A Trans-forming Night

It was supposed to be a quiet evening.

Your wife, Sarah, had messaged you earlier saying she'd be out with friends until late, so you figured you had time--time to finally try on the skin-tight dress you'd been hiding at the back of your closet.

The dress slipped on smoother than you expected. It hugged you in all the right places, and when you turned toward the mirror, something clicked. You stood there in awe, feeling more like yourself than you had in weeks.

You have always had a very feminine looking frame and with your hair mid-back length you got mistaken for a girl many times. It didn't help that your voice was also very high pitched for a guy. But tonight--tonight you got to actually see what the girl you would look like. The soft tight fabric against your skin, the shine on your freshly shaven legs, the small smile you let yourself have--it all felt perfect.

Until the bedroom door opened.

"Hey! I forgot my charger--"

You froze.

Sarah stood in the doorway, wide-eyed, lips parting in surprise, her hand still resting on the doorknob.

Time stopped. Sarah's fingers got slack against the doorknob, her breathing catching audibly in the silence that stretches between you. For a long moment, she just stands there--her gaze flicking from the dress to your face and back again, her face cycling through expressions so fast it's hard to track them all. Surprise, curiosity, something unmistakably warm.

Then she smiles.

"Oh my god," she breathes, stepping fully into the room and closing the door behind her. Her hands rise instinctively, but stop short of touching you. "Jake... you look incredible." You can feel your face burning, but there's no way to hide now. She's seen.

Sarah smiles, "I didn't know you were into cross-dressing. You look great in that!" Her smile was just as warm as you have always known. You begin to relax just a bit. Sarah walks over to you and starts to rub her hands over your body. Her hands glide over the fabric, feeling the shape of you in the dress, smoothing it gently. There's no hesitation in her touch, no judgment--just curiosity and appreciation. When she reaches your shoulders, she squeezes lightly, meeting your eyes in the mirror.

"Wow," she murmurs. "You have incredible shoulders. They look so delicate like this. I never realized how feminine you actually look." She smiles a bit wider and then she asks, "Jake, can I do your makeup? I bet I can really help you pull this dress off." Your breath catches as Sarah stands close behind you, her hands resting lightly on your shoulders as she looks at you in the mirror. The proposition feels dangerous and thrilling all at once.

"Yes," you whisper. "Please."

Sarah's eyes light up with excitement. She quickly moves to her vanity, rummaging through her makeup case with practiced ease. She positions herself in front you, adjusting your face to the right angle.

"I never realized but your skin is gorgeous." She says carefully applying the makeup. She applies everything like a master, eyeliner, blush, foundation, the works. Once done she looks at you and smiles like she has just completed a masterpiece. Then she moves out of the way and lets you look in the mirror. What you see stuns you.

The transformation is breathtaking. Your skin looks flawless--dewy and luminous in the soft lighting. The expertly applied eye shadow accentuates the curve of your face, drawing attention to your delicate features. You eyes and lashes look full as if they were naturally this way. Even your lips look fuller, more kissable. You're hardly recognizable to yourself.

Sarah watches you with undisguised pride, her hands clasped together under her chin. "You look absolutely radiant," she breathes. Her face flushes pink at her own words, but she doesn't look away. Instead, she meets your eyes in the mirror, her smile growing. You can't believe that the gorgeous girl staring back at you in the mirror is you. Your own mother wouldn't recognize you. You smile, finally feeling like the girl you have always been mistaken for.

While you are busy looking at yourself, Sarah rummages through the closet. She pull out silicon fake C-cup breasts that she had for a cosplay she did one year. She smiles and says, "Now lets finish the look." She carefully lifts the dress over your head, ensuring not to mess up your makeup. Then she fits the silicon breasts in place. Your breath hitches as she secures them, blends the edge in with makeup, and lets you look in the mirror. "What do you think? Look pretty real right?" She says with a smile.

You nod in agreement, words failing you.

