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? Over a dozen, I think
Bouncing from Friend to Friend (Pt. 2 of 4)
How long ago did this hookup happen? about 13 years ago
What was your relationship status at the time? Single
How would you best classify this hookup? Short fling
How long did you know the person before this hookup? For less than a week
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? “J.” was S.’s roommate (the girl from part 1 of this story). J. and S. were really great friends despite having only met a few weeks prior after being paired together as roommates. They were inseparable.
J. was not “sexy,” per se, but she was incredibly cute. She had a bubbly personality, smiled and laughed a lot, a cute button nose, and was overall very positive. She had long, dark brown hair, green eyes, fair skin, and a lot of freckles. She was top heavy- had some really nice breasts- but just an average ass.
Because I had been hooking up and hanging out with S. so much, J. eventually started to accompany us and we became a bit of a trio of friends each weekend. J. had a boyfriend back home, so I would usually pretend to be her boyfriend out at parties whenever a drunk guy would try to flirt with her. I enjoyed her holding my hand, sitting on my lap, or putting an arm around me each time she was trying to make someone go away. And rather than being jealous, S. would play along, sometimes pretending that we were in a three-way relationship. As much as I wish a threesome could have happened, S. was 100% straight.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After sleeping with S. every weekend had become a bit routine, I started to heavily flirt more with J. When pretending to be her boyfriend in front of some guy at a party one night, I kissed her. I knew she wouldn’t be able to say anything without revealing that I wasn’t really her boyfriend, but to my surprise, she went along with the kiss and didn’t seem to be the least bit offended. This led me to believe that I may be able to actually sleep with her, so I kept caressing her throughout the night.
When the three of us got back to J. and S.’s apartment, I was going through the motions of heading off toward S.’s room with her, as I always had, so that we could have sex. Only this time, as I made my way over, I could very clearly see J. giving me the fuck me eyes and a face that screamed “you should be coming with me instead.” One of my biggest turn-ons is the pursuit of sleeping with a girl I’ve never slept with before, so seeing J. give me this face was driving me wild. But, not wanting to insult S., I still went into S.’s room with her. S.and I had sex. She came, but I didn’t, and to my surprise, she immediately started telling me, “Why don’t you go check on J.? I think her and her boyfriend are having a rough time.” There was no denying what she was trying to tell me. She was telling me with complete sincerity that it was fine with her if I wanted to go have sex with her best friend and roommate. I was fucking excited.
I kept my excitement hidden, asked her if she was sure, and S. replied something to the effect of, “I had my orgasm. I’m happy. And tired. I’m going to sleep, dude.”
I put on my jeans but not my t-shirt and left S.’s room. I walked across the living room, gently knocked on J.’s door, and heard her answer “come in” in an inquisitive tone. When I peaked my head in the room, J. was in her bra and panties. I wasn’t sure if she was expecting me or her roommate, so I waited for her reaction to seeing that it was me.
“Did you lose your shirt?” Her eyes scanned my body and she had a small trace of jealousy in her tone. I tried to lighten the mood and told her, “Yeah, did I leave it in here?” as I walked in. She smiled, but still acted a tiny bit stand-off-ish. It was clear she was jealous that I had just fucked her friend, but I was quick and pointed out that she wasn’t allowed to be jealous since she had an actual boyfriend back home. She laughed, gave me a “yeah, you’re right” kind of look, and stood up.
It was incredible to see her tits in nothing but her bra. If they looked big behind a t-shirt, they looked absolutely splendid in her lacy bra. We moved closer to one another, put our arms around each other, and began to make out.
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? We had chemistry. J. was very submissive, I was very aggressive, and our bodies moved in unison without any effort. I could tell we were going to have great sex. I laid her down on the bed, and began to undo my jeans. I wanted to skip past the blow job since I had just been fucking S., but J. sat right up and began to stroke my dick and tickle my balls. I contemplated telling her that she may not want to put my dick in her mouth, but I decided not to run the risk of making her jealous again.
So J. put me in her mouth. She showed no notion of tasting S., so I quickly slid into enjoying her blow job. I cupped both of her tits with my hands, fingered her, and squeezed her ass. After getting me rock hard and sopping wet, I laid J. back, and slid myself inside of her. It was great watching her face scrunch up in pleasure as her big tits rocked back and forth each time I thrust.
If I’m being honest, I have to include this particular memory. After starting to get a bit tired of holding myself up (in the missionary position), I lowered myself so that I was still on top, but now laying flat on top of J. And that’s when I smelled her body odor. Arm pits. It wasn’t strong, but it was enough to take me out of the mood. I continued thrusting, making sure J. had an orgasm (she moaned very quietly and came rather silently), but I never got off myself.
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? From that point on, I was S.and J.’s private, secret fuck toy. We went everywhere together, I constantly flirted with both of them in front of one another, and we had what was as close to a three-way relationship as you could imagine. We made cinnamon rolls together, went to parties together, and I would fuck one or both of them (separately) once we got home. S. was totally cool with all of it, but I could see J.’s jealousy was slowly growing with time. It got so bad, that J.’s boyfriend back home became really concerned with who I was and why he kept hearing about me. He came up to visit J. one weekend, got to know me, and ultimately left having told me, “I was worried about you and J. But I can tell you’re a good guy. I’m glad you guys are friends.” If he only knew.
And then one night, when the three of us were at some random house party, in walked a girl I had known in middle school and absolutely hated. She’s the focus of what will be part three.
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), Thought it was an important experience to have, Intoxication, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, Power / Dominance, Making new friends, 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 didn’t give a clear ‘yes’, but didn’t give a ‘no’
To whom did you talk about the hookup? How did they react? S., J., and I never talked about our sexual relationships with one another. They both knew I was sleeping with both of them, but to keep the peace I guess, neither of them really acknowledged it.
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 had consistent sex every weekend with two beautiful girls who- neither- had no issue that I was sleeping with their roommate/best friend.
What was the WORST thing about this hookup? The body odor from J.’s armpits wasn’t a one-time thing. It was every damn time. It wasn’t a big deal, but I learned to keep my face away from her shoulders and surrounding area.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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