All posts by Cutieboy90

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

Milking Day – Part 4

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.

Continue reading Milking Day – Part 4

Milking Day – Part 3

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.

Continue reading Milking Day – Part 3

Milking Day – Part 2

By Cutieboy90

Cutieboy90 gay bondage storiesIt had been hours. I was naked, hogcuffed, ballgagged, with a huge electro plug humming away up my butt milking my prostate after five weeks of chastity. All I had to do was not orgasm until Mark said it was time.

Speaking of Mark, he’d been flipping through the various sports channels, watched a few games, a bit of news, and switched to a sitcom for a bit too before turning back to basketball. All the while, his big feet were all over me. In my face, resting on my shoulders, stroking my back. I was drooling heavily on my ballgag, and leaking constantly through my chastity cage, moaning as he pushed on that gigantic plug.

This was torture. Plain and simple, I thought to myself. Four hours, and I was still horny as hell, fighting back the urge to cum, and I was exhausted. I let out a whimper and a torrent of drool. Mark looked over, taking his feet from where they were resting on the small of my back. He leaned closer to me.

“Aww, whassa matter? Bored? Well I suppose you can’t see the TV…” His voice had such a patronizing tone, the teasing sexy bastard. I rolled my eyes, but mostly my fight was gone. Mark seemed to think for a moment, and then stood up, a twinkle in his eyes. “Got it! I know exactly what’ll cheer you up. Be right back.” He darted into the other room, and returned a moment later with some nipple clamps.

Continue reading Milking Day – Part 2

Milking Day – Part 1

By Cutieboy90

Cutieboy90 gay bondage storiesI had one goal. Just one. Over and over again I repeated that one rule, just the one; no matter what, I was not to cum within the next minute. And when that minue was over, then set the goal again for the next minute, and so on and so forth, until my boyfriend wished it.

I was on all fours, naked save for the blindfold tied over my eyes, the ropes keeping me in place, and the steel chastity cage that had been locked on my junk for the past three weeks. Now, this really wasn’t anything unusual, as my boyfriend Mark and I are bondage addicts, and while we’re both switches, I tend to be more submissive. Chastity, of course, brings out my submissive side, making it easier for both of us. Today was my milking day, and I was just so fucking ready for it.

My body was shivering with anticipation and horniness. Mark had said he had a surprise for me, and had left me here blindfolded, what seemed to be hours ago. Whatever surprise he had in store, no doubt it had something to do with my milking, or with bondage, or something fun for one of us. My mind would go crazy with all the wild ideas I could think of, each one making my dick strain in the cage, and my full aching balls churn. I’d shoot my three-week load if I didn’t mindfully tell myself not to.

Continue reading Milking Day – Part 1