Shemale
2008-07-06
Topic: A night of JoyShe worked at the local Doctors surgery, and had done so for quite some time, certainly I'd seen her there for years. In her early 50's Joy was aptly named as her presence in the place brought that feeling to many people. A bubbly personality, stunning looks, there was hardly anything you could fault with her. And from my point of view it was worth going to the Doctors just to see her smile at the front desk. We had always chatted over the years, luckily we shared some mutual interests so that made it easy. And if we saw each other in the street the same happened. Even driving along we'd spot each others cars and wave. Little did she know that each time we spoke I was fighting a raging erection and was always trying to sneak a better peak at her. You see most of the time she shunned the paints suits that the other women wore and was quite happy to show off her shapely legs. Resplendent in either black or natural pantyhose they always looked fantastic, and she wasn't shy about skirt length either. And why not, she was more than capable of carrying the look off. And not for Joy the dowdy flat, work-like shoes, she always made an effort and usually wore some nice heels as well. It was hard for me to talk to her when all I wanted to do was check out her legs and heels. I remember being lucky enough one day to spot at lunch time while I was sitting in my car and she was walking along the street. That walk, the swing of the hips, the sound of the heels as they hit the pavement. .
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. It was all I could do to hold myself back. I wanted her, but I wanted what she was wearing too. . . I'd always had a soft (well hard actually) spot for pantyhose and high heels. And the best thing of all was actually getting hold of some from someone that I knew. Over the years I'd amassed a small collection but it wasn't easy to do. To get hold of some of Joys would be a dream come true. Luckily enough I needed to call in to the Surgery to pick up a prescription the other week and as usual she was there. We chatted mindlessly about things and to be honest I can barely recall what was said. Of course all I was trying to do was lean over the counter a little more to see what she was wearing. All I got was a glimpse of leg, nothing more. I thought I was going to have to leave unfulfilled until she asked me"Hey you're a bit of a gadget man aren't you?" she asked quizically "I've seen you with lots of weird things and you always seem to be right up with the current trends"I admitted that I was lucky enough to have a more than reasonable understanding of a lot of stuff "Yeah, I get by I suppose""Look" she said "I've got this new handheld phone at home. It's the second one because I thought the first one was faulty, and it has all these features and such but I just can't get it to work.
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It wont work at all so I have to use my cell phone all the time. My husband gave up in disgust and now he's gone away for a week Interstate leaving me stuck without a home phone. You any good with phones?""Ha" I said "Phones are easy usually, I've done more than my share of them. I can certainly have a look anyway"She gave me her address, it was only 5 minutes away anyway, and we arranged to meet after she finished work. As it happened I got there early and I was able to watch as she swung the door open of her car and I saw those two shapely legs clad in black pantyhose hit the driveway. Shiny black patent stillettos which were patently unsuitable for her job caught my eye and he must have noticed that I was looking. "Ha" and she smiled "I know these sort of shoes aren't right for the work I do are they. I should wear flats I know, but I can't resist my nice shoes during the day"She let me in and we sat down and handed me the phone. Nothing special really, and in fact it was from the same manufacturer that my own was. "Where's the base station plugged in?""Oh it's in the main bedroom, next to the bed, on the bedside table" she said as she wandered off to get us each a drink. My heart jumped a beat as I walked into the bedroom and saw the base station on the table. I couldn't help wondering if the bedside drawers contained what they usually did in a womans bedroom. I kept talking loudly to her as I pulled the 2nd drawer open. Bingo, full of pantyhose. I grabbed 2 pairs quickly and shoved them into my pocket.
