tagTranssexuals & CrossdressersThe story of Karri-Ann

The story of Karri-Ann


Foreword. This story contains male bi-sexuality, forced feminization, and spanking. If you feel uncomfortable or do not like these subjects please do not read. Due to the length of the story, if you just want to read the sex parts, skip to chapter 5. But for those of you that wish to read it from beginning to end, I hope you enjoy. Please leave constructive criticism and positive remarks only. Thank you 57chevy for editing.


Chapter 1

It began with wanting to try something different. I had spent the last few years healing up from surgery. They had put me on some strong steroid medication, so I had put on more pounds than I wanted. It had taken 2 years just to get my weight down to 168 pounds. But to my chagrin, I still had man boobs from the rapid weight gain. Since I had been sick and recovering I had lost my career, and was unemployed. I was really hitting a depressing time in my life. I needed a change, I needed a pick me up that would get me back to where I had been. One of the things that I started to come up with was some of my sexual fantasies that had popped in my head these last few years, but I was feeling very unattractive at this time. I went online to the meeting sites and browsed around for a few months. I had always been on the fence about becoming a bi-sexual, I had thought about it since I had reached puberty. But I had always chased those thoughts away, for Pete's sake, I was a guy!

So, I finally decided to plunge in to my deepest desires. I had placed an ad in a couple of sites, seeking a relationship with a couple. I figured that would be my safest bet, if I didn't like being with a guy, oh well, there is the wife. Months passed by, with no response. I really became depressed, I was just too eager; I had wanted to feel good about myself again. I did get a few responses then, but it was always the same, not real, mostly a horny husband that wanted to do man on man stuff, without the wife knowing. One response never met me when we did agree to a hotel. I was even more despondent, and out 80 bucks. Jobs were almost non-existent, and my love life was going no where fast.

Then I did get a promising response. Dan and Sarah were their names and they wanted me to come over to their house to meet, and talk to see how we would get along together. The response told me they were a couple in there 40's, had no children. And they also wanted to try something new to make their relationship more "colorful" as they put it. I starred at their picture attached to the e-mail. Dan stood a good 6'1 it looked like, maybe 200 pounds, salt and peppered short hair, not a bad looking guy, Sarah was about 5'10, flaming red hair that flowed over her shoulders in waves, a thin build, and a set of piercing green eyes. My heart skipped a beat, and I rapidly sent a response back agreeing, asking when we could meet. I sat there for 2 hours watching the screen, waiting for a reply. None came; my heart sank like a thrown stone in a dark pond.

Two days later the reply came. "Tonight, 7 PM sharp!". That's all it said. Relief and excitement raced through me, then dread. I looked at my watch and it was only 9 AM. I must have taken 5 showers, tried on 5 different shirts and pants, trying to come up with the most appealing outfit to impress them. The clock seemed to slow down to a crawl. At 6 PM, I was pacing, then it struck me, were the hell was I to go? Panic gripped me, I raced to the computer, and they had not told me where their house was! I clicked on the email again; no; it didn't say anything on the address. I felt the pit of my stomach plummet. Then I noticed that I had new mail. Clicking on it I beamed a broad smile, there was the address.

I arrived at the driveway to their address. It was a long drive that led up and around a corner seemingly in the middle of nowhere. A sign stood next to the driveway, "Klicker Trucking" it boasted. I wondered if I was even at the right place. I continued driving up the road. I rounded the corner to see a large garage with several semi trucks parked around. There appeared to be an office attached to the garage. Behind the garage I saw the driveway continue to a 2 story house in a cloister of trees. I drove to where a pick up was parked and stopped beside it. Taking a deep breath, I opened the car door and stepped out.

The doorbell made a chime go on inside the house. I heard the tap tap of heals as they got to the door. The door came open and my breath was taken away. In a tight black dress Sarah stood in front of me, her legs were wrapped in black stockings, her hair pulled back into a pony tail, her faced beamed at me. "You must be Keith, please come in"

This was going great, I thought to myself. I stepped in and followed Sarah into the house. "Please have a seat; Dan will be out soon, as he had to finish up some work"

I sat on the couch and watched Sarah disappear into; what I figured was the kitchen. She called out and asked if I had found the place easy to find. I lied and told her that it wasn't a problem; knew right where it was all the time.

