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High School Sweetheart Chapter 1 It was 1971 and Halloween had come around once again and I was dreading it. It fell on a Sunday this year so I knew some time during the day my mom was going to tell me I would need to escort my brothers and sisters on their rounds tonight since my dad was working. I was in my freshman year of high school and felt that I had become too old to dress up and beg candy. I sort of regretted the candy part but I would probably extort some candy from my sibling's bags as an escort fee or something. "Tony!" my mom called out. "Here it comes," I thought to myself. "Yeah. I'm in my room." She appeared at the door. "Good, I need you to take the kids trick or treating tonight." "Really? What a surprise!" Sarcasm is big with me. "Funny," she answered. Then she stood for a moment looking at me. "What?" I asked. "I think you ought to dress up tonight while you take them," she observed. "Don't you think it is a little late to be trying to figure out a costume? It's 2:00 now, we'll be going out about 6:30. I don't think there is enough time. Besides, I don't need a costume to babysit them while they go knocking on doors." "Actually, I already have an idea. I'll be back in a couple minutes." I sat there staring at the empty doorway for a minute wondering what she was up to. I didn't like this at all. About 15 minutes later she was back at my door with an armload of clothes. She laid them on the bed and then tossed me a small bundle. "Put these on and then we'll work through the pile. This should only take a few minutes to decide. Come see me when you are ready with the first one." She pulled the door closed as she left. I looked down at what she had tossed me and it was a pair of white panties and nude pantyhose. My blood ran cold and I felt my stomach turn over. I went to the bed and sorted through the clothes. Dresses of varying lengths and one hot pants set. I recognized them easily enough because I had been trying them on occasionally when I was alone in the house. Was this her way of saying she knew and was calling me out? I leaned out the door and hollered, "Are you serious?" "Just get started. We have time but not all day." I closed the door and looked again. The terror was passing and I was feeling excited and anxious at the same time, it reminded me of the first time I got to ride the big roller coaster. I dropped what I had in my hands on the bed and stripped off the clothes I was wearing. I put on the panties and pantyhose; I loved the feel of them. I felt I was lucky in that I hadn't gotten a lot of body hair yet. Some of the other boys in my gym class already had large amounts of thick, dark hair which I thought was totally grotesque. I prayed often to be spared of that. I picked through the dresses and found a maxi peach halter dress. It was one of my favorites because the material felt so good against my skin. I put it on and checked myself. That started me reacting in ways I was accustomed to when dressing alone but a few adjustments and I felt I hid the excitement I was feeling fairly well. It turned out it wasn't really necessary as it quickly disappeared when I reached for the doorknob to go see my mother. I checked the hall, nobody was in sight. "Where are you?" "In the kitchen, don't worry, everyone else is outside playing." I went to the kitchen and found her sitting at the table brushing out a blond wig. "Come over here," she beckoned with the brush. I went to her and she put the wig on my head, the hair coming down well over my shoulders. She brushed and adjusted for a few moments. "OK, step back and let's have a good look." I stood in the kitchen wondering what she was seeing. I had a rough I idea of how I looked having looked at myself in the mirror on those other occasions. I was still young enough that I thought I would be fairly passable but I wasn't sure. Even without breasts I knew this dress looked good on me. I wondered how much the wig helped. "Why did you pick that dress to try first?" she asked. "Uh," I hesitated. I couldn't tell my mother the real reason. "I just thought it would work best." I spread the skirt out a bit. "Being long it would cover me up more." "Hmm, yes," she mused. "Hold on a second." She left me standing there. I started looking around for a shiny surface to see what I looked like in the wig. Before I could find something suitable she returned. "The color actually looks good on you but I don't think it will work tonight though; you don't have any chest. There is another long dress, go try that one. Oh, and put this on, too." I caught a bra that she tossed me. "For now, just wad up some socks or underwear to fill the cups. I need to see the dresses on you with a chest. Go on, next" I turned and went back again, hiking the skirt so I wouldn't trip. My knees were a bit wobbly. I took off the dress and put on the bra. I spent a few minutes trying to stuff it with various things until I found a way to ball up a couple t- shirts that seemed to fit the bill. I grabbed the other long dress, it had a black sleeveless top, high collar that appeared to be as choker with a triangular cut below it that didn't go far enough to expose the cleavage I didn't have. The skirt was an Indian print and a wide black belt wrapped around my waist. "Well, that took you a while, but it looks like you did a good job." This time she walked around me, then squeezed each of my breasts trying to even them out a little more. "Do you like this one?" "Yes," I blurted before I thought to stop myself from appearing too eager. I found I was really starting to get into it now. "I mean, I think it fits pretty well and it has me pretty covered up." "Yes, it does, but the length might actually be a problem now that I think about it. You'll be trying to keep up with the kids and needing to climb stairs. I don't want you to trip and ruin the dress. Next." So the long dresses were out. That was too bad really because I had found I liked wearing long dresses more than shorter ones. I looked through the shorter dresses and picked up a red dress next. It buttoned down the front to the waist where it flared out in a full skirt that would reach around my knees. A wide belt hung in a couple string loops. I put it on and plodded back to the kitchen. "This dress makes me think of Donna Reed," I announced as I came back in the kitchen. "Well it is actually shorter than the dresses she would wear," mom informed me. She tugged and smoothed it while I stood waiting. "It fits pretty well. Do you like it?" "Yes, it's comfortable," I answered. "OK, go try another," she waved me away. I nodded and went off to my room. Two more outfits remained: the hot pants, and a little black dress. The LBD was short, about mid-thigh, and very fitted. I decided to try it next because I hadn't tried wearing it before afraid I might stretch it out but since she wanted me to I didn't have that worry this time. Once I squeezed into it I went back to the kitchen. "Wow, that is a little tight. Sorry, but it is too tight where you don't want it to be. If you really like that one you'll have to try and make some adjustments" I tried looking down the dress but my breasts blocked my view. I had to mash my breasts down to see what she was talking about. I had a definite bulge where one didn't belong. Now that I was aware of it I could feel that it was about to become even more prominent. I quickly turned my back toward my mother pretending to try and examine the back of the dress. "Yeah, well I am sure you could find a way. With that dress I think I would put you in black hose as well. It's your choice." "What if I decide I don't want to do this?" I asked. "Oh, well tonight I am not going to include that as a choice. I think you need to do this. I can tell you've been going through my clothes and I understand you are probably curious. Tonight, you get to experience it and it is the perfect time for you to do it. Halloween is a dress-up kind of night. Not like you getting caught in a dress in July for instance." The bulge in the dress was totally gone now. Hell, I wasn't even sure I had a penis any more. I felt the color had drained from my face. "Don't worry about it. I'm not mad. I just think it might be time you stop sneaking around, at least from me. I think if you relax and let yourself enjoy this as a Halloween dress-up you might actually have a really good time. And maybe even satisfy that curiosity. Or maybe you will have more questions. This is life and sometimes it takes longer to figure things out. Now, last outfit, go!" I returned to my room and sat down on the bed for a few minutes. I ran my hands down across my knees, down my calves to my ankles and back up again. I repeated the motion over and over as I thought about what my mom had just told me. I thought I had been so careful when I borrowed her clothes trying to put everything back exactly as I had found it but she knew. I wonder how long she has known. "Are you coming back?" she called from the kitchen. "Yes," I shouted through the closed door. "Be there in just a couple minutes." I peeled the little black dress off and carefully laid it on the bed. I picked up the hot pants outfit. It was hot pink with white pattern lightly tracing all over it. I pulled on the shorts which felt smooth and sleek. They easily slid up the nylons on my legs and instantly got me turned on again. They were, of course, very short barely covering my butt cheeks. The top was the same material actually looking like a mini-dress. Once on, the skirt was just long enough to cover the shorts by less than an inch. The front of the skirt had clear crystal button of which the bottom couple were undone revealing the shorts whenever I took a step. "Oh, my! Your legs look so long!" my mom exclaimed when she saw me. "Hold on a second," she left the kitchen. When she returned she had a pair of white boots in her hands. "Here, put these on." I sat and squeezed my foot into the first one. It was tight but the hose allowed me to slide in. I zipped the side up and looked at it. It had about a 3 inch heal and the top was about an inch below my knee. I put the other on and stood up. I wobbled a bit at first but the heels weren't that narrow and after taking a few steps around the kitchen I was walking fairly well. "Well, first of all you look great. Secondly, if you were my daughter there is no way I would let you out of the house looking like that," she stated. "Third, you are my son so there really is no way I am going to let you go out like that." "Hey, these are your clothes and you wanted me to try them on!" I protested. "Besides, wouldn't this seem like more a costume for your son?" "Yes. Do you really like wearing that outfit that much?" she shook her head to show she wasn't really expecting me to answer. "Well, daughter or son, you are 14 and there is no way you are wearing that." "Great, so the one thing that has pants is no longer an option even though it looks great and would work as a good costume." She reached behind me lifting the skirt and running a finger across the bottom of my bottom below the shorts. "No, not appropriate for a 14 year old and especially since you are going to be walking your brothers and sisters. I am taking this option away. "So, we have eliminated the two long dresses and the hot pants," she went on. I watched her eyes as she talked, she couldn't stop eying my legs and I was feeling a little weird about it. I think she was too because she kept trying to look away at other things. "Which of the dresses do you like better? The black or the red?" she finally asked as she looked at something on the table. "I think I'd rather go with the red dress. The black is very tight, a bit short and I'm not sure I can be out in public in it. It is going to be tough enough wearing the red dress." I offered. "The black is too short but you want to wear the hot pants? That doesn't make a lot of sense to me but I can go along with the red dress. It makes sense," she nodded. "Follow me." We went to her bedroom and she started going through her lingerie drawers. She pulled out a red bra, black panties and pantyhose. She examined the hose, put them back and selected another pair. "Here, take these and change. Bring all the clothes back in here and I'll put them away," she commanded. "Oh, and don't stuff the bra yet. I have an idea for that." I returned to my room and stripped down again. I put on the bra and panties and as I put on the hose I noticed they had a fake seams running up the backs of the legs. I did my best to get them straight; I then put the dress on. It seemed odd looking down at the front of me now with a dress