Cruel to Be Kind

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Cruel to Be KindMy other life — the one I don’t talk about — started with a simple question.Brenda and I were sitting in a noisy pub, sipping our beers, listening to the music, waiting for our dates to come back from the men’s room.“Would you like to earn some easy money, Jane?”“Is it legal?”“Absolutely,” said Brenda with a smile. “A little unusual, maybe. Are you interested?”“I’ve no idea. What’s involved, and how much are we talking about?”“Okay, here’s the deal. There’s this old fart who gets off on wanking in front of women.”“In public?”Brenda shook her head. “No, no, all very private. We go to his house, we watch him jerk off, we come home. It’s as simple as that.”We saw our dates weaving their unsteady way across the pub floor. Before they got to our table Brenda told me how much I could make from this weird arrangement. Nothing earth-shattering, but considering the job content, definitely easy money. Brenda said she’d text me the details.She didn’t have to. Our dates got totally wasted and threw up in the gutter outside the pub. Brenda and I left in disgust and went down the road to an all-night café. Over a couple of coffees Brenda told me all I needed to know.The old guy’s name was Latimer and he lived alone. Judging by the photos on his mantelpiece, he was a widower with two grown-up sons. Years ago he’d made contact with a girl at our college. She’d introduced friends, and they’d introduced other friends. Brenda had visited his house a couple of times and insisted that he was perfectly harmless. Mr. Latimer’s little one-man shows took place every four weeks or so — depending on who was available and how much he could afford. One of the regular girls couldn’t make it that weekend, which is why Brenda had invited me. All I had to do was meet up with her and a girl called Trixie, and hop on a bus to Mr. Latimer’s house. It couldn’t be simpler.Mr. Latimer proved to be a charming old gentleman, nothing like the creepy guy I’d imagined. He welcomed us into his house and bustled around, bringing tea and biscuits from the kitchen. He sat down and chatted with us about the weather, about our studies, and about our interests. It was like visiting an elderly relative.He stood up, excused himself, and disappeared into a back room. I glanced at Brenda and raised an eyebrow. Brenda nodded.He came back wearing only a towel. He didn’t look at us and he didn’t say a word. He came to within a few feet of where we were sitting and turned his back on us, pulling away the towel as he did. It wasn’t a pretty sight. There were tufts of grey hair all down his back, and he was carrying a lot of extra weight. He spread the towel on the floor, bending over and giving us a good view of his bum and his balls. His left testicle was larger than his right.He stepped onto the towel and turned around. The first thing that caught my eye was his bulging belly. The second was the erection poking out from under it. He wasn’t big, maybe five inches or so, but he was surprisingly stiff. I’d read that older men had difficulty getting above horizontal. Mr. Latimer had no such problem. His perky little boner was standing to attention.“Oh, Mr. Latimer!” exclaimed Trixie, “what a splendid cock you have!”“And such beautiful balls,” echoed Brenda.There was something decidedly off about their comments. They sounded forced, as if they were reading from the script of a cheap porn movie. Maybe they were.“Very impressive, Mr. Latimer. Does it get any bigger?” That was me, saying what I hoped was the right thing. He looked at me and smiled. I breathed an inward sigh of relief. He turned sideways to give us a better view of his erection and began to work it with the fingers of his right hand. With his left he massaged his balls.Trixie and Brenda kept up their fatuous encouragement and I joined in. Still stroking his erection, Mr. Latimer took a step forward until he was standing right in front of Brenda, his cock no more than two or three feet from her face. I thought she would reach out and grasp it, but all she did was examine it with a show of great interest. He shifted his position and stood in front of Trixie, where the same thing happened.It was my turn. Neither Brenda nor Trixie had said a word while Mr. Latimer was standing in front of them. Maybe that was the right thing to do. I’ve no idea why I blurted out, “Why, Mr. Latimer, I can see your veins throbbing.”“Would you like to touch it, Jane?” he asked me. I glanced sideways at Brenda and picked up the slight movement of her head.“If you don’t mind, Mr. Latimer, could I just watch?”