First MM Experience



What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US – Nebraska
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 2-5

First MM Experience

How long ago did this hookup happen? 19 Years ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

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

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’ll call him Tony (honestly don’t remember his name). We met during a time in my life where I was a horny college student willing to experiment with men to fill my sexual needs. I was back home on college break and scouting the online world for potential MM encounters (think AIM chat rooms). Tony described himself as a gay, 24-year-old grad student at the local university with his own place. We exchanged pics of each other (first penis pictures and then headshots). He was the tall/giant type man where he was just best described as large (with a small gut). He wore glasses and had straight hair. His dick was 5″ erect (his quote – and it was hard to tell in the photo) with a cut head and slim shaft.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We chatted over two nights and he invited me to come over and to have sex. Now at the time, I was under the impression that we would likely end up masturbating each other, likely swapping oral and that anal was a potential, but I was more wanting to bottom. He said he had condoms and lube and we discussed our sex practices (as I was 100% concerned about HIV/AIDS and other STDs).

I drove about a half hour to his apartment building on the other side of town around 9 at night. He met me at the door and led me into his home. He asked if I wanted to smoke a cig and I said sure. So we stepped out on the patio and small chatted about our nerves. He seemed as nervous as I was and that gave me a sense of ease. We headed back in and sat down on the couch. He reached over and started rubbing my body over my clothes.

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? At this point in my life, I was very much just wanting the dick and had no desire to kiss or cuddle with a man. I did reciprocate his groping-like gestures and we leaned in for a hug. He asked if he could kiss me as he leaned in a bit aggressively to my lips. He strongly kissed me and my first reaction was to just kiss back, which I did briefly before backing away. At this point, my 6″ cut erection was straining in my underwear under my jeans.

He reached down and touched my cock under my jeans and I gasped. He asked if we should take our clothes off and we both stripped. We both stood up and took off our shirts and pants. I could see his underwear tenting and he left his socks on. My boxer briefs were also tented with a leaking spot on the front of them. I remember Tony getting down on his knees and pulling down my underwear so my cock would spring out. It was pointed directly in front of him and he looked up at me as he opened his mouth and sucked me in.

I get weak in the knees as he gave me a very hard suction blowjob, starting on my helmet head and working down my above average thick shaft for a couple of minutes. He licked down my shaft and sucked on my balls that he was caressing with his hand moments before. I was getting really horny at this point and asked to switch positions. He finally pulled down his underwear and he has probably a 4″ long, 1″ thick dick with a small set of balls. I felt a bit lied to as he was smaller than I wanted and what he had said. With that said, I also had remorse and guilt that I said I wanted to hook up and should hold up my end of the bargain. I took his cock in my hand and felt how firm yet pliable it was. I slowly jacked him and noticed he did get progressively thicker at the base, but overall it was a small cock. I felt his small sack and balls and slowly push his large frame back to the couch. He sat down and spreads his legs and I crawled on my knees in-between him to give only the 2nd guy I’ve met a blow job.

I could see the drops of precum on his tip and I leaned in with my tongue to give it a lick. His tip felt spongy as I opened my mouth and inhaled his cock. Given my newness to giving blowjobs, I could take only part of him in before I started to gag. I sucked his cock and licked his balls for a couple of minutes. He asks if I want to fuck, and I said I do.

At this point, he got up and goes to his bedroom and brought back condoms and a small bottle of lube. As he came back, he asked if I would fuck him. I hesitated to answer, but again my hormones were raging and I wanted to cum. I accepted and he rolled the condom onto my cock (love when a girl does this to me). He lubed up his hole and had me lay on the ground. He climbed on top of me facing me and guided my cock into his hole.

I could feel his tight ass engulf around my cock as he held my base and lowered onto it. At this point, I’ve kinda determined this night didn’t go how I wanted it to and I really just became interested in getting off and leaving. He continued to ride me and I focused on his cock bouncing in front of me and deflating as I could feel his ass pleasuring me. He put my hand on his cock and I started stroking him as he moaned and rode my cock. Probably 5 minutes had transpired and I announced to him that I am close to cumming. He took over stroking and said that I should cum in his ass. I moan as I am coming and he kept riding my shaft. It was a decent orgasm and as I was coming down from my euphoric state, I could feel Tony’s ass grab my still buried cock as he arched his back and sprayed my chest with cum. He slowly stopped rubbing himself as he slowed to a dribble. I remember sticking my finger in it and tasting it, finding it had an alkaline taste.

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? He got off me and handed me a towel to clean up with. I removed my condom and set it down and wiped myself off. I quickly got dressed and he put his clothes on as I was feeling anxious about what I had just done, meeting a stranger for sex. I actually didn’t feel great afterward and did have regrets, only because he wasn’t the type I was wanting and felt I was settling for sex in a way. We headed back out for a cig and have idle chat about the sex and I left shortly after. We messaged each other a couple of times the next few days, but I never talked with him again after that weekend.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, It was easy / convenient

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

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

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? I haven’t really spoken to anyone about this experience, except in my count of sex partners I’ve had.

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? Not at all

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? A little bit

Why do you regret this hookup? I do not regret the experience now, but marking as such because I did at the time. I was confused and didn’t know that I had some attraction to guys physiques and manners. He was well mannered but I didn’t have any attraction to him or his cock and so I shouldn’t have gone through with it.

What was the BEST thing about this hookup? Watching his cock erupt and cum on my chest and my own orgasm.

What was the WORST thing about this hookup? Lack of physical attraction.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, but not for a while. I am now more judge about photographs, but I still have random sex with hookups I meet online.

Also, I learned to own my actions. I was hesitant in some of the consent for the actions he led and I did have some remorse for my not saying no. However, I still feel I had complete control of the situation and just had hormones lead me versus more thoughts about my lack of attraction to him. I found that the lesson learned and to either judge more and call myself on it or own the situation I put myself in. I still have random hookups with men and have learned to just say no if it isn’t right.

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

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

Anything else you want to add about this hookup? I was really experimenting at the time and hadn’t discovered my true bisexuality until later in life.

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 think casual sex is something everyone who wants to can feel free to take part in as they choose. If society, when I was growing up, hadn’t still frowned on same-sex, err sex, I would have been way more open to attending say, my University’s BDSM club.

I think society needs another generation gone before we will see the tide towards true equality and no judgment on sexuality, which will lead to casual sex being more accepted.

What do you think about the Casual Sex Project? I think it’s great and will continue to add my experiences that I see fit to share and will help normalize sex.

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