For some of my long-term chastity slaves I give a monthly chance to put in a bid for cum. I call it the Golden Opportunity and this is how it goes: I tell him: “make your bid” and within my five second countdown he is allowed to make one offer. If I deem it satisfactory, he will be allowed to spurt out his manjuices before getting locked back up. It may seem simple enough, but consider being locked up for two or three months, and being teased in a session for an hour or two before being asked this question. What would be your price, my horny slave? A bid too low would only insult me, and you wouldn’t want to do. Then it’s just better to let the chance pass. There’s something intriguing in a slave voluntarily giving up his chance to cum in order to please his Mistress.
So it was time for his monthly session, and he had nearly completed his three months in chastity. Unfortunately for him, he missed his first Golden Opportunity, because of his bad behavior, and second time his offer was not satisfactory, so instead of empty balls and big smile, I sent him home with aching full balls, red sore ass and tears on his cheeks. For his third session he was very determined to earn his cum. I, of course, had teased him relentlessly over the last week in Whatsapp before our session and I knew that after the session I for sure could go online and splurge on dungeon equipment, toys or some sexy lingerie.
I was wearing my black dress that reveals my luscious curves and fabulous breasts, because I knew it would drive him crazy. But I also wanted him to be on his best behavior from the get-go. So when he entered, I told him to get undressed as soon as he closed the door behind him. I collared him and told him to get on his knees and kiss my feet for a while. “I hope you have come better prepared than last month, slave”. He replied “Yes, Mistress”, while kissing my toes. I then told him to fold his clothes and bring them to my dungeon before I sent him to shower. He crawled upstairs on his all-fours. I followed him and grabbed his chastity cage. “I think I will not remove this just yet, you’ll have to earn it first”.
After his shower he came back downstairs, where I was waiting on my throne with massage oil. Now he was fresh and clean, but I still wanted to inspect him. So I walked around him, dragging my fingers around his naked body, pinching him. I gagged him with a ball-gag and told him to give me a good foot massage. I fell into a very relaxed pampered bliss as he was doing his job surprisingly good. While he was holding my one foot and massaging it, with my other foot I kept teasing his chastity cage and verbally arousing him. I also spread my legs a little, just to test if he would greedily try to look what kind of lingerie I was wearing, or if I was wearing any at all. But to my surprise he had learned from his past mistakes and stayed focused.
“I am pleased with you, slave”. I removed his ball-gag. “Okay, slave. Time for your first bid. I want to give your ass a good spanking. If you can impress me, I will remove your cage.” I said while swinging the key to his chastity cage in front of his eyes. “So, my slave, how many hits do you think your ass can take? And remember that rules apply. This is your one and only offer to get your cage removed today.” He looked puzzled. He knew that a professional domme wouldn’t be impressed with 10 or 20, maybe not even 50. His lips moved, but no sound came from his mouth. He coughed and swallowed and with anxiety in his voice he said “I want you to spank my ass one hundred times, Mistress”. A hundred. More than I was hoping for. I stared into his eyes, raised my eyebrows quickly and gave him a cheeky smile. “So you think you can survive a hundred hits, slave? We’ll see. Let’s get to work. Get on the spanking bench.”
Before I started I grabbed a large butt plug and lube. “Spread you ass for me.”, I told him as I pulled a rubber glove on my hand. I fingered his ass quickly, before I pushed the plug in with force. “Nice and tight”.
I grabbed my favourite whip and started. Because a hundred hits takes an effort, and I didn’t want to be out of energy for the last hits, I didn’t start with full force. After a warm-up of 20, my swings started to gather momentum. I could hear it from his voice as he counted. When I got to 40, his ass was on fire and his voice was starting to break. I took a little break. “Do you really believe your ass can take as many hits as your pathetic cock is willing to offer?”. “But remember, slave. If you call out your safeword, the cage stays on, and I’ll send you home with aching balls.”, and as I said this, I rubbed his blue balls from behind. “So should we proceed?”, “Yes, Mistress”, he said.
I changed to a cane, just for fun. Again I started with light hits, just to see how he would react and anticipate the next hit to land on his ass, but the hits got stronger quite quickly and after everyone, he counted the number, cried of pain and thanked me for the hit. After 65 hits, I decided to go full force. And he felt it. No longer was he hopeful about finishing. His body could no longer just take the pain. He had clearly started struggling. Now it was time for me to pick up the pace and not give his ass time to recover from the previous hit. After 85 I decided to give him all I got.
