"Sissified": 12 Days of Sissy-mas

I grabbed the last note:

KENDRA

Although today is the last day... it really isn't. In truth, today is the beginning of stage two.

Stage two?

Today you begin the rest of your life.

What is she talking about?

Ready to find out who your benefactor is?

God, yes!

Ready to accept your place in the world as a cock sucking, cunt taking, sissy?

Yes!

Follow each instruction in order and don't skip ahead.

1. Take a shower and return naked to the box.

I quickly obeyed, resisting my urge to read the rest of the letter and rushing through a shower.

I wanted this final day to be special, and to last as long as possible.

I returned and read the next item.

2. Put on the garter-belt and stockings.

I obeyed, putting the garter on first, and then sliding the stockings on. Clasping the stockings to the clasps unassisted was more difficult than I thought, especially the back clasps.

So this task took me a good ten minutes to accomplish.

Like the other stockings, these were sheer silk and so fucking soft.

3. Put your tits on and then the bra (there are instructions in the box if you don't recall the exact procedure from yesterday).

I did recall yesterday, and did it the exact same way. It took me another thirty minutes to get them right, including going up to the washroom to use the mirror.

These tits were even bigger than the ones yesterday.

Today I was really stacked.

The bra made my big boobs look like they were home-grown.

4. Put the new plug in that cunt of yours.

I grabbed some lube and without much effort (after my anal/pussy training and yesterday's reaming) slid it inside me.

God, it felt good to have something inside me again, like coming home.

So natural.

Now I just needed something in my other fuck hole.

Fuck! I just referred to my mouth as a fuck hole!

5. Put your thong on (it should help keep your toy in place).

I put the thong on. It felt a lot weirder than panties, as the string went right up my crack.

6. Put on the sweater and skirt.

I did.

7. Put the heels on.

I did.

8. Put the wig on.

I did.

9. Text the word READY to the number on the bottom of this paper and wait.

I went to grab my phone and saw that Paige had texted me. I'm definitely going to fuck that pussy of yours. Yes, Mom took the photos and yes, she knows why I bought it. PS: She even gave me some tips on buying the perfect one for you (apparently she has pegged many guys in the past few years... go figure). She also explained it is a great way to balance the power hierarchy of the bedroom.

Wow!

Crazy.

A second text from Paige: No shame, Ken. I love you unconditionally and look forward to exploring our sexual identities together.

God, I love her.

Maybe she would be able to understand all I've been through while she was gone.

Maybe she could accept I was a cross dresser... a cock sucker... a bottom....

God, I hoped so.

I texted back: I love you too Paige, and am looking forward to doing EVERYTHING with you!

I returned to the box, found the number and texted it, assuming it would go to Mistress M.

I received a response: Be there in a few minutes.

Wow?

I texted back: Okay.

I finished reading the letter.

10. OBEY every command given you today without hesitation.

11. Stay home and wait... your benefactor will be over sometime today.

Mistress M

Was my benefactor coming over to fuck me?

My hard cock hoped so.

Yet, I wasn't sure I wanted to get fucked by anyone other than Paige.

Paige!

God, I wished she was here right now, as I began feeling that somehow she was going to be okay with all this. 'Unconditionally' was a pretty powerful word.

A few minutes later, the doorbell rang.

I walked over to it... in my heels, which I was pretty good in at the moment, and opened the door (wishing I had a peephole).

It was a young woman.

"Cute," she smiled, as she breezed inside right past me.

"Thanks," I said, as I closed the door.

"I'm here to do your makeup," she informed me, gazing around to take in her surroundings.

"Oh, okay," I said, as if that was obvious.

"Sit down over there," she pointed at the kitchen table.

"Okay," I nodded.

She then spent fifteen minutes doing my face and styling my wig. As she did, I thought how easy it was to be a man. No period of course, but also no lengthy morning war paint ritual and no shaving your body.

When done, she stood up without a word and left.

Weird.

Obviously, she wasn't Mistress M.

I then got a phone call.

From a number I didn't recognize.

I answered it. "Hello!"

"Kendra?" a feminine voice asked.

"Yes," I said.

"It's Amanda. I found three black actors for your scene," she said.

"Oh," I said.

