This is a print version of story My oldest by hulosayla from

My oldest

Its probably appropriate that Pat is my most recent and ongoing dalliance while being my ‘oldest’ as my libido slows to a more sedate pace.
I am now retired with the time to relate a lifetime of experiences and all with mature women. All my stories are true in essence and only some dialogue and scenes embellished to improve the story flow. I have spent my life seeking sexual exploits and each of my stories is either a real experience for me or related to me by one of the participants. Fortunately I had a career that allowed me the freedom to explore.
This story is presently ongoing but started about 18 months ago. I live near a retirement village and as such am familiar with many of the hundreds of residents there who pass my home regularly and with whom I pass the time of day. Of course many aren’t ‘old’ being the same age as my self – early sixties – and a number of the women are very nicely preserved at that age.
Pat is one resident with whom I had a very passing acquaintance as she always maintained an aloofness that indicated she was a bit stuck up and not over friendly so I never encouraged too much conversation. I prefer friends who can smile and laugh. Hence it was with some surprise that one afternoon one of the young gardeners stopped to chat on his way home from work and was beside himself with disgust.
“the old bitch asked me to take my clothes off’ he spat out. I enquired who he was referring to and when he said Pat my interest was piqued.
‘she invited me in for a cuppa and told me she was an artist and wanted a live model – fucking hell mate - not me, dirty old bitch’.
Maybe not him but I was intrigued and resolved to investigate since I’ve never been known to pass an opportunity of enjoying the company of an attractive mature woman. Pat was, no doubt, attractive even at 70. Tall at almost 6 feet and very slim and very well groomed. Dressed always in smart fashionable clothing for a mature woman and still used make-up . Her shoulder length grey hair was accentuated with a touch of silver colour. She never smiled though which made her handsome face somewhat sour and gave the impression of “shit on the liver’
I did not have to wait too long to catch her going by as she walked regularly for exercise so I engaged her in conversation on this particular afternoon. That was easy but her answers to my questions were usually short and somewhat curt. That was until I asked her about her art. She looked at me quizzically and asked who told me. I replied ‘one of the residents” to which she said “that must be Dot”.
I didn’t confirm or deny just continued by asking if I could see her work someday and she really opened out and for the first time ever, I got a smile out of her.
“Yes please come over when ever you like” she invited so I arranged to drop by the following afternoon.

I was interested that she had mentioned Dot as she was a lovely buxom girl of my age with a bubbly outgoing personality after whom I lusted but she always insisted she was being looked after by her young (50 ) friend George.

The following afternoon I dutifully arrived at Pat’s with chilled bottle of white under the arm as a gift for allowing me to see her work. She opened the door and let me in, taking me to the kitchen where she was busy making tea. I was able to admire her dress – tight white slacks with obvious sensible knickers underneath (not old ladies bloomers) and a loose black top with a little décolletage. She suggested we have tea first then look at the paintings so we sat down to enjoy what was a most revealing conversation about her life – I felt she was using me a confidente and almost pouring out her heart to me. She never married nor had c***dren but had a full life as a PE teacher until she retired (hence the well toned body) and had enjoyed close relationships with a number of friends but didn’t elaborate as to whether they were male or female.
After tea I followed her to a spare room which had paintings stacked against the walls - most still life stuff with flowers and the odd a****l which was skilfully done but not sensational. She then hesitatingly asked if I wanted to see life work. I enthusiastically said “that’s what I thought you did” . She said she was a bit embarrassed and didn’t want me screaming out of there like the gardener did a few days ago. I had to laugh at that as I wouldn’t be here now if he hadn’t, but I didn’t admit that to her.

She turned around about ten paintings of nudes. At least four were of a young couple either together or separately - a couple of individuals with faces turned away and two were obviously of Dot. I was genuinely impressed and said so. They captured a serenity and relaxed mood and very tastefully done. She had been able to capture the personality of each especially that of Dot who I knew. They were also colourful and bold in detail.

“ so you really do like them “ she asked and I was enthusiastic in my praise. Now losing some of her reserve she asked if I’d be comfortable seeing something a bit more risqué. I just said ‘ we’re both mature people here so nothing is going to surprise or embarrass me and I’ll maintain any confidences you need’’.
She stepped over to a cupboard and removed a cloth covering four paintings. She then displayed them against the wall. I admit to being amazed and could only stammer “YOU did these” and she proudly answered “yes’ . there was the young guy from the first paintings laying back on the couch with a nice hard-on masturbating obviously. The next was of his girlfriend doing the same with her fingers spreading her cunt lips while the third was of the couple together fucking doggy with his cock very obvious between the two of them. The fourth I loved – Dot with a larger purple dildo just parting her pussy lips and her head thrown back in such joyous abandon. I just said “I think we need to open that wine I brought over”.
“What a great idea ‘ she agreed.

After the first glass she was emboldened enough to ask if I would model for her. I revealed to her that nudity was no problem to me and was an avid exhibitionist. I further revealed that I enjoyed swinging from time to time so I was very comfortable performing naked in any capacity which sowed the seed of thought that I could pose for one of her risqué ones. She asked “what about Helen“(referring to my wife). I asked for discretion and said my wife knew nothing of my nefarious activities which always took place away from our home city.

