Cindy

by Jean M. Chambers

 

Part 4

 

It all started a few months ago when my room mate Cindy thought it would be cute if we wore the same hair style. I ended up with platinum blonde hair, cut in a page, just like Cindy’s. We looked like twins. That is when she got the idea to dress me up as her to play a joke on the doorman of our apartment high-rise. Then my neighbors got involved and things got way out of hand. I pretended to be Cindy and Cindy pretended to be my twin, Candy. When I went to switch back to being my normal self, Tom, Cindy got upset. She said she had always wanted a sister to bum around with and begged me to pretend I was her sister for a few days longer. I was an independent computer consultant between jobs so I said okay. Besides, it was kind of exciting being a girl.

 

Putting on makeup every morning and wearing pantyhose, skirts, bras, and heels all day got old fast. After a few more days of being Cindy I wanted to switch back to being Tom and would have, had it not been for the argument. We went out bar hopping as twins. When we got home I told Cindy I was changing back to Tom the next morning. She said that was fine, because I couldn’t make it living as a full time woman anyway. The alcohol from earlier that evening and my pride started talking. We argued and ended up betting that she or I could live as the other for several months. One thing led to another and the next day I ended up with the shape of a woman, compliments of a female plastic surgeon I had gone to for breast implants. Just prior to the operation I insulted her. When I woke up I found she gave me hip implants to boot. Shortly after my implants I started feeling sick to my stomach frequently and my nipples got sore. The surgeon said it would go away. She was right. It did.

 

Cindy had her hair cut and dyed like I had typically worn mine as my former self, Tom. With a few minor changes she looked just like my old self. I, on the other hand, looked just like her. To finalize the switch we exchanged all of our legal ID and documents, so that neither could back out of the bet. Cindy was to start a new job as an Executive Secretary that coming Monday. I went in her place. Working as a female Secretary was totally different than working as a man. The other girls in the office were nice and helped me learn my new position over the next few weeks. I was soon accepted as one of the girls and quickly fell into a daily routine. Get up, fix my makeup and hair, put on my bra, panties, pantyhose, and skirt suit, grab my purse, and run to the subway. Frequently, the girls from work and I would go out for lunch. Sally, Lee, Brittany, and Terry, and I became good friends. Sometimes we would go to a restaurant or shopping. At five I would go home on the subway, change out of my suit into a casual skirt or dress and do my nails or some other girl thing.

 

Lee was an oriental beauty. Petite but strong. Sometimes I had to ask her to move a box of copy paper or files because they were too heavy for me. She was very strong for a woman and seemed to be getting stronger by the week. I, on the other hand, was having more and more trouble moving things like chairs or office supplies. I figured it was from the lack of exercise. Lee and a few of the other girls did aerobics a few times a week. When I noticed my thighs getting wider I decided to start working out again and asked if I could join them at the athletic club. They were more than happy to have another in their group. I knew Lee had a thing for women. She had been hitting on me regularly from the day I started. I even let her steal a kiss or two in the ladies room. It was exciting to see the reflection of two women, us, kissing in the lady’s room mirror.

 

One night after an aerobics workout at the gym, Lee asked if I wanted to stop at her place for a drink. She said her apartment was on my way home anyway. I couldn’t see what it would hurt so I accepted the invitation. Her taste in home décor was impeccable. She opened a bottle of wine. Before I knew it she was opening a second. We sat side by side on the couch, talking and giggling like long lost girlfriends. I had made some silly comment and was laughing when she suddenly leaned close, put a hand on the back of my head and pulled my lips to hers. I resisted but she was strong. Our tongues met and I submitted. Her hand gently caressed my nylon covered thigh beneath my skirt. The kiss must have lasted for two minutes. My head was spinning. I couldn’t tell if it was from the wine or the kiss, but I wanted more. She let me go and told me she wanted me. I was entranced. Like a lamb I let her take my hand and lead me down the hall to her bedroom.

 

She pushed me down on to the bed and straddled my waist, leaning over to kiss me. Lee pinned my wrists over my head with one hand. I pretended to struggle. She held me tighter, broke off the kiss and smiled.

"I like to play too" she smiled, "it makes it more interesting. Don’t you think?"

A pair of leather wrist cuffs that I hadn’t seen had been tied to the bed posts. Lee attached one cuff, lovingly, to my right wrist. I saw what she was doing but figured a little Velcro strap couldn’t hold me so I let her do the same to my left wrist and ankles. When I was attached to the to all four corner posts Lee went around the bed pulling the slack out of each strap, until I was stretched spread eagle on the bed. Lee climbed back on top of me kissing me hard as I pretended to struggle. She started getting rough. That was when I really did struggle. The harder I struggled the rougher she got. I started getting loud and she loved it.

"I thought you might be a screamer," she giggled, "so I bought this."