and no boobs but I was certain that would be resolved soon. I put the rest of the clothes back on their hangers, gathered the used underwear up and took it all back to my mother's room. I laid it all on the bed and noticed a pair of black high-heeled shoes beside the bed. The heel appeared to be a bit higher than the boots and a lot narrower. I sat on the bed and slipped them on. There was an ankle strip and it took some work but I finally got them buckled up. Just as I stood up my mother came back into the room. "Oh, good, you found them and they fit. Can you walk in them?" she asked. I took a couple tentative steps and my ankles threatened to betray me but I persevered. It didn't take long before I was able to walk around the room without worrying about a trip to the emergency room. "I think you are going to need this too," she stated as she reached into the closet. She pulled out a black half-slip with the top part a solid silky material before it spread out in a stiff netted material. "It will make the skirt stand out some, like the old poodle skirts, but not as dramatic." I took it from her and put it on getting it all the way up to my waist. It was a challenge trying to do it in the heels but I managed without killing myself. I pulled the dress back down straightening it over the slip. It had more volume but it wasn't over kill. "Ok," mom started as she began unbuttoning the front of my dress, "now we fix your chest." She had brought a couple of sandwich bags, the type that fold over themselves to seal, and filled them with sugar. Placing a bag in first cup she molded it against my chest and into the cup of the bra. She added a bit more sugar from the other bag and after pulling the front of the dress open and closed a few times and adjusting she finally decided it looked right. "I need more sugar," she announced, "let's go back to the kitchen." She fixed my other breast and then sat me down on a chair. "Last step, let's do your makeup." I sat down on a chair and my mom went to work. She muttered to herself and said a few things to me as she applied all the various products instructing me to turn this way, turn that way, open your eyes, close them, blink them, and purse your lips. Just as she was finishing up, Joann, my mom's best friend, came into the kitchen. We rarely locked the doors during the day because of the kids playing outside and Joann rarely knocked when she came to visit. "What are you up to?" she asked as she sat in one of the chairs. "She's pretty, isn't that your dress she is wearing?" My mom didn't reply, she just looked at me, "OK, that should do it. Stand up and give us a spin. I want to see how it all looks." I nervously glanced over at Joann. Joann was a knockout. She worked at a bar near downtown and was obviously on her way to work. She had long dark hair that was lightly curled and reached down to her ample bosom. She had on a turtleneck sweater and tan shorts, they covered about as much as the ones as I had worn earlier. Dark hose and knee high boots covered her long legs. She smiled over at me, and then her eyes narrowed a bit as she tried to figure out who I was. I stood and moved to the middle of the room. I lifted my arms and did a little pirouette just quick enough to make the skirt fly out a bit. When I had done a complete turn I looked back at my mom. "Well, I think you look terrific," she smiled, obviously taking some pride in her work. "Joann, what do you think?" "I said before that I think she looks very pretty. Earrings and a necklace are a definite need. Your dress looks good on her. Maybe open the collar a bit more to sex it up a little." "No, that won't work. Boobs are bags of sugar, can't let them show at all," she answered trying to suppress a smile. "But you are right about the jewelry, I'll be right back." Joann's mouth dropped open. "Tony? Is that you?" I smiled and gave her a little curtsy. "Oh, my! That is unbelievable! Walk across the kitchen for me, let me get the full effect," she gushed. I did as instructed. When I got back to my starting point I asked, "Do you mind if I go look at myself? I haven't seen a mirror yet?" "Go use the one in my bathroom," mom responded as she returned. "And put these on while you are at it. She handed me a necklace with a pendant and clip on earrings. I left in a hurry barely able to contain myself. I wanted to run but didn't dare take a chance on the heels I was wearing. I snapped on the light at I entered the bathroom and positioned myself in front of the mirror while staring at the floor. I closed my eyes and raised my head. Taking a deep breath I opened my eyes. I was shocked. I didn't see myself at all in the mirror. My mother had done an incredible job on the makeup. I looked older, closer to 25 than 14. The dress helped to make me look older as well. I twisted back and forth looking at my profiles and feeling the slip swish around my legs. I ran my fingers through the blond hair coming down over my shoulders and just stared at myself. "Are you coming back sometime today?" my mother called. "Just a minute!" I called back and put the necklace around my neck. It wasn't very long so I was able to have it under the collar of the dress and be visible above the opening of the dress. I snapped the earrings on to my earlobes. With one last look I turned and went back to the kitchen. I noticed the clock as I was going through the bedroom and realized it was only 4:30. We wouldn't be leaving for another 2 hours. I got back to the kitchen and took a seat while my mom and Joann continued to chat. Mom was describing how I looked in the various outfits. "Well, Tony, I think you are an incredibly good sport to allow your mom to do this to you. I know a lot of boys that just wouldn't stand for it. I wish I had gotten here at the beginning of the trying on though, from what she tells me her hot pant suit was something to see, even before the makeup." "Apparently, I didn't see myself but she was adamant that I couldn't wear it. Said it wasn't proper for a 14 year old. I thought it at least had pants and might be a little better for being outside." I gave my mother a look trying to decide just how much Joann might have been told. "She bragged that you looked good in everything. I hope maybe the next time, if there is a next time, I'll get to be here for the whole tryout." She gave my mom a wink. "Hey, maybe I have a thing or two to contribute to the effort!" "Halloween is already taken care of this year." I pointed out. "I don't want to think about next year yet. I may decide not to be so good a sport." "Your mom said she had a really good time doing this with you today. I'm sure she'll want to do it again. I hope you have fun and are up for it." She gave me another radiant smile. I listened while the two of them talked, occasionally picking at something on my dress, trying to think of something I could do while waiting to take the kids trick or treating. They would be coming in soon for dinner and to get into their own costumes. I noticed both ladies glancing over at me regularly. "Hey," Joann said, "I forgot something at home. Tony, would you like to take a ride with me back to my place? It will only take a minute or two. You'll be back for dinner." I looked over at my mom who nodded. "Sure, I'll go." I wondered why she wanted me along. We got into her car and I gathered the dress into my lap, careful not to get it caught in the car door when I pulled it shut. The ride over was short, she lived about five blocks away, and I didn't say much in response to how much she couldn't believe it was really me. We got to her place and reached for the door handle. Before I could open the door she laid a hand on my arm. "My neighbor is here watching my kids," she started. "She's about your age, might even go to your school. I want to see if she can see you are really a boy. I'll call you Teri. Can you soften your voice a little?" I was terrified now. If this got back to school I'd be a bigger target for the bullies than I already was. It wasn't bad but it sure didn't need help to get worse. I swallowed and stammered, "I-I-I-I can t-t-try." Joan smiled. "Just relax. You fooled me, you'll be fine." She opened her door and got out of the car. I did a very unfeminine thing and stared at her ass and legs as she climbed out of the car. I felt a little better. I took yet another deep breath, got out of the car and followed her to her door. We walked in and I saw the girl sitting on the couch. I recognized her immediately as a girl from my homeroom. So much for maybe knowing her, we saw each other every day. "Oh, Joann!" she squeaked. "You scared me. I didn't expect you back so soon. Everything ok?" "Oh, everything is fine, I just forgot something," Joann answered waving a hand as though brushing something away. "JJ, this is Teri, a friend that lives over by Marie. Teri, this is Judy Jamison, we call her JJ" JJ waved, "Nice to meet you." "And you," I answered. Joann smiled and went to the bedroom to retrieve whatever it was she forgot. I stood there trying not to look at JJ counting the seconds until I could get out of there. "Would you like to have a seat?" she offered. "No, thank you, I'm fine." "That's a pretty dress. Red is a good color for you, goes with your hair and complexion so well." I just smiled and nodded as Joann came back in the room. "OK, we are gone again. Thanks JJ, be careful taking the kids tonight. Are you going to dress up to go with them?" "I don't think so. I'll probably just go as I am. I'll stay right in this neighborhood so there shouldn't be any problems. It's really too late to put something together." Joann laughed. "I was talking to Marie. Her son said the same thing so she stuck him in one of her dresses and made him up. He looks pretty good, too." I reacted by whipping my head around to look at her and my mouth dropped open. I almost said something out loud but caught myself just before it came out. Too late though, I'd blown my cover. JJ looked at me, then back at Joann. "Tony?" "Yeah," I answered looking down at the floor but not before trying to give Joann a dirty look. "Listen, JJ, please don't say anything at school about this. You know how bad it can get if this gets out." JJ snickered. "No, I won't say anything. But this is amazing. If you hadn't jumped when Joan talked about Marie's son, you, I wouldn't have made the connection." "Listen," Joann started, "why don't we grab the kids and their costumes and take them back over to Marie's? You guys can walk the kids together." "I'm sure the last thing she would want to do is walk the neighborhood with me looking like this," I offered. "Actually, I would like it. And I have an idea for what I can do for a costume. Joann, if you can get the kids together I need to run home for a minute." "No problem, be back here in 10 minutes. If you need you can change over at Tony's," she said. "I am going to have to drop you and head straight for work." JJ hit the door on a run. "Sorry," Joann offered. "I really didn't mean to expose you that way." She called for her two kids. I called my mom and explained what was going on while Joann got her kids changed and ready to go. Ten minutes later we piled into Joann's car and headed back to my house. Once there we got out and Joann drove off. We ate some dinner, my mom got the kids changed and then fixed my lipstick, JJ went to the bathroom to put on her own costume. JJ had decided to keep the theme in play. She dressed in a man's suit and had penciled in a mustache. It was a bit big on her but she didn't have the help I had gotten during the course of the day. Her hair was short already and she gelled it down for a slick look, tucking the little extra length she had down the back of her collar. She looked pretty good considering. My mom insisted on taking pictures of everyone before we left, of course a couple of them were of JJ and me together. We finally hit the road. We walked the kids from house to house and talked a little about school, the teachers and the other kids. We talked a little about what we did in our free time. Not much and a lot of it interrupted by needing to call out to keep the little kids from running too far ahead, or warning them not to eat the candy before we could get back to the house and check it. During the quiet moments I found myself thinking I could have been comfortable in any of the outfits I had tried on earlier and wondering what JJ's reaction might have been to them. As we walked away from the last house we let the kids run ahead back home, JJ stopped walking. I stopped and turned to face her. "Would you be honest with me if I asked you a question?" she spoke so softly I barely heard her. I looked