69 SHADES OF RED: Femdom Stories of Spankings and Other Sexual Punishments - Bend Over! You Know You Deserve It! Volume 2 of the WellHeeledDominatrix.com Collection

by Nika Bella Dea

  That really got me thinking. That was the kind of relationship I wanted; not the sham that I currently had.

  “Come around to my place tomorrow,” Michaela said. “Cliff has a friend who would love the kind of relationship we have. He just might suit you. You never know until you try, do you?”

  I spent that evening looking forward to the following day. I think I had finally acknowledged that there must be more to life than what I currently had. So, when I got dressed to go to Michaela’s, I had butterflies of excitement fluttering around in my stomach. When I got there, Cliff had prepared lunch for us and we had a lovely time all talking, and getting to know each other. Cliff seemed like a really nice guy, and kept giving Michaela loving glances. His friend Simon seemed cool, too.

  After lunch, we all had a brandy, and relaxed. I noticed how Cliff looked after everything Michaela needed and he was very attentive and loving toward her. I want that kind of relationship, I thought to myself. Almost reading my mind, Michaela said, “You want this, don’t you?” I nodded, unsure what to say.

  Simon looked at me, and said, “You can have it all, Jenna. You just have to want it.”

  “I do want it,” I whispered. “Tell me what to do.”

  Simon laughed, “Actually, you can tell me what to do!”

  And, then the realization hit me. I could do this if I wanted to!

  “Okay, um, get on your knees,” I said hesitantly.

  He did so immediately, looking up into my eyes. “I am here to give you everything you have ever wanted,” he said. “And, if I don’t do things correctly, then you must punish me until I get it right.”

  I looked at Michaela, who could see I was still hesitant. “Follow me,” she whispered, standing up, and lifting up her short skirt to show she had no underwear on. “Cliff, lick my cunt,” she commanded. He began slurping and licking her while I watched, fascinated. “Enough,” she said. “You haven’t earned the right today to make me cum. Besides, you were two minutes late bringing me my coffee this morning. So, what are we going to do with you?”

  “Punish me,” Cliff said. “I have not served you today as I should.”

  “You know what to do,” Michaela said. Cliff removed his clothes, and got on his knees. She left the room, and returned with a small paddle and cat-o-nine-tails, whacking him across the butt with the paddle.

  “More,” he moaned. “I’ve been a bad boy today. I deserve this.”

  “See? He wants this,” Michaela said to me. So, I followed her lead. I was surprised at how easy it was to turn the tables, but the difference was that these men wanted this to happen. It was also easy to see how excited they were, judging by the size of their erections.

  “Use this,” Michaela said, handing me a cat-o-nine-tails.

  I brought it down on Simon’s upturned butt cheeks and he moaned. “That’s so good,” he gasped. “Show me how to please you, Mistress.” I carried on whipping until his butt was bright red and I was shocked by how excited I got doing it.

  “I think that’s enough for now,” Michaela said. “He should not be allowed to cum until after he has done something for you. Just tell him and he will do it.”

  The next two hours were spent having the horniest experience of my life. I quickly discovered how far to push Simon towards orgasm, without allowing it. He fucked me when I told him to, he ate my pussy, and I finally allowed him to cum as well.

  “Please continue your training of me as soon as possible,” he gasped as jism shot out of his erection, covering his chest and face. I had wanted to see if he could get it into his own mouth.

  “Hmm, we’ll try that again soon,” I smiled. “But, for now, well done, Simon. I think we have the makings of a good partnership.”

  My soul might have been lost for a while but now I had definitely found myself.

  The Apprentices Go Head to Head

  by Estelle

  “Good morning, Craig and Daniel,” I smiled. Craig and Daniel were recently brought in as interns at my real estate office on the Florida coast. My name is Estelle and I am the CEO of a very successful agency. I have a staff of 30, and recently realized I needed more if we are to cope with the influx of buyer inquiries we are getting on a daily basis.

