September 10, 2001 8:44 PM BST
It was 5 o’clock in the morning of a cold winter day and as usual I was up alone and downstairs in the kitchin. On the surface I was awake and about because I was about to go on my paper-round but in reality it was too early for that. No, the reason I was up and about was that I was 14 and lived with my two sisters, my mother and stepfather and it was the only time I was safe from prying eyes. Or at least as safe as I could be in that house. I go to the garage door and as quietly as possible ease it open and then turn on the light. Behind the door is the washing basket and I quickly search in it for the things I have hidden there the night before. Finding them I take them out and go back into the kitchen, watching the dark stairwell leading to the others rooms as I pass hoping that no one is stirring. In the kitchen I put my treasures on the sofa there and gaze at them with longing - a pair of white Dorothy Perkins panties, all silky and lacey with a small bow at the front, a silky and flowery shortish skirt and a pair of my mothers tights. I am starting to gain that fantastic feeling that this always brings.
I rid myself of my trousers, trousers and socks and gently lift the panties from the sofa and slip them on, up over my shins passed my thighs and over my by now stiffening cock. My body shots through with pleasure, the way the panties cling to my backside and encase my cock is a feeling I lay awake at night thinking about. These are the panties I will dream about forever, the ones my sister allowed me to wear when she dressed me up, my first pair of silky woman’s undies I had really worn. I then inexpertly pulled on the tights, enjoying the look of my legs in the nylon and the way it pressed the panties against my cock and against my backside. Finally I put on the skirt and felt another thrill as the silky material touched and caressed the material of the tights, this was almost heaven. The finishing touch was supplied by the black platform shoes that were fashionable at the time that could be male or female and in fact where given to me by my mum. The fact that they were woman’s shoes did not occur to me until much later, how ironic that my mother gave me my first pair of woman’s shoes!
Normally the morning would progress with me staying dressed for a little while, reach a climax and then somewhat resentfully having to and undress in the downstairs toilet but today was different. Today I decided to put on my parka and see how my skirt and tights looked with the coat and then as if I was in a trance I picked up my trousers, socks and underpants and placed them in my paper-round bag. I was being driven my unseen forces of desire and my heart started to beat faster than ever as I turned off the light and approached the back door.
I open the door, it is black and cold out there and the night wind caresses my legs and brushes against my panties, if I was ever going to go back that feeling stopped any such thoughts. I stepped out, I can hardly breath, I am in the street dressed as a girl. I lock the back door and walk backwards looking up at my parent’s bedroom fearing a twitching curtain but the house is blind at this moment. I turn and walk out the gate and walk quickly, too quickly, slow down savour the feeling, this is fantastic, "god don’t let me meet anyone". I carry on across the green and down the road, the cold breeze is like an aphrodisiac as it envelopes by nylon encased legs and the feel of the skirt touching and gently banging them as I walk is wonderful. "I am free, I am free" I seem to sing inwardly as I walk, to be dressed like this and outside can it get any better?
I can’t risk being out long, other boys on their rounds might see me. I head to the woods and finding a safe looking place drop my bag and slip my hand up my skirt. I pull the tights down gently, not too much as I want to retain the feeling of them but enough to release my panties and get my cock out. I am wet, so wet it is so good. I caress it but it needs no effort and soon I rock back and forth in muted pleasure as I release my pent up excitement onto the grass. My first time and I know now that I want more of this.
August 20, 2007 9:33 AM BST
My first real outside walk outside was when I was living in Birmingham but was staying away on work in a nice old Cotswold hotel. As usual I was sleeping in a glorious Helen Stuart satin-de-lys full length nightdress, with a lovely full swirling skirt, which I still have even after all these years. Waking up at around midnight I got up and went for a look round the hotel, which is not very large. I had soon explored the stairs & hallways & made my way to the lounge. I was trembling with excitement & perhaps fear of being caught so was progressing very cautiously. However there was nobody about at that hour - I had the place to myself.
It was a warm evening so I sat in the chairs & sofas in the lounge enjoying the feel of the luxurious material encasing my body. Rock hard I was looking out of the windows at the road & coomon oputside when I though what fun & how exciting it would be to go out there. Right then! I went back into the front hall, made sure I was still alone & tried the front door - it was locked, but only very simply and readily opened. Making sure it couldn't shut behind me I went out. The hotel was only partly lit, btu not exactly dark outside. More excitement. I went across the road keeping a careful ear open for any cars! Up onto the common where I found great excitement & freedom
My skirts swirling in the wind I walked about in the moonlight for quite a while. A few cars came & went but nobody appeared to notice me. One gave me a fright when I thought it was going to the hotel. By now I couldn't control myself any longer and had one of the most intense cumings ever.
I hurried back to the hotel. Closed & locked the door and made it back safely to my room. what an exciting night. Such an experience has been repeated in various forms but never have it been quite like the excitement of the First Time.
Hi susan, I can relate to your story,mine was of mommies nylons that I put on and immediately became stiff and would rub my legs together until i climaxed,it was living the dream