Sissy to Military School Pt. 01

This is my first attempt at writing, it's the story about a sissy guy that goes to an opportunity school for challenged youths. And discovers himself.

This story depicts the explicit erotica of a transgender nature. If this material is offensive to you; or forbidden in your area, or you are a minor, please stop reading! All characters depicted in this story are of legal age.

This is a story with a plot and character development not a quick vignette of porn. I just realized how long this is. I hope you don't mind! I appreciate your feedback and comments!

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I didn't like school. I hung out with my friends drinking and getting high at the beach. I loved swimming in the ocean in the morning with a light buzz. Who had time for school? Everything I needed was provided by the beach!

My cell phone was a freebie the cell company gives with a subscription. The only money I needed was to pay my cell plan. To pay, I picked up alternate lifeguard shifts when someone didn't make their shift; or I would cover one of the beach vendor's stands for tips, as they took a break. The vendors also comped me free hot dogs and hamburgers. The guy that ran the surf shop would pay me an entire day's wage to watch the shop while he surfed for a few hours.

Consequently, I wasn't going to graduate because of my lack of attendance; who cares, life's a beach!

My folks thought it would be good to send me to military school upstate, to straighten me out, and complete my senior year. My stepfather couldn't stand me, so he was happy to ship me off to military school over a hundred miles away.

I should describe myself. My name is Stephen, I go by Stef. I'm 18 years old, I'm just 5'7. I get my looks from my mom. I have a slim build, but my hips and ass are disproportionately large compared to the rest of my body. I have blonde hair down to my neck. In the summer it seriously bleached out because I spend so much time at the beach with my friends. I have a soft face with high cheekbones and pouty thick lips.

I really detest that I have feminine or androgynous features.

I try working out, but my body doesn't beef up, it just tones, with definition. My abs are tight, My legs are defined, but my ass just doesn't want to cooperate! The more I squat, the wider and thicker it seems to become! The swimming keeps me trim.

It's really hot in the summer, and it's August, so I'm usually wearing cotton shorts, a tee-shirt and hi-top sneakers; no socks, and usually commando. Underwear doesn't mix with the sand of the beach or the saltwater! Consequently, my skin is tanned bronze to my shorts, and then a pearly white tan line under my shorts.

It was Saturday morning when I first arrived on the bus; as I stepped off the bus, I was intimidated.

A large administration building was in the center of a field about the size of a football field. The dorms were on either side of the administration building. I could see a gym and recreation center further off at the end of the field. We were hustled off the bus and into the admin building for registration and room assignments. There were three administrators at the counter, and three lines of students extending to the back wall of the room. I noticed a guy registering at the counter that was different than the rest of the thuggish types in line.

He was tanned dark. He was wearing glasses. He was about 6'0. He had a slim build and fine slender long legs. He had black hair, he was wearing cutoffs like me, but they were loose and high cut. They just barely covered the bottom of his dark tanned ass! His shirt kept riding up, and his tone abs kept peeking out from the bottom of his shirt as he stretched. I could see his treasure trail at the top of his cutoffs, that pulled your attention down lower past his waistband, which was slightly open.

He had a presence that was undeniable, exuding confidence.

I was in line waiting for my turn behind several Neanderthal types. There was one particularly obnoxious guy behind me. He was towering over me. he must have been at least 6'3. He was dressed in the biker outfit. Blue jeans, a metalhead tee, cowboy boots, and one of those chain wallets. He was wide. His back was almost twice the size of anyone I had ever seen. His biceps were the size of my waist! He was obviously a bodybuilder. He struck up a conversation with me, distracting me from the exotic guy at the counter.

"Hey what's your name? My name's John. Friends call me Jack."

I really wasn't interested, but to be polite I replied, "I'm Stef."

Jack replied, "Nice to meet you, Steffi."

Just then the line moved up. As I stepped forward, looking for that exotic guy with the black hair, shorts, and long tanned legs, he had disappeared.

It was time to move up in line again, and I needed to move my duffel bag. Actually, it was my step dad's from the navy. He was only too happy to give it to me and get me out of the house. I thought it was great when I was packing my clothes, books and x-box games; but now as I lugged it around, it was unbearably heavy!

Jack said, "hey that looks heavy, let me get that for you."

