Girlfriend Agrees
to go Topless
FIRST CUCKOLDING
Matt Coolomon
Adults Only
High level erotic content
Copyright © 2016 Matt Coolomon
All rights reserved. No part of this eBook may be reproduced, stored in a retrieval system or transmitted, in any form, without the written consent of the copyright holder.
This is a work of fiction. Any resemblance to any real life person is coincidental.
Other titles by Matt Coolomon:
Sweet Catherine’s First Experiences
Sweet Catherine is a Pretty Plaything
Sweet Catherine Can’t Say No
Sweet Catherine Really Likes Men
Sweet Catherine’s Open Marriage
Sweet Catherine at the Gentlemen’s Club
Glory Hole Wife
Party Girl Shared
Married Couple Visit a Swinger Club
Young Wife Gets a Sensual Massage
Wife Shared at the Lake
Wife Tries Oral at a Party
Young Wife Shared on a Desert Island
Wife Offered to the House Guest
Wife Shared with Dirty Old Men
Girlfriend Agrees to Sex with his Buddies
Bride-to-be Tries Other Men
Wife Tries Flashing and More
CHAPTERS: 1 2 3 4 5 6 7 8 9 10
1
“Are you kids thinking about getting married? Already?”
Lisa nods, unsure of how to take the older woman.
“Oh, dear, but you’re so young.”
“We’re both 20.”
“Well yes, in my day that was the done thing. But these days aren’t you supposed to be wild and free until at least your late-twenties? I have two daughters who didn’t marry until 30, and my son is still single at 34.”
“But we love each other, so there’s no point being free to look around. Neither of us want to.”
The older woman waves over the waiter, pointing to her empty martini glass. The two women are sitting on deck chairs beside the resort swimming pool. Their men are both in the water.
“My name’s Margaret, by the way, dear.”
“Hi. I’m Lisa.”
“And how long have you been together, Lisa? If you don’t mind me asking.”
“Since high school, kind of off and on. What about you, Margaret – did you marry young?”
“Oh yes. I was 21. Bert there was 25 – a soldier and very handsome.”
Lisa returns a smile. “I’m sure he was.”
Margaret chuckles. “And still is to me, dear.”
“Well, I hope Alan and I are still attracted to each other when we’re your age. That’s very sweet.”
“Oh, thank you. That’s nice of you to say…. And I’d say your young fellow there is going to grow into a handsome older man too, Lisa. He’s a good looking boy with some growing up to do yet. Is his father a big man or slightly built?”
“He’s a solidly built man. Alan looks a lot like him as far as facial features go.”
“Ah yes, but a lot of men don’t fill out until later. My boy had that slight build of your Alan at his age. His chest and shoulders filled out in his late twenties. Physically he changed very quickly once he finally got past that gangly boy stage.”
“Hmm – well, that will be good in case I put on weight as well,” Lisa said, looking down at herself.
The older woman laughs. “Oh yes, dear. Don’t we all wish we could have kept our twenty year old figures?”
Lisa joins in giggling. The waiter serves Margaret her fresh martini. After a little while quietly watching the people swimming, Margaret raises a brow. “So, dear, tell me – are you and your young fellow first lovers?”
Lisa’s blush rises. “Um – we kind of were at first.”
“Both you and him?”
“Yes. As far as actually making love goes, we were.”
“Ah – so you’ve had other partners?”
“Yes. Just experimenting and that. Nothing serious or anything.”
“And your young guy there knows about it?” the older woman presses, her brow cocked again.
“Mostly – but not about everything exactly,” Lisa confesses, whispering now, even though her boyfriend is well out of earshot.
“Well, that’s something at least…. It’s good that you have that.... I was a virgin when Bert and I married. I was very inexperienced – had hardly ever been kissed, and not by any real men. And had that remained the case, I don’t think my marriage would have lasted.”
“Oh really?” Lisa’s interest is piqued now.
Margaret chuckles. “No – I don’t think it would have, dear. I think a man named Warwick did my marriage the world of good one time quite a few years ago.”
Lisa’s eyes are wide. She’s looking at her by-the-pool mate expectantly. “Did you have an affair?” she asks flatly.
The older woman frowns in thought. “No – I think an affair is when you actually cheat. I never did. Bert knew….”
“He knew? About this Warwick guy?”
“Yes. Warwick was a friend of Bert’s father. We were staying for a summer vacation. We were very young – before the kids came along…. Oh, it was all very spontaneous – just animal attraction and the confidence of an older man.”
“Oh wow! And did you have sex with him? Did your husband know at the time?”
“Bert didn’t know until after the first time. He was asleep – quite drunk as a matter of fact – and his father’s friend came to me and seduced me. He took me into the basement where he was staying, and after having his way he sent me back to my husband…. Then it wasn’t until the next night that I couldn’t hold it in any longer and confessed to Bert…. But all turned out well, dear. I have no regrets now.”
“But what did he say – your husband? What happened when you told him?”
The older woman sips her drink, her sharply plucked brows raising again as she meets Lisa’s gaze. “He took a moment to think about it then asked for details, dear. He asked for every intimate detail then took me to bed himself. Then he made himself scarce each night for the rest of the week and let the other man have me over and over – and Bert has been quite the forceful lover ever since.”
