Coach's Sissy Ballboy Ch. 01

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Virgin sissy Alex wants to be his coach's girl.
3.6k words
4.45
14.5k
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Part 1 of the 5 part series

Updated 05/28/2024
Created 05/16/2024
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Part One

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I had always been a bit feminine in my body type. I was of average height -- about 5'8" -- and slender, about 120 pounds. Though I was thin, my ass was round and soft; sometimes I liked to kneel on my bed and stare at it in my bedroom mirror, imagining that I was offering it to a man with a big, firm cock ready to plunge between my cheeks.

My facial features were pretty feminine too I guess, with a small nose, and a round jawline below high cheekbones. My hair was dark-brown, and I kept it in something of a pixie cut. Otherwise, I had hardly any other body hair below my neck. I admit that I liked feeling somewhat feminine in my body; it made me feel sexy.

A lot of boys at my high school called me a sissy, which I secretly grew to like, even though they meant it to hurt me. Meanwhile, there were other boys at school who seemed to look at me hungrily, which I also liked. Thankfully though, I had a couple friends who were big and strong enough to keep bullies from messing with me too much. These guys, James and D'Andre, were my friends because I was on the basketball team with them.

You might ask why a thin, uncoordinated guy like me was on the team. The truth was that my father was to blame. He had always wanted a son who was athletic and tough; poor him ended up with me instead. But I joined the team to make him happy, and I actually made friends there, which kept me engaged when I was riding the bench. Most of the time, I was making sure the starters had enough water at timeouts, and I helped Coach keep track of the stats. Oh yeah, Coach. He was the other reason I stayed on the team.

But I'm getting ahead of myself. The truth is that I wasn't sure if I was gay or bi, I hadn't really thought about it too much at that point. Because my friends James and D'Andre kept me safe from bullies, I could just be myself without worrying about these things. I had had a couple different girlfriends in my first couple of years of high school, but those relationships always fizzled. One time I had found another guy locally on a dating app who I met a couple times. We made out a bit and did some heavy petting, but I think it didn't work out because both of us were too timid. I think then was when I realized I wanted someone who would take control, who would take me in hand and assert dominance. I wanted to be someone's sissy.

Truth be told, I found D'Andre more than attractive enough; early on in our friendship, I would imagine his big, ebony hands playing over my porcelain skin, arousing my little pink nipples as he plunged his black shaft into my willing virgin boy-pussy. But he was straight and in a long-term relationship, and I didn't want to obsess over a friend that way. I knew it could never happen with D'Andre; but at least I could daydream about Coach Cade.

Coach was muscular, but just enough to not seem unnatural. And he had a firm jawline and short curly hair. With that and his bronze skin, he looked like how I would imagine one of the Greek or Roman gods, in their virile power and grace. Sometimes when I was near him, I would imagine that he was Zeus and I was a servant in his temple, available night and day for him to use my nubile body to vent his insatiable libido.

One of the things that drew me to him was that Coach was always very kind to me, not making me feel inferior for being such a useless basketball player. He didn't treat me any differently than any of the other players when we weren't in a game, in fact he seemed happy to include me in conversations about the team and his strategy. It made me feel good to be included, but I also had a hard time starting up conversations since I was so attracted to him.

Coach wasn't terribly older than me, probably in his early 30's. In addition to his imposing masculine presence, I could never help noticing how big and strong his hands were, and his powerful forearms were distracting. Sometimes in the middle of a game as I watched him write plays on his dry-erase clipboard, my mind immediately raced to a picture of him grabbing my soft, round ass with those strong hands, my back arching as he pressed his hard frame against my soft one. Of course, then I had to make sure I didn't stand up from the bench for a while because of my raging erection.

