Cindy

by Jean M. Chambers

 

Part 3 -  Cindy for Life

 

I was having diner in a nice restaurant with a handsome man. The candle light flickered between us. I smiled at him and he, back. Beneath the table I ran my nylon covered foot up and down the inside of his calve, then gently put it on his seat between his legs and rubbed him there. A ringing bell could be heard in the distance. It got louder and louder. I glanced around the dining room to see where it was coming from. All I saw were other patrons having their evening meals. I went back to stroking my companion with my foot. He was hard…

I sat bolt up right in my bed, surrounded by feminine decorations, and shook off a cold sweat. It had been a dream and my alarm clock was ringing on the dresser. I swiveled around and sat on the edge of the bed staring down at a pair of smooth women’s legs with painted toe nails. My legs. I glimpsed myself in the full length mirror across the room. My room mate’s reflection stared back at me. Even after five days it was hard convincing my mind that the vision in the mirror was actually me, Tom, a male. It all started a few days ago when my room mate, Cindy, wanted us to wear matching hairstyles. We would look like twin brother and sister. Her friend Lynn, who owns a salon, colored my hair Platinum Blonde and cut it into a shoulder length Page exactly like Cindy's. The color change was a surprise. I thought we were just going to get the same hair style. Cindy quickly realized we actually looked like twin sisters, not brother and sister. For kicks and grins, I let her dress me in one of her skirt suits, as she would normally do to herself. The transformation was astounding. We looked identical.

Cindy got a crazy idea to play a trick on our high rise apartment building's doorman. She and I would dress the same. Then I would go downstairs, through the lobby, making sure he saw me. We would meet across the street in a small restaurant. On the way downstairs I ran into our neighbors, Jill and Bob, who thought I was Cindy. I told them I was meeting my sister Candy across the street for a drink. Forward as they are, they invited themselves to tag along. They asked where Tom, my real identity, was. Pretending to be Cindy, I told them he was away on business for a few weeks and that my sister Candy would be staying with me. At the restaurant I introduced Cindy to them as Candy. Bob surprised everyone by telling me I, who he thought was Cindy, got the job as an Executive Secretary under his boss. Cindy was to start Monday morning. Not wanting to put Cindy's job offer at risk, I signed her name to the job contract he produced from inside his jacket. Shortly after, Cindy and I excused ourselves and left. Neither of us had brought any cash so I used Cindy's credit card to pay the check.

When we got back to our apartment I found all of my clothes were all gone. Candy said she had dumped them all into the building's incinerator chute, but I suspected she had hid them on me for kicks. She told me she liked having a sister to bum around with and wanted me to keep pretending I was her for a while longer. She threatened me with some legal hog wash if I didn't because I had impersonated her, used her credit card, and forged her name on an employment contract for a job as an Executive Secretary. I didn't believe a word of it. There was no hurry for me to revert back to my real identity as Tom right away and I was having fun, so I played along with her the next couple of days. It was actually exciting being Cindy for a while and I got caught up in the role I was playing. I had completely taken over her identity, including her bedroom. After a few days of being Cindy I was ready to get out of women's clothes and go back to being Tom. Wearing makeup, pantyhose and skirts every day got old quick.

As a last, sister’s night out, saturday evening we dressed exactly the same and went to a few local pubs to have fun. The attention we received was incredible. I never realized how excited people got over meeting twins. Especially men. I'm not into guys, but they kept buying us drinks. Before we finished one, another was set in front of us. All we had to do was show them a little leg and smile. We were tipsy when we got home later that evening.

"That was great, but my feet are killing me" I said, kicking off my heels and rubbing my toes.

"And guys think it is easy being a girl" Candy snorted.

She was right. Shaving your legs, putting on makeup every morning, and wearing pantyhose and skirts was a pain, but I wasn't going to admit it. My male ego, assisted by the drinks, started talking.

"Oh, I don't think it is so bad"

"That is because you've only done it for a weekend. You wouldn't last a week as a girl."

"Really?" I asked, offended, "A week would be a walk in the park."

She reconsidered.

"Granted. Maybe you could handle a week or month. Living and working as a full time girl, I'd give you two months tops, then you would be begging to be a man again."

"Two months? Two months would be a breeze, six would be a walk in the park."

"I'm sure it would" she said indifferently.

"Yes! It would." I was getting mad.

"Care to wager that and put your manhood where your big mouth is?" she asked slyly.

"Absolutely!" I spat, determined to win the argument, "Under one condition. You have to live as a man, me, Tom, for the same time period."

For sure I thought she would back down from the challenge. Cindy thought deeply for a moment.

