The old man was an imposing figure and as he looked down at Michael he felt an involuntary shiver. The deep voice only added to his nervousness. “Do you have anything to confess?” Michael knew that his whole future would be decided in the next few minutes and so he thought very hard. After several minutes he replied “I did once take a train ride without paying”. Saint Peter paused and looked at the old man before him more closely before asking “Were you faithful to your wife, sober in all you did and never lusted after other men or women?”.
“Er..I guess that's right” Michael replied “I did work very hard and always avoided being alone with other women, I didn’t take drugs or ever drink more than half a pint of shandy or a small glass of champagne a few times at weddings.” “Very well, in you go.” said Saint Peter “You will find a few like minded souls there already but don’t expect to have much fun!”
Michael awoke with a start. For a moment he had thought he was standing at the pearly gates being judged. His life had indeed been blameless so far and all he had to look forward to was more of the same it seemed. He was alone in the bed as his wife was away seeing her ageing aunt and he had been planning to clean the flat thoroughly and surprise her on her return with a nutritionally balanced vegan meal. A noise from the flat upstairs reminded him about the new tenant.
She seemed to be a single young woman who had quite a lot of visitors, sometimes quite late at night. He had been taken aback when they had passed in the hall while putting out the rubbish - she had been wearing a very short skirt and a top that emphasised her large breasts. He had tried hard not to look and focused on her face which despite the makeup was pretty and her smile seemed warm and genuine.
He had been polite but nothing more but she had said “I like to get to know my neighbours so why don’t you come up for a coffee sometime?” as she ascended the stairs. He had mumbled something non-committal and tried not to look at her arse but she had turned and added “or something more if you like.” He had pretended not to hear and hurriedly returned to his own flat feeling his face turn red with embarrassment.
Despite his good intentions he had found himself wondering what she meant and it had taken a great effort of will to turn his thoughts to other matters like the charity fundraising work he had signed up to do later. As he tried to process his dream and its implications the image of her arse came back into his head and unconsciously his hand moved to hold his cock which started to stiffen. And suddenly he knew what the dream meant - living a blameless life meant missing out on a lot of fun so tonight he would take up her offer and perhaps, finally, do something he could regret.
Image from https://www.dreamstime.com/
“When is it too right but too wrong to be right?”
― Dominic Riccitello
He raised the glass to his lips and took a long swallow and as he placed it back on the bar sighed deeply and felt the tension begin to leave his body. It had been a long day and now he coil drelax with a few drinks before going back to his room and catching a few hours of sleep before it all began again tomorrow.
It was the exquisite perfume that caught his attention and he turned to look at the woman who had sat down on the next stool. She was dressed in a way that was classy but just sufficiently revealing to suggest that this was a woman who was comfortable in her own sexuality. She was also at least 20 years younger than him.
He knew that his looks had not completely faded but the paunch and the world weary demeanour were turn off even for women of his own age - even his wife. But even so he smiled at the woman and noticed she didn’t yet have a drink while his own glass was now empty. He asked her what she would like to drink and told the server to put in on the bill for Room 208. They chatted in a desultory way over the drinks and then he took his leave and went upstairs.
30 minutes later he was in his room watching some soccer on the TV when there was a knock at his door. To his surprise it was the woman from the bar holding a bottle and two glasses. “I wanted a nightcap and I never drink alone,” she said.
The glass she poured him was large but quickly disappeared only to be followed by another equally large. He wasn’t sure which was more intoxicating - the wine or the presence of a beautiful woman in his room who seemed unaware or uncaring about the fact that her dress had ridden up to reveal that she was wearing stockings.
Somehow the conversation had turned to films and she interrupted his description of how wonderful Liza Minnelli had been in Cabaret “I made some movies my self a few years ago but you probably won’t have seen them.”. He had to know and asked her to tell more.
The movies had been hard core porn he soon learned. “My speciality was taking two fists - front and back” she laughed “Sometimes a girl would put two in my cunt while a man put two in my arse” she added.
He could hardly believe what he was hearing from her - or from himself when he said “Can you still take a fist?”. Her reply took his breath away “I’m not sure - shall we find out?”.
When he emerged from the bathroom having washed and undressed he saw she was now lying on the bed, legs apart, wearing only the stockings and clothes and handbag were on the table. The tube of lube, rubber gloves and condoms on the bedside table surprised him “I always come prepared” she said “because you never know what life has in store”.
Early the next morning he lay in bed thinking back - had he really fisted a beautiful woman something he had only ever fantasised about? Yes he had and he had gone on to put his cock in her mouth and her vagina as well before ejaculating in her anus. Perhaps it had been a fantasy really but then he noticed the lingering scent.
At that moment his mobile pinged. It was early and that might mean it was important so he picked up and opened the message.
“I hope you enjoyed last night and that this little movie will remind you about it. My bank details are below and if you would be so kind as to deposit £500 on the first of each month your wife need never see your debut as a movie star!”.