“Of course,” he said and stepped back onto the towel. It took longer than I expected for him to come, but maybe that’s because I’m used to younger men. Eventually — I wasn’t looking at my watch, but it must have been several minutes — he shifted his weight onto the balls of his feet, and a glob of semen gushed from the tip of his cock, followed by another and then another. The thick white fluid ran over his fingers and fell onto the towel. Brenda and Trixie began clapping. I didn’t feel like joining them, but I did anyway. What I’d witnessed struck me as rather sad.Mr. Latimer picked up the towel and said, “If you ladies would like a little refreshment, there are plenty of soft drinks and snacks in the fridge. Please help yourselves. I won’t be long.”No sooner had he gone than Brenda and Trixie began chatting about some girl in college. They were still gossipping when Mr. Latimer came back, fully dressed, with three white envelopes in his hand.“This is for you, Brenda,” he said, handing over one of the envelopes. “And this is for you, Trixie.” The third envelope was for me. I noticed that it had my name written on it. I mumbled my thanks.Trixie and Brenda declined Mr. Latimer’s invitation to stay a little longer. It was obvious that they were in a hurry to leave.As we were walking down the street to the bus stop, Brenda said to me, “There, wasn’t that easy? Money for nothing.” I nodded but I felt bad about what had happened.I opened the envelope as soon as I got home. Inside was a sheet of neatly folded letter paper containing a couple of crisp bank notes. I almost missed the short message written on the inside of the paper. It said, “Jane, please call me if you have time,” and was followed by a canlı kaçak iddaa telephone number. For a fraction of a second I thought that Mr. Latimer had given me the wrong envelope, but that couldn’t be right: the message was addressed to me.I spent the rest of that day wondering what it was all about. Several possibilities came to mind, but none of them made any sense. I decided to sleep on it.I called Mr. Latimer the next afternoon. He sounded touchingly grateful for my call but took a long time coming to the point. Could I please visit him again? There was something he wanted to discuss. I told him I’d have to check with Brenda and Trixie. He said that it was something personal, and he’d prefer that I come alone. That set off an alarm bell. He must have sensed my hesitation. He assured me that he only wanted to talk, and that he would understand if I said no. I surprised myself by saying yes.I told him that I could come over the next day, at around eleven in the morning, but that I could stay for only thirty minutes as I had a lecture right after lunch. I figured that half an hour wouldn’t be enough for him to get up to any mischief. My excuse wasn’t a lie; I did have a lecture in the afternoon, from two o’clock, but I wasn’t going to tell him that.He was just as friendly and polite as on my first visit, only this time he began reminiscing about his wife. I’ll skip the details — suffice it to say that it had been a very happy marriage and he missed Wendy very much. He kept coming back to how compatible they were, how they shared so many hobbies and interests. I got the feeling that this emphasis on compatibility was leading up to something, and I was right.Alex and Wendy had been, for want of a better expression, a cheerfu
lly kinky couple. Wendy was something of an exhibitionist and Alex was into spanking. They enjoyed role-playing, with Wendy often taking the part of a strict headmistress and Alex that of a naughty schoolboy. He would confess to a litany of imagined misdeeds and Wendy would take a cane or strap to his bare behind. I could see the twinkle in his eyes as he recounted this and other stories.It was almost mid-day. Alex noticed the time and apologised for keeping me so long. I told him that I’d enjoyed his little tales and would love to hear more — all of which was perfectly true.“Before you go, Jane, there’s something I’d like to show you. I’ll be right back.”I half expected him to come back wearing only a towel. Instead, he returned carrying a rattan cane, a wooden paddle, and a rubber whip.“Some of the little toys that Wendy liked to use on me. I keep them hidden away. Please don’t tell your friends about them.”“Of course, Mr. Latimer. And thank you for taking me into your confidence.”“Please, Jane, I’d appreciate it if you called me Alex. And the pleasure’s all mine. Being able to chat about Wendy like this brings back so many happy memories. It’s almost as if she’s still with us, here in this room.”I didn’t know how to respond to that, so I pointed to the cane and asked, “Isn’t it painful?”“It can be,” he answered, swishing it through the air and then running it across the palm of his left hand. “But that’s why it’s so much fun. At least for people like me who enjoy a little discipline. Here, try it.”He held out the cane and I stood up and took it. It was about three foot long, with a crook at one end. It was much lighter than I imagined. I swished it through the air several times and couldn’t stop myself grinning. “So, how many strokes would a strict headmistress give a very naughty boy?”“Oh, definitely six. More if he wasn’t suitably repentant.”I swished the cane several times, making what I hoped was an angry-looking face.