'Under new management.' pt 7

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Trans erotica, Femdom, BDSM, Masters.
1.9k words
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Part 4 of the 6 part series

Updated 05/17/2024
Created 05/09/2024
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After the office gathering... standing out front of the upscale bar Jake saw Vanessa and Olivia talking. Still processing that the two women would be running things at work giving a wave he headed off on his own.

It was the first time in awhile that Jake could remember that he wasn't out partying with his boss Richard and his number two man Philip.

Though he hadn't put it together... ever since he'd taken the patch like they did things had been so different the last month or so. He couldn't understand where they were coming from. They could only be called feminine urges. He'd always been kinda' macho yet those feelings didn't seem to matter any longer.

Truth was he had been finding a weakness was overtaking him. It was enough he stopped working out. There was something lately about not being strong that he liked.

While Jake walked away from the restaurant towards his parked car Vanessa looked down to see a call.

"Master William...what's the latest on Jake....is that you across the street sitting in the car...I hardly noticed you."

"That's why I drive a Toyota ...they blend it well and people rarely notice they're being followed."

"Hmm....makes sense....any odd behavior by Jake?"

"He stays in a lot...no girlfriends to speak off...there's a local tavern he likes to go to from time to time...I checked the place out...and kind of gotten to know the bartender....he calls me by my first name only."

He paused ..."He's been spending a lot of time on line....I have a direct feed of what he's viewing...same as the other two but I'll talk about them in a moment...Jake likes ordering from Amazon and from upscale women's clothing stores though enjoys walking through lingerie stores as well>

" ...ummm let me see here..he weighs 152 but that's dropping...he's a size 8 mens shoe so that makes it a size 9 in women's...I'd guess his measurements are 34" hips...25" waist and up top he'll use a 32" band."

Clearing his throat he continued.

...'I've got him ordering women's high heels currently at 4 pairs....a couple of dresses from Ralph Lauren...and a feminine-cut skirt suit from Cristian Dior...and two different full make-up kits with extensive eye-shadow pallets....also he's developing a thing for lipstick...he's bought 3 different specials...you know where you make a 150 dollar purchase or more and you get add on's like 3 lipstick tubes and blushers ...one Clinique one Estee Lauder and the other Lauren again...some other odds and ends too. "

"Interesting ...well he's developing a taste for the finer elements of femininity."

"Him and his work-friends Richard and Philip don't hang out much any more....speaking of them...nothing on Philip yet... though...I do have access to their computers...Richard has connected with an on-line Mistress..a Dominatrix...calling herself a 'Femme-coach' in the past month she has put him on her feminization program...from what i can tell Mistress Raven is the real thing...she has plenty of 'before and after' pictures of men she has transformed....Oh yeah...he answers to the name 'Denise'.

"Oh like that...that sounds pretty."

"So Jake...likes getting high when not at work...free time on his hands he's been stopping by to see his mother a lot...At first she seemed surprised...there might be a certain motivation why behind just saying hello....quite lovely for 69 she was an actress on a soap opera back in the day."

Vanessa was impressed with how comprehensive William was.

William Hawley had spent his career in foreign service. That was a nice way of saying he'd been a spy. Like many in his field he took to starting a counter-intelligence business focusing on corporate clients.

William found the BDSM world was an outlet for his simmering controlled-aggression that quite often was needed for a lifetime spent in being a secret operative undercover agent. Thick chested and muscled-up the man knew how to handle himself. Being a Dom Master came natural to him.

"Looks like Jake's pulling out...let's talk while I drive....I placed a transponder chip in his car so no worries of losing him."

"Go do your thing William...we can talk later."

"Sure Vanessa."

Some 30 minutes later he watched Jake pull his car to the side out in front of a house in the wealthy suburb. Pulling up his bio William confirmed it was his mother's home. The woman was almost 70 years old. In her time she had been an actress. A stunning figure of a woman with a few notable credits to her name.

Getting married she divorced 20 years earlier when her only son Jake was in high school. A well maintained home William saw the light go on in the kitchen of the house. Creeping along the side hidden by shrubbery Bill could hear bits and parts of the conversation.

"Well if you think it might help someone Jake....thats stuff has been down there for quite awhile."

As best William could tell they were discussing donating clothing. A few minutes passed when he saw the basement light go on. Looking towards the staircase Jake pulled down good-sized cardboard box followed by another.

When he flung the top away Jake pulled a pair of women''s underwear. The vintage piece of lingerie looked to be of high quality.

Watching him thru the small basement window Bill saw a quick motion by Jake. He had his pants off and was sliding the full-cut panty-briefs into place. Trimmed with lace embroidering it was dripping in exquisite femininity.

Williams mind started planning his next couple of moves.

Jake took out a bra and looked to be praying it would fit. A glance at the staircase he bent and pulled what looked to be a bra-extension piece from his jeans. Sure enough it made the elegant-looking brassiere fit across his chest as though it has always been his. He took another bra out and this time it fit on its own.

