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The birth of a star. (SA and SKbm)

Sam's lips curved upwards into a mischievous smile when she touched his ass. The ideas she had planted earlier, during their discussion or hormones, were still taking root -- and he couldn't wait for her to show him exactly what she meant. He was excited to try all these new things. Fearful, certainly -- but he was excited regardless. He practically hung off her while she lead him around the store, bright eyes examining each and every thing she acquired. Handcuffs, a dildo even larger than the one she'd given him in the office, something to ease the passage among other miscellaneous things -- before a skimpy set of panties and a very revealing french maid outfit that he knew wasn't going to fit her, but likely would him. That sent a shiver down his spine.

Not too long ago, after all, he imagined himself fucking a maid rather than being the maid.

She found a latex outfit. He'd never really seen someone wearing one, if he was honest. The shiny material wasn't something he was sure he would wear much himself, but he was rather eager to see how it looked on Julia -- especially because it looked like it'd be a hell of a thing to squeeze into. Sammy turned his head towards her when she suggested they should see if the outfits fit...

"Yes, I would love if you used all these things on me." He whispered, a hand massaging her back briefly. "Let's go see if they fit... unless, of course, you just meant the dress." He said, smiling. He couldn't wait to see her in it -- his little cock got hard just thinking about it, tenting the dress from the front in a noticeable manner.
 
Julia could feel herself getting more and more aroused by Sam's closeness and his eagerness. "Maybe we should postpone the trying until we are at my place. Otherwise we risk ending up with a lot of cum everywhere. And I'm not sure the owners like their products stained, at least not before they are paid for." She smiled at him. "But I can assure you that I'll love to use all of this and more on you tonight." She pushed her ass back as he massaged her rear. "Fuck girl. You are making me horny. We need to get out of here very soon."

She headed towards the counter to pay for the things they had collected. "I want to stop by one more place and get you some perfume and other beauty products. But after that it's straight to my place girl and you are going to become my maid for the night."
 
Sammy's smile grew broad, perfect white teeth displayed prominently for her and her actions. It made him giddy, hearing her speak so frankly, so honestly. He tried to smooth out his dress, but there was nothing really to do. To Sammy's surprise, he didn't even get a strange look. Why would he, though...? It was a sex shop! He was probably not the first crossdressing little bitch to be walked in by a strong, dominant woman! His skin prickled with goosebumps.

"I can't wait to clean you off in that case, Ma'am!" He said, eagerly -- perhaps a little too loud, as his cheeks suddenly flushed with cute embarrassment. "will you do my makeup tonight again too, then?" He enjoyed looking at himself fully made up in the mirror more than without it -- he looked far more like a woman when that happened.
 
Julia pulled held him close as she payed for their wares. "I'll do your makeup baby girl. Then you can be my girl for the night."

They left the shop and soon they were on the road again, with the bag of naughty stuff on Sammy's lap. For their last stop Julia simply told Sammy to wait for her while she got some perfume, soap and skin lotion for Sammy. Soon she was back in the car and gave the bag to Sam. "Here you go baby. I hope you'll enjoy it."

Julia could feel she was extremely horny. It was a wonder her cock hadn't gotten hard and burst from it's confinements. But that were bound to happen sooner or later tonight.
 
Sammy waited patiently in the car with a bag full of naughty things. At least it was covering his crotch. Finally, she returned -- and he couldn't help but look himself. Perfume, soap, skin lotion? He took out the perfume bottle, and looked at her.

"One of your favorite things to smell, I bet?" He asked, playfully. "I've never even worn cologne... where's this supposed to go? Wrists and under the arms, right? Back of the neck? I'm trying to remember..."

But really, he just wanted to get to Julia's house!
 
As Julia drove (maybe a little over the limit) back to her house she explained Sammy how to apply the perfume strategically in the right places that would enhance his partner's experience of him. Never to overdo it and always remember that he himself had his very own smell that the perfume should help amplify.

Julia lived in a penthouse apartment with plenty of space and her own private elevator. When they got into the elevator she pulled Sammy into a deep kiss. Her mouth opened and her tongue forced it's way into his. "Oh fuck Sam. I want you so badly." She kissed him again and continued to kiss him until the elevator reached her floor. Then she handed him the bags, "Now go to the bathroom and make yourself ready for your mistress." She did however keep a single bag.. the one with her dress. "The bathroom is the second door to the right."
 