Life, as it sometimes does, has distracted me from sex itself let alone blogging about it for months now but I did so want to post this week. WW is wonderful thing and as a latecomer to it I wanted to say thank you to Marie who also somehow finds time to encourage us personally as well as doing all the hard work. Thanks to all the others who post, comment and have made a newbie feel at home (and a little less lonely!)
Time, as is well known, sometimes flies like a bird and sometimes crawls like a worm, but human beings are generally particularly happy when they don't notice whether it's passing quickly or slowly.
Photograph by Igor Wrapa, www.wrapashouse
He was utterly aware of the passage of time. He knew exactly how long it took for 400 hours, 24,000 minutes, 1,440,000 seconds to pass and as the 400th hour ended the phone rang.
It was the call he had been dreading, the call he had been longing for yet before he could answer it stopped and he felt physically sick - he had missed the opportunity.
Seconds later a text arrived saying "Be here in 1 hour. This is your first and only chance to please me."
He had been put in touch with her by a Dominatrix he visted who Madam had trained. He had submitted his application and eventually received a reply giving him a time and place to attend. He had been blindfolded on arrival and as far as he knew was never in her presence. He had no idea what she looked like anyway as she had no internet presence and only accepted referrals from those she trusted.
He had been met that first time by a young woman who described herself as Madam's amanuensis. She had told him to remove his clothing so that she could fit him with a penis cage which she then locked. Once he was dressed again she steered him to the door and whispered that after 400 hours he would receive a call which he must respond to at once. She then gave him a package, deftly removed his blindfold and pushed him back out into the street.
The package contained dietary and exercise instructions and three butt plugs of different sizes. It did not contain the key to his cock cage. During the next 16 days he followed the exercise and dietary regime and inserted the plugs each morning as instructed.
400 hours without ejaculation at first seemed an impossibly long time but he settled into a routine and learned that he could even forget that he was caged at least for a few minutes at a time.
He looked again at the text and began to do what he had mentally rehearsed so many times. His heart was pounding - never in a lifetime of sexual adventures had he wanted something this badly and now he was going to give himself to her to do with as she wished.
The same young woman met him at the door dressed in black latex and said "Madam has instructed me to see that you are scrubbed, shaved and given a high colonic. Please do as I instruct and do not speak other than to answer a direct question."
An hour later, satisfied that Madam would approve of her work, she led him into the next room. The cock cage remained in place but a steel ring had been added around his testicles. It had been impossible to stop him self becoming aroused as he was handled by the beautiful young woman and his semi erect penis was pushing against the cage painfully.
She had shackled his hands behind and placed a collar placed around his neck before blindfolding him again. He was acutely aware that his emotions were in turmoil and fear was close to the surface even though he also longed to meet the woman he had fantasised about so often.
At the young woman's prompting he climbed the stairs and halted as instructed. He felt her hand on his shoulder and responded to her gentle push by walking forward several paces. He stopped as she removed her hand and a moment later he heard a door close behind him.
He stood, shaking, for what seemed like many minutes before hearing the door open and then close again. He heard the unmistakable sound of high heels walking towards him and as they stopped he became aware of the heat of a body close by.
"Boy, you will answer my questions by a nod or shake of your head" The voice was warm and slightly accented. He nodded. "Do you consent to be used in any way I choose?" He swallowed hard and nodded again. "Have you ever been pegged? This time he shook his head. "Now take two steps forward" He did and felt something at hip height then rubber gloved hands pushed him forward while pulling his steel encased cock and ball down and below the board he was now lying on.
A strap was quickly pulled across his back and fastened tightly. There was no going back - he was utterly at her mercy. He heard the door open once more and again high heeled footsteps approach. He felt the gag being loosened and was told "Open wide".
The rubber penis was bigger than the gag and was pushed almost to the opening of his throat making him gag before being pulled back a little. "Start sucking" he was instructed by Madam.
As he settled into a rhythm he felt his legs being nudged apart and then the electrifying feel of a finger probing his anus. His cock was instantly hard but again he felt hard steel of the cage prevent him becoming fully erect.
The finger probing his back passage was replaced by something larger and colder that went deeper than he had ever experienced. It felt good but it too was soon removed. And then he felt something a softer and warmer nudging his rosebud. This felt like flesh and he wanted to scream but as if she had read his thoughts Madam said "Stay calm foolish boy - it is a strap on you can feel not some pathetic man's appendage." He relaxed and let it enter him - the strokes were hard, deep and repeated.
He lost all sense of time - surely he always been penetrated by two cocks? Then, without warning both were withdrawn and for a few seconds he thought his ordeal was over but the hard sting of a paddle told him he was wrong. His gag was replaced before the caning began and mentally he counted the strokes. He had never taken more than 25 before but that landmark was soon passed As he tried to avoid tensing he appreciated the skill with which he was being beaten - each stroke somehow finding a fresh piece of flesh.
