My First Time with a Guy (or Two)



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
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Accountant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Open when horny
How many sexual partners have you had in your life (including oral sex)? 25+
How many hookup stories have you here posted before? 0

My first time with a guy (or two).

How long ago did this hookup happen? 2 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? 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? I was cruising CL as I’d done a thousand times before. I had never met with anyone from the site. In the past, I had always just used it to masturbate while I message people using the email feature. That night, I had been smoking weed and was extremely horny when I got an email from a post I had messaged earlier. It was a gay couple in their early forties looking for a third. A tall blonde and a shorter lumber jack type.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After numerous emails back and forth, and sending them a picture of my dick, they emailed me their phone number and asked me to text them. I did. They said they want to suck my dick together. I had not cum yet and decided to give it a shot. They sent their address and I drove over to their house.

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 I walked in the house, I was very nervous. They were both in just pajama bottoms. They could tell I was nervous and offered me a drink. I took it and sat down on the couch. They sat on either side of me making small talk. After a few minutes, the blonde started rubbing my dick through my jeans. Then the other unzipped me and pulled mine and then his pants off. He leaned down and took me in his mouth while the blonde tried to kiss me. I turned away because I didn’t want that. He then started rubbing my balls while the lumberjack was sucking my dick slow and deep.

He stopped sucking me and stood up. He started walking to the bedroom and gestured for me to join him. We all walked into the room and I laid down on the bed. We are all naked at this point when they both start going down on me. They suck my dick together for about fifteen minutes, stopping whenever they can tell I’m getting close.

The lumberjack stops and gets off the bed. He walks over to where my head is and asks if I want to try. I’m so horny at this point that I decided to try it. I turn my body so that I can take him in my mouth. I start sucking him the way I’ve been sucked before. It was very awkward at first, but I started getting the hang of it. It was weird when I started tasting his precum, and I was worried that he was about to cum in my mouth but I kept going.

The whole time I was sucking the lumberjack, the blonde was switching between sucking my dick and playing with it while tonguing my ass. It felt weird having a tongue going in and out of my ass, but I liked it.

After about twenty minutes, blonde and lumberjack switched places. Blonde had a thicker dick and it was harder getting it into my mouth. He was holding the back of my head and was more rough than lumberjack. The whole time, lumberjack seemed more interested in licking my asshole than sucking my dick. After a few minutes, he started slowly pushing his finger in my ass while sucking my dick. It was the first time I’d ever had anything in my ass and it wasn’t bad.

He could tell I was into it, and I nearly came a few times. When it was obvious, I was close to cumming he got up again. I assumed he was going to switch places with blonde again. But blonde held tight on to my head and told me he’s close. I started focusing intently on what I was doing to blonde and didn’t notice that lumberjack had gotten on the bed next to me.

Then I felt him lift my leg up and position himself between my legs. I was laying on my side. He put his dick at my asshole and started pushing. I wanted to stop him but blonde started saying don’t stop don’t stop. I’m close. So I kept going. Lumberjack was pushing hard and it hurt. I felt the head of his dick enter my ass and I jumped a little and it came out. He started pushing again and it hurt. I don’t know how far he got in, but it felt like it was deep.

It was then that blonde started to cum. I wasn’t expecting it, and was surprised when it happened. He held my head in place so I couldn’t pull away and his cum was kind of just slowly flowing into my mouth.

Lumberjack started moving in and out very slowly, and it hurt, but I couldn’t pull away because blonde was holding my head. I had to swallow because I couldn’t pull away to spit. It tasted salty, but kind of bitter.

Blonde pulls out of my mouth, and lumberjack tries to roll me on my stomach. I stop him and roll on my back. He can tell I don’t want him back in me, so blonde comes over and bends over and starts sucking my dick. Lumberjack puts lube on his finger and puts it in blondes ass.

He then starts fucking blonde right in front of me while blonde is deep throating me. I cum in his mouth after about 10 minutes. Lumberjack keeps fucking blonde for another five minutes and cums in his ass.

When it was over, I felt really awkward. I got up, got dressed and said thanks and left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

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? I felt guilty and dirty the next day. They tried texting me a few times but I ignored them.

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, Intoxication, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish

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? Somewhat

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’ve never told anyone.

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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I’m straight.

What was the BEST thing about this hookup? The head.

What was the WORST thing about this hookup? Swallowing cum.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? I’m not gay, but I still masturbate to the memory sometimes.

What do you think about the Casual Sex Project? Pretty cool.

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