My Life in High Heels Ch. 03

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A prequal discribing my beginnings as a cross dresser.
4.8k words
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Part 3 of the 9 part series

Updated 06/08/2023
Created 06/03/2010
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cdandie
cdandie
122 Followers

Hello everyone. I've had a lot of people ask me how I got started cross dressing and being a play thing for men. I should have written this to start with so now that I've already written several stories this would now be considered a prequel.

I experimented with dressing in my youth and I never really had an early attraction to men. I was quite enthralled with women, the curves and allure of women got my blood boiling and still intrigue me. I dressed in hose and clothes I accumulated over years and pleasured myself when dressed. As time went by the male body and particularly the penis became interesting to me. I bought a dildo and began experimenting with it by inserting it in me. At the time the internet was in it's infancy and information about my interests was limited.

I lived for many years in an inexpensive apartment and lived in my fantasies in private. Sleeping and lounging in front of the TV in different outfits were my limits. I would order different forms of lingerie, cheap samples of makeup and shoes by mail. Invariably I would get magazines from these companies trying to sell me more stuff at later dates.

Next door to me lived a young Hispanic lady named Nina. She had a son Joaquin who was about eight or nine. I helped her as she was a dancer in a club and worked nights so Joaquin would watch TV at my place on evenings when she was at work and he was not at his dads place. I also helped him with homework and and cooked more than a few meals for the both of them.

One day I was getting my mail and Nina walked up next to me and saw one of the lingerie catalogs I got in the mail. She squealed and said how much she liked their stuff and I immediately offered it to her like it had been put in my box by accident. A week or two later I left town for about a week and my mailbox filled up quickly and the postman saw Nina and she offered to hold my mail for me.. When I got back she delivered my mail with a stare and then a wink. I was taken aback but didn't know how to react.

About a month later I was barbequing on the porch and she came out and pulled over a lawn chair and sat down next to me. I offered her a beer and we sat and chatted, Nothing special, just small talk. Finally she blurted out, "you're a cross dresser aren't you"? I very slowly and deliberately asked her why she would say such a thing. She said the first womans clothing catalog and the numerous others I got when she collected my mail were the first clues but sitting here like this she noticed my legs were shaved. Wasn't much I could say at that point so I said yes I was. She then surprised me and said that was cool. We sat silently for awhile then I broke the ice and asked if I could ask a question. She said sure and I said how do you women walk in high heels. Laughing she said practice and then added that I should try dancing in them like she has to at the club.

She asked if I needed help dressing and I said it would be to weird.. She said don't worry I had been the truest friend she'd ever had and she'd be there for me. After chowing down on ribs she insisted on getting started. Following me into my apartment she wanted to see my wardrobe. After going through everything she made recommendations. Then wanted to see me made up.

That I knew was a train wreck and Nina told me to come to her apartment where she spent almost six hours teaching me how to apply makeup. She also agreed to make my purchases for me and spent a week accumulated all the necessary accoutrements for me to look like a proper lady.

After taking my credit card, she purchased wigs, stockings, garter belts, pantyhose, all in an assortment of colors. Then she went with me to thrift stores to pick out dresses, blouses, and some of the highest heels I'd ever seen. We also spent a great deal of time getting the necessary makeup which was very helpful.

Once I was completely outfitted she watched me apply my makeup offering input when needed. Eyelashes were the toughest. She helped me into a black garter belt then showed me the proper way to get into stockings. She never gave me panties and I had noticed she never had purchased any for me. Not once did she comment on my never ending erection even when she reached for my woody and tucked it under the garter belt like she was simply hiding an offending object. . She helped me squeeze into the skirt she chose for me and the blouse then helped me walk in the some black six inch stilettos she had picked for me. She said I was definitely a first class hooker now and needed a name and the only name I could think of was Lisa, the name of the sexiest girl I'd known in collage.

We sat on the bed and talked endlessly about makeup, clothing and lingerie choices. Finally she asked me if I was bi or gay. I explained that I was very much attracted to women and even though I'd never been with a man I was certainly interested. Nina educated me on the pitfalls of men and the tasks I was going to be expected to preform. I told her that though hesitant I was looking forward to my "duties".

