Jenny; A Sissy For Kayla
My girlfriend was quite the business woman, owning several fashion related businesses. Her latest acquisition had cut into some of our together time and I was whining about it. She handled the complaint as she normally does, a sensual kiss that turned my mind to mush as she rubbed my male appendage with her hand. Two weeks later I was back to whining, she had spent the last five days at her new business, leaving me alone at my apartment.
We both were spoiled brats, our parents providing each of us with everything we requested as we grew up. Then when we graduated college a huge trust fund to handle most anything we might want in the years to come. The trust fund provided so much every month, to be deposited into our checking accounts. Jobs were not needed, we had no needs that we could not obtain ourselves. That is how she had acquired her businesses, each one researched and after careful consideration bought for a song. The businesses all had been in trouble financially, so the expense in buying them was minimal.
Where I was content to waste my time on the internet and play an inordinate amount of time on video games, Kayla wanted something to occupy her time, something to do with her free time. Each business she tackled was turned around by her, profitability returned to the business within the first few months.
I was the one suffering, of acute Kaylaitis. I pleaded with her, I begged her for some of her time, making a royal ass of myself in the process. Finally she had enough of my persistent whining telling, me she would pick me up at ten the next morning and I could hang with her for the rest of the day. She was truthful with me letting me know she was still going in to the business, but with a little luck she would be finished about three in the afternoon, leaving the rest of the day just for us.
That was better than nothing so I quickly agreed to her plan. When she pulled up in front of the store my mouth was open in awe. It was a sissy store, part of a national chain that I had read about, with her buying the local franchise of it. I followed her in, and she sat about getting the lights on and the store open. I found a love seat over in the corner and made myself comfortable. Kayla was setting up a display, having a photographer coming in right after lunch to take some pictures for an ad she was planning to run in the local newspaper.
The whole idea of her owning a sissy store left me a little unsure. This is a side of her I have never seen before. So I did what any red blooded male might do and retreated to a safe spot and observed. I was quiet the whole morning only speaking to her when she asked me to go down a couple of stores and get each of us a tea. The sweet shop had candies and assorted tempting treats along with coffee, tea and other beverages. I ordered two cups of tea and waited for them to be prepared. Returning to Kayla’s store I did as she requested, giving her a cup of tea when she had finished with a customer, quickly retreating to my safe spot and sipping my tea.
Several customers showed up during the morning, a couple of ladies by themselves shopping for their sissies. I was listening to them talk with Kayla, the conversations most interesting. Then a mother dragging her teenage son with her right before lunch. She picked out a couple of dresses for him, as he tried to shrink into the chair he had positioned himself on. He was dragged to the dressing room and soon emerged wearing one of the dresses. To say he looked different would be quite an understatement. The dress was so frilly and juvenile, he now looked like he was a member of a kindergarten class, although a little bigger size wise than most of his classmates. With his hair in a ponytail the look was almost complete.
He was obviously embarrassed, trying to hide behind his Mom. Kayla helped adjust the dress a little better on him then suggested some panties and shoes that would complete the look Mom was after. Mom agreed, the boy soon wearing the panties and shoes as Mom paid for his clothes. I noticed that the mother had left his clothes in the waste bin at the register, his dress apparently the new mode of fashion for him.
Kayla’s sales help came in right before lunch, they conferred for a few minutes then Kayla came to get me so we could grab some lunch. We walked a few blocks to a fast food place, ordered then found a spot on their patio to sit and eat our lunch. I did notice Kayla looking at me a little more closely, a cute little smirk appearing on her face. I tried to ignore her attention, not wanting to inquire about the smirk and what it might mean for me.
We made it back to the store, Laney her sales help telling her that the model for the photographer had called in sick, not able to make it, since she was throwing up every few minutes. Kayla called the photographer and postponed the photo shoot until five, when the store would be closed. She took her phone and started calling a few people, presumably ones that she had talked to about modeling her outfits. An hour later she sat down in the stockroom disgusted and depressed. I could see she was in deep thought than that smirk again as she was looking my way. I got up to take a walk, and made it as far as the front door of the store. Kayla grabbed a hand and dragged me back to the stockroom and sat me on some boxes of clothing that had come in that afternoon. She was quiet for a minute, figuring out what to say.
I knew I was in deep do do, but was at a loss as what to do or say to avoid what I was sure was coming. It didn’t take much intellect to figure out what she had in mind. The fact that I was not much taller than her and quite thin made her idea quite plausible. I thought back to the teenage boy that had been dressed as a sissy and shuddered. That boy was just a little thinner than me, and probably the same height. I had allowed my hair to grow down to my shoulders, and wore it in a low ponytail. A fact that now might fit in perfectly with her proposed plans.
