The Tomboy Tapes free porn video

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The Tomboy Tapes by Karen Elizabeth L. It was going to be another one of those mornings at the breakfast table, I thought as my mother and sister began arguing. "Why can't you dress up a little bit for school Cindy," Mom sniped. "It wouldn't hurt you to look a little more like a girl now and then you know!" "I look like most of the other girls mom," Cindy replied in between bites of toast. "The days of wearing dresses and heels to school went out with hoop skirts! Do you want me to look like some kind of freak?" "I just want you to look your best that's all," sighed mom. "I want everyone to see what a pretty daughter I have!" "You're sweet mom," Cindy smiled as she chugged down her juice. "Sweet but so old fashioned!" As Cindy ran out the door mom had already turned her attention to poor dad, hounding him about Cindy's looks and grades. "She could do much better in school if she were motivated, I know she could be getting A's and B's instead of the C's she gets now. If I could just find some way to motivate her to dress better and work harder," Mom lamented. "I understand dear but I can't suggest any new ways to motivate her either." Dad was just as upset as she was but Cindy remained cool and calm no matter how hard they tried to change her. Sometimes it seemed as if they were pushing a big mound of Jell-O, but that couldn't be right, I thought, Jell-O could be molded! Several weeks later I saw Cindy dumping several cassette tapes into the garbage then trying to cover them over to prevent their being found. "I've never seen you work so hard Cindy," I joked walking into the room. "What's up?" "Motivational tapes," she sneered as she mixed up the trash. "A little present from mom and dad. They figure that if I listen to them I'll work harder in school and it'll even spill over into my homelife. I sort of hate to disappoint them but they're not brainwashing me into becoming some little 'Goody Two Shoes'!" "Hold on a sec, I've heard a lot about those kinds of programs and they're supposed to be really helpful! Why not try them and see, what can it hurt?" I asked eagerly. It wasn't so much that I was eager to help Cindy, more that I saw a chance to be a real pain in her side! Cindy shrugged and pointed to the trash. "If you're so thrilled about them help yourself, have I mentioned lately that you are such a suck up?" she called, leaving the room. "But a well motivated one!" I laughed as I cleaned off my newly acquired treasures. Here was a golden opportunity to show Cindy up, I'd just listen to the tapes myself and when our parents see my report card I'll tell them about the tapes! I put them in the back of one of my desk drawers so that mom wouldn't accidentally run across them, no point ruining my own surprise! I put the tapes on before going to bed but even with the volume nearly all of the way up I had to listen intently to hear anything then closed my eyes and went to sleep. The next morning I tried my best but just couldn't remember much about the tape. I did know though that it had been a very sound night's sleep and that I was feeling very refreshed and anxious to get started! "You're looking good this morning Jim," commented dad. "Ready for that big test today? You need an 'A' to pull your grade up for the year you know." "Studied all evening dad," I smiled wondering what kind of an edge I'd get from that tape I had listened to. "I can't wait to take it!" "That's wonderful Jim," Mom said as she gave him a hug. "I'm sure you'll get an A!" "Suck up!" scoffed Cindy as she came into the room. I just smiled and stuck my tongue out at her. I enjoyed being mom's favorite and I wasn't going to start an argument with Cindy at breakfast, that was mom's job! Mom started up right on schedule. "How were the tapes Cindy, feeling more motivated today?" "They were great mom, I can't wait to get to school!" Cindy shot a quick look at me to see if he'd give her away. We both knew the only motivation for her to get to school was to see her friends but I'd keep quiet for now! "Gotta run, nice chatting!" she called on her way out the door. Mom smiled broadly. "I think they're starting to help her already," she told dad. "I can't wait to see her report card! This is going to be a turning point in her life, I just know it will." "Yes dear, I'm sure they've helped," he mumbled through his newspaper. "What was that about her report card?" "Go back to your paper dear," Mom said with an exaggerated sigh. "I'll let you know when your daughter makes the Honor Roll!" "Betcha I get there first!" I offered as I took small bites of toast and sipped at my juice. Somehow I just wasn't in my usual hurry to gobble down breakfast, must be that tape calming me down for the test today, I thought to myself. Mom smiled sweetly and patted me gently on the back. "We're sure you can make it dear, it's Cindy we're worried about. Of course with those tapes she may just pass you up!" "Fat chance mom." I was suddenly defensive. "Cindy will never be as good as me so passing me up would be a fantasy!" "Give your sister a chance Jim." Dad suddenly put down his paper. "You'll feel awfully silly if she beats your grades so don't start gloating." "Stupid too," I mumbled under my breath. Dad took a swipe at me with his rolled up paper. "I heard you, now shut up and give the girl a chance. We went through a lot of trouble getting her to listen to those tapes and we're expecting to see results." "All right, I'll keep quiet," I replied as I sulked out the door feeling very let down. "But don't expect too much, we all know there isn't that much to work with!" I wanted to add. "Especially since she's not even listening to them," I thought to myself, but I'll just bide my time! "Thanks for not giving me away at breakfast," Cindy told me later. "That was very sweet of you." "I didn't do it for you," I insisted. "If I gave away the story mom would've taken the tapes away from me and I want to keep them." "Hey I don't care either," Cindy shrugged as we walked to class. "You're welcome to all the stuff mom and dad give me. Maybe there will be lessons on being a better suck up in one of them!" She laughed derisively. "Suck up? Me?" I exploded angrily as my face becoming to burn. "Dad rushed to your defense at breakfast this morning, so maybe you've been doing a little sucking up yourself? Playing the old 'Daddy's Girl' routine again?" Cindy laughed and brushed her hair back with a quick flick of her wrist. "A little kiss goes a long way with guys, especially when it comes from their daughter!" "I bet them that you'll never be nearly as good as I am and kisses to dad won't make a difference," I scoffed unable to help but feel that she was somehow cheating. "I'm smarter, more motivated and with those tapes I'll pass you in a flash!" "Don't care, I'm still way prettier than you!" she laughed as she threw back her head and fluffed her hair. Weeks went by with Cindy and mom still occasionally arguing over breakfast. Cindy was a slacker, there was no doubt about that but her grades weren't that bad. They both knew that the argument had deeper meaning for mom. Cindy had never been the sweet little girl of mom's dreams, she despised baby dolls, and fought being dressed up in pretty outfits even as a child. Even if Cindy had made the Honor Roll mom would not have be satisfied unless Cindy accepted the award in a beautiful gown! "Are you doing better in school Cindy?" Mom would ask in an innocent tone. "School still sucks mom," Cindy would nonchalantly shoot back to mom's horror. "Sucked then, sucks now, and it will go on sucking forever!" "I saw a really cute outfit at the mall yesterday honey," Mom would venture in a vain attempt to move the conversation around to what she really wanted to talk about. "Maybe I'll pick it up for you, it would make a nice school outfit." "Got enough jeans and stuff mom thanks," Cindy would shoot her down in flames. "Besides I'm not going to school in one of those 'Little Miss Muffet' outfits you like so much. Too frilly for me!" Suddenly a picture of a frilly dress with puffy sleeves and a full skirt popped into my head. "Such a pretty outfit," I found myself thinking. "Cindy's so lucky and she just doesn't realize it! I'd kill for a dress like that." I nearly choked on my milk as I struggled to regain my thoughts. "What made me think something that crazy?" I wondered. "Why would I want to wear a dress?" "What's your problem?" Cindy asked. "Thinking of getting one of the cheerleaders into an outfit like that? I'd bet you'd love that!" "I wasn't thinking anything at all!" I insisted, afraid that somehow she knew about the words that wouldn't go away. "But now that you mention it mom's right, you would look nice in a pretty outfit like that. It wouldn't hurt to look a little more like a girl you know! Think of how nice you'd make mom feel." "If you're so concerned about mom's feelings why don't you take the job?" Cindy shot back maliciously. "What job, what are you talking about?" I asked puzzled that I had somehow lost track of the conversation. "Daughter of the family!" laughed Cindy as she waved her hand towards me. "There you go mom, your very own sweet little girl just waiting for you to dress her up in a pretty little dress with patent leather shoes, a little purse and gloves. You two could have a great time shopping for cute little party dresses!" "You're nuts!" I shouted ready to reach across the table at her. "You're a sicko too talking about stuff like that! It's just that..... oh forget it!" Cindy looked at me strangely for a second or two before rushing off to meet her friends. I suddenly had a terrible feeling in my stomach. "How did I let myself get involved in a discussion about my sister's wardrobe, I must be losing my grip!" "Gotta roll," I blurted, grabbing my books and running out the door. I pushed myself to think of an upcoming trigonometry test to prevent those strange thoughts from returning. "Here ya go Jim," Cindy announced as she tossed several new tapes onto his bed a few days later. "Mom's motivational series, part two!" She laughed as she threw herself into a chair. "I don't know if I want these after our argument," I said even as I pulled the tapes towards me. "You were awfully nasty to me that morning you know." "You're breaking my heart Jim," Cindy sneered. "I seem to remember that you jumped on mom's side and took a cheap shot at me! Now you've got the nerve to sit here and pretend you're precious little feelings have been hurt. Bummer!" "But honestly Cindy," my voice took on a tone of sadness, of being misunderstood, "I was really trying to help you, you could look so pretty if you got dressed up once in a while..." Cindy dropped to her hands and knees and began scouring the room. "Come on out, I know you're here," she called out. "I'm trying to have a serious conversation with you if you don't mind!" I shouted as Cindy continued her searching. "What in the world are you doing?" "Looking for mom of course," she grinned. "I know she's hiding here somewhere, I can hear her! I can't figure out how she got your mouth to move as if it were really you talking but I am impressed!" "Get out of here you idiot!" I screamed as I finally lost my patience. "You're too stupid to realize how nice you could look and how happy you'd make mom!" Cindy turned and smiled. "The job's still open and you can help yourself to any dress in my closet!" As she slammed the door behind her I threw myself on my bed and fought back the tears. Cindy was right, I had sided with their mother against her but why? It wasn't even my usual cheap shot at her, I was really trying to help! Now though Cindy thinks I should be some kind of sissy running around pretending to be a girl and if that's not bad enough there are those thoughts! The thoughts kept popping into my head at the most inopportune times, just that past week I had been in the middle of a History test on Victorian England and couldn't seem to force a picture of myself all done up in a pretty lace dress with a floppy hat and parasol from my mind. Not long afterwards I began to let my hair grow even though my parents badgered me daily to get it cut. "I think I look good with long hair mom," I patiently explained. "Lots of guys wear their hair long and some even pull it back in sort of a ponytail! It looks really great and it's the latest style." "The latest style for boys is to look like girls?" Dad asked with barely concealed scorn. "Sounds great, first you got an ear pierced and now you're letting your hair grow. Are you nuts or what?" "Gotta keep up with things dad or I'll end up as a