Sharon let him know she had to go out for the evening confident he would be up to no good the moment her car pulled out of the driveway. It was the first time in 5 weeks Fred had a slice of time to himself. She called it the pain pleasure dynamic ‘when feeling pain one must find pleasure’. Looking at her phone after hearing the ping she knew he had logged on to their home PC. The app was intended more for parents watching their kid’s activities yet might as well have been for errant husbands since they too often act immature especially when looking to view porn.
Both physically from the spankings that had become a regular occurrence as well as mentally she knew he was hurting. As with any male so used to rubbing one out masturbation was a quick fix as to having pleasure.
Watching her laptop feed the go-pro camera let her know naked he’d fallen asleep afterwards via wanking with the help of pornhub. Moving down the basement stairs quiet as a church mouse she secured the device that would further move him down the path. A few swipes on her I-phone and the app activated. If he tried to remove it he would get an electric shock.
The knock on the locked bathroom door brought a melodic response from Sharon. She felt like she was singing the rain even though it was just her in the shower.
“Who is it?....be there in a minute…I’m just washing my hair.”
Fred thought to him self ‘what do you mean who is it, we’re the only ones here’.
Sharon opened the door as with most any male that saw them her naked pretty c-cup sized breasts first grabbed attention. In the background Aaron Copland’s rendition of ‘Simple Gifts’ played as she’d vigorously rubbed the towel on her hair. At peace before the battle was to begin she had dried her hair before wrapping a towel turban style and sang along to the distinctly American song penned by the Shakers. Two verses in had her repeating them the 2nd time around as he stared hoping she’d stop.
‘In the valley of love and delight…..Tis the gift to be simple, tis the gift to be free’……
She saw the locked chastity cage and still managed to keep a straight face.
“Yes dear what seems to be troubling you?”
“What the hell is this thing on my dick. I’ve tried to get it off and can’t?”
“Don’t use that tone with me….who do you think you’re talking to?”
Her eyes looked at the cage on his naked body as though she was going to touch it.
“Hummm I’m sorry honey…please….don’t touch it…..I did and it gave me a heck of a shock.”
It pleased her the moment she heard his response yet wanted it to be even more deferential.
“Save the honey address me as Maam…now what is on your mind?”
“I’m sorry please excuse me Maam I didn’t mean to be rude…..”
Slipping into 3” mules Sharon turned away wanting what he had just said to stand-alone for a moment. Using her finger she brought out the wetness and scent to rest on the lips of her pussy. She couldn’t recall him acting so respectful in the last ten years. The thought floated in her mind ‘these hormones must really be working, like peeling an onion they’re stripping away his gruff masculine veneer’.
Turning her head over her shoulder she saw him staring at her pretty butt. It was time to start using pet names when interacting used consistently by a woman they subtly diminish a male further. All one needed to do was go to a mall and see how many husbands had been neutered and turned docile. The words 'yes dear' often came out as over time they learned to carry the purses and managed the shopping bags of their female spouses.
“You were saying my pet.”
“I was just wondering what this is and why I am wearing it Maam?”
“Step in to my bathroom from now on you do what you did when I was showering……be it ‘my’ bedroom or in here you knock first before receiving permission to enter. Is that clear?”
“Come in and slip to the floor I need help with my moisturizing, it will serve you well to learn more about how a woman maintains her feminine grooming regimen….the lavender one over there….start at my feet with their pretty toes.”
Fred picked up the plastic bottle squeezing out a handful he slowly rubbed his hands together almost afraid to touch something that smelled so good that only women used. Sharon feeling superior spread her legs and let her hands rest on her hips balled into a fist. It was brief yet there he was looking at the prettiness of her red polish painted toenails.
Stolen glances had him giving brief looks at her vagina as he slathered the body lotion on her leg.
“As to your little piece..…..It’s called a chastity cage, I never realized how small yours is compared to other male’s member, there was only one size smaller left.”
