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Kids are curious. That's all. That's what started it all. I wasn't being weird. I wasn't turning gay. I was just trying things on. I was just feeling the silk and the other fabrics and the silk. Don't most 16 year olds try things out? Doesn't everyone want to be pretty? There was a blue dress that my older sister Jenny had left. A simple blue dress, but it mesmerized me. It was a simple shift, but it fit me better than most of her stuff. It felt sensuous. It felt delicious. Hour after hour, I spent, figuring out the clasps and catches and tabs, the zippers and the velcro. It was a wonderful mystery to me. It felt heavenly against my skin. Except for a dab of lipstick, I didn't know enough to play in her cosmetics. I wasn't really attracted by her jewelry. Not then. But her panties. Her dresses. I could spend an afternoon dressing. I guess it was inevitable that I would be caught. My step-mom (no, this isn't an evil step-mom story) is named Charlotte. She's only 10 years older than me, hardly wizened enough to raise a teen- age boy. So when she came into my room with an armful of laundry, and I was in the blue dress, her jaw dropped open. "Oh, my," she said. "Oh, hi, Charlotte," I said. "I'm ...I'm just playing. You see, there is this party..." She grinned. She looked me up and down. I felt two inches tall. "So which is it, Mike? Is it a party? Or are you just playing? Tell me, pretty girl." "It's both," I stammered. "I was just trying things on to see how they looked. That's all." "Uh-Huh," she said. "Well, you look cute. Can I help you at all?" "Uh, no thank you," I said. I felt like pulling the dress off. But then she would see I was wearing a bra and panties. "I was just going to change and go play some hoops. I was looking for my sneakers." "Isn't that them there?" she asked. For some reason, that made me blush, too. I was saying everything wrong. "You know, Mike. I have some old dresses you could have if you want. It's okay. I know a lot of young guys are transvestites. It's normal enough." "Um, no thanks, Charlotte," I said. "I'm not. I promise. I was just wearing these." Wearing these? Of course you were wearing them, you moron. What else would you do with them? I disappeared into the bathroom. I couldn't get the dress off fast enough. Or the panties. Or the bra. I was never going to wear them again. I can't believe I wasn't more careful. I can't believe she saw. I hoped she wouldn't say anything to my father. He'd kill me. I tugged on my gym shorts. I pulled on a t-shirt. Yeah, I was all boy again. Wasn't I? *** She told my dad. Of course she told my dad. Parents talk to each other. They are sure it is them against their kids. So they talk. I would later find out it was that same night, when they were in bed. My dad reached over for Char, romance on his mind. And Char said, in those ominous words all all time, "Stephen, we have to talk." "What's the deal?" my dad, rising off her and sitting up in the bed. What guy wants to talk in bed? "I'm Mikey. I'm worried." "About?" "Okay, don't get upset. But I think Mikey may be gay." "What? Mikey? Why do you say that? Did he...." "No, I didn't catch him and another boy. I just went into his room today, and he was wearing ... a dress. I think he had on a bra, too. It was the bra that convinced me he had done it before. He seemed very comfortable. I think he's worn them before." "I can't believe this. Although...Mike is a little guy, and I he's a bit girly. He used to play with dolls. He and Jenny used to bake. But that doesn't mean he's gay." "Doesn't mean he's not. Look, there are a million gay kids out there. Why wouldn't our kid be one of them? He's still a great kid, you know." "I know. I guess every father is concerned about it, down deep. It's a hard life, being gay. You think it was the divorce?" "No, silly. Some people are just born gay. Our son just likes dicks. Ha. Doesn't make him evil." "I should go talk to him." "No. Not yet, Steven. He was terrified of you finding out. I think we should just educate him a little more. Leave some clothes around. Leave some magazines. Talk about homosexuality at the dinner table. Let him know it's okay." "Mikey's gay?" my father repeated. "Mikey's gay. Well, gays can get married in our state now. Maybe he'll meet someone and be a good wife. That's all I want. Is for him to be happy." "Me, too, baby. And pretty." *** I later heard about the conversation, and yes I know it was filled with misinformation. Being curious doesn't make you a transexual, and being a transexual doesn't make you gay, and being gay certainly doesn't make you someone's wife. But these were a pair of vanilla parents trying to do the right thing. They loved their kid. Even now, I find something honorable in that. For all their clumsiness, their hearts were in the right place. And so assorted dresses started to show up in my closet. Panties. Bras. There were transvestite magazines, some of them slick and gorgeous, some grainy and filled with porn. A vibrator showed up on my night stand. And, yes, I wore the clothes. I swore I would never do it again, but there they were. There was an ivory colored nightgown. A yellow sundress. A wig. A rainbow of lipsticks. If I wasn't trans when I tried on Jenny's blue dress, I was becoming one with my parents' encouragement. Charlotte knew I was dressing, and I knew she know, and she knew I knew she knew. I didn't play basketball anymore. I just came home and played dress up. One day, when my friend Larry was over, I dressed for him. He laughed. "Jenny's?" "Yeah," I said. And so he rifling through her clothes, and soon enough, he was dressed. No, nothing ever happened. Larry did it that one time, never again. He never acted as if I did again, either. We were just two kids playing in cloth. Looking back, I wonder if I wanted more. Maybe. I was awful curious. So, too, was Char. It was in mid-summer when Charlotte came in the front door and called to me. I bounded down the stairs - I wasn't always dressed - to see how I could help. Charlotte was as cheerful as ever. "I got you something, sweetie," she said. "Something