Dale - Work in progress

"Oops!" Connie said holding up the pair of emerald green panties.

"Somebody lost something. How does that happen? How do you lose socks and find other people stuff in your wash?"

She grinned and tossed the panties on the shelf.

"Uh, those are mine."

Connie blinked at him. "Yours?"

"Mm."

"Yours as in you have a thing for women's panties? Sneak through back yards, pulling them off clotheslines?"

"No. No, I wear them."

"You're joking." But she could see by the look on his face that he wasn't.

"How come I've never seen them? We've been together three months, practically live together."

"I don't wear them all the time. Not to work and not to the gym for sure." Dale shrugged. "I don't know. It's just a little something I'm kind of into."

She was quiet then, folding laundry.

Back in his apartment Connie said, "Is it just underwear or is it the whole cross dressing thing?"

"More the latter. I have some underwear and a couple of outfits. Only a dress and a skirt and blouse."

"Let me see."

He opened a dresser drawer. He had a couple of bras with rubber inserts, a half dozen pairs of panties, a garter belt, some stockings and a few pair of pantyhose. The dress was on a hanger under his overcoat. The skirt hung under a sports jacket. The blouse hid among his shirts.

Connie fingered everything and plopped on the bed.

"I'm having a serious case of disconnect here. I mean, you're not gay. You aren't are you?"

"No."

"And while you're a sensitive guy, effeminate doesn't fit in your dictionary from what I've seen. So what is it?"

Dale shrugged. "I can't explain it except that I get off on it. I like the way women's clothes feel."

"Well, I'm with you there." She held up the green panties. "These have to feel a whole better than those jockey shorts you wear."

There was a bit of a pause.

"Put them on." She shook the panties at him. "Here. I want to see."

Dales kicked off his boat shoes, unzipped his jeans, pulled them and his underwear off in one tug. He stepped into the panties and pulled them on.

Again the pause.

"Get dressed for me. By dress I mean d-r-e-s-s."

Dale unbuttoned off his shirt, took a bra from the draw, clasped it, turned it around, and shrugged into the straps. He slipped the rubber boobs into the cups. He opened a fresh package of stockings, rolled them up, slipped his toe in, unrolled it up his leg. Did the same with its mate. He clipped the garter belt, then attached the hose. He stepped into the dress. It was your basic little black number. He slipped his arms through the holes, reached back and zipped it. Lastly he dug out a pair of black pumps that were tucked away in a shoe box among many others.

He stepped into the living room. In the corner was his studio. Not really a studio, just a camera on a tripod and a couple of umbrella lamps, and the mannequin head. He removed the wig and placed it on his own head. Connie was leaning against the doorway.

"What about makeup?"

"I've tried, but I can't get the knack. I usually just shave and put on a bit of lip gloss."

"Yeah. The five o'clock shadow doesn't work at all." She grinned.

"So the whole shave your body thing isn't for swimming?"

"Oh, it is. It's kind of a chicken and egg thing. Whether I swim so I can shave or shave so I can swim. I'm serious about my swimming you know."

"Okay, this is turning into a case of t.m.i. Can you put your clothes back on? Uh, wear the panties if you want. Let me get used to this idea in bits and pieces, okay?"

Over the next few weeks Connie was apparently getting used to the idea. After sex one afternoon, she'd pulled on her panties and a t-shirt. He put on his jockey shorts. She handed him a pair of white, satin panties.

"Would you prefer these?"

He did.

"How about this?" she said holding up a white slip.

They settled on the couch, her in her panties and T and him in her panties and slip.

He acquired space in her closet and underwear draw. Connie wasn't a clothes horse, but like many women she had more than she'd ever need. Some of hers became his.

"Let's try some makeup," she said one day after he'd dressed.

"Hm," she said when she'd finished. "It's not bad, but it looks like you in drag."

Still, he allowed her to pluck his eyebrows, put a bit of color on his eyelids, a bit of mascara, lip gloss. It was subtle enough to wear in public. And she'd dragged him into public wearing panties and pantyhose under his jeans. She passed on the bra, but the shirt he wore had a definite feminine look to it.

"Okay, I'm not gay and making out with you dressed like that kind of creeps me out a bit. I'm okay with it. I'm getting used to it. I'm just being honest here. And it's weird that the buttons are backwards. Guy's buttons should be on the other side. And what is it with the bra? I can work my own snap, but have trouble with yours."

Dale smiled. "Welcome to my world. And speaking of worlds, how do you manage the whole public toilet thing. I mean, wearing pantyhose I can't just whip it out and pee; I have to use a stall and sit."

"Don't sit. You have to learn to squat and not touch anything."