They feel strange at first--too big, too heavy--but stepping back and looking at them more in the mirror, your mind really starts to make you feel like they are real. Sarah blended the seam so perfectly with your skin that if you didn't know already that they were fake, then there is no way you could tell that they weren't your actual breasts. You stare at your reflection, transfixed by the transformation. The fake breasts give your chest a soft, natural curve that amplifies your already feminine body. Sarah's hands linger on your shoulders as she admires her work, pressing into the muscles with gentle appreciation.

"Oh, I can't believe how good this looks," she murmurs. Her hand cupping one of your fake breasts. "You were gorgeous before with just the makeup, but like this..." She doesn't finish the thought, just lets her hands slide down your arms as she steps back. You turn to face her, and she gasps softly at the full view. Her hands rise instinctively but stop short of touching again.

Then she clasp her hands together snapping herself out of her gaze. "Now to complete everything, we just need to figure out what to do with that dick of yours." She thinks for a moment then it suddenly hits her. "Oh yeah!" She runs over to the bedside table and opens the bottom drawer. She pulls out the black box that holds all of yours and hers sex toys.

In the box is a perfect inverted flat cock cage that you have only experimented with once when she was feeling a bit dominate. She pulls it out with a smile and walks back to you, getting on her knees. Then she carefully locks the cage in place. She admires her handiwork for a long moment, her fingers tracing the edges of the cage where it meets your skin. When she finally stands, she angles your face toward the mirror with a soft touch under your chin.

"Look at you," she breathes, speaking softly. "You're flawless. Any guy would do you in a heartbeat. Heck! I want to do you like this!" Heat flares through you at her words. You both gaze into the mirror together, her reflection behind you as she holds you close, her chin resting against your shoulder. Her breathing is warm against your neck.

She smiles, "Now for the lingerie and then we will put the dress back on." Sarah walks over to her lingerie drawer and selects a delicate black lace bra and matching panties. "These should work perfectly," she says, holding them up.

You stand still as she helps you step into the panties, her fingers brushing against your thighs as she guides the fabric up. The lace feels impossibly soft against your skin, the delicate pattern hugging your curves in a way that makes you feel completely feminine. Sarah fastens the bra behind you with practiced ease, her hands working quickly yet gently. The band molds around your waist, supporting the fake breast perfectly. Then she slips the red skin-tight party mini dress back over you.

After she fixes your long hair, grabs the matching red stilettos that you had set on the bed to try on with the dress earlier. Once everything is in place she cheers stepping back to admire the full effect, her face lighting up with unbridled joy.

"You're absolutely stunning!" She exclaims, twirling her fingers at you to turn around. As you slowly spin, Sarah claps her hands together in delight, not taking her eyes off you for a second. She moves closer, her fingers lightly touching the fabric of the dress as she adjusts it here and there.

You take another look in the mirror now with everything on. Words cannot describe what you see. In the mirror, staring back at you is a gorgeous beauty. A solid 10 that honestly rivals your own wife's looks. There is not even the slightest hint of masculinity in the form you see before you.

"Gosh, Jake, You look so good that I am even jealous." She says with a playful wink, "Now let's get you out there and show off this gorgeous girl! You are coming out with me and the girls to the club."

She grabs her purse and phone. "Oh yeah! We have to give you a new name for tonight though. Hmm.. How about Julie?" She says. "Julie," you repeat softly, testing the name. It feels right on your tongue. Sarah claps her hands together with glee.

"Perfect! Now, try taking a few steps in those heels." She says. You walk across the room with ease. Sarah immediately notices, "Oh, I see this isn't your first time in heels." She laughs in a playful manner. "I started practicing months ago," You admit with a nervous laugh. The words feel both exhilarating and terrifying to say aloud.

Sarah grins wider, her eyes bright with excitement. "That's my girl! I knew there was a reason I married you." She takes out her phone and turns on the camera. "Okay, let's get some pictures of my masterpiece before we go." She guides you into poses with an easy familiarity, tilting your chin just so, adjusting the the dress to show more of your curves. Each movement of her hands feels gentle yet confident, like she's been dreaming of dressing you up her whole life.

