His First Time

Nervously moving towards the apartment door, Peter taps it gently. He’s feeling so uncomfortable about what he’s about to do. He almost feels like everyone who sees him knows about what he’s booked to do in apartment number 39

Feeling anxious, he taps again on the door harder. He’s desperate not to be seen.

As the door slowly opens, a well-dressed woman appears at the door. Instantly he can smell her scented perfume.

“Hi!” he nervously greets her. “I’m Peter.”

“Hiya,” the Lady replies, moving aside to let him in. “I’m Claudia, please come in.”

Bolting into the apartment, Peter looks around and feels like he’s made a mistake. He wants to back out, but Claudia stands between him and the door.

“Peter…?” she questions softly. “You look worried. Are you ok?”

Nervously rubbing his hands together, Peter nods. “I’m fine.”

“Are you worried about the service?” Claudia asks, moving slowly towards him.

Placing a gentle hand on his shoulder, she beams a comforting smile.

“Don’t be worried,” she continues. “We are completely discrete with the service. Anything you don’t want to do will be honored.”

“Ok,” Peter replies.

“You are safe here Peter,” Claudia says, gesturing for him to move into the next room. “No judgments here. You are safe to express yourself, Peter. You are safe to be who you want to be.”

Cautiously moving into the next room, he looks around at the wigs, dresses, and other female items strewn around the room delicately.

“People won’t find out…?” he questions, worried about what people might think.

“Only if you want them too,” Claudia quickly quips in reply.

Feeling extremely curious, Peter moves over to a stunning red dress with a sweetheart neckline. Holding the soft material between his fingers, he smiles.

“Would you like a cup of tea…?” Claudia asks, moving to stand next to him.

“Please,” he answers.

“Great! Claudia smiles, clapping her hands together.

As she leaves the room she turns back to face him. “How do you have it?” She asks.

“No sugar and strong,” Peter answers, feeling now a little more at ease.

“Take a seat,” Claudia says, giving him a wink. “We will have a cuppa and then discuss the look you want to do…ok?”

“Sure,” he answers, slowly taking off his jacket and sitting on the nearby sofa.

Moments later, Claudia walks back in holding two teas and a packet of biscuits. Placing them down onto the coffee table in front of the sofa, Claudia takes a seat on the armchair facing Peter.

“Thank you for sending your measurements beforehand,” she comments, dunking a biscuit in her tea.

Picking up his tea and taking a small sip, Peter takes the opportunity to apricate how lovely Claudia looks in her sequin dress and heels.

“I like your dress…,” Peter says, reaching for a biscuit.

“Thank you!” Claudia responds. “I’ve got one like this in your size if you’re interested?”

Going a little red, Peter dips his biscuit and looks over at the red dress he touched moments ago.

“If it’s ok….,” she says softly. “I’d like to wear something like that red dress over there.”

Claudia looks over at it and smiles.

“Oh sure!” she replies with excitement. “I do like a sexy red dress!”

Dunking her biscuit once more, she holds it over her teacup and looks Peter up and down.

“Do we….,” she says delicately “…..need to shave or have you done that already?”

Avoiding eye contact for a moment, Peter leans forward and rubs his leg.

“I-I already s-shaved all over,” he answers.

Taking another sip of tea, he can feel his skin feeling sore. He’d shaved all over for the first time before coming.

“My skin is a little redraw,” Peter admits.

“We’ve got lotion for that,” Claudia answers with a comforting smile.

Taking a sip of her tea, Claudia swings one of her long legs over the over and gently starts bouncing her foot.

Peter looks down at her shiny black heels and gulps at the prospect of wearing such footwear.

“Do you have an idea what you’d like your hair and makeup to be?” Claudia asks, noticing him looking at her heels.

Quickly looking back up at Claudia, Peter bashfully smiles and goes a little red.

“I’d like to look like….,” he says, but stops.

“Like…?” Claudia pushes for an answer.

“…..Zooey Deschanel.” Peter continues, quickly looking away with embarrassment as her name slips out of his mouth.”

Uncrossing her legs, Claudia looks up for a moment.

“Ah yeah,” she grins. “Brunette, with the fringe from that New Girl series?”

“Y-yeah….,” Peter replies. “Do you think I’d pull that off?”

Holding eye contact with each other, Claudia thinks for a moment before answering.

“Defiantly!” she replies with gusto. “I’ve got a lovely curly brunette wig with your name on it!”

On hearing her reaction, Peter smiles wide.

Seeing his reaction, Claudia quickly places her cup down with purpose and stands.

“Ok to business!” she commands with confidence.

Holding her hand out for Peter to stand also, Claudia softly takes hold and leads him into the next room.

“I want you to know a few things about me so we are comfortable with each other,” Claudia explains, leading him into a bedroom.

“I’m a transwoman,” she continues, moving around the room and gathering a few items. “I don’t want you to feel nervous about getting your body out. I’ve seen it all before.”

