WHAT’S YOUR PRICE?

Growing up poor meant I always had to do without. I was orphaned as a baby and became a ward of the state. I could never seem to catch a break, my life was one loss after another. After becoming 18 I was discharged from foster care with nothing. Now three years later I still had nothing. My prospects weren’t good and I couldn’t get by on my looks. I was 5’7″, with a light brown complexion, had no striking features and weighed 140 pounds. Basically I was easily forgettable. This made me feel like the future was bleek and my depression was never ending.

Having to make it on my own was proving challenging. I was staying in a rooming house and worked as a delivery guy for a downtown Manhattan deli. Most of my money came off of tips which varied from day to day. I delivered to a lot of office buildings especially during the lunch rush.

Who knew million and billionaire types could be so stingy when it came to tipping? The job kept a roof over my head, barely, but I wanted more. Visiting these offices I knew that their homes had to be plush. I was jealous of their lifestyles and carefree attitudes. The total opposite of my Fifth floor walk up, rundown room with only one window facing a brick wall. Little did I know that was all about to change.

I told Saul, my manager, that I would work the evening shift because one of the guys called in sick. I was glad to work a double because I needed all the cash I could get. Around six thirty I got a delivery for an office building over near Wall Street. I headed over, showed my I.D. to the front desk person, and headed up to the 6th floor. I walked through a set of glass double doors that read Titan Global. There was a receptionist seeming to be packing her things for the day.

“Excuse me Miss, I have a food delivery for a Courtney Shaw.”

“Sure, just head straight down that hall until you reach the end, it will be the last office you reach.”

“Thank you.”

I walked the long corridor, passing mahogany doors with glass panes with people’s name emblazoned in frosted letters. I envied them. I had never been a great student so this would never be in the cards for me. I reached the end of the hall. In front of me were two huge mahogany doors with a silver nameplate to the left of them. The nameplate read Courtney Shaw Chief Executive Officer. I could hear someone talking inside so I knocked lightly.

“Come in,” I heard a voice say.

I walked into one of the most luxurious offices I had ever seen. It was immaculately designed in a modern style. There were degrees and plaques adorning the wall to my right.To my left it seemed like floor to ceiling flat screen monitors. They all were tuned to different financial news from around the world. All the correspondents had a different accent. Directly in front of me sat a huge desk with a lady sitting smartly behind it. Behind her was a huge floor to ceiling window overlooking the street below.

“Jan, I will give you a call back, my dinner has arrived. OK, talk to you soon.”

She hung up the phone and stood as I approached the desk. She was extremely attractive for a woman who seemed to be in her early forties. She was wearing a gray business suit with a skirt that fell a few inches above the knee. It hugged her thick thighs nicely. She wasn’t fat, she was thick in the right places, a very curvy woman. She was about my height but she had on black patent heels that were at least four inches, and her legs were clad in black pantyhose. Her skin was a creamy mocha color and her makeup was flawless.

“Good evening, Miss Shaw, your order comes to $16.50.”

“One second, please,” she said as she took her wallet from her designer handbag.

She handed me a $100 dollar bill.

“I am sorry mam, I can not change a hundred.”

“Really?” she said surprised.

“Yes, for safety reasons we don’t carry that much cash on us.”

The night shift did get robbed a few times so it really was a safety concern. She looked befuddled for a few seconds.

“I will tell you what, you keep the change.”

“I can’t do that ma’am, that’s too big of a tip.” I was trying to be nice even though I could really use the money. A few of the guys had told me stories about getting huge tips from drunk executives from time to time. This was different. Though I often thought when was my big tip day coming. My conscience had got the best of me today.

“I will tell you what, I will be working late tomorrow so you can bring me the change then. I will call in another order and you can deliver it. How does that sound?”

“That’d be fine.”

I left the office and headed back to the deli. I worked the rest of the evening, cashed out and went home. It had started raining by the time I got back uptown to Harlem. I jogged to the building and went upstairs. I couldn’t stop thinking about this attractive woman. She had to be smart and successful to be the C.E.O. of a company like that. I couldn’t decide if I was more entranced with her looks or her apparent power. I munched on a sandwich I got from work.

