This is my first attempt at writing fiction. This story did not actually happen and is strictly a product of my fertile imagination. If you have a moment drop me an e-mail and let me know if I should continue with this story line and with writing TG fiction in general. Love ya.
Trannie in Training The Beginning
I was never a good student, so when I graduated from high school the easiest way for me to find a job was to go into the military. I was infantry pure and simple. Eventually I got picked up for security and endured that until the end of my contract. Once back in civilian life jobs were still hard to find. I finally got a job as a security guard at a large department store. It was on the night shift and didn't pay that well, but I figured it would do until I found something better. I found an apartment and a room mate. He worked a day job so we almost never saw each other. That was fine by me as I am not that much of a "people person". So what do you do all night long by yourself in an empty department store? No much. We had a small TV in the security office, but TV after midnight is the pits. I read some and played with my game boy. I only had to make rounds once each hour, so there is not a lot demand on my time. Out of boredom I spent a lot of time just walking around the store. On one particular occasion I noticed an advertising sign for some woman's high heeled shoes. The woman in the ad was drop dead gorgeous of course and was wearing red "fuck me" shoes. I stopped and began fantasizing about this babe and her shoes. I felt that familiar stirring in my pants and soon had my tool in hand. It had been a good while since I had sex. I have always had a particular fondness for ladies in high heels, especially red ones for some reason. It felt good to cum in the middle of the woman's shoe department (or anywhere for that matter). After cleaning up my mess I went back to my office and felt sort of bad about what I had done. (But not that bad!)
The next night during my rounds I had to check back with the babe in the shoe department. She was there with her fantastic shoes. I was thinking that I would love to see her walk in those shoes. No such luck. I thought about that as I continued my rounds and had that stirring again that made it difficult to walk. The next hour I took a slightly different track that took me through the shoe department. There on display where those lovely red shoes. I picked the display shoe up and turned it around in my hands. This shoe was pure sexuality. I was getting a hard on just handling it. It then occurred to me that I should try them on. I had no idea what size, but I knew where the stock room was. I got the stock number off of the shoe and headed for the back. What an enormous amount of boxes of shoes. I finally figured out the order and found the section with these shoes. I am not that big so I only wear a man's size 7. I did not know how woman's shoes sizes ran, but figured I would try a 7. I pulled off my boots and socks. The shoe was just too small. I tried an 8 and still no luck. I could get the shoe on, but it was real tight. A size 9 fit pretty well. I put on the other shoe and tried to stand. Whoa! This is not going to be easy. I spent a few minutes just getting used to standing. Then I tried a few steps. I nearly fell over, but persisted. After a few more tires I got so that I could walk, but not to gracefully. I was glad to sit down. My feet were hurting and there were marks from the shoes on my feet. I put my socks and boots back on and got back to work, for what that was worth.
Walking in those shoes became a game and I am just hardheaded enough not to quit until I could do it. Besides it made the endless nights pass by a little more quickly. I discovered that if I wore those little stocking things that they have in the shoe department that the shoes slid on more easily and didn't leave many marks. I also discovered that if I kind of moved my hips around like a woman does that it was much easier to keep my balance. After several hours practice over several nights I got pretty good at walking. I even made my rounds once completely in the shoes. I happened to walk by one of those low mirrors in the shoe department and seeing myself from the waist down in those shoes gave me an immediate boner. I actually had a pretty sexy walk and was turning myself on! Who would have thought that? That gave me another idea. What if I were to wear hose too? Only seeing the legs and shoes I could imagine that I was looking at woman. I found the lingerie department and picked out a pair of pantyhose. I did not realize that were different sizes, so I just picked up the first pair that I came to. I went back to the shoe department, pulled off the shoes and my pants. How in the hell to do you put on pantyhose? I tried to pull them on like socks, but that did not work well. I wound up tearing them. There were two pairs in the package, so I grabbed the other one. I remembered seeing pictures of woman rolling stockings up their legs to I tried bunching them up down to the toe and that actually worked! I had one leg pulled all the way up and now how to get the other one on? I eventually figured out that if I rolled up the first one to my thigh I could get the other one up too. Once I had the pantyhose and shoes on I went to for a walk by the mirrors. "Wow, this is good stuff!" I thought. My legs were bit too hairy for a girl and sort of muscular, but they didn't look bad. The pantyhose were just the ticket. As a bonus, the pantyhose felt kind of nice too. I began to stroke my hard cock through the hose. What a feeling. In no time I was spurting cum. Back to work.
Back at home I decided to shave my legs so as not to ruin the sexy look of my legs in pantyhose. Of course I never have shaved anything but my face and I tell you legs are a bit different. It is hard to get to the back of your legs and I cut myself several times. My legs were burning a bit, so I used some hand lotion to soothe them. Now, here was another new sensation. My smooth legs felt great. I was wishing that I had brought home those pantyhose and couldn't wait to get to work. Once alone, I headed straight to the shoe department pantyhose in hand. The hose felt really nice sliding up my now smooth legs. I put the shoes on and back to my now favorite spot in front of the mirrors. If I did not know that the reflection in the mirror was really me I would have sworn the legs in wearing those sexy heels belonged to a female dancer. While admiring myself I had a thought. If the shoes and hose are turning me on this much imagine what dressing fully in woman's clothes might do. I had no idea where to start as far as sizes, but I had plenty of time alone in the "candy store" to figure it out. Up until this point I had been returning the shoes to the shelf and stashing the pantyhose in my locker. I decided that if I was going to keep doing this I would need to take some of my things home or at least put them in my car.