Nina also said that she could see I'd shaved my legs but that I had done a feeble job at that and that I was going to have to remove a lot more hair to be a proper wench. She explained that at the club where she worked they were allowed to have pubic hair but none was allowed to be seen from the edges of the G string they were required to wear. The skimpy nature of her attire required that she have nothing more than a thin strip above her pussy. She told me she shaved in the bathtub and that the hardest part was the thin fine hairs around her asshole.

She told me to strip and fill my tub with hot water. As I did so she left but came back from her apartment with a cacophony of bottles . She poured some oils in the hot water that she said would soften my skin and make shaving easier. She had me lay in the tub and she handed me a razor. A triple bladed job that she said was best. She lathered up my legs and told me to get started. I methodically scraped my legs smooth. Then she rubbed lather on the few chest hairs and under my arms. I preformed the same task on these parts then she filled her tiny hand with shaving cream, reached down and grabbed my erection and began coating my pubic region in the foam. Taking the razor from me she began shaving me bare . One hand pulling the tip of my penis to one side, the other rhythmically sliding the razor over the exposed area till I was bald.

Nina then told me to pull up my legs which I obediently did. She ordered me "higher" till my knees were pressing my chest. In this exposed and vulnerable position she worked a handful of creamy lather into my crack and then began depriving this very private area of all traces of hair. I watched the intensity in her eyes as she worked, no visible sign of lust, desire or disgust. The blood pounding in my cock on the other hand was a very visible display of my randy mood. Once completed she told me to roll over and she would do my my back. I had very little chest hair and even less on my back so she had me bare in short order.

Once completed Nina ordered me to stand and she took the shower wand and rinsed me off. I told her it felt weird but great. She informed me that I now had to pay her back by trimming her as it was so much easier for another person to trim the intimate parts of ones body. In agreeing to I realized that in trusting her with my secrets she now trusted me to help with her own intimate responsibilities.

As she stripped I realized Nina was even more attractive than I had always thought. She was not the curvy voluptuous blonde classic pinup. She was however extremely petite, maybe 5' tall and 90 lbs. after a heavy meal. Her breasts were not massive, possibly filling a b-cup and actually pointed skyward. Her aureola's were large and pointed and topped with impressive nipples. Her pubic hair was simply a thin strip of hair about two inches long above her mound.

Once she was immersed in the water I rubbed soap over her body making a sudsy lather. She watched me, intently looking at my face, as I washed her body. After doing her legs and arms and having her lean forward to scrub her back I had her lay back and I softly cleaned her breasts. Cupping and sliding my fingers over her soft skin. Her rigidness gave way and when I went to her second breast her eyes closed and she had visibly relaxed. After finishing with her bosom I moved to her nether region. Instinctively she parted her legs. With a bar of soap in the palm of my hand I pushed forward. Using my three middle fingers I worked her bottom cleavage and opening clean, lightly fingering her bottom hole. Moving up I worked my soapy fingers in, out and around her vulva, flopping what turned out to be massive labial flaps. I then lowered the level of the water and proceeded to lather and shave her gorgeous legs. I lifted and shaved under her arms then proceeded to shave the stubble on either side of the thin strip of pubic hair on her pubic mound. For some time her eyes had been closed and she seemed peaceful. I hated to disturb her solitude. Sensing my dilemma she pulled up her legs exposing her puckered anus and beautiful pussy. With a dollop of shaving cream I smeared her soft cleft and proceeded with the removing all traces of hair from the crease in her impeccable derriere After clearing her of the tiny amount of hair around her ass I had to physically hold her impressive labia lips to one side in order to closely shave under the flaps that lazily laid open. I finished by rinsing her then massaged oils into soft olive skin.

I gave her a bath towel and she carried it to the bed then laid out on it. She pointed her finger to me and told me to lay with her. Facing each other and looking into each other eyes after sharing such intimacy she said we could do this once a week. She said she knew I was extremely excited which was no secret as my erection was at that very moment pushing into her soft belly but she would not have sex with me as she was not on the pill and she could not have another child. I nodded and though disappointed I understood. She told me to get dressed again. I reapplied my makeup, put on a bodice which she handed me and pulled up the stockings which I had on earlier and attached them to the garter straps of the bodice. I pulled on the wig and was reaching for the skirt when she told me that was enough. I slipped on my heels and stood.