I began watching TV on my little 19 inch, thinking about her office and all its grandeur. I pulled my blinds all the way up and watched the rain hit the adjacent brick wall. I laid back on the bed and started thinking about Courtney Shaw. The thought of her curvaceous body set me ablaze.

Her long straight black hair framed her face as it was parted in the middle. Her eyes were a light brown, big and attractive. Her full lips were delicately glossed. She looked beautiful with those curvy hips. Her legs encased in those sheer pantyhose sitting perched up on those stilettos. I could remember looking her in from head to toe.

Without even realizing it, my seven inch full erection was trying to break through my jeans. “What the hell,” I thought as I undid my pants and grabbed a towel off the floor. I didn’t bother closing the blinds, the brick wall wouldn’t mind. My mind drifted to bending her over that glass desk feeling her curves. Did a powerful woman like that get bent over desk? Courtney Shaw’s curves helped me explode into the towel a few minutes later.

That night I called my coworker Juan to switch shifts with him. I wanted to be on when Ms. Shaw called that evening. I spent all the next day anticipating her call. I was so anxious, I’d never felt that way about an order before. She called around six and ordered a grilled chicken avocado salad and a Perrier. I took the order over and went through the same drill as before. The front desk lobby to the sixth floor. This time there was no receptionist there. I knew where her office was and headed down the hall. Arriving at her huge intimidating doors I knocked.

“Come in, please.”

“Good evening, Miss Shaw, I have your order and here is your $83.50 from yesterday.”

“You didn’t take anything for yourself?”

“No ma’am.”

“I will tell you what, deduct my order from tonight and you keep that change.”

It still came out to about over a $60 tip. This time I didn’t put up a fight. She was obviously a wealthy woman. Who was I to tell her how to spend her money? My conscience had taken a break this evening, to which I was grateful.

“Thank you, Miss Shaw.”

“What’s your name?”

“Jason Brown.”

“Have a seat Mr. Brown. So tell me about yourself, young man.” I proceeded to dive into my pathetic life story. She sat and listened attentively. I went on about my lack of prospects and finances. While telling my story I felt a pang of guilt for rubbing one out to her the night before. Sitting across from her was intoxicating. Today she had on a navy blue pinstripe skirt, a white blouse, and navy pantyhose and heels. Her perfume smelled incredible, a light airy fragrance.

After hearing my story she told me her own. It was filled with business school, hard work and business triumphs. Her conquests added to her allure. She was a powerful woman and I basked in her aura. I did wonder why she was single. After hearing her schedule and accomplishments I concluded she was too busy. She was trying to let me know that anything was possible. It was falling on deaf ears, I couldn’t see it, experiencing the hard lessons that I’d had to. She got up to walk me out.

“Jason, you have your whole future ahead of you. You won’t get far without hard work and taking advantage of opportunities.”

As those words left her full lips I felt like my opportunity was right in front of me. I caught her mid sentence right on the lips. I felt her start to pull away but instead she parted my lips with her tongue. We kissed passionately for what seemed like an eternity. My hands had worked there way down to her round ass, so soft. She ended the kiss and told me to drop by the next evening around the same time. That night I rubbed two more out to Ms Shaw.

I knocked on her office door promptly at six thirty the rest of the office was empty.

“Come in Jason, how are you?”

“I am fine, thank you.”

“So, Jason lets get right into it. You say you would like to change your circumstances and I would like to offer you that opportunity.”

“A job?”

“Well, sort of.”

I was hoping she’d say something like she wanted me to be her sex slave or something. I had no idea. All I knew is that I was so drawn to her. I felt like I could get emotionally drunk from being in her presence. She reached over the desk and plopped down what looked like a contract in front of me. It was a contract.

I, Jason Brown enter into a binding contract of servitude. I will serve Courtney Shaw in whatever way she sees fit, I will obey her every command and never refuse any task. Courtney Shaw agrees that I, the servant will not be physically hurt or maimed in any way. The period of servitude will be binding for one calendar year from the date of signature. The servant will receive monthly payment of $20 000, and at completion of the year of servitude $1,000,000. All parties agree that this contract and any dealings regarding this contract will forever remain confidential between the parties.

