Roommate Dress-Up

"Michaela," she smiled wolfishly. "Halloween is only a week away. If you want to explore that feminine side of yours with my help, you can do it within the safe environment of Halloween, when everyone is wearing a costume."

Hearing her call me by the feminized name of Michaela for some reason excited me, as did her suggestion. I responded, "That sounds interesting."

"We're doing it," she announced, in a tone establishing the decision had been made.

"Well... maybe. Let's see what this looks like in the morning once we're sober," I joked.

"Oh, it's a done deal, there isn't any maybe," she adjudicated. "We're going to feminize you so well that nobody will think you're a man."

"I don't know," I said, suddenly feeling quite dubious about it now that it could actually happen.

"Look, bitch," she said, snatching her feet off my lap. "I'm dolling you up into a sexy slut, and that is it. You told me in secret you need someone to take control of you, and I'm just the person to take that control but no worries, it will also be in secret."

"Okay," I said, disappointed her feet were no longer in my lap.

"And going forward, no jerking off... at all... ever," she proclaimed. "You no longer have a cock, you only have a man pussy."

"A man pussy?" I asked.

"Your asshole is now a twat to be fucked," she said, and then added in response to a knock at the door, "Speaking of which, I'm about to get fucked myself."

She went to the door, silently welcomed in a tall black man, and led him past me to her room.

I remained on the couch and listened in as she said commandingly, "Strip and give me that BBC."

I couldn't help but wonder what it would be like to suck a black cock. I was curious about sucking any cock, but many of the hypnosis sissy videos I'd been watching had a BBC focus... and I couldn't deny a black cock looked particularly appealing. But in truth I found all cocks appealing, at least visually... and although the idea of being fucked in the ass... or... in my 'man pussy'?... hadn't ever been appealing at all... I suddenly found myself considering it, after the visual Joanne had given me of her wielding one.

I began to touch my throbbing cock as she begged, "Slam that big cock in my pussy."

But then I had to stop, recalling her order not to touch myself, and feeing compelled to obey her.

"Harder you fuck, let my roommate hear how a real man pounds a woman," she asserted, correctly assuming I was listening.

"That little man out there?"

"Little indeed," she agreed before adding, "unlike this massive fuck stick."

"You like my black dick, don't you, slut?"

"I love your black cock," she said. "And if you want, you can drill my asshole with it."

"Shit, you're real nasty tonight," he observed, as I got up and rushed off to my room, not wanting to hear any more, because touching myself or not, I'd be erupting a major load pretty quickly.

"Oh, fuck yes, fill my ass, she screamed, loud enough for our neighbours to hear her as well.

Shit, what had I gotten myself into?

.....

The next day I woke up late, a little hungover, and only vaguely recalling last night.

1. Had Joanne really offered to feminize me?

2. Had I willingly agreed?

3. Had I massaged her nylon-clad feet for well over half an hour?

4. Had she even answered the door to a black guy and invited him to come in and ass fuck her?

Answers:

1. Yes.

2. Yes.

3. Yes.

4. And yes.

5. Oh, shit!.

My cock was hard just like it was every morning, and as I reached down to deal with my morning wood, I recalled her also ordering me to not touch myself all week. Or ever again? Was that prohibition forever, or just until after Halloween?

And I clearly recalled her calling my ass a man pussy.

Fuck!

I got out of bed, doing my best to ignore my cock demanding my attention, then went and took a rather difficult morning piss (pissing through a hard on is always a lot more challenging).

I took a quick shower, got dressed, went to the kitchen for a late breakfast, and saw a pair of pink panties lying on the kitchen table with a note.

Michaela,

Here are the panties I wore last night both before and after I got ass fucked and had a big, hot load deposited in my tight little backdoor, which I invite you to visualize while you smell them; but remember, no touching yourself.

Put them on right away, and wear them all day.

Jojo

I brought the pink panties to my nose and smelt them... just like I always did, but this time I knew that she knew I was doing it.

So sexual.

So exotic.