"But unfortunately we can't film until tomorrow," she added.

"Oh, okay," I said, relieved, as Mistress M's instructions had been for me to wait here until further notice.

"Be here at eleven in the morning." she said.

"Sure," I agreed, knowing that Paige's flight was arriving at two. I could have one more wild adventure... day 13... before picking her up at the airport.

"Great," she said, before adding, shocking me, "your first video has already garnered over 7,000 previews, 673 paid downloads and twenty-four comments."

"It's online?" I demanded.

"Yeah, it was way too good not to release," she said. "I'll text you the web address, and tomorrow while you're here we can discuss what we'll need to pay you going forward. We don't want to lose a talent like yours, so a mere ten grand per shoot is history. Maybe you'll do better if we give you a percentage rather than a flat fee, but we can fine tune that as we go along. We'll also need to take some time to come up with a sexy name for you, unless you're happy to use Kendra."

"Okay, let's talk," I agreed, realizing there was nothing I could do to turn back time, and Amanda appeared eager to keep me happy long-term.

"See you tomorrow," she said.

"Okay," I repeated, in a sort of daze.

I received the website by text a moment later. I went upstairs to my computer, clicked on it and saw my scene was featured on the main page. I didn't watch the preview... I wasn't sure I wanted to.

I did read the comments, though:

-One hot sissy.

-God, I want that to happen to me.

-Best scene yet.

-That sissy is fucking hot.

-What a hot sissy. No one could fake those moans or that cum shot.

-I hope there are more scenes with this slut.

-Amazing believable scene. Hot shemale, hot sissy.

-Her cock sucking needs work, but wow can she take a cock and man, coming from getting fucked was so HOT!

-*****5 Stars*****

-I came twice.

-Best scene ever. I hope there is a sequel.

-Loved it. Only complaint... it is too short.

-Only a real sissy comes from getting fucked! I want to be a real sissy too.

-Love the nylons.

-God, I want that shemale cock.

-Please make more raw scenes like this.

-Best sissy on the site. I came when she came.

-Hot! Hot! Hot!

-That bitch is sexy as fuck.

-My cunt was on fire watching that scene.

-Sequel!

-Oh my GOD!!!

-That is a real sex scene. Sissy clearly loves cock.

-Best video website there is and this the best scene.

Wow! All were positive.

I was perceived as hot.

They wanted more.

Crazy.

Curious, now I watched the preview.

It was only thirty seconds long and showed me looking in the mirror, me on my knees, me sucking cock, me bent over, a close up of my orgasm face (which was so mortifying to see) and me ready for a facial.

It was hot and yet so disturbing.

I went back downstairs and poured myself some water, and the toy in my cunt suddenly began vibrating.

"Oooooooh," I moaned, from the instant pleasure. As I held the fridge door open, I wondered how the fuck the toy could just start buzzing by itself.

A moment later it stopped.

What the fuck?

I closed the fridge and downed the glass of water.

I started upstairs to watch the clip again... wanting to make sure I couldn't be identified (I was already pretty sure I couldn't), when the buzzing started up again, stronger than before.

I stopped walking and just allowed the pleasure to cascade through me.

Then I heard the front door opening.

What the fuck? I know I locked that!

The buzzing stopped again as I went back downstairs to the door, doing pretty well even on stairs by now in my five-inch heels, and froze as I saw the front door closed and my mother standing in my front entranceway.

"Hi, Kendra," she said with a delighted smile, looking me over and not at all surprised by my completely feminine makeover.

"M-M-Mom?" I stammered in shock at hearing her call me 'Kendra'.

"You look very pretty," she said. "I love how you look."

"Pretty," I repeated in a complete daze as I tried to process my Mom being here.

"You actually look a lot like me," she said, walking over to me after slipping out of her heels, which made me robotically glance down to her nylon-clad feet and red painted toenails.

"I do?" I asked, completely overwhelmed.

Now standing directly in front of me, she said, "If I didn't know it was you, I'd never guess who it was."

"Really?" I asked, struggling to process at least some of what was happening.

"Yeah, I thought the same thing yesterday," she said, walking around me. "But face to face is even better."

"Say what? Yesterday?"

