The Man In The Red Dress

"This is the one." She handed me her phone.

"You've not had a date so far?"

She shook her head. "We matched a couple of weeks ago and have been chatting since, but because of work schedules we can't get together until this weekend. The unusual name made tracking down the corresponding Instagram profile easy, so I poked around of course -"

"Of course."

"- and that's when I found this."

I could see why she was attracted. My eye was drawn to the red bandage dress, tight and flattering, taut across a slim body. Blonde hair tumbled down around the neck line, framing a perfectly made-up face, all smoky eyes and lips full of promise pouting in a playful 'O'. Where the almost-too-short dress ended a pair of long, slender legs emerged, enhanced by black fishnet stockings and adorned by black patent stilettos. The illusion would have been perfect had thick, lush black hairs not poked through the coarse weave of the fishnets.

"I'm assuming this wasn't his Tinder profile pic then."

"No! Although I probably still would have swiped right if it had been."

I indicated that I understood, and I did. I knew of her fascination with drag queens and gender roles and all manner of pretty young things. It was plain that her latest crush fell into this category no matter what or who he was dressing as. He was, in short, quite a beauty.

I handed her phone back as she continued. "According to the caption, it was for someone's birthday. They went on a bar crawl and then back to a house party which is where this picture was taken."

"Wow, so he looks that good at the end of the night? Imagine-"

"I know!"

She looked at the photo. I knew there was a catch, so we waited in a comfortable silence until she was ready to tell me.

"I was going to tell him that I wasn't bothered about meeting up. There was no spark when we chatted, he doesn't live all that close, he has a job with weird shifts. He was actually quite nice to chat with in a distinctly non-dangerous sense. Good looking, very good looking obviously, but lacking... edge. I couldn't see it working out."

"But now you feel differently?"

"But now I'm not sure, that's all."

"You're attracted to him dressed like this." No need to answer that. She still didn't look up. "There's something else?"

"He made a wisecrack that I didn't find amusing about women in the kitchen. He was just trying to be funny but frankly it came across as being a dick. He's apologised, like, a million times. And he keeps saying, 'if there's anything I can do to make it up...'" and in that moment I understood why we were having this conversation.

"You want to take him up on that."

"Yep," she sighed, wistfully. "To take him up on that, and maybe to make him reconsider a woman's place." She composed herself, sipped her drink. But now there was a hint of a smile, barely perceptible unless you knew her well. I thought I knew the answer but I asked her anyway.

"And what is it that I'm supposed to do here?"

"You're the biggest pervert I know," she grinned. Understood. I smiled back.

"I prefer to think of myself as an auteur, but whatever, I'm taking that as a compliment. What are we trying to accomplish here?" One raised eyebrow said it all. "Apart from that!"

"I get the impression he might be a game player," she said simply. "I want to checkmate in the fewest moves."

As though my subconscious had already skipped forward to this point I could feel the first stirring of a plan. "Does he have the usual array of basic hot selfies?"

"Not lots, but a couple. They're the type of papped, off-guard selfie that someone else took. Why?"

"Follow him," I said, "and like the picture immediately. Don't like anything else, just that." She grinned, her eyes brightening.

"And... done." she said. "What next?"

"He's going to notice that you liked that particular pic. He's also going to ask about a date. We're going to give him the chance of the latter by repeating the former."

"I like it!", she laughed, topping up our glasses. "Go on!"

"That's the plan. You need to be completely clear about it. You'll agree to a date, to allow him to make amends, as long as he agrees to go out in drag. We have to do something about those legs though."

"Agreed. But what?"

"Does he have his own place?" She nodded. I paused. "Okay. Don't tell him about the plan up front. Agree to a drink at his place and tell him you'll go round early, like half seven early. When you turn up at his, you'll be looking your absolute hottest. You'll have a bag with you, but don't tell him what's in it. Tell him that you've decided you'd like him to take you out instead. Dressed as you are, he'll agree immediately. That's when you tell him about the catch. Tell him you picked an outfit for him. Then, take it out of the bag."

"I pick his outfit?"

"The whole thing. Dress, underwear, heels, stockings, make-up. Think you can rustle up a wig from somewhere?"

"Sure, but isn't that a bit weird though, going out with a guy wearing my clothes?"

"As opposed to going out with a guy wearing another woman's clothes?"

"Point taken."

"Tell him you like his drag pic on Instagram, and you want a private viewing. Tell him that's the one condition of the date. And then when he's over the shock, tell him that he has to do something about the legs. The hair has to go."

"He's going to shave his legs?"

