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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? Single
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? A lot

The Math Nerd’s Ass

How long ago did this hookup happen? 12 years ago, when I was 20

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 6 months

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? “K.” was around 6′ or 6’1″, just a bit shorter than me. She had an alright face: light brown hair, pretty blue eyes, and great skin. But when it all came together she was just “sort of cute.” She had a horse mouth, really. Nothing really spectacular. Her breasts were sort of average (probably a 34 B), but her ass was absolutely stellar. She had extremely long, toned legs like a volleyball player and an ass that looked like it was sculpted by Donatello.

I was taking a math class in college and always sat in the same place. Each day when K. came into the class, she would make shy eye contact with me and then sit at the table in front of me. I could tell by the way she was looking at me each day that she wanted me to talk to her, but I wasn’t entirely sold on whether or not I wanted to pursue her. It can get awkward if you hit on a girl in class and it doesn’t work out.

Anyway, after about two weeks of her giving me very innocent “please come talk to me” eyes, she finally got up the nerve to sit next to me rather than in front of me. I took this as a sign that she was really going out of her way to try and get me to notice her, so I took the bait and struck up a conversation. God, she was a nerd. I got really great grades throughout college, but K. was acing every single one of her tests. She was a brain. And the stereotypes of a brain came along with her: shy, nerdy, reserved, and not a lot of self-confidence.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After becoming acquainted with one another, K. started to sit next to me every day. We talked every day and once I felt like she was comfortable with me, I asked her if she’d like to hang out sometime. She agreed and her excitement was pretty obvious.

The very first time we hung out, we kissed. Kissing led to making out. Making out led to me trying to undress her, but she stopped me. She told me that she was a virgin. I asked her if she was saving herself for marriage, but she told me no and that “it just hasn’t happened yet.” I told her that if she was anxious to lose her virginity, I would be more than happy than to help her. She giggled, but didn’t really respond.

After a few more get togethers and strictly making out, I finally found myself in K.’s bedroom with her. This time, when I went to remove some of her clothes after making out for a while, she didn’t stop me.

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? K. helped me remove her top and followed up by removing her bra herself. Her breasts were a decent handful. They were sort of small, but very perky. She stood up to take off her jeans, revealing a lacy thong underneath. She turned around to put something on her dresser and that was when I saw her almost-bare ass for the first time. Words cannot describe how perfect her ass was. I’ve shared stories on this site about big asses, plump asses, and nice asses. K.’s ass was all of the above AND rock hard toned. I immediately blurted out to her how incredible her ass was and she just blushed and talked about how squats are her favorite exercise at the gym. I’m telling you, this ass….god.

Anyway, K. came back to the bed and I guided her hands toward my cock. She pulled it out from behind my jeans and proceeded to give me a really, really great blow job. She was enthusiastic about her and you could tell she was trying really hard to do a good job. I played with her tits, focused mostly on squeezing her ass, and gently thrust my dick into her mouth as she sucked and stroked.

When she was done, I laid K. on her back and kissed down her body. I skipped over her pussy, kissed up her thighs, and finally started to lick her clit. She moaned passionately as if she had never experienced anything like it before in her life. I continued to lick and massage her clit with my tongue, eventually incorporating my finger- and then fingers- into her pussy. After a bit, she came hard. Her long, lotion-coated legs wrapped around me and I cupped her ass with my free hand while extending her orgasm.

After her body relaxed, I climbed back up to her, pausing to suck her tits on the way, and leaned in for a kiss. She kissed me passionately, reached down for my cock (still throbbing hard), and started stroking me. I raised myself, getting ready to enter her from a missionary position, thankful that I was going to take another girl’s virginity. And just as the head of my dick touched her pussy, she stopped me. “Can we wait until next time?”

Internally, I was dying. But, paraphrasing, I told her, “Of course. Whatever you’re comfortable with-”
“It’s just that I want to make it special and I wasn’t really planning on it being today…”

God dammit.

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? I crawled back up the bed, laid next to her, and she started asking me if I enjoyed the blow job she gave me. I told her I did and she told me that it was the first time she had ever done it before. I was pretty surprised. I knew she wasn’t the world’s prettiest girl, but she was more than attractive enough to have gotten to third base before. She proceeded to tell me that it was the first time somebody had eaten her out before, shedding light on her reaction to me doing it. I asked her if she had ever had an orgasm before the one I just gave her and she told me only from masturbating. At least I made some milestones.

In the days that came, I continued talking to K. and- looking back- probably pressed the sex topic too hard. She began wondering if I really liked her or if I only wanted her for sex. All I wanted was sex, but she clearly wanted something more. I wasn’t about to give it to her.

One night, when I was at another’s girl’s place and in bed having sex with her, K. called me. The girl I was with happened to be cheating on her boyfriend back home (see my story about being shared between friends, part 2) so she didn’t really have any right to get upset about another girl calling me and me taking the call.

When I answered, K. sounded like she had been crying. She asked me quite suddenly, “So are we dating? Or are we just friends?” And, being teased by the naked girl in front of me to come back to bed, I didn’t give it enough thought and replied a bit too honestly. “Friends, aren’t we?” “Oh…okay then.” And she made some excuse about having to go and hung up. I went back to fucking the girl in front of me, oblivious to what I had just given up.

At the next class, K. didn’t sit next to me. It wasn’t until then that I realized how badly I fucked up. Ultimately, it may have been for the best. All the girls I’ve ever slept with, I’ve been very straight-forward with them about not getting their hopes up or the sex being any more than what it is. With K., I feel like I probably would have had to feign love for her in order to get her to sleep with me. That’s not really my style, so this was probably a blessing in disguise.

I sure would have liked to take her virginity, though. And had I been able to fuck her perfect ass, I could have died right then and there and been a happy man.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely, Power / Dominance, It was easy / convenient

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 didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Since K. was just a girl I knew from class, she never met any of my friends. There wasn’t ever a need to tell anyone about her, so I never did.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Very

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I’ve interacted with a lot of girl’s asses in my days. K.’s ass was better than all of them put together. Her ass was better than a lot of “celebrity” girl’s asses who are known for their ass. I want to smack it right now just thinking about it.

It’s also nice to know that my dick was the first dick that ever entered her mouth. And that my tongue was the first tongue to ever run up and down her pussy. …and that my tongue and fingers gave her her first orgasm that wasn’t self-stimulated.

What was the WORST thing about this hookup? I was really close to getting K. to give me her virginity. That would have been something special. It also sucks that things were broken off on bad terms. She’s one of the only girls whom I didn’t remain on great terms with after we parted ways.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I think it reaffirmed the fact that no matter how buried down it may be, I still have a conscience. I don’t think I would have felt too proud taking a girl’s virginity for the sake of getting laid when she was looking for something much deeper.

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!