'Under New Management.' pt 11

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Trans erotica, Femdom, BDSM, Masters.
2.7k words
4.4
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Part 2 of the 6 part series

Updated 05/17/2024
Created 05/09/2024
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Harold began mentally preparing himself to accept that he was in the middle of being cuckolded. With Olivia and Mike seeming to get on so well ...a towel wrapped turban style around his hair he walked out of the bathroom feeling like it was meant to be that he was emasculated.

Her boyfriend looked so innocent resting with his legs tucked under him the knees stacked. The towel still on his hair the other removed his nude body sat by the collection of pillows. Mike strutted in naked carrying Olivia's luscious-looking body in his arms.

A playful toss had her landing on the mattress laughing..."Oh it's so nice to have a real man around the house."

Her hand reached out to touch Harold's leg..."You don't mind sweetie do you...I think you know what I mean."

Mike approached stroking his cock.

"Damn Olivia...you're a mighty fine woman....say that thing at his dick...what's that called?"

"Harold and I both talked about it...it's a chastity cage."

She looked at her boyfriend..."isn't it sweetheart?" She wasn't looking at Mike yet she was talking to him...

"He had a problem with unsupervised masturbating...so we both agreed that he should wear one to help him stop wanking whenever he felt like it."

She paused..."It's been so long since I've allowed entry ...Some days I forget he even has a dick...my darlin' has become so good at worshipping my pussy....he has the most delightful tongue and the softest lips."

Harold could feel himself blushing.

Olivia leaned up and put a deep kiss to her boyfriend's lips.

Mike spoke up.."Yeah I felt that when he was in the shower with my cock in his mouth."

The woman settled back her shoulders at the pillow her hand reaching to cup Harold's ballsac and chastity piece. He felt paralyzed to stunned to speak with the other man in the bedroom.

Spreading her legs wide Olivia let out a grunt as she and Harold watched Mike slide his member inside her vagina.

"Oh fuck...Mike that feels sooo good....I've always liked a man with a nice size girth and some heft to his balls."

Her long-tome boyfriend just looked on as the pussy engulfed the impressive length. Unconsciously his hand reached down to touch his caged penis. There was nothing he could do but give it a few shakes.

The thick muscles on the man's arms stood stiff as his hands balled into fists pressing on the mattress. The sound of the 'slap..slap..slap'..of his cock going in and out filled the room.

He looked at Harold... Olivia's hands around Mike's neck her body absorbing every thrust.

"A beautiful woman like this ...and you jacking off...no wonder she put you in a cage."

That's when he decided to do it. Mike made the decision to treat Harold like a gurl.

"Come here darling give me a kiss....slip off the towel lets see how long your hair is now that its dry....I bet it looks feminine."

Harold hesitated then removed the towel giving a shake to his long hair. His thin frame... the hint of a bosom from the hormone patch...he lifted up. Olivia watched as his lips kissed Mike softly...the man's hand holding around his neck until 'he' was finished kissing.

Her hand diddling at her clit Olivia moaned..."Ewww Mike ...your cock."

She looked at her boyfriend..."Baby maybe we've had it all wrong all along...maybe you have a feminine side we've failed to see."

Harold felt a band of estrogen roll thru him...unaware of the effects of the hormonal patch he'd taken to wearing... it had been happening more and more lately. A gentle manner came over him...part of what she said he knew to be true.

He just shook his head..."Yes Ms. Olivia I think you're right."

"Honey there's nothing wrong with it...some men are just men and other males are better accepting their femininity....we've both seen the way you have come to like cleaning the house....thats a girl thing."

Just then Mike flipped Olivia around putting her on hands and knees. HIs hands went to her hips..standing on his knees he slammed into her pushing the heated cock in and out...the skin of her bum rippling on every thrust. Her hand reached back and took off the ankle bracelet that held to key to the chastity cage.

Knowing she was the key-holder had become a turn-on for the woman. To think that she'd controlled a man's penis confirmed what Lady Anastasia had taught her. Not all men are alpha's and that a woman can be a dominant force lording over a beta-male.

A minute later his penis was set free. It was some kind of test. Would watching his woman Olivia get fucked by a man excite him? If so what would that say about him. Sure enough the 5" dick grew erect.

"Play with it honey...I can tell you like seeing a man's cock in my pussy....girlfriends are like that...as part of the sisterhood they enjoy watching another woman being fucked."

Harold began pumping away ...he couldn't take his eyes away from the sight of Mike's cock or Olivia's vagina. When he turned to see the woman looking at him it was enough to bring him to the edge.

"Baby we were right...you're just like a girlfriend."

Her hand slipped over cradling his balls.