After she is satisfied with the photos, both of you head out of the house to her car. You drive to the club and meet up with her friends. Sarah introduces you as her sister-in-law Julie, Jake's sister. Sarah's friends welcome you warmly, their admiring looks both flattering and slightly nerve-wracking. None of them realizing you are actually Sarah's husband.

One of them--Melissa, a curvy blonde with piercing green eyes--grabs your wrist and spins you around appreciatively. "Oh my God, you are stunning! I love that dress!" she says with a delighted laugh. You blush and softly say, "Thank you!" Your already high-pitched voice helping to disguise your true form.

You all enter the club, the pulsing lights and thumping bass overwhelm your senses momentarily. Sarah keeps one protective hand on your wrist as she guides you through the crowd. The bodies press close in the dimness, hands brushing against your sides as people move past. You, Sarah, and her friends make it to a back booth.

You all order a couple of drinks and start to have a real good time. All the while, no one suspecting that you are really a man. As more and more drinks arrive, you find yourself really feeling like one of the girls. Sarah and all her friends continuously compliment you and include you in the conversations. You sip your gin and tonic that Sarah ordered for you, listening to the music's thrumming beat. Melissa leans closer to Sarah and you hear her ask, "So is Jake... okay with this? You and his sister coming out to a club like this?" Sarah's hand finds yours under the table, squeezing gently.

"Oh yes! Trust me, Jake understands," Sarah says with a confident smile. "He's always encouraged me to dress up and have fun." She winks at you. She continues, "Me and Jake have always been okay with an open playful relationship. I know he wants his sister have fun as well. That's why I also encourage him to go out and have fun himself." She looks at you and squeezes your hand again.

You smile and squeeze her hand back. Then Melissa says to you, "Uh-oh Julie, looks like you have an admirer." She motions towards the bar where a big-muscled, tattooed, black guy is clearly checking you out. You catch the guy's gaze settling on your own, his attention unmistakable even in the dim club lighting. His deep brown eyes meet yours with something unmistakable, a slow appreciation that travels from your face down to your heels and back up again. He doesn't even attempt to avert his gaze when your eyes lock--if anything, his smile widens slightly. He gives a subtle nod as if beckoning you over.

Sarah gives your shoulder a little squeeze, speaking warmly in your ear. "You should go say Hi." You give her a hesitant look. "It would be a good way to test out your looks on a man." She says giving you a slight push. You hesitate for just another moment before deciding to get up and give your new look a test run. You walk over to the man.

Now confident that your very feminine voice covers your disguise, you say, "Hi. I saw you looking over at me. Were you seeing anything you liked?" The man's lips curl into a hungry smile as he looks you over again. He speaks with a deep baritone, smooth as velvet. "Damn right I do." His eyes flick down to your legs then back up, appreciative. "Name's Sam"

He extends his hand, his palm warm and dry against yours. His fingers linger just a second too long when he shakes, his thumb brushing your wrist. There's a confidence in his movements that isn't arrogant--just comfortable in his own skin. He motions to the open space beside him at the bar. "Drink?" he offers. "Unless you're already spoken for?"

You hesitate, "Well I am spoken for, but we have an understanding." Sam smiles, "Oh a naughty girl huh? I love that!" He reaches around you and with the confidence of a man who knows he will get what he wants, grabs your ass and pulls you in closer to him. His body radiates heat against you, his cologne--something woodsy and musky--filling your senses. He is much taller than you so at this distance you have to look up to meet his eyes.

His hand stays firmly on your ass, clearly claiming you as his own. He leans closer, speaking low in your ear over the music. "You are a sexy little thing. I bet you are a lot of fun." His fingers tighten slightly on your ass, giving a gentle squeeze.

You glance over to the booth and see that Sarah and Melissa are watching your interaction but don't seem to concerned about trying to intervene. Melissa whispers to Sarah, "Looks like Julie might end up having a good time." They both watch you intently as you continue your interaction with Sam.

You and Sam continue to talk for a bit, all the while his hand moves more and more under the dress. His hand is now on your bare ass, a finger playing with the edge of your panties, trying to find an opening. You welcome the attention, losing yourself in the persona of Julie. The thrumming music of the club vibrates through your body as Sam continues to talk in your ear, his talk becoming more and more sexual. He pulls you in tighter to him, his crotch now against your lower stomach. You can feel the hardness pressing against you.