She wasted no time in coercing me to help her, along with her pleas her stroking my male equipment and her kisses to my face and ears were making thinking difficult. I didn’t tell her no, but I also didn’t agree to do as she wanted. When she relented some I looked down at my body and discovered I was naked. She had managed to get me undressed stashing my clothes somewhere. Laney had closed down the store and register, wanting to know if Kayla needed her to do anything else. As she surveyed my naked body she giggled, then hugged Kayla and left. As she closed the door and locked it the photographer had showed up and she let her in, yelling to Kayla that the photographer was here. Kayla left me for a few minutes to show the photographer where to set up, then returned with a handful of clothes apparently for me.
My body was carefully appraised, then she went to a cabinet and removed an electric shaver. My little bit of body hair was quickly removed, then she grabbed a brush and brushed out my hair after removing the scrunchie that held it in the ponytail.
Still naked I had given up resisting her efforts, figuring the sooner I cooperate the sooner that I can return to my male persona. I was not looking forward to any of this, far from it. What male would want to wear a frilly dress and pose for pictures in front of a lady photographer.
The panties were first, a frilly pair with rows of lace on the rear portion of the panties. Kayla called them rumba panties. They were silky, and fit way too good. Snug in the crouch, and caressing my body with their silky embrace. Kayla came up to me, reached into the front of the panties and grabbed junior and pushed him back between my legs. When she released the panties they kept him secured there, a flat front now on that portion of my body. It was a little uncomfortable, but the dainty slip and dress that was slid over my head caused me to focus on how I looked now. I looked in a mirror a few feet away, the juvenile look of a pretty sissy the only image I could see. Kayla added some lipstick to my lips, then dragged me out to the display that she had set up earlier.
I took a look at it, not really paying any attention earlier when she was setting it up. A huge teddy bear was on one side of the display, a life size doll dressed like me on the other side of the display. Each one was held by me as hundreds of pictures were taken, the photographer wanting me to kiss the bear and doll, and hug it tight to my body.
I was blushing at doing something so girly, I am sure making the pictures that much more humiliating. I was later to learn that is a key part of being a sissy, actions and clothes all designed to humiliate the sissy, and make them dependent on an adult to take care of them.
The evening wore on, with me having to change into at least fifteen different dresses, each one frillier and daintier than the last. The photographer must have taken at least a thousand pictures of me each one showing only a sissy. My hair was brushed different ways, each one emphasizing the sissy image. I got a set of pigtails for some pictures and even one with my hair in curlers while I was wearing a nightie. That luckily was one of the last pictures she took of me. Sometime during the evening I was referred to as Jenny, my apparent sissy name now.
While Kayla and the photographer discussed the photo shoot I sat back on the pile of boxes, waiting for her to finish. I thought of what all of this meant to me, the fact that I could be easily recognized from the pictures taken of me today worried me quire a bit. If Kayla ran this ad in the local newspaper I would be a laughing stock in a very short time.
If I refused to let her use these pictures I doubt there will be much future for us as a couple. Of course refusing to let her use the pictures is such a laugh, here I sit in a child’s nightie with my hair in curlers and wearing makeup. Not exactly the epitome of a strong no nonsense male. Luckily for me there was not a job involved on my part, I can see how ridiculous that might turn out.
Kayla returned grabbing my hand and after picking up her purse led me out of the store to her car. All the time I was trying to escape her, looking right and left to see if someone was looking at me. I asked about my clothes, my wallet and ID still in my pants pocket. She informed me she had my wallet, but the remainder of my clothes are in the trash. No further need for any ID, a sissy named Jenny not requiring any. She did get me in her car, the passenger seat where I was placed. I slumped down in the seat not wanting to be seen by anyone. She fastened my seat belt like you would a child, forcing me to sit up some. I received a kiss on my cheek and she came around to the driver’s side and got in. I breathed a sigh of relief, figuring we were on the way to our home.
Wrong, she pulled into a drive thru, ordering us some food, then after paying and receiving the food she drove over to a near by park. She parked in a spot, overlooking the lake and proceeded to feed me my dinner. I tried more than once to feed myself but was scolded vigorously. Finally I placed my hands on my lap and let her have her way. She used a wet napkin to clean my face, then reapplied some lipstick to my face.
