2 comments/ 32664 views/ 7 favorites Jay Cross By: JayCross It was getting dark outside. I sat on my bed reading my favorite magazine, waiting. The sunset ment it was getting closer for my mother to go to work. I walked out of my room and looked down the stair case. I can see her getting her purse ready. I was already done with all of my homework and was ready for a little fun. "Jay, honey I'm leaving" "Ok mom, I'll see you later" I look out the window and see her get in the minivan. She's a nurse and just recently started working the night-shift at the local hospital. She accepted the shift change about a month ago right after my eighteenth birthday. She said they would pay her more and now that I'm older she didn't feel guilty leaving me alone. My parents divorced a year ago. After a rough period for my mother, she finally accepted the situation and had learned to deal with it. The divorce never really bothered me, I was never close to my dad. I see the van drive away. Now that she's gone I can have some fun. Most boys my age play video games or sports. I've never been into sports, which is the probably the reason I'm so thin. I do enjoy video games but it's not what I enjoy the most. I looked out the window again and made sure my mother was gone. I went to the bathroom and turned on the shower. I like to steam up the room a little. I took a nice long shower, washed my hair and blow dried it. I felt good tonight. I stared at my self in the mirror. My silky straight, black hair is covering half my face. I've always had a feminine look with large hazel eyes and unusually pouty lips for a guy. I have been teased for it in school. I didn't care though. I've gotten used to it. I pull out my favorite lotion and run it all over my thin body. I take my time to make sure every inch of me is shaved. It's easier now that I no longer need Phys Ed credits and I don't need to shower with other guys. I dress baggy most of the time so I don't wear shorts at all. I make it to my mother's bedroom, wearing just a towel and holding my special book bag. This is where I'll enjoy myself tonight. She has a large room with an immense bed to match but I go straight to her dresser. I pull out one of her older silk panties. She's gained weight since the divorce so it's easier for me to wear her old panties without her noticing. I look towards the bottom of the drawer where I find my favorite pair of nude pantyhose. I've always loved pantyhose. Ever since I was a little boy I would watch my mother dress for work. As a nurse she would always wear white pantyhose. I remember trying my best to touch her legs just to feel them and dreamed of the day that I would be able to wear them. I sit on my mothers bed and slowly put them on. Left foot first. I stretch my cute toes, admiring the gloss of the fabric. I carefully move them up. I then place them over my right foot. I continue to raise them over my smooth legs, the feel of the soft material always excites me. My dick is usually hard by the time the waist band goes over it. I dont have a large dick so it's easy to keep it encased. I wipe some of the precum off and walk towards my mothers closet. I put on the tallest heels she owns. There a little big on me but they'll do. I stand in front of her full body mirror and admire my self again. Standing there with a hard on wearing only my pantyhose and heels. I look hot and this is where my nightly tranformation occurs. At this point I'm no longer Jay the goth wearing nerd. I am now Bailey, a sexy nylon wearing slut. I open my bag and pull out a dress. It's a new dress I ordered online. I couldn't wait to try it on. It's made of a sexy spandex material and it's white in color. I always order my dresses a size smaller to make sure there as tight as possible. I squeeze my tight body into it, again going over my now rock hard penis. I pull the dress down and cover my pretty ass and now my outfit is complete. I stroll back in front of the mirror. I pull out red ruby lipstick that I also ordered online. I pretend to kiss the mirror and apply it. The transformation is complete. I look amazing, like the slut I wish to be. I sit on the bed again. I cross my legs and begin my pretend tease. A tease for my imaginary audience. As I cross and uncross my legs I pretend to feel wanting eyes running up and down my slim legs. I slowly run my hands over my legs, whishing my hands were someone elses. Someone that would appreciate such beautiful legs. Someone that would worship the perfect shape of my calves and thighs. I reach down to my nyloned feet and message them, once again imagining someone there wishing to kiss them. I would run my feet over the persons face and have them beg for me. They start sucking my toes slowly at first savoring the taste of my skin. They lick the bottom of my foot and bury their nose in between my soft toes inhaling my smell. The worship continues