Sarah poked her head out from around the corner "You're a lousy liar" she began laughing and went back to what she was doing in the kitchen.

Sarah popped out of the kitchen again, two glasses were in her hands and she handed me one. Dan then walked in from the back room. Dan greeted me with a hearty hello, and shook my hand. His hand shake was brutal; his hands were like steel vices. He was exactly like his picture, taller then me, a slight pouch, but nothing that made him look unfit, he had broad shoulders and the look of someone that has done hard labor all his life. We all sat down, I found out that he owned a small trucking company with a few employees. Him and Sarah had been married for 10 years, but had decided that they didn't want any kids. There was some more small chat, and then they started asking me questions. Dan found out then I was unemployed and looking for work. "Well you know what Keith, why don't you work for me, I can use someone in the office."

This was getting better and better. "Yeah, Dan, I could really use the job right now"

Sarah chimed in this time handing me my fourth drink, that I just realized must have had whiskey in it, I was in the middle of a good buzz. "There would be some really good benefits if you come work for us" Her mischievous smile took me back, and then when she winked I caught on to what she was hinting to.

Dan chuckled and agreed with her. "There would be a few things you have to agree to though"

I shrugged my shoulder and stated all jobs do. "Well Keith, you have to agree to do everything Sarah and I tell you to do, no arguments about anything we ask from you. We say something, you do it." Dan went on with describing that there would be a dress code and policy and procedures that I would have to agree with. With needing a job so bad, and the fact my rent was past due, I shrugged my shoulders and told them I was in. Dan and Sarah looked at each other and smiled. Dan excused himself, and Sarah picked up with some more small chat. The drinks were really kicking in now, my lips felt numb. I smiled, hoping it looked seductive to Sarah. Dan came back in carrying some papers. He put them before me and told me to go ahead and read them and sign them and then I would be full time employed, with housing. The buzz was getting to me, because I didn't catch the last part.

"Initial here, and here, and here, sign here....and here."

His voice seemed to make me tired for some reason. I scratched my initials and signatures, looked up and smiled with Dan and Sarah smiling at me, I had the feeling though that I was looking at two very hungry wolves. Sarah reached down and stroked my cheek. "Here my pretty little sweet, let me get you a different drink"

Sarah shuffled away and I looked at Dan and was about to ask what my title was going to be and when do we start working. Sarah came back in then, interrupting the sentence coming from me, handing me one of the three champagne glasses. Tipping the glass to them, I toasted them, they smiled as I up ended the glass in one swallow.

Dan gave me a knowing look, "well Kari-Ann, you start work immediately."

What a weird thing to say. I thought, and why did he call me, what was it? Oh yeah Kari-Ann, why....things were slowing down for me, things blurred and weren't making sense, I tried saying as much to Dan and Sarah, who stood above me smiling brightly. Sarah whispered in my ear.

"Go ahead sweetie, go to sleep, it will be much better in the morning."

The ocean of black over took me and I knew only darkness of sleep then.

Chapter 2

My mind began to struggle through the cobwebs and reality slowly entered my mind. There were thick blankets covering me, my body was sore and somewhat tingly. My head felt like mush, my body was a slug; I tried to will some strength into it. My breathing started to return to normal, and slow but sure, energy began to ebb into my legs and arms. My eyes batted open for a few minutes and I looked at a different ceiling. My eyes shut again. Thoughts began to form in their correct order. Where the hell was I? My mind worked harder then, and then the headache started. A wave of nausea hit my stomach and I instantly sat up. Bad thing to do, I cursed. Sparks flew through my head as I tried getting the swirling world to stop. I cracked open my eyes again and tried once again to get my bearings, I stopped when I noticed a bathroom. I immediately threw my legs over the edge of the bed and forced them to take the brunt of my weight as I tried to get to the bathroom as fast as possible. Like a newborn fawn, I managed to stumble my way to the bathroom and reached the toilet in time to empty out my stomach. After the heaving stopped, my brain seemed better capable of making rational thoughts. That must have been a hell of a party last night, I thought to myself. I looked around the bathroom; it was small, with a tub and shower. It looked like it belonged to a girl, pink and girly things all over the place. I then began to notice what I was wearing, or actually lack of wearing. It looked like a pink nightgown; I chuckled and thought again...Hell of a party. Then I noticed I had no hair on my body.