"I'm fine," I said as I tried to lift it and bent at the waist.

Jack immediately said, "whoa, whoa Steffi!"

He had one arm around my waist and my duffel bag in his other hand. As I said, this guy was huge!

Who did this guy think he is? I felt so indignant, and vulnerable, and embarrassed, all in one instant, and in front of everyone!

"Let go of me!" I said.

I could feel his crotch pressed against my ass. And his arm around my waist.

At this vulnerable moment, it seemed like everyone was staring at us! The guys in line around us were snickering. I even heard, "damn I'd tap that ass" from the general banter.

This only served to frustrate me even more! I wriggled and squirmed to release myself from this huge clown that had his beefy arm around my waist, and his crotch buried in my ass! I could feel his bulge slide against my crack while I squirmed to get free.

It didn't help that I was commando. I was aware that my shorts had dropped just enough that the top of my pearly white ass cheeks was bare, revealing my ass crack like cleavage!

One of the administrators at the desk then shouted, no horseplay! straighten up! Back in line, single file!

"You step forward to the counter."

I realized he was pointing at me.

Jack had released me at this point but was still holding my duffel bag.

I hiked up my shorts immediately, turning and scowling at Jack.

Jack apologized and said, "Sorry Steffi, I just wanted to stop you from throwing out your back. It's way too easy to hurt yourself. I've seen it happen in the gym countless times."

"You have to bend at the knees, not the waist! You could have seriously hurt yourself!" He called me Steffi again?! I let it go.

I thought about his explanation suspiciously, but he had a point.

Just then the administrator at the counter loudly said, next in line, That's you; step up to the counter. What's your name?

He was pointing at me. I was startled, and a more than a bit disoriented. "Steffi," I replied.

"Alright Steffi, if you would be so kind as to grace me with your presence, AND STEP UP TO THE COUNTER!"

I felt my stomach drop, and a chill went through me, as I stood frozen. I felt a hand palm the underside of my ass, Jack gently lifted and pushed me forward. I felt his fingers at the bottom of my ass and just under my balls. I turned quickly and glared at Jack.

The administrator at the counter was right out of central casting! He was bald, average build, but with a belly. He was wearing a cheap short sleeve teal shirt with a clip-on tie. Black slacks, that looked like they came off the Walmart rack.

He asked me the questions as he filled out the forms on the clipboard.

Then he placed bedding on the counter, two sheets, and a green woollen blanket. I looked at the wool blanket and grimaced, that looked miserable! I ran my hand over it. It was so coarse; how could anyone sleep under this?!

He noticed my disfavor of the wool blanket and said, "Not up to your standards? Would you prefer satin sheets and a duvet?" in a mocking sarcastic tone. I kept quiet, not wanting any more attention.

Next on top of the bedding, he placed three school uniforms, two pairs of running shorts and tee shirts with the school logo. I grabbed the pants and shorts to look at the size. They were a medium. I knew that wasn't going to work. Even though I'm short and slender, my hips and ass do flare.

"I have a 29-inch waist and 40-inch hips," I stated in a half-whisper.

The administrator seemed to soften his expression and looked me up and down, and exhaled.

Was he checking me out?! He then reached under the counter and replaced my pants, and shorts with large sizes of both the pants and shorts.

He then placed a pair of incredibly cheap blue sneakers on the top of the pile, these are your PE shoes.

"Can't we wear our own shoes at PE?" I replied.

"No, you wear a uniform for PE, Shorts, Tee Shirt, and sneakers, that are issued. And you wear the school uniform during class time." He then placed a cheap pair of black shoes on the pile. "After class time, you can wear your own clothes."

"Now here's the key to your room. You're in Dorm 2, room 40." dangling and jiggling the keys at me at eye level.

He then leaned over the counter slightly and said," I put you in the room next to the dorm supervisor to avoid problems."

I was glad the whole ordeal was over. I gathered everything from the counter, cradling everything with both arms. I then looked for my duffle bag. It was leaning against the counter next to Jack. Now I realized I had a problem. My arms were full, and my duffel was packed to the brim with my stuff from home. How was I going to get it all to my dorm room?

Jack turned and looked at me as he was stuffing his issued clothes and bedding into his oversized gym-travel bag.

"Move along, keep the line moving!" the administrator bellowed.

