Sissy Sessions Ch. 03

Note: Sissy Sessions is a series of short stories you can read individually. I'll use characters from previous chapters from time to time. The plan is to keep as many entries as possible as standalone stories. I hope you enjoy it. Thanks for reading, and don't forget to star and comment! 

One of his hands gripped my throat hard enough to let me feel the pressure without choking me. The other reached down between my legs. Legs that are currently raised and spread. Attached to my ankles are cuffs connected to restraints hanging from the ceiling. The restraints force my legs up towards my shoulders as I lay on my back. I'm almost folded in half, but not quite. Looking up past my captor, I can see my bright red toenails peaking through my open-toe heels. Bright red is this week's colour of choice. The colour of the heels matches my toes. He's fingering my hole rather roughly, with a sense of extreme purpose in his eyes. My caged member is leaking profusely as my eyes roll into the back of my head. 

I can't help but think back to the events that led us to this point. It's been a culmination of a variety of defining moments and events in my life. These past 2 years of being Gary's complete submissive have opened my eyes to my reality. 

I'm captain of my college's soccer team. This is my senior year, and my coach decided I deserved to wear the armband this season. Mom was so proud of me. We're coming off a rough season, and the previous captain graduated. A couple of our better players also transferred. With the depleted roster, I was the only logical choice for captaincy. I'm the longest-tenured member of the team and the official leading scorer by default. The three players ahead of me in goals scored are no longer with the team. Mom worked her ass off for this moment. Literally. 

She doesn't know I know her secret. All throughout my youth career and high school, mom sucked and fucked any dick willing to pay. We grew up poor, and she needed the money to give me an opportunity at a sports career. Mom always dreamed I'd grow up to be a star athlete. She had it in her mind when she saw all the players in the NBA and NFL who made it without fathers in their lives. She fell in love with the idea that her boy would become rich and famous. The number of times I would come home to her muffled cries of pain and pleasure. It left an impression. 

On occasion, she would get sloppy. I caught a glimpse a few times. The way the men treated her repulsed me. They degraded her. Some got physical; others were verbal. Oftentimes, it was borderline abusive. 

I never said a word. I couldn't bring myself to speak up. I was ashamed. I couldn't get enough of it. My poor little mind couldn't comprehend why my cock got as hard as it did. 

At 5'5" and 155 lbs, I'm not tall enough for basketball or big enough for football. I could never stand the blisters I got on my hands from playing baseball. It seemed hopeless, but mom's determination persevered. It turns out that my lean body and long legs make me a decent soccer player. Not quite good enough for my hometown college, but a couple of nearby schools were willing to take me. Scholarships were minimal, but mom said they gave me a fighting chance. Deep down, she was hoping for this challenge to help me build character. She told me she knew I would rise to the challenge and be the man she knows I am. 

I slowly worked my way from benchwarmer to starter over the years. In my freshman and sophomore seasons, we were unbeaten against my hometown school. Those two years living on campus, away from mom, helped me put all my focus on my game. I became a better player. I got stronger, and in turn, my performance improved. I became good enough to start in my junior year. That's when things started to turn. 

I faced him twice that season. Once on their turf and once on ours. I scored the game-winning goal in the first game. It was a great night. Mom and I ended up celebrating that night since I was in town for the game. We had pizza at her new apartment. It was a lot fancier than the places we lived in when I was growing up. Without me around, she didn't need to spend as much money. One less mouth to feed. I tried to ask her about work, but she deflected. She told me we were there to celebrate my big win, not talk about her boring life. 

Later that night, I woke up from my sleep to go pee. On my way back to mom's guest room, I heard it. 

"Yeah, you're such a good fucking bitch, Holly. Suck that dick. I'm gonna cum all over that pretty little face. You do such a good job of using all the makeup I paid for; I'd hate to let it go to waste."

I froze in my tracks. Mom's bedroom door isn't open. I can't see what's happening, but whoever's in there with her is doing a good job of describing it. I didn't dare move. I'm too scared to have them hear me. Too horny to turn down the opportunity to relive the feelings of my shameful arousal. 

I sat in the dark and listened for the next 30 minutes. I heard every moan, whimper, and smack. When it was over, I pretended to be asleep on the couch when mom's partner left. He didn't see me. 

