Eva Smithfield had proved to Trisha she was a demanding female boss for a secretary to work for. The t-girl was doing her best to improve upon her necessary skills.
The gift sat in her desk drawer for nearly a week. She guessed some woman she didn’t know who from the sales department had left the decorated box on her desk. As a whole the group of alpha females enjoyed reminding them all three had once been males yet now lived as women.
Opening it Trisha saw a pink anal plug and tube of lube discovering it vibrated on four levels after reading the instructions. Unique in its design the higher the vibrations the larger the cock-like piece expanded inside.
The message of the note card had a hint of meanness as she read ‘chastised and locked by a Woman…since you can’t stroke your plaything you might as well learn it’s time to ride a vibrator to get your rocks off like the rest of us do’.
His hand slipped under his skirt touching the slight bulge of his chastity cage in his panties. Things had gotten to the point he’d hardly remembered a time when he wasn’t wearing it as well as having once been a man free of the metal restriction.
The wild card of HRT is that it effects each person differently. For some it takes years to truly take on the characteristics of a woman driven by the female hormones while with others femininity flows like a fountain once estrogen is unleashed mingling with the personal DNA.
Such was the case with Trisha easily arrived at the t-girl had taken to her feminine-side as though deemed so by the Greek Goddess Venus.
With Lucille having moved in with him engaged to Hunter and Amber turned working housewife for Trudy just that morning she felt a pang of loneliness laying out her intimate wear.
There were days when she stared at her beautiful c-cup breasts with the pierced nipples and shapely body loving everything about being turned transwoman as she slathered on the daily requirement of moisturizer.
Call it a habit yet the t-girl would lay out three or four coordinated outfits after she moved past the decision point on what lingerie to put on. Sliding the bra on becoming 2nd nature she would spin it in back after hooking the clasps before lifting it in place.
Sitting at his desk the mere idea of using the gift brought a dampness to his panties. The pre-cum tears of chastity dripping from his little clitty of a plaything left the tell-tale wet mark on his teal colored thong as his mind filled with lust.
Trisha waited for the others to head outside to lunch before she decided to slip into the lady’s washroom.
Ms. Halfpenny opened the door of her office breezing by ready to leave for a quick spot of lunch.
“I’m going out for a salad Trisha.”
Walking back to her desk in her high heels the anticipation built on each footfall. She had no idea Ms. Eva had come back to retrieve her phone.
Both hands gently held onto the desk seemingly alone Trisha wiggled his butt back and forth never realizing ‘til then how nice a vibrating anal plug could feel. He felt so addicted to the feminine feelings he was having as the sensations expanded.
He looked at the picture of himself with the new hairstyle and pretty top sitting in the frame on his desk. Whoever sent it along with the gift playfully added a pair of ‘Snap-chat’ kitten ears with a colorful butterfly on each upper corner with little stars in between. Part of Trisha felt like a silly teenage girly girl seeing his look it presented.
Trisha’s hand lifted the plaid skirt for him to look at how wet his panties were getting. Dropping the hem he knew if he kept wiggling his hips back and forth driving it deeper the pretty lace thong was soon going to be filled with warm cream.
Lightly slamming her hands on the desk her climax was getting out of her control. Trying her best not to do it she let slip her girlish moaning.
“Ewwww, eeewwwwww, eeeewwwwww…..ohhhhhh yesssssss.”
The idea of it popped into her mind she couldn’t help but ponder what a real cock would feel like.
Just then Eva her boss opened her office door and quietly slid in behind her.
“Lift up your skirt show me your panties gurl….yes I thought you’d like that gift….”
The woman’s hand on her shoulder three clicks on Trisha’s keyboard had a picture of a stiff dick filling up the screen. As though reading his mind she added.
“…the real thing is even better…..that’s it Trisha push it deeper…just think you’re going to climax like any other woman does and that ‘clitty’ of yours wasn’t even touched.”
The woman gently took hold of Trisha's hair and pulled it back as the t-girl secretary squeezed her butt cheeks caught up in the vibrations from the plug.
“Be the woman you are now…a real man wouldn’t be caught dead wearing dresses and skirts….taking hormones….growing breasts….that’s it have your climax my lovely secretary the days of you going back to what you once were are behind you…so pretty…so feminine you’re far too past the point of no return to ever be a real man again.”