Jack grabbed my duffel, threw it over his shoulder and walked out the door! I followed behind him.

"So where we headed," asked Jack as we made our way to the Dorm building.

Dorm 2, room 40, I replied.

"Hey cool, I'm in Dorm 2, room 9," Jack replied.

We made conversation as we walked to the dorm. Jack didn't seem like the jerk he was earlier in the admin building.

When we entered the Dorm building it was the typical institutional setting. A single hallway, with rooms on either side. Fluorescent tube lights running the length of the hallway ceiling, linoleum tiled floors. Cylinder block walls painted dark brown on the bottom half and beige up to the ceiling.

The doors to the rooms were open as everyone was moving in. Jack's room, number 9; was next to the combined bathrooms, shower, and laundry room area.

Jack walked into his room, and I followed, surveying the room. It was spacious. It had two twin-sized beds on either side of the room. A wall locker for each person, 4 ft wide, and 6' tall. A small desk and chair for each person. In the corner of the room mounted on the wall was a flat-screen TV! My spirits lifted as I thought to myself, this isn't bad, I'll be able to play my x-box in my room.

Jack threw his athletic bag into his wall locker and said, "ok let's go see your room."

As we exited Jacks' room, someone brushed past us to the showers wearing only a towel and shower shoes, flip flops. I had to take a breath; it was that exotic black-haired guy from the admin counter! He looked back at us and flashed a smile as he turned into the shower room.

I had only seen him for a couple of seconds. He had a slim back, and it looked like a very tight muscular ass through the towel, and of course those long legs.

We kept walking to the end of the hall, facing the hall was the Dorm Supervisor's office. Next to it was a door marked 40. I guess that's my room I said. I pulled out my key and opened the door. My disappointment was evident. If Jack's room was spacious, mine was the opposite. The room was barely 10' long and 8' wide. The bed was against the wall, and the wall locker was at the foot of the bed. There was no TV, as there was in every other room! There wasn't even a desk. This was more like a closet than a room!

Jack put my duffel in the wall locker for me and said, "wow this really blows! You can come down to my room if you want to watch some TV or X-Box."

I thanked Jack and said I had to unpack.

Jack replied to me, "Me too, I'm going to the cantina at 6:00, want to come with?"

"I can't, I'm low on funds," I replied.

"My treat!" Jack replied and was off down the hallway before I had a chance to decline.

I hung my uniforms and put away my things. I put away my x-box games, I had the newest edition of metal gear, that I had just bought, and hadn't even opened it!

It was just at 6:00 when I heard a knock at the door, it was Jack. I was famished, and off we went to the cantina.

When we got to the cantina, it was a buffet style. There were a few other people seated and eating. Like I said, I was starving! I got tamales smothered in chili, beans, and rice, and oh my, they had Sara Lee chocolate cheesecake!

I felt odd allowing Jack to pay, but he said, don't worry about it and swiped a credit card, "My dad gave it to me for expenses." he said.

Jack was really engaging. He asked me about where I was from, and what my family was like. I vented to him about my stepfather, I told him about my circle of beach buddies. He really was interested in what I had to say. I babbled on, and before we knew it was 8:00.

Jack walked me to my room, and I thanked him for dinner. He said, see you tomorrow.

When I was in my room, I realized I really needed a shower before bed.

I took my towel and shower kit with me. I'm self-conscious about my body, as I've said before so I wore a tee-shirt and shorts.

When I walked past the laundry, and bathroom area and into the shower I was surprised! There were no stalls! There was a stainless-steel pole in the middle of the room with 6 nozzles, and faucet handles at waist level. There was a ledge, at waist level for soap and shampoo. There was a bench just outside the shower room with hooks above it for hanging your towel.

I hung my towel on the hook. I stripped off my shirt and shorts placing them on the bench and stepped into the shower room with my shampoo, body soap, luffa, and a washcloth.

I started the water and was pleasantly surprised at the water pressure, and heat! I let the water hit my face and chest like little hot beads. It felt great! I poured some Aloe Vera body wash into my washcloth and started to lather up my body.

I started at my long thin neck, working my way down to my flat hairless chest. I circled my nipples with the rough soapy cloth. The combination of the steaming pelting water and the rough soapy cloth felt delightful. I pinched and twisted my other nipple.

