First Time I Cheated…



What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? New Mexico
Highest education received: Some college (currently in college)
What’s your current relationship status? In a serious relationship (open)
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Open
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? None

First Time I Cheated…

How long ago did this hookup happen? 1 Year 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? I’ll nickname her O. O. was a gorgeous girl, short around 5’5″ with a little extra weight that complimented her thick figure. Long dark hair, dark skin with a sexy, shy smile. Medium sized tits with an incredible plump ass. She was 18, I was 20. I met O. on Facebook. We had a mutual friend so she hit me up and we started talking. She was flirty and cute. I was flirty and somewhat timid due to that I was in a relationship. I told her and she said she didn’t mind as long I didn’t, which I didn’t. I was ready for some side fun. We then flirted and sent naughty pics back and forth. She liked my abs and big cock. I loved her thick ass and naughty attitude. Needless to say, I was ready to fuck her brains out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It all started when O. said texted me one night thru a naughty talk. “I’ve never given a guy a blowjob.”  With my curiosity peaked and my cock hard, I said, “Oh really?” We then planned to meet up sometime and have her cross blowjob of the list of things to do. It ended up happening unexpectedly and we ran with it. O. had a bad night and didn’t want to be at her sister’s house late night. I ended up picking her up to take her to her friend’s house when we decided to pull into a discrete parking lot. It was very late at night.

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? So O. was venting to me about her night and we talked about it and ended laughing it off. It was our first time meeting so we were both nervous. I said something smoothed about her looking good in person and she blushed. I told her I want to kiss her already, she the smiled and grabbed my shirt to pull me into a hard make out session. She was younger and less experienced which made it hot for me. I kissed her passionately and sweetly, making sure she would have a wonderful experience. After playing her tongue for a bit, I proceeded to run my hands down O’s curvy and sexy body. Her tits were a good handful size and she moaned whenI squeezed them. I wanted O to be surprised and extremely turned on so I started to unbutton her pants and rub her warm pussy over her panties. She immediately, without second guessing started grinding back against my hand, making me gasp a little tighter to rub her clit harder. After this good, horny response, my fingers wandered under panties and into her very wet, very tight, young pussy. As our making out got more intense, I finger fucked O. while squeezing her titty with the other hand. She was in the passenger seat, I was in the driver’s when her hand reached across to find my hardening cock. Once her hand found it, she immediately starting rubbing my cock, then found a way to pull my shorts down. I pulled away from her assault of kisses and said, “You want my cock?” She moaned, “Mmm… Yes,” as I was still fingering her. I leaned back into my seat, O. adjusted herself so she could lean her head onto my hard and ready cock. I gotta say for her first time… she was great! She was so horny, she just took contorl of my cock with one hand and steadied herself with the other. She slurped and jerked my cock at the same time, not being cautious of any mess. It felt wonderful! After all the sexting and pic 4 pics, not only was her first blowjob going great, but I wanted to see her ass. I had seen it plenty of times in pics and I was ready to experience it in person. I moaned out to O., “Let’s hop in the back.” She gladly stopped sucking, looked up, smiled, and crawled into the back first, giving me an amazing look at her ass and an opportunity to spank it. She giggled and I told her cute panties, while I followed her to the backseat. Once in the backseat, O. looked at me and pulled her shirt up and over her head. She was wearing a cute bra and her she looked so sexy, bra and jeans still on. My shorts were off, so I took my shirt off alongside my shoes. She bent over again to continue sucking so I played with her titties and easily unhooked her bra. When she stopped to let her bra fall off, I gently pulled her up and gently pushed her back so she could lay on her back. This gave me the opportunity to pull her jeans off and slide her panties off to reveal her extremely wet and beautiful pussy. I leaned back into a seated position and O. instinctually leaped up and saddled me, positioning herself for a ride of her life. I squeezed her perfect ass, then grasped her hips as she looked at me, smiled and said, “Be gentle with me, your cock’s kinda big.” I replied, “As long as you kiss me.” Her lips attacked mine a second later while she lowered herself on my yearning cock. She felt magical, passion mixed with young raw horniness. We naturally fell into a rhythm of a good pace. As she ground harder and harder against me, I moved my hands from her hips to her ass so I could pull her closer into me. I also bit her bottom lip and used one hand to slap her titty rough but no to rough. She was moaning in ecstasy. Her humping was getting more and more aggressive and she her breathing turned into sexy pants and gasps, so I knew she was getting close to her blissful moment. With that encouragement of her enjoying herself on my cock, I then proceeded to pound her harder, thrusting deeper and rougher into her. I grabbed her hair into a ponytail and pulled her head back so she was looking at the ceiling of the car. She went haywire on my cock at that point, bringing her to a wild orgasm all over my hard cock. I was soo close too which worked out perfectly. She hopped off my cock out of bliss and exhaustion. I slumped back into a position where she could sit between my legs and finish me off with her mouth. I told her, “I’m so close, for your first blowjob I want to finish in your mouth.” She happily seated herself between my legs and started ferociously sucking my cock. It was extra hot that she was also sucking all her juices off my cock as well. Within 30 seconds, I started bucking my hips into her mouth, moaning and yelling, “I’m about to cum!” She handled her first load like a pro, slurped it all off of my cock and licked her lips. We both sat back and sighed, trying to catch our breath. Then O. said “Thank you for that, Really… Mmm… I feel so damn good.”

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? Next day we were back to texting and smiling about the previous night, already making plans for a future hook up. Which still hasn’t come… After my first time cheating, I was curious for more.

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), Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, Power / Dominance, Making new friends, Boredom, It was easy / convenient, To found out what it felt like to cheat.

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? No one. Can’t talk about cheating in such a small town. So I decided to tell everyone online lol.

How would you best summarize people’s reactions about this hookup? Other

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? Her ass… I love bigger, thicker asses so she was a dream fuck. Also finishing in her naughty, young mouth.

What was the WORST thing about this hookup? We didn’t fuck a second time.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Cheating is how you perceive it.

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? I led to other hook ups with other people, more stories 😉

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? For everyone to be more open to being more open.

What do you think about the Casual Sex Project? Neat, sexy idea. Got me to post, which is never.

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