Sissy to Military School Pt. 04

The continuing story of Sissy Steffi at military school. If you haven't read the previous chapters, please do for context and back story. All characters in this story are of legal age. 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.

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The next morning, I was startled awake again! There was an incredible jarring metallic noise coming from the hallway. Someone was yelling something I couldn't quite grasp in my half sleepy stupor. I pulled myself from my bed stretching. I had stripped off my shirt last night before climbing into bed. I was still wearing the thong panties Kay had gifted me. My butt plug's comfortably still in place. I had slept with it in as Kay had instructed. I looked at my phone, the time was 5:00 am?! "Oh my god this place is insane!" The metallic clanging still reverberating from the hall. I opened my door to see who and what was making that crazy noise! Halfway down the hall was a man dressed in khaki slacks and an under-armor V neck shirt. He had pepper gray hair with a buzz top crew cut. He was tall and thick. Not as thick as Jack, almost as tall as Kay. He did fill out his shirt nicely, and his thighs were encased in His Khakis. He had metal trash can lids in either hand, banging them together like symbols. I now could make out what he was shouting. "Reveille! Everybody up, five o'clock!" In time to his steps, as he was walking down the hallway toward me.

"This guy is a madman!" I said as I stared at him. I realized he was, in turn, staring at me, his eyes widening as he came to a stop standing in front of me. "I'm coach Bean, the dorm supervisor. You must be my new protective charge. What the hell are you doing out here in the hallway? In nothing but a pair of panties?" His head bowed; eyes focused downward at my sports thong.

I was now acutely aware of my near nakedness in the hallway. My confidence from last night had deserted me. It seemed everyone was staring down the hallway observing the exchange between Coach Bean and me from their room doorways. "You have, makeup on? It's a mess, you slept in makeup?!" Coach Bean queried.

I touched my face, foundation smearing on my fingers. "Oh god, I did," I replied.

"Get back in your room and put on something appropriate. These boys will be squirting all over the floor. You should do something about that makeup, it's a mess. Go clean yourself up in the shower." Coach Bean said, as he turned and shuffled into his office.

I turned to reenter my room, realizing everyone could see my nearly naked ass on full display, accentuated by my sports thong! Back in my room I pulled off my thong and threw it into my wall locker. I bent over, reaching between my legs, and with pop, out came my butt plug. "Eww, I see why these need to be cleaned every day," I said as I inspected and sniffed it.

I grabbed my shower kit and towel. "Wear something appropriate." I said to myself," remembering the recent scene in the hallway with coach Bean, and everyone in the hallway staring at me and my thong. I grabbed Jack's Jersey and threw it on. "My Jersey dress," I said with satisfaction. I could still smell Jack's scent on it. His scent giving me a renewed sense of confidence. I put the tubes of makeup remover and anal cream in my shower kit. I left my room wearing my jersey dress; with my shower kit in one hand, my towel over my shoulder, and my butt plug palmed in my other hand.

Once at the bathroom I made a beeline to an open sink. I placed my shower kit on the stainless-steel ledge below the mirror pulling my shampoo from the kit and immediately started washing my plug in the sink with shampoo. I looked in the mirror. Coach Bean was right. It was not a pretty sight. "No more sleeping in makeup," I said to myself. I put my plug in my shower kit and used my makeup remover for the first time. It did the job, much easier than I expected; but those damn hickeys were prominently back on display!

I finished up and went to the shower room. I was relieved that there wasn't a line at the bench. There were two guys in the shower at the shower pole. I stripped off my Jersey dress, there was a hiss from the shower. I half expected it when I revealed my ass. I turned and walked into the shower. Taking my place at the vacant faucet.

"Oh my god, that's a bald pussy!" One of the guys said pointing at me as I was pulling my shampoo and luffa from my shower kit.

I momentarily froze as I remembered last night's session with Kay and the shave. I resisted the instinct to flee from the shower and back to my room.

"Who put those hickeys on your neck? Want some more baby?" was said from one of them.

I looked them over. There were two guys in the shower with me. Neither of them was intimidating. They both were lanky pale nerdy boys. I regained my composure and said, "I'm totally out of your league." Closing my eyes and shampooing my hair. I rinsed and glanced over at the boys in the shower with me. I lathered up my luffa and ran it down my neck to my chest. I started tracing slow circles around my nipple with the luffa, "I'm off limits" I said. I started slowly down my belly with the luffa. I looked over and the nerdy boy to my right. He had his hand on his cock head staring intently at me. Down at my bald boy pussy.

