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Charlies Tribulations Ch 01

Charlies Tribulations Ch 01

by fluffyjan69
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As he left the hotel Charlie felt quite nervous, ever since he was at school he had wanted to date Catherine, she was the one girl out of his class that he seemed to have had a crush on Although too shy of the time to do anything about it. He had been rather surprised to receive a message from her around a month ago suggesting that they meet up to find out what each other had been up to for the past 20 years

The taxi pulled up outside the bar and he got out rather nervously, paid the driver, and went inside. He looked around quickly but couldn't see Catherine anywhere. Perhaps she wasn't coming after all he thought. Rather despondently he made his way to the bar and ordered a drink.

"Hello Charlie!" Came the familiar voice behind him.

He turned around to see Catherine standing there.

"Oh, hello Catherine" he stuttered "sorry I didn't see you there!"

"Not a problem Charlie" she smiled, offering her hand for him to kiss.

Charlie felt himself blushing slightly as he took her hand in his and kissed it.

"It's lovely to see you after all this time, you don't appear to be any different if anything even more beautiful" he blushed again.

"Oh you're very kind" she grinned "I see you still seem to be as shy as you seem to be all those years ago back in school."

"Yes I'm afraid that was always my problem, especially when you were around" he felt himself blushing again.

"Oh you're very sweet, Charlie. I can assure you there is nothing to be shy about with me" she smiled reassuringly.

"Of course" he found himself nervously looking for something to say. "Sorry Catherine, would you... Would you.. like a drink?"

"Yes, thank you Charlie. Just a Diet Coke please, I have to look after my figure you know."

"Oh, I'm sure you don't, you look quite stunning to me" Charlie looked quite uneasy as he said that as he turned and bought her a drink.

"Shall we find a seat, Charlie?"

"Yes, yes, of course, I see there's a small table against the wall over there should we go there?" He pointed across the room.

"That'll be perfect Charlie, lead the way please."

He walked quickly across the room to the empty table, waiting for Catherine to join him. He pulled out a chair for Catherine to sit on.

She smiled brightly at this gesture and slowly sat down.

"What a gentlemanly thing to do!" She smiled "not something that you see every day these days, thank you Charlie"

He swallowed slowly and felt himself blush again.

"It's important to treat ladies correctly, it appears not many men have any sort of manners these days, sadly"

"Oh, I quite agree, Charlie. It's lovely that you think that way, very refreshing. Now, let's hear what you been up to for the past 20 years, I'd love to know"

They talked for what seemed like hours, about their work, most of the things they are done since school, university, and their private lives. Charlie gradually became more relaxed and enjoyed talking to Catherine enormously. He was a little disappointed to think that Catherine was in some sort of relationship but she didn't go into detail about who was with except to say it was rather complicated. She did say that it wouldn't stop them from seeing each other if that is what he wanted. Charlie said it would be wonderful to be able to see her again and he looked forward to it immensely.

The sound of a phone ringing interrupted.

"Oops, excuse me Charlie, phone call..."

Catherine answered the phone, and after a brief conversation put it back into her handbag again.

"So sorry Charlie, I'm afraid I have to go now. It's been really nice to catch up with you and I'd love to see you again soon, if that would be ok?"

They both stood up and Catherine lent across the table and kissed Charlie on the cheek.

"Until the next time, Charlie, I hope it will be soon" she smiled.

"Take care Catherine, it's been really nice and I REALLY hope it's soon too"

"Oh, I expect it will be quite soon, take care" she smiled and turned away walking slowly out of the door, briefly turning back to smile at Charlie.

As she disappeared out of the door, Charlie sat down, got out his phone, and booked a taxi back to his hotel.

Finishing off his drink he stood up and made his way towards the exit. He hadn't got too far when he heard a voice that took him back over 20 years again.

"Charlie? Is that you, Charlie?"

He turned around to see the unmistakably sexy figure of his old French teacher, still looking as wonderful as the time he had a secret crush on her all those years ago.

She beckoned him over.

He found it quite a coincidence that the teacher in school that he had the biggest crush on was in the same bar as the girl from school he had a similar crush on.

He must have looked very surprised as she waved them across to the table.

"It is Charlie, isn't it?" She smiled.

"Yes... Yes, it is, hello, Miss..." He found himself blushing in reply.

"Not so formal, please, Charlie, please call me Angela, it is my name after all, and we're both adults! Come, have a seat." She casually patted the seat beside her and invited him to sit.

