Date: Thu, 19 Dec 2013 23:02:19 -0500 From: Andi Subject: Trailer Park CD 04 (Tramsgender-Teen) Disclaimer: My stories contain explicit descriptions of consensual and Non-Consensual sexual activities and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexual activity, cross-dressing and other fetishes and perversions. All characters and events are complete and total fiction and comes from the twisted and perverted mind of a long time cross dresser. All Stories are the property of the Author. Any feedback would be greatly appreciated. Thanks. You can Email me at SissyAndi@safe-Mail.net . Please consider making a donation to the nifty archives so that this great site can remain free and available to all on the Internet. Background Information I am Scott, at 13 I lived with my mom and my half brother in a run down trailer at the edge of town. We live in a fairly large trailer park. There were a lot of kids in the trailer park ranging from 6 to 17. Some were very pretty girls. My half brother David was 17. Mom had him from a previous marriage and then married my Dad, My dad left Mom when I was 6. Mom was a single woman but worked hard trying to support two growing boys. She had recently took a job at a run down strip club in a bad neighborhood. She tried to convince us that she was not dancing but waiting tables. I knew better after I found some of her dance costumes one night while exploring her bedroom. She left every afternoon around 6 and never got home before 2 in the morning, sometimes even later. She left David and me alone to fend for ourselves. I had heard some of the girls in the trailer park talk about how hot David was. He was 6'2", still a little thin but he had started to grow a mustache to match the black hair on his head. I felt so small beside of him, then I was just under 5 feet tall, barely 100 pounds. I had blonde hair and blue eyes. David never seemed to have trouble getting a date and I am not sure why. From what I seen, he was always rude to the girls and treated them like dirt but the worse he treated them the more they liked him. ******** Trailer Park CD 04 I was having a wild and erotic dream. I was dressed in lingerie and stockings. My boyfriend Art was standing over me, He was playing with his hard cock, occasionally he would rub his cock head against my lips coating them with pre-cum. God I wanted him to do more than just rub his cock head against my pink painted lips. I wanted to suck his delicious cock and swallow another tasty load of cum. I came awake with a start. It was not a dream, but it was not my boyfriend, it was my half brother David who was standing over me, he was nude and his cock was pressed against my lips. When I opened my mouth to protest he thrust his hips forward and pushed the entire length of his hard cock into my mouth. Instinct took over and I began to suck his cock like a common whore. David pushed more and more of his cock into my mouth and caused me to gag. He was nice enough to pull back allowing me to catch my breath. I started to complain but he cut me off with a light slap. He reached down to pull the blanket off of me exposing my nearly nude body, All I was wearing was my Moms pink lace panties that I had worn to bed the night before. "I have been thinking of what we did last night, how I had pretended to fuck you. I need to cum so bad this morning and pretending is not enough anymore. You know I am going to fuck your sexy sissy ass at some point but I will settle for a good blow job right now." He was bigger and so much stronger than me that I knew he would make me do whatever he wanted me to do and it was best not to make David mad and besides it would not be the first blow job I had given so I decided to do my best and get it over with as quickly as possible. David climbed onto the bed and laid down beside of me. He had me scoot around so that my butt was toward the head of the bed and my face was over his cock. We were in the position allowing David to play with my butt and crotch. As I took the head of his cock back into my mouth I felt his hands roaming over my panty clad butt. I sucked on the head of his cock for several minutes before I finally started to bob my head up and down taking more and more of the shaft in my mouth. I was on my knees now working his cock deeper into my mouth when David pulled my panties down to my knees. He surprised me when he squeezed my cock causing it to throb. He slapped my butt and told me to start jacking off my sorry excuse for a cock. My cheeks were burning from embarrassment but I started stroking my small cock like I was told. As I sucked David's cock and jacked myself off David spread my ass checks and pushed a finger inside of my ass. Oh God did that feel so good. I continued to play with my cock as he fingered my sissy ass. I knew I was heading for an incredible orgasm and