Sissy Awakening Ch. 01

"Where are we going?" I ask when I see we weren't headed for home.

"That shit wasn't cheap, you need to figure out how to pay for all that honey!" She said plainly

"What do you mean! I need to make money! I've made the money, I work a full time job!" I said shortly.

We pulled off the road and sat in silence for just a moment.

"You can either make money, or you can get out and walk home!" She said, not looking at me. I could see a small tear fighting its way out the corner of her eye.

We were maybe 15 miles from home headed into an entirely different city. I knew my way home but I also knew it would be absolute torture in these shoes. And if someone did happen to stop and offered a ride, that could be the best I could hope for. Violent ends await men dressed like myself, and I didn't want to risk any more tonight. I still didn't know where we were going.

Pulling through the industrial area of town, I noticed no homes or apartments. There were only businesses and warehouses. We pulled in to a stall, across the street from a bar with a couple guys standing out front smoking, mid block a flashing sign protruded from the block wall read 'XXX video booth' and on the corner stood two women barely covered in the hot summer nights heat. They were prostitutes!

"You need to make $200 before I give you a ride home" She softly said to me. "Either that, or walk home. Do you want to continue down this road?"

it was almost as though I were on auto pilot. I stepped out of the truck and stood, the door open and the safety of the truck on my left and the dark scary world to my right. With much fear and excitement I close the door of the truck and watched as she drove away.

"I'll meet you right here when you've made enough!" She said over the loud diesel motor of her truck as she left me standing alone in the darkness of the night.

There wasn't anything I could say as she left. I just watched as my best friend drive off, stranding me in the street, taking the only safety I had. I stood there for five minutes trying to decide where to go, until my feet decided for me. Walking as carefully as I could so as not to roll an ankle, i focused on each step. Toe first, then, just a microsecond after, heel. I couldn't walk like a man anymore, my stride was split in half. I'm sure I looked like a man trying to walk in high heels for the first time, but I felt like I was doing good. Tired from the exertion of trying not to fall, and my feet on fire I stood for just a moment on the sidewalk. The buzz of the flashing neon light brought me out of my trance like state and I realized I was exposed when 3 men rounded the corner near the hookers. Without thinking, I stepped through the door and into the sex shop.

The blinding light spilled out into the night, nearly blinding me. My eyes squinted hard to block out the light as they adjusted to the change. I could barely make out the rows of DVD's in the center of the room. Pictures of men and women engaged in lewd sex acts all arranged into categories, 2 entire walls of sexy costumes and clothes, games, toys around the outside. just to my left, the whole wall covered in dildos of all shapes and sizes. One huge black one caught my eye and I stared for a moment. It was roughly the size of a baseball bat but bigger around. I wondered to myself how practical it really was.

"The booths are in the back..." he said, pausing and then adding, "lady."

Could he really think I was a lady, or was he just being polite? I stood right around 6'10" and while hidden by professional hair and makeup, I still had quite strong masculine features. My arms and legs were still hairy, and my hands rough from years working construction. He had to have been being nice.

Walking without saying a word, I headed toward the back of the store to the video booths. I didn't have any money and didn't know what to do until I rounded the corner and saw the rows of booths spreading down the hall in either direction. Each had its own private door. I stepped into the booth directly in front of me.

Stepping in, I notice the floors covered in wet spots I could only guess were cum and a few used condoms lay with their contents oozing out the top. There was a small seat across from a video screen and a coin slot in the wall.

I gingerly sat on the seat across from the screen, not knowing what to do when to my right, two finger's breached the wall between the two booths. I reach out and pull the fingers a little when they are replaced with a crumpled $10 bill. Moments after taking the bill a small but growing uncut penis is pushed through the hole in the wall. Realization hit and I thought I knew what was expected of me. Reaching out, I grabbed the penis and gave it a slight squeeze. This was the first time in my life I had touched another man's penis and I wasn't repulsed. I was excited, I could feel the heat as his cock began to grow in my hand. Gripping the shaft I pulled the cock toward me. Without thinking I lowered my mouth to the head of his dick and took it in my mouth. Surprised by the softness of real skin in my mouth, I licked along the underside of the penis head. I was rewarded by a soft moan from behind the partition as the cock was pushed further toward my face. Giving light suction while moving my mouth along the shaft, I sucked the penis for about five minutes when, without warning, hot sweet liquid started filling my mouth. It wasn't a lot and really without thinking, I instinctively swallowed the what was in my mouth. I wasn't repulsed like I probably should have been, but slightly turned on. I had made a man cum! I did it, me and my mouth produced so much pleasure, a man came in my mouth! And I made $10 too!

