The Italian Dominatrix (Novel)

“Hey, I need your help.” a female voice started over the phone.

“What, no hellos first?” David responded, though tried to do it in a teasing voice. He was currently speaking to his girlfriend, a woman he had been pretty into for quite some time. He particularly loved her long blonde hair, which pooled into waves as it fell around her waist. She was sweet, affectionate, twenty years his junior, and was everything he had needed. Now, he was somewhat disappointed that she was leaving for business. He had the weekend off, which was quite unusual for his field, and was looking forward to spending some time with her.

He could practically feel her rolling her eyes over the phone. “David. This is serious.”

“Oh?” He asked, starting to feel quite concerned. He was sitting on his couch with a beer in his other hand, and was about to open it when the phone had rang a Britney song, which he had programmed just for her.

“Well, not really urgent but you know my friend Katherine?” She asked, somewhat hesitantly. He immediately perked up. He had met Maranda’s former sorority sister a few times, and she had always attracted him tremendously. She had thick curly auburn hair, almost to her waist, and sported olive skin as part of her Italian-Cuban heritage. She was always very serious, like she could read his every move, and it always unnerved him. Maranda always seemed so secretive about her too, like she didn’t really want to discuss Katherine’s personal life much.

Though, if he were to be honest with himself, Katherine wouldn’t be as attracted to him as he was to her. He was in his mid-fifties, a bit heavy-set, with a full set of silky brownish-gray hair, and glasses. Though he was wealthy in his position as CEO, women weren’t always immediately attracted to a man so much older than them.

“Yes, I know Katherine.” He tried to sound as nonchalant as possible.

“She needs her help with a computer issue, and I told her you’re great with that stuff, and could possibly help her. She needs it done ASAP, though.” She explained.

“Like you want me to go to her apartment?” He asked cautiously.

“Yeah, I’ll text you the address,” she said.

“Ok, I'll head over as soon as I can.” It didn’t seem like she was giving him a choice, anyways.

“I have to go, but let me know if you’re able to fix it.”

“Love you babe.” He said, it came out of his mouth just as it always did, he was so used to being with her now.

“Love you, too. I’ll text you again when my flight lands.” She hung up, and he set his beer down, immediately ready to set off.

—-

It took him only fifteen minutes to arrive at Katherine’s apartment, but his mind was clouded with intrusive thoughts, like how he could possibly handle the allure of this woman, and why Maranda even thought this would be a good idea.

She had anticipated him through the buzzer, and already had the door ajar when he arrived on the fifth floor. He knocked awkwardly before entering, looking around to find the woman he was desperately trying to avoid. “Hello, David.” She said, her slightly thick accent coming from her kitchen on the right.

He turned to face her, and was shocked to find her in a tight black corset, laced up the front and so tight her cleavage was pushed higher than normal. She wore matching black tights, which was revealed when she walked over with her heels clicking against the wooden floor. “Hi… Katherine.” He stammered. Oh gods, how was he going to make his way out of this one? He could already feel his dick stirring at the sight of her. He would have to fix the computer’s issue, and get out as soon as he possibly could. “I heard your computer has an issue?”

“Yes, I have to use it for work. I have a video to upload of my opera singing, and it’s not working,” Her voice… it was so seductive to him. Her hair was loose as usual, and with every step he could see it bounce around her. He didn’t understand how she kept it so smooth-looking and voluminous all the time.

He followed her into her office like a lost puppy, trying to be as professional as possible. She indicated her computer with a palm, and crossed her arms as she watched him sit at her station. He booted the computer up, and watched it awkwardly as the screen began to load. He could feel her watching him, and felt the heat crawl up his neck. Was he imagining this, or was there something distinctly heavy in the air?

“So… what’s the opera video for, an audition tape?” He asked, trying to break the silence.

“Yes, it’s due tonight,” she replied, then refused to say much else. He felt a line of sweat drip down his neck as he nodded, and began to try to fix the problem. He asked her a few lines of questions, and was surprised to find that the problem wasn’t very big at all, and only required a pretty simple solution. She must’ve been pretty new with using technology in general.

“Well, I’m glad everything’s resolved.” He concluded as he watched the upload reach 100%. “I’ll let Maranda know it’s all good now.” He turned in his chair to give her a smile.

“I should give you a reward for your services.” She said, with a distinctive smirk that wasn’t there before.

“Oh no…” he replied, showing her his palms, “you’re a friend. No charge.”

She ignored him, and suddenly grabbed his chair to turn him to face her. He swerved without being able to stop her, and was shocked to find his face now inches from her’s. She bent down, still sporting the grin, and brushed her long hair behind her head, like she was readying for something. “Wait, what are you doing?” He asked frantically. “You know I’m dating Maranda.” Despite this, he made no move to try to push her back.

“Maranda, who?” She joked, and began to pull his pants down. At this point, he was already sporting a semi-hard cock, and he tried to cross his legs to hide her influence on him.

“Your friend! My girlfriend!” He balked, as she unzipped his jeans, her fingers brushing against his crotch as she did so. He didn’t have a word to say as she pulled his pants down to his knees, then all the way down to his ankles.

“I won’t tell Maranda.” She made a zipping motion across her mouth. “This will be our little secret.” She promised.

He was wearing gray Calvin Klein boxers, and now it was obvious his dick was hard, and was ready for whatever she was about to give him. “You’re so ready for me.” She cooed, and looked up at him with her eyes, which he could now tell had thick eyeliner on top. Her lashes flicked as she looked down at his crotch again.

She moved her fingers in between the opening, and distinctly wrapped her fingers around his dick, making him let out a breathy gasp. “I can’t… what are you doing?” He stared at her with widened eyes. “This is so crazy…”

“I don’t see you stopping me, David.” She said matter-of-factly. “Non mi fermerò finché non mi respingerai,” she continued in Italian.

“What?” He asked, but she ignored him again. She pulled his cock out of his boxers, revealing how very erect he was, so much so that there was a little jewel of precum on top. She didn’t waste any time as she wrapped her mouth around his head, and gave him a very hard suck.

“Oh god.” He moaned, his eyes already moving to the back of his head. “Fuck, Kathy.”

She stopped at once, and moved back to look at him, her seductive look now turning a bit venomous. “Don’t call me any name except for Katherine, or mistress.”

“Mistress?” He asked, but she ignored him again, and wrapped her pretty red lips around his cock once more. She gave him another hard suck around his head, then went straight down to the base, taking him all in at once.

David’s cock was slightly larger than average, and this was the first time a woman had taken it all in with just one slide of her lips without adjusting first. He moaned loudly again. Fuck it, if this woman was so desperate to suck his cock, he was going to let her. She felt way too good to stop. She wrapped her fingers, which were colored to match her red lipstick, around his base, and began to bop up and down like her life depended on it.

He groaned again and grabbed onto her hair, lacing his fingers deep into the smooth and silky texture. He couldn’t believe he was actually touching something he had fantasized for months now. It was even softer than he imagined, just like her lips.

She was clearly an expert as her fingers moved up and down his base, matching the tempo of her lips perfectly as she bopped up and down. Her tongue swirled around the tip over and over, and it was driving him completely crazy. David couldn’t think of anything other than how she felt around him. She was already bringing him over the edge, so far gone that he couldn’t stop himself even if he tried.