“would you pose now for me “ she asked after the second glass. Of course I obliged so I immediately found myself sitting naked at her kitchen table while she prepared her materials and set up her camera. Her method was to take photos then draw the model and at subsequent sittings get the colouring and shading right. I happily stretched out on her couch in her lounge room – curtains drawn of course – and posed as she asked. After about 30 minutes she called a halt and I strolled naked back to her kitchen where she joined me to finish the wine. At my age I don’t spontaneously harden up just because I’m in the presence of a woman so I sat comfortably with her and chatted about things intimate. She admitted to bisexual relationships but said she had never lived with anyone.
I departed that day with a promise to return tomorrow for another sitting. Things were getting interesting.

I arrived as arranged somewhat earlier in the afternoon the following day, again with a chilled white in hand. This time she met me she was dressed in old track pants under a short painters smock , both of which were heavily paint stained. A lady ready for work with her hair pulled back into a ponytail and a light make up. I immediately stripped and after a quick cuppa got into the poses but today was more about colours and shade so I sat very still and made small talk. Again in 30 – 40 minutes she was done and suggested we open the bottle. We were part way through our first glass when she just casually asked “ are you ready to do the more erotic poses”.
“Pat as I explained yesterday, I’m always willing to oblige but I don’t arouse spontaneously so will need a little time and encouragement to get there “
“I don’t have any pornos or magazines “ she apologised.
“ You being here is helping and I’ll use my hand” I responded smiling. I’d already started stroking and knew I’d be ok soon as I had taken my chemical assistance that very morning. I was half hard and stroking slowly as she watched when she excused herself and disappeared to her room. A few minutes later I heard the toilet flush and Pat re-appeared. She had let her hair down and put on more make up including a very red lipstick. Her track pants were gone but her short painters smock was still there just covering her crotch so the nicely muscled slim legs were on view and were enough to assist an old boy in achieving his goal. I complimented her on her physique to which she did a little twirl and suggested I get comfortable in posing position on the couch and she would help me get “as big as you can”
Now I’m not one of those blokes who professes to have a 10 inch cock or capable of multiple rapid fire ejaculations. I just get a nice erection that varies according to the amount of arousal and some girls are capable of getting the best from me. It appeared that Pat was going to join them. She sat next to me on the couch and started to stroke my now already hard cock but seemed to manage an extra centimetre or two. I suggested it was unfair she was still dressed so she quickly stood and dropped the smock revealing total nakedness underneath. Her small tits were pendulous but pretty – small nipples and areolae. But her body was tight with a firm boyish bum and minimum weight anywhere – a bit skinny in fact with only a few bits of loose skin expected of someone her age. She immediately returned to the couch but kneeled of the floor and took my cock in her mouth. She was a sucker not a player when it came to cock. Just burying my cock as deep as possible in her throat and good at it. I felt for her bum and she shifted to allow me access. My hand snaked around her arse and in between her legs. I could feel a light covering of hair on her pussy lips which were closed and not readily parting – the vagaries of an older woman. Withdrawing my hand I spat in it a couple of times and returned to her pussy lips with saliva which readily helped to separate the lips and allow my fingers to slip between . Since she was a little dry, but obviously very keen, I suggested that we 69 with her on top. She didn’t need a second invitation. Quickly standing she knelt astride my face and I could look up into a sweet partially open slit of delicious pink with a light covering of greyish hair. Reaching up with both hands I gently pulled the lips apart revealing a pair of tight inner lips and traced a finger up to her pea sized clit which by now was already partly engorged. She was very happy to pose like this for me to play with her until I tapped her bum and said “ back to the cock ma’am”. She leaned forward and engulfed my cock once more as I raised my head to allow me to lick her cunt as it deserved.

I allowed my eyes to gaze at her tight puckered arsehole then directed my tongue around there to moisten it before returning to long slow laps of her cunt lips finishing at her clit. Using my hand I slid it around her leg to let my fingers just lightly tickle her anus and she reacted with a slight moan telling me that she enjoyed that. Sometime into our 69 I brought the forefinger into action probing deep into her cunt and finding the G-spot right behind her clit. By applying pressure to the G and licking her clit vigourously I knew I could bring her off so asked if she was ready to cum. She pleaded to keep doing what I was doing very gently as she was getting there nicely. I too was building up to a nice ejaculate but didn’t want to cum in her mouth on our first encounter. Asking her to slow down and putting pressure on her clit I could feel her motions taking her to orgasm. When she came a long slow moan escaped her lips and she clamped her legs together and hard down on my face. There was no gushing but she was very wet and lubricated. Her breathing shortened as she gasped for a minute or so. Then relaxing completely she let her full weight rest on my body.

I allowed her to remain for a few minutes then reminded her jokingly that she was to hoping to draw me in my aroused state.
“Oh fuck yes” she called, jumping off me and almost running to her easel and tripod. She started taking photos even coming over for close ups of my wet slick cock which hadn’t yet been relieved then back to her easel before exclaiming “fuck this , I’m too horny now – just wanna fuck”. I never expected to hear this from a 70 year old especially from such an outwardly prim and proper humourless woman.

