10 Button Dress free porn video

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Copyright August 1998 Don Darkdom all rights reserved. Permission to read and download for non-commercial purposes is granted.



10 Button Dress



by Don Darkdom



The first time I played the game, I was wearing a blue silk, ten-button dress. My college roommate, Sonia was trying to convince me to stay home and study instead of going out to dinner with Jesse, my new boyfriend. What can I say, Art History was a bore. I wasn’t failing, but well you know, I wasn’t working up to my potential.



I had gone into Sonia’s room to ask her if I could borrow a belt that matched my dress. She was curled up on her bed in a long T-shirt, studying. (Sonia is smart, beautiful, and had begun to sound too much like my mother.) She challenged me to a quick quiz. If I won, I got the belt for keeps, if I lost I had to stay home and study. Every incorrect answer I had to unbutton one button on my dress, get ten correct with no open buttons on my dress I win. A correct answer and I could redo one button. Open all my buttons, I lose. Simple rules. So okay it wasn’t the greatest idea, but Jesse wasn’t going to arrive for an hour and I wanted the belt.



I got the first two questions right, and then over the next half hour missed nine. Standing with my dress almost completely open, I was struck suddenly by the sexiness of the moment. it was a little disconcerting, I had never been attracted to women before. But, Sonia sitting on her bed, watching me, unbuttoning my dress. Wow. Under my bra, my nipples began to tighten and I could feel my panties getting damp.



Sonia jumped up from the bed. “You know you’re going to lose, Mai”, she said.



“A minor setback, nothing more”, I replied more confidently than I felt.



“Want to raise the stakes?”, asked Sonia.



“How?’, I asked.



“After you lose the last button,’



“I won’t”



“Yeah, yeah. One bonus question if you get it right I follow your orders all weekend, get it wrong and you follow mine. Simple, right. So….. deal?’



If I’d been thinking clearly I probably would have stopped things right there.



“Okay. Let’s get finished before Jessie gets here”, I answered.



I missed the next two questions and found myself standing in front of Sonia with my dress completely open, my undies showing and about to be told what to do all weekend. What was I going to tell Jesse? My jumbled thoughts were finally pierced by the realizations that this was actually exciting and that Sonia was talking to me.



“First of all, I want you to keep your date with Jesse. I need some time to prepare. But here are the rules for the date: no sex, you can tell him about the bet you lost if you want, and bring him home with you by midnight”, Sonia ordered.



“Yes, Mom”, I sassed.



“No more back talk. You lost fair and square”, Sonia said evenly. “Oh, and lose the underwear.”



“What!”



“You heard me! Panties and bra, off now!”



I was just able to hold her glare while my trembling hands removed first my panties, then my bra. We’d seen each other in various stages of undress before, but this was somehow different.



Now standing in front of her, naked except for my unbuttoned dress, I shivered in anxiety and excitement. I couldn’t hold her gaze any longer and looked down only to see my underwear staring back at me, confirming my humiliation.



“Pick them up and give them to me”, Sonia demanded.



I did as she told me and she smiled wickedly.



“Your panties are wet, Mai” she taunted.



I think I blushed from head to toe.



Sonia reached out and lifted my chin. She patted my hair and stroked my cheek.



“Don’t worry, Mai. Not only will you get a good grade on your test, but you’ll have great weekend and so will I”, she laughed.



She stroked a line from one shoulder to the other, several times, each time coming closer to my breasts. It was almost a relief when her finger finally brushed across my nipples. She noticed them tighten of course and smiled wickedly, again. She walked behind me. I could feel her body lightly pressed against my back.



“Don’t move, until I say you can”, she growled in my ear.



Even that sent a twinge of excitement through me. I could feel her nipples hardening against my back and pressed back against her.



“I said don’t move, Mai.”



She began again to stroke me, with both hands. First my arms then back to my breasts. This time she lightly scratched them with her nails. I could feel the wetness building inside me. The light scratching now roamed lower. Just before she reached my bush, she stopped.



“Is this exciting you, Mai are you very wet”, she asked?



