“Role appropriate attire?” Jon muttered, “does that mean what I think it does?” He looked over at his mother, already dreading the answer.
“I’m afraid so” she sighed as she began to open the chest of drawers her watch had been sitting on, “it’s that or another one of those headaches again” she added with a shrug as she pulled out a pair of large men’s trunks. Jon actually found himself weighing up the two options in his mind. Wear women’s clothes, or get a couple of quick nasty headaches. Then again, there was that threat of ‘corrective measures’. The head pain had been bad enough, especially the second time, and he didn’t want to find out just how far this place was willing to go in order to keep them in line.
“Just what kind of vacation did you sign us up for mom” he grumbled as he began opening the other set of drawers. The top drawer was filled neatly with panties, bras, socks, and tights. All of them arranged so neatly that it looked as though the drawer was divided into four. The next drawer down had a vast selection of cotton tops, from vests, to t-shirts with varying sleeve lengths, and again everything was folded and arranged neatly in a seemingly specific order. Drawer number three held a lot of sweaters, cardigans and a few scarves. Neatly folded and arranged sleepwear came next, with matching pyjama sets, night gowns, slips, and to Jon’s horror, some silky teddies and negliges too. Finally the bottom drawer held a selection of jeans, shorts, slacks and linen trousers.
“I never understood why women need so many clothes” he said with a half smile, trying to make light of his current situation.
“Well, you might just learn something if this doesn’t get sorted” his mother replied kindly, “you’ll probably find more in one of those closets” she added indicating the two large units on either side of the bed. Jon turned around and walked over to the one on the left hand side, the furthest away from the door and the one opposite ‘Joanne’s’ drawers. Sure enough, when he opened the double doors he was greeted by various dresses, skirts, blouses and jackets. There were two more drawers underneath, with the shallower top one containing an impressive collection of bags and purses, and the deeper bottom one was nearly overflowing with shoes of all different types, pumps, heels, boots, trainers, sandals and more.
“This is too much” Jon muttered, feeling a little overwhelmed by it all. As if reading his mind both his and Linda’s watches sounded again and their tasks flashed in their holographic boxes.
“We better hurry up, I don’t think they’ll let us take all day” Linda said as she turned back to her chest of drawers. She lifted up a pair of men’s trunks and held them out by the waistband.
“They certainly look my size” she said as she returned a pair of crew socks from the same drawer, followed by a forest green polo shirt from the second drawer and a pair of dark blue straight leg jeans from the bottom one. Reluctantly Jon returned to his drawers and selected a pair of white cotton panties, and a matching bra. The bra had no real cups to it, and looked as though it was designed to sit flat against his chest. He grabbed a pair of white ankle socks, followed by a white t-shirt with a deep v-neck and pair of high waisted, light blue mom jeans. With a sigh he looked over at his mom.
“Are we really doing….OH MY GOD!” He gasped as his mother just started removing her clothes in front of him. She had turned her back to him, but she had already removed her blouse, and was already undoing the front of her slacks.
“Sorry sweetheart” she said, her face flushing, “I just wanted to change as quickly as possible. I really don’t want another one of those nudges” she winced as she recalled the pain.
“It’s ok” Jon replied, “it just caught me by surprise, look I’ll face the other way so we won’t see each other…naked or anything” he added.
“Good idea,” Linda smiled softly, “we better get a move on” she added turning away from him again. Jon turned himself so his back was to his mother and after a moments pause, he kicked his shoes off, unbuckled the belt of his jeans and pulled them down. Next came his t-shirt and socks, and finally he pulled his boxer shorts down. As he straightened up again he accidentally glanced behind him. The sight that met his eyes was a strange one. His mother was also completely naked like he was and was hunched over stepping into a pair of men’s boxer trunks. She shimmied them up her waist and settled the waistband over her hips, the fit was perfect with the fabric clinging tight to her rounded backside. Jon realised he was staring and quickly turned away again. He snatched up the panties and stepped into them. He pulled them up his legs and found they were perfectly sized to sit like they would on a real woman, despite being tailored to fit his junk as well. It was a strange feeling wearing them as the elastic in the waistband wasn’t as tight a his old underwear, yet still held firmly around his hips and legs.