Lisa’s staring, mouth agape.
“Oh, I’m sorry, dear. Was that too much?”
“Was it true?”
“Yes – every word.”
“But what was he like before? Your husband – was he forceful before that?”
“No. Not at all. Before that he was a total pushover. It’s like Warwick gave him a wake-up call on how to make love. Like it was always in Bert, but he needed a shock to awaken it.”
“Oh wow,” Lisa cries under her breath. “That is so amazing.”
“I know, dear. And your young fellow strikes me as a lot like the way my Bert was, if you don’t mind me saying. I’ve noticed him with you the past few days. He seems quite timid with you.”
“Yes, he’s not very outspoken or aggressive. He’s a really nice guy, though.”
“Oh, I’m sure he is. But I’ve also noticed the way that older man you’re with looks at you, dear. And I’ve noticed that you’ve noticed.”
Lisa’s blush rises again.
“Who is he, dear? He’s not a relative of yours?”
“No – he’s just a friend. He was our neighbour growing up and has often invited us to stay for the weekend here on the coast.”
“I see…. And it’s just you and your boyfriend staying with him? Is he married or single?”
“
No, he’s single. He has a house on a small farm near here. We’re only allowed here at the resort because he manages the bar.”
Margaret nods, taking that in, it seems. “So, he would be in his forties? He’s quite attractive….”
“Yes, he’s younger than our parents. Kind of in between our generations really. He’s always been nice to me and lots of fun. It’s never really felt sexual before, though.”
“But it does now, right? The way he looks at you is entirely sexual, dear.”
Lisa sits forward, rubbing her shins. She takes a nervous breath. “But he knows I’m with Alan.”
“And no doubt he would see your young fellow as a mere boy…. Do you feel his eyes when your boyfriend is around?”
Lisa nods. “Yeah…. Alan even said something this morning.”
“What did he say, dear? Do you mind me asking?”
“No, it’s good to talk…. He said Evan seems a bit handsy and cuddly with me, and that maybe I should get dressed in our room before going down for breakfast – maybe not to wear my nightie around the house anymore.”
“Hmm – and this Evan, do you like him cuddling you?”
Lisa fights her blush as she shrugs. “I don’t know. He’s got such strong hands. It’s hard not to like it.”
Margaret nods. “Yes, dear, I knew it. This reminds me of my own experience so well. I knew I recognised the signs.”
Lisa giggles nervously. “Except I doubt Alan would be so happy if anything did happen.”
“No – quite possibly not! And please don’t read me wrongly, dear. I’m not suggesting for a minute that you should allow anything to happen. I’m just reminiscing and feeling a little excited to see another young woman in a similar situation to the one I experienced – the one that has meant so much to me over the years.”
Silence ensues for a while again. Lisa glances a few times before speaking.
“I’ve actually been the one to suggest we come here to stay with Evan each time lately. I can’t seem to stop thinking about him sometimes.”
“Well, that would explain his level of interest, dear. He’s no doubt picking up on what you’re feeling – the attraction going both ways.”
Lisa nods, chewing her lip. “But I really think Alan would be crushed if I let anything happen.”
The older woman holds Lisa’s eyes. “But you wouldn’t be upset yourself? The idea is just exciting and appealing to you?”
“Yeah – I guess…. It definitely excites me to imagine him kissing me.”
“Yes, I certainly know that feeling,” Margaret says with a smile. “But what about your young fellow – does he look at other girls much? Does he watch porn on the internet?”
Lisa giggles. “Um – I’d say yes but less than other guys – less than his friends do.”
“And do you ever complain to him about doing that, dear?”
“No. I don’t mind him looking.”
“But it’s not okay for you to be looked at? You know it’s the natural order of things for girls to dress sexily and for boys to notice. It’s perfectly normal and works both ways.”
Lisa smiles through her blush. “Yes – I suppose.”
“Suppose nothing, dear. My Bert there has checked you out plenty since we’ve been sitting here. His old eyes have been all over you in that skimpy little costume you have on there. As have the eyes of those two men across there with their kids…. Men like looking and we like them looking. It’s as simple as that. Otherwise you would have chosen a completely different costume, dear. And you can bet if I could still get away with wearing one of those little string ones I would.”
Lisa giggles. She knows the older woman is right. “But guys are so easy to tease,” she offers in reply.
Margaret laughs a little but cocks an eyebrow more seriously. “So, how revealing was this nightie you were wearing around the house for this other man to see?”
“I wasn’t wearing it for him to see!”
The other brow lifts – a challenge in the look of the older woman now.
“Well, a little bit, I guess. But it isn’t that revealing. It’s a pretty pink satin one – a chemise with lace trim.”
“How short? Where does it come to?”
Lisa indicates the level of the hem. “It covers me.”
“Anything underneath it, dear? Underwear?”
“Yes – down below.”
“But not up top?”
“No – I don’t like sleeping in a bra…. But it covers me quite well. It doesn’t show much cleavage or from beneath my arms – only a little.”