around to see that we were alone. "I think so." "Do you like me?" she asked looking off at other things in the area. I laughed. "Yeah, I like you ok. You spent the whole night with me walking kids around with me dressed like this," I twisted back and forth a few times making the dress shake, "and didn't give me a hard time about it or make fun of me or anything like that. We've had a nice talk, I think. Actually, I was thinking I might like to hang out with you at school if it would be ok with you." It was my turn to find something interesting on the ground. I pressed my dress back against my legs so I could look at my shoes. I was happy I had managed not to scuff them up. JJ looked at me and smiled, "That would be really nice. But why did you laugh?" "Because I was afraid of what question you might choose to ask. That one was an easy one to answer." We turned and walked back to the house and went inside. The kids were in the living room carefully spreading their candy out for examination. My mom would eliminate anything remotely suspect of being able to be tampered with. I sat on the couch, JJ sat down beside me, close but not too close. "Are you ready to get out of those clothes yet?" mom asked me. "Oh, I'm just glad to get off my feet. These shoes are just a little bit on the small side and they make my feet hurt. I'll change in a minute," I answered. Turning to JJ I offered, "if you'd like to go change that would be ok. I'll be here when you get back." "OK. I'd like to do that. These shoes are hurting my feet as well," she said as she stood up. "And I don't think it is just because you think your shoes are small. Welcome to a girl's world. Shoes like those hurt if you spend a lot on time on your feet." "OK," my mom called, "everyone get your candy picked up and in your bags. My kids, go get ready for bed, school tomorrow." I watched as they all complied. Leaning forward, I pushed the dress down between my legs as I spread my knees and reached for an ankle strap. Once the shoes came off I lifted my feet and spread my toes, examining them through the dark nylon that webbed them together. "You seem quite comfortable," my mom observed. She had taken a seat in a chair on the other side of the room. I let my feet drop back to the floor and evened the dress out again. "Well, actually, I am," I glanced back up the hall to be sure JJ wasn't coming back. "I'm glad I did this, you did this." Mom glanced at the clock, "Your father will be here soon. He is going to honk so JJ and the kids can be taken home. We'll talk a bit more after they go and before he gets back." JJ returned and sat on the couch with me again. We chatted about some of the costumes we saw on others during our travels that evening. After just a few minutes we heard the car horn and they headed on out the door. "I'll see you tomorrow at school," I called to JJ. She turned and waved. I grabbed the shoes and went to my room where I stripped off the wig, jewelry and all the clothes. I threw on a pair of shorts and a t-shirt and headed for my mom's room to return all her stuff. In truth I was a bit disappointed it was coming to an end. We headed for the bathroom where mom went about disassembling the masterpiece she had put together. "So, was that enough? Are you still going to be prowling through my things?" she asked. "And please don't lie to try and spare my feelings or because you're embarrassed. I figured it out once, I'll know again." I hesitated before answering. I finally decided the truth would be the best course. I waited a bit longer until she finished scrubbing around my mouth. "Actually, I wish it had gone on longer. Once I got over the fear of what someone might say or do and relaxed I had a great time. I loved the feeling of the clothes I was wearing. I loved the fact that someone thought I was actually pretty," I confessed. "I can see wanting to do this again next year. And, I can try and not got through your things, but sometimes my curiosity gets the better of me." She stopped cleaning my face and looked me in the eye for what seemed forever. Then she nodded and went back to cleaning. "Do you think JJ is going to be a girl friend or just a friend?" "I'm not sure yet. Just a friend for now, we only spent a couple hours together but we will probably be spending a bit more time together at school now." "I'm also trying to understand," mom went on. "I guess I am trying to figure out if you are gay, or want to be a girl, or what. I'll support you in whatever you are, some choices will make life a bit tougher but you've got to be happy with yourself." "Well, the way I feel right now is that I am not gay. The idea of touching another guy kind of grosses me out. But at the same time I like wearing the pantyhose and the dresses and all the other stuff too. I've seen pictures of girls in stockings with garters that I'd like to try some time. I've seen other things that I don't even know what they are called but they look sexy and sleek and I bet they would feel great to wear. "Thank you for making me do this tonight. I had a really good time." I fell silent. "OK, first, I am glad you enjoyed yourself but now I am not certain I made the right decision in having you do it. Maybe if I hadn't your curiosity would have eventually died out. But, what's done is done. "Second, do not expect me to be buying you things, or buying myself things for you to wear. I need to put some thought into where things are going to go from here. "Last, your father will not appreciate this. I was trying to decide if I was going to tell him about you secretly trying on my clothes but now I think I'll let it be just between us. Tonight was just an idea I had and it seems you have made a new friend thanks to Joann." We heard the door as my dad got home just as mom finished removing all the makeup. We left the bathroom and I said good night to both my folks and headed off to bed. It had been a long day for me but I couldn't go straight to sleep. I lay there reflecting back on the afternoon and evening for a long time. Eventually I did manage to get to sleep. Chapter 2 The next morning everything was back to normal. I got dressed in my normal boy clothes and after breakfast walked to school. I thought back on my night and remembered how the breeze felt against my legs. I also remembered how my feet started hurting in those high heels. I got to school and headed for my first class, homeroom didn't come until mid-morning so I didn't expect to see JJ until then. Others in the class were talking about the previous night, some had sibling duty like I had, others thought it funny to terrorize the neighborhood egging houses or covering them in toilet paper. Nobody admitted to dressing up. I finally got to homeroom and picked a seat. This was a short period used for announcements and other things, only 20 minutes. More kids rolled in taking seats around the room and finally I saw JJ come in the door. She took a look around the room spotted me and went to a seat on the other side of the room. I felt a sickness settle into my stomach. The announcements went by without my hearing a word. The bell rang and I went off to my next class. The end of the day came around and I headed out the door and down the block, as I turned the corner I almost ran over someone. I looked up and JJ was standing there. "Hi, Tony," she started. "I thought I ought to explain something. I don't want you to get the wrong idea." "I already have an idea," I snapped. "why don't you explain and I'll tell you if it is wrong or not." She jumped like I had slapped her. I didn't mean to be so rough about it but I was feeling very hurt and was certain my high school life was about to become hell. "I tried to catch you before you got into first period this morning but you were too quick. Tracy, in homeroom, saw us last night. She recognized me but not you. She wanted to know who I was with but I told her it was a neighbor who asked me to help her with her kids since I was going out with Joann's. I was afraid if I suddenly sat with you today she might start asking questions about when we started becoming friends, get caught with different stories and then she might figure it out. And you know what a big mouth she has. I'm really sorry." I felt like crap, a different kind of crap. How can you go from feeling bad to feeling bad and it is two different kinds of feeling. Add it to the list of things I really just don't understand. "No, I am truly sorry for snapping at you. Thank you for trying to protect me, I really do appreciate it." We started walking down the street. "So, do we find a way to start hanging out at school or blow it off?" "I still want to find a way to hang out. We have too much time left to ignore each other for that long. I really enjoyed talking the other night and want to be able to talk more." She confessed. I ended up walking her all the way to her house while we planned to gradually get to know each other. * - * - * The next day I took an extra-long time getting to homeroom so that when I got there the choice of seats was limited. The plan was to try this during the week each day until we were forced to take seats next to each other. JJ had arrived a minute before me and chose a seat with a couple empty seats around it. We got lucky the first day so I went and sat next to her. I always tend to be the class clown and announcements are usually good fodder. An announcement came on about a mandatory pep rally that would be held Friday afternoon and I made a point of saying they had to be mandatory or nobody would attend them. JJ immediately came back saying everyone should want to go and support the school teams. We exchanged a few more points when right on queue the teacher told us to be quiet so they could hear the rest of the announcements. "Fine," I answered, then turning to JJ, "where is your next class?" "Why?" she responded acting a little leery. "Because I think this might be a fun little debate and I want to continue it," I countered. JJ looked around at the others gauging their reaction. "306" "OK, I'm in 202. I'll walk you to your class then can drop down the stairs to mine," I smiled. "Unless you would rather concede the argument." "I'm not conceding anything," she replied sitting up a bit straighter. The announcements ended and the bell rang. I grabbed my books and jumped back into the debate with JJ. We continued it down the hall until we got to her classroom. Nobody from homeroom was around any longer. I gave JJ a wink and headed down the stairs. Lunch rolled around and I was sitting in my usual spot pulling my lunch out of a paper bag. "Do you always eat alone?" I heard JJ's voice come from behind me. "Yeah, just never seemed to fit in with anyone," I answered. "Well, why don't you come over and sit with me and a couple friends?" I looked at her a moment, this was moving faster than we had planned but I gathered my stuff up and followed her over to a table where there were a couple guys and a girl sitting. Introductions were made and JJ told them of the debate we had that morning. As lunch ended I thanked them all for allowing me to join their table and JJ for inviting me. They all insisted I join them again the next day. I walked away feeling as great as I could feel. The rest of the day flew by. I left school walking quickly down the street and when I turned the corner I literally ran into JJ. I managed to grab her arm to keep her from falling down. "Hey," I said, "we really need to stop bumping into each other like this." "I think you bumped into me." "Well, you shouldn't be hiding behind bushes. What's up?" I asked. "Not much, I just had such a good day today and everything went even better than I had hoped I wanted to have you walk me home again," she beamed. "I can do that," I smiled back. "But tomorrow I am going to fix this for good." * - * - * As lunch came to an end the next day I looked across the table at JJ. Looking right at her I said, "I want to thank you again for inviting me to join this little group, I'd like to thank all of you." I looked around at each of them. "I was wondering where your last class is, JJ. If you would like, I'd like to walk with you after school. I know you live kind of on my way home." JJ actually blushed a little. "Yeah, I'd like that. Why don't you meet me by the east door?" "I can do that," I grinned. School finally came to an end that day and I headed for the east end of the building. As I got close I saw JJ standing just inside the door. She started smiling when she spotted me coming closer. We turned and walked out the door together. The next day I left the house a little earlier and went to JJ's house first and we walked together to