I closed my eyes as I pulled my nipple, using two fingers to circle my nipple if only someone was sucking my nipples! I went lower with the washcloth feeling the ridges of my abs. Caressing slow circles across my belly until I made it to my belly button. I traced circles around my belly button and inserted the tip of my finger. I imagined it was someone tonguing me there. I was really getting aroused. I dropped my hand down and lathered my thicket of bushy blonde pubes. My cock is really tiny. It barely clears my pubes. It's more of a button. I started with two fingers and my thumb, pulling on the tip of my cock head, I rolled my thumb over my button head pulling my cum slit apart. I gasped at the sensation.

I still had my washcloth in my other hand. I used it to fondle my balls. I gently squeezed my balls, as I ran my thumb of the other hand across the top of my cock head again. I could feel the sticky fluid of precum on my thumb.

I put my thumb to my lips and moaned as I rubbed my salty-sweet pre-cum across my lips. I then licked it off. "Oh, that tastes good!"

I reached for my luffa and turned around so that my ass was facing the stream of water. I bent over letting that hot spray hit the tops of my cheeks and stream down my ass crack. I bent over at the waist, feeling the hot water streaming onto my anus. I used my luffa starting at my ankles and working my way up my shins.

I made my way up my thighs, lathering my peach fuzz blonde hair on my thighs. The water still teasing at my butt hole. Cascading down my crack, and onto my virgin anus. It felt so good!

I remembered the incident at the admin building. Jack's fingers had been at my taint, if only for an instant. I gasped his name as I ran my luffa up the backs of my thighs and started scrubbing the bottom of my ass.

I started tracing small circles around the edges of my puckered hole.

Delicately soaping the ridges and crinkles of my opening with my index finger, while using my luffa on the top of my ass. I hissed out his name again as I made circles on my ass cheek with my luffa. I probed my hole with my index finger. My fingers and anus were slick with soap, precum was leaking out of my little button cockhead, my balls were pulsing. "I'm so close." I fantasized about Jack behind me. His big meaty arm wrapped around my waist like it was earlier today.

His cock tip pressed against my rosebud, instead of the tip of my index finger! I slipped the tip of my index finger in, my anus twitched around my fingertip, and I squealed, oh Jack!

Just then from just outside the shower, someone asked, "Oh god honey, who's Jack?"

I froze, had my heart stopped?! I looked over and seated on the bench staring at me, was that exotic guy that I had seen at the admin counter, and when he had brushed past Jack and me earlier.

He had a towel wrapped around his waist, his slender toned legs parted, and both of his hands wrapped around his huge cock! It was a monster!

He was leisurely stroking his cock, almost conversationally, as he spoke to me. One hand slowly moving up his thick veiny shaft the other at the base of his nude pelvis. His hand on his shaft moved to his bulbous head. His huge purple cock head the size of a golf ball, contrasting with his dark-skinned shaft. He was shaved and smooth. There was precum oozing down his bulbous head, down his shaft onto his fingers.

"Don't stop baby, that's quite a show, you got me so worked up!" as he fondled his balls with his lower hand.

I know my whole body must have flushed red with embarrassment; I was mortified!

I was still bent over, with the tip of my finger in my anus, and this gorgeous guy was stroking his cock at my display!

I bolted upright and in one motion I lunged out of the shower, and to the towel rack, grabbing my towel that was hanging above his head. My stomach pressed against his face as I stretched to grab my towel.

He pushed his head forward to prevent me from slamming his head against the wall in my haste and ran his flattened tongue up my stomach! I felt his cock head graze the inside of my thigh; I felt a glob of his precum on the inside of my thigh. I turned to flee from the scene, and, SMACK, he slapped my wet ass! I yelped, that stung! If I was flush red with embarrassment before, I was beet red from head to toe now! There was now a bright red handprint contrasting with my pearly white cheek!

I wrapped the towel around my waist as I made my way into the hallway. Oh, the humiliation walking the length of the very long hallway to my room way at the very end! Time seemed to slow, and the distance seemed like a mile away. It seemed as if everyone in the dorm was milling at their room doorways!

I was walking as quickly as I could in bare wet feet on the cold linoleum floor, trying not to slip.

Someone shouted, "Damn that must be jelly, cause jam don't jiggle like that!"