"Sissified": 12 Days of Sissy-mas

True purpose?

Being a cross dresser?

A sissy?

Those are roles I should aspire to?

Her words were strange, borderline preposterous even, and yet as I recalled the many Tumblr gifs I had scrolled through during the past few months, I knew exactly where she was coming from... but online these were just silly fantasies... ways to get off... almost always followed by shame that they'd turned me on in the first place. Yet the cycle always continued as I returned to Tumblr a few days later and repeated the excitement, followed by the shame.

Today like every day from now on, you will wear a pair of panties and pantyhose, except when you undress at Claire's Salon.

Claire's Salon?

That was the ritziest salon in the city.

It was for women. It was a place Paige had said she dreamed of going. It was also the place I'd purchased a gift card for her for Christmas, that ironically, she would receive when she returned home. She would receive a three-hour diva experience that had set me back 400 bucks.

You have an appointment there today at 1PM under the name Kendra Winston. It is prepaid.

You're likely wondering why you're going there. It's a surprise, but is also an important step in your journey.

Remember, no coming!!!

Mistress M

What could she possibly expect me to have done there?

I couldn't fathom.

Although I sensed it would be something humiliating.

I ate breakfast, showered, put on a fresh pair of panties and pantyhose, got dressed (no socks this time, figuring I wouldn't be walking around without shoes anywhere, and headed out, as I wanted to do some post-Christmas Day shopping (so much is on sale the day after Christmas).

I bought a new 4K blu ray machine, since I'd bought a 4K TV on Black Friday (70 inches... size sometimes does matter... LOL) and then I'd learned you needed a 4K blu ray player to watch the 4K movies I had purchased (Both John Wick movies, The Spy Who Dumped Me, Justice League, and Mamma Mia (that last one for my girlfriend, I promise... okay, I'm not going to lie, I loved it too)). I also picked up the Harry Potter and Mission Impossible 4K box sets, and the just-released Venom (which I hadn't yet seen).

I also went jeans shopping and felt oddly liberated as I tried them on in the change room. Each time I took off a pair of jeans, I admired my legs in the mirror. God, I loved the look and feel of nylons... even on myself.

I bought a couple pair of jeans, had a quick lunch (Subway, honey roasted chicken on honey oat if you care), and headed to Claire's, even though I was pretty sure I didn't want to, it would no doubt be almost fatally embarrassing. I knew that the more I obeyed Mistress M's instructions, the deeper I would fall into this sissy transformation someone had orchestrated for me, and had even paid for. And even as I complied with everything, I still questioned whether this was a direction I wished to travel. I wasn't leaning strongly one way or the other, but I still kept going forward, which I guess said something all by itself.

Sure, I had liked the first task, gotten excited even, but there were ten more to go after today's ominous one. An even more ominous thought was that I could only fathom they would become ever more daunting and humiliating as the days progressed.

Yet my cock was hard.

Ultimately I felt compelled to obey.

No matter how much I wanted to deny it, I was enjoying this so far, and I wanted to continue. If things got too weird, I could always walk away. I think.

I reached the salon, walked just inside the door and froze.

Three feet inside the entrance was a prominent sign: No shoes past this point.

Shit!

I looked at the mostly high heels that had been placed on shoe racks along the left-hand wall.

I sighed.

I considered turning around to leave, and yet not seriously. No one was going to pay much attention to me, and the odds of my knowing anyone here was close to zero.

I placed my out of place runners on a rack and walked further inside.

Embarrassment hit me: five women were all seated, waiting their turn in the lobby.

They all looked up at me. Scary!

I went to the front desk and whispered, feeling five sets of eyes staring at me from behind (no idea if they really were, but in my head they definitely were), "One o'clock appointment for Kendra."

"Pardon?" the drop dead gorgeous blonde-haired, blue-eyed teen asked, far from whispering.

I leaned in and whispered again, "Appointment for Kendra."

"Oh," she said, studying me for a moment and then looking down at her computer. After a moment, "I see. Please take a seat."

"Thank you," I replied, feeling my cheeks almost bursting into flame. I scuttled over to an open seat and sat down, where I noticed a couple of my quintet of new companions gazing directly at my feet.

I kept my head down for a couple of minutes, unable to look anyone in the eyes, until my new name was called out almost immediately even though these (other?) ladies had gotten here first, only adding to the humiliation of the moment, "Kendra."

