'The Everleigh Twins ATF Ch. 05

Whenever Naoma was helping a woman like Marilyn turn her husband 'trans' she was always on the prowl looking to do the same with a younger male. Having a thing for being a 'cougar' of a dominant woman she had thought it ironic she had unconsciously started 'grooming' a new candidate over the past many months.

The awkward tussle of lover's hands roaming on each of the other's body mingled with the passionate kissing. With their clothing on the frustration mounted as the dating ritual grew heated. When the evening began with dinner at Rouseau's restaurant Dan could only hope that Ms. Naoma liked him as much as he secretly liked her.

In some ways he never thought he'd ever be going out with the older woman. Successful as she was besides being a stunningly beautiful woman Naoma Hastings owned her own IT company and he was just a server at a coffee shop struggling to get by. More polished more seasoned than him the fact she had him by a dozen years or so only added to the dynamic.

Like many males he never took college seriously enough what should have taken 4 years to go through ended up being 8. Some days it seemed he'd rather play video games than study curriculum that needed more than a passing glance of attention.

In his mid-twenties the maturity level of one younger he drifted from one menial job to another and found himself working at the café as he reached the benchmark of 30 years of age.

A creature of habit Naoma would come in every morning for her latte. Without saying his name she took to regularly expressing a cordial hello to the thin male with nice hair that looked more like a boy than a man. To look at his narrow arms one would think he'd never been in a gym much less even tried to lift weights.

A few inches shorter than her 5' 10 height Dan would personally walk over her 'grande sized' take-out cup and hand it to Ms. Naoma as he addressed her.

It had started as a light bit of kidding Dan was given an apron worn by the previous server who'd left being promoted to assistant manager at one of the other shops in town of the nationwide chain.

One morning ready to introduce estrogen to his life the woman decided to toy with Dan as he carried her drink to her.

"Thank you Sara?...I never would have guessed...you look more like an Abigail..."

The gender reference through him off.

"...your apron...its says Sara."

"Sara...Wait no I'm...Oh ...yes the name on my apron...I forgot it's just what my manger gave me...she said they have new ones on order...call me Dan."

Ever the alpha Naoma enjoyed making males feel uncomfortable especially one she knew she could intimidate. Figuring it to be just peer pressure from dead people she wasn't much for long standing tradition either. Whoever thought a woman should be the one to wait for a male to make the first move in conversation it wasn't her.

"I think I like Sara better...or as I said maybe Abigail...yessss...I'll call you Abby for short it'll be our little secret."

Dan started to blush yet didn't draw back in protest like any man likely would at hearing the feminine reference. Her hand reached out and lightly touched the hem of the apron.

"You look good in an apron it highlights that thin waist of yours Abby. I should let you try some of my special vitamins speaking as a woman I know lots like me that enjoy the feelings they'll bring with...I think you'd like them and the way they make you feel and look."

Dan stood frozen from her powerful feminine aura when her hand slid across the slim tummy. He felt an energy tingle run through his body as she lightly kissed his cheek.

"Yes Ms. Naoma...sure if you think I'd like them...are they expensive I don't make much money?"

"I tell you what I'll treat but you have to promise to take them every day...I can go over what's in them or we could just keep it a surprise."

"Ok I can do that...I like surprises let's keep it that way."

The cougar of a woman saw the potential in the young cub of a male. She'd long since stopped dating men her age or older knowing most often had an agenda or were put off by her wealth or business acumen.

So it went for the next six months the power of estrogen tabs swamping his endocrine network the two built up a rapport until she'd decided he was ready to follow in the direction she would lead.

'Thought you'd may look good in these for our first date. No pockets mean don't bring your wallet I'm paying.'

In his tiny studio apartment Dan read the gift-card that came with the box covered in delightfully feminine wrapping paper. Inside were a pair of new loafers, tapered slacks and a violet colored silk shirt. Absent a larger buttoned down one the short half inch collar design made it clear it wasn't intended to be worn with a masculine tie.

Truth was Naoma had always thought men's ties to be a subtle phallic symbol and something she didn't need to view. The woman was curious to see if Dan would take notice of his initial entrée into the world of feminine clothing.

