"Sissified": 12 Days of Sissy-mas

Ultimate effect... perhaps.

Easy to walk in... God, no.

Finally, her detailed advice:

1. When walking, place your heels first: as this stabilises your feet and gives you more balance.

2. Don't walk toes first: it looks and feels awkward and clunky.

3. Walk by placing one foot directly in front of the other: this is a great way to establish your signature walk.

4. When going upstairs, place your toes first.

5. When going downstairs, plant your entire foot simultaneously, and be sure to use the rail.

I'm not going to lie... at first the video didn't help me much at all.

Then I focused on how she was walking and tried to emulate it.

After a few minutes, a few stumbles and a fall, I was getting comfortable with my strut... I began to try walking sexily, as if I were on a runway.

I resisted going to online porn anymore... knowing I couldn't come without permission... so instead, I remained dressed as a girl and headed downstairs to grade papers.

It wasn't easy, as my cock begged for attention.

But I resisted like a good girl.

DAY 5: Saturday the 29^th

I slept in until almost 11AM, God, I love the holidays.

I had plans for the day: I was meeting a couple of buddies to watch basketball at my friend Derek's house.

I considered cancelling, but I really needed to get out of the house.

I had to get away from Tumblr.

Yet first, I had to check out today's task.

I opened the box and found two butt plugs and a tube of anal lube.

Today's task seemed obvious.

I was expected to explore anal with myself.

I read the note.

Kendra

Today we'll stretch your boundaries, and I mean that both psychologically and physically.

I expect you to wear the smaller butt plug in your cunt for four hours, and then to replace it with the larger one for the remainder of the day.

Of course... no coming. As a matter of fact, today you're not allowed to touch your dick at all, except judiciously whenever you pee.

Mistress M

No doubt anal sex had been intriguing me, especially yesterday.

What it would feel like to get ass fucked? Or in sissy language, to have my pussy pounded?

Yet like everything else, fantasy and reality were two different things.

I had breakfast, showered, and then examined the butt plugs more closely. The first was pretty small... the second a reasonable size... neither was massive, thank God.

I had to leave in twenty minutes and wouldn't be back for at least six hours, as we were watching a double header.

Feeling compelled to obey, I took the lube, coated the small plug, bent over, and gently pushed.

Nothing.

A little firmer push, and after a bit more resistance it slipped inside.

I moaned.

I'd expected a sharp pain... but all I felt was a slight awkward discomfort.

I put on my panties and pantyhose, which I assumed and hoped would keep the plug in place, added a pair of socks and jeans and a dress shirt that I tucked in to avoid any chance of the top of my pantyhose being seen.

Usually I wore my Celtics jersey to watch basketball games, so this departure would be noticed and I'd be called on it... but it was the only way to make sure if I bent over or something, the top of the pantyhose wasn't accidentally seen by anyone.

I walked around a bit, getting used to having something lodged in my ass that I intended to be there, and was surprised by how quickly I got accustomed to it.

I stuck the second plug and the lube in a knapsack and headed out, not sure how I would change plugs in four hours, but deciding I could figure that out later.

I sat down in my car and groaned as the plug was pushed deeper inside me... reaching new depths and providing me a bit more discomfort than before.

I drove over to Derek's.

Once I arrived, I was a little more careful when I sat down, and found that every time I moved, I could feel the plug shifting around inside me.

It felt weird, but good.

I took a razzing for the dress shirt, but I told the guys my jersey was dirty since Paige was gone, and I sure as fuck didn't know how to do my own laundry (which wasn't true, I did most of the laundry for both Paige and me, and I'd need to do some tomorrow).

We chatted like we usually did and once the first game was over... the 76ers beating the Raptors in overtime, I suggested we order pizza.

They agreed, and I offered to pick it up.

They said we should just have it delivered like we always do, but I argued that I needed to hit the bank, so I'd go pick it up.

They shrugged, figuring whatever.

I went out, drove to the pizza place, and went into the washroom with the knapsack containing the larger butt plug and lube.

I went into a stall, pulled down my pants, pantyhose and panties (the ultimate three P's...LOL), and pulled out the plug (two more P's).

The extraction made a little popping sound.

I wiped the plug off with toilet paper after dipping it in the toilet (I know: a little gross, but the better of two options, if you catch my drift) and stored it in the bag.

