The Green Dress

Stories come from all kinds of places, some sit and simmer for a while before coming to life, others like this one, seem to jump out of nowhere, perhaps an old memory long forgotten. I do enjoy stories about transition, especially happy ones, and if you've read any of my other stuff, you know I only do happy endings. I will admit I gloss over some of the details about transition in his tale, but I do so to move the love story forward, I hope you'll forgive me. 😊

Standard caveat, all the people in this story having any kind of sex are eighteen at the time of the event.

~Enjoy

It hadn't started out that way, it had been just another Saturday, chores were done and my four older brothers, home for the summer from college, had run off the to the park to play football or baseball with their friends, my twin sister Emily was upstairs doing whatever teen-aged girls do on Saturdays, my mom and dad had gone out shopping for something my mom wanted and I had curled up in my little hide out in the basement with the book I was currently devouring.

Three sets of twins, my brothers, Henry and James, were the oldest and had just turned 22, William, not Bill, William, and Joseph, had come along a year later. Her royal highness Emily and I followed two years after that.

My brothers were all athletic and my dad coached most of their teams, I was dragged along to watch, my mom hovered around Emily as if she were the crown jewels. Our parents loved all of us but I kind of just fell through the cracks, I'd rather curl up with a good book or draw something anyway, so I tried not to mind. We all got along as well as siblings do, but Emily was the youngest by a few minutes and the only girl with five brothers, she was spoiled rotten and if I were honest, I was jealous, jealous to the point that on occasion, I would try to be like her.

Mostly that manifested in me stealing pairs of her panties and sleeping in them, fantasizing what it would be like to be her, this afternoon that all changed. All I had wanted to do was read, just hide from my brothers, and read, my mom inadvertently ruined that idea for me. It was her fault in a way, I mean she just left them there, hanging on that rack all by themselves, the rejects from the options Emily had been given for some high school sorority formal she had attended.

I tried the light blue one first, it took a little engineering to get the zipper up, but I did it, the dress fit like it had been made for me, the chiffon flowed down around my legs, the bodice was tight against my chest, I pranced around a little and pretended that some boy had asked me to dance, it was fun. The red one was next, I didn't like it as much, and then the purple, and last the green. Satin, luxurious satin with ornate needle work all over the bodice, it fit tight against my body a long slit up the right side almost to my hip, it was all I could do to just stand in front of the mirror and stare at myself running my hands up and down the soft fabric.

When I couldn't stand it anymore, I pulled myself away from the mirror and started to work the zipper down my back; it stuck. It wouldn't go down and it wouldn't go up, I started to panic, pulling at the dress until I felt the fabric start to give, No I couldn't, my mom would know it was me, nobody else ever came down to the basement, she would know. I sat down and wracked my brain on what I could do, how I could get out of this, resigned to the least bad of several awful choices, I picked up my phone and dialed, "Emmy, can you come down to the basement for a minute please, I need a hand with something?"

When I heard the giggling behind me, I knew she was here, "turn around and let me see," I could hear her trying not to laugh.

"Oh, wow, that one looks better on you than it did on me," she pulled up her phone and snapped a quick picture.

"Emmy, no, please don't, please," I was begging. She took a couple more before she put her phone away.

"Ok, what's the problem, did the zipper get stuck? It did that on me too." she was enjoying this too much.

I nodded and turned around. Her hands started working on the zipper, "before I do this, I want you to know, you owe me, do you understand?"

"Owe you what?"

"I'll let you know, but just so we are completely on the same page, if I don't get what I want, everybody sees those pictures," she let out a laugh that almost sounded maniacal.

"Ok, whatever you want, just help me out of this dress."

"You promise, pinky swear?" she was enjoying this too much.

"Pinky swear," I sighed a heavy sigh as I hooked my little finger with hers and the zipper slipped down my back to the top of my butt. Emmy laughed as she ran back up the stairs, "remember you promised."

It started innocuously enough, and I did the dishes two days in a row, nobody noticed because there were six dishwashers in the house and if it wasn't their turn, they were oblivious. I vacuumed the downstairs because she didn't want to, things like that, little chores, not a big deal, I even painted her toes for her once, which was kind of fun. Then she had me do her laundry, that meant I had to pick most of it up off her floor, sort it, wash it, four loads, dry it, and put it all away while she went swimming with her friends. It took four hours, but I got it done.