Nina watched as I turned and gave her a 360 degree view of my feminized body. She rolled to the edge of the bed and said no intercourse didn't mean we couldn't satisfy each other. Taking my throbbing cock she engulfed it in her mouth. I looked down and reached for her bottom.. She shook her head and said if I wanted to be a woman I needed to learn how to give a proper blow job so I needed to watch what she does. She licked my shaft and bald balls then she guided me onto the bed keeping my cock in her mouth and a hand squeezing my testicles.

Looking up at me she removed her mouth long enough to tell me to relax and let her pleasure me. She covered the head of my penis with her lips and formed an O with her fingers and masturbated my cock into her mouth. She stopped long enough to explain what she was doing and making sure I was taking in every bit of this lesson. Her eyes never left mine and it struck me how she was concentrating on making love to me with her eyes as much as her mouth. A lesson not lost and one not forgotten by me. I warned Nina of my impending orgasm. She slowed her hand strokes but tightened the clench of her lips around my dick. I realized she intended on taking my ejaculate in her mouth. When the first pulse of sperm erupted in her mouth she involuntarily blinked several times but regained her composure and kept eye contact with me. She kept softly stroking my shaft with her hand, then using her thumb on the bottom of cock and two other finger on the top. I realized she was pulling or milking the cream from my dick.

Once she was satisfied there was no more cream to coax from my depths she pulled from my cock then sat up. I could tell she had my load in her mouth. She told me with some difficulty that men loved seeing their seed in the mouth of a woman and that a good blow job was not complete until the lady swallowed and that men loved seeing that. Nina then said since this was a lesson I had to swallow so she leaned over me and kissed me allowing my seed to flow into my open mouth. Our tongues danced in the cream. Pulling away she said for me to open my mouth and show her the sperm. Parting my lips she told me to swirl my tongue and play with the sperm. Then she told me to swallow in one gulp. In one gulp as ordered my freshly squeezed load of semen slid down my own throat. I found it not to be unpleasant at all. She then proceeded to lick all remnants of semen from my softening penis.

Afterwords she laid on my chest with my arm around her. She asked how I liked cum swallowing and I told her of my observation that the flavor was different but not distasteful. She told me at the club where she worked that they sometimes were asked to do private lap dances in the back and that for extra money the girls would have sex with men. She said she wouldn't have intercourse but would perform oral sex on the men and she found that she could make as much money by giving good blow jobs as the girls having intercourse. She asked me if I often wanted to be with a man. I explained to her that I didn't walk down the street looking at guys and say, "ooh I want to have sex with that guy", like I could with an attractive woman but that the thought of a hard, throbbing cock for some reason, deep in me brought up some deep lustful desire that I couldn't explain.

She asked me if I wanted the real thing and I said of course but in today's world one had to be careful and very discriminating. The other problem at that point in time was that there were no internet dating sites available in which to meet people. Nina asked me if I wanted to have man in my bottom. I told her my reoccurring fantasy of having my legs hoisted on a man shoulders as he took his pleasure in my depths. She asked if I had ever used dildos on myself. She immediately offered to use one on me. I asked for a rain check as I explained that I would need to clean myself so we could play for a length of time and that was something I still wished to do privately. Nina insisted on a date for the following Sunday as she was off and her son wasn't due back from his fathers until Monday. Once I agreed she said we needed a strap on and needed to go shop for one at that very moment. Once I agreed to this she begged me to go as I was dressed. I said I'd come "out " enough for one day and changed into my straight clothes.

We drove across town to an adult book store that I knew had a large selection of toys. We shopped and compared for over an hour. We decided on a strap on nylon belt that buckled in place and would accept a large variety of different toys and it also had a six inch vibrating penis that would stimulate the inside of the person wearing the belt. Nina picked an assortment of penis shaped toys of various lengths and girths. Once in the car she looked like she was unwrapping Christmas presents, giggling , oohing and ahing.

When we got home she begged me to use them now but I begged off saying I still needed time to properly clean out and Sunday would be best.. I thought at the time if I let her anywhere near my bottom with a dildo and that strap on, she was so ginned up on adrenaline that she;d of wrecked my bottom on our first time.