“Not very”, I blushed.



“Liar!” she hissed.



She spun me around quickly and pressed her outstretched finger between my nether lips. I could feel the liquid drip onto to her finger. She raised her wet finger to my face then to her own, and I could smell my own arousal undeniably.



“Spread your legs wider, Mai.”



I did as Sonia bid and her finger returned to my pussy. She began to saw back and forth through my lips. Each stroke making me wetter, more excited and more ashamed. Sonia’s finger was driving me closer to a spectacular orgasm, yet she hadn’t touched my clit, yet. I began to lean into her finger to get her to touch my clit.



“I said don’t move, Mai.”



“Please”, I whimpered.



She pulled her finger away. I moaned in frustration.



“Mai, I want you to close your eyes and keep them shut.



I did and her finger returned briefly to my pussy. She traced a line through my lips, graced my clit, and I almost came. Then her finger continued slowly upward, finally coming to rest under my nose.



“Suck my finger like you do Jessie’s cock.”



I moaned again in frustration, humiliation and excitement. As I sucked on her finger, her other hand began to stroke across my clit. She stopped just short of my climax and pulled both fingers out. I moaned, again.



“Bend over and grab your ankles.”



“What are you going to do, Sonia?”



“I’m going to finger fuck your ass, then spank you till you cum, silly. Now bend over.”



When I was in position she jabbed her finger into my ass. She stroked in and out for a few minutes and soon had me on the verge again. I felt her finger slide completely out of my ass and then two very hard swats stung each cheek.



That was when the knock on the door announcing Jesse’s arrival sounded.



“Don’t move, Mai,” Sonia hissed. “Maybe I should just show Jesse in so he can see how you really want to be treated.”



All I could do was whimper.



She went to the door and I could just hear her tell Jesse I was finishing dressing and would be right out.



She returned and pulled me standing. She took my head in her hands and reminded me of the rules for my date with Jesse. I shivered in anticipation of what she had planned for the rest of the weekend. Then she kissed me hard on the lips and told me to button my dress. Which I did.



“One last thing before you go, Mai.”



She was sitting on her bed. Legs spread brazenly apart and rubbing her own pussy. She didn’t need to tell me what she wanted and I fell to my knees and began to lap at her. Her hands pressed me tightly against her and I felt her spasm against me quickly. I rose on unsteady legs to meet Jesse with Sonia’s taste still on my lips.



II



Still shaking with excitement I stepped out of the apartment. Jesse hugged me, put his arm around my shoulders and we headed out to his car. As he opened the door for me, he bent over and kissed me.



“You smell delicious, Mai. Is that a new perfume”, Jesse asked? Without waiting for an answer Jesse headed for the drivers side. Trying to collect myself I leaned across to unlock his door. As Jesse got in, started up, and pulled out of the spot, I noticed how high my dress had ridden on my thighs. Apparently, so had Jesse. He reached over and began to stroke my thigh lightly. He was talking softly, casually, as he continued to caress my thigh. I wasn’t really listening to his words, I was caught up in the sensation of his fingers brushing closer to my super heated pussy. He hadn’t yet realized that I wasn’t wearing panties, but it was only a matter of time. When his exploring fingers found my nakedness, we both gasped. I felt the wetness, again begin to build and realized that I had to do something or ruin my dress before we even reached the restaurant. I quickly lifted the dress so that my bare ass was on the cold seat. I shivered and spread my legs further for Jesse’s fingers.



“What’s gotten into you tonight, Mai.”



With his fingers driving me closer to an orgasm, I began to shake and ride his fingers. Just as I was about to cum he pulled his hand away. I moaned in frustration. I was about to take matters into my own hands when we pulled up to the restaurant.



“Jesse, how did you get us into Flash In The Pan? I thought they were booked till forever.



Flash In The Pan was the new chic spot, with entertainment rumored to be top notch no names with a bizarre twist, entertainers and customers were encouraged to show skin. The food was rated five star. As we were being seated I realized that I was dressed perfectly for this. I quickly unbuttoned the top two and bottom three buttons on my dress. I was immediately rewarded with an appreciative moan from Jesse and a laughing leer from the maitre-de.