Feeling a little uncomfortable, Peter notices Claudia picking out some feminine underwear.

“Peter,” she says, stopping in front of him with a handful of lacey underwear. “First thing we need to do is get undressed. Once we’ve got you into your feminine underwear, we can start the process.”

Holding out the lacey red knickers and bra, Peter takes hold of them anxiously.

“Once you’ve put them on, we will look at body-enhancing underwear to give you the feminine shape your desire,” Claudia says, giving him a reassuring smile.

Wanting to give Peter a moment of privacy, Claudia leaves the room.

Now standing alone with the feminine panties in hand, Peter could feel himself getting excited. His heart had started beating and his breathing was heavy.

Anxious to get going, Peter places the panties on the nearby bed and immediately starts whipping his male clothing off. Once completely naked, he throws his male clothing onto a pile on the floor.

Excitedly grabbing for the red panties, he feels how soft the material is between his fingers. As he puts each leg into the holes, he can’t wait to feel the satin against his package.

Eventually pulling them up around his package, he’s pleased by the soft cupping of his balls and how the panties go between his ass crack.

Having never worn a woman's panties before, having them running between his cheeks was a thrill he’d never known existed.

Just as he looks down at himself, Claudia shocks him as she swiftly walks back into the room.

“Oh good,” she says cheerfully, holding more items. “They fit perfectly!”

Feeling somewhat uncomfortable, standing in just a pair of women's underwear, Peter was surprised at how happy he felt at her comment.

Now holding up two very different skin-colored items, Claudia smiles wide.

“This is a breast form breastplate,” Claudia comments, showing him one piece.

Peter looks at the fake breasts hanging from the vest-like garment. He’s thrilled when he sees the size breasts Claudia’s chosen.

“This is your hip, bum, and waist enhancer,” Claudia continues, showing the other.

“W-what does that do..?” Peter asks, pointing at the latter.

Placing the breastplate down, Claudia holds up the hip enhancer.

“Well….,” she says, showing him the pads and sinched in the top. “The pads give you wider hips and plump backside. It also sucks in your stomach to give you a somewhat more feminine waist.”

“Oh,” Peter replies, now feeling the cold on his skin.

“Want me to help you get these on?” Claudia asks, reaching for the breastplate and holding it up.

Giving her a nod, he lifts his arms into the holes.

After pulling it down over his head, Peter holds in a giggle as his new breasts bounce and hang from his chest.

“I hope you’re ok with being a C cup,” Claudia says, adjusting the fit on his chest.

Gently cupping the breasts, Peter feels the weight of them. He gently bounces them up and down.

“Perfect!” he grins.

Now holding the hip enhancer up, Claudia helps Peter pull the tight control wear up and other his backside.

As the tight garment sinches around his stomach, he can feel it holding his shape. He looks down at the pads and smiles at the shape and size of his hips and ass.

“This is tight…,” Peter comments.

Focused, Claudia holds up the matching red bra she’d given him moments ago. Holding the straps up, Peter instinctively knows to put his arms in.

As she clasps him into his bra, he feels the underwear take up some of the weight of his new breasts.

“I see why these are worn,” Peter says, feeling a new aprication.

Clapping her hands together, Claudia steps back from adjusting his bra fit. She looks him up and down then takes his hand and brings him back into the living room.

Peter follows behind and enjoys the feeling of the forms moving as he walks. He’s thrilled and so pleased he decided to do the makeover service. It was already worth it for him!

“Ok Hunny,” Claudia says, pulling out a chair and signaling for him to sit. “I’m going to do your makeup and fit your wig before we get you into your dress.”

Looking over the table, he can see a huge selection of makeup, brushes, and other such items. He also notices the huge mirror on the table.

“Are you warm enough?” Claudia asks before Peter sits in the chair.

Nodding, Peter sits gently in the chair. He smiles as the backside padding softens the chair.

Now standing directly over Peter, Claudia takes his hand and inspects his nails.

“So….,” she says, then moving to gently touch his face. “I’ve got some fake nails to attach and some eyelashes if you want to me too?”

Not wanting to miss out on any of the experiences, Peter nods gratefully.

“I’m happy with anything,” He tells her. “I trust you to do your thing!”

Giving Peter a soft smile, Claudia pulls a few items from her box of goodies. Placing them down the table, she holds a pot of bright crimson nail polish up.

“Thank you, Peter,” Claudia says, opening the pot. “Let's make you look super pretty!”

Sitting patiently, the relaxation of such personal attention sets in for Peter. Having Claudia show so much fuss and concentration in painting his nails was almost like a spa experience for him.

One by one, she glues the shaped feminine nails to each finger and paints them with one solid stroke.

Moving on to focusing on his feet, Peter holds his hands out and gleefully looks at the transformation.

