Roommate Dress-Up

Summary: Straight guy is feminized by female beauty.

Note 1: This story is dedicated to the real Mike who requested this story.

Note 2: This is a 2020 Halloween Contest Story so please vote.

Note 3: Thanks to Tex Beethoven and Robert for editing this story.

Roommate Dress-Up

"Shit," I sighed, as I saw my outfit for the wedding... I should have guessed she'd expect me to attend it in full feminine mode... but since it was a wedding for one of her closest friends, I'd assumed not.

Black stockings. Black four-inch heels. Black dress. Blonde wig. Fake tits. And that was just the part of my outfit people would see.

Today would be interesting... likely more interesting than I'd prefer. That said, this wouldn't be the first time she'd completely feminized me and taken me out in public... but the other time had been Halloween and if challenged, I could defend going along with it because of the nature of the holiday. Not that I expected to be challenged... except by my own constant anxiety about my self-image.

As I reached for the pink thong, that would also keep in place the butt plug lying next to it on the bed (those made up the other part of the outfit), I flashed back to how I'd first become a complete sissy for my female roommate.

.....

Lauren, my girlfriend of eight months, had gotten accepted for a six-month college exchange in France... which was awesome, and an amazing opportunity for her, but it was a bit of a disaster for me.

We'd moved into an apartment together just days before she received the surprise call saying she'd been accepted... which was a week after the announcement was supposed to have been made, so we'd assumed she hadn't been accepted and thus had gone ahead and signed the lease for the apartment we'd been planning to share when college resumed in the fall. The lease was unbreakable, of course.

But since I'd be away for most of the summer doing an internship in Los Angeles, at least we had a few months before we (but now I) were scheduled to move in, and Lauren was able to arrange a roommate for me while she was away, as I couldn't afford to stay in the apartment on my own.

She told me it was a girl she'd struck up a casual friendship with from her psychology class, and that I'd love her.

I thought it strange she'd choose a female for me to room with... but she trusted me, and I trusted her. So no big deal.

The summer over, my new roommate arrived the first week of school, and I couldn't help gasping.

For one, she was ridiculously hot.

For two, she was a girl I'd gone on a few dates with before meeting my girlfriend... but we'd never really clicked. I'd felt her up and she'd felt me up in my car, but that was it... I don't think my five-inch penis had impressed her overmuch, because that was our last date once she'd felt, hadn't even seen, what was inside my pants.

Fuck!

"Hi, Mike," she smiled as she entered the apartment.

"Joanne? You knew you were moving in with me?" I asked.

"Yeah," she shrugged like it wasn't a big deal

"But we dated," I pointed out. "And then we didn't."

"Barely," she scoffed. "It's not like we fucked or anything. And we agreed to remain friends."

"True, but following that agreement, I haven't seen you since you dumped me."

"Look. You have your girlfriend Lauren and I have boyfriends," she brushed it off. "We're just sharing an apartment." I noticed she used the term 'boyfriends' plural... which was odd, but I didn't question it.

"Yeah, fine," I said, figuring if I hadn't gotten to fuck her when we'd dated so briefly, it was unlikely either of us would be tempted, hot as she was. And since I was in a committed relationship with my absent girlfriend Lauren, just as Joanne had pointed out, no big deal.

Campus life got going, and other than Joanne always wearing pantyhose, my sexual kryptonite, which she knew about, we became friends. Not close ones, but definitely cordial.

She brought home a different guy every couple of days, and a couple girls too, and even though of course we had separate bedrooms, I couldn't help but hear her having at it, as she got very animated and nasty whenever she was fucked... or when she apparently was the one doing the fucking, since more than once I heard a girl begging for her cock.

I snooped around in her room after her first girl-on-girl encounter, and I found a strap-on, lube for both vaginal and anal entry, handcuffs, and a collection of vibrators and butt plugs. For a girl who looked pretty sweet and innocent on the outside, she was a total freak once she got going, something my ears had already informed me.

I also found her sheer pantyhose and sexy panties, and a week or so later, I got daring enough to sneak her soiled underwear and pantyhose out of her laundry hamper, and I took to wearing them sometimes when she wasn't home.