His nose lifted slightly before lifting a little more with the nostrils flaring. The fragrance was unmistakable as he took in the aroma of her vagina. Her thighs large though not unattractive had the sculpted curvature seamlessly connecting with the full rounded bottom cheeks. Centered between them her majestic vulva had its lips pouting glistening with wetness. On her mound a crisp ‘V’ had been neatly trimmed out of her pubic hair. Feeling her dominance expanding it may as well have stood for ‘victory’. His eyes looked up at her as hers looked down. The message was clear ‘not a chance, from now on you’ll only touch this when I allow it’.
“Don’t worry my pet I have the chastity key…..what have I told you before?.... masturbating is like cheating……you might as well have Stormy Daniels wanking you ….I’ve told you I believe any male in a relationship that jacks off….that is one of the many ways you describe it right?...well I look at as though one is being unfaithful. The attachment ensures you won’t try to touch your little plaything that is unless you like getting an electric shock. They use it to train puppies, like them I think you will find it quite effective in focusing your mind on other things more useful.”
“Yes Maam…may I say something?”
“What is it?”
“Its just your legs Maam… I never realized how smooth and soft they are…..they feel so nice to touch.”
“Very observant, lets use it as a teaching moment…stand…into the shower stall.”
Hands tied at the wrists to the small metal racks on the tiled walls inside the spacious shower Fred watched. Sharon spoke while lathering hair removal crème on him. Her words distracted while the crème began its magic.
“Yes, there is much you need to learn about grooming, it can improve your outlook for the day ahead…when one knows they are clean and have skin that is healthy and feels nice to the touch they seem to be happier doing their chores……ask any housewife and she’ll say the same. Mind you there is nothing wrong with feeling smooth in fact it lets one better see and monitor the condition of their skin.”
He let out a gentle sigh on feeling her hand jostle his ball-sac before moving to his mound.
“Let your eyes stayed closed for the time being to enjoy things….Knowing you are now responsible for the household chores for the foreseeable future…you would benefit from feeling clean and fresh.…and yes even smooth as you work about ‘my’ home. You’ll find you have a pep in your step as you move from chore to chore.”
Sharon left the room to look for a cigarette trying to kill ten minutes.
The first few seconds of the shower water was moderately cold until it was followed by warm water. Eyes closed he again let out a sigh.
“That feels nice Maam.”
“Yes this will too, stay closed you’ll like how this feels on your face.”
The facial epilator took a good few minutes as it slowly made its way around the facial hairs with Sharon guiding it. The slight pings of stings were masked by the warmness of the heat coming from the tool that gradually would eradicate his facial hair follicles over time. Sharon looked and was pleased with her initial efforts knowing she planned on having laser treatments permanently removing his ability to grow a beard later.
“There we go all set…..open your eyes…your nice and smooth….. and hairless now.”
His eyes opened to see the last of his body hair swirl down the drain as she untied him.
“Alrighty…out ya’ go lets have you slather on your scented body lotion just like you did for me.”
“Maam…all my hair...it's gone….my face too ….its so smooth.”
Though he didn’t know what it was he felt an estrogen rush on seeing how feminine his body looked without any hair.
“As I said you’ll learn to like it trust me.”
“Yes Maam…should I use the lavender like you have on?”
“Yes my dear pet.”
Being called dear felt nice as he ran the lotion on his legs.
She walked confidently striding into her bedroom that she had planned on making her own personal space.
“Lets go over your list of household chores before I go to ‘my’ office.…..I’ve decided if you don’t improve and meet my standards I’ll bring in some Polish cleaning ladies who will help teach you how to do it correctly.”
Suddenly he felt the urge to pee, turning he scampered to the loo. Moments later she heard him shout out.
Standing it front of the toilet he turned to see her standing at the door.
“Next time you need leave my presence you ask for permission first. What seems to be the problem?”
“I can’t piss standing up like I’ve always done with this thing…look I’ve gotten it all over my legs and the seat and on the floor.”
