Sissy to Military School Pt. 02

This is the continuing story of Sissy Steffi that goes to military school. Please read PT1 if you haven't already!

All characters in this story are of the legal age of consent.

***

It was Sunday morning; I was rudely awakened by the cacophony outside my room in the hallway. I looked at my phone. The time was 7:15 am. Who wakes up at 7:00 am on a Sunday; and from the sound of it, everyone in the Dorm?! I reached into my wall locker and grabbed the first things, I found, my issued P.E. outfit. I put on the P.E. shorts and a tee shirt. Did I mention just how thin the grey P.E. shorts are? Looking down and craning my neck at my bottom; I could see that both globes of my butt were predominately displayed. I swear the way they encased my ass; they could be yoga pants!

"These are supposed to be large?" I said to myself.

I grabbed my shower kit, and towel, slipped on my flip flops, and I was out the door to the shower. The hallway was teaming with everyone making their way to or from the shower room in various states of dress. Some wearing only a towel around their waists, others with robes, some with sweatpants. Shouting to each other from one end of the hallway to the other. I entered the bathroom which had 6 sinks lined against one wall, and bathroom stalls against the other wall. To the right was the laundry room, and to my immediate left was the shower room with the bench and towel rack.

There was a line to the showers, several guys seated naked on the bench waiting their turn to get into the shower.

I walked up to the open sink and brushed my teeth; to let the line die down before showering.

There was a black guy next to me. He was just slightly taller than me; around 5'9. He was slender, with a delicate build. He had a white towel wrapped around his waist. His chest was bare; and like mine, nothing there, no pecs. I could see a tiny tight butt encased in his white towel.

"Hi, I'm Stef, why is everybody up so early on a Sunday?" I asked.

"I'm Clay, the cafeteria stops serving meal plan at 9:00 am," he said.

"Meal plan?" I asked with a quizzical look on my face.

"You must be really new here. The cafeteria serves three meals a day to students. It's the meal plan, but they only serve during meal hours. They stop serving breakfast at 9:00 am." He explained.

I realized I had better get a move on, or I was going to miss breakfast! I rushed to the shower, and the line was gone. I stripped off my clothes throwing my stuff on the bench as I stepped up to the shower pole.

I was rushing; just a quick shampoo of my hair. A quick scrub of my pits, ass crack, and crotch, then I was out of there!

I grabbed my cell phone and rushed to the cafeteria. I jogged virtually skipping, to the cafeteria from the dorm with visions of omelets and crispy bacon, fresh fruit, and pancakes dancing in my head! I entered the cafeteria, grabbing a lunch tray and made my way through the line to the server counter.

I was so crestfallen disappointed! The server took my tray and sloped runny scrambled eggs, an unrecognizable patty of meat, and a dry piece of toast on the tray. I looked down and looked at my breakfast. It was a far cry from my fantasy Hilton breakfast I had envisioned on my way here!

The scrambled eggs had a green tint to them, powdered, instant eggs. I still couldn't identify the meat patty. It had white flecks throughout it. I walked away from the serving counter to the milk dispenser.

It was a stainless-steel box with a rubber tube teat leaking milk congealing in the catch tray below. "That is just too nasty," I remarked. To the left of the milk box was a table. It had juice boxes on it. I grabbed three and went to find a table. There was a partition dividing the cafeteria and the pay cantina section. I sat down just in time to hear and see Jack over the partition on the cantina section of the cafeteria. I could see him from the shoulders up, towering over the partition.

He glanced over at me, "Steffi, what ya doing?"

"Umm, about to eat breakfast?" I replied.

"There's nothing over there worth eating!" he said

I looked down at my tray. The runny, green tainted eggs, and the strange alien meat patty, he was so right!

"Let me buy you breakfast, come on over!" he said with a beckoning wave.

I didn't have to be asked twice! Jumping up from the table; I grabbed my juice boxes, leaving my tray of mystery meat and green eggs on the table.

I joined Jack on the cantina side of the partition. I sat down at the table and Jack immediately started a conversation.

I glanced at jack with a pretend annoyed expression on my face and said, "You promised me you would buy me breakfast!"

"Oh right, I was just happy to see you. I had a great time with you last night and..."

"Jack, breakfast?", I repeated, playfully stamping my foot.

"Oh right," he said as he bolted from his chair to the serving area of the cantina.

