The Ladies Who Lunch Pt. 02

The Ladies Who Lunch

Part 2

The Dorothy Simms Story

It was another lunch, followed by another gathering for coffee, as was now the custom.

This time, the hostess was Dorothy Simms, a forty-six-year-old housewife, mother and spouse to Graeme, a retired stockbroker and three decades older than Dorothy.

This is Dorothy's story.

Well, my husband Graeme is well into his seventies now. So, our sex-life is a mere memory now!

I'm sure you can imagine the consequences: erectile dysfunction, and loss of libido due to reduced testosterone, in old age!

A wave of giggling and a few sighs of sympathy rippled through the assembly of friends. In view of the age difference between Dorothy and her husband, whatever shortcomings their own partners had, were undoubtedly magnified in her case.

Yes, I see you can all relate to that!

But the sad irony of that, ladies, is as I'm sure you're all aware, while our menfolk's' sexual drive and capacity diminishes, our own libido increases with age!

Some barely restrained guffaws and a few, knowing nods emanated through the female gaggle.

Now, my own, personal paradox is that, when I was younger, I used to go for much older men, whereas now, my taste has reversed and the older I get, the more I fancy much younger men!

What is it, they call mature women who have the hots for younger men?

Amongst the epithets that her companions helpfully volunteered, were:

"Cradle snatcher!" "Sugar Mummy!" and, "Cougar"

Yeh, cougar! I guess I'm a closet cougar who'll pounce on a sexy young stud-muffin, given half-a-chance!

Little did I know, but this opportunity unexpectedly presented itself...'

"Do tell! Do tell!" her companions chided in unison.

Okay, okay! Well, where do I start? Dorothy pondered.

"At the beginning", somebody chipped in.

Have I ever mentioned my friend, Isabella? Isabella is a very attractive Spanish woman.

She's my next-door neighbour and very close friend.

She was married to an Englishman, whom she divorced him on the grounds of infidelity - he was screwing his 23-year-old bimbo secretary - his loss, because Isabella is stunningly beautiful.

Anyway, a few weeks ago, the weekend was coming up and Graeme was going up to London with his nephew for their annual pilgrimage to the Oval, for the opening of some, 3-day cricket test match, or other.

So, I rang Isabella on the Friday night, to see if she wanted to go for lunch on Saturday and generally hang out downtown, catch a show or wotnot.

"Darling, you must be a mind reader", she said, "I was about to phone you!"

She went on, to ask if I'd like to go with her to a party in Hove on Saturday afternoon. I asked, what sort of party it was, and would it be okay for me to turn up uninvited?

"Don't worry about that, you'll be my guest! As to, what sort of party it is, it was the kind where you eat, drink, are well looked-after and generally have a good time! Don't fret, it'll be fine. Trust me!"

Well, how could I refuse? I had nothing better to do in any case.

So, I agreed and asked what I should wear. I wanted to be sure that I was in line with the dress code, at least. The last thing I needed was to stand out in a crowd of strangers.

She told me to dress as if I were going to the wedding of a family member, or close friend, and to be ready to be picked up by 12 o'clock.'

And so, decked out in the nifty little two-piece I wore at my niece's wedding last month, I was picked up by Isabella, as planned.

Although the impromptu, out-of-the-blue invitation to the mystery party intrigued me, it also left me with a sense of unease so, I quizzed her enroute, all the way to the venue.

"Oh, you'll see, and you can thank me later!" was her stock reply to all my queries.

Well, we finally arrived at the venue. It was a huge, Victorian mansion which oozed affluence and class, set in its own grounds. There were several high-end motors parked in the forecourt. You know, Jags, Mercs, Bentley's and one or two Rolls.

I was thinking, "Wow! What is this place?"' I was soon to find out.

The house belonged to our hostess, the widow of a wealthy businessman who'd left his substantial fortune to her. Our hostess was an attractive and very personable woman in her mid-fifties.

The other guests were mostly women about my age, a few older ones.

There were no men present, other than a few, much younger men - some of them looked like they were barely out of their teens - who were fetching and carrying food and drink for the female guests.

"Must be the catering staff", I guessed. Though, they weren't dressed in a uniform, which was odd.