"Your shemale video," she tossed off as if it should be obvious, and now bending over behind me, as she lifted up my skirt. "Even your ass in this skirt looks feminine and hot."

"You saw the video?" I asked, mortified by her words and also that my Mom was checking out my ass.

"Yeah, it was pretty hot," she said, before adding, "and I see you're just like your father."

"I am?" I asked, every one of my responses being almost monosyllabic and a question, and every vague answer from Mom only creating more questions.

"Yeah, he too comes from being pegged without having his dick touched," Mom revealed, as she moved a finger to my butt hole and tapped on the toy in my ass just as it started buzzing again.

"You peg Dad?" I moaned, again the question seeming already to have been answered.

"All the time," she bragged, as she allowed my skirt to fall back into place.

"Wow!" I said, my body trembling both because of my cunt plug's activity and from all these surprises.

Even though it should have been obvious based on all that was happening, I asked, the toy in my ass distracting me with its varied vibrations, "W-w-what are you doing here?"

"I'm your benefactor," she revealed, sauntering back around to face me.

"Y-y-you?" I stammered again, like I suddenly had a stutter I couldn't control, as I helplessly glanced again at her feet. "You're Mistress M?"

"No," she said shaking her head. "She's an online Mistress who lives in London."

"Explains the accent," I mused, my brain unable to process as fast as the reveals kept coming.

"Yeah, she has a sexy voice," Mom said, as the buzzing stopped again.

"Why?" I asked, wondering why she would do this to me. Or for me, as the note had told me on the first Day.

"Well, I've always wanted a daughter," she said, my being an only child.

"Oh," I said. I mean what else could I say?

"And since you liked wearing my clothes as a teenager and since you enjoy sissy porn," she explained, "I figured it was the perfect Christmas gift."

"For me?" I asked, unable to utter more than a couple of words at a time.

"Honestly, no," she said.

"No?" I questioned, now even more confused.

"It was partly for you, but just as much if not more so, it was for your darling Paige," she listed, "Besides, I didn't want to do it at all without getting her approval up front." Just as she finished speaking, the vibrations started up again. I looked at both her hands and didn't see a remote, which only added to the multitude of questions I didn't have answers for.

"What? Why?" I moaned, somehow even more confused after her answer.

"Well, I wanted to help you discover your true self," she said.

"My true self?" I questioned.

"Your sissy self," she clarified patiently. "I realize this is difficult to absorb all at once, but you can stop worrying. Your situation is far better than you can imagine."

"Oh."

"I thought it was important to give Paige the gift of having her own sissy just like the one I had," she added, taking my hand.

I didn't say anything, although a moan escaped my lips as the vibrations inside me sped up.

She led me into the living room, where the next surprise hit me like a ton of bricks.

"Hi, honey," Paige greeted, naked except for a pair of black thigh highs, a black leather bra with nipple cut-outs, and a strap-on cock... the ten-inch monster from the picture. God, did she look hot, but also rather frightening.

"Paige?" I gasped and moaned at the same time. "But you said you were arriving tomorrow!"

"I lied, darling. I hope you don't mind, but I couldn't resist the chance to see the look you have on your face right now. You're gorgeous, astonished, busted, forgiven and horny all at once! You, my dear sissy, are a perfect storm, and I wouldn't have missed this for the world!"

"Merry Christmas, slut," Mom interrupted us, as she walked over and kissed Paige.

On the lips.

For a good, long minute.

While they fondled each other's breasts.

When Mom broke the kiss, Paige responded to Mom's earlier greeting, adding yet another shock in a compounding domino of shocks, "Thank you, Mistress; and a Merry Christmas to you, too."

My eyes went wide. I stammered, "M-M-Mistress?"

"Sure," Mom nodded, as she unclasped Paige's bra. "You do know that I knew Paige before you met her?"

"You did?" I asked, this getting weirder and weirder.

"Yes, she was a temporary secretary for me for a few weeks," Mom continued, as she snapped her fingers and gently guided Paige to the floor.

I stared in awe as Paige stuck her head willingly under Mom's dress.

"She became my submissive pet," Mom explained, before adding, "and she still is."

I was speechless.

Dumbfounded.

Bewildered.

Flabbergasted.

