Roommate Dress-Up

Summary: Straight guy is feminized by female beauty.

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

“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?

    1. Had I willingly agreed?

 

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

 

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

Answers:

    1. Yes.

    1. Yes.

    1. Yes.

    1. And yes

 

    1. 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.

“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.

“And fuckable,” she repeated.

“You really like the notion of my being fucked.”

“I really like the notion of making you my submissive little ass slut,” she said, slapping my ass, which had the butt plug back inside it. It didn’t hurt nearly as much today.

“Play your cards right, and I might just let you,” I said in a sultry feminine tone… feeling so caught up in the moment.

“Oh, I have all the cards you’ll ever want, you sexy slut,” she outdid me, as we headed out.

For the next few hours I drank… I danced with her three girlfriends, I even felt like I was one of the girls.

I was flirted with by guys and girls… and was crazy horny and drunk when we got back to the apartment, once again just the two of us.

“Pour me a drink,” she said, as she headed to her bedroom.

“Sure,” I said, pouring each of us a drink.

I wasn’t overly surprised when she returned still in her costume, but with one additional accessory: her strap-on.

She walked over to me and ordered, as she accepted her drink from me, “Knees, slut.”

“Joanne, I really enjoyed tonight, but….”

“Now,” she ordered, placing both of her hands on my shoulders and roughly shoving me to the floor.

“But I’m not gay,” I insisted for some countless time.

“Sucking my cock doesn’t make you gay,” she said as she slid her cock in my mouth. “I’m not even a guy, for crying out loud!”

I couldn’t utter a word of objection, since she was suddenly face fucking me.

“Taking my cock in your cunt doesn’t make you gay either,” she added, while more than half of her cock pumped in and out of my mouth, and a rush of adrenaline coursed through my body… at being used… at actually having a cock in my mouth… even if it wasn’t a real one.

After only a minute, she pulled out and ordered, “Beg for my cock, slut.”

My weak resistance having crumbled away completely by this time, I did reply… in complete lust, craving that cock back inside my mouth, loving to be used like a slut, “Please face fuck your bimbo sissy slut, Mistress Jojo,” I begged, saliva dripping down my chin.

“You will obey every order I give you tonight,” she clarified, “Instantly.”

“Yes, Mistress Jojo,” I agreed.

“Get this cock nice and wet for your pussy.”

I leaned forward, took her cock into my mouth and began bobbing, feeling another rush of adrenaline course through me at knowing I was at this moment a real girl. I had a cock in my mouth, I had tits, I was wearing sexy lingerie, and I even had a pussy! I slowly bobbed back and forth, taking more and more of her cock into my mouth.

“Such a natural cock sucker,” she purred.

“Mmmmmmm,” I moaned, excited to be her cock sucker.

“I’m going to fuck you so good, you’re going to be addicted to cock,” she said a couple minutes later as she pulled out of my mouth, and then she ordered, “Come to my bedroom; crawling.”

I crawled after her; the way I felt right now, I would follow her anywhere.

Once inside her room, she turned around and said, “Tell me how much you want to suck my cock.”

“I want to so badly, Mistress Jojo,” I replied without hesitation, as I crawled to within inches of her.

“Because you’re my sissy slut,” she said, slapping my face with her cock.

“Exactly so, Mistress,” I agreed, wanting that cock back in my mouth, “I’m your sissy slut.”

“And my cock sucker,” she added.

“Yes, and your cock sucker whenever you wish it, Mistress Jojo,” I mindlessly repeated.

She slid back into my mouth and face fucked me for a good couple of minutes so deeply, that I gagged on a couple of occasions.

When she pulled out, she ordered, “Get onto my bed on all fours.”

“Yes, Mistress,” I agreed without hesitation, willingly assuming the position to get myself fucked… the three days of wearing a plug getting me used to having something in my ass, and now having me curious what it would be like to be fucked.

“You kept doubting yourself before, but now you really want to get fucked, don’t you?” she asked, as she grabbed some lube from her nightstand.

“Yes, Mistress,” I admitted. “I want to feel what it’s like to be the one getting it instead of giving it.”

“Do you want to become a complete girl?” she asked as she lifted my dress, tugged my panties down, and pulled the plug out… making a popping sound.

“Oh!” I gasped, suddenly feeling uncomfortably empty.

“Such a needy-looking pussy you have,” she said, as she lubed her cock.

“I can’t believe I’m letting you do this,” I said, in a lustful daze.

“Do what?” she asked innocently, obviously wanting me to say it.

“Fuck my ass,” I said.

“You mean your pussy,” she corrected me as she tossed the lube aside and extended her strap-on cock to my pussy.

“Yes, Mistress Jojo,” I corrected, “I can’t believe I want you to fuck my pussy.”

“Because you’re my sexy slut,” she said.

“Yes Mistress, you’ve turned me into a beautiful, submissive, sexy, lustful slut,” I listed, feeling the truth of all those things, “and I thank you for it.”

“I own you now,” she clarified.

“Yes, Mistress,” I agreed, playing along.

“Which means you’ll always do anything I order you to,” she added.

