Threesome with Old Crush and her Boyfriend

by Rose

Race/ethnicity: Hispanic
Location: Los Angeles
Highest education received: Some college (currently in college)
Occupation: Student
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many hookup stories have you here posted before? None

Threesome with Old Crush and her Boyfriend

How long ago did this hookup happen? 2 years ago

How would you best classify this hookup? Threesome one-night stand

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’ve known Jessica since I was 14, when I went to high school in Mexico. We became friends when we were 15, though. We mostly were gym buddies and we had a lot of mutual friends. She was the sweetest, cutest girl in our class. I was ecstatic that she wanted to hang out with me. This was before I figured out that I was bisexual and had feelings for her. I just thought she was really cute. Sadly, I moved away when I turned 16, moved to Los Angeles from that little town in Mexico. After about 6 months I got a Facebook account and found her again and we reconnected from time to time. I still liked her enough that I didn’t forget her. I would keep up with her status and check out her pictures.

Alex was Jessica’s boyfriend that she met a few months after I moved away. I obviously had never met him before, but he had lived in Los Angeles before, so when Jessica told him about me, he decided to add me on Facebook. I accepted because I saw on his status that he was Jessica’s boyfriend. Surprisingly, he actually would send me messages and comment on my Wall. He would talk to me more than Jessica would. I thought he was interesting, from what he told me about himself, but I never got a clear picture of what he looked like. I was more interested in Jessica than in him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When I turned 19, I decided to take a trip to Mexico for summer break. I didn’t want to go, because I was pretty attached to my boyfriend at the time, and I had a bunch of trust issues. But I hadn’t seen my family and friends from Mexico in two years, so it was overdue. I updated my status, and who would comment on it but Jessica. She insisted I give her a call once I’m in town. I agreed. Once I arrived there, I gave her a call and we met up for coffee. She was even more beautiful than I remembered. She and I started talking about our lives and relationships. It turns out we had a lot in common when it came to our boyfriends. She wanted to introduce me to Alex. So we made plans to go to a bar in a few days (in Mexico, you’re legal at 18. Not that the barkeepers in my town cared much).

When the day came, Jessica picked me up and led me to her boyfriend’s car. She introduced me to Alex. He was tall, dark and had long hair. He reminded me of a Mexican version of my boyfriend (who is white), so I instantly found him attractive. He was chatty and excited to meet me, since we had been talking on Facebook and had heard so much about me. He drove us to the bar, where more of my old high school friends were hanging out (small town). They were all excited to see me and I them, and we started catching up. We all got to drinking and mingling and talking and goofing around. At one point, we started playing Truth or Dare with an empty tequila bottle. It was me, Jessica, our friend Sal, and the barkeep. The themes got more sexual the more we drank. In one of the questions, someone asked me if I had feelings for anyone during my time in high school with them, and I admitted to liking Jessica and Sal during high school (turns out Sal is gay). Alex overheard this. At the end of the night my cousin dragged me out the bar and took me home, and I tried to sober up. While I was getting ready for bed, I got a text from Jessica, but I could tell it was Alex texting cuz he was texting me in English, not Spanish. In the form of a joke, he suggested he, Jessica and I have a threesome. I jokingly replied sure. Then went to sleep. The next morning, I saw that I got another text from Alex saying to forget about it, that he was drunk. But I got the feeling he was just covering to avoid an embarrassing rejection. I thought about it. This could be my chance to be with Jessica after all this time, even if it meant cheating on my boyfriend. I loved my boyfriend, but I was not happy with him at the time. I felt like I needed a distraction, so I called Jessica to ask her if it was cool with her, and she said yes. So we set a date.

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? My parents have a two story house in Mexico, totally vacated since we all moved to Los Angeles. I managed to acquire the keys to the house, and snuck Alex and Jessica in. No one was home, of course, but the house had neighbors who knew me and my parents well, and I wanted to be discreet. We went up to my old bedroom, where luckily there was still a bed. After giving them the tour, we settled on my bed, nervous. Alex rolled a joint, lit it, and passed it around. We all smoked it, but I was so nervous that I couldn’t really relax. In the end, Alex got the ball rolling and commanded Jessica and I to make out.