I would stroke my hands up and down my silky sheer legs, curious why not every woman would want to wear such sexy, silky pantyhose on every occasion she could. It was so unfair that women were permitted to wear these garments every day and chose not to, while men couldn't wear them without being judged and stereotyped as gay, even though many of us would if given the opportunity (at least if people posting on certain internet forums are being honest).

I'd eventually spend time rubbing myself to orgasm as I watched videos online. My choice of videos began with guys fucking girls (the girls usually in nylon), until I discovered a new (to me) sexual niche of videos called hypno-sissy sessions. These were typically brief, rapidly-changing sex scenes of women sucking cock or getting fucked, accompanied by the soundtrack of a sensual female narrator describing to the viewer/listener how fervently he desired to be the woman. (The target audience was obviously men.) I couldn't explain my fascination, since I didn't have any interest in sucking a cock, and I certainly didn't ever want to be ass fucked, but these videos got me so horny that I'd shoot big loads of cum into Joanne's panties, which I'd be wearing, and would even leak a little of it into her pantyhose.

I'd then return her panties and pantyhose to Joanne's laundry hamper and she'd be none the wiser... or at least that's what I thought at the time.

I'd done this a few times prior to my birthday... when with Lauren gone, Joanne and I spent the evening together in our apartment, drinking rather heavily ... she'd even surprised me by quite sweetly buying me a birthday cake.

At one point in the evening we were both quite drunk, and I was undoubtably staring at her legs and feet in her black nylons a little, or perhaps too much at her toenails (they were freshy painted red), when she asked out of the blue, "Mike, you really love women's nylons, don't you?"

"You know that from when we dated," I deflected, belatedly looking away from her feet, and up to her eyes.

"Yes, but you really, really, really like my nylons," she clarified, stressing a couple of the words.

"You do look good in them," I admitted, unable not to indulge in another glance at her legs. Truth was, she was almost six feet tall, which was a couple inches taller than I was, and thus had amazingly long, beautiful legs.

"That's true, I do," she adlibbed a couplet (but didn't end the scene with it), sexily rubbing one foot up along her other leg.

After a brief pause, while I couldn't help but watch her moving foot, she asked, totally surprising me, "Do you particularly like them while you're wearing my used panties and pantyhose?"

"P-p-pardon?" I stammered, which only acknowledged my guilt.

"You heard me," she said, as she slid her other foot up and down her other leg, which again I couldn't help but watch in fascination.

"I... um..." I said, embarrassed that she knew my secret, but also completely distracted by her current display of cute nylon feet and toes... which she obviously knew was drawing me in.

"Your nylon fetish is even an obsession, isn't it?" she asked, wiggling her toes at me.

"Not an obsession, just kind of a kink," I denied, although obsession was likely the better word. I would always perv over a girl in nylons over one with a big pair of tits or a great ass, no matter how amazing it was.

"I think obsession is the perfect word," she said, swinging her feet onto my lap and directly onto my very hard cock. "Massage these for me." It wasn't a request; very definitely an order.

"Lauren is not only my girlfriend, but your friend," I pointed out even as my cock raged, and it actually flinched directly beneath her feet, meaning she'd have had to feel it.

"I'm not going to fuck you," she said. "It's just a massage... a platonic... albeit nylon-clad... massage, although to be totally honest, it will likely turn you on and get you all frustrated."

"Okay," I said, rationalizing that she was right... you could go out and pay for a massage, and if it was a reputable parlour it was completely professional and platonic, even if I left there feeling sexually frustrated. Plus, it had always been pretty obvious this time around she wasn't into me sexually... given her constant parade of really good looking men and occasional cute girls through our apartment.

"Think of it as your birthday present," she said, as my hands touched down onto her soft, silky feet.

"Okay," I repeated, although still unable to control my cock from flinching as I began fondling... I mean massaging... a very nice birthday present.

"So back to my original question," she resumed, "Do you enjoy wearing my panties and pantyhose?"

"Yeah," I admitted, figuring since she already knew, there was nothing I could say to convince her otherwise.

"Exactly what turns you on about it?"

"I don't know," I temporized, rather distracted by her silky sheer hosiery right now, and not wishing to admit to her or anyone that I secretly fantasized about becoming completely feminized.

"Oh, I think you know very well."

"Okay, I guess. But it's too embarrassing to talk about."