the feelings intensified when David worked a second finger into me. I was sucking David's cock for all I was worth and pushing my butt back to meet the thrust of David's fingers. I was working my mouth up and down the shaft doing all I had learned in the few blow jobs I had given my friend Art. With my free hand, I reached over and squeezed his balls as I sucked him. I wanted to make David feel as good as he was making me feel. I knew I was not going to last much longer and when David forced a third finger inside of me I came hard. I covered David's thighs with my cum. Seeing that I had finished shooting my load David pulled his fingers from my butt. I was already missing the feel of being stretched. David placed his hand behind my head and started forcing his cock even deeper into my mouth. His cock head seemed to swell even bigger and was throbbing, I knew he was close but I was still surprised when he forced the entire length of his cock deep into my mouth and held it there. I tried to relax and swallow as he shot load after load down into my mouth. When he was through shooting he pulled his cock from my mouth. While he laid there recovering I started to lick my cum from his thighs cleaning him up. "God that was good, we will definitely have to do that again." I tried to avoid looking him in the eyes. David slapped me again before grabbing my hair and forcing me to look at him. "tell me that you liked sucking my cock and you want to do it again." When I did not do as I was told he start twisting my hair causing me pain. Finally I gave in and said, "I loved sucking your cock and tasting your cum, can we please do it again!!" David let out an evil laugh, "I just told you to say you liked sucking my cock but I like your version better." He made me kiss the tip of his cock one last time and thank him before he pushed me away, got up and started to head back to his own bedroom. He stopped at the door and turned around. "Oh tell Art you can not go to the party with him tonight, you are going to a party with me and Clay." "But I have already promised Art I would go with him." David laughed, "I am sure you can make it up to your boyfriend later, just do what I tell you and no one needs to know about your secrets." After David left I put on a T-shirt and a pair of shorts that I had almost outgrown. They were tight but fit easily over the pink panties I had been wearing since the night before. Just walking around the house with panties on under my "boy" clothes kept my small sissy cock hard. Good thing it was so small and no one would notice it with a casual glance. I went to the kitchen to get a glass of orange juice and I was surprised. Not only was our mom already awake, she usually slept until noon since she worked so late, but there was a man sitting at the table with her. Mom introduced him as Mr. Stephens, her boss. As I shook his hand I did not like the way he looked me at me, it gave me the creeps. When he finally let go of my hand he said, "Now that I am your Moms boyfriend, you will be seeing a lot more of me around here, especially after the fun we had last night.", He even had a creepy laugh. Now he was glancing over and leering at Mom like she was a piece of meat. I had already decided that I was not going to like Moms new boyfriend. I had to reach up into a cabinet to get a glass and when I did I felt my T-shirt rise up. I quickly pulled it down hoping that my panties had not been exposed. When I turned around Mom was at the stove facing the other way but Mr. Stephens was looking intently at me and had a smile on his face as his eyes roamed up and down my body. I silently prayed that he did see that I was wearing panties. I finished my juice and went back to my room. I tried to forget the way that Mr. Stephens had looked at me because it made me feel so sleazy. It was not long before my Mom came to my room to tell me that her new boyfriend wanted to take her shopping before they went to work and that they were about to leave. Before she left my room she asked what I had thought about her boss. Mom seemed so happy that I did not want to say anything bad that might ruin it So I told her that he seemed like a nice guy. She hugged me and kissed me good bye and told me to be careful and stay safe tonight since it was Halloween. She was humming to herself as she left my room. ******** Later that day I called Art and told him the bad news that I would not be going to the local Halloween party with him. I explained that I had to do what David told me or he would tell our Mom and my Dad about catching me dressed up that first night. I did not go into detail about what all I had to do to satisfy my brother. Art was disappointed but I promised him that I would definitely make it up to him the next time we had some alone time. He was still grumbling about me not going to the party