He could feel his balls tighten, and he pulled her head even harder against him as she sucked him like a madwoman. “I’m going to come, Katherine.” He said, listening to her earlier order. “Is that okay? Oh… god…” His eyes rolled back again as he closed them.

She made loud gagging noises as his cock hit the back of her throat, and he could feel her saliva pool down her mouth and land on his lap. Fuck, this was the dirtiest thing that’s ever happened to him. His cock gave a tight jerk, and with one particularly long suck, he came, spurting jet after jet of white sticky goo into her mouth as she took it all down like a champion. She stopped as soon as he stopped cumming, and moved back to reveal smudged lipstick and a single tear running down her eye.

“Fuck… Katherine. That was insane,” he said while panting. “I don’t think I’d ever cum that hard.”

“I’m good at what I do.” She said, with a slightly hoarse voice. She stood up, and he assumed that this business was over with. He felt a flash of guilt immediately though, and had no idea how he was going to tell his girlfriend. He had truly fucked it up now.

“So, you’re going to tell Maranda, right?” He asked. “I really messed things up now…”

She grinned, like this is what she had planned in the first place. “You see, this was all a test to see whether or not you would be able to resist me.” She flipped her long hair again. “Clearly, you were not able to do so.”

“You tricked me?” He asked, feeling quite a bit angry now.

“Maranda has used me with many of her boyfriends before, to see if they could be loyal. Not many were.” She smiled a wicked smile. “Now, you have two options. First, I can tell exactly Maranda exactly what you put inside of my mouth, or I can punish you in whatever way I find appropriate.”

He gulped. “What do you mean? Punish, how?”

“You know exactly what I mean. You are to call me mistress throughout the whole punishment, and nothing else. The safe word is bananas,” she explained, like she had done this a million times before.

“I…” He sat back on the chair, rolling it back slightly. “This is the craziest thing that’s ever happened to me.”

“Well?” She asked, “I have your girlfriend on speed dial.” She fished her tight pants, and pulled out a large cell phone.

“Okay, okay!” He conceded. “I’ll accept whatever punishment you deem fit!”

“Good boy.” She grinned, her smile somehow managing to look even more wicked. “Follow me.” He reluctantly followed her, groaning slightly, but still sporting a semi-hard on. He pulled pants fully off and left them on the ground in the study room.

She arrived in her bedroom, and sat on a side pouf, looking up at him like he knew exactly what to do next. “Um…” He said awkwardly.

“Lie over my lap.” She commanded.

“Oh,” was all he could say as he walked over, his heart racing as he bent himself over her lap. Fuck, he couldn’t believe he was actually doing something this crazy.

“I’m going to spank you fifteen times on each cheek, and you’re going to count out loud every time I do so. If you lose count, or fail to count even one slap properly, I will begin again. Do you understand me?” Her voice was harsh and soft. He only nodded. “I said, do you understand me?”

“Yes, mistress.” He replied. He was prepared for her when her hand slapped across his right cheek, making him cry out. When she had said she would be using her hand, he had not expected it to be this hard. He was so shocked by the revelation he had forgotten to say the first count.

“You’re terrible at this, aren’t you?” She cooed. “You’ve already forgotten the first count?”

He shook his head. “One?” He said, knowing she wouldn’t count it anymore.

“I will begin again.” She said. She spanked him hard against the same cheek once more, and he cried out, though remembered to say ‘one’. She did the same to the other cheek, making him cry out, ‘two’. It repeated a couple of times, and the sting was worse with each hit. His butt was extremely sore, and he tried so hard to brace his body every time he knew a hit was coming. She seemed to realize what he was doing, though, because she started changing the intervals between every hit, making him unable to guess when the next one was coming.

He was shocked when, after hit number ten, she began to fondle his balls, gently stroking them in between the hand that was hitting him. He moaned loudly, realizing he was much more sensitive than before, and sporting a boner once more. In fact, he felt more horny than he had been his entire life. Was he… into this? Into the domination of this woman? Fuck, when did pain feel so good?

She spanked him again, and he was almost so lost in thought that he took a second before counting ‘eleven’. She continued over and over, giving him a few lighter spanks when she felt like he was reaching his breaking point, and fondling his balls for a few seconds to give him relief. He moaned and squirmed underneath her, trying to hard to focus on his numbers.

When he finally reached thirty, he let out a huge sigh of relief. It was finally over, he could go home now, and maybe relieve his aching cock again. “Thank you, mistress,” he concluded, knowing it would make her happy to hear him.

“Hmm…” She said, not letting him go.

“What?” He asked, fear now set in his eyes again.

“I don’t think thirty is enough, you know.” She said. “I think you’re enjoying this too much.” Fuck, now he knew the bitch was never going to let him go at thirty. “I will give you ten more, and if you can endure it, then I will know you can handle me.” He looked up to see her wicked grin again. Ten more? He could do that…

“Okay, mistress.” He said.

She pinched his chin and made him stare into her eyes, “good boy.” She sharply let him go again, and slapped him so hard this time tears came out as he cried out. He thought she was being rough before, but that was nothing compared to how this felt.

“Oh gods!” He yelled. “What the…”

“You didn’t count,” She said coldly.

“Thirty one! Thirty one!” He said, feeling fear seep in. She wasn’t going to start again, was she?

“I will give you a second chance.” She said, and slapped him equally as hard against the other cheek. This time, he managed to call out the right number, though was biting his bottom lip so hard to endure the pain he was almost bleeding from it. She slapped him nine more times, and he kept telling himself it would be over soon. When she was finally done, he learned not to be relieved this time. Instead of continuing, though, she stroked the back of his hair with one hand, and his bum with her other. “Sei stato buono,” she said, and he tried to remember the words to google later.

Suddenly, she wiggled as she tried to grab something hidden under the pouf. “What are you doing?” He asked, as he saw her fish out a brush from under the chair.

“Do you think you can handle one hundred spanks with this, my ragazzo dolce?” She asked.

“I…” He studied it, and realized he was at a point where he could never say no to her. He wanted to do anything she asked to please her. “Yes, mistress.”

It wasn’t as bad as he thought, just a completely different texture than her hands. As per before, she stroked his balls and even his cock while doing it, making little sounds of encouragement as he took every stroke. He groaned and wiggled, but thought he took it like a champ. When she was done, she let him up, making him shaky as he tried to stand on his own two legs. “This was quite enjoyable for me.” She admitted. “And you have endured the punishments well. I knew you would be a good pet.”

“Yes, mistress.” He replied, unable to get out of this headspace.

Her eyes flicked down to his cock, then back up to his face. “If you can survive another one of my BJs, then I will let you go permanently. If not, you will continue to be my plaything for as long as I wish, do you understand?”

“Yes, mistress.” He said again, though they both knew he would never be able to resist, not that he was desperately trying to anymore. She knew he wanted this, purely based on how hard he was right now.

She grinned and pushed him back down to the pouf she was sitting on, spreading his legs wide as she flipped her hair back. “Ready?”

He gulped. No, he really wasn’t.

She took her time this time around, massaging his balls first as she looked up at him, her eyes dark and meaningful. It promised all of the nasty things she planned on doing to him, and he realized he couldn’t wait to see what she had in store for him next.

She stuck her tongue out and began licking him from the base to the tip, making him groan and thrust into her. She held him steady with some sort of unnatural strength, and did the same thing again, from the base to the tip.

