Today's the day:The first Time
By
Skinnie Stallion
Part 1
Andy knew he should’ve realised it was going to be a long day when he was doing his Aunt’s make-up and helping her dress that morning. This had become a ritual on Saturdays and Sundays: she’d said that he simply wasn’t getting enough practice during the week because of his work, so rather than her doing play face painting with him in the afternoons, she now expected him to use her brushes and powders on her. ‘Practice makes perfect’ was one of her mottos.
some concessions: he’d bought a pair of Bliss Galore Skechers and socks to match the trainers’ liner. He thought pinky-mauve was quite a bold look for a boy like him. He was already a bit concerned about what others would say at the club that evening. Despite the time he’d spent selecting a new pair of skinny jeans with just the right distressed feel, she was very clear when he arrived on yesterday for their Friday Netflix evening that she was tired of his jeans and plain white tees look. And his baggy ripped Diesels definitely had to go.
He'd wanted to sleep in that morning, but Aunt Jane had insisted on a prompt start. He’d made their coffee and slipped back into bed for a final cuddle when she suddenly sat up and said: “Today’s the day. We need to go shopping.” He’d thought it was going to be just going to be another trip to help his Aunt choose dresses. He was going to protest and plead for another five minutes, even starting to slide down the bed to try to persuade her, but she was resolute. “I’m fed up with how you look,” she’d said. “You need a proper pair of jeans and shoes. Not those baggy things, and definitely not trainers. Not if we’re going out tonight.”
Maybe he should have realised after her shower when he was dressing her. She’d selected a pair of her tightest stretch jeans. He’d needed to roll her on the floor to get her into them. And then she chose the thigh boots that she’d worn to bed last night. Not the over-the-knee ones she sometimes had for day wear, but the thigh high ones. She normally only wore those in the bedroom. She knew he couldn’t resist her in them. He loved holding her leather clad calves or gripping her heels as her legs crossed and locked across his back. She’d been very clear with him that her stiletto heels would be the only shaft he would ever need to hold if he wanted to be amorous, and she had been right. He loved gripping their stiffness in his hand as her leather enveloped him, pulling him closer as her thighs grazed his cheeks.
He thought they’d be off to somewhere like Churchill Square with time for another coffee and maybe a croissant or pain au chocolat while they planned which stores to visit, so he was dismayed when the Tesla started heading away from town. “Where are we going Auntie?” he asked. “Aren’t we going into town?”
“No honey, the selection’s too small. We’re going north.”
“London?”
“Maybe.” Jane put some music on. Radio 3. Too early for bangers she said. Andy knew they would come later. But he did find ‘Composer of the Week’ rather dull.
It was more than an hour’s drive and Andy was gasping for that coffee when they arrived. But rather than stop at one of the coffee shops or even one of the stalls along the arcade, Jane told him to go straight to a shop called ‘Mademoiselle’ while she went to the loo and did some browsing. She said she’d drop by ‘Mademoiselle’ to collect him.
Andy walked with some trepidation into ‘Mademoiselle’. It didn’t seem to be a clothes shop. All the counters just seemed to be for make-up. Two attractive ladies in short white mini-dresses greeted him on the first counter: “Good morning, you must be Andrew. Lady Jane said to expect you.”
Andy was perplexed. Had Aunt Jane called ahead? He couldn’t imagine that she’d had much time given that she would have needed to spend a lot of time shimmying just to get her jeans down in the Ladies. “Errr, yes,” he acknowledged.
The shorter of the two with pixie platinum hair came out from behind the counter “You look worried, darling. Don’t be.” She took his hand. “Lady Jane has booked you in for a full pampering.”
“Are you sure?” queried Andy. “She said she was only going to be a few minutes. I expect she’ll be along soon to buy some make-up to top-up her supplies and get some new shades.”
“Oh, no. You’re booked in with us for two hours: a facial and make-up,” said the pixie
“I think you must be confusing the bookings. I think that must be for her.”