He turned around walking backward toward the cantina and looking at me, he asked, "What ya want?"

"An omelet, link breakfast sausage, some potatoes, pancakes, and a fruit cup!" I replied, flashing a smile at him. And just like that, he was off!

When he came back I almost giggled. He did look comical! This giant bear of a man gingerly, submissively carrying my tray to me! He placed the tray in front of me. It had everything I asked for.

The food looked like it could have come out of a cooking magazine! The hash browns were cooked crispy brown, just the way I like them! The fruit cup was wonderful! It was actually an 8 oz go cup filled with chunks of pineapple, strawberries, grapes, and banana. The pancakes looked fantastic. They were huge and fluffy, covering their own plate. Jack had even put whipped cream put on top! The omelet was a yellow half-moon on the second plate with four breakfast sausage links.

I mentioned earlier that I was accustomed to beach vendor food. This was the Hilton breakfast I had envisioned!

Jack started chatting with me while I ate. It was a one-sided conversation. I was stuffing my face; with a sausage link, and pancake.

I started glancing at Jack between bites. Listening and checking him out. I said he was huge, his biceps enormous a thick vein the size of my finger ran down the length of his biceps. He was wearing a tight jersey V neck tee-shirt that showed off his thick beefy pecs. His forearms were just as impressive, they were so defined, with veins crisscrossing to his wrists. His hands were massive. Each finger thick like beer brats! He mentioned the school had a football team, and he was going to try and make the team.

I said, "You certainly have the body for it"

He beamed a smile and said, "Thanks, I played in high school."

I realized that with all the conversation, which had focused on me, I didn't even know where Jack was from!

"And where did you play football?", I asked.

He beamed with pride and said, "Columbus Nebraska, we went to the NSAA championships, Division C2."

I had no idea what all that meant. I did catch the word, championship in his statement.

"Well that explains it, a big corn-fed boy from Nebraska", I said in a coy teasing tone.

He chuckled, he had a great smile, with a twinkle in his eye. I had to admit, Jack was attractive!

I wondered why he was here at military school, being a successful football player back home in Nebraska. I didn't question. I know we all have the issues that brought us here.

Jack asked, "So what sports are you into?"

"I told you, I'm from the beach. I like anything to do with the beach. Beach volleyball, boogie boarding, body surfing, and swimming." I replied between bites of my fruit cup.

Jack let out a huff and said just under his breath, "Volleyball, wish I could have seen that!"

I finished my fruit cup. I was content with a full belly and pleasant conversation with Jack. He really had a disarming and engaging personality!

He asked for my number and I immediately rattled off the number as he was entering it into his phone. He was typing something and then looked up at me and said, "User unavailable?"

I looked at my phone. It said, no service available. please dial 611 to make payment arrangements. "Oh no, my subscription just ran out!" I whimpered.

I usually picked up a shift, or tips on the beach to pay my cell, but here, how was I going to be able to scrape up any money to pay for my cell? I thought to myself.

"Let me see that," Jack said. His huge bear hand engulfed mine as he grabbed my phone out of my hand walking to the cantina exit. Once again, I was following behind him out the door.

He dialed and was talking on my phone to customer service. He pulled his credit card from his wallet as we were walking across the field to the dorms.

"Jack, no you can't do that!" I protested.

"Hush," he said to me. with his index finger in the air.

He hushed me; I can't believe he hushed me!

"Yes, my name is Jack, I'm Steffi's boyfriend, I want to pay her subscription. A month." Jack said into the phone.

He had referred to me as, her? He was paying my phone bill for a month?!

He said I was his girlfriend?! We were at the dorm entrance and as we walked through the door into the hallway.

Jack hung up and handed me my phone. We walked the length of the hallway, and Jack said, "There, all taken care of."

We were at Jack's dorm room. As he opened the door, I followed him in. I was annoyed, I was going to give him a piece of my mind!

"So, it's official now, I'm your girlfriend? Is that how it works where you're from in Nebraska? And don't ever shush me. No one ever shushed me!" I said, my hands on my hips as I stamped my foot with indignation.

"Wow, you're even hotter when you're pissed!" Jack said.

He grabbed me by the waist with his big meaty hands, pulling me to him. Jack pulled me tight against his body. My face was buried between his pecs. I could smell his musky alpha male scent through his tee-shirt. His hands slipped down from my waist under the band of my shorts. He cupped both my ass cheeks.