"Once you accept yourself for who you are, you'll have real power," Kay's words were echoing in my head. I smiled, I was feeling naughty and mischievous! How far can I use that power?

"You can't touch me, but maybe you can help yourselves?" I asked coyly as I ran the luffa over my bald boy pussy.

"Oh god I'm so horny, I can't stand it," said the guy next to me. He had his cock shaft in his hand. On the upstroke, he was gripping so tightly I suddenly had the vision of him popping his cock head off like a champagne cork!

I bent over, running the luffa from the top of my ass down my ass cheek to my thigh. I heard a whimper from the other boy. "My boyfriend would kill you both if you touched me. That's his Jersey that I was just wearing, but you could help your friend out, couldn't you?" I said looking at the other boy that had just whimpered.

I bent fully at the waist, turning so they had a better view of my ass. I began scrubbing my shins.

"Oh Kyle, I'm ready to burst!" said the guy stroking his cock. He was standing on his tiptoes, pumping his shaft.

"Kyle is it? You see your friend is in need. Have you ever touched a cock before? It's so soft and velvety. It feels great in your palm. Much better than your own." I said, as I stood and placed my fingers on my mound My index finger and middle finger on either side of my own hard cock 'Ette.

I pulled my balls over either side of my cock 'Ette, my bald boy pussy. I looked down satisfied with the display. My balls on either side of my penis were pushed against it. My cock head barely protruding from my makeshift vagina lips. It really looked like an engorged clit peeking out from a vulva.

I saw Kyle was hesitating yet on the verge of action. His face had that conflict written all over it.

I traced small circles on my balls-vulva. "Reach out and touch him, Kyle." I could see his arm hesitantly extending toward his friend; who now had his back against the shower wall his eyes closed as his fist moved up his shaft. I stepped forward so that I could whisper into Kyle's ear as I pinched my nipple and I massaged my cock head button clit.

"It's right there Kyle, you've always wanted this."

Kyles fingers gingerly touched the tip of his friend's cockhead."

"That's it, Kyle wrap your fingers around it." I pushed down on his shoulders gently guiding him to his knees. Kyle had his fingers curled around his friend's cockhead.

"Stroke it Kyle, make your friend happy," I instructed.

Kyle wasn't paying any attention to my boy pussy that was at the side of his face. His buddy's cock mere inches from his lips. "What's your buddy's name, Kyle?" I asked, my fingers playing with the hair on the back of his head. Circling my own cock head clit with the fingers of my other hand.

"Jay," Kyle replied.

"How long have you wanted Jay's cock?" I asked Kyle, gently pushing his head forward. He replied, "Since the first time we sat on the bed together playing X-BOX."

"Close your eyes", I coaxed as I pushed Kyles head the closing distance to Jay's cockhead. A thrill shot through me as Kyle's lips and Jay's cockhead made contact! I was pulling on my cock tip clit with my free hand.

"Stick out your tongue as far as you can Kyle," I instructed.

Kyle did as I instructed, and his friend Jay smoothly slid his cock across Kyle's tongue and past his lips.

I was pulling on my scrotum and massaging my balls, vulva. The control was overwhelmingly exciting!

"Tastes great doesn't it Kyle. You love the taste of cock, don't you?", I said nearly whispering. Kyle nodded his head. Jay's cock sealed by his lips.

"Do you like how Kyle's mouth feels Jay?"

"It feels incredible! Why didn't you tell me you wanted my cock?! I can't believe you were my roommate all this time and we could have been doing this all along!" Jay blurted out, as he started pumping into Kyle's mouth.

I knelt next to Kyle's face, to get the perfect view of Jay's cock sliding across Kyle's lips. I was sliding my fingers down my own shaft.

I was the virgin yesterday; I knew all too well what Kyle was going through. Now I had coached this virgin into his first blowjob! From my new improved vantage point, I could see Kyle's tongue was still out cradling the bottom of Jay's cock shaft like a curved ramp. Jay had now gained his rhythm pumping into Kyle's face.

I took note of Kyle's curved tongue ramp technique, "I'll have to use that sometime in the future," I said.