nerd." "You already are a nerd," laughed Cindy. "Now you're just a funnier looking nerd!" "Enough from both of you," scolded mom. "Jim, If you're going to have long hair you better make sure it's kept neat and clean or I'll cut it off while you sleep! And Cindy, listen to those tapes, I don't plan on throwing money away!" "Don't worry mom, I'm making good use of them!" Cindy assured her after a quick glance my way. I knew that I wasn't about to call her a liar, I enjoyed the tapes far too much to cut off my supplier. "And I'll keep my hair nice mom, I promise," I added feeling relieved that I could let my hair grow. Lately having long hair had become very important to me but I just couldn't seem to focus on a reason. "Maybe," I thought to myself, "I'm just trying to outdo Cindy again by showing her that I could look good in long hair when she insisted on keeping hers short." What I couldn't bring myself to admit though were the thoughts I was having of how pretty I would look with long curly hair! The arguments between my sister and mother continued on as did the tapes which as far as I was concerned kept getting better and better. The last bunch promised motivational messages mixed in with songs from some of the hottest rock groups, I would spend hours playing the tapes over and over while studying or drifting off to sleep. I kept waiting for my grades to take a giant leap forward, after all I played the tapes religiously and mom had promised Cindy they'd make a big difference in her life if she only relaxed and let the messages work. I 'd spent many an evening with just a small light on in my room, headphones clamped to my ears, relaxed, listening, absorbing, and waiting. One reason I concentrated so hard on those tapes was because those goofy ideas kept coming back to me, you know the ones about wearing pretty dresses and having long curly hair. No matter how much I concentrated on those tapes though the thoughts kept coming. One day I was reading a newspaper and suddenly find myself drawn to an advertisement for girl's clothes. I stared at that page for five minutes straight and when I was finally able to put it down I had an overwhelming urge to put on some of my sister's clothes! Luckily no one was home and I quickly raced upstairs and threw open the door to Cindy's closet. There, pushed to the back I saw what I wanted, a simple, pink minidress that Cindy had worn once when dad took us out to celebrate a promotion at work. I grabbed the dress and quickly ran back to my room and locked the door. I swiftly removed my shirt, undid my belt, unfastened my jeans and stepped out them. My heart was pounding and my hands were shaking as I pulled Cindy's dress over my head then tugged it over my hips. Just as I finished adjusting it I was overcome with the most wonderful, peaceful, feeling I'd ever know. I stared at myself in the mirror, unable to move, unwilling to change. "This is Heaven!" I thought. I must have worn that dress for nearly half an hour. I practiced posing in different positions, walking, and sitting until just as suddenly as the urge hit me to put it on I felt that I had to take it off. I couldn't stop for a second until I had the dress safely back in Cindy's closet and had my pants back on. My heart was still beating wildly and my hands were sweaty and shaking. I couldn't believe that I had actually put on one of Cindy's dresses but my unbuttoned shirt and loose belt were proof that something terrible had happened. Or had it? I just wasn't sure and it was driving me mad! After that I found myself doing strange things that made me think I was going nuts. One day I was taking a shower and reached to shut the water off only to pick up the razor Cindy used to shave her legs. I stared at the razor and then at my legs. Suddenly I was disgusted by the hair on my legs, lathering up with a bar of soap I sat down on the side of the tub and removed every strand of hair from my ankles to my butt! Whatever demon was possessing my mind wasn't satisfied though and without giving it a second thought I shaved my underarms too! I ran my hands along my now smooth legs and admired the shapeliness I never before realized they had. They were smooth, silky, very pretty and I was very happy! I smoothed lotion over them to help keep my skin soft and silky then carefully patted myself dry with the fluffiest towel I could find before reluctantly pulling on my briefs and jeans. It wasn't until I was sitting on my bed putting on a pair of socks that I realized with horror what I had done! "What's wrong with me?" I wondered as I absentmindedly counted the strokes of the brush through my hair. After it happened I was sure that everyone I met could somehow tell that I tried on my sister's dress, fortunately I quickly realized that there was no way for that to be possible. It happened in the privacy of my room, I took it off and put it away again and there was nothing left to show for it, I was safe. Or at least I was until now! Now I'd be stuck wearing long pants even though the weather was warming up and everyone else would be wearing shorts. I was stuck until the hair on my legs grew back, if it ever would! If that wasn't bad enough there was always the problem with my underarms, if I wore my favorite muscle shirts, I couldn't raise my arms lest my girlish underarms be seen. "Boy, I really screwed up this time," I thought as I began my hundred strokes on the other side of my head. Once I finished my daily brushing routing I gathered my hair and pulled it back into a ponytail. "Too bad I can't use one of Cindy's scrunchies to hold my ponytail," I thought to myself as I put a rubber band around it. "These rubber bands are giving me split ends." At school I tried to concentrate on what was going on in class but I kept getting distracted by the girls in my classes. I couldn't stop staring at some of them, especially if they wore a skirt or dress! I didn't care what Cindy said about not wearing dresses to school, these girls wore them and they looked great! Judging from the way they acted they really seemed to enjoy being dressed up, they walked differently, they sat differently, everything they did seemed so feminine that it drove me wild and to my amazement jealous! I had to be crazy! I'm supposed to be a normal teenage boy lusting after pretty girls yet more and more I was envious of their pretty clothes, the way they wore their hair, and the way they moved. I wanted to be just like them, to have long, pretty hair, to wear pretty dresses and nylons, to tantalize with a slight scent of my perfume. It was insane, positively insane but I couldn't control the feelings building up in me, I wanted to be the daughter mom always wanted Cindy to be! I wanted to wear pretty dresses to school, to do my nails in pretty colors, I wanted to experience the delightfully wonderful world of a pretty young woman! One day in school there was a pep rally and the cheerleaders were allowed to wear their uniforms to class. I was in Hell as I watched those pretty girls in their short skirts walking down the halls laughing and having the time of their lives. Why was I stuck in these awful pants and plain shirt when I should be wearing something colorful and pretty? I had to do something about it but until I got home I would have to endure the torture of seeing these girls so self confident in their femininity practically daring me to join them! I couldn't begin to figure out why I felt the way I did, I never noticed those things before but suddenly they seemed so important to me! I tried to force the thoughts out of my mind but as before they came right back, stronger each time. One day I walked into the house after school and was relaxing with a sandwich and cold glass of milk when I was overcome with a strange feeling. No one was home but I'm not sure that would have made a difference, I had something to do and I'd simply die if I couldn't get it done! I went straight to Cindy's room and quickly pulled the pink dress from its exile at the back of her closet. This time though I wasn't going to rush back to my room to try it on as I had many times in the past few weeks, this time I was going to do it right, the way Cindy should! I opened every drawer in her dresser until I found exactly what I wanted, a pair of pretty satin panties that still had the tags on them, a bra, white pantyhose that Cindy had worn once, and a white half slip trimmed in lace. Carefully cradling my treasures I hurried off to my room before I came to my senses and put everything back. Just as I had done so many times in the last few weeks I locked my door and carefully checked to make certain that it couldn't be opened. I considered pulling my drapes shut but there aren't any other houses close enough for anyone to be able to see in my windows but the possibility made what I was about to do all the more exciting! I quickly removed every stitch of boy's clothing I had on then with trembling hands I pulled the satin panties up to my waist. I had tried on Cindy's panties before but they had all been cotton, softer than any of my briefs but nothing special, just plain white cotton without even a pretty little flower to brighten them up. Of course it felt very exciting to wear girl's panties but the feeling was nothing compared to what was happening to me now. The satin was so soft, silky, and cool against my skin that I had an instant erection! What a contrast, pretty satin panties being pushed out of shape by something that they were never meant to hold! I thought of an assignment I had recently done for English class on contrasting things, too bad I could never write about the contrast of the utterly feminine panties and an utterly masculine erection! It took a bit of work to get the bra on, this was to be my first time, guess I was saving it for a special moment, but finally I had it hooked in back and stuffed with some socks until I had close to what I figured Cindy's bust size was. The pantyhose were tough, I'd seen commercials and movies where a woman would start pulling on a pair but once again it was my first time and I was scared to death of putting a run into them, I'd never explain something like that away. I carefully inserted my right foot then slowly pulled them as far up as I could before putting my left foot in. When I finally had them worked up as far as my thighs I hesitated for just a second feeling that I was on the verge of taking a very important step. A deep breath and I slowly worked them all the way over my thighs and unrolled the waistband, my heart pounding in my ears, goosebumps popping up on every piece of flesh! "What was wrong with Cindy?" I wondered. "I'm only partially dressed and I can't believe how wonderful these clothes feel! How could she prefer cotton panties to these dreamy satin ones I wore, why would she ever wear socks when she could wear these stockings which were making my legs look so pretty and sexy!" The slip made me look much better hiding the unsightly bulge in my panties. The pantyhose helped keep it in check but now with the slip on I looked more like a girl with my pretty, nylon covered legs extending beyond the lace hem of the slip. Even though I was still excited I was becoming much calmer, more sure than ever that I should dress this way! I lowered the dress over my head with all the confidence and self assurance any girl my age would have. Every part of my brain was now telling me that this was natural, I was a young woman and this is how I was expected to dress! Completely dressed I was shocked to see Cindy's reflection in the mirror. I nearly panicked until I realized that Cindy wasn't in the room, I was alone, the girl in the mirror was me! Sure there were a few rough edges, Cindy had a few more curves than I did but I was sure that with a little padding here and there I could easily look every bit as pretty as Cindy did on those rare occasions when she did get dressed up. I'd love to have her see me now and tell me that although I'm smarter she's prettier, I'd show her who the prettier sister was in this family! My time in Heaven ended all too quickly, I had to hurry to undress and put things away before anyone came home. I was sure of one thing as I put the clothes away, something had gone terribly wrong, I'm supposed to be a pretty girl, not an average looking boy! From now on I vowed, I'd work harder until I could do everything a girl did and do it the way a girl did. When I was finished my family would realize that although Cindy was just an overgrown Tomboy I was a young lady and they'd treat me like the young woman I was meant to be! I admired myself for a little while until the feeling vanished as