  Daniel and Craig are both 19 and I have employed them both on a trial basis. Their credentials are equally good so I decided it was only fair that they should both be given a trial run to see which one would end up being most suitable for the job. Okay, to be completely honest, the reason I couldn’t make up my mind is that they are both as sexy as hell.

  I need to see how they live up to every one of my requirements before I make my final decision. By the way, did I mention that I am also heavily into discipline? I set them about doing usual office duties for most of the day and there is already a certain rivalry springing up between them as they have been told that only one of them will be taken on at the end of the month. I can already see them trying to outdo each other in speed and efficiency and, as far as I can tell at the moment, Daniel is edging into the lead. But, wait, already Craig is on his way to bring me a coffee, having finished his task early.

  “Thank you Craig,” I smile, taking an appreciative sip. “Mmm, just the way I like it.”

  “I took the trouble to ask one of the other staff,” he smiled. “I wanted to get it right for you.”

  “Duly noted,” I murmured. “Carry on then but I want to see you before you leave this evening, okay? And, tell Daniel the same thing, would you please?” He nodded and I was pleased to see his head dip in a deferential manner. Hmm, the boy has potential, I thought.

  Five o’clock quickly came around and, as the rest of the staff filed out the doors, I was pleased to see Daniel and Craig holding behind. I walked to the windows, drew the blinds, and then locked the door when my office manager left.

  “Okay, boys, come closer.” They stood in front of my desk. “And, now your training begins,” I smiled. “Do you understand me?”

  “Yes, Estelle,” Daniel smiled. “We are both working hard and doing our best to impress you.”

  I smiled, and said, “I don’t think you understand yet how you have to impress me. Now, both of you step out of your pants."

  I could see them exchange a look of shock and Craig stuttered, “Wh-what do you mean?”

  “I think it’s fairly clear what I mean,” I reiterated. “I want to see the size of your cocks. Strip, NOW!”

  They looked at each other again and, out of the two of them, I think that Craig was probably the least frightened.

  “Oh, don’t look so much like rabbits caught in the headlights,” I laughed. “I assumed I was hiring men of the world, and not boys. Hasn't a woman ever seen your naked cock before?”

  Craig was the first to take the challenge, and pulled down the zipper on his suit pants. He had stepped out of them by the time Daniel was still fiddling with his own.

  “Do you want this job or not?” I said harshly.

  “Um, yes, of course,” he whispered.

  “Then you will both do everything I say. Okay, and now your boxers, please." They complied.

  "Now, I want you both to jerk off until you are erect. I need to see what I’m going to be sucking on!”

  They looked at each other with what could only be described as shamed acceptance of the situation. I have to say I was nicely surprised by the size of Daniel’s cock. He must have been a good nine inches when hard, and he was thick as well. Craig wasn’t as thick but he made up for it in length.

  “Hmm,” I sat back with my feet propped up on my desk, letting my skirt slip upwards so they could see I had no panties on. “Okay, so which of you gives the best cunnilingus? I will be awarding marks out of ten for technique so I hope you are both up to speed.”

  “But, I’ve never done that before,” Daniel said, his head pointing toward the floor.

  “Well, it’s about time you learned,” I barked. “On your knees, now.” I made him kneel between my legs, and used one hand to spread
my pussy, and the other to pull his face close to it.

  “See this?” I said, fingering my clit. “I want you to lick all around this, and then suck it into your mouth. And, then I want you to finger-fuck me here,” I said, holding open the entrance to my cunt. “Then, it will be your turn, Craig. You may watch and jerk off but I am warning you now, if you cum, that will be that. End of the trial. Do you understand me? You will not cum until I say that you may.”

  I could see from the struggle going on in his eyes that part of him was dying to jerk off as he watched my pussy being eaten...yet the other part of him wanted to win the challenge.

  Which side of him will conquer? I thought to myself and then I allowed my eyes to look down to where Daniel’s tongue was manfully working his way around my clit. I’m so looking forward to this month, I thought, closing my eyes as I felt my pussy becoming wet.