“The booking’s definitely for you. Here at Mademoiselle, we only do boys and young men.”
“I need to check. There must be some mistake. Please can I call her?”
“Don’t worry, honey, I will,” said the pixie. Her blonde colleague, who looked a little like his beloved Auntie, passed her a phone from behind the counter. “I’ll use call back. It’s ringing…. Hello….. Lady Fullerton-Jones? ……. Yes, it’s Mimi at Mademoiselle….. He’s here….. He says you’ve made a mistake. He’d like to speak to speak with you…… Oh, no need, you say……. He needs to learn to follow instructions….. Yes, he probably does…… Yes, thank you, Lady Fullerton-Jones…… Yes, we will but we will need another hour ….. No problem. He’ll be lovely and smooth for you when you collect him. ……. Pinky beige? ….. Yes, we can do that. ……. Thank you, Lady Fullerton-Jones. We’ll see you in three hours.”
She held the phone out so that Andy could hear his Auntie: “Be a good boy, Andrew. Auntie loves you.”
“Love you, Auntie,” Andy blurted and then blushed realising that the ladies had just heard what he’d said. He’d never said that in public before. But the ladies were smiling approvingly. He just hoped another boy and the lady accompanying him standing nearby hadn’t heard.
The pixie pulled back the phone, listened then said, “A pleasure Madame. Mademoiselle are delighted to assist. Giving a boy so early in his journey a glimpse of what is to come is such a loving gift.” She hung up the call.
Andy was puzzled. “Journey? Where am I going? And three hours!?”
“Don't worry, darling. You’ll find out. Your Aunt has big plans for you. Now go with Tracie to one of the cubicles at the back of the shop. Tracie will be looking after you today. She’ll start with your waxing and facial.”
“Waxing?!”
“Yes, waxing. Lady Jane was quite insistent just now when I told her you thought she’d made a mistake. She wants you nice a smooth. You’ll have gathered she’ll be picking you up in about three hours. Would you like a cup of coffee? Milk? Sugar? Tracie will bring it through to you when she’s got you started. Now go with Tracie and take your clothes off.”
Tracie had been behind him during the call and had held him firmly by the shoulders as if she was going to stop him running away. She towered over him in her 5” Louboutins, a bit like Auntie did. He wasn’t going to run away from her. She took his hand and led him towards the back of the store. As they walked away, he heard Mimi speaking to the couple who’d been standing near the counter. “….No, I’m afraid we won’t be doing his make-up for another two hours. If you’d like to come back in a couple of hours, I’m sure his Mistress wouldn’t mind. You can always look at some of our products while you wait. Maybe try some nail varnish? A manicure? A pedicure?” And then they were out of earshot.
Part 2
“So Andrew, how does it feel?” Jane asked.
“Chilly,” he replied. The boy watching sniggered. He and his lady companion had been observing him having his make-up down by Tracie. It was the first time anyone other than Aunt Jane or himself had done it, and definitely the first time anyone had watched him being prettified. Andy had to accept that the work of a professional was better, much better, than his own amateurish efforts or even his Aunt’s. His skin seemed to glow, and his cheekbones had an iridescent lustre that made then stand out against his bronzed and delicately rouged cheeks. And yet the shading was simple. Tracie had used a much narrower colour palette than he was accustomed to. Everything was beige or neutral with just a hint of pink on his lips and cheeks.
Andy shivered. Neither the boy, Thomas, nor his friend whom he called Mistress Firm, seemed at all
perturbed that Andy was naked now that Tracie had removed the cape she’d given him while she did his face. Tracie wanted to show off his smooth, fully depilated body to Aunt Jane. Andy had found it odd being observed while he was having his make-up down. Every time he looked up, he found that Thomas’s eyes were fixed on him while Mistress Firm spent her time either smiling at him or beaming with pride at Thomas. He found it both satisfying and oddly arousing having his make-up done by someone other than Auntie and having another lady watching. He was having his make-up done in a salon: what could be more normal than that? And then the shock would hit him that he was sure Jane wasn’t going to let him remove it, and that he was going to have to walk through the Mall in his jeans, sneakers and tee wearing make-up. It was all very well Thomas and Mistress Firm seeing him – they clearly understood - but not all the folk in the Mall. There would be men there. And he didn’t want guys or young girls making fun of him. He couldn’t decide which would be worse.