suddenly as it had come on and I found myself utterly disgusted by what I had done. I stripped off Cindy's clothes as fast as possible then quickly donned my own. After I finished putting my sister's clothes back I returned to my snack but found it difficult to eat with the tremor in my hands. What had happened to me? I had seemingly lost all control over my actions but I was too ashamed to talk to anyone about it. Things kept happening more and more after that, I had an unquenchable desire to dress in Cindy's clothes, to shave my legs and underarms, and keep my hair long and pretty and I wasn't feeling nearly as guilty about it anymore! Keeping my legs and underarms smooth and silky became a part of my daily shower ritual, brushing my long hair wasn't a job, it was fun! I even graduated from wearing Cindy's clothes alone at home to wearing panties to school! It was so scary yet exciting, I'd be dressing after a shower and boom the urge would hit me! I'd wait until Cindy was downstairs then sneak over to her room and borrow a pair of panties. In school I had to be extra careful in the way I moved, sat, or stood to prevent anyone from seeing the waistband of my panties peeking over my pants. I was trapped, terrified that I'd be caught! Every afternoon when school ended I breathed a sigh of relief that I hadn't been discovered and vowed that I'd never do it again but the next morning would find me once again pulling on a pair of panties! The feelings had grown so intense that I started to dress more and more often and wanted to wear different things other than Cindy's pink dress. I tried on her jeans, her shorts, and her nightgowns, if it was in her closet or her drawers I at least tried it on, sometimes as I did with her panties, wearing them with my boy's clothes. It was nearly impossible for example to distinguish her white socks from mine but it made me feel like I was fooling people when I wore them instead of my own! I'll never forget the first time I wore them instead of my own, I was sure that mom, dad, Cindy, and the entire world could somehow tell that I was wearing a pair of girl's socks but no one said a thing or even looked at my feet! After going through Cindy's boring wardrobe I somehow came up with the idea of checking out my mother's clothes. She and Cindy were about the same size and whenever she went somewhere special she wore some of the most gorgeous outfits! I figured if she hounded Cindy so much about wearing more feminine clothes mom might just have some really pretty things stashed away in her drawers and I couldn't wait to try them on. I held out for over two more weeks before I finally had to give in to the urges. Mom and dad were going to be spending a Saturday visiting some out of town relatives and Cindy would also be gone until late evening. The instant I had the house to myself I locked all of the doors then ran to mom's room undressing as I went. When I reached her closet I had a strange feeling of excitement seeing the dresses, skirts, and suits of every color and style which called out to me to try them on! The first outfit I picked to try on was a dark blue dress with sheer sleeves that mom wore when she and dad went out for their anniversary dinner. The material was very sheer but there was something like a built in slip under it to keep it from being totally see through. I couldn't wait to try it on but I wanted to check out mom's lingerie first in the hope I'd find something pretty to wear under the dress. When I opened her dresser drawer I couldn't believe my luck, instead of white cotton I was staring at satin, nylon, and silk in so many different shades it was as I was staring at a rainbow! Almost every pair of mom's panties were lace trimmed, some were made of nothing but a stretch kind of lace, while others were so sheer and sexy I found myself blushing! For a moment or two I was shocked to think that my own mother wore these kinds of clothes then my heart began to pound as I realized that soon I too would be wearing such feminine and sexy items! I picked out several different matching panty, bra, and slip sets to try on but the one I couldn't wait to wear was black, beautiful, shimmery, silky, black with lace at the waistband of the panties, lace at the bottom and side slit of the full slip, and if that wasn't enough to drive me crazy the top part of the bra's cups were nothing but lace! I couldn't get out of my regular clothes fast enough, I was all set to tear my shirt when my fumbling fingers finally undid the last button. I pulled down my briefs but instead of placing them on a neat pile with the rest of my things I gleefully kicked them across the room, I wanted to have nothing more to do with such ugly, confining clothes, I was a young woman exploring my femininity and boy's briefs had no place in that world! If I still had any insignificant doubts about what I was doing they were erased forever when I slid the dress over my head, over my bra, panties and a pair sheer black pantyhose. I wanted to run out into the street and shout "I love being a girl" but I hadn't yet gotten the hang of the black heels I had also borrowed from mom's closet. I found a string of mom's pearls and after a few seconds work I managed to get them around my neck and fasten the clasp. I slipped a delicate gold bracelet on my wrist, fastened a dainty chain around my ankle, then set off on wobbly ankles for mom's vanity and makeup across the room. I reached the vanity without breaking an ankle then smoothed out my skirt as I'd watched girls at school do before sitting down. My reflection in the vanity mirror was pretty good, I looked a lot like Cindy might look in this dress without makeup on, but that wasn't good enough for me. I wanted to be the pretty sister and in front of me were the tools I would need to complete my journey from plain to pretty. I just hoped I could master them without anyone discovering what I was doing, I wanted to surprise mom with a daughter who was pretty and feminine, a poised and confident young woman! I spent the rest of the morning and the entire afternoon in mom's room experimenting with makeup, clothes, and hair all the while worried about the feeling that I was supposed to have been a girl. Fighting the feelings wasn't possible any more, I was caught in a web of satin and lace and there seemed no way out. I began to think of how happy I would be to let mom buy me skirts and dresses to wear to school! Cindy might rebel at the thought of wearing a pretty dress now and then but I wouldn't! I would learn the proper way to dress, do my hair, wear makeup, and behave as a proper young woman and mom would be so proud of me! I had so much to learn but I wasn't finding a whole lot of time to study. Mom and dad were staying home more on the weekends and with finals coming up Cindy was actually coming straight home from school to study. Luckily I was able to sneak some of mom and Cindy's things into my room where I hid them in the back of my closet. In the afternoons I'd go to my room to study but it wasn't school work I was studying, instead I was hard at work trying to master makeup and hairstyling. One Saturday afternoon after finishing showering and shaving my legs and underarms I was sitting on my bed combing out my hair as Cindy walked past my room. "Your hair's getting pretty long," she laughed as she watched me carefully pull a comb though his hair. "Almost ready for some pretty ribbons and bows!" Cindy's comments brought the old feelings crashing back on me, I shouldn't want long hair and I certainly shouldn't have been wearing the panties I had on. I wanted to cut my hair off right then and there, to change into a pair of boy's briefs and burn the panties. I wanted to, but then I thought of how pretty my hair would look tied back in a ponytail with a pretty ribbon holding it in place. I thought of how smooth and soft the panties were and how rough and heavy my briefs were and it wasn't a contest. I couldn't do anything about what was happening to me and I knew it. Lost in thought I dropped the brush I had in my hand and bent over to retrieve it. "Those are my panties!" Cindy exclaimed as she spotted her satin panties. "What are you doing wearing my underwear you little pervert?" "I can explain Cindy, just gimme a chance," I begged. "What are you trying to pull?" Cindy asked suspiciously. "What are you doing with these things?" I spent a long time trying to explain things to Cindy who seemed to have a hard time understanding what made perfect sense to me, at least at that time. Cindy stared at me as if I came from another dimension. "I don't understand but I think you'd better tell mom. Dad's gonna freak, that's for sure!!" "I guess he will," I said sadly. "I can't help it though, I should have been a girl, just like you. Only thing is that I really like getting all dressed up and wearing frilly stuff, I want to be the kind of girl mom wants you to be, all satin and lace and stuff!" "So what do you need from me?" Cindy asked cautiously. "I can't do anything about dad, I'm sure mom will be proud of you, surprised as all heck but proud!" "I"m having a lot of trouble learning to apply makeup and fix my hair," I told her. "I was hoping you could help." "But you're a boy!" Cindy exclaimed, exasperated. "Boys don't wear dresses, they don't wear makeup, and they don't run around in their sister's underwear! "Look, you and I weren't exactly close friends but I just don't think I can handle helping my brother become a girl." "Please Cindy, I'll be a great sister I promise," I begged. "If you're that serious about being a girl, why not ask mom to help? She knows more about makeup and hair styling than I do," Cindy suggested. "You're going to have to tell her anyhow you know, why not do it now and let her help?" "You don't understand Cindy, I want to surprise mom. I don't want to say anything to her until I can do everything any other girl can do, until I'm as much of a girl as I can be!" "But what if someone finds out about you? What about the other kids at school?" Cindy challenged, obviously trying to weasel out of helping me. "I guess they're bound to find out," I shrugged. "But that's not going to make any difference at all. I'm going to be a girl whether they like it or not!" It took a lot of convincing before Cindy agreed to help but it's not everyday that a girl's brother asks her to teach him how to be a girl. She didn't wear makeup so she couldn't teach me much herself but she did promise to pick me up a few magazines and she even agreed to buy me my own makeup! She was never this nice to me as her brother, it was obvious that being her sister was going to be much nicer! Mom wasn't letting up on Cindy, the constant battle over Cindy's dressing continued but Cindy didn't complain as much anymore. She simply take the clothes, jewelry, and makeup mom would buy her and put them in her room for me to use. It was a good system, I got the latest styles, makeup that was perfect for me and since mom occasionally checked and found that the stuff was being used she eased up on Cindy. Mom was happy, Cindy was happy, and I was ecstatic! After a few weeks had passed Cindy seemed to forget her reservations about turning me into a girl and became very helpful in my drive to replace my boy's clothes with girl's clothes. The first thing to go were my briefs of course, replaced by the prettiest, silkiest panties Cindy could find for me. I replaced my white sweat socks with girl's socks, bought several girl's tee shirts like Cindy wore and even found a pair of girl's sneakers that were plain enough to pass as boy's sneakers. It was so wonderful for me to go off to school wearing panties, a girl's tee shirt, girl's socks and sneakers, the idea that I was somehow trapped, that I couldn't possibly change into boy's clothes was both scary and exciting! No one ever batted an eye though, I was just another long haired guy as far as my friends and family were concerned! One day after school had ended for the year though mom started picking on Cindy wondering why she'd spend so much money on makeup and pretty clothes then never wear them out of the house. "Don't worry about it mom," Cindy replied trying to avoid ruining my surprise. "Maybe someday when you quit bugging me about it I'll get dressed up and let you take me shopping. Until then don't bug me!" That was the wrong thing to say to mom and Cindy quickly found herself on the receiving end of a tongue lashing that would have gone down in the history books as the greatest of all time. She was being grounded for a month, her phone privileges were being taken away, and there was more to come until I spoke up. "Please