for me?" I asked. "For you." And she held out a lavender dress that shimmered in the light. It may have been the prettiest thing I've ever seen. I damn near swooned. "I don't want, Charlotte," I said. "I'm not..." "Mikey. We know. It's okay, sweetie. I'll bet Larry will love you in this." "You know...what? And Larry? What the heck does Larry have to do with it." "Sweetheart, we know you're gay. It's okay, baby. Some people are. We've talked about it. We joined an online group for parents of gay kids. Not all of you wear dresses. Just use protection, okay? And if you need to talk to someone, it's okay. We want you to be okay being gay." So there it was. My parents believed I was gay. It didn't matter how many times I told them I wasn't. They were so reassuring, so comfortable. "Sweetie? Don't you think it's time we saw you dressed up? I'll help you with your makeup. You can be the girl you want to be." Did I want to be a girl? Honestly, I didn't think so. I just liked wearing the clothes. But Charlotte was being so...nice. I found myself reaching toward the dress. I saw her smile. And I surrendered. When Daddy got home that night - and it seemed right to call him Daddy - I was in the lavender dress with purple heels and full makeup. He saw me and smiled widely. "Hello, princess," he said. "It's about time you said hello." I smiled shyly. I handed him a scotch, the way Charlotte had told me. He kissed me on the cheek. "Do you have a name?" he said. "A girl's game?" "Becky," I said. "Well, Rebecca, you're a lovely girl. I expect to see you more often." I glanced at the floor. This was embarrassing, having Daddy see me in a dress. The news that it would happen more often - that a page had turned - floored me. I had thought this would be a one-time costume party, not my entrance into womanhood. Was I ready for this? And did "this" care? *** Some parents are cool. Some parents like their lifestyles of their children no matter what they are. If their girls want to be boys, if their boys want to be girls, if they want to be gay or play dress up or whatever, it's okay. My parents went further. They wen't just accepting, they were assisting. Charlotte bought clothes galore. My dad introduced me to one of his junior execs, a guy who flirted with him endlessly. They joined pro-LGBT parental organizations and other support groups, They put rainbow stickers on their car for all the neighbors to see. One night, they were talking to another couple of parents. "And what kind of girl is Rebecca?" Charlotte asked. "What kind? What do you mean?" "Oh, baby, there are so many kinds. Lesbian. Tops. Bottoms. Dommes. Sissies. Tomboys. Girly girls." "Um, she's not a lesbian. She had a boyfriend. Larry. What were the others?" "Well, there are domination games. Mistresses and sissies, for instance. There are tomboys and girly-girls." "Well, she's pretty girly. Stephen, is she a mistress?" "Oh, I wouldn't think so, hon. She's sweet and quiet, a little shy. She likes to cook and clean. Does that mean anything?" "Well, she could be a sissy," the other parent said. "Does she like maid's dresses?" "I don't know. I've never bought one for her. Do you think I should?" "Maybe. A lot of girls like that. You say she cooks? Sissies love to cook. They like being told what to do." "Rebecca likes being told, too," Charlotte said, thinking pensively. "Last week, Steven brought home a boyfriend for her. Taylor. She didn't even kiss him. I'll bet she was waiting to be told to." "And maybe more." And everyone laughed. I seemed to be quite the amusement these days. I didn't know what to think when I saw the maid's outfit. I thought Charlotte was having more fun, I guess. There she went, jumping to conclusions again. Just because I had baked as a kid didn't mean I was a maid. Of course, it didn't mean I wasn't, either. It was Saturday, and I was up early. Already, I had on a sundress (all I wore were girl's clothes these days). My hair had grown out, and it draped my face. I padded into the kitchen to take my morning pills (yeah, my parents' idea), and there it was, a black ball of lace draped over the back of the chair. It was beautiful. It had white lace trimming, and an apron, and heavy petticoats. There was a small hat. I held it up against my body. It was so soft, so light. I felt a stirring in my groin. For all the dresses Charlotte had bought me, for all the times she had taken me shopping, clothing had never affected me like this. I unzipped the sundress. I had to wear this. *** Charlotte found me in mid-morning in the kitchen. I had a pot of tea on, and I was baking croissants. I had rearranged my hair to wear it was up in a bun. "Ooh-la-la," a voice from behind me said. I turned, and it was Charlotte. "You like?" she said. "I like," I said. "Is it asking too much for my maid to pour me some tea?" she said. And so another page turned. I was still short of my 17th birthday, but my father offered me a job as the house maid. I took it. I washed dishes. I did laundry. I vacuumed. I made beds. I was no longer that fumbling teenager of a few months ago, dabbling in femininity. This completed me. This was what I wanted. I no longer had to define if I was trans or gay or playing around. I was a sissy. I didn't care who knew it. In the days to come, everyone would know. Neighbors drop by. Support groups meet. Teachers have conferences. My parents couldn't tell everyone fast enough about their girl. Maybe this was good. It was embarrassing, but maybe people deserved to know. Maybe I deserved the laughter.Hey, everyone doesn't go to college and become a lawyer. Some of us are destined to wait on him. And so my life went. Taylor, the junior executive, asked me on a date. Yes, I went. Modesty prevents me from saying if anything happened, but I did learn how to get sperm stains out of a dress. Ha. Taylor had a beautiful body, hard and sweet. My was was softer. My breasts had developed into the perfect sissy's. Looking back, my parents were too eager. They made too many assumptions. They pushed too hard. But you know, they were mostly right. They enabled all of this. I loved them. I loved me. I loved life.

