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.
