Bully Pops my Cherry

I grew up in a small rural community and basically, half were rancher types and the other half were farmer types (yes there is a difference).

My family were farmers, not a lot of livestock on the farm, mostly grain and hay. Ranchers of course had the cattle, horses and all that.

I knew most of the kids growing right from kindergarten all the way to Grade 12 graduation and it was pretty much right down the middle in terms of farmers versus ranchers among the class.

Phil was the son of a rancher. He lived 20 miles east of town, and I lived about the same mileage west of town.

Phil was the class bully, plain and simple.

From the beginning he was always a rough kid.

Good at sports but mean and angry over everything.

I didn’t have much to do with him socially for the first six grades, but by the time we had hit puberty as teens, our interactions were more frequent.

Usually this meant him putting me into a headlock or pushing me around, pinning me against a locker, or some shit like that while the other knuckleheads in my class laughed and cheered him on.

A lot of teenagers will relate to this, but I liked the attention because he was hot (you know you’re gay when).

He worked out a lot, and had massive pecs and gorgeous arms, and more often than not, during breaks, even in junior high school, he would be shirtless running around playing football or something.

Shirtless, tight wranglers that fit him perfectly with a big belt buckle and cowboy boots.

Its funny the things you remember. Winters are long where I grew up so in the spring, when Phil would start to remove his shirt as the weather improved, he had the worst farmer tan you can imagine. But, after the weeks of sunshine and a little warmth in the air, he turned into a bronzed god.

In my eyes anyway (again, you know you’re gay when).

He and I were early babies so our 18th birthdays landed just after January which meant our last months of high school enabled us and a few others to get booze, go to bars and all that.

Bully’s need targets and I was easy prey.

Kind of geeky with glasses, always second or first highest marks in every class, and basically every bully’s dream come true.

But I wasn’t a scrawny kid or anything. At about grade 7 I had really gotten into my swimming and cycling so I was trim and fit from all the lanes, and had big legs and ass from the cycling.

I probably could have knocked him flat for all the times he knocked me around but I guess in retro, being a closet gay in a very small community, this was at least one way to get some male-on-male attention.

Had I been more in tune with things, I should have taken advantage of the signals he was sending when he bullied me.

He would grab from behind when it was just he and I and whisper through the choke hold, “I could split you in half you little faggot.”

And I should have said, “Fuck me stud,” but alas, I missed the moment.

There were times where I was pretty sure he was rock hard when he did these things, but again, I was kind of turned on by his bullying because of the sexual undertones.

He would brag about his big dick and although I can confirm it was big, for years in the change room, all I got was a glimpse at the urinal or more often than not, when he would drop his gym shorts and I would see the bugle in his navy briefs.

Despite the attraction, not surprisingly, Phil was not the most academic student and I nearly quit school on the spot when one of the teachers said that she’d like me to tutor Phil so he could finish high school.

I was so pissed off when I got home that afternoon. My folks wanted to know what happened and I said “There is no f*cking way I am helping that asshole!”

It is entirely possible that my resistance here was just for show because that night I jerked off into a sock a few times dreaming about what might happen. And of course, the next day I told the teacher that it would be good for me to help Phil out and get him at least a passing grade for his diploma.

I assumed that it would happen during school hours but the teacher said we’d have to carve out space and time after school and the weekends.

We could use the library until 6pm weekdays, but anything else we’d need to get together at my place or his.

I guess Phil was as excited at this prospect because he was very quick to suggest that we get started that very first weekend and we could study at his place because his parents were out of town.

In suggesting this, it was the first time that I saw something I liked in Phil. Maybe he realised how worthless life would be if he didn’t have a diploma and decided to be nice, or maybe it was just his teenage balls needing to bust a load, but either way, I found myself thinking about what to wear, what was I going to say etc.

Basically, I was a giddy little school girl getting ready for a date.

I got to his place at about 3pm and the plan was to study math for a couple of hours and do a practice test.

I got there promptly at 3pm and Phil came out of the house looking a little angry but at the same time, looking really sexy.