I was lubing up the larger butt plug just as someone entered the bathroom.

I tried to be quiet as I bent over and inserted the longer and wider butt plug into my cunt. (Yes, I was choosing to call it a cunt, but that raised a conundrum: if it was going into my cunt, then it couldn't be called a butt plug, could it? But if it wasn't a butt plug, what should it be called? I didn't think it qualified as a dildo. Enquiring minds want to know!)

Like the first one, my cunt resisted the invasion, but with a little extra oomph I was again full, and I let out a gasp, as this time there was a sharp pain.

I leaned against the stall door and got used to having the bigger toy inside me.

After a minute, I pulled up all three layers and stood up. Fuck, this was bigger.

I walked out, a little bowlegged as I tried to get used to my new passenger.

I went to the till, got my pizza and carried it out to the car.

I sat down gingerly, but the plug still forced itself deeper into me.

"Fuck," I groaned to myself at the discomfort... then noticed my cock was hard.

I drove back to Derek's and walked into his house, desperately trying to get used to the awkwardness before encountering the guys.

I set the box in the kitchen and called out, "Pizza's here."

They came in and grabbed slices and beer, and we all trooped out to watch the Celtics game.

I sat down slowly and very gingerly, and luckily the game was already on so no one was paying attention to me, and I ate my pizza and watched the game... trying not to shift around at all.

After a while I got used to it being inside me, which freed me up to change positions very cautiously on occasion. I felt a little slutty, knowing I was dressed in feminine undergarments beneath my clothes while sitting here with my best friends... and well... either I had a plug in my ass, or a toy in my cunt.

I did jump up once when Irving swished a three pointer with four seconds left to tie the game (unfortunately we lost with one second left, in case you care).

I made it through but headed home right after the game, wanting to get away without getting caught by my buds. During the afternoon I'd downed only one beer (a Budweiser, if you care).

I made it through the rest of the day, ending it with something having been in my cunt for ten hours... finally taking it out so I could, you know, go to the washroom and then to bed.

As I drifted off, my pussy felt a little empty and I wondered what it would be like to have something more active going in and out of my pussy.

Perhaps Paige pounding me with a strap-on.

Perhaps a black man reaming me with his massive cock.

Fuck!

Day 6: Sunday the 30^th

I got up, showered first and then feeling kinky, inserted the bigger toy (not calling it a plug) into me, before climbing into fresh panties and pantyhose. I then put on another of Paige's dresses and the red heels (although they didn't match the outfit), grabbed the laundry (I was now wearing my last pair of panties and pantyhose) and went down to the basement to toss my undies into the washer. For the first time in my life, I used the delicate cycle for my own clothes.

I then went and opened Day 6... realizing I was reaching the halfway mark of this surreal twelve days.

When I opened the box I found a red vibrator and a black dildo.

Oddly, this time there wasn't a note.

I was rather disappointed.

I looked at the vibrator and turned it on, discovering it already had batteries.

Was Mistress M expecting me to fuck myself with it?

I assumed so.

First though, I did what I did every Sunday morning... I called Mom.

We chatted for an hour... like we always did.

Although this was the first time I'd spoken to her while dressed as a woman.

I got off the phone, made grilled cheese and had lunch (I feel pretty confident you needed to know how much I love grilled cheese).

I went up to my bedroom, grabbed my laptop, and the phone rang.

It was a blocked number but I picked up anyway. Could it be...?

I answered, "Hello?"

"Cheers, Kendra," the sultriest English voice in history greeted me.

"W-w-who is this?" I stammered, even though such a greeting could only come from Mistress M.

"You know who I am, you silly girl," she responded, her accent so alluring.

"Mistress M?"

"Of course," she said.

"How did you get my number?" I asked, wanting to learn more about her.

"If I can get your address, how hard do you think it is to get your phone number?" she answered, giving me absolutely no intel.

"Fair enough," I said, feeling overwhelmed. Even over the phone, I felt awed by her presence.

"Are the heels on?"

"Yes, I assumed you would expect me to wear them," I replied, sounding so pathetically submissive.

"Are you used to them yet?"

"Getting there," I said, before joking, "you could have sent me a pair of wedges to start with."

"No need: I knew you would be a quick study."