up my legs. They search for the sweet spot between them. Small kisses and a begging plea is all I need to invite them in. They kiss my inner thigh and creep their way higher until they find my gorgeous hard cock. Grateful for the opportunity to view such a beautiful thing that there's is no hesitation and I feel the hot breath on me as they take my nylon covered cock deep in there mouth. My imaginary tease has me heated and I have to grab myself. I squeezed my hard cock through the pantyhose. My hairless member looks amazing, so inviting for a good suck. The pantyhose only enhances it. It feels even better. The soft nylon against it makes it impossible not to caress and stroke. I see myself in the mirror as I continue masturbating. The hot Bailey masturbating. I look like such a whore in the mirror. I continue to stroke my cock until I can't anymore and with a few more squeezes I feel the warmth of my own cum all over my stomach. I lay in bed for a few minutes after, enjoying my self and the view of naughty Bailey in the mirror.I'll get up soon and clean up. I'll wash my precious dress and hosiery so that I can play again tomorrow night. Jay Crossed and Mr. Johnson I wanted to thank everyone that's e-mailed me such nice comments. Jay *** It's Friday and I had a fun weekend to look forward to. I jumped out of bed and made sure to hide the special bag holding my hosiery. I planned to play with Bailey again tonight. I got ready the same way I did every morning. I hated school but I knew it was something I had to do. I quickly brushed my hair and wore my usual baggy jeans and shirt. I made my way into the kitchen where my mother was preparing her breakfast. "You're a growing boy, honey don't forget to pack a good lunch." my mother smiled and gave me a quick hug. I prepared my usual sandwich. I gave my mother a quick kiss good bye, grabbed my book bag and went on my way. I took a full breath of the morning air and began my walk to school. A few steps in, I noticed my next-door neighbor's front door open. Mr. Johnson walked outside to pick up his morning newspaper. When he turned to walk back inside he stopped and stood at his doorway. He was a wearing a large robe and holding a cup of coffee. "Hello, Mr. Johnson" He didn't reply, he simply waived and I kept on my way. Mr. Johnson has always kept to himself, always polite but quite. He retired from the military and had been living alone for years. He was a large muscular man in his early fifties. The entire neighborhood thought he was so handsome, including my mother. I've overheard her telling her friends how much she wanted to invite him over for dinner. "Jay" I turned around. "Yeah Mr. Johnson, what's up?" "Jay, come here for a second" I was surprised he had acknowledged me with a wave but even more when he called me over. I walked to his door. I've never really talked to him before other than the few times my mother stopped to say hi. He had mostly gray hair with the typical crew cut hairstyle. "Yeah, Mr. Johnson?" I asked. He looked at me, sipped his coffee and cleared his throat. "How's your mother doing?" "Umm she's fine," I answered. He seemed unsure of what he wanted to ask. I didn't want to run late to school so I asked him again. "Is there anything else?" "Well yes, I was wondering, what do you call yourself at night?" "Excuse me?" He had stomped me with the question. "I meant what do you call yourself when you're dressed like a girl?" My heart dropped! I didn't know what to say! All sorts of things were running through my mind. How did he see me? Did I forget to close my windows? Shit, is he going to tell anyone? The look of panic must've been all over me. I was so embarrassed I couldn't look at him. "Jay, you have nothing to worry about. It's ok. I'm not going to tell your mother." I looked down, too embarrassed to look up at him. "Jay look at me" I wanted to run away in the worst way. I couldn't think of a worst position to be in. "Jay, I said look at me" Mr. Johnson's voice was stern. I slowly looked up at the large man. "I said you have nothing to worry about. In fact I wanted to thank you." "W-What? T-Thank m, why? "I've been watching you for a while now and I have to admit you make an extremely sexy girl. Your legs look amazing" "Umm ok." I couldn't believe what I was hearing. Mr. Johnson, the most masculine guy I knew and the guy every neighborhood mom drooled over, including my mine was telling me how pretty I was! "I would like to see more of you, maybe tonight? Nobody has to know." I didn't know if he was asking or telling me. I replied the only way I knew how. "Ok" I started to slowly walk away. "I'm going to be late I should be going now" "Yes of course. I hope you have a good day but you didn't answer my question" "What's that?" "What's your name?" "Oh.... umm Bailey." " Bailey, very nice. Well then, Bailey I'll see you tonight and make sure you keep your