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My very first attempt at cross-dressed striptease.
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This is the story of one of the first strips I did in nylons, back when I was still at college, about 18 or so. I'd already jerked into shoes and tights but never gone any further. Our English teacher, Lynda (hence my name) one day told us a story about a girl friend of hers at college whose boyfriend was into dressing up (there'd been a documentary on the TV about trannies and the whole school was talking about it like mad). She said that at one party he had gone dressed up and some point did a bit of a striptease and shocked everyone at the end!! This resonated with me and I often thought about it while wanking off. Anyway, one day a mate of mine asked me if I could do him a favour and collect some books from his house at lunchtime because he had rugby practice and needed them for an afternoon lesson. He told me his mother might be in after 1 o'clock but gave me his key in case I went earlier.

We had English with Lynda in the last period before lunch and she spent some time sitting on the desk with her legs crossed in black tights, sometimes dangling her heels and giving me a raging hard on. When the bell went, I set off determined to have a wank at home, then remembered my mate's books. I decided to get them first and as I walked to his place an idea grew. His mother was what we'd now call a milf, had great long legs and was also a bit of a shoe dangler when we went round. I got to the front door and rang the bell, no answer as I'd hoped, so I let myself in with the spare key; just inside the front door I saw a pair of Mrs M's purple slippers (M&S style) - she'd obviously changed into heels before leaving. That decided me.

First, I went up to my mate's room and got his books and brought them down and put them by the door - explanation for being there if Mrs M came back before 1. Then back upstairs to the master bedroom. I pushed the half-open door wide open and stepped inside; To my delight and increasing excitement I saw two pairs of tights on the bed, black and grey, and a pair of black high heels under the dressing table. A dark grey skirt was draped over the back of a chair. I took the black nylons, skirt and the heels, then opened the top drawer of the dressing table and quickly found a flimsy pair of red knickers. That was it - off into the bathroom; In less than 5 minutes I'd removed the bottom half of my uniform and replaced it with black tights, red panties and the greyish skirt. Above the waist I wore white school shirt, tie, and black blazer. Now I slipped the heels on and that was it. Slightly unsteadily I walked along the landing, went into the master bedroom to look at myself in the wardrobe mirror (not great but not too bad) and then walked carefully downstairs. Halfway down I announced, "Ladies and gentlemen we present the Magnificent Mrs M, your lunchtime stripper". And my show was underway.

At the bottom of the steps, I bent down and picked up Mrs M's purple slippers. Dangling them from my fingertips, I walked into the lounge, swinging my hips as much as I could. I walked across to the chair that Mrs M had been sitting in last time I called round and placed the slippers in front of it, then went to stand in front of the sofa and looked out of the lounge windows, which had thin blinds which effectively blocked anyone seeing me. Now I shrugged my shoulders and let the blazer slide down my arms; A flick of the wrists and it fell on the carpet. I walked around in front of the sofa, undoing my tie; I pulled this from my collar, waved it and then let it drop. Now I undid a few buttons on my shirt before sitting on the sofa and crossing my nyloned legs.

The feel and sound of the nylon rubbing together made me harder and my cock pushed against the panties and skirt. I reached forward and hooked the high heel off my right foot, held it up and put it on the carpet. I stretched my leg, crossed left over right and took off the left shoe, put it next to the right one, uncrossed my legs and stood up. I prowled the lounge, swinging my hips and rubbing my crotch, working up my already stiff cock which was tenting the fabric of the skirt. I turned my back to the window and bent forward a little, pulling the skirt higher so that I could slip my hands up my black-nyloned thighs and ease the red panties down. With the panties at my knees, I straightened up and smoothed the skirt a little, then flexed my legs and Mrs M's panties were round my ankles. I stooped and eased them over my feet and turned again, dangling them from my index finger.

One hand rubbing her cock, Mrs M walked the length of the room, twirling her panties on her index finger. She turned and walked back to the armchair then tossed the panties onto her abandoned blazer. Now she sat down again and crossed her legs, right over left. She flexed her toes and stretched her foot, looking at the toes under the dark reinforcement and then slowly rubbing the tip of her cock through her skirt and tights. Then she leant forward and picked up her right purple slipper. She held it up and then slipped it softly onto her foot. Now she uncrossed her legs and picked up the left slipper, This time she ran the tip of her tongue around the toe before arching her foot and putting it on. Now she stood up to finish her strip.

