This fantasy comes to an end here but the encouragement I have received from such super writers has meant a great deal to me and has inspired me to write more - thank-you Marie, May, The Barefoot Sub and F Dot Leonara - you've made an old man very happy - hope you enjoy the finale.
You can read the whole story from the start here
It was a few minutes before 6.00 pm and Michael was once more experiencing that mixture of fear and excitement that made the anticipation of a sexual encounter so special for him. He heard his mobile ring and recognised Jenifer's call tone. He knew she would expect him to call back if he didn't pick up at once but he knew Gabriela would be waiting.
He picked up the phone desperately thinking how he could cut the call short and failed. Jenifer talked and talked about inconsequential things before finally saying she had to go. He put the phone down and looked at the clock - 6.20 pm.
He hurried up the stairs hoping that when he explained Gabriela would be amused and forgive him. What he saw when the door opened took his breath away. She was wearing thigh length black high-heeled boots, long leather finger-less gloves and a high necked body that nevertheless left her breasts exposed. Once inside he began to explain but was stopped by a hard slap to the face.
"Silence" she said with a commanding tone he had never heard her use before - perhaps he didn't know this woman as well as he had imagined. "You will only speak when I tell you to and call me Mistress without fail. You have already earned 20 extra strokes of the cane and any further errors will only add to that total. Do you understand?". "Yes Mistress" he stammered.
He was soon naked and face down on her bed with his arms and legs secured. Gabriela then tied a scarf around his eyes which restricted his vision greatly. She began to use the flogger but he found this more enjoyable that he feared - the harder strokes did sting a little but the feeling quickly faded and the long, slow strokes were most pleasurable.
The door bell rang.
Gabriela would deal with it he thought and then recalled how she was dressed. As she left the room he strained to hear. He was surprised when she said "Welcome and you look fabulous - come on through to the chamber of delights my dear" Michael was terrified - what on earth was happening? They hadn't discussed this.
Once both were in the bedroom it was Gabriela who spoke. "I've warmed him up and he is ready for the caning now you are here." They moved to stand either side of the bed and he heard the unmistakable swish of a cane as first one then the other tried it out. "As you know he was going to receive 12 but he has earned another 20 for lateness." she said and they both laughed. Michael was now very scared - he considered asking them to stop but realised that at best it would be the end of his relationship with Gabriela while at the worst they would cane him anyway as he was unable to move. Somehow he made himself whisper "Ready Mistress".
Finally, after what seemed to have been hours but was in fact just a few minutes, the caning was over and he was in real pain. He couldn't imagine what his arse must look like and wondered if he was bleeding. He flinched as he felt a hand touch him but realised that some lotion was being applied and it did help a little after a while.
He felt Gabriela's warm breath on the side of his face and one hand took hold of his while she placed the other on his shoulder. Her tone had reverted to the one he had come to know so well over the past weeks - soft, warm, reassuring and very, very sexy. It calmed him and took away some of his fear.
" You took the caning well" she said "you will have marks you can proud of but now you need to do exactly as we tell you.". He felt his anxiety start to rise once more. "My friend will prepare you and ydo not resist." With that he felt a finger begin to probe his anus. "Just let the muscles relax" Gabriela whispered. He felt a second finger enter him and then the two pulled apart stretching him wide open.
The fingers withdrew and he felt the stranger climb onto the bed and get between his tethered legs. Gabriela began to speak once more as he felt something much bigger than a finger begin to press against his anal sphincter. "Open yourself up and let her penetrate you." Michael tried to follow her instructions but there was a moment of pain as the rubber cock entered him. And then, as it went deeper, he felt an extraordinary sense of fullness and realised his cock was hard and deep in his balls there were the first stirrings of an ejaculation.
The woman began to slowly fuck him and as she did so she pressed he body down on him and put her lips to his other ear. He caught a familiar scent and then heard her voice and finally began to understand.
Jenifer said "We both owe Gabriela a great deal and we must thank her but first I am going to fuck you till you come. my love."
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.
We're gonna let it all hang out
We're gonna chug-a-lug and shout
We're gonna cause talk and suspicion
Give an exhibition
Find out what it is all about
J J Cale - After Midnight
Not really about "Ceremony" WW#390 although given half a chance I make it something of a ritual - not writing much at the moment so sharing this while its fresh
Once, before the internet, I lived alone in a part of town where there was a local paper published every Friday. At the back of the paper in the personals were advertisements for massage parlours and escort agencies. Sometimes I would find myself late in the evening wanting to fuck a woman and the newspaper would call out to me.