He finally leans in and kisses you. You instinctually kiss back as you are caught up in the moment. Then as you feel his tongue invade your mouth you come to the realization that this is the first time you have ever kissed a guy. The thought makes your cock twinge under the flat cage. You continue to kiss him, your tongue now playing with his.

Sam takes this opportunity to move his hand that was firmly on your ass, further in. His fingers now gliding under your panties and resting in your crack. Your skin tingles wherever he touches you, responding to the attention with unmistakable arousal. Sarah catches your eye from across the room and winks encouragement, clearly enjoying watching you be appreciated.

Sam's middle finger start probing your asshole looking for any type of give. You don't stop him as you are too caught up in the passionate atmosphere. Sam breaks the kiss and leans close to your ear, whispering, "I would love to have some fun with you." As soon as he says that, his finger pushes into your ass. The sudden intrusion makes you gasp. He quickly kisses you again in order to silence you, making sure no one hears you moan. His tongue tries to stretch deeper into your throat as his finger pushes further into your ass.

The burn in your asshole from Sam's probing finger sends tremors through your body. You've never been penetrated this way before, and the initial shock gradually transforms into something deeper--warmth spreads outward from his touch. He breaks the kiss once more as he nuzzles against your neck. "You like that, don't you?" He growls, the rumble vibrating through your back. You let out a soft, "Yes.." with a subtle moan.

You allow Sam to continue his fingering of your ass as you moan. Sam growls again, "I love a slutty girl who likes it in the ass." His finger curls inside you, finding that sweet spot that makes your knees nearly buckle. The crowded club around you fades away as he begins a slow, deliberate rhythm, working his finger deeper with every thrust. Your breathing comes in short gasps now, your face flushing as you realize people nearby can probably now hear your moans.

Sam then says, "Lets take this to a more private spot." He pulls his finger out and sucks on it for a moment before deliberately leading you by your ass towards the bathroom. You stumble a bit as Sam pulls you into the men's bathroom, your mind still foggy from the intense stimulation. The room is dimly lit and nearly empty, with just one stall occupied. Sam leads you into a stall and locks the door.

He sits down on the toilet, the bulge in his pants very obvious. "You're so fucking sexy," he growls, wasting no time to unzip his pants. His thick cock throbs through his jeans as he pulls it out. Your jaw drops as you stare at this man's member. His cock is massive and thick. It is without a doubt more than twice the size of your own cock. You can see the glim of precum forming on the tip.

The he says, "How about we start with a blow job? You can get it nice and lubed up for me to fuck your ass." His massive cock twitches in front of you, the thick veins standing out along the shaft as he holds it by the base. Your mouth goes dry just looking at it--you've never had something that size in your mouth before, or have even done anything with a man before. The musk of his arousal fills your nostrils, warm and masculine. He leans back against the toilet, his gaze burning into you with hungry expectation.

"Show me what that pretty mouth can do," He purrs, voice deep with lust. Your hands shake slightly as you kneel before him, the hard floor beneath your knees. You hesitate, wondering if you should even be doing this. You take a deep breath before your body leans forward on its own. Your lips now just a centimeter or so from the head of his cock. "Oh don't be shy honey." He says as he grabs your long hair and forces your head down onto his cock.

His cock flies past your lips and is quickly shoved down your throat making you gag. He keeps his grip on your hair not allowing you to back away. You struggle for a minute trying to pull away but his grip is unyielding. So you begin to breath through you nose and try to get into a rhythm. Slowly but surely your gaging subsides allowing you to take more of his cock down your throat.

He compliments you, "That's it girl, let it all the way in." His hand tightens in your hair as you relax your throat, allowing his massive cock to slide deeper. The thick shaft fills your mouth completely, pressing against the back of your tongue as it passes your tonsils. Your nose brushes against the soft curls at his base. His balls rest against your chin. Sam groans deeply, his hips twitching upward slightly to push even deeper. "Fuck yes," he growls, the sound reverberating through his body. His free hand moves to your face, thumb stroking your cheek as he looks down at you. His fingers flex in your hair as he guides your head into a slow, deep rhythm.