One day she said, "I signed up for cosmetology school and I need a guinea pig."

Over the next few months Dale was Connie's guinea pig. Nothing went terribly wrong, but he got an up close and personal education in all things feminine. His hair nearly reached his shoulders and Connie trimmed it in a feathered style, not too feathery, but it softened his face. She waxed his eyebrows. Waxed the rest of him.

"Lasts longer than shaving and the hair doesn't grow back as thick."

She showed him how to move, how to walk in heels. He had a high voice and usually focused on lowering it, but now he worked at making it even higher and a bit breathy.

He always wore girl's underwear now. Sometime during the weekend she'd dress him and do his makeup. She bought him clothes and underwear regularly until he had two drawers of underwear and half a closet of outerwear at her place. He had to get rid of most of his own stuff to make room back home. Still it remained a kind of special thing. Except for the panties and hose, he only got seriously dressed on Saturday.

Connie lived across from a park and when the sun went down she'd drag him out for a walk. This was definitely not in the plan. He was a guy who liked girl clothes. Wearing the panties was okay, but doing the whole dress thing was something he did rarely. Now it became the rule, not the exception.

She had taken an advanced course in laser technology. And again, Dale became her guinea pig. The doctor ran the wand over Dale's face. It wasn't painful, necessarily, kind of like being snapped with a rubber band. The doctor continued working over Dale's body, taking out the darkest hairs, leaving the lighter ones for a more natural look.

"And now the rest," Connie said a few days later.

The rest turned out to be multiple visits to the doctor. Dale wasn't a hairy guy, but still. The doctor worked on his hands and arms, again leaving things looking natural. When it came to his legs and feet, though, every hair went. Not just there, but his crotch. He got the high-tech version of a Brazilian wax. And it was permanent.

Then they started going out on girlfriend dates. Real dates. In daylight. In public.

She shopped for him. He used the ladies changing room. And, by the way, the ladies bathroom, too. His world tipped into the surreal. After work and a trip to the gym, he'd do his makeup, put on his garter belt and hose, panties and bra, tuck the inserts in the cups, pull on a dress. He'd brush his hair, which hung past his shoulders (he'd taken to wearing a ponytail at work). Even when he wasn't with Connie, he wore his pretty clothes in the apartment.

The Dale the world saw was no longer the real Dale. The real Dale was Connie's girlfriend or a doll she could play dress-up with. The sex was the same. She preferred old Dale to new Dale in bed. But all of the things he did as old Dale seemed a sham.

One night as she was undressing him Connie pulled the rubber inserts from his bra and said, "I hate these things. You know what? I'm going to buy you boobs."

"What!"

She pointed at her chest. "You know boobs. Not humongous things, just enough to fill out your clothes a bit better without resorting to those rubber things. Lots of guys have man boobs. And you've got nice pecs. It wouldn't take much. I set up an appointment, I mean, just to see."

Dale tried to figure out at which point exactly he'd lost control of the situation. Now it was implants?

"Lots of girls get 'em for their boyfriends." She shrugged. "What's the diff?"

At the doctor's office he examined Dale and said, "I see no problems. Implants for the chest and buttocks."

Buttocks!?

"I'd suggest lip implants also. Makes the lips just a bit fuller. It would complement your face nicely."

"Fine," Connie said.

Fine!?

It took six months for everything to heal. He couldn't see his ass, but he'd seen pictures. The cheeks were fuller, gave him a hippier look. He had to start wearing girl jeans. His new tits were small and perky, not quite a handful. He still wore a padded bra, but he didn't need the inserts any more. His face looked normal, except when he compared his new mouth to his old one. All told he was still himself, yet not.

He wore women's clothes exclusively now, but he wore them in a butch kind of way except when he was with Connie when he wore his pretty things.

They were out on a date, sitting at the bar. A guy came over.

"Can I buy you ladies a drink?"

Connie said, "No, no thank you."

He waved his glass and walked away.

Connie slid her hand under the bar, slipped it under Dales' skirt, stroked the bare skin above his stocking, moved it a bit further and tickled the tip of his cock through his silk panties.

Dale looked in the mirror behind the bar. A woman looked back. His twin - if he had one. Maybe in a way he'd become his own twin. The makeup was perfect. Connie saw to that. The hair softened further the already soft face. There was a generous amount of cleavage showing. Real tits, no more fake inserts.

He'd never planned for this. Never wanted it, really. But he belonged to Connie and this is what she wanted.

She had started talking seriously about him getting a nose job and maybe having his Adams Apple scraped. It was always something. A real work in progress.

 

23.10.11

story continues in Dale V2.0

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