Turning Sissy - Week 05 Pt. 01

ATTN: All characters are purely fictional. All characters are over the age of eighteen. This story contains elements of reluctance and non-consent.

We didn't have much contact in the following few days. It was Thursday by the time he had contacted me again. I hadn't done much in the days after Halloween, surrounded by shame at what had happened. I had begged him to alter our deal, begged to suck his cock. I tried to push the events of that night out of my mind but for at least two days after, I would occasionally smell his cock, despite my thorough showering. It's like the aroma had stuck to me somehow and there didn't appear to be anything I could do to get rid of it. I was dreading our next meeting more than ever knowing what he could do to me, or rather, have me do to him.

When he finally did contact me, it was for a full day session, so he had me meet him for 9 am Friday morning. He picked me up and we drove into the city with little conversation. I was wearing the plug he had requested and it was feeling uncomfortably large causing me to shift in my seat constantly.

"Can't get comfortable? Your ass can't still be sore from Halloween." he commented.

"No... It's just... you know, the plug. It's... big." I admitted.

He let out a loud laugh.

"I forgot I told you to wear that. Hang on."

He pulled over into a parking lot and turned to me.

"Okay, show me. Get your ass up." he said.

"Here?" I asked.

There wasn't a whole lot of traffic but cars were passing at a steady rate.

"5, 4, 3-" he counted, and stopped before seeing me get into position.

He pulled my pants down and grabbed the plug firmly, pulling it out slow. I felt the ridge of the cock head pop out of me and I let out a squeak. I pulled my pants up quickly and sat back down and he handed me the plug.

"Put it in the glovebox." he said.

At some point on the highway he took my hand and put it on his crotch, but thankfully nothing else was asked of me.

Our first stop was a beauty salon, and as we entered, the woman at the front desk greeted my master by his name. As they made small talk it became abundantly clear that I was not the first boy he had brought here.

"This one is cute! She's halfway there already. Don't worry about a thing, when we are done with her she will be just how you like them."

I was guided into the back and introduced to my esthetician, May, and asked to strip naked. My clothes were taken away and I was brought to a padded table. Before laying down, May produced a small key and unlocked my cage and removed it.

"Have you ever been waxed before?" I was asked before enduring the most painful hour of my life.

They began to spread a cream over me afterwards that felt cool on my skin and made me feel tingly.

"What's this?" I asked May.

"It's a soothing cream. It has some other stuff in it to stop your hair from growing back... At least for the next few months."

Months. I was now going to have a bare smooth body for months. As it sank in, I wondered why that was necessary when I only had four more days left owing to him after this one.

"We do laser removal too if you ever want something more permanent." she added as if I liked not having hair.

Soon the cream was washed off and I was given a robe and brought into another room. May had me sit in a chair and began working on my hair. She was brushing in some sort of paste and wrapping it in tin foil. I gathered pretty quickly that it was hair dye and realized that he was redesigning my look to suit his preferences. Soon the dye was washed out and I was sat down in front of a mirror. My hair was now a light pink and it took some adjusting to understand it was me in the mirror.

May spent the next hour going over hair styles and make up with me and when we were finished, I had a very cute natural look accentuating my lips and eyes with light lipstick and dark mascara and eyeliner. My hair, was left in a high ponytail with long bangs in the front.

"Where's the sink?" I asked before she took me back to the lobby.

"Oh no honey, you're keeping this on. Come to the wardrobe room, we will give you an outfit."

In the wardrobe room I was handed white cotton panties and a training bra. Next was a denim miniskirt with attached suspenders and a yellow crop top. I was given white stockings with rainbow stripes at the top around the thighs and pump sandals to complete the outfit.

"And one more thing." May said, holding up the cage with a smirk.

As I walked out into the lobby, my master beckoned and then led me back out to the car quickly.

"We have two more stops." he said, "I can't wait till we get home. Get started now."

He undid his belt and pulled out his flaccid member before starting the car and leaving the parking lot.

"Right here?" I asked, knowing the answer.