“Just avoid touching anything for a few moments,” Claudia says, putting the small nail polish away.

Pulling more items from her box, Claudia sets out a few soft-looking makeup brushes out.

“Just relax as much as you can,” See comments, opening a large-looking thin box, full of different soft colors.

Peter nods and smiles as he watches Claudia intently work her magic.

Talking Peter through every stage of the makeup process, Claudia explains why it’s important to his transformation

Starting with concealer, she moves quickly onto foundation.

Enjoying the feeling of the soft brushes against his smooth skin, Peter gently leans back in the chair. Just like the nails moments ago, he’s stunned at just how much he’s enjoying the personal attention.

Minutes later, Claudia moves on his eyes and eyebrows.

More soft brushes waft over his eyelids.

Time passes extremely quickly as Claudia gently moves from one eye to the other. Spending a little time on his eyebrows and his cheeks, she stands back and looks at Peter straight on.

“Mmmm….,” she mummers, gently touching his lips. “Nearly done.”

Peter smiles. “I’m so relaxed. Please take your time…”

Now focusing on his lips, she lines them and then gently runs lipstick across them. Asking Peter to blot the excess, and she gives him a massive grin.

“Finished!” she cheers. “Don’t look yet though! Gotta fit the wig first!”

Resisting the urge to turn and look into the mirror, Peter waits paitiently

Moments later, having left the room to fetch it, Claudia returns with the wig in hand. It’s just like Zooey's hair! Curly, brown, and with a large fringe.

Moving behind Peter, Claudia gently lowers the wig over his head. She pays close attention to ensure the long hair doesn’t fall into his face.

“You’re going to look so gorgeous!” Claudia says, carefully adjusting the fit.

Moving around him at speed, she pulls and tucks the wig into Peter's real hair. Adding a few discreet clips here and there, she reaches for a hairbrush.

Spending the next few minutes brushing the wig out, Claudia sprays a little hairspray to hold it in place.

Peter feels the hairs tickling his bare skin. As the fringe of the wig falls just above his eyes, he starts getting extremely excited about seeing his transformation.

“Can I look yet?” He asks, getting almost nervous with excitement.

Stepping back, Claudia holds the brush in her hands and gives a sideways glance.

“Mmmm…,” she mutters, moving closer to tidy up a few stray hairs. “Yeah, I think so!”

Thrilled, Peter slowly turns in the chair. As he moves, he feels the hairs of his wig move around his shoulders.

As he peers into the mirror, a stunning-looking woman stares back at him. He’s almost shocked at the sight.

“Is that me!” he gasps, bringing his hands up to his face to gently swipe away some hair from his eyes.

With the bright plump lips, the smokey eyes, and the flawless-looking skin, Peter is blown away.

“I can’t believe it!” he exclaims, unable to take his eyes off himself.

Claudia gently laughs behind him.

“Told you!” she giggles. “You wanna get into your dress now?”

Nodding, Claudia helps Peter up and out of the chair.

“Ok,” Claudia says, reaching for it and unzipping the back. “Just step into it and I will zip you up.”

Doing as he’s told, Claudia holds him up as he steps into the soft short dress. Pulling the straps up and over his fake breasts and onto his shoulders, he feels it clench and form around his body as Claudia zips it up behind him.

Moving around to adjust the neckline, Claudia smirks.

“Fits you like a glove!” she comments, gently pulling at the dress to adjust how it sits on his body.

Allowing Peter to gawk at his body wearing the dress, Claudia rushes to get some heels. Bringing them into the room, she holds them up and gives him a playfully smile.

“Gotta finish off the look,” she comments, placing them down onto the floor in front of his feet.

“Do they hurt?” he asks, nervous as he looks down at the bright red stilettos put in front of him.

Shaking her head, she holds he arms out to support him.

“They may pinch, but once you’ve got them on you’ll understand why we wear them!” she explains.

Holding him up as he slides on both heels, he stands in heels for the first time. Wobbling slightly and looking a little unsure of himself, Claudia steps back and claps with excitement.

“So pretty!” she cheers! “You wanna go look at yourself in the full length?”

Still wobbling in his heels, Peter gently brushes the hair from his eyes once more.

“I’d love that!” he says bashfully.

Holding out her hand with a big smile, Claudia helps Peter walk slowly back into the bedroom.

As she stands him in front of the mirror, Claudia can almost feel the emotions emanating from him. As Peter looks into the mirror at the feminine beauty he’s been transformed into, she can see the tears forming behind his eyes

“WHOA!” she laughs, fanning his eyes. “Don’t cry! You’ll ruin your makeup.”

Peter lets out a small, awkward laugh and turns to look at Claudia.

“Thank you for this!” he mutters, fanning his own eyes as Claudia does. “I’ve never felt so good about my body…….until now!”

“You’re welcome!” she replies, grabbing his hand tight. “My pleasure!”