‘This is fucking surreal’ he thought to himself as he picked up the bra. He knew enough from TV and other media that one of the easier way to put it on was to clasp it in the front then spin it round before putting your arms in the straps. Despite knowing this, he still managed to fumble with the clasp several times before he finally got it fastened. Once it was facing the correct way, he pulled each strap over his shoulders, and his suspicions about the cups were confirmed as they sat flush against his chest. Next he slipped the t-shirt on over his head, the capped sleeves ending just below his shoulders, and the v-neck sitting low on his chest would have shown off some tasteful cleavage if he actually had any. Finally he pulled the jeans up his legs, finding the higher waist a little strange. He sat on the edge of the bed and pulled on the ankle socks to finalise his outfit.
“They fit you quite well” Linda said as she finished buckling a brown leather belt. The outfit she had chosen fit her perfectly, although Jon could clearly tell she wasn’t wearing a bra underneath the polo shirt as the peaks of her nipples poked out the material.
“Thanks” Jon replied, “it’s the most masculine thing I could put together” he added with a shrug.
“Could I make a suggestion?” Linda asked, “just something to bring all this together” she added gesturing at his outfits
“Umm…I guess?” Jon replied uncertainly. Linda stepped past him and over to his open wardrobe. She plucked out a light tan coloured blazer-like jacket that was slightly tailored at the waist so it flared out at the bottom. She handed it to Jon who slipped it on. He stood and looked at his reflection in the mirror of the wardrobe door. He had to admit it did look good with the rest of the clothes he’d chosen. His attention was grabbed by the chiming noise from his watch. He held his wrist up and the pastel purple text box appeared in the air again.
NEW TASK
APPLY MAKEUP & JEWELLERY
Assistance temporarily permitted
Jon rolled his eyes, and felt his shoulder sag.
“Come on sweetie” Linda said guiding him over to the vanity “I’ll show you what to do, but I think you’ll need to learn to do it yourself so you might want to pay attention” she added as she sat him down in the swivel chair. She then set about gathering the various tubes, brushes and sponges assembled on top of the vanity. Jon sat there and reluctantly allowed his own mother to apply makeup to his face, listening as best he could as she told him what each item was, what it did, and how and where to use it. After each step she turned him so he could see himself in the mirror, and he surprised a shudder each time she did so as his face took on an increasingly feminine appearance.
“Aaaaand we’re done” she eventually said as she finished applying some setting spray, “I’ll try and walk you through it next time…if I’m allowed. Now let’s find you some accessories” she added as she looked around the room. Jon’s eyes fell on a drawer set into the vanity and slid it open. Inside were neatly segmented compartments with various earrings, rings, and necklaces that were perfectly organised.
“Ok, let’s start with something simple” Linda said as she looked over the collection, “I see a few clip-on earrings here, but it looks like you might need to get your ears pierced if things stay like this” she said thoughtfully. She selected a pair of small clip-on gold hoops and showed him how to attach them to his lobes. She then picked out a matching, gold chain that was thin and delicate. She encouraged him to put it on himself, and after some fumbling he managed to clasp it behind his neck.
“There” Linda smile kindly, “I think we’re done”
“Good” Jon muttered as he got to his feet “I feel ridiculous-OW!” Both him and Linda felt the sharp nudge pain behind their eyes, as their watches sounded again. Both their text boxes flashed up
DONT FORGET YOUR RINGS
“What the hell!” Jon groused as he pinched the bridge of his nose “I’ve got earrings and a necklace on, why the hell do I need rings too?”
“Not just any rings sweetheart” Linda said slowly, staring at a single spot in the jewellery drawer. Jon followed her gaze and saw a single circular compartment in the dead centre of the organiser. In the middle of the circle sat two rings, one was a simple thick silver coloured band, and the other was thinner, made of the same metal, but had a decent sized diamond in the centre with two smaller ones on either side of it. They were clearly wedding rings. Jon swallowed nervously.
“Oh” he said quietly.