Sharon looked for opportunities to diminish his masculinity. She subtly encouraged his entrée into more of a submissive womanly perspective that reinforced feminine cognitive behavioral patterns. The words of both her Femdom mentors Sylvia and Valerie were with her so often ‘I want you to look at him from now on as a woman in the making…..everything you do should have that focus’.
“Address me properly, I don’t like that word start over and say tinkle.”
“Maam I can’t tinkle if I’m standing up with this thing… I’ve gotten it all over my legs and the seat and on the floor.”
He felt so childish using the word.
“I’d say it leaves you little choice…..unless you’d like to wiz on yourself. Maybe that’s one of those BDSM things you spoke…that video did have you saying I love BDSM…..it’s one reason why I tied you up to administer your first of what will be many spankings….that reminds me we have other things to talk about as to the fetish aspect of that……yes I’ve looked up the acronym of it……”
Softening her tone for the moment Sharon let her hands caress his balls as she spoke. Aware the reptilian brain and the need for sex for a male lurks right below the surface just as she thought it would her words an action had him thinking about sex.
“….Some aspects of BDSM actually has its appeal as to me helping you change your ways....submission, dominance, bondage...the 'S' come from the Marquis De Sade yet the 'M' of masochism comes from an Austrian aristocrat author, Leopold von Sacher-Masoch. He wrote 'Venus in Pelz' or furs as we speaking english call it. Semi- autobiographical it's about a male who desires to be enslaved by a woman.”
His breath grew short while she tickled his ball-sac. A smile on her face she stopped and padded the cage gently as though she was about to welcome a new member to the tribe of females.
“As for your chastity cage you’ll find it best to sit like a woman does, in this home the days of misplaced urine on a toilet seat are over …lets make sure we add cleaning up this mess to your chore list for today.”
Sitting at her desk Sharon looked over the changes she had made to Fred’s old office. An interior decorator had her selecting the piece picked out at an estate sale. The 18th century La Maison Du Travial writing Desk gave a distinctly first class look to the femininely appointed office environment.
The knock on the door had her waving the new secretary in.
“Ms. Sharon Ms. Valerie called and would like you to call her back when possible. A package arrived I have it on my desk.”
“Ahhh good thank you Tiffany, tell me are the males left here giving you any problem?”
“No Maam, not really except for that one who enjoys being difficult the others just seem to stare at my boobies whenever they get the chance.”
“While I approve of your business-like clothing a pair of d-cups tends to do that with males around no matter what you’re wearing. With your Domina Valerie helping you become a woman you’ll just have to get used to that kind of treatment until I replace those 6 with other women like you and I.”
Turning to head back to her desk Tiffany was thrilled to be included in the grouping with her smile indicating she didn’t mind being ogled at.
“Hi Valerie……yes for a boy being turned gurl she is working out quite well. Tiffany is very bright and will make for a wonderful secretary."
"Though it's changing many trans people find it difficult to get hired in the normal work place. Many have no choice but to find jobs in the sex industry."
"Not that I wasn’t before but I am trans-inclusive now that I’ve become friends with you and Sylvia. I want a LGBTQ friendly workspace with women clients being a top priority. More and more it’s the woman in the relationship that is making the financial decisions and that includes their insurance needs. Did you know that 80% of couples that buy cars has the woman making the final decision as to what kind?”
Tiffany slipped in and laid the package on the corner of elegant French provincial desk only to see Sharon cover the mouthpiece telling her ‘Freshen your lipstick I’ll need you in about fifteen minutes’. Tiffany smiled knowing what she meant.
Sharon held the phone to her ear with her shoulder as she unwrapped the package. Holding it up she moved to the spot she had picked out to hang it.
An image of a mythical female warrior holding aloft two swords as she looked off in the distance from a mountain-top had the words underneath.
‘Fate whispers to the warrior ‘you cannot withstand the storm…and the warrior whispers back ‘I am the storm’.