The ‘Halfpenny’ account was the crown jewel in Ms. Smithfield’s stable of clients. The first four days of the week Trisha had been preparing documents readying for the meeting to be held in the conference room on Friday afternoon.
A hint of a BDSM ‘hobble-skirt’ to it the tight form-fitting slit-skirt ended at her calves doing little to hide Trisha’s gorgeous ass. Controlling as much of the dynamic as possible Ms. Eva had picked it out sending a semi-shear long sleeve chiffon blouse in ‘beach breeze lavender’ along with a pair of 3” heeled pumps with a note saying 'wear this outfit for Friday'.
Jay Halfpenny kind of slouched in the chair tired of going over all the paperwork in the conference room. Seeing Trisha walk in once more he watched as she laid the coffee on the table in front of him. His eyes took in the sight of her pretty bottom as the secretary asked ‘will there be anything else Ms. Eva?’
Catching him staring a little too long at the pretty chiffon blouse with its billowing sleeves first put the idea in Eva’s head.
“No Trisha that’s fine for now…..Jay if you need cream or sugar Trisha can add some otherwise it’s on the counter behind you.”
His eyes staring down at the papers he smiled politely without looking up.
“Thanks Eva I’m almost finished going over this.”
The longer the woman looked at the thinned framed on Jay the more Eva suspected it. Her mind kept adding to the list after noticing the tiny dark particles around his eyelids. It was likely at some point in the process he had given up on trying to wash them off.
As he read the documents her eyes stared at his lips on the smooth-shaven face. Many a crossdresser forgets the origin dye leaves behind a hint of discoloring when taking up the habit of using lipstick regularly.
She thought his eyebrows were just a little too thinned out and sculpted for a man. Most adult males take a certain masculine pride in having them appear bushy as though they’re too indifferent to trimming them.
When he handed the one document back to her Eva registered other signs. A woman always has an eye for details many males dismiss.
She could detect a slight pinkish look on all the fingernails kept a little too long with an oval contour while two of the fingers had the remnants of a line of polish along the sides of the nail’s edges. When a Cd uses nail polish it leaves behind a discoloring many don’t pick up on after they used polish-remover to rid themselves of the color.
Eva next took in the length of his hair. Jay wore it slicked back yet if done right the woman thought it could be made to have an attractive feminine look. Her eyes could see the tiny holes on each ear telling her they’d been pierced.
Looking up from the legal paper she spotting another telltale sign of a slight lace pattern found on women’s boy-short panties pressing against the slacks as Jay poured some cream in the coffee.
She couldn’t help yet think there is nothing else quite like panty-lines to expose a secret. Quickly processing she decided if handled correctly all could be leveraged enhancing the bottom line of the account on her books.
“You know Jay…it’s Friday and we could finish up at my place…why I could have Trisha join us…I was half thinking it might be fun to have Trisha put in uniform and wait on us.”
Her mind briefly drifted back to the former sissy-maid she use to have before he’d left after serving her for near two years.
Jay looked at Eva.
“Humm yea…maybe…what kind of uniform?...I mean for Trisha, you know I think she has a smashing figure…I hope it’s ok to say that.”
“Sure nothing wrong giving a woman like her a compliment, you do know she’s trans right?…I have a few maids outfits or uniforms …wait let me back up. I am the kind of woman that hires maids to clean my home and wait on me. My last one had to go back to Mexico for family reasons. I haven’t replaced her yet…good domestic help is hard to find…I guess I can be pretty demanding when it comes to hiring maids and other things as well I suppose.”
There she had done it…Eva knowing most Cd’s have a thing for dominant women not to mention maids uniforms she had laid the ‘Fem-Dom’ card on the table.
It was time to turn on the charm lifting up she walked over catching him sneaking a peak at her ‘Jimmy Choo’ 3” high heels. Her hand slowly undid his tie pulling the one end from under the collar.
“We’re in agreement on most of this…let’s head to my house and break out the champagne….”
Bending down she kissed him letting her hand linger lower as she moved her breasts against his shoulder.
“…hmmm what do you say?…I’d love to get out of this bra and put on something comfortable…..why if you are a good boy I’ll even let you take it off me.”
Her hand slid up and briefly let her fingers move across her nipple leaving it hard and pointed on retreat. Arching her back Eva let the twin globes entice Jay giving them a jiggle.