It doesn't take long for your throat to adjust to his size. You surprise yourself by really being able to now take his cock like a blowjob pro. You have never done anything with a man, and now here you are giving an expert blowjob to a man who is way more of a man than you have ever been. His musky sweat and precum fills your senses as you continue taking his cock deep, gagging only occasionally now. His grip on your hair tightens, guiding your head in steady, powerful thrusts. Your face burns with shameful arousal and exertion as your nose bumps against his pelvis during each descent. A thick vein throbs against your tongue during each stroke. Chin pressing against his sweaty balls.

Sam groans loudly, echoing in the stall, completely oblivious to anyone who might hear. "Fuck, just like that," he rumbles. His hips thrusting upward to meet your mouth, pushing your head down harder. The stall door rattles slightly with the force of his movements. After about 15 minutes or so, he pulls your head off by your hair. Long strands of spit connect your mouth to his cock.

"Alright girl, its time to fuck that sweet ass." He says as he stands up. He helps you up and immediately turns you around. He puts his hand on your back bending you over. To avoid exposing your cock, you take the initiative and lift your dress exposing your ass. Then you pull down your panties just enough to expose your asshole. Then you realize what is about to happen. You are about to let a guy fuck your ass.

You think to yourself that giving a blowjob is one thing, but are you really ready to let a guy fuck you? You don't even get time to answer your own question. Your heart hammers in your chest as you feel him spread your ass cheeks and the thick head of his cock pressing against your tight asshole. The tip smears precum and saliva against your wrinkled entrance as he guides himself into position.

Sam's hands grip your hips firmly, holding you steady as he slowly pushes forward. Your muscles instinctively resist at first, trying hard to stop his intrusion. But the combination of spit and precum lubricates the way as he begins to breach you with a sudden pop.

Immediately you are hit with an intense pain and heat burning in your asshole. The pain makes you moan out loud, which Sam enjoys. "Fuck, you're so tight," he groans, his voice strained with effort as he forces the thick head past your sphincter. You can feel your ass be forcibly stretched as the pain continues. The pain begins to mix into a strange heat as he pushes inch after inch inside you. Your fingernails scrape against the metal stall walls as he fills you completely.

"Oh god." Is all that escapes your mouth.

Sam groans as he finally sheaths himself fully inside you, his hips flush against your ass. His balls resting against your taint. "That's it you tight slut, take it all," he growls, giving your ass a hard smack. The burning pain begins to subside as he starts to slowly pull back out of you. Just before his cock is pulled all the way back out, he thrust hard all the way back in you. The motion sending shockwaves through your body. Another loud moan escaping your lips.

Your hands clench and unclench against the stall wall as he sets a steady rhythm, his cock stretching and filling you in ways you've never experienced before. "Fuck yes, such a tight little ass," Sam pants, one hand gripping your hip while the other smacks your ass periodically.

As he continues thrusting, the pain gradually transforms into a intense, unfamiliar pleasure. You feel your body begin to tingle all over as Sam continues to fuck your ass. You body molding to fit his cock as if expecting it to always be there. Caught up in the pleasure, you push back against his thrust allowing his cock to reach just a bit deeper in you with every thrust. You now let out deliberate moans enjoying every inch entering you.

The pleasure makes your skin become sensitive to the touch, Sam's hands exploring your hips and waist feel amazing. Each smack of your ass a welcomed treat. Just for a moment, you completely forget that you are actually a man. Your mind clouded with pleasure wants nothing more than to please this manly man fucking you, making you his personal toy. He pounds into you with increased force. The slap of his hips against your flesh fills the stall along with the sounds of your mingled moans. A trickle of precum leaks from your cock, caught by the flat cage. Sam's breathing grows ragged as he nears his climax.

"That's it baby," he grunts, his thrusts becoming erratic as his thick cock swells inside you. "I'm gonna fill that tight little ass of yours." You reply with, "Yes daddy fill my ass please!" Your mind is completely focused on pleasing him. Your body shivers as it begs for his release. Then Sam slams hard against your ass and lets out a deep and primal groan.