Sammy listened to her advice. Hell, if he played his cards right, he was pretty sure that he and Julia could get his own brand of perfume and with any luck, it wouldn't smell fucking awful like some of the perfume celebrities backed. He followed her into the elevator , watched her closely when she hit one of the top buttons... a penthouse? Oh, he should have known. She had a lot of high profile clients and ran a successful business, after all! It only further served to reinforce to him just how truly lucky he was. She was helping him, in every way she could... and she had shared her secret with him, whether by accident or not. That, and she was helping him explore his sexuality. Certainly not the sexuality that the media painted for a man... but one he found comfort in all the same.

Sammy made a noise of surprise when she all but attacked him with a kiss, forcing her tongue between his puffy lips and into the sweet confines of his mouth. Sammy's knees grew weak as he reached up to wrap his hands around her neck and returned the kiss, trying to match her force, fervor, and lung capacity. "I want you, too," He breathlessly tried to reply before she assaulted him with her lips once again. One of his legs kicked up a bit -- he could have kept doing that for hours, he felt like, but the elevator reached its floors and as he was handed the bags, Sammy knew he had more important things he could be doing. Mistress?

He quite liked the sound of that.

"Yes Mistress!" The boy echoed, practically prancing to the bathroom where he sat the bags on the counter and stripped completely down immediately. He sprayed the perfume in the areas she had directed -- lightly, of coruse! -- and then slipped into the slutty panties they'd bought. They were tight, constricting -- his cock was hard and that didn't help things, either. The head poked out from the black and white lace and frills. Satisfied anyway, the 'male' slipped into the slutty french maid outfit they had bought as well, finding it... incredibly kinky to wear, in all honesty. He touched it up by putting on that little, lace band that came with it on his right leg, and a black choker around his neck. He gulped, fixing his dress as he stared at the mirror. Make-up, definitely needed makeup. He slipped into the three inch heels that came with it and after taking a moment to find his balance, the boy turned to the side and bent over slightly in the mirror to test the length of the skirt.

As soon as he bent at all, his ass would be in sight, along with his teasing panties... perfect for what he wanted to draw out of her, he decided. He was excited. Nervous, anxious -- was this what it felt like to be in love? Was he even in love? He wasn't sure.

In either case, he stepped out...

"Ready for the makeup, Mistress!" He called, searching for her.
 
She came up behind him and spoke, "So my little maid is ready for her make over?" As she came into his view he would see her in the dress she had bought. It was a very tight black latex dress. It left very little to imagination. She had opted to go without panties so once her cock got hard there would be nothing but the dress to stop it. She had wondered how that would feel and look and she really looked forward to finding out.
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On her legs she wore 4 inch black boots that came up past her knees, and in her hand she held a leash, one that would fit nicely in the choker that Sammy wore. She looked at him sternly, while she clipped the leash onto his choker. "Get your ass into the bedroom girl. And sit in front of the vanity table." She pulled playfully on the leash to make him follow her to her bedroom.

The bed was very large but she kept pulling until they were in front of the vanity table. Then she pushed him onto the chair and began to apply his makeup. As she did it she explained him some of the secrets of makeup. How to get a good coating of lipstick and how to make sure his lashes looked marvelous. When she was done she smiled and gave him a mirror. "You look like a girl now. A really hot and sexy girl. So you want to be my maid for tonight?"
 
"Wow..." He said, when she came into his view. What he could he say? He'd been suspicious of the dress when she bought it, but now he felt foolish for ever even doubting she'd look good in it. From the way it hugged her breasts, outlining her nipples to the fact it left the skin of her hips showing, he was in love. And... he could tell she wasn't wearing panties! Surely if she was, he would see them on her exposed hips? And those heels... wow, he couldn't wait to get a look behind her. She approached, and he swooned as she clipped a leash into his choker.

"Yes, Mistress!" He said, by now so used to her calling him a girl and so prepared to be a girl for her it didn't even phase him in the slightest bit. He followed behind her on the leash, small cock wishing it had the clearance to tent the skirt at all, to make it known just how painfully hard he was seeing her in that dress. He watched her ass -- it barely fit -- as they walked to the room, and only tore himself away from it when he had to sit at the table. He sat still and listening as she explained how to do makeup, tried to say he'd remember it -- but he knew that he would need several more sessions of hands on training to make that a truth. It was no mater; soon he'd just leave it to his stylist.