  Who knows? I just might end up employing them both!

  Charlie Gets the Rent Sorted Out

  by Naomi

  Charlotte ‘Charlie’ Cunningham changed after her divorce from her husband, Frank. She is 43 and was, until recently, "respectable". She dressed appropriately for her age, and did ‘safe’ things, like knitting and playing golf. However, a lot changed when Frank left her for a woman in her 20s.

  Charlie thought, if you can’t beat them, join them, and started dressing like a woman half of her age. She literally blew most of her divorce settlement on her self. In fact, whatever she could fake, Charlie did. Hair, boobs, nails, eyelashes, the works.

  She also started buying her clothes from younger stores, and abandoned all her ‘safe’ friends. She developed a taste for drinking and partying with her new friends, and could often be seen with a boy toy or two hanging from her arm when she left the latest nightclub. The problem was her new lifestyle swiftly drained her resources so she had been forced to divide the luxury home she had won in the settlement into four apartments. She kept the whole of the downstairs to herself, and created two apartments on each of the remaining two floors. So, Charlie now had four men living under her roof, the idea being that their rent money should more than cover her expenses...but that didn’t always work out.

  Charlie was too lenient with two of the guys and, if they didn’t have the rent money, she would let them get away with it, until her one remaining friend from the old days put her straight. “Charlie, you can’t carry on like this,” Marie said. “You will be broke in no time at all. You have to get them to pay up somehow.”

  Marie was the same age as Charlie, and also divorced, but she was a lot tougher mentally, and didn't accept any nonsense. Marie always got what Marie wanted so she urged Charlie to take a page out of her book.

  “Make them work it off in some way,” she said. “Even if it’s cleaning your apartment, or doing your laundry, tell them that nothing comes for nothing in this world.”

  When Charlie got the latest bank statement, she realized that Marie was right and that she had to take action. When the next month’s rent money was due, she knocked on Derek’s door on the top floor. Derek was a mild-mannered guy in his forties who had never been married, and had always lived with his mother until she went into residential care. He had come to Charlie’s when his mother’s house had to be sold to pay for her care. He was a bank worker, and as quiet as a mouse.

  “Rent money, please, Derek,” Charlie smiled when he opened the door. If ever a guy coined the term nerd, it was Derek, Charlie thought. He was bespectacled, and wore a sleeveless jersey over his work shirt and sensible pants.

  He looked at the floor. “Um, I’m afraid I don’t have it again, Charlie. Mom’s money from the house hasn’t come through yet and I’m a bit short. Will next month be okay?” he asked hopefully.

  “Actually, Derek, no it won’t,” she replied. “Can I come in for a moment, please?”

  Derek held the door open uncertainly for her. “Oh, of course,” he stuttered.

  Charlie looked around, pleased to see that he was keeping the apartment nice. “I’m glad to see that you are keeping everything clean, Derek,” she said. “In fact, if you like cleaning that much, you can come down and do mine as part payment for your rent.”

  Derek looked surprised, but sputtered, “Well, um, yes, of course, Charlie. Whatever you say. Do you want me to come now?”

  “Ten minutes,” she replied. “And, bring your own cleaning stuff with you.” She stalked back downstairs, and waited for him to arrive.

  The hesitant knock at the door told her who it was and, sure enough, he was standing there with cleaning gloves on and a bucket containing sponges, detergents and other ‘useful’ stuff.

  Charlie held the door open, and didn’t say a word, apart from, “Get on with it.”

  As he started cleaning, she realized how powerful she was feeling. I could get used to telling him what to do, she thought, as he bustled around wiping surfaces down. A thought came into her head. If he does what I tell him to as easily as this, what else would he do? She missed having a regular sex life. Hmm, I wonder? she thought. Yes, the guy was a nerd, but he was also well built and quite muscular, and he had nice eyes.

  “I’m finished, Charlie,” he smiled at her.

