He to She

He To She by Lauren Westley

(Authoress Note: All disclaimers regarding characters, age appropriateness etc are in effect. I really advise anyone under 21 not to read my stories. It takes a certain degree of maturity to enjoy my writings without recriminations. Don't write a review if you don't like the theme of the story. That's just childish. But criticism is always good and helps me. fundipity@yahoo.com

HE -- Story from the Dom point of view

I knew the minute he walked into the bar he would one day be a she. Looking at him in his skinny jeans, colorful zebra print shirt and Keds sneakers.

He looked so young the bartender had to ask him for proof.

"You're twenty-three," the bartender said incredulously, "You look about sixteen. Sorry kid. What'll you have?"

And yes he looked about sixteen but as the bartender had confirmed he was twenty-three. Old enough to know better and soon to learn his better self. What I couldn't believe is when he ordered a white Russian. What a total girl drink. There was just one empty seat between a he-to-be-she and me: between 5'5" 125 pounds and 6'4" 240 pounds.

The bartender asked him did he live in the neighborhood and the kid answered `yes.' And the bartender was my friend and knew my proclivity so a few moments later he introduced us.

"William," the bartender said and then turn towards me, "this is Chopper." A little nickname I had picked up and although most people thought is was because I looked like a biker it was actually because I had flown helicopters in the army.

His hand reached out to shake mine. I delayed just a moment. It was an authoritative first moment and then my hand clasped around his and as I closed my fingers the soft skin of his hand was wrapped in my strong rough fingers.

"Nice to meet you Billie," I said as I looked into his warm yellow brown eyes my hand still enveloping his.

"Same here," he said. Not even knowing I had given him his girl name already.

We unclasped and I went back to drinking my Johnnie Walker. So many people had moved up to single malts but I still loved the simple taste of Walker and water. Billie sipped his white Russian with lips aching to be painted red.

The old black ceiling fan churned as if it was the percussion to the song, "Hotel California," playing in the background. Always amazed me how there were so many who hated the Eagles and so many who knew the lyrics of this song.

After he finished his drink Billie walked, to me swayed, to the bathroom just as the song finished with, "But you can never leave."

The bartender, Jake asked me if I was going to turn Billie into my latest girl? Jake knew me well.

"Jake, he is already on that road," I answered stroking my goatee. I had shaved what little hair I had on my head years ago and the goatee was my way of compensating. My left cheek sported a jagged scar from my military days. A piece of shrapnel had whizzed twenty yards from an IED explosion while I was lifting some troops out of harms way.

Over the past couple of years Jake had seen me take a couple of Williams" and turn them into luxurious Billies'.

Finishing my drink I got up and watched Billie, his creamy white flesh oozing sensuality and his auburn hair wisped from fan above as he was walking back. I thought just a bit longer, a few highlights, a proper cut. Oh yes and look at those lips they sing out for lipstick.

Something must have happened during the XY chromosome split since Billie appeared double YY so I guess I knew where the X must be. Funny though after all these years Billie could have had a schlong or perhaps it was just a tiny one. You can't judge by the outer layer. But it didn't matter because once they went girl it was just a clittie.

"Was nice to meet you Billie," I said. "I'm just leaving hope to catch you here again."

And wouldn't you know it his estrogen kicked in and said he was leaving too so we walked out together. Funny part is, it turned out, we both lived in the same direction except my building was two streets down from his.

As we walked we talked and I imagined him in heels. I could almost hear his heels clicking on the cement beneath.

"Well Chopper this is where I live," Billie said stopping in front of a nice six story brick apartment building.

"I'm just two blocks down," I answered. "We should get together again. I'll be at the tavern 7pm night after next. Hope you can make it."

Billie said he'd try to make it and turned to walk into his building. I watched his ass and thought how easily I'd teach him to walk like a woman. Then I headed home humming a tune from "My Fair Lady,' of all things. When you got past Billie's block the neighborhood deteriorated quickly and by the time you got to my old ramshackle house with a front porch sloping to one side you had entered a whole new world. Atlanta is like except for the wealthy enclaves like Ansley, Chastain, and Cherokee etc. But we weren't living uptown. We were downtown somewhere between the city and Decatur. It's an area I know well.

Thursday rolls around and I head down to Jake's at 7pm and who's sitting at the bar drinking his little girl drink? Billie! Ha the bait is in the water and the fish doesn't even know he's dinner yet.

