"Sissified": 12 Days of Sissy-mas

I just sucked whatever was shoved in my mouth... and I jerked off whatever was placed in my hands.

I became a complete, bimbo, cock-sucking, cum-craving slut.

I was a sissy.

I was a cock sucker.

Maybe I was even a faggot.

I just wanted cock.

I just wanted cum.

I just wanted to please.

Every cock.

Every load.

"Thanks faggot," someone said, when I finally had an empty mouth for more than a few seconds.

"Thank you," I replied, as I scooped some of the cum from my cheek and put it in my mouth.

So good.

"Eat it all, cock sucker," someone else urged me.

And I obeyed, scooping cum off my face for a couple of minutes as I ate a mixture of many guys' loads.

So fucking good.

"Oh, God," a voice whimpered.

I scooped the cum from my eyes and finally opened them.

The bathroom was almost empty.

No one was in view. Just two pairs of legs in a stall.

I stood up and walked over to a mirror.

My hair was coated in cum.

My shirt had white stains all over it.

I listened briefly, "So big," some guy, most likely white, moaned.

Fuck, I was going to have to try a cock in my cunt, and soon.

I listened a little longer as the guy began moaning like a bitch in heat, before I walked out and headed straight to my car.

It wasn't until I turned the car on that I learned I'd been in there for over an hour.

Fuck!

I really was a sissy.

I saw a black man walk into the building and was tempted to get back out and follow him in... but I resisted.

Barely.

DAY 10: Thursday the 3^rd

I woke up the next morning, actually it was 12:30 in the afternoon, following my marathon suck fest at the college, and I replayed yesterday.

Wow!

I was a massive cock slut yesterday.

Just thinking about it made my cock hard.

So I headed downstairs for Day 10, a little sad there were only three days left.

I went downstairs and eagerly opened Box 10.

It contained a fleshlight and lube.

I read the note:

Kendra

I bet you sucked more than three.

I bet you ended up in the black bathroom.

I bet you are craving cock and cum right now.

Yes, yes and yes, I thought to myself.

Today no sucking cock.

NONE!

Today you will practice self-control.

You will watch porn and use the fleshlight.

You will bring yourself to the brink of coming... and then stop.

Wait for an hour and do it again.

You will do this at least six times today.

This is called edging, and it's an important part of being a sissy... Self cock control.

Mistress M

I took the fleshlight and lube and went upstairs and turned on a hot lesbian scene with Whitney White and Penny Pax called 'The Sex Addict' (it seemed appropriate).

I lubed up my cock, slid it inside the fake pussy and slowly masturbated.

I wasn't even five minutes into the video when I was close to coming.

So I stopped, barely in time.

Fuck!

I won't bore you with the details, but I repeated this three more times that afternoon, my cock aching, and was making supper when Bill showed up.

Fuck!

He asked, "Hungry?"

I replied, "Not today."

He laughed, "It was a rhetorical question, cock sucker."

"Bill, I can't," I objected.

"You can and you will," he insisted, as he saw today's note on the table and picked it up.

"Bill, no," I panicked.

But he read it.

"What is this?" he asked.

I sighed. I then explained everything, leaving out a lot of the details, like how many cocks I'd emptied yesterday.

"No way," he said.

"So you see, I can't suck you today," I insisted.

"Okay, I'll respect that," he finally agreed as he pulled his pants down. "But you can still jerk me off."

"Really?"

"Yeah, I'm horny and I can still give you a nice facial."

"Okay," I said, arguing to myself that I would be obeying Mistress M and still be getting the thrill of a load on my face.

I dropped before him and jerked him off.

Not going to lie... as soon as I was on my knees, I wanted that sucker in my mouth.

I imagine like a dieting fat woman with a cake a few inches in front of her.

Thankfully, he didn't last long before he came on my face.

Once done, he said, "I'm gone for the weekend, but when I get back I'll be texting you and I expect you to be ready to suck my dick."

"I will," I nodded, as I felt his warm cum cooling on my face.

He walked out, and I went and washed up.

That night I marked papers and edged myself twice more to the point my dick was aching... and for the first time ever, I had blue balls.