I couldn’t believe what I was reading.There were two lines at the bottom with each of our names printed below them.

“So what do you think, Jason?”

“I think I have never seen that many zeros in my life.”

I took a minute and thought about how bad could it be compared to my current situation.

“So I’d get Twenty grand a month and a million when I have served a year?”

“That is correct, also you’d live in a gorgeous luxury apartment with me that overlooks the city.”

I took a pen from her desk and signed my name. I was nervous but anxious to see what was next with us. She was such an intriguing and charismatic woman. I didn’t have anything to lose. She signed her’s, took the contract and put it in a wall safe that was hidden behind one of the flat screen monitors. I belonged to her, at least for the next year.

She took me to her car that awaited downstairs with her driver. I felt like I was on cloud nine. I would never have to go back to that dingy room. I was making all types of plans in my head for when my year was up. We drove a few blocks over and went down a dark, sketchy looking alley street.

“Where are we headed?” I asked.

“You have to be to properly trained before I can take you home. You need all the right skills and training to be my companion. Companion?, I prayed that included sex. You will stay here for the next two weeks and learn all you can.”

We exited the car and we walked to a huge steel door. Miss Shaw rapped on the door. A voice came through an intercom.

“How may I help you?” a woman asked.

“Yes, this is Miss Shaw, I have one for you.”

A minute later the big steel door creaked open and a beautiful redhead stood there.

“Hello, Miss Shaw, we will have him in shape for you in the customary turn around time.”

“Thank you,” Miss Shaw said as she kissed me. She patted me on the ass and said “See you in two weeks.”

I watched her get into the car as her driver opened the door and she drove off. The inside of the building looked like an old warehouse or factory. The redhead led me across a long concrete floor to an old service elevator. We went down one floor.

I felt like I was ushered into a whole other world when we stepped off the elevator. Everything was done up in bright colors and well decorated like a posh hotel. The redhead took me to a bedroom.

“This will be your dorm room for your stay here. Make yourself at home and someone will be with you shortly. It was about Twenty minutes before someone returned. The lady was sexily dressed and she was holding a clipboard.

“Per your agreement with Miss Shaw you will have to strictly adhere to all requests made of you here at all times. Please stand.”

I stood and she measured me in every possible way one person could be measured.

“Have a good nights rest and we will come and get you in the morning.”

I took my clothes off and got into bed. I laid there wondering what had I gotten myself into. The thought of the money was motivating me to take on whatever Courtney Shaw had in mind for me. She had some sort of power over me and I was entranced.

Two weeks, the longest two weeks of my life. I took that long walk back across the concrete floor, that I had when I entered. My four inch heels clicking at each step. I never thought that signing a document would lead me into a crossdressing boot camp. A vigorous training course of makeup, hair, clothing, shoes, voice training and mannerisms.

I spent 16 hours a day for 14 days learning to be a woman but I graduated with honors. I kissed Vanessa, the redhead, as I exited through the big steel door. I had become close with all the girls since I entered the boot camp. Or as they called it, stiletto camp. All the girls were really guys, but I couldn’t tell, they were that good. Now I was that good. Miss Shaw was waiting for me as I exited. The alley looked even worse in the morning light.

“Let me look at you,” she said happily as she spun me around.

“You are gorgeous,” she said excitedly.

I really was gorgeous. I would look into the mirror and turh myself on. Having no discernable features, I had a feminine base to craft my makeup skills. The camp had trained me in makeup, dressing, walking in heels, mannerisms and speech. I was looking and talking like a lady.

“Good day, Miss Shaw.”

Rule #1: She could only be addressed as Miss Shaw.

“Let’s go home,” she said.