I walk up to Billie at the bar and give him a slap on the back. You know one of those manly slaps but I also let the weight of my arm spend a moment sensitizing him. It's still too early to sissify him. No, this girl will need lots of work. Lots of time! But she is going to be worth it. I wonder if she'll be all girl and enjoy sucking cock.

Billie looks up smiling. (I can't believe it. He's sipping the damn fag drink through one of those tiny straws. Next he'll be smoking Virginia Slims.)

"Chopper," he says as I give him the closed fist twist guy handshake and he bungles it.

An hour or so later after talking about movies I'm thinking he probably liked the "Notebook" or the "English Patient" (hey don't scare the fish) it's time to pack up for the night.

The long mahogany bar has some dribble white Russian marks from when Billie pulled his little straw out and licked the end. He won't be making messes once he's gone girl.

And then Billie gets up like the other night and he goes pees just before he leaves. Mental note. Next time I'll go into the bathroom at the same time.

We walk to Billie's apartment together and I wonder if he has good legs.

Now this happened for the next couple of weeks and we started getting real buddy buddy. And since I know when he's going to go pee I'm am either in at the urinal just before or just after he comes in. Now I don't want to brag but I do have a smiling seven inches and nearly six inches in girth. Our Billie though is a shrinker when he holds tiny dick to pee the head is lost between his thumb and two fingers under his pee clit. Life is great. I always wanted to find a `shrinker'. Believe it or not most boigirls aren't small regardless of the porn stories.

Then one night, of course I had planned it, at the time we usually left I told Billie to go on since I had a few things to wrap up at the bar. Off he went wearing those skinny jeans he always wore and his little lime green Izod sport shirt with his tummy full of two white russians. What a girl I thought.

Anyhow little did Billie know what would happen next? I exited the bar about 5 minutes after him knowing a tough group of guys would start to bully him as he walked home. Oh my deal with these guys was exactly as the same as before, money and perhaps more.

I walked up to the alley but before I turned in I listened to what was going on. I knew these four whack jobs would have had my script proceeding like a major motion picture production.

Billie was pleading for them to let him go. I knew the four guys in a tight circle were pushing him around. One of the gang was teasing Billie about how he was whining like a girl.

"You are such a pussy," he cajoled.

Billie would soon be a girl. And if I were lucky she'd turn out to be a good little sissy girl.

"You're such a FAG girl. You sound like your whining for my dick up your ass?" one of the other guys said.

This was my cue. I had figured about five minutes of insults to be followed by that line where I would come rescue my girl. I turned the corner and walked down the alley all 6'4" 240 pounds of hard ass muscle. (The "Chopper" enters stage right.)

Yeah just like a movie script the hero comes to rescue the girl.

"What are you fuckin' guys doing?" I asked with a snarl and fists ready nearing the closest guy.

The next minutes were a whirlwind of choreographed harmony. These thugs knew they might get a chance at Billie's ass someday depending on the type of girl she became. And anyhow the hundred bucks for five minutes work was compensation enough.

When I had the pack broken up a bit (some pushing and shoving) I yelled at Billie to run which, of course, she did. She scampered down the alley and to the right. I thought I'm going to have to teach her to run like a girl. Oh what fun the future would hold.

After she was gone we banged a few cans around and then we broke up. I walked back up the alley and of course little Billie wasn't to be seen. No my little piggie had run all the way home.

Walking down her block I texted her to come down and meet me. Everything was safe. Meanwhile I had a little stage blood dripping from the corner of my mouth. Billie was coming from her apartment building just about when I arrived.

"Hey, let's go over to my place," I said.

Billie of course said, "Sure," and a look of concern as her eyes saw the blood oozing over my lip. She wanted to know what happened to me. Was I ok?

"Well you should see the other guys," I muttered, "let's go to my place."

I never ask a sub to do something I want her to do and I wasn't going to start now. Billie and I walked over to my place. This was Billie's first invite so I knew she'd say yes. Billie's eyes darted around furtively as we left her block and things got a bit seedier. This block was much worse then the alley. I walked a little closer to her. Her protector. If she knew what I had planned for her there's no way she'd have gotten to the next block.

My block was demolition alley. They had just torn down most of the homes to make way for an upscale apartment building and an empty lot was overgrown with knee high brown grass. It adjoined my property. The faded light blue siding sagging from years of neglect and my decrepit porch didn't exactly say, "come hither" but Billie was here now. Filthy windows and frames painted a decade ago had faded and turned a dirty white more Freddie style then Martha Stewart.

"Home Sweet Home," I said, "Come inside."

Billie replied, "It's cool," but with a bit of nerves on edge sound.