“Ah, that sound is music to my ears, Jane.” He sighed deeply and said, “I won’t keep you any longer, but could I ask a very, very big favour before you go?”I was still pulling my angry face as I said, “Aha, Latimer, what have you got to say for yourself? Come on, out with it. Did you or did you not masturbate in front of three girls?”The expression on Alex’s face was priceless — surprise and delight all rolled into one. “I’m terribly sorry, miss. I promise not to do it again.”“You know the punishment for lewd behaviour, Latimer?”“Yes, miss. Six strokes of the cane.”“Correct. Bend over, you disgusting little boy.”My intention was to play out the little game by giving Alex a few light taps on his behind, but he was too quick for me. He unbuckled his belt, pushed down his trousers and underpants, and bent over.My subconscious took control. The cane whistled through the air and thwacked on Alex’s bare behind. Without waiting to check his reaction I gave him another stroke, and then another. Red weals appeared on his bum. At the end of the six strokes he straightened up.“How dare you!” I exclaimed. “Have you no shame?” With the tip of the cane I flicked his erection from side to side. “I’ll teach you to point that thing at me. Bend over!”At the fifth stroke of the cane he gasped. My immediate thought was that I’d gone too far. I was wrong, very wrong. Semen was dripping from the end of his cock and onto the floor.This time, as he straightened himself up, his eyes were closed and the expression on his face was one of pure rapture. Gingerly I put down the cane and waited for him to say something.He sighed and opened his eyes. And then he did something extraordinary. He got down on his knees and took my right hand, kissing the back of it after the fashion of an old-time gentleman.“Thank you, Jane. Thank you.” The next few seconds were very, very awkward. I helped him stand up and when he did, he just stood there with his pants and underpants around his ankles, one last drop of semen still dangling from the end of his cock. The drop slowly lengthened and fell to the floor, narrowly missing his shoe. I was disoriented, as if I were waking from a feverish dream. I mumbled something about wanting to use his loo and hurried out of the room. I didn’t need to pee. It was a feeble excuse, a way of giving him some privacy while he pulled up his pants and maybe used a few tissues to mop up the mess on the carpet.One week later I was back at his house, only this time I’d done my homework, browsing the web and checking out dozens of femdom videos. I reasoned that canlı kaçak iddaa if he wanted me to take control, asking him what I should be doing next would be totally lame. No sooner had he ushered me through the front door than I ordered him to strip naked. He eagerly obeyed. For the next two hours I told him what to do and where to do it, meting out creative punishments for any failure to comply. I addressed him as Slave, and insisted that he call me Mistress. By the end of our session his buttocks were a livid red, as were his knees. I took pity on him and ordered him to jerk off into the toilet while I watched. He loved every minute of it and although I pretended to be disgusted, I was secretly enjoying myself. Which is why I felt bad when he offered to pay me for two sessions. I knew that he was struggling to get by on a pension, and that three girls every few weeks was pushing his budget to the limit. We worked out a compromise. I told him that he could pay me once a month, or whenever his pension came in, and that our sessions would be off the clock. Yet again, he was touchingly grateful.With each session things got more and more interesting. In addition to punishments I began to offer little rewards. If he showed sufficient humility I would take off my shoes and socks and let him kiss my feet or suck my toes. That got him so excited that one day I stripped down to my bra and panties, just to see how he’d react. His eyes widened, his cock stiffened, and he began mumbling ‘Thank you, thank you’ over and over.Things took an unexpected turn at the end of our fourth session. He was kneeling naked on the floor, watching me get dressed.“May I speak, mistress?” he asked.“You may,” I answered as I sat down on a chair to pull on my socks. We were still in character.He told me that he was in contact with one of his wife’s oldest friends, a lady called Vera. This lady had a few kinks of her own, one of them being voyeurism. She’d been a regular visitor to the Latimer household, and loved to sit and watch Wendy and Alex play out their little games. Alex had told Vera about me. Would it be possible for her to come and watch one of our sessions? She would, of course, pay me for the privilege. Having an audience of one didn’t make much difference, so I agreed. Alex couldn’t hide his delight and told me that he’d phone Vera right away.She was already there when I turned up for the fifth session. She was younger than I expected. Like Alex, she was polite and well-spoken. I took an instant liking to her and any doubts I had about letting her watch quickly evaporated.The three of us were sitting in the living room, drinking tea. Vera was telling me about Wendy — how they’d met and how they’d become such good friends. I glanced at Alex and said, “Who gave you permission to eavesdrop on our conversation?”