Androshorts: Older Women

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A young man, in praise of the older woman, well two actually.
18.1k words
4.77
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Part 1 of the 2 part series

Updated 08/30/2017
Created 05/09/2017
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I can't say that my schooling was exceptional, over and above some reasonable exam results I did OK and wasn't in too much shit with either teachers or other pupils. I had a couple of girlfriends, none of which went past the making out in the park after school.

I went to college, on the basis of those results I got a good job in Engineering which would sponsor me through University and after a few years was looking for the right girl, or at least the wrong girl in the right place.

Don't get me wrong, I was no stud but I'd had a fantastic introduction to sex. Like all the best porn films I'd been led astray by an older woman. During my second year at University I couldn't get a place in the halls of residence and hadn't been able to get cheap rooms on campus and had to go out and rent a room. I was put on to a family member that lived on the outskirts of town, some way off from my University but my landlady worked in town and would drop me off as often as possible.

My landlady Amy was in late forties, extremely attractive, positive and vivacious and was nursing her husband Tom who was in the last stages of Parkinson's. Her husband was ten or more years older than her, and had been a high level non-medical manager in the health service who'd gradually succumbed to his illness. I'd met them a couple of times at family parties and weddings and the like but didn't know them that well.

Husband Tom was a 'work-hard play hard' type of guy that 'lived life in top gear' or at least gave that impression and liked to show off about his latest golf club, new running shoes and male menopause car, and my Dad confessed that he'd never liked him that much and he'd always seemed a bit 'up himself considering he was just a pushy clerk' but we were all saddened to learn of his illness.

Working with medics and knowing that his prognosis for Parkinson's was not good, when he reached a certain point in his condition he'd requested that he could stop eating and drinking, . While his doctors had said that he probably had a couple of years of 'quite reasonable' health he wanted none of it and could not, would not be 'a healthy brain trapped in a twitching, twisted, helpless, dribbling, doubly incontinent body slowly shutting down'.

And so with a wildly twitching head and hand he searched the internet on his laptop computer and impressed with what he found, he concentrated as hard as he could to read what was on the screen. It was simple, he decided he would decline food and drink.

He asked Amy for his favourite meal that he could still manage and she went to their regular Indian restaurant and remembering him and his sad decline they cooked him a special chicken biryani along with all of his favourite sides.

She propped him up in his bed and gave him his tablets, and he took them with his beer. They laughed and joked and he reminded her of their life together. She shed a few tears and he said that with her support, this was to be his final meal and his final drink, and that by his best guess his life should end in a week to ten days.

Having watched her wonderful, bright, active husband become this bed-bound twitching wreck had broken her heart and she wasn't sure that she could watch him undertake this final journey and said so.

Huge tears slipped down his face and that was enough. When the nurse came to help with his bed time routine he announced his decision. The nurse said that she would have to tell the doctor, but they helped him upstairs and into his own bed where he'd asked that he could spend his final days. His doctor called around the next morning and he knew his patient well; after some pointless discussion he agreed and contacted his staff to that effect.

That was that; when the dehydration began to cause him pain, the district nurses put him on to morphine and after 15 long days he finally slipped away.

I arrived ten days after his death and a week before his funeral. Amy was a first or second cousin of my Mum - extended family - and much as my Mum had said that I should give everyone time to get over the death and not move in until after, perhaps sleep on a mate's floor or a local B&B. Amy said that I was most welcome and would help to take everyone's minds off of the next few days so I moved in.

Amy was curvy and sexy but amazingly sad. I made myself as useful as I could, loading the washing machine, packing the dishwasher, vacuuming etc. I made tea and coffee and tried to help seeing as both of her children were due back from University for their father's funeral, both Tom and Amy had insisted that they should continue studying.

They came home the night before and I offered to move out of the spare room to give everyone time to grieve, but none of them would have it. On the day of the funeral I got up at six and threw myself into whatever needed doing, including making breakfast toast, gallons of tea and coffee, greeting the caterers, the funeral directors, mourners and generally making myself indispensable. Being close but not too close the funeral director kind of used me as the sensible family member that could be relied on not to break down in tears.