Wanting that cock inside me, desperate to be fucked, I replied, not at all worried about any possible consequences of such a boundless commitment, “Yes, Mistress Jojo, I’m your completely obedient pet slut.”

“Good girl,” she said, happy with my answer, as she slid the cock inside me.

“Ooooooooooh, yes,” I moaned, the butt plugs having prepped my ass for this longer and thicker cock. Yes, there was a bit of pain, but the pleasure quickly enveloped it.

“Such a tight pussy,” she said, as I now felt her skin resting against mine… all eight inches inside me.

“So big,” I moaned, feeling so full, so feminine, so slutty.

“I’ll be fucking this pussy often,” she promised, as she began slowly to fuck me.

“I sincerely hope so,” I moaned, the sensation of being fucked surreally different from being the one doing the fucking. Each vantage was pleasurable, but I couldn’t explain it… this was the position I was destined to be in.

I wasn’t gay.

I was just being pegged.

I was just being fucked by another girl.

It was nearly the end of 2020, and there was nothing wrong with a man allowing a woman to pleasure his prostate… even though my being completely dressed in feminine attire, even including makeup and wig, may have weakened my manly argument.

“Oh yes,” she said as she slapped my ass, “I’m going to make you into the biggest slut in the dorm.”

“Yes, Mistress,” I agreed, not considering all the activities that description might encompass, just wanting to continue being fucked… my cock raging.

Another slap… “And that’s for keeping your sissy secret to yourself during our time dating, you coward. Imagine the things we could have been doing together all these months if I’d known!”

“I didn’t know how to bring it up,” I moaned, in awe of her capacity to understand, and even to accept my shameful brand of sexual depravity. I wondered what exactly we could have been doing.

“Oh, don’t you worry little girl, I plan to make up for lost time,” she said ominously, as she began fucking me faster.

“Oh yes, fuck me, fuck me hard,” I moaned, my moans sounding very feminine.

“Imagine if Lauren could see you now,” she taunted me, as she obliged and began slamming my ass like a real cocksmith stud.

“Oh God,” I moaned, having not even thought of my girlfriend at all during this entire transformation… I’d been so completely drawn into my newfound feminism.

“I bet she would fuck you too.”

“I can’t imagine,” I said, a wave of guilt at what I was doing suddenly washing through me, even as the pleasure increased inside me, and I no longer had any control over my actions or my decisions.

“Oh yeah, she’d pound this pussy, while I face fucked you in a nasty spit-roast,” she elaborated wickedly, as my guilt overwhelmed me even while my cock raged and my body burned in pleasure.

“If I could only be so lucky,” I said, not sure how I could possibly explain what I’d done… and was still doing… to her.

“Bounce back and take it as deep as you can,” she ordered.

I obeyed, and soon I was whimpering like a bitch in heat as I fucked her and she fucked me.

To my surprise and puzzlement a couple minutes later, she unstrapped herself from the strap-on, but left it buried deep inside me, then pushed me onto my back making me yelp, and… WTF?!… straddled me!

My eyes went wide as I realized she was about to ride me… to ride my cock!… and that would be cheating. Everything else I’d done with Jojo had been activities I could never do with Lauren, but this one I could do, and had even done!

“Don’t worry,” she said, “this isn’t for my pleasure, your cock couldn’t ever get me off.”

“But I…” I protested weakly as she dropped onto my actual cock, and started bouncing up and down. I couldn’t say a word, but it was true without a doubt that my cock was inside her pussy right now no matter whose pleasure it was for, so I was undeniably guilty of cheating on Lauren!

But regardless of my severe qualms, the cock deep in my ass rubbing my prostate wildly added to the wild intensity of this entire night and her wet, warm pussy engulfing my cock were all too much, and in a humiliatingly short amount of time… ten seconds… I grunted and spewed my load inside her!

“Shit, that’s a new speed record by an order of magnitude,” she laughed, as I filled her pussy with my seed.

“I’m so sorry,” I said, mortified I’d cheated on Lauren, and that I’d come so quickly.

A moment later she straddled my face and ordered, “Get licking, slut. Lauren tells me you’re at least good at doing that.”

My cum dripped on my face as I obeyed, licking my own cream pie from her pussy.

It tasted amazing…. The mixture of her pussy juice and my cum.

“Eat it all down, slut,” she ordered, as she ground her pussy all over my face.

I continued licking, thrilling to her entrancing moans and then… after ignoring her clit the entire time… I attacked it.

“Oh fuck, don’t stop,” she moaned, clearly enjoying my tongue licking.

A few licks later, she grabbed the back of my head and forced me deep into her pussy, as she erupted all over my face.

I hungrily lapped up all her sweet pussy cum as it poured into my open mouth.

A long moment later, once she’d recovered from her orgasm, she released my head and said, “Shit, Lauren was right; you are indeed very good at that.”

“Thank you, Mistress,” I said, as she got off the bed.

And then she kind of blew my mind by adding, “You know Michaela, I’d originally planned just to give you a pantyhose foot job tonight, but you were just too damn sexy not to fuck.”

“Really?” I replied. “I have mixed feelings about that, Mistress. It was great while it was happening… incredible even… but I still can’t believe I cheated on Lauren by letting you fuck me.”