Finally I would give in and look at the ads, circle an agency and call the number. The receptionist would begin by letting me know who was working that evening but back then I wasn’t looking for any particular kinks just a good looking woman who was ready to be fucked. Back then I could drink a lot but still get rock hard without any assistance so it was straightforward hard cock in tight vagina I wanted. Once we had established that someone like "Blonde Jennifer aged 25" was available and could be with me in 30 minutes, we agreed on the length of her visit and the price and I put down the phone.
My heart would be racing by now and I had to get ready. I would take a shower but I didn’t pay the same attention to personal grooming as I do now. I certainly didn't shave my genitals but then it was very unlikely that Blonde Jennifer would be shaved either but I would be clean and sweet smelling when she arrived. The anticipation was excruciating as I imagined what she might look like, whether she would be wearing stockings, how she would speak but above all how she would behave. Would she be businesslike and just want to get it over with or would she accept my offer of a drink and chat for a while letting me feast on glimpses of her thighs and breasts before kissing me?
The street door buzzer disturbed my reverie and I felt my cock instantly harden. This was it – she was standing outside the block and I quickly moved to the door and let her in saying I’m in flat 14 on the second floor. It was nearly 1 am and the noise of her heels on the stone stairs seemed incredibly loud as she made her way up. I now faced a dilemma – did I open the door fully and watch her as she emerged from the stair or wait until she was almost outside? Despite my excitement I would make myself wait until I could hear her approach the door.
Now it was game on – in a few second I would see the woman who would be ready to open her legs and let me push my penis into her cunt. The thrill of seeing the face of that stranger is simply one of the best things I did, and still do – what comes later will be satisfying but nothing compares to those first few seconds. This time she is beautiful, she is smiling, she is dressed in a way that emphasises her figure and she is here to be fucked.
I have no idea how many times I did this and albeit in a different ways that thrill is something I still pursue and those escorts who don’t reveal their faces like Jade or Carla have given me some utterly memorable sessions. Two of those encounters from that time stick in my mind. There was the girl with long brown hair who dressed like she was heading for the local pub rather than a sexual encounter. She was pretty and spoke openly about only working occasionally as an escort. She said she enjoyed having sex and if she didn’t have a regular boyfriend she contacted the agency and asked them to arrange a few clients for her. The mind plays funny tricks and I remember clearly that she was wearing a pair of really good fishnet stockings that I took great delight in caressing as I move towards her vagina to prepare it for penetration.
The other was a a slim short haired blonde in her early twenties who seemed a little nervous when she arrived and reluctant to remove her clothes. Eventually she confessed that she wasn’t really an escort at all! She was the receptionist and when I called she was knew that all the escorts were busy and wouldn't be making any more visits that night. She was, of course, well aware that they would be paid more for having sex with a single client than she would for a whole shift and she had decided to take the booking herself. My first reaction was to tell her to leave but she persuaded me that she really was happy for me to fuck her and removed her her skirt and knickers to prove it. Strangely she insisted on keeping her tee shirt on however. She proved to be an enthusiastic partner but years later I realised what an opportunity I missed. A young pretty girl was giving me the opportunity to be her first paying customer and I should have given her encouragement and support and taught her how to please me rather than just fuck her. It is something that I really only learned later – the best escorts will be very clear and even matter of fact about sex but if you make an effort to ensure the experience is enjoyable for them too you will be rewarded! I know escorts who have orgasms with me and I am certain they are for real and I am always clear that I am happy to do whatever it is that they enjoy in return for the pleasure they give me. It would never have occurred to me back then that some girls really do get a kick out of fucking men with a strap on but I am glad I found out.
The wider world has changed just as my private world has changed in the years since but the thrill of hearing those high heels clicking toward my door remains with me still. In fact I think I shall have very soon have to go to a hotel and arrange for a complete stranger to come knocking at my door after midnight one more time!
