First Time Cheating



What’s your gender? Woman
How old are you? 26
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? GA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? 0

First Time Cheating

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

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? This happened over ten years ago and to this day, I still remember every detail.

Jamie transferred to my high school a year prior. He was skinny tall & lanky, brownish red shaggy hair, beautiful green eyes, freckles and a year older than me. He always wore tie-dye and was a loner. I didn’t think he was attractive but I noticed the popular girls were always hanging out with him. I later found out he was as a source for pot. His parents bought a farm outside of town and they lived in the run-down home on the property. Jamie lived in a separate apartment that was once a garage. His parents were cool and left him alone to do is own thing. He didn’t have a car but he always had a ride home. The girls would share stories about giving him a ride home, smoking pot and have sex with him. I heard more than one girl say he had a huge penis. I was not part of the popular crowd in school because I was the awkward dorky looking girl. I was tall for my age, 5 ft 9 in, flat chested & thin. I ran track and played volleyball. My parents were super strict & wouldn’t allow me to hang out with the ‘in crowd’. I had a boyfriend and we’d been together for a year and a half. He was shorter than me, heavyset, and shy. We started out being friends then our parents agreed to let us go to a matinee at the local theater and we became exclusive. I had just got my license and with help from my parents, I was able to buy my first car. We were both virgins and two weeks prior, we finally decided to have sex. Looking back, the first time was just like everyone describes, quick & awkward but it got the job done. We had sex two more times, with the same results. He left a few days later with his family for a two-week cruise.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was driving home from my part-time job at a fast food place and I noticed Jamie walking on the sidewalk. I honked and asked if he would like a ride. He hopped in and I took him home. He told me his parents were gone to a retreat and asked if I would like to come in to hang out for a few. I knew what he meant. I’d never tried pot so I was excited he asked. I called my parents with an excuse. I told them I was working an extra shift and would be meeting my girlfriends for dinner later. We went inside and the place was a wreck. There were clothes on the floor, empty food boxes everywhere and I was afraid to touch the cloth brown couch. He went to his bedroom and came out with a ziplock bag of joints. We went out back and the flower garden was beautiful. We sat at a picnic table and he lit up. He coached me through the first few drags then it became natural and I started to feel relaxed. Naughty thoughts kept popping in my mind about the rumor of his penis size.

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? I slid over to him and slid my hand down his shorts. I felt his warm penis. We kissed. I pulled his shorts off and confirmed all the rumors. He was big. I kept massaging him with my hands then took him in my mouth. I was aroused and took off my black uniform pants. He was nice and said, “I know you have a boyfriend. Do you want to do this?” I nodded yes. He went inside and brought out a condom and said, “If your sure, you need to do the work.” I put the condom on and got on top. I lowered down on him and we began to have sex. He felt so good inside me. I sat on the edge of the table and he rubbed his penis at my entrance and said, “What do you want?” I was so horny and I told him I wanted him inside me. He thrust himself inside me and kept up an amazing rhythm. He was hitting the right spot and it didn’t take him very long before I had my first orgasm. My body was shivering and I felt numb as he kept his rhythm. Then he finished. He lit another one and I called and paid for a pizza to be delivered. We ate and smoked another one. We had sex one more time. I bent over and he took me from behind. I hung out till my head cleared up to drive and I went home.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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 never hooked-up again but we would talk on occasion at school.

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

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Marijuana, hashish

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 didn’t tell anyone but I’m sure he 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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Having my first orgasm.

What was the WORST thing about this hookup? I can’t think of anything.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I was not experienced at the time & I think Jamie sensed that. He was patient with me and I had a wonderful time with him.

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? Jamie and I had amazing sexual chemistry from the start. Even though we only had sex that one time, he was experienced and knew how to pleasure me. I’m still amazed by his stamina. It took lots of practice but my boyfriend finally gave me an orgasm months later.

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 think it’s good to experience other people. I was inexperienced before I had sex with Jamie. After that experience, I was able to have better sex with my boyfriend.

What do you think about the Casual Sex Project? I found this site through an online magazine I read. I was hesitant at first on posting my story but after reading a few stories, I decided to post it.

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