"You're a treasure Terry," Amy said on that and so many other occasions.

The funeral was one of those 'celebrations of life' and I saw many of my relatives, including my Mum and Dad attending the crematorium and listening to the funnies that Tom's brother Hugh told of his older brother. It was upbeat, sweet but dreadful to the point of cringingly painful and Hugh was trying just too hard. It made the final closing of the curtain all the worse and Amy, the two grown up children, Tom's widowed mother and even comedian Hugh lost it as they slid shut.

There was a large wake afterwards in a local pub, and being the only sober one, I drove my landlady and her two children home, all three the worse for the booze they'd put away on that happy, awful day.

Amy's children went back to their universities and life carried on; never for one moment was there a suggestion anything at all 'naughty', sorry. We never passed on the upstairs landing with her in a filmy, flimsy see-through negligee, I never saw her in her underwear in the kitchen, had my own bathroom so there was none of that bumping into each other in the mornings.

However, she had phone calls from both of her children and seemed very upset one evening during my third month there. It turned out it was his birthday and then a few days after, her silver wedding anniversary and she was of course very upset. I was supportive and despite homework just stayed with her the whole evening.

At a little after ten she said I should go to bed, as I had to be up early and I kissed her hand and left. I woke up at about one o'clock to Amy getting into bed with me.

"I just... I just want... need to hold your hand Terry," she stumbled in her tears, "can I sleep in your bed tonight?"

"Of course," I said, throwing my duvet back and seeing her in her cotton PJ's. Fortunately for me I was wearing boxer shorts, something I always did when not at home, and she slid into my double bed. We lay together in silence and we reached out for each-others hands, she giving mine a gentle squeeze and a whispered 'thanks Terry.'

I woke at six to find the duvet pushed off of her and Amy lying with one arm across my bare chest, and in the pale early light coming through a gap in the curtain I could see one of her boobs down the gap of her PJ top. Similarly, the stretchy trousers had slid down just enough for me to be able to see the rise or her bottom and the beginning of her buttock cleft.

I had a late tutorial that day, so was in no rush to get up. Unfortunately that didn't apply to my penis and I could feel it straining against my shorts. I desperately hoped I could get out of bed without her seeing. My bedroom was quite small and my bed pushed against the wall so technically I would need to climb over her if I wanted to get up first.

So I closed my eyes and hoped that I could drift off to sleep and that she'd get up before me. I did sleep for a while stirring when Amy woke up and but obviously not enough to fully realise where she was.

Her hand slid down my chest, over my stomach and stopping just above the waistband of my shorts, and touching the top of my erection.

"Hmmmm..." she said sleepily and with some contentment. She stroked her hand along the length of my rock hard cock making it even harder!

I felt Amy's hand whipped away from my groin as she obviously realised where she was and who she was with. I thought she'd get up and leave, but instead she must have been doing what I'd done a few minutes before and was ogling my body and penis as it strained against the elastic of my boxers.

I left her to it, and after it was obvious I wasn't going to get a repeat performance I 'woke up' and she grinned at me,

"Thanks Terry," she said pecking me on the cheek, "I slept like a log; I'll go and get some tea." She got up, pulling up her trousers, the shape of her lovely buttocks momentarily clear through the thin worn cotton; she did have a lovely bum, no two ways about it.

This was recreated the next night only this time she came in with two mugs of tea, and asked if she could hold my hand again. The PJ's from the night before had changed to a loose vest top over an unrestricted bosom, and clingy shorts and I appreciated the change. She leaned forward to put down the two tea cups and I could see straight down her top at her still full breasts and they looked great.

We lay there and chatted easily about Uni and what I wanted to do afterwards, and then she talked about her hopes for her children and the future. Eventually, she turned out the light and we lay back just holding hands. I was dead nervous.

Like randy twenty year old virgins of my age I was a prolific masturbator and fantasist, but here I was terrified. In the shower that morning I'd pulled myself off just thinking about her stroking my cock for that brief moment and her wonderful arse I'd all but seen, and my orgasm was almost painful, spitting my youthful semen against the glass wall of the shower stall.