drapes open." I nodded and walked away. I couldn't concentrate for the rest of the day. From the walk to school all the way to my last class, I couldn't stop think of what he had said. I was still bothered that I had forgotten to cover my windows but that wasn't the worst of it. What did Mr. Johnson want? Did he just want to watch me? I've always wanted to have someone watch. Someone that I could tease and play with but now that I have someone interested, I didn't know what to do. The day dragged horribly but I finally made it to my last class. I kept picturing how the night would go. What should I wear? I sat there in math class conjuring up all sorts of ideas. I couldn't help but wonder what he doing last night while he was watching. Was he jerking off? The different scenarios were arousing but I felt a little unsure. This was another guy that was asking me to dress up. I haven't had a girlfriend in close to a year and I've been teased for it by some of the other students. I didn't care though, I didn't pay much attention to anyone in school not just girls but I never thought I was going to ever dress up like a girl in front of a guy. Although, I didn't think it was going to bother me. Finally the clock struck three and the school day ended. I walked fast to make it home. Ignoring the typical trash talking kids and the other usual after school distractions. I slowed down when I reached Mr. Johnson's house. I looked to see if he was outside before I went in but no sign of him. I was excited. In a couple of hours my mother will be heading to work and I was going to dress up prettier than ever for my first audience. I immediately started counting down the minutes. Hi jay? My mother asked. "Hi mom" I sat down in the kitchen table to chat with her while she finished cooking. I was too excited to be hungry but I figured I could finish my homework and keep my mother company until its time for her to leave. Then at that moment my mother almost ruined my night. "Before I forget your John might be coming over to stay for the night." "What? -Why!?" "Sweetie you know he likes to play in the school tournaments and it's too long of a drive for him to drive home." "Mom his always messing with me, I can't stand him!" "Sweetie he just likes to play around. He likes you; you're his favorite nephew. He means no harm." My mother had just ruined everything. John was my twenty three year old uncle and the biggest asshole I knew. He would constantly pick on me about every little thing. He comes over so he can play basketball at the local college and always ends up partying too hard. I was furious! With him here there's no way I would be able to play. She did say he might be coming. Maybe I'll get lucky and he won't show up. Dinner came and went and my mother was now getting ready to go to work. I sat in the room with her while she changed clothes. She asked me about my school day and I lied and told her it was good. I watched her slip into her white pantyhose and the rest of her nurses uniform. I smiled as I hoped to be putting mine later on that night. It was getting late and my uncle had not shown up. It looked like I might be in the clear. I might be able to have fun after all. I was getting excited again. Once again I watched my mother drive away for work. I rushed upstairs to my bedroom and opened the curtains. I looked out the window towards Mr. Johnson's house. All of his lights were off. I waited a couple of minutes to see if I could see him but nothing. Oh well, I thought, disappointed but I understood if he changed his mind. I continued my routine and stepped into the shower. I lathered myself up well and shaved all of my thin body. When I was done I stood in font of the mirror as I always do. I love the way my body looks after a fresh shave. I walked to my mother's room while still drying my hair. I already had my pretty little dress laid out on my mother's bed and for tonight I had my favorite nude seamless Wolfords. I was dry now and poured my mothers new body lotion all over my chest, legs and feet. I was glistening beautifully. A light turned on it grabbed my attention. I looked out the window and saw a light in Mr. Johnson's house. It was the room directly in front of my mothers. I smiled as I saw the silhouette of Mr. Johnson sitting by what appeared to be a desk. My stomach fluttered with anticipation and excitement, it seemed my audience was ready. I acted like I hadn't seen him and walked towards the dresser and pulled out my mothers ruby lipstick. I usually don't wear any make up to play around in for fear of staining my clothes but tonight was special. I wanted to look my best. I looked at myself in the mirror and smiled. I pretended to kiss myself to apply the lipstick on my luscious lips. As I walked to the bed I briefly looked out the window and saw Mr. Johnson sitting in the same spot as if enjoying a new movie. It was