I Cheated On My Fiance With Two Brothers



What’s your gender? Woman
What’s your current relationship status? Single
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 40

I Cheated On My Fiance With Two Brothers

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? One of the guys was just my type. Let’s call him Mario. He had some meat on him, and he was about 5 inches taller than me with a goatee, but his personality was what really struck me. He was very outgoing and could really light up a room with his humor. In fact, I had a huge crush on him before I got into a relationship with my fiance at the time. The crush actually never went away. I had met him through mutual friends. The other guy, his brother, had a crush on me at the time. Let’s call him Lorenzo. I had met him at a party and we were “talking” before I got into a relationship. I wasn’t very interested in him back then, but we kept in contact consistently as friends. I had never hooked up with either of them prior to this.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I actually had never stopped contacting either of the men when I got into a relationship because I trusted myself not to do anything with them and I was being completely transparent with my fiance about it. Our conversations weren’t of a sexual nature, per se. That changed when I noticed Mario would always ask about my relationship and make vague sexual suggestions that could have or could not have been just him being humorous. Initially, I brushed it off. Then, he would leave me missed calls. I would ask him about them but he would just try to play it off. One day, he texted me to pick up when he called, so I did. Keep in mind I did suspect he was going to try something but at the time and it was not my intention to entertain it. I should have just left him alone in the first place, but unfortunately, a part of me still had feelings for him. I wasn’t sure what I wanted at the time, actually.

He went on to basically ask if we could become friends with benefits. He knew that Lorenzo and I used to talk, so he intended to keep it a secret from him. I felt so guilty, but at the same time, I felt so alive. There was so much feeling in that kiss for me. I loved my fiance, but I couldn’t deny what I felt for this guy. In the back of my head, I knew this wasn’t going to be the last time. About three weeks after that happened, my fiance and I got into a huge fight. I was really upset and contemplated texting Mario. At the end of the night, I finally decided I had to do something for myself. It wasn’t the right thing to do, but in a way, I felt it was going to liberate me. I performed oral on him in public. Somebody actually caught us, but kind of just laughed and walked away. Everything about it felt so good. I loved the thought of getting caught. His dick was the perfect size. I could tell he was enjoying it and that turned me on. When he finally came the first thought in my mind was that I wanted to keep his cum in my mouth forever. I wanted to take the rest of his cum and rub it on my pussy. I just didn’t want the moment to go away.

I kept it from my fiance for a month. I’m not the best liar, so I broke down and confessed to him. In an unexpected twist, he still wanted to be with me, but he was extremely hurt. After all of this, you would think I’d have the heart to do the bare minimum of not cheating on him again. I didn’t. I was young, stupid, and vying for attention. I ended up seeing Lorenzo somewhere. We were both drinking. We’d always been flirty with each other, but in our minds, it was “harmless”. We ended up holding hands and kissing. It was admittedly the best kiss of my life to this day and somewhat cute. I know, my feelings are all over the place. Anyway, we started feeling up on each other. I stopped him for a second. Instead of telling him that I had a boyfriend and I respect our relationship, in a drunken stupor I told him I had already messed around with his brother. Naturally, he felt some type of way. However, we continued and I performed oral on him. We ended up having sex a few times but that’s a different story.

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? I felt guilty, but at the same time, I can’t deny that I enjoyed it. I ended up developing deeper feelings for Lorenzo, but it never worked out. Surprisingly, I’m cool with all three guys now.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To cheer myself up, Power / Dominance

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? I went to my close friend’s house right after it happened and told her all about it. She wasn’t surprised, but understood what got me to that point and comforted me. A month later, I told my ex-fiance.

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? Very

Do you regret this hookup? Somewhat

Why do you regret this hookup? I was engaged to someone who I genuinely considered my soulmate because we fit like two pieces in a puzzle and I just threw it away. I hurt him and that’s what upsets me the most.

What was the BEST thing about this hookup? If I hadn’t gone through with it, I wouldn’t have learned a very valuable lesson which was to never take the people you love for granted.

What was the WORST thing about this hookup? Hurting the person I loved.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It hasn’t changed my view of casual sex or my sexuality, but I realized that I personally cannot commit myself to someone if I am not fully ready to move on from someone else. I tried to bottle up my emotions about this person and they just exploded in my face, literally.

All things considered, how POSITIVE was this experience? A little positive

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

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 personally think safe, casual sex is great, but it’s DEFINITELY not for everyone. I don’t want to ignore the fact that it has its consequences. I feel like a lot of people lose their sense of self-worth after engaging in casual encounters. Personally, I believe that I’m secure enough in terms of my self-worth to responsibly engage in the encounters I engage in. Admittedly, I have a “ridiculous” (too many people) amount of notches in my belt. However, I’m not mad about it, I’m clean, I’m healthy, and that’s all that matters to me. We live in a very sexualized era. There’s nothing wrong with that. It’s great that now everyone is much more free to do what they please than, for instance, in the 1950s. Whatever people want to do should be to their own discretion. However, STDs and unplanned pregnancies are still very serious and real circumstances that could happen to anyone. In sum, I really would like for society to eradicate the stigma that is associated with casual sex, but also I would like to see people educating themselves on the consequences of casual sex.

What do you think about the Casual Sex Project? I love it! Thanks for giving me an outlet to share my story!

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