Sexual Adventures with Older Women Pt. 02

Another extended episode continuing Gary's story.

You should perhaps read 'Summer Adventures with Older Women' before moving on to this one, although I think this can stand alone.

An introduction:

In the summer before going to uni, and after his girlfriend Chloe dumped him, he joined a dating app. Eighteen years old, he meets a whole series of women, Megan, a neighbour, Debbie, an adult party host, Elena, Chloe's mum, Jane, a teacher at his school, and a few more that lead him to further his sexual experience.

Pure fantasy of course, but fun!

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"Jane Hunter is a bitch!"

It wasn't exactly the first thing Chloe had said to me in the coffee shop, but it very nearly was.

Chloe had dumped me a couple of months before, citing her need to work for her exams. I was heartbroken, but eventually it led to my recognition that life goes on, and my mate Darren then telling me about the dating app.

The infamous Jane, who'd taught both of us at school, had manipulated us both, however it led both Chloe and I on a journey of exploration. Chloe into her sexuality, indeed her relationship with women, and mine into a discovery of my abilities to 'influence' older ladies.

Her relationship with Jane ended when she walked in on her dad kissing Jane. It seemed she would stop at nothing to have relationships that cut across other relationships. Elena, Chloe's mum, wasn't too happy either, even though both her and her husband seemed to lead a fairly 'open' lifestyle, as in going to swingers' parties. However, Chloe definitely didn't know about me sleeping with her mum.

"I'm so sorry Gary, I probably didn't realise how much you cared for me, I feel very sad about that."

I looked across the table at the girl I'd really adored, and who I'd made love to so many times. Flashing through my mind were the memories of bringing her to orgasm, and then the imagination that those same cries she'd uttered with me, she'd probably uttered with Jane.

"Mum told me I was a stupid cow when I dumped you, but I'm afraid I'd already 'slept' with Jane, and I was so confused about sex and everything. Then when I caught her with dad..."

I could see tears coming, so I quickly said, "Hey, it's water under the bridge, we all have regrets."

I couldn't tell her that I'd had sex with her mum, and with her dad's knowledge too, that would have really finished her.

I was being guarded, I didn't want to reignite our relationship after what had been an eventful summer.

"Look, we're both off to uni in a week or two, Southampton and Warwick are too far apart to see each other regularly, let's just stay friends, and see each other in the hols."

She looked both disappointed, and relieved at the same time. She had confessed her cheating to me, and now it was great that we could still be friends.

"Would you come round tonight, I hate talking in public, just to chat, just for the evening," adding, "I won't jump on you?"

I must have hesitated, not because I didn't want to discuss things with her, but more about seeing her mum and dad.

After agreeing to go round to hers' later, we finished our coffees, hugged, and went our separate ways.

In slight trepidation, later that evening, I pressed the door bell and waited.

"Hello Mrs Davies, long time, no see."

I lied as Elena opened the front door, looking quite sexy in leggings and flowing blouse.

"Hello Gary, Chloe's just upstairs on her phone, Nikki Phillips I think it must be, come in," she added, pulling a face, "Bryn's made himself scarce, in the garage."

Nikki was a friend from school, and could talk for England, so I was prepared for a long wait.

As I stepped into the hall, Elena whispered, "Not got a hug for me then?"

Awkwardly I gripped her hips, and Elena put her arms around my neck, kissing me full on the lips, forcing her tongue between my teeth.

It was a few seconds before I managed to pull my mouth away.

"For fucks sake Elena, if Chloe caught us..."

"I can't help it Gary, I want you, and I've decided I'm going to the party on Saturday, I hope you're going to go too. I've told Bryn to 'Fuck off,' because I'm gonna go along and shag everyone!"

Elena was clearly upset by Bryn's clandestine behaviour with Jane Hunter.

"I'm not sure. I want to go, but I'm off to uni the weekend after."

I was finding it difficult to talk normally, because Elena was massaging my crotch.

"Please do try, I want you to fuck me."

To have this older woman pleading for sex while her daughter was upstairs felt really odd. Quickly we stepped apart when we heard Chloe exit her bedroom, and come downstairs.

"Hi Gary, you're early."

"No I'm not, you're late because you've been chatting with Nikki!"

We both giggled, and the three of us went into the lounge.

Elena told us, "I'll leave you two to chat, I guess you've got some catching up to do, I'll bring you a beer Gary, if that's ok?"

