Crystal's StorySite


My First Time In Stockings

by Molly CD


I am a closet crossdresser myself and have worn all sorts of sexy feminine things, such as nylon stockings, suspender belts, High Heels, silky satin panties and slips, lots of lovely Red creamy Lipstick. After all why should women be the only ones to enjoy the sexy feel of sheer nylons, satins and silks?

Your story reminded me of when I first wore stockings. They were my older sisters, I must have been about very young too and she was 22. I think it must have started when I saw her snag one of her nylons when getting ready to go out. She was late so she just hitched her skirt up there and then in the hallway outside her bedroom, rolled the stocking down her leg, slid out of her high heeled white Go-Go boots after unzipping it down the inside (what a lovely sight and sound that was), she opened a drawer and pulled out another pair of barely black stockings Taking just one of them she rolled it up her leg, stroking her leg to make the nylon smooth and equal to her other leg. Then she stepped into her GO-GO boot and zipped it up slowly so as not to snag this one. She threw the other (new) stocking and the one she had snagged onto her bed. She caught me looking at her as I was going to bed and said, "Be a dear Hon and put those away for me please". With that she blew me a kiss with her full red lipsticked mouth and rushed out.

I didn't feel too much at that stage, all I knew was that I loved the sight of her showing me things I felt I shouldn't really see. As I picked up the stockings from her bed I noticed that one seemed bigger than the other. Then I realised that it had stretched compared to the new one from the packet, as yet unworn. I put my hand inside to see where the snag was. It was quite a way down so I had to roll the stocking up my arm. By the time I found the snag point I could see my arm encased in the sheer nylon. It looked a little like a woman's nyloned leg. As I gazed at my nylon-encased arm I pulled it higher and pondered how my elbow looked a bit like a knee in nylons. At that moment I felt a strange sensation tingle within me. I just had to see what these stockings looked AND FELT like on my legs!

Mum and Dad were still busy downstairs watching TV. (I came to know in later years that 'I' would be our first 'TV' in the bedroom - giggle). I removed the stocking from my arm and gathered it up like I had seen my sister do. Without taking them off I pulled my pyjama bottoms up to reveal my leg, then sat on the edge of my sisters bed, I bent over and slipped my foot into the gathered stocking. I pulled gently, letting some of the nylon fall from my fingers as I slid the stocking slowly over my foot, around my heel and up my calf, again as I had seem my sister do only minutes before. I had to gather my pyjama bottoms up higher to the top of my thigh (luckily they were lose enough) so I could wear the stocking over my knee. I moved my hands back and forth from the front of my thigh to the back as I released the last of the nylon material onto my leg. I noticed how much darker the stocking top was to the rest of the stocking. This was only something I had only glimpsed before, but now I could drink it all in before my eyes. I reached down and wrapped my hands around my stockinged ankle gently sliding them upwards smoothing the nylon to my leg as I went. This was such an exquisite feeling that by the time I reach the stocking top, I had such a stiff erection! My bunched up pyjamas looked more like shorts on that leg but I didn't care. I could see the snag now. She must have caught it with the zip of her boot.

I looked longingly at the packet and one remaining new stocking. I read the words on the packet. "15 denier, Micro-mesh one-size, Stockings, Colour: Barely Black". These would always remain my favourite. I couldn't resist. All was still quiet so I gathered up the other stocking and "smoothed" it onto my other leg mmmmmm. What an even more exquisite feeling; as the stocking was new, it gripped my leg even more than the first one! I walked around my sister's room in the stockings until I felt them slip down a bit. I really needed something to hold them up. I opened her drawer a bit more hoping to find something. Hmmm a suspender belt, looked complicated at my young age but then, yes, two black garters! I slipped them over the stockings and thus was able to prance around without them falling down.

I knocked something under her bed with my toe, whoops. I froze as I hoped my parents would not hear. I waited. Still OK. Phew! I looked under her bed to find a lovely pair of high-heeled shoes. They were shiny black (patent courts) with a strap. I just had to slip my stockinged feet into them. I sat on the bed and put on her shoes. Wow what another sensational feeling. I could see now that the strap was to go across my ankle to hold them on. I did them up and then stood up. mmm a little wobbly but the wide strap on my ankles held my nyloned feet into the shoes. I walked slowly in short steps and they felt fantastic. I looked at myself in her full length mirror; There was a pair of sexy ladies legs reflected in it. mmmmmm There is nothing more I could do but work my cock up and down at the gorgeous sight and feelings of my legs encased in sheer nylon stockinged delight. I walked up and down, sat on the bed, crossing and uncrossing my legs, this was heavenly. I gazed at her lipsticks all lined up on her dressing table, her silky slips with pretty lace trim on the hem. How I longed to put them all on but that would have to be another day. I had stayed where I shouldn't be for long enough. It wouldn't take much to get caught. Besides I was so close I dare not spurt over my (I mean 'her') stockings or my sister would know my secret for sure. I undid the shoes, slipped out of them, being careful to put them back under her bed. Reluctantly slid the stockings down and stepped out of them. I crushed the new one to make it look unused and unstretched. Folded it gently and placed it in the packet. Folding the other one I carefully closed her drawer. I let my pyjama legs fall down, even that was a nice tingly feeling, and crept to my bedroom. In bed I couldn't sleep I was so excited but eventually fell into a semi sleep, the kind where you know you are asleep but can control your dreams to an extent, they are the best dreams of all.

That night I dreamt that I was dressed-up and feminised by my sister, forced to wear stockings, high heels. Satin and silk underwear swished over my nyloned thighs as she applied full make-up including deep red creamy lipstick whilst she straddled my lap, our stockings rasping gently as they touched. We later danced as she held me close in a rhythmic slow dance. Asleep I lay face down lying on my front as I rhythmically ground my pelvis into the mattress until I came.


That's all for now. I hope you like it. I will have to tell you of other encounters where I went further and was almost caught by her friend sitting on her bed in her short black skirt, stockings and boots.

Love hugs,

Lipstick kisses and nylon caress






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