It took you a moment or two to find it - Randall's handbag being choked full of all kinds of stuff, just as he'd told you. There was his purse, keys, tissues, iPod, deodorant, tampons, perfume, as well as a whole host of different kinds of make up. It being no wonder then that he was always complaining about losing things inside. Women really did seem to go overboard when it came to what stuff they carried around with them, and Randall it seemed was no exception.
Pulling the lipstick out and making sure it was the right color - red, just as he had wanted - you then made your way back towards the bedroom, assuming that he must be dressed by now, seeing as he wanted you to bring it to him. Even so, you decided to give a little knock on the partially opened door, just to be on the safe side (recalling what had happened the last time you'd walking in on him changing).
"I got the lipstick, dude," you said, from the other side of the door.
"Cheers. Just stick it on the vanity will you."
Taking this as an all clear, you stepped into the room, ready to be amazed by the sight of Randall in that long, figure hugging, strapless red dress. Instead what you got, much to your surprise, was the image of Randall facing away from you, in the middle of fastening his bra. The sides of each gigantic mound visible even from behind.
This sight made you stop instantly, having once again, not been prepared for this. Randall's exquisite derriere similarly clad in a slinky little pair of lacy black panties to match the strapless bra.
"I hate these fucking things," he grumbled, turning then to face you. At complete ease with the fact that he was dressed like this in front of you. "They give you no support and my tits pretty much refuse to stay in them." Clearly he was taking about the bra, as you watched him then jostle with all the excess breast meat that was bulging out from the material. Trying to reposition each one within the cups and causing a wonderful display of wobbling and jiggling flesh that made your penis twitch with excitement.
"I'll... I'll bet," you somehow managed to squeak, growing mesmerized by the movement, and feeling rather hot and bothered all of a sudden.
He looked so damn incredible standing there that you couldn't help but grow aroused. Having not experienced such a blatant show of his new sexuality since that night he'd come home drunk, and gotten everything out in the open. It was something you had of course longed to see again ever since, yet at the same time, it still made you feel a little strange that this was your Auntie's body. As well as hugely intimidated by just how damn sexy and incredibly busty your best friend now was.
Shit. Should I even still be standing here? Should I have just put the lipstick down and left? you questioned yourself, being unsure of what exactly you should do, or even how to act normal around him while he was like... like this!
That decision was made for you though, as happy with the placement of his overabundant bosom in the tight, only partially covering bra cups, Randall then said, "Just stick it down over there, dude", indicating to the vanity near by, "Then if you want, you can grab me out some black stockings and a garter belt from the dresser. I'll probably need them in this weather."
The mere mention of the word "stockings" immediately got your brain moving again, it being clear now that Randall had no problem at all with you being there, and actually wanted you to help him get dressed.
"Shu-sure," you told him, pulling your gaze from his chest and quickly setting the lipstick down, moving quickly towards his dresser. Though you knew exactly where the stockings were located from your last little excursion into his underwear drawers, you made out for a moment like you didn't and worked your way from the top down to the bottom. "Third drawer", Randall directed you, having now moved onto blow drying his hair. Opening it up and pulling out a pair, along with a matching garter belt, you asked him if they were alright. To which he answered, "Maybe one of the ones with the lacier tops. Those ones I usually wear for work." It was rather thrilling to note that he was indeed in the habit of wearing them to the office (and it wasn't just a one off occurrence), and while you picked out another pair, you couldn't help but think to yourself, Holy fuck... This is awesome! Is he actually gonna put them on in front of me? Really hoping that he would.
Watching him then as he finished up drying his hair, gave it a quick brush, and then pinning it up with some sort of fancy clasp - as if it was as natural to him as breathing - you were struck by how truly incredibly this really was. Getting to watch a beautiful woman get herself dressed being something that your average, teenage boy was never usually privy to. He just looked so damn classy and elegant, as if he really was the voluptuous 36 year old woman he appeared to be.
It was only when he spoke that the fantasy was shattered. His words having none of the poise or allure that his overtly feminine figure had.
