"You could come and work at the salon on Saturdays."
That was how it started.
"Annie, our apprentice, just quit. She was useless anyway. I'm sure Carol could do with some help, I'll ask her."
They'd been going out together, sort of, for a couple of months. They got talking at a club when they noticed that their rubber dresses were almost the same. She found it quite amusing, going clubbing with a guy who dressed the same as her. And they were great in bed together.
He started work at the salon the following weekend, or rather Cindy, his feminine alter ego, did. His duties were simple enough - keep the floor swept, make coffee and tea for the girls and for the customers, keep everything spotlessly clean, help with shampooing and other odd jobs. He wasn't being paid, his normal job paid well enough and he was doing it for the pure pleasure of spending the whole day dressed as the woman of his dreams. Clubbing was fine, but he wanted something more like real life, and where he couldn't just go off for a quick wank after half an hour which is what happened if he tried it at home.
He wore five-inch stiletto heels, black stockings, a thong that held his cock tightly in place but left his bottom bare, a short skirt, and a shirt which covered his false tits but still left a bit of false cleavage showing. With makeup and an expensive hand-made wig, he could pass for a real woman even under quite close inspection.The other girls knew the truth, and over time so did quite a few of the customers. He was a hit with both.
He had a wonderful time. Strutting round in public in his heels was a huge turn-on. At the end of the first day they rushed home together and fucked like animals. Later, they sometimes couldn't even wait that long. They'd go into the storage room at the back and do it there. A few times they'd sneak out there during a quiet moment and he'd lick her while she stroked him to an orgasm inside his strap. He was damp for the rest of the day but it was worth it.
It was the longest he'd ever worn heels like this. His feet and legs hurt, but the constant excitement made it worthwhile. And there were always quiet moments when he could sneak into the scruffy lounge behind the salon and take his weight off his feet for five minutes. Often some of the girls would be there, and they'd gossip among themselves just as though he was a real girl, talking about their boyfriends and their girl problems and everything else. He loved every minute of it. Sometimes he'd have an intimate chat when he was alone with just one of the girls. He learned things that she would never have told a guy - well, one who looked like a guy. All the girls were intrigued by him, and some were quite turned on too. He loved giving head and some of them found out just how good he was at it too. His girlfriend loved to spank his bare bottom, lifting up his skirt, making it sting just nicely.
When the salon closed at the end of the day, all of the girls went home. While Carol, the owner, cashed up and checked stocks, he would clean the place, sweeping and mopping the floor, polishing the mirrors and all the glass. He took his shoes off for this - his poor feet were so tired and it was such a relief. And the feel of the hard, tiled floor through his slippery stockings felt quite sexy, too. Carol would look on approvingly while his girlfriend waited in the lounge.
Carol was a very good looking woman in her thirties. She knew exactly what was going on, and thoroughly approved of it. She didn't expect her customers to be shocked - it wasn't the kind of place used by old ladies for their weekly rinse. She'd paid a designer a lot of money for the interior, all stainless steel, glass and mirrors, softened by black leather. In her mind a transvestite "apprentice" just added to the effect, and her customers seemed to agree. She hired girls who fitted in with the image she'd created, and she encouraged them to be a bit exotic and sexy. Carol herself nearly always wore tight black leather pants and a tight top that all showed off her excellent figure. Other girls wore short skirts that revealed their bottoms when they bent over, or shorts, or tight stretch jeans. One always wore high platforms - a good idea since she was tiny, but still quite surprising for a job that involves standing up all day. The atmosphere of the place had a constant sexual charge to it.
One Saturday, after a few weeks, he came into work as usual and was surprised to find his girlfriend wasn't there. He hadn't seen her for a few days, and Carol told him she'd called in sick.
"Is it OK to work here still today? I mean, just me, without her...?"
"Of course it is, you silly girl. We'd be lost without you now. Come on, get started, make some coffee for us all."