Mom was in her bathroom. From the sounds of things, I knew she would be in there for a bit. I took this chance to look out the window to see if I could catch a glimpse of the man who just fucked my mother. Instead, I found myself making eye contact with Gary for the first time. He was getting into the car outside the apartment building. It was only a brief moment, but we made eye contact, and he winked at me. 

It sent a chilling shiver down my spine. I don't know what it was, but I felt this shiver all the way down to the tip of my cock. When Gary drove off, I scurried back to my room and jerked off relentlessly. 

A couple of weeks later, I still couldn't get it out of my mind. That wink. The amount of cum I was spilling on a weekly basis was becoming ridiculous. I had to take a break because my cock was becoming sore. It got so bad. My performance on the pitch was beginning to suffer. My promising junior year was nosediving. The first half of the season saw me drawing interest from pro scouts. The number of scouts dropped from 3-5 per game to 1. I was lucky to see two scouts in the stands who were there to see me. It only got worse from there. 

I was so productive in the first half. Even I started to believe I could go pro. I knew I had to stop. My career was slipping away with every spurt of cum leaving my balls. 

"Hey. Took awhile to find your profile on here. You do a good job of keeping a minimal social media presence. I like that." 

It was a message from Gary on LinkedIn. 

"I'm sorry, I think you have me mistaken for someone else," I replied. I knew he had me, but I didn't want to bring my depraved sexual fantasies to a professional social site. If I wasn't going pro, I would need to have something to fall back on. That's the only reason I built this stupid LinkedIn account. I never thought it would be my downfall. 

"Meet me for coffee. There's a coffee shop about 30 minutes from you. I'll send you the address." 

My phone on the nightstand behind me beeped. I turned in my chair to reach for it. I received a text from an unknown number. Inside was the address of a coffee shop. 

"Your mom, Holly, gave me your number," the next text read. 

"See you in 30, bitch boy." 

My heart started to race. It was becoming hard to breathe. I had to slow down my thoughts. Before I knew it, I was on the road in my beat-up old car. My cock was the hardest it had been since I first found out my mom was a prostitute. 

There were a few people in the diner-style coffee shop. I could see Gary sitting in a booth off to the side. He spotted me sitting in my car in the parking lot and waved at me. To his credit, he never once rushed me. He waited 15 patient minutes for me to work up the courage to go inside. I set my mind to it in about 5 minutes but needed the extra 10 to let my erection calm down. 

"Hey, I'm Gary," he said as he shook my hand. 

Things escalated in a hurry. 

I was compliant, meek, and docile. Despite his brash tone, following Gary's lead came easy to me. 

"Seeing you prance around on the pitch, I can't believe you got that lucky goal. Steve's so shit, no way you score on a competent goalie. I always knew you were a faggot." His words stung. The truth hurts. 

"Follow me back to mine. My dad's spending the night with your mom. We'll have some privacy," he said before he paid the bill and left the shop. 

This dominant, arrogant piece of shit had me eating out of the palm of his hand. Like I said, those early days with mom left an impression. Looks like she and I have the same taste in men. Imagine if she could see me now. Her sweet star athlete. Little did she know. She was right about one thing. Playing with balls would be a prominent part of my future. 

It didn't take long for me to find myself completely naked in front of Gary. His room was bigger than the apartment where I first saw mom get fucked. There I stood in my bare glory. My cock was as hard as it could be. He smirked with a knowing smirk. Not that there was any doubt, but it was nice to get confirmation of his suspicions. 

"Not much hair. Nice. We'll have to do something about that little bush, though," he remarked. 

"On your knees," he said as he pushed me back a step. 

I lost balance and had to brace my fall with my bare ass. The floor was cold, but my blood was running hot. I rushed to my knees for him. I finally understood why mom let those men treat her the way they did. I used to tell myself it was only for the money, but mom didn't stop even after I got a part-time job to pay for my own stuff. She liked how those men made her feel. She liked feeling powerless at the whims of powerful men. I didn't understand then, but I do now. 

Gary held me steady. He had a handful of my shoulder-length hair in his right hand. I bet it looked like he was holding me by a dirty blonde ponytail. We maintained a steady rhythm as he explained my new life to me. 

