Sally and the Charity Night

Story Info
Sally was nervous but at least no-one would know her...
3.3k words
4.25
23.6k
17
7
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It may have been the alcohol but Sally found herself wanting to know more.

"You mean men would enjoy looking at this body? But I'm overweight. Just plain plump!" she said, unbelievingly.

"Nonsense." Ted replied. "You aren't overweight -- and you certainly aren't plain either."

Ted hoped he hadn't said too much. He did find Sally attractive but that wasn't why they were meeting for a drink after work. He knew she would prove extremely popular at his charity do -- if he could only persuade her to ditch the dowdy outfits and show off the body he was sure she was hiding under them.

"And these women ... these plump women. They don't perform sexual acts with the men? You know I am active in the church -- and I have never been with anyone other than my husband." she continued.

"They don't have intercourse, if that is what you mean." said Ted. "And masks, wigs and the like are provided to ensure no-one recognises you. There is a certain amount of touching but mainly the guys just like looking. And it is in a good cause. The community centre couldn't survive without our annual donation -- not that we give them all the details of how the money is raised, of course."

A part of Sally did get a little thrill out of imagining herself dressed in some naughty outfit, exciting those younger men who had made a donation to charity so they could see her. Sex with her husband happened less and less after they were first married. Sally was fine with that -- being a headmaster was a stressful job for him and she was sure that her putting on weight over the years hadn't helped. Perhaps she could pick up some tips from the other hostesses to get him interested again -- and it was charitable work, even if it happened to be a little unconventional. But then she shook her head. "No -- you're winding me up, aren't you? You probably get some skinny young girl to strip in front of them and I would be the comedy warm up act, overweight and making a fool of myself."

"I can assure you that the people who will be there on Friday aren't the slightest bit interested in young or skinny." Ted insisted. "They all have the same taste or they wouldn't come along and spend that much money, year after year. Do you realise we have a waiting list for this year's event? That's why we can't go ahead without filling all the hostess roles."

"And your wife is fine with this?" asked Sally, raising an eyebrow.

"If you mean with me taking you for a drink and trying to persuade you to wear sexy outfits for the benefit of paying customers, the answer is yes. And if you mean with her being the lead hostess ever since we started these events, the answer is still yes." Said Ted. "And before you say it -- yes, I know I'm a lucky man."

"Well, I suppose if you let her take part then it can't be that bad. Go on then, I'll give it a try. But don't blame me if those paying customers of yours take one look at me and demand a refund."

But Ted was confident there would be no refunds. He had a feeling his customers would be very happy indeed.

And that was how, later that night, Sally found herself in a village hall with half a dozen other plump and mature women, being allocated her outfits for the evening. Everyone else was holding the outfits up to their bodies and laughing. "Well, too late to back out now." She thought, and started trying on her allocated outfits.

Each hostess had half a dozen outfits, some smart and sexy and some quite kinky. The idea was to circulate throughout the room wearing one of the outfits and when Mike rang a bell, everyone disappeared behind the curtain and changed into the next outfit, the outfits getting gradually more erotic with each change of clothing. The gentlemen attending the event were allowed to ask the hostesses to pose in specific ways so they could get a good view of them. Anyone was allowed to touch the hostesses but only over the top of their clothes and only for up to 30 seconds at a time.

Some of the girls started straight away with a sexy schoolgirl or French Maid outfit but Sally looked for something a little less revealing for her first outfit.

The little black dress looked classy when she held it up but as soon as she tried it on, she realised how short it was. She had chosen seamed black stockings and suspenders rather than tights, as she didn't want to seem a fuddy-duddy -- but she knew she couldn't wear a dress this short with stockings as they would be completely on display.

She dropped the LBD and next chose quite a thick, woollen plaid skirt thinking it would be a bit more "normal" but again hadn't realised how short it was.

Just as she was about to choose a third outfit, she heard a big cheer from the hall and the curtain started opening. Mike's voice announced "Gentlemen -- our hostesses for the evening. If you like what you see then please give them a round of applause." And the hall erupted in a wave of applause, cheers and whistles.

