[TG/TF] Caught in the Act (Commission) (Patreon)

A Commission for Rosenile on DeviantArt

When your domineering wife catches you crossdressing she decides to take things one step further. 

~

You stare at the outfit, meticulously planned and laid out across the bed. Your wife had finished putting it together not long before she left to meet her girlfriends and you have been staring at it ever since. The centrepiece was a gorgeous chiffon dress, orchid purple and with a flowing skirt and deep V neckline. You had ached with jealousy watching her try it, along with a dozen others, yesterday afternoon at the mall. She always insisted you come with her when she went shopping, not because she needed you to pay, but because she needed an audience. Sonya loves to play dress up, even now that she’d reached her thirties; hiding your jealousy at her freedom to do so took more will power than you would ever openly admit.

You run your fingers across the smooth fabric of the sash, imagining what it would feel like cinched at your own waist. How the dark heels she’d paired with it would feel against the soles of your feet. You smile, knowing that soon you would no longer be wondering. Sonya had left almost twenty minutes ago; the coast was clear.

Eagerly you undress, ripping the briefs and other male clothing off; it never felt quite right, all those suit pants and sports jackets. Shedding them was like shedding a cocoon and soon, you would emerge a beautiful butterfly. Almost reverently you pick up the light pink panties laid out on the bed, enjoying the slight scrape of lace against your thighs as you pulled them on. They were tight against your groin, not built to accommodate the bulge there but you ignore it. Despite the slight discomfort these already felt so right compared to the briefs you wore every day. Before you got married, you’d been able to wear panties like this under your clothes every day. Now you had to wait and savour these special occasions.

Next the matching bra, after so many years of secretly trying on clothes this way you are adept at hooking it around your back. It helps that you’re sligh; your lean frame easily fits into most women’s garments, something you are thankful for. It was as if the universe was telling you this was right, the way things were supposed to be. For a moment you gaze down at yourself and sigh with disappointment. Of course, you have nothing to fill the bra with, you’d always made do with socks or other cloth but you hated it. You wanted to feel the soft cups of the bra against your bare skin.

How many hours had you spent over the past few decades wondering how it would feel to have breasts that could fill that space? You remember vividly as a young teen, lying in bed wishing for it, trying to will them to grow. How each time your mother had looked at you with such disappointment; she never had forgiven you for the crime of being born a boy. You’d wanted to make her proud, be the daughter she so wished for, but it wasn’t to be. Instead, you were stuck in this flat, angular body.

Shaking off the dark memories you return to the task at hand, delicately picking up the dress by its short sleeves and holding it against your skin in a warm embrace. You step in front of the mirror and admire the it against your form. The fabric felt silky against your smooth skin, which you secretly moisturise every day in anticipation for these rare moments of privacy. Reverently, you lower the dress to the ground and step within, taking your time lifting it up your body and enjoying the lose fabric tickling your skin. You carefully reach around and do up the zip before turning ahead and taking in your reflection. The dress is beautiful and you feel beautiful in it. The fit isn’t perfect, your straight and narrow body lacks the necessary curves to fill it out but still. With a soft smile you sway your hips, letting the skirt flow around your ankles in a soft wave. The purple compliments the tone of your skin perfectly, even better than Sonya’s, a realisation that fills you with confidence.

You know just the shade of lipstick to match.

With a spring in your step, you move to Sonya’s make up table. You know it as intimately as she does, having secretly sat here many a time when she wasn’t home. You know where she keeps every tube and powder and exactly how to use them without her noticing. Opening the drawer, you run your fingers over the cool metal tubes of lipstick until you find the one you are looking for; a deep blush pink. Gently you run it across your pouting lips, feeling the cool pigment stain your lips. Smacking them together you smile, what was once thin now looked full and sensual. Soon you are working faster; lengthening your lashes with mascara, dusting your cheeks with bronzer and carefully applying matching eyeshadow. Each time you are conscious to put the items back exactly where you found them, lest Sonya realise what you have been up to. You love this face, with its high cheekbones and large eyes, you only wish you had the gentle, sloping jaw to match.

Placing down the eyeliner you sigh with contentment. You are finally complete, the real you has emerged from that cocoon of maleness at last. Feeling free and confident you stand, twirling on your toes so you can feel the air beneath the skirt. A breeze flows under and brushes against your panties, sending a thrill through you. You feel as if you could fly when suddenly-

“What are you doing?”