school as well. We spent the next month spending extra time together, even studying together on occasion though we were in different classes, a couple of our classes were on the same pace. We talked about everything: music, books, cars, what we want to do when we grow up, other kids, our lives. Of course we eventually had to come back around to Halloween night and whether I would do it again. I told her how much I enjoyed it but also how much I enjoyed seeing girls wearing dresses. I liked long hair and nice legs. I didn't care too much if they had big boobs or not, I was more into legs. She told me about what she liked about guys. Muscles, but not overly developed, nicely groomed, tall. There was no jealousy involved. We were becoming the best of friends. We talked about everything and kept each other's secrets. It was a week before Christmas when I got home from walking JJ home from school and I got to my room and found a bag on my bed. I opened it and inside was a package of panties and four packages of pantyhose of various hues. There was a note: Tony, I am giving you these items for your use. I've decided that it isn't going to do you any harm to have them. I've also decided I would like for you to stay out of my lingerie drawers but may borrow from my closet if you need as long as things get back as quickly as possible. You should keep these things hidden. If you absolutely need something more let me know and I may accommodate you. Also, I know you and JJ are spending a lot of time together now and if you decide you don't want these things leave them in the bag on your bed tomorrow morning and I will return them. Love Mom I went to my closet and looked around. I found a box that I stored old calendars in and carried it to the bed. I opened the packages and added the contents to the box then put the box back in the closet on the shelf. Nobody else should be going into that box for anything. I took the empty packages out to the trashcan in the back and pushed them down into the existing trash. Later that night I caught my mom's eye and gave her a smile and a wink. She gave a little nod in return and we had an understanding. JJ and I got through our freshman year together and got our schedules for the next year managing to arrange it so we shared a few classes together. We were spending a lot of time together but we were still treating it as a friendship. I was starting to look at her a bit differently, though, and I think she was making some changes to help me. I noticed after Christmas she started wearing more skirts and dresses to school. When I asked about it she said she got a lot of new clothes under the tree and decided she liked dressing a little nicer. Her hair was getting longer as well. I hadn't told anyone, even JJ, about the care package my mother had left me. I was making use of it when I could and I was in the mood. And I kept to our arrangement, borrowing clothes only and putting them back as soon as I could. Life was good. Chapter 3 Here it was, October again. I was really looking forward to it this year again hoping it would be as big a thrill as last time. I was preparing for it and I wasn't afraid of all the "what ifs" I was confronted with at the last moment last year. Halloween was going to fall on Tuesday this year and that meant rushing home after school and getting changed in a hurry. My mom suggested picking out the outfit Sunday afternoon so we would have that taken care of. That would allow us to get right to work Tuesday evening when I got home. Sunday rolled around and the kids all got sent out to play. JJ and Joann both showed up to help me decide on what to wear. Joann contributed a couple outfits to the cause. My mom collected a few of hers and a bra, something she hadn't provided for my stash. I would be wearing my own panty and hose. By popular demand I modeled the hot pants suit first. The boots barely fit my feet and I am not sure the skirt actually reached the bottom of the shorts any more. It was really close. But the looks on all the faces told me I could still pull it off if I wanted to. And that my mother felt the same way about letting a 15 year old out of the house as she did the previous year. I just smiled and went back to try something else. The little black dress was back and I changed hose to a dark pair and went back to the kitchen. I had practiced over the last year and found I could conceal the extra bulge fairly well. I got some appreciative comments from the ladies. My mother had provided a new long dress she had gotten. Nude hose again (I should have grouped the clothes so I wouldn't need to keep changing). It was floor length, very gauzy in three layers in the skirt, the top looked like a wrap around and the sleeves just draped over the tops of my shoulders. I absolutely loved it but it was totally wrong for Halloween. I went back to the kitchen. "OK," I told them, "first I absolutely love this dress. But I think it is totally wrong for Halloween. Definitely a spring dress." JJ and Joann just looked at me for a minute. "I think you might be getting a little carried away here, Tony," Joann stated. "This is a Halloween costume after all." "Yeah, right," I laughed. "I just got lost in the moment. Last year was terror but I had fun. Joann, you said you hoped I enjoyed myself and would want to do it again. I was actually looking forward to it. Anyway, I better try something else." I got back to my room and took the dress off. I wondered if I had really messed up but I decided to not let it get to me. I looked through the dresses still yet to try and decided to go with a mini-dress that Joann had brought. It was a lot of crazy colors and sleeveless. Reminded me a lot of a 60's go-go dancer. Would work well with the white boots I wore earlier. "Well?" I asked. "That is awful short," mom pointed out. "You won't be able to sit down!" "No, you just have to be very aware of what you are doing," Joann added. "I've worn it a few times. Of course, you could put a pair of hot pants under it." JJ blushed a little. "Next!" I turned and left. The last outfit was actually a blouse and skirt. The skirt was a brown leather mini with fringe, the blouse was mustard yellow silk with big billowy sleeves. I got them on and returned to the kitchen. "Well, that's pretty nice and the skirt is just long enough," my mom observed. "Actually, I think you need more chest for that blouse," pointed out Joann. "You can't see that there is anything there, it just kind of hangs there." "Well, this is what I have to work with," I pointed out. "No, I don't think so. I'll be right back," Joann spoke as she left the room. She came back just a minute later. "Here, try this on," she handed me a bra. I just stared at it for a second and looked at Joann. I realized her breasts were moving more freely under her shirt and I could see dimples in the fabric caused by her nipples. She had removed her bra to give to me. She was as observant as I was though. "Yes, I took it off for you, and I'll take that new lump in your skirt as a compliment. I guess we know that girls turn you on. Now, go on, let's give you a bigger chest." I started to leave the room but they stopped me. No reason for me not to leave the room for the change. I looked at JJ and then I took the blouse off feeling a bit embarrassed, took the bra I was wearing off and put Joann's on. We got more material to stuff the cups and I put the blouse back on. It really did make a difference, making my waist appear a lot narrower. "What about shoes with this?" I asked. "What size were the other boots?" Joann asked. "8 ?," my mom answered. "I have size 9 brown boots that work with it. If you think that is the one to wear this year, you can borrow them," Joann offered. I looked over at JJ. "What do you think?" "I like what you are wearing now for Tuesday," she answered. "And the go- go mini-dress for Saturday." "Saturday?" I asked. "What is going on Saturday?" "Oh, I found out yesterday that there is a costume party Saturday night. We've been invited. I know our friends won't think anything of this for the party." "So, I have gotten shanghai'd into another new experience," I moaned. "What are you going as?" "I haven't decided yet," she giggled. "But, now that I know what you are going as I'll find something appropriate." "OK, all decided. I need to get back home," Joann said as she started for the door. "You can return all my stuff next week, perhaps when you come by to pick up JJ for the party Saturday." * - * - * I got home from school Tuesday and rushed to change clothes. Once I was dressed I headed for the kitchen so my mom could do her magic once again. This time she went through the steps and explained why and how she was doing each thing. "You are going to do your own make-up for Saturday," she explained. "Are you upset with me?" I asked. "No, I just think this is going further than I expected. If you are going to keep doing this, then I think you should know how to do it for yourself." She finished up and I headed for the living room to wait for JJ to arrive. When she did arrive she wasn't wearing a costume. "Do you need to change?" I asked. "No," she murmured. "I just decided not to dress up tonight. I'll save it for Saturday." "Do you still want to walk with me?" "Yes! Sorry, just not in the mood for a costume tonight just to walk around the neighborhood." "OK, well why don't we gather the kids and hit the street?" We trouped on out the door, once again shepherding the kids from house to house. It was chillier out this year and I was wishing I had chosen a longer skirt. I couldn't figure out how the breeze seemed to be coming straight up from the sidewalk at times. I did like the feel of the fringe brushing against my legs. "You really like wearing dresses and all, don't you?" JJ suddenly asked. I almost fell off the heel of the boot as I stepped. I hesitated just a second longer before answering. "Yes, I do," I confessed. "Don't you?" "Well, yes, sometimes. But I'm a girl! I'm supposed to be wearing dresses, high heeled shoes, pantyhose. Are you wearing panties too?" she asked. "Yes, my regular underwear wouldn't look right under the dresses, too heavy, thick seams. No shorts either, this skirt is too short." "Last year were you wearing shorts under that dress?" "No, all women's wear." I was not feeling as chilled as I had been. We walked along in silence for a while. "I don't understand this. All year long everything seems normal. I thought maybe," she suddenly stopped. "Thought what?" I prodded. "Thought that you might want to be more than friends one day," she hesitated. "With me." "Really? Because I confess that there were several times that I wanted to take your hand when we were walking home, or even see if you would let me kiss you," more confessions. "I like our friendship and was afraid to push it to another level because you would not want me to." "Uh, really? I've been just waiting for you to give me any kind of an indication for the last half a year," the exasperation evident in her voice. "I'm sorry. The first time you really talk to me I'm in a red dress. I was thrilled to have you as a friend but afraid if I said or did something that got you upset with me you might tell someone about it. Because for me it was more than that one, well now two, nights. The panties and hose I am wearing are mine. I occasionally borrow clothes from my mom's closet when I'm alone because, as you guessed, I like wearing women's clothes. She figured it out last year and made me dress up hoping to discourage me from wanting to do it any longer. When that didn't work she bought me some underthings and told me to stay out of her lingerie. But she said I could borrow her dresses. "I'm blurting everything out now. I'm sorry. If you didn't know enough to hang me out to dry with everyone at school, you do now." She turned and took my hand in hers and instead of saying anything she kissed me. I was shocked. It was the first time I had kissed a girl, or been kissed by anyone not a relative. I wasn't sure what to do at first. She stood back and stared me in the eyes. It couldn't have been that easy on her because once she was really looking at me she saw eye liner, eye shadow, lipstick, etc. I leaned in and kissed her back. Our arms wrapped around each other. The kisses weren't bad for a first effort. A first for her as well I found out later. They were old style movie kisses, closed mouth, but they lit me up. We leaned away a little, still holding on. "I'm not sure how I feel," JJ started, "first the kiss felt nice, even with your lipstick, which I sometimes wear but not now. And I found myself thinking the blouse feels really nice and wonder if it