He was wearing a nice cowboy-like shirt (not plaid or anything but clearly from the western wear store) He had on his trademark cowboy boots and wrangler jeans that accentuated all the right bumps and curves.

I remember a year or so earlier getting caught out by him in a physics class because of the way he filled out the crotch of jeans. He was sitting in the desk and his thighs were pressed wide but his crotch was this mound of yumminess and I was like a deer in a head light staring at it.

He leaned over, “Whatcha staring at fag?”

I was mortified, but today, he came out of that house, and if i didn’t know better I would have thought he was hard. But as I would learn over the next months, he was hung like a horse and both a show-er and a grower.

“Let’s get this over with, I have chores to do,” he mumbled as if to put me in my place.

I laughed under my breath because this was not an 18 year old dressed to do chores.

Both of us had clearly dressed to impress the other.

Anyway, off we went to hit the books and I walked him through various calculations showing him little shortcuts and ways to remember formulas.

I honestly don’t think he understood a word of what I was saying but during the tutorial I caught a second glimpse of why I would like this guy, he was listening so intently, almost gazing toward me. the sides of his mouth would curl up a little in a sexy little smile as I nattered away about formulas.

I confess it turned me on but it was easy for me to remember the bully in him and sure enough, when we finally finished the practice exam, almost like a light switch his mood changed and he started to berate me.

“How often do you check me out little faggot? Huh? I’m talking to you.” He said as he went into the kitchen to get a beer.

He came back from the kitchen into the dining room where I was still sitting and walked around behind my chair.

He put both arms around me and plopped two cans of beer on the table and got me into a choke hold (his signature move).

Again, I probably could have sent him tumbling but he persisted, and I relented.

“Whatcha gonna do about it fag, huh? Gonna fight me?” He asked.

I was feeling particularly bold and blurted out, “we don’t have to fight, I could just suck your dick Phil.”

He got so mad at that.

He was raging and he pushed me out of the way.

I flew across the room toward the wall.

His face was bright red, fists clenched towering over me on the floor.

“Whoa bud,’ I said putting up my hands in defence, “take it easy, I thought that’s what you wanted.”

“I’m not a fuckin’ faggot asshole” he shouted back.

That seemed to defuse things a little and he extended his hand to lift me up to me feet.

I should have known what would come next.

“Sucker!” He shouted as he resumed his choke hold.

I laughed and said “you are such an asshole.”

He whispered more about his big dick splitting me open and kept going.

It was more of his way of hugging than wrestling and at one point he says, “I like tormenting you, it’s cute.”

His hold wasn’t so tight that I couldn’t speak so I teased him, “yeah, you’re totally not gay man.”

“I’ll fuckin’ kill you faggot,” he mumbled and I thought to myself, “what have I got to lose?”

As he continued to hold me, I reached around to the front of his jeans.

This was no easy feat because every inch of his body was pressed into mine, but I reached around, parted his body enough to get in there and with nothing left to lose, I caressed and rubbed his dick through his jeans.

Phil let out a little shudder and somehow I knew it would be ok.

His grip weakened around my neck and he moved away slightly so I had easier access to the front of his jeans.

I was grabbing handfuls of dick through the denim and with each tug or squeeze he let out a soft grunt.

His choke old by this point was nothing more than his arms draped over my shoulders and I felt emboldened to take things further.

I grabbed his right hand as if we were doing a dance twirl and spun around to face him.

Placing his right arm over my shoulder, he instinctively, put his other hand into position and within a few seconds we were in a lovely embrace.

Phil was a little taller but we looked into each other’s eyes and I realised then and there how pretty his eyes were.

Green-blue and the whites were perfectly clear.

I smiled a little which got a smirk from him and we moved in for a kiss.

When our lips touched he pushed back and shouted “I’m no faggot!”

I relented and put my hands up, “ok ok ok, whoa there tiger, take it easy, not making us do anything here.”

“I’m sorry man,” he said, “I don’t know what this is.”

“But it feels nice doesn’t it? I asked.

“Yeah it does, around you it feels normal, whatever the fuck that is.”

The tension in body relented a little and he resumed the embrace pulling me close.