It sucked.

But I sensed this training would be rewarded tomorrow.

Or at least I hoped so.

DAY 11: Friday the 4^th

When I awakened in the morning, I found a text on my phone from Paige: Here's a little something I picked up for us in Amsterdam.

She'd attached a photo of herself, naked except for a large, black strap-on. She was holding a ruler next to it, demonstrating it was a hearty 10-incher.

I immediately texted her back. WOW! I can hardly wait for my stud of a fiancée to get home.

I headed downstairs, still a little raw down below, and realized someone had to have taken the picture of Paige with the strap-on.

Who could have taken it?

I went back upstairs and texted, dying to know: Who took the picture?

I stared at the screen for a minute or two waiting for a response, alas didn't get one, and headed back downstairs on my original mission.

To open Box 11.

When I did, I was slightly disappointed.

It was empty again, except for a note.

Kendra

Today you will be rewarded for yesterday's obedience.

You will go to Diva's Salon at 1PM. You will be occupied there for a least couple of hours... perhaps much longer.

Enjoy.

Mistress M

What else could be done to me at a salon?

I'd already had a complete body Brazilian. I didn't think I needed a perm.

I arrived on time and headed inside. Except for my panties and pantyhose, I was wearing ordinary guy clothing.

After establishing I was the Kendra Winston they were expecting, I was taken right back to a room, where I was left by myself after being told to remove my shoes and socks.

I did, and then assumed my pantyhose would be an issue, so I removed my jeans and pantyhose and then put my jeans back on, stashing the pantyhose in my knapsack.

Shortly afterwards someone led me to a larger room containing several stations, most of them occupied by women.

I was then given a manicure and pedicure.

I'd always assumed these were just for girls, but the pretty woman who did both for me explained that twenty percent of her clientele was men. And once they'd had one, they usually came back.

I could see why.

It was relaxing.

Especially the pedicure.

The hot water.

The massage.

The pumicing away of dry skin, especially from my heels.

The feet in a cozy warm bag.

It was weird, sure.

But man, was it relaxing.

They then trimmed and filed my nails.

Then... the first surprise... they painted my toenails.

Red.

I thought about questioning it, but I didn't. I assumed this was what was already paid for. What Mistress M had instructed them to do.

This was going to be even tougher to explain than the Brazilian.

Once done, the manicure followed, although thankfully they didn't paint my nails.

I was thankful for only a couple of minutes however, before they glued on fake ones, also red.

It hurt.

All of this was done without a word, although I did get a few peculiar looks from the other female clients. (Yes, I do realize that phrasing implied that I too was female.)

Once that was done, the woman ordered me to follow her and she took me into a room that seemed to be a photo shoot area.

Weird.

The woman instructed me, "Wait here. Amanda will be right with you."

"Okay," I said, wondering what was about to happen.

Of course, it should have been obvious.

Amanda walked in, a large but pretty woman, and said, "Welcome, darling."

"Thank you," I said.

"Ready for your photo shoot?" she asked.

"I had no idea I was doing one," I admitted.

"Well, that's why you're here, silly," she laughed in a boisterous way that made the room echo.

"So it seems," I said awkwardly.

"You're cute," she said, as she did a complete 360 around me that took at least a couple of minutes. She then ordered, "I think I have the perfect outfit to start for you."

"Okay," I agreed with trepidation.

"Follow me," she ordered.

I did, into a room that was deceptively large, filled with many racks of clothing, for both men and women.

She said, before disappearing into the abundance of clothes, "Please remove your shirt and jeans."

"Um, okay," I said, this feeling very weird.

I was soon standing in a room wearing only my pink panties, my dick awkwardly hard, for a couple of minutes before she returned.

She looked at me and smiled again, "Cute, very cute."

My face burned with shame at being seen in no more than pink panties. At least I wasn't wearing my pantyhose.

"Okay, first let's get you some titties," she said.

"Titties?" I asked, as she studied my flat chest.

"Want big ones?" she asked, before laughing, "of course you do, they always do."