"Look Mike," she said. "We're friends, and I'm certain the walls in this apartment are thin enough that you know some of my intimate secrets. You've probably even sorted through my kinky toy collection, although I've never detected your ever using any of it. So given all that blackmail-worthy knowledge you have (and I'm not at all worried you'd ever use it against me without genuine cause, don't worry), you can tell me anything at all, completely safe in the knowledge that I'd never be so stupid as to out you about anything you might share with me."

"Share something with me first," I bargained, hoping to learn something hot and crazy.

"Okay, I can do that, no problem. And each time you share a fantasy or secret, so will I," she offered. "I'll even go first: I really like a nice, fat dick up my ass when I'm drunk."

"And you're well past tipsy right now," I pointed out.

"Yeah, you're right. A couple more drinks, and I'll likely be texting one of my fuck boys, and you'll be able to listen through these aforementioned thin walls to my being sodomized by a big cock."

My cock flinched from that visual and her nasty talk.

"I see you like that idea," she said, "are you picturing me getting ass fucked wearing nothing but my stockings right now?" obviously feeling my cock flinch underneath her feet.

"What guy wouldn't?" I asked, sure that a hundred and five percent of all men would get excited from that nasty visual.

"True," she said. "I do have an amazing ass."

"Yes, you do," I agreed.

"Hey, I'm a friend of your girlfriend, remember?" she teased. "You even said so."

"I can look... and even drool on occasion," I joked. "I just can't touch."

"No, you can't touch this," she sang the MC Hammer song while playfully spanking the ass in question.

"Please stop doing that," I asked, although I was laughing.

"Okay. But don't you stop," she scolded, as I'd paused from massaging her foot even though the foot was still cradled in my hands.

"I could do this all night," I admitted, really enjoying the feel of her silky soles.

"Now we've broken the ice, you'll be doing this regularly," she informed me as she removed her foot from my grasp, replacing it with her so far neglected other foot.

"Anytime," I agreed, knowing there was no way I could resist an opportunity to touch her nylon-clad feet.

"So it's your turn; what's a favourite fantasy of yours?" she asked, bringing us back on track after our foot play distraction.

"Wow! Where do I start?" I joked.

"With your wearing my panties and pantyhose," she said, swinging the conversation once again back to the worst possible topic. "Tell me about that."

"Well, I...." I started, but then stopped, too uncomfortable to continue.

"Tell me... Right... Now," she ordered, her tone suddenly authoritative.

"Well... I've always liked the feel of silky panties and sheer pantyhose, and so I was curious what it would feel like to try yours on," I blurted out quickly and sheepishly.

"That was brave to tell me, thanks for sharing. And you'd never tried wearing them before borrowing mine?"

"No," I admitted, "I've been curious about it for quite some time, but I always resisted the temptation, because it's considered unmanly."

"Then why mine?" she asked, as I continued massaging her nylon-clad foot... my cock still rock-hard (probably obviously so) beneath her resting feet.

"I don't know," I said honestly, then added, "I guess I figured you wore them so often, you wouldn't notice."

"I noticed the cum stains in my panties right away," she pointed out. "If you'd wished to remain an undetected pervert, you would've had to wash and dry them afterwards, but then they'd be noticeably clean and unworn, so you'd still be out of luck."

"Oh," I said, feeling guilty for leaving my cum in them.

"What were you masturbating about?"

"It's too embarrassing to say," I objected.

"Look, everything is on the table here," she said. "No kink is judged. For example, I like wielding a strap-on."

"Oh my," I said, a visual of her fucking my girlfriend Lauren popping into my head... which made me feel guilty.

She then added, her tone sultry sweet, "And I fuck both girls and boys."

"Oh my," I repeated, not having expected that.

"What?" she asked. "It's 2020, and guys can take it up the ass just as well as girls can."

"I don't know about that," I cringed, having been a little curious what it might feel like to have a real cock in my mouth after watching so many cock sucking sissy videos, but I hadn't even contemplated taking one in the ass.

"Most guys consider themselves too manly to let a girl take their asshole," she said, "but the ones that do discover how amazing a prostate orgasm can be."

"I can't imagine," I said, wondering if she'd fucked any of the guys she'd invited over... all the ones I'd seen had appeared very manly.

"I bet you'd moan like a bitch in heat if I ever pounded that cute backdoor of yours," she said wickedly, pressing her foot down on my cock.

