An Unexpected Wee in Chastity

Chapter One - Saturday

My head throbbed as I awoke to the sun's rays streaming through the window early on a Saturday morning. "Fuck me," I mumbled to myself wondering how drunk I was to forget to close the blinds. I am twenty-five now, I chided myself, and not in college anymore, I should never have gone to that college bar. My whole body ached like it was out of alignment as I lay there massaging my temples recalling what happened. The cute college boy, fuck I already forget his name, had hit me up on the Binder app and like a fool I agreed to meet the eighteen-year-old twink at the bar by Metro Uni.

Details of the night were just starting to come back into focus when my bladder reminded me I had more pressing concerns. As I gingerly swung my legs to the floor something felt off. My balls felt tight like I accidently left a cock ring on but that was not quite right, when I reached down my hand felt something hard inside my briefs. I carefully pulled them down and seeing the matte black cage locked over my cock I started to remember the details from yesterday. I shuffled to the bathroom, realizing I would need to sit down and pee like a girl, to avoid making a mess as I recalled the night.

At first, I thought the little twink had stood me up and a I started to drink earlier then I should have. Two hours later I had a strong buzz going and was about to leave when my date finally showed up. I wanted to be angry but the freckles on his youthful ginger face were so cute that it melted away any frustration. After we locked our lips together and I tasted his wet tongue as he probed it aggressively into my mouth in the dark back corner of the bar, he had me wrapped around his finger. Between his cute twink looks, his domineering aggressive tone and me being one too many drinks past rational I would have done anything he said.

As the bar was closing, I sloppily begged him to come home and fuck me which only got a wry smile from him. "You're cute but drunk," he whispered in my ear, "I will make sure you get home safe, and I promise I will fuck you, but we do it my way and when I say so." Of course, I agreed to anything the cute ginger twink said. I had caught only the briefest glance of his pale flat and firm abdominals under his shirt, but I knew I would agree to anything to be allowed to lick them.

As promised, he took me home and even agreed to a second date next Friday. But his terms were that I agree to wear a chastity cage until our next date, with him keeping possession of the key. I had never worn such a thing, and my memory is fuzzy, but I must have agreed because here I am sitting on the toilet peeing though this cage. Before standing I opened the Binder app looking at his cute face in the profile picture and reminded myself his name was Chris. "Well Chris," I spoke aloud to myself, "don't lose that key and I will see you Friday."

I decided I needed a jog to clear my foggy head and pulled on my usual compression shorts looking down at the odd bulge. I decided it was not too visible and opted to risk it. The first half mile was a little awkward as I got used to the hard cage between my legs, but I soon found my stride. As I was completing my usual laps around the park, I noticed one of the skater boys, who hangs out there, staring at me as I passed. After the last lap I was surprised when he waved me to him behind the maintenance building. I had seen him before hanging out with the other skateboarders in the park, he always stood out as the tall one, but I never talked to him nor knew his name.

Curiosity got the better of me after pausing to mop the sweat from my brow I walked over. "Psst back here," he called waving me further back into the shadow of the concrete maintenance building. Before I could ask him what he wanted I felt him push me into the wall, his hand grasping my caged crotch. "See I told you he was one of those caged submissive fags!" The tall skater boy declared. As my eyesight adjusted to the darkness, I noticed there were two other skater boys with him and began to get nervous.

"Look I don't want any problems," is what I started to say but I did not get past "want" before I felt a punch to my gut shutting me up. With my back to the wall the other two boys, one with a black emo mop of hair the other with dyed green hair in a buzz cut, moved up so they stood on either side of me. Clearly deferring to the taller one who had waved me over as their leader. Each of the shorter boys grabbed an arm holding me pinned to the concrete wall as the leader put one hand on my neck the other still fondling my caged crotch.

I am fit in a lean jogger way and at twenty-five I am older then these boys who could only be eighteen or maybe nineteen at most. One on one I could fight off any one of them but three on one and with the element of surprise I was powerless in their hands.

"Listen to me faggot, you speak when I say you can speak!" the tall leader emphasized his words by squeezing the hand on my neck briefly cutting off my air. "Now have you ever sucked cock?"

I hesitate, but I was too scared to lie, "Yes, but..." this time a hard face slap cut me off mid-sentence.

