Roommate Dress-Up

"Hey," I said, a little sheepish.

"Man, you must be sweating in those pantyhose, especially with the jeans on top of them," she observed, today being unseasonably hot for late October.

"Yeah, they are a little sweaty," I agreed.

"Well, soon you'll be naked."

"Usually I'd love to hear those words," I joked.

"Oh, you'll love the sexy new you as well," she said, taking possession of my hand and leading me into the salon... I noticed there was a cocktail lounge attached to it.

"This may be going too far," I worried to almost no one as she led me inside, released my hand, and whispering so I couldn't hear, chatted up a very pretty Japanese girl at the front desk.

The girl looked at me and nodded a few times, as Joanne spoke to her.

"Come with me, Michaela," the Japanese woman said, making my cheeks burn red.

"That's your name whenever we're out together," Joanne informed me, noticing my surprised look.

'Yes, Mistress Jojo," I agreed sheepishly, guessing that was also required now, as I followed the short, slender woman, glad there was no one else around to hear my humiliating response.

"Good sissy," she approved, "well done," before adding, "and have fun."

"I will, I think," I said, unsure what else to say.

I was led into a room with a tall bed in it, about waist high, and the Japanese woman instructed politely, "Please get completely naked and lie over there on your front, Michaela."

"Completely?" I asked, that seeming a bit much.

"Completely," she confirmed. "We are waxing your legs, your ass, and all around your penis." I found it rather impressive she could say something I found so embarrassing with such professional detachment.

"Oh," I said, that sounding even more extreme than I'd expected, although I had noticed most guys in porn are completely shaved, and it appeared to make their cocks look bigger... an advantage I could definitely use.

"Shell will be with you in a couple of minutes," she said, before leaving me alone to get undressed. Completely.

"Okay," I acknowledged, and then got undressed, finding the sweetness of the aromatic oil diffusers quite relaxing, and the room quite warm.

Once I was naked, stuffing the panties and pantyhose inside my jeans so they weren't apparent, I lay face down on the bed, which was quite soft, and draped the sheet, which was surprisingly bamboo and silky soft, like my parents' sheets (but too pricey for my bank account) over my body.

A moment later there was a knock at the door and a voice sang out, "Are you ready, Michaela?"

"Yes," I answered, still finding it odd to be called a feminized version of my regular name.

A black woman, quite large, dressed all in white: nylons, and skirt and blouse, walked in and greeted, "Well, aren't you a cute thang."

"Thanks, ma'am," I responded, unsure how to take what I think was meant as a compliment.

"Jojo says we're completely feminizing you," she said, as she casually pulled the sheet right off of me.

"Completely? I asked, wondering if there was even more in store for me than just the extensive waxing I'd already been told about.

"Well, we're not performing surgery or giving you any hormone treatments, but we are making you the belle of the ball, Sugar," she said brightly, as she came over to me and began applying warm wax to the back of my legs.

"Jojo took my off-handed comment a little further than I'd intended," I pointed out, trying to hang onto a bit of my manhood, even as I was being waxed.

"Don't you mean to say Mistress Jojo?" she scolded archly.

"Yes, sorry ma'am, it's Mistress Jojo," I corrected myself, shocked she knew I was supposed to refer to her that way.

"She's brought a few pets here before for makeovers," she said, "but you're the first boy."

"I can't believe I'm here myself," I said, as she applied some paper stuff to my legs.

"Well, you do have a great pair of legs, and a cute little perky white ass," she said, her small talk rather more personal than I was comfortable with.

I was about to say thank you, when she ripped off a long strip of the waxed paper. "Thann.... FUCKING HELL!"

I probably needn't mention that pain was suddenly burning through me like she'd just seared me with a blow torch!

"I think it's always better if you don't know it's coming," she said mildly.

I began to agree, when without warning she did it again, "Yes, I, oh my fucking God!!" as two more strips were yanked away.

"Sorry, Darling," she said with a soft laugh that revealed she was far more amused than sorry.

"It's okayyyyyyyy!!!" I screamed as the last of the waxed paper was ripped from my mutilated and bloody body. (It wasn't really, but man oh man, did it feel like it!)

She said, as she went to grab something, "Halfway done already."

"Only half? I think you may kill me," I said, my legs still hemorrhaging like crazy. (Again, not really.)

