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What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Elkhart, IN
Highest education received: High school diploma
What’s your occupation? Sex God
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Masculine, Bi-Top, Horny 24/6 (Even God had to take a day to rest)
How many sexual partners have you had in your life (including oral sex)? 60+
How many hookup stories have you here posted before? This is the first.

Bi Man’s First Gay Threesome

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? Group sex

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? Two males, one 39 years of old with short ginger hair and balding on top, glasses, goatee, green eyes, average build, 5’9″, 6.5″ average cut cock, a submissive bi bottom. The second was 44 years of old and had short black hair, a mustache, brown eyes, slender, 6′, 9″ thick cut cock, masculine top. Met through AFF, and was excited to have my first all-male threesome. I had only started chatting with them one week earlier and was very nervous, but thrilled to gain some more experience with men in general, and specifically with more than one man at a time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? They invited me over for an evening and I skipped a college class to make the appointed time they wanted to get together. They had approached me, and though I had some experience with some people older than myself already, this was the first time a woman or more than one man was going to be the scenario.

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? I met them for frozen pizza dinner and we talked about what they liked and had experience doing. Quite frankly I was a little intimidated because I had only fantasized about much of what they told me they’d done already together and with other people. I was also getting a hard-on listening and couldn’t help but let it show. The 39 y/o bottom knelt down in front of me at the couch and pulled me up to take my shorts and boxers off. My cock nearly hit him in the face when he freed it. My 7″ cut dick sprang forward at his face and he pushed me back to a seated position before starting to swallow my meat whole.

As this went on I watched the 44 y/o top across the room stand up from the chair and get naked. His cock was no joke at a thick 9″ with a pinkish/purple mushroom head. After undressing, he came to me and urged me to play with it and suck it if I liked. I stroked his length tenderly to enjoy how long it was in my hands before I grabbed it by the based and pointed it to my watering mouth. I tongued his peephole first and then sucked in the head. I quickly found this was as far as I could let this monster in my mouth. I gave him head as best I could while trying to enjoy the ministrations going on in my own crotch.

As I sucked, the top told me that their fantasy and reason for picking a young 19-year-old like me was so they could play with someone who was clean and disease free so that no condoms were needed with a 3rd person in their attempt to put two cocks in the bottom’s asshole at the same time. You would think that the 9″ thick sword that the top had would be enough, but no, the bottom wanted to be stretched by more dick.

This got me very excited and I told the bottom to stop sucking or was going to bust my nut right in his mouth. With that, we moved our play to their bedroom, and to bottom went to the bathroom to clean out his ass with an anal douche. The top laid down and stroked his dick in front of me and I had a little fun while waiting by touching my cock to his for a little bit of frottage stroking. His dick was oozing precum as much as mine was, and I took a moment to taste its salty goodness.

The bottom came back and laid down on his back, grabbing his legs at the knees to expose his ass to me. The top handed me some lube and I stroked my cock with it and used a couple of fingers to slowly get the bottom’s asshole ready for me. I pressed my cock to the brown eye and pushed into him steadily but slowly to allow him to adjust to me. It didn’t take long, and I should have anticipated he used to a bigger dick than my own entering him there.

After a few minutes of fucking him, I pulled out and came all over his balls and asshole. Then the top nudged me aside to press his own hard cock inside his partner; not before slathering his length and tip with the remnants of my cumshot splattered across the genitalia of the bottom.

I watched closely as he plowed that ass quickly and vigorously. What amazed me was the fact that the bottom was not stroking his cock the entire time, yet had a hard-on and it seemed to be aroused like he was about to cum. I took this as my opportunity to please him a little too and bent over between them to suck the bottom’s cock. I had not even sucked him into my mouth more than 2 inches before I was surprised with a pulsating sensation of cum filling my mouth. I nearly gagged before I could slip away from his cock with his entire load in it. I wasn’t sure what to do with it as I wasn’t very experienced in swallowing yet. I looked at the top who held out his hand like a cup and told me to spit it into his hand. I did as instructed.

