Dale V2.0

(story continues from Dale - Work in progress)

Dale V2.0

Dale fidgeted, shifting from one foot to the other. He had to pee, but didn't dare. Dressed as he was he'd have to use the women's room and he had an irrational fear that when they checked his ID and saw he was male, well, there'd be trouble. Last thing he wanted was a strip search by another guy.

As if reading his mind Connie said, "What's the matter?"

"Gotta pee."

"Well go. I'll hold our places. I know you don't like using the women's room solo, but ..." Connie shrugged.

"No. I'm okay."

Dale was dressed all in white. He had a white, pleated skirt that hung just below his knees, a white v-neck blouse that showed a bit of cleavage, white stockings, white pumps, white beads around his neck and white beads in his ears. Even his underwear was all white, soft satin and lace.

The line inched forward. Time stood still. But, eventually, it was his turn. He showed his boarding pass and ID to the agent. He glanced at them and at him, handed them back. Reached for Connie's paperwork.

Dale didn't know if he was relieved or annoyed, but he set his purse on the conveyor and walked through the scanner. Again nothing. He gave a sigh of relief.

They headed down Concourse D. Connie steered him into the bathroom. He'd just stepped out of the stall when she pushed him back in and shut the door. She pulled a box from her bag, opened it.

"Pull your panties down."

He did. The object was unrecognizable, a bent piece of plastic, a ring. When Connie reached between his legs, the proverbial light came on.

"What the-"

"This is my trip and you're going to be my girlfriend every minute of every day and this," she said tapping his encased cock, "doesn't come out unless I want it out."

She finished fussing with the chastity tube, snicked the lock in place, pulled up his panties, and planted a kiss on his cheek.

"There!" She patted his crotch.

"Oh, by the way, the tube and lock are plastic. You can go through security wearing it. And the lock has no key. It's industrial strength nylon and can only be cut off. It came with five locks, but I don't see the need for more than one extra, I mean we'll only be there a week."

A few minutes later they were settled in the lounge.

"Stop fidgeting."

"With this thing between my legs? You try it!"

Connie laughed and sipped her drink.

"So what's this surprise?"

"Well, if I told you it wouldn't be a surprise, now would it?"

Dale tossed back his drink, ordered another.

He caught sight of his reflection in the window. Once again he was startled by his own appearance.

It was a little over a year ago she'd found a pair of his panties in the laundry. She'd asked him to put them on, and then the dress and all. The idea bothered her at the time and she'd agreed to only the panties until she got used to the idea of it. She got used to it.

A couple of weeks later she'd offered him her slip and a pair of her own panties. She started buying him clothes. They went out on their first girlfriend date. Connie enrolled in cosmetology school and Dale became her guinea pig. She'd been accepted into the advanced course in laser treatment and, long story short, Dale was hairless from the waist down, as was his face except for eyebrows and lashes. The doctor was an artist, removing only the darkest hairs on the rest of his body, leaving only the soft, downy ones behind.

Dale became an expert at makeup, doing his hair. Connie taught him how to walk, how to talk.

He started dressing up daily. And over the course of time he had more girl clothes than guy clothes until the only guy clothes he had were his work clothes: jeans and a couple of Oxford shirts. He spent every other waking moment wearing his pretty things. Then came the surgery.

Connie had scheduled the appointment "Just to see." Just to see turned out to be just to schedule: Butt cheek implants, breast implants, and, as an added bonus, lip implants.

The butt implants filled out his ass, turning it into something of a firm, bubble butt. The breast implants were more subtle. They say more than a handful is wasteful and Dale had just a handful: perky little, champagne-glass shaped tits. He didn't need the inserts in his bras any more, but he took to wearing a woman's jog bra to hold his new tits in place, flatten them out a bit, especially at work.

He accepted the nose job and having his Adam's Apple scraped, but he drew the line at having ribs removed.

"We just remove the bottom two ribs, then we'll put you in a corset and you'll have a nice little waist in no time."

"I don't want a nice little waist."

Long story short, Connie agreed that she'd gotten carried away and just like that they went back to the way they were. Well almost. He was her boyfriend and liked wearing girls' clothes, but the keyword was "boyfriend." Yes he had tits and a bit of an ass, but in no time flat his closet was free of pretty things. He kept that stuff at Connie's place. Except for his panties and jog bras, he was the old Dale again.

They still had their girlfriend dates, usually once a week, sometimes not. Connie pretty much set the schedule. She liked being in charge, not that she dominated him necessarily. It was more like a dance and she led. He liked it that way.

A couple of months ago she told him she had a surprise. They were going on a trip and he needed to get his passport and driver's license redone to match the new Dale and so he had. She told him she'd do the packing and he only needed himself and his ID. When he got to her place she did his nails. Not the usual, cheap paste-ons. These were acrylics, near permanent. She did his makeup and dressed him. She handed him his purse and carry-on case. And out the door they went.

"Do I get a hint?"

Just then the announcement came over the intercom: Now boarding flight 207 for Amsterdam.

"There's your hint."

He blinked, replayed what he'd heard.

"Amsterdam?"

"Mm hm. Let's go."

Okay. He'd figured they were leaving the country when she asked him to update his passport, but Europe?

Needless to say the next 12 hours were the worst of his life. Wearing his pretty summer clothes, crammed in with 300 strangers, and the damn guy next to him kept brushing against Dale's leg.