would fit and I could borrow it. It's so confusing." We started walking again and just before we got back to the house I stopped. "JJ, what about Saturday? Do you really want me to wear that short dress?" "Would you rather not? You've confirmed what I was thinking, which was that you might like wearing dresses, and that was my favorite for the party." "So, yes, I would like to but I don't want to push you into thinking I have to dress up like that because it is a costume party." "No, I want you to wear that dress. Actually, it got me a little turned on when I saw you in it." She turned away as she said it, I was sure she was blushing. "Still more confusion." "OK. What time shall I pick you up?" We settled the arrangements as we walked back into the house. I went to the bathroom to clean off the make-up and noticed my lipstick had gotten smudged. JJ waited in the other room while I changed into my regular clothes. She had ridden her bike over to the house and I was going to follow her back on my bike. * - * - * I spent the week after school in my room practicing wearing the mini- dress. I set up a mirror across the room so I could watch myself sit and see if I was flashing anything. By the time Friday rolled around I was pretty good at everything. Next test came Saturday, time came for me to get ready and I got completely dressed this time with stuffed bra (mom's), wig and jewelry. I sat at the desk in my room with a mirror and tried putting on my make-up by myself for the first time. I had several do-overs as I had to clean up mistakes. After about 90 minutes I looked in the mirror and decided I had done as best I could. I went and looked for my mom. "You did pretty well," she nodded approvingly. "I think you'll be fine, at least as far as make-up is concerned. Are you sure you can manage that dress? There isn't a lot of room for error and you are going to be in a room full of other kids." I smiled and walked over to a chair. Giving the dress a little tug and laying my hands atop the gap between my legs as I sat dropping lightly into the chair. I turned my knees slightly away and with another tug on the side crossed my legs. "OK," she smiled. "Looks like you have things well in hand. Have a good time tonight. No drinking! Or drugs!" "Yes, Mom." I gave her a hug. "I promise." I grabbed the rest of Joann's clothes up and put them carefully in a shopping bag, including her bra. I decided to walk over to JJ's house. It occurred to me how much had changed in the last year as I walked. It was still light out as made my way down the street. I was also aware of how tight the white boots had become after the slightly larger boots I had worn earlier in the week. This would be the last time I would be wearing them. I was about 2 blocks from JJ's house when a car full of boys, probably from my school though I didn't recognize any of them, rolled past hooting and hollering at me. I ignored them and continued along until I noticed they had pulled over just up the street. Either they had business there or they were waiting for me. I decided I'd rather not find out. I walked past the house I was in front of and up the stairs of the next house. I had no idea who lived there but felt it would be better than facing the boys. Fortunately, the house had two apartments and the front door was to an entryway that housed the front door of the downstairs apartment and the stairs up to the other apartment. I stood inside and tried to see through the beveled glass window at what the car was up to. After about a minute and a half that felt like an hour I saw someone go across the sidewalk to the waiting car, he got in and they drove off. I hadn't realized I was holding my breath until I let it out. I opened the door to leave just as the door to the downstairs apartment opened. "What do you want?" a lady who looked to be in her 80s screeched through the crack in the door. "Nothing, wrong house," I answered trying to keep my voice soft. "Sorry." I went out the door and down the stairs as quickly as I could before she could ask me anything more. As I turned up the street I saw the curtains part out the corner of my eye but I didn't turn to look, I just kept on moving down the street. I finally arrived at JJ's place. I knocked on the door and her father answered. "Tony?" the disapproval evident in his voice. "Is that you?" "Yes!" I waved, "it's me." "Come in, JJ is almost ready." He turned and left me there without another word. I was looking around trying to figure out what to do when JJ came around the corner. We were practically twins. "Oh, my God!" I cried. "You look great!" "Both your dresses are too short!" her dad hollered from the other room. "You had better not be getting up to no good tonight. I'm not old enough to be a grandfather." "Dad!" JJ blushed, clearly mortified by his remark. "Not to worry, sir," I called back. "I'm not ready for that responsibility either." "Be back by 11:00 or I'll come looking for you." I just looked at JJ. She sighed, took me by the hand and we left. The party was only a couple blocks further down. We arrived and everyone was shocked, as much at JJ as me I think. She usually dressed rather conservative and not a lot of make-up. Tonight her dress was every bit as short as mine, and her make-up made her look in her 20s. I had a hard time taking my eyes off her. We talked with everyone, danced a bit (almost a requirement for the go-go dancers), ate snacks and had a generally good time. Someone snuck some beer in but I wasn't interested. JJ came up beside me and wrapped her fingers in mine while I was talking to someone. "I think we better go before my dad comes looking," she whispered. I nodded to her even though I noticed it was only 10:00. It wouldn't take more than 15 minutes at a slow walk to reach her house. "It looks like you two have become an item," Brian observed. "Holding hands, matching outfits. How did you talk him into it JJ?" "He just couldn't pass up the opportunity to see me in a short dress and this was the only way I would do it," she answered as she tugged my arm toward the door. "It was just a matter of time before you two made it official," Brian called after us. "See you in class." We waved and walked out the door. I waited until we got a couple houses away before I said anything. "Everything OK? We left a lot earlier than we needed to," I put my arm around her waist pulling her closer to me. "Yeah, everything's fine. I just wanted a little time to ourselves," she laid her head over on my shoulder. We walked along a ways and I suddenly felt her hand slip down off my waist. "What are you doing?" I pulled away a little. "I want to see your panties. I'm curious. I watched you all night and you worked that dress well, and believe me I know how hard that is. I could feel some of the boys at the party trying to get a peek at mine all night." "So you think I'm going just pull my dress up right here on the street?" "No, of course not. I just said I wanted to see them, I didn't say I expected you to show them to me," she pouted a bit. I put my arm back around her letting my hand wander down. "I'll show you mine if you show me yours," I answered. "That is really juvenile, you know?" she shot back. Then, after a minute she said, "There is a park just a block from here. Let's go by there before you take me home." We walked to the park and saw it was deserted. There was a playground with swings, jungle gym, slide, and concrete barrels. We sat on the swings facing opposite directions talking for a few minutes. I reached out and grabbed the chain on her swing and pulled it closer. Leaning over I kissed her, I didn't rush it and after a minute I let my tongue slide between my lips and touch hers. She jerked her head away. "What are you doing?" she exclaimed. "I was trying to kiss you. It seemed like the right thing to do," I answered defensively. She looked at me for a minute. "OK, try again." Our lips met again and I slowly let my lips part and touched her lips with my tongue. She parted hers and I pushed it further in her mouth. Her tongue touched mine and then slid around it caressing it. I felt a small fire light somewhere inside me. Then I felt her hand on my thigh, barely an inch from touching my panties and all that was there. I intensified the kiss from my side and pulled the swings closer together. I dropped my hand to her thigh feeling the silkiness of the nylons, but my fingers brushed higher that I had planned. She seemed to take this as approval as her tongue surged forward into my mouth and her finger lightly rubbed the front of my panties and the erection that lay beneath. She snatched her hand back quickly and broke off the kiss. "I'm sorry. I was just curious about what kind of panties you were wearing. I didn't mean to get you all excited," she rattled off the words so they almost ran together. "It's ok," I assured her. "I get excited a lot when I wear dresses, and when I kiss you, too. I really didn't mean to touch you that high. Think we ought to stop?" JJ nodded. Then she looked around and seeing we were alone she backed up like she was going to try and swing up high but stopped and raised her dress up displaying a pair of pink cotton panties with a little lace trim at the top under the sheer hose. I couldn't stop myself from staring at her. I could see a slight indention from the lips of her vagina. I wanted to reach out and trace my fingers along it. Instead I backed up my own swing and raised my dress. I watched her eyes as they moved down to take in the view I was offering. My panties were yellow with a satiny finish. They were very tight in an effort to keep my dress from getting that betraying bulge so I was certain she was getting a fairly detailed look at my penis. I waited a second longer and then dropped my dress back down. I watched as her panties slowly disappeared as she lowered her dress. Both our chests were moving quickly up and down as our breathing had become very fast. About that time a car came around a corner on the far side of the park. I recognized it as the same one from earlier in the evening. "Come on," I commanded, "we better go. I think there will be trouble if those guys come over here." I took her hand and we left the park in the opposite direction from the boys. A few minutes later her house was in sight. We slowed out pace as we got closer. "I liked that kiss," JJ said barely above a whisper. "I don't think we did too bad for a first try," I answered. "If we did much better I think we might have gotten into some trouble," JJ giggled. "By the way, I like your panties." "I like yours too." I grinned. As we approached the house the porch light suddenly snapped on. We both knew her father had been watching us come up the street. I walked her up to the door; we kissed briefly and said good night. She went inside as I started my walk back home. I practically danced all the way. Chapter 4 We tried to be good over the next year. We kissed a lot. We still were limited in our privacy. A couple times JJ did some baby-sitting for Joann and I would go and visit. A few of those times she would give me things from Joann's closet to wear after the kids were in bed; we didn't do any more exploring under the dresses, just too afraid of not being able to stop. But as with most teenagers, that didn't last forever. I wonder if Joann ever figured out how many of her dresses I wore. In June I celebrated my 16th birthday. I went out and found a job at one of the local stores and worked full-time during the summer. I made enough money to buy myself and old car and be able to treat JJ to a burger and a movie. JJ turned 16 early in August. I saved enough to take her out for a nice dinner. I dressed up in a suit and tie. She was dressed in a beautiful dress, she looked radiant. Her dad gave me a look when I picked her up but let us go without any threats. I understood the old threats were still in effect. After dinner JJ asked if we could take a drive before going home. We were still a couple hours short of curfew so we drove around a bit and found ourselves out at the lake. I went to an area that was void of any other cars and turned off the engine. I left the radio playing softly. "What do you think of my dress?" JJ asked as she adjusted the skirt slightly. "I think you look beautiful, I told you that when you first got in, but I don't mind telling you again." "Thank you," she beamed, "but I want to know how you feel about the dress! As a guy you take a more unique view than other guys." I reached over and ran my hand down the skirt feeling the material against her leg. "Mmm," I murmured. "I really like the feel of the material; I like the shape of it and the style.