When she was done, there wasn't a hint of boy left in the mirror. Just a gorgeous, flat chested slutty little maid with beautiful lashes and pretty pink lips. Sammy decided that he would have a little fun; he struck a pose and kissed at the mirror, before turning his full attention to her.

"Yes, I want to be your sexy little maid-girl for the night, Mistress -- tell me what to do." More over, he wanted to be her bitch. It was a strange thing, to think of himself so vulgarly, so submissively -- and yet he was deriving immense pleasure from this experience already. He would have done anything for her in that moment, and that was made clear in his eyes. He'd even actually clean her apartment, if that meant teasing her cock into view with copious bending and brushing.
 
"First of all," she looked him in the eyes, "I want you to know that you can trust me completely. Whatever happens here is your wishes only. I won't do anything you don't want me to." She seemed very sincere. She wanted him to understand that his journey into womanhood would be of his own doing and no one else's. Only in that way would he truly embrace his new identity.

"But then I've ordered lunch from a restaurant across the street. I want you to get it..." She looked at him and smiled as she drew out the time to see if he reacted, "..... get it in the elevator. It should arrive shortly. And then serve my lunch in the dining room. I think I'd like a glass of cold white with the salmon." She pulled the leash to get Sammy very close to her, "And make it a little quick girl." She didn't bother to tell Sammy where the kitchen were or anything else. She wanted him to find out himself and see how many mistakes he made in the process.

Julia unclipped the leach and wrapped it around her hand before she left Sammy and went to the dining room herself. There she lit the candles and put on some light music.
 
Sammy nodded. That was actually very reassuring to hear. He wasn't really thinking things through, to be honest. He was moving from moment to moment, living in the present -- having her stop him, however briefly, and remind him that anything that happened between them was safe, sane and consensual. He was definitely picking up on some BDSM theme, at least, being lead around on a leash while she wore a latex dress...

He did react. Sammy's cheeks flushed with embarrassment as he briefly struggled with whether or not he had the courage to get it dressed like a little french whore. Luckily, she spared him most of that. Only from the elevator? Some delivery boy was going to get a very lucky eyeful, as far as he was concerned! Man, who would have thought I'd be giving guys an eyeful? Suddenly, he was pulled forward, his lips brushing against her chin as she finished it off.

"Yes, Mistress." He whispered, with eagerness. He wanted so badly to touch her in that moment -- but restrained himself. He turned around to start getting to work... but couldn't help himself. He felt sexy as hell with that short, flared out skirt brushing against his skin... and he showed it, by shaking his little ass and giving her a brief show of his panties before walking away. It took him time to find the kitchen, and no sooner did he determine what cold white was did he realize he was supposed to meet the elevator, and rush away in his heels -- as fast as he could -- towards the door just in time to catch the deliveryboy...

"I'll take that for Miss Wright!" He said, in his most feminine voice. Would he get made as a boy with a ridiculous fetish...?
 
The delivery got the sight of the year when he saw Sammy. There was no way he thought that Sammy was anything but a girl. The rapidly growing bulge in his pants were evidence that he liked what he saw. "I... errrr... yes.." was all he could mutter as the sexy maid took the package he was carrying. As the elevator doors closed again the last thing that was heard from him was, "... the guys are not going to believe this..."

Surely Sammy had passed a great test. Julia would be proud of him once she heard. She had actually made an arrangement with the restaurant that they'd leave the delivery in the elevator if no one answered the door. So even if Sammy had chickened out he could just get the delivery in the empty elevator later.
 
Sammy kept the straightaway face he could as he quickly made his way back in to the penthouse. The last thing he heard as the elevator closed sent him in to a high pitched laughing fit as he closed the door behind him, took the food out in the kitchen, and plated it for Julia. He finished preparing her drink and, with skin still flushed with color, made his way to her. He was a bit hungry himself, but he was in a rush!