Just the sound of his voice I knew voice lessons could change him to sound like the girl I saw in him. He'd say kewl' instead of cool' when I was through with the transformation.

Now you may be wondering why didn't I just go get me a sub chick. There are plenty of them but the making of a boy to a girl is a bit like Van Gogh painting Starry Starry Night' and mixing Edward Munch's The Scream' in just for color. I know most who heard this story would condemn me but not one of my girls ever wanted to go back.

And Billie was a blank canvass. What kind of girl would she become? Oh I had one who wanted to be a little girl in the end. I finally sold her to a Mistress who was more then happy to play with her. And this wasn't some sexual toy but instead a cute 7 year old girl and her Mom.

What you may not know are the many variations of Sissyhood.

That just made me laugh. I thought about the "The Sissyhood of the Traveling Panties."

There's the baby girl, little girl, school girl, slut, maid, nurse etc. and once you train a girl to accept who she is and live it she finds her slot. In other words a `baby girl' will never grow up to be a slut. Though there are sluts who like to wear diapers. And as I said little girls who need a Mom or Dad but those who need a Dad usually have a sexual nature to the relationship as well.

Billie walked into my pad. The old wide oak planks had seen better days. Some of them were so worn I wondered about their integrity. The place was a typical guy mess. Kitchen dishes needed to be done. The old blue blanket crumpled covering the worn out and now faded original fabric of the sofa. And of course there was my easy chair. It was perfect. A first class Lazy-Boy for the Chopper to have some down time and either play a video game or watch TV.

"Hey Billie why don't you go to the fridge and get a beer," I said and he started straight there as if he had rehearsed this part so many time. "Oh and get me one too," I continued once he neared the kitchen. Hey you know what they say, `manners begin at home.

Are you wondering why I haven't really quoted anything Billie has said? There's a simple reason. Nothing he says is important until he goes to she and then she'll be trained as to her permissible convo.

If all went well today this would be her beginning. She came back with my beer and handed it to me with a folded paper towel and then went to the couch put her beer on the broken down coffee table and proceeded to straighten the blanket. She was looking more and more like a maid. Perhaps that was her calling.

Now I need to give you the layout. The TV was cattycornered in the far right corner. If you came up on the wall on the left you'd arrive at the sofa. So to relax and watch TV one would prefer to lie down. My easy chair was at the far end of the sofa so I could easily watch who was there but they'd have to turn to talk to me if they were lying down.

And then Billie said her first girl words, "This place is a mess Chopper." She was sounding more like a maid every minute. But would she be simply a maid or would there be more to her.

I turned on the TV to a boxing match. Hey great way to see how she'd react. Especially when I said I was going to clean the place up but now my shoulder hurt from the fight. (Yeah a lie but so what)

I had a DVD of the best knock out punches and I could see from how she was turning her face away from the TV the earlier event was playing through her mind and realizing how punishing those guys could have been on her.

And then her next girl phrase, "Chopper you saved me back there. I'll clean up for you while you watch TV." Oh, when she finally had voice lessons I'd have to get her to repeat that phrase in a Kate Winslow voice.

What I was doing was finding her hidden spot. Everyone has a place in their mind where they go alone and contemplate what they think are unspeakable desires. If you can unlock that part into the reality the person is forever changed into who they are and not what others expect them to be. I was looking into Billie's secret corner and I began to see her as a submissive maid. I would watch to see if she was a slut as well.

Maybe I was more like a sculptor. I think I once heard Michelangelo simply removed the stone, which was blocking the beauty of the Pieta. So I was simply going to remove the conventions of society and expose the beauty beneath.

Just to clarify a bit more. Many of the he's I help find their she I didn't ever have sex with. This wasn't about sex but if I found a particular kinky girl who once exposedÉ Well let's just say the rare occasion did occur. Looking at Billie I enjoyed the thought.

"Hey Billie there's an apron in the broom closet. Put it on. You wouldn't want to ruin your shirt," I called back as I sat watching Ultimate Fighter.

I heard the broom closet door open. Oh yes she was a submissive girl maid. If she could have seen me she'd have seen me smile.

The next decisive moment came a week later when she came over to my house. Almost instinctively Billie washed the two glasses in the sink. My plan was about to unfold. One of the hoodlums had run into her, intentionally, in front of her home and had said he'd fuck her in the ass except, "Chopper is your protector."

Billie had told me about it and I had told her not to worry since as long as she was with me no one would bother her. Remember I'm a big guy to anyone but to her 5'5" I am a giant.