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Psych eval, coffee, hallway, metal detector, commissary. That list could go on for a while. It’s a word-association of an experience I wish had not been necessary. An experience borne of someone else’s lie, and one that will stay with me, as well as everyone else involved. I will never forget the night I was at a party, went to my car to get my phone, called her back. ‘They arrested him,’ she said. I can think of no more fitting analogy than the environment in which I was in when I heard those...

2 years ago
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THREE SHORT STORIES ABOUT JOAN

I was scrolling through porn here on xhamster & I saw several images of buxom ladies all done up in corsets, with their boobs all spilling out, etc at Renaissance Faires & it reminded me of a story ... well, three stories actually.I."Joan" is probably my wife's closest friend. They've been friends since college. Long time. For nearly ten years we used to go on vacation with Joan, her (ex)husband & their three boys in Mexico.The boys were little - the youngest was five, the middle...

2 years ago
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City Romance Ch 03

Monday The weekend went off without a hitch. After spending the night at my place, the girls and I went shopping and decided to stay at Dawn’s place to utilize the hot tub and swimming pool. ‘God Dawn, if I lived here, I’d never leave this pool!’ This was the typical response for Ariel, who had coincidentally been on our swim team in high school. ‘And we’d find you frozen like leftovers in the middle of the winter you idiot. Come eat and let your skin stop looking like a raisin before...

1 year ago
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Fucked in Mexico

I'm a 43 year old mother of 3, I'm 5.10, 220lbs. could be described as chunky with large tits and very wide hips. My husband and I were on holidays in Mexico at an all inclusive resort. My husband loves golf and played almost every day while we were there. On Wednesday morning we got up had breakfast then Chuck left for his tee time. I was wearing my blue Bikini, that didn't cover much but hey what the Hell I'm on holidays and I'll never see these people again. I sat by the pool for a couple...

4 years ago
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Our new baby sitters mum 4

Introduction: Wendy goes on birth control, Helen thinks about getting pregnant, first Friday night party starts This is the sequel to Our new baby sitters mum (1), (2) & (3) It is almost certainly better if you read them first. Veronica, my GP and Friday night playmate, was not the slightest bit surprised that Helen wanted her 13-year old daughter, Wendy on birth control. Is there any chance that you might be pregnant, Wendy? No. None. So you havent had sex with anyone yet? Yes. Ive given...