At the bottom of the package wrapped in its own tissue paper was a shimmering deep-red crimson thong accompanied by its own note. 'Thought this would look nice with your figure 'Abby'. Pick you up at 7. Cheers, Naoma.'

Other than the moment Dan needed to be told what fork to use for the salad the dinner went smoothy with Naoma steering most of the conversation. Like many that spent any time with her she came across as an intelligent and beautifully statuesque woman. Full-bodied kept taut from steady workouts with luscious d-cup breasts she always wore the finest lingerie thinking it to be her birthright.

Her Mercedes pulled up along the driveway the crushed gravel groaning a sound out on feeling the weight of the car she pulled to a stop in front of her impressive house. Dan felt a little out of his element taking it all in.

Inside the home his contoured 1" heels added a lift that made his butt cheeks roll a bit as he walked on the imported tile in the foyer. Absent any pockets the cut of the slacks restricted his gait yet gave his legs a shapely look.

Parted in the middle his hair gave off a sway near the shoulder line as he turned to see Naoma looking at him while she left her car keys and phone on the table.

Dan spoke when he realized he'd been walking alone while she looked on.

"What?"

"Nothing...just admiring the way you move...I hope you don't mind me saying yet you have a really cute butt."

The comment caught him off guard thinking it was something one might say to a girl.

"It's been awhile...I'm not used to wearing fancy clothes. I was surprised to see my slacks have the zipper on the side...and these shoes. Are they European or something?...they kinda of make me walk funny."

Aware he was in a pair of woman's loafers Naoma smiled

"Not funny just different...I think they highlight your legs...come take my hand let's sit in here."

Reaching out he felt Naoma lift his hand up a touch like one would with a girl in need of assistance. She guided him in to walk into the room slightly ahead of her as she took in the sight of the triangle patch of the thong pressing against the lightweight slacks in back. Moving in behind Naoma put her arm around his shoulder as the two made their way to the couch.

Slipping his shoes off the dim light in the living room added to the romance of the moment. Her arm around Dan pinning his right one taking it out of play she pulled him close kissing and touching like lovers do.

In the battle of dominance to see who would lead her assertiveness won out. Naoma next started to unbutton his buttons the anticipation building to see if the effects of estrogen had taken hold. Looking on he held still to her feminine carnal aggression.

"You know Ms. Naoma the buttons were on the wrong side of my shirt."

She thought 'that's because it's a women's blouse and not a men's shirt'.

"I know baby...didn't the silk feel nice on your skin?"

Not waiting for Dan to respond she kissed him again. Leaning into him keeping his arm back both her hands slid his slacks off after undoing the side zip. A few seconds later Naoma slowly removed his blouse.

The dominant woman had done it...the alpha female cougar had her 'cub' near naked but for the pretty thong. She thought to herself...'It appears he's been keeping his body hair free...oh yes the development has taken hold...such lovely girlish nipples pouting out... he'll have the most delightful pair of breasts in the months ahead'.

"Abby Honey spread your legs for me...that's it...very good...I like my lovers obedient."

His arms dropped passively alongside his body. A nervous smile he looked at Naoma.

"You like calling me Abby."

Running her hand up and down his body she felt him quiver lightly brushing the growth of his breasts as they moved slightly. She wanted him totally naked while she remained fully clothed knowing it would help even more in bringing out his submissive side.

"Yes I do...I think you like me calling you that...hmmmm...don't you Abby?... maybe I'll even call you Abigail sometimes."

Dan felt a kind of tingle in his tummy on hearing the feminine name and its emasculating impact. He sensed his cock firming up. Her hands went to the pull the thong off. 'Abby' let a whimper escape on seeing his penis pointing straight out.

"How cute...It seems someone likes being called Abigail."

Saddling up closer to him her hand gently stroked the 5" penis. Spreading his legs even wider his body limp they both knew he was hers to play with. Slow gentle strokes bringing him along he could feel a gentle yielding nature rise up within him.

"That's it darling just lie back Abigail your woman is in charge...oh I have so much to teach you...so much to show you...hmmm is my honey ready to learn a different way to do things...a new way to live?"

Short choppy breaths he looked at her silently nodding his head.

"Abby do you know what the term Mistress means these days...are you aware of what it means to be a Mistresses protégé...to be obedient and willing to learn..."