"But I'm expecting a taxi" he replied.

"Oh, forget that my car's outside, I can give you a lift if you like?"

"Well, if you don't mind Miss... Sorry, I mean Angela."

"Of course not, Charlie, it would be my pleasure. It's lovely to see you after all this time. Cancel that taxi and tell me all about yourself." She grinned..

Charlie sat down, phoned to cancel the taxi he'd just booked, and for the next 20 minutes or so they discussed what they had both been up to since Charlie had left school. It seemed that Angela had left teaching shortly afterwards and had a very successful career in business management, which he thought was a suitable career for someone who always thought had quite an imperious aura.

"I retired from that after my divorce" she added,

"Oh, are you retired now?" He asked.

"Well, sort of. I now run a kind of mentoring organisation, where I feel I can help others find their true place in life. I'm more than financially secure, and can spend the time needed to guide others!

"I'm sure you're very good at it!" Charlie found himself replying. He could tell from her broad smile that she knew that she was indeed, very good at it.

"It's getting quite late Charlie. We should think about getting you back to your hotel."

"It's very kind of you to offer, Angela. That would be wonderful, thank you."

"Come, follow me." She stood up and walked slowly towards the door. Charlie followed close behind, his eyes transfixed on her still hourglass figure and her heels as she walked slowly out of the door. He followed her across the car park to her car, a very low sporty model. She unlocked the drivers door and stood by it looking at Charlie.

"The gentleman should always open doors for a lady, you know, Charlie."

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"Oh, yes... My apologies Angela please allow me to..." He stammered nervously.

"Thank you Charlie, that's much better" she smiled as she elegantly slipped into the driver's seat.

"Now hurry up and get inside, it's getting quite late you know!"

Charlie hurried round to the passenger side, opened the door, and tried his best to climb into the low seat as best he could before closing the door behind them.

"Buckle up Charlie!" She smiled turning the key in the ignition "I do like to drive quite fast!"

He fastened the seatbelt as the engine roared into life, looking across at Angela he couldn't help but notice that she had pulled her skirt up slightly exposing her fully fashioned stocking top. He felt his heart beat a little faster and he swallowed slowly looking at the tantalising sight. His eyes were drawn towards the gear stick where her elegant fingers appeared to be caressing it sensually, wrapped around and stroking it. He glanced up at Angela's face to see her smiling as if she knew what he was thinking.

"Tell you what, Charlie... What would you say to a nightcap? My home is nearly on the way to your hotel and it'll be a lovely ending to the evening."

"Oh..." He hesitated slightly "well... I'm sure that would be very nice, thank you." He was beginning to wonder just what was happening.

"Good! Hold tight!" She grinned as she put the car in gear and drove out of the car park turning left onto the main road.

They drove for around 10 minutes out of town into the countryside until eventually, they came to what looked like the grounds of a large country estate.

"Here we are Charlie..." She said slowing down and pressing a button on the dashboard which opened the huge gates in the high walls. Charlie was quite aghast.

"This is where you live?" He asked glancing across at her.

"Yes, of course, Charlie I told you I'd been very successful, and I had to have an impressive base for my mentoring operation." A grin breaking out across her face as she spoke.

Charlie was quite speechless as they drove along the extensive drive eventually coming to quite a large country house where they pulled up outside of the front door.

Pulling on the handbrake, and turning off the ignition, Angela turned to Charlie and looked at him square in the eyes.

"Don't forget my door, remember what a gentleman should always do!"

"Oh, of course, Angela, one moment..." He fumbled trying to unlock the seatbelt and then clambered out of the car and closed the door. Walking around to the driver's side he carefully opened the door and waited for Angela to get out before closing it again.

"Thank you Charlie! I'm sure you'll remember next time, should there be one of course"

He seemed to be slightly confused... 'next time'? What on earth was she talking about? This was turning out to be a very strange evening indeed.

"Come on Charlie! Follow me!"

His heart was beating faster as he followed her to the front door which then appeared to open automatically as the approached, the lights inside already turned on as if planned. they both stepped inside and the door closed behind them. Once inside the entrance hall, Angela opened a door to the side.

"Have a seat in there, anywhere you like Charlie, make yourself at home, I'll get us some coffee."

"Thank you, Angela, that's very kind" he smiled, entering the room, looking around at the exquisite surroundings, obviously no expense had been spared in decorating the house. He found a chair and sat down.