"Ah, this must be a ladies-only do?" I asked Isabella. She just smiled condescendingly.

This was not Isabella's first such party so, she explained to me what was going on.

Turns out, our hostess held these parties on a regular basis for her friends and close acquaintances.

The sundry male guests were in attendance for the delight and delectation of the female guests.

There is a different theme each time. Today, the theme was 'Young Boys' - no younger than 18 and no older than 20. Past events included 'thirty-somethings', 'ethnics' - Latino / Mediterranean, black.

A buffet meal is laid on, as well as α well-stocked bar, manned by a couple of the male attendees.

The drill was: the male guests mingle and make sure the ladies are amply provisioned with food and drink, as well as providing any other diversion that the ladies request, but they were not to initiate any liaison with them. The women always made the first move.

There were a number of well-appointed bedrooms upstairs that were available to the guests to consummate their illicit trysts, if they so desired. The number of women rarely exceeded the limited bedroom accommodation. I counted ten at some point in time.

Or else, if their marital and domestic circumstances allowed, they'd drive their partner of choice home and have him shag her in her own bed.'

"So, now you know the drill, good luck and good hunting!" Isabella enthused.

"You can thank me later," she said, and with that, Isabella made a beeline for a tall, blond, broad-shouldered boy who was serving behind the bar.

There was a short exchange between them, then they headed off to the staircase leading up to the upper storeys of the house, and as she sauntered off, arm - in - arm with the teen stud-muffin, she turned and waved to me with a sly wink,

So, there I was, feeling like the proverbial bacon sandwich!

Boys carrying trays of filled wineglasses circulated continuously, offering a selection of wines - red, still white, brut, and rose.

I was on my second glass of Chardonnay, when I spotted this thin, lanky lad who was hovering by the buffet table and looking as lost and dejected as I was feeling.

Mm, I thought, a kindred spirit! Perhaps, an introduction could be mutually beneficial?

So, he was young enough to be my son, but what did I have to lose?

I didn't see very many options at that point. So, I plucked up the courage to go over and say, 'hi!'

He looked startled when I walked up to him and introduced myself.

"Hi, I'm Dorothy", I greeted him, with the warmest smile I could muster.

"I'm Malcolm", he stuttered, and reached for my outstretched hand. He shook it firmly and vigorously.'

His hand was soft and warm. That was my first positive impression of the timid youth.

The poor thing! It turns out, it was his first time at this event, and he almost trembled in trepidation.

"This your first time?" I ask him. He shook his head as he exhaled, "Yes".

"Mine, too," I reassured him, which made him smile. He had a nice smile.

Hm, the second positive impression, I mused.

Also, I couldn't help but notice his beautiful, deep blue eyes, behind his rimless glasses.

Positive impression number three!

That was a hat-trick so far as the first impressions were concerned, which got me wondering, what other features on him would impress me?

I explained to him that I happened to be there, quite by chance and that a friend had brought me along, without any explanation about where she was taking me.

He said he was in a similar predicament. In his case, his friend told him it was a posh party and there'd be loads of guests of the opposite sex but omitted to mention that the guests would be older than his mum.'

He blushed and apologised for the age-ist remark. I didn't react to his oblique inference to my mature years.

"So, you, see? We're both in the same boat!", I said, in an attempt to deflect his inadvertent slight.

He was a very sweet boy and obviously a lot younger than my youngest boy, Eric.

I had begun to warm to him, in spite of his tender years - or maybe because of it?

I don't know, but I think what clinched it was when I glanced around the room, to see the other women deep in conversation with some of the boys and even a few couples strolling out of the room, hand-in-hand, with obvious intent.'

So, I thought, "What the heck! Why not?"

I turned to the timid, young boy whom I'd met five minutes earlier, and propositioned him.

"Listen, Malcolm, shall we see if there's a room?"' I said, albeit with my stomach in a nervous knot.

To my amazement, he said, "Okay, I'd like that very much!"

There were still a couple of keys remaining on the key holder, behind the bar.

I took a key and, arm-in-arm, Malcolm and I made our way to the stairs leading to the upper floor, where the bedrooms were located.

