The Time I Cheated on My Boyfriend and Almost Had a Threesome

by Melody

Age: 22
Race/ethnicity: Southeast Asian
Location: Australia
Highest education received: Some college (currently in college)
Occupation: Student
Religious affiliation: Islam
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many hookup stories have you here posted before: 0

The Time I Cheated on My Boyfriend and Almost Had a Threesome

How long ago did this hookup happen? A few weeks ago

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

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 met both Bryan and Brandon that night, at a friend’s party. Brandon was skinny, of average height, with dark longish hair. I can’t remember his eye color, it could have been brown or green. Bryan was tall and awkward, with blond hair and I think brown eyes. Brandon was easier to talk to and I was more attracted to him than to Bryan.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I slowly got very drunk at the party. I don’t know who initiated it, but Brandon and I began flirting with each other. We played Spin the Bottle and Brandon had to kiss me on the mouth, which I warmly welcomed. After the game, Brandon said something that was basically challenging my kissing skills, and we began making out. I noticed Bryan witnessed it and I saw what I thought was envy in his face, so I pulled him closer and started making out with him. I might have drunkenly suggested a threesome during our interaction, which both of them may have taken seriously. I can’t remember how, but Brandon and I ended up in a dark room with a single bed (presumably a guest room).

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Brandon and I made out on the bed. He took off my clothes and I took off his. He put his fingers inside my vagina and began pumping in and out. We kissed some more. He kept saying, “You’re so wet,” and played with my vagina and breasts. He asked me to do 69, and then doggy style. It was rough and fast and amazing. I almost had an orgasm, but he didn’t, so we ended up just lying on the bed, naked, drunkenly talking. Brandon was friendly and sweet. It was pleasant and nice, and I forgot about my boyfriend for a while.

Bryan then entered and offered to drive us home. I lived far away, but it was decided that I would be spending the night at Brandon’s. Outside of Brandon’s driveway, Bryan asked me to go to the backseat. I obliged. He and Brandon began taking off my clothes. I started giving Brandon a blowjob while Bryan put his fingers up my vagina. He was rough, though, and I kept being pushed back. Brandon said it was too crammed and he needed a drink. He went inside his house and left me with Bryan. Despite his sweet and awkward appearance, Bryan was extremely rough. He bit my lower lip, he bit my nipples, he jammed his penis inside my vagina and pumped hard. I was in pain, but I was enjoying it. We did it with him on top, with me on top, and from behind. Luckily, he came quick. After he was finished, we went inside Brandon’s house. I was tired. I laid down on Brandon’s bed while he took off his clothes and asked if I was uncomfortable if he slept in the nude. I told him I didn’t care. We probably had two hours of sleep before he woke me up, started kissing me again, before mounting me and putting his penis inside of me.  He finished 15 minutes later, and we both went to sleep with his arms around me.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Brandon wore a condom the first time he fucked me. Bryan didn’t have a condom when he first put his penis inside me, but Brandon gave him one. He came inside the condom. Brandon didn’t wear a condom the second time he fucked me, but I asked him not to come inside of me and he came on my stomach. No STI history was discussed.

What were your REASONS for having this hookup? I was drunk and I enjoyed the attention both guys were giving me.

Were alcohol or drugs involved? If so, how much? I had 250 ml of vodka with me that night and I possibly finished three-quarters of it within three hours.

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? I felt a mixture of things. I felt remorse from the betrayal that I’ve committed, but at the same time I enjoyed it. I hope to continue being friends with Bryan and Brandon. I am not romantically interested in either of them.

To whom did you talk about the hookup? How did they react? I never talked about it to anyone. I can’t. My friends would not understand, obviously I can’t talk to my boyfriend. I have tried multiple times to write it down but have been unsuccessful until today.

Was this a consensual and/or wanted experience for you? For your partner? Yes, it was consensual for all of us.

Do you regret this hookup? If so, why? I slightly do. It makes me question my morals and my feelings toward my boyfriend, which I realize hasn’t changed… he has just been unable to fulfill my sexual needs.

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 thing was that it was very enjoyable for me – it was one of the only times I could experience orgasm with men. The worst thing was that it happened while I am in a committed relationship. I have now given up the thought of being monogamous. I am unable to do this. If this relationship fails, I will probably never try being monogamous again.

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

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

Anything else you want to add about this hookup or anything else? Sex does not constitute love, and being the very damaged person that I am, I have the ability to compartmentalize sex and romance. Sex is just sex. It’s a biological need. It’s a physiological experience. My relationship with my boyfriend is separate from my sexual pursuits and I wish for it to remain that way for as long as I can manage.

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