Yet horny as fuck.

"She's an excellent pussy pleaser," Mom continued.

Finally I said, "I don't even know what to say."

"You can say thank you for my setting you two up in the first place," she offered.

"You set us up?" I asked, as she moaned, and I moaned.

"Yes, I made sure she went into Kennedy's Coffee shop while you were there, pointed you out through the window, and I had her walk into you, knowing you would think it was your fault, and then I encouraged her to seduce you," she explained.

I was again speechless.

Mom set us up?

That day I thought fate had brought us together, it was Mom?

Nothing I thought I knew was real anymore.

I was flabbergasted.

Speechless.

Bewildered.

"I didn't know you two would find love," she added. "I just thought you might be a good match. At the time I had no plans to turn you into a sissy."

"Wow!" I said finally.

"But then a couple months ago Paige found your sissy porn searches and rushed into my house, all upset," she continued as my fiancée licked my mother's pussy... although I couldn't see her doing it because of Mom's dress.

"I consoled her until she stopped crying at first, then I fucked her for the first time since I set you two up, and soon afterwards came up with this plan. First of course, I had to explain to her who you really were, deep down," she finished.

"How could you know I was a sissy deep down?" I asked, not disagreeing with her, but wanting to know. Needing to know. Trying to understand my own confusing, evolving sexuality.

"You showed all the signs: you're just like your father," she answered. "Plus, whether you've ever noticed it or not, you've always displayed a lot of feminine characteristics and mannerisms."

"I never noticed," I said, "except for my liking panties and pantyhose."

"I always knew about that of course, the amount of times I found dried cum on my panties and pantyhose was too many to count," she said, moaning softly.

"Sorry about that," I chuckled awkwardly.

"Don't be. I'm sorry I didn't do this sooner."

"What?"

"It's obvious you're a woman living in a man's body."

"Can't I be both?" I asked, not wanting to be restricted to one or the other.

"Of course," she nodded. "I don't mean to belittle your masculine traits. I mean, your cock is bigger than most sissies have."

"Thanks," I said, finding it weird to hear my mother praising my dick size.

"I'm serious, if you had a small dick, we would cage it," she said. "You know, like putting a tiny cock in a cage because it's useless except as a curiosity to look at."

"Oh," I said.

"Give me a moment, your sexy little cunt licker is really working Mommy's pussy," Mom moaned, as she rested her hand on the arm of the sofa and closed her eyes.

I was watching my fiancée lick my Mom, and Mom seemed about to show me her cum face. Never thought I'd ever see that!

Fuck!

"That's it, eat my cunt you eager little slut," Mom moaned. "Show your sissy-man your secret side before she shows you hers."

I noticed the pronoun change.

"Come closer and watch, Kendra," Mom ordered.

"Really?"

"Don't think I don't know about your Mommy fantasies," she said, raising her dress to reveal she was wearing crotchless pantyhose and my fiancée's face was buried in her wet, swollen pussy.

Feeling slightly brave, I said, as I stepped over to her and lowered myself to get an up close and personal look at this surreal sex act between two women I loved and lusted after, "I don't think you could possibly know about all the fantasies I have about you."

"Perhaps not, but for starters, you want to have Mommy suck your cock, you want to come all over Mommy's face, you want to fuck Mommy's cunt and pound Mommy's asshole," she listed. She then added, moaning, as she grabbed Paige's head and held her deep in her cunt, "And of course you want a nylon foot job."

"Don't forget eating your cunt and getting pounded by your strap-on," I added.

"How could I?" Mom laughed and moaned simultaneously as she turned her attention to Paige, "That's it sweetie, suck on my clit, get Mommy off."

Paige's head was quivering with intensity, as was her tongue, as she ate Mom's pussy like it was her final meal. God was it hot!

"Oh yes, fuck yes, eat my cunt, fuck, yes, you dirty fucking slut," Mom babbled as she came all over Paige's face.

When Mom let go of Paige's head, Paige turned to me and shoved my face into Mom's flooding pussy.

"Eat your Mommy's cunt, baby," Paige ordered me, holding my head as I did what any guy would do with his face shoved against a wet, leaking pussy regardless of whose it was... I got straight to work licking and swallowing.