I thanked Mrs Davies, and sat down with Chloe on the sofa.

It soon became obvious that Chloe wanted me back. Her body was quickly leaning into mine, and her hand casually found its way onto my thigh. I really didn't want this. I wanted Chloe to give it time for us to re-establish trust, and I knew being in separate unis was going to be a problem for any relationship happening again.

"Here you are Gary, I'll put it down there."

Elena was leaning over the back of the sofa, putting the bottle of lager on the table beside us. As she did so, out of sight, she gently gripped my shoulder, and squeezed.

"I'll be in the kitchen, I'll make some coffee later," she said, and she left us alone.

Chloe had her own ideas about our chat. After just a few seconds, she began to snuggle up against me, nestling her head on my shoulder, and rubbing my thigh. I could smell her characteristic perfume, and it triggered the memory of being in Jane's bed, wondering where I'd smelt that perfume before.

Predictably my cock began playing tricks. Whether it was the thought of fucking Jane Hunter, or Chloe's hand moving inexorably towards my crotch, or indeed, the thought of her mum being in the kitchen, but it showed it's presence, under my jeans.

"Chloe, your mum's just through there, and we've not chatted, we said we'd talk things through. Stop it!"

I was trying to keep my voice down, I'd grabbed Chloe's wrist, but she seemed determined to be intimate in some way or other.

At the same time she was kissing the side of my neck, instinctively I was becoming aware of possibly hurting her wrist.

Releasing her briefly was a mistake, my zip was soon pulled down, and frantically I was looking over my shoulder trying to assess where her mum was.

"Fucking hell Chloe, for god's sake stop!"

I could hear Elena had turned on the tv in the kitchen, just at the moment when Chloe somehow flipped my cock out through the opening in my boxers.

"Jesus!" was all I could say as Chloe lowered her head and took me in her mouth.

"Stop Chloe, please stop, your mum'll catch us."

But she was on a mission. Her head had started to rise and fall slowly as my cock was reaching its full size, and I found myself sucking in air very quietly. I knew it might be best to cum quickly, otherwise there was going to be hell to pay.

I was trying to stay quiet, be calm, but to summon up any power I had to ejaculate as rapidly as I could. Chloe was not quiet. She was slurping her way up and down my cock, the bobbing of her head increasing in speed.

And then I suppose I half expected it. Out of the corner of my eye was a movement, I turned my head to one side, and in the doorway was Elena Davies, casually leaning against the door jamb, watching the final moments of her daughter's blow job.

On her face was a sarcastic smile, and the pleasurable recognition of me being caught in the act. She raised her eyebrows just as I started to cum. I could see her putting her hand to her mouth, stifling a giggle, as I tried to stop myself grunting. Chloe was swallowing every drop as I pumped her mouth full of spunk. I held the back of her head until Elena had given a little wave, and retreated back into the kitchen.

"You little brat," I muttered, "just wipe your mouth, quickly."

I was hurriedly squeezing my cock back inside my jeans when Elena reappeared and deliberately said, "Do you want a drink Chloe, I'm just making coffee?"

I saw Chloe's face turn puce, and I turned towards her mum, trying to buy time for Chloe to regain her composure.

"I'd love one Mrs Davies, if you don't mind."

As soon as Elena had gone I looked at Chloe and said angrily, "You wait, I'll get you for that!"

She giggled, and provocatively licked her tongue around her lips.

We did continue to talk quite sensibly for the next couple of hours, mostly about our upcoming uni courses. Bryn appeared briefly, and the frosty atmosphere between him and Chloe was self evident.

Before I left, Elena found a moment to whisper, "See you on Saturday, I hope!"

I nodded, and left for home.

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It was next morning, Tuesday, that I got Megan Anderson, my neighbour's text. While I'd been on holiday with mum Mr Simpson, across the road had been up to mischief.

'Welcome home. Hope you and your mum had a good time. Mr Simpson's become a pain. He knows about us and is causing problems. Can I see you tomorrow?'

I knew he couldn't have any direct knowledge about me having sex with Megan, he'd probably just seen me visiting, and put two and two together. However, next morning I told mum Mrs Anderson might have some work for me, so I was popping out to see her. Just two doors down, I was there in a minute.

"Gary! come here, give me a hug." As soon as I was inside the front door Megan grabbed me.

