Part 4

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.


Part 3

I was lucky when I was growing up to have a sister four years older than me. Our size was pretty similar and I was able to use her clothes. Thats is not to say that I was in her wardrobe all the time but she had one outfit that caught my attention. It was a black velvet skirt and jacket. You have to remember this was the 80’s and she was a fan of Madonna and the Breakfast Club movie. This outfit fitted that style and I loved the look of it. This outfit marked my journey from knicker wearer to cross dresser. At the time I did not realise this and again just thought of myself as experimenting (how naive was I).

By the time I plucked up the courage to raid my sisters wardrobe for this velvet desire I was now regularly wearing tights for my sexual release but I had also discovered a body suit. It was black and snapped together between my legs. It was so tight fitting. I can remember the excitement I felt putting this on and how sexy my body felt to touch. The feeling of being sexy was earth shattering and I remember pressing myself up against a mirror to imagine what it would feel like to have another person on me. I loved that body suit and to this day I prefer them to basques.

On this particular occasion I remember pulling on the tights and then the body suit. I snapped the poppers shut and felt my body becoming enclosed. I then entered my sisters room. I carefully opened her wardrobe and after making a mental not of how everything looked I pulled out the hanger with the skirt and jacket. I pulled the skirt on and then the jacket. I was hooked. It felt as wonderful as what I had hoped. It made a crinkly noise when I moved and the feeling of the netting touching my nylon legs was electric. I felt so light headed but not dizzy. The feeling was excitement mixed with sexy. I felt beautiful but needless to say it did not last long the emotions were too much and it was all I could do to strip before I climaxed.

I remember that feeling so fondly. For the first time in my young life I had truly felt free. Unfortunately whilst I laid on the floor breathing heavy after my climax the thoughts of disgust returned but now they brought a friend. This time the penny dropped. It was not normal what I was doing and therefore I must be gay. That was horrifying. Here I and was barely 13, I had just climaxed after dressing in my mothers tights and body suit and topping it off with my sisters skirt and jacket and now I had to contend with the belief that I may be gay. I hated myself. I cleaned up, I scrubbed at myself, I cried a little and then I put it all in a box in the side of my head and denied it. I promised myself I would not do it again. I promised myself that I was not gay because thats not what people were in my friendship group. I settled on being confused and weak.

Needless to say. I could not keep my promise to myself of not doing it again and my fears of being gay grew every time. I must say at this point I have no issue with people being gay. My fear was based on my age, location and how I perceived the world at that time. It was scary and I had nobody to talk to. The internet did not exist and the battle I started to face then is  a battle I have faced up to a few years ago when I realised crossdresser does not mean gay. There were lots of other things that made me think I was not gay the main one being I did not find men attractive. The problem with this was I did not find men attractive but I like to dress as a woman to climax so surely that meant I was a woman in a mans body and at my age that meant gay.


Part 2

When I think about cross dressing the woman from the story in my first blog is never far from my thoughts. I remember the story describing her slender body in jeans that hugged her figure and the blouse that was billowy but showed enough shape and definition that the firm breasts were obvious. I remember how the woman was confident about who she was and that it was her, that noticed the man, it was her that called him into the shop, it was her that challenged him on staring at her and it was her that instigated sex by taking control of the matter.

It was the confidence of this woman that appealed to me and still does. I recognised in this woman a level of confidence and authority that I lacked when I wore my jean and t-shirt. I found the confidence she had in herself intoxicating. At the timeI did not realise these feeling and I just found her confidence a turn on and for years I craved this type of woman. Somebody who will take control and put me in my place. I have since discovered that this level of control manifests itself in my desire to have a woman strip back my masculinity by dressing me as a female and taking on the stereotypical role of a female.

The woman in the story awakened my sexual urges but I found that those urges were never truly reproduced until I slipped on the first pair of silk knickers. The actual thought process from looking at the lingerie pages of a catalogue, to looking in the knicker drawer of my mother to touching them and then wearing them escapes me. I can only assume that I was suitably curious enough to make each of those steps and in the heat of the moment saw nothing wrong with the actions but just assumed thats what all boys do. However, what I do know is that when I stepped into those knickers the first time I felt a level of sexual confidence that I had never felt before and it to was intoxicating. I did not know it at the time but I had started to feel how I imagined the woman in the story had felt (it took me a long time to make that connection and by the time I got there I was well on my journey of crossdressing and self realisation). At first I was happy to just use knickers to satisfy my craving for this sexual feeling but soon I discovered nylons. It was when I plucked up the confidence to put a pair of tights on for the first time that the sexual brain cells exploded. I have never felt something as empowering as tights. To this day they are still the my favourite item to wear and they instantly transform me from feeling like a weird man in knickers to a confident human who has sex appeal. This is heightened by the addition of heels (but we will get to them later).

The downside to these initial footsteps into crossdressing was the guilt, the hatred and the disgust I felt towards myself as I took the clothes off. This was of course coupled with my worries of being caught. Would my mother discover her tights had been worn?, would I put the clothes back in the wrong place?, would somebody come home and see me in knickers and tights with a “hard on”. I hated myself but I was constantly drawn back to repeating the actions over and over again. I am not a religious person but I found myself believing I was going to hell. over the years I have even prayed to god and asked for help in moving away from the feelings. I have since realised that these feelings are wrong and that it is ok to crossdress but for a long time I viewed myself a degenerate. It is hard to truly explain the roller coaster of emotions that I felt but if you can imagine a 13 year old boy sitting in the bath scrubbing at his skin and praying to a god, asking for forgiveness and help in not repeating the actions you will start to understand how the elation of feeling empowered was easily replaced after I had released my sexual energy.


My Crossdressing Journey

Placeholder ImageI cannot remember the first time I wore female clothes. I know I was young, a teenager going through the mind field of puberty. I remember reading a story in an adult magazine (yes i read the stories) and it talked about a woman working in a shop window and a man noticing her pubic hair sticking through a rip in her jeans. One thing led to another and they had sex. I remember being turned on by the thought of this woman’s body and pubic hair. At the time I thought it was the normal way to feel but when I came to explore myself i did not picture the woman I tried to imitate her. I put on some knickers and a dress. I was lucky that I had an older sister and I raided her skirts but it was my mothers knickers that I went for as they were nicer, more like what I imagined the woman in the story would have worn. I put the clothes on and I remember feeling excited as the crush black velvet skirt touched my bare legs. The excitement was amazing and I became very aroused. I loved the feeling right up until I came and then I found myself disgusted but what I was wearing. I assumed this was normal. I took the clothes off making sure that I had not stained them and returned them to their place. I told myself thats what all boys do but somewhere deep down inside of me I knew that was not true. I made sure that I did not tell anybody and that was how my journey started. It was a journey that has lasted until now and will continue. I hope to use this blog to write about my experiences and to express the journey that I have been on. A journey that has resulted in self loathing and finally acceptance.