So he worked just as usual. But it felt different, he felt vulnerable without her there, like a lamb in the lions' den. He felt as though people were staring at him, just like the rare occasions when he ventured outside in his girlie clothes. Still, he tottered round on his heels, ignoring or maybe savouring the discomfort in his legs and feet, sweeping and fetching things and making coffee.
Towards the end of the morning one of the girls pulled him out to the back and into the store room.
"Can you get your cock out of that thing?" she asked. "I've always wanted to give a blow-job to a tranny, I didn't dare ask while your sweetheart was here."
He was surprised, but he undid the strap. She went down on her knees, took his soft cock into her mouth, and soon he was hard. She was really an expert. She kept him excited for a long time before finally moving her tongue to a different position. He started to pull out of her mouth when he was about to come but she grabbed his bottom and held him inside her. He exploded into her mouth. When he'd stopped she stood up and gave him a sloppy, cum-filled kiss.
"That was good. Funny how you men think we girls don't want cum in our mouth, that's the best bit. Lovely! I'm all wet now, how about it's your turn?"
She dropped her tight, stretchy designer jeans to her ankles, bent over some boxes, and tugged her little thong to one side. Giving head to girls was just about his favourite thing. He dropped to his knees and put his tongue and lips to work around her pussy and her hard little clit. She really was sopping wet, and she came quickly.
"Better get back now, they'll all be wondering where I've gone," she said with a big smile as she tugged her jeans up and arranged her clothes. She gave him another big kiss and was gone.
After lunch, Carol led him into the lounge and shut the door. Nobody ever shut the door, so it must be pretty serious. Was she going to fire him over the little incident this morning? He certainly hoped not.
"You seem to be settling in well. All the girls seem to like you, and the customers too. It was a bit of a risk letting you work here, but it seems to be working out really well."
He didn't know what to say. She didn't seem cross, that was something to be grateful for.
"I'm glad to have a chance to talk to you on your own. I think she protects you a bit, and you need to spread your wings. I think I'm going to have to take you in hand myself a bit."
He wondered what she meant. He found her incredibly sexy and had often fantasised about her, so he was excited by the idea whatever it turned out to mean.
"You make a good girlie, but I think you need to learn a bit more about how to really serve women, how to be a woman and yet be one of your pathetic inferior sex at the same time. I think I can help you learn. What do you think?"
He just nodded dumbly. His fantasies were all about serving her, being her slave. Could that be what she meant?
"Good. How would you like to lick my boots for me? If you do a good job, maybe I'll let you polish them with your cum."
He couldn't believe his ears. He dropped to his knees and bent his head towards her feet. She laughed.
"I suppose that means yes? Alright then, go ahead. But I want you to really work on them, kiss them as though they were my body, not just a quick lick."
He did as she said. She was wearing black leather boots, polished to a shine, with a modest stiletto heel. He pressed his lips and tongue to them, tasting the leather and the remains of the polish. She didn't say anything, so he licked all around the toes, then up her foot towards her ankles. Still she said nothing, so he started work on the spike heels, running his tongue up and down, trying to copy what the girl had done to his cock a couple of hours earlier.
His tongue was beginning to ache when she finally said, "That's enough. Now you can polish them. Get your cock out from that thing."
As soon as he unfastened the strap, his cock shot up, rock hard. He crouched down by her boots, wanking furiously, the realisation of a fantasy he'd had so many times since he met her. Soon his cum spurted out onto the polished black leather.
"Spread it round with your cock, rub it into the leather," she commanded. Then, when he'd spread it round, she told him to lick it off again. That hadn't been part of his fantasy. He'd never eaten semen before, his own or anyone else's, and he wasn't really prepared for it. He looked up at her but before he had a chance to speak she kicked his balls, not hard but enough to make him yelp, and said, "When I tell you to do something, you just do it. No questions, no hesitation. Right?"
He mumbled an apology and started licking. He was surprised at the taste and texture, he expected something strong, gooey and unpleasant but it barely tasted of anything, a little salty but masked completely by the leather. Soon he was licking enthusiastically, as she encouraged him.
