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DILLONS FIRST TIME

I have always had feminine features. My Mom is Spanish and I am told my dad was Irish, but I never met him. The combination gave me tan skin with blonde hair. I nice look. My parents also past on their petite size. I was always smaller the other kids at school. My relatives would laugh and joke at what a cute little girl I would make. I guess somewhere in the back of my head the thought sank in. So when I was 12 I began experimenting with my Mom and sister's clothes.

My family was right, with just pantyhose and a slip, I looked very pretty. I knew if I grew my hair I would be undetectable as a girl. That night I had a dream. I was wearing my sisters pantyhose and dress. There were boys teasing me and calling me names, but they kept touching me. I woke with a shudder and realized I had made a mess in my underwear. It was my first wet dream, and the image never left me.

I continued to dress secretly. Thinking of the boys I would let use me as a girl. Sometimes girls were in my dreams, but mostly boys from school. They dressed me and taunted me then made me please them. I had quite an imagination. My hair grew longer and my features became even more girlish. My complexion was clear and smooth, my body was slim but firm. I was 5' 6" and weighed 118 pounds. I grew very little body hair and my voice had a throaty quality, one that could not be described as either male or female. All the play acting came to an end just after my fifteenth birthday. My sister had gone away to college, and my Mom was preoccupied with her new boyfriend, spending a lot of time at his place. So I was alone much of the time. I had just turned 18. I was still in high school. During the vacation a boy named Jarred invited me over his house. Jarred was an athlete, very handsome, strong and could have his pick of girls. He was one of the best wrestlers in the city, and he had graduated with my sister Lisa the year before. So the fact he even new who I was thrilled me. He invited me over because he wanted to learn to play guitar he said, something I am rather good at. I said "Sure" and immediately packed my stuff. Jarred's parents were away skiing, leaving him alone for a few days. We talked for a while, Jarred said he always liked how I played guitar and sang at school. He wanted to learn because he thought it would go over well with girls. As he talked he smoked a joint. Something in his voice didn't ring true. Instead of lessons I played and sang about 60 songs. In some way I guess I liked entertaining him. I wish I could have done more, but this stud would never be interested in a boy like me. Halfway through my performance, he offered me a joint, which I smoked. It was the strongest pot I ever had and I felt buzzed right away. I sang a few more songs and was rewarded with another joint and some wine. Now I was totally high and feeling great. Jarred excused himself and returned a few minutes later with a shopping bag. He opened the bag and pulled out a pair of black pantyhose a full black slip with lace trim and a pair of black 4" heels. I thought I recognized the slip and heels, but didn't make the connection until Jarred said "Here these are your sister's She left them here over Thanksgiving. Make sure she get them."

I knew Lisa and Jarred were friends. They moved in the same circles, she was a cheerleader and he was a varsity athlete. I never knew they dated or were intimate. But Lisa was a quiet person that way. She didn't talk much about her love life to me. I picked her slip up and ran my fingers along the lace.

" Sexy ain't it" Jarred said as he swallowed a mouthful of beer. "Your sister looked so hot in it. I came all over the slip. That's why I have it. She washed it here, but had to leave before it was dry." Jarred looked at her things. I wondered how many times he jerked off in them over the past month. I could tell by his tone things didn't go to well that night with my sister. He seemed to be growing angry.

"You know your sister is a real whore. She let three guys on the basketball team do her an I know a few guys on the football and wrestling team that fucked her to. They say she likes being used and treated like a slut" He was slurring his words a bit. I knew I should have been angry and at least protested what he was saying about Lisa. But all I did was lower my head. '"I'll see she gets these" is all I could muster and I started putting her clothes in the bag.

Out of nowhere Jarred said "Are you a fag?"

I didn't answer.

"I think you are. You look like a girl. In fact you are probably one of the prettiest girls in school, since your slutty sister left. Do you have a cock?" As he said this he reached across and grabbed me hard, squeezing my balls painfully tight.

" Jarred stop!" I pleaded. He laughed and grabbed my hair with his free hand.

"I want you to put her clothes on, Now! "

For a second I hesitated, and I considered leaving, but two thoughts stopped me. One, Jarred looked like if I didn't do as he said I was gonna get a beating and, two, I was getting turned on.

Sheepishly I asked "May I dress in the bathroom?" "Yeah ya little bitch, and make sure you look as pretty as your sister." Jarrod said with a smirk.

I took Lisa's longerie and heels and went in the bathroom. Like I said I didn't have much body hair, and I shaved myself clean for my own pleasure. I used some of Jarred's mother's makeup for my eyes and lips. I pulled up Lisa's Pantyhose and slithered into her slip. I fit into her things nicely. They were a little tight, but it made me look sexier. I wasn't sure what Jarred had in mind for me, but I was going to make sure I looked as pretty as possible for him. Lisa's heels were a little tight but I squeezed into them. One last look in the mirror and out I went.

