tagTransgender & Crossdressers"Sissified": 12 Days of Sissy-mas

"Sissified": 12 Days of Sissy-mas


Summary: Straight man is turned into a submissive sissy by....

Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross dressing, sissification, hypno videos, Tumblr gifs (so sad to see the site recently shutting down the porn aspect of it), stockings (of course), feminization, interracial, shemale, cum craving, sex toys, submission, humiliation, anal and even more.

Note 2: Thanks to Tex Beethoven, Wayne, goamz and Robert for editing.

"Sissified": 12 Days of Sissy-mas

DAY 1: Tuesday the 25th

It was Christmas morning when I heard a knock at my door, which was, of course, very odd at ten AM.

At noon I would be heading over to my family's for Christmas, and I seldom had unexpected visitors.

Still in my robe, I went to the door and was surprised to see a man standing there, holding a large box.

"Are you Ken Winston?"

"Yes," I replied, perplexed at his presence.

"This is for you," he told me, handing me the box.

"It is?"

"Yes," he nodded, as I took it.

"Who's it from?" I asked. There was no writing such as my, or a sender's name or address on the outside of the box at all. Just shiny green wrapping paper and a big red bow.

"I have no idea," he said, as he turned to walk away.

"How did you get the box?" I asked, this all seeming rather weird. He was dressed in regular winter clothing, no UPS uniform or anything. I had no recollection of ever seeing his face before.

"It was delivered to me to deliver to you," he answered unhelpfully.

"Okay," I said, finding this encounter very strange. I remained on my doorstep watching him walk back to the sidewalk, wondering whether he might climb into a van with some company's logo on it. But he didn't even get into a car; he just turned left at the sidewalk, then left again at the corner three houses down, and disappeared.

I took the large box into the house and into the kitchen. Curious, I opened it, where I found a collection of smaller boxes, and a pink envelope on the top saying in big bold letters: READ ME FIRST.

I opened the envelope.

Unfolded a letter.

It was addressed to me.

Dear Ken,

Merry Christmas!

You have been gifted with a very special, rare, 12 Days of Sissy-mas.

I goggled. Sissy-mas? What the fuck is that?

Okay, truth be told, I knew what a sissy was. I'd become a little intrigued and perhaps even slightly obsessed by sissy Tumblr pictures and gifs, as they recalled an obsession with nylons I'd had when I was a teenager.

I continued reading, both intrigued and baffled.

You will OPEN each box on the date indicated.

You will NOT open any of them early.

You will OBEY each instruction given without hesitation.

Do this, and you will find the sexual bliss that has eluded you for all these years.



Sexual bliss? I have a live-in fiancée, and she's great.

What the fuck?

Yet I also noticed the all-caps words... similar to the Tumblr gifs that so intrigued me.

You may be experiencing 'what the Hell?' at this moment.

I understand.

But it is my job to guide you through a 12-day journey that will culminate in a full discovery of who you really are, and all you are meant to be.

This was like the most fucked up fortune cookie ever.

Yet I was undeniably curious.

If you are wondering who sent this to you, I am someone who cares about you. And you are fortunate, as only ten of these box collections are given out each Christmas.

Only ten!

You are one of ten recipients in the entire world... yes, the world... to be presented with this intimate exploration of who you are and who you NEED to become!

This just kept getting stranger and stranger.

I'm one of ten in the world?


Who could possibly have sent me this?

The main thing I couldn't get past was the sissy reference.

I mean, I used to get off on wearing my Mom's panties and pantyhose to masturbate in back when I was in high school, but I'd refrained from doing anything like that ever since.

Oddly, the next few paragraphs added some clarity, even as they raised more questions.

In the past, gender roles were very clear: the man worked, the wife stayed home. But recently changes... from the feminist movement, to the cost of living, to redefinitions of common sense, have reshaped how society is run, and perceptions of stereotypical gender roles have evolved with them.