I went over to the refrigerator taking a 32 ounce bottle of Campbell Tomato juice and pouring myself a 16 ounce glass. Billie wasn't wearing her apron (well I thought of it as hers) but had on white pants and a white shirt. How sweet. Little did she know she had worn the perfect color for today's event?

At the right moment I did a pretend trip and spilled the whole glass of tomato juice all over her dropping the bottle at the same time which broke spraying the deep red juice all over her pants and mine as well.

The look on her face was precious.

"Oh accidents will happen," I state as I put my glass down. Never apologize and never ask.

I started to take off my pants and told her to take off her clothes and we could run them through the washer and dryer. What amazes me is that some will protest and others won't. Billie didn't and ever more surprising to me she wasn't wearing underwear. It was a bit chilly in the house. Nothing a little clothing wouldn't fix.

"Do you have something for me to wear," Billie asked, as she stood naked wiping off tomato juice. She had very little hair on her body. And best of all she had a cute ass and perfect shaped legs.

"Take a shower and I'll look for something for you to wear," I said.

Billie sauntered off to my shower unaware of what would come next. I left all the clothes in a pile on the floor and was walking around in my t-shirt and briefs. Briefs are an eye catcher and we still had some stuff to do. This was a critical stage. I had left just a hand towel in my bathroom. And had all the rest wiped with my sweat, snot and some yellow stains in a hamper. Just in case she asked.

I went into my bedroom and took out two items putting them on the bed. One was a simple pair of white cotton panties. No sense putting her into satin yet. And the other item was a black and white knitted short sleeve housedress. I figured she'd be a size 4 now. Later we'd get her into a 2. The black was block letters spelling things like LOVE and I'm sure you can figure out what other girly words were covering the dress in all sorts of angles and overlapping.

Billie called out to me, "Hey do you have another towel? There's only a hand towel in here."

"No Billie I don't. All my clothes are dirty and need to be washed. But I found something for you to wear."

Billie came out of the bathroom holding the little towel in front of her privates. How dainty. A real man would just walk out dick and balls to the wind.

"I only found this," I pointed to the bed, "for you to wear. It was an old girlfriend who left it behind. And it appears to be your size," I said. Then I mentioned how we two were the only ones here and the top would keep her warm and almost just be like a large t-shirt.

What would Billie do? Would Billie object? Would she simply put them on? Would she walk naked around for the next couple of hours? I really didn't care since there were only two choices for her, naked or wearing this outfit. I sort of apologized not having anything else for her to wear and explaining how this would fit much better then anything that would fit me with her being 5'5" 125 lbs and me 6'4" and 240.

She walked to bed. No protestations. Nothing. She simply took the panties and pulled them up over her shapely legs and slipped the dress over her head as if she had done it a thousand times.

Yes, she knew in the hidden part of her mind she was a girl and she trusted me. We were crossing the line.

Now it's important to understand Billie did have hair on her body and although it was fine it was visible on her pretty legs and arm pits. Also, as much as I enjoy the process I've come to realize each girl is different. Not every one of them will go through the difficult process of removing all body hair. Even less will let their eyebrows be shaped. Some dream of jewelry adoring their ears. Others want belly rings too. A few are so sub they succumb to a master who may even adorn their genitals and/or have tattoos applied. But having Billie in this dress and panties was good enough at the moment.

This goes for both boys and girls but it's the ones like Billie that can be the most interesting. Sometimes their hidden little place has dreams of fantasy that should never be a reality.

As much as fantasizing about a rape can be tantalizing it's really not a good thing at all. It will never fulfill a dream. There are some fantasies others do recreate in reality that I have no part in. Fantasies of bestiality, brutality, scat holds no court in my passion. However, I do enjoy the pleasures of spankings, bondage, transformations and other sports.

"Chopper," Billie said as her doe eyes looked up at me almost pleading me to come take her from her hidden spot.

"Yes Billie," I replied.

"What about my clothes?"

We walked from the bedroom to the kitchen. There on the floor were the tomato juice stained clothing sitting in a pile as if someone had been murdered and their body vaporized leaving only blood, clothing and shards of broken glass. Okay tomato juice doesn't look like blood but you know how much I see things like a movie.

I was hoping this was the metamorphosis of Billie from wimpy boy to submissive toy.

"Billie the washing machine is on the back porch," I said, "and I'm sorry I don't really know how to operate it. I have a friend come over every week and she does it for me."