Kissing my neck, she spoke, muffled against me, "Gary, that bugger across the road had the bloody cheek to make a pass at me. He came over and knocked on my door with some excuse about neighbourhood crime. He invited himself in, and somehow insinuated he'd seen you creeping into my house, and "did my husband know?" Bastard, when he started trying to flirt, I got rid of him pretty quick."

"I think you're jumping to conclusions," I said, I shouldn't have laughed, but I did. "Even if he did speak to Dave, he knows I've been doing work. Just call the guy's bluff."

That seemed to calm Megan's panic, and she took my face between her two hands and kissed me.

"Fuck, I've missed you, young man, god I want you."

Even as she said it her, she was pressing her body against me.

"Steady on Megan, I can't stop long, mum's wanting help with something this morning."

"Gary! My pussy is soaking wet! I need it, here, fuck me on the stairs."

Immediately Megan turned around, hitched up her skirt, and bent over the bottom few stairs. It was clear that she was prepared, I could see her naked pussy, with its plump swollen lips, peeping between her ass cheeks. There was a hint of her readiness with a thin line of glistening wetness seeping between her labia.

"Now do it, PLEASE!"

In no time I'd unbuckled my belt and unzipped myself, pushing my jeans and boxers down past my knees. My cock was almost erect, and the moment I directed it towards Megan's pussy, it had no problem in sliding inside.

"GOD! How I've wanted that," Megan exclaimed, as she shoved her ass back against me, "now fuck me... hard!"

Her elbows were leaning on the third step as my thighs smacked against her fleshy ass. Her pussy was so wet with juices, that my balls were soon dripping.

"YES... YES... YESSSSS!... GO ON!... GO ON!... oh my god... oh my god... GARY... I'm going to CUM!"

Megan must have anticipated my visit because she was already aroused so much. As she shuddered, I had to grip her hips, holding her up, her legs beginning to crumple.

I continued to pound into her, desperate to cum myself, and a combination of Megan's pussy pulsating, and her colourful language I was almost there. She realised that and turned her head.

"Cum in my mouth, let me suck you, quick!"

I pulled away and Megan turned to sit on the stairs, as she offered her mouth up to me. I pointed my cock towards her, and started to cum. A spurt of semen looped it's way across her face before she took me between her lips, the second spurt dribbled it's way down her chin and onto her blouse, before she was able to suck the rest of my spunk onto her tongue. Sucking and swallowing she eventually lifted her spunk covered face upwards, scooping my semen onto her fingers, and licking it off with a mischievous smile.

"Gary, that was fucking great!"

"I don't think I've heard you swear as much as that before," then looking at her blouse I said, "I'm afraid I've made a bit of a mess."

Megan laughed, "You get off, back to your mum, let me know when I can see you again. I've only got another week and a bit before you're gone?"

"Yes, I'm off to Warwick the weekend after this one."

When I got back indoors mum asked if Mrs Anderson had more work for me, and I hurriedly made up the excuse that she was discussing with Mr Anderson the idea of putting a pond into the garden. I was surprised at how easy it was becoming to lie.

Chloe was continuing to bombard me with texts, she seemed desperate to see me again before she went to uni in a couple of days time. I was resisting that, and I knew Elena and Bryn were taking her down to Southampton on Friday for freshers' week, returning on Saturday. It remained to be seen if both she and Bryn turned up at Debbie's party.

When Saturday arrived I'd lied to mum once again that this was an all night party for a few guys who were all leaving to go to uni. She kindly paid for another taxi fare and I arrived at Debbie's around eight fifteen.

I felt a lot more confident this time compared to the last party. Debbie greeted me, saying how great it was that I could come before I left for uni. Immediately Pauline pigeon holed me, showing a massive amount of cleavage as her ample breasts overflowed her party dress.

"Gary! I was hoping you'd be here, do you think we might have time together tonight?"

"You never know!" I answered, winking, but not committing myself either way.

"Tease," she retorted, pulling a fake 'disappointment' expression.

"I'm just going to get a drink, I'll see you later!" I replied, and gently I escaped.

As I moved through the room between various couples, I felt all eyes on me, but this time I felt a sort of confidence, even a hint of arrogance, as I caught the glance of some of the ladies, and just smiled.

I picked up a bottle of lager and a voice behind me said, "Hello."

I turned and saw Millie's face smiling at me, with quite a stony faced guy beside her, who I immediately guessed was the jealous Mark.

"Hi Millie, nice to see you again, this must be Mark?"