Gods, he didn’t understand how she could make everything feel so damned good. She kept licking him over and over again, and it was driving him completely mad.

“Mistress…” he groaned.

“Yes?” She asked, knowing exactly what she was doing to him.

“Please put my cock in your mouth…” he begged. He didn’t know someone could get him to this state so quickly.

“Hmm…” She smiled wickedly. “What do I get in return?”

“You win, okay? I’ll be your slave. Just put my cock in your mouth!” He couldn’t believe he was already conceding, but she was clearly not someone he would ever be able to win against.

She seemed pleased, and wrapped her mouth around his cock, making him jolt upwards. Fuck, that felt so good. He groaned loudly as she pushed his cock down her throat again. He pushed his fingers gently in her hair, though didn’t push or pull her at all, knowing she wouldn’t want to give up her authority. She began making choking noises, but didn’t stop for even a second as her head bobbed forwards and backwards. He felt as if his whole body was shaking, and that he might fall apart.

His balls were tightening, signaling he was about to cum, and he moaned her name loudly, unable to help himself. As soon as he did though, she stopped all at once with his cock still embedded in her throat.

He gasped loudly, “why did you stop?”

She released his cock with tears running down her eyes, though she still managed to look smug, “you said my name instead of mistress, I can’t allow that.”

He groaned and leaned back on the pouff. Fuck, he was so close to having the best orgasm of his life, and it had been taken away. He was just about to tell her this when he felt her hot mouth around him again, filling him with lust once more. She sucked him even harder than before, making him grab onto the fabric around him tightly as he tried to contain himself.

No use, the orgasm was coming again. He swore when he came, his cock jerking over and over as he unloaded himself once more. He could feel it explode into her mouth with each jerk, but she took it like a champ again, swallowing every drop.

His cock made a loud ‘pop’ as it came out of her, and she looked completely and utterly unfazed.

He could barely remember where he was again, let alone what he had agreed to. He arched his back, feeling the sweat drip down from him. She only stood up and looked down at him, looking like she had won - and she definitely had.

“When’s Maranda back?” She asked.

“In a week,” he admitted, knowing he wouldn’t ever be capable of lying to Katherine. Even if he did, she would see right through him.

“Good, I’m moving in with you then,” she said, her Italian accent a bit heavier than before.

“Wait, what?” He asked, completely flabbergasted.

“You can’t retract your promises after you cum, that’s not how it works, David,” she grinned.

“I remember what I promised,” he emphasized. “I just wanted to make sure I heard you right. You want to move in with me for a week?”

“I do. I like to play with my slaves whenever I can, and it’s easier when we live together,” she replied matter-of-factly.

He could only stare at her blankly and give her a nod. “I guess that’s okay…”

“Great. I’ll see you in a few hours after I pack,” he assumed that was his cue to leave. He drove home, completely shocked. He couldn’t believe what he had walked into just a few hours before, and what he had agreed to now. Could he really handle Katherine for an entire week - potentially forever? He adored Maranda, and he couldn’t see himself breaking her heart, but he felt like that was what he was doing now. He felt like a shitty person, yet he could still feel the humming underneath it all, telling him he was so excited for the next week, while living with someone had only met a couple of times before.

It was almost like the beginning of a completely fun and exciting new relationship, something he hadn’t felt since the beginning of his time with Maranda.

—-------------

The next few days were just as terrible and as great as he had imagined. She teased him repeatedly, making him beg and concede to anything she wanted. She was an absolute queen, and spent almost the entire time giving him punishments, spanking him until his ass was red and sore and needing a good rub. She had brought almost all of her contraptions, and hid them all over the house so he never knew what was coming until it was too late. Even worse, she exercised the counting technique, making him lose focus from hard spanks, and having to start over again. He didn’t know how many times she hit him total, but it must’ve been close to the thousand mark. And yet, he loved every second of it, and realized what a masochistic he really was.

It was Thursday evening when she announced she had something planned for him that weekend, and to cancel all of his plans, even on Friday. He couldn’t believe her - she commanded him at home, but he didn’t think that would translate to the workplace. “Don’t you think you should’ve given me a little bit of warning first?” He asked, his comb stopping halfway through her hair.

“Keep going,” she commanded, and he began brushing her once more. “It was a last minute decision, I just found out today, and you know we can only do it this weekend before Maranda’s back.”

The guilt burned through him again. “Are you sure we shouldn’t just tell her? I feel like she’d be understanding… maybe…”

She barely thought about it before nodding, “eventually. I’ve always thought of her as a potentially good domme.” He could feel himself getting hard just thinking about it. Maranda? Spanking him with her soft fingers?

“Wait, you’ve distracted me,” Katherine continued, “don’t you want to know what I have in store for you?”

He chuckled softly, “you make it sound like I have a choice in this.”

“Well, tell your secretary immediately to cancel your schedule,” she said. He nodded and moved back, though she grabbed his wrist, “finish my hair first.”

He didn’t have to be asked a second time. He loved brushing her hair, feeling the soft material between his fingers. She always kept it so smooth and luxurious, and he found himself getting addicted to combing her every day. He definitely had a type for women with long hair he could pet, “please mistress, tell me what we'll be doing.”

“I have a mentor named Mistress C. We’ve stayed in contact for years now, and have decided to offer a three-day weekend course for women that want to learn how to punish men. I have decided that you will be our plaything and slut during these three days.” He didn’t understand how she could make everything sound so simple, when it sounded entirely crazy to him.

“A three day dominatrix course?” He asked. “How did you even plan this so quickly?”

“I have my ways,” she replied. Now that he thought about it, she hadn’t been doing much in terms of work these past few days, other than submitting a few audition tapes as an opera singer. She must’ve been planning all this behind his back.

“Where are we doing this?” He asked, knowing there was no point in trying to argue out of this.

“I rented a large cabin out in the woods, so we could have all the privacy we need. You know, especially since you scream a lot,” he sighed and put the brush down, finishing his task for the day.

“I’ll talk to my secretary,” she watched him with sharp eyes as he left the room, picking up his phone to text her and update Maranda as well. He told her he would be trying out fishing with a few friends at a cabin one of them owned, and immediately felt terrible again for finding it so easy to lie to her. He shook the thoughts out of his head, wanting to focus on the upcoming weekend instead.

He went back to his room and began packing, though wasn’t exactly sure what was expected of him. He ended up putting a few pieces of swimwear in his trunk, lots of dress shirts (which was what he wore most of the time), and a few nice shorts and black dress pants. He could practically hear Katherine stuffing all of her tools into her bag in the next room. He would have to comb through the place after she leaves, making sure she didn’t end up leaving anything behind for Maranda to find.

—----------

They left early in the morning, and David was confused until he realized it would take them a couple of hours to get there. Katherine made him desperate and needy by playing with him almost the entire car ride, licking his ears and moving lower until she eventually sucked on his cock, but refused to let him cum.

He begged her over and over to suck on him like she really meant it, but she only teased him further, forcing him to stop at rest stops with a raging boner. Fuck, he didn’t know how he could possibly do a full weekend of this.

