Lying on the carpeted floor next to her bed Tracy awoke the Saturday morning glad there was a break in classes for the seasonal holiday. A quick tug to the blanket he fluffed out his pillow hoping to get a few more minutes of shut-eye.
The night before he had brought the last of his 4 boxes from his dorm room leaving them in the hallway before retiring to sleep at her side. ‘What light through yonder window breaks?’… Tracy knew upon waking up he would slip down to the kitchen and make Lisbeth her breakfast.
Perhaps for some ‘Uneasy lies the head that wears the crown’ yet with Lisbeth she had established herself as his queen and loving female authority figure ready to move Tracy to the next level. Skilled in the art of transitioning a male student into a t-girl for the past 6 years of teaching her course Lisbeth had accumulated a fine collection of outfits and lingerie to go with the HRT regimen.
Prepared to move past the subtle sin a laying the ground work through covertly putting him on HRT she figured as Shakespeare declared ‘to do a great right do a little wrong’.
As Tracy picked up around her bedroom he noticed Lisbeth looking at him while she sipped her hot tea taking an occasional bite of one of the fresh muffins he’d made. Slight yet noticeable the jiggling on his chest as his nipple-suckers went about their purpose pleased the woman on seeing it. The time for enticement was at hand.
Opening her robe letting her milky breasts be put on display Lisbeth spread her legs wide motioning with her finger. Tracy had been dreaming of worshiping at the alter of her vagina since his first day in her class. The offering almost too good to believe he slipped his thin frame on the bed nuzzling close to the glistening lips centered in her holiest of holies between the woman’s legs.
Watching him lick at her pussy as she had done with the other males turned t-girls Lisbeth had decided to select a name from one of the classic Shakespearean romances. In Tracy’s case it would be after ‘Olivia’ the aristocratic royal character in ‘the Twelve Night’.
The potent juices slipping down his throat made him feel docile and quite compliant. 20 minutes in Lisbeth was ready to introduce him to the tactile feel so many women enjoy. The campus near empty for the next 5 weeks the woman figured it would be the perfect time.
“Come dear remove your nipple enhancers…let’s have you see your new room you’ll be living out of.”
His lips moist from her fermented juices Tracy stood up naked from off the bed unconsciously toying with his chastity cage as he replied.
“Yes Mistress Lisbeth, should I go downstairs and bring my boxes up?”
“No I have a feeling you won't be needing them so we’ll leave the boxes down there for now.”
A gentle benign feminine nature showing itself more and more he smiled as he tilted his head letting his fingers run through his long hair. At 18” the hair felt so silky smooth while Tracy had come to realize like most female’s it needed to be tended to daily.
“You've come to enjoy obeying me…I can tell…it seems to bring out a side you’d like to experience more of….bring me my 3” mules with the burst of faux feathers on the tips….be a darling and kneel down and slip them on my pretty feet.”
Likely a product of an estrogen rush a wave of feminine gentleness fell over him bringing him to nod his head silently. Kneeling at her feet he felt so small and non-threatening as she slid her feet in to each one. Bending at the waist her large breasts lightly swayed as she touched her ankle.
“Like you seem to be developing I have such pretty areolas…yours remind me of when I was just blossoming into young lady.”
Scooping them in a hold using her thumb and forefinger she gave a tweak to each nipple. Still in a bent position looking at him below her she added.
“Ohhhh I do love how sensitive nipples can be made to be.”
Lisbeth let her fingers slide along the inside of his wrist taking him by the hand she led Tracy down the hall. The room had been locked since he’d first started as her assistant. With Tracy not knowing what lay inside he drew curious.
“In the previous semesters or perhaps I should say past years those who have been of service to me have enjoyed using this room.”
Opening the door Lisbeth moved into the feminine appointed bedroom with its girlish looking wallpaper adding definition. A queen-sized bed had a pink and white quilted comforter moving lower yet allowing the bed-apron near touching the floor to be seen as it made its way around three quarters of the frame.
Two large Euro square pillows in white were behind the decorative pink and white pillow-shams awash in ruffles matching the apron. A collection of small boudoir throw-pillows were arranged in front creating a touch of feminine whimsy.
Folded half-way down his hand touched the matching duvet.
“It’s so soft Ms. Lisbeth.”
“Indeed it is yet it feels even softer if one is wearing a lovely nightgown….or perhaps a cute little ‘Babydoll’ nightie…you know the kind…”
Lisbeth slowly ran her hand on his bottom.
“….the one’s that let a pretty bum peek out at the frilly hem.”