"What doesn't kill you makes you stronger," she shrugged before adding, "this is just one of the many hardships of being a woman. Or in your case, of becoming one."

"I guess," I agreed, wondering how many times women had to do this in their lives to look good for a man. "And they say childbirth is even worse? Suddenly women everywhere have my profound sympathy."

"Plus," she said, as she flipped me onto my back, "at least you don't have to carry a baby inside of you for nine months."

I nodded, as I was suddenly gazing up at the large breasted black woman with a heavy southern accent, "Thank God. I don't do pain very well."

"Well, if you're going to be a beautiful bombshell, you have to do the work that goes with it," she said, as she began waxing the front of my legs, which, thank God, had a lot less hair on them.

"Do many men come in here for waxing?"

"Sure," she nodded.

"That makes me feel better," I said.

"Most are strippers though, since it's part of the stripper allure," she said, deflating me as quickly as she'd inflated me.

"Oh."

"Other men do just their Johnson area so they'll look bigger," she continued.

"Does it work?" I asked.

"Well, it doesn't make your dick any bigger, Darlin'," she chuckled wholeheartedly, "but it definitely gives the illusion that it is."

"Nice," I said, anything to make me look bigger than I was.

"It will do that," she said, before adding, "although that isn't the purpose in your little clitty's case."

Her too? Damn, I wish people would stop calling it that! But not revealing my thoughts, "I know," I said sheepishly, as she stuck the waxed paper to my legs.

"But don't worry, I'll have you looking so fuckable, you'll be able to choose whomever you want," she said.

I clarified, "I'm not interested in that."

"That's what they all say at first," she said, before yanking waxed paper off both of my legs.

"Oh, bloody hell!!" I screamed, this hurting just as much as the back of my legs.

"Almost done," she assured me, then yanked off the last two strips.

"Fuck! JUST GO AHEAD AND KILL ME!!" I screamed again, hoping this room was soundproof.

"All done with the painful bit. You actually took it pretty well," she said kinda sorta sympathetically, as she went and grabbed some lotion and began generously slathering my legs with it... it instantly cooling the fire burning both outside and inside my legs.

I didn't say anything, just basked in the sudden soothing sensations.

"Now spread your legs wide, and don't move," she said a minute later, as I opened my eyes and saw she had a straight razor in her hand. You know, the old fashioned kind like Sweeny Todd used.

"Those are words no man in the history of mankind has ever wanted to hear," I joked.

"Funnnnnnnneeeee!!" she laughed uncontrollably hard, which I realized was a mistake, with my penis so close to her literally razor-sharp blade.

"I'll be quiet now," I said, as I watched her advance her potentially lethal weapon to my groin area and begin cutting and trimming.

I closed my eyes, finding watching her in action a little too stressful, and just trusted her as a trained professional. She lifted up my balls, shaved them, moved my cock around, shaved it, and at last I was completely hairless down there.... And itchy.

"Just one final spot," she said, after applying soothing lotion all around my groin.

"Okay," I said, not knowing what could possibly be left.

"Roll back onto your stomach," she instructed.

I did.

She pulled my ass cheeks apart, and reminded me "Don't move a muscle."

"I hear you!"

She shaved between my ass cheeks, which I assume had very little hair anyway (I've never had the ability, nor even the inclination, to check) before stepping away from me and saying, "Grab a robe and follow me, Sugar."

"Okay," I said, my legs still burning a little.

I followed her into another room where she gave me a pedicure and a manicure, and painted my toenails ruby red. (I assumed my fingernails would wait until the evening of Halloween itself, for which I was grateful.)

The experience (totally unlike the waxing) was actually quite relaxing, although it got a little embarrassing when two middle-aged women (wearing actual clothes) were sitting on either side of me, watching me get my toenails done while wearing nothing but a pink satin robe.

I got dressed, and saw a text from Jojo on my phone: Hope you had fun. See you at home.

I arrived home and found a pair of bright red heels sitting on the kitchen table, four inches tall, with a note:

Michaela

To be a proper woman, you need to be able to walk in heels with elegance. You will spend the next two hours walking and dancing around wearing these.

Have fun,

Start slowly and VERY cautiously.

Mistress Jojo

This was a task that excited me! I'd always wondered what it would be like to wear high heels, but my feet were too big for anyone's I'd ever lived with... and knowing the statuesque Jojo had selected these ones especially for me was kind of cool.