Sally blushed under her mask as she noticed a few of the men ducking down to try to look up the hostesses' skirts -- including her own.

"Now ladies," continued Mike, "Please make your way into the hall and meet your audience."

With her heart in her mouth, Sally followed the other women and walked down the four steps and into the hall. Almost immediately, a tall chap, around 25 years of age, made a bee-line for Sally. She moved aside to let him pass and was astounded when he said "No -- it's you I was coming to see. You are new to this, aren't you? Could you just hold your skirt up at the front for me please?"

Sally blushed under her mask but she supposed she was getting off lightly really. She looked away -- she couldn't look him in the eye -- and slowly lifted the front of her skirt.

"Oh stockings! Lovely." the young man said. After moving closer and taking the time for a really good look he eventually stood up and said, "I'll be back for another look later." And with a pat of her bottom -- well, more of a fondle, really -- he was off.

The next few men to approach her all wanted her to lean forward and lift her skirt to show her stockings and panties from behind.

Sally knew she was getting off lightly but also wondered if she would be expected to provide a little more as the evening went on.

Then the bell rang and Mike announced "Time for a change, ladies. Gentlemen -- you have five minutes if you wish to top up your drinks."

Sally picked up a French Maid's outfit but a large breasted woman next to her said "No -- save that until later. Try this first." And handed her a black mini-skirt with matching top, red high heels and flesh-coloured seamed stockings. "The trick is to slowly build the excitement -- don't peak too early."

Sally smiled a thank you and quickly changed into the outfit, finishing just as the curtains opened again and Mike announced, "Gentlemen -- your 30 second touching time limit is now extended to two minutes." And a great cheer went up throughout the room.

As Sally strolled around the room, eating up the many compliments she was receiving about her cleavage or her shapely legs, she suddenly noticed a very familiar face and froze in her tracks. Her husband was in the room and he was heading straight towards her.

"Sally? Is that you?" The poor man couldn't believe his eyes. His wife was strutting around a room full of men in little more than her underwear. "What are you doing here?"

Before she could reply, a tall young man tapped her husband on the shoulder and said "Excuse me ... if you aren't doing anything with the lady?"

"Of course -- feel free." He replied, without realising quite what he had given permission for. The young man immediately reached for Sally's large breasts, wasting no time in utilising his 2 minutes of touching.

First, he eased her top up and fondled her breast over the top of her bra. Then, he moved in front of her and enjoyed himself fondling and groping her breast-filled bra cups.

Sally wished the ground would open up and swallow her. Why did her husband allow this to happen -- and right in front of him?

Then he hoisted first one and then the other breast out into the open and made the most of his remaining time, cupping, stroking and gently squeezing each breast, occasionally licking and sucking a nipple.

"I thought you were only supposed to touch over the clothes!" gasped Sally.

She was burning with embarrassment as she looked pleadingly at her husband while having her breasts lovingly fondled by a stranger. Her husband also looked uncomfortable and that was partly from seeing a strange man fondle his wife's large breasts right in front of him and a room full of other men but also for another reason. He was confused to find that he was extremely aroused.

When her admirer reluctantly removed his hands from her now tingling breasts, gently kissing each one before walking towards a shapely brunette dressed as a nurse, Sally blurted out an apology to her husband but he quickly stopped her. The more Sally apologised, the more he assured her it was alright -- and the more aroused he became. Sally glanced down to his trousers and saw a clear bulge -- what did this mean?

"Well at least there is no-one here that knows me." Sally started, "At least no-one except you."

"Well, there is one person here who knows you." Mike said, hesitantly. "Pete came top of the trainee lab assistants and won the job at the school so the heads of department chipped in to treat him to a ticket tonight."

"Pete my nephew? Oh, that's wonderful news." Cried Sally, "At last a bit of down to earth good news."

