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? Many

Four Years Later, Finally

How long ago did this hookup happen? 12 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 more than 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? “Ali” had quite the proportionate features. She was around 5’8″, 125lbs, and had a solid 34C rack and tight ass. Her stomach was flat, her hips were wide, and her waist was thin. She had long, dark hair, brown eyes, and big lips. Her teeth were tiny, but it was a minor flaw on an otherwise flawless figure.

I first met Ali when I was 16 and walking around the mall with some of my friends. We were both mallrats in different social circles. My circle was normal teenagers who created a few pranks but never got into serious trouble. Ali’s circle was full of actual criminals. She herself was incredibly sweet and came from a great family, but for some reason she decided to hang out with people who sold drugs, committed felonies, and got into a ton of trouble.

We were drawn to each other, engaged in a brief romantic weekend (with only a few kisses), and then she cut things off with me with no real reason given. Being that I was so young, it was extremely painful. I remember having quite the heartache after she didn’t want to see me anymore.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Fast forward to about 4 years later: I’m usually away at college but happen to be down home for the winter holidays. As luck would have it, I run into Ali at the mall we used to frequent when we were younger. Her face lit up when she saw me and she seemed really eager to strike up a conversation. I had no hard feelings toward her since so much time had passed by and I couldn’t help but notice what an incredible body she grew into having. We were both around 20 years old now and hadn’t seen each other in about four years, so we decided to make plans and get together.

Ali invited me over to her house while her parents weren’t home, so I definitely expected to get some. The only problem was that Ali was now a “devout Christian,” attempting to remove all of the bad people in her life. I learned that a lot of her friends were in prison, addicted to hard drugs, or in one case, had been murdered. It was crazy to see this beautiful girl living in a wonderful home still struggling with the type of people she insisted on surrounding herself with.

No matter her new-found religion, I still wanted to fuck her brains out. I felt like it would give some closure to my 16-year-old self and was clearly something I had wanted for a long time. Ali wouldn’t give in to having sex with me that day, but she did let me kiss her numerous times. When I asked her why she was so hesitant about allowing me to kiss her, she informed me that she had a boyfriend. But- wouldn’t you know it- he was in jail at the moment. So now I’m wondering if pursuing Ali is worth potentially having a criminal come after me in the future. Not being able to make a decision in my mind, I let my dick decide. That guy’s always up for a good time no matter the consequences.

A short time later, Ali and I make plans to go to the beach late at night. I bring a blanket and condoms. She wears a tight white t-shirt that’s both low cut for cleavage and high cut to reveal her flat stomach. She’s looking smoking hot. She’s wearing extremely tight jeans, just the right amount of make-up, and a perfume that was absolutely delicious. For somebody who had a boyfriend, she definitely went out of her way to make herself very presentable. But, given her new-found religion, I knew I still had to be on my persuasive game if I was going to get my dick wet.

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 on the beach, I was relieved to see that it was completely empty. We found a stretch behind some hotels under construction so we had as far as the eye could see to ourselves. I laid down the blanket, joined it with Ali, and we talked. I spent most of the time attempting to seduce her with her “really wanting to” but determining she “shouldn’t.”

As this game of back and forth often goes, “shouldn’t” became “just a kiss,” which became making out, which became clothes coming off. I got Ali out of her tight jeans and marveled at the incredible curves of her body illuminated by the moon. She had such an incredible figure. I positioned myself on top of Ali and she spread her knees apart to make both of us more comfortable. Now, with my hard-on pressed against her pussy (and only our underwear between us) it was inevitable that sex was brewing. I continued kissing her, gently massaging my cock onto her pussy, doing my best to get her turned on and soaking wet. It worked. After only a few minutes, Ali’s hand was reaching down my boxers and stroking my cock. I caressed her shirt and bra straps over each of her shoulders and gently tugged her shirt and bra out of the way. Her tits were hard. Not the type of hard that indicated they were full of silicone, but the type of hard that you can only associate with really perky tits. They were a splendid handful- a 34C if I had to guess.

Now, when we spoke to one another, Ali was using a very delicate, high-pitched voice. The type of voice that tells you you have her right where you want her. The sex voice. You know how a girl’s sex voice is so much softer and “vulnerable” sounding right when she knows she’s about to let you inside of her. It was everything I wanted from years ago and I knew I was free to make the final move.

I reached down, rubbed Ali’s pussy, slid her panties down her thighs, and re-positioned myself on top of her. She grabbed my cock, guided it into her, and gasped when I entered her. That first gasp is heaven.

I slowly thrust into Ali, watching her face enjoy each and every thrust. Rather than having her hands roam all over my body, they reached back behind her- bent at the elbows- and dug through the sand. Her head tilted back, eyes shut, and she let out little whimpers of pleasure every time I thrust into her. When I found the angle and speed she responded to best, I kept the rhythm and drove her to orgasm. Her body shuddered as her vagina tightened its grip around my shaft.

After she had her orgasm, I shifted my body and positioning so that I could get into a rhythm I needed to cum. I raised my upper body a bit so that I was thrusting upward as well as into her, thereby rubbing the head of my cock on where her g-spot was supposed to be. Just as I was about to cum, I heard Ali starting to moan and scream like she was about to cum again. But since I took myself to the point of no return, I had to pull out. I shot a stream of cum across her flat stomach, creating a pool in her belly button. She watched me stroke myself- smiling to herself- as I finished my orgasm. She used the blanket we were laying on to wipe herself off, turned to me, and said, “I’ve been wanting to do that for a very, very long time.”

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 walked back to our cars, kissed passionately, acted cute with one another, and gave each other some genuine affection. If it wasn’t for her choice of friends (and tiny teeth), I could see myself really liking this girl. But, because of the aforementioned, I mentally prevented myself from falling for her at all.

We saw each other a few more times (once having sex in the back of her car), but ultimately she told me that she didn’t want a fuck buddy. I didn’t want to give her the relationship I assumed she wanted, so we both sort of just amicably drifted apart.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel more desirable, To feel more confident, Power / Dominance

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’

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? 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 definitely Ali’s body. She had a rocking, tight body with full tits and a soft, cushioned ass. She was without a doubt a head-turner.

What was the WORST thing about this hookup? I spent a brief amount of time wondering if her jailed boyfriend would come after me when he got released. I later found out that Ali told her boyfriend about seeing me, but that we were just “old friends.” He was a lot smaller than me and if there was a fair fight, I’d have been able to easily defend myself. It never got to that, however, as he presumably believed her story.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Ali told me that she genuinely thought I was “hotter than Brad Pitt,” as if it was the world’s greatest compliment that she had given me. She had a huge celebrity crush on him, and she was being totally genuine when she told me. The sincerity in which she gave me the compliment always stuck with me as one of the best compliments I have ever received.

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