Tracy felt his caged penis lurch forward slightly. Lisbeth slid in behind letting her soft yet firm muscled body touch his as she caressed him. Silently together not wanting to move they looked at the matching Armoire and vanity table. In the corner was an empty vase on a stool near the window. Next to it was a small bookcase.
“I’m afraid things needed to be dusted and that vase…well every morning you’ll put fresh-cut flowers in to maintain the rooms décor.”
“….Now where is that feather duster?...it must be here somewhere.”
Lisbeth threw open the twin doors to the closet. The first thing Tracy saw were 3 different colored French-maid’s uniforms with matching aprons and petticoats on the hangers next to them. Alongside the three one in grey the other black were a pair of functional ‘Mayfair Hotel’ maid’s uniforms.
The soft whimper escaped from his mouth as he reached out to touch one of the petticoats. Beyond the maid’s uniform sectioned off were different colored dresses and attractively styled skirts all hanging neatly arranged with shelving next it holding an assortment of pairs of high heels.
Towering over him in her 3” mules Lisbeth pointed to the other side of the closet.
‘There are those nighties I spoke of…much like the satin flat-sheets or high-count Egyptian cotton bedsheets they caress the skin so delicately….”
The call of the feminine expanding Tracy could feel himself being attracted to everything he looked at.
“…there’s that feather duster…above the maid’s uniform…yes Maid Juliet from last year looked so pretty going about her duties…taking to the way the petticoats bounced on her thighs doing her chores in her stockings and high heels...I must tell you... by years end she had met her Romeo.”
Lisbeth gently cupped his balls letting her fingers roll them around.
“Of course being in a maid’s uniform I require all my servants to wear the prettiest of lingerie and intimate wear.”
Her breasts felt so soft brushing up against his back.
“Hmmm…shall we have a look in the drawers of your Armoire?….oh I do love the mystery of women’s lingerie….it certainly makes a maid feel so feminine the way it caresses the skin on a body made soft and alluring.”
The doors open Tracy spotted a collection of 4 different color and style chiffon blouses along with other ones and tops just as pretty.
“I would say if you open those drawers you won’t be able to resist what lay inside….yessss perhaps it’s time you asked your mistress for permission.”
Tracy turned a quick glance at her luscious breasts he looked into Lisbeth’s eyes.
“Mistress do you think it would be ok if I tried a few things on?”
“That is so sweet……very well then…let me think for a moment….you’ll need an appropriate name…. Yes, I’ll call you Maid Olivia….you’ll have to learn how to curtsy…I’ll expect to be greeted that way every morning upon entering my boudoir."
Her finger lifted his chin.
“You should know you are entering a whole new world yet I’m certain there are a few padded bras to add lift to your bosom along with the others…open the top drawer Maid Olivia everything inside fulfills a purpose….after that I’ll introduce you to your first boned corset.”
The bounty of colors and designs seemingly knew no bounds. A lacy ruffled-butt hipster panty eased on Tracy held still feeling Lisbeth wrap the bra band around his waist.
“Now you spin it in back and slowly lift higher letting your hands slide through the opening of the bra straps…..just like that ….very good Maid Olivia…things are developing nicely for you…you have all the makings for a pair of lovely breasts….pick up your matching garter-belt then we’ll have you learn how to ‘ladder’ your stocking’s into place before slipping into your high heels….there is nothing quite like the feeling of layered petticoats on the texture of patterned stockings to make a maid feel at ease with herself.”
Mistress Lisbeth stood back to see the finished product.
“Do you know how to get to Carnegie Hall?....the same way you learn how to put on a pretty face…practice, practice, practice…..lots of trial and error with your makeup during your early morning free-time.”
A stern look sent his way she spoke.
“In the evenings before bed you will begin to read all of the Shakespearean classics…by the time classes begin next semester you’ll be much more comfortable in the material with a greater understanding of where his misogyny separates from his noble truths.”
Lisbeth pretended to adjust his petticoats giving a pull on the hem of ‘Olivia’s’ maids uniform.
“All my students study and progress I can just see you now a cute top or sweater some tight skinny-jeans …perhaps even a pretty look put in a skirt and dress or a coordinated outfit… learning along-side the other females in my classroom.”
The father hadn’t thought it odd when Josh told him he was driving home the 3 hours for the holiday break with his ‘special friend’ Thad. Tracy’s roommate Josh wasn’t sure how the man that was a corn-fed, right wing conservative farmer might feel when he let his parents know their son was coming out gay.
Packing his bags in his dorm room Josh now had the attractive look that came with being a ‘twink’ of a thin waisted weak-muscled boy so devoted in near all matters to Thad Hilltower his youthful BDSM master.