A few days later, she called me into her room, "How much more of this am I going to have to go through Emmy?" I let out an exasperated sigh.

"Sit," she pointed to the chair at her desk, a big grin on her face. I complied.

"Now, hit play," she pointed at her laptop, again, I did what she asked. I was mortified, there on her screen was a nicely edited video of me doing her laundry, picking up her clothes, feeling the soft fabrics, sometimes running them across my face or holding them to my nose, inhaling deeply, she even had video of me holding a few dresses and skirts up to my body and admiring myself in the mirror, and then I was folding it and putting it away, it was obvious I had made a small pile of panties that never made it into her underwear drawer.

Numb, I put my face in my hands and tried not to cry, "so what do you want this time?"

"I have decided that I don't want to punish you, I should be helping you, so you and I are going to play dress up, do you understand?" the way she said 'helping' sent chills up my spine.

"Emmy, no, please don't, it will be humiliating."

"Any more than what you just saw?" I shook my head no, "and you can keep the panties, I think you should wear them all the time, maybe I'll even do spot checks just to make sure."

I blushed bright red, "Oh, my, god," she spaced the words for emphasis, "You're wearing some right now aren't you, come on, let me see." Emmy was giddy.

I stood up and unzipped my pants, pulling them down just far enough that the pink bikini briefs with purple flowers were visible.

"Ooh, you like the pretty ones," I just nodded. My life was over, and I knew it.

Emmy left me standing there and started digging through her dresser, turning around with a bra that matched the panties I had stolen, "Ok, shirt, off now," from the look on her face, you would have thought it was Christmas. A few minutes later she was stuffing a pair of stockings in the bra to help fill it out, I was dying.

She had me try on a few of her dresses, a couple of skirts with matching tops and even a couple pair of her heels, I never thought my sister could be this sadistic, or that I would actually start to enjoy it. When she finally had me in an outfit she liked, she had me sit down and painted my toes a shade of pink that almost matched the panties. As hard as I tried to stop it, I could feel the little smile that crept across my face.

"Charlie, Emm, dinner is almost ready," mom called from downstairs, Emmy was trying to teach me to walk in heels and I was pretending to be annoyed by the whole process. I stepped out of the shoes and turned around so Emmy could unzip my dress. I grabbed my jeans as the dress fell to the floor, stepped in, and pulled them up, reaching behind me to unhook the bra.

"Leave it on, with your baggie shirts, nobody will ever know," I didn't even bother to argue with her. She hung up the dress and I pulled my shirt and shoes on and headed downstairs a bundle of nerves the size of my fist churning in my stomach, convinced everyone was going to be able to see through my shirt as if it weren't there, but Emmy was right, no one noticed.

And so the summer went, Emmy treating me like one of the Barbie Dolls she had played with when she was little and me too afraid to do anything about it while enjoying it a little more each time. As she had instructed, I wore panties every day, and after a couple of weeks, the bra was required too. My toes stayed painted and Emmy made me shave my legs and under my arms, what little hair was there anyway.

By the time my brothers went back to college, Emmy was teaching me how to put on makeup and had me sleeping in her nightgowns, even running around in her jeans, shorts, and a few of her more androgenous tops, the slow transition went unnoticed by everybody except me and Emmy. The thing that scared me the most was that she was running out of boundaries to crush.

School gave me some respite since she could only really force me to dress on weekends, but the panties and bras were always there and the threat of some new boundary about to fall to her whims was never far from my mind.

With October came Emily and my eighteenth birthday, I got a nice used car for going off to college next fall just as my brothers had, nothing flashy, just good reliable transportation, when he gave me the keys at dinner, I could see in Emmy's eyes, the cost of her silence had just gone up, she had gotten the promise of my mom's Lexus when my mom got a new one for her birthday In February which meant for the next four months, I was Emmy's chauffeur.