Dale drank more from nerves than thirst, which meant he had to climb over the moron and make his way up the aisle a dozen times.

And the tube pinched and he didn't dare fuss with it. At least it let him pee.

* * *

"Mistress Barbra."

"Please, you can call me Barb."

She pointed a finger at Dale. "You may not."

"Has he had any training?"

"No. None."

"Transsexual? Transgender?"

"Nope. Just a straight guy who likes wearing women's clothes."

It was a bad thing the time shift went the way it did. They slept in the next day and woke late before the appointment. Dale was wrung out, but a bit of makeup works wonders and he wore his peach colored, wrap around, jersey dress - no bra or any other underwear. He had on his rainbow sandals and rainbow beads to match.

"Walk for me."

Dale walked.

"Mm. Not bad. A bit affectated, but ... And the modifications?"

"All healed."

"Mm."

Dale's head spun. He looked around.

Mistress Barbra's lair was just what you'd expect. Black leather furniture, rings in the walls and ceiling, a couple of cages, a rack, an X-frame, a right proper dungeon. And she, too, was in black. Black leather skirt, black satin blouse, black leather corset, black pumps that laced up her calves, short black hair, and makeup a bit over the top.

"And your goal?"

"A properly trained sub. Straight, mind you. He's not gay or bi. He has a thing for cross-dressing, but that's it. We can work with that. So whatever scenes we have during his training-"

Training?

"have to be boy/girl."

"And what about you?"

"From a training aspect, sure, I can deal with other guys ... or girls. I don't know. I'm still a bit confused by the fact that having him like this is a turn-on and I can't lie, I've considered the girl-girl thing. And if he, er, interacts with other girls, that's cool."

Mistress Barbra nodded.

"Dale strip."

He hesitated a moment.

"Dale. You obey me or there will be hell to pay - a hell you cannot imagine."

Dale undressed.

"Kneel."

Dale knelt.

"The proper way to kneel is with your hands clasped behind your head and your legs open. As with all of my instructions, I will tell you only once. Do you understand?"

Dale nodded.

"When I speak to you, answer me. The correct response is, 'Yes Mistress.'"

Dale's world flipped off its axis.

"Yes Mistress."

* * *

Dale fidgeted. The new, custom cock tube was comfortable enough, but the rubber plug in his ass wasn't. The flight had been delayed and several passengers changed planes, so they had the row to themselves. He dozed most of the way home.

Flash: Dale kneeling at Connie's feet, kissing and licking his way up her leg to her crotch, then back down. He removed her shoes, licked and sucked her toes.

Flash: Dale kneeling at Mistress's feet, licking her pussy. The cock tube off. Connie tugging on his cock, forbidding him to come until Mistress had. They brought in another girl and she sucked Dale's cock the whole time. That was Thursday night, nearly four days with the tube. When he came he thought his eyes would burst.

Flash: Tied to the X-frame, his hard cock trapped in a rubber cock-ring, clothes pins on his balls and tits. Connie whipping them off with the small cat.

Flash: Wax! After Connie had cut off the plastic lock, his cock immediately sprang to full hardness, only to shrink under a cover of hot wax. "Do you want me to wax your cock?" she'd asked. The only appropriate answer was, "Yes Mistress, please wax my cock." So she did.

Flash: The finger-size plug sliding into his ass. Things were supposed to come out of there, not go it. But go in they did. Connie was enthralled by the strap-on and within days he was taking the full length of it. The thing inside him now was a traditional butt plug, though a hair smaller than some he'd endured. Still it would not come out unless he really pushed and if he did that he'd rue the day.

Flash: Connie's training. "To be a good Domme you must learn to be a good sub." Dale spent the session in a cage watching Connie submit to Mistress Barbra. It was apparent that Connie hadn't expected that, but she submitted to the lash, the clamps, the wax, the foot worship, the pussy licking and rim job.

Flash: Dale tied back-to-back with another guy. Blindfolded and gagged he could only hear the other's gasps, grunts, and moans. Could only image what he was enduring ... until the women went to work on him.

Flash: Bound over the padded saw horse. Harness ball gag. His cock and balls bound with thin, scratchy cord. Connie with a strap-on, pounding into his ass. He watched her in the mirror, tits bouncing, obscene grin.

Flash: Photo op. The whores had these little windows on the street. Connie convinced a girl to let Dale take her place for a few pictures. He stripped down to his underwear and sat as the passersby strolled. Some approached, made offers. Connie clicked the shutter.

It was pretty much back to old Dale again, except for the panties and jog bra - and the cock tube. He had to admit the sex was better. Instead of jerking off daily, he was allowed to get off once or twice on the weekend and it was pretty damn good.

He wore his old Oxford shirts and jeans to work, the bulge a bit more obvious. During the week he was old Dale, kind of. On weekends, he was Connie's slut. She hooked up with the local BDSM scene and every month they'd go to the club. They never participated. It was enough for her to have him there, dressed pretty, but kinky pretty, knowing that most of the guys and not a few girls would take him home in a heartbeat.

Dale had fewer pretty clothes now. Connie was seriously getting into leather or latex or, what the hell, the flavor du jour, but still and all Dale was happy.

 

12.01.12

story continues in Dale 3: A Day in the Life

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