Standing staring at the framed picture Sharon could feel what she once had returning…the woman had reclaimed her sense of self-agency and vowed to make the insurance company successful on her own terms.
The office door locked had Tiffany slipping out of her short dress after unzipping it in back. She loved the feeling of being in heels on all fours in just her bra and panties and tights. The way her d-cup breasts hung down captured in the pretty lace bra made her feel so sexy. On her knees under the desk Sharon leaned down to look at Tiff before speaking.
“Just pull my panties to the side honey.”
The response came back slightly muffled with the t-gurl’s mouth on the vulva of her boss.
“Yes Ms. Sharon.”
Inside the elegant home the woman looked like she could give ‘Moose Cholak’ a run for his money inside a wrestling ring.
“You two upstairs…fresh linens on the beds and bring the others down here …I’ll have him start with the laundry......first your cleaning smock.”
Fred looked at Sharon then back at the Polish cleaning woman who ran herd over her group of cleaning ladies. Holding the cute cobbler apron she slipped it on him and brushed the lint off the embroidered logo ‘Stella’s best cleaning services’. It felt like the next thing to being in a maid’s uniform as she adjusted it at the shoulders. The stern looking woman moved the short scarf folded diagonally over his hair before tying it back near his neck. Her hands slid it to rest further up his brow and over half his ear.
“Nice earring studs, gold always best. All my cleaning ladies wear these, pockets on front left for clean towels right for dirty rags.”
Her hand turned letting the back of it run along his former beard line. It came out as more of a question then statement.
“He no shave here no more?”
Sharon smiled knowing a half dozen laser treatments had robbed him of the masculine grooming discipline. A brief look into the hall mirror had Fred feeling emasculated in his appearance. With the floral print bandana keeping his longish hair in place to go with the cleaning tunic a case could be made he looked prettier then two of the four polish cleaning women.
“Stella you’re in charge, he needs to learn everything. Now I am moving things out of his closet that’s in my room, some stuff I’ll donate to charity…yes what is it?”
Stella stopped her mid-sentence.’
“I take clothes…no charity…..I know people can use.”
“Sure that’s fine we’ll use the anteroom bench here by the front door as a holding area. I’ll try to sort things out with the hefty bags. Just take them with when you leave….you know how I hate clutter.”
Sharon looked at Fred who was in just a pair of shorts and socks and t-shirt with the name Riptides splashed across its front.
“Bring all your clothing it’s time we went through them anyway…every thing from the closets down here and I’ll figure things out while you shadow Stella as she cleans and instructs you.”
The prompt response surprised even Stella being her regular cleaning woman for years she couldn’t ever recall him lifting a finger to help. Nearing the end of his 5th month on female hormones he was to be given tutoring in keeping the home clean and in order.
The next half hour had Fred creating three piles next to two that Sharon had made from her pruning the linen closet and attic. Dusting the window sills along the winding staircase he listened to Stella. Sharon looked up to see them on the landing near the 2nd floor.
“Stella I have to step out …I left hefty bags neatly placed near the pile…you may want to get them in your car before the rain comes.”
Looking over the railing in a heavy eastern Slavic accent she yelled back down the stairs.
“Vill do Ms. Sharon…tank you.”
Looking at Fred Stella commanded.
“You stay, you clean, make spotless no dust.”
By four that afternoon Stella and her crew had left by then the home could pass the white glove test. With new curtains put up and a freshly purchased comforter with pillow shams put over new satin sheets he had watch the cleaning women turn Sharon’s and his old bedroom into a one now distinctly feminine.
The guest bedroom down the hall had been made up also with new linens and a pretty comforter with floral colored throw pillows. It too had been femininely appointed having its own vanity table and bench and armoire. As they were fixing it up he learned from Stella that it was to be his room from now on.
The feminine grooming regimen became easier to adapt to the longer he was on female hormones. Though unaware of it there was just something about having estrogen flow through his endocrine network that made sitting in the warm tub feel better then it used to. Having cleaned the home all day taking a late afternoon bath only seem to make sense.
