Sissy to Military School Pt. 01

It seemed like the whistles and hoots were coming in all directions!

Tears started to well up, and someone said, "awe baby, don't cry, come here and let daddy make it better."

I finally got to my room, closing the door behind me; I sat on the bed my face in my hands sobbing. I was overwhelmed, it seemed like I sobbed forever. I was a tear-soaked; snot covered mess! This was the worst day! I hate this place! My bare ass on that miserable coarse green woolen blanket! I clenched my fists into the blanket, standing up and with a twirl, throwing it to the floor.

Just then there was a knock at my door. "Hey, it's me, Kenny, I brought the stuff you left at the shower."

Oh god, it was that exotic guy from the shower. Could this day get any worse?! I cracked the door open; because I was naked, my towel having gone to the floor with my blanket.

I reached through the door to get my things, but he pushed on through into my room.

"My name's Kenneth Raynes," he said as he handed me my shower kit, flip flops, tee-shirt, and shorts.

"Friends call me Kay," he said in a casual conversational tone. As if nothing had happened, and I wasn't standing in front of him naked, and the door to my room wide open! I squeaked out, please close the door! He closed the door behind him.

He was wearing a white terry cloth robe, that came down halfway to his knees. I hurriedly put on my shorts, and tee-shirt that he had just handed me.

He reached out and softly caressed my face, as he maneuvered me to a seated position on my bed.

"Oh girlfriend, you've been crying," he said in a soft reassuring, and feminine? voice.

I had my head down still sniffling, staring down at the floor and his feet. He pulled my chin up with his index finger. My gaze traveling up those long slender, dark smooth legs. Unlike my legs, which were covered in blonde wispy peach fuzz, his were bare, clean, smooth, not a single hair!

From my seated vantage point; my head level with his waist, my focus directly at his crotch, and the bottom of his robe slightly open, I saw his huge bulge barely covered in a triangle of shiny blue material. I caught a scent, not a manly musky scent, but the fragrant smell, like flowers?

Kay pulled my chin up until I was looking at his face and said, "Their silk, I like nice things. I was going to the shower to shave my legs when I walked in on you."

"Oh, please don't tell anyone!" I said as I turned away in embarrassment.

"Oh god no, It's a secret between us girls. You have nothing to be ashamed of! That was the hottest show I have ever witnessed!" he said.

"I brought you an apology, or thank you present in your shower kit. To take the edge off."

"Apology, for walking in on you, and my actions. Thank you, for making me cum!"

"You have a lot of issues to work out; stop by my room, and maybe we can talk them out, girl to girl."

He kissed me tenderly on the lips.

"I hope we can be girlfriends." and was gone out the door.

"Present in my shower kit," I said out loud, as I opened it. There inside was blunt, and a lighter wrapped in a small plastic bag.

"To take the edge off," I repeated as I lit up the blunt and inhaled. I get so horny when I'm high, this blunt's strong, compared to what I'm used to. I stuffed my hand down my shorts, thinking about this crazy confusing day.

Jack had been such a jerk at the admin building, but so nice later, and bought me dinner. I was running my fingers through my pubes.

That horribly embarrassing event in the shower, followed by my walk of shame down the hallway. I slid my fingers to my balls. My middle finger was at the base of my shaft. My index finger was on one ball, and my ring finger on the other, as I simultaneously pressed and ground on my balls, and the base of my shaft.

Then Kenneth, or Kay, had come to my room and made nice. He had said, "I hope we can be girlfriends." He shaved his legs?! He was wearing blue silk panties?! He smelled like flowers down there. I pulled on my scrotum.

He said, "I had made him cum with my display?!" My fingers started pushing on my taint and lifting my tiny ball sack. I ground my hips against the mattress.

"You have issues, stop by my room, and we can talk them out as girlfriends," Kay said. Kay had such a huge veiny cock, dripping with precum! Kay had to use both hands; it was so huge! I had all three fingers between my balls, furiously massaging like I had a vagina!

"Oh, this place is strange. These people are so different. I'm so confused!" I slid my hand down, my fingers massaging the edge of my anus.

I had felt his cock head on my leg, he had left a glob of precum on the inside of my thigh! I was truly pumping, and gyrating my hips onto my finger, I slipped in another. I took another hit of the blunt. I was sliding my two fingers knuckle deep into my hot depths. I could feel my anal walls as I ground my hips. I came into my free hand.

Well; now that's a mess I thought. I can't walk all the way down the hall to the bathroom with cum in my hand!

I licked each finger, the cum leaving a thin glistening strand from my fingers to my lips. I put my palm to my mouth and slurped the pool of cum into my mouth.

Fuck it, I've got a buzz. It's not so bad. I said to myself contentedly. I put out the blunt, placed it, and the lighter back in the plastic bag, and then into my shower kit. I turned out my light and slipped between my sheets. In my post-orgasmic bliss and my buzz, I was blissfully asleep almost immediately.