“No one, mistress. I’m sorry, mistress.”“Stand up and drop your trousers!”“Yes, mistress.”“And your underpants.”“Yes, mistress.”“Pathetic, simply pathetic,” I said, pointing to his shrunken penis. “Get those filthy pants out of my sight and bring me my cane and whip.”He picked up the heap of clothes and, dressed only in his shirt and socks, hurried out of the room. I looked at Vera. Her expression hadn’t changed but something in her eyes told me she was enjoying herself.Alex came back and I made him bend over, giving him several lashes of the whip. I ordered him to take off his shirt and made disparaging remarks about his cock. Throughout all this Vera
sat quietly in her armchair.When Alex and I took our games into the kitchen, Vera followed us and watched from a distance, saying nothing.One hour later I was down to my bra and panties, and my feet and toes were very clean. Alex begged my permission to take a leak. I accused him of trying to sneak off for a quick wank. He protested that he really did need to pee. I ordered him to prove it by bringing a glass bowl from the kitchen and pissing into that. He held the bowl with his left hand and his cock with his right. Most of the pee splashed into the bowl but some missed. I scolded him for being a filthy old man and asked Vera to hand me the cane. As she got up from her armchair she said, “Yes, mistress.”Well, well! Could it be that Vera was more into this than she’d let on? There was only one way to find out.“Stand beside him and count the strokes,” I ordered.“Yes, mistress.”I stopped at four and told Alex to remain bent over. “Slave,” I said, looking at Vera, “are you willing to do my bidding?”“Yes, mistress.”“Then take this cane and deliver another four strokes, and do not spare the rod.”“Yes, mistress. Thank you, mistress.”Without any hesitation she brought the cane down on Alex’s buttocks. I was tempted to see how far I could go with her, but now was perhaps not the best time. I ordered her to kneel in front of Alex and hold up the glass bowl half-filled with piss. I gave Alex permission to jerk off into it, and stood back to watch. When he came, his semen plopped into the bowl and separated into long white filaments.I praised Vera for her fine work and dismissed Alex, ordering him to flush his revolting mess down the toilet. Vera remained standing, waiting expectantly for me to say something. “You may sit down, slave,” I said.“Thank you, mistress.”With Alex out of the room, there was no reason for Vera to keep up the pretence. She could have reverted to her normal self and we could have picked up our conversation about Wendy while I got dressed. The fact that she hadn’t meant she was very much into role playing. I wasn’t in the least surprised when she begged me to let her to come again.Having two willing slaves to boss around meant twice the fun and twice the income. It also brought a slight complication. Calling both of them ‘slave’ was confusing, so I named Alex ‘Adam’ and Vera ‘Eve’. A little odd, but it served its purpose.Vera was a far more complex character than Alex. I couldn’t quite place her on the S & M spectrum. She assisted in punishing and humiliating Alex with great enthusiasm, but she was also into submission. I was wary of ordering her to strip naked in front of him, so I began by making her remove various items of clothing, one at a time. She obeyed immediately and revealed a full, attractive figure.The next step was a tricky canlı bahis şirketleri one. I scolded her for being too slow in carrying out an order, and asked her, “Do you know the punishment for disobedience, Eve?”“Yes, mistress. A spanking, mistress.”“Correct. Adam, go and stand facing that wall, and do not turn around. Eve, remove your panties and bend over that chair.” Both of them hurried to do my bidding. I held back on the first stroke of the cane. Vera didn’t cry out or flinch, so I put a little more effort into the second stroke. By the fourth I was hitting her as hard as I hit Alex. When I’d finished she stood up and said, “Thank you, mistress.” I ordered Alex to turn around and go fetch the panties Vera had tossed onto the sofa. He did as he was told, not giving Vera a second glance, even though she was standing in the middle of the room wearing only her bra.“Kneel on the floor, Adam, and help Eve put on her panties.”The panties didn’t stay on for long. Fifteen minutes later both Vera and Alex were crawling naked around the carpet. I chased them into the kitchen with my whip.“Stand up, Eve, and choose three utensils from the drawer over there.”“Yes, mistress.”She choose a spatula, a ladle, and a whisk. I nodded to show my approval and ordered her to fetch some butter from the fridge. I could tell by the twinkle in her eyes that she knew what I had in mind.“Eve, you will grease the handle of the whisk and then you will teach Adam a lesson he will never forget. Do you understand?”