Sandy; Trading My Gender For Heels

I was definitely not a morning person, the grumbling as I made my way to the bathroom a sign of my unhappiness at the beginning of another day. I liked the evenings the best, but surviving the morning these days was getting to be difficult. I did my business, deciding a hot shower might help make some of my problems go away. I leaned into the shower stall to turn on the water and saw the handles on the hot and cold water were missing, so resigned myself to taking a bath. I briefly wondered why the handles were off, but brain activity does not go with being a grouch first thing every morning. I filled the tub and eased my body into the bubbles. Mom must have left some of her bubble bath in the tub after she used it since the tub was now overflowing with tons of bubbles. Oh shit, now I recognize the fragrant smell of her bath salts, I am going to smell like her all day. Oh well too late to do anything about it now.

I laid back in the tub letting the hot water do its thing on my body. The water was definitely cooler when I woke from my impromptu nap, but at least, some of my grouchiness seemed to have vanished too. I toweled off, then wrapped the towel around my waist and headed to my bedroom. I opened the dresser drawer looking for a pair of my briefs. I reached in to grab a pair of briefs, but what I had in my hands was not a pair of briefs. I blinked my eyes twice trying to focus on the object in my hand. Oh gawd, they are panties, brief ones at that and oh so silky. I was rubbing them in my hands when I stepped closer to examine the contents of my drawer more closely.

My first thought was I must have walked into my sister’s room by accident, and was in her dresser. I looked around, nope this is my room and my underwear drawer is filled with panties. I moved them around in the drawer, then found a garter belt, some stockings still in their original packaging, packages of pantyhose and a girdle with garters attached. Maybe Mom is trying one of her mind games on me, not sure the reason but she does engage in this type of behavior on occasion, but never before with female underwear.

Then a thought invaded my mind, I know it is way too early for such weird activity. I ran to the closet, slid open the doors and stared at the floor of the closet. Oh Gawd, she has found my one pair of high heels. Then added many more pairs to keep them company. I quickly looked around for my male footwear, but they are now missing, even my sneakers that I always kept by my bed are gone. After looking at the bed I turn back around and Mom is standing in the doorway, a huge smile on her face. Now at least I know who the culprit is regarding my new underwear and heels.

I waited for her edict on what happened and what I was in for, but it never came. She issued a way too cheery good morning, told me I smelled nice and breakfast would be ready in twenty minutes. Just like that she sashayed off, leaving a very confused male child standing in front of his closet. I debated just pulling on a pair of jeans and a t-shirt and making an appearance, but knowing Mom she would make a big deal out of that, so resigned myself to dress in the underwear and slip on a pair of heels for breakfast. I selected a pair of panties, then tried to figure out how the garter belt went on. I succeeded finally but not sure if how I had it hooked was the proper way.

I rolled a stocking up my leg, noticing for the first time that my short hair on my legs was now missing. Further inspection of my body revealed that all of my hair except for what was on my head was gone. I don’t know how it was accomplished but a few random thoughts led me back to my bath this morning. The feeling was so different, causing all kinds of unintended responses from my male equipment. It was all I could do to get the stocking up my leg and not come all over the place.

That was what I had the heels for in the first place, my girlfriend always wore them and they turned me on so much. After lots of frustrating dates spent with her, I finally succumbed to buying a pair of heels, slipping them on my feet to jerk off to. I know, not much of a male if I get off wearing ladies heels. I had to go to three different thrift stores to find a suitable pair that I could wear, the lady catching me trying them on over in a corner of the store was most helpful, though she smirked the whole time I was paying for the shoes.

Now I presume I will be wearing them quite a bit. I finally got the other stocking up my leg, and after twisting my body every which way, I managed to get the garters attached. The pull of the stockings against my leg and their sliding against each other was about to cause a huge eruption. I set on the bed trying to regain some composure, but caught myself staring at the closet and my choice of footwear. I walked over to the closet and reached down for a red pair, with stiletto heels and a five inch heel height.

Common sense would have me picking a pair with lower heels and maybe a block type heel. But no, the part of my mind that was still functioning picked these to wear. I picked a pair of my jeans to wear, and a t-shirt and after donning them slipped my feet into the heels. My foot was much more arched than normal, it taking me a few moments to be able to take a step or two. The stockings allowed my foot to slip right into the heel, the shoe fitting much better than the ones I had obtained at the thrift store.