It’s one thing to be in chastity for a fun night of sexual kinkiness or even for the two or three days of a weekend yet being in prolonged chastity changes a male. His caged penis hadn’t been touched in months in a sexual way. It seemed like it had shrunk from being locked for so long and appeared harmless behind the metal restriction as it bobbed in the water between his legs while he conditioned and washed his hair.
He took to dipping under the water to let his pouting nipples come just above the surface. Secretly he enjoyed how they were starting to look on his smooth hairless body. Along with moisturizing every morning for 8 minutes Sharon had him using nipple suckers attached to each. Gradually over the weeks then months they began to lift and grow outward expanding in size and width and length. As the female hormones kicked in they became even more sensitive.
Sitting back his headed rested on a wet towel. Suddenly he realized after bringing them down he hadn’t separated his clothing in the front hall. Drying off having seen Sharon do it so often he swirled the towel around turban style before wrapping one around his waist to go check on the pile of clothing. Fred stared and knew it would be best if he pulled the towel up further to conceal his upper body growth. Padding down the hall to the stairs one hand held to towel close to his breasts while the other hand glided along the banister as he made his way to the first floor.
“No,no that can’t be…that was everything I owned….that was all of my clothing.”
Chewing on a slice of apple Sharon stepped out from the kitchen to stare at him.
“What is it honey…..Baby you’ll catch your death from cold like that…I should let you have one of my robes they feel so comfy after a shower.”
“My clothing Maam…it’s all gone Ms. Sharon…..that was every thing I had….what am I going to do?”
The plan had worked to perfection and she knew it. Feeling his anxiety build she let him stew for a while longer before drawing near to wrap her arms around him. Her tight squeeze reminded him she was regaining her former athletes muscled up look.
It was slight yet she heard it .
“Ouch…..what am I going to wear, everything I had was in those piles?”
“Well we’ll just have to find some things of mine that will work, what with you being much thinner these days things will be fine. Lets head up to my bedroom you’ve earned yourself a reward for your efforts today.”
Sharon wanting it to be more then just a one off essentially ‘Milking a male’ can go down two ways. She planned on leveraging every milking session to win concessions from her pet he normally might resist had he not been aroused. A milking can be benign with little sexual pleasure coming as for health reasons he is drained of his cream. A male often stares in disconcerted concern while the feminine alpha has amusement on their face as ‘drip-by-drip’ sperm oozes out.
The other more fun way has it becoming a sexual delight while also creating a level of concern in a male with the acceptance of a phallus in the act. A male discovers much like a women’s vagina he can derive pleasure from being penetrated by a dildo or even a vibrator inside his anal track.
Sharon stood in front of the bed while on all fours her budding t-gurl held still as she finished turning his hair-style into two cute ‘pigtails’. Her hand gently ran along the length of his smooth naked body. It brought a quiver as he for the first time felt his body being used more like a woman’s often is.
The band of lube running down between his slit of a crack was followed by her finger sliding in as though probing.
“Now you just hold still baby….you know I never realized just how pretty your bottom looks it reminds me of a friend of mine from university, Regina…we’ll have to keep that in mind when we select clothing you can put in your new closet…..Regina always made sure to show hers off.”
Wearing the latex glove her chatter went on acting as a distraction as she replaced her finger with a dildo.
“I think you’ll enjoy having your own room…..Stella said the two of you had fun…..and that you looked like you enjoyed making it pretty with her today…..its such a lovely Vanity table and matching bench that’s in there now. I picked it up at a house sale.’
The moans started out soft.
“This way you can get up early to prepare for your day at my home without disturbing me.”
He could feel his pigtails brush along the sides of his head as he turned slightly.Having been put there a month earlier a tiny pair of bells chimed out hanging down from his chastity cage.
“Ohhh Maam ….that feels nice…ohhhh its sliding in so easily.”
Her hand dropped down and gently tweaked his nipple.
“Eeeewwwwww that’s so senstitive.”