"Okay... but you have to get breast implants so you can really pass and live as me, Cindy" she spat back.

I hadn't expected that, but I couldn't back down. I had my pride to think of. Besides, I didn't think implants were a big deal. Everyone got them these days, and they could be removed. Even if I didn't have them removed after the bet, it wouldn't be hard to hide them. Baggier shirts would do it.

"You are on lady! Oh, you are so on! It will be fun watching you try to fill a man's shoes."

"It will be worth it," she spat back, her temper rising visibly, "Living as a woman will improve your attitude! Tomorrow mister! We start tomorrow."

"Tomorrow!" I yelled back.

The next day I ended up with breast and hip implants. Lesson learned. Don’t piss off your plastic surgeon. Hip implants were compliments of mine, to give me a ‘real’ feminine shape I couldn’t hide, because I insulted her just before the operation. Now I was stuck with a real feminine body that clothes couldn’t hide. As per our agreement to completely swap lives, Cindy and I swapped bedrooms and all legal documents.

Today, Monday, was the first day I was to take over living as Cindy and I had a new job to start. My stomach was full of butterflies. I had only gone out as a girl, Cindy, a few times in the past couple of days. In fact, a few days ago was the very first time I ever even dressed as a girl. The few times I did go out it was with Cindy. I had never gone anywhere alone as a girl, and certainly not to work a job. For sure someone would realize I wasn’t really a girl. I slipped out of Cindy’s camisole, correction, my camisole, on the way over to the dresser. After a little digging in the lingerie drawer I found a pair of Cindy’s pantyhose and sat on the edge of the bed to put them on. The thought occurred to me that Cindy, the real Cindy, had worn the very same pair last week. She probably even wore them to the interview of the job I was starting today. I rolled the right leg up, inserted my foot, and pulled the hose half way up my calve, doing the same with the left foot. Then I worked the hose the rest of the way up my legs. They were snug to a tee. A minute later I strapped on the extra padded bra the doctor who did my breast implants gave me. It had more padding so as not to hurt my breasts which were still sore. The bra made my breasts look even larger.

I stared at my own cleavage for a moment. That thought sounded funny. My ‘own’ cleavage. Never would I have imagined I would have breasts like a woman. Like a woman? Heck, I was just one step away from actually being a woman. Remove my man hood and… No. I couldn’t even think about it. The bra was uncomfortable, but now I had no choice but to wear one, even if I didn’t want to. I had quickly found that not wearing one was worse. It was embarrassing to walk around with your breasts bouncing like jelly beneath your blouse. No wonder women put up with bras. I drug my self over to the closet and stood there looking at all of the different skirt suits and dresses I had to choose from. Not a pair of pants in the closet. Cindy never wore them. Unlike for a guy, the choices of styles and colors were astounding. I just stood there staring.

"The pink one with the white collar" a voice from the bedroom doorway said.

It was Cindy, now posing as Tom, my old self. I threw her a look over my shoulder. I had to admit she looked good in one of my old suits. Too good. With her hair cut and colored like mine used to be, and the bushier eyebrows, nobody would ever guess she wasn’t me. Calling her Tom would also take a little getting used to. She had to use a lower pitch when she talked, but that was easily done. "Men like women in pink. It’ll make you look very feminine and make a good impression on your first day."

I pulled the suit out of the closet, tossed the jacket on the bed, unzipped the skirt and stepped into it. It had a nylon lining and felt sensuous when it slipped against my pantyhose clad legs as I pulled it up, buttoned it in the back and zipped it. It fit snuggly around my new, wider hips and thighs.

I went to find a blouse, but Cindy, now Tom, said women’s suit jackets were meant to be worn without a blouse. I slipped my arms into the sleeves and buttoned it up. It fit my thirty six inch bust like a glove. Tom smiled.

"Nicely done. I like watching a woman get dressed. If you need help with your makeup I’ll be in the kitchen. You don’t want to be late on your first day and the subway ride will take forty five minutes alone. You will be doing a lot of walking so wear the low shoes until you get used to wearing heels all day. Then you can switch to the higher, sexier ones. Even then, some girls prefer to wear sneakers and carry their heels to work in their bags."

Tom disappeared down the hall. I sat at the vanity and spread an even coat of beige foundation over my face.

"Eyeliner, rouge, and pale lipstick" called Tom from the doorway. He was holding a cup of coffee. "Most women don’t wear eye shadow or lipstick at work."

I carefully outlined my eyes and darkened my pencil thin brows with a black eyeliner pencil while Tom watched.

"Good" he said, "You’ll fit right in. Grab your shoes and purse and I’ll walk you to the subway."

