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What’s your gender? Woman
How old are you? 28
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? U.S.
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Dating casually
Religious affiliation: Christian
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 2

Taboo Workout

How long ago did this hookup happen? A little over a year ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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 had joined a gym close to my apartment while I was in grad school. I wanted to get back into a workout routine while I was in school, so I went at night after my classes about 3-4 times a week. One day I was using a glutes machine and sat down on the machine next to it to rest between sets. Two men approached me to say hello. They were black, tall, and relatively in shape. One of them was taller and more muscular than the other (but not necessarily more attractive), and I later learned he was a regular at the gym and interacted with the patrons often. The other, “Rob,” was darker-skinned and had slightly thinning hair in the back and a little gray at his hairline. He looked to be in his mid-30s. I thought his face was cute, and he was obviously the more aggressive of the two. He introduced himself and teased me, saying my arms were more cut than his. I was glad they at least approached me, since most guys in the gym (and elsewhere) just stare but never speak.

I saw Rob in the gym regularly after that. One day I was doing lunges facing the mirror, and Rob, his friend, and a woman were near me. The men were helping the woman with a workout, but they seemed to be showing off a bit too. Rob spoke to me and said something funny so I laughed. The woman kind of stepped between us and turned Rob’s attention back to her. I assumed she must be his girlfriend.

She didn’t come to the gym with him all the time, though, so whenever he was alone, he and his guy friend would come near me to show off, flirt, and try to show me new workouts (which I wasn’t interested in learning, since I was focused on my own routine). One day Rob asked for my number. We started texting fairly regularly and he asked to come to my place. I told him I was hesitant since I don’t usually invite men over. So we compromised and he said he would just park outside my building and we could sit and talk in his car.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The first time I sat with him in his car (which was nice and roomy), we simply got to know each other better. I asked if the woman in the gym was his girlfriend and he said she was, and they lived together and had two kids together. This was a bit of a turn-off, but it wasn’t a complete deal breaker. At that point I just thought this was a friendly flirtatious thing for the most part, with the faint possibility of casual sex in the future if it felt right.

He also told me that he and his girlfriend were swingers and enjoyed FMF threesomes, but he wasn’t quite ready to have a MFM threesome and allow her to fuck another man (eye roll). He propositioned me to join them in a threesome sometime, and I pretended to consider the idea. He said if I was down, the three of us would hang out first, maybe at a strip club, to get comfortable with each other. I told him I had reservations since I wasn’t bisexual…and later I turned down his offer completely. He accepted my answer, but continued to see me in his car outside my building.

Once the flirtation had become heavier, he showed me his dick voluntarily, and it was 7-8 inches and really thick. I expressed surprise because it was so big, but I told him I wouldn’t be doing anything with it just yet. He told me he liked that my body was tight, and it looked like I had good pussy. We also discussed our sexual preferences, and he said he wanted to make me cum. I told him I only orgasm from my vibrator, and he said he would make it his mission to make me cum since he always makes his partners cum. I’d heard that line so many times, but I left it at that since I didn’t want to kill the vibe or bruise his ego. After we had gotten comfortable kissing each other with tongue, he started greeting me outside the car by kissing me and grabbing my ass. This made me shy since I didn’t want other people in my complex to see this display from their windows.

Inside the car one day he was being pretty aggressive, which turned me on and made me loosen up a bit. He marveled at my tits and reached down my shirt to rub my nipples, and I moaned. Encouraged, he exposed my breasts and sucked my nipples. I threw my head back and continued moaning and he got really turned on and tried to reach under my skirt. I stopped him, as I was still hesitant to sleep with him, and told him I needed to go. He insisted that he at least walk me to my door, and I warily allowed him. As he followed me up the stairs, he swiftly lifted my skirt and felt my ass, which startled me and I giggled loudly. I whispered to him to stop so the neighbors wouldn’t hear, but he kept on and I was dying of laughter. When we reached my door, I unlocked it but didn’t open it yet because I didn’t want him to be encouraged to come in. He suggested that we just fuck right there outside my door, but that was so absurd that I said absolutely not. He turned to leave, but I felt kind of bad since he looked so worked up and his clothes were even a bit disheveled.

A few days later we agreed that he could finally come up to my place. We knew that we would be having sex and he said he would free up his whole day for this, and that we could take our time and watch movies too. He also said he was bringing some batteries so that I could use my vibrator in front of him. I wanted to wear something sexy that would give him easy access to play with my tits, since that’s one of my biggest turn-ons. I decided to wear a loose white crop top with no bra, and white shorts that made my ass look like a bubble.

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? When he got there we sat on the couch and started talking and watching TV. He noticed my hard, dark nipples poking through and played with them through my shirt. I was briefly in heaven and wished he would’ve done that longer. He told me to stand up and take off my shorts, and I complied, bending over so that my ass was in his face. He stuck his face between my cheeks and licked my pussy a bit through my thong. Then he rubbed my pussy lips and marveled at their plumpness.

