Bouncing from Friend to Friend (Pt. 1 of 4)



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, 55-60 if counting oral
How many hookup stories have you here posted before? More than a dozen, although only 3 were approved and went live (so far)

Bouncing from Friend to Friend (Pt. 1 of 4)

How long ago did this hookup happen? about 12 years ago

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? 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? Four girls who were friends with one another passed me back and forth between each other during my sophomore year of college. It all started with S.

S. dated one of my really good friends when we were in high school. She had gone to a different school than the two of us, so I didn’t see her often. But we were polite to one another and there wasn’t much there. She was quite thin, had small boobs and a small butt, but a very beautiful face. She had dark brown hair, green eyes, fair skin with lots of freckles. She did a bit of modeling. She was really into track and soccer, and thus had a very athletic, toned (albeit thin) frame.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? During my sophomore year in college, I randomly ran into S. on campus. We recognized each other, chatted, and exchanged contact information to “hang out sometime.” After some online conversations, I found out she had lost her virginity to my friend back home, never slept with anyone except him, but had broken up with him just before leaving to go to college. She left him heartbroken. Immediately, I began to fantasize about fucking her. My friend and I had had a bit of a falling out our senior year, so the idea of fucking his ex-girlfriend- whom he was still in love with- enticed my ego.

S. and I eventually started to go to parties together, as friends, since she was a “one of the guys” kind of girl. However, one day when talking, the conversation became sexual. She was telling me how she was always super paranoid about getting pregnant, always made my friend wear a condom when they were dating, etc etc. I made a pass at her and, to my surprise, she responded positively. Suddenly we were making plans to have sex, no strings attached the next time we got together and went to a party. She made it seem like what we were doing was extremely taboo. Having only been with one guy, she thought she was living on the edge and being naughty just by making these plans.

The next time we went to the party, S. was drinking a bit more than usual. You could tell she was nervous. When we left the party, we drove to her house. I was acting normal, but she was acting pretty nervous and awkward. I was loving the fact that I was having this effect on 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? When we made our way to her bedroom, S. turned around to look at me and said something awkward like, “Okay, so do you want to start?” It was definitely a potential mood killer, but I didn’t let it get in my way. I pulled her close, began kissing her, and she (rigidly at first) slowly got into it. Within a few minutes, S. was finally feeling more comfortable and apparently had convinced herself that it wasn’t as big of a deal as she was making it out to be in her head.

We each stood there, taking our own clothes off, and then re-embraced to continue kissing. There’s nothing quite like that first time your bare cock presses into a girl’s stomach and you feel her tits press against you for the first time.

Anyway, I was trying to be slick and intentionally “forgot” to bring a condom. I knew from previous experience that I was going to need a Magnum XL and I assumed she was only going to have the regular sized ones. I hoped that this would allow me to fuck her bare, but I underestimated her paranoia for getting pregnant.

S. made me wear the regular sized condom. It was awful. It restricted blood flow, prevented me from getting more than about 60% hard, and made my dick feel void of sensation. I shoved it into her regardless, not wanting to miss out on getting laid, but the sex was sub-par. S. was moaning a bit, but I could tell it wasn’t great. After about 15 minutes of sub-par sex, I drunkenly decided I was going to try and remove the condom without S. noticing. I continued thrusting, but every time my dick came out, I started to unroll the condom. She was drunk enough that she didn’t notice and I eventually got the entire thing to fall off. I pretended to reposition myself, gave myself a few strokes, immediately got incredibly hard, and went straight back to fucking her. “Oh my god!” she cried. “That’s so much better!”

I figured she knew that I removed the condom, given the obvious change in our mutual pleasure, the hardness of my cock, and the ease of which I was slipping in and out of her. Now, with no restrictions, I thrust into her and found a rhythm she could get into. Within minutes, her cheeks and chest were flushed red, her eyes were shut tight, and she was rocking her hips as she came. She panted, moaned, and sucked air. It was fucking great.

Now that she had cum, I wanted to make myself cum. I wanted to take advantage of her skinny body, bend her over the bed, and try to break her in half while fucking her. Unfortunately, the moment I pulled out, she saw that there was no condom on my dick, and freaked out. “Oh my god! The condom fell off! When did that happen?!” I played dumb and said I hadn’t even noticed. “It must have happened once the sex got really good.” I just went along with it.

She spent the next few minutes being paranoid that she got pregnant (despite me not cumming) and the mood sort of died. I tried to allow her to let me finish, but there were no more condoms and there wasn’t a chance she was going to let me back inside of her bare.

How sexually satisfying was this hookup? Somewhat

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? After the hookup, we continued to be great friends. She never got jealous, never got clingy, and we continued to have sex on random occasions. From then on out, I always made sure to remember to bring a Magnum XL, as I wasn’t going to have her freak out again- and I surely wasn’t going to try and squeeze into a regular sized condom anymore.

This story segues into part two when Sydney introduced me to her roommate, Jessica.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, Intoxication, To feel more desirable, To feel more confident, To cheer myself up, Power / Dominance, Revenge / Getting even, Boredom, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

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

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? 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? Sydney told her roommate Jessica about the hookup. She actually bragged about it. That’s the beginning of the next story…how I was handed off from Sydney to Jessica.

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? I felt really proud of the fact that my ex-friend dated this girl for years, took her virginity, and was never able to fuck her without a condom. On our first encounter, I had my bare dick grinding into her, feeling her juices against me without a pesky condom in the way.

What was the WORST thing about this hookup? I never came. I had to console her and explain to her that she wouldn’t get pregnant so easily. It was somewhat annoying and she never really got over it.

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!