with him but he did not want word to get out about us so he said he understood. If he had known what I was planning with him I think he would have been very happy. ******** It was 4 in the afternoon when David told me to get my duffle bag and put the cheerleading outfit in it along with whatever I thought I would need to be a convincing girl tonight. We were going over to Clays and I could get dressed there. He assured me that Clay would be the only one home. After we got to Clay he handed both of us a beer. I had never taken more than a sip of Moms beer when she drank and she did not drank often. They encouraged me to guzzle the first beer and soon got me a second one. David then informed me that there was a change in plan. They were not going to go as football players and that I was not going to go dressed as a cheerleader. Clay had borrowed two suits from his cousin and they were going as gangsters. I could go dressed as a flapper girl from the roaring 20's, Clay had already put together the outfit from his Moms clothes. I was not sure what a "flapper girl" was but I had a feeling it would be something I would be humiliated to wear in public. They left me on my third beer as they went to get dressed. When they were done they called me into Clay's Moms bedroom. They were both dressed in dark pin striped suits and were wearing old fedora hats. They looked the part and made convincing gangsters. David ordered me to strip. I was hesitant but did what I was told. When I was completely naked and standing there trying to hide my small but growing cock, David handed me a pair of black lace panties to put on. After I had slipped them up my legs he handed me the matching black lace strapless bra. I finally figure out how to fasten it properly. Clay said OI could use two old stockings to stuff the my bra with giving me a nice size 34 B breasts. Clay's cell phone rang and it was a girl who wanted to talk to my brother. David took the phone and went out of the room for some privacy leaving Clay and myself alone in his moms bedroom. Clay walked over to me and without a word he pulled me into his arms and gave me a kiss. I was shocked. I had done a lot of things with Art and My brother but neither had ever kissed me. I had very little experience kissing anyone but Clay was a good kisser and his kisses became more passionate and I felt his tongue brushing against my lips. I instinctively open my lips and felt his tongue enter my mouth. His tongue explored my mouth and for some reason I started sucking on his tongue like a little cock. While we were making out Clay put his hands on my panty clad butt and started to rub and squeeze my ass cheeks. I started grinding my crotch against Clays. We made out for several minutes and when I was on the verge of cumming Clay pulled away. I let out a moan of frustration but Clay said that David would be back soon and I needed to finish dressing. He handed me a black garter belt and told me to put it on. I did and then I was handed a pair of black silk thigh high stockings. I had watched enough Internet porn while over at Art's house to know I had to sit down on the bed and roll the stockings up my legs before attaching the stocking tops to the garter straps. Between the friction of the bra rubbing against my nipples and the feeling of the stockings and panties I was incredibly turned on. My cock was small but it was still straining against the panties and my nipples were hard and seemed to be very sensitive, When David returned he commented on the small bulge in my panties and said that maybe I needed to go into the bathroom and take care of my problem. Clay surprised both of us when he stopped me and said that he would take care of it for me. Clay rustled around in the top drawer of the dresser in his moms bedroom and pulled out what at first I thought was another stocking but turned out to be a knee hi. Clay walked up behind me and then reached down to undo his jeans and slide them and his boxer shorts down to his knees. He started kissing me on the neck and grinding his hard cock against my panty clad butt. With his right hand he stared pinching my hard nipples through my bra. He had pulled the knee hi over his left hand. He pushed my panties down to expose my hard cock. As he continued to grind his hard cock against my butt and pinch and twist my hard nipples with one hand, he reached around and started stroking my cock with the other. I gasped from the incredible feelings that Clay was causing to course through my body. I could not stop myself from pushing my hips back against Clay's cock. I felt the head of his cock lodge between my ass cheeks. he had not entered me but it would not take much effort on Clays part for him to start fucking my sissy ass and to be honest I was thinking it might be hot if he did. I was so close and when Clay squeezed the