"Food for you, my Mistress!" He said, placing it before her with a slight bend, giving a good show of his legs. "The delivery boy could have dented the elevator door the moment he saw me." He shared, hoping she would understand the innuendo
 
Julia was glad when he arrived. "That's good girl. You make me proud. Like I told you: You are a very beautiful and sexy girl and we'll make you even sexier." Then she put the leash back on Sammy and pulled it. "Get down on the floor girl. And sit between my legs while your mistress eats." she pulled Sammy under the table and spread her legs slightly.

From Sammy's vantage point it would be clear that she wore no panties. It was also clear that her soft cock was not as amazing as it was hard. Actually it were barely 5 inches as it hang between her legs, the growing capabilities of her cock were rather amazing.

Julia began to eat and from time to time offered Sammy a little salmon or bread or lettuce as he sat between her legs. "So girl. Tell me; how does it make you feel to turn a guy on like that delivery boy?"
 
Sammy felt a surge of pleasure as she reconnected that leash to him, and wasted no time at all complying with her wishes to get down on his knees, between her beautiful legs, and remain there while she sat. He did exactly that, smoothing out his skirt as she spread her legs and gave him a front row seat to her cock. He was right; there were no panties. And, embarrasingly enough, her cock soft was longer and thicker than his hard. He truly was a girl next to this beautiful woman... or any man, he bet. He could scarcely keep his eyes off it, and was pleased to receive bits of food -- though he was a little disappointed his mistress wasn't as hard as he was. Was he not doing enough to drive her wild?

Sammy looked up when she asked her question, beautiful light eyes searching for her own.

"It made me giggly, honestly. He thought I was a girl -- he's got no idea he just got an erection for another boy, and something about that made me laugh really hard." He said, though that probably wasn't exactly what she was looking for. He put his hands forward, placing them on the edge of her seat. Slowly, he moved them between her legs, towards the center as he spoke. "But... I guess it made me feel really sexy, too. Because that meant he wanted to fuck me. I guess it's easier to find out who wouldn't want to fuck a sexy maid... but still, it was a totally unique feeling." Finally, he grew brave.

"May I touch you, Mistress?"
 
Julia was happy to see that she made Sammy feel so good. And the excitement of having him on the floor between her legs were starting to have an impact on her. She could slowly feel her cock start to harden. She knew that once it was hard the little maid were going to have her hands, mouth and ass filled full and she was looking forward to it.

She listened to Sammy's words and she really seemed pleased at this progress. "You are such a naughty." she chuckled, "That's my girl. Perhaps next time you should give him a blowjob just to thank him."

She let that comment hang in the air as Sammy asked his question. She looked down at him. "So my little maid wants to do some cleaning? So tell me girl. What is it you want to touch so badly?" She spread her legs even further to give Sammy a good view of her slowly hardening cock, her balls and her ass. Because of the tightness of the dress, it rode upwards when she spread her legs. "Do you see anything you want to touch my little maid?"
 
Sammy was overjoyed when it started to stiffen. It was an amazing thing, watching it slowly begin to grow before him. A tantalizing, mesmerizing thing. Julia's words hung in the air, alright, and he didn't seem as if he was going to say anything at all to that suggestion... but finally, he did.

"If you watched, maybe."

She looked down at him, though this time he didn't look up. He couldn't tear his eyes away from her most private areas.

"Your... cock, your balls... your ass... I want to touch it all, Mistress." He said, his hands stopping just short of her sack, the shadow of her slowly hardening cock cast over his tiny hands. "May I? May I please?" He asked, sounding desperate.
 
Julia smiled wickedly, "Oh baby girl. You can touch all you want. But you have to kiss everything you want to touch before you touch it." She said and spread her legs even further. Her ass was almost hanging freely, giving Sammy free access to whatever he wanted and to please his mistress as he seemed fit. Her cock was still growing, giving a clear indication that Julia loved what was happening and loved to have Sammy between her legs.

She took her wine glass and sipped the wine and then looked down at her slutty maid between her legs, wondering what move she would make.
 
Sammy could get behind those rules. Immediately, she turned her head to the woman's thighs, planting a short, sweet kiss on them both. Her hands shifted, to rub and squeeze at them while her face went further. The cock grew larger, and she knew any moment now it was going to be poking her in the face, or going past her ear with it's massive length. Sammy shifted his positioning only slightly, moving so that her legs were on either side of one of her own, and her crotch was pressed against her smooth skin -- the right shin. Then, Sammy continued his kissing escapades.

