Tag Archives: Cutieboy90

Locktober Part 1: Thoughts From a Solo Self-Keyholder

By Cutieboy90

“Damn…!” The thought of being locked in chastity for an entire month sent a thrilling rush through my being. My dick was instantly hard, and I felt somewhat high. I knew in that instant that my dick had just signed me up to participate in the Locktober challenge. It was already October 1, but not too late to start!

Now, a bit about me. I’m a single 26 y/o gay man, into bondage, chastity, and various forms of light role play and power exchange. But I also have significant trust issues which get in the way of most social, romantic, and play endeavors. So I take care of my needs myself, and engage in self-play. Chastity, of course, is no exception, and I hold my own keys for Locktober. After all, what kind of dom would I be to deny my Number 1 sub of an exciting experience?

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The first item of business, is the cage itself. It needs to fit properly! The cage I use currently is an “Adaptus” cage from Malechastitynow.com. It fits very well, though it is not entirely custom. The cage is a touch longer than ideal, it’s heavy, and the front bars are just a bit too far apart for total security. It’s a nice, comfortable fit for just under two weeks. But it’s the cage I have, and it’s a vast fit improvement over the Holy Trainer V2 I also own. (That could be an entire article. Another time..)

Continue reading Locktober Part 1: Thoughts From a Solo Self-Keyholder

Bro to Ho – Part 4: Gabe’s Story

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

Bro to Ho – Part 3

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

Bro to Ho – Part 2

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.

Continue reading Bro to Ho – Part 2

Bro to Ho – Part 1

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.

Continue reading Bro to Ho – Part 1

Hide and Seek – Part 2

By Cutieboy90

Cutieboy90 gay bondage storiesI took my time sneaking down the halls, up the stairs, and towards the kitchen, for I’d be damned if I got caught now. I wouldn’t normally take the risk, but after what just went down in basement, I needed some air to process what was going on.

Tyler was straight. Yet he let me, a gay guy who had a huge crush on him, show off for him, tie him up, and jerk him off. It was Tyler who sought me out in a confined space knowing we’d be there for a good amount of time. Tyler was gorgeous, of course, and didn’t seem to have much more than air between his ears. He couldn’t be toying with me. He wasn’t smart enough, and he wouldn’t be that cruel…

I tiptoed around the corner into the kitchen. I carefully took several pieces of fruit, berries, a few bagels, rolls, and some bottles of sparkling juice, and put them in my messenger bag. No, I thought as I looked around the kitchen, Tyler wasn’t playing me. He was just a stupid, horny young man. Unfortunately for him I wasn’t playing either, and he was completely at my mercy. So my record hiding time was seven hours and thirty-five minutes. But… I eyed the spray cans of whipped cream, and grinned to myself. I could easily smash that record playing with a hot, submissive straight boy like Tyler, and enjoy every second. Maybe even ten hours? I slipped two cans of whipped cream into my bag, and closed the door to the fridge. Time to go back and have some real fun!

Continue reading Hide and Seek – Part 2

Hide and Seek – Part 1

By Cutieboy90

Cutieboy90 gay bondage storiesSeptember was our 20-year high school reunion. This time, we’d go to Eric’s old family estate, like we always used to. It was a large, late Victorian monstrosity out in the country, with nearby hiking trails, lakes, a river, and woods.

Traditionally, the first night everyone was present, we’d play a huge game of hide-and-seek. The aim was to hide for as long as you could. The winner got to decide all the activities, meals, and got the best room in the house for the entire trip. I won almost every year, but I usually shared the winner’s privileges with everyone. Tonight, Eric would start counting whenever he felt like it, to keep us on our toes. As it was, he started counting immediately once everyone was present.

Everyone scattered as quickly and quietly as they could to find hiding spots. I always knew the best spots, and tonight I was going to try the ultimate hiding spot: inside the console of the pipe organ in the basement. It was one of those places that was so creepy, no one even thought to look in the basement, let alone near the pipe organ. Years ago, Eric himself had tried to hide there, but got creeped out after a minute and changed spots.

Continue reading Hide and Seek – Part 1