head of my cock I lost it and started cumming and grinding my butt against Clays cock even harder. The large head of Clays cock rubbed up and down between my ass cheeks. I guess that pushed Clay over the edge and I felt his cum landing on my back and butt. I am not sure how long he came but I knew the back of my panties were soaked from his load. Finally Clay lifted his hand to my mouth and without thinking I licked what cum that was not soaking the knee hi from his hand and wrist. Clay pulled my wet sticky panties back up into place. Imagine my horror when I looked up to find David with David's digital camera and that he had videotaped it all. I just hoped that David would not show anyone since it included his friend Clay. My cock had went limp and there was not even a small bulge in my panties. After we both regained our composure Clay handed me a shiny purple dress with black fringe. I slipped it over my head and fixed it in place. It came to just above my knee and when I turn quickly the fringe would flair out. Good thing the bra was strapless since the dress has small spaghetti straps. David commented that he had always thought that bare shoulders were sexy. Apparently Clay's mother was part of the local theater company and that the dress was part of a costume she had worn while doing the stage production of Chicago. His mom even had a pair of black 3 inch heels that I could wear. Clay them took a wig out of his Moms closet and had me to put it on. It was a blonde wig that went halfway down my back. After the wig I had to put on the black head band that went with the costume. After I was dressed I looked at myself in the full length mirror on the back of the closet door and to my surprise and pleasure I looked like a pretty young lady all I needed was some makeup. I had not learned how to put on make up yet but I did manage to figure out how to put on some purple eye shadow that matched my dress and some cherry red lipstick. At this point Clay was passed worrying about what David thought about what he did to me so he took me in his arms and kissed me again. After he was done I had to touch up my lips stick before we could leave. I found a small silver purse in the closet and put the lipstick and some tissues in it and took it with me. We took Clays car to the party which was way across town at one of their friends house. The friend went to another school so I did not expect to know many people at the party which was a relief to me at the time. When we arrived Clay introduced me to the guy who was throwing the party. His name was Brandon and even though he was black you could tell right away that he was a rich and spoiled preppy. He was looking me up and down when he asked Clay how old I was. Clay told him that I looked younger than I was and that I was really 17. Brandon gave me a smile and said that he liked young white girls. Then he apologized to Clay and David for the comment but they told him not to worry about it that they liked young girls also. Brandon asked if I was David's date. They shared a laugh as David told him that we fooled around some but no he was not my boyfriend. Brandon took me by the hand and led me into the house, David and Clay followed. I was still a little woozy from the earlier beers and I was unsteady on my heels so I was glad that I had a sturdy arm to hold onto. We went to the kitchen where there was a keg set up. After Brandon made sure everyone had a fresh beer he told David and Clay to mingle with the rest of the people at the party while he gave me a tour of the house. We went from room to room and then he led me up stairs. He opened the door to his bedroom but closed it quickly when he seen his friend with a hot little redhead on the bed making out. After that he said he needed some fresh air and led me out to the backyard and we found a bench in a dark secluded corner at the edge of a small garden. When we were alone, Brandon pulled me close and kissed me. Clay was a good kisser but Brandon was even better. Brandon sat on the bench and pulled me onto his lap. As he continued to kiss me I was squirming on his lap and could feel his cock getting hard. We made out for several minutes before Brandon placed his hand on my right thigh. His touch sent ripples of pleasure coursing through my body, When we broke the kiss both of us were breathing heavy. Brandon started telling me that I was so pretty and asked me if I had a boyfriend. I lied and told him no that my Mom would not let me date yet and that I had to sneak out to come to the party with David and Clay. He kissed me again before asking if I was a virgin, I was not sure if he could see me blush in the bad light as I told him I was. That seemed to fuel Brandon's lust even more and he kissed me even more passionately. This time as we kissed he started rubbing my thigh. He started working his