What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Virginia
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT Systems Engineer
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
Any other term(s) that describe your sexuality or sexual identity? curious
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

The Girl From the Bookstore

How long ago did this hookup happen? 22 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For 1 to 3 years

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? She was a short and very fat Italian girl, with curly black hair, a cute round face that always had a smile, and an outgoing, slightly sarcastic, personality. We were both assistant managers at a bookstore, worked together for about 2 years, frequently had time to chat after the store closed, and sometimes confided in each other about our relationship issues. I liked her as a friend, but didn’t consider her as more than that.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? As time went on and we got to know each other better, we flirted with each other quite a bit. I saw it as simply friends/coworkers passing the time and being silly. We started confiding in each other more frequently, and I started to see her as maybe something more than just someone to goof around with at work, but as I was engaged, I didn’t pursue it.

Late one afternoon we were in the office together making snarky comments at each other, she was leaning against the door, made an overtly sexual face then smiled with a “what are you going to do about it?” look. Taking the bait, I leaned over and squeezed her breast, leaning in as if to kiss her with my lips only and inch or two from hers as I looked into her eyes. We broke it off and quickly went back to doing our work. Later that evening after the store closed, I casually asked if she wanted to do something after we finished up. She asked what I had in mind, and deciding to just go for it I said “Maybe we could get a hotel room?” She looked away for a minute, then back at me with a smirk and said “Sure”.

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 decided to go to a motel just down the street from work, and took her car on the very remote chance that someone would see my car parked there. I gave her cash and she went inside to get us a room. When we entered the room we just sat talking for a while, neither of us sure how we should start things. I don’t remember who eventually made the first move, but once we began we were all over each other. I had doubts that this was the right thing to be doing for a minute or two, then got caught up in the moment and just let things happen.

She wasn’t self conscious about her body at all, which was refreshing. I had always gone for curvy girls, and they often had body image issue. She was easily the largest girl I had ever been with, but was so confident and sexy I never even gave her weight a second thought. She was soon down to her black panties and bra, and I had just my jeans on. We stopped making out for a bit, and just sat on the bed talking, admiring each other and casually touching each others bodies.

She sat up on her knees and took off her bra, letting her firm, medium size breasts out, which she cupped and asked if I liked. I got on my knees as well and began sucking her tits, my hands making their way into the back of her panties. Eventually I worked them down and she lay back as I took them off, and I looked at her well trimmed pussy for the first time. I leaned over to kiss her just above her pubic mound, and noticed that her lips were quite long, and she had the largest clit I had ever seen. It stood out at least an inch, and was as big around as my finger tip. The sight of her clit and labia turned me on immensely, and my already hard cock got even harder.

I lay between her legs and began licking and sucking on her beautiful lips and clit, with her hands on the back of my head pushing my face into her pussy. I had been going down on her for about 15 minutes when she suddenly tensed up, moaned, and I felt her clit throb slightly as she came. She pulled me up from between her thighs and used her fingers to wipe the pussy juice off my face.

She got up and went into her purse, coming back with a condom which she quickly rolled down on my cock. She lay back, spread her legs, and said “Come on boy, fuck me.” Eager to comply, I crawled up on top of her and she guided me into her pussy. We lay there for a bit, just slowly rocking, then I started fucking her hard, with her holding onto my waist tightly as she pushed back against me with every thrust. I distinctly remember rocking back and forth on her very large belly, and thinking that this was fantastic, a perk of being with a really big girl that I had never imagined. I still think of that feeling occasionally, and it never fails to arouse me. We fucked for a while, then she told me to bite her tits. I bit her softly, but she loudly insisted that I bite hard. I complied and ended up leaving large bruises and teeth marks on her breasts and belly, and bit her nipples until they were bright red and raw. She LOVED this, and I continued doing it throughout the night.

We fucked on the bed, on the floor from behind while I massaged and smacked her large round ass, and with her lying on the edge of the bed as I stood and fucked her. I don’t know how long we fucked, easily more than an hour. I remember at one point reaching down between us and stroking her clit and pulling on her lips as we fucked, which made her gasp and shriek with pleasure. I was getting tired at this point, and we ended up with me on top of her again, and I fucked as hard as I could until I came, moaning loudly, holding her tight as I gasped from pleasure and exertion.

After lying together for a bit, we got up and went into the shower and cleaned each other off. We kissed a little more after getting dressed, then she drove me back to my car and we said goodnight, knowing we would see each other the following day at work.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

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? We pretended nothing had happened for several days, then ended up making out again after work one evening in the store, but it went no further that night. We left things open to getting together again if/when the time was right and we both wanted to.

If given the chance, I’d like to catch up with her, see how she’s doing these days, and maybe laugh about the time we spent working together and the night we had.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, To feel more confident, I was feeling lonely, Just happened, I don’t know why, just went along with it, 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? Somewhat

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? Nobody

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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I was engaged at the time, and had some guilt about cheating on my partner. We were having a difficult time and having very little sex, so I felt that it wasn’t unreasonable of me to look for it elsewhere.

What was the BEST thing about this hookup? Honestly, the best thing was getting to go down on the largest labia and clit I’ve ever seen. It was a huge turn on. The sex was damn good, too. It was very freeing to just be having sex with no expectations of a relationship or anything more than making the other person and myself feel good.

What was the WORST thing about this hookup? Feeling somewhat guilty and knowing that if my partner found out it would be the end of our relationship.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me realize that a woman could be sexy and attractive even if she was far from the standard of beauty that we have in modern American society.

I had never really had casual sex until this, so it was a new experience, I felt very free afterwards, knowing that it was possible to have good, even great, sex without being “in love” with someone.

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

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

Anything else you want to add about this hookup? I’d do it again if given the chance with her.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I haven’t had much casual sex, but the few time I did, it was a positive experience. I wish that we didn’t have a double standard in our society, where it’s considered normal for a guy to want/have casual sex, yet it’s considered wrong or slutty for a girl to do the same.

What do you think about the Casual Sex Project? I think it’s a great idea, both for research purposes, and for sexual arousal.

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