“Yes, I can see you’re cold: we need to get some clothes on you. But you look so much better without all that nasty hairiness.” Andy looked around for his jeans and t-shirt, but it seemed Tracie had removed them. Then he saw that Aunt Jane had some shopping bags with her. “If you could just slip into these.” Then she turned to Thomas and Mistress Firm: “It was so nice meeting you Fenella. You’ve got my number. Maybe we can meet sometime and compare notes? It's always useful to learn how other ladies train their boys. Now, if you and Thomas can give my nephew some privacy, I’d like to get him dressed so we can go shopping, please”
Tracie ushered the couple out while Jane started to delve into her bags. “Right, here we go: shirt, jeans and shoes.” She started to unbox the shirt. To Andy it looked less like a shirt and more like a blouse. A bolero cut, silk blouse with slightly elasticated blouson cuffs and delicate little poppers rather than buttons. “Oh, silly me,” said Jane, “we need your jeans first.” Another bag was opened. Andy was pleased to see it was a stone-washed pair of blue denim jeans, but gasped when she unfurled them and he realised that it was a pair exactly like the ones Jane was wearing. They looked super-skinny. “I think I got the size right. But don't worry, they do stretch. A little.”
“Can I have my pants first, please Auntie?”
“These are your pants, honey.”
“No, Auntie. Not like American. Underpants. Briefs.”
“Oh, you mean panties. You don’t need to wear those. Not in these jeans. They’ll be far too tight, and you won’t want to upset their lines. You have to wear these jeans ‘au naturel’ like I do. Now be good boy and slip them on.”
“I can’t. I won’t.”
Aunt Jane looked at him stony-faced. She didn’t say anything. He could sense her disapproval. He took the pair from her and pointed the toes on his right foot like a ballerina. His heel just got through. Then he did the same with his left. He started to pull the jeans up his legs. They pressed hard against his calves and then his thighs. ‘How did Auntie wear these all day?’ he thought. ‘What on earth did they do to her circulation?’ He got them to the top of his thighs and then wondered what to do. There was no way everything was going to fit.
“You pull, and I’ll push,” said Jane. She came close to him and her hand pushed his little protuberance back between his legs. “You are lovely and smooth down there. It will be so much easier tonight with no hairs getting in the way and so much easier to get you clean after.” She gave a knowing look and a little wink at Tracie who smiled and gave a slight nod of acknowledgement. It was clear that Tracie was not in the least surprised. “Now, pull hard.” And then the jeans were over his bum but he still had to fasten them. “Lie down like I do with you, then breathe out.” To Tracie’s amusement, Andy laid down on the floor and wriggled and writhed. “Breathe out, darling,” instructed Jane. “Aren’t you glad I didn’t take you for that croissant when we arrived.” Andy drew the sides together, fastened the button and pulled up the fly. Jane extended a hand to pull him up. “There! Doesn’t that feel good? Look at yourself in the mirror.” Andy had to admit that the jeans suited him and made him feel very sleek and slinky. “Now put on your blouse, I mean shirt.” Andy was embarrassed to find that he had an exposed midriff. “If you like darling, we can get you a belly button piercing. It would look so good with that blouse.”
“Not today, Auntie, thank you. Now can I have my trainers. Though I don’t know how I’m going to bend down to do up my laces.”
“Don’t worry, I asked Tracie to bag your up your Skechers with your other clothes. I got you some slip-ons.”
“Oh good, thank you Aun…..” Andy stopped abruptly as he saw Jane unbox a pair of mules with transparent vamps and delicate marble print heels and mini-platforms. “I can’t wear those!” he protested again. This time Jane’s gaze was withering. “But they’ve got heels.”
