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What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (currently pursuing)
What’s your current relationship status? In a serious relationship (monogamous)
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many hookup stories have you here posted before? 0

Titfucking My Coworker

How long ago did this hookup happen? eight 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? For less than a year

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 met this very cute, very curvy, short half Brazilian girl. She had absolutely enormous breasts, but somehow had a flat stomach. She was athletic, played volleyball. She was a relaxed kind of person and was a big stoner. We got along pretty well at work. I was pretty shy but we would occasionally flirt.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One of her friends asked me casually what I thought ‘Sarah’s’ bra size was. I didn’t really want to answer one way or the other but she kept pushing. Finally I guessed 36C. She giggled and walked away. Later on that night, Sarah messaged me, and teasing me saying that her tits were actually 34D and that I need some more practice. I had only slept with my long term ex at this point so I was pretty nervous, but I invited her over that weekend when my parent’s weren’t home, under the guise of watching some movie that she liked.

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 went to my room and laid down on the bed while I put on the movie. I awkwardly make a move on her, putting my hand on her shoulder and then start playing with her hair. She turns around and I start to ask her if this is a good idea but then she grabs my face and kisses me. We make out for a bit. I go to get on top of her and start grinding on her, but she stops me. We continue to make out and she takes her shirt off but leaves her bra on. Her tits looked so fantastic. She had a pierced bellybutton and a tattoo on her ribs. I place my hand at the clasp of her bra and give her a look to ask for permission. She shakes her head and says not yet. She moves her hand down to my cock and starts rubbing. This is the second girl that has ever touched me like this so I am really turned on and exhilarated. She starts to unbutton my pants and pulls my boxers down and starts giving me a pretty bad handjob. At that age, a lot of girls don’t get that circumcised guys need lube of some sort. I didn’t really care though, she was hot and was jerking me off. She asks me to hold on and goes to take her bra off. Her tits were just as good as I had imagined, small nipples, a little saggy but that’s only normal for the size. She asks me if I’ve ever titfucked anyone before. I say yes and grab my lotion that I keep on my computer table. I squirt some on her lovely tits, pull off my pants, and start fucking them. She was holding them together with both hands and moaning lightly. She knows how much all the guys stare at her rack and gets off on the power she has over them. I don’t last very long, maybe a minute, and start to cum all over her neck and tits. After catching my breath and getting her a towel, we spoon on my bed and chat for a while.

How sexually satisfying was this hookup? Very

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? It got awkward because her parents didn’t want her dating an older guy (I was one year older, big deal), so I only saw her one more time.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

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 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? No one, I figured it was our business and no one elses.

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Seeing her awesome tits then getting to cum on them. In high school everyone was obsessed with this girl.

What was the WORST thing about this hookup? Not getting to have sex.

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

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

What do you think about the Casual Sex Project? I love it

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