His fingers at the curve of my cheeks at the back of my thighs. I couldn't see it, but I could feel his hard cock against my stomach. I distinctly felt his bulbous head against my navel. His hands were massaging my ass under my shorts in circular motions. He was kneading my ass like bread dough. I let out a breathy sigh. His fingers gripping my ass crack, his palms on my cheeks. He pulled my ass cheeks apart. I could feel just a hint of breezy air on my anus. A slight hum escaped from my lips. He pulled me up on my tiptoes by my ass cheeks. He leaned in and kissed me. It started with a closed mouth kiss on the lips. He ran his lips sideways across mine. It was like an Eskimo kiss. Rubbing noses, but oh so sensual! His tongue slipped past my lips and probed my mouth. I moaned into his mouth.

My mind was in a fog.

I was annoyed with him a minute ago. what was I so upset about? oh yeah, he called me his girlfriend!

Jack broke our kiss and said, as he hooked the waistband of my shorts, and with one fluid motion, they dropped to my ankles. "That's the way we do it in Nebraska," he said.

"Oh, that's a clever trick!" I said with a mischievous grin. I was now nude and completely exposed from the waist down.

Jack went to kissing and sucking on my neck. I arched my back. He tongued my ear. Oh my god, nothing I had ever felt was so exquisite! I squealed with delight! He was palming my entire pubic mound in his hand. I could feel my precum on the tip of my tiny nub and, smeared on his palm. His other hand was on the top of my ass, at my ass crack. He slipped his middle finger down my crack. I could feel his middle finger inching slowly to my anus, as he ground the palm of his other hand against my pubic mound. He was mashing and grinding my tiny nub cockhead between his palm and into my own pubic mound! His fingers fondling my balls! I was whimpering with delight!

I felt his fingertip on my anus, I gasped, it was thicker and wider than my entire hole! I told him, "No I'm too small, I'm a total virgin!"

I felt his bare cock head which was now above his waistband. I looked down between us. I slipped my fingers around the tip. This was the first cock I have ever touched besides my own. I was fascinated by it. Momentarily caught up in my own little world. I loved the silky texture of the head, as I brushed my thumb over it. I rubbed my thumb across his cum slit, knowing the reaction I had when I did it to myself.

"You're a total virgin?" Jack asked.

"I've never been with anyone, man or woman," I replied, as I slid my fingers down his bulbous head to his shaft.

I didn't look up to speak. I was concentrating on the cock in my hand.

I was snapped out of my little daydream as Jack moved us to the bed. Jack sat me on the bed and dropped his shorts. As his shorts dropped his cock sprang out from his waistband. There it was, staring me right in the face! I reached out and grabbed his cock by the shaft. I inhaled deeply, there was that heady alpha male musk overwhelming my senses.

He pulled off his shirt, I was oblivious to what he was doing. I was focused on his cock, inches from my lips. His cum slit glistened with precum. His cock was nice-sized, just about 7 inches. I was surprised considering his body size, and the size of his hands!

"Thank god it's not like Kay's!" I thought to myself.

I cupped his balls with my other hand. I pulled on his cock head and down stroked onto his shaft.

Jack then interrupted me by pulling my shirt off. There I was completely naked; sitting on the bed with a completely naked man standing over me. A long strand of precum was now drooling out of his cock head. I was fascinated! I moved my head in, opening my mouth and sticking out my tongue to catch it. The fluid coated my tongue. It was sweet and salty. I closed the gap to his cock head with my lips. I held my lips to the very tip of his cock, kissing it. He slid his cock head across my lips, glossing my lips with more precum.

I pulled on his balls. He gasped as I pressed forward, opening my lips just enough to let his cock head slide through them. I moaned with his cock in my mouth. I put my tongue on the underside of his cockhead. My lips inching down his shaft as I played with his balls. His pubes were the only thing in my field of view, starting to brush my nose.

He groaned, "Oh god Steffi that feels so great! You sure you never did this before?" I shook my head with his cock still in my mouth. His big hands were caressing my cheeks.

I tried to bury my nose into his pubes taking the entire length of his cock into my mouth. But his cock head bumped the back of my throat and I choked. I pulled off him, gripping his shaft. A mixture of precum and saliva streaming from my mouth and his cock. My eyes were watering. I looked up into his face and said, "I'm sorry." as I stroked his shaft.