I slipped into a pair of pumps with two inch heels, grabbed my purse from the dresser.

"Where are you going all dressed up?" I asked as we left the apartment building.

The city sidewalk was full of people hurrying here and there. One of my heels got stuck in a sidewalk grate and walked right out of my shoe. A man behind me almost walked over me when I stopped abruptly. A giggle came from a red headed woman as she passed. It was embarrassing. I stooped down to dislodge my shoe. A man gently bumped against my rear, which made me stand instantly, bolt upright, and commented about my nice ass. All this within a few seconds. Tom flashed me an evil smile.

"The next few months are going to be very long months for you. Long enough to last a life time. Trust me. You’ll get used to it, though. After a while you’ll just accept treatment like that. Now. Where were we? Oh, yes. I’m going to line up some job interviews. Tom needs to work you know."

"Really? Where?"

"Can’t say. It’s a surprise. Anyway, I don’t want to jinx it."

Tom left me at the subway entrance, where he grabbed me tightly around the waist, pulled our loins together, and kissed me hard, bending me over backwards. He let me go abruptly while I was still bent over backwards. I stumbled backwards, almost losing my balance in the two inch heels. He chuckled.

"Guys think that is funny for some reason. I never thought it was, until now. But then, I was always on the receiving end."

I scowled at him and hurried through the subway gates, moving with the flow of the early morning commuters. My train arrived shortly after I arrived on the platform and I fell in with the crowd that had been waiting to board. Seats were claimed quickly. I was fortunate enough to get one. With my shoulder brief at my feet and my purse on my lap I settled down for the ride. The train was quite full. A man kept staring at me from the opposing seat across the isle. His eyes lingered on my breasts, then my legs, then back to my legs. It made me uncomfortable. Instinctively, I clenched my legs together even tighter. I didn’t even think about it, I just did it, then realized that was what any woman in that situation would do. Tom would have laughed and made some comment about me adjusting to being a woman very nicely. The man just kept staring and I ignored him the best I could. He got off a few stops down the line, but not before leaning close to me and telling me I had nice legs.

It was a relief to get out of the subway and back on the city streets. It was warm and my legs started sweating in the pantyhose. So thin, yet so hot. The skirt suit, pretty as it was, was hot too. I never would have thought a skirt could be hot, but it was. My brief and purse kept slipping off my shoulder, needing constant attention. I followed suit with all the other women in heels on the sidewalk and avoided the sidewalk grates. The address for the building where I would be working was only a couple of blocks from the subway station. I found it easily enough. When I stepped inside the lobby the cool air felt like ice on my wet pantyhose clad legs. Without hesitating I approached the receptionist. She looked up and smiled.

"Hello. May I help you?" she asked politely.

"Hi." I said softly, "I’m Cindy Rodgers. I’m here for the Executive Assistant position."

"Yes, Ms Rodgers." She smiled pleasantly, "I’ve be expecting you. Let me introduce you to the other girls and show you where your desk will be. My name is Terry, by the way."

She slid from behind her desk like a cat. I followed a half step behind her and to the side. Something about her was electrifying. She had grace, poise, and elegance. Not to mention the looks of a model. I couldn’t keep my eyes off her swaying rear. I couldn’t help imagine doing her. Of course, women aren’t supposed to stare at other women so I forced myself to look away.

"We are pleased you accepted the job. I think you will like working here, as long as you don’t let Mr. Bonnetti get to you." she confided.

I detected a little hostility in her voice towards Mr. Bonnetti. We entered an elevator and rode to another floor. I smiled and giggled, rolling my eyes like I’ve see women do to indicate the unthinkable.

"Uh, oh. That doesn’t sound good. Is there something about Mr. Bonnettie I should know about?"

"Lets just say," she paused to consider he words carefully, "he can be a bit forward with the ladies. Administrative Assistants don’t seem to stay on here very long."

"Oh" I said and let it settle at that.

We stepped off the elevator on a large open floor divided into cubicles. Terry led me down a few isles to a coffee maker where three women my age were standing, laughing. She interrupted them to introduce me. There was a red head, named Sally, an oriental girl named Lee, and a blonde named Brittany. They were all as pretty as Terry. I could see that one of the prerequisites of the job was being pretty. We shook hands like girls do. Lee made a point of looking me up and down.

"I think you’ll fit in nicely" she said seductively with a Chinese accent.

It was an open pass and kind of took me back. Sally leaned forward and touched my arm.

"Be careful with Lee here, or you’ll find yourself handcuffed to her bed!" she laughed.

"I can’t help it if you guys lead boring lives." Lee defended, "Besides, bondage is exciting, with the right person."