I heard Mom calling me to breakfast, now is the time of my reckoning. I made my way to the kitchen, the noise of my heels on the hardwood floor of our house loud and unmistakable. I did sway often, even stumbled a time or two, but eventually made my destination. I calmly sat down at the table, and served myself some of the sausage and eggs she had prepared. The discussion of me wearing heels never came up, we ate and talked about the weather. When we got around to discussing what we were going to do today, I pulled up short. I just remembered that I was planning to go to the mall with my girlfriend, Nina. No doubt wearing heels would change everything. As I washed my dishes at the sink I head the doorbell and Mom went to answer it. She returned a few minutes later with Nina right behind her. I started to run for my room, but Nina grabbed a hold of my arm and led me to the living room.

I was pushed down on the sofa, then she parked her body right next to mine. She looked at me, patiently waiting for me to tell her what this is all about. The fact that she was rubbing my leg through the jeans, the denim sliding over the silky stocking causing a total brain meltdown. Then to make matters worse Mom joined her on a side chair facing the sofa. It took me a few moments to work up the nerve, but I decided a one time confession to all things perverted, might be the best way forward. I knew I would lose Nina, not sure what Mom might think or do to me, but things had progressed too far to let it go without telling the truth on my part. I guess Mom had done a good job raising me, instilling some honesty in my behavior. A guilty conscience probably having a lot to do with my soon to be confession too.

I started at the beginning, giving every detail I could remember. Nina laughed when I remarked about being so frustrated after a date with her. Mom was just sitting there, taking in all of my confession with no obvious signs of emotion. An hour later I finished up with getting dressed this morning and my two near accidents as I donned my clothes. Mom’s first words during all of this, sent a shiver right up my spine. She wanted me to drop my pants and show them what I was wearing, then tell them why I chose each piece of underwear and why the red shoes.

In a near whisper I did as she instructed, both of them scooting closer so that they could hear my barely squeaked out words. Then total silence in the room, as I tried to get my jeans back up, having to stop at my groin due to an obstruction. Mom smiled then told me to go to the bathroom and take care of it, then pull up my jeans the rest of the way. I was redder than my shoes as I click clacked in my heels to the bathroom, my one hand trying desperately to hang on to my jeans. I got the offending item out of the panties and one touch of my hand and I was squirting like a volcano. I washed up, the erection handled, although the red in my face did not fade away. I think I will be forever ashamed of having to do this, even though they were not in front of me at the time, they no doubt knew what I was doing in the bathroom.

When I returned I was told to sit in one of the side chairs facing them on the sofa. Both of them staring at me, I presume thinking of what I had just done. More red, although I doubted there was any blood left in my lower extremities, all of it rushing to my face and cheeks. There was silence for a while, Nina apparently waiting for my Mom to start. I was still shocked that Nina was still here, her boyfriend dressed in female underwear and heels not showing any signs of masculinity, at least in the lower extremities.

“From your actions and choices up to today, there are too many things that were not divulged, both to Nina and myself. So we are going to explore this side of you, where you want it to go and how far. For the foreseeable future you will wear heels both in the house, at your part-time job and when you are out on the town. The only exceptions are when you are in bed and when you are taking a bath. Now to determine if this is just something to get off on, or something deeper we need to cut off your thingy. It will only hurt for a few minutes, then your new underwear will fit so much better. I promptly fainted, I don’t think that was the reaction Mom was looking for.

As soon as I came to, I immediately reached for my male organ, to make sure nothing had happened to him. I let out a big sigh, Mom chuckling in the background. No time like the present to take care of him, putting it off will only make it worse when he gets covered up. My arms were grabbed and I was escorted to Mom’s car, not necessarily willingly. But in the red heels traction was not to be had. I held on to Nina tightly, hoping for her to step in and save my male essence. When we pulled up in front of Mom’s beauty salon, I didn’t know what to think. Swiftly before I could get any thoughts put together I was led to a room at the back of the salon. A technician was preparing something for me, I couldn’t see around Mom to see what it was though.

Mom placed a hand each side of my face making me look at her. “We are going to cover up your male apparatus, a cute female sex organ instead of your male thingy. Nothing is permanent, we are just removing temptation to see what your true desires are. I have my ideas, so does Nina, so consider yourself part of this test to see who may be right. Since you are eighteen years of age, you are old enough to refuse this treatment, but for all concerned I think we need to see where your true feelings reside. So do we welcome Sandy to the household, or go back to what we had before. Either way you are wearing the heels, so what is it to be?”

