What a first time gay sex experience was powerful
By: Connor
“When was your first time?” my friend recently asked. It’s one of those “rites of passage” questions we all get when recalling our first gay experience.
Haven’t you ever been asked?
So I’ll tell you the answer to my bud’s question. But first, it’s probably a good idea that I share a little background so that you know how things went down (figuratively speaking).
When I was 15-years old, I was sent to a military boarding school. In fact, my brother and I both ended up getting sent away.
There were numerous reasons for this, including the reality that we came from a “broken homes”. That’s a polite way of saying that our parents ended up getting divorced. Today, it’s not as big of a deal but back in the 80’s, it still was frowned upon.
Anyway, once our p’s split, we ended up going with our mom; a woman who could barely take care of herself, let alone teenage boys. But it was better to live with her than dad because he had his own issues with alcohol and drugs.
Without going into it, I’ll share with you that we were a handful. If we weren’t causing problems in the neighborhood, we were getting into trouble at public school. The tipping point happened when my brother and I got busted joyriding in a car we hot-wired.
So after that happened, my mom’s side of the family held a pow-wow and decided it was best we went to “Bryson Academy*”.
It’s a military boarding school that has been around for over 100 years. When it was originally founded, it was called Bryson Reform School. But as the years went on and times changed, it morphed into an “academy”; a place that boys from broken homes were sent to.
In case you are wondering, Bryson offered a sliding scale fee so that any family could afford it. The bulk of the money that allowed the place to operate (and still does) came from private donations and charitable gifts.
I think my family thought Bryson would be a good place for us because the school offered three things that were sorely missing at home: Responsibility, Respect and Self-Discipline.
What my family didn’t know when they shipped me off was that I was gay. At 15, I knew deep inside that I was and probably younger than that. I was still a “virgin” but I didn’t need a sexual experience as confirmation – I liked guys. A lot.
And so being sent to an all-male school was almost a dream come true. Oh sure, I was scared shirtless. And I threw a fit when they broke the news. My brother did too.
But secretly, I knew that going to Bryson would be way better than running the streets of a large city. Plus, it would be my first time being around nothing buy guys.
My first few years at the academy were difficult. Like me, most of the guys came from difficult homes. But unlike me, a few of the boys could be classified as “at-risk”.
Here, I’m talking about young men who were on the knife’s edge of becoming criminals. In fact, several of the guys I went school with moved firmly in that direction.
Some are in jail right now others are dead – no joke.
So at Bryson you learned to keep your mouth shut and do as you were told. And even then, trouble had a way of finding you. If I had a dime for all of the fights I got into I’d be rich.
You see when you go to an all-male school, it’s all about appearing tough and not showing any fear – not even a little. The minute someone smells it, it’s game over. I knew guys who were relentlessly bullied for showing just the slightest hint of weakness.
One of cadet I would constantly get into fights with was named Martin. He was basically my age, maybe a year older? The both of us were active in intramural sports and played on competing teams.
At Bryson, he ran with the “Latin Boys”.
I guess I forgot to mention that. There were clicks at the school which were mostly split along racial lines. If you were black, you hung out with the black kids. White? That was your group. And Latin guys had their own gang.
The reason Martin and I fought so much was I never gave into his crap. A lot of the other guys did because they feared him. Word was that at home, he (and his three brothers) belonged to the Avenidas, a notorious street gang in LA.
There was no way I was going to become anyone’s punching bag or endure non-stop harassment for being a “pussy”.
So every time he picked on me, I’d give it to him right back. When we’d get into fist fights, he won just about every time. But see it wasn’t about who “won” but instead, manning up and not wimping out.
If you did that, you could trade your scars to gain the respect of others. Yes, I know that sounds like something out of the toxic masculinity handbook but I’m just telling you how it was.
In any event, all of us were assigned to “cottages” at Bryson; a term that was a carryover from reform school days.
I was assigned to River Cottage and my brother to one called Sky. Out of the 10 units on campus, “River” was considered the best because the house parents who ran it were most lenient.
I stayed at River from the time I was 15 until I would graduate and went to college.
So why am I telling you this?
Well, because it was during my senior that the guy I told you about earlier, Martin, was transferred to River.
In an effort to create greater diversity among the student population, Bryson leadership decided to mix things up. This meant guys who had all White roomies were now paired with blacks. Latin guys, who almost always shared the same dorms, were made to split rooms with white and black guys.