She gestured for me to get in first and I struggled a little as my tight pencil skirt impeded my strides. I pulled my skirt down as it had ridden up. I sat and slid over to make room for her. She got in and the driver closed the door and we headed home. My room was amazing, it was huge and decorated so nicely. My walk-in closet was bigger than my old room 5 times over. I was excited as it was filled with clothes and shoes. Oh, how I had fell in love with shoes. They made my calf muscles look so amazing.

Rule #2: Always carry yourself like a lady. Never appear before Miss Shaw in Men’s attire or without a Wig, makeup can be removed before going to bed and must be reapplied during the morning routine.

So many rules, I hoped I could remember them all. I sat at the makeup vanity in my walk-in and just took it all in. Crossing my legs and hearing the zip of my pantyhose rubbing together brought me to the here and now. Just a week and a half ago I would have cum in my panties at that sound. I was learning how to control it better.

“Knock knock,” she said as she entered my closet. “I hope everything is to your liking.”

“Yes Miss Shaw, everything is excellent.”

“That’s great.”

She sauntered over so sexily and began to ravish me. Her kiss was so passionate our lipsticked lips locked together. Our tongues were exploring each other, making my tucked manhood so erect. She backed me against the wall. I teetered before regaining my balance.

She looked me in the eyes as she took both her hands and grabbed the hem of my skirt and pulled it up around my waist, exposing me. She looked me up and down as I stood there in panties and pantyhose, my slip had come up with the skirt. I was hoping she liked what she saw. She reached inside and untucked me. She began to jerk my rock hard cock as she talked to me.

“Whose bitch are you?” she said in my ear.

“Your bitch, Miss Shaw.”

“Whose bitch?”

“Your bitch.”

She stopped suddenly. “Excuse me?” she said irritated.

“I’m sorry, your bitch, Miss Shaw.”

She led me out of the closet by my cock, holding it like a leash. I never felt more like a bitch in my life. I was trying to keep up with her in my heels, skirt up around my waist and panties and pantyhose down around my upper hips. I felt so sexy as both our heels clicked the hardwood floors.. She took me to her room and pushed me down onto her bed. I just laid there. She hiked her skirt up and straddled me. She hovered over me and began to have her pantyhosed ass rub slowly against my exposed erect cock. As she hovered she talked to me.

“Do you know how I got to be one of the most powerful women in the world?”

“No, Miss Shaw.”

“By making men my bitches. You motherfuckers think it is so easy to run the world. Why don’t you try it in a 2 sizes too small girdle, pantyhose and heels? Do you know what it’s like to go to a board meeting, and know every jerk-off in the room is thinking they want to fuck you, how good you suck dick or if you’ll let them titty fuck you?”

“No, Miss Shaw.”

“I know you don’t, but tonight I am going to fuck you, see how good you suck dick and titty fuck you.”

“Yes, Miss Shaw.”

She left and returned wearing a 8 inch black strap-on and her heels.

“On your knees.”

“Yes, Miss Shaw.”

I was scared shitless. I did as commanded. It seemed as if she towered over me on my pantyhosed knees. She took her time as she relished every moment of it. I was also basking in the moment. The strap on was right in front of my eyes. She grabbed it at the base of the shaft and got closer. Her heels were outside of my hips as my knees were together.

She unbuttoned my blouse and exposed my skin toned custom breast forms bounding from my low cut leopard print bra. She began to run the strap on over and between them watching my face for my reaction. My reaction was of course one of being so turned on. I hadn’t been dominated like this since I was in the group home. I had been taken by the older boys several times, before I was transferred. Each time they had taken me I was ashamed I had came.

The truth was I was starved for any attention. In fact being on my knees like this made me feel desirable, which I never had before. These type of feelings I’d take any way I could get them. As she proceeded bending at the knees in her heels my erection was solid rock. It was grazing the waistband of my pulled down pantyhose exciting me even more.

This went on for a while before she moved the cock to my face. She ran it over my makeup and I could feel it smudging. I could see my lighter brown foundation on the sides of this jet black cock. She parted my lipsticked lips with the tip and slowly slid it in.

My emotions were confusing to me, I never saw myself ever being in this position. I’d never sucked a cock before but I didn’t gag. I tried my best to act like I knew what I was doing. I had watched enough porn, and tried to mimic what I’d learned. She grabbed the back of my head and moved it back and forth. I felt sexier than I’d ever had before.