4 years ago
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Explorations beyond my expectations

I was nineteen at the time and Lili was my first college girlfriend. She was a virgin when we met. I had only had one intimate girlfriend before her. We loved to explore together and every weekend her roommate would leave town on Friday night and wouldn’t return until Sunday evening, giving us plenty of time to explore and play. She knew I liked ass play from conversations about things we’d done in the past and I held no secrets back about how I really wanted to explore those feelings...

2 years ago
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Mrs Hill

She was my granny’s neighbor. She was a fat elderly woman of about 65-70 with huge boobs and enormous ass. That summer I was helping my granny with the house and her neighbor Mrs. Hill often asked me to help her too. She lived alone, her husband died, and her relatives didn’t visit her often. Now and then I felt her looking at me in a strange way, but didn’t really pay attention to it at all. It was Sunday, I spent the whole day helping both of the ladies round the house, it was night, and I...

3 years ago
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Pretending Ch 09

Pretending Ch. 09 © 2009 All Right Reserved Connie let the water run down on her from the shower head after she'd finished. The hot water felt wonderful after such a long day. She turned off the water, wrapped her hair in one towel and grabbed another for her body. While she'd been in there, she'd gone back over what Emily had said. Her sister was right. She needed to tell him, and tell him now. She tucked in the corner of the towel and stepped into the hallway, then tiptoed down the hall to...

Love Stories
1 year ago
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Kathy White Trash Whore Part 11

She also told him to wait up for her. It was only just after 8pm and he was sitting on the sofa in his bath robe, watching T.V. when she came home. She stood in the living room doorway, her messy red hair falling on the shoulders of the black leather jacket, which was open down to her waist perfectly framing her firm and ample boobs. Jeff loved her to wear jeggings; the skin tight denim look really showed off her legs and backside, and the knee high, black leather, full laced boots,...

2 years ago
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crazy public adventure

So this is an experience I had back when I was 17 or 18. I’ve never told any one of this story until now. This adventure took place back when I lived in NC and I used to work at these public soccer fields opening the gates, putting out flags on the fields, and maintaining the overall daily functions that take place at the facility such as making sure games run smoothly.On most days the fields would mainly be utilized by high-school teams,clubs and adult leagues. For the most part the job was...

4 years ago
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The Beardsley School for Girls 52 Carleigh

The pain was secondary to the pleasure she felt. She fucked the plank, slid along the old wood, her juices made the trip back and forth easier as her pussy slid along. She felt a familiar tingling between her legs, but this time it was different. It wasn't her fingers aroused her but a torture device, her pussy forced to rub harshly up and down the edge of the plank, raw, but still brought powerful bursts of pleasure. Headmaster Michael had taken his cock out, his hand wrapped around it,...

4 years ago
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Battlemage Book 4 the Red DragonChapter 3

"Hey Anne-Marie, what's up?" asked Rayne as she dropped into a chair across from the guild master crossing her legs out in front of her. "Rayne how was your visit with your family?" asked Anne-Marie smiling. "Great. Those two knuckleheads are still stirring up the family and they are still getting into trouble. And Jaden has something over on his wife now, but it's only a matter of time before I figure it out," said Rayne as she smiled. As she talked on, Anne-Marie noticed that she...

2 years ago
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Zaks Encounter with Louis Part 1

When I arrived at the door the gym was locked. I pulled out my badge to get in. As the door was closing someone called out for me to hold the door. I turned to look, and it was Louis.We walked back to the locker room and Louis took a locker next to me. Louis had blonde hair down to his shoulder and was medium build and six feet tall. While I was taking my clothes off, I felt that Louis had an eye on me. I was down to my hipster panties.Louis was taking his pants off and I noticed he was wearing...

Gay Male
3 years ago
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Kennel Girl

It's kinda weird how it happened I guess. I was always interested in dogs but just a normal everyday kind of interest nothing “K9”, but I'm getting a head of myself. I didn't event know it was called that back then. All I knew was I wanted a dog and I had pestered and pestered to try and get one for ages promising to take care of him and exercise him everyday but my parents just wouldn't bend, “No” was the answer. Finally, after months of pleading, they made a bargain with me, if I took a...

4 years ago
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Lottery WinnerChapter 8

She took a half step forward and I pulled the zipper all the way down her dress. She let it fall forward off her arms, slide down her body and fall to the floor. She was wearing a black bra that hid little of her breasts and black thong panties. She reached behind and unfastened the bra as she turned. She then slipped off her heels. “It’s up to you to remove my panties, dear man.” It was said in that same low voice that was sending shivers through my body. I pulled her to me kissing her and...

