Sissy Whore Ch. 01

Story Info
An online fantasy chat leads to a career change.
2.8k words
4.35
52.2k
44

Part 1 of the 4 part series

Updated 06/08/2023
Created 02/28/2018
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I suppose it started as a game really. Born out of the frustration and boredom of countless meaningless encounters with nameless men from chatrooms who would call to my house late at night. Although each proclaimed themselves to be dominant, still none seemed to live up to my own expectations, leaving me drenched in their seed but ultimately unsatisfied. It had become a regular routine for me to trawl the web searching for the next cock to suck. I never knew their names and few returned for a second helping. Despite my efforts to convey what I believed I needed and wanted, I had yet to meet a man who I was happy to invite to return for more. What relief I found invariably came as a result of hours of trolling porn sites. I'd read about the various cruising spots near me but never had the inclination to venture outside. I consoled myself with hours of watching porn and reading the accounts and profiles of others who were far away and seemed to have found what I yearned for.

I became addicted to sissy porn and began to experiment with makeup, heels, lingerie and wigs. Posted a few pics on my profile and began to attract a different sort of trade. Mostly these guys were closet married guys who described themselves as 'discreet' and were paranoid about being seen entering or leaving my apartment. But again, there was something missing from these encounters for me. Too much pretence and role play when what I really wanted was something closer to reality.

My cross dressing tendencies grew, spurred on by the countless hours of sissy hypno videos I devoted my spare time to. My confidence grew as my skills improved and soon I was heading out to gay bars and clubs in full female mode. I dreamt of getting my ears pierced and growing out my hair but would never commit to it. I settled for keeping my finger nails long and manicured and a total body shave every morning.

Some of the guys I met told me I was convincing but I knew that if they saw the real me, the me beneath the wigs, corsets and fashionable dresses, they wouldn't look twice. And at the end of the day the clothes and make up had to come off. I guess I became my own girlfriend. Designer clothes, expensive lingerie and, god, all those shoes.

Some of the videos and stories that turned me on the most were the ones concerned with hooker role play. You know the sort, a young skinny boy turned out on the streets and put to work at the hands of strict controlling pimp or Daddy. Some little bitch boy passed around from trade to trade like a shared joint. It was never more than just another fantasy that I toyed with in the empty hours before sleep.

Around this time, I was made redundant from my job and suddenly found myself with more and more time on my hands, time I spent playing with wigs and make up or glued to the laptop watching even more sissy porn. My wardrobe started to become more slutty in appearance. Thigh high suede boots, stripper heels, tight shorts and revealing mini skirts. I played with my make up skills, learning how to make my lips look bigger and applying heavy lashes on top of dark painted eyes. I was beginning to resemble more the fantasy hookers in my online videos than the convincing attractive girl of my dreams. I uploaded some pics to my online profile and started to get mails from Dom guys that claimed to be looking for the same thing, but none of them local. Just more nameless Daddy bulls from thousands of miles away who could certainly talk the talk but nothing could ever come from it.

With more time on my hands, I had more opportunity to meet guys, especially during the daytime. I had more than my share of afternoon hook-ups from older businessmen taking an extended lunchbreak for a quick blowjob from a fantasy tranny hooker. I'd come to the conclusion that this was all I could expect.

One morning, after scouring the web for some new job opportunities I decided to go online and check my messages. Taking time to slip into a pair of fishnet stockings attached to a sheer black basque with matching lace panties and my seven inch platform heels, just to get into the mood. While I was checking my messages the chat window popped up and out of boredom more than anything else I decided to play along.

"Where are you slut?"

"At home on the sofa." I typed back.

"Cunt, you should be working your patch."

"Where's my patch?" I sometimes liked to tease the time wasters.

"Don't fucking talk to me like that bitch! I'll knock your teeth in."

Something stirred in me, I was beginning to get turned on by this faceless stranger. 'What the hell', I thought, 'this might turn into something for the wank bank.'

I clicked on his profile and as expected there was not much to see. A blank picture and a brief description - 'Dom guy, Dublin'.

'Is that you in the pics?' He asked.

'Of course it is.'

'I don't believe you whore.'

I don't know what compelled me to do it, but wanted to shut this guy up. I'd encountered my share of time wasters and fakes and I didn't like being called a liar. I clicked the camera icon and my web cam sprang to life in the chat window, I jumped across the room to grab one of my wigs and place it on head in a hurry before sitting back down on the sofa in front of the web cam.

