Symposium Day Ch. 04

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Jen turns us both on as she tells me of her first time.
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Part 4 of the 4 part series

Updated 04/12/2024
Created 10/14/2022
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This story follows on immediately from Symposium Day Ch 1,2,3

The story so far:-

Ch1. Dave, Jen and I are at a symposium in Barcelona. I am the new boy at nineteen, Jen is late thirties, and Dave, a brusque northerner with an eye for the ladies, is somewhat older. After a meal in Las Ramblas, Dave heads back to the hotel leaving me with Jen, who he's been chatting up all day. Back at the hotel, Jen took me to her room where I got my first lesson in giving oral sex, something her 'shag about' husband won't do for her.

Ch2 Jen realised that this might have been a mistake and summoned me to her room to explain. She's worried that I am very young, one of only four people who know about her snake tattoo, and that I might not be discreet. When I made it obvious that 'What happens in Barcelona, stays in Barcelona', she invited me back to her room that night, where we discovered we both like talking dirty. (If you haven't read Chs 1&2, the head of the snake tattoo starts on her inner thigh, winds its way round her belly until the tail vanishes into her vagina)

Ch3. Jen decides that you can't have too much of a good thing and we arrange a tryst back in England. Over a month had passed when we got together on a Sunday while her husband was playing golf. My education continued and I made some more discoveries. This story continues on that Sunday.

With Jens words,

"I definitely think we could have lots of fun together. I have plenty more ideas about how to spend a Sunday!" Ringing in my ears, I lay face down, spreadeagled on the bed. I was enjoying the afterglow of a rumbustious fuck, that had culminated in her taking my post orgasmic, hypersensitive cock in her mouth. It hurt, it hurt like fuck, but....I have to say, I enjoyed it! She finally let my tortured glans slip from her lips, sore but strangely satisfied.

"You better get your carcass off that bed, I have laundry to do. I can't have the sheets covered in your cum when hubby gets back. So unless you want me to spank that lily white bottom again, shift it!"

"It's just so comfortable! Besides I quite enjoyed it when you spanked me as I was about to......."

"When you were about to cum!" She exclaimed, "You really are a mucky little toad, and kinky with it!" She grinned, as she approached the bed, still naked.

"I'll go and fetch my long handled shoe horn if you stay there, it's just the thing to teach your bum exactly whose boss."

"Only if you wear your glasses." Said my mouth.

"What! What is it with you and my glasses?"

"Don't know, they just make you look incredibly sexy."

"Am I not sexy anyway?"

"Of course you are: extremely sexy. I love watching you walk about naked with your breasts hanging free and that snake tattoo, but your glasses just add a little something.

"I think it has something to do with the fact that I once had the hots for a teacher who wore glasses, maybe that's it."

"So how far did your 'hots' go?"

"Nowhere actually, but she did feature in my dreams."

"You mean your wanking fantasy."

Again I was taken aback by her language. Do grown up women use the word wank? I muttered something unintelligible.

"Come on admit it. You used to lie in your bed, stroking your stiff young cock, thinking of Miss Whatsername in her glasses until you shot your load, I bet.

"Anyway, there's nothing wrong with a good wank? If I don't cum fucking, I often finish off that way, I usually use my fingers as Mr Rabbit makes such a racket, that it might make hubby feel nearly as inadequate as he is."

This is getting more and more bizarre. Jen was standing beside me stark naked, snake tattoo right in front of my eyes, talking about her masturbation habits, her husband's lack of sexual prowess, and threatening to spank me again..

"This isn't getting those sheets in the machine, can't have them covered in your spunk when hubby gets back. Shift!" And she smacked me firmly on the bum. Much to my surprise I enjoyed it, nearly as much as I had when she spanked me as I came.

"Sorry Miss, I don't want to."

"Want to! Want to! That has nothing to do with anything!"

She opened the wardrobe door and grabbed a long handled shoe horn. Long and fat.

"I warned you!"

"Dare you!" said my mouth seconds before I heard the resounding impact of plastic on flesh. The noise was incredible but the pain was minimal.

"Sorry!.....

"So sorry, that was much harder than I intended."

The startle factor spread across my buttocks and turned into a rosy glow of satisfaction.

"I said, only if you wear your glasses!"

"Fuck! You want me to do it again, don't you?"

"Only..."

"Yes, I know!" She grabbed her glasses.

"Go on then!....

"Double dare you!"

Thwack! Fuck! That smarted! The pain again gave way to a rosy glow.

"Shit! You have two bright red weals on your bum!"

I rolled over.

"And a fucking erection! I don't believe it you kinky bastard!"

"It was sort of nasty and sort of nice at the same time. On balance, I liked it."

She leaned over and stroked the injured flesh.

"And I like that too!"

"You are one mucky little toad! But we can't send you home with that stiffy."

She grabbed an item of silk clothing, and wrapped it round my cock.

"Have you ever had a silky wank before?.....

"Didn't think so!.....