"Eww...Ahhh...ewwwww" ...the warm jizz spooled out onto both his fingers and Olivia's wrist. Her body moving back and forth Mike caught up in shagging her ...she lifted the inside of her arm. Harold knew it meant he should lick off his own cream.

"Sweetie...your tongue is sooooo nice... I'm going to have you lick me clean once Mike's finished...I think they call it a 'cream-pie'....come draw nearer...look at my breasts...think how nice it'll be to have your own...doesn't Mike look so masculine the way his cock keeps going in and out."

She moved his face to her's giving Harold a soft kiss. She whispered..."See you can tell he's close...cuz he's stopped talking and just focusing on his climax....men do that...they're self-centered ...watch he'll lets us know when he's about to erupt...men do that too....you'd love feeling a man leave his seed in you...not that I am one... yet there's just something about a submissive girl that likes being bred by an alpha."

Remaining circumspect and quiet Mike thrusting was picking up pace.

"Baby will give you a makeup change after he's through....maybe find you some cute lingerie...Hmmm would my darling like that?...we'll go in search of that woman within."

Pursing his lips Harold smiled nodding his head in agreement. Unsure of what would happen he'd finally given in to her sway over him.

"Of fuck...damn woman...hold still Olivia...just like that...Ugggg....ohhhh...eww yeah...I am going to come."

She snickered out...'Stop the presses....stop the presses....Mike's going to come.' Now that he'd released the bull-stud was a good sport and laughed along.

Turning She smiled at her boyfriend...'See...what did I tell you my darling."

Rolling off her Mike huffing and puffing laid on his back. Olivia adjusted before laying back next to him. When Mike's eyes closed she knew he'd likely grab 40 winks for a quick snooze.

Taking Harold's hand she guided her boyfriend between her legs. The warm semen was gently pooling at her slit. A moment of trepidation Harold slowly pushed his lips towards the glistening folds of her pussy.

He began licking and slurping at the come of the man who had fucked his lady. Every lick seemed to drive him further away from thinking himself to be her boyfriend any longer.

It had been building over months ....Harold held still as Olivia layered the foundation on evenly...Putting away her lingerie regularly...organizing her drawers ...in and out of the closet keeping her slacks and skirts and dresses and tops crisply ironed. Cleaning the home, keeping the necessary items stocked for a woman's grooming regimen he became so familiar with the aspects of femininity...

The hormones too...a simple patch put to the skin her boyfriend learned to enjoy the feeling of being first emasculated then led the edge of transitioning...The couple had stepped across into the new frontier when his body took on the curves and breast development females take for granted.

Sucking the cock of Olivia's bull-stud was the catalyst. It was Mike who inquired what name he would answer to. The woman asked her boyfriend if he had a favorite girls name...when he replied 'Linda' Olivia gave it her blessing. From then on there was no good reason why they shouldn't just go all the way to New Ladyland.

An hour and a half to go before they were picked up Linda had a concern. It was to be a double date like back during University days.

"Ms. Olivia?..."

"What dear?"

"What if Mike's friend doesn't like me?"

"Oh Linda don't be silly...you're too pretty not for him to like you."

She eased him to the floor-mirror pulling down the cups of the bra made pretty with lacy embroidering. Teetering in the high heels he glanced at his polished nails before looking at what he saw.

The sloping appearance of the pear-shaped breasts had the areola's and nipple stand out crowned at the tips.

"Sweetie you've got boobies...and these nipples of yours...my goodness Linda...they're gorgeous ...he'll be stealing glimpses of them all night....come let's lube you up and get your anal-plug in...I have a feeling you're going to need it."

Before pulling up the lacy panties Olivia eased the top part of the small-cap chastity piece in place. Open slats near the edge of the molded plastic using a cotton cue-tip the woman pushed the tip of the pee-hole so that it stuck out just enough to be called a t-girl clit.

Pulling the panties in place made it appear as though he almost didn't have a penis but only a set of balls.

On the way to the tavern the two sat in back chatting about women things while the men sat up front. Linda found herself thinking her date Zach was attractive in a manly kind of way. The bar was known for its burgers and brats yet the two women begged off and ate salads.

When the pool table was open it was Olivia who went over to claim the next game.

Sitting on a stool Linda watching the pool match she got a rush out of crossing her legs at knees and the way her skirt hiked up a little. She let her foot bounce a little like she was showing off the fact that she was a gurl with gorgeous legs in 3" heels.

A vagabond-chic look to the gypsy-peasant blouse it was sheer enough to give off a glimpse of her pretty bra and attractive b-cup breasts. Her fingers held the small glass of wine delicately the pretty nails colored red.

When a stranger approached her Linda wasn't sure what to do.

"Hey sweet cheeks...how bout' you and I go out back."

Just then Zach stepped in...."Hey pal...get away from my girl."

