I suggest you might like to first read my introductory tale about my elderly widow neighbour Dorothy which will set the scene before you read this
So, whether you've read my introductory tale or just want to dive straight in here's an update about my elderly widow neighbour Dorothy, as things have got quite kinky recently since I told Dorothy about my dear deceased Aunt Jane who took my virginity when I was a teenager. And whenever my parents were away I had to spend the night at my Aunt Jane's house round the corner, a very sexy buxom woman, always wore tan stockings (sometimes seamed) and stiletto heels with a flowing skirt and blouse, fifties style, and my inspiration for many a hard wank at the time.
Anway the long and short of it is that Aunt Jane liked to slump back on the sofa and pretend to have taken some sleeping pills whilst I hitched her dress up, pulled her knickers off, spread her stiletto heeled stockinged legs wide apart, and pumped my hard young cock into her until I exploded my hot cum deep into her womb. I loved Auntie Jane very much and continued to fuck her on a regular basis all through her life until she sadly died a few years back in her late seventies of cancer. She always loved to wear stockings whilst I fucked her. I even gave her a good hard fucking a few weeks before she died whilst the nursing help was out, we both knew it would be the last time so I really gave it to her, she was bed ridden but I dressed her in her favourite seamed tan stockings and black patent stilettos, spread her legs high and wide and rammed my cock in and out really hard into her withered pussy until she came then filled her with my hot spunk and licked her out afterwards. A wonderful woman.
Hearing this tale turned my elderly widow neighbour Dorothy on immensely and prompted her to confide in me that in her younger days she had often fantasied about fucking her then teenage grandson but had never had the nerve to do anything about it back then, other than close her eyes over the years and regularly use the naughty thought to help her achieve a climax whilst having sex with her husband who had sadly been rather limited in his ability to satisfy her, she instead resorting to imagining it was her then still sweet and innocent grandson whose cock was using her.
Anyway last week I got a text mid-afternoon from Dorothy as follows;
"Hi my naughty neighbour, I've not sure if I mentioned but I've not been sleeping too well lately so the doctor has given me some stronger sleeping tablets. I'm going to take them about 7pm and take myself off to bed early. The doctor says they should take about half an hour to act so could you just look in on me mid-evening and make sure I'm ok and tucked up fast asleep in bed. I'll leave the side gate and back door on the latch."
Damn, I thought, I'd been half intending to nip over the road to Dorothy's this evening, take her by surprise and give her a good seeing to, earlier that day wondering whether as I I hitched her house dress up and forced her legs open if I'd find her lower half clad in her favourite seamed tan stockings with big white granny knickers to be pulled down, or in her normal day wear 30 denier micromesh dark tan tights for me to tear open and rip her granny knickers off. Either scenario, I had fantasised, my cock hardening at the thought, would be very acceptable for a nylon and older lady lover such as I.
But hey ho, I sighed, never mind, another time. "Yes, no problem Dorothy", I messaged back, "I'll pop over and check on you about 8-ish".
8pm duly came round, and over I went to Dorothy's house, through the side gate which was was on the latch as Dorothy had stated, and round to the unlocked back door and let myself in, trying not to make too much noise as I did so. I had no idea if the new sleeping tablets were any better than her previous ones but not wishing to wake Dorothy I made my way quietly though the kitchen into the hall and then up the stairs into the main bedroom.
I'd expected to find Dorothy tucked under the sheets but to my surprise the bed was made but she certainly wasn't in it. I quickly checked the two other bedrooms, which were similarly unoccupied. Ah, I thought, shes probably flaked out in the lounge in her dressing gown, oh well I'll have to get her upstairs and put her to bed.
But then my cock twitched with thoughts of my earlier fantasy. Better still, I pondered for a moment, if shes really out of it maybe I could lay her on the bed, pull her dressing gown wide open, dress her in some stockings or tights and fuck her in them whilst she was out of it. MMMMMMMMMMM now there was an idea, I thought.