“Of course, they have. You can’t wear skinny jeans and not wear heels. Silly boy, how else are you going to show off your legs and hips? Now put them on and see how they look.”
“Must I?”
“Why not, they’re only three inch heels. When you play in mine at home you’ve gone up to five inches.” Another glance and little smile from Jane to Tracie.
“But not here.”
Another withering look. “You’re embarrassing me in front of Tracie. Just slip them on. I know you're going to like them,” she said firmly
“Must I? Really?” Wearing make-up in the Mall was going to be bad enough, but a blouse and high heels! With those skinny jeans, anyone might think he was a girl. That would be terrible.
That stare again. “Yes.” Andy stepped into the mules and looked at himself in the mirror again. He paused. He had to admit he liked the look. The heels really worked with the jeans. He didn’t just feel slinky, he felt sexy. Tracie smiled at him approvingly. “Would you like lunch now or shall we finish shopping?” asked Jane.
“I’m not sure I can eat a thing in these jeans.”
“Well, like Kate nearly said, nothing feels as good as skinny.”
“I just want to go home Auntie.”
“But we need to finish our shopping.”
“OK. Let’s finish your shopping.”
“Not mine, darling, yours.”
Part 3
When they walked out of ‘Mademoiselle’ and along the arcade, Andy felt all eyes were on him. He was used to his Auntie attracting attention, and always felt privileged to be seen as her escort, but this was different. As she held his hand leaving Mademoiselle, he felt he looked more like her girlfriend than her ‘boyfriend’. Not that he could ever describe himself as the latter, even though he found it a source of great pride to be seen with such a beautiful, if somewhat older lady. Maybe a nephew with a loving aunt? Except now that would make him her niece. But he was sure that some of the ladies observing them could tell Jane wasn't holding the hand of her girlfriend but of a nervous, feminised boy. They’d assume they were a couple in their lookalike jeans: a dominant mature lady accompanied by a petite, elfin beauty. She was so obviously in charge, in her dominatrix thigh boots.
Thankfully they’d only gone a short distance before Jane turned and led him into another shop: ‘Miss-Defy’. “I found this place while you were having your pampering,” she said to him and, to the assistants, “Yes, me again. I’m back to make those final selections.”
The assistants stood back and left Jane to get on with it. Soon she was rifling through the racks of lingerie. With mounting horror, Andy realised that she was selecting items for him. And she wasn’t being discreet about it: “If you want to do more of these casual weekends, Andrew, I think you need to start wearing something pretty for me beneath your school uniform.”
He could hear the assistants who’d gathered in the doorway speaking to one another:
“No, it's a boy! I heard the lady calling him Andrew. She’s dressing him.”
“Sounds like she may prefer undressing him. Look at the arse on him: he’s got such a cute bum.”
“Nice tight buns.”
“Those jeans must have been sprayed on. And that figure!”
“They’re dressed very his and hers.”
“Yes. He’s hers.”
“Have you seen she’s moved on from the silk and lace to the latex?”
“I’d love to see how he looks in those.”
“It looks like it could be a big order.”
For some reason, their chatter gave Andy confidence. It didn’t matter whether they thought he was a boy or girl. He was a customer. And being with Auntie was so nice. Perhaps he could manage a little lunch while they were at the Mall. Who cared whether people thought he was a boy or a girl? Trixie and Mimi hadn’t. Mistress Firm hadn’t. Even Thomas hadn’t. And Auntie certainly didn’t. And only Auntie really mattered. (Well maybe his Mum and his Gran, but he knew they’d approve if that’s what he wanted and was happy. And his Mum knew he was very happy with her closest friend. She knew he was being well taken care of. Very well.) He started to look more closely at some of the styles Aunt Jane was selecting. Did girls really wear all that?
Part 4
“Now come along darling, you’ve done so well so far. Just this little frilly slip.”
“But I feel hot Auntie.”
“You certainly look hot, honey. Very hot.”
‘Don’t you like how you look? You helped select these.”
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