Amy was more than twice my age, gorgeous, and a distant relative and I lay there holding her hand and trying not to get an erection, which was of course precisely what happened.

I eventually managed to drift off to sleep, but came round at about two to find that I had rolled to one side and that Amy had backed up into me so we were spooning, and somehow my right arm was now across her waist and she was holding it to her flat stomach - under her T-shirt - with my thumb just brushing the underside of her boobs.

I so wanted to extend my thumb to touch her breasts; just once, just so I could kid myself that I'd touched real ones which would then inform my masturbation fantasies. Of course my cock swelled just at this thought and the beautiful half naked woman I was holding on to. I tried to get back to sleep, and thought getting my hand back and rolling to the other side, because I'd moved so far away from her I didn't have room, so I was pretty much stuck; what's worse my throbbing cock was bound to touch her at some stage if I stayed as I was.

To make it worse, she must have felt me move, or tense up or something because she sighed and moved back into the space I'd just made and rubbed her bottom against my erection and I could feel her wriggle until it was pushed between her buttocks; she gave a slightly stronger sigh, the tiniest wiggle, before taking my hand and pulling it up to lay on soft warm breast. To make matters worse she squeezed my hand with hers and I kneaded soft tit flesh for the first time. As I felt her nipple extend into my palm it was all I could do not to come in my pants there and then.

I woke up a while later and my right arm was under me and starting to suffer pins and needles. I tried to get it out from under me, but I was feeling brave seeing as my other arm was still holding her breast. I managed to slide it out from under me, and in a strange wriggly manoeuvre I slid it up and under my pillow and her pillow, so it ran across her shoulder. Inspired by my own bravery I laid it across her and, more by luck than judgement, it went under her vest top and straight on to her other breast. I squeezed both and pulled her tight to me, and this elicited a further sigh and the addition of her other hand over my other hand, and further push against my now rock hard penis with her bottom. I fell back to sleep almost immediately not thinking how we'd explain this in the morning.

When the morning came we were still snuggled up really closely and I was still holding her bare breasts under her T-shirt and she still had one arm across both my hands, with the other reaching back pushed through the waistband of my boxers and on to my thigh. Yes, my erection was pushing between her buttocks.

It was obvious she was awake, and it took no time for her to push my hands against her boobs and gently stroke my thigh, her nipples hard again. She turned her still sleepy face back to me and smiled.

"Thank you again Terry," she again pushed my hands against her bare tits, "I slept like a log again," she rubbed her arse against my penis, "and it seems like you've woken up with one!" she giggled. She rolled over and I disentangled my hands from her boobs and vest top. She took my hand and rested it on her still bare midriff, and looked into my face. "I can't thank you enough Terry," she said dropping her eyes, "I don't think I've 'slept' properly in about five or six months. With Tom's last few months, he could only sleep in a hospital bed downstairs, then he insisted he wanted to go up to our room to die, and seeing as he was staff they let him." She choked up a bit and looked back at my face, "I actually tell people that I lost Tom about six months ago, as that was when he stopped being 'him';" she dropped her eyes, shook her head a bit and looked back at me again. "It was so lovely to actually be held by someone again, thank you Terry." She kissed my cheek tenderly and rested her forehead against mine. She rolled over and got up, her arse looked wonderful. "My turn for the tea and breakfast again Terry, what time do you have to be in college?"

"Usual time," I said pulling the duvet back over my erection. I'm sure she noticed.

"Well you jump in the shower Darling, and I'll do breakfast." In the shower I lasted about half a dozen strokes before I shot my come against the glass wall.

We had a very relaxed breakfast of marmalade toast and tea, and I took her up on her offer of a lift to college even though I wasn't due in for nearly two hours. I sat in the refectory nursing a coffee and thinking about the last night. She was hot, sexy but as they say in the movies, 'just not that in to me'. I finished my coffee and headed off for my lecture.

Would probably never happen again, and what the fuck if I did get a stiffy, she'd spent most of the previous evening rubbing herself against it already. I got a several handfuls of boob into bargain.