Sometimes I was daring enough to wait until everyone else had left the showers and I would lather myself up and picture Coach coming in and noticing me there. In my mind, he would come over and push me up against the wall, and begin to caress my nipples as he kissed my neck. Slowly, he would slide his hand down my smooth, hairless chest and belly until he grasped my firm cock, sliding his other hand around to slip his fingers inside me, making me squirm and moan. This always ended with me shooting my load all over the shower.

Other times at home, I would lie in bed and imagine that Coach invited me into the sports equipment closet and grabbed me from behind, tearing my clothes off and bending me over as he plunged his throbbing pole into my boy-pussy. As I lay in bed, I would cum all over myself. I didn't have to worry about my parents walking in, since my dad worked until late at night and my mom was busy with her stuff, like volunteering and visiting my grandma who needed lots of care. I had an older sister too, but she was off at college. My parents wanted me to go to college after this year's graduation, but I wasn't sure. At 18 years old, I would rather work and save some money.

Still, I was a decent student, and for fun I would swim, or hang out with the guys from the basketball team in my free time. Life was pretty normal. That is, until a fateful day when my life took an unexpected turn.

That day started normally enough. Since I was the coach's assistant, I was picking up basketballs and towels after practice, getting ready to head home, when Coach walked into the gym. My heart immediately began beating faster, but I knew he was just checking to make sure everything was being taken care of. But then he waved at me and walked over. "Hey Alex, looks like you are about done, thanks for picking up. When you are finished, why don't you pop in my office. I have a thought to run by you." As he said this, he put his hand on my shoulder, and I was immediately filled with thought of what Coach Cade might do to me in the solitude of his office. I knew this was just a daydream, but it came automatically, along with a stirring in my loins at his touch. "Oh, sure! No problem" I managed to say, my face a bit flushed. He smiled his handsome smile and nodded his thanks as he turned and scooped up a loose ball, giving me a moment to appreciate his tight backside.

A few minutes later I stood in his office. "Go ahead and grab a seat" he said. I sat in the comfy chair in front of his small desk. He continued, "I was talking to your parents when they were here at parent-teacher meetings, and I was telling them what a great teammate and assistant you are." I smiled and looked down at the floor, hoping he couldn't see my cheeks redden slightly. I didn't get compliments very often.

He cleared his throat, and then continued "Your dad was asking how you were doing at basketball. I told him honestly that you always play hard, but that you could use some more help with the fundamentals; dribbling and defense. But unfortunately, I don't always have time during school hours to work one-on-one with people as much as I would like." I nodded.

He continued, "I suggested to your dad that, if you were okay with it, you could stop by my house some days after school and work on the fundamentals. He seemed supportive of that, and since your mom was concerned about making sure you get your homework done, I mentioned I could help with that if you needed it too."

I was shocked. I must have looked it, because Coach immediately held a hand up in a calming gesture "There is absolutely no pressure though. If you don't want to spend your time that way, it is totally fine. Just a suggestion if you want to work on your game a little."

I stammered a bit, and then said "I feel like it would be a big time commitment from you, I wouldn't want to..." but he interrupted gently, "I sometimes have free time on my hands, so it isn't any kind of inconvenience. It's worth it to me if you think it would help."

I thanked him and told him I would think it over and let him know. He smiled that smile again and went and opened the door for me. My mind was clouded with the idea of Coach and me alone at his house as I stood up. I began to walk past him and couldn't help but look down to avoid his intense hazel eyes. I was afraid he would be able to read my thoughts, or at the very least see my burning cheeks. As I passed him, I swear I could feel the heat of his body, and I quickly left, lest he see my cock straining against the front of my basketball shorts.

I walked in a daze out of the building and towards my car. It was like my fantasies were bursting into reality; but I honestly didn't know if I could handle being alone with Coach. I would probably make a fool of myself, or have a non-stop erection the entire time I was at his house!