Sitting there smiling to myself holding my $10 bill another bill was pushed through the hole in the wall on the left. This one was a $20, and then a large black cock was pushed through the hole. It had big veins poking out the sides and a mushroom head that looked like an upturned nose. It seemed to bounce there, slightly pointing up in the air. Touching it, the cock was hard and unyielding. A small dollop of precum dropped from the tip landing on my leg. Scooping it up with my finger, I brought it to my lips, stuck my tongue out and licked the cum off my finger. Salty but not like potato chips, I imagined egg drop soup. It made me want Chinese food, and his cock. I opened my mouth as far as I could to engulf the huge member. With my mouth barely covering the head I sucked hard, working my tongue asking the underside of the shaft like before. I could feel the ridges and ceases along the underside of his cock head. Jacking him off with both hands for 15 minutes, he erupted in my mouth, completely filling my mouth I tried to swallow as the second blast hit me tongue. The butter smooth texture of the cum felt wonderful in my mouth but the salty taste became bitter, almost like an unripe fruit. Streams of cum dribbled out the sides of my mouth and dripped toward my lap. Moving out of the way, I stood up and let his orgasm subside while I continued sucking on his head. I watched as the escaped cum pooled at the base of the hole.

Fingers were touching my ass, almost searching for pleasure and an unoccupied hole. Turning, I see a $50 placed through the hole! I snatch the money and wait for the cock to come through, maybe a little nervous from the last cock to come through. A thin cock with a pronounced downward turn is shoved through the hole and I am sucking on it instantly. I'm working the underside of his cock head with my tongue while jacking him off with my free hand when the cock is pulled from my lips.

"No, not your mouth!" I heard as the man on the other side of the booth placed his hard dick back through the hole.

"If he didn't want a blow job, what did he want?" I thought to myself.

"Gimme that ass girl!" The man said sharply as he pumped his cock in and out the hole. "Or the money."

His hand was now stuck through the hole in the wall. Palm upturned, and fingers doing a 'come hither' motion.

I didn't want to lose the $50 but I'd never been fucked in the ass either. I'd toyed around before with dildos and butt plugs, but that was a long time ago!

Resigned, I dropped my shorts to my ankles, undo the clasp on my crotch and placed my ass close to the hole in the wall. I reached back and spread my butt cheeks as he started poking at my ass cheek. I had to move my ass into the right spot and line my ass up with the cock.

Pushing out like I was trying to shit, I tried to accept the strangers cock into my unlubed ass. I pushed all the way back into the wall behind me as my unknown lover started pumping his dick inside me. The initial searing and burning pain turned into short small bursts of pleasure. I felt like I had to piss, almost like I WAS pissing as a steady stream of precum pooled on the floor below my. Reaching down, I ran two fingers through my own sticky stream, I wanted to taste myself! I swirled my precum around my mouth as my ass started to tighten and my balls exploded. Catching all my cum in my hand, I greedily lapped it up like a hungry dog. It tasted so good but felt so wrong in such a sexy way!

Another $20 bill was placed through the hole, right near my head. This booth was so small that with my ass placed firmly on one wall, I couldn't get my head down to another cock from the opposing hole. Taking the $20 I figured I could just give him a hand job as I was being pummeled from behind. Jacking the new guy off, I wanted his dark brown cock in my mouth, but the angle was difficult to work with. Straightening my neck like a sword swallower, I lowered my throat down in a line with the hole in the wall. The cock thrust itself deep into my throat and I began coughing and choking.

The man began grunting each time he pumped his dick into my throat and I became aware that I was loving what was happening. Where did these feelings hide? I was being fucked vigorously from behind while another man fucked my throat! I felt like an object of pure sexual desire.

