He Wanted Me Bareback

by Jay

What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? California
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? Over 100
How many hookup stories have you here posted before? None

He Wanted Me Bareback

How long ago did this hookup happen? A week ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Fuck-buddies / Booty call

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 met this guy at my workplace. I’m the manager of a retail store. He was a customer. He is a tall, handsome African American man in his mid-forties. It started when he asked me about a product, and we started talking. I noticed that he would engage me in conversation daily and always use my name repeatedly. At first, it was a little uncomfortable that he was flirting but I wanted something to happen.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After about the 4th day that he came in, I knew I wanted to give him my number. I told him that if he had any questions he could text me, but just don’t tell anyone. He said that he wouldn’t want anyone to know, so I figured that he knew what I meant. I felt guilty after I gave it to him, and almost didn’t want him to text, but he did that night. His first text was asking how I was. I hesitated in answering, but I had an urge to see where it would go. I said that I was doing good and asked how he was. His response was that his wife never gave up the booty and he might need to look elsewhere. I knew then that what I said next would determine if we wound up in bed or not. I didn’t want to push the issue, so I just said that I know how he feels and that I wish I could help in some way.
He didn’t respond for like an hour, and I felt a little disappointed until I got a text that asked if I had a GF? I said that I did. He said that I probably got a lot of attention because I was cute. I said thank you for the compliment and that I like the attention. He said, “Do you like attention from anyone?” I said, “Yes.”
He waited 20 minutes to respond with saying he liked how I wore my pants a little tight. At this point, I was getting really nervous but turned on. I have been with other men but it always makes me nervous about getting caught. I said that I like them a little tight but I have a big butt. He asked for a photo, and I sent him 5 pictures of myself naked and in a pink g-string. He sent back a picture of his black penis and a full frontal nude and it looked really good. I told him he had a nice body and he said that I had a super nice ass. He asked if I could host him, but I said I couldn’t, but I said I could rent a room if he wanted.

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? The next day I called in sick at work, so I could rent a room. I took about an hour in the room to get prepared for him and then texted him my room number. I wore a pair of sweatpants over my pink panties and a silky blouse. There was very little talk before he took his pants and shirt off, so I just turned around and took my pants off so he could see my butt. He said, “Man you have a hella sexy ass.” I asked if he wanted to lay on the bed and he lay down. I got on the bed and started giving him head for less than a minute before he got up and said, “Man, I want to play with that ass”.
He asked if I had lube, and I handed him some anal lube and asked if he wanted a condom. He said not with that ass, I want to feel it. I was hesitant about going bareback, but I didn’t resist, and he was already positioning me into the doggy style position on the side of the bed. He pushed my head down further and wanted me to hang my butt over the side. First I felt one finger lube up and then two. It felt really good. He didn’t pause to really loosen me up before sliding in all the way. And immediately started pumping hard without trying to be gentle. I think it was his way of being dominant and feeling like he needed to take my ass as hard as he could. He pumped for only a couple minutes before I could tell he was about to orgasm, and I felt it shoot. He left it in for a minute and then pulled out. He just put his pants back on without washing and said he needed to go, and asked if anyone knew I was gay. I said nobody knows and he left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? After he left, I went to the toilet and then douched. After I got out of the shower I wanted to masturbate, but I resisted until I got home. I texted him later that night and said thank you and that he could fuck me anytime. He said that I had one sexy ass again and said that he had an SUV with tinted windows. Last night we met in a dark parking lot and he fucked me again in the back. It is clear that I turn him on, but it is just a booty call.

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), To feel more desirable, Submission / Relinquishing power, Just happened, I don’t know why just went along with it, It was easy/convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? I don’t know

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? Nobody

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

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

Do you regret this hookup? Somewhat

Why do you regret this hookup? I don’t know. I love to get fucked, but I was uncomfortable with bareback.

What was the BEST thing about this hookup? Him being black and me being white is pretty hot. A lot of men have fucked me discreetly, but I have never been humped so hard. My anus is pretty sore, and I think that that was his goal to dominate a cute white guy.

What was the WORST thing about this hookup? I would like to be kissed or massaged, but it is clear he just wants to cum and then go.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I knew I was bisexual tending towards gay already, but it lowers my self esteem a bit.

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? Casual sex is good in moderation, but I don’t want to hurt anyone. I always find myself trying to find new partners while knowing I shouldn’t

What do you think about the Casual Sex Project? I would need to investigate more

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