It was so sweet and soft. I felt extremely lucky to be able to make out with Jessica, even though she had a different style to her kisses. Alex then simultaneously unsnapped our bras one-handed. We removed our tops and bras and began feeling each other up. She had lovely breasts.  Alex then proceeded to strip us and again simultaneously finger us. Jessica then reached down his pants and stroked his dick. I laid Jessica down and started giving her oral with flavored lube. This was my first homosexual encounter and I was excited. She started sucking Alex off while she fingered me. Then we switched, with her giving me oral sex while Alex fucked her. Alex kept watching me. I avoided kissing him, as I wasn’t comfortable kissing my friend’s boyfriend. But I had no problem kissing her. Then they decided to switch, and Alex wanted to have sex with me while I gave Jessica oral. She sat on my face while Alex got on top of me and entered me. It was then did I notice that he had a small dick. I was so absorbed in Jessica that I hadn’t noticed before. I was so surprised and a little disappointed. But then he started really fucking me. He had MOVES! I was actually starting to get excited. But I faked it and got him to pull out so he could finish with Jessica. We switched condoms every time he switched girls. He and Jessica kept it going and I just watched at this point, and when they finished, I lounged on the chair, continuing to watch them and thinking about what we had just done. We had a fucking threesome.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used condoms, and I told them I was clean. I didn’t ask them if they were clean though, and considering where Alex has been, I should have asked.

What were your REASONS for having this hookup? I was in a relationship with my boyfriend at the time, but I had confused feelings. I was depressed because I had found out he hooked up with a girl whom I thought was my friend during a time when he wanted a break from me. We would still hook up during this break time, so it felt like we were still together. So when I found out a few months later about what he had done, I was so confused and angry and hurt. I loved him too much to leave, but I hated him so much for betraying my trust like that. I guess that while I was in Mexico, away from him, I decided to have this three-way to get back at him. And being able to do it with the girl of my dreams was definitely a selling point. I jumped at the chance to kill two birds with one stone: get even with my boyfriend with the girl of my dreams. Alex was just icing on the cake.

Were alcohol or drugs involved? If so, how much? We smoked one joint of weed between us, so not a lot. Not enough to relax me.

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? The aftermath of the hookup was not ideal. Jessica and I kept talking as if it didn’t happen, and we all swore we wouldn’t tell anyone because they live in such a small town that word would spread and tarnish our reputations. They lived in a town where having threesomes and having homosexual encounters were taboo. Scandalous. They lived among closed-minded people, even amongst our peers.

As for Alex, that is another story. He became infatuated with me. He and I met up to get to know each other more even after the threesome. We got to talking and we found out that we had a lot of things in common. I was like the female version of him, except I was sweeter. He saw me as Jessica, only that I understood him better since he and I were so alike. Needless to say he fell for me and hard and fast. I was stupid enough to indulge him. He took me to the woods and we talked, and then he kissed me. I didn’t stop him, and soon we were in the woods, getting frisky. Only it started raining and there was mud and bugs everywhere so we didn’t do anything. I felt guilty because this wasn’t a setting where Jessica would be okay with it. Sure, I’ve had sex with her boyfriend before, but in this other instance, it would have been behind her back. He would have cheated on her with me, and that made me feel like a horrible friend. Thankfully, my flight back to LA was the next day, so I got to escape it all and put it all behind me. Alex saw me before I left for the airport, saying he had become undone, that he was in love with me. I just didn’t know what to say. I just left and reminded him that I have a boyfriend waiting for me in Los Angeles, and that he had Jessica. I broke his heart, and I felt like I made a mistake doing this threesome. But I certainly had not expected that.

To whom did you talk about the hookup? How did they react? I didn’t tell a soul about this. We had sworn to keep it secret for the sake of privacy from their small town, where everyone was in everyone’s business.

Was this a consensual and/or wanted experience for you? For your partner? This was planned, and consensual. I was curious to try it out, and so were Alex and Jessica. I was the only girl they knew who was open-minded and discreet enough to pull off a threesome with them.

Do you regret this hookup? If so, why? I do, yet I don’t. I like the fact that I can count myself as one of those people who’ve had a threesome. I like the fact that I can count myself as one of those people who’ve had a lesbian experience. I like the fact that I got to do it with my old high school crush. But I do regret the aftermath of the experience. I regret that my friend’s boyfriend fell for me. I regret that I led him on a little, then broke his heart. And I regret not letting her know for fear of losing her friendship. This hookup got more complicated than it should have. It should have been casual sex. But instead it became drama. Thank goodness I got away.

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 about this hookup was the sex with an old crush. The  fact that sometimes size doesn’t matter, but moves do matter. The fact that I got to do something so naughty and got away with it in my parent’s house. The fact that we have a dirty little secret that none of our other mutual friends have a clue about.

The worst thing about this hookup was the drama. The fact that I had to break a fragile heart so coldly even though I don’t consider myself a cold person. The guilt. The fact that Jessica and Alex broke up a few months later, probably because Alex realized he didn’t want Jessica anymore.

This experience has led me to steer clear of threesomes with other couples. I still have other casual encounters, but no threesomes, and no females. I’ve explored my sexuality and came to the conclusion that I don’t need women to make me feel good. I’m still attracted to them, but a man satisfies me better. I try to be careful around my guy friends with girlfriends. Don’t want to spark any drama.

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

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

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