My limp penis was now draining like a small faucet, the sticky stream slapping wildly below as my useless cock swayed from the torment in my ass. I swear I could feel the man in my ass start to tense up, and just as the cock buried deep in my throat started to erupt, I felt a flood shooting inside my intestines. The cock was buried so deep in my throat, I couldn't taste the cum at first but when I pulled away to clean him up I was surprised with a sweet taste that had a hint of spice hidden somewhere in the undertones. I'd have liked to had that load fill my mouth!

Half way there I thought to myself as I felt the cum drip out my ass and down my leg. It felt wonderful, I could feel a slight breeze as air was sucked into

My asshole in almost ached to be filled again. Licking my lips.

"That's either two in my ass, or between five or ten in my mouth to go." I thought.

Moments later, a crisp $5 bill was pushed through the hole behind me.

"Money is money at this point" I said aloud. And bent over taking the small penis in my mouth.

It wasn't until about 4am that I'd made enough money for Sarah to give me a ride back home. Walking back to the parking lot, I was glad it was still dark but the cool breeze was like ice wherever I had cum drying.

Standing outside the door of her big blue truck, Sarah stood with her arms crossed, tapping a foot impatiently.

"How much money do you have?" She asked.

"All $200, just like you said!" I said hoarsely.

"You have work in 2 hours slut... " she said, opening the door for me. Adding,

"A lot of things are going to change around here."

- Spa Day -

The drive home was quiet, and I was glad for it to be quiet. I'd done some things that I probably shouldn't have but I was so caught up in the evening that I'd done them anyway. I didn't feel bad for having done them but I wasn't ready to talk about it yet either.

Pulling in to the driveway just as the sun started coming over the horizon, I was glad there was still enough darkness to hide the mess I'd made of myself at the sex shop. I could feel the drying cum become crusty and start crackling as I walked to the front door. My body ached and both my throat and asshole were sore. I was headed right for the bedroom so I could undress and get ready for work when Sarah stopped me, and briefly hugged me from behind.

"Some things are going to change around here for a while babe. I'm going to ask you some questions and you need to answer them before we move any further, are we clear?" Sarah asked.

"Yes dear" I replied.

"Can you promise me you'll stop wearing women's clothes and be a man for me now that you've got that out of your system?" She asked

"I can't make that promise." I replied

"I've moved you into the spare bedroom for right now, until I can decide what kind of relationship we will have moving forward. Are you okay with that?" She asked.

"Um... I, uh, what, um, yeah... I guess I get that." I replied.

"Good, now then. You will do as I say, when I say it from now on. Do you agree?" She asked.

"Um... Yes dear" I replied.

"Okay, if you find something unacceptable with what I tell you, this is your chance, do you understand?" She asked.

"Yes dear" I replied again.

"Let me spell it out for you then... I've replaced all your boy underwear with panties. You'll wear panties only from now on. Clear?"

"You will accept any body modification requests I have and do it happily. Clear?"

"If you misbehave, or talk back, there will be punishments. Clear?"

"From now on I will only refer to you as either sis, or sissy. Is that clear?"

"And I may add to these rules whenever I choose. Okay?"

I nod yes to each of the rules. I was a little disappointed to be moved into another room, but she was right... things probably did need to change. I had certainly changed!

"Now go shower, and make sure you shave both your arms and legs. Don't worry about anything else right now." She instructed.

Stepping into the bathroom I dropped the shorts, kicked off my pumps, and dropped the blouse in a heap on top of it all. I finally got a good look at what a mess I'd become. It was hard to imagine that just twelve hours earlier I was standing in that very spot wearing the exact same thing but just starting my adventure into whatever I had become.

My hair had come out of the lattice pattern in a couple places, my lipstick was smeared all over my face, I thought I could see patches of stubble poking through my makeup too. The once beautiful teddy was quite soiled, spots from unknown sources were scattered across the whole piece. My pantyhose were running in two places and one of the claps had broke as well.

Pushing the thigh highs off my legs, they lay atop the pile like used up condoms. And dropping the whole teddy down free from my body left me feeling exposed. I longed to have it on already but lacked the time to keep it on right then. Reaching back, I felt the tender entrance of my asshole, and winced slightly at the pain. There had been 4 cocks in there that night. I was so ready for a shower!