Over the next couple of weeks I spent a lot of time trying on first panties, bras and slips. Once I figured out the right sizes I started trying dresses, skirts and blouses. As a kid my sister was always trying to get me to play dress up. I always refused. Oh, what I missed. I amassed a number of outfits, underwear sets, and shoes. I found necklaces and clip on earrings. I started looking at fashion magazines, but most of that stuff was way beyond what I could do. I did get an idea of what looked good together and I think I looked pretty good for a guy. Each new discovery and outfit caused the same reaction. I had cum so many times during my explorations that I thought my cock might fall off. As you may have guessed I then progressed to makeup. That was maybe the most challenging part of all. I had lots of makeup to choose from and those huge pictures of sexy models in the makeup department as a guide and inspiration. Putting on makeup became my favorite part of the game (except for the shoes). Much to my disappointment the store did not sell wigs. I spent a little time on-line at home searching the Internet. I found a few long wigs in various colors and styles and placed my order. Once I had my wigs my transformation to a sexy babe each night at work was complete. I would spend nearly the entire shift in drag with at least one or two outfit changes each night. What started out as a curiosity had turned into an obsession. I was sneaking out clothes, shoes, and makeup. I was storing them in my car's trunk, but eventually had to take them into my apartment. Soon there were almost more women's clothes in my closet and dresser than there were men's clothes. On my nights off I was dressing up as a sexy babe and surfing the Internet with my web cam. I had a lot of fun fooling some guys and chatting with other crossdressers. I never realized how many other guys shared my hobby. I got many compliments on my looks. I really got turned on chatting with the other "girls" and seeing how great they looked. I found myself jerking off to their images and was spending a lot of my time looking for "trannie porn" on-line. I happened to find a web site called Nifty Archive and felt like I had hit the lottery.
Discovered I suppose it was inevitable that I would get caught at my game. It was just too perfect. All of the free time. The almost unlimited access to clothes, makeup and shoes. Especially the shoes. I got really comfortable spending most of each night at work dressed as a woman. I did my job of course. Made my rounds did my hourly checks mostly dressed as a hot babe. And I came a lot too. Several times each night in fact. My poor cock was worn out. Anyway, I suppose I got very careless and a bit too comfortable taking home my objects of my new attraction. I borrowed (permanently) a lot of stuff and eventually someone was bound to wonder were all of that stuff was going. On the fateful night I was making my usual rounds in drag. I was actually looking really hot. I stopped to admire myself in front of the full length mirrors and had just pulled out my cock for the first wank of the evening when a voice form the dark said " Well, ain't that the cutest thing!" I just about shit in my panties. Out of the dark stepped my supervisor. I tried to explain, but no words came from my mouth. I am not what I was going to say as I was caught and I knew it. He said " So, is this how you spend every night shift?" I could have tried to lie, but instead replied a feeble "Yes. Pretty much." He then asked " You must have been doing it for a while. You actually look pretty good." Well that took me by surprise! I was expecting to get chewed out and fired at the lease and maybe my ass kicked in the process. He then said " Are you gay?" To which I replied "NO!". He said, "Well, I am not so sure. Come over here and let's find out."
What could I do? I walked over to him and he said "On your knees." I struggle to get off those heels and on my knees. Once there he said "Unzip my pants." I did as told and was surprised to find a semi-hard cock in black nylon panties. I looked up at him and he just smiled. "Pull it out." he said. I was so so surprised that I pulled out his cock without really thinking about it. He moaned a bit and said to play with it like he had seen me doing with my own. I did as told and in no time he was very hard. He stopped me and unbuckled his pants. As his pants slide to the floor I saw that he was wearing a garter belt that matched the panties and dark seamed hose. He pulled of his uniform shirt to reveal a matching bra filled with latex breasts. He then said "Let's find me a pair of pumps like yours. I am sure you know where they are kept." He helped me to my feet and I led him to the ladies shoe department. I asked him what size and he said size 10. He sat down and I went into the back and found the right size. I helped him put on the shoes and then helped him to stand. He walked around a bit with at very sexy little walk. It was obvious he a lot more practise as I had. He swayed back over to me and said that obviously I approved of the shoes and his walk as he reached down and stroked my now hard cock. My attraction to a sexy walk gets me in trouble all of time! We kissed again and I reached down and began to stroke his cock as he stoked mine. It only took a moment and he was cumming in his pretty panties. That is all it took and I came too. He kissed me again and said "I think I am going to have to spend a lot of time supervising the night shift at this store." I said that I probably could use more supervision and smiled. We walked back to the security office and I had to ask why he came to the store at night. He explained that there had been a larger than usual amount of women's items missing at the store. After the last inventory there were many fairly costly high heeled shoes were missing, too. The store rarely had high heels shoplifted as only one shoe is on display while the other shoe is in the stock room. He decided to check the security camera recordings to see what he could discover. He did not find too much on the day time disks. Just the occasional suspicious character, but no repeat offenders and no shoe thieves. For some reason he checked the night recordings and was totally amazed at what he saw. There was a woman walking around the store all night and the security guard was no where in sight. He finally figured out that it was me walking around and decided to use it to his advantage. He had been an avid crossdresser since high school and figured there was no way that I could protest as he had video evidence of me wearing the clothes in the store and wearing out my cock too. I must admit that I would not have chosen to get caught, but now am glad that I did. He comes around every night and has become my mentor in all things feminine. We have had some great times. I am becoming a fairly proficient cock sucker and we even gone out to a drag bar a few times on my night off. But that is another story.