Groomed to Depravity Ch. 01

I kind of liked it. The feeling of black sheer stockings on my legs. I rubbed my legs together to enjoy the smooth, silky sensation. I looked in the mirror and take the sight in: a thin Korean boy, just about 5'6" in height, dressed like a cute skater girl.

I was getting ready for the big college Halloween party. As a long-standing tradition, the college held a cross dressing party every Halloween. The girls come dressed as boys and the boys come dressed as girls. As an American-born student from a conservative catholic family, such an event was on the risqué side for me. But as it being my freshman year and all, I had to give it a try just once.

Some of the other guys from my course picked out some very stereotypical costumes from the local party shop, but I felt a French-Maid costume with fishnets was a bit too much. Instead, I grabbed a couple of pieces from the local charity shop. I had soft features with hair down to my shoulders already, so it didn't take much to make me look feminine.

I had a yellow tube-top with denim booty-shorts on, and a pair of converse sneakers. I also bought a spaghetti strap bra that I stuffed with some tissue paper to really look the part. I felt more comfortable than I thought I would, the only part that bothered me was the shorts. They were really tight so I couldn't wear any underwear with them. My penis was less than two inches while flaccid, so luckily there was no bulge showing. The only time it was convenient to have such a small cock.

Ding. A notification came on my phone.

ELLEN: We are pre-gaming at my house. Come by and I'll do your make up ;)

Ellen was a student from America like me, I was always a bit shy and hadn't yet made any real friends, but she fit in with the Brits just fine. I supposed she was as close as a friend I had out here. It was she who told me about the party.

I took one last look in the mirror. I blushed as I saw how cute I looked. I wouldn't mind asking myself on a date, if I could work up the courage. I stuck one of the hairpins I bought at the drug store into my hair as a finishing touch, and walked out the door.

I took the bus to town centre, my dormitory being a couple miles out from most of the college. I got a couple of looks and a few snickers here and there, but no one said anything. I might have looked feminine, but a lot of people could tell I was just a boy playing dress up. I felt embarrassed but kept reminding myself it was just for Halloween.

I stopped by the supermarket to pick up some wine for the pre-game. Ellen's house was still a 20 minute walk away. I was sincerely beginning to regret my choice of dormitory. A single room was not worth all this commuting.

As I walked along the High Street I noticed that an older man was following me. For about 5 minutes now, he'd been just walking along my side. Our eyes locked and he gave me a smile.

"So you like Halloween?" he asked while eyeballing me from top to bottom. The man had a thick middle eastern accent.

"Yeah, heading to a party right now," I replied, not wanting to be rude.

"Party? We can go party at my place right now."

"No thank you," I said with a nervous laugh. I quickened my pace in the hopes that I could lose him.

The man, not discouraged in the least by my response, kept up.

"Where you from, are you studying here?" He asked.

"Yes," I answer nervously. "America."

I turned the corner into a side street heading to the direction of Ellen's house. I hoped the man wouldn't follow me now that we weren't heading in the same direction. I was wrong.

"Me I'm working here, I am Egyptian." He said as he walked closer and closer with me. His arms now occasionally brushing my bare shoulders. "Are you Chinese?"

"No, Korean," I answered. It became apparent to me that the street was rather dark, no other pedestrians save this man and myself.

"You got a boyfriend?"

"No." I said as goosebumps raise on my exposed skin. At first I was uncomfortable, but now I was genuinely scared. I didn't realize, but I had stopped walking altogether in my fear.

The man gave me a dirty smile. He took my pause as a sign of willingness.

"I live not far from here, let's go there and party."

"Sorry I already got somewhere else to be," I replied as I backed away from him. Just two steps and my back was up against a wooden fence.

"You look like you're ready for some fun." He said as he closed the distance between us.

With a strong shove he pinned me against the fence. In my shock I dropped the bottle of wine in my hand. It landed with a loud clang, but there was no one in this deserted street to hear.