“Yes, mistress. Perfectly, mistress.”She squatted down beside Adam, making no attempt to hide her exposed and rather hairy crotch. With one hand she spread the cheeks of Adam’s bum, with the other she spread butter on his anus.“Are you ready for your punishment, Adam?”“Yes, mistress. Thank you, mistress.”Vera slowly inserted the handle of the whisk. Alex must have done this before. He offered no resistance and it slipped easily into his rectum. I ordered Vera to stand up.“Adam, you will crawl around the kitchen until I tell you to stop. If you dare drop the whisk I will flay you alive. You may begin.”I struggled to keep from laughing. With a stainless steel whisk sticking out of his butt, Alex crawled very slowly and very carefully around the kitchen. After one lap I ordered Vera to pull the whisk out and insert the spatula. When the handle was all the way in, she twisted it so that the blade was facing upwards. As Alex set off for another circuit of the kitchen it looked as if he was ready to flip pancakes with his butt.The ladle looked a little heavy so I decided to spare Alex the indignity. He was still on all fours and Vera was standing next to him, both of them waiting for instructions.“I believe it’s time to clean up the mess. Adam, pick up the utensils and wash them in the sink.”As he hurried to do my bidding, Vera said, “Mistress, may I have your permission to break wind?”Now that was something I never expected. Not from Vera, at least.“You may indeed. Adam, put aside those utensils and kneel down. You will kiss Eve’s buttocks while she farts.”“Yes, mistress.”I immediately regretted giving the order. Fortunately neither Alex nor Vera seemed disconcerted. They obeyed promptly and with enthusiasm. Vera released two long and very audible farts. I held my breath as long as I could. “Excellent,” I said. “I am very pleased with both of you. Eve, you may go into the living room and pleasure yourself on the sofa while Adam kneels in front of you and watches. And if he behaves himself I’ll allow him to masturbate while you watch.”“Thank you, mistress, thank you,” they said in unison.If you’ve read my story thus far, you can probably guess what happened next. After one of our sessions Vera told me that she’d like to introduce another client. His name was Philip and he was married to the daughter of one of Vera’s friends. Philip was into submission and discipline, his wife wasn’t. He had to find other ways of satisfying his needs. Would I consider taking him on?I asked for more information and it became clear that Philip wasn’t interested in a threesome with Alex and Vera. He wanted a private session in a hotel room. That sounded risky to me — being alone with a stranger. Vera assured me that she could vouch for Philip; there was nothing to worry about. But if it would help, she could arrange for Philip to come to Alex’s house for a short meeting.A week later Vera introduced me to a tall and very handsome young man. She and Alex excused themselves and went off to the kitchen, closing the door behind them. I asked Philip about his background, his family, his work, and his sexual preferences. I also asked him about the hotel arrangements. He was very open about it. He’d hired escorts before and used one of two hotels. He’d check in and text the ladies from his room. The hotel staff turned a blind eye to smartly-dressed women crossing the lobby and taking the elevators to the higher floors. That left only one other thing to discuss: the financial side of the arrangement. Philip was clearly far better off than either Alex or Vera, and I’d been wondering how much I should ask for. Philip saved me the bother by telling me how much he paid his escorts. I had to suppress a gasp.Struggling to maintain my co
mposure, I said, “I believe that will be acceptable, but could you give me a few days to think about it?”“Of course. And if you have any other questions, please text or call me on my personal cellphone. I’d prefer that my wife didn’t know about this.”He got up from his armchair and extended his right hand. I remained seated and ignored the hand. “Philip, would you please turn around slowly? I’d like to have a good look at you.”I have absolutely no idea what made me say that. Some kind of filter in my mind must have shut down.“Certainly,” he said and did as I’d asked.“Thank you. Now remove your clothes.”He glanced at the door leading to the kitchen and took off his jacket, hanging it on the back of a chair. The rest of his clothes followed until he was standing naked in front of me. He turned around a couple of times without waiting to be told. I could feel my heart thumping. Philip was one very, very well-endowed gentleman. I was already imagining all the fun things I could do with his pendulous penis.Philip is still one of my regulars, but now I’m busy three or four nights a week, and I no longer have any worries about repaying my student loans. I haven’t forgotten about Alex and Vera. I still see them whenever I can, and the three of us are the best of friends.

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