At the time, I didn’t understand what was going on. But looking back, it made a lot of sense. I mean it was bad enough there were so many racial clicks, you know?
In any event, guess who got placed in my room? Yep, Martin. One of my roomies was sent to his old cottage and he came to ours. I tried to tell my house parents that they shouldn’t put us together. But they said it was out of their hands.
And honestly, it probably was.
There’s something about having to live with someone in a dorm that forces you to get along. The first few days were hard and we were constantly at each other’s throats. But that faded away pretty fast.
Plus, the third guy in our room, Nathan, was bigger than both of us told us both to keep our shit shut.
At Bryson, you were either on the “7-Day Plan” or the “5-Day Plan”. The difference? If you were on the “7”, you stayed on campus Monday-Sunday. If you were a “5”, you went home on weekends.
I was a 7, thanks to my family. You see at Bryson, your parents made the choice or not if they wanted you home on weekends. I was always jealous of the 5’s because by 4pm on Friday, they were being picked up by their mom or dad.
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There was one way, however, a 5 could be temporarily made a 7. It was called “restriction” and you were placed on this status if you got into trouble. Think of it as being grounded, military school style.
So you probably know where this is going.
Martin mouthed off to our platoon leader during morning formation and got written up. That resulted in a two-week restriction, which meant he was forced to stay in the cottage, with the exception of going to school or the dining room.
Up until that point, I had enjoyed having the dorm all to myself on weekends. You could be alone, think, read and like most guys who are 18, sexually fantasize and beat off.
So the weekend Martin found himself tethered to the brick and mortar of River, I was none too happy. But what could I do?
I don’t know how it happened but it just did. Around 9 pm at night on a Friday, when it was dead silent at River, Martin started about talking about his girlfriends back home.
Like a lot of guys, he bragged about his conquests. I rarely talked that way unless I had to but only because it was better to lie and make up “girlfriends back home” as opposed to getting my ass kicked.
As he sat in his bet, I could see that his tone had changed from being the tough street guy to something else – something more vulnerable.
And his stick was tenting up in his fatigues.
I continued to lie and talk about women. The conversation continued to heat up.
At some point, it just happened.
We started to beat off. I can still remember him shutting the door to our room before doing it. While he sat on his bed and I across on sat on mine, we both released. When we were done, we used a boot polishing cloth to wipe up; standard gear all Bryson cadets were issued.
The next evening, Saturday, was just as dead as Friday. I had plans to go off campus and check out a movie. Yep, being on the 7-day plan didn’t mean you were confined to campus on weekends. But if you were on restriction, you had to stay.
And that meant Martin was stuck.
Long story short, he asked me if I wanted blow off the movie and stay in for a game of monopoly. Given what we did the night before, I kind of knew he was looking for more than just companionship.
I agreed to hang.
Somewhere between my winning Water Works and him winning St. Charles Station, the topic once again turned to girls. But this time, he started asking curious questions like, “Why do girls like sucking d*ck” and stuff like that.
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We took to our respective beds. The game was over but the conversation about women continued. It was probably around 2 am.
We were both stroking it and talking – watching each other.
I remember him getting up to prop a chair against the door. But instead of heading back to his bunk, he swung over to mine.
He started going down on me. He didn’t have to ask me if it was cool. There was no need to.
We traded this activity back and forth. I was nervous but excited at the same time. I was also really inexperienced with giving head.
We never kissed or anything like that but I do remember that just before I was about to release, he swallowed me – and then quickly spit it out.
“Hey, the only way to know what chicks like is to try it,” he said.”
**
During my last six months at Bryson, Martin would find himself on restriction at least 3 times. And on each occasion, during the weekend, we’d “talk about girls”
Nothing more. No anal, no making out. No cuddling. It wasn’t like that. But it was a way for us to explore our sexuality. And for me, it was confirmation of what I had always known – I liked men.
All of this went down decades ago. I haven’t seen Martin in years, although I do see posts from him on Facebook. He’s married now with kids and lives in a different state.
Was(is) Martin bi-curious? Probably. It’s hard to believe I was the first guy he messed around with. After all, it was an all male military school.
And my brother? He’s straight. He never shared with me anything from Bryson that made me wonder. But then again, I never told him what I’ve told you hear. Who knows?
Anyway, that’s my story. My first gay sex experience happened at military boarding school. Ever since then, I’ve been into getting serviced from other guys.
Standard stuff, huh?
Thanks for reading!
*The name of the school has been changed per the author’s request.