“You didn’t let me,” she pointed out. “I was controlling you every step of the way. Isn’t that true?”

“I suppose so,” I said, as she went to her phone and typed something… assumedly texting someone.

“And since you weren’t the one making any decisions, it wasn’t your responsibility, and therefore it wasn’t your fault! So, I realize you’re feeling guilty as hell right now for cheating on your girlfriend, but in point of fact you didn’t cheat on her. The worst that can be said of you is that you were a victim of circumstances. So, get over it.”

She then added, “And to be perfectly clear, you’re still not the one making the decisions around here, and my next orders for my little sissy slut are,,, that you’re to be dressed all pretty for me… every single day… from now on.”

“Every day? Ongoingly?”

“Every day at least until Lauren comes home, and then we can make other arrangements,” she nodded, just as there was a knock at the door. “This is not only who you really want to be, but who you need to be.”

“Well, I….” I began, as my phone rang.

“Hey, it’s your girlfriend,” she informed me without even glancing at the phone.

“Shit,” I said, walking into the living room to grab my phone.

“Answer it dressed just like you are,” she ordered, “wig, makeup, the whole ball of wax,” as she followed me into the living room.

“Really?” I asked, retrieving my ringing phone.

“Yes, really,” she ordered, even though she knew we always facetimed.

I went into my bedroom and said hello.

Lauren burst out laughing the moment she saw my face. “Wow, you look even hotter than I do!”

“Not a chance,” I said, seeing she was dressed up as a slutty maid… still. Even though in France it must have been five or six in the morning. Judging from her ruined makeup, she must have spent the night doing something of note. But given what I’d been doing, I wasn’t about to ask.

“There must be an exciting story here!”

“I don’t even know where to begin,” I said lamely, pondering what on earth to tell her.

“No worries, just tell me what happened tonight, and how you felt about it; I know about the rest of the week already. My small-dicked love, you’ve been well and truly set up!”

My mouth dropped open like a cartoon character’s, and then l began deducing my way through what she’d just revealed.

She knew.

She knew everything.

She knew about my week of feminization.

She was the one who’d set Joanne and me up as roommates.

Joanne had known I was a cunnilingus wizard, and she’d heard it from Lauren. What kind of ‘casual friends’ shared information like that?

For a start, it would have to be ones who each knew Joanne and I had a past, albeit a very limited one.

And Lauren said she knew about my entire week, so Joanne must have been keeping her informed.

Plus, Lauren had just told me I’d been set up, which implied Joanne must have arrived here already planning something nefarious.

And the plan must have morphed into getting me feminized once I’d spilled my guts to Joanne, and Lauren must have been on board with that new plan.

So here I was staring into my phone, with my girlfriend staring back at her own girlfriend!

And… she seemed totally okay with it. Congratulatory even!

“Whatsamatter?” she asked jovially. “Cat got your tongue?”

I shook my head, barely coming up to speed and asked, “So does this make you my Mistress Lauren?”

She smiled, pointing to a collar on her neck, and then she moved her phone close enough that I could read, ‘Jojo’s pet’, “Well, not exactly. I’m Jojo’s submissive lesbian pet, so my options are just about as limited as yours, but you’ll definitely be my pet in some fashion once I return, so long as we both do whatever our real Mistress tells us to.”

My bedroom door opened and Jojo came in, carrying a collar in her hand. “Don’t worry my new slut, I’ve got one of those for you, too.”

“Hi, Mistress Jojo,” Lauren greeted eagerly.

“Hi, my pet, have you missed my cunt?” Jojo asked, as she buckled the collar around my neck and I stood there motionless and speechless.

“Badly,” Lauren replied.

My life-defining collar in place, Jojo hooked a leash onto it, took my phone away from me, and tugged me down to my knees, where I discovered she was once again wearing her strap-on.

“Show your girlfriend what a good cock sucker you are,” Jojo ordered. “You may think of it as cheating if you really have to, but somehow I don’t think she’ll mind in the least.”

“Yes, Mistress Jojo,” I replied, my mind spinning out of control with the nine million new realities of this situation.

“Yes, baby, suck that cock for our Mistress,” Lauren cheered me on. “And for me, too!”

I took it in my mouth and began bobbing, while definitely not cheating, while Jojo and Lauren chatted about their respective days for a few minutes. Apparently Lauren had spent a long night servicing a French sorority of dominant lesbians.

Jojo then asked, “Want to see me fuck your boyfriend?”

“God yes, so badly,” Lauren replied, as Jojo pulled out of my mouth and pointed to my bed.

“Want to get fucked while your girlfriend watches, sissy slut?” Jojo asked, as she moved behind me.

“Yes please, Mistress,” I begged, dying to feel that cock inside me again, and feeling so completely liberated that my sweet girlfriend actually not only knew about my sissy desires and indiscretions, but she was highly in favour of them!

“Fuck her, Mistress, fuck my baby’s cunt good,” Lauren exhorted Jojo, sounding so hot saying that.

“You two are perfect for each other; you’re both good little slutty babies!” our Mistress Jojo praised us as she slid her cock back into my pussy.

THE END