They arrived at the cabin first, and he was greeted by quite a spectacular sight. The entire cabin itself was constructed out of large pieces of lumber with black metallic accents scattered throughout. The ceiling itself was vaulted and two floors high, and the windows in the back were built floor to ceiling, so one could see the crystal clear lake out back. The women in the program would clearly be enjoying themselves this weekend. David wondered if he would be extended the same curtsy. He didn’t feel like he had a vacation in quite some time, and being surrounded by beautiful women like Katherine might be the icing on top of the wonderful cake.

“David, go set our things down and stay in the room. I don’t want you to be here when the girls start to arrive,” Katherine said in her usual commanding tone. David was a little insulted, but kind of understood. It must’ve been a little scary for the girls, especially if they didn’t have experience in BDSM.

He went into the master bedroom, which he assumed he would be staying with Katherine. They hadn’t had sex the past few days, but they had been sharing David’s bed, and he had been quite fond of it. He almost didn’t want the week to end.

He was still lost in thought when he heard the door open, and could hear two female voices talking to each other. He couldn’t make anything out, and didn’t want to piss Katherine off by showing himself, and so he turned the TV on, trying to find something to watch to relax his nerves. For the next hour, four more women arrived, to make a total of six including Katherine. Fifteen minutes later, a knock came at the door, and he opened the door to see Katherine standing there, examining him. “Ready?” She asked. He nodded, and began following her.

They walked down the narrow hallway to the living room, and David stopped in his tracks, feeling completely speechless. It felt almost like a horror movie come to life.

Mistress C, or Christina, was standing at the front alone. She was in her fifties, though didn’t look it at all. She had long jet black hair with bangs, and had red lipstick on and a grin on her face. She wore a tight red corset and black shorts, and looked like she was already ready to start spanking David with the look she was giving him.

Four women were standing in front of her, and he recognized all four of them. They had all dated him at one point, with various levels of length and pitiful endings. He hadn’t imagined seeing any of them again, let alone all standing together in the same room. He turned to Katherine, accusing her with his eyes. “Oh, do you know all four of these women?” She asked, grinning back.

How could she have possibly figured out all of their names and contact information? David had always thought of him as a discreet person, but that was clearly not the case. From left to right, the four women were Emily, Erin, Stacy and Cindy.

Emily was in her mid thirties and was a paralegal. She had long curly black hair, which he had always liked about her. She was his previous girlfriend before Maranda, and had always been submissive when they had dated. He couldn’t imagine how she would possibly want to be a domme now.

Erin was taller than Emily, in her mid thirties, and very slim. She had thick and wavy brunette hair down to her waist, and wore her usual bright red lipstick. She was one of the most flirtatious women he’d ever met, and that was what drew him to her in the first place. She was submissive as well, and had always wanted David to tease her.

Stacy was in her mid forties and had darker blonde hair. She was quite the cowgirl, winning multiple rodeo contests, and taught riding and coached rodeo contestants. She constantly drove a large pick-up truck, and had loved driving around the countryside with David. He hadn’t spoken to her in years, though it was clear she had done well for herself.

Cindy was standing furthest away from him. She was a brunette and had the shortest hair of them all. She taught Latin at a prestigious private high school when they had first met, and was also a yoga and fitness instructor, which meant she was pretty fit herself. She had always been a little wild when they were together, and loved to have threesoms with her friend, though thankfully, she wasn’t there that day. David didn’t know if he could handle even more women, especially since they were all currently smiling at him with what seemed to be evil grins, like they had plotted this all together.

“Well, hello,” he said, wanting to run back into the room and hide.

“Hi David,” Mistress C said, “nice to finally meet you.”

“I…” He gulped. “Why are all of my exes here?”

“Because they’re all interested in learning how to be a proper domme,” Katherine said, “I thought that was obvious.”

“Obvious? But why specifically my exes?!” David didn’t think Katherine was capable of shocking him more than she had done already, but it seemed she always had another trick up her sleeve.

“Oh, it’s not all about you David, perhaps it’s just a mere coincidence,” the wicked grin she was sporting said otherwise.

He sighed, giving up yet again. It wasn’t like he could possibly escape now, he was already too far into this to stop now. He walked up to the front next to Christina, giving her a polite incline of his head before standing to the side, letting the two ‘instructors’ talk.

“My name is Katherine, I’ve been the one in contact with you the past few weeks. This is Mistress C, my mentor and also an instructor in this program. And here we have Emily, Erin, Stacy, and Cindy, though I think you all have something in common already,” she winked, and David almost wanted to groan. Katherine knew exactly what she was doing. “Here is David, your plaything for the next three days.” The girls giggled and whooped.

“Here the rules - you can punish David whenever you want, but there must always be another student or instructor present to either help or observe the situation, since you’re all new at this.” They nodded, like it made sense, “I know you’ve also all fucked him before, but that’s banned for the next few days. Blowjobs are allowed, and pegging is as well, though you’ll need to get permission from either one of us first.”

“Wait, pegging?” David said. He’d done it before, but a really really long time ago. He didn’t know if he would be up for it now, especially with everyone watching.

Katherine ignored him, “We will have multiple lessons including positions, implements, teasing and denial, cock and ball torture, and pegging.”

“Cock and ball torture?” David asked again. Gods, what had he signed up for here? And why wasn’t there another guy to handle the rest of it? He can’t handle six women on his own!

She ignored him again, “any questions?” The women shook their heads, clearly ready to get started. “Well, I’m sure you’ve also noticed that we’re at a beautiful cabin, with a wonderful lake out back. Feel free to enjoy as much as you want when you’re here. We’ve also fully stocked the fridge and cabinets.” David was impressed, though it would’ve been way more enjoyable without being the butt of every spank this weekend. Well… if he were being honest with himself, maybe not.

“Now, feel free to set your things down, and we can get started with our first lesson before dinner.” Katherine said. The women all nodded, and he watched them file out one by one. He didn’t want to speak to any of them, feeling quite too nervous. None of the relationships ended super poorly, but it was still jarring seeing them after all this time.

He walked back to his room, needing some space to breathe and sort it all out. Eventually, Katherine called on him again, and he came out, his heart beating fast. Mistress C took the reins this time, and began showing them most of the toys they brought, almost all devices to beat someone with. They ranged from small to large, soft to spiky, and sometimes had matching cuffs and collars. To David’s mortification, the two instructors also showed off a couple of dildos for pegging purposes, some larger than others, though nothing David didn’t think he wouldn’t be able to handle - to his greatest relief.

The girls were mesmerized through the entire thing, some even taking notes about the devices they thought they’d like to use the most.

“Now, I think the best thing we can do is a practice session, where we can teach you exactly what you’re doing wrong and correctly,” Mistress C said.

“You won’t be demonstrating first?” Emily asked, looking a little shy to be speaking up.

“No, it’s better for you to start and for us to see how you’ve imagined yourself as a domme,” Mistress C explained patiently. All four women nodded and she asked, “who wants to start first?”

“Oooo, me!” Erin said, grinning from ear to ear. David would’ve guessed it would be her.

“Great. Begin,” Mistress C said, letting her go without further instruction. Erin’s cheerful mood subsided immediately as she realized everyone was now anticipating her next move.

“I… what do I do first?” She asked, biting her lower lip. It was almost pleasing to David seeing her like this, when she was usually so excitable and eager.

“Your slave is in front of you, willing to do anything you ask of him. You have all the tools you’ll need in front of you as well as your own palms. Do as you wish, we will inform you if you’re doing anything wrong,” Katherine said. Her voice was smooth and soothing, and Erin began moving forwards, gazing at David.

