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Bro to Ho – Part 5

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By Cutieboy90

To start at Part 1, click here

Cutieboy90It was another rainy winter afternoon. I sat on my futon relaxing for once, and enjoying the silence. Shawn had taken Gabe out for a walk, something they’d come to appreciate only recently. They got along nicely, even if it had taken a little while for Gabe to get used to it. I smiled as I looked over the progress reports I kept on my tablet.

Shawn had been working very hard, and had turned his life around. His grades had improved this semester, all A’s and B’s. His performance on the swim team had also improved, and he was able to compete now. Of course, his status at the Frat house was still the same. Unrelenting bitch duties, always in some form of sexual slavery for a bunch of bored, horny frat boys whenever he wasn’t in class or at AA. He still struggled with the concept of it all, but he was being punished far less frequently, now spending most weekends with me.

Gabe had taken a bit longer to settle into his new role as my dogslave. Unlike Shawn, Gabe’s changes had stayed being closed doors, and only Billy, Shawn, and myself knew about it at all. The biggest external difference for Gabe was that we’d decided to take him off the wrestling team and the football field, and keep him closer to the aquatic center where we could keep an eye on him.

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Bro to Ho – Part 4: Gabe’s Story

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By Cutieboy90

Cutieboy90 gay bondage stories“Show some respect. This is Ari’s brother!”

The words are still as chilling now, as they were then. I still see his face, as he sat there sipping a pumpkin spice latte. How could I have missed it? He even looked like he could be Ari’s brother. Maybe that was why I’d been so aloof at first?

I’m still wracked with guilt. Ari and I had been friends. Close friends, classmates, and frat brothers. He was straight, I was gay, and though we did make out a couple times, it never meant anything. We were bros, and friends forever. Until suddenly we weren’t. He got married to his perfect woman, and they had a son. But then he was in that accident, and it all ended so quickly. We never got closure, but his wife and son visit the University every year. I since dove into my masters studies, work, and started drinking more.

His name is Robert. He’s like a cuter, younger version of Ari. The same dark eyes, and a old-world calmness about his manner. Unlike Ari, he’s shorter, a little hairier, clearly gay, and kinkier than one could believe. Watching what he was doing with Shawn was both terrifying and fascinating.

Continue reading Bro to Ho – Part 4: Gabe’s Story →

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Bro to Ho – Part 3

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By Cutieboy90

Cutieboy90 gay bondage storiesThe rest of the semester flashed by in a blur of exams, finals, studies, and presentations. For me, it wasn’t a big deal, it was just the end of another semester. No distractions, no worries, just the expected tedium and routine. I knew it was very different for Shawn, and the idea of a whole house of horny, stressed out frat boys using him harder than usual was one I jerked off to most nights when I had the time to do so. The other image I got off to? Well…

Billy called at the end of Thanksgiving break, with a top-secret agenda. Before I’d volunteered Shawn to be the house bitch, Billy had been considering someone else: Gabe, a hot, muscular stud with a quick temper. The sinewy young man had short sandy blond hair and deep grey eyes, perfect grades, and was a valuable asset on both the wrestling mat and the football field. He’d returned to grad studies after taking some time off. Billy’s idea was to temper Gabe’s hot-headedness by locking him up and humbling him until he learned to keep his cool. As Gabe was an openly gay member, the bitch duties wouldn’t be as much punishment, rather a reward for improved behavior. The only real catch was that Gabe considered himself a total top, an alpha, like most of these guys thought of themselves.

First things first though, Billy wanted me to check Shawn’s progress myself. Surely I could also see what I thought about Gabe too at the same time.

And that’s how I got an invitation to the party.

Continue reading Bro to Ho – Part 3 →

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Bro to Ho – Part 2

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By Cutieboy90

Cutieboy90 gay bondage storiesI am not a sadist, a fact that might surprise many considering the extreme methods I employed and allowed with Shawn. For the past month, he’d been locked in an indestructible titanium chastity cage, and was adjusting an entirely new life in the frat house. He’d wake up at 4:30 on the dot, shower, groom, workout and stretch, and offer morning blowjobs. The inconsistent sleep he got was on the floor, or in a metal dog crate in the basement. Normally, he wasn’t allowed to speak or move without permission or specific orders. The frat house was brutally strict in that regard, and the only things that took precedence were Shawn’s classes and treatment-related appointments and therapy. Which meant that a great majority of the time, he was available for bitch duties.