The tables surrounded a circular stage. Our table was on the second of three levels. I realized that those on level one could look up and see Jesse and I, likewise we could look up and see the third tier. I spotted a man sliding his hand up a woman’s skirt, her hand appeared to be buried in his trousers. I thought about all that had occurred this day and tried to think how I would be able to not have sex with Jesse in this atmosphere.



I sat with my dress adjusted so that my bare butt was on the chair, with my legs slightly parted. Stimulated by all of the other diners, the entertainers, and Jesse’s roving hand, I was barely aware of dinner until dessert was served.



Tall men and women dressed in desert costumes served dessert. Thin, almost transparent linen dashiki’s open at the front, and billowing at the bottom. Men and women wore the same garment. Jesse was being served by a dark, almond eyed beauty, who was feeding him strawberries and cream, mouth to mouth. Jesse was still fingering my pussy. With his other hand he was reaching up and pinching the serving girl’s breasts. We were both moaning with excitement. My attention was suddenly pulled away from Jesse by the sight of the serving man lifting his own dashiki, revealing an enormous erection covered by the strawberries and cream. I practically dove on to his cock.



Sucking, licking biting, I grabbed his ass and pulled him closer to my face. When I had him completely engulfed, I began to suck him harder and was soon rewarded with a dose of his cream. He flipped me onto my back and using the cream and my juices, pressed his still hard cock deeply up my ass. I screamed once but then he began to stroke in and out and my excitement was raised to yet another fever pitch. Jesse’s hands were still busy with the other girl so I shuffled over and dove onto his cock with my mouth. As I stroked him with one hand and sucked him harder and harder with my mouth, I felt us both reaching another immense climax.



As we began to come back to reality, we shuddered together as our companions helped us to look more presentable. We could also hear applause from the rest of the room. Embarrassed, but satiated we headed for the exit.



In the back of my mind I was still worried about what Sonia had in store for when we returned.



III



On the drive back, I told Jesse about my bet with Sonia. He nodded and laughed when I asked him not to tell Sonia about our quickie in the restaurant. All too soon, we were standing in front of the apartment. I opened the door with some anxiety and not a little excitement. Candles dimly lit the living room, dance music played softly in the background and I could see Sonia stretched out on the couch.



She was dressed, or nearly so, in a red rubber mini-skirt and a white lace bustier. Her nipples poked out impudently. She looked hotter than I’d ever seen her. “Did you tell him?” Sonia asked. I nodded. Jesse snickered. I poked him with my elbow. A tactical error I realized as Jesse proceeded to tell Sonia the details of our adventure at Flash In The Pan.



“I knew you would break the rules, in fact I was counting on it”, Sonia laughed. “Are you ready for your punishment, Mai?”



Not really, I thought, but my body betrayed me again as I felt my head nod affirmatively.



“Jesse, would you rather spank her bottom or have your cock sucked?” Sonia asked?



Jesse paused to consider and decided to spank me. Sonia directed Jesse to sit on the couch, me across his lap with my face buried in Sonia’s delightfully soaked pussy. As Jesse spanked harder and harder, I licked and sucked Sonia harder and deeper. I could feel Jesse’s hard on pressing against me as he continued to pound my ass. Sonia came explosively and locked her legs around my face. Jesse suddenly stopped spanking and shoved a finger into my already sore asshole. Then two, three and soon it felt like he had his whole fist up my ass and I was coming despite the pain, or maybe because of it. Once a semblance of calm returned, Sonia directed Jesse to tie me to a chair with some rope she had handy. He followed her instructions and I was soon immobile. Sonia explained that my last punishment for the day would be to watch as Jesse used his cock on her. Tomorrow we would begin studying, and other punishments and delights awaited me. But that’s a tale for another time.



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Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

4 years ago
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An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole deal at least one time to see if I’m really as into it as I thought I was. I also mentioned that it wasn’t...