He didn't respond and I froze. We were driving in a pretty populated area and I was terrified someone might see. He cleared his throat and, reluctantly, I unbuckled my seat belt to allow myself room to work. As my head neared him I was hit with that familiar smell that I had only just ridden myself of. I took him into my mouth immediately and felt his hand rest gently on the back of my head. His cock began to harden as I sucked and massaged with my tongue and lips, every bump in the road causing my head to push further down.

The drive was quicker than I expected and soon enough I felt the car come to a rest and back into a spot. Gripping my pony tail he pulled my face off his dick and vegan rubbing the head and foreskin around my lips and chin, marking me with his aroma once again.

"Let's go." he said, finally releasing me.

When I got out of the car to follow him I saw the name of the business and stopped dead in my tracks.

"No..." I said quietly.

It was a tattoo shop. There was no way I was going to allow him to put any sort of tattoo on me. Not for all the money or blackmail in the world.

"You're not getting a tattoo. Come on" he reassured me pulling me by the hand.

I felt embarrassed walking into the shop with him, even with the fact that I was so convincing that everyone might assume I was a real girl. He was just so old and I was so young and pretty in comparison, it didn't make sense. That was an upside, I thought to myself. At least I was just a girl now to anyone who saw me, I didn't have to be embarrassed about that.

"Well long time no see!" the girl at the desk immediately came around and gave him a big hug and kiss on the cheek before doing the same to me.

"And who's this pretty one? Niece? New girlfriend?" she asked.

"No, this one is for work." he said.

"What? Really? I mean I thought the last one was good but this one... There's just no way..." she exclaimed.

She was looking at me in a funny way now, part admiration, part curiosity. Eventually she shook her head and spoke again.

"Okay, well I'll tell Dale you're here. The usual?" she asked.

"No no... This one isn't quite committed to it yet, just ears and bellybutton. We will do some temporaries as well, I think Dale still has the ones made up from last time." he responded.

"He does, we were just looking at them the other day. I gotta say I'm surprised you got one that close." she began and then looked at me shaking her head once more in disbelief.

Soon enough I was in a chair in the back with Dale sat next to me. He was readying a piercing gun and after some small talk with my employer he turned to me.

"You ever been pierced before?" he asked.

"Nope." I answered curtly.

"Okay, well, it shouldn't hurt that much... At least after the first pinch. Here we go."

It hurt a lot in fact. The second one might have even hurt more but the endorphins must have kicked in. He gave me a couple tylenols and let me wait five minutes before putting in the bellybutton ring. When I had recovered from that pain he handed me a small album and I was told to flip through it, and pick two of my choice.

"Your daddy's picking the third. His rules. Don't worry about getting weird with it, they are only temps. A week or two max."

The book had twenty or thirty tattoo designs ranging from cartoon cocks shooting cum to 'cum slut' in cutesy lettering. I really didn't want to choose and the pain I was feeling in my ears and bellybutton was excruciating.

"He can pick all three." I said, biting down to fight the pain.

"Wow, that's a first." the artist said, handing the book to the man who brought me there.

The tattoos were applied just above my groin, on the backs of my thighs, behind my ear, and on my lower back. I wasn't given the opportunity to see any of them before he ushered me out of the shop. Walking by the window I caught a glimpse of the big silver hoop earrings now on my ears. Seconds later we were back on the road and his cock was halfway down my throat.

The last stop was another store, this one a sex shop. He pulled out a list and began reading it in his head. I knew that going inside was going to be embarassing but it would be even moreso with him. I but the bullet and spoke up.

"I can go in for you if you'd like... You know, get whatever you needed on that list."

"Oh you, will. And I'll be with you every step of the way." he began, handing me the folded up paper, "Here's the list. You can take a look when we get inside."

As I stated at the paper my heart sank. There was no way I could do this without passing out from embarrassment. I looked at him horrified, shaking my head rapidly, tears forming in the corner of my eyes.

"Please..." I said quietly but I knew it would fall on deaf ears.

He exited the vehicle and came around to my door and opened it. I stepped out and composed myself, praying that I could find the items without any intervention from the staff.

He entered first, and I followed behind. He stood there, waiting for me to move forward at which point he put a hand on my shoulder. A lady with a name tag reading Claire approached almost immediately.