Immediately you feel hot liquid pouring into you. You can feel Sam's cock deep inside you twitching as more and more cum is pumped deep inside your ass. The thick, hot cum fills you up more than you thought possible, his thick release seemingly endless as he keeps slam thrusting into you to make sure every last drop is deposited inside you. Each twitch of his cock makes more heat pulse through you. The feeling is unlike anything you've ever experienced before. Your own cock dribbles precum in the flat cage, your body overloaded with pleasure.

Sam groans loudly as he finally empties himself fully inside you, his strong hands gripping your hips as he holds himself deep to ensure nothing leaks out. When he finally pulls out, you hear an audible pop. Then its like a sudden pressure is released and your ass feel empty without his cock. You asshole twitches trying to milk a cock that is no longer there. You can feel his cum beginning to ooze from your stretched hole, dripping down your thighs. Sam slaps your ass again, admiring his handiwork.

You straighten up with some effort, adjusting your dress, wiping away the stray cum from your thigh, and pulling your panties back up. Sam tucks himself back into his pants with a satisfied smirk. His cum leaks out of your ass in a thin stream, already starting to make a wet spot on your panties. You both catch your breath, the musky scent of sex hanging in the air.

"That was incredible," Sam says, rubbing his hand over your ass where he smacked it multiple times. "You've got one hell of an ass." He kisses your neck, then steps back to examine you with hungry eyes. "I wouldn't mind fucking your ass again sometime. Let me give you my number and maybe we can hook up again." Your stomach flutters at the proposition. He gives you his info and gives you one last smack on your ass, then he unlock the stall and leaves. You walk awkwardly over to the mirror, you legs feeling like jello. You stare into the mirror and just take in everything that just happened.

Your reflection shows a man whose transformation for tonight is complete--your eyes still slightly glazed from the intensity of your experience, your lips reddened and swollen, makeup just slightly smudged. The black lace bra peeks through your dress where the top has come down just a bit during your encounter, your hair a mess. You can't help but notice that you look like a drunken hooker after a rough night of constant clients. Most strikingly, you feel the damp spot on your panties growing as Sam's cum continues to drip out of your well-used hole.

Your hand unconsciously traces your ass as you process what just happened. The flushing sound of water and distant music snaps you back to reality. You shake your head, fix your hair and dress, and walk out of the bathroom heading back to booth where your wife Sarah and her friends are still sitting. Your heels click on the tiled floor as you make your way back to the booth.

As you approach, you notice Sarah and Melissa looking at you with raised eyebrows and knowing smiles. Your face flushes as you recall the details of what just transpired in the bathroom. You smooth down your dress and slide back into the booth, doing your best to act natural despite your body's reactions. Sarah moves closer, her voice tinged with playful curiosity. "Have a bit of fun did you, Julie?" She runs a hand down your arm, her touch sending shivers through you.

The rest of the night goes on though you don't remember most of it as you were too focused on the experience you had. You and Sarah say bye to her friends at the end of the night and you both head home. Once home, Sarah ask for all the details. You explain everything, from the bar to the bathroom. Her eyes remain excited and glued to you as you go through everything. Sarah listens attentively, her eyes bright with curiosity as you recount the details of your encounter with Sam.

"That's so hot," she murmurs, her voice warm and approving. "I knew you'd love that kind of thing. The way he just took what he wanted from you..." Her fingers absently trace patterns on the couch. You find yourself blushing with renewed arousal as she reacts to your story. "I... I didn't expect it to feel so good," you admit, shifting slightly as the memory makes your ass clench around nothing.

Sarah's smile widens. "Oh I can tell." She continues, "Well you better go shower and clean yourself out. Then we can talk about what I have next in store for you." You smile and head to the bathroom. You can't believe how accommodating and supportive Sarah has been with all of this. Having a wife that helps you to explore such fantasies is like a dream come true.

You begin to take off the dress as you turn on the shower. Then her words finally hit you. What she has next in store for me?