by

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? Very many

Lined Up in Advance

How long ago did this hookup happen? Age 19

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 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? When MySpace first became popular, it hadn’t yet become weird or creepy to send or receive messages from strangers. Since smart phones and hook-up apps didn’t exist yet, MySpace was easily one of the best methods for meeting attractive, local girls whom you could eventually hook up with.

When I was a freshman my first year away from home at University, I decided that I was going to search for and message a bunch of hot girls back home a few months before I went home for the summer. I met a lot of girls this way (many of whom I’ve submitted stories about), and the one I’m going to share a story about today was “Sarah.”

Sarah’s profile pictures were exactly what I was looking for. She appeared to be quite pretty (white-skinned Hispanic, brown hair, brown eyes, a very tiny waist with a great, big, round ass, perky 34 B tits, and a really, really tight body). She didn’t come across as slutty, but she had a few obligatory bikini pictures that had been taken at the beach. She was one of the many girls I sent messages to that day and thankfully one of the handful to reply.

We began sending messages back and forth to one another quite a bit before moving the conversation to AOL Instant Messenger. She quickly became one of the girls I spoke to the most and we made plans to see one another when I came back home for the summer.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I don’t exactly recall how we made plans, but I know the evening started at Chili’s. Sarah was 21 and able to order a margarita, but I was only 19 and couldn’t get anything alcoholic. I was embarrassed, but luckily for me Sarah didn’t mind the age difference and we engaged in wonderful conversation throughout dinner.

As with most conversations at this age, it quickly turned to a sexual nature and Sarah told me how her boyfriend (what?!) never wanted to do the things in the bedroom that she wanted to experiment with. I ignored her boyfriend comment- wanting to keep her focused on a sexual topic- and asked her what type of things she wanted to try. She told me how she always wanted him to pull her hair, spank her, and fuck her really rough, but he was completely unwilling to be rough with her. I played my cards right, giving her some bullshit about how it was important to be able to try new things and be accommodating…blah blah blah.

(It turned out the guy Sarah was dating had a kid and ex-wife; so Sarah was often treated as a last resort when it came to him making plans and treating her in a way that she felt she ought to be treated. Thus, she decided to “get out there” and date more, hoping to find someone to treat her right.)

After dinner, we wound up in my car together just driving around. We found an isolated parking lot and began to chat. There was definitely some incredible chemistry between us, as well as sexual tension. Sarah was a bit giddy (not from the alcohol) and I pounced on her. We began making out in the front seat before making our way to the backseat.

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? Once in the backseat, Sarah dropped to her knees the best she could given the space, undid my pants, and began to give me head. At that point of time in my life, it was far and away the best head I had ever received. She swirled her tongue around the head of my cock, stroked me with two hands at the same time, and massaged my balls while deepthroating me. It was extremely rare for me to cum during sex because of how I was jerking off nearly every day; and me having an orgasm from a blow job had never happened before. But when Sarah was going down on me, there was no doubt I could feel an orgasm building. Rather than giving her the impression I was about to cum, I just gently brought her up from her knees and lead her toward my lap to initiate having sex.

Sarah asked if I had a condom, but I told her I didn’t. We told one another we were clean, believed each other, and she took my soaking wet cock in her hand. Her mobility was improved by the fact that she was wearing a short dress, but limited by the fact that the roof of my car was so low. Regardless, it wasn’t difficult for her to slide her panties to the side and guide my cock into her pussy. She let out a sigh into my ear as I slid into her and I firmly grabbed her ass cheeks with both of my hands. She started bouncing up and down on my lap with her long brown hair in both of our faces while we continued to make out. She kept hitting her head on the roof of my car, so I took over the thrusting. She remained on top of me, but rather than hopping up and down, I just raised her body a little bit off of me and then thrust in and out of her from my seated position.

No longer having to hold herself up, Sarah took her dress up and over her head, removed her bra, and introduced me to some of the perkiest 34B tits I’d ever seen before or since. My mouth was immediately on them, sucking her tits, licking her nipples- and then I remembered her bedroom preferences. As my tongue worked her nipples, I began smacking her ass. The first spanking caught her by surprise and she let out a small scream. Any concerns I had about having spanked her too hard were quickly put to rest when her facial expression went from sexual ecstasy to pure, carnal lust. Her eyes focused in on me, her mouth was slightly agape, and she wrapped her arms around my neck like I was the greatest thing in the world. I hadn’t ever spanked anyone during sex before, so I wasn’t sure how hard to hit her. Being limited in my “wind-up motion” by the seat in front of me, I told Sarah to get on her knees so I could fuck her from behind. She let out a small whimper (presumably because this meant we had to stop for a moment), but obediently got on her knees in my back seat.