He pulled out of the bottom and carefully maneuvered to lay down before placing the load of cum transferred from my mouth to his hand all over his cock. His partner, the bottom, straddled him and squatted down to impale his ass upon the 9″ length once more. I was witnessing the second round of cum being used as lube this evening.

It was clear what was expected of me at this point, and I had to give it a try. The only thing that worried me was the risks I’d been taking so far this evening having unprotected sex with two older men who’d been around with other men before. I didn’t know if they’d lied about their HIV test results or not, and here I was plunging my cock into ass and playing with other men’s cum. The very thing they warn you in high school not to do.

I knelt behind them and steadied my cock to the already impaled asshole. It was lubed enough yet from earlier and with what the cum had already done to pave the way for me to enter him as well. I just needed to press forward and into the bigger cock below me to get wedged in with it. From there I was able to push forward more and stretch to bottom’s asshole wide enough for two decent size cocks to pound him.

We gradually were able to keep a rhythm that allowed us to enter the asshole at the same time over and over for about five minutes before we heard the bottom moaning in orgasm again. His top partner scooped up some of the cum from his stomach and reached back to re-lube the asshole we were both penetrating.

After a couple more minutes the bottom was urging us to cum inside him. It was a moment later when I realized I was the only one still moving. I felt the spasms of the large cock under mine and I looked down to see a torrent of thick white cum oozing out from around my cock and the top’s cock. He was one of those rare guys that could shoot like a real pint of cum when they wanted, and he could have filled my school milk container easily with one load of his ejaculate.

I couldn’t help but be overwhelmed by the thought of my actually fucking a cum filled asshole. My load erupted inside the bottom’s ass to join his partner’s river of cum already flowing out of him as I fucked my cock deep into him. I thought for a moment just then that all three of us had our cum in the same place now. The bottom’s cum was used to lube the way for the top’s and my cum to join it.

I pulled out and saw the now softening cock of the top flop out of his partner’s ass. The rush of remaining globs of cum followed the exodus of activity from that stretched hole and landed on the top’s cock and balls. I don’t know what came over me, but I immediately placed my hand on to top’s cock and stroked him with all that gooey mess. I even scooped up a bit in my fingers and gave it a taste not knowing if it was mine or one of theirs I was tasting, but it didn’t matter, it was hot as hell.

We all got up and went to their standing shower to clean up. While in there I had felt the need to try and get the top off one more time as both the bottom and I had cum twice while playing. I knelt in the shower and with his partner’s help and encouragement, I stroked and sucked the top until he was blasting one more powerfully thick load onto my face and in my mouth for me to swallow. His initial spurt in my mouth gagged me at first and I slipped off him while he shot twice onto my forehead down and across my left eye. I was half blind but put him back in my mouth to swallow the rest and it had a wonderfully salty-sweet mix in flavor. After that, I got cleaned up and thanked them for the exciting evening.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

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 met with them many times over the years, playing 1-on-1 with both, as MMM threesome, and even when they had other invited guests over. I even took my wife one time and we all played with the bottom in one way or another.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, Power / Dominance, Submission / Relinquishing power, Making new friends, It was easy / convenient

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? Other male partners I’ve had, some couple’s that have bi male halves, and my wife.

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

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? How comfortable I became with playing in more than a 1-on-1 mm situation, and also learning to like cum play in different ways through no-condom sex.

What was the WORST thing about this hookup? Just the initial anxiety of wondering about HIV status.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It significantly improved my ability to feel comfortable with men the way I already felt playing with women.

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 told all there is to tell about this one.

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? If not for open sexuality and being bisexual myself, I would probably find sex to be boring and without challenge and excitement. Being sexually adventurous keeps it fresh and allows for more sharing of ideas and pleasure with my partners. In my opinion, everyone should learn early on to be bisexual and enjoy what everyone has to offer.

What do you think about the Casual Sex Project? Great site, looking forward to sharing more stories about my experiences and reading about others’ experiences.

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