Chapter 1: Sadistic Roommate

My Sissy Life

Chapter 1: Sadistic Roommate

My first college roommate was a psycho killer whose skin and hair had an unnatural yellow and brownish color to them. The other guys in the dorm, the drunken fools, the ones who harassed me for studying, lived off beer and pretzels. I didn't fit in. I didn't want to join that crowd. Hidden in my closet, in a duffel bag, I had makeup, heels, thigh highs, a blouse and a wig that I had bought at Goodwill.

On sleepless nights, I'd walk off campus to a road that led to a convenience store and low rent apartment complexes. One night, a pickup truck rolled up next to me. The guy in the truck looked down on me from the driver's seat. His hair swept back in a greasy wave. I meandered slowly just off the road, near a ditch filled with rainwater, listening to the frogs croaking. The engine rumbled loudly.

"Are you gay?"

"No."

The truck disappeared into the distance. As I walked, I lingered, looking over my shoulder. The street was dark, windswept and quiet. I liked being out on the streets alone. My hormones raged with unspent energy. Before the session ended, I went to the housing office and got a list of apartments and rooms for rent. Most of the landlords wanted hundreds of dollars more per month than I could afford.

Just before finals, I looked at a room for rent. There was a beat-up pickup truck and a motorcycle in the carport. He opened the door to let me in. He was a big, burly, bald white guy who looked like Shrek. The room had a musty smell to it. The carpet in the room needed to be cleaned. Heavy drapes covered the windows.

"Eight hundred a month?"

"Unless you got more. I got other people looking."

"It's kind of small."

A long wooden shelf inside the closet was broken. The hinged door to the closet didn't close.

"How long are you looking to stay?" he asked.

"I don't know. A year maybe."

He leaned against the door frame.

"Well, thanks," I said.

I went back to my car. It was the cheapest room available for a hundred miles. It might look better with a bed and desk in it. If I didn't take it someone else would. I knocked on the door. If I could have a bed frame, mattress and desk delivered there over the break, I'd take rent the room. He agreed. I put my suitcases and duffel bag in the closet. As I drove away, my mind turned to my finals.

I had no idea my life was about to change. I got the key to the house when I got back into town. We walked into the bedroom together. The bed and desk were built. The mattress was in place. The bed sheets neatly folded. My luggage and duffel bag were on the bed. The closet had been painted. The wooden shelf inside the closet had been fixed. The hinged door to the closet had been repaired.

"I painted the closet."

Had he looked inside my duffel bag?

"Fixed the closet door," his hand brushed against my butt.

Did he just touch my butt?!

I was about to blurt out something angry.

He raised his hand, as if to say something important.

"I'll be in my room if you want something."

He walked out and closed the door.

I sat on the bed. There was no way to know for sure if he had looked inside my duffel bag or not. Should I ask him? Did he touch my butt on purpose? I emptied the duffel bag on the bed. My black four-inch heels were beautiful. My long sleeve black blouse was super cute. I opened my canister of bright red lipstick. I locked the door.

What if I got dressed up like a girl and walked down to his room and knocked on the door? My mind was consumed with sexual fantasies. He was big and burly. He knew I had female clothes! He must've looked inside my duffel bag. That is why his hand brushed my butt. He likes me! I had to find out. I walked down the hall to his bedroom door. I was scared to knock but finally did it. He opened the door.

"I-I just wanted to say thank you. For putting my bed and desk together. And cleaning my room. You didn't have to do all that."

I waited for him to say something.

"Okay, goodnight," he said.

"Wait! Wait. Is there. Anyway. I Can UMMM."

His eyes went up and down my body.

"Thank me? You know what you want to do."

Oh my God. He knows. I know he knows. He knows that I know he knows. I ran back to my room and took my clothes off. I used my finger to put makeup on my face. I put my thigh-highs, blouse, and wig on. My heels went on last. Lipstick! Don't forget the bright red lipstick! I moved to the master bedroom as if dreaming. I knocked on the door. He opened the door and looked at me.

"Come on in," he said.

Pornography was on the TV on his dresser.

Being in heels, and a wig, and everything else, and having a much bigger guy touch me, knowing what was about to happen, is impossible to describe. His finger grazed the roundness of my ass.

"I want a pet. A sex slave. A whore. A cum dump."

He handed me a pink chastity cage.

"You'll be caged around me."

My mind was already being rewired.

"You can cum when I say so. You'll get a discount on rent."