Newspaper headline "Middle East Deadline"
Jazz musicians are down on the breadline
Soho (needless to say)
I'm alone on your streets on a Friday evening
Soho (needless to say), Al Stewart
This week's prompt is "Unmentionable" and while some of the things Carla and I did might be unmentionable in polite company that isn't the link. The very fact that I had a joyous two hours with her is unmentionable to my friends, my family and in particular, my wife, which is a shame because it was a lot of fun but at least I can share it with you! PS - Isobel will be back next week
Picture of Carla James used with her permission
It felt good being back in Soho with sex on my mind but the nerves that usually reach a crescendo as the time of an appointment approaches were strangely absent. I was about to spend the afternoon playing out an extended scene with one of London's most accomplished role players yet I wasn't nervous! Had I known what the next two hours would involve I would have been but Carla's warmth had shone through our email exchanges as we worked out the roles we would play - I the "Master" and she the "Submissive" albeit one who knew what she wanted and how to get it only too well.
And then there were the masks! I have long harboured a fantasy about sex with a complete stranger while we are both masked - only when my cock is deep in her cunt are the masks removed and we see each other's faces for the first time. By the time I left that particular itch was going to be well and truly scratched.
The flat had a delightfully decadent feel while the four poster hinted of pleasures to come. When I emerged from the shower I found "Miss James" standing tall in heels, stockings and exquisite underwear - she looked me in the eye and handed me a collar and leash. I resisted the temptation to lay hands on her arse and spank it because she needed to be collared and then made to kneel before me so she could take my cock between her lips for the first but not the last time that afternoon.
I knew Carla could switch and I had given her free rein to take her character where she wanted but there was a palpable tension in the air when Miss James first asserted herself and made it clear that if I was to continue to enjoy her body I would need to let the alpha female out to play for a while. In that mood she was just a little frightening and I really shouldn't have encouraged her read my about the caning given to me by Julia because before long I understood what the four poster was really for as I was first tied to it then flogged.
But there is only so much a man can take and I reasserted myself making it clear that it was now time for her to present that marvellous rear for some attention. I let her know that if she behaved herself perhaps an orgasm might just be permissible too Unfortunately for her she allowed herself to come much too soon so now she too would feel the sting of the flogger and the paddle. Yet this punishment only served to cause her to demand yet again that I, despite being the master, should actually submit to her perverted desires.
However I have been called a gentleman on occasion and it is rude to deny a lady her wish to have a little fun so I felt obliged to do as I was told. Being half choked by Miss James's strap-on cock as it was rammed down my throat may not have been uppermost in my mind earlier while I wandered the streets of my old stomping ground but here I was on my knees learning what a face fuck feels like. When told to present my arse ready for a serious pegging I knew that I would have to make her regret this outrageous behaviour before we finished.
The creator of Miss James had told me during our planning that she enjoys giving A play and she now set about demonstrating just how skilled she is at it (and here I must thank Julia who has been mentoring me for some time - had this been my first time I fear I would have been overwhelmed by the extended fucking I had to take).
Nevertheless being penetrated so expertly and deeply was a challenge to my self control and I knew that if something wasn't done I would find my self repeating Miss James's error. So I forced myself to call a halt and once more I asserted my dominance of this extraordinary woman by insisted that it was now her turn to kneel and see just how far down her throat she could take a cock - quite a long way as it turned out!
Finally it was time for me to fuck this gorgeous, infuriating and alluring creature - and so I did. After a few deep thrusts into that lovely cunt she in turn mounted me and the moment I had been waiting for so long had arrived. As Carla looked down at me first she removed her mask revealing just how pretty that face is and then removed mine too although this revealed a somewhat craggier visage, of course.
In my fantasy at this point I not only kiss the beautiful stranger but ejaculate as I do so. I at least managed to kiss those sweet lips however as for the latter I am man of advanced years who had just undertaken an afternoon of extraordinarily vigorous sexual activity - well that's my excuse. Fortunately another of Carla's many virtues is patience so with more than a little manual assistance from her matters eventually reached a highly satisfactory if messy conclusion.
Now out of character we chatted for a while and I moaned about how Soho wasn't the same since Jimmy's closed down like I do while Carla told me about where she spends some of her private time and other matters which are no one's business but ours.
Carla James is a very special person - you quickly realise that if you met her in any circumstances her warmth and humour would draw you to her and being in her company would help make the world feel like a better place. I don't know what the path was that led her to become the exquisitely skilled professional she is today but for the time we were together she committed herself totally to making our private, intimate drama become a performance that would have merited a standing ovation had there been an audience to witness it.
I am a fortunate man to be able to occasionally enjoy such pleasures and I thank Carla for making it possible and I even have a sufficiently large ego to believe her when she said that she too had found it to be a rather "hot" afternoon.
Carla James web site can be found here - she is also a rather good advert for the Kinky London Escorts group (KLE)
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......