The First/Last Time I Cheated



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? Arizona
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Retail
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? None/First Time

The First/Last Time I Cheated

How long ago did this hookup happen? 3 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? Just met that day

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? Her name was Yesinia. We had just met at a party that I was invited to by another girl I had planned to fuck later that night. Yesinia was very attractive. Very short, thick in all the right places and great assets. Approximate measurements below:

Age: 19?
Ethnicity: Latina
Height: 5’1
Body: petite
Tits: huge
Ass: thick and tight

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In my car. We sat and talked for hours about nothing I can remember. Then there was that deafening moment of silence where you’ve got to make your move so I did. We started making out in the car heavily. Hands were exploring places when she crawled over to my seat and straddled me. She began dry humping me and that’s when I made an executive decision.

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 it was clear that she wanted to have sex, we migrated from the car back upstairs to the apartment where the party we met at happened. All the bedrooms were occupied so we took the action to the couch. We continued to make out and remove the clothing from each other very quickly. Before I knew it, I had her sexy little body on top of me where all I could see was her silhouette in the dark. I sucked and kissed her breasts to get her warmed up before tossing her to the ground where she let me eat her pussy. She thoroughly enjoyed this so I continued until I got her to the edge of her first orgasm. I quickly transitioned from licking her to fucking her on her back. I had her legs spread wide open and began thrusting harder and deeper with every pump. She was very vocal and saying all the traditional dirty shit that most guys like to hear when they’re pounding out drunk. This entire situation was particularly difficult for me because I already had a girlfriend at the time (I know I’m a piece of shit cheater) but at the same time it was happening and I didn’t want it to stop because it felt great. I fucked her on her back until she came and then she insisted on letting her ride me so like any good cheating bastard I obliged. She rode for less than 2 minutes before I was about to cum. I pulled out and came all over her pussy, thighs and tits. A couple minutes later we made a trip to the bathroom together and had round two which was much better than the first time. We were already completely naked from fucking earlier and she was in dick heat or something because she was practically drooling over my cock, biting her lips and licking them profusely. I turned her around facing the bathroom mirror and started spanking her and toting her pussy. She couldn’t wait anymore and demanded that I fuck her so once again I obliged. I fucked her from behind for a very long time and in the process we managed to knock over all the shit that was sitting on the bathroom countertop (not very stealthy) She was whimpering while reaching back with one of her hands and digging her nails in to my arm which I wasn’t used to but enjoyed still. We decided to move to the toilet eventually. She guided me there and sat me down on the closed toilet seat. She straddled me, edging and teasing my cock before I grabbed her by the hips and pulled her on to me. She grinded on me for almost another hour before I came inside of her.

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? After the bathroom bang session, we went back to the couch and put our clothes back on and went to sleep together. I woke up the next morning in a panic and felt particularly guilty and disgraceful for cheating on my partner at the time. Yesinia needed a ride home so I drive her and we never saw/spoke to each other again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication, I was feeling lonely, Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

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

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 talked to Yesenia’s best friend the next morning since we worked together. She had already heard all about what happened and gave me some very constructive feedback about my performance in the sack according to Yesenia. I told a good friend of mine about it and he just shook his head because I didn’t use a condom which in hindsight was and always is a horrible decision when hooking up.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Very

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? Very much

Why do you regret this hookup? Because growing up I observed the effects of cheating on my parents and what it did to my mom. Because of my dad’s disloyal behaviors, I always swore to myself that I would never do that to any woman.

What was the BEST thing about this hookup? I didn’t get heroes for one which I’m very thankful for. It showed me that I didn’t really value the relationship I was currently in and eventually led to me breaking up with my partner.

What was the WORST thing about this hookup? I cheated and there’s no excuse for that behavior. I’ll never do it again and I do not recommend it to anyone. The guilt is relentless and in many ways, I still haven’t let go of it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It has. It showed me that a meaningless one night stand is fun but its consequences far outweigh any benefits associated with it.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Don’t cheat. You’re hurting yourself, in the end, every time. Be true to yourself and those who love you.

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? Casual sex can be/is very normal and I believe healthy as long as it’s being executed properly (not cheating) It has shown me many times before that sex doesn’t always equate to loving a person but showing a mutual respect and expressing your attraction to another human being is a great gift all together. I had many one night stands when I was single and I think I needed that to show myself that the grass isn’t always greener on the other side. I took the hard road, yes, but I wouldn’t change a thing with life being as it is for me now.

What do you think about the Casual Sex Project? I think it’s a great outlet for any and everybody who has a story to tell. Thank you for this CSP.

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