Crossdressing
2 years ago
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Hypnotized Into Wearing Dresses

"Hypnotized Into Wearing Dresses" By Alana Gloria knocked on the door of the dressing room, and Dr. Specks invited her in. He sat at his dressing table getting ready for his stage show. "Can I help you?" he asked. "I'm Gloria Stoner. I understand you were once able to hypnotize a man into wearing dresses. You got him so he experienced severe stomach cramps if he didn't dress like a woman. Is that correct?" Dr. Specks motioned Gloria into a chair, and said, "That was...

3 years ago
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Wet Dreams to Crossdressing

Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to...

2 years ago
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An Introduction To My Crossdressing

Many of the crossdressing life stories I've read on Lush have similar beginnings. The early adolescence, the mother's or sister's clothes, the masturbation! It's fifty years since my first urge to dress in feminine garments, and ever since then, it has been an integral part of my colourful life.I remember the day fairly vividly. I was settling down in our bathroom, to do what EVERY adolescent does at that age. Wank! My inspiration back in those days were my mum's pals, her sister, and a couple...

Crossdressing
4 years ago
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The Hairdresser

He walked into the New Horizons Hair Salon. It was a unisex salon but the majority of the clientele were female, mostly middle aged and upper class. He had stumbled upon this place when in desperate need of a haircut some two years ago. He was to be the best man at a wedding at the time and thought he ought to make more of an effort with his grooming.He had been shown to a seat by Paula, a tall brunette. She was late twenties and very attractive. Long hair held back in a ponytail, beautiful...

1 year ago
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The hairdresser

This happened in 2010Donna used the same hairdresser for over ten years. She was an Indian girl, really pretty and only recently married. She's called Gina, 30 years old, 5'5", thin with dark hair and extremely pretty. As Donna wanted her hair doing for a party we were going to Gina offered to open her shop late so she could have her hair done the same evening.Friday came round quickly, as I dropped Donna off at 6pm, the town was quiet and there was no-one in the salon, I told her I'd be back...

4 years ago
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Girlfriends Hairdresser

“Look, honey,” proclaimed Kamron as he held a mirror in front of his client.“I like it,” she declared with a smile. “How much,” she asked.“Fifty-five,” the five-foot-nine-inch big booty effeminate hairdresser replied.“Alright,” she said digging through her purse. “Oh damn. I left my billfold in my other purse. Do you mind if I get Tavares to drop it off when he gets off work,” she inquired referring to her live-in boyfriend that worked at the auto parts factory in town.“Yeah, chile. That’s...

1 year ago
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Button down and lacy panties

You were away on a business trip. I was very lonely. You called me late one night so say goodnight before going to bed. I was busy but I answered, continuing what I was doing. “Hello?” I asked irritated. “Hey baby.” You replied. You continued to tell me you wouldn’t be home for a few more nights, I sighed. We said our goodnights and hung up. I was angry but I wasn’t going to let it ruin the rest of my night. I sighed again, but this time for an entirely different reason. I had one had holding...

Erotic
3 years ago
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Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

Crossdressing
2 years ago
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my life as a sissy crossdresser

it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

1 year ago
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Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

4 years ago
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Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

3 years ago
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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

1 year ago
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My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

3 years ago
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The Pink Dress

The Pink Dress All Michael wanted to do was to wear the prettiest dress he ever saw; he knew he'd look so lovely, but he faced challenges from strange places By Katherine Day (Copyright 2007) During the Depression of the 1930s, even a 10-cent child's haircut was a luxury that Michael's parents could hardly afford, and Michael's light brown hair was long, giving him an a most girlish appearance. Even as a little boy, he...

2 years ago
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Next Time Ill Wear the Dress

Next Time I'll Wear the Dress I was shoving paper around on my desk keeping half an eye on the clock waiting for lunch to come around. I had a date that I was really looking forward to. Doris and I had been friends a long time ago but hadn't been in touch for a while. We ran into each other over the weekend and decided it was time to meet up for some long lost conversation. Beep! Beep! Beep! The phone on my desk alerted me to an incoming call. I snatched the receiver from the...