don't yell at her mom," I pleaded. "She's only trying to help me surprise you." Mom stopped suddenly, her momentum in the argument lost. "You're not involved in this Jimmy, please mind your own business." "That's just it mom, I really am involved and I'll prove it!" I told her as I left the table. I went to my room and from a box I had hidden in my closet removed pictures that Cindy had taken of me modeling different outfits. Returning to the kitchen I laid them in front of mom and proudly announced, "This is my surprise, the daughter you always wanted Cindy to be!" Mom studied the pictures for a few seconds then smiled broadly. "I'm sorry Cindy, you look lovely in these. Were you planning on surprising me?" "Not exactly mom," Cindy hesitated for a long time then glanced towards me. "That's not me those pictures." "Of course it's you?" Mom seemed puzzled, glancing at the pictures then at Cindy. Finally she took note of Cindy staring at me. "If it isn't you then who is it?" she asked looking straight at me. "It's me!" I replied filled with pride. "I hope I look good enough to make you proud of me!" "T..t..this is you?" Mom gasped as dad pulled the pictures from her hand. "What in God's name are you up to?" "Oh my Lord," Dad uttered softly. "Tell me this is some sick joke you're pulling Cindy." "I thought so too at first dad but Jimmy convinced me that it wasn't," Cindy explained, "believe it or not, that's Jimmy in those pictures." Mom looked at me dumbfounded. "Jimmy?" She asked, her voice strained. "You'd better have an awfully good explanation for this." "How can he possibly explain these!" Dad thundered as he threw the pictures in front of me. "This is sick!" "I don't understand," I said sadly. "It just seemed to happen all of a sudden, I don't know why." "Will everyone please calm down," Mom interjected stepping between me and dad. She laid the pictures in front of me. "Now young man would you please explain why you're wearing girl's clothes in these photos?" I thought for several seconds on just how to answer mom's question before deciding not to drag things out. "I want to be a girl, that's why." "You what?" Dad asked seemingly stunned at my announcement. "Are you serious?" Mom gasped. "You can't be serious!" "A girl, you want to be a girl?" Dad was obviously shocked, his face had lost all color and his eyes were bulging. "When did this happen? You've never mentioned anything like this before." "I can't remember wanting anything more than I want to be a girl," I explained as best I could. "Maybe I didn't realize it before but now I'm absolutely certain that I want to be a girl." "But why?" Mom asked trying to remain calm even though she appeared to be on the verge of crying. "What made you decide you want to be a girl?" "I don't really know how it happened mom, I tried to ignore it and be like any other boy but I couldn't help feeling that something was wrong. I started trying on Cindy's stuff and then I knew for sure, I should have been a girl." By now I was on the verge of tears. "Please daddy don't be mad at me, I can't help how I feel." Dad stared at me but the look of disgust was beginning to fade. "When did you start thinking that you should have been a girl? What could suddenly make a normal boy decide that he'd rather be a girl?" "I'm not sure," I said as I wiped a tear off my cheek. "The idea of dressing up seemed to come a couple of months ago and it just got worse and worse. I tried not to give in but the feelings were just too much for me, one day I was taking a shower and wanted to shave my legs and underarms, before I knew what was happening I was wearing Cindy's dresses then mom's underwear." "Wait a second," Cindy announced, an odd look in her eye. "Mom, when did you start getting those tapes for me?" "I don't know," Mom replied offhandedly. "Three, maybe four months ago why?" "And they were just supposed to motivate me more in school right, nothing else?" Mom hesitated before answering. "Not exactly, school was just a minor part of it, actually they were supposed to make a young lady out of you but I guess they were a waste of money." Cindy started to laugh and soon had tears rolling down her cheeks. "No, actually they would have been worth every penny you paid for them, if I listened to them!" "I'm confused," Dad said. "Those tapes were supposed to make you act like a young lady but you never listened to them, what's the joke?" "I wanted to throw them away," Cindy laughed as she dried her eyes. "But Jimmy stopped me, he's been listening to them all along! You got the sweet young lady you wanted mom, it's just that she's your son!" "Oh my God," Dad gasped in shock. "This can't be true!" "I did listen to them," I agreed. "But they didn't seem to help my grades at all!" "There has to be some way to reverse this," Mom sobbed. "I never meant to turn him into a girl, it was all meant for Cindy!" "I know dear," Dad consoled her with a hug. "I went along with it to make you happy. Don't worry, we'll find some way to fix it." "What if you can't?" Cindy asked. "What then?" Knowing what had happened seemed to strengthen the little resolve to stop that I had left. "Please, there has to be a way," I sobbed. "I was never meant to be like this, there has to be some way to change me back again!" "But you said you wanted to be a girl, I wish you'd make up your mind!" Cindy sighed. "First you want to be a girl, then you don't, I'm confused." "So was I!" I cried. "Those tapes did this to me! I never ever wanted to be a girl, it's not my fault!" "Calm down, quit crying," Dad told me. "This whole thing is crazy but there must be a way out. Just be patient and for God's sake don't let anyone see you dressed up!" Mom and dad contacted the company that made the tapes but they had never faced a problem like this either. It turns out that the tapes were a new addition to their line of products which were used to help turn men into women! They were so successful with a line of tapes that helped mothers turn their sons into sweet young ladies that they branched out into tapes to help women due the same to their Tomboy daughters! I was unlucky enough to have used a series of tapes meant for a girl. After numerous visits to Psychiatrists and weeks of testing mom, dad, and I were called in to a counselors office and given the results. After much research with the company that made the tapes it was found that the tapes had an ingenious feature built into them which while planting and reinforcing the suggestion of increasing femininity built a defense against removing the suggestions! The counselor explained that by listening to the entire set of tapes I had unknowingly allowed this defense to complete its work and there was absolutely no way to overcome it. That explained the gradual loss of resistance that I had noticed, little by little the feature had broken my resistance and changed my thought process. Having completed the change it welded shut the door to the area that it had changed to prevent any reversal. It was all very precise and scientifically done, I would never again be able to go back to being a normal boy. For the rest of my life I would feel out of place as a male, my actions would become increasingly feminine and I would find myself drawn to feminine clothing and lifestyle. If I expressed my feelings I would be a social outcast, if I tried to suppress them there was no telling the extent of mental problems I would experience. I heard the counselor pronounce my death sentence. "The only thing that I could possibly recommend at this point is that your son undergo treatment for gender reassignment," he told my weeping parents. "It would actually require very little adjustment on his part and would avoid a lifetime of torment and mental anguish." "Very little adjustment!" I screamed. "How can you say that, I'd be a girl right?" "That's right, but mentally that would not pose any problem for you, actually you'd find it very pleasurable. Remember I told you that mentally you'll be developing into one regardless of what you do." "What would happen to me if I went through with this reassignment thing?" Even though I was becoming more and more interested in the idea by the second I tried to seem turned off or at least neutral to it. The counselor saw right through my act, smiling at me and my parents he continued. "You would immediately be started on a program of female hormones which of course will cause you to develop female secondary sex characteristics; smooth skin, fatty deposits on your hips and buttocks, breasts..." "Breasts!" I blurted involuntarily. "I'd have breasts?" "You'd have all the secondary physical characteristics of a girl your age in about four to five months," the counselor said smiling. "You'd look perfectly normal in a dress or any other feminine outfit you might choose to wear. "Frankly with your size and current level of development you'll become a very lovely young woman." "But what about..." I asked shyly glancing towards my crotch. "I recommend that as soon as possible you undergo complete reassignment surgery as soon as possible," I was told. "You'll feel much better about yourself when you're completely female." I couldn't believe that we were all sitting around calmly discussing my changing from a boy to a girl as if we were talking about the weather. It just didn't seem right to me, what about all the years I'd spent as a boy, how could we just pretend they never happened? "I'm scared mom," I said softly. "It's like planning my own funeral and I'm way too young to die." "Let me assure all of you that it's nothing like that at all," the counselor advised us. "Jimmy, you'll still have your family, and in today's society you'll still be able to do anything as a female that you ever wanted to do as a male. You'll live the rest of your life as a female but you'll have a life to live." Apparently my parents had heard enough to convince them. "When should he begin the change?" Dad asked after taking mom's hand in his. "Wait a minute, don't I get a vote in this?" I asked surprised that they had made such a decision. "Think about it for a few seconds," I was told by the counselor. "Do you really have any objections to becoming a girl Jimmy?" It was more time that I really needed. "No," I sighed. "Not really. I think it would be so wonderful to be a girl." "That's what I expected given the amount of time the program has had to influence you," the counselor said with a smile. "There are a few details which I was asked not to divulge before you made your decision, the company which made the tapes did not want to try to influence you in any way. The tapes were designed with the intent of making Tomboys into young ladies, they were never meant for use on boys. Your predicament however provided them with an entirely new market, changing males into females! You provided all of the testing they needed to successfully market a line of tapes for that purpose and they want to express their appreciation." "They're happy about this?" Mom was puzzled. "What if we sued them?" "That would expose your son here to a lot of needless publicity and embarrassment. They're very willing to make Jimmy's life very pleasant in return for his unexpected help in making the company unimaginably successful." When the plans were all laid out mom and dad were impressed and I was amazed. I was going to be a young woman there was no doubt about that but I would be a very well dressed and well educated one thanks to monthly royalty checks. "Wow, they've thought of everything haven't they," I whistled in amazement. "Not quite everything," laughed the counselor. "If they had you wouldn't be here today!" We left the office with a large packet of information detailing the changes that would occur and the promises the company was making. Maybe a normal boy would've been scared out of his mind over the idea of permanently becoming a girl but by now I was not a normal boy by any stretch and I couldn't wait to get home and out of my boy's clothes! Cindy was waiting for us when we got home. "Well, what's up with Jimmy?" she asked barely able to control herself. "Jamie," Mom corrected her with a grin. "She's Jamie Lynn from now on!" "Are you serious?" she squealed in delight. "He's going to become a girl?" "We'll talk about it later Cindy," Mom told her as she took my hand. "One tomboy for a daughter is enough, Jamie is going to learn to dress right! At least she'll know how to look and act like a young lady should." "Oh wow!" Cindy exclaimed, following us to my room. "My brother is going to become a young lady, this I've got to see!" I took off my shirt and pants to change into a pair of Cindy's jeans and one of