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I walked to the bathroom, my head was whirling with thoughts of last night. " Damn" Mom had giving me the best Birthday party I could ever of had, and , finished it off with the greatest of all presents......."Her " I could smell her all over me yet, my cock was getting hard just thinking of her , and what we had done together. I reached in and turned on the shower, and crawled in . The water felt great, I soaped up my body, and slowly stroked my cock with my soapy hand, ...

1 year ago
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Schoolgirl and schoolboy

This story is a two part. We did it my way, then her way. Enjoy The first part is about how a schoolgirl fantasy, that I wanted to do with my girlfriend. The second part is how my girlfriend did the same kind of fantasy, but she had a twist of her own to do it. It all started, when we looking up costume on what to be for her Halloween company party. She wanted to be something sexy because everyone in her office think it's kind of boring, and she wants to change that. We were looking online and...

Straight
4 years ago
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My VIRGIN Highschool Sweetheart

Graduation Ball By now we have been spending a lot time together and sometime spending hours on the phone, you know lovers do.  From the multiple invitations, I was so happy that she accepted to be my grad ball partner.  I rented a new car to take her to the ball and couldn't take my eyes off her all night.  Even though she wore little makeup and a rather conservative gown, but her perfect figure was very well enhanced.  Lots of fun with ballroom dances that we learned and practiced for this...

3 years ago
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Romys Sexual Journey from Schoolgirl to Schoolgirl Part 2

The final day of term was mighty hectic. A lot of tears and taking of phone numbers, addresses, future education plans, ‘I’m sure going to miss you ladies. It’s been a real gas. We’ve had some fabulous times together and I just hope we’ll bump into each other sometime in the future,’ I said. And then it hit me! That’s what it was - Paul. I had really been missing him since our liaison and, stupidly I didn’t even know what his surname was! Later that day I would be even further away from him...

1 year ago
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Happy Anniversary Sweetheart

July 9, 1992 is a day that changed their lives forever. At 4:30 PM on that hot and humid Florida day, Phil and Jeanne were married in the backyard of Phil’s parents’ house, next to the pool. They sometimes laugh about that day for several reasons. For one, they only decided and announced that they were getting married 3 days earlier and had made arrangements to stand before the Justice of the Peace at their county courthouse. Both of their families were not going to have that! They were gonna...

2 years ago
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Sweetheart

Welcome to Sweetheart! In this story you will be going back to high school and get back into the dating game. Throughout the story you will meet many different girls with different personalities that you can try to get with. Your ultimate goal can very. Whether you want to just get them in bed or get them in your arms, Sweetheart will offer you many opportunities to do so. So good luck and have fun!

Teen
3 years ago
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Jenny My Childhood Sweetheart

I have read many stories on this site and most of all i feel are heartless due to fairy tales. But now i would like to post a real and true incident of my first sex experience with my childhood friend jenny. I am a christian by birth and my mom gave me my name as david .I am fair and handsome 32 years man with 6″ dick.In my childhood i used to visit church with my family most of the Sundays and sit on bench and praying in front of god. We were accompanied by a very charming family of josephs...

1 year ago
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Hot Wife KatieChapter 34 Katie is Americarsquos Sweetheart

Katherine Jackson turned down her street after another long day of appearances. Her life had been thrusted into the public spotlight since winning the beauty pageant. She had been interviewed by a host of national news networks and was dubbed ‘America’s Sweetheart’ by Ryan Seacrest during her appearance on the morning variety show ‘Live with Kelly and Ryan’. Her answers during the finale of the pageant resonated across America as the sexy beauty queen was bluntly honest about how everyone...

3 years ago
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High School Softmore II

High School Softmore II I'm not much for writing sequels to my stories but for some reason this story has been a favorite for many of you. Even months after writing this story I keep getting so many request for this story to continue. So I have decided to give you one more chapter. I hope you enjoy it as much as the first one. You can reach me at, [email protected] My head was spinning out of control with my nylon covered legs rubbing with my best friends silky legs. To...

3 years ago
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High School Again Ugh Ch 01

Author’s note: I started writing this a long time ago and enjoyed the way it was going (At least in my head). I’ve held off posting this first chapter because I wanted to get more done, but I’m curious to see if people are really interested in this story line before I go too much further. Please feel free to comment. I do read them. I also make an effort not to delete any comments that people make, as long as they’re not offensive. In other words, I’m old enough to take constructive criticism...

1 year ago
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High School Nurses Exam

Chapter  1 –        High School Nurses Exam or Welcome to Hell, Boys        15 Year old Jordan Haystack shifted anxiously in his seat as he awaited the mandatory nurse’s exam for freshman year of high school.  The knot in his stomach grew tighter and tighter, and he felt sicker and sicker.  The line of boys in front of him looked just as terrified.  The boys filing out of the nurses office ahead of us kept their gaze fastened straight to the floor, their cheeks bright red.        It didn’t...

3 years ago
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High School Reunion Drinking Games 5th in the Golden Series

A few years ago I went to my twenty five year high school reunion. Coincidentally, I’d also begun a fitness regime about a year ahead of the reunion. I didn’t really do it for the reunion, but over that year the reunion date did provide some motivation. After all, the desire to impress a group of people that you shared five years of your life with in the distant past seems a common condition. Since I wasn’t famous or rich, the only avenue left to me to impress was through a regime of workouts....

Fetish
4 years ago
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High School Softmore

High School Softmore By Jeffanie As I peered into the window of Karen's bedroom my eyes were glued to her as she undressed in front of me. What an ass and tits she had, she was truely the prized senior in school. As her skirt dropped to the floor her sheer pantyhose covered legs and perfect ass came into view. God what a sight! When her blouse was off I got the whole picture and then I snapped a couple pictures with my camera high in the tree aside of her...