“Yes, but your nipples are quite prominent though, dear – and beneath satin….”
“So? I can’t help that, can I?” Lisa defends, looking down at herself and plucking at her bikini top.
Margaret laughs. “No – I always used it myself. I used to dress to show off what I had. That drove my man crazy and got me lots of special attention from him when he got me home and into the bedroom.”
“So, you teased him by dressing for other men?”
The older woman glances and smiles. “Exactly.”
“Hmm – that sounds interesting,” Lisa says.
“Personally, dear, I think it’s perfectly reasonable to wear a nightie around a house where you’re staying as a guest. And I suspect defying your young fellow on that one might just get him going a little…. I’d suggest an experiment where you stroll around looking sexy tonight and see how he responds physically when you get into bed – not what he says, but what he does.”
Lisa is chewing on her smile and shaking her head. “I think you might be a bad influence, Margaret. Do you tell your own daughters stuff like this?”
“Of course, dear. What are mothers for when you’re all grown up?”
2
The women’s chat ends when Margaret’s husband gets out of the pool and approaches dripping to grab his towel. He’s talking with Margaret but Lisa feels his eyes upon her – just furtive glances. She has on a white string bikini. Her thighs are slender, her breasts B-cup. She’s lying back with her arms by her side and her knees apart. She inches them a little wider as the old guy continues rolling his eyes down to look at her. She catches his glance and blushes.
“This is Lisa. Lisa, meet my husband Bert,” Margaret says. “And stop ogling you old pervert, you’ll make the girl uncomfortable.”
“Nice to meet you, Lisa.” Bert offers a hand.
Lisa accepts it, sitting up a bit. “Hello,” she offers sweetly.
“It’s hard to avoid ogling,” the man confesses with a smile and flash of his eyes over Lisa’s body again.
“That’s okay. I don’t mind…. I’m flattered.”
“Oh, don’t encourage him, dear.” Margaret says with a laugh. “Here, do my back, tubby,” she says, handing her husband a tube of sun cream and rolling over.
Lisa squirts her own lotion into a hand and applies it to her shoulder. She does her other shoulder and the back of her neck. The older man is watching her breasts while still rubbing cream into his wife’s back. Lisa averts her gaze as he glances up from them. She then does her legs and enjoys his attention to them as well, allowing them to stray wider open for him.
“Hey, Lisa,” a voice calls from behind, startling her. It’s her vacation host Evan. “How are you going there – ready to head off soon?”
“Oh, are we leaving?”
“Well, you guys can hang around all day if you like. I’m finishing up early and need to get home to do some stuff in my office. I could come back and pick you up later.”
“Or we could run you home,” Margaret offers, smiling up at Evan. “We’re new friends of Lisa,” she explains to him.
“No, I’m starting to burn, so I might leave off sunbathing for today. I could see you tomorrow,” Lisa says to Margaret. “Will you still be here?”
“No – we’re leaving in the morning, dear.”
Lisa waves her boyfriend over and packs up her gear, slipping on a sun dress while
the old guy continues watching her from his deck chair. She tugs it straight and catches his glance lifting from her legs, her blush rising, his smile broadening. His wife smacks his arm, and Lisa meets her eyes as they roll, the women exchanging a giggle. Alan pads over from the pool and dries off. “Evan’s finishing early. We have to go,” Lisa tells him, then she turns away and quickly pulls the strings on her bikini top.
She catches Margaret’s smile again as she pulls her top from her dress, and she blushes at the older man still watching her. She checks herself and tugs at the sides of her dress beneath her arms, where it’s a little revealing. The sundress is halter neck and swoops to her waist at the back, the edges not quite covering the swell of her breasts.
Margaret catches her hand as she’s leaving, pressing a folded piece of paper into Lisa’s clasp. “Good luck. Promise you’ll write and tell me what happens?”
“Okay,” Lisa utters, and she blushes a final glance at the old husband as she hurries away.
“Who was that?” Alan asks.
“Just a nice older couple I was talking with.”
“Oh right…. So, what are we doing this afternoon? I might see if Evan will lend me some fishing gear. I want to try the pier down the back of the farm.”
“Okay. I want to have a rest. I want to read my book and have a sleep.”
“Cool.”
Evan has pulled up in front of the resort in his old pickup truck. Alan opens the door and Lisa climbs in and scoots across the seat, meeting Evan’s smile. There’s a big gear stick that she has to keep her legs clear of. She sways them to the side but Evan’s hand touches her thigh as he works through the gears. He has on black trousers and a white tee-shirt, his collared shirt scrunched on the seat beneath Lisa. His shoulder is huge, his arm muscled. It’s pressing against Lisa’s as he continues working the gear lever through the streets. The two men are talking about fishing and Lisa is just sitting there bumping from one to the other as the old truck sways and lurches around corners. Her nipples are hard against the fabric of her dress.
“You’re awfully quiet,” Evan says, grinning at her. “What are you daydreaming about?” he adds, giving her side a poke.
Lisa flinches and giggles. “Nothing…. I just don’t like fishing.”
Girlfriend Agrees to go Topless (First Cuckolding Book 11) Page 1