I could see stains in her crotch area and that of her ass... obviously her own cunt cum, as well as some male cum that had leaked out of her ass.

I went back to my room and obediently changed out of my boxers and into the well-used pink panties.

I then had a late breakfast, and headed to my second class of the day, having slept through my English class.

It felt oddly liberating to be wearing panties out in public. Sure, I knew and so did Joanne, but nobody else did, and this was the beginning of the guided exploration of my femininity.

I arrived home and Joanne, wearing a white blouse, plaid skirt and mocha coloured nylons, asked, "How's my sissy boy?"

"Sissy boy?"

"I assume you're being a good boy and are wearing my panties."

"Yeah," I admitted sheepishly, my hidden apparel now feeling more gay, while I was talking to her.

"Then you're a sissy," she shrugged, and then added, "Show me."

"Show you?"

"I want to see you wearing my panties," she said, sounding a little annoyed at my hesitant response.

"Oh."

"Right now, chop-chop," she said impatiently, snapping her fingers. "I need to see what I'm working with."

"Okay," I belatedly agreed, feeling compelled to obey.

"You didn't come last night from listening to me getting fucked, did you?"

"No," I answered, as I nervously undid my belt. "But I did need to retreat to my bedroom, or I would have."

"Good boy for retreating," she praised me, but only in passing. "Now hurry up," she got back on track. "There's nothing you've got I haven't seen before, except it was in larger packages."

The reminder that she considered me small hurt; I was just over five inches, which was pretty average, from my understanding. My penis was smaller than any of the porn stars', but except for Joanne's reaction when she first felt it, I'd never had any complaints. Besides being equipped with an average sized penis, I'd also become really good at licking pussy... both of my serious girlfriends to date only coming from oral sex, but not from penetration.

I pulled down my pants and she ordered, "Take them all the way off. Shirt, too."

I did, feeling so insecure, as she looked down at me with an expression that could only be described as 'not overly impressed'.

"Well, we won't have to shave your chest at least," she said, as she took in my hairless upper body.

"I've never been able to grow any chest hair," I sighed, a failing (or so I'd always thought) I'd always been self-conscious about.

She said, as she walked around and examined me from behind, "Considering what we're going for, that's actually a plus. In fact overall, your body is already quite feminine."

"Thanks," I said, although I wasn't sure it was meant as a compliment.

"Your ass does look hot in those pink panties," she said, as she brought her hands to my ass and gave it a squeeze.

"Oh!" I gasped in an embarrassingly high-pitched tone, surprised by the sudden grab.

"It's an ass that was clearly made to be fucked," she added, as she came back around to face me... my cheeks burning red with shame, and yet I was also turned on.

She looked down at my hard cock, more or less contained in her panties, and said, "Your clitty is so small."

"Clitty?" I asked, my already red cheeks now burning like they were literally on fire.

"Yeah, your clitty. You see, a sissy doesn't have a cock, because cocks are big, and they're useful for fucking. A sissy on the other hand has a clitty, and even that's a generous term, since a clit is incredibly useless for most purposes, although it's admittedly very pleasurable to its owner," she continued, while gazing contemptuously at my penis. She then concluded, "while a tiny pee-pee is pretty much completely useless. Even on the occasions you're allowed to come, prostate stimulation is far better at achieving that end."

I had nothing to say about any of that, since how can you possibly reply to such a statement, when someone is not only questioning your manhood, but trashing it completely and tossing it on the dung heap.

"So I'll arrange a waxing for you tomorrow, for your legs," she moved on.

"A waxing?"

"Yes; if you want to be completely feminine, you can't have any hair on your legs," she said before adding, "or, of course, in your armpits."

"I don't know, that seems like going awfully far," I whined, feeling very uncomfortable standing in front of her almost naked in just her panties and my socks.

"I wasn't asking for an opinion," she said. "Or for permission, either. I'm now in complete charge of you, and I'm going to make you look so fucking hot for Halloween, you'll have guys swarming all over you."

"I don't want guys swarming all over me," I pointed out. "I just want to feel like a woman."