3 years ago
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High School Reunion

All characters are over the age of eighteen.Finally walking off the plane from my first class seat on a Thursday evening, it feels good to be home. I’m back in town for my ten-year high school reunion. This time I’m going to be the one everyone’s jealous of. I’ve got the perfect job, making more money than I know what to do with. Well… being an accountant for a huge tech firm, I obviously invest my money to earn interest and make more money… but my point being, I’m far better off than all the...

Trans
1 year ago
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High School Sweetheart part 4 of 4

High School Sweetheart Chapter 4 By Lauren Bliss Sunday morning, I awoke to a breakfast of sugar smacks, and coffee. Mrs. Connolly seemed to always have her hands full, so it was no surprise that she fixed the family's morning meal by taking the path of least resistance. Still, I thought it nice that their whole clan, all eight of them, had breakfast together. Archie had stumbled in pretty late, well after we went to sleep, and it showed. He shoved his cereal into his mouth in...

3 years ago
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High School Pimp

I was only thirteen years old throughout most of my freshman year in high school. I was only four years old when I entered kindergarten and I had not failed any grades. I was a nerd and had no friends. I just didn’t fit in. High school was nothing like grade school I’ll tell you that. Then one day in March a senior boy talked to me. I thought that he was talking to someone else and turned around to look. He walked right up to me and then I figured that I was going to get beaten up. He...

3 years ago
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High School Fall Festival for Slut Wife Terry Webb

High School Fall Festival for Terry WebbHigh School Fall Festival for Terry WebbHigh School Fall Festival for Terry Webb 2High School Fall Festival for Terry Webb 3High School Fall Festival for Terry Webb 4High School Fall Festival for Terry Webb 5High School Fall Festival for Terry Webb 6High School Fall Festival for Terry Webb 7High School Fall Festival for Terry Webb 8High School Fall Festival for Terry Webb 9High School Fall Festival for Terry Webb 10High School Fall Festival for Terry Webb...

1 year ago
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HIGH SCHOOL REUNION TAKE FOUR THE STUDENT HELPERS

It is the annual alumni reunion event at the Lauderton High School, which they hold in the large gymnasium in the main school building. The events in these stories take place at various times during the evening, and to different characters; they are not chapters of the same story, but a series of separate takes. We are the invisible camera, panning around the scene and then zooming in for a close-up ... TAKE FOUR Jenny Neustein, the teacher who had done most of the work of...

2 years ago
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High School Part 5 Graduation

High School Part 5 - Graduation [In which Shaun's Mother helps him with his makeup, Jeff defends Shaun from two bullies at school, Shaun begins wearing high heels and gives Jeff a blowjob.] I was sitting at the kitchen table just after finishing breakfast this morning, buffing my fingernails and getting ready to put some polish on them when Mother looked over at me and said, "Shaun, your new clothes are really nice and make you look so much more attractive. But, and I hope that...

4 years ago
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Late For DinnerChapter 40 Goodnight Sweetheart

Kathy could hear the crickets singing through her bed room window as she wrapped herself around Christi. "It was really sweet of your mom to let Becky and Kim stay at your place until Billy's birthday." "Mom's really happy to have the company," Christi snuggled close. "I think she gets a little lonely on the nights we stay over here. And," she smiled sleepily, "she'll enjoy having a little house slave for a few days." "I can't imagine being a widow and not being owned by...

3 years ago
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High School Again Ugh Ch 02

Author’s note: Thanks for all you kind words. I was surprised by how many of you were interested in this story. Here is the second chapter. I hope it doesn’t disappoint. JD. ********** The car ride was painfully quiet as we made our way toward my high school. My father was driving and to say he wasn’t happy with me was a vast understatement. Mom was sitting next to him and looked like she hadn’t slept much at all last night. I knew they were worried about me and I could certainly see why. I...

1 year ago
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High School New Friends New Experiences

Introduction: this is a partly true story Ah, high school. The best and worst times of our life, supposedly. I had been living in the south since I was 8, yet at age 14 I was still a bit of an outcast because I was different and not from here. Thus is the mentality of the town I grew up in in the south. My freshman year wasnt too bad, I did have a best friend who liked my same kind of music and understood my sense of humor perfectly. We met the year before in 8th grade middle school. We were...

1 year ago
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High School Dilemma

High School Dilemma Part One By Lauren Westley I should have known better. It was such a stupid thing and it didn't even work out. Here I was graduating from High School. I had just turned eighteen and it was the last week of school. How could I have done it? Why did I take the chance? Kelly was probably the prettiest girl in school. Her hair was long and blond. Not much different then mine. Actually we were both about 5' 5"...

3 years ago
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High School Dilemma

High School Dilemma: Part One By Lauren Westley I should have known better. It was such a stupid thing and it didn't even work out. Here I was graduating from High School. I had just turned eighteen and it was the last week of school. How could I have done it? Why did I take the chance? Kelly was probably the prettiest girl in school. Her hair was long and blond. Not much different then mine. Actually we were both about 5' 5" and weighed around 120 pounds. But, Kelly was Joe's...

2 years ago
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High School PimpChapter 6

The loss of the head custodian put a crimp in Hellboy's plans. With no head custodian to keep the brothel clean and orderly and no principal to hire his replacement, the whole brothel operation had to be put on hold until something could be done. Initially, Hellboy had been considering having the whores clean up after themselves, but that was going to cut into the revenue-producing fucking time. Besides, adult men were needed to haul around those heavy metal refuse containers that the school...

1 year ago
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High School Sweetheart part 3 of 4

High School Sweetheart Chapter 3 By Lauren Bliss It was prom night, and I was ecstatic. I was dressed in a pink, strapless, diaphanous gown that fell to mid thigh. The bodice clung to my developing curves, but the neckline was high enough to remain tasteful. My opera length gloves fit snugly around my arms. I wore my mother's pearls, and carried a small drawstring purse, while I paced nervously around our living room. Ela was there, dressed similarly. We stood for photos while our...

2 years ago
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  • 32
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High School reunion3

Logan maybe, he was at least smart enough to get good grades, Devon, on the other hand, was a complete tool and an absolute idiot. Unless he made it to the NFL, which he didn’t, there’s no way he achieved anything with his life. But it’s Logan I want to show up. He always went out of his way to put me down. He tried to act so manly, but honestly, his voice sounded so girly. I’m surprised Devon didn’t give him shit for it. Even though he was shorter than me, being the state champion in...

2 years ago
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High School New Friends New Experiences

"Aww man, there's no 'home room' in high school?" I exclaimed, disappointed because Chris and I always goofed off in home room. We checked eachothers schedules and compared them. "Damn dude, looks like we only have Science and Lunch together" Chris pointed out. He sounded as disappointed as he could...Chris wasn't the most emotional kid. He was a 'burn out child' as we liked to call him and slightly pick on him because of his hippie parents. Chris didn't mind though, he was...

4 years ago
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  • 24
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Husband Wife and Schoolboys

THE HUSBAND, THE WIFE AND THE SCHOOLBOYSPart OneLet me explain. My name is Justin. I am a healthylooking 40-year-old married guy and in quite good shape. Not film star shape but I can still pull acompliment or two. I was lucky to marry an extremelypretty, little women called Carrie. She is still 30and we have been married for 10 years so you haveprobably guessed that she was 20 when we married. Iwas lucky, O.K? She has certainly stayed in shape andher slim body pert little upturned breasts and...

2 years ago
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High School Lovers0

Michael? Where did you go? Ashley taunted from behind a nearby tree. I snuck up behind her quickly and quietly, scooped her up and hugged her tight. She screamed and then giggled. I kissed my sisters’ forehead and said, (gotcha.) No fair it was my turn she squeaked. Can we have pizza, Ashley asked? As we walked back to the house from Sanctuary, our little fort in the woods, the cool November air kissed my cheeks even through the trees. Birds scarcely sang in the distance, most having...

3 years ago
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High School Lovers3

Family and friends Michael? Where did you go? Ashley taunted from behind a nearby tree. I snuck up behind her quietly and quickly, scooped her up and hugged her tight. She screamed and then giggled. I kissed my sisters forehead and said, (gotcha.) No fair it was my turn she squeaked. Can we have pizza, Ashley asked? As we walked back to the house from Sanctuary, our little fort in the woods. A little about us, my sister and I are from (Mass-a-two-shits, yes I said that right, the state is...

1 year ago
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  • 23
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High School French Teacher

(This story is part fact, and part fiction. I won't tell you what is what, you'll have to figure it out on your own…Sorry, I guess it's a little long, but I hope you enjoy it.)I was a highly under-sexed, but extremely horny high school student. This was back in the big-hair days of the ‘80s. I still think some of the best porn came from those days. Beating the cum out of my cock watching a young Ginger Lynn, Nina Hartley, Taija Rae, Barbara Dare (a secret crush of mine back on the day) Christy...

2 years ago
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HIGH SCHOOL REUNION TAKE SEVEN THE BEST FRIENDS

It is the annual alumni reunion event at the Lauderton High School, which they hold in the large gymnasium in the main school building. The events in these stories take place at various times during the evening, and to different characters; they are not chapters of the same story, but a series of separate takes. We are the invisible camera, panning around the scene and then zooming in for a close-up ... TAKE SEVEN Kirsty Sheraton was thirty-three years old, and had graduated from...