4 years ago
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Latent DesiresChapter 2

The next day I did my chores in record time and then went out. I had shopping to do. It was going to be a very special night -- candlelight dinner, wine, and the biggest surprise of Ron's life, not necessarily in that order. When I returned home I placed the fresh daffodils in the center of the dining room table, between the two silver candlesticks holding long, blue candles. The yellow flower brightened the room. And then I ran upstairs, throwing my packages on the bed and then placing...

4 years ago
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Una hermosa mujer llamada Carla Prt 4

Como están queridos amigos, ante todo mil disculpas por la ausencia pero estuve recavando mas material para las historias.Una vez dicho eso continuemos con el relato.... Esa noche al llegar al hotel estaba a mil por hora por lo que había sucedido con Viviana así que me dirigí de lleno al penthouse de Dña. Tere, pero grande fue mi sorpresa al ver que estaba acompañada por otra señora que al verme se puso colorada, imagine que casualmente estaban hablando de mi, al ver esto me acerque a a saludar...

4 years ago
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Her Tongue Tasted of Rye Whisky and Cloves

Cheaters never prosper, they used to tell me. I've made a life of cheating, and while I wouldn't say I've prospered,  I wouldn't complain. My wife never really understood me. Hell, I never much understood her. But over the years, we managed to develop an "understanding". We don't pry too deep into each other's affairs, business or otherwise. I still remember the first time I broke those solemn vows to love no other but my lovely, frigid, back-biting, bitch wife. I mostly remember that girl's...

Taboo
3 years ago
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Modern Relations part 08 Its Complicated

Wendy: 4:40 PM “Okay, Okay, hold your damned horses,” Wendy yelled at the door. After ringing constantly for half a minute the door buzzer finally relented. Fresh out of the shower and dripping water all over her apartment, Wendy checked the time as she ran for the door. Andy was twenty minutes early. Wendy jabbed the intercom button, “that better not be you, Andy.” Jerking her finger off the button, she added, “because I’m getting tired of your fuck ups.” “It’s me, can I come up?” “Alex?”...

4 years ago
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Fucked Hot Bhabhi In Front Of Her Husband 8211 Part 2

Hi readers , Thanks for your comments. This is a continuation of my first story in which I fucked Namrata in front of her husband. Without further adieu here is the next part. The fuck that I and Namrata had sitting in a chair while her husband was sitting in the same room brought out the slut in Namrata. After that incident we used to fuck like rabbits when ever we got the house to ourselves. The problem was since Raj worked in a bank he used to come home fairly early and had a lot of holidays...

2 years ago
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Breakfast with Tiffany

Chapter 1. Unexpected InterruptionKNOCK.KNOCK.My heart began beating out of my chest to the rhythm of every hard knock at the door. My pants were around my ankles, and I was positioned in my desk chair, crouched over my hard cock, explicit content splayed across my computer screen. To my left was the narrow kitchen that led straight to the front door that --KNOCK.KNOCK.KNOCK.I swear I could feel my heart beating through my shaft and pumping more blood into the head of my dick while I stumbled...

Oral Sex
1 year ago
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Special Delivery Part Three Repost

As Brian drove to the shopping center to pick up Jamie, he couldn’t contain his excitement. She was literally offering herself to him earlier and he had to admit, it would have been incredible if he had taken advantage of the opportunity… An obnoxious HOOOOONNNNNNKKKK! Snapped him out of his daydream before it had even started. The stoplight he was at had turned green and the driver behind him was less than happy with his lack of attention to driving. Brian had spent the last couple of hours...

Erotic
3 years ago
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Skyrim Fanfiction Part 3

CHAPTER ONE Farkus was a werewolf, he had just killed all of the Silver-Hand, and he was staring hard at Jahel. She had never felt her heart squeeze so hard in fear, felt her adrenaline rushing through her veins so quickly. It was causing her vampire blood to boil, she knew now that she had never been so close to her mother’s kind. Everything else she had experienced had just a taste of what she could become if she allowed it. Her concerns though were focused on the werewolf in front of her...

2 years ago
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The Perfect Husband

Previously, I told a story of how I cheated on my ex-boyfriend, at his request I might add, but he refused to believe it occurred. Needless to say, that opened a few doors for me. He lived about 7 hours away and after that I had no qualms about hooking up with who I wanted, when I wanted, but the fact was he never asked again, and even if I would say something about it he would ignore it as me trying to upset him. Finally, he caught me in the act. It was my Junior year in college. He was home...

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