She kissed her ass, on both cheeks -- though it seemed to stop there as she traveled up and slightly over. She kissed the balls... and then began to lick them, to fondle them and shift them around with her tongue. She inhaled deeply, taking in the scent and taste. This alone made the 'girl' shift, to grind herself lightly against her Mistress' leg. Shortly, she began to suck on them, to tease and play with them. She wanted that big cock -- the object of her utmost affection -- to be hard and leaking before her tongue laid upon it.

Or maybe, she'd do something different now. Yes, perhaps that was what she'd do! Still, she wanted it hard.
 
Julia forgot to eat as Sammy began worshiping her legs and balls. She could feel her little maid's stiff dick rub against her high boots as the hot tongue licked her balls. "Ooohh yes girl." she cooed, "That feels so good."

Her cock was hardening and growing at an alarming rate. Luckily Julia's dress had been pulled up or she'd been in serious trouble in that tight thing. Her cock grew to it's full potential in a matter of seconds giving testimony to how horny she felt. She also put one foot up on the chair to allow Sammy better access to her cock, balls and ass.

Julia moaned and tried to get something on the table. The dildo she had bought earlier. She took it and were about to hand it to Sammy when the girl's tongue teased her sensitive balls and she felt her cock rest on Sammy's forehead. It felt so wonderful that she forgot everything else and let go of the dildo. The fake cock landed right next to Sammy while Julia moaned with pleasure.
 
Sammy had to dodge that dildo that fell down under the table. He stopped to look at it -- a nine inch beast -- and considered something... He wondered, would Julia be opposed...?

"Mistress..." He began putting a quick kiss on her cock so that he could start to stroke it with his two small hands. "Would... you want me... to use that on you?" He asked, hoping she'd understand. Because if not, damn, he was going to shove it right into himself!
 
Julia moaned as he began to kiss and stroke her cock. She could feel the dizziness of her mind as the blood rushed to her cock. When she asked for permission to use the dildo on her, she moaned again. "Oh yes baby. I want you to fuck me with it while you suck my cock."

It was rare for Julia to be fucked. But she did like a hard large dildo in her ass, but had rarely done it with a partner. But Sammy was so sweet and cute and sexy and she really felt she wanted her and wanted to make her feel good. So she had decided that there would be almost no limit to what Sammy would be allowed to do. Of cause the little girl would never fuck her mistress, but Sammy would be allowed far more than anyone had ever been.
 
Sammy was eager to please, and eager to try out his idea. After all, what better way to explore what she meant than by trying to bring a partner to that same experience? He might have tried his cock, but it was so small and pathetic that he wouldn't even ask to put it anywhere on her -- well, maybe her mouth, but only if he felt exceptionally deserving. The boy spoke up, then:

"May I have the lube, Mistress?"

He wasn't going to shove it in her dry, after all. After asking his question, Sammy went to give attention to the head of her cock, to flick his tongue out across it and brush his face against her massive girth lovingly.
 
Julia gave the lube to Sammy as her maid licked her cock head. This was such a turn on for Julia. She loved how Sammy adored her, how her little maid seemed to be totally devoted to pleasing her. And she looked down at Sammy, "OH yes. My beautiful little Sammy. Suck my cock fuck my ass."

Julia put a hand on Sammy's head and caressed the girl. "You are such a pretty girl Sam. You really are." She said it both because she meant it but also to reinforce Sammy's own self image as a girl.
 
Sammy squirted some of the lube on the dildo, and began to make sure to cover the dildo rather liberally with it. It was a strange feeling, surely... but he didn't mind. She looked up sweetly at Julia, responding to her praise by nuzzling her face lightly against the woman's mighty shaft.

"I'm glad to be your pretty girl." Sammy said, cheeks flushed. Finally, Sammy sprayed a bit more lube just to be sure onto the Dildo, and then wrapped her lips around the head of Julia's cock. From there, Sammy began to bob and suck. The maid's hand reached forward and lightly touched one of Julia's large balls before finding the hole between her cheeks and, lightly but insistently, started to slowly push in against the woman's tight, pink hole...
 
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