“Trisha would look lovely in all those petticoats under her maid’s uniform.”
Jay let out a whimper as his mind contemplated the thought. Eva kissed him once again leaving his lips colored in dark plum. Pulling away her pinky finger went to take off the smudge on the corner.
He tried lifting his hand bringing it to her breasts. Eva easily slapped it away playfully.
“You’ll have to wait baby….maybe I shouldn’t say this but I love having my nipples kissed by someone wearing lipstick.”
Her eyes holding his Eva let her finger undo two more buttons on her blouse. The pair of d-cup breasts pushed against the restraints of the pretty lace bra as they came slightly into view. Standing back the woman looked at him waiting to hear his consent.
“I’ll need your address Eva….I can use google maps.”
“No you’ll leave your car here and come with me…I want to know exactly what color those lovely panties you’re wearing are.”
Eva let Trisha know the three of them would be leaving together. Out in front of the elevator she sent the text to Delilah pleased to see a reply by the time they got into her Mercedes.
Walking into the spacious bedroom Jay turned to see Eva standing with her hands on her hips as she followed behind. Her powerful feminine energy was spiking filling the room with a sense of her dominance.
“Trisha let’s have you undress Jay down to his panties then the two of you gurls into the bathroom.’
Jay cringed at first yet felt comforted as Eva came over and hugged him from behind. The two looked to see Trisha getting down to her intimate wear.
“Isn’t she beautiful….such a doll.”
Hearing her Trisha blushed pleased to hear the compliment as she slipped off her high heels.
“We’ll talk more after your bubble bath…go in enjoy yourself…nothing makes a girl feel so pretty as soaking in hot bubbles.”
The oversized tub was room enough for both holding his arms up he watched as Trisha slowly ran the razor down leaving smooth hairless skin behind. Jay’s eyes seemed mesmerized seeing how pretty her shapely c-cup breasts looked with the nipple piercings. For years he had used breast forms while being envious of the real things.
Trisha held her smile on hearing it.
“Do you like being on female hormones?”
“I never knew how nice it can be becoming a woman. If you had seen me a few years before you wouldn’t recognize me. I was this asshole of a man who did his best to hit on women…but now I’m more caring…loving….I’m in touch with my emotional side and try to treat everyone with kindness.”
Trisha held out her thin arm caressing the body oil on it. It spoke to the feminine vanity she’d acquired in saying it.
“Do you like my nail polish?…I was thinking of changing the color before work this morning.”
The t-girl’s hands move behind to collect her damp hair before letting it drop as she next held them under her breasts giving a short wiggle.’’
Jay said what she was thinking.
“They’re so beautiful.”
“You ask if I like hormones…who wouldn’t want to have these pretty things. Now I really think women are more evolved …they’re so in touch with their feelings. I think it is a privilege being let into their club …if you know what I mean.”
Her head tilted a pretty feminine smile on her face she gently ran the body oil over the twin ‘girls’.
“Being a woman….it’s so nice…we get to wear the prettiest things…so Ms. Eva said you like to crossdress….stand Domina wants me to shave your legs and pubes off…I mean most of them.”
Cleaning the area with the wash cloth she rubbed some oil on the area. Seeing her cup his balls he let out a gentle sigh as she carefully shaved the hair off.
“I started dressing up after my mom divorced…I was 13 or 14 or something… I never really stopped….I can’t tell you how many times I purged all my female clothing only to be back at it a month or so later.”
The two caught up in their own world hadn’t yet noticed Eva in her leather slacks and matching stiletto heel boots with crimson colored corset proudly displaying her milky breasts. She remained silent enjoying hearing Trisha and Jay interact.
“Sometimes I dress and go out to clubs…but that is still dangerous…I had a Cd friend get beat up a few months back….what about your chastity cage…was it hard to lose control over your penis”
“My clitty….At first I guess…I don’t really think about it too much these days…I like vibrators now…speaking about control I have a feeling you’re going to find out.”
His eyes looked down the hairy mess gone he saw the single thin trim line looking so feminine. His penis grew hard as Trisha gave it a few strokes.
“I’ve always wanted to have it look like that….it’s pretty isn’t it?…I was too afraid of what the guys in the locker room at the gym would say if they saw it…..Ohhhhh Trisha….your mouth is so soft.”