They all giggled. I couldn’t tell if they were serious or not. After a couple of minutes Terry excused us and took me down the isle to an empty cubicle.

"Well, it isn’t much, but it will be your home while you’re here. Lee sits across the isle there. Sally and Brittany have the cubicles on both sides of yours. They’ll show you what you need. Again, welcome to the group. Now, I have to get back to the lobby. I’ll see you later. We’ll all do lunch soon."

I told her thanks and she hurried away.

I caught Lee eyeing me as I sat at my desk throughout the day. She often touched me while explaining something to me. Once while speaking with a couple other office girls, Lee stood close beside me and slid her hand smoothly down the back of my skirt. Just before quitting time I stood up at my desk and snagged the back of my hose on the chair.

"Damn!" I exclaimed without thinking. Lee giggled.

"Don’t you hate when that happens?" She said asked from across the isle, "I’ve an extra pair in my desk here that you can have. Come on, I’ll walk to the restroom with you."

I had never been in a ladies room before and was hesitant, but I had been holding it all day and had to go. Since I was now living as a full time woman I really had no choice. With my new looks I certainly couldn’t use the men’s room any more. So, I took a deep breath and followed Lee inside. Our heels clicked on the tile floor and reverberated off the walls. The interior was done in shades of pink. Stepping into one of the stalls I locked the door, quickly changed my hose, and sat down on the potty to pee. Some one else entered the stall next to mine. I couldn’t help think how odd it was seeing a woman’s nylon clad ankles and high heels showing underneath the partition next to me, where normally a man’s pant legs and wing tip shoes would be. Sitting there on the potty in the lady’s room with my skirt up and pantyhose around my knees I wondered what I was doing. How did I let things go so far. Ego. Plain and simple. I was never a good loser. Looking down at myself I could see what it had gotten me. A woman’s body. Complete with thirty six inch bust and a culture shock change in life style.

Lee was fixing her makeup at the sink when I stepped out of the stall. She looked approvingly at my legs, then stepped close to me and gazed into my eyes. Her arms slid around my waist and she pulled me close. Her advance took me by surprise. I didn’t know what women did in the restroom, but I was sure this wasn’t it. She examined my face.

"You are very pretty" she said softly.

"Thank you I said," nervously, placing my hands on her upper arms and pushing gently. She held me firmly. I could feel her muscles beneath her silky blouse. She was strong for a woman.

"That shade of lipstick suits you" she breathed, moving her lips close to mine.

Her hot breath caressed my face. Lee’s sexual attraction was intense. She brushed her bright red lips against mine while never breaking eye contact.

"Lee, I…" started to say.

Then she kissed me hard. I tried to pull away but she just kissed me harder. She slid her panty hosed knee between my legs and slid it up and down my inner thigh, raising my skirt. Her tongue explored my mouth. Our lipstick coated lips slid smoothly against each other. I melted in her arms and stopped resisting. I kissed her back, wanting to do her right there in the rest room, but a small voice in the back of my mind screamed no. I didn’t know what she would do if she found out I was really a man. Then she gently let me go.

"Fix your lips, dear" she commanded softly with a smile.

She pulled her lipstick out of her purse and stepped over to the sink to apply a fresh coat. I did the same. The restroom door opened and another lady came in, going directly to a vacant stall. Lee smiled at me.

"I’m sorry," she said quietly, "I couldn’t help my self. You are beautiful. I could tell you liked it too. There will be plenty of time to get acquainted later, if you want to."

"Yes" I said.

Lee smiled and started for the door. I realized she mistook my response. I meant, yes, I understood. Not, yes, I wanted to. I really did, but I couldn’t. Too late. She was out the door before I could stop her and explain. I spent the rest of the afternoon avoiding eye contact with her. Sally spent the rest of the day showing me how to use the phones. It was weird doing office work in a skirt and heels. I had to stoop like a lady. I had to sit like a lady. I had to stand like a lady. The men in the office constantly eyed the women’s bodies. Including mine. It was something I would have to get used to. I was now a woman. At the same time though, it was exciting working in an office as a woman. There was a camaraderie between the women that I never felt between the men. It was like a girl’s club. A sister hood. It was nice.

The trip home after work was uneventful. It felt good to step out of the heels. Tom came in a short time later carrying some packages. He wanted to take me out and had bought a new outfit for me. I opened the packages. He had bought me a short, red, mini skirt with black, see through, lace piping down both sides. Another bag contained a white lace bustier, black seamed stockings, and a pair of four inch, red patent pumps. The outfit was hot, although a bit revealing, even for Tom’s taste. He said he wanted to take me dancing and that was how the girls usually dressed at clubs. Tom wanted me to experience first hand what it felt like to be dressed so seductively at a club. To be dressed the way the I, the old Tom, always wanted Cindy to dress. Me? I didn’t care. I just wanted to try the clothes on and was in them within seconds.