"Come on, I got you some things too," Emmy grabbed my arm when we got home and dragged me toward the stairs, a huge sigh of resignation was my only answer. I knew the routine, no sooner was the door closed than I was getting undressed, Emmy seemed almost giddy as she watched.

"All the way," she giggled as I reached for the package on her bed; the only thing I had on were the light-yellow panties, I slipped those off too. I opened the box; a matching thong and sheer nightgown were on top. Emmy had made me wear thongs before but nothing like this, my penis showed through the flimsy lace, when I added the nightgown and looked in the mirror, I might as well have been naked.

Next was a shoulder length blonde wig," really, Emmy, do I have to?" she just cocked her head and raised her eyebrow. I put it on and did my best to adjust it, Emmy brushed it out. I looked in the mirror and I almost looked like a girl. Emmy made me prance around a little, doing a few spins, she seemed very pleased with herself.

"One more thing," she pointed at the box, "this one is going to be so much fun."

"Shit," I said to myself as I reached into the box, I almost fainted when I pulled out a dong that had to be at least eight inches long.

"No way Emmy, this has to stop," I dropped it on the bed, "what are you really trying to do to me?"

"Charlie, we have a deal, you do what I say, or I show everyone the videos, remember?"

"What? Videos? Plural?"

"You didn't think I was going to have you do all those little dress-up sessions and not record them, did you?" she smiled at me.

"All of them?" my heart was in my feet.

"All of them, now let's see what you can do with your new toy, a girl needs to know how to please a boy after all."

I picked it up and looked at her," get on the bed, Charlie, then kiss it and lick it." I did what she told me to do, kissing and licking the huge phallus, taking it in my mouth and running my tongue and lips up and down its veiny exterior. I closed my eyes and tried to pretend I was someone else, anyone else, as she coached me to take it deeper and deeper in my mouth.

"Charlie, you are so good at this, aren't you just loving it?"

It went on and on for what seemed like forever, I didn't remember it happening, but I realized I was rock hard and sticky precum was leaking from my own cock, I took the toy as deep as I could, my spit running down over my hands as they held it in place. Almost unconsciously, I started to stroke it, my hand following my mouth up and down the slippery shaft, my own excitement growing as I went. I let out a moan and it slid down into my throat, it base against my lips, my own cock pulsed spewing rope after rope of warm thick liquid across my thigh and stomach, I held it there until I was finished.

"You did like it, you little slut, Happy Birthday," Emmy was beaming at me when she saw the nightgown stuck to my body by the sticky mess. I just laid there, confused about what had just happened but enjoying the afterglow of one of the best orgasms I had ever experienced, and I hadn't even touched myself.

I walked down the hall to my own room in a daze, still wearing the wig, thong, and nightgown, the huge dong hanging loosely in my hand, my mind numb with strange thoughts, wondering what it all meant. I didn't even bother to clean myself up, I just crawled in bed and curled up in a fetal ball.

The silicone phallus was nestled against my chest like a cherished doll when I awoke, the soiled nightgown still stuck to my thigh and stomach, someone had covered me with a blanket, I got up and headed for the bathroom, carrying the dong in my hand as much because I didn't know what to do with it as I just wanted to. I set it on the counter and stripped noticing the gentle tug as I pulled the gown away from my body, the crusty yellowish stain so obvious on the thin material, the gown and the thong fell into a pool at my feet, I left them laying there in the middle of the floor.

The hot water of the shower felt good as I stood under the spray trying to understand what had happened last night, Oh, I knew what Emmy had made me do, what I couldn't figure out was why I so readily agreed to whatever she asked, part of me was starting to realize that I would probably do most of it even without the blackmail, that and my reaction to shoving the fake cock down my throat, I cast furtive glances across the bathroom, half convincing myself the darned thing was laughing at me.

Taking the time to shave under my arms, my chest and stomach, sitting on the edge of the tub to do my legs, I thought about everything that had changed, the panties and the bras, the other clothes, I thought about how I had started to enjoy the dress up sessions, even look forward to them. No closer to any kind of an answer than I was when I got in the shower, I turned off the water and got out to dry myself off grabbing my silicone albatross as I headed to the door, it was stuck to the counter top, the convex design of its base formed a vacuum when I set it down.