On the other hand, I imagined that if I actually spent time with him, my fantasy world might come unglued in the face of reality. Regardless of my cum-soaked imaginings, there would be no sexy shower times, or me riding his throbbing manhood up and down in his bed. Most likely it would just be spending normal time together, working on basketball and homework. But I realized as I drove home that I might enjoy that just as much. Losing the fantasy in exchange for time with a man who was kind and thoughtful seemed like a fair trade, even if he wasn't going to fill me with his cock.

The next day, I arrived at school with my mind made up. I would take Coach Cade up on his offer. I might have to find a new target of my inner sexual escapades, to keep from embarrassing myself around him, but it was probably worth it.

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Part Two

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Coach Cade seemed genuinely happy to hear that I was on board with his idea. I had told my dad before I left for school that morning, and he seemed happy too. I asked Coach when we would start. He replied "Whenever you want!" Then he paused and corrected himself, "Well, I should say, the earliest would be this Thursday. You could also come over Saturday if you have nothing better to do."

I thought about it; Thursday was a school night and I was usually tired after class all day followed by practice. But Saturday was the weekend! In spite of the idea of losing weekend free time, I decided it was probably the best option, so I said "Saturday sounds good. Maybe in the afternoon?" He nodded, "Sounds good. Let's plan on it."

The rest of the week was a whirlwind of thoughts. I fluctuated between fantasies of taking Coach's pulsating cock into my mouth, and mentally splashing cold water on myself. I didn't know what to think! I began to get more nervous as Saturday drew nearer. The only way I knew how to blow off steam was to pleasure myself to some femboy hentai while using a homemade dildo -- a thick, whittled down candle -- as I imagined a beefy dark stranger ramrodding me with his big, thick member. I filled many tissues that week.

On Saturday morning, I couldn't help myself; I used my dildo to stretch my hole, and then used a makeshift enema to clean myself out. It wasn't that I expected Coach to take advantage of me, but it felt sexy to be prepared as if he would. I managed to restrain myself from masturbating since I didn't want cum oozing out as I practiced basketball moves with him.

When I arrived, Coach was working on his gutters. He had already worked up a sweat, and I knew this was going to be trouble. His shirt clung to his sculpted abs and biceps, and I knew he would smell strongly of the kind of musk that drove me crazy; I had caught the scent before, during games and practices. It was like his scent called to me, making me sweat. I swear I even felt my boy-pussy inflame with desire when I smelled him.

He waved as I pulled up, and climbed down the ladder. I tucked my erection upwards before I stepped out of my car.

"Hi Alex! How's your weekend been so far?" I shrugged, "Fine I guess, nothing too exciting." I wished I had more to say, but I still felt so nervous and unsure of what to expect. He smiled anyway and said "Same here, unless you count housework as something to get worked up about!" As I stared at his clinging shirt and beefy legs below his tight shorts, I thought to myself 'You have no idea'.

We walked into his house, and he showed me around. It was fairly small but comfortable. He had a serviceable kitchen and a small office. As he pointed out the bedroom with attached bath, I was glad that it was relatively dark in the house, because as I glanced at his bed I flushed slightly at the thought of what I wanted him to do to me in those sheets. I could picture immediately his ass as it thrust up and down, pumping his meat into my tight, virgin hole. I shook my head to clear it as we moved on.

Next, we walked out the back, where a quarter of the yard was a small half-court with a basketball hoop. "I installed this myself, with some help" he said with a satisfied smile. As he stood with his hands on his hips gazing at his pride and joy, I shot a glance at him out of the corner of my eye, and my eyes ran down his clinging shirt to the decent-sized bulge outlined by his tight shorts. I bit my lip as naughty thoughts poured into my mind. I realized then that there was no way I would be able to resist the temptation of fantasizing about Coach ravishing my body. That decision seemed to actually allow me to relax, and I felt more myself around him. I snapped out of it as he turned suddenly, and I wondered if he had caught me gazing longingly at his manhood.

