by Kris Stewart
What’s your gender? Man
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (currently pursuing)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? 7
What was your relationship status at the time? Single
How would you best classify this hookup? Sex with an ex
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? I will call her M. She played volleyball for our high school, so was naturally athletic looking. Close to 6 feet tall, blonde, slim, with A-cups and a firm butt. We dated for close to a year before I decided to end it, but we never really stopped talking. At the time I was holding on to my V-card, and the more we talked outside of being in a relationship, the more we wanted to be more sexual. In essence, we were friends looking for benefits.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There were encounters before the real hookup. I would leave for school early to meet her in the parking lot and then take her back to my house when my parents weren’t home to mess around. The first time we did that, we played strip basketball, where whoever scored a point on the other on a Nerf goal on my closet door got to take off the other person’s clothes. I scored a shot, and peeled off her red sweater to reveal a form-fitting silken tank top beneath. She scored and removed my T-shirt. I let her score twice more to bring me down to my boxers before I just started kissing her.
One hand ran down the small of her back to push her hips close to mine while the other caressed her firm belly under her shirt. We kissed long and deep. Soon my fingers gently curled beneath the silken tank top and slowly brought it up and over her head to reveal a black, lacy bra. By now my heart is thumping hard in my chest and my member has begun to press against her now exposed belly. Up to this point, I had never taken off a woman’s clothes before, and my teenage hormones were a pulsating storm. After her tank was removed, she stepped back, reached behind to her bra, and unclasped it. I’ll never forget the small jump the bra makes as the slack is taken out, the snap of the clasp, and how she shrugged it forward to lower the cups down slowly, revealing shaped, perky, and bouncing breasts. Her nipples were erect and pink and begging to be tasted. I obliged. But before I got more than a taste, I looked at the clock and realized we had to get back to school before the first period.
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? One night, I decided I wanted to lose my V-card. I asked if she was willing, and she grew excited. Around 1 in the morning, she snuck from her house and parked at a nearby school where I met her to walk her back to my house. She had come in a short jean skirt and a fitted sweater over a tank top. We snuck into my room and I closed the door behind us. I placed her on my bed and knelt in front of her. From here I began kissing her while one hand caressed her thigh. She responded with gentle moans and slowly parted her legs, encouraging me to go farther. I traced my hand, all the while kissing her, up her inner thigh beneath her skirt to find the silky lining of her panties, soaked through. I peeled one side away and found pussy shaved, wet, and warm. As soon as I did she gasped and opened her legs wider to give me better access. I slid one, then two fingers in and slowly fingered her to satisfied moans. After a bit, she pushed me back, stood up, and slid her skirt down. She stepped forward to me as I still knelt, and told me to take her panties off. I obliged, and slowly slid them to her ankles. She stepped out of them and I was met with her shaved pussy dripping inches from my face. “Eat me”, she said and spread her legs. I tasted her for the first time and enjoyed the moans and small convulsions she couldn’t contain as I worked my tongue the best way my teenage self could manage. It must have been good enough because she suddenly gasped “Don’t stop!”, dug her fingers into my hair and pushed my head deeper into her mound before convulsing and shaking uncontrollably. Stepping back, she said “your turn”, and brought me to my feet. She put a finger to my lips and said: “Don’t move”. She peeled off her sweater, then her tank, and unclasped her bra. Her athletic form, now naked and glistening before me, drove my member wild. Noticing, she slid a hand into my shorts and gently stroked the underside of my dick. I nearly came right there. Sensing I would not last long, she finished undressing me and unrolled a condom on me. She then laid me down with my dick sticking up like a flagpole, and swung a leg to either side of me into a straddle position. “It’s ok if you cum quick, you took care of me, now it’s my turn to take care of you.” With that, she knelt forward on her hands, her breasts inches from my mouth. Reaching back, she found my stiff dick and guided it to her entrance. When it was aligned, she slowly sank down with a soft sigh. I remember feeling intense warmth that enveloped my dick and sent electricity to the depths of my groin. With more silent moans she slowly slid up and down my shaft, sending more waves of uncontrollable sensation over me. Her tits lightly swung to the rhythm of her pumping, and I was mesmerized. I looked down to see my dick disappearing into her pussy and then reappear, slick, wet, and throbbing with an aching need for release. Seeing me looking at her she whispered, “Cum in me.” I couldn’t stop it, the waves to my groin welled and suddenly I erupted, pumping what seemed like gallons of cum up into her. Over and over my balls pumped, draining every ounce I had up unto her waiting pussy. After what seemed like an eternity, it slowed and ceased, leaving me breathless.
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 met once more before she became serious with her now husband.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms
What were your motives for this hookup? Fun, pleasure, horniness
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? A few friends
How would you best summarize people’s reactions about this hookup? Relatively positive
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? A little bit
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? First time having sex
What was the WORST thing about this hookup? Being up so late for class the next day
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m more into pleasing my partner than myself.
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? No
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? Just be careful
What do you think about the Casual Sex Project? Educating for sure
You have a hookup story to share? Submit it here!