Reaching into my hair as I let the hot water sooth the aches in my back, I started pulling out the seemingly microscopic rubber bands that held my now long hair in an intricate lattice pattern. The small free strands of hair snaked their way down my shoulders to tickle at my nipples. Deciding that I would just be rinsing my hair, I lathered up my hands and started washing my face off. I'd never wore makeup so I had no idea how hard it'd be to remove. Clamping my eyes shut tight I washed vigorously around my eyes, and almost scratching the entire surface of my face I felt the make up coming off in clumps. Rinsing off my face I noticed the stained water washing down the drain. I had gotten quite dirty through the night. Rubbing my soapy hands down across my chest I pause and pinch my nipples hard. I wondered quietly what it would be like to have real breasts. Lathering up my arms I take a razor just laying there and start to shave large clumps of hair off of my arms. Moving down to my legs it's much the same, I found it quite difficult to remove the hair from behind my knees and at the back of my thighs. Feeling my hairless arms and legs gave me a little thrill, and I noticed my cock begin to swell. Tugging at my penis I felt it engorge itself at the thought of being hairless. I tug for only a moment until I drip little streams of cum into my own hand. Placing the glob of cum at my lips I lick the pool to have a taste. It really isn't that repulsive like I used to think, so I lick the pool again, now taking a large glob on my tongue. Feeling like I'd had a decent taste, I washed the remainder from my hands feeling satisfied.

Stepping out of the shower I try to get my long hair to dry much like I had seen Sarah do so many times before, I flipped my head forward and dropped my hair down the front of my face I pulled a towel over the back of my head and spun the ends of the towel around my hair flipping it up over the top of my head I moved on to towel off my body. Once dry I noticed several patches of hair I had missed on my arms and legs. Using my Gillette shaver I ran small circles over each patch of hair until it was gone, then quickly shaved my stubbly beard and mustache clean.

Looking in the mirror I noticed my eye make up did not come off at all. There was no eyeshadow and my eyebrows were somewhat lighter than they had been but eyeliner and mascara lingered quite dark. Five minutes later with my eyes burning from the soap I realized I probably wasn't going to get to my make up off on my own.

" Sarah can you come help me please!" I called out almost frantically.

Stepping into the hot steamy bathroom Sarah looked at me with pity. Flipping the fan on and wiping down the mirror, she begin assessing the situation.

"What's the problem sis?" She asked me.

"It is this I make up! It won't come off and I don't know what to do!" I said frantically, and nearly in tears.

"Calm down, let me have a look." She said.

Tugging at my eyelashes, and scratching at the corners of my eyes she shrugged her shoulders.

"Sorry, we need a special make up remover. I don't have any so you'll just have to go to deal with it for right now." She said

"Bend forward sis, lemme help you with your hair." She said

She took the towel from my hair. Flipping my long hair up over my head to my back she began combing it out with a hair pick. Once it was all straightened she began patting it dry with a towel.

Lastly grabbing the loose towel at my waist she pulled it up under my arms and tucked a small corner in just under my right armpit.

"We can't be showing our boobs not even at home." She said to me as she slapped my ass.

Standing there feeling pampered and slightly humiliated as Sarah combed and dried my hair I wondered if all girls had this experience as their "mothers" helped them with their hair at one point or another. After blow drying my hair, Sarah dropped the pick and started braiding my hair down my back.

"You'll have to learn how to do this on your own. I'll help you for the first little bit but that's it." She said.

When she finished my hair, she kissed me on the cheek and patted my ass... saying,

"Off to work you go sissy!"

Standing in my new bedroom I looked around and saw that all of my effects had been moved. I was almost late so I couldn't waste too much time getting dressed, and thought, "What a waste!"

Opening the doors to the closet I saw all my pants neatly hung right next to my shirts. Opening the drawer in the closet I saw a pile of neatly folded panties laying next to several bras. remembering that she had replaced all of my mens underwear for panties, I snatched a pair that had caught my eye immediately. Holding them up I saw yellow nylon material with white polkadots in a cheeky cut, with wide white lace sewn onto the perimeter of each leg opening. they were super cute and I'd known I picked the right pair for the day when I slide them up my legs and into place. Pulled tightly they encapsulated my penis and slid delicately into my ass crack. They felt wonderful.