At 8am on Sunday I was trembling in anticipation myself when she called me and asked if I was ready. I told her not yet and she barked back "well whats taking you so long". So much for her relaxing a bit.

I commenced the process I had found to be the best for me when it came to cleaning out. I had a vinyl hose that fit tight in the shower pipe that came out of the wall. I laid down in the tub and once the water temperature was comfortable I probed my anal opening with the hose. As soon a it finds its mark the warm water flows into me. I squeeze making the water fill me deeply. Once I feel it flowing far up I pull the hose from me and stand and bend over and side to side. This seems to hasten the action of the water usually provoking some cramps. I lay back in the tub with my legs laying on the side and allow myself to empty then simply wash down the drain. I'll repeat this process several times then end by simply allowing the hose to flow deep in me and relaxing my bottom. The water will flow out just as quickly. The whole process takes at least an hour this way but I've learned I'm still able to play about eight hours later so the time spent is well worth it.

Once I was clean, inside and out I began the process of applying makeup. Since this was my first time with anybody while dressed I was in a sense a virgin so decided to go soft with the makeup rather than vampy. My eye lasses were still the most difficult. I chose a light pink, boned corset Nina had found at an estate sale. I laced up as tight as possible making my waist as thin as I'd ever seen it. I attached to the garter straps some white seamed stockings that actually had a glossy sheen to them. The corset had six garters which I was fast learning was the minimum number needed to properly keep stockings in place. The corset was an under bust design so I put on this white bullet bra with spiral stitching that seemed absolutely incredible to me. I wished I had some breasts to fill those incredible cups with but breast forms were not widely available yet at that time. I put on a pink sleeveless sweater and a white nylon, lycra form fitting skirt. Then with some difficulty, as bending in that tight corset was nearly impossible, I buckled the strap on some white six inch stiletto heels I had.

I called Nina. She picked up and asked if I was ready. I said I was and she said I needed to walk to her apartment and escort her to mine. I balked at leaving my safe zone but she insisted. I relented and was heading for the door when I realized I needed a wig. I went back and chose the long wavy blonde one. After fitting it in place and a quick once over I was off. I left my apartment and went straight to Nina's After knocking waiting then knocking and ringing the bell and waiting some more she finally opened the door. She giggled and smiled broadly as I sternly looked at her knowing she'd delayed opening her door intentionally. Luckily nobody walked by but I was trembling in fear, excitement and anticipation.

She walked at my side to my apartment and after walking in and closing the door she stood back with her arms crossed and one hand holding her chin as she appraised my look. Clapping she agreed with my choices and said I was beautiful. Hot but still beautiful. Taking my hand she led me to the bed room. She stripped off her sweats and began pulling up her strap on belt I watched closely to she her reaction when the rubber penis meant for her entered her. She simply spread her legs pulled it up and once up gave it a jerk up to get it in place which caused her to close her eyes momentarily and she quickly yelped ever so slightly.

I could tell by her slight trembling that she was excited and no time was going to be wasted on foreplay. Nina then put her hands on her hips and with a smile ordered me to take off my sweater and my skirt. Once I was exposed, wearing only my lingerie and heels she told me to sit on the bed. She strutted to me and unceremoniously ordered me to suck her cock. Obediently I took the 7 inch cock she had chosen for me and began licking the shaft like I had seen her do. I then moved up the shaft and put the tip of the penile behemoth in my mouth I began jacking it off in my mouth. I knew Nina had the vibrator going already in her pussy as she was rotating her hips and moaning I felt her hands on the back of my head and she began fucking my face. Soon I couldn't catch my breath and she was going nuts. Finally she relaxed and told me to lay on the bed and let my head hang off the edge. After doing so she nudged my mouth with her new cock. I parted my lips and she slowly slid in me. As Nina worked it deeper the head of the cock hit my gag reflex I started to gag and she stopped going deeper but she also held it in place. She told me to concentrate on not gagging and to force myself to relax. By doing so I found having this monster in my throat became much more tolerable. I could tell I was going to have to practice over riding may gag reflex.

cdandie
cdandie
122 Followers
12