What It’s Like Hooking Up with Two Guys at 19

young sexy man reflecting

Fantasy and reality can be two different things

My first time, at 19 years old, was with Rob, a mid-20’s air force officer.  I was still very much in the closet.  He worked at the SAC (Strategic Air Command) headquarters in Omaha.  We had met with him making the kind of eye contact that screamed ‘I’m gay and want to do you.’

We became friends, ran around a little and I eventually ended up making several trips to Omaha just to see him.

The last trip was when it all happened; my first time with a man.  Giving him head, I remember him accusing me of having done that before.  I must have been a natural.

Men, ever since, have always commented on my oral skills as being up there with the best; p-rn star quality they’d say.  Anyway, it was my first time ever going down on a man.

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It was my first time, instinctively knowing that I should allow him to lay back and enjoy as I got deflowered.  Where I had happily started off with my face between his legs, it eventually turned into the hot military man lying on top of me, gently taking my virginity from me.

You NEVER forget your first and I remember him being slow, patient, kind and rather hung.  His comment once it was all done?  “You’re gonna be walking crooked for a week.  Don’t be surprised at how sore you’re gonna be in the morning.”

He held me until I fell asleep and long after that.  The next morning, he inquired but I felt fine.

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I never did hurt or feel sore from taking all of him and I do mean ALL OF HIM!  That first time confirmed what I enjoyed, complete submission to a man, and how naturally I accommodated his severe endowment.

Fast forward six years and well after my own college years…  I was what my few new gay friends called a ‘baby queen’ back then; a twink by today’s verbiage.  I’d not been out for very long and still had very little experience with men.

However, I knew what I liked and I loved getting drilled by a man, as rare as it was, with my being naïve and quite shy.

All my life I knew I was gay and had always incorrectly associated that with bottoming.  By the time I came out, my experience with a few toys further confirmed my passion for receptive anal play.  I was 26, blonde, blue, 29-inch waist and weighed 160 pounds.

I’m not trying to sound stuck on myself, but I was an absolute hottie and I knew it.

I had men coming on to me all the time but I just didn’t know what to do about it except to flirt and be a prick-tease.  Again, I was shy, naïve and, being incredibly attracted to big, strong Alpha male types, scared to death of my desires becoming all too real with someone overpowering me and… well, you know, that fantasy meeting reality might have not gone well.

I did go out frequently but rarely hooked up back then.  However, I was at the cruisiest club in town watching a go-go boy dancing away.  Actually he was a man.  He was well into his 30’s, muscular, about 6’ 3” tall and, from the looks of his thong, packing some major sausage that I was hungry for.  Then he caught me staring from across the room.

Being shy, I looked away.

He’d caught me again and smiled.  His grin was so enormous that it intoxicatingly drew me in to him even further.  My drink ran dry and I was forced to get right up next to him, at the bar, to get another libation.

He hopped down and spoke to the bartender.  “Chris, it’s on me!”  I thanked the tall, muscular, curly-headed, hung hunk and started to walk back to my corner.

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He grabbed my arm and led me back to his perch, the box he was dancing upon.  I finally took out a five spot to tip him.  “No, huh uh, I don’t want your money.”  He obviously wanted something else.  “You staying ‘till close?”  I smiled.  “Sure, I can do that.”  I grinned myself, knowing I was going to be giving in and getting laid.

I think I had five or six drinks total, over four hours, so I wasn’t sloshed, but I was quite relaxed.  At 2 o’clock in the morning, the lights went up.  Chris and the doorman started shuttling everyone to the door.

The dancer, Blake, said, “It’s okay he’s with us,” referring to me.  The two dancers went into the back store room to get changed with me in tow.  I soon discovered that he and Joe, the other dancer, were lovers and both tops.

I was so chilled out that I no longer cared and went with them to their hotel room.  Joe kicked back on one bed while Blake and I got more comfortable together on the other bed.  After I got him good and fluffed up, he was enormous.

That thing grew to to an impressive size before becoming completely like a steel rod. That’s when he commented, “You wanna sit on it?”  I didn’t even answer but hopped up as he put some lube on himself.  It was slicked up quite well.  I got about half of him inside of me before he started thrusting back and forth.  I hovered over him as he took control from below.

I had completely forgotten about Joseph until I felt his finger alongside of Blake inside me.  I could hear Joseph saying, “Oh yeah, take that big d—,” just before I started feeling two fingers inside me which eventually turned into three.

The next thing I knew, Joe had gotten right up behind me, reached around my torso and held me as he started into me – at the same time as Blake.  I was riding one while the other was giving it to me from behind.

I’d never heard of, or even thought about, taking two men at the same time but he’d worked on fingering me until I had stretched enough to take them both at the same time.

The drinks had surely helped.  Once I’d become the middle of that hunky sandwich, Blake started thrusting upward deeper and deeper until I could feel his entire length bottoming out within me; something that I would have never thought could happen and feel so incredible.

The two guys went at me for nearly fifteen minutes until I shot my wad and then heard Blake say, “Oh man I’m close!”  That’s when Joseph pulled out and Blake lifted me off of him and to the side saying, “Get on your belly.”  I couldn’t have rolled over quick enough.


The entire ménage à trois thing exploded off the ‘hot’ scale and I was more than into it.  Blake lay down on top of me, with my sticky mess gluing us together, before he shoved himself right back up inside me and went at me even harder for about another minute until I sensed him physically building up to an explosion.

Just before he released, he quickly pulled heaven out of me. That’s when he finished on my back.

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Joe was right there standing next to the bed and when he watched that massive milk load over me. Not long after, my shoulder and arm were covered in his aftermath.

I lay there not feeling used in the least, but instead was feeling completely desired with what had just gone down.

Blake hopped up, cleaned himself up and brought back a hot, wet washcloth but instead of just handing it to me, he gently cleaned everything up from my backside and dried me off before he crawled into bed and said, “Come here.”  I cuddled up next to him just before Joseph turned out the lights and crawled into bed on the other side of me.

The three of us not only had the hottest sexual encounter that I’d ever had, they were genuinely intimate with me, expecting me to snuggle up and sleep with them all night long and I did.  The next day…  Mmmm!

A True Story Written By M. H. (Michael) Sebastian

Author of Gay Romance and Gay Themed Novels