I swallowed hard, but the smile on Nina’s face did me in. I told them to go ahead and make me a woman, just don’t leave me alone. Nina came around the table and gave me a kiss, holding my head close to her breast. That felt so good, to be held tightly. I felt a hand on junior and then nothing. I tried looking down there, but Nina kept my head close to her chest and my eyes focused on her breasts.

When the tech was finished, Nina lifted my head so I could gaze on my groin, all that was left was a cute slit with a little pubic hair at the entrance. Mom grabbed my other hand and I was helped up, then they re-dressed me and made for the front of the salon. Mom paid the bill, giggling as I walked a little funny towards her car. Nina had my one hand firmly in her grip, I guess to make sure I didn’t try to inspect the new arrangement or run for the hills, before we got home. Believe me it was tempting, but the damage had already been done.

Once home Mom did allow Nina to show me my new female sex, with Junior tucked away there wasn’t anything I could do anyway. I looked everywhere for some seam, or a part of the vagina that was not secured against my skin. The slit in the middle of it the only part accessible, one finger entering that part sent shock waves all over my body. I quickly withdrew my finger, still visibly shaking from the touch just moments before.

Nina was going to head home and change, then we were going to the mall. I did everything I could to kill off that thought, me in heels but everything else looking male sure to give any friends lots of laughs at my expense. Mom did pull me aside and gave me the female facts of life, including how to go to the bathroom properly.

As she was covering what to do after sex, she was almost laughing out loud. But she continued, covering douching and the proper use of a tampon and pad. The giggles were not far away though, a few interrupting her discussion from time to time. Of course, that only made my embarrassment that much worse. Way too much information that I really did not want to know about. I guess she did actually help me some, brushing my hair into a decidedly feminine style, something that Nina swooned over as soon as she returned to pick me up.

I tried again to avoid the excursion, whining about not needing any clothes, and definitely no more heels. Mom did hand me her credit card, as I was being dragged out the door. We got into Nina’s car, since she is a year older than me she has had her license and recently her parents bought her a car. I did have my driver’s permit, but any talk about me driving or getting my license was just that talk. Nina wasted no time in heading for the mall, my stomach doing flip flops at what was ahead for me.

I tried again to stay in the car, telling her I would wait here for her to return. No such luck, I was soon walking towards the mall and my imminent doom. As we entered the mall, several of her friends were waiting for her, I guess she had arranged this too. I was introduced as Sandy, a friend and we started walking the mall. I looked around often trying to see if any of her friends were laughing or giggling at me. I might have looked a little feminine with my hair down like this and the heels, but no breasts and hips kept me far from looking like a real female. I guess luck was with me, they ignored my looks and took me for face value, a tomboy friend of Nina’s.

Apparently I was just a female friend, quieter than normal, but okay since I was wearing and walking in five inch heels. Most of the girls had flats on or low heels so I was looked up to. I even got compliments about my red heels. Several asked where I got them, Nina giving them the name of a shoe store on the other side of town. What few words I managed to get out of my mouth were almost whispered, not trusting my voice to do much more.

Several times groups of boys would come up to us, trying to engage the girls in conversation. Luckily for me none of the boys were ones the girls were interested in, so they were promptly dispatched. It took me about an hour to relax enough to join in the conversations some, a word here or there. It was weird how easy I seemed to be accepted as a fellow female, well maybe just a friend of Nina’s, not sure about the female part.

At our last stop I even tried on a skirt that looked promising. It looked even better on me and I actually bought it with Mom’s credit card. I could see myself explaining to Mom how I just had to have it, it will look so good with my uniform shirt where I work part time. Then that thought and its implications sent my mind into panic, I had forgot all about my part time job, just now realizing that I had to work tonight too. I looked at my phone for the time, only two hours until I have to show up to work at the drive in. I tried to get Nina’s attention, mouthing work. She told the girls we had to get going, Sandy has to work tonight and we need to head in that direction. I was thankful for getting away from the girls, not sure about showing up for work dressed this way.

I pleaded with Nina to allow me to go home first, but to no avail. I was dressed as far as underwear is concerned, I had the red heels and now a skirt that would go perfectly with my uniform shirt. So Nina said I was ready to work a shift.

I actually had met Nina when I used to eat at the drive in. Her step father owned the restaurant and drive in, often Nina would work as the cashier if someone didn’t show up. I met her there when she was filling in one night, and went back often to see her. One day she suggested that I take a part time job there that would give me an excuse to visit her more often. I guess my attraction to her was pretty obvious to everyone, especially her.