I never even glanced at the faces of the seated women as I got up and followed a short, slender Asian woman, again feeling their stares stabbing into my back.

Once we'd arrived in a room, the woman instructed me, "Get undressed and lie on your back beneath the blanket."

"Yes, ma'am," I responded, realizing how subservient my response was.

"Your pantyhose and panties as well," she added, before walking out.

My jeans are still on! How could she know I'm wearing panties?

My question unanswered, I got naked and climbed under the thin blanket, feeling massive trepidation for whatever was coming.

A minute later there was a businesslike knock at the door and the same woman's voice, "Ready?"

"Yes," I responded.

She walked back in, grabbed something from a table and walked over to me. She lifted the blanket off my left leg, and wordlessly began smearing sticky goo all over it. My eyes went wide as I realized she was about to wax my legs.

Oh, fuck!

Yet, I didn't stop her. I lay there in shocked awe as she coated my (thankfully not too hairy) leg.

Once done, she pressed some strips of something onto my legs and warned me, "This may hurt..." she took hold of one of the long strips and yanked it completely off in an instant before finishing, as I screamed, "...a lot."

I peered up at her in terror as she smiled with a hint of sadism and yanked off the second one while I was still sobbing in pain from the first.

A few more painful yanks... if I hadn't looked I would have thought she'd pulled off all my skin... and she said routinely, "First leg is done."

"Holy fuck," I groaned far from routinely, wondering if this was the pain women always endured when they waxed their legs. (I've since learned that the first time is usually the worst.)

"Just relax," she encouraged me, as she uncovered my second leg.

I chuckled weakly, "Relaxing is the one thing I won't be doing."

The pain returned a few minutes later, just as bad.

She then surprised me as she pulled the blanket completely off my naked body and ordered, "Spread your legs."

"Excuse me?" I asked, having heard her but not believing what I'd heard.

"Time to shave your private area," she explained.

"Really?" I asked.

"That's what was paid for," she told me.

Then for twenty plus minutes, shaving being a lot less painful, every hair in my crotch area was removed. I desperately tried not to get an erection... thankfully I succeeded, even though she cupped my balls many times and casually moved my cock around whenever it was in the way.

She then ordered, "Roll onto your stomach."

"What's left?" I asked, then realized I shouldn't have.

"Your buttocks, of course," she answered, as I obediently rolled into place.

"Oh," was all I said, as she spent the next while getting rid of all the hair not only on my ass, but even between my ass cheeks... easily the most macho-crushing moment so far.

She then did my back, rolled me back over to gain access to my front, and did my chest, which was already almost hairless, something I'd always been embarrassed about until now. She also shaved my arms and my pits.

She then announced, "Done."

"Thank you," I replied, it seeming the right thing to say.

"You're welcome,' she said, handing me a bag. "Use the lotion on all your depilated areas for the next few days, and you should take a long soak tonight with the salts I've provided."

"Okay," I said, accepting the bag.

"You may feel itchy or get rashes if you don't take care of your skin, especially your delicate areas," she explained.

"Yes, ma'am," I nodded, feeling she was speaking to me as if I were female.

"You may get dressed," she said, and walked out.

Standing up, I turned slowly around in place, studying myself in the mirror. I was completely hairless except for my head.

It made my six-inch dick look way bigger.

Although the procedure had seemed rather emasculating, the truth was, it actually made me look better: my cock looked bigger, I looked better. Truth be told, I kind of looked like one of the porn stars I watched, who were always shaved down below.

I put my panties (were they mine?) and the pantyhose back on, surprised so sexy I felt with the smoothness of my legs. I finished getting dressed and walked out, feeling a little itchy and sore as I did.

I went to the front desk to pay. The blonde reminded me, "It's already paid for."

"Oh, okay," I nodded, walking to the entrance and putting my shoes back on.

I drove home via McDonalds (getting a quarter pounder without cheese meal in case you care).

I ate dinner at the kitchen table.

I watched some television.

I resisted scratching my itchy skin, as my crotch area especially was begging for attention.

I took a lengthy bath with the unique bath ball that had been given me, feeling somewhat decadent, kind of like Julia Roberts in 'Pretty Woman'.

