Always Turns Up Ch. 02

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Reminiscing about an adventurous past with an old lover.
9.9k words
4.45
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Part 2 of the 7 part series

Updated 06/10/2023
Created 05/15/2020
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This is the second part of the sequel to my series "Bad Penny" which I published here a few years ago. That was a semi autobiographical story (enhanced of course for fun, names changed to protect the guilty).

A related series "If I knew then" is also referenced in this story. It is a fantasy based on what could have been in a perfect world. A third series, "Life Sentence" also gets a mention - it is an horrific nightmare inspired fantasy, in which Penny is featured.

I hope this story is readable and enjoyable as a stand alone, but obviously, if you read the first chapter in this new series and all the others first, it will make more sense. This series, as a sequel to Bad Penny, is of course also semi autobiographical. And all names are fictitious. But a great deal of it is based on the ugly truth...

"Well, if we are going to spend the afternoon in reminiscing, we need somewhere more comfortable, and private, I think. Would you like to go upstairs?"

Penny gave me a most flirtatious Look, one eyebrow slightly raised, a half smile making her lips look full and kissable. A look I new well from long ago.

I hesitated. Since we were in the foyer of the Ritz Hotel in London, and in hotels the upstairs is where they keep the rooms... she laughed. "Oh Sean, it is a good job you never played poker. They have a wonderful roof garden with a bar here, with much comfier seats than these. Come on, the lift is over there."

She walked a little in front of me, so I took the opportunity to admire the view. When we had first met over thirty years before she was a slightly rounded teenager. "Puppy fat" some would call it. But time we parted she was a skinny hardbody, toned by hours in the gym, which I had actually found a little too masculine for my taste. Now she was slim, but curvaceous, womanly, and elegant. She was wearing small heels, and there was a seam up the back of her black tights. Or stockings. In the past she always wore stockings, because she knew I liked them. It made me wonder.

I looked up as we passed the table of young women that were taking afternoon tea and chatting near the lift. I had noticed them before, of course, but this was the first time I had been close to them. Four beautiful girls, I would guess in the early twenties at most, all well dressed, relaxed, simply naturally amazingly attractive. One smiled at me, and gave a tiny nod, as if in recognition or acceptance of my admiration. I smiled back quickly, and switched my gaze to the beautiful woman I was accompanying.

The lift attendant held the door open, and bowed to Penny as she entered it. Really. A proper bow. Then he gestured for me to enter, saying "Signori," with a little nod. Penny told him "The Roof, please, Carlo."

He made a little bow and said "Si, Contessa."

Penny spoke to him then in Italian, chiding him, amused, but serious, and Carlo spoke respectfully, perhaps a little sadness in his tone. I could not follow it exactly, but I got the gist, so as we walked across the roof garden, towards the corner where Penny said there was a suitable place to talk, we walked side by side, and I said "I understood most of that but there was a word I missed. 'Frisi.' You said it a couple of times"

Penny laughed again, and said "When did you learn Italian?"

"I have been able to travel a bit myself. I picked up a little, and what you were saying wasn't that complicated."

"Well, here we are. My favourite table. It isn't bugged, by the way. I had it checked."

I raised an eyebrow myself at that, but of course I had heard the stories in the papers about the owners of the hotel bugging their own meetings as the family was in dispute about the business. We sat, each in a comfortable armchair, and ordered drinks from the attentive waiter, before she answered me.

"I met Carlo a long time ago. When we stayed in a London we always stayed here. So he knew me as the Contessa. Did I mention Angelo was old Aristocracy? The Italian government does not really recognise the titles, but, many still do. Carlo is old fashioned. But as you heard me tell him, for the hundredth time, I am not Contessa anymore, just Dama. Frisi was once a village, then a hamlet, and by the 1950s, abandoned entirely. The young went to work in the cities, the old died. But it all belonged to Angelo's family, one of their minor estates. So when we divorced he let me keep the title, Dama Frisi. It wasn't a courtesy. It allowed him to refer to me without using my name, and it allows him if he ever has to talk about his children's mother, to pretend she was proper Italian nobility, not just a foreign commoner. And it is also a subtle insult. You know how the English make Irish jokes, and the Irish make jokes about people from County Kerry, and in Kerry they joke about the people from the islands off the coast? Frisi was a byword for idiot peasants, the butt of the local jokes. And the women of Frisi were said to be not only idiots, but of easy virtue. So he made me Lady Stupid Whore." She shrugged.