her tops. As I was fastening one of the bras I had bought for myself it suddenly occurred to me exactly what had happened. I had spent months dreaming about how great it would be to wear girl's clothes but now it was so very real. I wasn't just going to dress up in some of Cindy's things for an hour or so then change back, I was going to spend the rest of my life wearing bras because soon I'd need them to support the breasts that I would develop! Every morning from now on I would slip the straps of a bra over my arms, I'd shave my legs and underarms every time I showered and when I finished my shower I would pull on a pair of panties. Mom was busily gathering all of my boy's clothes from my drawers and closets. I wouldn't be wearing them again, ever. I tied my hair into a ponytail and spent the rest of the afternoon listening to mom and dad explain what was going to happen to me. I was going to be a girl from now on I was told but for a few weeks I was to wear jeans or shorts until mom and dad got used to seeing me as a girl. Then I could wear dresses or skirts if I wanted to. "There are a lot of things you'll have to think of from now on Jamie." Mom poured some juice into my glass and set two small pink pills in front of me. "This is going to be an everyday thing for you now." I picked up the pills and looked at them strangely. They had no obvious markings yet somehow I instinctively knew what I held in my hand. "Is this what I think it is?" "Estrogen along with a testosterone suppressant," was dad's contribution to the morning's conversation. "One will stop any further development as a male and the other will make a female out of you. In about a month or so you and Cindy will be closer than ever before." The weeks dragged by so slowly I was beginning to wonder if mom and dad would ever let me dress up in something pretty. I spent my time helping with housework, practicing feminine mannerisms, and signing all kinds of forms which I never got a chance to really read, and of course listening to a few more tapes to reinforce my new lifestyle. Once in a while I got a chance to run a few errands with mom, I was terrified at first but whenever people mistook me for Cindy mom quickly corrected them and introduced me as Jamie. To those who knew about Jimmy mom simply said that I had been suffering from a recently discovered hormonal problem which made me seem like a boy although I was really a girl. Mom explained that it was thought that the best thing to do was to let me finish high school as Jimmy before setting things straight. People, especially women, ate it up! Instead of being considered some sort of pervert I was first pitied then admired for having the courage to become the girl I was meant to be! The story line was very helpful to dad since now people felt sorry that he had lost the son every man wants through no fault of his own while Cindy was considered the perfect sister introducing me to life as a girl! A totally win - win situation! Since Cindy didn't have enough jeans and tops for both of us mom took me out on our first mother daughter shopping trip to pick out a few things I'd need. I borrowed a cute little clutch purse that Cindy didn't use, packed a couple of tubes of lipstick, tissues, perfume that I'd bought because I loved the way I felt about myself when I wore it, a compact and blush for touch up work. I held the clutch purse tightly, smiled and waved to Cindy and dad as if there was nothing in the least bit unusual about what I was about to do then started for the door with mom. Mom must have sensed my true feelings or maybe she just heard my knees knocking but she was right there beside me whispering encouragement and helping me through the door. "You're doing just fine Jamie, you look lovely," she told me. "Just relax and let your inner feelings take over." Of course mom was right, once I took a deep breath and relaxed all of the feelings which the tapes had created in me took over. I was going shopping with my mom to buy some pretty outfits, just like any other girl my age I couldn't wait to get to the mall. I found the dreamiest blue dress with an empire waist and embroidered trim around the neck and arms within minutes of entering the first store. I stared at the dress trying very hard to picture what I'd look like in it. "Don't just stand there, take it and try it on if you like," Mom's voice broke into my concentration. "Take a couple of outfits with you though, it's such a bother to get dressed and come out for more!" "I can do that now, can't I!" I was overjoyed at the thought of being able to go into a girl's dressing room to try on clothes. This was so much better than trying to get Cindy to model for me! "You certainly can Jamie," Mom smiled. "You have as much right in there as any other girl!" Mom's words of encouragement pushed me to new heights of shopping pleasure, I may not have been a girl for long but I was determined to make up for lost time! Within minutes I was heading for the dressing room with an armload of skirts and dresses with one or two pairs of slacks thrown in for variety! I was heavenly to strip off my jeans and top then slip that gorgeous blue dress over my head. It fit very well against my padded bra and ended just an inch or two above my knees, nothing flashy just a very tasteful and pretty dress that would look good anywhere. I smoothed it out as the tapes had taught me to do then hips swinging stepped out to show off to mom. "That looks prefect on you Jamie," Mom beamed in pride. "With the right accessories it'll be just right for some special event this summer!" "I was thinking about white sandals with a medium heel, possibly nude stockings, Opal earrings, and a gold chain, what do you think?" I asked as I admired myself in a mirror. "Too much?" "Not at all," Mom assured me. "I think you have wonderful taste!" "I can't wait to show you some of the other outfits mom, I feel just like a princess!" I was bubbling over with joy as I hurried back to the dressing room. I modeled six dresses, five skirts, three tops, and four pairs of slacks before I was through and if I must say so myself I looked great in each outfit! One skirt was a gray, black and red check with wide pleats that was a little shorter than any of the other outfits but I felt it gave me a sexy look without being slutty so of course I just had to have it! Mom said that with my legs it would certainly catch a boy's eye which made buying the skirt a necessity! I hadn't mentioned it before, not even to Cindy but I desperately wanted to have guys look at me and to want me! In school I used to daydream about some of the cute football players and what it would be like to be their girlfriend and be held and kissed by them. After choosing several outfits including a couple of pairs of silk slacks, sundresses and shorts mom and I made our way to the shoe department where I picked out several pairs of summer sandals, six pairs of medium height pumps to go with the different outfits I bought and a pair of white sneakers with pink trim. The sneakers weren't the prettiest shoes I would have but I thought the pink trim would go far in offsetting their dull white look. Mom and I made a sales girl's day at the makeup counter when we purchased a deluxe makeup kit for my dresser at home, and enough foundation, powder, blush, shadow, and lipstick to that I could do makeovers on every girl in my senior class. Mom thought I was going just a bit overboard on the makeup but I assured her I'd need it to match the many different outfits we'd bought for me! Mom had saved the best for last, our final stop being the lingerie department! "Mom, I'm so happy I could cry," I whispered as we approached the racks of silk, lace, and satin in pretty pastel shades. I selected about two dozen pairs of panties in pink, blue, lilac, and yellow. I wanted some of the sexy little bikini styles but mom said that for now the full cut style would be a much more practical choice, later, when certain physical adjustments had been completed the naughty little bikini styles would fit much better. I spared no effort to examine every style of panties and bras the store had, I'd walked past these departments so many times in the past dreaming of being able to take my time and shop for just the right lingerie I wasn't going to be rushed now that the time had finally come. I found myself blushing as I held up a pair of very sexy panties, I wanted to buy them but I still wasn't sure I felt comfortable enough as a girl to be able to wear them. "I think you may be rushing things just a bit Jamie, they're just a little too much for a girl your age," advised mom. "Maybe in a few years when you've found the right man and settled down, they'd be a perfect treat for a romantic evening!" "Do you really think that could ever happen mom? Could I ever really fall in love with a guy?" Mom smiled at me. "Since you started listening to those tapes, have you noticed any different feelings towards boys?" I could feel the heat burning up my face and knew I must be as red as an apple. "I was so upset at first," I told her. "Suddenly I was noticing how cute some of the boys were and wondering what it would be like to be their girlfriend. I didn't know what to do until I found out about the tapes, I was so relieved!" "And now?" Mom goaded playfully. "What do you think about those boys now?" "Some of them are stuck up jerks," I admitted sadly. "But others!" "Others?" laughed mom. "Do tell!" "Others," I mused. "I want to make them forget that there are any other girls in this world! I want so badly to have them hold me tight, kiss me, and make me forget that there ever was a Jimmy!" "I think some boy is going to be very lucky!" Mom hugged me and smiled. "I'm sure you'll be the woman he always dreamed about!" We shopped a little more while I selected a bit more conservative lingerie than I had first looked at then headed home where I spent hours modeling my treasures for mom and Cindy, it made me feel very sad but dad still wasn't ready to see me in anything more feminine than slacks and tops. I took my new pills every day and it wasn't long before I started to notice small changes to my body and mind. My butt was beginning to fill out as were my hips and my chest was becoming so sensitive that I would occasionally get a cheap thrill from my padded bra rubbing across my nipples! I hadn't needed to shave yet before I started listening to the tapes and now the combination of blocking male hormones while increasing female ones had teamed up to make it unnecessary ever again. The changes to my mind started of course with the desire to wear pretty clothes and act like a young lady but took an interesting turn once the hormones had kicked in. Now I was feeling much more emotional, things that had never entered my mind before were now important to me. I started to notice things like the flower bed in a neighbors yard, the way items were displayed in stores, and of course boys! I had told mom when we went shopping that I had started looking at guys differently some time ago but now guys weren't just different, they were cute, well built, dreamy, and in some cases very desirable! To a guy it may seem silly that a girl would take a little extra time in the mall restroom making herself look good but when I was anywhere that guys could be found I made extra certain that my hair looked pretty, my outfit was perfect, my makeup just right, and that there was a happy look on my face. I knew from personal experience that nothing but nothing caught a guy's attention the way a smile would so whenever I saw a cute guy approaching I always tried to smile. I didn't care if I had just broken every nail on both hands, I was going to smile! A few weeks after our shopping trip mom came into my room one Saturday for a little talk. She solemnly announced that she felt that dad was taking far too long to adjust to his new daughter and that we were going to do something about it. "I managed to talk him into taking us to a really nice restaurant and then a show tonight," she announced. "This is going to be the night when your father realizes that you are a beautiful young woman and he's just going to have to accept it! I've already booked you with my hairdresser for a complete makeover!" "Are you sure this is the right way to do this mom?" I was barely able to conceal my excitement, Finally I was going o show daddy the girl I wanted to be and had become! "It's the only way left now honey," Mom assured me as I climbed out of bed tugging my baby doll nighty down over my panties. "We tried giving him time but he's having trouble accepting you as a girl. You're never going to be anythin