In the slippers I walked to the centre of the room, turned, thrust my arse out a little and unzipped the back of the skirt, then pushed it down over my hips and let it fall round my ankles. I stepped out of the circle of the skirt and turned to face the window, wearing just shirt, black tights and the slippers. The last buttons on the shirt came open, then I held out my arms and opened the cuffs in an exaggerated way and eased the shirt back off my shoulders a little. I rubbed my hard nipples and then sat down on the armchair again.

Mrs M rubbed her cock through the nylon over her crotch and moaned softly. Getting close! Now she crossed her right leg and, with her left hand, flicked the heel of the purple slipper free of her foot. The slipper dangled on her nyloned toes and her cock hardened even more watching it. She arched her foot and the slipper dropped softly onto the carpet. Mrs M stretched her leg out and ran her hands from ankle to thigh, smoothing the nylon. Then she crossed her left leg and hooked the slipper off. Now she held the slipper up and ran her tongue round the instep, before dropping the slipper onto the carpet and standing up.

Cock straining against my tights I walked towards the sofa and slid my shirt down my arms, letting it pool with the rest of Mrs M's clothes. I sat down and swung my legs up and then lay flat. Bucking my hips, I eased the tights down over my cock and crotch and then kicked my legs up to tease the nylon off them. First the left leg, nylon off the foot and then the right, leaving the tights dangling from my foot before tugging them off. I stood, holding the tights in my right hand and then rubbing them over the tip of my throbbing cock. Closer! I quickly picked up the purple slippers and walked behind the armchair, dangling tights from one hand and slippers from the other. I placed the slippers together behind the chair and then put the tights on the back of it and knelt down. I pulled the foot of the tights towards me and grabbed it with my teeth. Slowly I began to suck and chew on the nylon while gently massaging my hard-on. With my mouth half full of black nylon, I thrust my right hand into the other leg and moved the nylon glove to my cock, still sucking the tights. I brushed my cock over the instep and toes of the slippers and that was it.

A thick blob of cum oozed from my slit onto my nyloned hand and then two spurts jetted over the slippers. I moaned into the nylon and kept tugging as fast as I could. More spunk pumped out over the slippers, coating the toes then the instep of the left one. I spat the tights out and gasped for air and coaxed a last gush into my nyloned hand. Sweating and shaking a little I stood up and, with the spunky tights still on my hand, picked up the creamed slippers and went back into the centre of the room. There I dropped the slippers in front of the armchair again and sat down where Mrs M had sat the previous week. Now I raised my nyloned hand to my face and rubbed some of the cum on my burning cheeks, before holding up my hand and licking the cum off the palm in long strokes.

Pushing the cum round her mouth with her tongue, Mrs M picked up her slippers and held them out for the audience to see the cum before pushing the toe of the left one into her mouth and slurping the cum off it. The right slipper she rubbed over her face, transferring a glob of cum onto her cheek. She tossed the left slipper onto her discarded clothes and gave the right one a last lick before throwing it after. Wearing just the nylon glove she stood, walked to the pile of clothes and picked up her right high heel. She rubbed the last traces of spunk from the glove to the heel, sank to her knees on the clothes and licked the heel clean. Then she held her hand up, took the toes of the tights between her teeth and pulled them off her arm. A shake of her head and the tights joined the rest of her outfit. She gave the audience a big spunky smile and said, "Well, boys, I hoped you enjoyed your lunch like I enjoyed mine. I'll see you soon" and her strip was over.

Needless to say, I'd lost all track of time while doing this and had to scramble about gathering up clothes and getting dressed before the real Mrs M did arrive. In about 10 mins I was cleaned up and back in my school uniform and all Mrs M's clothes were where I'd found them, albeit a bit spunkier. The spunked slippers I put back by the front door as I let myself out. It was almost 1 o'clock so I'd missed lunch, but what the hell, it was worth it. As I got to the end of the road and turned back up to the school, I heard a car horn and saw Mrs M turning into the road. I waved to her and she waved back as I held up my mate's books to show why I was there. All afternoon I was hard thinking about whether she had changed back into those slippers when she got home!

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cruiser_2015cruiser_2015over 1 year ago

Wow! That was so kinky! Loved it!

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