Calling a guy a sissy used to be the ultimate insult. It meant you were weak, pathetic, small-dicked, and an utter failure in fulfilling the responsibility of a man to be a provider and the head of the household. Of course even back then it was all a façade. Women have always ruled the home and have worn the pants, metaphorically speaking. Yet the perceptions we usually feel compelled to avow in public have remained decades behind what are becoming ever more common attitudes and practices in private.

Now however, with the growth of the #metoo movement, mixed with the power of the Internet, much of society at long last is changing openly. An increasing number of people are making lifestyle choices that they never before felt permitted to make.

Even as larger numbers of women are exploring their same-gender sexuality, so are men. The number of men who consider themselves straight, yet who nevertheless suck cock, has skyrocketed. (And I know that you, KEN, have in the past considered doing this.)

Shit, although this had never been a serious consideration of mine, I would be lying if I told myself the idea hadn't popped into my head on occasion. As I'd been scrolling through Tumblr gifs, or while I was watching porn and saw a girl sucking a big cock, I would sometimes wonder what her experience would be like. Then I would come, and afterwards be mortified by the 'gay' thoughts in my head.

I didn't find men attractive.

I wasn't gay.

I had a fiancée, and she was amazing. Our sex life was pretty good, although right now Paige was gone until January 5th (the last day of the 12 Days), spending Christmas travelling with her Mom (her dad long out of the picture... a story that perhaps one day I would learn more about) in western Europe.

The idea and even the practice of transitioning from a man to a woman, or from a woman to a man, has also increased in frequency, as has the acceptance in wider society of this self-realisation. Although many judgemental people are still critical of transsexuals, that number is dropping with every year that passes.

Yet what is happening more commonly now, is not so much the full transitioning to another gender (although that also is increasing), but rather the exploration of simply appearing and behaving as the gender a person wasn't born into.

In men this is often known as feminization or sissification, where a man gradually emerges as being more of a female in mind and spirit, although not in body. It is typically a systematic process of psychological change and self-emasculation, wherein a man learns to appear, to himself and to others, more like a woman. Sometimes he (or psychologically she) goes no further than simply wearing girls' undergarments (panties, bras and pantyhose), but may progress to more obvious cross dressing (the above in addition to heels, dresses, and wigs). Sometimes the person will progress to taking on roles that are typically perceived as feminine (sitting cross-legged, walking sultrily), sometimes even to a full feminine exterior (make-up, nail polish on toes and fingers, shaved legs) and sometimes he (she on the inside) will serve as a sexual being for another man (sucking cock or taking it up her cunt. (A sissy doesn't typically have an asshole, at least not during sex.)

Why was this collection of boxes and this dissertation being sent to me?

And from whom?

I paused and took everything out of the box and found twelve smaller boxes of widely varying sizes. Each of these boxes was pink, with a red lid and a white ribbon. Each had a white linen card attached to the ribbon, displaying a conspicuous number: one for each day of the 12 Days of Christmas.

I sighed.

Did someone know about my online searches? I had read it was too easy to hack into someone's laptop computer.

Equal portions of curiosity and frustration swarmed through me: I was intrigued by this letter and yet terrified that someone had discovered that I frequently checked out sissy gifs.

Understand that there is a major difference between a transgender transformation (which means physically changing genders) and becoming a sissy (where a man willingly allows his psychological masculinity to be compromised and perhaps even obliterated).

Also understand that unlike becoming transgender (which includes hormone treatments and surgery, and which is permanent), it is possible for a sissy to revert back to being a man, although that seldom happens. Once a sissy discovers her true self and allows herself to explore her true nature, she seldom wishes to go back. She will have discovered pure pleasure and fulfillment in the role of a submissive... a role that paradoxically is often even more fulfilling when it's humiliating.

And Ken, someone who cares about you has discovered that deep down behind your professional high school teacher persona, behind your outer manhood and even athleticism, is a deeply hidden secret: YOU'RE A SISSY!


Who would possibly think this?

Who would send me this?

