"Sissified": 12 Days of Sissy-mas

Cum shot options: She, not you, decides where to shoot her load.

Damn it.

Now there were two scenes I was dying to do.

Well, in truth I'd love to do all seven.

But a shemale was the ultimate attraction.

I could admire her feminine beauty and still enjoy her masculine cock.

Fuck!

I was re-reading scenes three and seven when Amanda returned.

She asked, "Make a decision?"

"It's hard," I said.

"I bet it is," she mused, peering down at my crotch.

I laughed, "Well, that too."

"Which ones are you most intrigued by?" she asked.

"Just the first seven," I joked... well, kind of joked.

"One scene is paid for already," she said. "Any extra ones you want to create will come out of your own pocket."

"Wait a minute. Isn't this prostitution?" I asked.

"No, because we're filming it. If call girls always brought a cameraman and some lighting along, maybe they and their clients could avoid any legal difficulties."

"Interesting thought. How much?" I heard myself asking.

"Seven hundred for a one-actor scene," she said, "plus two hundred more per extra."

"That's not bad," I said, thinking that over time I could enjoy doing a few of these.

"It's very reasonable," she said, before adding, "and any scene is free if you're willing for us to post the pictures online, and if you allow the video to go online, you can walk away with ten grand in your pocket."

"Wow!" I said. "Well, let's start with just one and go from there."

"Which one?" she asked.

"I can't decide between scenes three and seven," I admitted.

"Two very different scenes."

"I know."

"If you want to do the shemale scene, we can do it in the outfit you're currently wearing and begin in a few minutes," she said. "The classroom scene would have to be tomorrow or another day."

"Well, shemale scene it is then," I said, deciding I was definitely doing one now.

"Great," she smiled. "You have only two model choices who are available right away for this one."

"Okay."

She grabbed another binder and handed it to me. "Only Zoey and Channa are available now. Angela or Kim could be later tonight, and Winnie is out of town for a few days."

"Oh, okay," I said. I looked in the folder to see three pictures of each girl: One fully clothed, another showing her topless, and the last one a close-up of her cock.

Angela was a blonde beauty with an average sized cock and big tits.

Channa looked Filipino with small tits and a seven-inch cock.

Kim was Asian, very elegant and pretty, with small tits and a small cock.

Winnie was a brunette who looked a lot like Angelina Jolie, with huge tits and a massive (frighteningly big) cock.

Zoey was a gorgeous redhead with big firm tits and a nice eight-inch cock.

It was a no brainer.

"I choose Zoey."

"She's very aggressive," Amanda warned.

"Good," I said.

"Okay. Wait here," she said. "Someone will come and get you in a few minutes."

"Okay."

Then I waited.

Was I really doing this?

Of course I was.

It was then I realized I still had no idea what I looked like.

I looked around and saw there was a bathroom near the hallway entrance. I walked into it and looked in the mirror.

Wow!

If it weren't for my Adam's apple, there would be no evidence I was a guy.

I looked... hot!

Feminine.

My chest was voluptuous.

My make-up feminine.

Wow!

I wished there was a full-length mirror, so I could enjoy the entire package.

I stared at myself for several minutes, in awe of the transformation.

"Kendra," a voice called out, drawing me out of my daze.

I walked out and froze.

It was Amy.

A student of mine. She was an excellent student, was always courteous and well-spoken, diminutive, very pretty, and seemed to be well-liked. I was amazed to find such a sweet apple-faced girl working here.

Fuck!

"Follow me, please," she invited, not appearing to recognize me.

I didn't speak, I just followed her, keeping my head down.

We walked out of the room, down the hallway away from the street entrance, down a flight of stairs (as I learned this place was massive) and to one of eight rooms (I assumed each of them was for one of the seven scenes... I wondered what the eighth was for).

"Go into room three," Amy instructed.

I nodded, avoiding eye contact as she added sweetly, "Have fun."

She trotted back up the stairs as I walked into the room, my cheeks burning, but with a slight relief that I didn't think she'd recognized me.

I entered a bathroom setting, an elegant one.

A nice long mirror with a sink and wide counter. Three stalls with the doors closed. A couch which would ordinarily seem out of place, but in this upscale setting, it worked.

Amanda was already there with a camera, with another girl, in her twenties, with a video camera on a tripod, who asked, "Do you want a video?"

"Sure," I nodded, figuring it was only for me.