Several people passed by my side of the car, looking in as they passed. No outright laughing but I heard a giggle or two and several turned around so they could get a better look at me as they went down to the lake. Kayla asked if I wanted to go down to the lake, there were several children there and she was sure I would be welcome to play with them.
I looked at her with sheer panic etched on my face. Kayla meanwhile giggling at my facial expressions. She did resume the drive home, once in sight I heaved a huge sigh of relief. I was taken into the house, then straight to her second bedroom. As she opened the door my mouth opened in awe, a super frilly girl’s room was all I saw. I tried to grab the door jamb as she led me into the room. She reached for my thingy and soon I was led over to the bed. She gave me a sizzling kiss, then laid me down on the sheets. She reached for something on each side of me, fastening them together over my waist. I looked down to see what she had done, figuring I could easily unfasten them after she had left. She removed my rumba panties, washed my thingy real good and then slid a diaper under my butt. This was done while she played with my thingy, as I raised my butt up off the bed so she would caress it some more. It was pinned tightly to my body, then a second pair of panties was slid over it. As she slid them up my leg they crinkled some, with me finally realizing they were plastic panties to keep my diaper from leaking. Of course I was beet red, not able to utter any protest to Kayla. Way too much for me to get a grip on, much less figure out what to do about it. Then she removed a pair of mittens and slid them on to my hands. They were finger less, just one pocket for my hand. They had a strap that fastened around my wrist keeping them from being removed. I tried to wiggle my fingers, but the mittens would not allow that movement. She slid a blindfold over my eyes, then raised my nightie up to my neck. She squeezed my nipples some, getting them erect and standing out, then fastened something on to the erect nipple. I felt the pressure from whatever she had attached to them but it was not painful. She pulled the nightie back down after tightening the strap holding me to the bed. Tucking the sheets tightly under my body. I was now trapped in the sheets unable to move or do anything to free myself. I was blind now, listening carefully to see if Kayla was going to do anything else to me. I was kissed on the tip of my nose. Then she left the room, apparently turning out the light as she left. The room seemed to get darker, as my eyes tried to adjust to the darkness of the blindfold.
Why I had let her truss me up like this, never saying a word to her in protest. I suddenly felt the need to pee, moaning out loud trying to get her attention. I finally realized that was the reason for the diaper, she had no intention of releasing me to go to the bathroom. I held out as long as I could, but the urge was greater than my willpower. I flooded the diaper, then thought of how I would have to wait until the morning before I could be changed. I did succumb to sleep, not able to free myself from my sheet prison, muck less remove the strap holding me down to the bed.
The next morning Kayla woke me with another kiss to my nose, then felt the diaper to see if I had been forced to use it. She smiled, then started releasing me from the bed. After waking up from my sleep, I started to ask her about why she was doing this, but her finger on my lips implied that I was not to talk. She changed my diaper, but slid the rumba panties over the diaper to cover it up. I smelled like a baby now, the amount of powder she used on me enough for several babies. The nightie was removed then she removed the clamps that she had placed on my nipples last night. Once the blood reentered the nipple I was suddenly in severe pain. They stayed erect though as the redness slowly faded away. I move a mittened hand up to touch them, but soon found out they were now super sensitive. Another one of Kayla’s sissy dresses was slid on to my body, then a pair of girls shoes were slipped on to my feet. A collar was attached around my neck, then I was led through the house and out to her car. Being led by a leash attached to my collar, left me confused and bewildered.
I thought about speaking up again, but decided not to, all of this really confusing me about our relationship now. A short while later she pulled up in front of a beauty salon, a few doors down from her sissy shop. She spoke to the receptionist and then someone from the back came to lead me away, the leash used to get me headed in the right direction. I was sat in a chair and leaned back my hair apparently the focus of today’s visit. She washed and conditioned it after removing the curlers from yesterday’s photo shoot. I had forgotten all about them, once I got used to the feel of them as I tried to get to sleep last night. In the mirror I saw my head covered in curls. Even washing my hair didn’t relax the curl. She cut my hair into a feminine style, with bangs I might add. Then she started weaving in longer strands of hair from my bangs all the way to my neck. The longer hair erased any masculinity I might have had left, The hair now a mixture of curls and straight hair. She separated it into little bunches, then wrapped a piece of paper around the bunch then around a smaller curler. This took quite a bit of time to accomplish. Then a smelly liquid was soaked into each curler with me figuring out I was being given a permanent. Another huge sigh, my time as Kayla’s boyfriend now over, a sissy for the foreseeable future. I guess I could put up with it, at least I will still be with her. I kind of zoned out for a while while my permanent was processed.