so exciting. I wanted to see more of him but there were too many shadows in his room. I wondered what he was wearing and if he was enjoying himself. I sat down, picked up my hose and stretched out my right leg. I placed the pantyhose at the tip of my toe and started covering my feet, slowly up my ankles and finally my thighs. The fabric was amazingly soft I was hard instantly. I placed it on my other foot and did the same. I stood up to continue putting them on. I was surprised that I wasn't being shy. As introverted as I was, I was standing showing my full, freshly shaved hard on in front of the window. I took my time making sure Mr. Johnson got to see all of me before covering it with my seamless nylon. I turned around and showed off my tight pantyhose covered ass. I moved around a little, feeling a little silly not knowing how to dance. It didn't matter though I was enjoying myself. I found my stilettos with my toes and slid them on adding inches and curves to my long slim legs. It didn't take long to squeeze in to my new dress. The spandex material easily hugged and revealed every inch of me. I was wondering if he was getting as excited as I was. "Was he getting as hard as I was"? "How big was he? At that second someone stumbled into the bedroom. Slamming the bedroom door open and calling my name! "Jay are you in here? It was my uncle he was obviously drunk. He stood there looking straight at me. He moved his shaggy blonde hair away from his eyes to get a better look. He was confused and didn't say anything for what felt like forever until he realized who he was looking at. I was in a shock of embarrassment and didn't have the nerve to say anything. "Well look at what we have here." "Holy shit! I knew you were a little soft but not like this. This is crazy". I sat on the bed reached for a blanket and covered myself. It was an immediate reaction, even though there was no way I could hide what I was wearing. "Don't stop, I want to see what you were doing", he said with a sly smile. I was horrified and stared at the floor with tears beginning to show. He didn't seem to care though and he sat next to me on the bed. "Go ahead keep moving around." No, I said, almost whispering. "Why are you shy?" "Uncle John, you're drunk." I whispered again. "Listen, you little fuck I just caught you dancing around like a girl. I think you should do as I ask?" his smile was now gone. He stopped and burped under his breath and for a brief instant seemed to have lost his train of thought. His alcoholic stench reached me and I cringed. "You want me to tell your mom about your little show?" his voice was much louder. I looked over at the window and saw Mr. Johnson still sitting there. I shook my head but I decided on getting up anyway. "Good, get up like a good little girl." I stood in front of him. My dick was still showing life and I tried to cover it but he reached over and pushed my hand away. His eyes combed over me from head to toe and stopped at my nylon-covered dick. It was obvious he liked what he saw. I slowly walked by the window and thought of Mr. Johnson. "Was he still watching?" "Come here sit next to me" I did what he asked and sat next to him. At this point my night was ruined. I felt like my life was ruined. He's never going to let me live this down. "Do you always dress like this?" he asked me. I didn't respond hoping he would just leave me alone. He was looking straight at me and instead of asking me another question he reached over and placed his hand on my thigh. I pushed his hand away. He frowned and reached again. I didn't push him away the second time. His large hand covered most of my thigh. He started caressing it slowly at first. I was mortified; my drunken uncle was feeling me up. He ran his big hands down my shiny legs. He was obviously enjoying it. He told me to place my feet on the bed. I asked why and he yelled, "Just do what as I ask and be quite." I lifted my self and raised my panty hosed legs on the bed. He took off my shoes slowly and held my feet. He smiled as he caressed my soft ankles and my pretty toes. "Man you do make a hot bitch" He was turned on. It was evident by the huge tent that was growing in his pants. I just sat there waiting for him to finish. He continued feeling my legs. He came up to my knees and to my inner thighs. His large hand slowly crept up until one of his fingers reached me. He felt my hosed dick with his fingers but stopped. His pants were now too small for the caged monster he was holding back. He reached for his pants to unbuckle them, I tried to stop him, "wait, I said" but he ignored me and opened them anyway. What sprung out of his jeans was amazing. It was huge, so much bigger than mine. I've never seen another guys hard on up close before and definitely nothing like this. I've always thought what it would be like to see a real nice cock up close but this was beyond nice. It