As his pain intensified he desperately wanted the beating to cease yet he dreaded the last stroke. Once past 50 part his mind began to think about the significance that had been given to the number 400 and he knew that he simply could not survive 400 strokes. But at 75 the caning ceased.
There was a long silence though he was aware of the two women moving about the room and finally Madam spoke but to her assistant not to him. "I am done with it. You can send it on its way or play with it some more if you wish. The rest of the night is yours but I shall expect my breakfast brought to me at 9 sharp."
He realised that he still had not seen her face and now he never would as he heard her heels move to the door and out. The young woman removed the strap, gag and blindfold and he saw that she was wearing a strap on. "May ask which you were" he asked hesitantly and was surprised when she giggled and said "I was face fucking you - Madam always likes to stretch the little rosebud of virgins like you. We'd better get you cleaned up" she said briskly "follow me".
His pulse had begun to slow as she gently but expertly cleaned him and applied salves to his many wounds. Finally she took a key from around her neck and unlocked the cock cage. She washed his penis and held it in her hand. "It doesn't seem very hard now" she said smiling at him which made it twitch a little "Shall I see if its still working properly?" she added as she leaned down and took the rapidly hardening cock between her bright red lips."
And then he realised that while the ordeal might be over extraordinary pleasures still lay ahead before the night was over.
"The Girls in their Summer Dresses" is a short story written by Irwin Shaw in 1939 that addresses a way some men behave and it is as fresh and relevant as when it was written 80 years ago. I wish I could write half as well but it served as the inspiration for this piece which had been half written for ages. Bridget's prompt is "Turns ons" - and it all came together because right now my response is simply "Girls In Their Summer Dresses"
For three days the city had grown warmer and that morning he rummaged through the wardrobe to find a linen jacket and a shirt that would have been overly bold for a man of his years most days but was acceptable when the sun shone this brightly. As he made his way to the Underground station, he couldn’t fail to notice the girls too had rummaged through their wardrobes and were wearing flimsy pieces of cotton that revealed long pale legs or last year's tops that were now just a little tight but very revealing.
The train was crowded and he tried hard not to stare at the legs and breasts on display. Some belonged to girls who were young enough to be his granddaughter and it would have been utterly inappropriate for him to give even a hint of appreciation. Others though were below faces of mature beauty, faces that betrayed the fact that they had witnessed some serious living. Here he felt he could allow his gaze linger just a little longer.
Once he would have looked for the prettiest young girl and smiled his special smile, the one that always seemed to elicit a smile in return. Sometimes that was all but once in a while it led to something more in the naive way it can when you are young. The older women brought back memories of a different time however. A time when it wasn’t the smile but the Saville Row suits and Rolex watches that made clear what sort of man he was and might lead the right woman to make the signs he was seeking. A shy smile and a slight opening of the legs and as she moved to the exit an accidental touching of hands and a backward glance.
And once in a while that glance would ascertain that he was indeed following. Those were the women who understood instinctively how it was going to be and were on their knees as soon as the door closed but others took longer to accept that while he would be gentle and generous to them, first they must submit to him. Now it was only women in their fifties who gave him those small signs indicating their availability and try as he might they simply did not arouse him and so he had learned to avoid eye contact with them.
These days he found it better to pay for his deviant pleasures. The women were beautiful and knew exactly what was expected but they were kind too and told him what they both knew were sweet lies about his looks and performance. He did, however, believe that at least they appreciated the effort he made – no wandering nasal hairs or foul breath for him.
His reverie was interrupted by a young woman with face of quite extraordinary prettiness who stood up and approached him.
“Sir, please take my seat”
This was thing he feared most. He knew his looks had faded yet he believed he was still “interesting” but seemingly this morning his appearance had evoked only pity. Nevertheless he was nothing if not a gentleman, or so he liked to believe, and he demurred but she responded by saying that she was getting off soon.
“Do please have the seat, Sir, it is so hot this morning my legs are sticking to the seat!"
Without thinking he glanced down at those legs which were as pretty as her face. He thanked her and took the seat feeling conflicted in the extreme - both humiliated and turned on. Now he was seated it was hard not to look at the girl and he noticed that her arms were lightly tattooed and it also appeared that there was a hint of a larger one just emerging below the hem of her flowered dress.
He had not registered the facial piercing either when she offered him her seat but it did nothing to lessen her attractiveness - indeed it hinted that there might be other, hidden, treats to be explored. He looked up again and was surprised to realise that she was smiling down at him and he couldn’t stop himself smiling back despite feeling so old. The train was now slowing down and she moved towards the exit and he looked away and in doing so missed her backward glance
As the train began to move again, he realised she was standing on the platform looking at him through the train window and as their eyes met, she shrugged and smiled again but this time rather sadly and then turned away.
He was puzzled by this and for several moments struggled to make sense of it. Then it came to him and his heart sank and he silently cursed his own stupidity. No one under 50 ever calls someone “Sir” these days unless they are preparing to submit…
An old man called Mike remembers sex in London before the internet, rants about the hypocrisy of today's society and shares some links to the best companions around today......