"We don't script the scenes, we just go with the flow," she explained.

"Okay," I nodded.

Amanda handed me a lipstick and directed me, "Go over to the mirror and reapply your make-up and so forth until Zoey comes in."

"Okay," I agreed.

"Great," she said, before she banged on the door I'd walked through a couple minutes earlier and called out, "One minute."

This was really happening.

"Action," she instructed me.

I looked into the mirror, pulled out my lipstick and reapplied.

God, was I nervous.

Although as mentioned before, I thought I looked pretty hot.

I was just running out of things to do when Zoey waltzed in as if she owned the place. Dressed in a fire red gown. She swanked up to the mirror beside me and stood there admiring herself.

I stared at her. Partly because that was the plot, and partly because she was fucking hot as hell.

She looked at me and asked, her tone harsh, as I stared at her huge tits and her hard nipples poking out against the dress (obviously she wasn't wearing a bra), "What the fuck are you looking at?"

"N-n-nothing," I stammered

"You're calling my tits nothing?" she demanded, turning to me.

"N-n-no," I stammered again, this feeling very real.

"You're the bitch who bumped into me during the catwalk aren't you?" she accused, glaring at me with venom in her eyes.

"Yes, I'm so sorry," I apologized abjectly, playing along.

"Oh, you'll be sorry all right," she growled, as she pushed me roughly to my knees.

"W-w-what are you doing?" I worried, trying to play the role of a shocked woman.

"Teaching you a fucking lesson," she answered, raising her dress to reveal a cock underneath it.

"Y-y-you have a penis?" I quivered nervously.

"It's called a cock, Missy," she corrected, wrapping her hand around it. "It's a big cock, and you know what it needs right now?"

"No, I..." I tried to get up.

"Sit back down, bitch," she roared, roughly shoving me back into place, "It needs a slut mouth to get it hard and ready for that cunt of yours."

"Please, no," I said, before she shoved her cock into my open mouth.

God this is so hot!

I swirled my tongue around her head in both fear and aroused eagerness to please as she moaned, "That's it, slut, get it nice and hard."

I kept using my tongue and my left hand as it hardened in my mouth.

Fuck, there was nothing better than the feeling of a cock hardening in my mouth (the vibrating butt plug being a close second).

Once it was hard, I began sucking energetically.

"That's it, get it nice and wet for that cunt of yours," she said. "I'm going to fuck the hell out of you."

I bobbed faster, showing her I couldn't wait for that... which was true... although I was also still quite nervous. Her cock was longer than my largest plug, and a similar size to the dildo so it wouldn't rip me apart... but a real cock seemed a whole new level of submissive debauchery.

"My balls too, cock sucker," she ordered.

I took her cock out of my mouth and slithered my tongue down her hard shaft and across her hairless balls.

I had no idea what I was doing, since Mr. Dawson at his desk hadn't given me any feedback, but I sucked her ball bag into my mouth and just as before, found one round ball.

I sucked it into my mouth and swirled it around gently.

I found the other ball and replicated the ball pleasing.

"Now stand up and bend over," she ordered.

I stood up, braced my hands on the counter for balance, and watched nervously as she stalked behind me.

"Cut," Amanda called out. "Lube her up."

The camera girl hurried over, raised my dress, pulled down my panties, lubed my asshole, finger fucked me for a couple minutes, wiggling three fingers inside (is this what really happened in porn? That would explain a lot) and then pulled out. She pulled my panties back on and returned to her tripod, cleaning her fingers with a wipe.

"All right, and... Action," Amanda ordered.

Zoey lifted my dress up past my waist and scoffed, "Fucking panties. Do sluts wear fucking panties?"

"No, ma'am," I apologized, as she roughly yanked them down to my knees.

"You're a dumb fucking slut," she said, slapping my ass smartly. She wasn't holding back, that hurt!

It was so humiliating.

So, of course, my cock was rock hard.

I weakly apologized, "Sorry," as I prepared to feel her cock fill my virgin hole.

She grabbed my hips, positioned her cock and slid easily in. "Fuck, only a slut is ever this wet."

"Oh God," I whimpered as she filled me.

She then fucked me for several minutes like I was a cheap slut made only to be used... which I was discovering might actually be my sexual calling.

It was the ultimate humiliating sexual high.

I normally loved being the one doing the fucking... but that was nothing compared to my being the receiver instead of the giver.