Trisha slid even closer one hand slowly pumping the other gently caressing the smoothness of his mound she slid her mouth back and forth along the shaft of the penis.
“Eeeewww fuck…oh yessss…eeewwww.”
It took a minute or so as the oral fixation kicked in that sense that one needs to feel something moving inside her mouth. She closed her eyes relishing the sensation of the penis pulsating and throbbing covered by her mouth.
“That’s enough for now Trisha…I told you that you’d like the real thing.”
Jay turned to see the beautiful Eva looking quite dominant in her outfit of leather and corset.
His skin never felt more alive. Sitting still as Trisha slid the last of the hot rollers in the hair he looked down at the stockings attached to the frilly tabs of the suspender belt. Matching bra and panties on Jay silently had held still as Eva put his penis into the chastity cage before turning the lock. The key on her necklace had him wondering when it would next be set free.
Like two girls sharing makeup tips they both helped each other do their faces until they were pretty as a picture.
“Brush her hair out Trisha…lots of pretty curls for Maid Tanya.”
“Yes Mistress Eva.”
He let his eyes look in the mirror to see the woman standing tall in her black leather boots he’d always wanted to be dominated by a female like Eva.
“The question is who shall I put in pink and who will wear black?...you two hold hands and follow me I have a feeling you’re going to become good friends.”
Sometimes the anticipation is half the fun as Eva opened the twin doors Tanya let out a gasp. Lined with a collection of 50’s housewife dresses and maids uniforms he swooned at seeing the end of the rack with different styled petticoats. Thinking he died and gone to heaven the closet was like a crossdressers wet dream.
“Tanya you pick out your favorite looking petticoat and I’ll help you slip it on….you too Trisha let’s see what kind you like.”
Near 30 minutes later Jay fluffed out the petticoats letting the hem settle on them before making the adjustment to have things look even. Trisha looked at Ms. Eva finishing fluffing out the large bow of the apron in back on Tanya.
“I like how I look in pink Ma’am…..oh this maids uniform makes me feel so pretty.”
“So true Maid Trisha…let’s have you and Maid Tanya slip your arms in mine while we go downstairs…I do enjoy bringing the woman out in two so lovely looking.”
The timing couldn’t have been better. Careful to watch on each footfall as the group hit the bottom step the front door opened. Jay could feel his heart beat faster the moment he saw the men and woman.
Ms Delilah stood still as the two beefy males 6’ 2” and 6’ 4” respectively took in the sight of the t-girl maids and Ms. Eva.
“Bill I think we’re in for some fun tonight.”
“I would say so Tom…look at this doll in the black uniform…thanks for the call Ms. Delilah.”
“Hi Eva……I told you guys you would like what you see…lets have that champagne.”
The woman glided over to hug Delilah it had been months since Eva licked her pussy to an orgasm.
A look of both fright and excitement came on Trisha and Tanya’s face. The two holding each other’s hands moved close letting the fluttering petticoats push together.
Trisha thought to herself ‘I think I’m finally going to find out what it feels like to have a man inside me’. Tanya could feel his ‘Jay’ persona disappearing he’d been dressing on and off for a while yet this was different he could feel an attraction to the taller one called Tom.
He whispered to Trisha “I kind of like that Tom…who do you like Trish?”
“I like the looks of Bill…I haven’t told you but I’m a virgin.”
“Me too…I’ve gone out dressed up with friends but we usually only wank each other later.”
Tanya squeezed Trisha’s hand.
“I wonder what it would feel like to have a cock pulsating inside me…oh Trisha I’ve never felt so pretty….do you think they like us?”
“I’m not sure like as anything to do with it…I mean they might but I think they both just want to get their …uh oh…here they come…..does my lipstick look smooth?...oh dear me…do you think they’ll come inside us?”
"Say Doll-face I’m Bill you look good in pink…give me a spin…you look like you were born to be in petticoats and heels.”
Trisha smiled back at Tanya as he whisked her away.
Tom took a step towards Tanya only to see the t-girl maid step back as though afraid he could do little about the man should he want to resist the advances. Not more than 10 minutes later Tanya held still while on all fours on the bed. Staring at the floor mirror wearing the bra and panties he took in the sight of Tom as he undressed.
Jay couldn’t help yet think he was going to enjoy being taken by a man. He briefly considered maybe he should live as a woman full-time after all he had the money to do it.