"Mistress? ...Mistress Naoma?"

His penis let slip a tiny squirt of pre-cum fluid on saying it. Running her palm over the moisture the woman used it to make the head of the cock get wet.

"Yessss Mistress... I think my Abigail is going to make a lovely submissive... a pretty protégé for her Mistress Naoma.'

She stopped her stroking on hearing him moan he wasn't entirely sure what the woman meant. His penis lurching Naoma ran her hand along his unkempt pubic hair.

"This is going to need some tidying up...something more smooth and clean shaven ...perhaps a cute thin little line."

It was time she pulled him deeper out to sea with her enticing intimate wear. Naoma moved between his legs adjusting his body onto the couch with her on top.

"Baby undo my blouse I want to show you my pretty bra...say yes Mistress Naoma."

With Naoma on top she arched her back lifting up a touch as he started to undo her blouse.

"Yes Mistress Naoma...these buttons...they're just like mine...I mean the way they unbutton.'

"Sweetie they should be ...we both had on lovely feminine blouses...see you spent the entire evening being dressed in clothing any girl would enjoy wearing ...even your heels were a pair of women's loafers...and that pretty girlish thong...I knew you'd look good in it...the server complimented you on your outfit didn't he?"

Her blouse undone hanging alongside her body he stared at her luscious breasts held captive in the embroidered lacy brassiere. Naoma bent down kissing his neck she whispered in Dan's ear.

"He told you how nice you looked...you found out how good it is to receive a pleasant comment on your outfit."

Captivated by the sight he stared at her milky breasts before he looked up at her once more. She let the comment come out with a smile.

"...oh I love being a woman ...we get to wear the prettiest lingerie Abigail."

"Yes Mistress...your bra looks very pretty."

The woman gave off a shake letting her sumptuous breasts jiggle before bending to again whisper in his ear.

"I'll let you in on a secret...it feels even prettier to wear."

For months his skin had been taking on a softness with feminine curves developing. His nipples and areolas became more sensitive than they ever had as they sat crowned on his developing breasts.

The idea of wearing lingerie percolating in his brain Naoma could tell he was thinking about her comment.

"Slip in to your heels Abigail I'm taking you to bed."

Naoma had a thing for being fully clothed while having her novice t-girl lovers naked. Dan's hand passively resting around her waist with her arm around his shoulder the two made their way up the stairs.

Nicely appointed having the money to do it the feminine décor in her bedroom

had everything a woman of wealth would want. Removing her blouse she eased him to the floor as she stood looking at her image in the mirror above her low-rise dresser. The bed in behind her Naoma looked down at 'Abby' in more ways than one.

"Baby take my trousers off."

As though a confirmation of who would wear the pants in their relationship he knelt in front of Naoma unbuckling her belt as she kicked off her shoes. Flaring at the hips her legs came into view as the slacks lowered.

"Abby honey help me slip my high heels back on."

His hands glided along the stay-up thigh highs after he slowly slid the heels on each foot. Her hand reaching in back without looking Naoma unhooked her bra letting it tumble to the floor.

She seemed so confident so majestic looking in a superior feminine way. Her legs spread wide with Dan kneeling between them he stared up at Naoma before dropping to gaze at her lace panties and the treasure that lay behind them.

Closing his eyes he took in the fragranced scent of her vagina. It had been so long since he last smelled much less seen a female's pussy.

Naoma looked at her captured prey of a boy thinking 'if you could only read my mind...you'd know how much I'm going to transform you in the coming months'.

It was as though he knew he needed to ask for permission before touching Naoma.

"Take your tongue out Abigail...one single lick...move it along the slit of my pussy."

He knew he should have protested being called the girls name yet he couldn't work up the nerve instead just accepted it. Felling the urge he commented on seeing the exclusively feminine underwear.

"Your panties look pretty Mistress."

She thought 'yours will too come morning time'.

Tongue out Dan let it slowly move up along the pouted lips pressing against the material. Naoma hooked her thumbs in lowering her lace panties. The woman enjoyed this part of the ritual for it was where most men realized in some ways they in fact envied women for having a vagina.

She lowered to sit on the edge of the bed as her fingers slid into his hair bringing his head closer and his lips to her mound.

