Lucky Man

[lovesthepain72]

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Victor was a very lucky man. The day he turned eighteen, on a whim really, he bought a lottery ticket. Growing up he watched his mom play all the time and never win a damn thing, but this time he won. Not only that, but it was the biggest jackpot in that game’s history. After ensuring his family was set for life, he wisely invested a large amount and was a billionaire by the time he turned 21. Even though he didn’t need to, he went to college after highschool. Partly for the knowledge and general experience, but mainly for social reasons. He wanted to meet new friends, find a girl, fall in love and get married. Once he got there he realized two big problems to his plans. The first was people trying to take advantage of him for his money. After a few bad experiences with would-be gold diggers, he found it very hard to trust anyone he met. The second was his secret desire to submit to a woman. He discovered he was a very kinky boy. He was drawn to the idea of being a woman’s slave. Visions of being tied up, spanked and whipped, teased and denied, dominated his mind. He wanted to explore these feelings, but had no idea how with his current trust issues. One night while searching online for some adult entertainment, it finally hit him.

He typed into the search bar “professional dominatrix” and spent the rest of the evening looking up and researching every pro domme within a 50 mile radius of him. He thought it was the perfect arrangement. He had no worries about being taken advantage of, it was a straightforward business transaction. He would pay their fee and they’d fulfill his fantasies for a few hours. In a way it was much more honest than the women he’d met in college. After spending a few hours that night he picked the one who’s listed interests best matched his own and he also found physically attractive. She called herself Mistress Alexandra and she was gorgeous. According to her site she was 5’5” and a D cup. The pictures showed a beautiful woman with long blonde hair. She was very curvy, just his type. Once he had decided, he filled out an initial contact form on her site. After submitting, he looked at the clock and was surprised to see it was 3 am! As excited as this new prospect was, he quickly fell asleep.

What followed became Victor’s new obsession. She responded the next day and offered a few times they could meet. He picked the earliest date he could. The session went better than he could have imagined. He was no longer just interested or curious submitting to a woman, he now knew it was a necessity. For the next several years he had a weekly session with Mistress Alexandra. She was only five years older than him and was just starting out when he first visited her, so she was working out of a shared dungeon. He had no illusions of them being a couple, but nevertheless they grew close. Occasionally, they would share a meal after a session. It was during one of these meals she shared how she’s been saving to acquire her own private space. At a minimum it would be something she could call her own and have full control and access, able to session whenever she wanted and for as long as she wanted. Even rent out the space for some extra cash. But her real dream was to become the head mistress at her own dungeon where she could work with other dommes. Victor was impressed with her entrepreneurial ideas and how passionate she was about being a pro domme. Probably one of the reasons they got along so well, this wasn’t an act or cash grab for her. Plus he had for some time been wanting to experience lengthier sessions, perhaps even over several days. Until now she wasn’t able to accommodate that, and he had no desire to find someone else who could.

Victor had recently graduated and had been wondering what to do with his life when the obvious idea hit him, “You know, I could finance your dungeon.”

She froze mid-bite, “You want to give me the money? I don’t know.”

“Well, not exactly. I would just be investing. Consider me a silent partner and I’d get a percentage of the profits, but you’d still be majority owner. I can have my lawyer write up contracts and…”

She stopped him, “Whoa whoa, slow down. This is a lot to take in, are you serious?” Victor simply nodded. “I need to think about this. The whole point of me doing this is I don’t want to work for anyone else or owe anyone anything.”

“Like I said, you’d still be the owner and in charge. We can write up the contracts anyway you need to be comfortable. Just think about it and think of how much you realistically think you need.”

She thought it over for a few weeks and decided to take him up on his offer and become business partners. Alex was very careful about their arrangement, even hiring her own lawyer to ensure the contracts were to her liking. He was a little hurt at the lack of trust, but ultimately understood and gave in to every concession she brought up. Fast forward six months and they were putting the finishing touches on Mistress Alexandra’s own personal dungeon and play space. While he could have hired people to do everything, she insisted on saving some money and they did a large portion of the work themselves. During this time they grew even closer, getting to know each other better outside of their session personas. If Victor didn’t know better he’d think there was a mutual attraction, but she made it clear early about not getting involved with someone she has a business relationship with and he didn’t like the idea of dating someone who sessioned with other men, even though it was her job.