"Just relax!" She gently started to move the silk up and down over my cock. It felt good: no it felt fucking amazing! With each down stroke the purple head of my cock appeared, then vanished again as the silk slid sensuously along its length.

Her other hand now started to manipulate my balls. All these new sensations combined to produce the result that nature intended and I came, and came vigorously.

"Fuck! Again! More spunk! Even on your second cum."

We lay there and giggled for a few moments before we got up and started to dress.

"Be careful who you take your clothes off in front of for a few days! Those stripes could be difficult to explain."

We said our goodbyes and arranged the next time with the proviso that I wore a crisp white shirt?

So, duly wearing the required crisp white shirt, I found myself approaching her house on a foul Sunday, the heavens were just chucking it down and I wasn't thinking. Too late!

As I walked up the drive I noticed two cars! Two! Not one! Oh shit!

A man was unloading golf clubs from one. Double shit! To turn and vanish would be a bit obvious! I summoned all the courage my nineteen years could muster and continued towards the door. What to say? What to do?

"Oh hi," said the golf club man, "Jen said you might call. Something to do with the Barcelona symposium, as I recall.

"I hope you'll excuse me but the weather is so foul that the boys and I have decided to go to the pub in stead....

"So I am going to have to leave you two alone.....

"Don't you two be getting up to any mischief!"

My jaw must have dropped. I'm here with the sole purpose of 'getting up to mischief' with his wife, and he's made a joke of it.

"Sorry," he said, noticing my expression, "just my sense of humour. Silly of me, I know Jen is nearly old enough to be your mother. Forget I said it. Ridiculous really. Sorry."

I recovered my composure as he climbed into his car and vanished. Jen ushered me inside.

"I thought you might not realise that very few people play golf in this sort of weather, so I spun him a yarn about you and Barcelona. Actually it's all an act because he's really off to shag Sally."

My jaw dropped again, "What!"

"Well it's obvious really. He always goes out on Sunday morning, hail, rain or shine, either to golf or to the pub with the 'boys'. He always wears his best aftershave, best shirts and so on. We never have sex on Saturday, while he saves himself, and he's always too tired on Sunday! A bit of a give away.

"Don't get the wrong idea. We are very, very married. We get along brilliantly and probably would never separate no matter what, it's just that we are bored with each other sexually. I don't know why we can't just be honest. If we just agreed that Sundays are our days to shag a friend, it would be so much simpler!"

My young brain was trying to compute all this new information. When my blood pressure finally returned to something like normal, she made me a coffee, sat me on the sofa, and vanished upstairs. She returned in a bustier shrouded, but only just, in a diaphanous peignoir and sat beside me.

"So tell me about Miss Watshername, what was her name?"

"She was Miss Peters."

"Go on! Tell me about Miss Peters."

"She was my French teacher, not all that much older than me and, you're right, very attractive."

"French?"

"No, but had a very sexy accent, long blond pony tail and even longer legs. The square glasses made her look even more sexy for some reason, but the crisis really started when she got married. I just couldn't get her out of my mind."

"What's so special about her getting married?"

"Well, you know. She was obviously doing 'it' and I was still very much a virgin....it...."

"You mean, she was married and you couldn't get the image of her, flat on her back, with her legs in the air, welcoming her husband's rampant cock into her juicy cunt! That's what you mean!"

"I suppose it is."

"So you wanked yourself stupid imagining it was you between her splayed thighs, burying your virgin cock in her married pussy! You really are even muckier than I thought, but in a good way!

"I bet she wore stockings in your fantasy, didn't she? Did she keep them on while you fucked her? I bet she did. You men are such suckers for suspenders and stockings."

She produced a pair, as if by magic.

"Would you help me put them on please."

She turned towards me, raised a leg onto my lap, displaying the taut fabric of her panties struggling, more or less successfully, to cover her sex, smiled, and offered me a stocking. Who knew how sexy putting on stockings could be, not I for sure!

After being shown how, I slipped the sheer fabric over her foot and slid it slowly up the soft pliable flesh of her inner thigh. I have to confess I didn't rush. She offered the other leg. How soft can flesh be? How warm? How fucking sexy?

I admit that I had an erection even before she stood up and guided me through the fastening procedure of attaching them to her bustier.

"No! Not like that.....

"The suspenders have to go under my panties......

"Otherwise I have to undo every thing just for the loo."

I was learning, I carefully threaded each fastener under the top of her panties and out of each elasticated leg. If placing the rear ones over her delicious buttocks was sexy, then doing the front ones, offering a forbidden glimpse of pussy, were on a whole new level of eroticism.

Once my trembling fingers had completed this task, my cock was bursting to be released from my boxers. I admired my handiwork and the slightly plump flesh as it emerged from the squeeze of her stocking tops.

"Oh fuck! That feels so good. It brings back memories. Just like when I gave my virginity to George."

"George?"

She snuggled up beside me.

