I enjoyed the feel and look of feminine clothes from a very early age. I am fortunate that I have a sister a couple of years younger, so I was able to try on her clothes in private when no one was around, as well as my mother’s, as I got a bit older. I do remember wearing my sister’s swimsuits, the shiny, sleek Lycra-type outfits in their bright colours with the high-cut styles.
I was small for my age, so despite the two-year difference, we were similar in size, though as she grew older, she developed fairly large breasts quite early for her age, so she attracted a lot of interest from older boys. I was also very shy with girls; I didn’t have any girlfriends at school, preferring the company of other boys. I recall at the comprehensive school in my early teens that two attractive boys were clearly gay, one of whom, Paul, lived fairly locally, so we walked to school and back home together and became friends. I often went up to his bedroom before going home, as both his mother and father worked and didn’t get home till later in the evening.
We would watch TV or play games together. But quite often we would look through his father’s collection of porn magazines, which Paul had discovered. Paul openly admitted that he preferred the naked men to the women. I admired the women’s bodies and outfits, but also the men’s figures and large, erect penises. Paul and I used to compare our own smaller penises with the male models. Mine was much smaller, but similar in size to Paul’s, mine at about 5″ in length, his slightly larger with a little more girth. Neither of us was circumcised, and both of us were fairly hairless in the pubic region. In fact, we both looked quite dainty. This early exploration also led to light touching and holding of each other’s penises, rubbing them together whilst looking through the magazines we would both get small erections.
We also used to practice kissing while lying on his bed. Neither of us had any facial hair at this age, so I imagined that kissing Paul was like kissing a girl. I remember the first time Paul kissed me and put his tongue into my mouth. I was surprised but enjoyed the experience, so we honed our French kissing skills. To enhance the experience, we also took turns being the “girl” by wearing his mother’s lipstick. We also took it in turns to dress up in his mother’s lingerie, pretending we were the girls in the magazines, though we were obviously lacking in breasts. Often, whilst naked, we also explored each other’s bodies with our fingers and hands and had fun leaving lipstick marks on each other’s necks and chests.
This friendship continued for several years until I left school at 16 and started work in a large male-dominated firm as an office boy, which mainly involved making and fetching tea and coffee, an hourly chore. The department had a regular badminton group, which I joined, but I was always quite shy about showering together with the older men after our games.
As a late and rather slow developer, I had very little pubic hair and body hair generally. I was fairly short at 5’6″ and had a slim 26″ waist, no chest to speak of and a girlish figure with a bob-type hair, and long eyelashes. I also had a fairly high-pitched voice, which sounded rather feminine. This often led to me being mistaken for a girl; in fact, I recall one of my sisters’ many boyfriends thinking we were sisters, much to my sister’s delight, which she used to tease me about. I’m not sure if she was aware that I was dressing up in her clothes. I always thought I was being careful, trying to put them back in the drawers as I had found them.
John, an older work colleague, in his late forties, then introduced me to squash on a one-to-one basis. I was 18 at the time. We met up and played together every week. He would stand closely behind me to show me the right stance and grip of the racquet, and I slowly picked up the technique. Squash is a very energetic sport, so I built up quite a sweat running around the court. Afterwards, we showered in the large communal shower, where he encouraged me to wash his back when no one else was around. He did the same for me.
Again, I was initially quite shy and embarrassed at first, but slowly found I enjoyed the feel of his soapy hands on my skin. Initially, this started fairly innocently with washing each other’s backs, but that developed into all-over washing and hair washing, though only when no one else was around. We played squash together each week after work, and I must admit I began looking forward to the shower afterwards. John would book an early evening 5 pm slot, and it was generally not busy in the showers after our game at that time of the evening.
This experience with John, my older work colleague and squash mentor, was quite eye-opening. I was very naïve and unsure of my sexual feelings at the time; my experiences with Stephen had left me wondering about my sexuality. I was also at an age where my hormones were still racing around. In the shower, I did get aroused by his touch, and it was clear that he was equally aroused. I was confused by my feelings but also flattered by the attention. I enjoyed John’s soapy hands sliding across my body. He would tell me to stand perfectly still with my arms up whilst he soaped me down, washing under my armpits, over my chest and gliding down my body. Then he worked up my legs and thighs to my pubic area.
By this time, I would be erect and totally absorbed with what John was doing. John would tell me that it was important for my hygiene that my testicles and penis were well cleaned. He would soap up and then gently pull and squeeze my genitals before soaping my penis with both his hands, then grasping the now hard shaft he would pull the head back to clean around the glands, I recall that the shower gel used to feel strange on the head of my penis, John used one that seemed to have a menthol smell and this would lightly sting my purple head, but I didn’t find this an unpleasant experience, quite the opposite.
Sometimes John would tell me to wash myself similarly; often this was when we were not alone in the shower. I would start at the top of my arms and work down to my genital area. I had found that I was now growing more confident about being naked in the shower with other men around, so I would wash my penis in the same way that John had shown me. While I was quite focused on this, I would see John watching me while he was washing, and I noticed the other men in the shower were furtively watching me too. I found I rather enjoyed the attention of these other men, too, and John would tell me that I should be proud of my youthful figure and flaunt it more.