"Semantics," she shrugged.

"I just want to know what it feels like to be feminine for a day," I drilled down.

"And that's exactly what I plan to do for you," she said, grabbing her phone.

"I don't want to be perceived as gay, though," I clarified.

"Semantics," she shrugged again. "Nobody's going to think you're gay, they'll think you're womanly. Which is what we're going for."

"I'm serious," I stressed. "I'm not gay!"

But instead of answering, she studied my face for a few beats before musing, "Do you know you have perfect cock sucking lips?"

"That's something only gay guys do, and I'm not gay I'm trying to tell you," I insisted yet again, even though I had been wondering for a while what it would be like to suck a cock.

"I'm not saying you are gay," she shrugged. "I'm just saying you have cock sucking lips, an ass made for fucking, and a penis too small ever to completely satisfy a woman. And besides, I'm not gay; I'm bi, and I love sucking cocks."

I winced at her dig about my not satisfying women, yet another reminder of many throughout my life about my inadequacy at satisfying a woman... an insecurity I'd always had... for although it was true that nobody except Joanne had ever actually complained about my size or my lovemaking abilities, nobody had ever orgasmed on my penis either, which is why I'd worked so hard to develop my pussy-eating skills.

"I'll have new panties for you tomorrow," she said, before correcting herself, "well, new to you, but well-used by me."

I watched her slip into her heels before heading out. But just as she was about to leave she turned around and added, "And remember... no touching that clitty. It isn't yours anymore."

"That won't be easy," I said.

"If you touch that clitty of yours... at all, I won't help you anymore... at all," she warned.

"I understand," I said, finding it so strange to have a conversation where a woman compared my penis to a clit.

"Trust me," she said. "When I'm through with you, you'll be a completely new person."

"That's what scares me."

"We both know you want, even long for... to explore life as a woman... as a beautiful, sensual woman," she said, walking back to me.

"That is my fantasy," I admitted.

"So do as you're told, no more and no less, and I'll make all your dreams come true," she said, leaning down to give me a possessive peck on the cheek. "Now I'm off to sit on a professor's face before fucking her with my strap-on."

"Which one?" I asked, my eyes going wide at that wicked admission.

"I don't face sit or ass fuck and tell," she shrugged, adding, "I did mention Mrs. Walker by name that one time, but you'll never meet her because she lives in Canada," as she went to her bedroom and returned with a black strap-on harness. She waved it at me cheerily and said, "Maybe I'll use this on you some day."

"I can't fathom," I said, even though I couldn't help wondering what it would be like if she did ass fuck me.

"Go online and research the pleasure of being pegged," she said. "That's your assignment for tonight."

"Okay," I said, 'pegged' not a word I knew except in the card game called cribbage.

"Bye," she waved, as she dropped the strap-on into her bag and strode out.

That night I researched pegging, and learned it was a term for a woman wearing a strap-on to fuck a guy.

I read a few articles, primarily consisting of both men and women reporting their experiences doing it, which definitely sparked my further curiosity... it suddenly didn't seem gay to be ass fucked... it was a novel sexual experience, a way of building both physical and emotional closeness with your lover, plus a means of exploring the (long neglected by many) stimulation of the man's prostate.

I happened upon a twitter account called OnTheKnees, and I ended up scrolling through it for over an hour... in awe of many of the statements and quick gifs therein, including:

-Pegging taps into the submissive male fantasy of being dominated by his Mistress, of submitting to her desires, and offering his mind, body and soul to serve her needs. When a man expresses his submissive self and is anally penetrated by his female lover, he learns to relinquish control. Among other benefits to a relationship, this practice typically also results in the release of potentially debilitating stress in both parties.

That made pegging sound so erotic and sensual. Not to mention therapeutic.

The love, the control and the vulnerability. Many male submissives (and also female ones, but that is off topic in this forum) relish the opportunity of being the submissive, the vulnerable partner - the one who's still loved and cherished, despite not being the "alpha male" that society expects. And when guided by a perceptive and caring dominant partner, he needn't worry about being judged.