This is who I was.

A sissy for cock.

A bimbo for cock.

A fuck toy for cock.

And I loved it.

Each deep thrust sent intense waves of pleasure through me as I discovered how responsive my cunt was (truth be told, I was learning I had a very sensitive prostate).

I could feel every movement.... every twitch... every thrust.

It was like I was made to be fucked. I knew without a doubt I was a sissy. I knew vaginal sex alone would never again be enough for me.

Each nasty name she called me triggered increased mental euphoria because of the knowledge I was completely at her whim.

I was her bitch.

Her slut.

Her whore.

Her bimbo.

Her cum bucket.

The entire time my moans were feminine as I became my true self... as my body gave itself fully into acceptance of my sissy-hood.

I begged for more, this pleasure more intense than anything I'd ever experienced, "Oh please Miss, fuck me harder. Use me as your slut!"

I had never felt so good, and I knew I was going to come once again without having my cock touched. There was no way in hell I'd be able to control myself.

The fucking lasted only a few minutes before I could sense she was going to come... and that I might too.

"I'm going to come in your cunt," Zoey declared, as her deep thrusts continued.

"Yes please. Fill my cunt with your cum," I begged, as I felt my own balls boiling like the room was a hundred degrees. I was dying to know what it felt like to have cum spewed inside my no longer virgin cunt.

"Take it all, slut," Zoey ordered, and I felt her cock twitching as she tensed up.

I could feel her cock starting to pulse in my cunt, and then a lightness and warmth as she came inside me.

This triggered my own orgasm, as I screamed, "OH, GOD!!" reaching a powerful anal orgasm and spewing my load everywhere as my cock swayed every which way from the deep, hard fucking.

I went lightheaded and almost fainted as cum spewed into me while more of it spewed out of me, and I wondered if maybe I wasn't completely gay.

I mean I loved cock.

In my mouth.

In my cunt.

I loved cum.

Down my throat.

On my face.

In my cunt.

She kept fucking me throughout our simultaneous orgasms.

When she pulled out, she pulled up my panties and said, "You can keep my cum in your cunt as a reminder of who just bred you."

"Yes, ma'am, thank you, ma'am," I murmured weakly, completely spent.

She spun me around, pushed me back to my knees and shoved her cock in my mouth.

"Clean me up, whore," she ordered, yet one more delectable humiliation as I sucked her cock that had just been in my dirty fuck hole for several minutes.

I bobbed for a couple of minutes before she pulled out, pushed me onto the floor and said, "Thanks, slut."

As she strutted away, I said dazedly, "No, thank you."

A moment later Amanda said, "Cut."

"Holy fuck, that was amazing," the other girl said.

"Did you get him coming all over the place?" Amanda asked.

"I sure did!" the girl exulted.

"This will be a huge seller," Amanda said.

"I've never seen anyone come just from getting ass fucked," the girl said.

"Me neither," Amanda said, as she snapped her fingers and the girl immediately dropped before her, under her dress and began licking.

I stared in awe at my first live lesbian show... until I realized the girl was bobbing. I looked more closely and realized Amanda too had a cock... and (how did I miss this until now?) also an Adam's apple.

Amanda said, "Come back tomorrow. We'll do the black cock scene for free."

I asked, "Really?"

"Oh yes," she said. "You're a natural."

"A natural?"

"Natural porn slut," she elaborated.

"This video is just for me, right?" I asked, no longer so sure.

"We can chat about that tomorrow," she put me off. "This could be a huge scene."

"Really?" I asked, more flattered than worried for some reason.

"A sissy who comes without having his cock touched is like a needle in a haystack," she said.

"Oh," I said.

"We may be able to turn this into a full feature movie," she continued.

"I already have a career," I pointed out.

"You may need to change careers," she refuted, as she grunted and came in the girl's mouth.

I got up and said, "I can't believe I just did that."

"I can't believe how raw and real it was," she replied.

"It was my first anal except for a dildo," I pointed out.

"Fuck off," she gasped.

"Seriously," I said.

"Well, that in itself will double the popularity," she said, as she added, "Susan, get this to editing."

"On the double," Susan agreed, getting off her knees and grabbing the camcorder.

"You won't release it without my consent, will you?" I asked.

"Of course not," Amanda said, but in a tone that told me it would be released with or without my consent. "Keep the dress and lingerie, and you can give me a call in the morning."