'You look like shit bitch. Put some damn makeup on.' Came his reply.

'That will take a while.' I typed. I wasn't planning on getting dolled up in the middle of the day so that some asshole could toss one off looking at my chat window.

'You better check your tone slut. I don't want to have to tell you twice.'

'I'm being serious' I typed, 'It takes about an hour to do my face.'

'You've got forty minutes bitch. Don't leave me waiting.'

His chat disconnected and I was left staring at my own boyish features reflected on my web cam window. I was pissed at this guy for some reason. I knew how this was likely to pan out. I'd spend the rest of my morning painting my face and be left waiting. On the other hand he certainly had a way with words that pushed all my buttons. I had a choice to make, if I got into girl mode then that was it for the rest of the day. I couldn't exactly go outside looking like a cheap whore. If this wasn't going anywhere, by the time I removed all the make-up and got back into boy clothes the day would be wasted and I'd be thoroughly pissed off. But there was something in this exchange that intrigued me and there was that leopard skin print mini dress that I hadn't had a chance to try on yet. 'Fuck it.' I decided. 'If he's a time waster I can play with my camera and get some new pics online. Write it off as a dress rehearsal.

I put down the laptop and skipped upstairs to the bathroom to slap my face on.

I decided to go heavier on the make up than usual. After all, I was just messing around. I shaved my face quickly and closely and applied a thick layer of pan stick foundation, taking time to work the pigment into my eyebrows to hide them a little before drawing them in again with dark brown brow shadow. I covered my eyelids in dark blue metallic cream shadow and worked the socket line with some black shadow, blending it out and high towards my temples. Next I dabbed some silver onto the centre of each lid and blended it all in. Next I took a thick black kohl pencil and lined my upper lash line, adding a cat flick to the outer edge of each eye. I finished off the lower lash line with some more black shadow before a thick coat of mascara on both my upper and lower lashes. Then I rooted around my make-up bag for a suitable pair of fake lashes and carefully placed them on top of my natural lashes, adding a second and third layer of mascara to seal the deal.

Then I applied a heavy contour to the ridge of my cheekbones topped off with some highlights beneath my eyes, on my forehead and below my lower lip. I chose a maroon mat lip paint and carefully lined my lip line with a dark wine pencil. I know you're supposed to do that the other way round but I'd learnt that it was easier to exaggerate my lips by lining them outside my natural lip line after they had been painted. A couple of heavy dabs of dark blush in the apple of my cheeks before blending and adding setting powder. Last, I took a couple of strips of surgical tape, stuck one on each temple and pulled them back tight, adding a subtle feminine arch to my natural brow. I took a second to clock my face in the mirror before deciding to dot a small beauty mark below my right cheekbone and pulling one of my favourite blonde wigs on top of my head to hide the ends of the surgical tape. Then I set the whole look with a layer of powder and set my mouth with a heavy coat of clear lip gloss.

This whole routine had taken most of the forty minutes so I rushed into the bedroom to stuff my C cup breast forms into the basque, squeeze into the tight leopard skin pattern mini dress and cinch my waist even more with a wide patent leather belt. Then I grabbed my thigh high suede boots and rushed back downstairs to the laptop. Pulling each boot over my stocking clad legs as I waited to see if the guy was going to show. In all I'd managed to make it within the hour that I'd estimated, and that was without the time I'd usually spend primping and preening in front of the bedroom mirror. With a little more time I'd have made myself a bit more presentable but I figured it was good enough to call this asshole's bluff via webcam. I grabbed a pair of large hooped clip on earrings from the coffee table as I was waiting for my webcam to pop up.

"You're fucking late bitch. I've been waiting."

The chat window popped open almost immediately.

"Sorry"

As I typed I realised I hadn't painted my nails, it wasn't really going to matter for a web chat but the realisation annoyed me a little.

"Sorry what?" Came the reply.

"I wanted to look good for you."

"Sorry SIR!"

Another chill ran through me as another of my buttons was pushed.

"Sorry Sir." I typed with slightly shaking hands.

"That's better slut."

My excitement increased and I felt the blood begin to rush to my crotch.

"Stand up, let me see what you're wearing."

I complied, giving a little twirl to show the shape of my ass.

"What size are those titties?"

"They're a C-Cup Sir" I replied.

"You need to get bigger ones and a lower cut dress. Big tittied whores make more money."