I couldn't deny that I felt very much like a woman.

After the bath, I applied the salon's lotion as my skin, especially my legs, was noticeably redder than usual.

I then called Paige, telling her about the shopping part of my day, not the rest... although at some point soon after she returned, she would discover what I had done and require an explanation... I mean hairlessness wasn't something I could hide from someone I shared a bed with.

I would need some time to figure out how to explain why I'd decided to get a complete body wax.

Fuck!

DAY 3: Thursday the 27^th

I woke up and applied the lotion again, as my legs looked redder than they had yesterday.

My balls were itchier.

Thankfully the lotion really helped.

Then, wearing only my pink panties, my lavender pantyhose and my robe which I left hanging open, I headed down to the kitchen and to the box, and opened Day 3 with the odd excitement I used to feel when I was a kid on Christmas morning.

Unfortunately as you get older, opening presents gets less and less exciting, as they are usually gift cards, or exactly what you'd asked for. Thus, not many surprises. But these pink gift boxes were intriguing.

This one contained a shot glass.

Weird.

I read the note:

Kendra

Do you feel the changes inside you?

The excitement of wearing panties?

The sexy feeling of wearing pantyhose?

The unnatural sensations of being hairless?

The femininity of it all?

Yes, I could feel changes like these ones inside me, although I couldn't explain them.

I enjoyed wearing panties.

I did indeed feel sexy in the sheer pantyhose.

I wasn't sure I felt natural, but looking in the mirror last night (putting my... yes, definitely my panties and pantyhose back on after the lengthy bath because I wanted to sleep in them... which in retrospect is definitely rather sissy-like), my legs looked sexier and more feminine without the hair.

You're probably wondering about the purpose of the shot glass.

Yep!

Today you get to come.

Awesome!

Into the shot glass.

Then you'll chug it.

Oh God!

I know you've been wondering for a while what cum tastes like.

So today you'll find out.

Go to Tumblr (I know you love the site) and look up 'You May be A Sissy if...' and scroll through them all.

How could she possibly know that about me?

Who the fuck orchestrated all this?

Why am I already fucking hard?

Then you may come.

Then you will drink it down.

Enjoy your treat.

Mistress M

Fuck!

Yet I'd be lying if I pretended I hadn't pondered what cum tastes like... and pondered it a lot.

More than once I had considered eating my own jism, especially when I was hard as hell and scrolling through Tumblr gifs.

Yet as soon as I came, that curiosity always faded.

So, after a morning of grading papers, I turned on the television, I had six episodes of Manifest to catch up on, flipped open my laptop and found the sissy page she referred to.

My cock got rock hard just from the first picture: a hot blonde slamming her strap-on into another hot blonde with her legs spread and obviously in the midst of an orgasm, with the caption: IF YOU WANT TO BE THE ONE WITH YOUR LEGS OPEN INSTEAD OF THE ONE DOING THE FUCKING... YOU MAY BE A SISSY.

Truthfully, I could imagine myself being either. The idea of being pegged was another fantasy that had been awakened in the past few months.

It first popped into my head watching Deadpool, and then heated up some more when I saw it on a variety of Tumblr gifs.

The next one was a brunette sucking and stroking a hard cock with the words: IF YOU'RE CHECKING OUT THE COCK INSTEAD OF THE HOT GIRL WITH THE BIG TITS... YOU MAY BE A SISSY.

Damn it! I sighed. I realized I was indeed staring at that big cock sliding in and out of the girl's mouth in this brief gif, and I hadn't noticed those massive bouncing tits at all.

That was followed by another gif of a pretty brunette slowly sucking a big cock deep into her mouth with the words: IF YOUR FIRST THOUGHT IS 'I THINK I COULD DO THAT'... YOU MAY BE A SISSY.

I guess I wasn't too far gone, because it wasn't until after I'd read the caption that I wondered ... Could I do that? Could I take a cock that long all the way into my mouth? This hot girl made it look so easy... so natural.

I probably should have stopped scrolling down, as I could feel myself getting drawn in like I always did... but like always, I kept scrolling so I could take in each gif.

I'm not sure whether I actually did open my mouth, but I was in awe of a massive load spewing out of a white cock as two cute redheads stroked it together while attempting to catch at least their share of his load with the words: IF YOU OPENED YOUR MOUTH TO CATCH THAT ROPE OF CUM... YOU MAY BE A SISSY.