She went to a dresser and pulled out what looked like two breasts and returned. "Completely shaved chest, good. Trust me, you don't want any hair when these girls come off."

"Good to know," I joked awkwardly.

She then grabbed the breasts and held them to my chest. She adjusted their placement for a good couple of minutes before ordering me, "Hold them right there please, and don't move them at all."

"Yes, ma'am," I obeyed, looking down and thinking Man, am I stacked. Then shaking my head slightly at my silly thought.

She grabbed an eyeliner pencil and returned to draw a circle around each breast.

She grabbed a spray can, shook it, and sprayed the back of the breast (I would later learn they're called 'breast forms' in case you were wondering... I mean if you're still reading this story, you may be a sissy too, and will want to experience this for yourself).

She then placed each breast directly in the drawn circle.

To my surprise, after about thirty seconds she removed them.

She then added something else I would later learn was called Skin Tac both to the back of the breast and to my chest. She said, "Now we wait five minutes."

"Oh, okay," I said, still finding it weird to be here with her in my panties only.

She walked back over to the dresser and returned with a pair of mocha stockings and a garter-belt. "Here, put these on."

"Okay," I said, completely overwhelmed by what was happening.

I put the garter on and then the stockings. As I did, she came over and helped with the clasps saying, "No dear, the suspenders go beneath your panties."

Once on, she came over and pressed the breasts back on me, after positioning each one carefully.

She backed away and studied the effect. "Perfect," she said. I wished there was a mirror for me to look at myself.

She grabbed a pink bra and fastened it on me.

"Very pretty," she nodded, as she brought me a dress. A gold dress.

She draped it over my head and zipped me up.

She walked away and returned to place a curly blonde wig on me.

She then had me sit down on a short stool and brought me a pair of silver five-inch heels. "Put these on."

I did.

"Are you ready for me?" a pretty Asian girl asked as she came in.

"Perfect timing," the woman said. "Doll her up."

"Yes, ma'am," the girl nodded. She walked over to me and for twenty minutes or so, she did my make-up. My eyes, my cheeks, my lips.

"Amazing," Amanda approved, coming back in.

"Thank you, ma'am," the girl said, standing up and leaving.

"All right," the woman smiled, "now let's take some photos."

"Okay," I said, speaking for the first time in an eternity.

I followed her out and saw there'd been a backdrop set up since I was last out there.

"All right," she said. "We'll take some simple ones first."

"Okay," I said, walking to the backdrop, which looked like it was a red carpet for the Oscars.

"Start at the end and strut towards me," she ordered.

I obeyed, trying to draw out my most feminine walk.

"Nice, good, good," she said approvingly, snapping picture after picture.

"Now pose," she instructed.

I did... really getting into it. I posed in a variety of positions, all while imagining I was a beautiful female celebrity.

She took tons of pictures.

"You're a natural sissy," she complimented, using that term for the first time.

Feeling so free and wild, I joked, "You should see me with a cock."

"I could make that happen," she replied without missing a beat.

"You could?" I asked, as she nodded and handed me an envelope.

I opened it. It was from Mistress M.

Kendra

Enjoying yourself? Of course you are.

The PG photo shoot is done.

If you don't want to do any more, you may call it a day.

On the other hand, if you feel adventurous and really want to explore your inner sissy slut, just tell Amanda, and she will do a much wilder photo shoot with a live model or two.

Be warned: there will be photos taken and you will almost certainly have a cock or two in both of your holes.

But this is up to you.

PS: The photos will be yours to keep and won't be used anywhere else (unless you give permission, as these photo shoots can be sold for a couple thousand dollars; ten grand if you're willing to have it all filmed and posted online)... although I will also receive copies, as will your benefactor.

Mistress M

PS: If you agree to this additional shoot, you may come.

Holy fuck.

My cock is hard as fuck.

I have permission to come.

I can suck cock.

I can get fucked by a real cock.

I can become a full-blown sissy.

I realized my initial thoughts were all about the sissy side... and almost nothing about the risk.

"So?" Amanda asked. "Are we done here or no?"

"I don't know. How would it work?" I asked.