A penis gag dangled from her hand. I started to scream for her to stop but she jammed the rubber penis all the way into my open mouth and fastened the straps tightly around my head. The gag went all the way to the back of my throat, almost choking me, and making it impossible to make anything but a muffled sound. I pulled violently on the Velcro wrist and ankle cuffs, but they held fast, and I realized my mistake. I was helpless.

 

"I’m going to tease you until you are insane with lust."

She unbuttoned my blouse down to my naval and unhooked my front hook bra, letting my breasts fall loose. She rubbed my nipples gently with her finger tips, making them hard, then pinched them hard. My back arched with the pain. She giggled, then put her lips over one and played with it with her tongue while she rubbed the other. Being fondled while tied down and helpless, by a beautiful woman, turned me on. She slid down to my knees and flipped my skirt up, onto my stomach. "Now," she smiled, "I’m going to have some real fun."

She grasped the waist band of my pantyhose and panties and pulled them down. I yelled for her not to, but only a muffled gurgle came out. My manhood sprang into sight. She was shocked and sat there dumbfounded, looking from my manhood to my face and back again. I couldn’t hardly make a sound with the gag in my mouth. The dumbfounded look was slowly replaced by a sinister, mischievous look.

 

"Oh, my. What have we here?" she asked, taking my manhood into her hands and caressing it. I was hard. "Seems our little Cindy has a secret she has been hiding." She stroked me. The look in her eyes turned cold as she sat gazing at my manhood as she gently stroked it, making me harder and harder. "Are you having fun pretending to be a girl? You are so naughty." She was in deep thought. Without warning she leaned forward and took me in her mouth, getting me wet by sliding my member in and out, between her lips. Then she raised up onto her knees, lifted her skirt, pulled her panties to the side and went down on me. I was so horny I almost came. She stopped. "I’ll make you a deal. You do what ever I ask, without question and I won’t tell anyone your secret. You’ll be my private little pet. After all, us girls have to stick together." She giggled. "Work will be much more exciting from now on. I can promise you that." Lee rode me again, slowly, until I came harder than ever before. My body bucked beneath her and I pulled at the restraints with all of my strength, but couldn’t get loose. She teased me for hours before she finally let me go, reminding me of our deal.

 

I found a note from Tom on the table when I got home. It read, ‘Cindy, you’ve been a great room mate and friend. I’ve become addicted to being Tom and do not wish to return to being Cindy, ever. There is so much more freedom being a man. I’ve moved out and won’t be coming back. Please, don’t try to find me, because you won’t. I’ve started a whole new life as Tom. Unfortunately, this means you will have to remain Cindy, permanently. I’ve terminated the apartment lease as of the month’s end since my name, Tom, was the only name on it and you were just rooming with me. With your looks I’m sure you will not have a difficult time finding a new place. Whatever remains is yours for the taking. Also, you may as well know the reason your breasts have been sore, you are more emotional, and look more feminine with each passing day. The plastic surgeon, doctor Judy, gave you a female hormone implant at the time of your breast augmentation. It is a two year, time released implant. By then, not only will you look feminine, but your psyche will be also. All the best. Tom.’ I wilted to the floor on my knees and started crying. I couldn’t be stuck being Cindy for the rest of my life. It wasn’t fair! I wasn’t even a real girl.

 

No wonder I was finding men more attractive and was more emotional. The female hormones were slowly changing me into a real female and there was nothing I could do to stop it. Going to the police was out of the question. They would think I was crazy. I really couldn’t prove I had ever been Tom. My mind screamed that this couldn’t be happening. A quick look around the apartment confirmed it was. I didn’t know what else to do so I called Lee. Lee knew my secret anyway. She came over and I told her the whole story. How easily we swapped identities and I, a man, had no choice but to live as Cindy, a woman, intrigued her. Lee sat quietly thinking for several minutes. Finally, she told me to grab my purse and some clothes. She wanted me to move in with her. We would move the rest of my things the following week.

 

Soon after moving in I found that Lee had a kinky side and loved role playing. She liked making homemade love and bondage films. Lee coerced me into staring in her films by threatening me with my secret. Once I posed as a maid who came to clean. Another time I posed as a Secretary and she the boss. There was always bondage involved and we always ended up making passionate love. I admit. Some of the roles I played for her were a real turn on. Filming our little skits was thrilling. To all appearances it looked like two women in the films. Most nights, after filming one of her little choreographed encounters, we would sit down and watch ourselves in action. She wrote a script that she called her crowning glory. It was more daring than any of the others we had done. She wanted to film this one at the office, after hours, when no one was around. I didn’t want to do it but again she threatened me.

 

She pretended to be a secretary working at a desk outside one of the executive offices. I was to be a man, disguised as another secretary working late, approach her desk, drag her into the office, bind, and rape her. Simple enough. We took our places, her at the desk and I around the corner, down the hall. I rounded the corner with a leather bag in my hand. She looked up as I approached her desk and smiled.