You stop, horror and humiliation filling you as you lock eyes with Sonya standing in the doorway. You had been so caught up in what you were doing you hadn’t heard her come home.

“I…” You don’t know what to say. What can you say?

Her eyes are scanning over you and you feel yourself going red with shame. You have never been the most macho of men but still, what must she think of you now? She takes in your face, make up expertly applied. It is painfully obvious this is not a one-time occurrence.

“How many times have you done this?”

You look to the ground, you don’t want to lie to her but at the same time, you can’t just admit you’ve been doing this since you were a child. You lick your lips nervously and she repeats the question but this time, something about the tone compels you to meet her gaze.

There is something different there, her eyes seem sharp in a way you have never seen before. Like a predator taking in prey and despite everything, you feel a shiver pass down your spine. That piercing gaze compels you to answer.

“Years.”

To your utter shock Sonya’s eyes narrow and a small, almost vicious smile appears on her lips. Like a deer in the headlights, you find yourself frozen as she slowly approaches, circling around you like a shark and taking in your dressed form.

“Years you say.” She purrs, “Is this what you really are on the inside then? I always knew you had a feminine side darling but this…I will admit this is a bit of a shock. Your make up skills are impressive.”

“I’ve…had a lot of practice.”

“So I see. You know, I have a secret too darling.”

You blink at her in shock as she leans in, her hot breath tickling the shell of your ear. This is not how you imagined this confrontation would go.

“I like women just as much as men.” She whispered, “Especially good little submissive ones like you.”

You balk. Both of you were from conservative, old money families. To admit such a deviance was…well unheard of. Then again, cross dressing would likely be considered even more taboo in their circles, if he ever breathed a word of what she just admitted it would be mutually assured destruction. She doesn’t give you the chance to respond though, moving away quickly, back to the door before glancing back at you over her shoulder.

“Undress. Then we shall talk.”

~

You hate cleaning off make up. Normally it was because you knew it meant going back to being your boring male self but today there was a new layer of dread. Had you just ruined your marriage? How could Sonya ever respect you as her husband now that you had disappointed her like this? She knew you were no alpha male sure but there was a difference between having a husband who was soft spoken and sensitive and a full-on cross dresser.

When you finally emerge, back in your normal clothes, Sonya is sitting on the couch. She’s laying back, arms spread and legs crossed, that same sharp look in her eyes.

“Sit.”

You do so. You’ve never heard Sonya use this domineering tone before, it makes your knees tremble. You open your mouth to apologise and explain but she holds a hand up to silence you.

“When I married you, I knew you had a sensitive side.” She started, “Women are supposed to be submissive to their husband, so I thought marrying you would allow me more control than other options.”

You swallow.

“Had I known you were into dressing up as a lady well…I’d have put you in your place a long time ago.”

Her final words are punctuated with that hard stare. Sonya had always been a demanding wife; she knew what she wanted but she never steps far out of what was expected of her as a woman. To know she picked you for that reason is both humiliating and…exhilarating.

“Is it only dress up?” She asked after a few moments of silence, “Or is it…more?”

“More.” You have a feeling lying right now would be a bad idea.

Sonya’s face lights up like a kid at Christmas. You see a fire in her eyes you don’t recognise and you realise it’s desire. Your answer seems to have been the right one. She stands and walks over to you, taking your head in her palms.

“To think, we could have both been so much happier all this time.”

You open your mouth to ask what she means but a finger on your lips stops the words in your throat. Sonya clucks her tongue at you and smiles.

“Don’t you worry, little girl. I am going to take care of everything.”

~

The next few days are tense. You feel like you are walking on eggshells. Sonya never elaborates on what she meant by ‘take care of everything’, you are forced to simply wait and see. She does not leave the house in order to ensure you do not try on her clothes again.

“You hid something very important from me.” She says, “So I must punish you. You will get to play dress up again don’t you worry. But it will be when I say.”

You don’t know how to feel about this new Sonya. Her overwhelming dominance leaves you feeling weak at the knees; the small words of praise, the pats on your head when you submissively comply with her wishes make delight and pleasure coil inside you. Moreover, the promise of being able to try on her clothes with her express permission is nothing short of miraculous. The best possible carrot to dangle in front of you.