"I'd give you a few choices of stories and actors, you would make your choices and then act it out," she said. "I would take photos and if you wish, it could also be filmed."

"Wow!" I said.

"It's a once in a lifetime opportunity," she said. "Should I show you the options?"

"Please," I said; it was at least worth seeing them.

She handed me a thin binder and said, "I'll be back in five minutes."

"Okay," I said, as I opened the binder.

SCENE 1: Gloryhole Surprise

You go to the washroom, sit down like a good girl and are surprised a minute later when a nice cock pops through a hole you hadn't noticed. You, of course, become intrigued, stroking it first. Then sucking it. Climactic cum shot is either:

a. He warns he is close, and you jerk him off and take a nice facial.

b. He comes into the stall, fucks your mouth and coats your face with his load.

Oh my!

Wow!

It was intriguing, but truth be told, I'd already done that.

SCENE 2: Step-dad's Dick

You come home late from a party dressed in drag. You wake up your step-dad and he tells you angrily if you want to dress like a slut, he will use you like a slut.

Note: this one includes simulated rape and will have you roughly face fucked and thoroughly ass fucked.

Cum shot can be on face, on ass, or in ass.

Wow.

The idea of just being taken was kind of hot.

Plus, it would get me past the insecurity of taking a real cock in the ass.

At the moment, this was exactly what I wanted: to suck a cock and to get fucked like a slut.

Before making this choice (if I was going to make a choice... although let's be real, was there ever really a question about it?) I figured I should check out all the scenarios.

SCENE 3: Black Attack

You're a teacher in your classroom. Two black students come in and are upset with their grades, calling you a racist. You defend your grading practices, but offer them a chance to improve their grades by doing some extra-credit work. The students decide to improve their grades by spit-roasting you.

Of course you protest, but once they show you the size and majestic beauty of their black cocks, you give in.

Cum shot options:

a. Double facial.

b. One facial one in ass.

c. One facial one on ass.

d. Two loads in ass.

Holy shit.

This was one of my actual fantasies that I jerked off to, on occasion.

To be seduced and taken at school.

Blackmailed or bullied into sucking cock... it didn't necessarily have to be black cock, but that added detail did indeed enhance the fantasy.

This one was the sure-fire winner.

Yet I kept flipping through.

SCENE 4: SISTER'S BOYFRIEND

You arrive home and your sister's boyfriend is there. Since you're in drag he sees that you're a sissy and decides since your sister is on her period, he should use you. He dresses you up in your sister's cheerleading outfit before using you for his own pleasure.

Variation: Sister is involved in making you a slut.

Cum shot: Face, asshole, or if using the variation, sharing a facial with your sister or even licking the cum off her ass, pussy or face.

Again, this was hot, but not as hot as scene three.

SCENE 5: WIFE'S GIRLFRIEND'S STRAP-ON

You walk in to see your wife getting fucked by a younger woman with a strap-on. The girl takes control and forces you onto the bed where she takes turns using both of you.

Cum shot: if you cum, you do it on your belly and they feed it to you with their fingers.

That would be an amazing fantasy come true if I walked in on that situation with Paige.

SCENE 6: CUCKOLDED BY WIFE'S BOSS

Your wife is working late and you go to drop off supper for her, but you walk in on her getting fucked by her boss. She demands you come over and watch. The boss fucks your face and your ass while your wife watches, and you are humiliated. It ends with your wife catching the cum and sharing it with you via snowball.

Variation: This could be done with an interracial slant if you wish.

Again, this was quite hot. Although the idea of tasting another woman seemed like cheating.

Now I know this is all cheating.

Yet, in my pathetic sissy mind, everything I was doing was something I couldn't do to Paige, so I rationalized it wasn't cheating.

Again, I know... pathetic.

But at the moment I was being led by submissive lust, not common sense.

SCENE 7: SHEMALE SURPRISE

You're cross-dressed and in the girls' washroom fixing your hair when a very pretty girl walks in. She too is checking her make-up in the mirror and notices you staring at her. She confronts you, pushes you down to your knees and surprises you with her cock and ends up using both your holes for her personal pleasure.