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Fairy Boy and Tomboy

Fairy Boy and Tomboy by Peggy Sue I was always a fairy boy, even before I started dressing in girl's clothes. I always cried at sad movies and stopped to admire flowers. I had long pretty hair from the time I was seven. The bullies taught me early that I'd better learn to defend myself, so I was a tough street- fighter when attacked. None of the bullies ever picked on me twice. I lived alone with my mother. I must have had a father once but no one ever talked about him. By the...

3 years ago
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A Bisexual Jock And His Tomboy

I think that love and friendship really shouldn’t mix. Seriously. It doesn’t matter if you’re a man or woman, black or white, straight or gay. If you are friends with someone and madly in love with them at the same time, you’re going to end up doing or saying something really dumb. You might succumb to the urge to tell this special man or woman how you feel and it might prove disastrous for your relationship. How else would you explain what almost happened between me and my friend the other...

2 years ago
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tomboy named Sue

This is a re-write of a story I did a few years ago. Hope you all like it. Tomboy named Sue The story is fiction, however, it is based on some of my early life’s happenings, and Sue was real (but not her real name).Our parents owned houses next door to each other. The neighborhood was lower middle class, so almost all families were living hand to mouth. Her Dad was a union machinist and did well enough so her mom did not have to work. My Dad’s goal in life was to own a home, something his...

3 years ago
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Wife Delivering Porn Tapes

Cheryl was eating her cereal when she heard her husband calling her name from upstairs."CHERYL," he screamed yet again."What honey?" she shouted back.She continued to eat her breakfast. It was nine thirty in the morning, she cleaned the house and sent the k**s to school, she was entitled to some breakfast."Can you come up here for a second?"She slammed her fists down into the table. "Yeah, I'll be there in a minute.""Thanks babe."She swirled her spoon around in her cereal bowl, counting...

1 year ago
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Dads tapes

Her dad didn't even know that she knew about his cache of X-rated videos he had hidden on the top shelf of bed room closet. Danni had found them purely by accident when she was looking for an extra blanket last winter. What she found under the blanket, was a box filled with about twenty videos that had just about every type of sexual orientation you could imagine! When her folks were gone, she would take one out and watch it, totally fascinated by the action on the screen. Being eighteen, she...

Lesbian
2 years ago
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Pool HouseChapter 8 Watching Tapes

The summer ended and we closed up the pool. We had moved a TV and VCR into the pool house so the kids could watch movies with their friends during the winter months. As far as my voyeurism went, I had to be content with watching tapes that I had made during the summer. My favorite was of course the one of Gena, Rachel and myself. In early November, one of the VCRs broke and I had to replace it. I waited until a weekend when Gena had taken the two kids to visit her parents for the day. I had...

3 years ago
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The Immortal Witch Inn Part 2 Tomboy

The Immortal Witch Inn Part 2: The Tomboy By M W Lord Heather's mother died giving her birth. Heather's father raised her the best he could but that was like a boy. She liked sports and building things. For as long as she could remember she felt like she was a guy. But sometimes she just had to go a long as a girl. In high school she even took classes in carpentry while the other girls took home economics. She never was attracted to the boys in school but she found...

3 years ago
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The Tomboy

?Are you still going to our gig tonight, Laney??, asked Mikey, as they bounded through the mostly-glass doors of Franklin High School. Mikey’s real name was Michelle, but she hated that name with a burning passion. It was too girly for a metal-head tomboy like her.  ?Of course. Knowing that I’ll be going to it is the only thing that got me through this hellish week,? replied the auburn-haired Laney, flinging her backpack over her shoulder. Mikey laughed, knowing exactly how she felt. Her week...

4 years ago
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Tapes

Tapesby Deirdre (address defunct)***Four people who enjoy one-upmanship end up playing and bondage and voyeurism, sometimes even a little blackmail to get their way with each other. (MF-cpls, reluc, bi, anal, bd, voy, blkmail)***I was a bit drunk at that party. That is really my only excuse. As if I really had an excuse when my wife, Sara, caught me outside with Judy, a woman with one thing on her mind that night. And I admit that if Sara hadn't caught us, I can't say how far things would have...

4 years ago
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Tomboy named Sue2

The story is largely fiction, however, it is based on some of my early life’s happenings, and Sue was real (but not her real name). Our parents owned houses next door to each other. The neighborhood was lower middle class, so almost all families were living hand to mouth. Her Dad was a union machinist and did well enough so her mom did not have to work. My Dad’s goal in life was to own a home, something his parents couldn’t do. My mother worked as a book keeper for a woman’s clothing...