She was now eight inches deep into my overly moist mouth. I groaned in delight of being face fucked. My hands squeezed the back of her hips as we swayed in unison. She pumped my head faster and harder, as she rocked on her heels. She cummed and I could see it run down her leg. Her body jolted like she’d received a shock.

“Undress and leave your heels on and get onto the bed.”

“Yes, Miss Shaw.”

I did as commanded. I removed my clothes and slid back into my stilettos. I was trying to prepare myself for what was coming. I crawled onto the bed on all fours.

“No no sweetie, on your back.”

“Yes, Miss Shaw.”

I did as commanded. She took a pillow and put it under, me propping my ass into the air more. I didn’t want to watch. I heard her squirt what I assume was lube onto the strap on. She took my legs and put them onto her shoulders.

“Open your eyes.”

“Yes, Miss Shaw.”

She entered me, slowly penetrating my tight ass. I could feel the girth of the cock filling me. I groaned from the pain. I couldn’t remember if I had groaned like this as a young boy. She was on her knees looking down at me. I was looking up at her face and my stilettos in the air behind her. Once she was fully in she began to move in and out slowly.

It was a few strokes before it became tolerable. I tried to focus on the paydays I had coming, with the big one at the end: $1,000,000. In the midst of thinking about the money it started to feel good to me. It went from tolerable to pleasurable. My sudden pleasure was interrupted by her talking to me.

“How does it feel, bitch?”

“Great, Miss Shaw,” I said mid moan.

She then went on a tirade.

“You fucking bitch, you don’t belong here. You belong somewhere getting fucked or with a dick in your mouth, not here taking over our companies. You’re only good for a bedroom, not a boardroom.” I didn’t know what to think, she clearly was somewhere else in her mind. Maybe, she’d heard these things from people in her past. I wasn’t sure, but I was definitely feeling the brunt of all they had done to her.

The more she ranted, the harder she fucked me. The harder she fucked me, the more I moaned. Without realizing it I was matching her thrust. I was thrilled to be getting fucked for once on my terms. I never thought it would be with my stilettos in the air. I’d always been under the belief that I was straight. I’d been fucked before but not by choice. This time was by choice but I was being fucked by a woman. I clearly didn’t have a clue of my orientation.

My thoughts were interrupted by my quivering erection. I focused in on what was happening. I reached up and released her bountiful breasts from their lycra prison. They seemed to spill over as I tweaked her chocolate nipples. I bucked against her thrust, as we both cummed in a cum filled bliss. I had never seen my cum in the air before, it was exciting. She pulled out of me leaving me feeling empty but relieved. She then told me to pick up my clothes, clean myself up and she’d be back this evening.

I drew a hot bubble bath and soaked. I had a lot of tough questions for myself. Was the money worth it? It was a lot of money and I probably wouldn’t make that in a lifetime. It is not like I had better prospects coming my way. Could I handle getting fucked everyday? If it was by her I sure could. It wasn’t my first anal experience. The first times were as a teen in a group home. The sex wasn’t consensual but I had cum those times as well. I also thought back to leaving boot/stiletto camp and thinking I wasn’t the first to be dropped off by Miss Shaw.

Done with my bath I sat at my vanity and finished up my makeup. What should I wear? I settled on a black and beige tweed skirt, black blouse, and black hose with black suede heels. I fixed my long black wig and walked out to the kitchen. It was now early afternoon and I was starving. After perusing the fridge and cabinets I settled on a turkey and Swiss on wheat. I had taken my first bite when I heard what sounded like a beeping noise. It was coming from her office. There was a box on her desk with a post-it that said open me. Inside the box was an iPhone with one new text message.

“From now on refer to yourself only as Maya. I will be home around 6. I have a chef coming over around 5 to start preparing our dinner. Let him in and direct him to the kitchen. That was an amazing ride. We will talk over dinner. Love, Miss Shaw.”

