I Never Thought I Would, But I Did

by Xena

What’s your gender? Woman
How old are you? 35
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Student
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Free Lover
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 0

I Never Thought I Would, But I Did

How long ago did this hookup happen? 10yrs

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

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? Well, I had heard of him (Lamar) and seen him before, but it was never good stuff. However, I did find him attractive. He was so different from my fiancé. He was more thuggish and bad boy like. He worked at a shoe store in the mall with my roommate and she always spoke about how arrogant he was and that he had slept with all the nastiest girls in the city. She shared this with me while my fiancé was around and we all expressed how he better never try to flirt with either of us because he had no chance with girls like us as we only got with more respectable and clean guys. She even mentioned that she heard he had at least one STD, maybe more. It was such a turn-off. I did end up in his store once though, and he ended up helping me and giving me his card and he wrote his cell number on it. I saved it in my phone just in case I needed some help in the future with shoes…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One night I went to the club with my fiancé, dressed as my normal slutty self (short dress and no panties). We had a somewhat open relationship so my fiancé let me dance on the stage and sometimes let my goods show. I’d get down afterwards and dance and make out with the guys I noticed and that I found attractive. Sometimes I let them finger me on the crowded floor while we danced. My fiancé always knew and we had these looks we gave one another as communication when it was happening. Some of the guys got lucky and we ended up having sex after the club, but only after hubby’s permission.

Well, this night, I was actually dancing with my fiancé when I saw Lamar across the room standing with some other guys. I had downed a few amaretto sours so I was a bit tipsy, but he looked soooo sexy to me. I danced a bit more with my fiancé and as soon as my drink was empty I went to get a refill, but I took the long way so I could walk by Lamar and tease him. I rubbed across the front of his pants, and across his dick. It was MUCH bigger than I anticipated. I kept going and went to the restroom before going to the bar.

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?

As we began to leave, Lamar told me to come see him after I left. I told him I couldn’t because I’m with my man. He just said, “figure it out, just come”, and that was soooo sexy to me. I had to figure it out, so I started showing my fiancé extra love by snuggling against him and giving him lots of kisses. I knew he was getting curious but I had to decide what kind of lie to make up in order to go see Lamar. Once we got to the car and I was still clueless as to what to say. I kept showing love to my fiancé and he finally asked, “Okay what’s wrong with you?!” I was just honest and said it. “I want to go see Lamar.” He said, “What? Are You serious?! You know how nasty he is! Even you said it!” I said, “I know baby, but I wanna fuck him.” He asked me if I was serious and he really grilled me for a couple minutes, but I needed it. I kept begging and started rubbing my wet pussy and he saw me. That’s when he eventually gave in and said, “Fine, if you want it that bad.”

He drove home and then I texted Lamar that I was driving to his house. When I got there, he left the door open and told me which room to come to. I went in and went to his room where he was under the covers. He just motioned for me to come on over, so I did. He was naked and waiting. I didn’t bother taking any clothes off, I just got under the covers with him and we started making out. I felt his dick poking my hip through my dress. I wiggled my hips just enough to let my dress ride up and his dick slipped between my legs. It didn’t go in, but I could feel it throbbing against my lips as we kissed. Eventually he couldn’t resist. He got on top of me missionary style and fucked me sooo good.

It lasted forever and he put me in so many different position that I had two orgasms. I passed out asleep after my second orgasm and I work up later and he was laying beside me, stroking his dick. He reached over and gave me a glass of water which woke me up a bit. Then he told me to get in top so he can finish. I climbed on top of him and he did all the work. He pounded me so good for like three minutes and then he came. I just let him finish inside of me. Then I laid next to him and fell asleep again. Next thing I knew, I woke up and the sun was rising. I panicked and said I needed to go. He just laid there as I got up, pulled my dress back down, grabbed my phone and left.

My fiancé had texted twice just to see if I was okay, so I texted him back immediately after getting in the car, but he never replied. When I got home and walked in I was gong to get a quick shower and hop in bed, but as I walked pass the bed, my fiancé sternly said to me, “Come here!” I obeyed and sat by him on the bed. He asked where I was all night and was honest. I asked him was he upset and he he pulled the cover down showing me his quickly growing dick. I knew he was waiting on me to come home, so I knew what I needed to do. I climbed on his dick as he started telling me how he couldn’t believe I went to fuck him. Then he said, “…And I love it. I love how nasty you are baby. I don’t know why but it turned me on more than ever.” At this point he started fucking me really hard and fast. I started to detail what happened but then he let loose a powerful orgasm deep inside of me.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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 was freaking out the next day. I got all kinds of antibiotics to take just in case. I was too frightened to even consider doing it again with him. I just don’t really think about him anymore if I can help it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication, Power / Dominance, Submission / Relinquishing power, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? I don’t know

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? My fiancé and a few girlfriends. Fiancé had mixed emotions initially but eventually encouraged me to re-tell the story as we were having sex. My friends were worried I may have caught something initially, but one of my girlfriends ended up hooking up with him a little while later.

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? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The fact he was said to have an STD but we still did it with no condom. It was a thrill.

What was the WORST thing about this hookup? Honestly he lasted too long. It hurt towards the end.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It did. I had sex behind my fiance’s back many more times with no hesitation and never was in a rush to confess. Sometimes I even confessed years later and it turned him on even more.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Honestly, It gave my fiancé a desire for me to seek out another guy rumored to have a STD and sleep with him. It’s a weird fantasy that turns him on still to this day.

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 love the freedom to be sexually actively with anyone I desire and having the blessing from my husband to do so makes it so easy have fun while out partying. I think casual sex is great but should have at least some sort of agreement in place if you’re in a relationship. At least that’s how we started.

What do you think about the Casual Sex Project? It’s amazing. I’m happy to have a safe place to share these stories.

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