3 years ago
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Patti Was a Tomboy

Chapter one. Patti was a tomboy, 16 years old, hair cut in the schoolgirl style and pretty quiet for the most part. She didn’t seem to have a girlfriend or a boyfriend and I didn’t know very much about her even though she was my next door neighbor. Our parents had no contact with each other mostly because of indifference. I had never really paid any attention to her. She was actually very good looking, blond with clean, flawless skin and a nice face and small but obvious tits, however she...

2 years ago
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Carmen the Tomboy Giantess

Carmen chugged from the can of Coke in her hand and let out a monstrous belch. “URRRRRrrRP!” She bellowed before tossing the empty can over her shoulder. Carmen Thompson was a total tomboy who was known to be quite the delinquent around her town of Bayweather. She had been to juvenile hall once before, and came back even worse behaved than she had previously. She was also quite the bully, which made her very feared within the halls of her high school. She had a total lack of respect for anyone...

Fetish
3 years ago
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Patti Was a Tomboy

Chapter one.Patti was a tomboy, 16 years old, hair cut in the schoolgirl style and pretty quiet for the most part. She didn't seem to have a girlfriend or a boyfriend and I didn't know very much about her even though she was my next door neighbor. Our parents had no contact with each other mostly because of indifference. I had never really paid any attention to her. She was actually very good looking, blond with clean, flawless skin and a nice face and small but obvious tits, however she walked...

First Time
2 years ago
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Tomboy

I'm a little old to be banished to summer camp," I said toSpike. Spike was my best friend, had been since I was eight. "I mean,I'm fifteen." I was sitting on a branch in an old apple tree, the lastone in the orchard. I had my back propped against the tree trunk. Shewas lying on the branch below me. Spike said, "Wish my folks would send me to camp, Kip." Herreal name was Danica, but I never called her that, just like she nevercalled me Clifford. "Yeah," I said. "Right." "No, really. First of...

3 years ago
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Tomboy

Tomboy By: Light Clark Synopsis: Sam likes to roll with the punches, both in fights and in life. Well, life gave him just such a punch when he manifested, but this one is a lot harder to just roll with than most. That's not going to stop him from trying to, though. Warning: This story is 'technically' set in the Whateley universe. It uses no characters or places from that universe; just borrows a few terms and general thematics. It is certainly not canon. Chapter...

3 years ago
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Hot Tomboy Little Sister 1

I always thought my little sister was pretty hot, but my fantasies began to become a reality when she was sixteen, a junior in high school. I was two years older, still living at home and working at the local hardware store to save money for college.She was five-foot-three with dirty blonde hair cut short enough to stand up, nerdy hipster glasses, and full soft lips. Her narrow hips gave her a boyish figure that was belied by her full breasts. You could see a bit of cleavage when she wore a...

Incest
3 years ago
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Its a Sin to Kill a Tomboy

He hated her, little overachieving, athletic, ripped teen girl who made his son look as he operated in slow-motion. She could pitch, catch play any position infield or outfield. For years, his son had played her on opposing teams or he had coached her on his son's team. She out ran, out hit, and out hustled everyone else. At 15 years of age, she played baseball for nine seasons. The team she was on won the championship six years and second place three years. She had lost a single game as...

2 years ago
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Tomboy

The year - 1835. The place - the Wild Wild West. John McNaughtin was the typical Wild Western family man - he lived on the outskirts of a sleepy town whose only trouble came from the wild hogs that sometimes ran their way. No gun slinger had ever set foot in this town, and the sheriff was a quite cheerful seventy-year old man who hoped that he he still had the star when his age became three figures. The houses were wide-spaced, and had sizeable grounds of their own. The neighborhood was...

3 years ago
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Teaching The Tomboy

With input from Homer Vargas Toni had just finished fixing the neighbor's car sitting in the family driveway when she heard her mother call her. "Toni hurry up and take a shower before you go" Toni winced. She had dreaded this day. She was going to be stuck all summer helping her mother's friends at some kind of day care center. She much preferred working on cars for people though it didn't pay much. Even though the job would mostly be landscaping, Toni was sure just being around a...

2 years ago
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Antheas baby 1

“What’s wrong? What’s wrong?”Anthea looked up at her mum as she sat down at the dining table. “Nothing is wrong,” Anthea responded watching as her mum hurriedly dried her hands with a tea towel.“Is the baby okay? Are you okay? Is Jack okay?” she asked as her husband came into the room and pulled up a seat at the table.“We’re all fine Mum,” she responded exasperated with her mum’s anxiety. “I have something to tell you.”“Sit down Helen,” her dad snapped. “Give the lass a chance to speak.”Anthea...

2 years ago
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A rough tomboy

“who is a bad bitch?! You are! Yeah, that's right!” Jamie hardly ever lost a fight, and she was a skilled fighter. She hit him one more time except for this time not as hard. “fuck for a girl, you hit like a man. Must be embarrassing to be beaten up by a woman. Shit, you're not a woman. You're a fucking man.” she hits him again and knocks him out and she got up looking over at me. Stares for a few seconds and then she walks away, surprisingly, she hadn't told me anything. I wonder if I...

4 years ago
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Uther

Uther By Ellie Dauber (c) 2006 Introduction According to the legends of King Arthur, Merlin changed Uther Pendragon into a double for Duke Gorlois, so he could spend the night with Ygraine, the Duke's wife. Ygraine and Gorlois had three daughters: Elaine, Morgause, and Morgan le Faye. During their time together, Ygraine became pregnant with the child who was to become King Arthur. Uther's men killed Gorlois that same night. This is my TG (of course) version of what...

2 years ago
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Carruthers Bride

The the wind howled around the quayside as I stepped onto terra firma for the first time in weeks, the wind threw sharp shards of ice to sting our faces as we looked up at the sails as they were finally furled and stowed as our captain grinned at our discomfiture, "Au revoir!" he joked as if he knew we should soon be recalled. Those such as were left, and we were few enough, I shuddered. My best uniform packed securely in my Valise, awaited me, and just a few more duties before I...

1 year ago
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Motherless Vintage

Do you know of the porn site Motherless.com? You should. I’ve reviewed it a few times on my site, The Porn Dude, although it was for different genres every time. This time around, I’m going back to this place and looking at a specific and niche little category many of you are just begging me to cover. We’re looking at vintage porn today. While it doesn’t have the same resolution and quality as the porn you can find today, it’s definitely a genre of porn that has a lot of personality to it and...

Vintage Porn Sites
3 years ago
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Althea

I should have known better. I should have remembered that old saying, "If it looks too good to be true, it is." I was in love. She was damned near all I thought about with the exception of my studies and it didn't make sense to me. I prided myself on my intellect and my ability to think logically, but there wasn't anything logical about the way I felt about Althea. She was beautiful, smart and very popular and I was not. I wasn't a bed looking guy, but I was nothing exceptional. I was...

1 year ago
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Motherless Images

Motherless. A one-word website title that says everything it needs to say. This is a site where the rules are, more or less, completely thrown out the window, morality means absolutely nothing, and there is nobody to save you from it. Hedonism is God here.The site likely is also called this due to the fact that the girls who end up on motherless.com likely have no positive female influence in their lives to keep them from it. Motherless is the place parents spend their whole lives fearing that...

Porn Pictures Sites
1 year ago
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Motherless Amateur

I always considered Motherless the “4chan” of porn. Not only because Motherless was somewhat popularized there, but because Motherless also encourages users to share their own content in a very open way. This means minimal bullshit like moderation and censorship, and a strong “anything goes” attitude that leads to free and extreme content. It encourages people to create and upload their own homegrown content, like videos of their girlfriend pissing or spycam videos of their cousin....

Amateur Porn Sites
1 year ago
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Motherless BBW

What is it about Motherless that makes me fucking cum every time? Maybe it is how raw and amateur the porn on the site comes across as, or the content is just that fucking hot. Perhaps it is the fact that there is an astronomical amount of pornography just waiting for a dumb fuck like you to beat off to! I really don’t know, and frankly, I’m not going to pretend that I do.But what I do know is that if you love BBWs, the Motherless.com homepage will not be of much use! Preferably, head on over...

BBW Porn Sites
1 year ago
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Motherless Voyeur

Have you ever heard about a website called Motherless? Home to all kinds of kinky porn niches, with a side of the mainstream crap? If you are into some questionable fap content, you might want to check this website out. Plus, Motherless is a free porn website, so you can browse as much as you fucking want. Now, I am not really here to talk about the website in general… I am here to tell you about their amazing category, called voyeur porn.The world of voyeur fucking is a rather interesting one....

Voyeur Porn Sites
2 years ago
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Aether Guardians

The Five Kingdoms of Arstoria had been embroiled in the Great Ancient War for centuries. The war came to an end when Kalace, the Wizard King conquered the five lands and brought them under his rule. Kalace, the Wizard King of Arstoria, conquered all of his opponents who were unable to deal with his overpowering magic. When Kalace had united the five kingdoms, he brought peace to the warring kingdoms and was revered and celebrated by his later generation. Kalace, however, had a dark weakness in...

Fantasy
1 year ago
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Motherless Creampie

Woah, did Motherless.com get a facelift? I know I suggested it in my review, so I guess they listened to me! Well, I’m not going to brag too much about it, and instead, I’m going to focus on what I’ve set out to bring you today. We’re looking at an amateur website, and I just know that many of you are begging for amateur creampie content, so that’s what we’re looking at. I know how much you think Motherless can look sickening and pretty gruesome at times, but the creampie content can be quite...