He stood up and asked for head, so I got on my knees. I knew I couldn’t take all of his dick in my mouth, so I began to use my hand too, but he told me not to use hands. He then grabbed my hair and held my head in place while he fucked my mouth steadily. Then he guided my head to his balls and I licked and sucked them gently. I came back up to his dick and started slapping my tongue with his dick. He took over and continued slapping the heavy dick on my tongue as I just knelt there with my head lifted and tongue out. I usually don’t enjoy giving (or receiving) head much, but this time it was so enjoyable since his dick was so massive and it made me feel like a porn star.

When we were ready to fuck, he laid on his back on the floor and I got on top. I had removed my thong but was still wearing the white top. He wanted to go raw, but I made him put on a condom since he had brought some anyway. My pussy was super wet and I lowered myself onto his dick. It took a while for my pussy to adjust to the huge dick that was filling it up, but once it did, we got into a rhythm. As I rocked back and forth, he pulled my shirt up to reveal my breasts, gathered the cotton material in his fist, and held the cloth against my back so that it was tightly wrapped around my body, right above my nipples. I looked down and the sight of my erect nipples poking out underneath, coupled with being restrained in some way, turned me on immensely. It seemed to turn him on too, because his eyes remained wide as he stared at my underboob and nipples as I started bouncing up and down on his dick. He looked completely animalistic, since this was pure lust at work.

We eventually moved to the couch and he spread my legs and entered me. I told him to go slowly and gently so my pussy could get used to his dick again. He started off slowly, then suddenly thrust deep into me and made me scream. We laughed together and I told him not to do that again. Soon he got to thrusting steadily and once I was comfortable I asked, “You like this pussy?” He apparently wanted to maintain control since he responded, “You like this dick.” I wasn’t about to battle egos during sex, so I submitted and told him I did like it. After a while, my legs were getting tired and sore, so I asked to take a break. He laughed at this but complied. We laid on the couch together, spooning, and found a movie to watch. Soon after it started, he entered me from the side and I moaned loudly since I love this position. He picked up the pace and before long he was steadily pounding me.

We didn’t end up using the vibrator, and neither of us came (I think he wasn’t used to wearing condoms, and he wanted me to cum first). It was still good sex to me though.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

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? Rob and I hooked up a few more times after that, once with him only giving me oral. We would see each other in the gym and he would flirt with me openly now, sort of marking his territory to the other men. I saw his girlfriend there occasionally, and she remained oblivious. At one point I joked to Rob that she was cute (as I do appreciate women’s beauty), and he brought up the threesome idea again, but I told him I still didn’t have that desire.

After a couple months or so, I felt he was treating me more and more like a booty call (we started out as sort of friends) and being somewhat emotionally manipulative whenever we would communicate. One day we were texting and I was telling him how I was frustrated that men who had shown interest in me lately were married. He then came clean to me that his “girlfriend” was actually his wife! I don’t really mind having sex with a man with a girlfriend, but marriage is where I draw the line, and Rob didn’t give me the opportunity to make that decision about getting involved with him (neither he nor his wife wore rings). I gave him a piece of my mind, and in response he told me I needed professional help. I blocked his number and of course we haven’t talked since. Luckily I never see him at the gym after that because he had switched gyms (prior to our argument).

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Submission / Relinquishing power, Didn’t want to disappoint my partner, It was easy / convenient

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? No one

Did you get emotionally hurt as a result of this hookup? A little bit

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

Do you regret this hookup? A little bit

Why do you regret this hookup? I don’t regret the sex itself because it was a great experience, but I regret the fact that he was married (if that makes sense).

What was the BEST thing about this hookup? Having sex with an older, dominant man. Older, experienced men with dominant personalities get me every time! The way I gave him oral was a huge turn-on, as well as how he restrained my breasts a bit during sex. It’s still one of my fantasies to be fully restrained. Also the fact that everything we did together, sex or not, was risky and that was thrilling.

What was the WORST thing about this hookup? The fact that he was married and deceived me. Also his dick was just a tad too big for my taste and was a little painful at times.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me think about what types of sexual acts I would be open to if I ever engaged in a FMF threesome. I’m not interested in kissing a woman or touching pussy in any way, but I might enjoy playing with tits or ass if the woman was attractive enough and had a body type I liked. Usually people in threesomes want the females to go farther than just that, so I don’t think threesomes are for me.

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

All things considered, how NEGATIVE was this experience? A little 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? If you’re going to engage, I think it’s important to know and enforce your boundaries. I believe casual sex, if approached without shame, can help give women the confidence and sexiness that we all secretly want…the kind that becomes a part of us and is present even outside the bedroom. 🙂

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

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