Alex decided to take some time off to recharge before opening her doors, going back to her home town to visit family, but promised Victor would be the first client when she returned. The next few weeks dragged for Victor. It had been a couple of months since he last had a session. He didn’t notice at the time since he was still spending every day with Alex, helping to get her dungeon ready. In a way, he was serving her constantly, but now that he isn’t with her, the cravings to serve again are strong. To make matters worse, a long time ago he agreed to give up total control of his orgasms to Alex. He only ever cums during a session with her, but of course not every time. His last orgasm was three months ago! A new record for him by far. He felt weird bringing it up while they were working on the dungeon, and can only assume Alex either forgot or she thought he was masturbating anyway. Unfortunately for him, he stayed true to his word and was hornier than he could ever remember.

He did his best to distract himself by spending time with some of his other hobbies. After three disappointing weeks of not hearing from her, late Sunday night he was about to go to sleep when his phone alerted him. He had a text from Alex! She wanted to meet for lunch tomorrow to go over any final plans for their grand opening. His excitement quickly turned to disappointment again. While he was looking forward to seeing her, he was really hoping she’d want to schedule a play session, but of course he texted her back that he’d meet her.

At lunch the next day he had never seen Alex so relaxed and excited. The time away did her good, and she seemed thrilled that her dream business was about to become a reality. As they were finishing up lunch she suggested they visit the dungeon. She had put some “finishing touches” on it and wanted to show them off. Victor was surprised, but was happy to see what she had done. As they entered Victor could immediately see how much better everything looked. Alex must have spent quite some time there decorating and rearranging. Everything looked perfect. They toured the various rooms, each with a different theme. Dungeon/torture chamber, medical, a more personal bedroom, large dressing room or changing area complete with various dresses and outfits, both for the dommes and those into cross dressing. Even a place for longer visits, including a jail cell and smaller dog cage. They spared no expense to make this the best play space in the city. As they finished the tour, Alex asked, “So what do you think? Ready to break this place in?”

Victor was taken off guard, “Everything looks amazing, but what do you mean?”

“Come on, Victor, don’t play dumb. It’s been forever since we played together. I haven’t seen any clients since we started building this place, and I’m assuming you haven’t been to anyone else?”

Victor stammered, “N-no. Of course not.”

She smiled, “It would be ok if you did, it’s not like we’re dating, but if I’m honest I’m glad you didn’t. But I’m curious, have you had an orgasm since the last time I let you? Again, it’s okay if you did. I released my other clients from those obligations but somehow forgot to mention it to you. Oops. But I’m guessing you did too otherwise you would have said something by now, right?”

“Actually, no. It’s been about four months now. I’ve stroked and edged myself, but no orgasms.”

Alex’s eyes went wide, “Really? Holy shit. Well done. And not once did you ask or beg to cum. I’m impressed and that’s kind of hot. Well we definitely need to play now, what do you think?”

Victor couldn’t agree more and soon found himself naked and bound in the dungeon room. She started him off on the St. Andrews Cross, an upright x-frame with his wrists and ankles bound at the four edges, leaving his legs spread and already hard cock completely vulnerable. Once he was secure, she wheeled in a custom fucking machine they had designed. What made it so special was the small tablet attached to it that controlled the speed and depth of the thrusting. It could even be programmed to change randomly, keeping the subject guessing. On the end was a fleshlight, which was now approaching his erection. Alex rubbed some lube on him and rolled the machine forward so it completely enveloped him. After locking the wheels into place she went to the tablet and after a few settings it whirred into life. She set it so it would very slowly go down his cock then quickly up, pausing after each up stroke ranging from one to fifteen seconds. “There, that should keep you entertained while I go change and get ready for you. Hope you don’t have any other plans, we’ve got a long day ahead of us.” She left the room, closing the door behind her. The walls were covered with a faux stone design to give the room a medieval dungeon aesthetic, complete with decorative windows with bars on them. When the door closed, it blended into the wall perfectly, so you really felt trapped with no way out. Hanging from the walls were various whips, floggers, and canes. Other bondage equipment completed the room. Chains and shackles on the wall and ceiling complete with a winch hookup, a spanking bench, and a bondage chair perfect for CBT were just a few of the other items. A large dresser completed the room, to hold any other various restraints and implements needed. Instead of being impressed with all of this, Victor could only endure the teasing, wishing he had made himself cum at least once in the past few months. He quickly lost track of time, another feature of the room’s design, so had no idea how long he was left there to suffer. Victor only knew this was maddening. It was never enough to get him to the edge, and never stopped long enough to let him relax, he was just constantly stimulated and going insane with lust. He knew begging was pointless, but he couldn’t help himself as he pleaded for mercy to the empty room. Of course, he completely forgot about the cameras and microphones they had installed so the dommes could monitor the clients for their safety when they left the room, which is what Alex was doing right now. As much as she was enjoying the show, she knew he had enough for now and went back to join him.