So... are you ready to begin your journey?



What the fuck?

This is humiliating!

And that's when I noticed my cock was hard.

Don't deny it, you'd rather be a girl.

Wouldn't you, Kendra?

Maybe? I didn't know what I wanted.

Sure, I'd been intrigued by the sissy Tumblr gifs and captions, but I was also intrigued by incest videos (although I would never do that except in fantasy... I thought my mother was really hot), cuckold videos where a guy (often black) with a huge cock fucks someone's wife or girlfriend (also something I would never want to witness for real), and lately I'd developed a little interest in the idea of being pegged. I'd even joked about it with Paige after we watched Deadpool 2. She'd laughed at my joke, even saying maybe she should buy us a strap-on... but that was it.

Which was the point... fantasy is fun... as a fantasy.

If you are ready, go ahead and open the Day 1 box. Once you do, you will obey without hesitation every order I will give you for almost two weeks.

Do as I say, and I will lead you to understanding who you really are and to accepting your true purpose in life... being a sissy.

Mistress M

Mistress M?

I wasn't convinced I wanted to commit to twelve days of obedience to a complete stranger, but I had to admit I was curious.

So I picked up Box 1, which was larger than most of the others, and opened it.

Inside, I found a half dozen pairs of pink panties and a half dozen pairs of pantyhose in a variety of colours. There was also a note printed on a card.

DAY 1:

Starting today, beneath your clothing you will always wear pink panties, plus any colour of pantyhose you wish.

Go to your room right away and put on both.

Remember, you are to obey all my orders without hesitation.

Do not open Day 2 until tomorrow.

Mistress M

PS: Going forward, you're not allowed to have an orgasm except when you receive permission from either me or another woman.

I'd like to say I ignored the order.

I'd like to say I threw the box and the collection of lingerie in the garbage.

Of course, then I wouldn't have a story to tell.

Also, I wouldn't have embarked on my journey and while it may not be obvious yet, that would have been a personal tragedy.

No, I did exactly as I was instructed to do... with a hard-on and excitement.

I went upstairs to Paige's and my bedroom, opened my robe, stripped off my boxers, and slipped the pink panties on... God, they were so much softer and silkier than any male underwear. I would be lying if I said I didn't love the feel of them, as well as the way my hard cock felt as they slid snugly into place over it.

I then put on the pantyhose, oddly excited. It took a bit of time to get them on and to smooth the wrinkles out, but once they were in place, I noticed they felt expensive. They were glossy, which I found hot on women. They were sheer silk. They were the sandalfoot variety that displayed the entire toe, unlike the less sexy kind with a reinforced toe.

I was looking into my girlfriend's full-length mirror and tracing my hands up and down my legs, savouring the soft sensations on my hands, when my phone rang. It was my mother.

I walked over to my dresser to answer it, feeling oddly sexy and comfortable sauntering across the floor in the sheer hosiery. "Hi, Mom, Merry Christmas."

"Hi, honey," she replied. "Merry Christmas to you, too."

"How's the cooking going?" I asked. Mom cooked a full Christmas feast every year for over twenty of us.

"It smells amazing," she answered.

Playfully, I sniffed audibly. "Yeah, it really does."

"Silly! When are you coming over?"

"In an hour."

"When you stop at 7-11 will you grab a couple gallons of milk?" she asked.

"What makes you think I'm stopping at 7-11?" I questioned with a smirk.

"You always arrive with a slurpee."

"You know me so well," I laughed, my major addictions being porn and slurpees.

"See you soon," Mom said.

I hung up and couldn't help but picture my pretty Mom walking around in her nylon-clad feet all day. Although I didn't imagine it ever happening in real life, in the past few years I had spent many hours staring at Mom's stocking-clad feet, and then later jerking off, thinking of her and them. No doubt my nylon fetish is because of her. Not only did she wear them while she worked as a financial analyst, but also at home. She wore them every day, seven days a week, and always under a dress or skirt. Truthfully, I had never seen her in slacks or jeans. Not once. And as I mentioned before, as a teenager I used to wear her panties and pantyhose on occasion.