"Ah. Charming. He was a bit petty then?"

"Oh he took it further than that. Pride would not let him let his children's mother starve, so he arranged that I should be paid a royalty for the use of the title as a domain label for the low grade fizzy white wine he produces. Mostly for the English market, the name is famous for being cheap and associated with drunken teenage girls from backstreets and sink estates who are of a promiscuous nature. So even here the name is tainted. A Frisi girl in Essex is more 'drunken slut' than 'stupid whore' but not really much better, is it. Mind you it proved very successful, so these days the royalties are larger than he intended, and the title does still open doors. So in London, in public, I am mostly known as Lady Frisi. Americans like it too. And the income is welcome. For a while I didn't have anything else. But that is all getting a bit ahead of things, I suppose I should really tell you more about the years before I was married.

"Well, my Lady, if I am to be your Watson, you had better tell me more stories."

"Hmmn. Now that it comes to doing it , you know I am not that good a story teller. How about I give you the scenarios, as vignettes, and you can expand them into real stories?"

"You don't have to tell me at all, you know. Or at least, not just launch into a raunchy tale. I would love to just hear more of your adventures without needing the detailed sex parts."

Penny smiled, and said "Oh darling, all my adventures are about sex. Well, very nearly. How about I tell you one story, for now, and then you can tell me more about your life. Deal? Okay. Hmmn. Where to begin? I suppose I had better start where you left off. The airport, Belfast, leaving you in the lurch. Sorry about that. I wasn't... in my right mind. Tilly was... addictive. Very clever, very insidious. Yes I shall tell you about my life with Tilly.

She had me in her thrall. Literally, I had sworn to be her slave, and she had me rock solid convinced that she was the be all an end all of my existence. So I got on the plane. I didn't even have hand-luggage. In London we got a cab to a hotel, not this one, and she kept me there for a few days. Naked of course, except for collar and cuffs, chains or ropes. She brought a couple of London friends around to meet me. Some I simply served, silently, standing by to top up their glasses while they chatted and ignored me. Others, well, how much detail do, you want? Tilly enjoyed sharing me. Mostly it was just three or four in a bed, the usual fun. Sometimes she had me perform in the middle of the room with all the other guests in turn. Or made me play with toys, as a show for her guests, who might, or might not , then use a toy on me, or get me to pleasure them. Which if I am honest, really appealed to my exhibitionist side.

After about a week she threw a party in large house in Kensington belonging to a friend, at which the guests all wore formal clothes and there was no sex allowed in public - apart from one young man who was brought by one of the other guests to perform with me all evening. We did requests; if guests wanted to see us pose, or fuck in a different position, or orifice they only had to say. He was quite insatiable, I think he had taken some drugs. He didn't orgasm the entire time, but he made me come until I was exhausted. Tilly allowed us a break every hour or so, to have a very fast shower if we needed it and something to eat and drink. We had costume changes each break as well. It was frankly quite exciting, and I was really enjoying the whole experience, as it was so anonymous and public. I could feel the desire and admiration of the crowd, and knew my submission was judged worthy, but after four or five hours of it I begged her to let me stop. No amount of extra lubrication was helping the bruised flesh that was being constantly pounded, and I was just dropping from fatigue. That was the first time she really punished me.

I had let her down, so she rounded off the evening's entertainment by tying me up in Japanese style, demonstrating the Kinbaku technique for her guests, and then she bent me over a chair and whipped my bottom with a cane. Then I was left on the balcony, naked for the rest of the night. In September. It wasn't freezing, but in the morning I was so cold and stiff that they had to carry me to the bath to warm me up, and I could barely walk for days. To give her a little credit I think Tilly was a little sorry for me. Although more sorry for herself, as my need to recover slowed down her ability to party. But after a week more, during which my bottom was thankfully spared, an older man came to see her and she had me make him tea, then stand by his chair, as he talked finances with her.