"Oh baby, you have nothing to be sorry about. You're incredible!"

He put his hands on my shoulders and gently pushed me down to a lying position on the bed. He got on top of me and started smothering my face with kisses. He started kissing my closed eyes. His big meaty hands on my chest. His cock grinding on my pubic mound. His shaft sliding across my cock which was raging and throbbing! I was harder and more aroused than I had ever been before! He was rolling and pinching my nipple between his finger and thumb. I gasped at the intense pleasure he was giving me. He started kissing, and nibbling, and sucking on my neck. He repositioned his hips and his cock shaft was sliding between my balls. His cock head rubbing my taint. He was covering my balls and taint with a combination of my saliva and his precum. "Oh my god, I feel like you're actually fucking me! I feel like I have a vagina down there!" I breathlessly gasped.

Jack whispered into my ear; it feels like a vagina to me too baby." He then took my entire ear into his mouth tonguing the inside of my ear. I gasped, "Oh how did you know that would turn me on so. I didn't even know it myself!"

Jack chuckled and sat up to a kneeling position over me. His thighs against mine.

"Oh my god please don't stop. I'm so close!" I whimpered.

Jack looking down at me and asked, "What do you want baby?" as he stroked his cock.

"I want you Jack", I replied.

"What part of me do you want, say it", he replied as his other and cupped my pubic area, his fingers on my taint, his palm grinding my balls and cock.

"I want your cock Jack, please quit teasing me!" I whined!

He then flipped me over on my stomach. "Wait I wanted you to keep doing what you were doing." I protested.

"What was I doing?" he asked as his beefy strong hands were massaging my ass.

"You were fucking me," I said in a pleading whimper.

Jack pulled my ass cheeks apart. I could feel the exposure of my anus. He kissed my ass cheek. Then he bit it! that was a shock. He was massaging and kissing and licking my ass cheeks. I was grinding my hips into the mattress. My cock rubbing across the sheets. This was a whole new experience! I could feel his fingers on either side of my crack, as he spread me wide open. Suddenly I felt a wet sensation on my rosebud. A jolt of electricity went through my body. I felt the electricity in my nipples they had become so sensitive! "I can't believe you did that!" I said breathlessly. I raised my hips off the bed, arching my back, pushing my ass into his face; encouraging him to continue.

"You have such a perfect boi pussy, tastes tangy," Jack said.

I giggled when he said that.

Jack resumed his assault on my anus with his tongue. He slipped one of his hands onto my pubic mound. He was fondling my penis with his fingers and palming my balls. I felt his tongue flattened and sliding up my ass crack from my anus. He covered both sides of my crack with his flat tongue. I had never felt so totally exposed and submissive to anyone in my life. I was in bliss. It seemed like Jack possessed me from my anus to my core. I absolutely loved it! I was gasping, "Yes god, oh Jack that's it!" My opening was now expanding and contracting as Jack drove his tongue all the way in.

I was completely wet from the top of my ass, and down my ass crack. My anus was drenched! My entire pubic mound, cock, and balls were covered in my own precum thanks to Jack's palm and fingers! I was thrashing my head side to side in ecstasy!

He pushed down on my hips forcing me onto my stomach. I was so disappointed that he was no longer tonguing me! Jack was sitting on the back of my thighs his knees on either side of my hips.

His cock head was at my taint just under my balls. I felt him reposition and his cock head slid from my balls to my anus. I felt the tip of his cock at my rosebud entrance!

I pleaded, " No Jack. I'm a virgin. I'm too small. You're too big for me!"

SMACK; Jack slapped my ass cheek hard. I yelped. It really stung! My anus convulsed involuntarily, my anal ring gripping the very tip of his cock.

"That's not what I had in mind." He said.

He then smacked my ass again as if to drive his point home. I buried my face in his pillow.

To my relief, I felt his cock tip slide up away from my anus, up to my crack between my cheeks. He was hot-dogging me. His hands-on either side of my ass cheeks pushing them together as his cock slid up my crack. He was literally tit fucking my ass! On his downstroke, I felt the tip of his cock at my anal ring again. It pushed slightly meeting closed resistance. I gasped worried that he would force it in, hurting or tearing me. It was only then for an instant, and then down further sliding against my balls, and then further along my taint. I was moaning into the pillow. I kept feeling his cockhead at my tight rosebud with every downstroke. Jack wasn't inside me, but he was definitely fucking me!