First Time Regrets



What’s your gender? Man
How old are you? 20
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? Chicago
Highest education received: Some college (currently in college)
What’s your occupation? Sales Clerk
What’s your current relationship status? Single
Religious affiliation: Raised Christian, don’t really care for affiliation.
How religious are you? A little
What’s your sexual orientation? Gay/lesbian
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

First Time Regrets

How long ago did this hookup happen? August 7th, 2016

What was your relationship status at the time? Same as current status

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

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? He was a man in his late-30s, possibly 40 or 41. He was very well built, but was putting on some weight as he aged. White, a bit shorter than me, dark hair & eyes. I had downloaded Grindr for a few days, considered the possibility of hooking up for a first time, but either chickened out or didn’t find many guys attractive in my area. He messaged me, and included a face and naked picture. I only found out that those pictures of him were several years old when I met him in person, as he was far slimmer and better-looking in the pictures as opposed to in-person. We were messaging back and forth, and when he proposed hooking up I thought to myself, “fuck it, just do it” and agreed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He gave me his address, and I drove over a few hours later. There was no planning, other than trying to clean myself up beforehand.

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? He invited me in, gave me a kiss, turned on some porn, and then we began to undress. I did not like kissing him. He had brushed his teeth, but it probably was several hours ago since his mouth a slightly stale taste. We went to the bedroom when I layed on my back and he laid on top of me for more kissing, worked his way down my body, and then he began to perform oral sex on me. We then changed to a 69 position and performed mutual oral, then he began rimming and fingering me while still in 69 position. After some time of this, he put me back onto my back and lifted my legs up to rim me some more, before breaking out the lube and preparing me and his penis. He then attempted to penetrate me (but I don’t know if he used a condom!), however I was too tight and his penis was quite thick. We then changed positions for me to sit on his cock, but it was still too much. We moved back to the living room where he performed more oral on me while I gave him a handjob.

However, the pain/trama from the aborted attempt at anal plus a rising feeling of disgust kept me from getting hard and cumming. He, on the other hand, came 3 times. After some time of attempting to jerk off myself, I finally admitted that “nothing seems to be happening”, and then he got some towels to help clean up. After some brief conversation, I dressed and left.

I feel that my partner was a little too aggressive for my first time. I don’t think I communicated that this was my first time clearly enough.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? No, not even close

Did your partner have an orgasm? Yes, multiple

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 didn’t feel anything. Kind of relieved that it was finally over. Never talked to him again, and deleted Grindr. I did regret it, but did not feel shame. However, I do notice that my sex drive has fallen a bit since it happened (writing this over a week after it happened). It’s almost like it didn’t happen, which I feel strange about, but that’s probably a result of excessively high expectations on what sex should be like (combination of porn and fantasies).

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms, I don’t know if my partner was on any (other) method, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, Boredom, Just happened, I don’t know why, just went along with it

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? A little bit

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? Just a friend who knew I was gay. Unfortunately, I did this just a bit more than a week after he had told me he was interested in me, and while he was understanding of how conflicted I felt, he also let me know that it was a bit disturbing to him as he had just told me that he liked me. We haven’t spoken for a week, and I am afraid that his opinion of me has changed for the worst, as I do value his friendship and this was a very “un-me” thing to do.

How would you best summarize people’s reactions about this hookup? Relatively negative

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? I don’t know / I’m not sure

Do you regret this hookup? Very much

Why do you regret this hookup? First of all, I am generally not a very sexual person, compared to other men my age. Virtually everyone in my peer circle has casual sex with their significant others and will occasionally hook-up. I do regularly watch porn and masturbate and fantasize about having sex with other men, but generally don’t act on my impulses as I generally feel that I want to have sex with someone I know, and being a closeted gay, this is difficult.

I regret agreeing to it, I regret not saying anything when I met him in person and saw that he was very different from the pictures that he had originally sent me, and I regret not telling him that he was being a bit too rough during sex.

I was very disappointed and unsatisfied with this experience. We went too hard, too fast, and I was not comfortable with all that was going on in multiple places of my body that made it hard to concentrate and, combined with the pain, caused me to lose my erection.

However, despite strong feelings of regret and disappointment, I do not feel much shame or disgust with myself. I actually feel fairly neutral, like, “Oh. That was a dumb idea.” *shrug* I thought I was going to feel either totally transformed by the experience, and either a strong confidence boost if it was a good experience or severe disgust with myself if it wasn’t, and none of that happened. I feel exactly the same as I did before.

What was the BEST thing about this hookup? Well, I finally had sex! Good to know what it’s finally like.

What was the WORST thing about this hookup? Quite a lot.

I have a very conservative and risk-averse personality, and have developed a repuation among my friends as The Virgin of the group. I listen to my friends (male & female) describe their sexual experiences, and am unfazed by it. This was very much a, “Fuck it, stop being a coward and just do it” kind of impulsive hook-up. I feel that I was not true to myself, and that I was not prepared for it.

My partner seems like a nice, accomplished guy, but he was far too aggressive and was dishonest when he sent my pictures of a younger him.

This experience on one hand, has shown me what sex is, and while it has turned me off from hook-ups and sex in general for some time, I do still think that sex can be a wonderful thing if I have an attachment of some kind to my partner.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? My opinion of myself and my sexuality has not changed very much.

However, my opinion of casual sex as an empty, negative thing hasn’t changed. I know that some readers will probably think, “what a prude/loser”, but I think that many young people my age don’t take into account the implications of casual sex. I know several people who have had unplanned pregnancies and chosen to have the baby, and have been negatively affected in terms of work and school by becoming young parents. I also have heard of much emotional & relationship drama that comes from hook-ups.

I will not be engaging in casual sex ever again after this. It was a stupid idea.

All things considered, how POSITIVE was this experience? Not at all 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? I feel that our culture is too permissive of casual sexual activity and too focused on it. Every month I hear of various sexual assaults and sex scandals coming from universities because the combination of young, horny students, alcohol, drugs, and college campus culture leads to people being reckless. And this is despite several years of having classes/lessons dedicated to educating us about sexuality and sexual assault prevention.

I do think that we need to be more frank with young people about casual sex and its implications, as we merely educate them on the mechanical functions with no regards to the risks of STDs, unplanned pregnancy, rape & assault, and the emotional & relationship problems that may arise from it. This is not, however, and endorsement for abstinence-only sex education or shaming people who engage in casual sex. Everyone is different, and we need to include a wide variety of experiences.

What do you think about the Casual Sex Project? I don’t know much about it, but I think it is a worthwhile project that may help us understand why we have casual sex, as well as allowing people to read honest stories about a wide range of sexual experiences before they engage in them themselves.

I hope that my story will help someone understand that it’s okay to not have a good first time, and that it’s okay to feel that casual sex isn’t for them.

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