I've been browsing the site for a long time and I've not posted yet, but today seems like the day!
I've been a sissy pretty much ever since I can remember. When I was about 9, I remember stealing a pair of my mum's panties and trying them on in my room. It felt so naughty, and so nice in a way I can't explain. I can't really tell you what made me want to slip on that pair of cotton frilly briefs, but as soon as I did I felt all warm and nice and I got a little stiffy.
When I got a bit older, about 12, I started playing with myself while wearing mum's knickers. It felt great and I loved it. I suppose if I didn't already know I was a sissy, my body would have given the game away. I was an overweight child, and like many overweight teenage boys I had breasts. But mine were MUCH bigger than anyone elses, even most of the girls! In addition to that, it was becoming pretty clear that my willy was never going to be very big. Now, it's just over 4 inches long. Too small!
I used to get teased at school constantly about my breasts. Luckily no one got to see my willy, but I knew how small it would always be. When you consider that, it was no wonder that I used to slip into mum's panties in the evening, and of course I started wearing her bras (which fit perfectly.) I absolutely loved it.
I sometimes wonder if she ever knew. One of my greatest fantasies when I was younger was having my mum dress me up like her little girl. The thing I longed for most was for her to point of the obvious: that my breasts were so big I could really be doing with a bra, and then to be made to try on one of hers in front of her. She would then make me pull down my trousers, exposing my small willy to her. Measuring it with a giggle, she would declare that it was so small that I should be wearing frilly panties, and put me in them too. A dress and make up would follow, and for the rest of the day I'd be her sissy girl.
Of course this never happened, but I truly wish it did. I have no idea whether mum knew I was borrowing her clothes, but I have a pretty shrewd idea that she must have. I used to do it almost every day, and I'm sure I wasn't careful. She probably thought that i was discovering that I was a sissy on my own and left me to it.
I stopped dressing when I was 18 and moved out of home, I no longer had any access fo my beloved bras and knickers. Of course I used to fantasise about it all the time, and went on lots of websites like this one to get my sexy thrills.
I didn't get a girlfriend or lose my virginity until I was 20, and I started going out with a girl. At that point I didn't dress, but I did tell her that I used to. She sometimes tried to put her knickers on me but I wouldn't let her.
Eventually after a few months it became clear I wasn't satisfying her sexually. She would drop hints, or I could just tell from the sex we had that she wasn't satisfied. It took a while to get her to admit it to me, but when she finally told me that I wasn't any good in bed, for some reason it felt amazing. It was just such a relief almost to know for sure. We broke up soon after.
It's been a long time since I had any girly clothes to wear, but this morning I went and bought some bras, some panties, and a little bit of make up.
I got 3 bras and 9! pairs of knickers. So happy. I forgot how AMAZING it feels to wear a bra, and of course my boobs still fit like a glove. I've got all sorts of knickers too, pink one, frilly ones, lacy ones, polka dot ones and even a nice thong! It's amazing how well girls knickers fit me. It felt so good to pull on a pair of frilly knickers and a bra, and do my makeup today.
I live in London, and what I'm really looking for is a special lady to share my fantasy with. I'm not looking for a relationship or anything, just a woman who enjoys humiliating me, spanking me and dressing me up like her dolly and showing me off to her friends. I know that's what a lot of people are looking for, so I don't hold out much hope, but if you are a woman in the south of england who would like a giggle at a sissy with boobs and a little dick, then get in touch. :)