"Yea George. Back then, nice girls didn't, you know, do it, well not without putting up a struggle anyway. George and I were 'going out'. We were snogging in his dad's car in a quiet lane. I know, corny or what? Anyway that was then, this is now."

"No, go on. It's interesting."

"Really?"

"Yes, really."

"Well George had his hand on my knee while we snogged, then it moved a little up my thigh. I knew that nice girls didn't allow this, so I moved his hand away. In truth I was hoping he wasn't going to give up.

"Back then, us girls had a rule of three. If we gave in before the third try, we weren't 'nice' girls; and if he gave up before three tries he was a wimp.

"He continued to try. The hand was now half way up my inner thigh, still on my stocking but getting close to my flesh at the top. It was delicious! I was juicing. I moved his hand, but I didn't want to, and I was thinking, please don't stop: don't give up!

"Every fibre in my body was screaming, this is life! This is what you are here for! To reproduce! He wants to put his dick in you to inseminate you and, truth to tell, you are busting to let him.

"He didn't give up! The hand returned. It slid up to the bare flesh between stockings and knickers. Oh fuck! Do I move his hand again? I know I should, I also know I don't want to. I'm flowing. My knickers are wet! Evolution is telling me to mate with this boy, but society is telling me to resist. I moved his hand. Three down!

"I don't know why, but my hand brushed over his crotch. This encouragement caused his hand to return with more confidence. It slid up my stocking. He kissed with more passion. It found the bare flesh at the top! Sparks flew! I am incredibly wet, I so want to fuck even though I have no idea what fucking feels like, or why I want it, but I do: I so do.

"His hand reaches the edge of my knickers. Oh fuck, decision time! A finger slides under the elasticated leg. It finds my moistness. God I'm wet. Sparks fly. He touches my clit. Our tongues battle. I am about to cum. Fuck convention it's decision made!

"Somehow his cock is in my hand.

"He slides my knickers off.

"I am about to mate for the very first time.

"I have tossed boys off before, but never actually fucked one. I am about to become a woman.

"He is not taking my virginity, I am giving it to him: willingly: wantonly.

"Legs spread wide, I stare at him in the half light, the most sexually aroused I have ever been.

"If he looks down he'll see my pussy lips glistening with my lust.

"My eyes say it all.

"Fuck me!

"Penetrate me!

"Inseminate me!

"There is a fumbling moment, a ripping sound, as he puts on a johnny.

"It is really about to happen!

"He kneels between my thighs.

"The moment is now!

"Will it hurt?

"Who cares?

"I want it.

"There is a first for every virgin.

"His cock touches the outer lips of my flowing pussy.

"Bloody disaster! He cums! I feel the end of the johnny fill, and he's not even properly in yet! Then nothing. Fuck all. Nada!

"Is that what all the fuss is about? I thought.

"I may well still technically be a virgin! FUCK IT, all that for nothing!"

During the story, our hands had involuntarily followed the script. I had caressed her stocking clad leg all the way up her thigh. She, reliving the tale, had removed it each time.

Finally, I reached the elasticated edge of her knickers. My finger slid inside. She was wet: just as wet as in her memory. I stroked her flowing sex with my index finger, while she rubbed my crotch.

I slid her panties off. She lifted her bum in compliance. I dropped my trousers, and knelt between her splayed thighs. Just as she got to the bit about the disaster, I entered her forcefully.

She actually cried out loud, clutched my buttocks with both hands, holding me deep inside her and, judging by the spasms I felt running along my cock, she came: I came very soon after.

"Fuck, fuck, fuck, I've been waiting for that for twenty years. God, that's how it should have been: how I imagined it would be. Stars, tingles, lightning bolts, the works.

"Maybe I should take you out in my car?" I said, carefully extracting my cock from her slickness, lest I spill cum on her settee. Fortunately her peignoir offered some protection.

"I don't think we could work that magic again, not to the same extent." Her thighs were still quivering.

"Best let it be a memory. But I do have another idea."

"Go on."

"How's your bum?"

"Fine! Actually I found it really sexy. Particularly the aftercare!"

"That's what I want to talk to you about. I think you find some pain erotic. You know, the spanking, and when I sucked your cock, just after you'd cum......"

She paused.

"Would you like to explore that a bit more?"

My blood pressure shot up again. I had tried to rationalise the erotic feelings I got from certain pain, but failed. I knew I had enjoyed it but I didn't know why, and before I had time to think my mouth had agreed.

"So next Sunday, I'll be Miss Peters and you'll just be you, a naughty student. I warn you I'll probably be a lot stricter than her. The only lines she'll give you will be with a long handled shoe horn on your bum! So if you find anything you don't like, or can't cope with, just tell me to take off my glasses and I'll be Jen again. Agreed?"

"Agreed." .....Continued.

As always, if you can spare a second or two to comment I would love to hear from you. Feedback is my main motivator. Did you like it? Did it bring back memories? It certainly did for me as I wrote it, I've always had a thing for older women, particularly if they wear square framed glasses and have a long handled shoe horn!

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