Boxing everything up but the lace trimmed panties Jake lifted both boxes in his hands. Stopping he grabbed one more. A short shout out had him yelling.... "See you later Mom." William scurried back to his automobile undetected.

Parked out in front of Jake's flat Williams was pleasantly surprised to see him walking outside shortly after getting home. He figured he'd gotten high. Just as he thought Jake might...he followed his car to the 'Tavern in the Woods' bar.

Sitting at one end of the bar William kept an eye on Jake without letting him catch on. Sipping on a beer the youthful look of 33 year old he seemed lost in his own world. With the crowd small and thinning out William slowly moved his location until he was a few seats away.

Lost in thought the glassy look in his eyes let the man know he was buzzed.

"Barkeep...another cold beer here...for my friend and me."

"Sure William."

He knew he'd get anther good tip at the end of the night.

"Umm thanks I guess."

"You seem lonely ...I'm William."

"Uhhh Hi...I'm Jake....I dunno know things are lousy lately...none of my old friends seem to want me...things are changing at work...we're 'under new management'......I use to be tight with the boss but that's over...can you believe it...I'm going to be working for a woman...two actually...I'm not sure if I'll even have a job."

It was typical ego-based thinking An ego likes to convince one that there is a secret payoff in feeling bad. It tends to promote a sense of looking to the future with fear and anxiety and thinking of the past as it only having regrets and remorse and resentments.

"There's other jobs you'd be good at... I know we just met...but I've seen you around here once in awhile... I'm not going to dessert you...you could use some companionship on a night like this."

"Thanks Mister....I guess you're right....speaking of work what do you do?'

William gave a nod to the bartender. Jake didn't catch it as the barkeep slipped him a 'Mickey' in the drink.

Mickey Finn was from turn of the century Chicago in the early 1900's. A tavern in the notorious section known as the Levy District later made famous by Al Capone. He slipped what was to be called in the future 'a Mickey Finn' ...a knock out drug put in the drink...once the patron passed out he rifled through his trousers stealing what money he could then dumped him outside in back of the bar.

"Me... I do a lot of different projects...companies hire me because I am good at making assessments...you know ...sizing people up....you get it right?"

"Uhh uh sure."

"You for instance ...I can see you have a gentle side...maybe even a vulnerable side...it seems like you're changing or maybe want to change."

His hand went along Jake's face giving it a soft brush as one would with a woman.

"You have an interesting face."

Williams finger went to move through the hair sort of parting it thru the middle.

"This hair is nice...you have good volume to it...it looks like you're growing out....thats good ...you should...You ever been in movies?...why with a little work you could present with a different look...something that lets your best features stand out more."

"No I never been in movies."

"I scout locations for different film productions...currently I'm living in one that's very interesting...just to check it out...it seems the person that owns it has an interest in the BDSM scene.'

"I'm not sure what that is."

"It's a different kind of lifestyle...you know dominant and submissive...slaves and Masters."

William paused and took a drink..."Some people who know me say I'd make a good Master....I mean I've dabbled in it before."

"Umm...why's that?"

Once more his hand slid onto Jake's face. It seemed so much larger than his own hand. The space at the bar took on a sexual undertone or atmosphere....It was like when a girl is getting picked up by an alpha...as she lets her feminine pheromones release at the thought of being taken.

"Well for one I'm good and getting people to obey me."

His hand cupped Jake's face..."Pout your lips."

It was happening right in that moment. Jake was obeying the BDSM Master.

William slid his thumb in moving it in and out letting it act as a temporary phallus.

"Suck on it....You like that I think...I can feel your tongue licking at it."

Feeling a band of submissiveness flow thru him Jake sort of nodded his head.

"Let me hear you say yes Sir."

The man's eyes penetrating he couldn't take his own eyes away from them. A gentle band of feminine feelings came from an estrogen rush. Jake couldn't help it...sucking on the finger...he pulled up a girlish blush to his cheeks.

The thumb in his mouth he gurgled out a "Yes Sir."

"See...you like obeying me...you know I must say...you have a certain cuteness to you....it reminds me of a pretty girl I use to dominate....she loved submitting to me."

This time Jake volunteered it...'Yes Sir.'

William just let his hand brush along the the cheek-line once more.

"Yes...very similar....she said being my submissive brought her to new heights of sexual satisfaction she'd never experienced before."

Jake felt his dick getting aroused...the thought of being dominated by a man had touched something inside him.

Suddenly he started to slump over before passing out. William caught him and looked at the barkeep ...tossing him the keys to Jake's car he said..."Just put it along the side of my house....I left your tip here."

"Sure thing ....my lady friend is going to pick me up afterwards."

Carrying Jake into his home Master William could feel his loins stirring...there was always a part of him that enjoyed bringing a new protege into his BDSM world.......especially when it was a male who would come to live a feminine life under his rule and guidance.

End of part 7 ...

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