I ran my hand up and down the soft rubbery surface noticing how realistic it looked, wondering if it was actually made from a mold of some porn star or something, imagining what it would feel like if it were the real thing, my thumb caressed its tip and I felt my own cock start to stir, shit, I knew what I wanted to do.

The dong stuck to the door as well as it had the counter, I laid the ruined nightgown on the floor underneath it as I began to lick the tip and then slowly suck as much of the now slick shaft into my mouth as I could, my right hand fondling my own growing erection. It didn't take long before the pressure started to build, closer and closer, as my toy went deeper and deeper down my throat, when I couldn't stand it any longer, I shoved my face into the door impaling my throat and exploded all over the gown at my knees, I collapsed into a puddle of sated flesh and cried; it was so wrong and I wanted it so badly.

By the end of the next week, the nightgown was so gross, my only option was to throw it out, but I could take all eight inches of the dong down my throat without even thinking about it, holding it there for as long as I could hold my breath, my dreams and fantasies filled with images of what it would be like to do 'it' for real, I had lied to Emmy telling her I had thrown it all away after the first time, she probably knew I was lying.

When my parents announced plans to go visit our brothers, Henry was going to be starting this week since the guy in front of him had gotten hurt, Emmy begged off complaining about how she had plans and it would ruin her life if she had to go. As always, my parents caved to the demands of the princess which meant I had to stay home too, to take care of her and drive her wherever she needed to go. I wasn't about to complain, the last thing I wanted to do was sit amongst eighty thousand people going crazy over a game I couldn't care less about, even if my brother was playing.

Saturday morning came and we waved goodbye to our parents, expecting them back sometime Sunday afternoon, I knew what I hoped Emmy had planned and she didn't disappoint, my parents hadn't been gone an hour and she had me fully dressed with full make up and the wig. When she was satisfied, she gave me a purse and told me to put my wallet and keys in it, we were going out.

A mix of outright terror and elation filled me as she locked the front door behind us, I had spent the past three months living in abject fear of her telling someone about what I had done and now I was going out into the world, I took a deep breath as I put the car in reverse and started to pull out of the driveway, "where to?"

I recognized the car outside the nail salon when we pulled in, it was Emmy's friends Rachael and Carla.

"Oh my god, he's as cute as you said he was, Carla, isn't he adorable?" Rachael gushed; Emmy had told her friends all about me.

What little confidence I had been trying to nurture on the drive to the salon evaporated in that instant, there wasn't a hole deep enough on the planet for me to hide in, my face and neck burned as my embarrassment grew and the deep red covered my face, Emmy grabbed my arm before I could try to leave.

The up side was she had booked a mani-pedi for me too, I leaned my head back and tried to enjoy the experience as Emmy and her friends chatted away about whatever girls talked about, The girl working on my feet had started digging her thumbs into my arches and I didn't care about anything else.

"No really, ask him, he'll do it I guarantee it," I could hear Emmy's voice, "you'll do Carla a favor, won't you Charlie?"

I opened my eyes and looked at the girls, their faces were pregnant with anticipation, "What exactly are you offering me up for, Emmy?" I knew it didn't matter, I was going to do it, with the dong, it had gone past her forcing me, I wanted to do what she told me.

"We want you to dress up for Halloween with us," Carla was grinning from ear to ear, "it will be fun, I promise, I have all the costumes already," she cast glances at Rachael and Emmy.

"Sure, I mean you guys have already seen me like this and it will be Halloween, so why not? What are the costumes?"

"You will just have to wait and see," Carla's grin turned into a huge smile.

My nails a lovely shade of pink, Emmy and I followed Rachael and Carla to the mall to go shopping and just hang out, the longer I was with them, the more I started to get involved in their conversations. They weren't the vacuous airheads I had always seen them as; they were smart and nice and, believe it or not, interesting, Carla had a rapier wit and Rachael was her perfect straight man, I laughed more than I had in a long time. I even found some of the talk about boys interesting and not just because it might give me a little edge to know how girls saw boys if I ever got a date; Rachael had actually given her boyfriend a blow job and told us all about it. By the time we headed home, I almost felt like one of the girls.