The man grabbed my crotch and began kissing me on the neck. I tried to push him away but the heft of his body was too much. He began to rub my small cock like a clit. I was ashamed of how good it felt. Pre-cum dribbled out as the man continued fondling me.

"Yeah you like this, don't you bitch." He said as he gave my balls a squeeze.

I let out a whimper, sounding just like the punk slut I'm dressed as. My arms gave up on trying to push him away.

"It's Daddy's turn to have some fun." He said as he pushed me down onto my knees.

"Suck on it bitch." The man unbuckled his jeans and took out his dick. It was almost 8" long flaccid.

I refused to move and shook my head at him. The man drew his hand back and slapped me hard across the face.

"Don't make me say it twice, sissy."

Not wanting to get slapped again, I obediently opened my mouth. Without even waiting for me to make a move, the man shoved his cock inside. I put my hands around his hips to balance as I bobbed my head and sucked on his large dick. Spit drooled down the side of my mouth as his erection engorged itself. I could barely fit it in my mouth.

I never even had sex before, and now a man was forcing his dick inside my mouth. The very thought of it filled me with shame. On my knees sucking cock in drag when no girl had even touched mine. The salty taste in mouth reminded me that I could never call myself a real man now. Not after I let him do this to me.

"Shit, you ever sucked cock before?" He asked, disappointed with my performance. With his cock still in my mouth, I shook my head in response.

He let out a sigh and grabbed the back of my head with both his hands. I felt his grip tighten on my hair and let out a moan from the pain. The man forced my head in place as he started to thrust his cock deep inside my throat. I gagged on his dick, but this only encouraged him. He quickened to his pace as he shoved his cock deeper and harder. My throat tightened as I gagged harder and harder from the throat fucking.

I felt like I wanted to vomit, but his cock was so far down my throat nothing could get passed. Tears streamed down my cheeks as I choked on his huge dick. Just as I started to feel faint from the lack of air, he drew his dick out of my throat. I felt a rush of adrenaline as I coughed up slime out of my mouth and nose. Did I feel excited by this? There was no time to think as he quickly shoved his cock back in and resumed fucking my throat.

I saw a some people walking in the corner of my eye. Maybe if I got their attention I could escape? But, then they'd see me like this... Before I could make a decision, they had moved to the other side of the road. I guess they must've seen us and decide to leave us alone.

I began to feel faint again and once more he withdrew his cock just enough for me to get some air. Again and again we repeated routine, and shamefully I could feel myself getting hard from being skull fucked by this stranger. A puddle began to form underneath his feet, filled with my spit and his precum.

I had lost sense of time, just trying to keep conscious in this rollercoaster of sex and asphyxiation. I felt his cock get even larger in my throat as he fucked me even harder and faster. Once again I began to feel faint but this time he didn't pull out. I mustered up all my strength and pushed hard against his waist.

I managed to free myself as he came, cum spraying all over my face and chest. At the same time, a tremendous head rush filled me as I grasped for air. He jerked himself to empty out his remaining cum and dragged his cock across my face.

"I was trying to finish inside you to not make a mess, but actually this is a much better look." He said as pulled out his phone and took a picture of my cum covered face.

I sat there in shock, not knowing what to do. I just stared upwards as his camera flashed on and off in the night.

"You can't go around looking like that. Since you've been so good, why don't I let you come to my place to wash up?" He said with a cruel laugh.

Not knowing what to do I just nodded. I supposed I can't really go walking around with cum streaked across my face.

The man dragged me up and began walking me toward what I assumed would be his home. He had his hand in the back pocket of my booty shorts, giving my ass the occasional squeeze. I kept my head down hoping not to run into any passers-by. I could feel the night air drying the cum caked onto my face. My stockings had ripped from my kneeling, completing my image as his cheap used-up whore.

"What's your name," he asked.