After another rinse, she combed through my hundreds of curls and then started wrapping them around colored curlers, many different colors depending on where on my head they were used. It had been at least two hours since she started and I was needing to use the bathroom. I started to ask the lady if I could use the bathroom, she looked over to Kayla, who shook her head no. Kayla came over and pushed on my lower stomach and I flooded the diaper. She smiled again and returned to her chair. I never realized she was just a few chairs down from me, my attention only focused on what the lady was doing to my hair.
As my hair was drying under the hair dryer, my nails were worked on, after she removed my mittens, It felt so good to have them off, my fingers flexing in their new found freedom. I received a manicure first, then extensions were added, my nails now extending a half inch past my fingertips. Again I thought of asking why, but silence reined and after the hair dryer shut off I had ten highly polished nails in a pinkish color, my formerly male looking hands now like part of an advertisement for a sissy store.
Then a sudden realization forged to the front of my small brain. Kayla is going to use me as advertisement for her sissy store.
Then back to the new curly hair as the curlers were removed from my hair. Oh gawd, what am I going to do now. I looked like what I imagined a sissy looked like, an exceptional girlish sissy. Not a hint of anything masculine left on my body. My nails, my sissy curls leaving no doubt about my apparent gender.
Kayla was also finished coming over to reclaim her sissy. The leash was reattached and I was led from the salon. A short walk and right into her sissy store. I was taken to the back, my diaper changed them out front to the same display where the photos were taken yesterday. I was positioned in the middle of the display and my leash attached to a beam over the display. She kissed my nose again and then went to take care of other business. I stood up and tried to reach the end of the leash, but my new fingernails prevented me doing anything. I tried where the leash was attached to my collar, the same result. I even tried to undo the collar. but could not find any seam or catch.
There were some customers in the store so soon my appearance was being appraised. They had a frock picked out, asking Kayla if they could see it on the live model. Of course, it was not a problem, my current dress was removed and the new one slipped over my head, right in the middle of the store. I tried to hang on to the dress I was wearing but soon found my hands slapped away, as she made the change. The changing of the dress happened several more times that afternoon, Kayla suggesting it even if the customer did not. Of course having to use the bathroom popped up again, but I knew better that to ask Kayla to free me. A short while later I flooded my diaper again, not even realizing I was doing it. So much for being potty trained, I would imagine I will be totally unable to control myself soon if this keeps up.
It was after five when I was unleashed from my display, and taken to the back. Diaper removed and I was totally washed and cleaned. She had something in her hand when she approached me again, her rubbing my male organ unexpected and bewildering. It was short lived however as she held an ice pack against my thingy, junior shrinking to a mere nubbin. I felt her doing something down there but since everything was still so cold I tried to ignore what was happening. When I did look down there a few minutes later I was shocked, my thingy locked into a male chastity device, the length of it only an inch with my balls locked into a ring snugly behind it.
Again no words spoken from me, just another long sigh, wondering if there was anymore surprises in store for me. I was shedding moisture from my eyes, although I will steadfastly deny that I was crying. Taken to her home, and straight to my new bedroom. The new routine continued on for the next few weeks, staying with Kayla at night and at the sissy store during the day. I now wasn’t even aware when I wet my diaper, the weight of the diaper the only clue to me flooding it yet again. I wore a never ending array of sissy dresses both to model them and also for the customer to see how they looked on a live model. The chastity device stayed on, any attempt to swell up quickly aborted as the points inside of the device dug into my soft flesh.
Then a change in the daily routine, as Kayla took me back to the salon for who knows what. In a private room at the back Kayla sat opposite me and explained what she wanted. She did ask me to listen to her first before I made any comments. First she wanted me to marry her, but the union will not be between husband and wife but between a sissy and her parent. She will see to my care, although the chastity device is permanent. A sissy has no need for any kind of sexual release.
I was to move in with her, sleep with her and she will take care of all of my needs. I will be loved, caressed, and fondled as appropriate for a sissy. The diapers are an another requirement, she loves me being dependent on her for diaper changes, so that is not negotiable.
Sales at the sissy store have soared since I have been there as a model, so that too will continue. She will take extra time to be with me, taking me places dressed as her cute sissy. I will never have to worry about being kept busy, out and about dressed in one of my frilly dresses, at the sissy store or at home with her as she changes my diaper and plays with me.
I hesitated in my response to her, realizing if I accept I will be forever a sissy, diaper dependent and unable to care for myself. I then realized I was already trapped, living the life as she wanted. A sissy for Kayla named Jenny.
© 2016 thru 2024 by Francesca