As the days pass packages begin to arrive. Sonya doesn’t let you see what is in the first but when the second is delivered she sits you down in your living room, a pot of tea between you. She makes you sit in silence as she prepares, unwrapping the cardboard box and removing a small glass phial. You feel your eyes narrow in confusion, that was the last thing you expected.

“This.” Sonya dangled the phial of cloudy liquid between her fingertips, “Is a special concentrated female hormone. It is very rare and very expensive, understand?”

You nod, a feeling somewhere between nervous and excited begins to well up inside you.

“You will drink it.” Sonya smiled, “And then you’ll be exactly what we both want you to be.”

“Where did you even get this?” You ask, eyes full of wonder.

“Connections.” Sonya’s tone implies she is not going to elaborate further.

Sonya pours the tea with a grace and mastery that only an old money upbringing could achieve. You watch with blood roaring in your ears as she pours the phial of liquid into the cup in lieu of milk and slides it across the table to you. You take it in shaking hands and hold it, letting the heat seep through the porcelain into your skin as Sonya regards you. Her eyes now hungry.

So many emotions are swirling inside you; excitement, trepidation, eagerness, desire. You swallow them all down along with the tea. It is so hot it burns your tongue but you don’t care, you gulp it down so fast you don’t even taste it. You feel the hot liquid make its way down your throat and settle in your stomach, heating you from within.

“How long will it take?” You ask, Sonya sips at her own tea and shrugs.

“Not sure, but I don’t want you to move from that spot. I want to watch when it happens.”

At first you sit filled with anticipation, muscles clenched and hypervigilant for any sign of change but as the minutes pass so does the adrenaline. Time drags on, with Sonya sipping at her tea and you find yourself becoming bored and disappointed.

It is gradual, so slow that it takes you a few moments to even notice, a slight prickling of skin across your chest. Almost like pins and needles, not quite pain, not quite pleasure. You bring a hand up to the skin and rub at it through your shirt and gasp as the sensation increases tenfold as you make contact. You can feel it spreading, down the planes of your stomach and legs, nestling between them.

“Undress.” Sonya ordered, that same hungry look in her eye increasing.

Obediently, you comply. Each touch of fabric, no matter how light, sets your nerves alight as you slowly strip before her. Once or twice, you are forced to stop as the sensations begin to overwhelm you only for Sonya’s stern stare to force you to continue.

You watch with fascination as your body begins to change, it is slow but if you focus you can see it, the slight movement of your skin. Shaping itself like clay under a sculptor’s hands. Excitement fills you as you see the slight raise to your chest, the smooth skin slowly but surely becoming rounder. Your dark, useless nipples begin to grow, turning a bright pink against your tanned skin. The temptation is too much and you press a finger against one of them. The touch is electric and you gasp at the pleasure mingling with that strange tingling.

“No touching.” Sonya says sternly, “No touching your body until I say.”

You nod and remove your hand, the submission sending a thrill through you. It takes hours and Sonya forces you to stay naked the entire time so she can watch the transformation take place. You ache to touch your new skin as it stretches but each time you try, she stops you with that same hard look. You have to make do with the feeling of the change alone.

Soon a cleft begins to form between your breasts as they swell; going from small and perky to full and round as the hours pass. You can’t stop staring at them, your lovely new breasts, they are just as beautiful as you dreamed they would be all those years ago. The skin even manages to stay smooth, not a stretch mark to be seen. You want to hold them so badly, to feel their weight against your palms but you know Sonya won’t allow it. You walk about the room, twisting and turning in order to see each change that takes place.

Almost as exciting is your ass, now round and heavy against your hips. You realise as it grows that it’ll match your breasts perfectly, giving you that coveted hourglass figure women would kill to have. Sonya grips the flesh firmly under her palm, causing you to gasp as the pins and needles spread across your skin. You want her to keep going, to take the other cheek in her free hand and squeeze but she doesn’t. Ever the tease she simply slides her hand across the smooth curve before walking away, leaving desire coiling in your stomach and groin.