"Don't worry about being good. Right now, you focus on becoming familiar with how it feels. Remember the feeling of the veins and the taste of my skin. You're naked now, but you won't always be. I own you now. I want you to feel completely stripped of your livelihood when I break you in tonight. We're going to break you. Then we'll build you up again." 

I couldn't help but remain silent in my submission. Never once did I object or complain. I wanted this; no, I needed it. All I knew growing up was that mom provided for the family by serving cocks like Gary's. She sucked and slurped like I'm doing right now. She never knew it would have this effect on me. Hell, I didn't know either. 

My life today is possible because of rich men's cocks. It was almost as if this was part of my conditioning. My entire life, I found sexual ecstasy while masturbating to the image of other men's manhoods. 

Gary made love to me that night. It remains the most intimate night of my life. I'll never forget how my naked body felt. The way he touched me. It felt as though every touch left an imprint on me. The way he gripped my waist and leaned his chest onto my back. Feeling the heat of his hips on my rear end. The way my butt shook when our bodies collided. The weight of his arms and shoulders on my calves and the backs of my knees. It was all so intoxicating. I loved it. I loved him. He made me feel helpless, like when I was younger. 

He knew he had me. He allowed me to experience a night of love. Gave me something to strive for. Gave me something to chase. 

From there, I became addicted to his approval. 

He began to take control of my life. I couldn't think of anything but him. We lost our second game against his school that season because of crucial mistakes by me. Two giveaways resulting in two goals in the first half are hard to come back from. 

Tonight was the last time we would face off on the pitch since I was a senior. It also happened to be my birthday. It was a 1-1 game, and it came down to my penalty kick. I managed to draw a penalty on Gary in the box. I couldn't believe it. Mom was in the crowd, and I didn't want to let her down. By now, she knew I wasn't going pro, but I wanted to show her that I could still step up and be a man. It was all a charade. I was too scared of her discovering my relationship with Gary. I couldn't stand having her find out that the boy she so desperately wanted to raise into the type of man who used her ended up just like her. The shame of knowing her baby boy is a slut for the same type of depraved sex she is would devastate her. 

I won the game for us that night. Instead of celebrating with mom like last time, she thinks I'm out on the town with my teammates. I kissed her goodnight and made my way to Gary's penthouse. 

I showered and moisturized. My body is now completely hairless below my eyebrows. Laser treatments meant none of it was coming back. My cock, the release valve for all my sexual frustration in my youth, is now caged. The stainless steel felt warm because of the hot water in the shower. It's a snug fit in the cage section, but the ring is deliciously tight. It's pulled into my pelvis and held in place by a band that runs around my waist. The tightness causes my scrotum to hang low. Gary loves the way it swings when he takes me from behind. 

Gary's left my outfit for the night by the vanity. A pair of bright red high heels and my collar. The tag was the logo for some club I know nothing about. The shade of red on the heels matches my toenails. He left out a bottle of polish for me to do up my fingers too. I took my time to make sure each nail was perfect before I moved on to the rest of my hair and makeup. When I was ready, I used plenty of setting spray. Daddy doesn't like when my makeup runs. He fucks me extra rough to test the durability of my work. One last twirl in the mirror while I stand in my heels. A quick flash of his initials tattooed on my ass sent a familiar shiver down my spine. Branded like cattle. 

Tonight's my birthday. I thought he would make love to me tonight. He did on my last birthday. 

It was a shock to find him seated in his playroom with my leash in his hand. Without a word, I walked over to him, kneeled at his feet, and took him in my mouth. 

I felt him reach down and attach the leash to my collar. Then he reached over his head to attach the other end to a gear in the ceiling. I continued to suck without a waiver. He hasn't showered since the end of the game. He's not in a good mood, and he hasn't said a word to me yet. 

"Up!" he grunted as he pushed me off his cock. I started to rise to my feet before I felt a tug on the leash. The remote in his hand was forcing me to rise quicker than I intended. The mechanism in his ceiling began to drag me across the room toward the bench. He only used this pace on the chain when he had a lot of pent-up frustration. It became clear he was not happy to lose tonight. 

"Please," I pleaded. 

Whack. My ass was on fire. 