“Turn around,” she said, issuing her first command. He did as she asked, being kinder to her since he knew she was probably feeling nervous. She began pulling his pants down, and Katherine tsked at her.

“Let him do it himself,” she said. David took that as a command, and began pulling his shorts down, showing all six women his gray underwear underneath. Surprisingly, he wasn’t feeling quite nervous, probably because they’d all seen him naked before. Well, except for Mistress C, but she’d definitely seen it all already.

He took his boxers off next, tossing them both to the side. His round ass was now the most amount of skin shown in the room, and he knew they were all staring at it. What man wouldn’t get hard knowing that?

Erin began petting his ass, then gave him a hard spank. He jolted, not expecting her to hit so hard right off the bat. Encouraged by the lack of instructor’s comments, she began using her palms on either side of his ass, making him brace himself in anticipation. “Usually, we warm our subs up by rubbing them, or starting with lighter strokes,” Mistress C said.

“But it seems like he doesn’t mind,” Stacy said, pointing out his erection, which he had hoped he was keeping hidden between himself and the couch he was leaning on. It didn’t matter now, they had all noticed.

Mistress C chuckled, “it seems you’re right. Continue, Erin.”

Erin hit him even harder this time, and as he cried out, he felt her grab something else to use. He could only brace himself as he felt something smooth and leather hit his ass. Fuck, she was really going all out with him. Probably to vent out her frustrations of their break up. “I didn’t think of you as such a sub, but you’re really enjoying this, aren’t you, David?”

He groaned as she hit him another time. “I think… Unh! I think Katherine really brought it out of me. Unh!”

“Look at how hard you are,” then she did the unbelievable. David held his breath as she draped her hair over his body, the entire length covering his back as she began taking his clothes off from behind. She knew exactly what she was doing, as he had told her many times of his hair fetish in the past. It hung over his head on either side, and he shivered from how soft it was. “Oops, is my hair getting in the way?” He shuddered, and she pulled his shirt cleanly off of him. “Hah. Precum is starting to ooze out!”

“Well, it seems Erin has mastered the act of teasing her slave, making him completely weak for her. Good job, Erin,” Mistress C said, “I think that’s good for now. Who wants to go next? Emily?”

Emily also looked a little shy, but seemed to be encouraged by how well Erin had done. David saw her take the paddle from Erin, and throw it between her hands. “Does he count as warmed up now?” She asked.

“I would say so,” before Katherine could even finish her sentence though, Emily slammed the paddle against David’s ass. It hit him so hard he pushed against the couch, making it creak on the wooden flooring.

“FUCK!” He cried out, making all of the girls giggle, which somehow made him produce even more precum.

“So… how’s Maranda, hmm?” She asked. Fuck, he knew all his exes would have some sort of vendetta against him, and now they all had the tools to get him weak for them. She hit him again, and no matter how much he braced, he still couldn’t contain the pain.

“Maranda’s good…” he said honestly. “We’re still together, actually.” SMACK! Gods, he really shouldn’t have said that.

“Wow, his ass is really red now,” Cindy said.

“It’s warm too, want to try?” Emily asked. Cindy walked up to grab something David couldn’t see, and then proceeded to hit him with it. It was a flogger from what he could tell, a long one that made a loud whooshing sound as it landed.

Katherine immediately went up to her, teaching her the correct way to hold it and where to aim on his back and ass. All four women were attentive, though some of them had been flogged before and had some idea how it was like. Then, everyone stepped aside so Cindy could have proper room to flog him. Thankfully, this time it wasn’t quite as bad as the leather paddle, and he began enjoying the sensation of the suede’s length hitting him over and over from the bottom of his ass to the top of his back while avoiding his spine. Honestly, Cindy was doing a great job.

“It’s better to add some commentary from time to time, to see if your slave is okay, but to also make sure he knows exactly who’s in charge,” Katherine said, “isn’t that right David? You know who’s in charge.”

“Yes, you are,” he replied, already feeling so conditioned after one week with her.

“And so are all the other women here today,” she added. “Now, go on Cindy.”

Cindy nodded, and began flogging him again, bending her wrists with every stroke. “Has this always been your secret fetish, David?” He didn’t respond, waiting for her to continue, “you seemed to always want me to be the submissive one in our relationship, and now you’ve completely changed.” The other three women voiced their agreement. “Is it because of Katherine? Did she somehow dig out a part of your subconscious?”

“I…” He started, though didn’t know how to continue. His ass was getting rubbed raw at this point, and his dick felt like it was going to burst. First the car ride teasing, now this… he desperately needed to cum. “I don’t know…”

She suddenly grabbed his cock, giving him a hard stroke. He buckled so hard he landed on the ground, his ass hitting the hard wooden flooring. “Wow, clever girl,” Katherine said, “surprise is always fun - for both parties. Now, Stacy, you’re last.”

Stacy walked up to him, swinging her body back and forth and staring at him like he was her next horse to tame. She let him get up, adjusted his position again, and began rubbing him gently against his ass, “it's been a while, hasn’t it, David?”

He nodded, “I’ve missed our car rides. Still got that truck?”

“Of course,” she said, and smacked him with her palm.

He moaned and wiggled a little, “wow, you really are warm.” She began playing with his balls, tugging at them as she continued to talk, recounting their previous experiences. Honestly, her voice was incredibly soothing, and almost helped with his sore ass.

“I need to cum so bad,” he admitted.

“Don’t make him cum yet,” Katherine said, “he deserves to suffer a little more. A pet always needs to be played with before they get their satisfaction.”

Stacy listened, and kept spanking him. He lost count at that point, ten, twenty, maybe forty times? She stopped for a second and looked back at her two instructors, “wow, this is really hard on your hands.”

“You get used to it. Feel free to use any of the tools to practice,” Christina said.

“I don’t know… I kind of like using my hands, it feels more personal this way,” Stacy said, and hit him again.

“Palms hurt the most,” David groaned as he felt her palm slap against him.

“I know.” Stacy said, draping her blonde hair over him. “That’s why I’m doing it.” Fuck, he didn’t understand how all of his exes could all turn out so sadistic, but it was such an insane turn on.

“Katherine… please can I cum? I feel like I could just touch myself and burst.” He turned around, trying to look as pleading as possible.

She thought about it, nodded, and knelt to the ground. She wrapped her mouth around his cock, and he groaned loudly. This was everything he needed… and he was right, he felt as if he could cum right away. She began bobbing up and down, and his balls were already tightening. He didn’t think he’d ever cum so quickly during a blow job before. He gripped his hands on the sofa so hard his knuckles were turning white, and then came, releasing a pent up load he felt like he’d been saving for months. He didn’t care who was watching as his eyes rolled back and his hips thrust forwards, cumming so much in Katherine’s throat he didn’t know how she was keeping it all down.

“Fuck mistress, you’re amazing,” he groaned.

She finished swallowing and stood up, “lo so,” she said back in Italian. “Now, I think that was good enough for the first lesson. Let’s start preparing dinner, and we can relax for the rest of the evening.” The girls all looked pleased with their progress, murmuring to each other about what they learned.

David had no idea how he was going to handle two more days of this.