After a few minutes, the door opened again, and Angela reappeared carrying a small tray with 2 cups, one of which she handed to Charlie

"Thank you, Angela" he smiled, taking a sip of the coffee before putting it down on the table at the side of the chair. He watched closely as she walked across to a chair opposite his and slowly sat down, crossing he legs as she did.

They chatted some more as they drank the coffee, Charlie began to feel a little more at ease, enjoying Angela's company.

It was only then that he noticed she had changed her footwear, and now appeared to be wearing knee length boots, something that had always fascinated him when she was teaching. He briefly glanced up, noticing that Angela was watching him intently.

"Charlie, you always did like me wearing boots, didn't you?" a knowing smile playing across her face.

He suddenly felt quite uneasy, knowing that she knew. Knowing that she had always known, He looked down at the floor and felt himself blushing.

"No need to be shy about it, Charlie!, I find it wonderful that you used to like them. It's wonderful that you seem to like them now as well!"

"Y.. Yes, Angela, I used to fantasise a lot about them, and you, if the truth is told...." He had no idea why he had just said that out loud.

"Oh, Charlie, how wonderful! Would you like a closer look at them?" She smiled as she ran her fingers along the leather covering her calf

"A... closer look? wh.. what do you mean?" he stuttered.

"Come..." She curled a manicured finger, beckoning him closer. "Come and kneel at my feet"

Charlie could hardly believe what he was hearing.

"Could I Angela?"

"Yes, of course, Charlie, don't be shy!"

His head was spinning with what was happening, but he couldn't resist following her invitation, standing up and walking slowly across to kneel at her feet.

"Mmmm... now Charlie, what would you like to do now? Hmmm?"

"I..I don't know, Angela..." he hesitated.

Glancing up briefly, he saw her point down "You may kiss them, if you would like to, of course..."

Charlie's breathing became quicker "Oh... Yes, Angela... I would love to kiss them" he looked down at her exquisite leather boots, swallowed slowly and licked his dry lips.

"Would you like to run your tongue across the soft leather too, Charlie?.... Would you?" She tilted her head inquisitively.

"I think.... I'd like that a lot, Angela, if I may.... Please..." He whispered, his voice trembling a little.

"Of course, Charlie, you have my permission!" Slowly she lifted a leg until the tip of her boot was pressing on Charlie's chin. She looked at him directly in the eyes and whispered, quite seductively, "Lick!"

He didn't need any further instructions, moving his hand up to cup the heel of her boot he gingerly ran his tongue across the tip of the toe. Slowly he ran it around the edge of the sole. He moaned slightly as he moved to kiss the top of her foot, the sight and scent of the leather filling his senses. Within a few moments, he found himself eagerly kissing and licking her wonderful boots, his breathing quickening as he did. He glanced up briefly to see Angela's face, eyes closed, soft moans playing across her wonderful lips.

"Don't forget the delicious heels, Charlie... You may lick, kiss, and suck those!" She whispered with a smile. "Would you like to lick, kis and suck my heels, Charlie?"

He could tell that she said those words with glee. "Suck them, Charlie, you know you want to!"

He did want that, more than anything... Quickly lifting her leg a little higher and fastening his lips around the spike heels. Taking it deep into his mouth, he could hear Angela moaning in pleasure.

"Mmm, now the other one, Charlie!". He needed no prompting, carefully placing one foot on the floor before lifting the other to his lips and eagerly lavishing attention on that one.

As he worked his way around the leather, he felt her other foot pressing against his groin, and stroking down his inner thigh

"Excited, Charlie?" he was concentrating on worshipping her boots too much...

"Charlie!" She exclaimed, a little louder, startling him a little.

"Yes Angela?" he sheepishly answered, moving his lips away from the exquisite leather, and looking up.

"Are you excited, Charlie?"

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He blushed

"Cat got your tongue, Charlie?" she laughed

"Sorry, Angela, Yes, very..."

"Good.. I could tell, I wanted to hear it from your own mouth... Now... how would you like to get your cock out for me? I can see you have quite an erection going on there" She smirked

"Oh.. I.. I don't think that would be... appropriate, Angela"

"Not appropriate?" She grinned "Don't be silly, it's not like I haven't seen enough in my time. Now, do as I ask, please..."

It felt more like an instruction than a request.