The guy gave him a push which Zach answered back with a punch. They barroom brawl was on. Linda scurried off the stool to huddle with Olivia her hand touching her face thinking she might have caught a bruise.

Oiivia shouted.

"Isn't this great...men are fighting over us."

One could hear the 'swoosh' of pool sticks in the air...mens bodies seemed to flying all over. 10 minutes later things had simmered down the stranger Zach hit with his fists was skulking away.

Her date looked her while Mike and Olivia went to get fresh beers....."Hey babe...you Okay?"...

Linda looked into his eyes shaking her head replying ..."Yes I think so."

It was the opportunity to let him know she appreciated his chivalry. Her arms going around his neck Linda kissed him long and deep pressing her girlish frame against his body. Pulling back she whispered ..."That's for my knight in shiny armor."

Just then...Olivia's arms around the waist of Mike had her shouting..."I got a 12-pack...lets get out of this dive and go to Look-out point."

It felt like being back in the days when they were 18...Olivia and Mike up front Linda and Zach in the back seat of the car they were at the make-out spot many a male and female teenager had lost their virginity at.

A 50's channel on the radio playing 'doo-wop' music in the background... the two couples began kissing and caressing. Olivia looked towards the backseat before she quietly slipped out of the car with Mike.

Zach slid his hand under the blouse in hope of touching Linda's bra. A second later he was squeezing it wishing it was off..."Hold on lover...just a sec." Linda flipped the blouse up hoping he noticed how pretty her bra looked. The brief pause she undid the hooks hoping he noticed how pretty her breasts were.

The twin b-cups glistened in the moonlight. Zach dropped his mouth to tug at the firm nipple. His hands in search of a new target zeroed in on her panties hidden behind the short skirt.

It was a new feeling to have a man spread her legs after pulling off her knickers. She took a worry...they hadn't had the 'talk'...she didn't have the chance to let him know she was a 'different' kind of girl.

"Don't worry about it babe...Mike told me all about you Linda...he said when you fluff his cock before he fucks your lady ...that you have the softest lips and could suck the chrome off a silver trailer hitch...besides I think its hot to have a t-girl."

Her hands drifted lower trying to unzip him. Zach stepped in and pulled his jeans and underwear down to his knees. Bending at the waist silently lowering down Linda slid her mouth on his cock.

"Damn...Oh baby...Mike was right...you've the softest lips."

Linda slurped at the cock...it was a taste she'd come to enjoy.

"Sweetie....honey...I need you now."

Flinging off his flannel shirt he lifted her up in the cramped quarters. Her legs on either side of Zach's legs Linda was so turned on to be in the nude having a feminized body about to be taken.

"Just a sec Zach...my plug....some lube."

Linda fished thru her purse pulling the tube of lube out.

Her thin little tummy...her cute b-cup boobies lightly swaying...Zach's hand held at her waist... guiding her down on the stiffness....the tiny chastity cage an afterthought.

Linda let her soft hands rest on his shoulders...her lower body lifting up and down..a shake of her hairdo...he was in charge and she didn't want it any other way.

"Oh Linda darling...yeah...that's good....you like having a nice hard cock in you."

It was 'man-talk' and Linda liked hearing it.

"Ewww...yes daddy....you're little girl needs you."

That was t-girl talk and Zach liked hearing it.

Riding the man cowgirl style she got into a steady pace moving up and down. Linda was determined to give her lover the best orgasm he ever had.

Her inner-canal was alive with sensations...the way the cock moved felt like it was touching all the nerves inside her. Zach let his hand move lower. The next thing Linda knew he was flicking at the tip of the extended t-girl clit.

She started whimpering like a little girl....this time her words were full of meaning ..."Ewww daddy...ewww daddy...ewww my little clitty....

The warm cream slipped out from the tip spewing forth. To have a t-girl get wet like that was a revelation for Linda. In some ways it was the best of both worlds.

It only made her concentrate more on her man. She started squeeing her butt cheeks every time he would pull out a bit...before pushing back in.

"Oh fuck...yeah just like that gurl."

Linda closed her eyes the moment she felt the first burst of hot semen. His dick kept on erupting leaving behind more man-juice on every thrust. By the time it had ended Linda started wondering what it would be like to become his wife....how nice it would be to have a man make love to her whenever they wanted.

Olivia and Mike came back to find him and Linda in the back seat with her wearing just the panties and Zach's flannel shirt.

The woman felt she had fulfilled her purpose...Olivia had made her boyfriend a t-girl and given him a man to love and obey. She could't help yet think in some way it was a powerful display of female dominance at its finest.

End of part 11...

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AnonymousAnonymous13 days ago

It sucks she fucked over his life just to cuck him and dump him.

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