Victor was relieved when the door finally opened. He was about to beg for any kind of release, but was suddenly speechless when he saw her. It had been awhile since he saw her in her professional attire and forgot just how perfect her body is, and it looked like she went out of her way to show it off for him today. Dressed all in black with high heel shoes, fishnet stockings and garters that connect to a push-up corset. That corset was working overtime pushing up her massive breasts. It was like she walked out of his dreams and into reality. Her voice broke him from a trance, “What happened to the begging? You were sounding pretty desperate a few minutes ago.”

Seeing her in that outfit was making him throb even harder in the fucking machine, “Wow. You look amazing!”

Alex giggled, “Thank you, I thought you’d like this. And how are you liking our toy there?”

Victor moaned, “It’s working too well. I’m so horny right now! This thing won’t even bring me to the edge. Please Mistress, may I finally cum?”

She laughed while walking towards him, “Hell no. We’re just getting started,” and turns off the machine, pulling it away to leave his cock to bounce in the air, desperate for more stimulation. She then shocks Victor by grabbing his penis and slowly stroking it. Mistress Alexandra always had a strict policy of no nudity on her part and no sexual contact. The only times in the past she touched his cock was to position it into something and even then she wore latex gloves. Any time she permitted him an orgasm he either did it himself while she watched or she used a vibrator or some other toy. So feeling her hands on him for the first time felt amazing. In fact, no one has touched him like this except for himself since he started seeing Alex. Couple that with the fact he hasn’t cum in months and just spent who knows how long being teased, and he was ready to blow almost as soon as she touched him. Unfortunately for him, they have sessioned together for so long now that she could read his cock like an expert and knew exactly when he was on edge. Slowly she stroked, using a similar technique as the fucking machine, driving him closer and closer to the edge, but taking her sweet time to get there. The entire time studying his penis for the tell tale signs of an impending orgasm. Victor quickly began begging again for relief, much to her delight, “That’s it, that’s what I want to hear. Tell Mistress how bad you want to cum.” Of course, he did. He was a blubbering mess as she excruciatingly slowly took him right to the edge and stopped, letting his cock throb and bob in the air while he continued begging. “There there, hush now, slave. You seemed upset the machine never took you to the edge, and since I’m so good to you I gave you exactly what you wanted. Thank Mistress for being to generous.”

After a short moan, “Thank you Mistress for edging me.”

“That’s a good boy. Now you aren’t the only one who’s been itching to play. I haven’t dominated anyone since our last session a few months ago. We’ve been so busy getting this place ready, I never had the time or energy. That means I have a whole lot of pent up frustration of my own I need to let out. Not sure if that’s good news to you or not, but I hope you remember your safeword?”

“Yes, Mistress. It’s red.”

“Good boy.” She placed her hands on his stomach and let them roam up his body, wrapping her arms around his neck. She pressed her body against his and whispered into his ear, “But I hope you can hold out for me and not use it. Be my good little slave and take everything I give you and I promise you’ll be rewarded.” Victor could only nod, hoping he could endure whatever she had in mind. It wasn’t long before he found out as she slowly backed away from him, kicked off her shoes, then kicked him in his exposed balls. He howled in both pain and surprise, and before he had a chance to catch his breath she kicked him again and then again. After the tenth one she stopped and placed her hands on her hips watching Victor struggle in his bonds. Her face was slightly flushed and with a heavy breath said, “Fuck, I’ve missed this! Having a helpless boy at my mercy, willing to suffer for me. We’re going to have so much fun today!” Victor could only sag in his bonds. He was definitely out of shape when it came to taking pain and she would usually ease him into it, but he was determined not to safeword for her. Alex walked back towards him, “Poor slave. I’ll bet your balls are really swollen holding all that cum, aren’t they? Here, let me help.” Her hands were back on him, one gently massaging his balls, the other slowly stroking his cock. Once again she agonizingly slowly took him right to the edge and stopped. After waiting several seconds she brought up a knee to smash against his balls, giving him ten blows in total.