"Well yes. But there is something else." He continued, anxiously. "It is tradition that we all chip in for the winner and pay for him to have a private appointment at the charity night. It turns out he wants you -- that is why I was coming over to talk to you. He hadn't quite recognised you -- and nor had I. In fact, he said you remind him of his Aunt Sally and it would be like living out a fantasy to have you dressed in outfits she would never wear and do things to you that she would never permit."

"But I couldn't let him see me up close -- he can't find out I am here, allowing strangers to fondle me." Then, dropping her eyes and her voice, she continued, "It's bad enough that you found out."

"Don't worry about us -- we can talk about this tomorrow. But you have to go through with this with Pete. It would just draw even more attention to yourself if we had to back out of giving him his prize. We can get you a better mask and wig and make sure the lighting is kept low. He'd never believe you would actually do something like this so we have that in our favour."

Sally started to protest but her voice was drowned out by Mike again announcing that it was time for a change of outfit. Her heart sank as her husband said "Just get changed and make sure you have a full mask and wig. I'll get Pete another drink -- that might stop him recognising you." And with that he was gone.

Sally hurried over to change and was relieved to find a long wig which totally transformed her appearance. "At least he shouldn't recognise me." She thought, torn between the conflicting emotions of complete embarrassment that her nephew wanted to fantasise about her while he did goodness-knows-what to a woman he didn't even know -- or at least the believed he didn't know -- and the forbidden excitement of a younger man being sexually excited by her.

Excited though she certainly was, Sally just couldn't go through with wearing a blatantly sexy outfit for her own nephew. She chose a sheer top which made a feature of her large breasts and high heels and stockings. Then she swapped the stockings for tights, thinking that would be less likely to excite Peter.

As she made her way back down the steps, she saw Peter and her husband, eyes fixed on an exotic, shapely woman, pulling up the back of her dress to expose her stocking tops and suspenders.

Then, she turned and started removing her clothes, exposing her large breasts. For some reason, Sally was fascinated by those breasts.

Then, when she was dressed only in her stockings, suspenders and high heels, she slowly walked over to a man sitting on a sofa and eased his erection free of his pants and slowly masturbated his shaft.

Then she leaned over and slipped the head of his cock in her mouth. Sally's eyes flitted from the act of her sucking a cock to her plump, shapely legs -- then back to her sucking the chap.

Sally gave a gasp as she realised that both Peter and her husband had released their erections from their trousers and they were slowly masturbating as they watched the woman teasing the lucky guy in front of her. Sally was glad she hadn't gone for anything too sexy to wear this time. Her plan was for Peter to have a little excitement -- nothing too much -- and then for her to slip away and get home before her husband did. Sally hadn't realised just how sexy her full figure looked in the little top, sheer tights and high heels -- but Peter soon realised. And so did her husband.

Peter rushed over to her gasping "Oh she's perfect -- she looks just like her. She's even wearing tights rather than stockings -- just like aunt Sally would."

Sally was a little uncomfortable with how Peter was looking at her legs and her breasts. In fact, she didn't need the wig as he hadn't even glanced at her face. He walked around her and she jumped when his hand stroked her nylon clad thigh. But before she could do or say anything she was surprised by her husband coming up to her and kissing her full on the lips.

So surprised was she that it took her a full minute to realise that Peter was not just stroking her thighs with his hand -- he was rubbing his extremely erect penis against his aunt's tights-covered bum.

"Oh! Don't look at what he's doing, darling." Cried Sally, with shame and embarrassment in her voice.

But he was looking. Not only was he watching his nephew fondling his wife's nylon clad bum, he even asked Peter if he was enjoying it.

"Oh yes, she's perfect!" gasped Peter, with emotion in his voice. "It's just like fondling auntie herself -- not that I have done that, of course!" And Peter and her husband laughed, as if sharing a private joke.

"You have to make him stop." Hissed Sally. "He might realise it's me."

But instead of telling his nephew to stop, Sally's extremely aroused husband reached for her breasts and said to his nephew, "Enjoy yourself, lad. Imagine it is Sally's plump bum you are fondling -- like I am imagining these are her breasts I am playing with. Not that she would ever allow that to happen, of course. But we can pretend it is her -- so why don't you just enjoy yourself while imagining it is your aunt. You can even slip a hand inside her tights and play with her."