My memory convinces me that what happened next was right out of a Hollywood love scene but in reality it was probably the most awkward kiss between two people in the history of man.

But still, we did kiss and make out standing in the dining room of his parent’s house.

I had learned the lesson about pushing him too far too fast and although I had only sucked my first dick a few months ago while checking out a nearby University, I really wanted to suck him off.

He must have wanted the same because he broke away from kissing and grabbed my hand.

Leading me to the bedroom, he closed the door behind us and grabbed me close for more kissing.

Even in a few short minutes, our technique had improved significantly and I could tell he was more relaxed and enjoying the sensation.

In his Wranglers, I could see and feel his cock arched to the left and I was getting very hungry for a taste.

While we were kissing, my hands were around his waist and I slowly started moving them to the front, fiddling with his enormous cowboy belt buckle and testing the water to see if he would object.

He didn’t and I was somehow allowed to proceed.

He was leaning against the door.

I broke from his arms and dropped to my knees while caressing his pecs though the fabric of his shirt.

My hands inched down to his waist, and after unzipping his jeans, I tugged them down around his thighs.

I wanted to suck his dick so badly that I didn’t even give a kiss or a lick through the fabric of his briefs, but pulled them down and released a beautifully thick and cut dick dripping precum.

I think he would be a good 8” and it was thick and stuck straight out.

I had zero restraint at this point and started to lick his knob, kiss and stroke his dick.

His precum tasted so good and made me hornier than ever.

I was new to sucking so I wouldn’t say I was an expert at it but I got my lips wrapped around his dick and blew him as best I could.

He was obviously enjoying it regardless of my novice status.

Moaning, groaning, pulling my head in to gag me, whispering things I could barely understand.

“Oh fuck, I’m close” he said pulling me off his dick.

“Is it ok?” I asked.

“Amazing,” he replied pulling me up to my feet.

“Have you ever?” He asked while kissing me. “You know, fucked?”

I shook my head and with a tenderness uncommon to bullies, he asked, “do you want to?”

Up to this point I had only played with my ass a little and once used a small butt plug which felt amazing, so I knew in my soul that I wanted to be fucked, but I was nervous and rejected the offer.

He didn’t get mad or show the angry bully side of things, but pushed me down to clearly finish what I had started.

My right hand was stroking his cock in sync with my sucking and it was not long before he grabbed me head and blasted a nice load of cum into my mouth and all over my face.

I was a cum-hungry pig at that moment (once again, you know you’re gay when). I couldn’t get enough of seed and while he shuddered and grunted I milked his dick for every last drop.

I realise the title of this story is “Bully pops my cherry” but to manage your expectations, that didn’t happen until after a few more tutor sessions.

When it did happen, it was a magical moment.

The bully was gone and not only did he pop my cherry but we spent the next two months after high school fucking our brains out all around the countryside.

He once even rode a horse all the way from his place to mine one afternoon and took me out into the middle of nowhere and fucked me on a blanket under a tree.

During school he was still a dick head to me, but after school and on the weekends, it was all a bit of Brokeback Mountain.

Sadly, the summer came to a close and I was off to University, about a 90 minute drive away.

Possibly the saddest day of my life to that point was trying to convince him and myself that we would continue the relationship.

We both knew that a) he would likely never come out of the closet, and that b) university would change my life and pathway completely.

And so it happened.

We lost touch and about 4 years after high school I happened to call my folks and mom said, “did you hear that Phil shot himself?”

I cannot lie, I was devastated and had to hold it back tears on the phone because even then, my mom said things like “god he was such a bully, wonder what was going on in his head?”

I saw Phil’s mom in town a few years after that and we had a little chat. She still wore the anguish of his death visibly and you could tell she just didn’t know why he had taken his life.

Maybe she knew something of Phil’s and my romance because in chatting she said, “you know, he always was so kind when talking about you, you helping him graduate, not sure why he treated you so badly, and you know, he didn’t have many friends,” and she started to sob here, but continued, “thank you for being nice to him.”

That was probably the second saddest day of my life at that point and to this day, I wonder how things could have turned out differently.