"Right. Give them here, will you," he said, holding out a hand while he double checked his now expertly fashioned hairdo in the mirror. "I've got to get a fucking move on or I'm gonna be late."
Passing him the stockings and garter, you watched with great interest as he put the belt on first of all and fastened it around his thin waist, before leaning down then, raising a foot and stepping into one of the stockings. Pulling it up his gloriously smooth legs in a quick and concise fashion. Your cock was literally throbbing watching as he attached the little straps to the stocking top, repeating the same with the other, his huge breasts threatening to spill out of his bra at any moment as he leaned over. This being, without a doubt, the sexiest most hard on inducing display you'd ever seen in real life, that wasn't on a computer. This wasn't Beth, a sweet and bubbly 16 year old. Nor was it even Allison. This was a gorgeous, impossibly large busted mature woman - and the sister of your own mother - standing before you like some sort of sexy seductress. It was insane!
Finishing sorting out the stockings and giving himself a quick little appraisal in the mirror - allowing you yet another opportunity to ogle his perfect rear (which looked even better somehow with the addition of the stockings and garter belt) - he said, "Okay. Now to see if I actually fit into this dress or not." Heading over to the bed and picking it up.
Stepping into it and pulling it up his lingerie clad body, you had to admit you were slightly disappointed you'd no longer be getting quite the same show. Mind you, it was probably just as well. You weren't exactly sure how much longer you could take looking at him like that, fighting the urge to touch yourself. It almost being like **** in a way. Wishing perhaps that your best friend/Auntie's body didn't turn you on quite so much. Then you might actually be able to function while he was dressed like this, and it wouldn't seem like such a big deal either... For you anyway. Randall seeming completely at ease.
Struggling with the zip at the back, he then looked over at you for assistance and said, "...A little help here, Tim." Either his boobs were just way too big for it to fasten, or it was merely at an awkward angle, but you were of course were happy to oblige. You also couldn't help but take a moment to once again appreciate his big round ass as you stepped behind him, the silky red material of the dress hugging it ever so tightly.
Reaching for the zipper at the small of his back - trying to ignore the sight of both his bra strap and his incredibly alluring silky, smooth back - you began pulling it upwards, finding it to be somewhat of a struggle yourself. "Geeze, this is kinda tight," you grunted, forcing the zipper as best you could.
"Tell me about it!" Randall replied, "You're not the one fucking wearing it."
"I think you might have to breath in a little."
Agreeing with this assessment, he looked back over his shoulder again and instructed, "Alright. On the count of three then", to which you nodded. "One... Two... Three... GO!" Taking as deep a breath as he could, you quickly pulled at the zip, finding it moving with a lot more ease now, as you finally manged to fasten it at the top.
"Fuck me!" Randall loudly gasped, clutching at his stomach. The dress looking like it was on pretty damn tight.
"You okay?" you asked, worried that it might be crushing his internal organs or something.
"No, it's cool. I'm fine. Just takes a moment to get acclimatized is all," he assured you, standing up fully and stretching out his shoulders. Telling you then that, "The Zatanna corset was way worse than this."
Jesus, you thought, The things women have to go through to look nice. Men didn't have to go to half the effort.
Having obviously gotten used to the feeling, he then turned to face you again and asked, "So, what do you think?" His eyes then following your own.
While it may not have been quite as bad as the corset according to Randall, the dress certainly did seem to have a similar effect. Randall's top heavy chest being so tightly packed into it that each breast had been compressed into two perfectly spherical domes, half of which were being **** upwards towards his chin. Christina Hendricks in even her most impressive boob lifting dress couldn't even compete with the amount of cleavage on display right now. It almost... almost looking obscene. Fortunately the rest of the dress fitted perfectly. Clinging tightly to his thin waist and flaring out at the hips. A long slit up the skirt allowing his stocking clad legs room to breathe. The whole outfit screaming sexy and yet sophisticated, and no doubt exactly the kind of thing Randall's boss had been after.
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