Sally started to protest but then, as Peter's inexperienced finger slipped inside her pussy, she heard him say, "Oh she's soaking, uncle. Her pussy is squidging it is so wet."

And for the first time, Sally realised that she was wet. She was aroused at the idea of her nephew fondling her in front of strangers -- and in front of her very excited husband.

And then, as he gently tugged on her nipples, she heard her husband say, "Go on, lad. Enjoy yourself. Pretend it is Sally's pussy you are fingering. Pretend it is her nylon-clad thighs you are rubbing your cock against. Would you like to shoot over her nylon-clad bum cheeks? You can, you know."

"But uncle, you know I have more of a leg fetish," replied Peter, "I've told you I dream about her nylon clad legs squeezing my erection."

Sally's eyes widened as she hissed to her husband, "Have you really been having these sorts of discussions about me? My own husband and my nephew having lewd thoughts about me -- and discussing them with each other?"

"Shh!" he replied. "Remember you are supposed to look like his aunt -- not actually be her. Let the boy have his fun."

"But .. he is sliding his erection against my legs. He's masturbating himself using my legs -- his own aunt. And right in front of my own husband and a room full of strangers!"

And with that, Sally's husband continued to tug at a nipple with one hand while the other slowly traced its way down her body to her pussy as he whispered, "But he's only having some fun. You know he has always had a crush on you. You've never discouraged him. I've seen the way you have crossed your legs as you sat on the sofa, opposite him, letting him see up your dress."

Thinking of those times as Peter squeezed his erection between her legs and her husband played with her nipple and her pussy made Sally blush. "He's only living out a harmless fantasy -- he doesn't know it is really you."

"Yes, but I do." Hissed Sally, wondering just how she got herself into this situation.

"Then do it for me." Pleaded her husband, taking her hand and placing it around his extremely aroused penis.

"Oh!" said Sally. And she was distracted enough for Peter to run his hands up and down her plump, nylon clad legs as he thrust between them and for her own husband to watch the scene unfold as he thrust his hard cock -- harder than she had ever known it to be in all their marriage -- into her hand as his finger rubbed her pussy lips and smeared her moist juices over her nub.

And though she wondered what turn life was taking, as Peter placed thrust his cock between her plump calves, she squeezed his orgasm out of him, while he was lost in the sensation of his hands groping her nylon covered thighs. Her body started trembling and she felt the waves build from her knees, up through her legs until, prompted by her nephew spurting over her legs and her husband simultaneously spurting over her hand, her orgasm swept over her.

Panting, out of breath and more than a little embarrassed, Sally extricated herself from her husband and rushed back behind the curtain. But not before Peter grasped her in a big hug and gave her a big kiss, right on the lips. As his hands roamed her plump bumcheeks and even cupped her breasts, he said the words which she both dreaded and yet which also excited her so much. "Thank you so much. I have fantasised about my aunt since I was at school and it was wonderful to live out that fantasy with someone who looks so much like her. I do hope we can do that again soon."

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
7 Comments
ToughSailorToughSailor6 months ago

Nice story, however Rubenesque and stockings aren't really my thing . . . .

BaldguyIND59BaldguyIND598 months ago

I love the husband watching aspect and the family angle and how a plump woman can be so sexy. Always love the nylon aspect. Keep up the hot writing!

AnonymousAnonymous8 months ago

Very exciting for her to know that her husband is excited for her to be on display and available. I am sur she is hoping for more

Show More
Share this Story

Similar Stories

Confessions of a Soccer Mom How and when everything began to change.in Incest/Taboo
Emma Visits Home Incest on the family farm.in Incest/Taboo
Mom Sucks Dick! She can't live without it. So, when Dad's out of town...in Incest/Taboo
My Son's Lap Mom accidentally sits on son's cock when dressed as Santa.in Incest/Taboo
Jen's Trip to the Beach Pt. 01 How could a mother be so tempted?in Incest/Taboo
More Stories