Was Billie already there? She motioned for me to go watch TV and she'd figure it out. She even bent over like a girl doing a deep knee bend instead of just bending over ass high her feet just outside the glass and tomato juice. Oh how nice her toes looked and a sweet pedicure would be perfect.

I went to the living room. You may want to call it the `over-lived-in room' sat down waiting for Billie. This was her time.

A few minutes later I heard the washing machine begin it's cycle and then Billie puttering around a bit in the kitchen. I could also hear the shards of glass clinking as she swept them up.

I stood up. Best to approach a subject like this on high ground.

She walked barefoot into the room. I could see how pretty her nails could be with a bit of color. Her toes and feet looked like a pedicure photo before shot at a nail parlor. I bet she does get pedicures.

"Billie let's talk. Sit down on the sofa," I said in a mild authoritative voice.

"What's up Chopper?" she asked inquisitively as she went to the sofa and sat down. Such a good girl I thought as I sat down again and turned my chair to face her. I could see her panties. She hadn't completely gone girly unless she was slut material. Too soon to tell.

"Just hear me out Billie. No protestations while I talk. When I'm done I will let you tell me what you think."

I began with a rhetorical question and answered it before Billie said a word.

"You know we all have a secret spot in our mind where we go and play. Some thoughts are formulated by the news of the day. Like when some world leader pisses on the USA I sometimes go there in my mind and imagine I'd do hand to hand combat with him."

This was not the kind of thought Billie would have but I wanted to instill my power position before we got down to brass tacks.

"Billie you have a secret place. Don't you?"

And before Billie said a word I began the deeper explanation of this hidden sexual playground. I had to shush Billie a couple of times while I exposed her hidden garden. I told her it was safe with me and I would be glad to enjoy the exploration with her if she was honest and sincere.

At first, when I was done, Billie tried to cover her tracks to her hidden home. But as I reassured her and we talked further Billie began to open up. When she talked about having dressed up as a girl she also was quick to say she wasn't gay. I explained to her girls like her weren't gay. In fact this split personality was a product of both intellect and learned experience.

During the hour we talked I didn't bring up sex. It was way to early to dig into the deepest part of her mind.

"Billie would you like me to give you an opportunity to unlock your hidden palace and test your mind in reality?"

She was hesitant at first but answered haltingly, "yyyyyees."

Billie had kept this so bottled up inside her that once she started talking about it she couldn't stop. She said many reasons she wanted to find the she in her; some went back to her earliest childhood days. Others came from high school and continued. But she said, "I've never done anything but try on panties."

And so it all began. I told her we would try our experiment out here at my place and if she trusted me I would lead her to sublimation. I stood up and walked over to where she was sitting and sat next to her. I saw her eyes gaze at my sack which filled my briefs but that was just a clue to perhaps her deeper desires. We wouldn't go there till we had passed many other hurdles first.

If you remember I mentioned I was an artist at this. I loved the caterpillar to butterfly as if it were my hand unwrapping the cocoon. But, having done this before I was much accomplished in all aspects of the transformation including patience.

"Okay Billie why don't we plan to meet three times a week here instead of the bar for a few hours. I will not do anything you don't want me to."

We sat back. I turned on a romantic comedy, "Fifty First Dates," and waited for her clothes to be dry. I did ask her if she had a preferential type girl she dreamed of being. She said the schoolgirl or the maid.

"Those are both great thoughts," I said, "leave it to me. I'll surprise you with one of those two as an outfit when we next meet."

I also explained how I would need her measurements so I could order appropriate wear and finally when she was here I would only treat her as a female but never expose her outside this house unless she asked me to. I informed her, her name in the house was Billie spelled with an ie and not a y.

Billie asked only one thing. Would I pick her up at her apartment since she was scared to walk over alone? Of course I would oblige. What she didn't know was I would call the hoods and telling them to disappear, at least for the time being so there was nothing to fear.

Below is the start of the second part of the story. Depending on the response I will finish it.

SHE -- Her story

Well Hi, I'm Billie. Chopper wanted me to write this part. I won't bore you with all the details of the past weeks. Yes I'm aware now of how Chopper coaxed Billie out of Billy but at the same time I know she was in me all the time.

From the first moment I saw Chopper in the bar I twitched inside and felt his testosterone as a powerful drug to my psyche. I didn't know where I was going but I did feel subliminal feelings especially the time I was in the bathroom and he came in. Just having Chopper stand next to me seeing his pee rod in comparison to mine was breathtaking.

Of course I had seen other men at urinals with their dicks out all were bigger then my stub. It was just for some reason Chopper exuded more male producing an intoxicating desire in me.

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