hand up my thigh. I did not want him to figure out that I was not a real girl but was unsure of what to do. I decided that the best defense was a good offense. I stopped his hand before it got to the edge of my panties. He seemed like he was getting mad but he just smiled as I slid off of his lap and kneeled in front of him. I quickly looked around to make sure that we had privacy and that no one was watching us. Then I reached up to undo his jeans and work them down his legs. Brandon was not wearing underwear and was ready for action. . I gasped as his very large black cock came into view. It was at least 8 1/2 inches long and very thick. I was not sure if I could even fit it in my mouth but I was going to try my best. It continued to get harder as I stroked it a few times before I kissed the tip. My lops were stretched to the limit but I managed to take the head into my mouth. I greedily suck the head before I tried to take more of his delicious cock into my mouth. Brandon was moaning as he ran his right hand through my hair. he placed his hand behind my head and held it in place. I soon realized that i was not giving Brandon a blow job but that he was face fucking my painted lips. With every thrust he forced his cock even deeper into my mouth Soon I was having to fight my gag reflex as the head was slamming the back of my throat. I was not sure how much more I could take and I was starting to get dizzy from lack of oxygen when Brandon moaned and pulled back some. I started to gulp air into my lungs when my Black stud started to cum. It was either swallow or choke to death. I swallowed as much as i could but there was so much that some started running down my chin and landed on my chest. Thank god it was above the neckline of my dress because the last thing I wanted to do was get cum stains on Clays Moms dress. I raised up and tried to kiss him but he pulled away. After he had fixed his pants he pushed me away, he said that I looked like a nasty white whore, and told me to get cleaned up. I took out the tissues I had in my purse and cleaned up as best as I could then went to find Clay and David. David was mad because a girl had teased him then would not follow through. We all decided to leave the party. David noticed my smeared lip stick and the dried cum on my chest which made him comment that at least one of us got lucky. It was still early and to my surprise they dropped me off at our trailer before they went to Clays house. I had the bad feeling that David was going to work off his frustration by making me do things so I was glad that they left me alone. I called Art's cell phone thinking he was at the party that I was suppose to go with him but Art said that he had decided to stay home. I sexily asked him if he wanted some company and to my relief he eagerly said yes. I made sure that he was home alone before I told him I would be over soon. I took off the flapper dress I had been wearing and cleaned up. I gargled several times trying to get the taste of cum out of my mouth. I loved the taste but I did not want Art to know what I had done earlier. I found the cheerleading outfit and put it on over the lingerie I had worn under the dress. I wanted to make the night special for my boyfriend to make up for not going to the party with him. The cheer skirt was short and did not come to my stocking tops. I knew I looked like a common street walker as I made my way over to Art's house. It was not a long walk but i felt self conscious hearing my black heels click on the sidewalk. At one point during the walk a car slowed down and I head the catcalls from the boys in the car. I was scared that they were going to come back and try something but they drove off. I was still shaking when I rang the doorbell over at Art's. A big smile came over his face when he seen the sexy cheerleader at his door. "Sadie you look so hot, I am glad you could come over tonight after all." Instead of saying anything I leaned in and kissed him. We dispense with the preliminaries as we rushed to his bedroom. I pushed Art down on the bed and with him watching my every move I started to dance for him. I was seductively swaying my hips as I started to unbutton the vest of the cheerleading outfit. I took off the blouse and threw it onto the floor. I pulled the T-shirt up and off exposing the black lace bra I had on underneath. I turned my back to Art. As I lifted my skirt and wiggled my butt at him it caused him to gasp with excitement. I unzipped the short skirt and let it fall to the floor, I stepped out of it and reached behind me to unhook my bra. When I was topless I dropped to my knees and crawled across the room to where Art was setting on the bed. He already had his hard cock out and was playing with it. As I kneeled before him I slapped his hand away. Then I lovingly took the head into my mouth and