—-----------------

David spent the rest of the evening feeling more relaxed, and actually began talking to some of the girls, learning more about their recent goals and ambitions. It was nice to know none of them harbored any ill will against him, though still found it delightful that they would be able to punish him all weekend.

He sipped on some beer, watching the sunset as he enjoyed some well needed relaxation. He wished Maranda was here, but he knew he would have to come clean soon, and hoped she wouldn’t kick him right out the door.

It was getting pretty late, and he wondered if he should turn in for bed, perhaps find Katherine to join him if she was done drinking with the other girls and sneaking in lessons here and there. He was about to stand up when he felt a hand on his shoulder, warm and small.

“I was about to take a shower, do you care to join me?” He turned around to see Mistress C and a smile spread across his face.

“Of course,” he was used to morning showers, but he would never say no to showering with a woman like her.

They walked to her private bathroom, and he wondered at once how many there were in the cabin - it was huge indeed. He stripped in front of her, knowing she had already seen everything. He was transfixed as she began taking her own clothes off, and stuttered as he said, “would you like me to do it instead?”

She grinned, like she had hoped he would offer, “what a good sub you are, yes, I would be pleased if you could assist me.”

She was still wearing a corset, and he wondered how she could possibly keep it on for so long, knowing it was largely constricting on the body. He walked behind her and began unlacing it, and pushed her beautiful hair aside to work it properly. Fuck, her hair was just as smooth as Katherine’s, maybe Katherine even learned how to care for hers from her mentor. He finished unlacing her, and the corset fell onto the ground, revealing her breasts underneath.

If he wasn’t currently her submissive, he would’ve wanted to approach her and suck on her nipples until she moaned for him. Instead, he politely tried to look away, and helped her pull her shorts down instead. She grabbed onto his shoulder as he placed a single kiss on her thigh and pulled her panties down, revealing her naked body at last.

She was being much kinder than Katherine, but based on what the woman had explained about her mentor, Mistress C could be quite the sadist indeed. He stood back up, not ashamed that his cock was now hard again. How could it not be, with a naked woman standing in front of him, looking at him like he was her prey?

They walked into the shower together, and no words had to be exchanged. He knew exactly what she wanted, and he desperately wanted to do it as well. He picked up the shampoo bottle provided by the cabin owners, squirted it onto his hands, and rubbed it into her hair. Luckily, he was slightly taller than her, and managed to do it at a comfortable height. She let the hot water run down her body as she closed her eyes, letting him dig his fingers deep into her scalp, just like how he knew women liked it.

He made sure every inch of her luscious locks were completely covered in the shampoo, and when he went back to rubbing her scalp again, she let out a low moan. Fuck, that was too much, he could feel himself getting even harder than before, and she looked down at his cock at the exact moment it happened.

She looked up at him, giving him a wickedly disapproving glance. He almost shuddered at the intensity of it, “is my little plaything getting hard washing my hair?”

He gulped, “yes… I’m sorry. I can’t control it.”

“And did I give you permission to get hard while taking care of me?” She asked with an equally curt tone.

“No, you didn’t.” Fuck, he was in for it now. Was it possible for her to be even crueler than Katherine?

“Then I believe you need to be punished for being such a horny mess,” she said. He couldn’t think of any words to say, and could only stand there as he watched her sit on the side of the tub, looking at him as he stood there naked. “Well? You know what I expect of you.”

He nodded, and reluctantly draped himself over her lap, using his legs to keep himself steady. He was confused when she reached over and turned the handle, though immediately understood when the water suddenly turned scalding hot, and aimed right at him. “Oh god…” he moaned, trying to not jump away from the shock of it.

Behind him, she grabbed a long-handled bath brush, which he had planned on using to comb her hair after the shampooing and conditioning was done. She turned it around, and planted one large hit against his ass. He yelped, feeling the sting of the plastic against his still sore ass. Fuck, the combination of the hot water and the hair brush… It was almost too much. She hit him over and over again, the sound of the brush hitting his ass making a sound that echoed through the bathroom.

He groaned and struggled, but it was no use. She was gripping him firmly, and making sure each hit was landing exactly where she wanted it to land. He could tell she’d been doing this for years. SMACK! SMACK! SMACK! He was about to beg her for mercy when he suddenly felt her other hand reach around and grab onto his cock. Finally, he was about to get some release. Instead of stroking him, though, she began squeezing hard. It began with a light pressure, then continued to be so hard he thought he was going to burst. Fuck, he’d never had a woman play with his cock like this before.

He closed his eyes and tried to calm his body down. He felt like he was being attacked on all parts of his body, with no way to get any release. Soon… she must be stopping soon. “I didn’t expect you to be so quiet, but I guess Katherine has trained you well.”

“Argh! No, Katherine doesn’t like when I complain or beg for mercy… she just makes it even worse… Fuck!” She slammed her hand all the way down his cock, and then back up again. He had never been jerked off so hard before. She continued making the same motion - quick and rough, over and over as she paddled his ass.

Fuck, was he actually going to cum from his? “Mistress, do I have permission to cum?” He asked, knowing that the punishment for cumming without her permission would not be worth it.

“You do,” she said, and her smooth voice alone was what pushed him over the edge. He groaned, and his cock began pulsing and squeezing as he came, covering the floor of the bathtub with his sticky goo, which immediately began washing down the drain. “Good little slut,” she said, her strokes beginning to slow down and eventually becoming less rough. He was completely slumped over her lap, panting loudly as his body quivered.

It wasn’t the best orgasm he’d ever had, but it was certainly one of the most intense. God damn, he almost wanted to do it again. She let him take his time getting up, though eventually stood up with him and turned the heat down. “Finish your job,” she said coldly, and he began rinsing the shampoo off of her hair. He took his time conditioning her as well, and was glad his cock wasn’t acting up again. It seemed to have learned its lesson the first time around.

He still enjoyed every second of it, mesmerized by the way it fell around her and flowed between his fingers. He knew he could wash her hair every day and never get tired of it. After rinsing the conditioner off as well, he grabbed the brush that had just been used to spank him fifty times, and took his time to untangle every part of her hair. They must’ve been in the shower for more than an hour at that point, and neither of them seemed to be in a rush to leave.

She finished washing her own body, and he did as well, with the two of them beginning to make small talk, mostly about their relationships with Katherine. Mistress C was laughing loudly at Katherine’s trap, congratulating her for being so devious. He sighed, and knew it was mostly his fault for ending up in this mess in the first place.

She wrapped a towel around her hair, put on her sleeping clothes, and exited the bathroom, letting him take care of himself.

He eventually kissed her goodbye on the cheek and left her bedroom, seeking his own. He knew he would have excellent rest that night, though worried what the next day would bring. Katherine was already in bed sleeping, and he rubbed some lotion on his sore ass before joining her, falling asleep almost immediately.

—----------------------------

The next day began with Katherine commanding David to make everyone breakfast, then using him as an implement to teach the girls multiple lessons. He hadn’t cum by mid afternoon, and was getting hot and bothered again, mostly from being the focus of so much attention. The worst part was, they all had beautiful hair, and were all women he was insanely attracted to, despite how much they teased and played with his emotions and body.

By four p.m. he was feeling exhausted. He wanted to sneak out of the cabin and cum, then maybe take a three hour nap to satisfy himself. Katherine seemed to know exactly what he was thinking though, because she planned the polar opposite. She announced to all the women she had something incredibly fun planned, just to congratulate them for doing so well for their second day of lessons.