I thought he was a lawyer, or something, but he had some unprofessional habits. He kept running his hand up and down my leg at intervals, gripping my calves, or my thighs, or sliding up the inside, and brushing his finger over my slit. Then just dropping his hand again and carrying on with the business talk. Tilly didn't take any notice. When they had finished their conversation she said "I am going out for the evening. Would you like my slave to entertain you for while?"

So I was instructed to do whatever he wanted. "He is your Master for the evening" and she took her bag and left. It was the first time she had left me alone with a new Master. He was also the first Master I ever had who was not just a friend playing the role. No man before had ever looked at me like that. No man had ever really thought of me just as a nameless slave. For the first time I was really truly powerless, truly under his control. I was terrified.

Fortunately he was not cruel. Not very cruel anyway. He had me kneel, move my knees apart, put my hands behind my back, lean my head back, open my mouth, close my eyes, stick out my tongue, and then... Just waited a while. I had expected that he would make me lick or suck something, but he just waited. The position became uncomfortable, my mouth dried out, and I began to shake. He told me close my mouth, and go down on all fours. I was happy to do so. He had me move my knees further apart, and drop my head, stick my bottom up further. All with my eyes closed. But I could hear him walk around me, and knew he was in position to get a full view of my bottom, my asshole and shaven pussy. Tilly shaved me frequently, or had me do it, or let one of her friends do it. There was a slightly submissive young man called Charles who had taken to coming over each morning and shaving me in the last week. He never did anything else. He might just run a finger along my slit after it was finished, and of course he touched my lips and sometimes held them when he was shaving me, but that was all. I was happy enough to allow it, since he seemed to enjoy it so much. Anyway, there I was with my bottom in the air, my privates on display, and the probable gaze of a silent man to make me wonder what would happen next. He made me hold that position for some minutes. Then he told me to open my eyes, and to follow him, crawling on my hands and knees of course.

We went to the bedroom in the suite, and he got me to crawl up on to the bed, and turn around to face him. He simply undid his fly, and put his cock in my mouth, so of course I did whatever I could to please him. He liked the fact that I could take his whole length in, and he could just fuck my throat. Practice with Mike had helped there."

Penny laughed. "When I think of it now, how innocent we were, you and I when we played those games with Mike and Tara. How innocent I still was when that man took me in that hotel room. At first I thought that he didn't understand that I enjoyed it. This strange man fucking my face, grunting as he crushed my nose against his stomach. Even though I could not breathe and half gagged, and began to struggle simply because my body could not do anything else, it wasn't a mental effort. I had reached a submissive nirvana. I had no guilt, no desire, it was all just physical pleasure, even when it was uncomfortable. Even when it became painful. But I began to think he might just keep going until I died. Maybe even longer. And despite my need to please him, I still had a little tiny bit of self preservation in me. I feared him. I would do anything he wanted.

So he throat fucked me until I nearly passed out. I am sure I had gone purple, and was left just gasping for air, collapsed on the bed, and I just didn't follow what was happening for a few minutes probably, until I felt him pulling my legs open, and climbing onto my back. I was face down on the bed then, and felt his naked chest rub on my back as he probed between my legs with his cock. It was neither very long, nor thick, but he was hard, and simply thrust deeply into me as soon as he felt the tip against my lips. I think he liked the way I gasped. At least he laughed, and then did it again, and again, and again. After maybe a dozen thrusts he held it in me, as deep as he could, and said in my ear, "Open wider, slave."

I did, opening my legs as wide as I could, so he could thrust more deeply. But it wasn't enough. A few more hard thrusts later he pulled out and said "Up on your knees, slave" and took me again, pulling me back on his shaft as he hammered forward. I knew he could get no deeper. I could feel his balls slap against me. And then he put his hands around my throat.