"Hi, can I help you find anything today?" she asked with a big smile.

"N-" I began to decline but was cut off.

"Yes, she will need help. It's her first time in an adult store."

I must have looked embarrassed because she gave a compassionate laugh and reached four for my hand.

"Oh don't worry honey, I will be your guide."

She was young, in her twenties or thirties, exceedingly fit, and had tattoos gracing almost every exposed bit of skin she had. Her hair was blue and she wore very light makeup in an alternative style.

"Okay, let's see this list." she suggested.

I opened it up and immediately closed it.

"Uhhh... It's okay, I should be able to manage..." I said.

The list itself was pretty plain but there was more on the page I really didn't want her to see. The picture of me kissing his bulge was printed directly on the paper. The title at the top of. The list read: Sissy Cocksucker's Supplies.

"Well? What's the first thing?" she asked.

"Uh... a..." I couldn't quite say it out loud.

She placed her hand on my back and rubbed.

"Honey, it's okay, breathe. I've seen it all." she said, convincingly.

I took a deep breath and felt a small but welcome wave of relief fall over me. Of course she had seen this all before, probably much worse too.

"Anal beads" I stammered out quietly.

"Ooooh, we have at least a few, all of them are right over here... Near the plugs" she said as she motioned toward one wall of the store. I walked ahead of her heading toward the wall feeling lightheaded as a result of the embarrassment. A wolf whistle from behind me snapped me out of my state.

"Nice tattoo! You're brave to have that displayed loud and proud!" she said.

"Thanks" I replied with a pit in my stomach.

I knew it must have been bad if a sex shop worker thought it was risque.

"Now here are the most popular ones, for beginners, they can be a lot of fun." she handed me two packages of small anal beads.

I looked at them for a moment and then back at the list, noticing a measurement in brackets that he had written in.

"Umm... Is there anything bigger? Like maybe over an inch wide?" I asked.

She looked surprised for a moment and then a small smile creeped back in her face.

"Adventurous! I love it. Sure, over here in the XL toy section." she said bringing me a through a beaded doorway into a small room, lit with red lighting.

"Okay, let's see... Maybe these would be good? Two inches? Or we have these over here, two and a half I think... Oh! These too..." she pointed out a few but I stopped her before she could continue.

"The first ones are fine... Nothing too big" I said trying to play it off.

She reached for them and handed them to me. It was three big baby blue balls, each one two inches in diameter attached to a string, ending in a loop.

"Well I'd consider those huge personally" she said laughing, "What's next?"

After I stammered out the next items on my list she led me out of the room and whisked me around the room collecting a new dildo, a new plug that was just over two inches at the widest part, nipple suckers, and last but not least, a vibrating wand. As she brought the last item to the counter, the shop attendant commented on it.

"I have one of these and I love it. Have your boyfriend tease your labia with it before going for your clit, trust me it's life changing. I do it to my girlfriend and it blows her mind every time."

As she said this I realized that she wasn't aware I was actually a guy. I was fully passing as a girl thanks to the alterations made that day.

"Thanks..." I said shyly.

As she began scanning the items, my master approached, dropping another item on the counter. A new chastity cage, seemingly smaller than the one I was currently wearing. The cashier looked at it confused and then back up at my master.

"I could have sworn you were the dominant one!" she exclaimed picking it up to ring it through.

"I am. This is for her." he said, "Her other one is a little loose for my liking, she still gets a little hard during play time. With a tighter fit hopefully we can condition the erections away quicker, or at least shrink them down."

The woman looked at me up and down, mouth agape. It was then I noticed how attractive the girl was and the shame that had been in me since I walked in multiplied. She must have seen this because a smile crept across her surprised face and she spoke up quickly.

"You're a very convincing girl. I know real girls that would give a lot to have your looks." she complimented, putting me at ease a little.

"Claire," my employer said taking her attention back, "My sub here was hoping she could try out one of her new toys on the way home. Would you happen to have a bathroom she could use?"

The girl gave a knowing smile and looked around and sighed before answering.

"Well we really aren't supposed to, but seeing as she's so cute... Sure, just in the back here."