"What the hell.." I was confused once again.

I heard the bedroom door open and a female say "Kari-Ann you awake yet?"

I came out of the bathroom seeing if this was Karri-Ann's room mate, and find out where the hell I was and why was I shaved bare. Instead I looked on a stunning looking redhead. Things fell into place then, well most of them anyway.

"Sarah, what the hell happened last night I can't remember a thing after our toast"

Sarah took two steps in and slapped me across the face as hard as she could. Stars erupted in my head again

"WHAT THE HE....."


Again confusion. Why was she yelling at me, why did she hit me, why does she keep calling me Karri-Ann? I was about to ask her again, but her hand came up and cocked itself ready to slap a filling out of my teeth. I rubbed my cheek and remained silent.

"Good girl Karri-Ann, Now I know you have some questions."

She brushed past me and went to a closet.

"The first thing you must know is that you signed the contract for the next year to doing whatever we tell you."

"And you will do whatever we tell you! Or else!"

Sarah was getting things out of the closet and placing them on the bed.

"You WILL always refer to me or Dan as, "Yes Ma'am, or Yes Sir", " Its always a positive answer from you at all times, no questions from you unless we give you permission"

She once again went to the closet and bent over to get something out of a drawer.

"There will be things you have to do when you go to sleep and when you awake in the morning, There is a strict regiment that you will follow, as you complete tasks given to you properly, you will earn new tasks and responsibilities"

My mouth was open in awe at this orientation. I was in shock of what I was hearing.

"Close your mouth dear, its un-lady like." "Now," She sighed and looked at me with a scrutinizing eye.

"We will begin with your morning regiment."

My tongue finally found its place in my mouth. "Excuse me Ma'am, may I ask a question?"

Her eye's burned brightly as if she was about to beat the hell out of me, but then softened.

"As this is your first day I will give you a slight leeway to knowing things."

I took a deep breath and began, "I don't know who you people think you are, but I want out of here, this is not what I agreed to, and I feel it is highly illegal, probably even criminal, however if you let me go now, I will never speak of this to anyone."

Feeling this would bring Sarah back to her senses and I would be home soon to shower this incident off of me, God knows what they did to me when I was passed out, and I also made a note to myself, never to drink that much again.

Sarah cocked her head and stared at me for a minute, then turned on her heal and walked to the door, where she pushed a button on an intercom.

"Dan, would you come down here, we are having THAT issue we were talking about."

Good, I thought, I am making headway; Dan will talk sense into this woman. I heard an outer door open, then a click as the door to the room we were in open with a rush. Dan came in abruptly, a very angry look on his face, his brown eyes almost glowing; in his hand was what looked like a paddle you would find in an old school house. With two long strides he reached me as I was trying to back up from his charging form. In one move, he grabbed my arm in a strong hand grip, sat down on the bed, and flung me face down over his knees. I then found out what the paddle was for. WHACK!

"KARRI-ANN!" WHACK! "YOU SIGNED A CONTRACT!" WHACK! "IN IT, YOU AGREED TO FOLLOW THE EXACT ORDERS OF MYSELF AND SARAH" WHACK! Tears flowed from my eyes and I whimpered each time the paddle struck my now bare ass, which must have glowed fire engine red by this time.


I was in full sob mode now, the pain was unbearable.


Embarrassment burned through me at what was happening, I was sobbing like.....well I was sobbing like a little girl. Dan sat me up suddenly; grabbing me in another vice like hand he turned my face to meet his in a forced kiss. I began to immediately struggle in his grasp, but he had me pinned tightly, I could not move. Soon, I realized I was not going to be able to break out of his grasp; I went limp and let him kiss me. It was a strange feeling, having a man kiss me. After a few moments he broke off the kiss and looked into my eyes.

"Do you understand now what I said" he said softly, "Do you understand that you can't go anywhere? Do you understand; that you will never question us again after this?"

My sobbing was irritating me now, but I couldn't stop. I worked his words over in my head; it stopped on one of the things.