My car was small, so there was barely any room for me to get behind her. Also, I’m pretty tall, so I had to completely hunch over her. To regroup for a moment and paint the proper picture, just imagine a tall guy fucking a girl doggy style in a really small car’s backseat. My ass was pressed against one side, her head was slamming into the other side with every thrust, and I was bent so far over her that I could easily kiss her shoulders and neck.

Despite our awkward position, I kept thrusting and smacking her ass. She let out a small yell with every ass-smack and provided me with my first introduction to dirty talk. “Yeah, smack my ass!” “Fuck me harder!” and “Pull my hair!” I had forgotten about this last one. I grabbed as much of Sarah’s hair as I could in my left hand and gently- but forcefully- yanked back on it. Sarah’s face was forced to look upward as I used her hair as the leverage I needed to thrust into her with rhythm. What was once really awkward sex now became absolutely incredible. With both hands clutching her hair now, I was able to get the leverage I needed to hold myself up properly and fuck her with a consistent rhythm necessary to make her cum. It wasn’t long before she was screaming out an orgasm.

As her slightly-sweaty body started to relax and stop trembling, I let go of her hair. She turned her head, looked me in the eyes, and told me in the sweetest, most innocent sounding voice, “I still want you to cum.” I had been conditioned to believe that I couldn’t cum during sex (see: jerking off too much), but I quickly remembered how Sarah had almost made me blow my load from going down on me. So, now with my focus being on giving myself pleasure, I went back to thrusting into Sarah from behind. Having let go of her hair, Sarah’s head was now back to getting slammed into the side of my car. It had to have hurt her, but she didn’t complain; so I focused on trying to cum.

Finally, with my hands wrapped around her body and holding her tits, I knew I was going to explode. I asked her if she was on birth control, she quickly screamed, “yes! don’t pull out! fuck me!” and I exploded inside of her. She fell on her side, I fell on top of her, and we sat there in that awkward position- sweaty bodies and all- kissing and caressing each other lovingly. For having fucked on the first date, it felt like we had known each other forever.

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? The next day, Sarah kept texting me telling me how she couldn’t stop thinking about the sex we had. She also told me she had a huge lump on her head where her head was slamming into my car. Lastly, she told me about how from having her hair pulled and her ass spanked red, she had had the best orgasm of her life.

We continued to see each other and have sex for years. Throughout the entire time I knew her, she was “on and off” with the same guy who refused to commit to her. Because of his failure to commit, Sarah would refuse to let him sleep with her. To satisfy herself, she would always call me and we would engage in really great sex. We had sex in her parents house, her car, my car, and in a few public places. Being a professional photographer, she would also send me pictures of herself in extremely pornographic positions. Bent over, fingering herself. Spread eagle on her bed while she played with her tits. It was great.

We developed a trust with one another over the years that made us extremely comfortable with one another. We knew what we had wasn’t ever going to turn into a relationship, but when we were with each other, we treated one another as if we were soulmates. It’s difficult to explain. It’s almost as if we were fuck buddies who acted like we were in a long-term, committed relationship (without any negative aspects like arguing).

Eventually, I said something to Sarah about how the guy she was continuing to see wasn’t any good for her. I didn’t want her for myself, but I was trying to do her a favor. It didn’t turn into a fight, but she got offended. She stopped talking to me for a while. I missed being able to fuck her, but I had so many other girls in my life at the time that I never really tried to patch things up with her. We drifted apart and never spoke again.

From a bit of Facebook stalking many years later, I found out she’s still with the same guy, but they never got married and never had any children together. I wouldn’t be the least bit surprised to learn that they’re still on again off again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

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

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? I never told anyone about Sarah. She was my secret.

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? A little bit

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The best thing was Sarah’s body and personality. She had a very stereotypical Latina body that featured a small waist, great big ass, and firm tits. And she was extremely sweet. She was always very kind to me, which in turn prevented me from ever treating her like a fuck toy. This lead to how our “fuck buddy” status had such a unique, emotional twist embedded in it.

What was the WORST thing about this hookup? Honestly, it was probably the fact that Sarah was being strung along by the same guy for such a long time. If I had considered her marriage material, I would have talked her out of seeing him and treated her right. But, because I didn’t have an interest in keeping her around long term, I was sort of forced to witness the misery he laid on her over and over again until I couldn’t take it anymore and spoke up.

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

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

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

Story Views: 2,776