We joked a bit together as we went back inside. "Well Alex, do you want to practice first or take care of any homework?" I had thought about this, and I wasn't sure that I could practice with him without getting hard. But it might be best to get it over with right away. "Let's practice first" I said. He nodded and said "I was thinking that afterwards I could make a protein shake for us both while you do your homework." "Good idea!" I said, as I thought about a different kind of Coach Cade's protein that I would like to swallow. Man, this was going to be bad.

I went in the bathroom and changed into my shorts and t-shirt, gazing at the large, luxurious walk-in shower with transparent glass sides. I was surprised to see two shower heads on opposite walls of the roomy shower stall. I could imagine Coach and myself in there, with steamy, hot water pouring down on our naked bodies as we made love. I waited for my erection to subside so I could use the toilet and then I washed my hands.

When I went out, Coach was already warming up by shooting the ball. I grabbed a second ball and joined him and we shot around for a bit. I wasn't too bad, but Coach gave me a few pointers about how to position my arms when shooting. That is when things got more intense; he had been at my side giving advice on how to hold my non-shooting elbow for support, when he suddenly stepped behind me and put his arms around me to better show how to hoist the ball.

His presence flooded my senses. His scent filled my nose, and I could feel the heat of his body nearly pressing up against my rear. His hands lightly grasped my thin arms, and I couldn't help but quiver. I only just stopped myself from leaning back into him to feel his solid, sweaty torso against my back. My penis immediately began to stiffen and throb. 'Oh my god' I thought; I could swear he'd be able to hear my heart beating, because it was hammering so hard. He must have noticed something, because he paused for a half second, and then continued.

After he finished posing my arms in a shooting wind-up, he stepped away. I felt weak at the knees, yet I thought for just a split second that I might have seen the shade of a sly smile on his face, before he continued talking as if nothing had happened.

We shot around a bit more, then he said "Okay, let's practice some of those fundamentals. We are going to work on posting up and backing down." I looked at him, a bit nonplussed, and he clarified, "I will play defense, and you put your back to me. Just practice dribbling while backing me down towards the hoop." I swallowed silently, and nodded.

Then he took his shirt off.

My mouth actually began watering, and I felt a warmth in my loins as I saw his sculpted abs and pecs. His chest shimmered with sweat, and my mind immediately pictured me rubbing my hands over that sexy chest while he penetrated me in a missionary position. He tossed the shirt aside and clapped his hands. "Okay!" I snapped out of it, breaking off my stare.

I began by dribbling with my back to him, and as I backed up, I made contact with his body. My senses began to go wild again, but it was more restrained this time since I was distracted by bouncing the ball. I still dribbled the ball off my foot the first time, which I almost never do.

Once I got back in position and began backing up, I didn't make much headway. Finally, Coach paused us and said "Here, try this" and put his hands on my hips.

My dick immediately began to harden yet again. How many times had I dreamed about his big, strong hands grabbing my hips and taking control of my pliable body? He gently but firmly grasped my hips and actually drew me backwards onto his crotch. I flushed and began panting slightly.

"So, you want to back right up into the defender, like this. And just keep bumping them with your butt as long as they give space." He then held onto my hips with one hand and pushed my upper back so I was practically bending over, my ass rubbing on his groin. He came in close so it felt like he was about to mount me from behind. His bare torso was inches from my back and my thoughts were racing.

He continued, "So you are making space with your rear, pushing the defender away while dribbling, like this." I was dribbling alright, precum oozing from my throbbing cock. I was incredibly thankful to be bent over so he couldn't see the tent I was pitching.

We worked on this a bit longer, and I swear I felt his manhood a couple times brush up against my ass. He didn't seem erect, but his cock definitely felt large. I had trouble thinking straight, because I kept thinking of his arms wrapped around my body and taking control.

After working on that and a few more things for about 45 minutes, we were both breathing hard. Coach said "That should do it for today," and he walked over and poured me a glass of water from a pitcher on a table by the back door.

As he handed the cup to me he said "After a cool down, we can shower up." I almost dropped my glass.

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