I was a bit annoyed by this. There are certain practicalities to wearing breast forms on a male chest. I started to think that this guy was just another fantasist. I've been there before with guys like that, it's impossible to live up to whatever twisted fucked up ideas they have in their heads. Their expectations formed by porn aren't really possible in real life. At least not without surgical intervention and I never saw myself going down that path.

"They're breast forms Sir. With a lower cut top they would be obvious."

"Bitch, I'm getting tired of your attitude."

"Yea well, I'm not here to play games."

There was no reply for a couple of minutes. I knew it. I thought. Another fucking dreamer.

Eventually a link popped up in the chat window with the words "Like these." I clicked on the hyperlink and my browser opened a page showing a latex breastplate with large fake breasts on a shopping site I'd never seen before. The breastplate came up to the neck and the join was hidden with a large necklace. They came in all sizes from D-Cup up to G. They were priced at six hundred dollars for the smaller set.

"I can't afford them Sir." I replied eventually.

"What?"

"I'm not working at the moment Sir." I explained.

"I can see that cunt. You're sitting on your sofa when you should be out making money, working your patch."

"I don't have a patch."

"Don't make me repeat myself again."

"I don't have a patch Sir." I was kind of mad at myself for feeding into his fantasy.

"What kind of whore doesn't have a patch?"

"I'm not a whore, Sir"

"Look in the mirror bitch. You look like a whore."

He had me there. I was still struggling on the verge of giving up on this guy but a part of me was inclined to take it as a compliment. I resolved to play along for now.

"Thank you Sir."

The screen went idle again for a few minutes. I was just about to give up on this when he eventually replied.

"Slut. I'm going to ask you some questions and I want straight answers. O.K?"

"O.K. Sir." I answered.

"How many cocks have you sucked?"

"I don't know Sir."

"Bitch I want straight answers."

"I haven't been counting."

"You forgot the Sir."

"I haven't been counting Sir."

"That many huh? Give me an estimate."

I did my best to do a literal head count. "I don't know, maybe thirty? Sir."

"When did you start?"

"A couple of years ago. Sir"

"OK so that's what? an average of one a month?"

"I suppose so Sir."

"You could do more than that. At least five a day I reckon."

"I had a day job Sir"

"But not anymore?"

"I got laid off Sir."

"How long does it take you to suck a cock before the guy cums?"

I'd never had a conversation like this before. I could feel my pride and denial urging me to quit but on the other hand, it felt kind of good to be talking about my secret life for once.

"On average, I'd say about half an hour. Sir"

"Hmm. I suppose that's O.K. given your lack of practice. Just imagine how quickly you could manage it with bigger titties. You could have them done in no time at all if you put the work in. Say ten minutes all in. Maybe four every hour if you allow for slow times. Even at bottom rate it wouldn't take more than a couple of weeks to pay of them titties. Then you're in profit. Add in a few extras and you'd have them covered in a couple of days."

"Extras Sir?"

"Fucking."

"Oh" I'd never actually done more than blowjobs up till now.

"You've never had a cock in your ass?"

"No sir."

"Would you like to do that slut?"

Of course I'd fantasised about being fucked but I was still kind of scared about doing it for real. Something had always stopped me from going all the way with a guy. It was a line I was never prepared to cross. Until now.

"Yes Sir." I answered.

"Good Girl."

I didn't reply. I was still processing what was going on in my head. Mixed emotions of excitement and shame conflicting my brain. After a few minutes he continued.

"I gotta go now baby. But I'll be back online in a couple of hours.

"O.K. Sir"

"We should continue this conversation. What's your number baby."

"My number?"

"So I can call you when I'm free."

I hesitated.

"I might be able to help you out."

"Help me out?"

"You've got potential baby. Gimme your number."

Without thinking I typed my cell phone number into the chat window.

"Good girl. You think about our conversation and I'll talk to you later."

The chat window closed and I was left looking at a blank screen. My mind racing with mixed emotions. I knew that in the course of that conversation something had changed in my mind. Staring at my reflection. Sitting on my sofa dressed like a whore. A cheap filthy sissy whore.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousabout 6 years ago
Abusive Dommes!

I'm not sure that I can empathize with abusive Doms, but the story shows promise. I'll read the next chapter and see if I'll follow it more.

Sissy_BillySissy_Billyabout 6 years ago
Great start!

Definitely looking forward to reading more. :-)

AnonymousAnonymousabout 6 years ago
Potential

This story, like you, has potential. Keep it up!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
Turning Him Into A Whore She turns him into a trick turning whore.in Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
More Stories