She opened the curtains leading to the staff area behind the counter. My master turned to me, holding up the balls and removed them from the packaging. He held them out to me and I took them, my eyes wide and my mind racing. They were quite big and I was already dreading working them inside me. Before I could scamper away to the washroom he also gave me the new cage as well as the key to the old one, without instruction necessary. As I walked past Claire she whistled back to me and I turned to see her holding something.

"You're probably going too need this" she giggled handing me a bottle of lube.

Inside the bathroom after shedding my panties I applied the lubricant to both my hole and the balls. My hole may have gotten a good workout with all the toys in the past few days but I realized how tight I actually was while working the first ball in. It was certainly an uncomfortable stretch and I tried my best to relax as I slowly pushed it in. On the bright side, as soon as the ball was at the halfway point my ass suckled it in the rest of the way, allowing my sphincter to shut over the small string. The second was a little easier however the third was a little harder. As I pushed it in, there seemed to be something stopping its progress. After some pushing the other two balls moved deeper and I could feel the last one finally sinking inside with only the string hanging out. The discomfort from stretching so much had caused my little penis to shrink to an embarassing size and although I removed it using the key I was sure I could get the cage off without it. The new cage was definitely smaller and I knew that anything resembling an erection would now be impossible. I quickly wiped away the excess lube, pulled up my panties and left.

As I exited the back room I saw Claire writing down something on a card and handing it to my master.

"Really, call me, that sounds great." she said giggling and blushing before they both turned to me.

"Feel good?" he asked knowing that I would respond how he wanted me to.

"Yes Daddy" I said.

"Wait" Claire said as I walked by her.

She bent down behind me and I felt her pull my skirt up and then a little tug on the balls inside me made me gasp. Something was tucked in behind my panties and the skirt was pulled back down.

"There. The string was hanging out. All good now, no one knows but us." she said and gave me a light slap on the butt.

"You were checking out her ass!" my so called daddy said.

"Can you blame me. After the five star review you just gave it?" she laughed.

Blushing I thanked her and we said our goodbyes and left.

My mouth found its way to his cock again for the ride back home and we arrived at about noon. He pulled into the garage and soon we were in the house. He had me fix a drink for each of us, a whiskey on the rocks for him and a couple vodka shots for me followed by a vodka cranberry. My head was already spinning by the time we had finished the first drink and I began to make us a couple more. As I returned to the living room with them I saw there was a camera sitting next to him on the couch.

"What's that for?" I asked.

He ignored me only to take his drink from me and point to the ground in front of him. He pulled out a leather band covered in hot pink fake fur. Stitched into it was the word *Bitch*. He fastened the collar around my neck before pulling his pants and underwear down around his ankles. His cock stood straight out, almost staring at me.

"Mouth open and tongue out" he said.

I slowly opened my mouth and leaned in allowing him to place his cock head on my tongue just barely fitting in my mouth. He reached for the camera and I pulled away.

"You made the deal." he reminded me, "No one you know will see."

I returned with hesitance and allowed him to place his cock back on my tongue and raise the camera.

*Click*

He stood up, placing a hand on each side of my head. He pulled my head down, forcing his cock down my throat. I gagged immediately and he withdrew although not completely, leaving his head in my mouth. As soon as I was composed he pushed in again just as deep causing a repeat of my gagging fit. This time he pulled his cock all the way out, a thin strand of saliva trailing from my upper lip to his head.

*Click*

He took another picture of me as I looked up at him.

"Wrap your lips around your teeth." he said before pushing his cock back in me. I did as he asked and once again his cock went in, this time right as it filled the back of my throat it pulled out before pushing back in. He repeated his three or four times and then left it deep inside for a moment. I fought the urge to gag as long as I could but it overtook me. Instead of pulling his cock out, he left it in and let me gag around it for a moment. When he did pull out, the thin strand of saliva had been replaced with multiple trailing down from his cock and my chin.

*Click*

I cringed at the idea of him having these photos of me. This time I didn't wait for his hands to pull me in. I took him into my mouth again, taking him deep until I felt my gag reflex begin to kick in. I fought it harder than before and he seemed to know I was trying. He placed a hand on either side of my head and held me there as I focused on keeping his cock in my throat.