That desire seems to meld with the tickling sensation, spreading across the skin of your ass and hips and round to your front, burying itself between your legs and increasing the tingling there. The intensity makes you dizzy, you flop back onto the couch, still feeling your hips rise ever so perceptively as your ass continues to inflate.

“Here comes the interesting part.” Your wife purrs, her eyes locked on your lower half as you lie on the couch and writhe.

You can feel it, your manhood, the cause of so much disappointment and strife in your life, disappearing. You close your eyes, focusing on that strange feeling over all the others. At first it is simply smaller, then something seems to invert inside you; where solid flesh once was an absence forms. You can feel a hole opening and your insides roiling as they transform.

“You are gorgeous.”

You feel yourself blush with delight at the praise. Finally, you open your eyes to peak as the sensations subside a little. There is still a mound of dark curly hair between your legs but it’s neater than ever and perfectly curves over soft pink lips. Without thinking you trace a hand down the plane of your stomach to touch it only for Sonya to grab your wrist. Wagging a finger back and forth she grins at you.

“Naught, naughty. Not yet.”

You whimper; already you can feel a subtle wetness forming down there and you ache to explore your new pussy. You have waited so long for it but you know disobeying Sonya would be a bad idea, especially when she is looking at you with that domineering gaze. You are forced to continue laying back on the couch as wave after wave of sensation flows down your body. With the major adjustments complete you can feel the hormones filling in the last details. It is as if an airbrush is being smoothed over your entire body, rounding all those angular hard edges into smooth curves. Your feet become dainty, your fingers long, lips full; it’s exhilarating and terrifying feeling each nerve come alive as they change.

You resist the urge to scratch at your head as you feel the hair begin to spring forth from your skull. Soft and wavy, it tickles at your shoulders as you sit up. You desperately want to run to the bedroom so you can see what it looks like but you know Sonya will make you wait. That same itch spreads to your eyebrows and lashes as they too grow and shape to fit your new face.

Finally, that odd prickling begins to subside entirely. You skin feels alive; sensitive and new, electricity seems to spark across it at the subtlest of touches as you shift on the couch.

“I think it’s done.” You whisper; the voice that emerges from your throat is light and lilting.

Sonya nods approvingly and you feel relief surge through you. If she hadn’t liked what she saw you didn’t know what you would do. Her face splits into a devious grin as she pulls you to your feet and begins to drag you toward your shared room.

“Let’s get you fully made up.”

Your heart soars; finally, you will wear those clothes you always loved but now they would fit you perfectly! Sonya lets go of your thin wrist and reaches into her cupboard, revealing the package she forbade you to open a few days earlier. You watch with baited breath and she unwraps the soft tissue paper, unfurling it to reveal a pair of panties

They are pale pink, with a swirl of lace patterned to look like petals across the front. A single satin rose sits in the middle of the waistband. They are far more girly than anything Sonya had ever worn and you feel your heart begin to thump against your rib cage as your excitement increases; they are for you.

Sonya says nothing as you run your fingers across the smooth material, she simply gives you a satisfied smile. Even through silence the order is obvious and you slowly bend over and step into the panties. You raise them up the smooth contour of your legs slowly, sparks flying across your skin as the lace softly brushes against your new skin. It’s a tight fit, you suspect deliberately so, your ass cheeks are still half uncovered by the bikini style underwear and to your utter delight you can still feel a slight breeze between your folds. The panties were crotchless.

“Now you can keep them on at all times.” Sonya speaks up as you notice, “No matter whatyou are doing.”

You look down at yourself, still unable to fully believe the body you’re seeing is yours. The pink panties match your skin perfectly, contrasting against the darker tone. You can’t wait to see what they look like in the mirror but Sonya sits you down on the bed facing the other direction.

“Once we complete you look, then you can see.”

You smile to yourself in anticipation as Sonya collects various items from her make up table, having to force yourself into a neutral expression when she returns and begin to apply. You revel in the tickle of mascara and the sweet scent of fruit wafting from the peachy coloured gloss she applies to your lips. The anticipation builds as Sonya takes her time, you resist the urge to bite your lip, lest you smudge the gloss.

“There, my perfect girl.” Sonya purrs, eyes roaming over your form.

Filled with excitement and nerves you jump to your feet, running around the bed to the full-length mirror to finally see your new form.

You gasp.