Again, I wasn't sure if I had... but I was undeniably captivated by the image of all that cum shooting out of a cock. And because it was a gif, it continued shooting over and over and over...

The next one made me think of today's note from Mistress M and my task, as I watched a hot blonde in glasses (looking nerdy hot) wiping cum off her face and into her mouth while licking her lips seductively, and the words: IF YOU'VE EATEN YOUR OWN CUM AND LIKED IT... YOU MAY BE A SISSY.

I felt a chill go up my spine at this reminder of today's task.

And no, I hadn't done it before.

Yet I knew I'd be doing it soon... I'd be eating my own cum whenever this load burning in my balls finally erupted... although I wanted to hold out as long as I could.

The next one wasn't a gif, but a picture of a brunette in a dress and her feet in nylons with the words: IF YOUR NAME IS UNISEX SUCH AS PAT OR CHRIS... YOU MAY BE A SISSY. EVEN YOUR PARENTS WEREN'T SURE HOW YOU'D TURN OUT.

Until Christmas Day, I'd never once pondered that my name could easily be turned into a feminine one. Yet for three days now, a stranger (or maybe someone close) had been calling me Kendra.

And right now, the name I wanted to be called was Kendra instead of Ken.

Next was a hot black and white gif of a girl with her hands bound behind her back, on her knees, sucking a cock, as a guy held her head and used her roughly. The caption was: IF YOU WONDER WHAT IT WOULD BE LIKE TO BE USED LIKE HER... YOU MAY BE A SISSY.

FUCK!

I'd been thinking exactly that... minus the being bound part, as I hated being confined in any fashion.

But the rest... the idea of just being taken and used... was strangely hot... and I considered how hot it would be to make this fantasy into a reality.

The idea of sucking a cock was hot, but the idea of the reality was scary, if that makes sense.

The next one had apparently been borrowed from the blacked site (which was a hot interracial site of white girls being used by black men... although the scripts were terrible) of two blonde girls sucking two black cocks with the caption: IF YOU CAN'T DECIDE WHICH COCK IS JUICIER... YOU MAY BE A SISSY.

I looked at each cock: one was thick and straight like a rocket; the other was thick and curved.

Each was indeed captivating, and each made my mouth water.

Equally hot was each girl with a juicy cock in her mouth and her eyes looking up at the dominant black man.

The next one was also hot. A normal looking blonde was in awe of a huge black cock as she stroked it, seeming to say 'Oh my God' in complete awe of its majestic beauty before sucking it as if it was the last cock on earth with the caption: IF HERS IS ALSO YOUR OWN FIRST REACTION TO THIS DICK... YOU MAY BE A SISSY. AND IT IS, ISN'T IT, SISSY?

I'm not sure I was that excited, but I was in awe of the huge cock... I mean I realized I'd just called it majestic. And that did indeed seem the exact right word... majestic.

I kept scrolling... each entry making my cock throb... the next one was a cute girl with a ponytail in the midst of receiving a massive facial with a big smile on her face, with the caption: IF YOU'D RATHER BE THE GIRL ON HER KNEES THAN THE MAN STANDING OVER HER... YOU MAY BE A SISSY.

And although I liked the idea of being either... I had to admit that at the moment I preferred being the girl.

The next one made me smile and laugh, even as I agreed with it. Two redheads (God are redheads hot) sharing only a single black cock. One girl had it in her mouth, while the other looked on in jealous hunger with the caption: IF YOU'RE AS JEALOUS AS THE GIRL WITHOUT THE BLACK COCK IN HER MOUTH... YOU MAY BE A SISSY.

And indeed, I did feel envious... I wanted to try a cock in my mouth... and in a perfect world it would be a big, black cock.

Fuck, do I need a cock in my mouth.

I needed to try it.

I knew that until I did, I'd be obsessed with curiosity.

The next one also made me smile, as I looked down at what I was wearing.

Panties.

Pantyhose.

As well as my robe, but that was just hanging open, leaving my girly attire fully visible.

The picture was a cute girl in a blue baby doll nightie and beige pantyhose, posing with the caption: IF YOU'VE EVER WORN PANTYHOSE... YOU MAY BE A SISSY.