"Hi, Cindy. I thought I was the only one working late."

"I have a surprise for you."

"Oh, what?"

I stepped around her desk, sat the bag down, and pulled out a ball gag.

"This!" I smiled at her while I dangled it in her face.

"What is it for?" she asked, looking perplexed.

"Why, you of course." I said, quickly climbing onto her lap and pinning her into her chair.

She gasped. A look of horror spread across her face as I roughly pushed the ball into her mouth and buckled the straps firmly around her head. Lee pretended to fight back. I knew she could have easily fended me off if she really wanted to, but she was playing the weak female. With the gag in place all she could do was make grunting sounds as she pulled at the unyielding straps.

 

I grabbed the bag off the desk and pulled her roughly into the vacant office by the arm. Lee lost one of her high heels enroute and stumbled to the carpeted floor and onto her back. Her acting was great. I pulled a black, adjustable spreader bar out of the bag as I sat on her chest pinning her arms to the floor. The bar had one leather cuff attached to each end and two mounted a third the way in from each end. I buckled her wrists to the ends of the bar, then rolled her over and buckled her ankles to the two remaining cuffs. When I was done I helped her onto her knees. Lee struggled against the restraints, but it was useless. She was in a kneeling position with her arms extended out, away from her sides. Her skirt had ridden high up on her thighs. I let out a cruel laugh. She struggled more and grunted through the gag.

 

"We’re going to have some fun now, you and I. You’ve probably noticed me watching you. That is because I want you, Lee. I’ve wanted you for some time. You’ve brushed off all of my attempts to flirt with you. Now we’ll have to do this the hard way. If only you had been more receptive. I lifted the skirt of my suit and pulled my panty hose and panties down, exposing my male member. Lee’s eyes got big, feigning surprise. "You see, Lee. I may look and act like a typical woman, but I’m not. I’m really a man, posing as a woman." I walked behind her and eased her forward so she was kneeling with her head resting on the floor and her bum in the air. I worked her skirt up around her waist and panties down. Lee was wearing a garter belt with stockings under her skirt suit. She was totally exposed and struggled against the spreader bar, but could do nothing.

 

I rubbed the tip of my penis against her vagina and entered her. She moaned. We both came within seconds. To finish the scene I stood up, straightened myself out, laughed, and left the room, closing the door behind me. A few moments later I went back in and released Lee. We made love again on the desk, except this time she was on top. The next night we sat down to watch our handy work. I couldn’t help thinking how real it looked while watching it. It really looked like I was raping her. Then I noticed the angle of the camera was different than I remembered.

 

"Looks pretty real, doesn’t it, Cindy? Have you ever wondered what it feels like to be taken, instead of being the taker? To be taken as a woman? To actually have a man’s penis inside of you and unable to stop him? To have his sperm injected into you, unable to wash it off afterwards?" Lee mused out loud to me, Then she looked me straight in the eyes "No? I didn’t think so. But… you will. Next time you’ll be the girl being raped."

"Okay. That will be fun." I said innocently.

"Maybe not" Lee said coolly.

"What do you mean?"

She smiled devilishly.

"Instead of pretending you are a girl… lets say you actually become one. Then you won’t have to deceive anyone any more."

"Now wait a minute! If you think …"

"No, Cindy! I know. That is exactly what you are going to do. You probably noticed the video looks a little different than normal. That is because it is. You see," she held the tape up for me to see, "this video came from the office security cameras. If you don’t do what I say, this tape will go to the police and I will tell them that you forcibly raped me. What do you think a woman’s prison is like?"

"I… I…" I stammered, "You can’t be serious!"

 

"Totally." she stated flatly, "You’ve already lived and worked as a female for the better part of a year. A few trips to a psychologist and you’ll be ready to go. That, by the way has already been arranged and so has your Transsexual group meetings. Marilyn is your counselor. She is very nice by the way. And helpful. She told me everything I needed to know. You’ll be able to have the operation within a few months."

"You’re crazy, Lee, if you think I’m going to go along with this. Just because I was forced into taking Cindy’s identity doesn’t mean I actually want to become a female."

"Why not? Look at yourself! You already are. You look, dress, act, talk, and live like one. Heck. You’ve stood bare butt naked, except for panties, in the middle of a girl’s shower room and no one looked twice at you, except to admire your beautiful breasts. I know. I was there! Several times. One small adjustment and you’ll be complete."

"I don’t want to be complete! What you are talking about is permanent. There is no changing back! I would be a girl for real then, permanently."

"Exactly." Lee stated with finality, "I’ve got plans for you. You’ll do it, or else."

She held up the tape. I grabbed for it but she was quick and pulled it away. Then she shrugged and tossed it at me anyway.

"Here. I have copies."

 

 

 

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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.