sucked on it for a few minutes. I pulled my mouth away and looked up at my boyfriend. Speaking in my most seductive feminine voice I asked him if he liked what I was doing and all he could do was groan approval. I gave him my sexiest smile and asked him, "Baby do you enjoy having your cock sucked as much as I love sucking it?" "Oh God Sadie I love everything we do together." I licked his cock some more before asking, "Art I really love being your girl friend and I want to do something extra special with you tonight." "Oh really? what do you have in mind sweetheart?" "I want you to take my virginity and make me yours. I want you to you to fuck my sissy ass." The look on his face was priceless as he started shaking his head yes like he was unable to talk. I crawled a little bit away from Art and shaking my butt at him, Looking back over my shoulder I smiled at him and told Art to come and take me. I was breathing heavily as I watched Art finish undressing. His cock was long and hard. I loved the way it bobbed up and down as he walked over to where I was on all fours. I was worried about it hurting and I tried to relax. I started to pull my panties down but I had to stop and undo the garter straps before I could finish taking them off. Art had stopped at his desk and he carried a bottle of hand lotion as he approached me. I watched him lather up and stroke his cock. I was back on all fours and waiting for my deflowering. It was only right that I lose my virginity to my boyfriend. i had been afraid that David would lose control and take me roughly. I jumped as Art pushed one finger into me, lubing me up. Art worked a second then a third finger into my ass stretching me and getting me ready to take his cock. After several minutes of Art ramming his fingers in and out of me. Art asked if I was ready. I took a deep breath and shook my head yes. Then I asked him to please go slow and be gentle. Art got behind me and pressed the head of his cock against my butt. I had read on the Internet that during anal sex it was best to push out as the guy entered you. It would make it hurt less. I was pushing out when Art thrust forward and the head of his cock entered me. I wanted to scream but I heard myself squeal like a little girl As Art pushed even more of his cock into me. He held me by my hips. and was rocking his hips back and forth He was in a rhythm and as he fucked me deeper and deeper the pain started to decrease. Art was picking up the pace and I started to feel pleasure from getting fucked. He was not being rough intentionally but lust took over and he started fucking me faster, harder and deeper. The harder and deeper he rammed his hard cock the better it felt. I still fantasized about girls at times and that I figured that I was bi at best. Actually while my boyfriend was fucking my ass I realized that I had become a sissy who craved hard cock. Actually it hit me that Art was the fourth guy I had fooled around with today and that I had become such a slutty cock whore and even more, I loved every minute of it and hoped that guys would continue to either desire me or want to use me in the future. I started to push back to meet Art's thrusts, my actions forced Art's cock even deeper into me. I reached down to squeeze the head of my cock. It was hard and dripping pre cum from the excitement of getting fucked by my boyfriend. Art started to slap my butt as he fucked me. The harder he thrust into me the harder he slapped my ass. My butt was stinging from the spanking he was giving me and the pain mixed with the pleasure and it was quickly sending me over the edge. Without warning I had the most intense and incredible cum of my life. Art let out a groan and came just seconds after I did. We collapsed in a heap on the floor. I laid there feeling Art's cock starting to shrink and felt empty when it slipped out of my butt. After we recovered Art stood up and pulled me to my feet. He let go of me long enough to let me put my panties back on. He led me over to the bed and pulled me down to the bed with him. We snuggled together and I fell a sleep in his arms. The next morning Art woke me up rubbing his hard cock into my butt as he hugged me from behind. He was still asleep. I moved away from him carefully because i did not want to wake him up yet. I twisted around until my head was even with is cock. I took it into my mouth and started giving my boyfriend a morning blow job that I hoped he would enjoy as much as I enjoyed sucking his cock. His body went stiff and his eyes came open right before he shot a load of tasty cum into my waiting mouth. I had not thought about going home in day light when I walked to Art's dressed as a cheerleader the night before. I decided to borrow some of Arts clothes. I figured it was only fair since I had been borrowing his sisters clothes. To be continued.........