Throughout my teenage years the journey continued as you would expect. I spent hours going through the catelogue looking at the women clothes and fantasising about wearing, especially the lingerie. I would delve into my mothers underwear drawer when I could. Every now and then I plucked up the confidence to buy my own tights due to be scared that my mother would notice hers were stretched. I would wear them and throw them out. I noticed that the girls I dated all had big breasts and I loved to touch them and please the girls. Sex was not a big driving factor but being with a girl and pleasing her was. Outwardly I was a standard typical boy but internally my desire to dress was growing.
I lived like this through my teenage years and through my early 20’s. I still debated the whole concept of if I dressed as a woman did that make me gay but I still did not find men attractive and I loved being with a woman and so my confusion continued. When I was in Uni my chances to dress disappeared. When I was home my sister had moved out and by now I was bigger than her anyway. I survived by sticking to wearing tights every now and then. My girlfriend at the time discovered a porno mag I had and she went nuts. If she had looked a bit harder in the bag she would have found the tights I wore when looking at the mag. Now that would have been an interesting conversation. Over those years I had many near misses. My step father coming home earlier than expected when I had just slipped my sisters skirt on, was one of those. Luckily I heard the car door and I was able to strip and pretend I was going for a shower. My heart was racing and I must have been flushed. Another time was when I tried on my mothers lipstick. I looked stunning (in my opinion) and I felt great. Then came the time to take it off. It was not so easy. I scrubbed and scrubbed. I was convinced everybody knew when they came home and I kept rubbing my lips to make sure there was none on there.
It was not until I moved in with girlfriend after Uni that I started to embrace the cross dressing. At first I dabbled with her clothes but none seemed to fit and her underwear sadly was not sexy. It was at this time that I started to purchase my own clothes. The first shop I went to was Asda. I bought knickers, a bra, a skirt and a blouse. everything was on sale. I had no idea on sizes and I was scared that the shop assisted was going to point and laugh at me, whilst calling me a dirty pervert. My hands were shaking at the till and I had guilt written all over my face. My heart was pounding and I was sweating. Bizarrely I have none of these feeling when buying my wife clothes but on this occasion I was convinced the woman knew they were for me. I rushed out of the shop as quick as I could. I drove home, locked the door stripped naked and started to put the clothes on. Pink knickers, barely fit. Pink bra, too small and left marks. Plaid skirt. stunning. Blouse, too big, looked like a sack. My heart sank. I removed the clothes that did not fit and noticed the bra marks. Panic set in. all the clothes were removed, bagged and hidden in the attic. I then set about what can only be described as beating myself to try and remove the bra strap marks. I did everything I could. By the time my girlfriend came home I was stressed and unsatisfied. It was a disappointing night and my spirits were low. I promised not to waste money again and give up this cross dressing for good. Fast forward two weeks and my girlfriend was visiting her parents for the night. I had bought her a little Miss Naughty silk nightie and there I was laying in bed in cased in silk and feeling beautiful.
Stephanie 