While I do believe it was necessary to maintain his normal routines, I did not need to keep up the hellish conditions and protocols of the frat house. I enjoyed letting Shawn have a bit a of a break to recharge and recover. He slept in the bed with me, and he was allowed to speak and move as he wished. I kept him naked, collared, and shackled, but otherwise he was free. He’d wake up at 5:30 on the dot, shower, groom, workout and stretch, and offer a morning blowjob. I had him practice with dildos and butt plugs to keep himself limber for when the break ended. He was very polite, respectful, and quiet. I could tell he appreciated the affection he got from me. The week went by quickly. As the last day dawned, he showed a bit of a mood change.

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Bro to Ho – Part 1

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By Cutieboy90

Cutieboy90 gay bondage storiesShawn was your typical all-American dumb frat boy. Muscular body, cute face, ripped jeans, and Abercrombie T shirts. He partied, drank, played around, and took everyone and everything around him for granted. Now, one would think that a guy who had flunked out of college twice already, and chose to try again a third time would have learned something from his mistakes, or at least cared on some subconscious level about his future.

Not Shawn. The first week of classes he acted like every other high school jock ready to get up to no good with their new adult life. He was rarely on time for classes, never studied, barely participated, except in anything athletic. We were both on the swim team, and though he could almost keep pace with me, he was never seriously considered for competition due to his lack of effort. Every night, he’d stumble into the dorm, drunk off his ass, shuffle around for a while, before passing out anywhere but on his cot. As a serious student with early morning lab classes, this was not an acceptable situation.

But I knew his kind, sitting down for a conversation mediated by the RA was not going to be any help. Logic and reason are lost on these guys. I would find another way.

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Milking Day – Part 4

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By Cutieboy90

(To start at Part 1 of Milking Day, click here)

Cutieboy90I stared at the wall, like I had for the past hour or so. No, not by my own choice. I was strapped in this position, my ankles spread with a bar, and my arms behind me. A thick leather muzzle kept me quiet, and there was a tether attached to the top of it keeping me in place. There was also a tether around my full, aching balls, which were already feeling a squeeze from that infernal steel chastity cage that’s been locked on them for over two months.

I huffed into the thick leather padded muzzle as Mark finally approached. I heard him set something down behind me, before he came into my field of vision. He patted my head, and kissed my gagged mouth.

“You look so fucking pissed!” He teased, pinching my cheek. I huffed a muffled obscenity at him as he chuckled. “Now now, don’t forget who’s in charge here,” Mark firmly slapped my nuts, instantly making me double as much as the restraints would allow. My nuts were already so tender, I was close to tears at the third strike of his palm. But of course, my sadistic boyfriend just smiled and continued to tap his palm into my package until I was on the verge of passing out. Damn did it hurt.

He kissed my forehead, and stepped away while I caught my breath. Much to my surprise, he began to unbuckle the heavy leather muzzle from my head. I didn’t get to say anything, as he kept his hand over my lips once the leather was pulled away. I kissed his fingers, knowing it would probably be several hours before I got the chance again. I closed my eyes, as he fingered my mouth. Evil he might be, I still loved him.

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Milking Day – Part 3

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By Cutieboy90

Cutieboy90 gay bondage storiesIt’s been three weeks since the last milking day, when my boyfriend Mark sabotaged my chance for release. Three weeks, and just one more to go before I could try to reverse the roles, and lock him up for a while. To date my dick has been locked in a steel cage for eight weeks, and I really miss stroking it.

Mark had been having some difficult weeks at work. Layoffs meant there were fewer people to do the same amount of work, but the work still had to be done. Mark’s had longer days, and he was so tired when he got home. Too tired to go to the gym, too tired to eat, too tired to even jerk off! I was worried about him.

One late afternoon, Mark pulled his car into the garage. I heard the door close, and waited for him to come in. I’d been preparing dinner, and was surprised he was home so early. Even though he had gone to work so early, it hadn’t made any difference as he still came home so late. Today was odd, that he was home early. And he was taking his time coming inside. Huh, how strange, I thought as I washed my hands. Better go check on him.

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