The room was on the top floor, and it took us a while to find it.

All the while, Malcolm held my hand in his big, soft hand. I recall thinking at the time, if it was true that the size of a man's hands are an indication of his cock size!

We found the room and once the door closed behind us, Malcolm put his hands on my shoulders.

At six feet tall, he towered over me, his bright blue eyes drilled into mine as he asks,

"Dorothy, can I kiss you?" What a sweet, naïve boy, I mused.

I replied, "Sweetie, of course you can! And not only! I want you to fuck me, too! I'm a very good fuck, as it happens!"

Our spectacle frames clashed as he bent down to kiss me. He laughed and pulled off his glasses, before kissing me on the mouth.

I put my arms around his waist, and he pushed his face close in, to mine. We stood there, snogging for a while. He was a good kisser and we kissed open-mouthed, our tongues probing each other's mouth.

He was wearing a loose-fitting sports jacket, but I could feel his taut, athletic body beneath. His shoulders were not very broad. Turns out he was a runner, a track athlete, so his leg-muscles were more developed rather than his upper torso.

I was getting wet by this stage, in anticipation of what else was to come. I could feel his male member pressing against my tummy so, I surmised that, you know, it was time to move on to the next phase.

"C'mon, then, let's undress!" I commanded. I was dying to see what was under that ungainly, juvenile façade.

Malcolm was the captain of his school's track team, so he was in great physical form.

He was tall, lean, with muscular legs and a total absence of hair, apart from a tuft of curly pubic hair. I was right, about his cock, it was a robust eight-inch shaft, which looked totally out of proportion to his slim, sinewy frame.

I really felt old and dumpy in comparison, I can tell you, to the point that I was too embarrassed to strip off in his presence. Luckily, there was an ensuite bathroom, so I excused myself for an urgent call of nature and made for the bathroom.

I was hoping to find a bathrobe that I could wear. I was, in fact, actually bursting for a pee, so I wasn't totally fibbing. Fortunately, there were two robes hanging on hooks behind the door.

So, I stripped off, relieved myself in the Royal Doulton then, rinsed myself off in the bidet and put on the smaller of the two, cotton towel robes.

When I got back into the room, Malcolm was already under the sheets. So, I went and sat on the edge of the bed, deftly slipped out of the bathrobe and slipped under the sheets, next to him.

I rested on my elbow to face him, smiling, while my free hand slid across and down the sheet, onto his dick. It felt thick and hard.

Malcolm gazed at me expectantly and asked if he should wear a condom. I said that it was up to him, as I wasn't likely to get pregnant and he didn't seem the type who slept around, so he wasn't a high risk for STD's.

It was blatantly obvious that he'd never been with a woman before, not even his girlfriend. By all accounts, they'd indulged in some heavy petting, but they'd never actually 'gone all the way', as he quaintly described it.

So, it was down to me, to move things along! It was ages since I'd had sex, so I was keen to make the most of this opportunity, and for it to last as long as possible!

"Why don't you kiss my breasts?" I prompted, "And, pay special attention to the nipples!"

'Sweet boy, he did as he was bidden, and I could feel my juices building up again.

I was irresistibly drawn to his huge cock. I'd never been with anyone who was so well endowed, before. My hand barely encircled his thick shaft, as I slid my fist up and down its length.

He had no foreskin, so the tip was like a fat, shiny bulb. His cock was already stiff and pre-cum was oozing from the tip.

I took his hand and moved it down, onto my fanny.

"Put your fingers in there and get me nice 'n wet, so's you can fuck me!" I commanded, softly but firmly.

Malcolm's foreplay was working its magic, as he sucked and licked my boobs. My nipples were stiff and so hard, they almost hurt!

He was fingering me all the while. First, with one finger then, two, in a circular motion inside my fanny. He didn't require much instruction on this, as he was apparently well practised with his girlfriend.

The only instructions I gave him, was to avoid over-stimulating my clitoris, as I'm prone to climax at the slightest touch, once I'm aroused, and I wanted his cock to be inside me when I climax.

I don't know about you gals, I'll quite happily masturbate to orgasm, but when I'm fucking, I want my partner's cock deep inside me when I climax!