They all gathered around the master bedroom’s king sized bed, and Katherine commanded David to lie on the bed with his belly facing upwards, completely naked. Gods, he knew this wouldn’t be good. He stripped quickly, listening to her as he avoided all six pairs of eyes. Katherine began explaining about how to properly restrain someone, making sure they had enough blood flow but wouldn’t be able to escape. She emphasized the importance of safe words, then made Cindy and Stacy attach him on either side of the bedpost. It was almost like Katherine designed the bed to be perfect for tying someone up.

He had expected them to do his legs as well, but instead, Katherine told Erin and Emily to climb onto the bed as well, and put his legs their shoulders. Damn, this was an incredibly embarrassing position, all of them could see all parts of him clearly - his asshole, his balls, his cock, and his taint. He felt mortified, and wondered how he would ever be able to get past this.

Katherine, clearly content with this, began whispering in all of their ears, not wanting David to hear exactly what she had planned for him. He wondered if he should escape now, before it got really rough. She was far too happy about this for it to be a normal session.

He was about to say something when Erin began brushing her hair on his chest, with Emily following her movements as well. He didn’t think his dick had ever gotten hard that quickly before, but it was erect straight away, making the women watching chuckle amongst themselves. Then, Stacy stepped forward with a smile on her face, and began spanking his ass.

Thus began the delightfully cruel combination of pleasure and pain, as Erin and Emily sucked on his nipples, played with his chest hair, and cooed at him while Stacy did her best to smack his ass as hard as she possibly could. In between spanks, she would tug on his balls, even putting it in her mouth once or twice and grazing her teeth against it. Then, the spanking would begin again, and his mind frantically tried to make sense of both the pain and the pleasure. Katherine knew exactly how to fuck with his mind, because this was way too good.

After one hundred spanks against his ass, the girls decided to switch positions, with Cindy and Stacy holding his legs up and Erin doing the spanking. She picked out a cane, and began hitting him with it, starting with a small distance from his ass to larger and larger swings. She looked at her two instructors for guidance a couple of times, but they seemed to tell her she was doing a good job, because she continued her ministrations all the same.

Cindy and Stacy were driving him wild by continuing to tease him, beginning by sucking and pulling on his earlobes, then licking down his neck, nibbling and biting all the way down. There were way too many sensations going on at once, and he knew his body was definitely getting over stimulated. The caning was becoming harder and harder, though with enough breaks and stroking in between that he never felt like it was too much for him. He endured the entire way, though he had groaned loudly with each stroke by the end.

The women switched again, this time with Cindy doing the spanking. She picked out a leather paddle with small circular bumps on the entire surface, then proceeded to count to a hundred. The two women playing with him began lowering their attention, moving further and further down to where he most wanted their lips and fingers.

Erin grabbed his cock and began stroking it, squeezing at the tip with each stroke. He jerked upwards, his restraints holding him down as he moaned. “I don’t think I can take any more of this…” he admitted.

Katherine’s face appeared above him, “it’s been a while since you’ve admitted defeat. I’m surprised you couldn’t last longer.”

He didn’t want to disappoint her, and said, “it’s the combination of the pleasure and pain. Fuck, it’s driving me crazy.”

“I know. It’s one of my favorites, Cindy, finish your count to one hundred,” Cindy nodded and continued, with Erin stroking his cock even harder than before. She had always been good at that. With the last of the hundred strokes with the ribbed paddle, the spanking was finally over, and David knew this broke the record for the most spanks he’d ever received in one session. He hoped the record wouldn’t be broken again. He needed to ice his ass somewhere, and wondered why Katherine hadn’t let him go yet.

“Oops, did you think we were done with you?” Katherine asked sweetly.

“My ass is already going to be bruised for a week!” He complained. He was so preoccupied talking to Katherine he hadn’t noticed Emily putting on a strap-on. Mistress C had been whispering to her on the side, and making sure it fit on her perfectly.

She approached now with a cock sticking out of her, one that was a perfect six inches. David glanced at her, then at Katherine, then back at her. “What are we doing?” He asked, his voice shaking a little.

“The girls need to practice pegging you, of course!” Katherine said with her usual matter-of-fact voice.

“Oh gods have mercy on me…” he whispered. “All four of them?!”

“Sorry, but you signed up to be the only plaything, and they should all get to take a turn,” Katherine explained this as Emily climbed on the bed with a bottle of lube in hand. Mistress C began explaining to her how to rub it on her cock, soaking it before turning to David.

“Before you start, let me show you how to get an ass ready for you,” Katherine said, and moved forwards to spit on her fingers. She pushed a single long-nailed finger into his exposed ass, making David cry out.

“Fuck Katherine… your nails…” Again, the perfect combination of pleasure and pain. Her nail was long enough she could arch her finger and reach his prostate. He’d never felt such a bizarre sensation, but it was driving him crazy. She stuck another finger in after a few strokes, and began explaining to the girls how to loosen an ass up while giving pleasure at the same time. As she said this, her fingers spread apart, pushing his hole to its limit.

He couldn’t believe how many eyes were currently staring at his asshole being played with. His dick was twitching, begging to be touched again, and oozing an incredible amount at the tip. He wanted to spank his own body for being so greedy for attention all the time. That’s what got him in this mess in the first place!

After Katherine felt it was sufficient, she pulled her fingers out, stepping back to let Emily approach again. Emily aligned herself against David’s asshole, pulling him forwards so he was in perfect position for her to fuck. She then pushed her way in, but couldn’t manage to do it on her first try. The two instructors walked up to her, giving her words of encouragement and aligning her again. This time, Mistress C helped Emily guide her fake cock against David’s asshole, and together they pushed the head in. David immediately felt stretched again, just like how Katherine’s fingers felt, but even fuller. Emily made her way slowly inside of him, eventually hitting the base.

He felt his asshole flex and adjust, trying to make sense of the intruder inside of him. Fuck, it had been a very very long time since anything had been up there, and he couldn’t quite make sense of how he was feeling. Emily seemed to finish adjusting as well, because she pushed out and back in again. This time felt better than the last, with the pain slowly shifting into a pleasurable sensation. Katherine anchored both her hands on Emily’s waist, then began helping her thrust back and forth just like how a man would typically fuck a woman. It was quite different than the gyrating motion a woman usually made when she was on top, and seemed to take quite some time to get used to, especially since Emily wasn’t feeling the sensations herself and couldn’t tell exactly what she was doing.

She eventually made sense of it, and began holding onto David’s legs as she fucked him, looking like she was having a lot of fun doing so. She eventually finished her turn, and Erin was next, with a dildo already strapped on, this time more ribbed than the last.

Erin seemed to get it even quicker than Emily, and began fucking him quickly, making sure to stroke his cock as well as she did, “how does that feel, hmm?” She asked, looking him in the eyes.

“So… good…” he moaned, his eyes rolling back from the pleasure of the ribbed cock. Erin definitely knew how to use her hips well. She began pumping his cock with her fingers every time she pulled out, and the combination of the rhythms were driving him completely mad. He could feel himself getting close for the third time that weekend, his cock begging him for release.

Right at the edge though, Erin stopped all at once, smiling down at him like she had just won a big prize. “Remember when you did this to me in the past? I’m getting my revenge now…”

“Fuck… ugh I was so fucking close…” he moaned.