"He's going to shave the whole damn thing. From the cleavage you can see in that shot, it doesn't look like he has a hairy chest, so it's just the waist down." Her brow furrowed as the full import of that sank in.

"Not just the legs?"

"Back, sack and crack, the whole works. And if he says no, you can either threaten to walk, or, you know... you can be persuasive. The key thing is that once he's agreed, you have to make sure he does it properly. That's why you need to watch. And this is key; this is about establishing who is in control. Not only is he going to go out looking as feminine as possible, he's going to do it on your terms. So when he agrees, tell him - don't ask - that you're going to watch."

"What if he..."

"If he can't control himself, that's his problem. It's not like he's going to lather himself into a frenzy anyway. Sit in the bathroom while he showers. Pay close attention, don't read a magazine or play on your phone. The main thing is, he's naked in front of you, shaving himself, because they are your terms and unless they're met, there's no date."

"Then why-"

"Just so he knows who is in charge." I left her in silence to take it in.

"If he gets an erection, ignore it. Once he says he's done shaving, check. Make him turn round. Make him bend over, stand with his legs apart. Tell him to lift his cock and balls so you can see under and all around them, for a little bit too long, but look at them in a detached, medical way. Then find fault, somewhere."

"I'd be surprised if he could shave his legs right time anyway," she harrumphed.

"I'm quite sure I wouldn't know but I'll take your word for it. If you need to touch him to see how smooth it is, do it asexually, that's the main thing. He can find it sexual, but you can't show him that you think it is."

"Okay. So he shaves, I send him back in. Then what?"

"Then you transform him. Get him into the dress and-"

"Makeup first!"

"Really? Okay-"

"If you dress first you'll get makeup on your clothes." That gave me a thought.

"So - get into lingerie first?" She nodded. "Right. Even better. Once he's out of the shower, let him dry and then take the towel off him. When he's stood naked in front of you, make a show of going into your bag and showing him the lingerie that you've selected for him. Tell him all about it. Tell him how the material feels against your skin. Talk about the way that wearing it makes you feel. Show him how exquisite it is, and make him touch it. Tell him how expensive it is."

"Then, dress him. Don't leave him to figure it out himself, help him with everything. While you're doing that, make sure there are lots of 'accidental' touches. Smooth the material down, run your fingers around hems, make sure straps aren't twisted. Make sure he... make sure he's comfortable inside the knickers. Do you know what you might make him wear?"

"I have a black set with some shorties. He should be comfortable in those."

"No... I don't mean 'comfortable' so much as 'barely fits inside'."

"A thong then?"

"Yes, I think so. He should be able to get it on and wear it, but any sort of erection should be very awkward for him."

"I think a thong will do that."

"Good. Just that and bra?"

"We can go as far as you like. I was definitely going with thigh highs, but we could go with suspender belt, corset, waspie, whatever you think?"

"No, bra, thong and thigh highs are fine. Make sure that the dress is just short enough to keep revealing the leg bands. When you're out, keep an eye out for his dress riding up and tell him off for it. But we're getting ahead of ourselves. Once he's dressed, tell him you're going to do his makeup. Tell him why he can't get dressed yet, and then he'll understand why you need to take your dress off too."

"What?"

"You said yourself, don't want to get makeup on your clothes. So, once he's into his underwear, you strip down to yours. He has the humiliation of being in your underwear whilst trying not to be aroused by you being in yours. Make it slow, but not too slow. It's part of the seduction, but don't make it look like you think so. While you undress, tell him what's going to happen. Tell him about the colours, and the process, and the different things you're going to use, and what they do. Explain why you picked the colours and why they will suit him."

"I have a colour scheme in mind, actually. I think he'll look better as a brunette, and I have the perfect red lipstick in mind."

"Good. When you're done with him, I should find him attractive. Think he'll need lessons in walking in heels?"

"No idea. At least we know he's spent one evening in them, so that's something. I think I know where I'm going to take him. We'll take a taxi there."

"When you're out, you're just girlfriends. If it looks like anyone has realised he's in drag, ignore it. Try not to let him see. If he makes any comments, starts to doubt himself, you can start paying him compliments about how good he looks, but not until he has at least one or two drinks inside him. Once he's a little more settled, you can start flirting with him. Touch him a lot, especially on the legs--"

"I think I have flirting figured out, thank you!"

"Sorry! Was there anything we didn't think of yet?"

"Yes, just one thing..."

"What?"

"I really wanted you to be here to join in when I bring him home afterwards. Can we send the kids to your mum's for the weekend?"