A firm believer that pussy-worship leads to obedience the woman guided his mouth to her vulva ready to train the boy of 30 in the ways of a t-girl in the days ahead. Having tamed and broken many a male in her time she also knew once obedience becomes a habit a level of submissiveness develops.

It was from there a male could be led into a new life filled with sensations and delights never previously experienced.

The minutes passed as Abigail licked away digesting her powerful fluids. It seemed the longer he did it the more he enjoyed the way they tasted. Patting his head like one would a cherished pet Naoma spoke.

"That's it darling...you must know my juices have estrogen mingled in...just like those special vitamins you've been taking...take my fluids in...feel them flow throughout your body..."

Lifting her feet she let one of the heel's almost puncture the skin on his back. Ten minutes went by before she pointed to her bed. Abby quickly slithered on to the soft brushed high-count cotton sheets.

Slipping off her shoes Naoma turned to see Abby lying on his back on the bed. He looked so helpless so inexperienced. The woman had always enjoyed mounting a male especially one so innocent and naïve to the ways of an alpha-female 'cougar'.

She slid forward easily slipping in his 5" penis.

"Baby you look so sexy with your legs spread."

A sign of welcoming acceptance even Dan knew the person that spread their legs was the submissive one. Together their bodies acted as one. Abby lifted his legs letting them glide along the outer smoothness of Naoma's hips. Lifting and lowering the woman rotated her pelvis grinding down on his dick.

Her breasts so appealing in their size and appearance gently rubbed along his chest. It felt so nice against his softening skin. For the last few months his thin body had seemed so different. He could feel a heightened sense of sensitivity to the touch of it. All but his pubic hair it was enough he began to keep it smooth and hairless.

"Eewwwww...ahhhhhhh...ohhhhhhhh...I think I'm going to...ugggggg."

Lacking the staying power of muscled up virile man in a mere 6 minutes of time Naoma had drained him of his seed. A few minutes after he was cuddled in her arms falling asleep.

The sun peeked through the bedroom windows it was enough to wake Naoma ready to bring her protégé further along. Pressed against the tightness of her panties the strap-on remained out of his view as the two kissed lightly. Horny he felt like any male only more diminished after being taken the night before.

Naoma's hand slipped under it and cupped his tiny breast. She gave it a pinch with her hand to make it seem fuller lifting his areola and nipple out. 'Abby' looked down to see Naoma suck the sexy looking nipple.

He felt so much like a woman feeling her lips toying with the nub. The sensations amazing it made him feel attractive in a feminine kind of way as though his body could bring her joy by simply playing with it. His heart beating fast the declaration came out.

"I feel so different inside Mistress."

"Roll over sweetie I have something for you that will also feel different inside."

The strength in her arms much greater than his Naoma eased Abby on to his tummy. He hadn't even known it was there until her tongue licked around his rosebud entrance with the anal plug in place.

Her hands spread his legs wider before doing the same with the cheeks of his bottom. Licking around the entrance she slid the butt plug out. A dollop or two of lube had the woman sliding the strap-on dildo inside.

It came out in a soft quiet lovers voice.

"Just hold still Abigail let your pretty bum adjust to the size."

Naoma gently ran her hands along his body her touch seemed to activate so many of the numerous erogenous zones. With her body on top engulfing Abby's he could feel the movement of the phallus. At first it hurt yet the discomfort soon gave way to new more pleasant sensation.

The dildo sliding in and out she lifted up bringing his hips with her. Abigail found himself on all fours accepting her cock as the woman pushed and pulled. He felt so docile...so passive...so accepting...so feminine. The gentle movement of his budding breasts made him look down to see them. The nipples crowned on the blossoming pair soon grew hard and pointed.

His hand reached back to rest on top of hers as she fucked him. Naoma let it stay knowing her firm grip on his waistline was helping to drive the action. A few minutes later Abigail took to moaning as much as any submissive young girl would.

The sensations felt amazing all he had to do was accept that he was being made to feel much like any woman.

Naoma began to think of the feminine grooming and make-up session that lay ahead. She'd done it time and again with others the seduction of glamour after being fucked like a girl was too enticing to resist. Within a few hours he would be as pretty as a picture welcoming his official entrée into a gurls world.