"I won't ask again, Charlie, I want you to get your cock out for me!" She looked quite stern as she spoke.

Charlie swallowed slowly "Yes, of course, Angela." he slowly unzipped his trousers and pulled his erect cock out "As you wish..."

"Lovely Charlie!" she said, looking down at his cock, leaning forward "Not bad at all..."

He blushed again.

"Would you like to wank for me?", she tilted her head inquisitively again, smiling.

"W..wank? Angela?"

"Yes, wank, I'm sure you know how to. I expect you used to wank thinking about me and my boots years ago!"

Charlie moaned quietly

"You did, didn't you?" She laughed

Charlie blushed looking at the floor again knowing that she knew exactly what he used to do.

"You DID!" She shook her head slowly, sighing.

"Well, now you can... for real... wank for me, pull back that foreskin and let me see just how hard you can get.. show me how much you want to, show me how much I excite you... I DO excite you, don't I Charlie?"

He nodded slowly, blushing profusely.

"Then DO it Charlie, do it for me!!" She suddenly sounded a little stern and authoritative

Without a word, he began stroking his cock as instructed, slowly and purposely, his cock hardening with his excitement

"That's it, slowly, gently.... There's a good boy. Show me how big it gets, show me how excited you are"

He felt Angela's eyes fixed on his cock, enjoying the sight of him doing exactly what she wanted.

"Look at me, Charlie, Look into my eyes as you wank for me"

He looked up, their eyes meeting as his hand stroked up and down his shaft, he could peel pre-cum seeping over his glans, he could tell by her eyes that she was enjoying this, very much.

"Do let me know when you think you're about to cum, won't you?"

"Yes Angela, I'm very close..." he stroked harder "Please?"

"Not yet.. not until you have permission!"

"Oh God..." he was on the edge, but couldn't cum just yet.

"Please, Angela...."

"In a moment!" she laughed "Rub your cock on my boot, continue wanking, and when I say, you may cum on there, certainly not before, and I don't want to see a drop on the floor, understand?!"

"Yes, of course, Angela!" he didn't need any further prompting, rubbing the head of his cock along her leather boot as the orgasm built.

"Cum for me! Cum for me NOW!" she commanded. Charlie screwed his eyes up as he felt his balls tighten, and his hot spunk begin to spray over her boots, his whole body convulsing with pleasure at his release.

"All over my boots, Charlie, there's a good boy!" She said softly as he felt the orgasm slowly subside.

He opened his eyes as the spasms tailed off to see copious amounts of cum dribbling down Angela's boot, he looked up to see her smiling at him.

"That's a huge amount of cum, Charlie, have you been saving it up?" She chucked "Saving it up, for me?"

He blushed again "N.. No Angela, I... haven't had the opportunity to cum for quite some time and it was wonderful for you to allow me to tonight!"

"It was, wasn't it Charlie" she grinned "Very good of me to allow it"

He looked down, not knowing what to say.

"You may, of course, thank me... if you enjoyed it, of course?" She let out a soft laugh

"Oh, of course, Angela, thank you, it was an awesome experience."

He looked down to see her hand slowly moving along down the boot he'd ejaculated over, and watched as she placed a manicured finger in the cum and moved circled it around a couple of times.

"Ever tasted cum, Charlie?" Her tone became a little more serious, looking into his eyes.

"Oh.... No, Angela, I... Haven't " he replied nervously.

"Time to change that... Don't you think, Charlie?"

"Well.... I....."

"Open wide, Charlie!" She exclaimed, holding her cum covered finger to his lips. "There's a good boy..."

He nervously opened his lips as she pushed her finger between them, "Suck..." she whispered, "Lick all your cum off, now"

Charlie slowly licked the warm, salty cum from her finger, not really liking the taste.

"Good!" she exclaimed, "Now... you can clean it up from my boot! Good boys ALWAYS have to clean their mess up!"

Charlie hesitated a little, "Do you have a towel, Angela, please?, or some tissues?" he asked meekly

"Oh, no, Charlie, messy boys don't get towels or tissues, messy boys have to clean up with their tongues!"

"My tongue, Angela?"

"Yes, your tongue, Charlie. You may have to get used to cleaning up after yourself!, And, while we're at it, it's time for you to address me as Miss again. I think that would be quite appropriate given the last few minutes, don't you?"

Charlie listened to her words "Yes.. Miss, I believe so."

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