"250,000 dollars?" I whispered.

Dan smiled largely at me; showing his teeth.

"Yes, it will be deposited in a bank account for you at the end of the year, everything is taken care of for you, you just do everything we tell you for the next year, and the money is yours."

I mulled it over in my brain, which was a lot of money. I thought about it, how bad can this be, they want me to behave as a girl, it would just be for a year, then I am out. I did 4 years in the military, how much worse could it be?

I sniffed "ok"

Dan smiled, gave a wink to Sarah, and then stood me up off his lap.

"You will do as you're told now?" he asked.

"Yes sir." I sheepishly said. This is going to be really weird, I thought.

Again the smile, then a nod to Sarah and out the door he walked. Sarah gazed at me with a cocked eyebrow.

"Ready now?"

"Yes ma'am" I responded.

"Good! Now as before I was rudely interrupted."

She paused to give me a peeved look "You are expected to do morning and nightly regiments to keep with policy and procedures."

Sarah went into the bathroom, opened a cupboard underneath the sink, and pulled out a bottle.

"Strip off your clothes"

I was about to say something, then caught myself. I felt the heat of my face as I pulled off the nightgown that I had on. I let it fall to the ground. A disapproving look was instantly on Sarah's face.

"Cleanliness is Godliness" She muttered.

I instantly bent over and picked up the discarded clothing. Folding it up, I gazed around to find a place to put it. Sarah cleared her throat and pointed on the wall across from her. A chute was on the wall, with a sign saying "dirty clothes". I sheepishly grinned and walked over to it, I placed the nightgown in to it, then slipping off the pink panties I let them disappear down the chute also. Turning I covered my crotch area. To my surprise I found I really had no hair anywhere on my body. My skin felt like I had a sunburn.

"Don't worry about being modest, I saw plenty last night, After all how do you think we got all that hair off you?"

She lightly laughed. I still stood with my hands covering what now felt like a very inadequate sized genitalia.

"Go ahead and lay down on your back on the floor."

I sat down and laid back, watching the ceiling intently as if it were going to fall on me at any time.

"Relax girl, it will be much easier, you will be doing this every night before bed, each morning when you get ready and any time you have to defecate."

She went on in a very clinical way, almost sterile, like it was brushing my teeth.

Grabbing my legs under the knees she lifted and folded me backward so my ass was pointing straight in the air. I felt a pinch as she inserted the tip of the bottle into my ass. Cold liquid shot into my orifice startling me.

"Hold it there for a little bit."

She stood up and went into the bathroom again. I heard a rush of water into the bathtub I had seen before. After a few moments she stepped back out and looked at me for a bit.

"OK sweetie, stand up, and for God's sake hold that water in."

I did as she had instructed, there was a feeling of an intense urge to let loose what was being stored in my bowels. I hurried into the bathroom and shot straight to the toilet. I needed no further instruction on what to do. I let loose and felt relief at once. I looked over to see her filling the bathtub, steam drifted up from the suds that churned in the tub. She reached over and turned off the faucets. She then turned to the shower, opening the door, she turned it on.

"Step over here, now." She shooed me into the shower unit. "Squat down" she commanded me.

Squatting down, I felt her hands push on my back until I caught myself on the shower wall. She pulled a hose that was coiled on the hook next to the faucet knobs. A long nozzle was attached, which she unceremoniously shoved right up my ass. I gasped and clenched my ass.

"Relax" she cooed, and stroked my head, I tried unclenching, but it was very difficult.

I noticed soon, that clear water was being flushed down the drain. She saw it too, and re-coiled the nozzle, placing it back where she had gotten it from.

"You are to do this as I said, before bed, in the morning, and anytime you shit."

I grimaced at this thought. I began the mantra in my mind, $250,000....$250,000.

"Now; in the tub with you"

The hot water burned as I stepped in, I was about to step out again, but Sarah grabbed my shoulders and pushed me down. I sat down. The hot water was intense on my skin. Sarah plunged her hands in the water; pulling a wash cloth from the depths, she began scrubbing me. I was wondering if I was ever going to have skin again. Sarah washed every inch of me, humming to her self as she did. I wanted to fall asleep again. Sarah sensed this and smacked the back of my head.

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