A beautiful woman stands before you; with a heart shaped face framed with soft brown waves that come to rest curving around the underside of her breasts. Her long lashes made her eyes appear even wider and her pert, glossy pink lips were open in surprise and wonder. Experimentally you turn, taking in the shape of your body from the side, looking at those wonderful new curves. You were still more petite than Sonya; where she was voluptuous you were almost doll like and delicate. The pink panties were snug against your ass and crotch, no longer was there a bulge to distract from them. You find yourself beaming with happiness, you have never felt more beautiful or at home in your own skin.

Sonya appears behind you in the mirror, placing a firm hand on your shoulder and facing you straight forward again before slipping them down to cup your breasts. Your eyes flutter closed for a moment as you marvel at the feeling of those warm hands holding your tits. They were so much more sensitive than your old flat chest had been. Slowly, Sonya tightened her grip, rolling the flesh below her fingers almost like a massage. You watched, hypnotised by the movement in the reflection; watching Sonya pressed your breasts together over and over again before letting them go and watching them bounce slightly with the sudden pull of gravity.

Sonya takes your chin between her thumb and forefinger, squeezing it tight and forcing you to look at her over your shoulder. You swear you can almost see fire dancing in them.

“From now on, I make all the rules.” She whispered, “You belong to me.”

You feel your stomach somersault as you nod silently. The submission melting into your mind and pooling in your stomach. It felt so good to just listen and obey, to not have to think or worry about anything. With firm hands Sonya turns you around and pushes you down to kneel before her.

“Time to put those pretty lips to good use.”

You swallow nervously, desire pooling inside you as you gaze up at her. She lifts her long skirt with one hand and places the other on the back of your head, guiding it between her legs. Obediently you slip your now slim fingers beneath her underwear, lowering it down to reveal folds already glistening with moisture. She steps out of the panties, kicking them away before resuming her stance, legs wide and guiding your face into position. Even as a man you had never done this for any woman, especially not Sonya. Your sex lives had been ordinary affairs with limited positions, looking back you wonder how she managed to keep this dominant side to herself hidden for all this time.

You are powerless to resist her now though and you obediently open your mouth, placing it over her wet pussy in a kiss. You run your tongue down her folds, feeling her skirt fall down your back so that you are nearly fully enclosed. Through the fabric Sonya’s hand comes to rest back at your head, holding it in place as she gives orders; how fast to lick, where to position yourself, how much pressure to apply. You obey without question, feeling her legs squeeze around your head as she starts getting closer.

Pleasure at the submission pools in you. You feel your new pussy getting wetter and wetter with each stroke of Sonya’s hand on your head. You want to touch yourself so badly but you know you can’t, Sonya would never allow it. You are forced to kneel, desire building in your core as you pleasure your wife instead. After a few minutes she shudderes, wetness flooding out of her and onto your lips. She orders you to lick her clean and you do so before finally drawing back.

Sonya pulls you to your feet for a moment only to then push you backwards onto the bed before leaping atop you and pinning you down with ease; knees either side of your hips, hands pinned above your head. You barely have time to take a shaky breath before her lips are on yours, tasting herself on your tongue. The kiss is rough, authoritative; she is confirming what you both know; she may be about to pleasure you, but she would always be in control.

“Now,” She purred, lips still brushing, “Stay still and don’t cum until I tell you.”

You whimper. Your pussy is throbbing with need, wetness pooling between your folds; if the panties were not crotchless you know they would be soaked through. You’ve lost count of how many times in your life you’d imagined this; what it would feel like to have your body touched as a woman. The anticipation and desire overrides everything other potential thought as Sonya lets go of your wrists and crawls down your body till her lips are resting against your stiff nipples. Your body arches against your control as she takes that sensitive nub in her mouth, swirling her tongue around it slowly and flicking it against her teeth. You keen, you’ve never felt anything like it. It simply couldn’t compare to all those nights you’d spent lying awake tweaking your nipples with your fingers imagining this. The pleasure was tenfold what you expected and you can’t help but pant and moan as Sonya starts to suckle at you, electricity lancing from your tits to your lower stomach with each suck.

The pleasure doubles as she takes the other nipple between her thumb and forefinger, rolling it almost lazily. You bite down on your lip, tasting a mixture of peach lip gloss and Sonya’s own residual juices. The slight pain does nothing to alleviate the near overwhelming ecstasy, in fact, it almost enhances it.