Jarred had lit another bone. When I walked into the living room he stopped in mid hit. I could tell he was impressed.

"Oh you are a little girl. Get over here Lisa!" He growled. I did as I was told. I was going to be Lisa for Jarred. I stopped in front of him. He reached under my slip and felt my cock through the pantyhose. "I don't want to see or feel cock. You understand bitch!" "Yes Sir. I can tuck it away." I said. I fell into the submissive role so fast it occurred to me it was natural for me. I reached down and tucked my hard penis between my legs. Jarred told me to pull my pantyhose down and bend over. He pulled out a stocking from his pocket and tied the foot end around my cock and balls. He then pulled them tight between my legs and tied the other end of the stocking underneath my slip and tied it around my neck. "if I see that cock I'll strangle you !" He threatened "Now pull up you pantyhose" I did as told.

"Lisa wouldn't let me fuck her. Said my cock wasn't as big as the black guys she fucks. You think my cock is to small?"

I looked at his crotch and could see the bulge. " No Sir." "How can you tell from there" He pushed me to my knees. "Take it out" I undid Jarred's zipper and released is already hard cock from his pants. I don't know what Lisa is use too but Jarred sure looked huge to me.

"Lick it you whore"

My first gay experience. You would think I would hesitate, think about what I was about to do. Instead I opened my mouth and took Jarred's cock deep. He grabbed my hair and wouldn't let me release it from my throat.

"Choke on it you whore" and indeed I was. Finally he let my head go.

"Taste good?"

"Yes, Sir"

"Want some more?"

'Yes,"

"What are you?"

"A whore"

"Well you are going to get all the cock you can handle" He pulled me by my hair and dragged me to the coffee table.

"Lay across the table" Jarred ordered. I obeyed. He tied my hands to the legs He stood behind me and admired my ass and legs. Jarred slowly pulled down my pantyhose exposing my butt.

" Time to get fucked I think" He said ."But first lets play" He took off my shoe and rubbed the heel on my ass.

"Feel good whore?"

"Yes," I answered but in fact it hurt. The rough edges scratched as he pushed it into me.

"Right now its a tie. You and your sister can both take a cock deep in your mouth. Lets see who can take one the furthest in their ass. " He withdrew the heel and I felt pressure on my hole. the head of Jarred's cock pushed through my never before entered ass.

"Please Jarred it hurts me" I cried. He responded with a punch on my head. He grabbed my shoulders and entered deeper. As he did he pulled on the stocking tied to my cock and balls. The pain seared through me. "Beg me to fuck you whore or I'll rip your cock right off!"

I begged "Fuck me Jarred"

"I want better then that" he said accenting his demand with a tug on the stocking, " Tell me what you and your sister and that hot mother of yours are."

"We're whores" I said

"Go on"

"We are all whores. My Mom and sister and me all want you to fuck us. Please Jarred fuck me and then do my family. Make us watch as you fuck us all. " As I spoke and humiliated myself Jarred pumped harder into me. Then he grabbed my hair and thrust deep. I felt his cock pulsate in my ass as the warm milky cum shot deep into me. Jarred spasmed then relaxed. Slowly he withdrew his cock from me. He walked around the table and knelt with his glistening penis in front of my face.

" Clean me!"

I ran my tongue down is softening shaft, tasting his semen and juice and some of me. I opened my mouth and he ran his cock in so I could finish the job. Jarred stood up and left the room. A few minutes later he came back and immediately began shoving something in me. I couldn't tell what it was, only that it was cold and a little thicker then Jarred. He ordered me not to turn around. I closed my eyes and half -heartedly tried to free my hands. After positioning whatever it was in my ass he told me to look over at him. As I did a flash blinded me, then another, and another. Three Polaroid's of me in pantyhose a slip and heels, tied to a table and a cucumber shoved in me. Written on white poster board was "Little Dillon loves his vegetables" Jarred laughed. "Now listen whore, these pictures are mine to do with what I want. I might pass them around in school or I might put them on the Internet. You know what that will mean. So you are my whore slave. Understand?"

"Yes, Sir" I was at once sick and excited.

"Next week you will be here and bring some of your Mom's nicer things.

This was just the beginning of your life as a slut." Then he added.

"Oh by the way. You know big Marvin Mac?"

"Yes, Sir" Marviv was the biggest, blackest person I ever seen, and he hated white boys.

"Well right now he doing something similar to your sister at the college they go to. Next week you and her are going to be the entertainment for about ten or so people. Soon we will find away to get that Mom of yours. I felt the cum shoot out of me and run down my leg.
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