First Time Cheating

by Daedalus

Gender: Male
Age: 20
Race/ethnicity: White
Current location: California
Highest education received: Some college (currently in college)
Occupation: Drug Dealer
Relationship status: Girlfriend
Religious affiliation: Absurdist
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

First Time Cheating

How long ago did this hookup happen? 3 days ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling

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? My sister had gone to school in New York but had to come back due to personal issues. While there she made a friend who I happened to meet on Tinder during my winter break. We talked a bit about life and our personalities and we both decided we liked each other and wanted to meet. She was chubby with short hair and had a great ass and tits.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met up at a Starbucks and talked a bit, I could tell she was shy and had low self esteem. I gave her some advice and generally told her to think more highly of herself, as I had dealt with the same shit when I was her age (18). We went up to a park that overlooks the LA sprawl and started kissing. I put my hand down her pants and she eagerly reciprocated. I told her to take her pants off and I ate her out for a bit before climbing on top of her and putting on a condom. I came pretty quick after which we went to fingering her and she came. She sucked me for a little while and then I tried to get inside her again but we were out of condoms.

We rushed down to the drugstore, bought a threepack and spent the rest of the night parked in a deserted lot fucking. I came several more times.

Next day we met up, ate breakfast and found another good secluded parking spot. She was wearing no bra no panties and a dress with leggings. I ripped a hole in the leggings with my keys and fucked her till the sun came up. Then I came in her mouth. We did some shopping afterwards and decided to go see a movie. While waiting for our showtime we found a parking spot out behind the movie theater and I fucked her again.

Then we watched the movie and I dropped her off at her house.

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? She was much more naughty than her innocent exterior belied, which was a welcome change from my girlfriend back at my school whose virginity I had taken and was just getting acquainted with blowjobs and positions other than missionary. Once she told me that she wished we had a bed so I could take her from behind.

She had clear emotional issues. Cried after we first fucked and told me that she thought she was ugly, which, for the record, was untrue. I sympathized with her and tried to provide as much encouragement as I could.

Did you have an orgasm? Did your partner(s)? She had one, I had several.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? She insisted on using condoms. Smart girl.

What were your REASONS for having this hookup? I had rushed into a committed relationship at my college because I thought I was not attractive enough for casual sex. So when I came back home for break I decided to fuck around.

Were alcohol or drugs involved? If so, how much? None

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We agreed to keep in touch despite being on opposite ends of the country. Hopefully our breaks line up again in the future. I tried to make the experience as empowering for her as possible as I know what it is like to struggle with self doubt and mental illness.

To whom did you talk about the hookup? How did they react? I told one of my LA homies. He made a joke and we changed the topic

Was this a consensual and/or wanted experience for you? For your partner? Consensual for both

Do you regret this hookup? If so, why? I experienced mild guilt afterward but it quickly faded.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best was how naughty and eager she was once she was comfortable with me.

The worst was that we only got two days of fucking in before we had to split.

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

All things considered, how NEGATIVE was this experience? A little negative

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!