“I know. That was the point,” she pulled out of him so suddenly it made a loud ‘pop’ noise, and Stacy was ready behind her with her own larger black dildo strapped onto her.

“Ready for some fun, cowboy?” Stacy joked, stroking her cock in front of David. He groaned and slapped his head back down on the bed… he didn’t know how much more he could take of this.

Stacy squirted a large amount of lube on her cock, stroked it, and aligned herself against his now puckered asshole. Mistress C made sure she was in the right position, then let her shove her fake cock deep inside of him. He felt like he was being stretched to the limits, and yet there was still one more to go after Stacy. She fucked him like she was in a rodeo, making loud noises as she used his used body as leverage to fuck him as hard as possible. Even Katherine was a little speechless as she watched it happen, though was clearly amused by how much Stacy was enjoying herself.

In contrast to Erin, Stacy didn’t bother stroking David’s cock, and let it hang there against his stomach, so desperate to cum he thought it was going to turn blue.

At last, it was Cindy’s turn, and the yoga instructor approached him with her pink dildo, which was long and had a large head. “Is this okay?” She asked.

“Yes, you’re doing perfect,” Mistress C said. Cindy had always been extremely flexible and strong, and she used this to her advantage now. She could rest both of his legs on her small shoulders as she wrapped her arm around him and onto his cock, beginning to stroke it again as the large head tried to fit itself inside of his already sore ass.

She slammed all the way inside of him suddenly, and he almost screamed from the onslaught as it struck his prostate. She fucked him like she had done it hundreds of times before, and knew she would be the one to finally make him cum. The room was silent except for the sound of skin slapping against skin and David making unintelligible noises with every thrust.

Suddenly, he felt her hot mouth suck the head of his cock, and that was the breaking point. He came at once, his cock exploding inside of her as he screamed her name. He thrust over and over, and his cum almost felt never ending. He could feel his prostate contract inside of him, and that was heightened by the sensation of the large dick hitting him on his insides.

David felt incredibly lightheaded, and as soon as she stopped everything, he felt like he was close to fainting. Katherine undid his bindings, and his hands fell to the bed. He wrapped his fingers around them, stroking them with his eyes closed. “I have never… ever felt anything like that in my life,” he said. He didn’t even know who was even left in the room any more.

He could briefly hear Katherine conclude her lesson, and her move into the bed next to him. She began taking care of him, wiping his body down with a warm towel and asking him if he was okay. He told her he was, but he needed some time to regain his energy. She grabbed him water, then let him nap for the rest of the evening.

—------------------

He woke up the next morning completely startled, and realized he had slept for more than fourteen hours, and it was now past seven a.m. He grabbed a quick shower, then headed to the kitchen, making some breakfast for everyone before they woke up.

He was less worried about what the day could bring. He had faced the pegging, and had come out on top, and knew there wouldn’t be much left before they went back home. He wondered how his relationship with Katherine would continue after this experience was over.

During breakfast, he was informed that there was one more lesson planned, then there would be a party to celebrate such a successful course, with the women all confident about being new dominatrix. He was actually pleased that he was able to help all of his exes blossom into something new, and that they were all doing well in their own personal lives.

After lunch, the party began, and David walked around shirtless as he finished barbequing their final meal. Katherine had a few bottles of champagne for the occasion, and they all toasted to a wonderful time, with everyone deciding they would have to come back again to play for another weekend. David agreed as well.

In the middle of the party, Katherine announced she had another game for them to play before it was all over, mainly to thank David for being a good sport about the whole thing, and always being open to experiencing new things.

He was shocked about how sweet he was being, but knew he wouldn’t complain. She told them she would blindfold David, and he would have to guess whose mouth was around his cock after he came inside of it.

David was delighted - he would never say no to a blow job, though kind of worried about the punishment if he did choose the wrong woman. He would have to try and find out.

Katherine wrapped a piece of cloth around him, blinding him to all as he felt his pants being pulled down as his cock exposed for what felt like the hundredth time. He wasn’t hard yet, but he was definitely getting there.

He knew the mouth like the back of his hand - it was definitely Katherine. This game would be a piece of cake. No one could take him to the back of her throat like Katherine could. She started off rough and unrelenting, bobbing up and down again like she always did. Yes, this was exactly how he liked it. He pushed his fingers into her hair again, feeling the long and soft texture he adored so much, realizing he had missed his chance to comb it the night before. He was about to announce it was her when he suddenly felt a shift, and another mouth wrapped around his cock.

Damn… Katherine had made it sound like it would only be one of them. He hadn’t expected multiple mouths! This one was way less familiar, licking him from the base to the tip while she teased him. He thought of the one most likely to tease him, and guessed it was probably Erin. She didn’t wrap her mouth around his cock even once, and only let her tongue do the work as she licked every part of him.

Another mouth began sucking on his balls, taking them in as she grazed her teeth against them. He felt Erin leave, and the one on his balls move up to take his cock inside. She played with the tip of him, swirling her tongue over and over around the edge. He buckled into her, and realized he could cheat by feeling her hair. Yes.. this was definitely Cindy with her short hair. She seemed to have realized what he was doing, because she forced his hands back behind him, not letting him touch her anymore.

On and on the mouths switched, until he couldn’t tell what was going on anymore. He couldn’t remember how many times they stopped and started playing with his cock again, and could only focus on the sensations as one of his senses was completely taken away. He could hear their whispering in the background, but couldn’t tell whose mouth it was anymore.

Eventually, he felt his cock harden to its limits, telling him he was about to cum. “I’m cumming…” he announced, “gods, I need to cum so bad…”

“You have my permission,” he heard Katherine’s voice from somewhere. The woman began fucking her own mouth with his cock, driving him completely wild with lust. He came with a roar, still obediently holding his hands behind him as he thrust deep into her.

He couldn’t tell if she had swallowed every drop, but could feel her mouth withdraw from him. “Who was it, David?” Katherine’s voice said again.

“I… fuck. I can’t tell.” There was giggling in the background again. “Was it Stacy?” He knew he didn’t have a chance of getting it right at all.

“It was me,” Christina’s voice said, and he pulled the blind off, looking down to see her kneeling in front of him.

“Fuck…” He groaned. He knew that would mean more punishment. He was about to ready himself when Katherine shook her head, laughing.

“I think you’ve had enough of that this weekend, mi amore.”

“Seriously?” David asked. “When did you get so nice?”

“Don’t push me, David,” Katherine winked.

They spent the rest of the party finishing up their champagne glasses and cleaning up, packing their belongings to prepare for the drive back home.

He messaged Maranda again, informing her he would be home soon. She confirmed her own arrival the next morning as well, and he was honestly excited to see her after a long week. He knew he would have many meetings the next day, but hoped he would be able to see Maranda that evening.

He waved goodbye to all the women as he set off with Katherine, promising to see them again soon to do this again. They all had a great time, after all.

Katherine stayed quiet throughout the car ride, and he wondered if she was also thinking about how they were going to approach the Maranda situation, since it was rapidly approaching. “Do you want me to drop you off back at your place?”

She was startled by his talking, but nodded, “yes, that would be wise.”

He turned left towards her apartment, his head still spinning with everything that had happened, and for once, David was completely lost for words.