The thick muscled arms reached out letting his hands pull Tanya back by the hips. He turned to look over his shoulders.
“I’ve never done this before Tom.”
“I’ll be gentle babe….we’ll lube you up so you’re nice and wet…I got to tell you I think you’re one fine ass looking t-girl darling….seeing you wearing that petticoat really turned me on.”
Tom let the heat of his penis be felt on the back of Tanya as his hand squirted lube in before he swirled a couple of fingers inside the anal canal. His two fingers created a gape of a hole as the rosebud entrance accepted the head of Tom’s cock. Tom spooled out lube onto his dick the first few times in and out.
Tanya squinted his eyes almost bracing thinking it would feel painful as Tom held still letting the anal canal adjust to the size of his thick girth of the cock. The meaty fingers tried to take off the bra one handed. When that failed Tom tried using both hands.
“God-damn I can never get the hang of these darn bras….how do you girls do it so easily?”
Tanya turned and smiled
“Here daddy…I’ll get it…it’s easy…see.”
The comment earned him a fanny slap. It was as though the distraction made Tanya forget about the initial pain as the discomfort disappeared giving way to a whole different batch of sensations.
There was just something about the way the glued-on breast forms swayed that drove Tanya to wonder what it would be like to have the real thing.
The Cd turned budding t-girl discovered he liked it the way the hard cock moved easily in and out. Tanya could feel the woman within being freed to experience sex as a female does. If anything it was as though he’d always had a gentle yielding nature that was finally allowed to show itself. Tanya just loved the way the strong hands glided over his smooth pretty butt.
Surely an angel of femininity had shot a cupid’s arrow hitting the heart searching his soul he knew he wanted to live his life from now on as a woman. The two started moving in rhythm making them each feel as one exchanging their sexual energy back and forth.
The voice light an airy he gently spoke.
“Ohhh Thomas your cock…it makes me feel like your woman….the way you fuck me feels so nice…..you know I had been an anal-virgin….now I know what I’ve been missing.”
Tom held the t-girl’s hips as he pushed his pelvis against Tanya’s butt creating the sound that always turned him on. The ‘slap, slap, slap’ sounded out with Tanya enjoying the feeling of the pair of man-balls hitting his pretty butt.
The t-girl cooed in delight knowing she’d never go back to being just a part time Cd.
Tom leaned down close to releasing, His body on her back he whispered.
“Once you feel this hot cream explode inside you babe…..you’re going to want it all the time.”
“Yes daddy I know you’re right….ohhh fuck…eewwwww I think I’m going to get wet too.”
“Let’s do it together…wait ‘til I spank you then let it ooze out…damn you’re as tight as the bark on an Oak tree……eewww yeah.”
One hand on the lower back Tom looked down enjoying seeing his lengthy 7” cock sliding in and out at will. It was enough he flexed his muscular upper body. His arms made stiff he swatted Tanya’s pretty bum.
“Oh Daddy that kinda’ hurts…eeewwww, eeewwww.”
“It’s supposed darling…just another reminder I’m your man and I like my t-girl feeling weak and helpless…you should be thinking about hormones after this....oh fuck here it comes….ready or not.”
“Me too Daddy…I’m dripping down my legs…..ohhhh fuck me that feels soooo warm….oh you keep letting it out…my lord how much cream do you have?....ohh, ohhhh, ohhhhhh, oooohhhhhh you’re filling me up…eeewwww…yessss daddy.”
The post-coitus embrace made Tanya feel loved. He’d never been a very muscular man to begin with yet now he knew he’d much prefer to be a woman. Tom took a tug on the half empty beer bottle. Holding the bottle moving his index finger in front of his lips a little of the beer spilled out on to Tanya.
"Shhhh….you hear that Tanya?”
Hearing Trisha and Bill in the next room she giggled. Tanya next smiled that smile a girl does when she feels connected to her man sharing something. Eyebrows lifted in amusement her hand held in front of her mouth fingers pointing straight all in a line showing off the long red polished faux-nails.
“Sounds like Bill’s got a screamer on his hands….you t-girls make the sexiest noises once you get a cock inside you.”
“You’re right….He does have a screamer daddy.”
She kissed his cheek.
“…and now so do you too.”
End of part 5 …