Creampie Porn Sites
1 year ago
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Motherless Cuckold

No matter what type of porn you may be in the market for, Motherless has an ample supply of it, and cucking is no different. Actually, this might help to explain how you ended up being such a pussy little cuck.The journey that brought you to my website reading cuck porn reviews started in your childhood. A fair portion of my readership is actually motherless. Why, you ask? Your guys' moms chose a life of cucking and riding cock instead of raising you fucks properly.Don't worry, gents. I'm in...

Cuckold Porn Sites
1 year ago
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Motherless Horror

I browsed the horror stash at Motherless all morning, and now I don’t know if I should jack off or go hide in the closet until the danger has passed. Then again, hiding out might give me the perfect opportunity to rub one out in the peace and safety of the dark. Who knows who—or what—might be peeping in the windows with nefarious intent if I sit at my desk and shake my dick at the screen. Just like when I masturbate at the local Starbucks, I’ve got to be sure to balance the potential pleasure...

Extreme Porn Websites
1 year ago
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Motherless Incest

Incest porn has been a staple of pornography since the very first incel caveman realized that he couldn’t find fresh pussy out and about. He resorted to sniffing a whiff of his mother’s loincloth when she wasn’t looking, and beating his old cave meat into a leather sock.Now personally I’m not into the whole mommy-son dynamic – I’m a classy guy. But it’s no secret people like to get freaky when the lights go out, and if you’ve got a stiffy in your hand and you’re on Motherless, you gotta go...

Incest Porn Sites
2 years ago
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Absinthe Makes the Heart Grow Fonder

Thanks to my usual cast and crew of Editors and Advance Readers, most of whom prefer to pretend that they don’t know me and wisely wish to take no responsibility for any part of my addled writings... Il n’est rien de réel que le rêve et l’amour - Nothing is real but dreams and love (from Le Coeur innombrable, IV, Chanson du temps opportun by Anna de Noailles) She was my one true mistress and ever faithful lover, my Green Lady and guardian of my dreams and now that I was back home...

2 years ago
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Thea Chapter Four

When the car with Jake in it became a dot on the horizon, Thea turned to go back in the house. Suddenly Floyd appeared. “Mrs. Thea, how you be?” Smiling, she knew immediately what he wanted. He had that look and a glance at his crotch confirmed it. The imprint of his cock was prominent as it pushed against the material. “Looks like everyone is gone.” Floyd said. His eyes looking out over the farm. “Yes, I am by myself for at least the next few days.” She replied in an...

3 years ago
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Thea and Sam

“Well, hell,” Thea said as she wiped the beads of perspiration from her face. “I guess ‘spring’ is here, huh?” “Yeah. It’s supposed to be cooler at higher elevation,” I replied. We took a few minutes in the shade by the rocks before rejoining our boyfriends. The four of us had driven up into the pass to hike. According to the weather report, the last coolness of a fading winter was supposed to continue through mid-week, but they were wrong. Actually, from our view from Eagle Point, where we’d...

1 year ago
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Motherless

Motherless.com! What an original name for a porn site, don't you think? The title doesn't fuck around: your mother would never allow you to watch the kind of filth they’ve got on tap. They pride themselves on being a moral-free zone for sick fucks, where you can find damn near anything. I’m talking about desperate chicks fucking anything that resembles a dick and crazy bitches literally eating shit. When you’re done fapping to the weird vids, you can even find "normal" porno to pass the time....

Free Porn Tube Sites
1 year ago
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Motherless Interracial

Ah, motherless, here we are again. A site known for offering such a variety, that no matter how fucked up your needs are, there is a high chance that you will fulfill them here. However, I am not here to blab about the site in general; I am here to talk about one particular category, interracial. As for those who want to know more about the site, there is a whole different review on my website instead.As for those who came here to learn more about that interracial lovemaking, I got your back....

Interracial Porn Sites
1 year ago
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Theos LIfe as a Weresquirrel

Theo had been changing into the squirrel too much, he knew that now... as a pulse of heat raced through his body from his groin. He realized that he shouldn't have come to the office.He had been spending most of his days at the squirrel in his home deep in the countryside. Teleworking most of the time, as the squirrel he felt no need for clothes, his heavy furred balls resting between his thighs as his paws raced over the keyboard. The sharp claws on his paws clattering loudly as he typed,...

Fantasy & Sci-Fi
1 year ago
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Motherless Scat

It’s time to go to the land of chocolate fountains and golden showers. That’s right. Scat, piss, shit, and every fluid in between. Ever fuck a chick in her ass and freak out when you see that little bit of shit on your dick? Then I’m sorry to say that scat isn’t for you buddy. Were you the only one of your friends that saw two girls one cup and didn’t get grossed out? If so, it’s time to celebrate it! Don’t get pissed off, get pissed on! Scat porn has the craziest, kinkiest chicks and dudes...

Scat Porn Sites
1 year ago
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Motherless Fappening

I’m not saying anything controversial when I say men love seeing women naked. It’s a fact of life as fundamental as gravity. It’s a force of nature that cannot be stopped by beast, man, or God. It’s an eternal truth and a divine mandate. As sure as the sun will rise, men will attempt to view as many women naked as they possibly can. Any man not doing so is either a sad or a gay one.This means that any woman a man sees regularly is mentally stripped down during every interaction. If any women...

The Fappening
3 years ago
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Absinthe Dreams

‘To me it’s not really a green. When I think green, I think of grass. That’s more like lemonade color.’ Erica’s nose was far too close to the glasses for my taste. Pouring the nearly clear absinthe over the rough-cut, cane-sugar cubes I favor, I tapped my spoon for a second to get her to back up. I wished I had my full setup here like I have at home, my Absinthe fountains water drippers are missed when I began to try and slowly pour water over the sugar cube. ‘Don’t you light it on fire?’ she...

1 year ago
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Motherless Arab

Have you ever heard about a wonderful site called “Motherless”? I have a feeling that was a dumb question, of course, you fucking have. Well, I am here to talk about Motherless, but I shall also pay special attention to their Arab category. If you think Arabian sluts are hot, well you are in for a tasty treat, believe me.First, I should probably warn you that the name of this place comes from the fact that their content might be a bit too hardcore or questionable for some of you. Back in the...

Arab Porn Sites
1 year ago
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Motherless Facials

Fuck yeah, life’s a bitch! So here I am, awake at 3:45 AM, after dreaming I was fucking this freaking hot MILF neighbor with heavy boobs, a flat tummy, a nice bubble butt, and sexy long legs. It was all hot and steamy, up until when she was sucking me off and just as I was about to obliterate her cute face with hot cum canon, my dream cut right off and I woke up with a tent on my pajamas.That dream ain’t coming back, but damn it! I sure gotta cum, so I boot up my laptop and type “cum facial” in...

Facial Cumshot Porn Sites
2 years ago
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The Tomboy

This story is dedicated to my great friend BobbyLynn. I met Bobby when I was 18 and she was 9. I had just moved to Ohio from North Carolina. I was living with my older brother in his little two bedroom house. I had just graduated high school and was planning on going to the local Tech school to take auto mechanics. I already knew quite a bit about cars and spent most of my free time working on them. My brother, Todd owned his own auto shop and was letting me work for him doing what I did best.

2 years ago
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A Humiliated Tomboy

Alex sat on her bed, playing video games. She was a cute high school senior in a baggy hoodie and basketball shorts, her orange hair cropped at her shoulders. She was sucking at her braces in concentration when she was interrupted by a knock on her bedroom door.

2 years ago
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Teen Tomboy tamed

I rolled my eyes as my parents dropped me off in front of the green house. I made my way pass the white picket fence and up to the door, knocking. I barely gave the massive man a glance as he let me in. My short blonde hair hangs in my blue eyes. As I size up the towering bear of a man. The threat of military school if this doesn't work hangs over me like the sword of Damocles. I glared at the back of his gray suit as he lead me to my new room. Apparently my mom knew him from college and...

BDSM
2 years ago
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Basement Experimentation With My Tomboy Pal

The smooth, white skin on the inside of Tara's thighs was soft and sensitive. I slid my hands up and down from her knees to her girlish shorts, taking in the flats and the curves, noting the hem of her white panties poking out from beneath the pink and yellow denim. She watched me with interest while I explored her. It was the first time I'd been this close to a girl's body and the intimacy was as exciting as was the forbiddenness of it. We knew we had to stay quiet in my parent's basement. No...

4 years ago
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Tentative Tomboy to Girly Goddess

Tom walked down the suburban street, head buried in his phone. He had walked this path for years, picking up his friend Zoie on the way to school, and at this point, his feet moved almost on autopilot. More than once, she had grabbed onto his shirt, stopping him from stepping out into traffic when he was distracted by their conversation, a wandering thought, or some equally momentary diversion. Today, though, was different. For two reasons: Tom's green eyes, normally hidden behind...

4 years ago
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Hot Tomboy Little Sister 2

One warm spring day, after Cait got home from school, we went for a walk in the woods. I enjoyed letting her get a little ahead so that I could watch her tight ass pumping with each athletic stride. We walked until we came to the nearest lake, then sat on a flat rock, taking our shoes off and cooling our feet in the shallow water.I sat close enough to feel the side of her thigh against mine, sensing the muscles tense when she splashed her foot out. We talked about nothing, her school gossip,...

Incest

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