My earliest memory of anything kinky is from when I was about 11 or 12, when I started to be interested in women. I’m not sure if this is early, late or average since it’s never been the kind of thing I talk about with friends.
I used to raid my mums underwear drawer and wear whatever I found. This gave me funny feelings I’d never felt before, feelings I now recognise as arousal. What it felt like at the time was that I needed a wee. I remember going to the bathroom to use the toilet, wearing a bra and panties, with my pyjamas on over the top, because I thought I needed a wee.
There was one occasion when my Mum was in the bath, so I knocked to ask if I could use the loo. She let me in, I tried to wee but couldn’t. She asked me what I had round my neck – I was shocked, startled, how did she know? My naive brain had failed to realise she would see the straps. I tried to make some crappy excuse about a game I had been playing with my brother, but she knew what was going on.
So I was forced to go downstairs and then suffered a verbal telling off from both my mum and my dad. Although smacking was a punishment used by my parents, this was only a telling off. I can’t recall what was said, but I remember I was in deep trouble. From this moment on I knew I had to be more secretive.
I carried on raiding my mums underwear drawer until I left home at age 18. It even got to the point where I was wearing stockings & suspenders with bra and panties on under my usual clothes. I don’t ever recall going out like this, but I have many memories of wearing ladies underwear. It wasn’t the fact it was mum’s, it was the fact it was for ladies, and mum’s were the easiest to get my hands on. I have no idea if she knew I carried on doing it, she must have noticed the occasional panty/thong or suspender belt missing!
Although I don’t recall exact timings, it can’t be that long after that incident in the bathroom that I decided to see what it felt like if I rubbed it. I certainly have memories of both these things associated with the same memory triggers.
Quite early on in my masturbation experiences I managed to snap my banjo string. This is the only time to date that blood has been involved in my pleasure. Needless to say it hurt like crazy, but I still carried on until I came. I was also unable to leave it alone long enough for it to heal properly; what else is a young boy exploring himself to do. Luckily I have suffered no long term damage from this (at least I don’t think so!)
I remember that I would often wear a lacy white thong whilst masturbating. I remember the feeling of it restricting my cock as it grew harder, feeling the lace pressing into my head. I also remember that I used to love the feeling of the thong string pulling into my bum crack as my cock stretched the material. I remember quite vividly one time where I was pulling the lace onto the head of my cock so hard that I tore through the material. I remember that this little hole I’d tore in the material was really tight and restrictive and that that felt so good around the hardness of my cock.
Sometimes when I wore the underwear, I liked to tuck my penis between my legs so that I looked more like a woman. It soon followed that I’d try masturbating with my cock in this position.
This soon became my favourite way of doing it. I really loved the pain it caused to force my cock between my legs as I wanked. I also remember quite clearly the feel of the warm cum running down the back of my thighs.
Is it any wonder that I now get my kinky kicks from CBT, punishment & pain and mild sissification?