I put on a pair of jeans and socks, I sure didn't want to show anyone I was wearing pantyhose (there were no shoes allowed in Mom's house (yes, my Dad lived there, but it was Mom's house) ... ever). I put on a dress shirt I could tuck in, and then after I finished getting ready, I loaded some presents into my car and headed out of the garage.

I stopped at 7-11 and got my usual slurpee (Coke in case you care) and milk (1% in case you care) and continued on to Mom's.

I won't bore you with the day. It was fun, but typical. I felt slightly excited to be wearing panties and pantyhose. I had a hard-on for much of the day because of that, as well as from watching Mom and my Aunt Rosemary both pacing around on nylon-clad feet. And I couldn't ever get my mind completely off the obvious questions: who sent me the box? And why?

I got a new iPad and a few gift cards, and once I got home I called Paige, as we'd planned earlier. I didn't think it could possibly be she who'd sent the box... it wasn't at all like her. She was, in truth, a rather shy girl, although she could get pretty spontaneous and kinky when in the mood and nobody but the two of us were around.

She asked how my day had been, what I got for Christmas and so forth. I asked the same, but neither of us said anything to hint she had anything to do with the mystery box. I was certain she would have nothing to hint at, and I sure wasn't going to ask her... who knows how she would react.

After hanging up, I still wracked my brain with the obvious questions: WHO? WHY? WHO? WHO? WHO?

Of course, I had no leads at all... I couldn't think of a single person who would send me such a present, especially via such a generic yet anonymous courier.

No one knew of my crossdressing past, or of my more than slight curiosity with sissy gifs. I'd never shared this secret with a single person... ever.

This, of course, led me to wanting to go online and scroll through Tumblr, which had a wide variety of accounts I followed focusing on incest, cuckolding, interracial and, of course, sissies.

I couldn't help wondering over and over, Who the fuck is Mistress M? Is she someone I know, or someone hired to train me?

Train me! What a weird concept, but from some erotica I'd read, that seemed to be what Mistress M intended. I also puzzled over her prohibition to come. I felt some perverse compulsion to obey.

Why? I had no idea.

My cock had been raging all day.

My balls had been boiling all day.

Yet I used all my willpower and resisted, instead deciding to end my Christmas Day with the best Christmas movie of all time, Die Hard (yes, it's a Christmas movie).

DAY 2: Wednesday the 26th

I woke up still in my (my?) panties and pantyhose. I know that's pathetic, but now that I was wearing them for the first time in several years, I didn't want to take them off, and since there was no way Mom would catch me like there had been a risk of in the past, I figured why not).

Curious to know what was in the Day 2 box, I traipsed downstairs in just my robe, panties and pantyhose, not even pausing for coffee, and went directly to the box. I opened the box... this one very small and light as a feather... and saw it contained only a printed letter on a sheet of perfume-scented stationery.


How was Day 1?

Did you get excited putting the sexy panties on?

Did you rub your hands up and down your legs once the nylons were on?

Did you admire yourself in the mirror?

Did you feel sexy?

Were you horny all day?

Was your cock dying for release?

Did you obey me and not come?

Of course those are rhetorical questions, since I already know the answer to each of them is a resounding Yes; because you're a good girl, Kendra. Aren't you? Say it! Say out loud that you're a good girl, Kendra!

How could she know I'd done all that? How did she know I felt like that?

As I pondered, I heard myself say out loud, "I'm a good girl."

As I spoke the required phrase, I felt two things in rapid succession: exhilaration, then humiliation.

Why did saying it feel good?

Why did wearing these sexy lace panties and the sheer hosiery make me feel good? Sexy? Worse yet, natural? Why did feeling humiliated turn me on?

Good girl. With true obedience will come true self-discovery. With true self-discovery will come a realization of your true purpose in this world.

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