3 years ago
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High school days 2

"Well, that was what we agreed to Mom. I would share a sexy adventure of me and my friends and you would return the favor."I tried hard to maintain my composure, to keep from acting surprised that Mom would volunteer re-stating our previous "agreement". She could have easily dismissed that weak arrangement since neither of us really made a point about the rules of our sexy story exchange. Mom looked at me intently, as if trying to see if I would break-down and release her from this flimsy...

3 years ago
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  • 7
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My High School Sweetheart

In my 20's I met a girl online that lived about an hour away. She was a sweet little high schooler and we naturally got along well. We talked about sex a lot, and the first time we met I rented a room at the cheapest motel in town. This turned her on by itself.This dark haired, dark eyed little bombshell didn't waste any time when she parked in front of the door to the room. She got out of her car, came up and started making out with me on the spot. She led me by the hand into the cheap...

2 years ago
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High School PimpChapter 1

"Horsey" had started his business at an unusually early age! Not many boys become independent businessmen before they leave middle school. Of course, Horsey had a great mentor in his oldest brother, who was one of the most successful pimps in their housing complex. Horsey's brother ran a stable with women of all ages, starting with his mother who was 39 and their youngest sister who was 17. That brother had taught Horsey all he needed to know to keep his whores in line and how to extract...

1 year ago
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  • 17
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HIGH SCHOOL REUNION TAKE ONE THE FORMER STUDENT

It is the annual alumni reunion event at the Lauderton High School, which they hold in the large gymnasium in the main school building. The events in these stories take place at various times during the evening, and to different characters; they are not chapters of the same story, but a series of separate takes. We are the invisible camera, panning around the scene and then zooming in for a close-up ... TAKE ONE Nashiko Giancona had graduated from the high school five years ago, and...

1 year ago
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  • 15
  • 0

HIGH SCHOOL REUNION TAKE SIX THE OLDER TEACHER

It is the annual alumni reunion event at the Lauderton High School, which they hold in the large gymnasium in the main school building. The events in these stories take place at various times during the evening, and to different characters; they are not chapters of the same story, but a series of separate takes. We are the invisible camera, panning around the scene and then zooming in for a close-up ... TAKE SIX Catherine Rankine had a preoccupied air as she exchanged small talk...

4 years ago
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  • 11
  • 0

High School Hypnotist

Story Summary - Brad Taylor enjoys his work as a high school guidance counselor and hypnotist. Note – This is a work of fiction, make-believe and sexual fantasy. It is not based on real people or actual events. You must be 18 or over to read these stories. The author does not condone any sexual activity among persons under 18 in real life. It is OK to have fantasies, but turning a fantasy into reality can destroy lives. Don't be a dick with other people's lives! Yeah, I have it pretty...

1 year ago
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High School Girls

High School Girls A Rings of the Oni Story by Jaana "Three teenage boys find their simple lives completely overturned, and their friendship put to the test, when an unexpected find grants them both nightmare and gift beyond price." *** WARNING: The following story contains graphic depictions of sex, female transformation and female arousal. You have been warned! *** "Accept the things to which fate binds you, and love the people with whom fate brings you together,...

2 years ago
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  • 20
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High School Again Ugh Ch 06

Author’s note: If you haven’t read the previous chapters then I suggest you don’t bother continuing until you do, especially if all you’re interested in is the sex scenes. There is one, but in order to keep the reader enmeshed in a story of this length most of this chapter is character and plot development. I think you’ll be lost and disappointed without the background the previous chapters supply. For those of you who have read the previous chapters and are willing to continue to read the...

2 years ago
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  • 11
  • 0

High School Girls

High School Girls A Rings of the Oni Storyby Jaana"Three teenage boys find their simple lives completely overturned, andtheir friendship put to the test, when an unexpected find grants themboth nightmare and gift beyond price."*** WARNING: The following story contains graphic depictions of sex,female transformation and female arousal. You have been warned! ***"Accept the things to which fate binds you, and love the people withwhom fate brings you together, but do so with all your heart." -...

4 years ago
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  • 11
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Lets Try Something New Sweetheart

"Alright, sweetheart, I need to leave for work now. I don't wanna be late today," said Trisha, putting on her clothes. "I am gonna see you in the evening then." "Please don't leave me like this. Please come back to bed, we still have so much to do," I almost begged her. I knew she wouldn’t stay. She really had to leave. "You are gonna be home all day right? Please clean the house today. You never do anything. Don't just stay lying on the bed whole day, move that ass of yours, and clean the...

BDSM
1 year ago
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HIGH SCHOOL REUNION TAKE THREE THE PRINCIPAL

It is the annual alumni reunion event at the Lauderton High School, which they hold in the large gymnasium in the main school building. The events in these stories take place at various times during the evening, and to different characters; they are not chapters of the same story, but a series of separate takes. We are the invisible camera, panning around the scene and then zooming in for a close-up ... TAKE THREE Moira McIver, the Principal of the school, had been standing near the...

3 years ago
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  • 12
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High School Flasher Club

High School Flasher Club I wanted to start a photography club in my high school but no one wanted to join. I was always considered a nerd and photography just wasn’t cool. Their loss. I got my sister to help me out. Natalie was a year younger than I was but she was certainly no nerd. In fact Natalie was part of the cool group. She was very pretty, well built, and quite popular too. At fifteen and in the ninth grade Natalie was always good to me. I was sixteen, in the tenth...

3 years ago
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  • 27
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High School Class Reunion

The last time I had seen Rose was at our ten-year high school class reunion. In high school, Rose had been the one girl I wanted to date, but she barely even knew I existed. At the ten-year reunion, I confided that I had always had an immense crush on her and that if I had to do things all over again, I would have said as much.To my surprise, Rose told me she had a crush on me as well, but that she had been too shy to approach me. Both of us had gone out separate ways, married and started...

Cheating
2 years ago
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HIGH SCHOOL DAYS

High School Daysbynikkis©When I look back at those days I realize that the height of my most memorable high school sexual experiences started in one week. It was the week that would change the relationship between me, Mom, Karen, my girl friend, Brad my best friend and his girl friend Sasha, forever. I was an 18 year old high school senior cross country runner at the time. Mom also ran she actually got me started in the sport. Mom had been running for years just to stay fit and it showed. Her...

3 years ago
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  • 7
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High School PimpChapter 5

Bill paid a visit to the next man up the ladder in the loan sharking ring. Somewhat reluctantly, this man supplied the names and locations for four more of the men who actually made the customer contacts. This guy reported directly to Archie, so Bill learned that the loan sharking ring was not very thick and could be easily broken. There was nothing more for Bill to learn from him, so Bill sent him to the hospital with the usual complement of broken joints. By the middle of the following...

3 years ago
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High School Stud

It was 1980 and I was a senior in high school. There was a guy in my grade and we had gone to school together all four years. We both did sports and we both played football and basketball all four years.During our freshman and sophomore years we were also required to take physical education. Fortunately for me we both had the same PE classes all four semesters and back then everybody showered after practice as well as Phys Ed.  I don't know why the school seem to have stopped this unless they...

Gay Male
1 year ago
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  • 22
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High School Teacher Scandal

"Damn! You my sweet bitch, ain't you? You sure know how to lick some good pussy, girl."Megan raised her head from between Kathy's black thighs. She didn't make eye contact, just starred off into space, detached. A stray black pube was glued to her cheek and the musty stench of Kathy's muff filled her nostrils and mouth.Kathy stroked her blonde hair as she stared into her ice blue eyes. "You still missin' them football players, snowflake? Ha! Damn! They must've fucked you good. Why don't you...

1 year ago
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High School Undercover

Your career is stagnant and dull. Your name is John Doe and you are an investigative journalist. You are young, having just turned 23, and your pieces have earned you a few awards. But as of late, you haven't gotten any good subjects to write about. You've been relegated to beat coverage to pass the time, mostly because your editor isn't willing to pony up the bucks required to undertake a good investigative report in these trying economic times. Though the gig has been boring the last year or...

2 years ago
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High School Fall Festival for Terry Webb

To all those who follow my posts you already know I am very adventurous sexually. I often meet people directly from websites who respond to my postings or I often repeat similar adventures that work for us such as being a truck stop whore or being a bar slut or a beach cum bucket. All of these continue to work for me. But instead of posting adventures that are nearly the same as previous adventures, I try to keep it fresh by sharing new extremes I've tried. So yes I remain very active sexually...

2 years ago
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High School Cocksucker Outted another story

When I was 16 I slept over at Kyles a lot. Mostly I slept over because he'd fall asleep while we were playing video games and watching tv. It was up to me whether I stayed and slept or went home. Kyle is black about 6'2 and has a strong build. He has a white Mother (Molly) and a black father (Wayne). He has a sister named Jazyln who just entered high school. She has her mothers facial structure and a tight little body with breasts that seem to spring over night to about a large B cup. She was...

3 years ago
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HIGH SCHOOL REUNION TAKE TWO THE ANTAGONISTS

It is the annual alumni reunion event at the Lauderton High School, which they hold in the large gymnasium in the main school building. The events in these stories take place at various times during the evening, and to different characters; they are not chapters of the same story, but a series of separate takes. We are the invisible camera, panning around the scene and then zooming in for a close-up ... TAKE TWO Hayley Statten was restless and bored, wondering why she had come to...

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