Thad looked at Josh.
“Why are you fidgeting with putting all that stuff in your luggage…you’re nervous right? all you need is to know that I love you and things will work out….you said your mother Rosemary has always been a reasonable open-minded person let me handle your father…maybe when Angus finds out I’m an Olympic athlete that will make a difference...3 years ago I came in fifth for the decathlon and this next year have a good chance at getting a medal."
“Yes sir, it’s just I’m not sure how they’ll react….maybe I shouldn’t say anything at all….what if they catch me wearing my chastity cage?”
“Slip in your fox tail and ears and come here sweet cheeks…need I remind you of what I bring to your life.”
Josh put on that smile a submissive boy of 22 does when he knows his master wants him. Shimmying out of his shorts and ‘T’ he opened his drawer shuffling through it until he found the headband an anal toy that had a 15” furry tail attached at the end of the bullet plug. The boi-toy of a twink slid close wanting to feel the taut muscles of Thad engulf his body.
He never grew tired of touching the large, man-sized organ delighting in how hard it got. Slipping to his knees Josh opened his mouth hoping to slide his lips on the cock. A quick look up he knew he was to wait until given permission.
Staring at the cute look of the fox ears Thad his fingers under Josh’s chin slid his thumb in the subby-boi’s mouth. In and out it over the lips it moved bringing Josh to feel even more docile. For years he had tried dating girls yet they always moved on after a few dates telling him he was a nice guy just not for them.
“Wiggle your butt…let me see you jiggle your tail my pretty-boy twink.”
Thad’s thumb in his mouth Josh lifted the pair of thin arms showing off their weakness as he moved his hips shaking his ass to and fro. His hair a styled mohawk of sorts was trimmed short along the sides while on top a gelled look had it fashionably styled chic for a boy of 22 like him.
Thad pulled his thumb away nodding his head when he heard it. Free of his chastity it amused him to see Josh’s penis of 5” get stiff.
“Please daddy…please let me suck your cock.”
Wet with saliva Josh eased his mouth back and forth flicking his tongue on the underside. The boi let his hands glide along the muscled thighs. He himself was too short and small to ever be a real athlete yet he was amazed that a man could have such massive leg muscles.
Josh dipped down to lick at the dangling balls awash in hair while he took in the musky scent. His thin fingers stroked the cock never stopping as his mouth swirled at the balls as best he could.
“Ohhhh fuck yea….that’s it my twink….such a good little subby boi…..eewww damn…get on the bed I need to come inside you.”
It was a playful look yet one that would bring a hard spank to his bottom. On all fours Josh wiggled his furry looking tail as he smiled. Thad slapped his cheeks a number of times before pulling out the anal plug. Arching his back accepting the meaty cock slick with lube for some reason Josh thought of his mother Rosemary.
The woman had always been so understanding aware the couple’s only child would never be an athlete his father could brag about.
Based on their conversations the last few years he could tell she was becoming more of a feminist and woman’s rights advocate. It was something that put her on a collision course with the views of her husband Angus and drove her to demand running more of the finances of the successful farming business and home they owned.
Slap, slap, slap….hands gripping the waist tightly the sound of Thad’s hips hitting Josh’s butt took him away to that place where a boy feels good he can please his master and lover with his body.
Josh was flipped over onto his back without the pulsating dick ever leaving its sanctuary. The twink pushed both hands against his muscled-up chest. A smile on his face knowing they couldn’t hold him back Thad let his upper body slowly press down against Josh’s thin frame grinding the cock in to its deepest point.
Ever since the day in high-school after football practice with his best friend sucking him off Thad knew he’d always been gay. Gifted with size and strength Thad soon learned how to dominate another person.
Lifting up his cock still moving in and out Thad took hold and stroked Josh’s penis.
“What do you say boi?”
“Please let me cream sir.”
Thad could tell by how hard Josh was that he had a chance of reaching it. The athletic man aimed the head of Josh’s dick letting it spurt forth. The warm cream splattered straight out onto Josh’s face. The jizz sliding down his cheek Josh took hold of Thad’s butt cheeks knowing he was about to come.
“Ohhhh fuck eewww sir…yesssss, yesssss fuck me Daddy….fuck your lover-boi.”
Seconds later the come came erupting out inside Josh’s anal tract.
A few minutes after finishing Thad spoke.
“Maybe you better not wear the single earring…we’ll wait for a good time to tell them.”
Held in his embrace Josh licked at some of his come that had slipped lower nearing his lips.