He'd nearly finished licking her second boot, his erection hard again already, when the door opened.
"Oops, sorry, didn't realise you were in here," said the girl.
"That's OK, come on in, Cindy's getting a lesson in how to treat a woman. Come and join in. I'm sure Cindy won't mind."
Actually Cindy did mind, it was one thing to live out a fantasy and another thing to do it in public. But there was nothing she could do about it, so she just kept on licking.
"Cindy has been polishing my boots with her special polish, and now she's just giving them a final finish. Maybe you should show your appreciation of Dawn's shoes, too."
Dawn was wearing trainers, fancy designer trainers it's true but still just rather unattractive assemblies of nylon and plastic. He looked up again, and once again Carol kicked his balls gently. So he did as he was told. They tasted horrible, much worse than the leather and cum that filled his mouth. Dawn thought it was funny and started laughing.
"That's enough, it's worse than being tickled'" she said. "That's not my most sensitive bit, you know. Not that I'm up for that right now, I'm a girl who likes to take her time. But I wouldn't mind giving you a good spanking on that bare bum of yours."
So he found himself bent over the sofa, his skirt pushed up around his waist, while she spanked him with her bare hand. She did it really hard, much harder than his girlfriend, and soon he was squealing and crying in pain. She stopped briefly to admire her work.
"There, that's nice and red. You can even see my fingers. I love doing that, and you've really got a beautiful bum. I had a boyfriend once that like being spanked, but his bum was nothing like as cute as yours. But you'd better make a bit less noise or they'll hear out in the salon. We don't want the customers to hear, they might want to join in." Then she carried on. When she finished and he stood up again, his poor bottom was really stinging but his cock was rock hard. It took quite an effort to convince it to fold up inside the strap again.
"You'd better get back to work. But you'll have to redo your makeup first, it's all streaky where you've been crying, you big baby." Both the girls laughed and went back into the salon. Poor Cindy had to spend ages putting her makeup back. For the rest of the afternoon her bottom stung terribly, as she tottered round sweeping and cleaning. All the girls soon knew about what had happened, they'd look at him in funny ways and giggle. He was terribly humiliated.
When it came to closing time, the girls all said their goodbyes as usual. Dawn patted his bottom and whispered, "I hope it still stings," and pecked him on the cheek. It did. Then Carol closed the door, and he took off his black stilettos as usual, to start the end-of-day cleanup.
"What do you think you're doing?" demanded Carol.
"I'm, you know, cleaning up, like I always do."
"Get those shoes straight back on again. I never said you could take them off. From now on I never want to see you without your heels. And another thing, I never want to see you sitting down, either. If you've got nothing to do, you stand quietly in the corner. If you're allowed to rest - which won't be very often - you get down on your knees. In future, you do exactly what I tell you, when I tell you, no questions. And if any of the girls tell you to do something, you do that too, well, as long as it's legal. Understood?"
"Yes Carol," he said, nodding.
She slapped his face. "I'm not Carol, to you. You call me Madame. Every time I speak to you, you say, 'Yes Madame,' or 'No Madame', or whatever. And you don't speak unless spoken to. Get it?"
"Yes... Madame." He put his shoes back on. His feet really hurt now, and he had a lot of trouble walking up and down with the broom and then with the mop. But he really was her slave... that was something to be proud of. His cock was hard under its tight strap. It took him much longer than usual to clean up. By the time he finished, Carol was waiting impatiently.
"If you can't do it quicker than that, I'll have to lock you in here all night. I can't hang about forever, I've got a life to lead."
He apologized, humbly, remembering to call her Madame.
"Good. It's been a good day, and I think you've learned a lot. One other thing. Those shoes you're wearing, you seem to walk quite easily in them now."
"You need to get some higher ones. Get some with six inch heels for next week. With your big clumping feet, five-inch heels are barely worth bothering with." And with that she sent him home.
To be continued