I responded, “Yes, it was amazing and I would love to talk over dinner. See you soon and hurry home. Love Maya.” I wrote it but I didn’t love her, though I could love this year as Maya. Dressing had made me feel like I had found something, I never knew was in me.

There was now no doubt I could get use to this. Living in the lap of luxury and all I had to do was be her bitch. I could definitely do this. My time at the boot camp made me fall in love with dressing. They made it seem fun and sexy. I totally embraced it so was I gay, I didn’t know.

Around 5 the doorbell rang and I was completely terrified. Would the chef know? I opened the door slowly and said a soft “Hello.”

“Good evening, you must be Ms. Maya?”

“Yes, yes I am.”

“I am chef Drew and I will be cooking for you and Miss Shaw tonight.”

He took my hand and kissed the back of it. It sent a chill down my spine. I felt flush.

“This way, Chef.”

He followed me to the kitchen. I could feel his eyes checking out my curves as I walked. As I approached the kitchen door he said, “Let me get that for you.”

He opened the door for me. I felt like a lady. I showed him where everything was.

“If you need anything just give a holler,” I said.

“I will. I hope you will like everything that’s on the menu tonight.”

“I am sure I will,” I said slyly.

I walked out of the kitchen and my incoming text message startled me. I was still caught up in every bit of the 6′ 3″ chef in the kitchen. The message read:

“I see that Maya likes flirting with the chef.”

I stood there with my mouth open.

All I could imagine was this whole place outfitted with cameras. What if she was at her desk watching me on all of those monitors.

I responded. “I wasn’t flirting, I was just being courteous.”

“Just checking, you’re my bitch.”

I felt like I dodged a bullet. I didn’t want any problems with Miss Shaw.

Ms. Shaw walked in around ten after six. I greeted her at the door.

“Good evening, Miss Shaw.”

“Good evening, Maya.”

I took her briefcase and handbag and she had a seat on the sofa. I poured us both a glass of wine and returned to sit next to her. I handed her a glass.

“How was your day, Miss Shaw?”

“It was good Maya, I got a lot of work done. It went by quickly because I knew I was coming home to you.”

That made me smile and my tucked member stiffen.

“That is very sweet of you, I couldn’t wait until you got home. This place is so big, I have to get used to it.”

“You will baby, you will.”

I could see her checking out my legs. My legs were crossed towards her and they did look pretty good. I pulled my skirt down a little as it had ridden up some. We both went on about our days for a little while. We were interrupted by chef Drew as he let us know dinner was done. We took seats in the dining room in front of what smelled like heaven. He pulled out our chairs.

“Ladies I offer you this evening pan seared duck breast. I also have grilled asparagus with a light cream sauce and wild Jasmine rice.”

There was also soft dinner rolls and a side salad. Miss Shaw thanked him for everything and said good night. He packed up his things and was gone a few minutes later. I did enjoy watching him leave. I made sure I was discreet. This transformation was going to my head. Miss. Shaw returned from walking Chef Drew to the door.

“So Maya, do you think you could do this for a year?”

“I think I can. I have been thinking about that all day. I plan to try to make you as happy as I can. The past 2 weeks has gone so fast. It’s been incredible.”

“How do you feel about dressing?”

“I was reluctant at first. The boot camp was extremely fun once I began to enjoy it.”

The truth was my life wasn’t going so great. What if I could live the life I dreamed of? Dressing like a woman would be a small price to pay. More importantly, feeling like a woman was an extreme high. I didn’t know that these feelings were in me. The money would be great but I think I would do this for free if she asked. I just hoped she wouldn’t ask.

The next two weeks consisted of fucking and sucking. My biggest worry of the day was what I was going to wear that day. My only job was to follow Miss Shaw’s orders. Who knew I was so submissive? I fell into being Maya pretty hard. I had never got in touch with my feelings before.

It was October 1st. I officially made it through my first month. The first thing I did was go to my laptop to check my bank account. It read $20,064.32! I nearly wet my panties. My bank account had never been past the very low 4 figures. What did the new month, October have in store for me?

Also read: Sissy Makeover Stories