"Don't forget Jay's balls, Kyle," I said in a breathy tone. Kyle was quick to cup his friend Jay's balls as I had directed. He was really into it now; pulling on Jay's cock shaft with one hand, fondling his balls with the other, and bobbing his head down, his lips sliding down Jay's shaft. His friend Jay had placed his hands on top of Kyle's head and was moaning. I knew Jay was close. I put my hand on the back of Kyle's head preventing him from pulling back. Jay's hips rose, he was on his tiptoes. I could see his cock pulsing, and his balls contracting. I was watching intently as he was shooting his hot load into his friend's' mouth! I saw Kyle's throat reflex. He was swallowing his friend's load! "Milk those balls Kyle!" I nearly yelled.

Kyle was massaging Jay's balls, cum leaking out of the corner of his mouth. I stood up and went to my shower kit. I retrieved my butt plug and anal lube. Still watching Kyle and Jay, I coated my butt plug and inserted it.

I walked out of the shower drying myself off when I looked over my shoulder at the two.

"Thank you," Kyle said, still on his knees holding Kyle's cock shaft in his hand. Cum leaking from his lips to his chin.

"I'm glad I helped you discover yourselves," I replied, putting on my jersey dress.

"I'll bet you two won't be teasing me in the shower again," I said as I turned the corner and walked down the hall to my room.

Coach Bean's office door was open. He was at his desk filling out paperwork. He looked up at me. I smiled. He smiled back at me and returned to his paperwork. I turned and entered my room.

I stripped off my jersey dress throwing it, and my towel in the bottom of my wall locker. I slipped on my sports thong and started dressing in my school uniform. The pants were a cheap polyester blend. I pulled the pants up over my ass. "I probably should have asked for extra-large," I said, craning my neck viewing how my ass was sheathed in the cheap fabric. "At least they stretch," I observed. The collared short-sleeved shirt fits my flat chest well enough. It had two breast pockets and buttoned down the front. I was unaccustomed to wearing anything except my high-top sneakers on the beach. The cheap black hard leather shoes fit uncomfortably at my Achilles heels. I felt as if I was clunking down the hall in Dutch wooden clogs as I trod to the bathroom and applied my foundation. I went back to my room putting my foundation back in my shower kit and made my way to the cantina to meet up with Jack.

Jack was waiting outside the cafeteria building for me. "Oh, that's so chivalrous of him!" I said under my breath. I didn't think anyone would be able to look good in this cheap fabric polyester uniform. I got my first glimpse of Jack in his school uniform. He looked incredible! His pecs bulging from his shirt. His biceps threatening to tear open his shirt sleeves. I didn't even know I had a thing for guys in uniform until now! "Is that really my man? You look fantastic!" I said as I approached Jack. He opened the door for me and replied, "You look fantastic in your uniform Steffi." I looked over my shoulder as I passed through the door. Jack's focus was on my polyester encased bottom "I know what part of me you think is fantastic." We went through the cafeteria to the cantina section and took our seats at a table in the rear corner of the cantina. As soon as I was seated, Jack was off to get our breakfast.

"I could really get used to this," I said as he left. Jack returned with a tray in each hand. The same breakfast I had ordered the last time. There was an additional item. A piece of cheesecake. We began eating our breakfast together. Jack was telling me about his plans for the coming year. He was going to try out for the football team after classes today. "I really miss the braid in my hair!" I thought to myself. Do all girl's minds wander when their man is talking to them? I had finished eating, my belly was quite full. My mouth still had the taste of cheesecake. I wasn't used to eating so much, and so regularly. At the beach, I would usually grab a hot dog or burger only when I was hungry.

"We need to get moving for orientation," Jack said. When we entered the school auditorium I stopped and took it all in. It was an old movie theater with faded blue fabric seats. There was a stage in front of the screen with a podium placed at the center of the stage. Jack and I took our seats in the center of the back aisle against the wall. Jack sitting to my right.

The guy to my left started chatting with us. He had strawberry blonde hair. He was slightly taller than me. He was thin, but I could see the definition in his arms. He had beautiful hazel eyes. He was polite and congenial. He was keeping both Jack and me engaged in conversation and humor. Jack laughed several times at his jokes. Humor is so sexy I noted. He said his name was Rene and was from Shreveport Louisiana. Jack chuckled and said, "That's a girl's name. "I snapped at Jack, "Don't be so rude to our new friend." And turned to Rene," It's a lovely name." Rene replied, "No offense, I'm fluid in my preferences. Mon surcree Cher." I wasn't sure what he said, but French sounded so smooth!

The lights in the auditorium dimmed. The screen lit up with a computer display emanating from the projector room directly above us. "They're going to give a powerpoint presentation," Rene said.

