sounded like they were coming from the depths of her soul. When she finished, I pulled out (not having had an orgasm of my own), and we kissed a bit before falling asleep.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

Did your partner have an orgasm? Yes, one

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 next morning, the ugly girl in the middle was giggling the entire morning. She made jokes about how everyone was getting some besides her and both Jenna and I were taken by surprise. Jenna took her sister aside and interrogated her. As it turns out, her sister Jessica gave her virginity to my roommate!

After Jenna gave me that information, I had to ask my roommate about it. I needed to know what those tits were like. But when I asked him, his response stuck with me forever. He told me about how he had started to put the moves on Jessica soon after Jenna and I started to have sex. He said that she opened her legs for him, but he only lasted less than a minute. I remember him telling me, “I was trying so hard to last longer, but I kept hearing Jenna moan and…and it was just too much for me.”

Jenna and I remained fuck-buddies for the next 5 years. We wound up developing a pretty good friendship, too. There’s quite a few more stories that involve her, which I’ll be sure to contribute in the future.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? 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? Well, I talked about it with my roommate, but there wasn’t much to tell since he was there and heard all of it first-hand.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The best thing about the hookup was unquestionably the fact that a girl drove 8 hours just to spend the weekend with me having sex. And her enormous breasts.

What was the WORST thing about this hookup? The worst thing about the hookup was having to pretend that nothing was happening since there were 3 other people in the room.

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

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

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

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