I slipped them on, and they fit perfectly. Not Jojo's then, she must have bought them for me, which was very generous of her. I stood up, and fell right back down onto my chair after a brief wobble... lucky to fall backwards onto the chair instead of forward onto my face or worst, sideways and break an ankle.

I stood back up slowly and yes, VERY cautiously, and over the next hour, I practiced walking. It was one step forward, two steps back, sometimes literally, but eventually, like learning to ride a bike, I got the hang of it.

I learned to stand up perfectly straight... which helped me to keep my balance, but also to look elegant.

I learned not to look down at my feet, but rather to look straight ahead.

I started to sway my hips.

I started to saunter.

I started to feel confident in my heels... did I just call them my heels?

I was doing just that, when Mistress Jojo and a tall white guy strolled in the door.

"Looking good, Michaela," she said.

"Shit, man," the guy said, looking at me standing there in my red heels. But at least I still had my jeans on, so he couldn't see my pantyhose.

"Keep practicing," she said, as she led the tall guy into her bedroom. Twenty minutes later, after hearing a lot of loud fucking sounds that had my cock raging, he walked back out, looked at me again for a long moment and then left, shaking his head.

"Come in here, Michaela," Jojo called out.

I was surprised to hear that, as she hadn't ever allowed me into her room before, other than the first day to help carry her things in (of course I'd been in her room without permission more than a few times, to steal her panties and pantyhose).

I walked in and said, as she sat on the edge of the bed, completely naked other than a pair of ripped pantyhose, "Yes, Mistress?" and paused to gawk, as I couldn't help but perv on her body, which I'd never seen before even partially naked.

"Knees before me," she ordered.

"Really?" I asked, surprised.

"Now, sissy," she snapped, clearly annoyed by my hesitance.

"Sorry, Mistress," I apologized, as I quickly dropped before her.

"Actually, lie on your back," she ordered, reconsidering whatever she'd been planning.

"Yes, Mistress," I repeated, again obeying her, and now doing it much more readily.

"And it's Mistress Jojo," she clarified tersely, as she stood up, straddled my face, and lowered her pussy (yes, hairless just as she'd described it) above me. "Catch the cum," she ordered, just as a big gob of cum dropped directly into my eyes... making me snap both of them tightly shut.

"Open your mouth, you dimwitted cum bucket," she ordered, as I felt more cum dripping down onto me. So I opened my mouth and caught the tall white guy's cum that continued to leak out of her.

I caught a few swigs of cum in my mouth, and felt more land on my forehead, cheeks and chin.

"Good girl," she purred.

I felt such conflicting emotions! Humiliated at being treated this way and eating another guy's cum. Excited at being guided in exploring my feminine side in new ways I'd never imagined. Confused at the feelings swarming inside me as I swallowed the guy's cum, and found that I wanted more.

A moment later she said, "You may go."

I opened my eyes and saw she was putting a robe on.

"Yes, Mistress Jojo," I agreed, feeling so ashamed as I stood up, but immediately fell forward in my heels onto her bed.

"Much more practice," she prescribed. "We can't have any slips like that on Saturday."

"Yes, Mistress Jojo," I nodded obsequiously, as I walked carefully out of her room, and spent another hour practicing, wanting to be perfect on Saturday.

.....

The next morning there were "new" panties and pantyhose waiting for me, plus a tiny butt plug with lube.

Michaela,

A good sissy slut should be able to wrap her pussy around a nice big cock.

Here's a nice little one to start you off.

Put this in your pussy immediately, and wear it all day.

Mistress Jojo

This was flying more and more and more out of control.

I'd been wearing girls' undergarments to school.

I'd been waxed clean.

I'd eaten another man's cum somewhat like a cream pie.

Now she wanted me to wear a butt plug. To start me off.

As I examined the plug, which was very small actually, Jojo came out dressed for school in a cute plaid skirt and beige nylons, and she ordered, "Get into the panties and pantyhose right now."

"Yes, Mistress Jojo," I obeyed, having just showered.

"So obedient," she said, as she watched me drop my robe and butt naked, put on her garments. "The red toenails look really cute."

"Thanks," I said, looking at my toes, that did look cute, as I put the sheer hosiery on.

Once I had both garments on, she ordered, "Bend over the table."