Jack placed his hand on the top of my thigh just behind my knee and firmly squeezed. He slid his hand from the top of my thigh to just below the knee. Stroking slowly from the inside of my knee almost imperceptibly closer to my groin. I was holding my breath I was so anxious!

Jack had his hand on my leg, touching my groin. I hissed with a combination of sexual excitement and the anxiety that we would be discovered. "Jack stop we're in public, all these people will see us!" I whispered.

The presentation had started, "Honor, Integrity, Morality. We are a proud military school that was founded at the turn of the century. Those are the founding principles here at our school."

The person at the podium was rambling about how the school's corporate sponsors had made change directives that would be implemented with the new incoming year, our class. The school had run into financial hardship and had to accept a merger with a national education corporation. The corporate board had developed an LGBTQ tolerant position. The corporate board had directed that the mandated military haircuts would be eliminated. There would be no extreme hairstyles; and no florescent hair colors. The education corporation had a network of schools throughout the area. The pictures of different schools superimposed on the American flag displayed on the screen. The light emanating from the projection room diffused above us; obscuring us from the people surrounding us greater than had we been sitting in darkness on either end of the aisle.

Jack had his thumb on the tip of my penis clit and was grinding it in small circles through the cheap polyester of my pants and the thong underneath. It was all I could do stifle a groan. A whimper escaped my lips as I squirmed in my seat. I was sitting straight up. I was so skittish! "Are you wearing that thong from last night?" Jack whispered and I replied, "Yes I am, just for you!" I gasped as Jack unsnapped the waist button of my pants. I let out a long exhale as Jack started unzipping my pants. The sound of my zipper seemed to reverberate throughout the theater! "Who's my girlfriend?" Jack asked. "I'm your girlfriend," I whispered in reply.

Rene looked over at us and whispered. "Fille chaud folle, are you going to let him do that right here?" Jack leaned across my body, his face at my chest, looking Rene dead in the eye and gruffly said, "Shut your mouth and you can watch."

Rene was staring intently as I had slid down in my seat. Jack had spread the fly of my pants open. Jack's big meaty fingers slipping under the elastic of my thong. His fingers sliding down my now smooth slick pubis mons.

"I love it, my cock's going to feel great sliding across your sweet bald pussy," Jack whispered into my ear. "Mon Ami, C'est Chaud," Rene said. I glanced at Rene. I saw the outline of his cock on the side of his leg. He was gripping it through his pants. "You should take that out or you'll stain your pants," I whispered to him. I was dying to see what his cock looked like.

Jack's fingers were now down my thong, over my cock head clit. He made circular massaging motions on my balls with his fingertips. Rene unzipped the fly of his pants. He slipped his fingers into his fly as he watched Jack's fingers massaging my boy pussy.

I closed my eyes and tilted my head back against the wall behind us. Jack had me at a delirious state of arousal. The fact that our new friend Rene was masturbating to our show heightened my arousal. The fact that we were masturbating in a theater full of people had me quivering with the combination of excitement and anxiety. The presenter said something about our sorority school.

Rene had pulled his cock head from his fly. He was uncut. He was stroking and squeezing his cockhead pulling on his foreskin as he looked into my eyes. Jack rubbed his hand across my mound and asked Rene," Isn't she the hottest girl you've ever seen?"

The presenter went on to announce a Halloween dance party would be sponsored at the local sorority school. I was hearing these details, but they weren't registering in my mind. Rene had his shaft out of his pants stroking his uncut cock, watching Jack masturbate me. My fly wide open, my bald mound slick with my precum, Jack's palm was over my penis clit his fingers massaging my balls.

"I love your hot slick pussy. Look how hot you've got Rene; I think he's about to pop." Jack said as he stuffed his hand further down my thong. Rene's finger and thumb wrapped around his cock head. Precum had pooled in the cup of Rene's finger, thumb, and the tip of his foreskin on his upstroke. Jack's hand had slid under my bottom. His fingertips playing at the edge of my jeweled butt plug. Tilting the butt plug in different angles around my anus ring. "I think you're the one that's got us both so hot Jack. I think we're both about to pop! Don't make me cum in my new thong!" I whimpered in Jack's ear. I heard Rene grunt. I looked over to see he had cum in the cup he had made with his fingers, thumb, and foreskin. The erotic image was more than my senses could endure. I came in Jack's hand.