This one sounded a lot like me. I didn't want to be judged for my feminine fantasies, yet if Joanne could be as knowledgeable and non-judgemental as she appeared to be, I definitely wanted to explore them.

Ideas To Humiliate Your Male: Frequent, mandatory performance of sexual services such as erotic massage, cunnilingus or analingus, without permitting either reciprocal acts or intercourse.

This one made me think about the way Joanne was treating me... making me perform for her benefit sexually, but not allowing me the tiniest bit of penile stimulation, or to come.

I ended up watching a few pegging videos, and I found the more verbal the woman would be, and the more the guy would moan in very unmanly, very feminine ways, the more my cock, or rather my clitty, got to raging, and thus my interest in exploring this previously unknown act was suddenly consuming me.

If I hadn't been ordered not to touch myself, I would have been spewing my load in seconds.

So instead I took a very, very cold shower... which sure as fuck didn't help much. Who advocates those things?

......

The next day, a Tuesday, I got up and found a fresh pair of panties (or rather the opposite of fresh), and this time pantyhose as well and, of course, a note.

Michaela,

Here are the panties I wore last night, as well as the pantyhose... I took two loads in them last night.

Put them on and wear them all day.

Jojo

PS: I scheduled you a four o'clock waxing at Le Chateau Salon on Boyle Street. Be there.

My cock flinched at my seeing the panties and pantyhose, but my body flinched in a different way at knowing she expected me to get waxed.

Wearing panties and pantyhose didn't seem gay to me, but getting waxed did.

Wearing panties and pantyhose I could hide, but getting waxed could fairly easily be noticed by someone.

I put the panties and pantyhose on, feeling giddy doing so, particularly upon seeing more than one cum stain against my feet, as well as my ass. I couldn't explain it, but the cum stains somehow enhanced the titillating sensations of wearing Joanne's soiled pantyhose. I rubbed my hands up and down my legs, loving the feel of them... I really resented not being allowed by society to just wear such lovely, sensual garments anytime I wanted... I resented that these were perceived as female-only garments.

I put on my jeans to hide my feminine undergarments, plus socks and runners, and headed to my classes again, enjoying my secret rush.

At 3:30, Joanne texted me: I'll meet you there, my silky sissy.

I still didn't particularly love being called a sissy, but coming from Joanne, it didn't seem as bad.

I responded: You're coming?

She texted back wickedly: Not at the moment, but likely tonight.

I shook my head at her naughty bluntness... she literally got fucked (or similar I guessed) every single night. Yet feeling an overwhelming need to obey her, I responded: See you there.

She responded: Good, my sheer sissy slut.

I was a lot of things... but a slut definitely wasn't one of them... even if the term sissy was perhaps becoming applicable... at least her definition of sissy.

I responded sarcastically: Yes, Mistress.

I instantly realized my mistake, when she responded: Excellent thought! I like it. From now on, you may address as Mistress Jojo.

I clarified, even though I kind of liked the idea of having a Mistress, of someone just making my decisions for me: I was being sarcastic.

She responded: Don't care. You will now address me as Mistress Jojo. Is that clear, or will I need to punish you?

I sighed to myself, even as my cock flinched in her panties and pantyhose: Fine.

She responded: FINE WHAT, SISSY SLUT?

I realized I'd gotten her mad, the all caps a clear message, and also realized what she was demanding, so I clarified: Fine, Mistress Jojo.

She responded: Better, but don't pretend you don't like this. It was your own idea, and even if you thought it was just sarcasm, your subconscious was lobbying for it to happen.

I sighed, responding: You and your psychology classes.

She answered: They definitely help me train little bitch sissy sluts like you.

I said, my cock raging: You're loving this, aren't you?

She replied: Agreed. As are you. See you soon, my sheer, sissy, submissive slut.

I replied: See you soon, Mistress. And yes, you're right.

As I headed to the salon, I couldn't believe I was actually going in there. I was willingly about to get my legs shaved with no wild horses or anything.

I arrived a few minutes early, and Jojo was already there.