"Hot! Totally hot!" was all Tom could say.

I was too. He handed me a pair of long, dangly, gold earrings, a necklace, and several gold wrist bracelets to go with the outfit. They made me look kind of like a Gypsy woman. Every guy in the club would be wanting to dance with me. Not that I wanted to dance with other men. It made my heart pound just knowing I would be lusted after by every guy that saw me.

Tom drove us to a part of town I had never frequented. It looked a little seedy. He told me he was supposed to meet a man named Mike there at ten, but had to run another quick errand. He didn’t want to miss the appointment so he told the guy I, Cindy, would be meeting him. All I had to do was pick up the payment for the guy’s new computer system and Tom would deliver it the following week. Nothing difficult. Computers were what I used to do when I was Tom. Now that the real Cindy was playing Tom, she was picking up my old line of work, the same as I was taking over her position as an Administrative Assistant. Tom said he would be back in forty five minutes to pick me up. I watched the tail lights of his car disappear down the busy city street. That was when I realized I forgot to ask what this Mike guy looked like. I stepped back against the front of the buildings and waited. It was a busy sidewalk. Lots of people walked by. A man in a suit approached me.

"Hi!" he smiled.

"Hi. I’m Cindy." I smiled back, "Are you Mike?"

"Sure am, if you want to call me Mike."

I tried to make small talk and thought I’d ask about the system he was buying.

"What type of package are you buying, Mike?"

"From the looks of it, a beautiful one" he grinned.

"Do you think it is worth the money?" I asked.

"From the looks of it" he smiled again.

"Eight hundred and it is yours" I held out my hand and gave him the most seductive look I could muster.

I was thinking Eight hundred dollars for a descent computer wasn’t a bad price when Mike grabbed my hand and slapped something cold against my wrist. It was a hand cuff.

"Hey!" I yelped, as he roughly spun me around.

I stumbled to keep my balance in the four in heeled pumps and felt cold steel bite into my other wrist as he wrenched my other arm behind me. My hands were cuffed behind my back.

"Cindy, I’m placing you under arrest for prostitution. Any thing you say…"

He dragged me towards the back of a police van that had pulled up to the curb and droned on while I tried to tell him I wasn’t a prostitute and was meeting a guy named Mike. He didn’t care. I couldn’t believe this was happening to me. I wasn’t even really a girl. He pushed me up into the back of the van which was crowded with other prostitutes. As I sat on the bench, sandwiched between a girl wearing fishnet tights and six inch stilettos and a girl wearing hot pants with thigh high boots, I realized how I could be mistaken for one of them.

"First time?" the fish net girl asked.

"Yes. But I’m not a prostitute!" I exclaimed.

"Sure, honey. I’m not either." she smirked sarcastically.

"No. You don’t understand. This is a horrible mistake. I was meeting a guy."

"Imagine that. So was I." She snickered.

The other girls in the van started laughing and cajoling me. I gazed around at all of them making jokes at my expense. It was unbelievable. I was being arrested as a female prostitute. The way I was dressed, you couldn’t tell me from any of the others.

They marched us into the police station in single file and handcuffs. Some of the cops jeered us as they passed. I wasn’t even allowed to speak when my turn came. They sat me down beside a desk and shot questions at me like name, address, city, state, did I have any diseases. Conversation other than answering the questions was not allowed. Then they finger printed, and photographed me. Since it was my first arrest, I was given the option to sign a guilty plea and pay a fine or appear in court. I signed the plea and paid the fine. I was now, officially, on record as a prostitute. Of all things, a prostitute. Tom picked me up and I told him what had happened on the way home. I was too upset to go dancing.

"Do you realize what this means, Cindy?" he asked.

"Yeah! I’m a prostitute. A call girl. A hooker, for God’s sake."

"No. Worse than that."

"Worse than that? What could be worse than being a prostitute?"

"Cindy, for life!"

"Cindy, for life?"

"Yes. You are now officially on file as Cindy Rodgers."

"I’m not. You are!"

"No. You are honey! They took your finger prints as Cindy Rodgers. Not mine, yours. That means, from here on out, according to your finger prints, you are Cindy Rodgers, not me. You! Cindy for life."

My jaw dropped open as her words echoed in my head, ‘Cindy for life’.

 

 

 

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© 2002 by Jean M. Chambers. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.