Before I could get back to the time clock to punch in and change into the skirt her step-father caught me and giving me a careful appraising look. Nina mentioned as I was getting ready to change clothes, that I could be the hostess tonight instead of a waiter. She already has a skirt just perfect for that job. A smile lit up his face, telling her to make sure I got a little makeup too. I changed, scowling at Nina for getting me right in front of everybody that came into the place. I got a kiss, then she added some lipstick and mascara and led me to the front of the restaurant. At least I was not outside working the drive in spots.

I whined, stomped my feet and protested my situation as she got me to the front reception area. She had totally ignored any verbal comments and physical protests of mine, a trait she has indulged in quite often in our relationship.

She stayed with me for a while, making sure I was doing the job right. I ended up seating a lot of my friends, not one single person recognized me or made any comment. After most of the crowd had come and been seated I helped the waitresses with drinks and busing the tables. It was sure different, walking in the high heels changed the way my body moved, the skirt seemed to leave me so exposed and the lipstick and mascara were certainly unusual, although the lipstick tasted and felt pretty good on my lips. It was a long night, I was so ready for it to end.

At ten before eleven I seated the last group, with any luck we should be finished and cleaned up by midnight. Nina hung around, after the first hour she left me to do my thing and she talked with some of her friends, then set near the front and ogled my legs and ass. She would make little comments about them, most of her comments quite embarrassing especially for a former male. Of course, never vocalized loud enough for others to hear. I did have an almost permanent blush on my cheeks that evening from her comments.

Since I was doing the duties of a hostess, I missed out on my tips, although I did receive many compliments on my appearance and helping the other servers. Jason her step-father pulled me aside at the close telling me that he wanted me as a full time hostess, Tuesday through Saturday from four until midnight. I hesitated but his offer of ten dollars an hour had me agreeing before I realized what I was getting myself into. Of course, Nina heard all of the conversation, anxious to get me alone so she could show me how proud she was of me. She might have been proud of me, but it wasn’t twenty minutes later when I fully realized what I had done to myself. Now a five day a week job as a female, a female wearing skirts, heels and makeup. Who needs enemies when I can do this to myself with such utter ease.

Several more days wearing the underwear and the different heels brought me to a judgment day. Do I continue or give it all up. I knew I should revert to male clothes and stop wearing the heels, but they tend to grow on you. From the first moment I slip on a pair of panties in the morning I finish dressing as a female never even thinking of my former male existence.

I embraced it, Nina and I went shopping for more skirts, and I really liked how they felt when I wore them, now infatuated with all things feminine. My wardrobe grew exponentially, a new skirt requiring a blouse to match, then of course a pair of heels in the right color.

Mom saw to it that I had more underwear, my male clothes slowly disappearing from my closet. Then one day after spending the morning shopping with Nina we arrived back at my house to see the Goodwill truck in my driveway and boxes being loaded in it. Sure enough the last of my male clothes were now gone, Sandy is indeed here to stay.

Along with everything else Nina had made sure that I received a weekly salon appointment. First my hair was dealt with, then some longer nails, then the biggy, some breasts to help fill out my numerous blouses that I was acquiring. I knowingly signed the permission slips for these treatments, on a couple of things I eagerly looked forward to the new enhancements.

About six weeks after all of this started Mom laid some papers on the kitchen table right after breakfast. They dealt with a legal name change, making Sandy official. Several days at the salon where the few remaining masculine features were eliminated and Sandy became official.

Nina has always been a big supporter of Sandy, our love making strictly female to female, something she adores and I have learned to enjoy. My part time job morphed, now I am the evening supervisor, a job that I am really proud of. Her Father has officially approved of our relationship, we stay in her room when over at her house. The loving is strictly female to female, maybe later when we consider having kids things might change, but until then what we have is mutually enjoyable. Of course, Mom has been treating us as a couple for months.

The few pair of heels that were lower than four inches have disappeared, now only the taller heels have a spot in my closet. I have worn them so long I even have to slip into a pair to use the bathroom at night. Do I regret getting caught owning a pair of heels, nope it was one of the luckiest days in my life. The day I traded my gender for heels.

I am sure there will be lots of adventures as Sandy, life will certainly not be boring. With Nina at my side I look forward to each adventure, an adventure wearing heels.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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