I did, as obedient as you please, even knowing it would result in my having a butt plug stuck in my ass.

"Such a good girl," she purred as she pulled my panties and pantyhose down below my ass, and then grabbed the lube. She brought a finger to my asshole and rubbed the lube all around it. "Such a cute and tight man pussy my widdle girl has," she said, crooning again.

"Thank you, Mistress," I said, as yet again the opposing sensations of humiliation and excitement joined together in swarming through me.

"Ready to have your pussy penetrated?" she asked.

"Yes, Mistress," I answered, meaning it, curiosity and obedience consuming me far beyond the point of any resistance.

"I can't wait to fuck this man cunt," she said wickedly, as she slid the tiny toy into my ass.

"Ohhhhhh, I moaned, experiencing only a slight burn as it slid inside, but startled to hear a woman actually use the word 'cunt'.

"Tomorrow you get a bigger one," she promised, as she pulled the panties and pantyhose up and slapped my ass, sending the toy a little deeper.

"Ohhhhhh," I moaned again.

"Bye, sissy," she said, and headed out.

I had breakfast, sat down, and thus felt the slight discomfort of the toy in my ass. Luckily it was quite small, and after just a few minutes I became used to it.

That night after she was fucked by some guy, she marched into my room and silently pointed first to her mouth, and then to mine.

At first I was bewildered by the charade, but I soon realized she had a mouthful of cum.

Finally comprehending what she expected of me, even though I didn't like the idea at all, I opened my mouth and she pushed the cum out of her mouth, to pour it into mine.

Once done, she said, "One day soon, you can retrieve your own treat; It's way better directly from the source."

I swallowed the gooey cum, surprised this batch had almost no taste at all and said, "I'm not sure I'm ready for that."

"No worries, all in good time," she smiled unconcernedly, striding out.

.....

The following day, Friday, was almost like the movie Groundhog Day.

A new pair of soiled panties.

A new pair of pantyhose.

A larger butt plug.

Lube.

All that was missing was Sonny and Cher singing on the clock radio, 'I Got You, Babe'.

Mistress Jojo once again lubed me up.

She once again slid the toy into me... it was very noticeably larger.

This time it really burned. "Oh fuck!"

"The bigger the better," she tossed off unsympathetically as I felt this longer and wider toy tearing my ass apart.

"Shit," I whimpered, feeling an uncomfortable burn.

"Such a fuckable ass you have, girly," she said, as she pulled my panties and pantyhose back up, to keep the bigger plug in place.

"I can't imagine ever taking anything bigger," I said, still bent over the table, kind of afraid to move a single muscle.

"Oh, a good sissy slut can take anything up her slut box," she said, "all it takes is enough practice," slapping my ass and thus hammering it down to even deeper depths inside me.

"Oh, fuck!" I screamed.

"Maybe later," she quipped as she headed out.

I ended up missing my first class, since I needed to practice walking around with the new and improved (yeah, right) plug in my ass, without it being totally obvious why I was walking so funny. Eventually I got mostly used to it, although every time I sat down a new pain would leap forth... yet despite my discomfort, I was inexplicably hard all day.

As the day progressed my cock was dying for attention, as the toy constantly rubbed against my prostate whenever I walked... or sat down.

That night I massaged Jojo's entrancing feet for over an hour with the plug still deep in my ass, but greatly distracted from the pain, because I was fervently wishing I could fuck those nylon-clad feet.

She promised that tomorrow on Halloween Night, she'd make all my girly dreams come true.

I stressed yet again I wasn't sure I wanted to go any further with this, but she just said, "Tomorrow it's a girls' night out."

HALLOWEEN NIGHT

Jojo, already dressed in a sexy Harley Quinn outfit, like I'd predicted back when I had my pedicure, painted my fingernails to match my toenails.

She had me get dressed in a white garter-belt and stockings, panties over the top (in case a proper girl needs to pee, or to fuck someone), and silver heels... and then she gave me a padded bra, making me look like I had a nice rack... followed by a blue dress and a blonde wig, which is when I discovered I was going out dressed as Cinderella.

Fifteen minutes of make-up, and I was ready.

"Beautiful," she said.

I looked into the mirror and gasped. If it wasn't for the Adam's Apple, no one could have a clue I was a guy. "Wow!" I said.

"You look so fuckable," she said.

"I feel so sexy," I said, admiring myself in the mirror.