“89, thank you Mistress”
“88, thank you Mistress”
“87, thank you Mistress”
“86, thank you Mistress”, he sobbed.
But now he was ready to beg for mercy. Only he knew, that it would mean another month of no cumming for him. But he looked like he was about to say his safeword. So I patted his ass, gently. “11 more, you can do it.” Then I rubbed his balls and yanked at his chastity. The spanking had taking away his erection, but I could tell that he still enjoyed that I touched it. “Keep going Mistress”, he said.
So I continued to deliver his spanks, and by the time I finished, his ass was all red, bruised and striped. “Well done, slave. Seems like you really wanted to get your little dick out of that cage.”, I said as I oiled his ass. Then I unlocked his cage and allowed him a supervised shower to have his dirty little dick cleaned.
When he came back, I secured him into my bondage bed, and started teasing his dick. I poured some warm oil on it and barely touched it that he constantly kept wanting me to touch him more, faster and harder. I made a ring with my thumb and index finger and told him to hump my hand. Because he was tied to the bed, he could only barely move, but he surely did his best to get any pleasure out of the situation, as he thrust his hips upwards as fast as he could. “How much have you waited to cum”, I asked him. “A lot Mistress”, he answered. “Please let me cum today”, he continued almost crying out of desperation.
As our session reached its halfway mark and I had edged him twice, I gave him another task. I took a dildo with a suction cup and slammed it into the floor. Then I released him from the bed, removed his butt plug and told him that if he could ride that dildo like there’s no tomorrow, I would allow him to place his bid today. I didn’t have to tell him twice, but I had another plan. “First I want you to get on all fours and suck that dildo”, he got into action as fast as you probably can imagine. He wasn’t a shy cocksucker, but started deepthroating like a pro. With amusement I looked as tears flowed from his eyes, as the discomfort of having a cock in his throat grew, but he kept going. Then I gave him the lube and told him to start riding. It took him a while to get comfortable with the large dildo, but as I hinted that I wasn’t particularly pleased of what I was seeing, he started riding faster. I squatted next to him and teased his oily cock with my fingertips to give him motivation. “How does this feel, slave?”, I asked. “Fantastic, Mistress”, he replied. “Don’t forget to tell me when you edge”, I reminded him. As he started to leak precum, I started feeding it to him, and when his thighs started to get tired, I encouraged him to keep going, if he wanted to cum. We had about ten minutes left of the session, and then I decided to tell him to stop and get up.
I went around him and and started whispering things in his ear while I reached around to play with his cock. I made sure that he got right to the edge and told him to hold it. He was so desperate, he was whining and crying. Then I asked him the question. “Slave, how much are you willing to pay for an orgasm?”. Then I started counting: 5… he was still catching his breath. 4… He was trying to say something, but he was clearly struggling. 3… I reminded him that he only gets to place one bid. 2… “500 euros, Mistress”.
“Hmmmm, five hundred you say…”, I told him. “Okay, but get it fast before I change my mind.” He ran to his wallet as fast as he could, counted the money and came back to me. “Get back on the bed on your back and roll your legs over your head.”, I commanded him and he obeyed. So there he was, in this uncomfortable position and the tip of his dick pointing towards his face. I grabbed the dildo from the floor and shoved it in his ass with force. I started fucking him with the dildo and gave him permission to play with himself. “And don’t forget to keep your eyes and mouth open and aim the cum at your face”, as I moved the dildo faster and faster in his ass. It didn’t take him long to ask for a permission to cum. I teased him a bit, before gave him the permission and he spurted his big hot load all over his face. But I didn’t end just there. I wanted him to remember this orgasm, so I took advantage of his uncomfortable position and gave him a good post-orgasm torture. I started stroking his cock as his pleasure started to become more and more painful.
“You wanted to cum, so now you can cum, slave”, I laughed. “Stopstopstopstopstop”, he begged. “You slaves, always begging for your Mistress to touch your cock and now you don’t want it. Make your mind up already”, I teased him. The pleasure of the orgasm had already passed and intense sensation of pain had overcome him. After a while I already got bored and sent him to shower himself, but before that I wiped my hands on his face and told him to suck my fingers clean.