My First Gay Experience With Two Guys

by Richard

What’s your gender? Man
How old are you? 23
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Usa
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Student
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Bottom with gay sex. Just normal guy with straight
How many sexual partners have you had in your life (including oral sex)? 27
How many hookup stories have you here posted before? 0

My First Gay Experience With Two Guys

How long ago did this hookup happen? Last week

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

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? Both partners are a bit older, John is 42 and Brian is 44. We are all kind of in the same circle of friends so we see each other every now and then. We are all in a running group together, we are all fit.

John and I have hooked up several times, he was actually my first to have gay sex with; after I learned he was a gay top, I told him I was curious about taking a cock in my ass and sucking cock. He obliged and “showed me the ropes”.

Brian and I hooked up twice before this. He is attractive but was in a relationship for a long time. He confided in me his depression of breaking up and I decided to help him get over it by sucking his cock.. apparently his last partner was quite boring in bed, so i asked him to shoot his load over my face. The next time we saw eachother it was a booty call, I called him and we had some quick anal sex. He was actually really good left me a bit sore after.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I have a girl who is my friend was my friend with benefits and we had sex twice earlier in the day. I came inside her both times and after that I don’t really have good erections so I like a day to recover.

Still it was like 6pm in the evening and I was lonely and wanted to be with someone. I texted John first to see if he wanted to come over and hang out. He didn’t reply so about 30 minutes later I texted Brian and he agreed to come over and hang out. Within 2 minutes of that, John messaged me and said he could come over. I was straight forward with both guys and told them both that each of them was coming and they both agreed it was ok.

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? Brian arrived first, remember how we are all friends, so he just came into my apartment and we started just watching a little tv and he had some wine i offered him. We made out with our clothes on, waiting for John to come over. He took my shirt off and played with my nipples and while doing that, John arrived, dressed very well in a suit and tie.

I instructed both gentlemen to remove their clothes and get completely naked and I did the same. Brian was already hard, and John needed to relax so i asked him to lay over the bed and I started to suck him. Brian, who knew my bedroom, went over to my night stand and got the lube on it. Splat, he put some lube over my asshole. I then felt his finger start pushing it way into me, taking some lube in with it would be slippery inside me, he used his other hand to stroke his cock. As John was hard, I noticed Brian going to the bathroom to wash his hands as they had been in my ass and I was happy he was respectful about that as I find it a little gross.

I then asked Brian to come over and get his dick sucked. I had both guys on their knees on the bed, alternating sucking them and stroking the other with my hand. Eventually Brian pushed me over and firmly grabbed my ass cheeks and spread them. Then I could feel his bare cock pushing its was into my hole. He got about 2 inches in when I started to feel some pain and told him to just keep it there. I wanted him to just not move but he pumped a little, not hard or anything, and while it was a bit uncomfortable, it started feeling better. John was patient as he was stroking himself while I got acclimatized to Brian’s cock in my ass. I asked John what I could do for him, and he put his cock in my mouth. Brian was all the way in me by this point and he was very hard. He started pounding my ass and I told him to keep it up. Focusing on sucking Johns cock was a little difficult as I was trying to stay in a good position for Brian, but that going to end as Brian said he was close to cumming. I told him to cum wherever he wants, and he pushed all the way inside me, giving me an anal creampie. I now felt better as I now had more flexibility to suck Johns cock, and could feel Brian’s cum start to leak out of me, down my balls.

John then said he wanted to fuck me ass. I was a bit surprised as my asshole was full of Brian’s cum, but I wasn’t going to argue. He got me to lay on my back with my legs up to have sex with me in anal-missionary. I had only tried this position as few times and it was very intoxicating as John had lots of control and could fuck me very hard. It wasn’t long before he lost his load inside my ass too, John had this powerful orgasm that shot into me, I could feel it squirting and he stayed in me after he came, kissing me with my legs pushed up against my chest. What happened next is what surprised me, Brian came over and asked me to get down on hands and knees, and get my ass high up. I did as told, thinking he was going to fuck me again. But instead he put his mouth to my asshole and started sucking the cum out. He spread my hole apart with his fingers and stuck his tongue in as far as he could put it. Gulp Gulp Gulp.

We all went and had showers after. The guys hung out and we had sex again but it was more one on one.

How sexually satisfying was this hookup? Very

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? Well, the party actually didn’t end there. I had more anal sex with John and he came in me again.

I sucked off Brian. Swallowed his cum.

I will continue a friends with benefits relationship with both guys and maybe do another 3 way soon.

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, Emotional intimacy, closeness, connection, I was feeling lonely, Submission / Relinquishing power

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? 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? Just here

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? Not at all

What was the BEST thing about this hookup? It was my first group sex. I knew both partners and had unprotected sex with each them already so the fear of catching something wasn’t there. I didn’t have to be alone that night and had a fringe benefit of being creampied which I love.

What was the WORST thing about this hookup? This is very minor but my colon felt a little awkward for a few days and I gaped afterwards so the cum leaked out for quite awhile after.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I would like to be more open with my sexuality, especially with existing partners.

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? It was just good, consequence free sex.

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? Well I started having more casual sex with men more often and it’s easier on the mind than women. I’m always worried I am going to get a girl pregnant, whereas with existing sexual partners, as long as there is a degree of monogamy and intelligence about cleanliness, its easier on the mind.

What do you think about the Casual Sex Project? Its awesome. I love the stories and would like to re-enact some of them.

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