Lesbian Experience

by Jake
Gender: Male

Age: 28
Race/ethnicity: White
Location: Chicago
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Student
Religious affiliation: None/agnostic
How religious are you? Not at all
Sexual orientation: Gay/Lesbian
How many hookup stories have you here posted before? none


Lesbian Experience

How long ago did this hookup happen? 6 days ago

How would you best classify this hookup? 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? This was a guy I’d met on OKCupid. I thought he was really cute, so I was excited when he messaged me. He was Indian, tall, very thin, pretty eyes.

When we hooked up, I found his dick to be quite big. Not terribly thick, but quite long. He was cut. He had a lot of hair in his asscrack and on his taint. His fingernails were slightly too long for me – every time I looked at them I was grossed out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We started flirting pretty hard and pretty fast, but once we started getting into sex talk, we learned that we were both bottoms. I was ready to call it off then, because I’m 100% bottom – I never top, because it just doesn’t do it for me. And I wouldn’t want to be with someone who sometimes wanted to get fucked, because I know he can’t get it from me. I’ll get soft. But I love getting fucked.

But this guy was willing to give it a shot – we joked that it would be a lesbian encounter. I’ve had a few lesbian encounters (as in, two bottoms) before and they’re never really that satisfying. We end up just making out a lot and fingering each other. Kind of boring. But this guy was cute enough that I was willing to try it out.

We exchanged some shirtless pics and then he pressured me into sharing my dick pic. I did, and he claimed he didn’t have one on his phone. I called bullshit on him and said that I knew he had an iPhone, so he should just take a picture. He wouldn’t do it at first, but I guilted him pretty hard and eventually he sent me one.

We made plans for him to come to my house on a Friday night. He wanted to stay the whole night – he said we should promise to stick out the entire night together, even if we turn out to have no chemistry. I again called bullshit – he was trying to make it sound kind of whimsical and romantic, but I knew that he was from a strict Muslim household and lived with his parents, and that he was going to feed them some lie, which would fall apart if he had to return home at 2am because I’d kicked him out. I told him that’s what I thought was the actual case, and he confessed. Which was fine, because I expected him to stay the night anyway. I’d just rather he tell me the truth about why than make up some bullshit story.

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? He came over and we pretty much immediately got busy. There were a few minutes of awkward standing around, but then we started making out. He was very thin in person, and his face looked quite hollow – he’d clearly had really bad acne as a child. He was still cute though.

As much as he came across as being very much a bottom, he turned out to be quite dominant with me. He ate my ass and sucked my cock for a while, and then we fucked. He was quite forceful – I was surprised. I’ve flip-fucked with bottoms before and they usually go soft pretty quickly (I do too), but this guy stayed hard the whole time. He seemed to actually be into it. Nevertheless he couldn’t cum by fucking me. He kept asking me if I was close while he was in me, and I would usually say yes. I’m usually always close when I’m being fucked, but I like to cum at the same time as the other guy. Nothing is worse than unsynchronized orgasms. Then one of you has to wait around and pretend to still be horny while the other jerks off. Boring and awkward.

So neither of us would cum, because he couldn’t cum from fucking and I wouldn’t cum until he did, so he pulled out and we jerked off together. Afterwards, we talked about morality. I asked him which was the most moral act: (a) a rich man who gives a huge amount of money to charity, and is publicly lauded for it, (b) a poor man who gives his last dollar to a blind man while no one was looking, so no one would ever know he had done something good.

He felt that the rich man’s gift was the more moral act, because it had a bigger effect. He’s a utilitarian. I, on the other hand, thought the poor man’s gift was more moral, because it was a bigger sacrifice, and because it was purely selfless, with no capacity for any sort of return gains – unlike the rich man, who gets praise and respect, the poor man gets nothing aside from the knowledge that he helped someone.

After that we watched an episode of Sex and the City and then fucked again. Again he couldn’t cum from fucking, so again we jerked off. We went to sleep and then he woke up early and left.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used condoms, but we didn’t discuss STDs or anything.

What were your REASONS for having this hookup? I was horny. I hadn’t been fucked in a few weeks.

Were alcohol or drugs involved? If so, how much? No. We were both sober.

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? I was glad it was over. It was fun, but he was a little too forceful in fucking me, it hurt a little at times. Also, he was a little too lovey-dovey afterwards. I usually prefer physical closeness after sex, but no lovey-dovey words. Ideally, we would fuck, then we’d put on our pajamas, eat ice cream and watch Downton Abbey. He wanted to gaze into my eyes. No thanks.

He wanted to hook up again. I said no thanks. Nice guy, but too lesbian for me.

To whom did you talk about the hookup? How did they react? My friend. She rolled her eyes at me and said she wasn’t surprised. Later she called me a slut. That made me hate her a little bit. She gets very judgmental about me having sex, but she’s fucking this guy she’s in love with and who is in love with her, but she’s also fucking other people on the side because she “doesn’t know what we are” (in terms of the guy she’s in love with. She can’t tell if they’re in a relationship or just fucking.) What’s more, she doesn’t EVER use condoms, and only gets tested maybe once a year or less.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for both of us.

Do you regret this hookup? If so, why? No. I don’t generally regret hookups, unless the hookup involved unsafe sex that happened because we were both too horny to get out a condom.

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? His dick was good. His creepy long fingernails were bad. The morality talk after was good. The lovey-dovey crap was bad.

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

Anything else you want to add about this hookup or anything else? It was super lesbian.

Contact me anytime. I have lots of stories. This was just my most recent.

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