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If nothing else I'd already got my bounty. "Oh Joy this is easy, the base station is hooked in incorrectly" I reached over and switched the plug around into the correct socket. I turned around and she was standing in the bedroom doorway, two wine glasses in her hand. "Really? That's all it was?""Yes, who plugged it in, a monkey?""Close, just my silly husband, and he was in a hurry anyway. Oh well, no need to waste these anyway" and she handed me a glass. We went back in, sat down and continued chatting again. I tried the phone and of course it worked now. We both laughed and keep talking. After half an hour the bottle of wine had almost gone and we were both getting a bit silly. "So" she said, putting her hand on my knee "What's the deal with grabbing my pantyhose out of the drawer?"I was stunned, I thought she'd been in the kitchen getting the drinks, she must have been standing there watching all along. "Yes I saw you do it, and I was waiting for an explanation but it hasn't been forthcoming. I'm not worried, I've seen you looking at my legs a lot and I figured it was just a harmless fetish. So, is it?"She reached over and pulled them out of my pocket. She would have had to have been blind to not also notice my hard cock nestling right nest to her hand. "Oh Joy, I'm sorry.
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. . I just couldn't help myself, yes it's a harmless fetish but you must think I'm a fucking weirdo or something. I should go, you don't want to be associating with the likes of me after this revelation"I went to get up but she pulled me down again. "Don't be silly" she said "I think it's kinda cute and I must admit I'm intrigued. It's not like you can smell me on them or anything, they're all clean. So what would you normally do with them?" she giggled a little and poured herself some more wine. I could feel my face turn red, but the hardness in my pants just became more pronounced as I told her my story. "It's no big deal, I just like to wear them, to feel them on my legs and imagine that they're your legs that I'm feeling. It really is just that simple""So you masturbate in them do you?" she asked"Usually, but I like to prolong it as long as possible, to enjoy the experience""Just pantyhose is it? Or other things? Bras? Panties" the evil twinkle in her eye was intriguing. "Well shoes too Joy. . . I love high heels. I suppose that explains to you why you can usually catch me checking out your legs and feet all the time"She seemed confused now "But your feet are a bit bigger than most womens, how could wear the heels anyway?""Well I can't, but I can just slip the end over a little, just to look at.
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I know it's weird, but its a fetish I can't shake and provided it doesn't impact on anyone else I suppose I can live with it. I just hope you can understand"She smiled at me and said "Don't worry, by comparison with some of the weirdos out there you're almost a saint. I have no intention of telling anyone, or doing anything about it. In fact, you can can even keep the two pair you pinched, provided that you. . . " her voice trailed off a little and I waited. . . "model them for me. . ""Oh come on, you can't be serious. I mean. . .
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" and I saw her hold them up to me. OK this was probably my wildest fantasy but I was so scared still. . . "Yes, do it for me, I want to see your legs. Tell you what, I can even make it better for you" she rushed off and came back quickly holding a pair of white patent Mary Janes with killer 4 inch heels. "These are my daughters special 'going out' shoes. She has feet almost the same size as you I think. Let's see what you look like"I sat down on the sofa and took my shoes, socks and jeans off. I saw her glance down "I see you DO enjoy this don't you" It wasnt hard to see my cock straining against the cotton underpants that I had on. I pulled the pantyhose over my legs "Hmmm you put them on very well, completely correctly, you have done this a few times haven't you" and she smiled as I pulled them up fully.
Joy was tall so I managed to get them up quite a long way but they were a little tight still. "Not a great fit are they" I said. "No and something about it doesn't look quite right either. Take them off again and remove your underpants before you put them back on"I stared at her in disbelief.
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She nodded. . . so I did as she asked. This time my cock was almost bursting, the tip straining madly against the nylon of the pantyhose. "Lift up your t-shirt a little" I did as she asked and she could now clearly see my cock. Moisture from the end dribbled down through the nylon. "I have to admit, this actually turns me on a bit" she said "Now the shoes"I pulled on the heels and they fit perfect. "Walk around, model for me" she saidI walked around and around the room, all the time my cock a good 6 inches in front of me, waving in the breeze. "My god you walk better than most girls do!" and she laughed wildly. "Come over here" and she grabbed me and pulled me closer to her. "Maybe its the wine talking, I'm not sure, but seeing you like this is really, really turning me on" and she kissed me firmly and passionately on the lips "But if you're going to be dressed a bit girly, then I'm going to have to treat you like one too! Come into the bedroom" and she grabbed my hand and lead me into the bedroom. We writhed for a few minutes on the bed at first. Kissing and exploring each others bodies. By now she'd removed most of her clothes leaving only her own pantyhose and heels on.