Mark had left her at the last party when he got jealous about her going with another guy. He grudgingly offered his hand, and as I shook it, I wondered if he was imagining me fucking Millie, and I was pretty sure he was.

"Hello," he said, and then quickly, "C'mon Millie, there's Ollie and Rachel over there."

Millie just had time to raise her eyebrows and say, "See you later Gary, maybe," and Mark dragged her away.

I decided to wander, and it was obvious that there were a few more people at this party. Outside the hot tub was bubbling, although no one was in it so early in the evening, and there was also a 'buzz' about the lucky draw that was going to take place.

Debbie was circulating, speaking to all the women, and encouraging them to take a ticket. I stood slightly fascinated watching the giggling faces, some embarrassed, some definitely refusing, and some being dared by their partners. When Debbie approached the couple closest to me, I listened in.

Apparently in one of the bedrooms upstairs was a 'Sybian.' Now I'd not really heard that name before, but it was clear it was something you 'rode.' From the amount of conversation in the room, and the shouts from one couple to another, it was going to be the show stopper!

"Go on Barbara, if you get a ticket, Gill will get one too!"

"Stop it... you can't really want me to... not in front of everyone..."

These were just some of the comments flying around.

Pauline was close by so I asked her to explain.

With a couple of glasses of wine consumed already, she was giggling, "A Sybian is a machine, a bit like the saddle of a horse, you sit astride it, but it has a dildo-like cock and a pad. The cock's inside you, moving and vibrating, the pad vibrates too. It's a complete masturbation machine controlled by remote control."

"Wow, so why the tickets?"

"Ahhh! So whoever's ticket is drawn wins a bottle of champagne, but also has to ride the Sybian for at least fifteen minutes."

"So can people watch?" I was really interested.

"OH YES!" Pauline beamed, "See the tv screen on the wall over there? Well..."

She could see my smile.

"You've guessed it, but that's not all."

Pauline explained gleefully, "A guys number is drawn as well, and he gets the remote control!"

"Fuck, that sounds like fun," I was imagining all sorts. "So how do guys get tickets?" I wanted to know.

"It's the number on your box, you know, the one you put your clothes in later."

"Oh my god, it could be me!" I burst out laughing.

We all laughed, and Pauline raised her ticket up to show me that she'd got one.

"It all happens as soon as everyone has their kimonos on. We all assemble in here and the draw takes place."

I looked around the room and there were still couples arguing excitedly about whether their 'ladies' should take a ticket. There was one couple where the guy had taken a ticket for his wife or partner and she clearly wasn't happy.

I took another beer, and just as I was about to go outside, Elena Davies arrived. She was accompanied by a couple who were not at the last party, but were vaguely familiar.

She caught my eye straight away and came over.

"Hello Gary, you made it. Bryn's not coming, but this is Shirley and Martin Blake, you knew their daughter at school, Chrissie?"

I did indeed, Chrissie had been fucked by my best friend Darren over the bonnet of his mum's car, something that he told me about with great relish.

"Yes, she went out with a friend of mine for a while... hello."

Mr Blake shook my hand, and Mrs Blake held my gaze a little longer than she should.

"Would you get Shirley and I a drink Martin, white for me," Elena was anxious to get her first drink.

Martin asked his wife for her preference, and disappeared to the drinks table.

"Shirley and Martin are regulars here, but they weren't able to come to the last party."

"No, a prior engagement disappointingly, we do enjoy these 'get togethers." Shirley's voice was deep and sexy.

Perhaps a strange term to use, but I could see from her constant staring that she might have an appetite for a younger man. What fascinated me about her, was the similarity to her daughter. Shirley was quite short, like her daughter, with long black hair, full breasts, and deep brown eyes which invited you in.

Elena continued, "Well you know about mine and Bryn's 'upset,' don't you Gary? I told him to stay behind, he's persona non grata at present, but Shirley sometimes 'lends' Martin to me on these nights. Perhaps you might join us later and amuse Shirley?"

Despite my new found confidence I flushed bright red.

"Oh poor boy, you've placed him in an awkward situation Elena, he may not want to."

Elena leaned forward towards my ear, and loud enough for Shirley to hear, whispered, "He'll want to, and he knows I'll have him after you!"

Thankfully Martin arrived back with the drinks, and I was trying to regain my sense of it all. Shirley was certainly someone who was very sexy. She was extraordinarily so for a woman in her early fifties, and those eyes kept drawing me in.