I had meantime walked into her kitchen and poured myself another wine sitting at her table when she came in and standing facing me she said “ just fuck me Lew right here on this chair” and she proceeded to squat over my thighs impaling herself on my still hard cock. Our faces were at equal height and she proceeded to kiss me with full tongue tangling spit swapping kisses which I just loved and responded too. They went right to my crotch as she started to move hard and fast on my cock. “cum in me Lew , cum in me you bastard, fill my old cunt” and a whole lot of other wild language which I’d never believe came from a sophisticated spinster. I did as I was told and let her have two weeks of pent up juice as deep in her cunt as I could manage. She loved it – tightening her cunt muscles and giving little grunts as she rocked into her second orgasm for the day.

We rested in that position, locked together by our genitals and I poured her a wine as I sat at the table. That was her first fuck for two years – the last being the young model in her paintings. He and his girlfriend were German backpackers who usually stayed the night after a modelling session and she admitted she had sex with them both on each occasion. Her only other sexual relief had been with Dot who loved a good licking and using toys. She promised she would show me her stash of toys - “plastic’ as she called them – some day. As my cock subsided within her we chatted about past sexual exploits, delighting each other with tales that turned the air blue. She eventually climbed off my lap and as we sat at the table discussing today’s events we resolved to keep this absolutely secret and meet when our urges coincided. I also wanted her to shave her cunt as I’m not partial to munching on hair. We did this together the very next session and she’s remained delightfully bald to this day. I did say that I wanted to fuck Dot and all she would promise was that she would invite her over one day but claimed she kept her fanny exclusively for her man George.

I strolled home that afternoon with a smile from ear to ear – one spends his life chasing interesting sex with mature ladies and here I find it on my door step. Our contacts were real fun after that. We had a signal to give to each other as she walked by each day to acknowledge if we were up for a good rut or not. At our age we didn’t always have the urge or need and thus our sessions together were always mutually satisfying – exploring, exciting and never boring. Dot did join us and happily joined us but, true to her word, I couldn’t fuck her vagina or arse. She sucked or I should say worshipped my cock and balls with her mouth and taught Pat how to do the same and the girls often got it on for my entertainment. Something perversely exciting about seeing two mature women working each other over with toys and going down on each other when perhaps they’d be more suited reading stories to their grandc***dren. Love it.

We met on average a couple of times a week always at Pats over the first year but our ardour has dampened a bit recently so its only a couple of times a month. However yesterday was special. I suggested we should have a whole day together. Knowing my wife would be at work all day I asked Pat over early to spend a whole day having sex. We rarely used a bed in our trysts and I intended to take her in every location I could in my house.
I met her at the front door naked and within seconds I had her thin dress off and bent over the dining table as I was ready with a nice morning glory. She had worn high heels which I find very arousing and only her dress. I never knew her to wear any exotic lingerie – it was always commando or very conservative and sensible. I asked her to keep her shoes on and nothing else as we could roam the whole house including a large secluded deck in the sun. When I was about to cum and after her first orgasm of the day she asked me to slow down as she had a surprise and wanted me to save my juices. Sometime later as we were sitting on the deck in the sun her phone rang and she got up to take it inside the house. I was half asl**p in the morning sun when I felt a pair of hands over my eyes and heard a “guess who”. She couldn’t disguise her voice and as guessed it was Dot as naked as the day she was born and her long waist length grey hair flowing freely. Very very arousing especially as she immediately got down to action with Pat on a rug that she threw on the floor. She had Pats legs spread and was licking her with a very determined action which I knew got Dot as hot as it did Pat.

As Pat neared her orgasm she called me to “fuck this bitch hard Lew” - Dot raised her head to protest and Pat just ordered her to keep licking and “forget that fucking George today, it’s Lew who’s going to ream your cunt and he has a cock full of cum that he has saved for you”. I didn’t need a second invite and moved behind Dot whose cunt was glistening in the sunlight with her considerable juicing capacity. I parted her inner labia which were protruding outside her outer lips (I guessed she’d fucked George last night or even this morning). Quite roughly I shoved my cock up her. She may have been recently fucked but had delicious muscle control keeping a tight grip on my prick as it pounded mercilessly into her. I felt myself building up to a copious ejaculation and was even tempted with the thought of pulling out and reaming her arsehole which was winking at me. However nature took its course before I made up my mind and I emptied my load into Dot’s warm tight cunt. As soon as Pat realised what I had done, she instructed Dot to sit on her face and she eagerly lapped at my juices. Her face and hair was covered in second hand cum and it was one of the sluttiest scenes I had ever seen of Pat.

The whole day continued like that. They managed to get me hard a couple more times and at least I can last the distance if not shoot loads of cum. I fucked both their holes and eventually extracted a promise from Dot that I could fuck her as often as I liked but only when Pat was present. Yes, I am enjoying retirement and there’s many a good tune to be played on an old violin as they say in the classics.

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