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Our legs locked together most of the time and the feeling of the nylon was divine, I was in heaven. I found my way down to her feet and slowly removed her heels. I sucked each toe in turn through her pantyhose and I could feel her relax and then tense as I went through the cycle. All the while I ran my hands up and down her legs, feeling the softness underneath them. I looked up at her face and she was obviusly enjoying it and she smiled back at me "It's your turn now" she said. She turned me over onto all fours and came to me from behind. I felt her tear a hole in the pantyhose and then a sensation that I had never felt before surged through me. She was rimming me. Her tongue was darting through the torn pantyhose and caressing my ass hole. I could feel it flick and burrow at my hole time and time again. It was am amazing feeling and my cock was responding tenfold. I could see ribbons of pre-cum drippng down from it, soaking the bed below. My cock almost hurt it was pressing against the pantyhose so hard. Joy kept going and then I felt her pull back a little and then a slightly cold sticky sensation washed over my ass. Then something butted up against my asshole.
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I turned around to see Joy smiling and a 6" strap-on dildo firmly attached to her. "Well my dear if you want to wear girly things, you'll have to DO girly things too! But don't worry, I think you might even enjoy this. . " and she started to push against me. . It wasn't like I had much choice in the matter really and I felt my hole slowly giving way. It didnt hurt so much as just feel uncomfortable and much as I tried to relax it was difficult. I glanced across at the bedroom mirror off to the side of us and I could see the whole ludicrous scene playing out before my eyes. I could see Joy with a wicked smile on her face slowly inserting this big dildo into me. And I could see myself. Tan coloured pantyhose, white stiletto heels and being fucked. . . Joy started to thrust in and out, each time inserting the dildo further on the inward thrust until finally each stroke was the full length of the dildo. It was only then that I realised that it was a double ender and she was essentially fucking herself at the same time.
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While it was still uncomfortable I couldnt deny that it was pleasureable as well. I started to get into the rythmn of it myself and push back against her. I think she was enjoying it even more though and after a few more strokes she screamed and settled down on top of me, her orgasm slowly ebbing away. The dildo now firmly wedged in both of us. I rolled us both over and turned her to face me, my asshole now free of its invader. She kissed me again and said how much fun she was having. I thought about taking her anally as well but all I really wanted to do was finally shoot my load. Given that Joy was well aware of my fetish now I felt I could pretty much do anything without worry. I picked up one of her discarded heels and inserted my cock into the peep-toe at the front. I poured on some lube and started to fuck the shoe. Joy laughed and put her mouth onto the shoe. At the end of each stroke the tip of my cock just touched her mouth. . and I started to fuck the shoe furiously. Joy finally grabbed the shoe off me and took my cock in her mouth.
She sucked me briefly and then just as I was about to cum she drew away. She pointed my quivering cock at the shoe and jet after jet of hot sticky cum spurted all over it. It dripped off and all over its mate laying at the foot of the bed. Long strings of the stuff dripped everywhere. . . I struggled to stand upright as I was wobbling around in my own heels. Finally I collapsed onto the bed beside Joy. "Well, you are a surprise aren't you" she said, her lipstick all smeared and covered in its own stickiness "I never would have picked you for being like that but there you go"We lay there for a while and she spoke again "Well a successful mission all round really. My phone works and I think you've got yourself some more heels and pantyhose. I dont think I need any of those any more, they're a little bit sticky! Ha ha"We both laughed again. We kissed again, them embraced. "The hot tubs on" she said "Care to play some more?"and the story shall continue. . .
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