"It's Yes Sir to you faggot!" Feeling utterly helpless I replied as he instructed, any lingering thoughts of trying to talk my way out of this evaporated. His firm grip back on my neck and his skater boy minions holding my arms pinned he continued. "Those cages are for sissy submissives and slaves, which are you?"

I didn't see myself as either, but I knew he would want an answer and I didn't want him to think of me as a slave, so I replied meekly, "I guess a submissive Sir."

The lead skater boy grinned widely. With a gesture he instructed the other boys to push me to my knees and pull my arms behind me. As I was face to face with the waistline of his sagging jeans, I could see the outline of his bulging cock clearly aroused. His minions bound my arms with clothing line while the tall leader was grabbing a handful of my hair. Pulling my head back he spit on my face.

"Open your mouth fag!" he ordered, I obeyed. His next glob of spit fell slowly from his full glistening lips. Together we watched its slow-motion descent down the string of saliva into my gaping mouth. As I tasted his spittle his boys were tying my ankles together hobbling me. The leader pulled down his waistband unveiling his hairless twink cock as it popped out already erect and throbbing. The cock tip landed on my open lips and his glare made his expectation clear.

Knowing I was helpless to resist I licked the wet tip and wrapped my lips on it. "See boys I told you he would be a good little cock sucker." He growled as his hand in my hair pulled my face forward and he thrust his hips sinking the cock deeper into my mouth. I sucked down on his tasty meat reflecting how hard my cock wanted to be but all I could feel was it straining against the confines of the cage, the base ring pulling on my balls painfully. As the skater's cock rammed my mouth with increased vigor, I carefully wriggled my arms and ankles behind me, but the boys must know what they were doing as I felt no give or slack.

The pace intensified, I could taste the precum in my mouth and knew he was close. The skater arched his back and with a final thrust he shot warm ropes of his youthful cum into my mouth. He held my head tight to his body the softening cock still deep in my mouth until I swallowed down his load. Without being instructed I licked and sucked his cock and pelvis until it was all clean, earning me a laugh from the other boys.

"Ok faggot here is the deal you can pay the fag tax and go about your day, or my boys here get a turn." I wriggled helplessly in the ropes, his tangy taste still in my mouth. I was surprised how extremely horny I was with my cock locked in its hard confines, but I could contemplate the implications of that later, for now I asked him what the tax was. "I think a grand would do it," he sneered.

Once I admitted I didn't have that kind of cash they wasted no time in standing me up and ripping down my pants. The tall one easily controlled me with my arms and ankles bound. The boy with one side of his head shaved the rest of his long green hair flopping over, spit on his fingers and started to open my ass. I was shocked with how different and erotic it felt to be fingered with my manhood locked in a cage.

I didn't get a lot of time to reflect as the boy with the black EMO mop of hair pulled my head to face him and rammed his hairless twink cock into my mouth. My senses were in overdrive, my cock was emitting small pathic spurts of cum leaking into my cage, a pale shadow of a real orgasm. I tried to focus on the cock in my mouth trying to pleasure the EMO, I didn't want to contemplate what would happen if he was unsatisfied with my performance.

As soon as I got a good tongue and lip rhythm going, in a way I could tell he was enjoying, my concentration was ripped away again as the green hair boy switched from fingers to sliding his cock into me. I had dreamt of being split roasted before, but I never expected it to happen with random skater boys in the park while tied up. To make matter worse the tall skater was not idle as he held me, he kept slapping my sore balls and twisting my nipples while mocking my pathetic caged cock dripping seed.

I lost track of time as the three boys abused and used my body, but eventually I tasted the flood of EMO twink cum shoot down my throat and not long after my ass filled with the other skater's juices.

"Ok bitch that will cover your fag tax for today but if we see you in the park again you better be ready to pay in cash or come and service me." After I promised Sir, I would obey his commands he had his boys untie me and they let me go.

Like when peeing, I discovered showering after my jog was also a whole new experience. Standing in the water I let my soapy hands run around the cage feeling it slick on my wet skin. I was so wound-up thinking of the skater boys I wanted to grab my cock and whack off but couldn't. Soaping up my pinky I found I could slip it between the ring and cage the tip just barely touching my shaft. But this was more frustrating than helpful as the shaft had nowhere to go. Feeling unexpected pent-up energy, I did a full set of chest and abs workouts with my limited home collection of weights before bed.