“Yes up early …..you’ll be close enough should I need you….You’ll be able hear my little bell ring when I call you.”
He felt himself give a couple of shakes to his butt shimmying it back and forth as the dildo went in deeper.
"I think you bells sound so cute baby, I've gotten used to hearing them before you enter a room."
Along with a vibrator Sharon leaned forward and placed one of her realistic 6” dildo’s so he could see it on the bed. The mere sight of it activated the trigger as his inner voice declared ‘what a gorgeous looking cock’.
“Of course one of your many rules will still be in place….you’ll have to knock first…a woman like me doesn’t like to be disturbed.”
“Eeewwwww, eeewwwww oh that feels good Maam.”
The woman had one primary mission to ferry him across to a rebirth in the Lady pond.
His eyes opened and looked down to see how much nicer the nails appeared now that he was being made to grow them longer and keep them shaped and contoured with clear polish.
“I mean I should still need to teach you the lesson on how the masturbating you used to do was like cheating….I suppose I could bring home a bull-stud to service me in my bed…that’s one reason why it'll be best that you knock before being allowed to enter.”
A simple ‘yes Maam’ came out. He didn’t care how he looked he soon began pushing his butt back on the dildo while feeling the slight movement on his chest each time he moved.
Once more Sharon bent down and tweaked his nipples.
“Having these pierced with pretty barbell’s would also feel good…hmmm darling would you like me to do that?”
He hesitated as he processed her words. Sharon immediately pulled the dildo out stopping the ride on the pleasure train.
“I said would you like to ask to have your nipples pierced…..tell me?”
“Please pierce my nipples Maam.”
His head drooped and had him looking between his legs to see the plate. There was already some cream on it as he saw more drip down from his caged penis.
Sharon let one hand glide along the soft skin of his back as she coaxed him.
“That’s it that’s it…let it all out dear…I think if I move this cock of a dildo a little I’ll find that g-spot of yours.”
Shaking his butt busting a move 30 seconds later he softly screamed out.
“Oh my goodness ……yes, yes, yes, yes ….ohhhh that feels amazing.”
“You know you sound so much like my old college roomie I think its time we gave you a new name…..don’t you?”
Fred didn’t want her to stop like she had few minutes earlier nodding his head he looked at Sharon ‘yes Maam’.
“Very well then like her I’ll call you Regina…now shall we see if we can make you climax Regina?”
“Yes please Mistress Sharon.”
‘Regina’ had finally said it for months he had been wanting to call her what she really was to him….a superior woman that had earned the title ‘Mistress Sharon’.
She spanked his ass twice and turned on the vibrator of the dildo.
“There Regina enjoy yourself …I don’t know any woman who doesn’t like the feeling of being penetrated with a cock that vibrates.”
Having his first womanly-like orgasm both pretty bottom cheeks started to spasm uncontrollably as he slid back and forth. It pleased Sharon to see they were developing a loose roundness to them.
“Ooohhhhh yessssssss….eeeewwwww eeeewwwww, oh my….that is so nice.”
Sharon simply pushed his head gently down having moved the plate with his discharge on it she place the piece of fine China below him to watch his lips slurped up his warm cream.
Leading him down the hall to his new bedroom his woman walked out after slipping a frilly Babydoll nightie with matching panties on him tucking her ‘Regina’ in bed. Her last words to him let him know from now on it was best he be kept in lingerie. Smiling up at her he simply nodded his head in agreement. As she headed to the kitchen alone Sharon dropped his shorts and t-shirt and last pair of male underwear into the trash.
The next morning was a whirlwind of activity Sharon organized the new clothing while she had Regina put them up according to category in the closet and drawers. No longer feeling like her husband 'Regina' looked with glee at seeing an array of lingerie fill two drawers in his armoire. Stealing a glance Sharon looked on as she saw her budding t-gurl look at the new bra’s that went with the collection of matching panties and camisoles and slips. It was as though he was wondering when he would be allowed the privilege of wearing them.