It was Friday night and I got home to find that she had prepared a really nice meal, had taken the afternoon off to shop and prepare it in fact.

"Go up and shower and change Terry," she said, "I've prepared us something nice to celebrate the weekend." She was wearing a stretchy floral dress that clung to every wonderful feminine curve and looked so fucking hot it was unbelievable. I showered, and put on the smartest clothes I had. I was a student and not that well supplied with them after all. I went with my black 501's and a blue denim shirt that I buttoned up under a matching tie. I added a splash of aftershave. As I came into the room I noticed she had turned off the main lights going instead with candles.

"Look at you," she said, "all dressed up," I could see some red in her cheeks and she turned her back on me.

"Least I could do Amy," I replied, "have to apologise that I don't even come close to your sexy outfit..." I put my hand over my mouth; shit, I used the S word and that was the one thing we were both trying to avoid, or so it seemed to me.

"You look sexy as well Terry," she said turning to face me, "trust me!" She popped the top on a bottle of Asti and she poured us both a glass, next she reached into the oven and returned with two plates piled with steak, chips and mushrooms, next the fridge revealed two plates of salad.

She sat down opposite me, and raised her glass,

"This is a toast just for me," she said looking to the ceiling, "to my wonderful late husband Tom on the occasion of our silver wedding anniversary, with who I never shared a cross word or deed and who I miss every day," I saw a single tear in her eye, "to you my Darling Tom-Tom, hoping heaven's golf courses never close and you can finally get your handicap below 13." She closed her puffy eyes and took a long draught of wine, draining it in one go.

I tried desperately to think of something to cheer her up, and raise the mood just a bit. I stood,

"To Amy's Tom," I said looking from the added height straight down the front of her dress at the black bra responsible for her great shape, "You must have been well hell of guy. But playing off of a 13 with a wife as beautiful as this in love with you? You must be in heaven," I emptied my glass as well.

It worked and she giggled, and topped up both of our wine glasses and I sat back down. We spent a very pleasant hour chatting and eating the splendid steak and chips. Amy asked if I could manage something else and said she had an Eton mess in the fridge. I stood up and got it from the fridge placing the large bowl between us and two smaller basins. She spooned out large portions and we tucked in with gusto.

I love Eton mess above all other sweets, and it was wonderful, made with my favourite black cherries rather than strawberries. I ate my portion, then laughing Amy took another spoonful for herself then pushed the bowl over to me. AND I finished it.

She had already started to make coffee, so I began to scrape plates and load them in the dishwasher, along with all the cutlery and crockery we'd used that night.

We headed back to the living room with a tray which I carried; we sat on the large sofa with and she turned to face me, knees drawn together and up on the cushion, she rested against the back of the sofa her head on her arm.

I'd never been on a date before, and I'd drunk half a bottle of Asti Spumante. I was slightly tipsy and because I'd never been on a date, I didn't realise I was on one. As the night drew on I noticed we were no longer talking about Tom, and it was more about me. She started to yawn and I stood and indicated that I was heading for my bed. She grinned and said she would follow a bit later.

"Goodnight Amy," I said, taking her hand and kissing it, "I had a wonderful evening, thank you so much."

"You are most welcome Terry," she beamed at me.

I headed for my bed with just the slightest wobble and I heard her chuckle. I got to bed and stripped out of my clothes and rolled into bed. I lay awake for a few moments wondering if Amy would come and join me again, but my long day and my great evening soon had me sound asleep.

I felt the bed dip as she got in, and I rolled to my side lifting the duvet so she could take up the same spooning position we had the nights before. This time I wrapped both my arms around her and took hold of her great boobs and felt her bottom push against my groin. The message finally reached my Asti fuddled brain some moments later that she was naked, and so was I.

I didn't have an erection, at least not when I fell asleep.

When the late autumn sun started to creep through the curtains, I definitely did mind you. Her soft skin felt wonderful against mine, and my cock was not flat against her buttocks or resting in the crease as it had done before but thrusting and pinched between her thighs and resting against her bare pussy. I flinched and she must have felt it.