"Sam." I answered, not knowing why I told the truth.

"Is that short for Samantha or Samuel?" He joked while pinching my ass. "Mohamed." He said as he pointed to himself.

Soon we arrived at his home, a terraced maisonette not too far from where he forced me to suck him off. He led me inside and put his hand around my waist, gently shoving me past his tiny living room into his bedroom, where I could see the door to an en-suite toilet.

"You can wash up in there," he said pointing to the bathroom door. "But first, we're not finished."

Mohamed grabbed my arms and bent me over his bed. I struggle briefly before I realized that he was too strong for me. Sensing my resignation, Mohamed put took both my wrists in one hand and unbuttoned my shorts to reveal my naked ass.

"No panties? You are a slut." He spit onto my asshole and stuck his finger inside. I felt violated, somehow even more than when he was throat fucking me.

"I bet you were just waiting for a guy like me to come along and find you. What party? This is the party you were looking for." He said as he fingered my anus. I felt him push on my what must've been my prostate. It felt good and I couldn't help but let out a soft moan.

"Yeah, found your sissy g-spot didn't I?" Mohamed massaged it slowly, and I tried my best to suppress my desire to moan out in pleasure. I could feel a constant drip of pre-cum coming out of my tiny limp dick. God, I couldn't believe I liked it. I turned red from the humiliation.

He pulled out his finger and yanked me up by the hair. He dragged me like a ragged doll toward his crotch.

"Suck Daddy's dick a little more bitch."

Wanting it all to be over as quickly as possible, I obediently took his semi-hard cock into my mouth and started sucking.

"Good, you're starting to learn. Might make a proper whore out of you yet." He laughed, pleased with the improvement of my cock sucking skills. I felt his dick get harder and harder, and once more he began to fuck my throat. He was tougher than before and I gagged hard from the brutal thrusts. Just when I could barely take it anymore, he pulled his cock out, a long trail of sticky gag spit still connected his cock to my mouth. I gave him a dissatisfied glare, my only protest of this violent skull-fucking.

"Be grateful bitch. I'm doing this for you." He said as he rubbed my spit all over his enormous erection. He shoved my face into his bed once more and placed both his hands on my ass.

I felt him parting my asscheeks and braced myself for what was coming. I let out a high pitched whine as he inserted his cock into my ass.

"That's tight, you a virgin?" He asked. He inserted his cock all the way in. It hurt, like my ass had a fire inside of it.

"Mhm," I nodded.

"Yeah I bet a sissy bitch like you never fucked a girl, have you?"

I shook my head and Mohamed let out a laugh. He started to move his cock back and forth, thrusting in and out of my ass. The burning pain never went away, but it felt good each time I felt him push past my prostate. I felt a little pre-cum leak with each thrust and let out a little moan, from pain or pleasure I couldn't tell anymore.

As my ass loosened to accommodate his large cock, Mohamed increased the speed he thrusted himself into my ass. He soon pounded me at full pace, his cock ripping in and out of me as fast as his fat hips could move. The pain became unbearable and I began to squeal out loudly from the brutal rape.

"Shut the fuck up, bitch." shouted Mohamed. He threw a punch to the back of my head, and another, and another until I fell silent. My hands squeezed his sheets to help me cope with the pain as he kept on relentlessly fucking me. I still let out the occasional shudder and moan, which didn't seem to bother him.

The fucking seemed to stretch on forever. Every thrust felt as it was ripping me in two. I was sweating from the pain, but every stab of his cock also filled me with pleasure. To my shame, the pre-cum coming out of me was now a constant trickle.

"Looks like you did a such a good job sucking my cock, it's going to be hard for me to finish." He laughed. Mohamed slowed his pace to give himself a rest. It felt as if over an hour had passed. The pain subsided and gave way to pressure as he moved his cock in and out of my ass in slow, deep thrusts. I couldn't help but moaning as I felt myself building to a climax.

