Kimmy the T-girl

Introduction:

Hello. My girly name is Kim, but in my every day life, I am known as Ken. I am 5"5, 135 lbs. I'm eighteen years old, and this story begins on the last day of school before spring break. I have been a closet cross dresser for the past two years. I started off from stealing my sister's panties and bras and wearing them when I was home, alone, and I've since started to buy my slutty clothes in real stores. I live in Miami, Florida.

--1--

Friday morning. I woke up, got dressed in my ugly, every day, men's clothes and came downstairs for breakfast, only to find a note taped to the fridge in my mom's hand writing:

"Kenny, your father and I are going to visit your sister in college until next Saturday. We've left you two hundred bucks on the counter. Use them only for food.

Love, Mom."

Needless to say, I was totally psyched! I had the whole week to be dressed up. I could even go to a glory hole, if I'd had the guts.

I quickly swallowed down some breakfast and got on my bicycle to school. Classes went by agonizingly slow, and the worst was the last period- PE. I was never good at sports, given my slim and small body frame, and I was constantly teased about this since middle school. I could do reasonably alright in swimming, but no better. Just my luck for coach Barry to choose Football for today.

My class is filled with players on the school Football team, and I was, as usual, picked last. Coach assigned me to play corner back. For most of the game I was humiliated, until the last play. I managed to tackle the shit out of the big, black tight end, Andrew. Obviously, he was not pleased.

I quickly went into the locker room to shower. As I was getting out, towel wrapped around my waist, I saw Andrew grinning deviously at me. It was then, I noticed that the changing room was empty but us two. Andrew quietly locked the door.

"Its just you and me, fag."

I should have known it was pointless. I made a dash for the door, but he caught me in one huge black arm. He raised his other hand and slapped me hard across the face. I yelled and he slapped me again.

"Quiet, you fucking faggot! I'm gonna fuck the shit out of you!"

Andrew pushed me away, and dropped his shorts and boxers to reveal a large, 8 inch boner. I stared at it with wide eyes for a bit too long. He laughed and said, "Come here and suck it, sissy."

I hesitated at this, but he gave me no choice. He grabbed me again and pulled me towards his dick, and then he forced it into my mouth; my first taste of cock. He started fucking my face quickly, and I was starting to get into it. I felt his cock beginning to harden and I was anticipating his semen, but just then, he pulled out and released his jizz all over my face and chest. He laughed and said,

"Tomorrow, 10 AM. I'll be at your house. Wear something pretty. Oh, and don't try anything funny. You'll be sorry." He dressed and walked out, leaving me just lying on the floor, dazed, and with cum all over my body. I loved it.

~2~

Saturday morning, 9:00 AM. I wake up to the sound of my alarm clock going off, loudly reminding me of my soon arriving guest. I got up and went to the bathroom to freshen up. I smiled when I saw my reflection in the mirror. I could still see remains of my make up from yesterday, and my blonde wig, my night shirt and black thong were still on. I sighed, wishing I could be dressed like this all day, every day.

My little girl cock was rock hard, but I avoided masturbation. I knew it would be worth the wait.

Next, I started getting dressed. I removed my nightie, and started glueing my fake 32 C breasts to my chest. I fastened a pink bra, and replaced my thong with a matching pink bikini bottom which barely covered my clit and balls.

I smiled when I saw the clock showing 9:20 AM. It meant I had plenty of time to make myself pretty. I turned my head and walked over to my wardrobe and, after some hesitation, picked out a green mini skirt which barely covered up my round butt along with a colorful blouse and black heels. Before dressing in these, I started applying my make up. Red lipstick and eyeliner worked very well, along with my clothes, to make me look and feel like a complete slut. I was really nervous, so, for the finishing touch, I inserted my butt plug into my tight hole so I could get ready.

I readjusted my wig and sauntered downstairs to wait for Andrew, despite the fact that fifteen minutes were left until he was supposed to get here. I was a desperate, cock hungry slut and proud of it!

Finally, the door bell rang. I got up and walked over to the door, heart beating. I opened it up to see Andrew in his usual gangsta clothes. He looked at me for a moment before recognizing me, and then he doubled over in laughter.

"You really are a sissy fag."

He pushed me in and slammed the door behind him. Then, he smiled, and started groping my ass cheeks.

"I hope you're ready to have that cherry of yours broken, bitch."

I just smiled at him and blew him a kiss, before lifting up my skirt to give him a glance of my bikini covered bottom. He gave me a playful slap, to which I whirled around and pressed my red lips to his and pushed my tongue into his mouth. He moved his hand to rub my ass under my short skirt. I could do nothing but moan appreciatively.

To my dismay, he pulled back from the kiss.

"Suck my dick, you tranny slut."

I eagerly dropped to my knees and quickly began unbuttoning his baggy jeans. After lowering them and his boxers, his big cock sprung out. I hungrily opened my mouth to accept it and began sucking it and moaning. As he fucked my face, he reached his hand into my bra and began squeezing my fake left breast.

Just as I felt he was about to cum, he pulled out of my mouth. I was expecting him to release it all over my clothes again, but instead, he said, "On your knees, bitch."

I got on all fours as Andrew positioned himself behind my ass. He pulled down my skirt and panties to reveal the butt plug. He laughed at this, "I wonder what the football team will say when they hear this."

My eyes widened, and I turned my head around to Andrew. "Please, lets keep this between us..", I begged.

He was not understanding. He gave me a stinging slap again and yelled, which I hope the neighbours did not hear, "SHUT UP YOU STUPID SLUT!", and he slapped me again.

I moaned in pain and grudgingly turned back around. He quickly pulled out the plug, which left my hole wide and gaping. I heard him spit on his black cock and, seconds later, I felt him pushing at my hole. I moaned in pain and pleasure as he began pushing his cock up my bowels. It took him a few minutes to reach the hilt- I felt his hips pressing against my ass cheeks. His hands slid up my bra to my boobs.

He quickly pulled out and started fucking my ass. I winced at the suddenness of this, and then I started to moan. I felt my clitty getting harder as my orgasm approached and I reached down, hand shaking, to take it out from my panties, pointing up.

Our rhythm increased, and my hole began to tighten around his cock. He grunted as he released his semen in my ass and, at the same time, my cum spurted all over my blouse. We both lay there in bliss after our mutual orgasm until his cock shrank enough to slip out of my ass. I sighed at the loss.

Andrew got up and walked out the door wordlessly. I just stayed there, with cum leaking out of my ass and down my chest, smiling widely. I was no longer a virgin, and I had a feeling more was to cum.

To be continued..

Disclaimer: This is my first story. I'd appreciate feedback and advice for the next time. Hopefully, I'll find time to complete it soon.

Love and kisses,

Sissy in denial