I took the card she handed me, and she left.

I stood there for a full minute in a complete daze.

I had officially fallen in deep.

A minute later the door opened, and my student Amy beckoned, "Please come with me."

I followed her up the stairs and back to the original room.

"That was such a hot scene," she gushed as we reached the changing room.

My eyes went wide.

I stammered, "Y-y-you saw it?"

"Of course. It was streamed live into our office," she explained cheerfully.

"Oh God!"

"Yup. That's what you screamed when you came," she said. "Without your cock even being touched!"

I kept avoiding eye contact with her but learned it was futile as she added, "It was the hottest scene I've ever seen, Mr. Winston... sorry, Ms. Winston."

Fuck!

I pleaded, "Please don't tell anyone, Amy."

"Of course not," she said. "What happens here, stays here."

"Thank you," I said.

"But I have to tell you since we still are here," she said, "you dress up as one hot girl."

"Thanks," I replied awkwardly.

"And since I know a secret about you..." she offered, lifting up her skirt and revealing a rather large cock where her cunt should have been.

"Oh my," I gasped, staring at my student's hard cock. Is she hard because of me? She did call me hot.

"If you ever need a cock to serve at school, just let me know," she smiled, "I wouldn't mind having a third teacher pet."

"Third?" I asked, shocked just as much by the big appendage between her legs as by the implication she was fucking two of my colleagues.

"Yep," she smiled, as she put her cock away.

"Who?" I asked, curious.

"I don't fuck and tell," she said. "But one is male and the other is female."

"Wow," was all I could say as I began mentally going through all my colleagues.

"See you at school on Monday," she farewelled.

"See you, Amy," I said, as she walked out, and my secret sissy life was now even less secret.

I found my clothes, changed out of the dress, laboriously ripped the tits off my chest, but kept the garter and stockings on, put on my jeans and shirt, put the dress in a bag and headed home... my head spinning... what had I just done?

What could possibly be next?

Could I stop this downward fall?

Did I even want to?

Fuck!

Back in my car, I saw I'd missed a few text messages from Paige.

What are you doing today?

I went lingerie shopping with Mom today. You won't believe what she bought me.

I'm learning a lot about my mother I DID NOT know.

Off to bed... a picture for you to jerk off to.

It was a picture of her wearing the same strap-on as before, but now she was also in black thigh highs and boots and a black leather bra. The makeup on her face looked completely Goth. She looked like a formidable Mistress.

Fuck!

Did her Mom take the earlier photo?

This photo too?

Her mother looked exactly like Paige, just in her late forties. She was a very flirty woman who touched my arm often, dressed like she was in her twenties (she dated guys in their twenties, some of them younger than me) and even had grabbed my ass twice (both times while drunk). She even joked once that if she'd met me before Paige had, she would have been "all over that" (while she pointed directly to my crotch).

So in retrospect it was obvious her mother must have been the one who took the pictures.

Fuck!

Nothing in my life made sense anymore.

And now that my Pandora's Box was blown wide open, there was no going back.

The question wasn't whether I was going to tell Paige at some point... the question was how the hell I could do it without her blowing up in my face.

I texted her back: I can't believe your mom took that picture. What did you tell her? Does she know you are going to pound my pussy when you get home?

I pressed send and then noticed I'd called my ass a pussy.

Fuck!

I sent another text: Oh, my God why did I just write that? See you soon.

Since it was late on the other side of the pond, she was clearly asleep, I didn't expect a response.

That night I tossed and turned for a while, worried what she would think of my response.

Day 12: Saturday the 5^th

Tomorrow there would be no box.

Tomorrow Paige would arrive back home.

Tomorrow if my world didn't crash and burn, everything might return to normal.

Although... what would normal now mean?

Could I go back to before these watershed days?

Could I quit sucking cock cold turkey?

After yesterday, could I resist my cravings for a cock in my ass?

Could I become straight again?

Did I want to?

Could I?

Was I going to make that second movie today?

I had just gone two whole days without a black cock.

That seemed like a long time.

Shaking my head at my dependence on these 12 days, I went downstairs to open my final box, which was larger than any of the others.

It included: a strap-on cock with a harness; a white garter-belt and matching stockings; a new butt plug; a white bra; a white thong; another pair of tits and the accessories needed to glue them in place; a red sweater; a green and red plaid skirt; a blonde wig; and finally a pair of five-inch stiletto red heels.