"Oooooh," I moaned, which wasn't because I fancied getting ass fucked, just because of the extra pressure on my cock... although her nasty tongue was also enhancing the pulsing in my cock... and further, I noticed she'd called my ass cute.

"Most guys squeal like moaning sluts once I'm pounding their assholes," she shared wickedly, clearly enjoying the stunned look in my eyes. She added, "You can't tell me you've never once wondered what it would be like to take something in that cute ass of yours."

"It isn't high on my list," I said.

"That's not a denial," she appraised, adding, "So what's your biggest fantasy... besides fucking my cute little hairless pussy? Which, since you'd like to ask, is sopping wet right now, but for various reasons you can't touch it."

"Thanks for the inappropriate visual. But my biggest fantasy is fucking Lauren."

"Yeah, yeah, you love her eternally and will always remain faithful, yadda, yadda, yadda," she said, waving her hand around dismissively. "But what's your biggest secret fantasy?"

"My biggest?"

"Yes, your biggest, most secret fantasy," she said. "The one you'd dive into in a heartbeat if nobody would judge you for it."

"Well... it's even gayer than wearing your panties and pantyhose."

"That's a start, but say on," she encouraged. "Remember, between the two of us, there's no judging."

"I'd want to be completely femininized," I blurted out, feeling oddly liberated just to say it out loud... I'd never once told this to a single soul. And then I couldn't help cringing, just knowing she'd be horrified!

But she wasn't... at all! "You would make a cute girl," was all she said as she looked me over.

"I would?"

"Yeah, you're slender enough that your body would look hot once we gave you some tits, and your high cheek bones would also help."

I decided just to say it all. "Well since you're not condemning me so far, what I'd really like is to be dolled up to the full nines. Sexy lingerie, with silky nylons of course, a lovely dress, high heels, glamourous make-up and long hair."

"Mmmmmmmm," she said, obviously pondering this reveal.

"Am I freaking you out?" I asked.

"Actually, you have me intrigued," she said thoughtfully, as I continued massaging her feet.

"I do?"

"Yes, I've done a lot of kinky shit in my life," she said. "But feminizing a guy? I haven't explored that yet."

"Oh," I said, both excited and nervous about where this might go. I then asked, still testing the waters, "Like what kind of kinky shit?"

"God, where should I start? I've fisted my mom's best friend, was gangbanged on prom night, I golden showered my high school English teacher Mrs. Walker, some of it even going in her mouth while her daughter Carolyn filmed it, pegged my next-door neighbor while his wife was gardening in the backyard, turned a straight church mom into a compete lesbian, and even made her eat me out in the church bathroom while her husband the minister babbled on and on about resisting sins of the flesh," she listed, before pausing to take a deep breath and smiling, "just to name a few."

"Wow!" I said, my cock flinching a few times during that litany of taboo kinks.

"But the idea of turning you into a hot, fuckable woman is intriguing," she said, once again looking me over.

"There's more to it," I said, now feeling I could tell her anything, since after all I'd said already she wasn't judging me.

"Glad to hear it; go on."

"Well," I said, suddenly apprehensive about actually revealing the next bit, even though I was the one who'd opened the door. "I sometimes imagine a woman taking complete charge of me, and training me into a completely feminized woman."

"Interesting," she said. After a pause, she added, "I haven't ever done that precisely, but I did train my roommate to be a completely submissive lesbian slut over the last semester before summer."

"Really?" I asked, before asking, remembering her shy, nerdy roommate, "You mean Amy?"

"Yeah," she smiled, reminiscing, "I trained her to crawl between my legs and lick me at the snap of my fingers, or lick any of my friends for that matter; and to take a strap-on in all of her holes; and never to orgasm except with my permission."

"No way... Amy?" I repeated.

"Yeah, hiding underneath her shy exterior was a natural submissive," she said. "Not so hidden anymore, of course. I'd handcuff her to her bed and leave her there with a vibrator in her pussy and a butt plug in her ass for hours; I had her wear a collar with a leash whenever I had guests, and she'd even eat their assholes when ordered."

"Wow, I want to be treated like that!" I let slip before realizing I'd even said it. I tried ineffectively to cover myself by stammering, "I-I-I mean, wow. Just wow, and please forget the rest."