"Thanks, but I still feel weird in them," I responded, for some reason wanting this conversation to continue for as long as possible: partly to learn more about her, and partly because her voice was so fucking sultry and hot.

"Practice makes perfect," she dismissed my concern.

"Okay."

"29 pictures and gifs?"

"Yeah, I guess I got carried away," I admitted.

"No worries. You may already be in the advanced stages," she said.

"Of what?" I asked.

"Sissification," she said, her tone implying the answer was obvious.

"Who set this up?" I asked, that being the question I wanted answered more than any other.

"I'm sure your benefactor will inform you when he or she sees fit," she said, before adding, "just be assured it's someone who cares, and is doing this for you!"

"For me?"

"Before Christmas, were you at all curious about sucking cock?" she asked, the word 'cock' sounding so hot with that English accent, almost as if it were spelled 'kawk'.

"A little."

"Be honest," she pressed, "only a little?"

"Well it was becoming more intriguing even before Christmas," I admitted.

"Good. And now?"

"Now it's all I can think about," I admitted to this enchanting stranger.

"Good girl," she purred, making my cock flinch.

"And do you want a kawk invading that virgin pussy of yours?" she continued, my cock once again flinching in my panties.

"Maybe," I answered timidly.

"Don't ever answer me with a maybe," she scolded. "It's a yes or no question, Kendra."

"Yes, then," I responded too quickly.

"Then maybe you need a nice spit-roast."

"That would be crazy," I said, having recently imagined taking a cock in both holes almost nonstop.

"It's what all good sissies crave," she explained.

"I guess," I said.

"Ready for today's training?"

"Yes."

"Yes, what?" she prompted.

"Yes, Mistress," I caught on, addressing her as 'Mistress' for the first time.

"Good girl. Go to your laptop, search for 'Rulestobecomeasissy' on Tumblr, and find the list of positions," she instructed.

"Okay," I said, going back to my bed and finding the account. The first was a gif of a brunette on her knees, in a short, very short skirt, sucking just the head of a cock between her lips, looking up at the man whose face was outside the picture, with the words flashing: SISSY POSITION 1: ON YOUR KNEES: the most natural position for a sissy.

"Found it," I said.

"Good girl," she approved. "Now get the vibrator and dildo I so generously left for you."

"They're down in the kitchen," I said.

"Go get them," she ordered.

"Yes, Mistress," I agreed.

"Good girl."

I put the phone down, went to the stairs, and walked carefully down in my heels. Step by step, planting both my heel and toes simultaneously and bracing myself on the rail almost desperately, still not doing too well on the stairs with heels.

But once I left the stairway I was able to actually saunter into the kitchen, flaunting my new feminine persona even though I had no observers, placing each new step directly in front of the prior one.

I grabbed the vibrator and dildo and returned up the stairs, toes first, again relying heavily on the rail for balance.

Back in the room, I grabbed the phone and reported, "I'm back."

"Get into the same position as the gif," she ordered.

I knelt.

"Copy it as best you can, using the vibrator as the cock," she ordered.

"Yes, Mistress," I said, as I held the vibrator in front of me with my right hand while taking just the head into my mouth, pretending I was looking up into the face of a woman standing before me with her strap-on in my mouth.

After twenty seconds or so, she said, "Move to sissy position two."

I did.

It said; ASS UP: Your most natural cunt fucking position. It was a woman on a bed lying on her stomach with her ass rearing up and a black man slamming into her from behind.

"Get into that position and position the vibe near your pantyhose clad cunt," she ordered.

"Yes, Mistress," I responded, getting into the position.

"Turn on the vibrator and place it at your cunt, Kendra."

I turned it on and it started buzzing.

"Put your phone on speaker and set it down near your face."

I did.

"Now press the vibrator against your cunt more firmly and hold it there."

I did. The vibrations tickled, making the plug still in my cunt also vibrate, and I tried to press it directly against it, but that was awkward. It did make me curious what this would feel like without the panties, pantyhose and toy cushioning the contact.

I'd almost forgotten I was on the phone because of being so lost in these unique pleasure sensations when the sexy voice told me, "Switch to position three."

"Yes, Mistress," I repeated, completely drawn in by her voice, and compelled to obey without hesitation.