A lady boy on the big screen was getting her brains fucked out.

Her clit was flopping up and down and she got pounded.

"Have you ever been fucked?"

"No."

He dropped his pants. A big cock lolled out. I had never seen one up close before. It was thick even semi-hard. I took off my panties and clipped the chastity cage on and got on my knees. He was overflowing with masculine energy. The kind of guy that got into bar room fights and kicked asses for fun. A brawler. An ex-marine.

My mouth was open.

My eyes closed.

"I want sex on demand," he said.

He put the head inside my mouth.

I let it slide in and out over my tongue.

It filled my whole mouth.

I didn't know what to do so I just relaxed and let to go to the back of my throat. I couldn't breathe.

"Get it all the way down. All the way."

I couldn't get it all the way down without choking. He forced it down my throat and when I gagged, he let me have air. I had to breathe in as much air as I could before it was shoved down my throat again. The more he choked me the harder he got. He held the back of my head and forced his cock as far down my throat as it would go.

I nearly blacked out. I squirmed. My hands flailed around. My mouth was completely wide open but there was no way I could breathe. I couldn't breathe through my nose either. Tears of panic and utter fear streaked down my cheeks. He slapped me on the side of the face. Not hard. But enough to get my attention.

He slowly pulled his cock out.

I gasped for air. Down it went again.

Even deeper. I was going to black out.

"Open," he commanded.

He slapped me. I gave up.

I went limp.

He pumped his cock deep into my throat.

Suddenly, I could breathe again.

"Good girl," he said icily.

I opened my eyes and saw him looking down at me. He rubbed watery tears away from my cheeks. I opened my mouth and down it went again, all the way down, all the way to my tonsils.

I felt a stupid mind-numbing mix of feelings and sensations. My mouth being stuffed, my lungs burning for oxygen, a simmering fear that he was going to choke me to death and bury my lifeless body in the woods and a tingling, tickling feeling near my clitty that was hopelessly trapped in the plastic chastity cage he told me to wear.

It didn't feel real.

It felt like I was watching a movie with me in it.

"Get up," he ordered.

I got to my feet.

"All fours," he commanded.

I got on the bed head down and ass up. He lubed his thick, throbbing cock up. I didn't think it would go in. The head was a giant lightbulb looking thing. The shaft was red and veiny. He loosened me up with his thumb and I nearly came from that. He got the head up my ass and slowly eased the rest in. He fucked me nice and slow, nice and slow, it was my first time, as I whimpered.

I could hear him moaning. I could feel his hairy balls against my ass. When he pumped me; my whole body rocked. My brain had long sense stopped working. I was a zombie. He was a man. A man's man. Something I knew I could never be. He changed my life. I would never be the same after this night. He filled my ass with his cum. "You're my fucking worthless slut pet now," he boasted.

The next few weeks passed like a blur. He fucked me three times a week. There were rules and expectations. There were punishments. There were rewards. I was not a man. I was a pretty girl. Pretty girls are ready to have sex whenever they are told to be ready to have sex.

He had a rubber paddle that I truly feared. It left red welts on my ass. As soon as I saw the paddle, my attitude changed immediately.

But, the paddle was better than having my nipples clamped which made tears run down my slutty cheeks until I had no tears left to cry.

He was a sadistic Master. The more I cried, the harder he fucked me. There were rewards too. Not paying rent was a reward. Swallowing cum was a reward. Being allowed to cum was a reward. I was studying at my desk, one night, when he knocked on my door. I didn't feel good. But, I knew better than to make excuses.

I had new white and pink sissy outfit with pink bunny ears. I wore a black dog collar. I put on my make up in the bathroom. I put on my heels, strapping the straps around my ankles. If I was late, the paddle would be waiting for me. He let me in.

His eyes betrayed brooding anger. He had a bad week and he was going to take it out on me. He had just come back from the gym and he was sweaty. He clamped my nipples. The pain seared through my body but I didn't say anything. He wanted to use my mouth as a fleshlight.

"Get on your knees."

He fucked my mouth as hard as he could.

I waited for him to give me some air. I stood up.

"I need a break. Please. I'm sorry."

I wiped my tears dry.

"You're hurting me," I confided.

He gave me a long, hard glare.

He opened the side table and took out the rubber paddle.

I kissed him. He was unfeeling.

I kissed him again, sweetly, vulnerably, offering my soul.

He softened.

I got on my knees. I closed my eyes.

He pounded my mouth until he came.

I swallowed every last drop.