stood up in attention. Waiting for me, asking for me and I realized that it was that hard because of me. I was feeling so conflicted, he is such an asshole but yet I couldn't stop looking at his huge cock. My uncle lifted one foot and placed it on his lap. My foot was just inches away from this monument of a cock. I reached closer with my toes and touched it. It was like concrete. He moaned and grabbed my other foot and placed it also on his lap. I stretched my legs and put this beautiful beast in between my sexy hosed feet. I stroked up and down slowly. I continued to stroke watching his reaction. It was an amazing sight. He had to have been at least ten solid inches and it was so thick. It was like giving a beer can a foot job. I continued stoking him. After about five minutes. He stopped me and asked to sit straight. I pulled my legs down and sat up. He reached to my face with his large hand and held it under my neck. "Damn you're hot," he said. I looked down and didn't answer. "I want you to kiss It." he said. He wasn't asking he was demanding me. "No I can't do that", I said and tried to offer my feet instead. He didn't care; He wanted me to blow him. There's no way I could do that no matter how pretty his cock was, after all he's my uncle. My drunken asshole of an uncle. "I'm not going to ask you again" I sat there next to him. His cock in full bloom in front of me I didn't know what to do. Until he decided for me. He grabbed the back of my head and lowered it to his cock. He was so much stronger than me I couldn't push back, but honestly I didn't try too hard. It was so big and pretty and about as thick as my forearm. I resisted at first and he slapped my face with it. I complained but he didn't care and held my neck even tighter. My neck began to hurt he was too strong. He continued pressing his cock into my face. I finally gave in. " Please stop," I begged. I opened my lips and slowly tasted the salty tip of his cock. I started slowly and careful. He made me feel like I had no choice. I put the large head in my mouth, slowly stretching my soft red lips. He put his hand on the back of my head and pressed down. I held back, he pushed down harder and started moving his hips up and down, and began fucking my face. His cock went in deeper and deeper I could feel it hitting the back of my throat. I quickly began gagging and slobbering so much that his legs were being covered in my saliva. I thought he was going to cum in my mouth. Everything was happening so fast. He was fucking my face so hard I didn't think he could last much longer but instead of finishing in my mouth he pulled me off. He lifted my head and slid his rock hard rod out of my face. He looked straight at me before lifting me up and throwing me on the bed. He put his hand on my legs. Feeling more of the pantyhose in his hands. He looked so hungry lusting after me. I could see his cock, I couldn't believe it could get any harder but it looked like it had. He reached down to my ankles and grabbed them. " No wait what are you doing" I didn't know what he was going to do to me. I thought he was going to do something terrible. He grabbed my ankles as hard as he could and brought my feet to his cock and cupped it. He then started fucking my feet even harder than my mouth. My ankles began to hurt as he ran my pretty hosed feet furiously up and down on his baseball bat of a cock. He was quicker and harder to the point that the hose ripped on my right foot. At this point I couldn't believe I was actually beginning to enjoy it. I realized I've always wanted a audience to tease. This is the ultimate tease my beautiful, sexy feet are getting fucked harder than I would ever imagine. My dick was getting hard now. My uncle noticed it and smiled. He squeezed my feet one last time, I thought he was going to break them and I yelled in pain. He let go of my feet and took his cock in his own hands shooting his load all over me. H dumped four or five strokes of fluid on me. He finished, stood up and smiled. I was covered in his cum and he loved it. He looked at me for a few minutes before he got up put on his pants and left the room. I was left there with my hard on and my dress covered in cum. I reached to find my dick and through my hose began to stroke it. I looked to the window and realized that Mr. Johnson was still watching. He had seen everything. I wondered what he thought of what I had just happened. I wished he was in the room with me and imagined that it had been Mr. Johnson fucking my feet instead of this asshole. I stroked my self through my wet hose for seconds before the thought of Mr. Johnson pumping his cock in my mouth made me shoot my own stream of delicious cum all over my dress. I settled down. I was now completely covered in cum and exhausted in my hose. I looked out the window again and saw Mr. Johnson walk over to his lamp and turn off his bedroom light.