I dunno, I'm funny that way, I guess! I come very easily, but it's always a long, intense orgasm.

By this stage, we were both fully aroused and, inexperienced as he was, I was sure Malcolm would cum very soon after he was inside me. This suited me, as we would probably climax together.

And so, I was ready, he was ready, and I was gagging for a good shag after so long a period of abstinence. I rolled onto my back and lifted my thighs, opening up to assume the position for him to enter me.

"Okay, Malcolm, I want you inside me, darling"' I proclaimed."

He put the bulbous tip of his cock against my crack, and I reached down to guide it in as he pushed it inside me.

I was overwhelmed by that feeling of exhilaration, tinged with, what I would describe as a pleasurable discomfort, as his thick, hard shaft parted my fanny. I must have let out a moan which he took as a sign of distress, and so he stopped, mid-thrust.

The first few inches were easy and quite pleasurable, but two underlying factors were at play here.

First, of course, his big cock! I'd never had one that big inside me before, so I wasn't accustomed to having so much man-meat inserted into my relatively under-used vagina.

Secondly, I'd had a prolonged period, months in fact, without sex so there was no slack or flexibility, either.

"Are you okay, Dorothy?" He asked, with a look of concern on his face.

"'Yes, darling, yes! don't stop! I'm fine", I reassured him.

So, with that, and a bit of guidance and direction, as well as some subtle repositioning of my hips, he resumed the penetration of my tight, under-employed fanny.

At this point, he lay between my open thighs, with his upper torso held at an angle by his arms, either side of my supine body, and which supported his weight

Anyway, he managed to penetrate me to the full length of his monster shaft and the feeling of fullness and tightness of it in my vagina was excruciating and pleasurable.

I urged him to hold me, so he folded his arms around me, and his mouth met mine in a long, languorous smooch. I was so aroused, I oscillated my crotch to-and-fro on his cock.

"Fuck me! Fuck me!" I pleaded.

Malcolm followed suit, with in-out thrusts of his hips. He pumped my fanny gently at first, then faster and harder.

My orgasm came, quick and hard, as my vagina twitched around his cock and my body convulsed with wave after wave of pleasurable sensation.

Malcolm ejaculated almost immediately, and his body trembled as his orgasm took hold.

He must 've shot quite a load in me, as it came squirting out of me and continued to ooze out when he pulled out.

We lay together still for a while. We were totally spent. Malcolm lay on his back, and I curled round him with my head on his chest.

"Thank you, Malcolm, that was wonderful!" I murmured and added, "Your girlfriend's a lucky girl!"

"Actually, it's me who has to thank you, and you were right, you are a great fuck!" he replied.

I chortled at this and told him that I wished I was eighteen again, so that he could be my boyfriend.

My hand was on his nether regions, with his plump ball sac cupped in my palm. I gently squeezed his testicles and teasingly ran my fingers up and down his cock which was now semi-flaccid but still thick.

"Mmm, 'I wish I could take this home with me! If you could market this, you'd make a fortune!" I said.

I looked up at his serene face and asked, "Ready for another?"

"You bet", he snapped back, "This time, can we do it doggystyle?"

"Hm, the boy's been watching porn videos", I thought to myself.

Actually, I like doggystyle, 'cos the man's cock is clear of the clitoris, so it delays orgasm.

So, I assumed the position and Malcolm mounted me from behind. His cock was hard and fully erect again. This time, his cock met less resistance, since my fanny had been well lubricated with our combined juices which still oozed out of me.

Anyhow, he fucked me with brisk, deep, strokes and I didn't orgasm until a good while after and, even then, Malcom kept going.

He'd shot most of his load earlier, so there was no ejaculation on his part until I'd come a couple of times.

Anyway, we stopped after almost an hour of copulation as I was getting sore with the hammering my fanny was getting and Malcolm was all cummed out, in any case.

He gave me his mobile phone number and we parted ways. I did ring him a couple of weeks later, but he was busy cramming for his exams, so he couldn't promise anything until after.

I haven't been to another of Isabella's parties, either as the opportunity never arose. I'm waiting for when Graeme is out of town, again.

By the way, I've still got young Malcolm's number, if any of you ladies are interested?