"Please, Daddy, I'm sorry," I continued to beg. 

"Shut the fuck up," he commanded as he grabbed me by the back of the head. He walked me over to the bench and pushed me down onto my back. He wound the chain up. The tension was keeping me from moving my neck too much. Then he strapped my wrists together behind my back beneath the bench. In this position, I'm stuck on the bench. I couldn't get up if I wanted. For good measure, he cuffs my ankles and attaches them to the other ceiling restraints. 

"Uhhhhh," I groaned in pain as he flicked my sack. 

In went his fingers. My ass is already lubed as a result of my post-shower routine. 

His hand grips my neck as he fingers my inner crevice. My eyes are in the back of my head as I lose myself in the pleasure. 

"Open your fucking eyes, bitch!" he shouted. 

My attention was quickly drawn to the computer monitor above me. It looked new. I don't remember that being there last time. That's when my eyes widened. 

It wasn't the device itself that scared me. It was what was playing. 

"No, please, no. Not this, Gary. Stop. Please!" I begged. 

On the screen were my mom and Gary's dad. She was on all fours, getting railed by the hairy man. Like his son, Gary's dad had a penchant for grabbing a bitch by the hair. The way he held my mom's head as he fucked her like a dog was causing me to leak out of my cage. 

The camera for this livestream was on the ceiling. It pointed down at my mom, so I couldn't see her face. 

"Michael?" she asked between his heavy thrusts. 

"It's Michelle now, bitch," answered Gary's dad. 

Another monitor turned on, followed by another. I was now given a scene of my mom from different angles. I can now see the look of shame on her face in high definition. Another angle showed that Gary's dad held mom's held firmly to prevent her from looking away. He wanted her to watch his son destroy the last remaining semblance of her son's manhood. 

"You worked so hard to make sure he would grow up to be a good, strong man. You convinced yourself that not having a fatherly figure wouldn't be a detriment. Now look at him," I heard through the speakers. 

"He told you he was out with his teammates, but you watched the same thing I did. He came running here to pamper himself and take a dick in his ass like the good bitch he is," he continued. 

Gary's dad then looked into the camera and nodded. 

It was a cue for Gary to impale me. 

"Ahhhh," I shrieked, as I was not expecting it. 

The sound echoed through the speakers as my mom watched on. Mom's head turned left before Gary's dad wrestled her back in place. 

"Now you know this is real. He's in the room right beside us," he explained. 

"You know the safe word. Say it, and all this is over. Say it, and you'll both be free," I heard Gary say. 

"We'll let mom go too." 

Gary began to stroke my ass with his cock. It was sensual. He was making love to me again. 

"I'm sorry, mom," I thought to myself as my pretty red lips remained sealed. I'm unwilling to give up Daddy's cock.

"That's what I thought. Good girl," Gary said before he changed his pace. He went from making love to me to a brutal fuck. His hand once again found my throat. My whimpers sounded suppressed with his grip on my airway. My rear canal ached with a familiar pain. I've become accustomed to the feeling. It often felt like Gary was trying to split me in two with his thrusts. He humped me with a purpose. Once he took away my ability to jerk off, I felt like my body was rewiring itself. With every agonizing stroke, I started to feel more and more pleasure. The amount of clear fluid leaking from my cage made that evident. 

The appendage, formerly known as my cock, looked like it was salivating whenever I had Gary's cock up my ass. In a twisted and perverted way, Gary was Pavlov, and I am his dog. Leaking in my cage is now my natural response to being sodomized. 

"He takes it rougher than you ever could." Gary's dad was taunting mom, who's now panting like a bitch in heat. 

"Bitch loves it too. He comes over here all the time to bounce on my boy's cock. You should see how fast he gets here to swallow my grandkids. I guess I must have good genes. Like mother, like son. Neither of you can get enough of our cum." 

The way he talked to mom was only making it harder for me to keep from spewing a load all over myself. 

By this point in the evening, Gary had repositioned me to match my mom and his dad. It gave the cameras a better angle of the action. Where I kneeled, a special camera pointed directly at my leaking cage. It served as a constant reminder of how much I was loving this.   

Gary continued to slam into my ass. The sound of our flesh meeting was deafening. I could see my ass was turning pink from the repeated impact.