I can't believe I'm actually doing this, you thought as you closed the door, turning then to face the mirror. You'd never had even the slightest desire to wear women's clothes before, not even when you were younger and Randall would joke around with his step-mother's bra, so looking down at the delicate female underwear clutched tightly in your hand, all you could think about was how much of a fool you were about to look. Still, it was only for the rest of the night (at most), hopefully if you did this now, you'd get it out of the way, Randall would get to have his fun and there'd be no more surprises. At least you hoped there wouldn't be. Lets just get this over with then...
Placing the clothes down on the sink and letting out a sigh, you pulled your t-shirt over your head and quickly removed your jeans. Picking up the panties (which you had to admit were really hot), you realized there was no way you could wear them over your boxer shorts - there really being very little to the actual material. While not quite a thong, they were pretty much verging on it, so it was with great **** that you removed your boxers and pulled the lacy underwear up your legs.
Jesus. you groaned, looking back in the mirror, your junk pretty much bulging from the material now, leaving little to the imagination and looking pretty darn ridiculous. He is such an asshole!
Moving quickly onto the next item, the 'Cutie-Pie' top, you slipped that on as well, finding that it didn't even manage to cover your belly. With his massive breasts you doubted it even fitted Randall, but then, even with that, you were certain he'd look a hell of a lot better in it than you did right now. Girls and tight crop tops were a perfect combinations. Guys... not so much.
Looking at what was next - the garter belt and stockings - you kicked off your socks and grabbed the lacy slip of material, stepping into it and pulling it up over the panties, fitting it around your waist. It was kind of funny, garter belts and lingerie had always been a big kink of yours when you'd been flicking through your mom's clothing catalogs, or looking up porn Online, and this, you realized, was actually the first garter belt you'd ever actually seen for real. You'd certainly never imagined you'd be the one modeling it back then. I'd much rather see this on Randall, you mused, picturing him dressed up for you again, beckoning you between his legs, wishing you could remember a little more from the night before when he had actually been wearing this kind of stuff...
This line of thinking however, resulted in you starting to get a bit of a boner. Mixed with the slinky little panties you were currently wearing, it wasn't exactly a good look, and your penis was quickly finding it harder and harder to breath. Shit!
It took you a minute, but thankfully you managed to tame your rising semi with thoughts of your crabby old chemistry teacher, Mrs. Naismith. She did have some use it seemed after all, and boy did you need her tonight. You might currently be putting on women's clothes for your best friend's amusement, but so far today you've done and seen things that could keep your hard for weeks. This was admittedly a small price to play for getting to spend a weekend with your fantasy woman and her mind blowingly awesome body. You could only pray to God that the mood takes him again and more sex would be included later on.
With the garter belt on then, you quickly pulled on the stocking, fitting the four hanging little clips to each of the tops, before returning to the mirror again to see the finished article. "Fuck you, Randall. Fuck you." you said as you stared at your reflection, unable to stop yourself from letting out a laugh. The sight was just as hilariously awful as you'd initially thought. With your hairy legs showing through the stockings and the camisole and panties stretched to the limit around your body, you really did look like a transvestite who'd got dressed in the dark. "Boy is he gonna get a kick out of this." You could picture the look on his face already. In fact, he was probably already out there, laughing his ass off in front of the bathroom door.
Seeing no point in delaying the inevitable, you turned and reached for the door, announcing as you did, "Alright. Here you go. You happy now?"
Instead of finding him rolling around on the floor, what greeted you as you stepped back into the bedroom was the flash of his digital camera - Randall having obviously retrieved it to take a few snaps.
"Oh yes. Yeeees! You look simply divine darling!" he laughed as he stood there taking picture after picture, aping the sleazy photographer accent you yourself had tried earlier. "Work it for me! Let me see those sexy gams!"
"Come on, dude! What the fuck are you doing?" you squealed, grabbing for the camera. It was bad enough you were actually dressed like this, you didn't want photographic evidence of it too.
Randall however continued snapping away, avoiding your grasping hands and continuing his pretense. "That's it, baby. But sexier. We need more sexy!"
"Give me the fucking camera, dude! Give it to me!"
"What... No way!" he protested, jumping backwards onto the bed, telling you as he did that "You look too damn good not be photographed!" (making no attempt in the slightest to even try and keep a straight face).
"That's not fair, Randall. You've already got me dressed up like an idiot."
"And?" he quickly countered, lowering the camera, "You took pictures of me remember." That was hardly comparable, seeing as that was his idea in the first place and he looked incredible dressed up as both Lara Croft and in that sorry excuse for a swimsuit. "Besides, that top, those panties... they... they really show off your figure!"
"Screw you!" you reluctantly sniggered as he fell into yet another fit of giggles, finding his laughter actually kind of infectious. "We can't all look like a walking wet dream you know."
"You look so fucking gay, dude. It's hilarious!"
"Yeah, well if you're quite done laughing your ass off, can I get changed back now?" It kind of felt like you'd had enough punishment already for one day.
Randall wasn't going to let you off that easy unfortunately. "No way!" he said, putting the camera down on the bed (while you made a mental note to delete those photos as soon as humanly possible) and stepping back off it. "That's your uniform. You don't get to take it off till the end of the night, as per our agreement." Then, as if suddenly remembering something, he said, "Which uh, which reminds me. It's not quite complete", skipping joyfully over towards his closet and pulling something out. "You need these to go with it."
What he was holding was a pair of shiny black pumps, with what looked to be at least a 4 inch heel.
"You've got to be kidding me?!" you balked as he presented them to you, this definitely being a step too far. "I'm not wearing those. I'll break my freaking neck!"
"Tim, they're only heels. Once you get used to wearing them they're really not that bad." hel told you, playing this whole thing down again once more as he gestured for you to take them. "Besides, I want you to see what I have to put up with everyday."
"Oh so now you're taking it out on me? Just because you're a woman and Miss. Card's shoe collection is mostly made up of heels?" You hardly saw how that was your fault. You hadn't **** him to wear them or anything. Why were you then paying the price for his disgruntlement?
Apparently you weren't, as Randall replied with a grin, "No. I just wanna see if you fall over or not." It simply being yet another opportunity to humiliate you.
"You're such a dick, you know that." you told him, taking the shoes, aware that you weren't going to get out of this one either. I'm totally gonna get him back for this one day.
"Says Captain bulge over there." he chuckled, pointing towards your inadequately covered crotch as you bent down to put them on. "I think you were right though, that stuff definitely does look better on me."
Ignoring your friend as he continued to laugh at your attire, you struggled to actually get your feet into the shoes (Miss. Card clearly being a lot smaller size than you were). After a minute or two you eventually managed, and standing up to show him the result, you asked, "Okay? Happy now?" feeling your legs start to wobble slightly as you did.
Your torment wasn't done quite yet however, as Randall then informed you that "I wanna see you strut, butler boy. Come on. STRUT!" barking at you like some sort of Army drill Sargent.
And so reluctantly you did...or at least tried, falling about the place and tripping over the heels for the next several minutes, much to Randall's continued amusement. He was clearly having a blast seeing the shoe (literally) on the other foot, telling you that "See. It's not as easy as it looks, is it?". Not that it was exactly fair mind you. You were a dude. The pumps didn't actually fit. Plus, you didn't have whatever weird muscle memory thing he seemed to have left over from Miss. Card. He could do all this girly shit without thinking all that much. You were just a doofus who'd lost a bet, stumbling around aimlessly while dressed in women's clothes. It was hardly a fair comparison.
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