Her fingers leaves your nipple, tracing trails of heat down the plane of your stomach until they rest on that mount od wet hair between your legs.

“Please!” You plead; around your nipple you feel Sonya smile at your begging.

Far too slowly, she slits a single finger between your folds. The soft pad of her finger strokes across your clit and down your cleft with a featherlight touch and you feel as though you’ve burst into flame. Heat washed over your body and you feel your skin blushing deeply as the sensations take hold. Slowly, Sonya’s finger strokes up and down, never quite reaching your clit again or delving into your hole; it is simultaneously too much and not enough, one giant tease.

You moan and writhe only for Sonya to bite down on your nipple in punishment for moving too much. It’s so difficult to stay still, electrical currents and flowing through your body, making it jerk and buck against your will with each new bolt of pleasure.

After what seems like years and seconds simultaneously Sonya finally slips a deft finger into your aching hole. The feeling is indescribable, your male body had never experienced a sensation such as this. You felt yourself squeeze around that digit as it pushes its way inside, there was a kind of burn, a pleasure mingled with a slight pain and stretching of muscle that was satisfying in a way no other touch could be. You can feel the finger curling inside you, rubbing against your inner walls and sending even stronger waves of pleasure radiating down your legs. They begin to shake with the sheer intensity and Sonya begins pumping the finger in and out, timing it so hit alternated with her sucking. Your body was helpless against her, there was no respite from the ecstasy that is slowly starting to overwhelm you.

You can feel something building within, all the muscles in your body slowly tightening as pleasure pools in your lower stomach. You’re getting closer to the edge, you know you have to try and hold back, Sonya hasn’t given you permission to cum yet but it’s so hard to resists…

“Not yet.” She growls, stopping her sucking for just a moment, “Don’t you dare cum before I say.”

She continues with her ministration, in fact, she seems to double in her efforts. Rough tongue pressing down on your oversensitive nipple, finger pumping harder and faster inside you. She even places a thumb against your clit so that with every thrust of her fingers inside of you she presses down on it. It’s too much, you can’t escape it; pleasure is filling every inch of your body and you can do nothing to stop it. Your moans are becoming higher pitched, breathy and short as you near the edge. You try to hold back but it’s impossible. Your insides tighten and suddenly release as a wave of ecstasy washes over your body, you writhe and shudder as you cum; feeling a jet of liquid squirt from somewhere deep within you. It’s stronger and better than any orgasm of your life and leaves you reeling, seeing stars for a few moments afterwards as the waves of pleasure reside.

When you finally come back down you see Sonya still sitting on your hips, she’s frowning at you with that same steely gaze that makes butterflies dance in your stomach.

“I told you not to cum unless I said so.” She glares, “Naughty girl. You’ll have to be punished for disobeying me like that. Don’t you agree?”

You nod obediently, mind still in a haze of pleasure. With a gleeful smile Sonya leans back, slipping her hand back into your folds and stroking. Post orgasm the skin is so overly sensitive it almost hurts but she doesn’t stop.

“Admit it.”

You can only gasp, the sensation between your legs…it’s too much…

“Admit. It.”

“I-I’m a naughty girl.” The words are choked.

“And you deserve to be punished.”

“I deserve to be P-puh-punished…”

She continued to stroke, so slowly that building to another orgasm was impossible, ensuring to alternate her technique just often enough that your body cannot adjust. It’s torture, you’re stuck on the edge and there is nothing you can do about it but gaze up at your wife; you are completely at her mercy. You lose all sense of time and control; you beg, you try to writhe but Sonya’s bodacious form pins you down. After what seems like an age Sonya finally speaks:

“Have you learned your lesson?”

“Y-yes.”

“What did you learn?”

“Not to d-disobey you. I won’t do it again I s-swear.”

“Good girl.” She coos, “You’ve earned your reward.”

Finally, she increases the pressure and speed of her touches, swirling around your clit. It takes only seconds before you are coming again, having sat on the edge for so long. You feel your eyes glaze over, unable to comprehend anything but the pure pleasure you are finally receiving from her. You’ll be a good girl from now on, you’ll listen to everything she says, do everything she asks, so long as it means more of this.