1 year ago
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Tight Dresses

Reddit Tight Dresses, aka r/TightDresses! I love to see sexy girls dressed up and ready for action, and seeing them in a tight little dress, just gives my dick life. Lucky for all of the perverts online, /r/tightdresses/ is a subreddit filled with pictures of horny girls who are wearing their sexiest dress. Of course, all the dresses are tight and showing off their curves quite nicely.Lots of images of amateurs and known models.The whole point of this subreddit is to focus on the babes who love...

Reddit NSFW List
3 years ago
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My First Dress

My First Dress by Sissy Susie It all started the day mum had to take my sister Sandra to London for the day. My sister's school orchestra were playing in the regional finals of a competition. As there would be a lot of waiting around mum had decided that I would spend the day with my aunt Caroline and my twin cousins Becky and Kirsty. I did not mind because although the twins were fourteen, two years older than me, they enjoyed things like football and we even played it together,...

3 years ago
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Sisters Party Dress

SISTER'S PARTY DRESS By Beth Ann My name is Andy; this is the story of how I got caught wearing my little sister's dress and the circumstances that followed. I have embellished the story, but the basic events actually occurred. School came to an end; it had been the first year of school for my little sister Jenny. Kindergarten was good for Jenny, she made many new friends and was well liked by everybody. Jenny was a particularly cute and bouncy little girl who loved to wear the...

2 years ago
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WWAC The Unpleated Nondress

WWAC: The Un-pleated Non-dress by Ashley B. D. Zacharias?I hereby call this meeting of the Wicked Women’s Adventure Club to order.? Lydia looked at the four women sitting around the table and nodded. ?I would like to take this opportunity to introduce our newest member, Miss Amelia Cox.? The four other members nodded at the young woman with the short blond hair and muttered soft words of welcome. She nodded back, nervously. The introduction was needlessly formal because she had met three of...

3 years ago
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Wedding Dresses

My name is Jason. I am 24 years old and work as an apprentice with a pretty good photographer called William. As well as his normal weddings and portraits, William does photo shoots for clothing and product brochures, and other similar projects. William charges a lot of money for the brochure shoots but offers the guarantee that if his work is not to the customers liking he will retake the pictures for free. I have worked with William for nearly 3 years and so far he has never had an...

4 years ago
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The Periwinkle Blue Dress

The Periwinkle Blue Dress A man buys a dress for himself ... and then pays for it. That was the set-up from my first story, "The Green Dress." This is an alternate version of that story, with the same initial premise and same characters from my "The Dress" series. But people and events are different, leading to a different place. I hope you like the alternative. The Purchase "Can I help you find anything?" the salesgirl said. It was just after opening, and I was...

2 years ago
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SRU The Prom Dress

I rarely do stories in which the narration is in the first- person view, but for some stories it's appropriate. For some it's not. And I thought this story would seem better with first-person narration so I did it. It has more vulgarity than my stories would usually have, but the main character (who narrates it) is a male jerk, and that's how people like him talk, so I did it to make it seem more real. I decided to do this story, because my other stories were talking a bit too...

2 years ago
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The Gold Dress

It was the summer I was 17, and I had just finished school. Both my parents were at work, and both my younger brothers still had school. But since my exams were finished, I was on holidays. During the day I was free to hang around the house alone, and do what I wanted. We were quite a happy family. I felt like we were always blessed with good health, and reasonable wealth. My parents both had good jobs and were able to afford a big house. In fact, back then, my parents were the only...

4 years ago
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My Sisters Wedding Dress

My Sister's Wedding Dress A lot of people have asked me why I do what I do. To be honest I can't really explain it. It has just always been a part of me. While I can't explain why, I can only tell my story. This is my true confession and it is nice to be able to say what cannot be spoken. I have to admit I have had this fantasy & deep desire to be a bride since I was little. I'm dying to tell my story! Confession helps bear the secret. Growing up, secretly I loved seeing...

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