This position was demonstrated by a skinny girl sitting on a couch leaning against the backrest, with a guy standing above her, his hands resting on both sides of her head as he face fucked her with the caption: Lean back and get face fucked.

I got into position leaning back against the head of my bed and said, "In a similar position, Mistress."

"Use the vibrator and face fuck yourself, my slut," she ordered.

"Yes, Mistress," I obeyed, a chill going up my spine as I heard myself called a 'slut' for the first time.

I pumped the vibe into my mouth; it was still buzzing.

"Don't hold back as you fuck yourself," she encouraged me.

I obeyed and got more vigorous, but I gagged when I pushed it in too deep.

She revealed herself as being skilled in interpreting my sounds when she told me to "Breathe through your nose."

I took her advice as I focused on breathing and sucking at the same time. Sure enough, I stopped gagging.

"Good girl," she purred.

After a couple more minutes she announced, "Final position. Get the dildo."

"Okay," I said, and grabbed it off the bed.

"Suction it to the wall," she ordered.

"Okay," I repeated, as I looked at the butt end of the dildo and realized it did have a suction cup.

I found an open space on the wall and placed it at the right height for my pussy, as it seemed pretty clear what was coming next. "Done."

"Lube it up," she continued.

"Yes, Mistress," I said, oddly excited that I was about to fuck myself.

"Ready to have that cunt of yours fucked?" she asked.

"Yes, Mistress," I responded, indeed ready to do just that.

"Good girl," she purred, as I lavishly lubed the dildo.

"What are you wearing right now?"

"Panties, pantyhose, heels, a dress, and I have the larger butt plug lodged in my ass."

"Oh my," she chuckled, clearly amused. "I never even told you to wear a dress: you get extra credit for that. You really are a sissy already."

"Thank you, Mistress," I responded absurdly.

"Now that I know what we're working with, pull down your panties and pantyhose, but only to your knees, and remove the plug from your arse," she ordered.

"Yes, Mistress," I said, the word 'arse' sounding so nasty.

"You should probably remove your heels too," she added, as I pulled the plug out. "Once you begin enjoying yourself, it would be a shame if you lost your balance."

"Yes, Mistress, thank you," I acknowledged, the anticipation of fucking myself growing in intensity.

"Now get on all fours, feet not knees, and slowly back up to the wall," she instructed, before adding, "this cock is a little bigger than the plug for that virgin fuck hole of yours."

God was this degrading.

But as I slowly backed up on all fours like a bitch dog, my cock was completely hard, and I was completely and willingly subject to her every whim.

"Yes, Mistress," I repeated, as if those were the only words I knew.

"You're such a good girl," she said. "You're going to be a great sissy slut."

"I hope so," I responded, as the tip of the dildo poked into my slightly gaped hole. God was I thankful I'd been wearing a plug for a while to prepare me for this. And, although this entire experience was baffling, and was crushing my masculinity, I really did long for what was about to come.

I was ready to be fucked.

I was ready to become a submissive sissy for real.

"It's time, Kendra. Press your cunt against your wall-kawk hard enough for it to penetrate."

I took a deep breath and leaned back, the cock going more easily into me than either plug had done earlier. I moaned as I self-penetrated. "Oh God!"

"That's it, let the kawk slide gradually into its natural home," she coaxed, her sultry voice making this seem so natural... like it wasn't at all weird I was dressed as a girl, on all fours, with a dildo sliding ever deeper into my 'arse'.

"Feels good," I reported, which was true, even though it was spreading my virgin pussy wide, and therefore causing me some discomfort and pain.

"Oh, wait until that cunt of yours experiences a real throbbing kawk slamming into it," she foreshadowed as she made it clear in a single sentence that there was much more in store for me... although with six more days to come (or not to come, depending) I guess that shouldn't have come as a surprise.

If I were a real man, or at least a stereotypical one, this would have scared me... and yet it didn't. If I were a real man, I wouldn't be on my knees with a dildo inside me. If I were a common man, I wouldn't be dressed as a woman.

So my next words came as little surprise: I'd already given in completely to this sultry stranger, and I said exactly what I felt at the moment: "I can't wait."

"Kendra, you may be the most natural sissy I've ever trained," she said; I was unsure whether it was a compliment, or a statement of how pathetic I was.