People call it "breath play." I didn't know that he was playing. There were no safe words, no consent. I had no idea what was going on. As I started to black out again he released me, and I gasped in air, and shuddered, and he laughed again, and then squeezed my neck again. I was so overwhelmed when he released me the second time that I collapsed, and hardly felt him rolling me over to then enter me again on my back. I imagine I was like a rag doll in his hands, easily splayed open for him to take as he wanted, unable to resist. The third time he did it physiology took over. I had a rush. The brain reacts to asphyxiation by flooding with dopamine, and it is a bit like an orgasm. My whole body shook, and that was what he wanted, to fuck me while I was shaking. That is what finally got him to come. I was just aware enough to know he was coming in me, and that he kept fucking me as he came, and afterwards, until he came a second time. Then he just collapsed on me, all his weight, and I couldn't breathe again, and I couldn't move. I was so confused. I had nearly died, then had a sensation so intense that it was beyond any orgasm, and then my Master had come, so I must have been good for him, and I was full of a strange triumph. And about to die, but not unhappy about that. I truly thought if I died with him lying there on me, in me, it would have been worth it. Tilly would be proud of me."

Penny looked up at me, and said, "Oh. Oh, Sean, I didn't mean to upset you. I'm sorry. Perhaps this was a bad idea."

I shook my head, not knowing what to say, and tried to smile. "My dear Penny. When I wrote 'Life Sentence' I was writing my fears, not my desires. I truly hoped nothing as bad would have ever happened to you."

Penny smiled again, and said "I know. But nothing that bad did happen to me, don't worry. Even that encounter was not as awful as the things you described. I was just tying to explain how truly screwed up in the head I had become. But be assured, it was the start of a turning point. Because despite the weird orgasm, later on my head cleared, and I began to question things, for the first time in months. Frankly I was probably not in very much danger that afternoon. He had a lot of experience at half strangling women, and as far as I know never killed anyone. The man wasn't a lawyer, he was Tilly's uncle. But it has to be agreed he was not a pleasant man. But to return to events as they happened...

Tilly arrived back the next afternoon. Her uncle had left me tied up on the bed, after fucking me again in the morning, while flogging me with a curtain tie back. It was a soft rope thing, the cords only a centimetre or so thick, so it did t have much weight and didn't cut me, but he applied some force, so my bottom was quite a pink picture to greet her as she walked into the bedroom. She had been calling me, and was most annoyed that I had not been kneeling by the door to greet her, but when she saw me she laughed. She came and lay beside me and stroked my hair and my back, and asked me what her uncle had done. She wanted details, of course, how deep, how long it went on for, if he came, if I did. While I was telling her about how he took me from behind she slipped her hand around my bottom, and began fingering me, rubbing me, penetrating me, trying to make me come again as I described what he did. I tried to describe the orgasm I had when he choked me, and she was intrigued, and stopped before I came. Then when I had described it in detail she told me that we would be going to stay at her parents' house the next day, and that her uncle might be there, and that I was not to mention my encounter with him. And said that as I had obviously had such a good time with him I didn't deserve another orgasm until I had licked her pussy to make her come. So that was how I spent the evening.

The trip to the country took several hours, and I was frankly impressed when we arrived. The house was enormous, the parkland around it was incredible. Tilly's mother was apparently unwell. Chronically. I met her for a few moments, as she was sitting in a chair on the lawn, taking tea, in the shade of large tree, about a week after we arrived, but that was all. Her father though... well he had been introduced to me the first evening. That is to say, after dinner with Tilly in a sort of family room which she called 'the old nursery.' She had me strip and don my collar and cuffs, and lead me on a dog leash down the hall, to her father's study.

My hair had grown back a little, on my head, a few millimetres, as she had not shaved it since we left Belfast. But she had shaved me everywhere else before dinner in her bathroom beside her room. So outside the door she said "Daddy likes hairless pussies. I want you go and sit on his desk and show him yours. He may play with you if he has the time, but he probably won't fuck you. If he does, he will want you on your back, and for you to let your tits bounce back and forward as he does it. Simple tastes. From now on, anytime he wants you, you know what to do."

She knocked, and entered when her father said to do so. She lead me in, and went over to him, and kissed him on both cheeks as he sat behind the desk. They chatted as if I wasn't there for a few minutes, although I had seen him look at me, and raise his eyebrows, and smile, when I came I to the room. And then Tilly said "Daddy, this is Slave. She has something you might like to see." She pointed at the desk, and I did as I was told, hopping up on to it and spreading my legs without any further instruction. Her father laughed. "Well, I was just about finished with the books, so... I shall send her back later. Thank you my dear." He rose and kissed Tilly again on both cheeks, and she left us alone.