Not that it came to that if you'll excuse the pun, as you will read.
I found Dorothy in the lounge slumped on the sofa fast asleep, still fully dressed with the lights ablaze. Ah, I surmised, noting the bottle of sleeping pills and a half empty glass of water on the side table, I bet she's taken the pills and they've taken effect a bit faster than she expected and she's dozed off before having a chance to get herself off to bed.
And subsequently, I could see, was fast asleep in the middle of the sofa, slumped straight back with her head leaning back against the head rest whilst still fully dressed in one of her yellow stretchy polyester house dresses, with her legs stretched out straight in front of her, clad in her regular daily wear dark tan micromesh tights twinned with brown patent low heeled day shoes on her feet, her granny shoes as I used to joke. Thats when my cock twitched again. Memories of my dear old Auntie Jane came flooding back, how I used to fuck her on the sofa when she pretended to have taken sleeping pills. And, I recalled, Dorothy had got very excited when I'd relayed the story to her, in fact she'd even said maybe I should do that to her one day if she was out of it. And had added for good measure, she'd have loved for her grandson to have fucked her like that when he was young but she'd not had the nerve to ever do anything about it. Well that was good enough for me. So that decided it.
"Hi Dorothy" I whispered gently, "erm are you awake?"
There was no answer.
I leaned into her, I could hear her breathing nice and regularly. I gave her a little shake of the shoulder and tried again, this time raising my voice.
"Dorothy are you awake?"
But there was still no response.
"OK Dorothy", I said full voice, "I'm just going to get you up to bed". I lifted her arms up firmly. But they were just a dead weight, there was no response whatsoever, she was completely out of it. I dropped her arms back down either side of her.
Excellent, now for some fun. I knelt in front of her and tried to pull her knees apart. The polyester dress stretched tightly round her hips restricted the movement. Now I'm not so into naked sex, I like clothes sex, preferably with the subject of my desire wearing tights or stockings underneath, plus of course some form of footwear. And call me kinky but I often enjoy leaving my paramour's top half still fully dressed as I fuck her, savoring her nipples straining against the fabric or her tits bouncing up and down beneath the material as I pump in and out of her pussy. Sometimes (but not always) ripping open her top clothing at the last moment and exposing her tits, simultaneously calling her a dirty slut or similar as I explode deep into her cunt. And conveniently Dorothy's house dress had buttons all the way up the front to make my life easier.
Accordingly I undid the bottom four buttons of Dorothy's dress to her waist and splayed the material either side of her thighs, then forced her legs wide apart with my knees and stopped to take in the sight. And what a beautiful sight for a nylon and older lady lover - dear old widow Dorothy slumped directly before me in a deep sleep with her legs spread wide open in cheap dark tan micromesh tights with no gusset. And to my surprise with NO knickers underneath, her neatly shaved old pussy lips clearly visible beneath the nylon.
"Oh yes Dorothy", I murmured delightedly, not that she could hear me "Tut tut you naughty old slut, I didn't know you'd stopped wearing knickers under your tights. Well", I grinned metaphorically, "we shall have to do something about that won't we?". By now my cock was straining at the leash to get out. I quickly pulled my jeans and underwear down, my big hard cock springing out.
So, at this juncture of the story lets just recap for a moment and picture the scene again... Its just past 8pm, I'm in my elderly widow neighbour Dorothy's lounge, the lights are ablaze with the curtains shut and she's slumped unconscious on her sofa in front of me with her head back, the bottom half of her house dress pulled open to her waist, she's wearing dark tan micromesh tights with no gusset and NO knickers underneath, brown patent low heeled granny shoes on her feet, and her legs are splayed out wide apart in front of her with her neatly shaved old pussy clearly visible through the nylon. And there I am kneeling between her legs with my jeans and underwear pulled down and my cock at full attention with my cock head just a few inches from her nylon covered pussy.