  “But, I don’t think you are, Derek,” she replied.

  He looked puzzled. “You see, I have other things that need sorting around here,” she said, crossing her legs on the chair, and letting her skirt ride up her thighs. She had no underwear on and Derek’s face turned red when he realized.

  “Like what?” he asked uncertainly.

  “Like this,” she said, opening her legs, and spreading her pussy lips wide. “This needs licking clean. Come over here, and get on your knees, NOW!”

  He walked over to her in a daze, and fell to his knees. “Just here,” she instructed, pulling his head closer. He made a valiant attempt, but obviously didn’t had a lot of practice. Charlie smacked his face. “You fucking useless cunt,” she snarled. “Do it properly or you will find you owe me more money than before!”

  Derek’s face was bright red from humiliation, and had a clear set of finger-marks across it. “I-I’m s-sorry,” he stuttered.

  “Do it again or you will get worse,” she yelled. She closed her eyes as he attempted to get his tongue to do what she wanted, but to no avail. He simply didn’t have the necessary skills.

  “You’re no fucking good!” she screamed. “I imagine your mother told you that all the time, didn’t she? It’s no wonder she couldn’t wait to get into care, and get away from you.”

  Tears sprang to Derek’s eyes and Charlie felt powerful and stronger than she had in a long time. “I’m going to have to teach you a lesson,” she said, her voice now cold, and devoid of emotion. “Pass me that scrub brush.” He handed it to her fearfully.

  "Now, pull down your pants and bend over!" Visibly shaking, he did as he was told. “Now, the lessons begin,” she added, as she brought the brush down onto his naked ass.

  I think I’m going to enjoy collecting the rent money from now on, she smirked to herself as Derek yelped in pain.

  Janet and Susan Take You to the Cleaners

  by Chloe

  “Come on, then, let’s get this last lot into the machine,” Janet said. It had been a long day and she and Susan had more than their usual number of customers. They ran a laundry and dry cleaning service in the heart of New York and most of their clientele were wealthy businessmen and women who came to have their work suits cleaned. For an additional price, there were special services available. Most of the clients knew about this service, and would take full advantage when they were waiting for their clothes to be ready. Janet and Susan were dominant, to say the least, but that was what their special customers paid for.

  In the back room of the laundry, a heavy steel door led through to their dungeon, where high powered business people would be allowed to hand over all control. Some of them spent so much of their lives in charge, and making decisions, that it was a welcome change for someone to be telling the
m what to do. A new client had entered the shop the week before on the recommendation of a work colleague.

  His name was Matthew and he was an attorney. All his life, he had been the one who made the decisions, and handed out the orders, until now. He was different from the run of the mill clients in that his requests were slightly more exotic. As far as Janet and Susan were concerned, as long as he paid well, he could have whatever the hell he wanted.

  “Matthew’s due in half an hour,” Susan said. “So, let’s get this stuff finished and then we should be ready for him. Here, have another glass of water while we are waiting.”

  Janet took the proffered water, and said, “I think my bladder is going to burst if I have much more!”

  “That’s the general idea, hun. After all, he’s paying enough for his hot bath, isn’t he?”

  “He sure is,” Janet laughed. “I don’t know if I will ever get my head around it. But, hey, whatever floats his boat!”

  “You will be producing enough to float whatever he wants!” Susan laughed.

  Matthew had already paid the ladies a thousand dollars in preparation for that evening and there would be plenty more coming from his direction if they got this one right! They never actually had sex for money and, if some guy wanted to part with a wad of cash in exchange for being humiliated, long may it continue!

  Matthew turned up smack on time. He believed strongly in punctuality and efficiency. “Good evening, ladies,” he smiled pleasantly as he came through the door. As usual, he was dressed immaculately, and had a smart suit over his arm. “Can you get this cleaned for me? I have an important awards dinner tomorrow evening and I will be wearing this.” He handed over an Armani suit. What he paid for their services was obviously not a problem for him.