"Yeah, moan like a good little whore." He smacked my ass as he picked up pace again. The pain returned, but the pleasure became overwhelming.

Mohamed fucked me as fast and hard as he could, his bed creaking as my body rocked back and forth. I moaned and leaned my ass back as I felt a rush of pleasure from my prostate. I came harder than I ever had. With each thrust I ejaculated more and more cum onto the bedroom floor.

Feeling spent, I felt myself sinking into his bed. I wanted to bury myself alive, to escape the humiliation of cumming while being anally raped.

Mohamed, however, wasn't close to being finished. He kept on fucking me as hard as he could. My prostate was overly sensitive from my orgasm, and the sensation from the constant stimulation was overwhelming.

"Please, I need a break." I asked. The first words I spoke since I entered his house. To my surprise he actually stopped, withdrawing his dick from my ass. I felt my anus continue to gape even in the absence of a cock.

"Looks like you made a bit of a mess on my floor." I heard the click of a phone camera as Mohamed took a picture of the scene in front of him, the gaping ass of a transvestite oriental slut over a pool of cum. "Stay here while I get some water."

I obeyed and didn't move an inch. Tired from the fucking, I used the time to catch my breathe. Less than minute goes by and I hear Mohamed return to the bedroom.

"Lean your ass out slut." I comply and arched out my back. He was still hard and immediately resumed pounding my ass.

I moaned from the pleasure and the pain. It still hurt, but less intensely this second time. Mohamed alternated between slow deep thrusts and fast fucking.

Once again I felt my orgasm building. My moans got louder and more frequent, and Mohamed picked up his pace. I cum again, spurts of ejaculate coming out with each thrust of his cock until I was completely empty.

"Did you just cum a second time from being raped? You really are a sissy rape slut." He teased, not relenting in the least from the intense pounding he gave me. Again the sensitivity was too much for me to bear and I try feebly to push his hands off my ass. He grabs my hair and pulls me up close to him.

"I can tell you want me to stop, but a good sissy doesn't get to finish when she cums. We only finish when I say so." He whispered into my ear. He drops my body back onto the bed and fucked me faster and faster. I started to struggle but he pinned me down with my arms behind my back.

Finally I felt a rush of warmth inside me as Mohamed let out a loud groan. I could feel his dick pulse inside as he filled my ass with more and more cum. Slowly he withdrew his cock, leaving a trail of cum dripping out my still gaping ass.

"Now you can go clean yourself." He said as he walked away to the living room and flicked on his TV.

I got up and pulled up my shorts. The inside was covered with my cum, some dried and some still wet. I went to the bathroom and washed out the cum from my face and hair. As soon as I finished I made for the door without saying a word to Mohamed.

"Let's do this again." He said to me as I walked out his house.

I had left my phone back home because it wouldn't fit in my short pockets. I wandered aimlessly around the neighbourhood, looking for a way back to town centre. The whole time, cum slowly dripped out of my ass, reminding me of my violation. The cold wet spots made from my own cum reminded me how I enjoyed it.

I heard the noise of some drunk students stumbling home and made for that direction. People were already heading back from their parties, making me wonder just how long Mohamed had used me for.

I finally reach a familiar street and began to make my way back home.

"Sam?" I heard a voice call out as I turned the corner onto the high street.

I turned around to see Ellen, dressed like a lumberjack.

"I didn't see you all night." She said as she ran up to me.

"Sorry, I left my phone home because it couldn't fit in my pocket. I got lost and just headed straight to the party." I lied.

"Weird that we didn't run into each other all night. And what are you doing around here..." Ellen paused as looked at my chest. I looked down and saw a cum stain I missed.

"Off having some fun I see." She said with a teasing grin.

"Please don't tell anyone," I begged her, my entire face flushing red with embarrassment.

"Oh don't worry Sam, your secret's safe with me." She winked at me and went on her way. "Have a good night, you slut."