This was her first game of the day. Bring him to the edge, then ballbust him. After the kicks and knees, she then slapped them, punched them, and squeezed them. Victor was just about at his limit when she asked, “Well that was fun, ready for round two? I want to go again.” His begging was genuine this time, desperately pleading for mercy. “Uh oh, did I break my slave already? Maybe I can give you some incentive to take more. Did you like feeling my hands on your hard, denied cock?”

“Yes, Mistress! They felt amazing!”

“I thought so. Well, would you like to feel my lips?” Victor was speechless. She wasn’t saying what he thought she was...right? He could only dumbly stare as she continued, “You’re a very special slave to me. Definitely my favorite. So what do you think? Another couple rounds and I promise you’ll feel my lips on your cock.” How could he pass up that offer? He quickly agreed and Alex repeated that routine two more times. Edge, kick, edge knee, edge slap, edge punch, and edge squeeze. Victor desperately wanted this to end and would have used his safeword long ago if not for the promise she made to him. His focus on the upcoming blowjob is what kept him quiet. Well, not quite as he was constantly screaming in agony, but he never tapped out and took everything she had to offer.

Once she was done Victor had tears on his cheeks as his body went limp. He would be a crumpled mess on the floor if not for the straps holding him securely in place. As he struggled to catch his breath he saw Mistress Alexandra put her heels back on and walk towards him, once again throwing her arms around his neck and pressing her sexy body against his. She held him as he got himself under control and soothed him, “That’s my good boy. You took all that pain just to make me happy. It’s why you’re my favorite slave. Are you ready for your reward?” That perked him up a bit as he nodded vigorously. She stepped back and smiled widely at him, “Okay. Get ready.” His erection had started flagging, but it perked back up again with what was to come. He watched eagerly as Alex slowly went down to her knees in front of him, her mouth mere inches away from his again rock hard cock. His heart was racing as she leaned forward and placed a kiss on his cock head, but to his horror that was all she did. Instead of feeling the inside of her mouth, he felt the straps around his ankles being removed. Then his waist, and finally his wrists.

Victor was still in shock as he now stood in front of her, wondering how she could be so cruel. Alex was still all smiles as she said, “Was it as good as you hoped? Now get down on your knees and thank me like a good slave.” He wanted to complain, argue, cry, anything but do as she says. Then he realized she was true to her word. She promised her lips on his cock, and that’s exactly what she gave him. Defeated, he fell to his knees and began kissing her high heeled feet, thanking her as he did. Alex beamed at the control she had over him. After letting him worship her feet for a few minutes she picked him up and led him out to the room for overnight stays. After cuffing his hands behind his back, she put him in the small dog cage, “Now be a good boy, I’ll be right back. I left some water for you if you need it.” After locking the cage door she left the room and Victor was alone. The cage was about three feet high, two wide and four deep. He was stuck on his knees, and with his hands behind his back, it was a struggle to keep his head off the floor, let alone move around. In the back of the cage was a bowl of water like Alex had said. Victor was very thirsty and forced to drink like a dog if he wanted any, which he did. After waiting a few minutes he managed to lay down on his side to try and relax while he waited for what Alex had in mind next.

He was so relaxed, and worn out from earlier, that he started to doze off, and of course that’s when the door opened and Alex returned. “Wakey wakey! I have a new surprise for you.” She opened the cage door and helped him out. After removing the cuffs she ordered him to crawl behind her as she led them back to the dungeon room. Once there she had him position himself over the spanking bench where she again secured him in place and left him alone in the room.

A few minutes later he heard the door open but to his surprise it wasn’t Alex, some other woman he had never seen below walked in! She had a very goth look to her, jet black hair, dark makeup with a couple facial piercings. She was dressed simply in jeans and a t-shirt, but again all black. In his shock he asked, “Who are you? Where’s Miss Alex?” The mystery woman stared at him with a raised eyebrow then walked to the dresser fishing something out of one of the drawers. She turned holding a ball gag and walked towards him. He knew what was next as she forced it into his mouth and secured the buckles behind his head.

“I was told that you were a well behaved slave. Guess I heard wrong. I am Domina Amethyst, but you will simply refer to me as Domina, assuming I let you speak at all. I will be working here under Mistress Alexandra. She asked if I wouldn’t mind helping her out today. My specialty is corporal punishment, which I’m going to demonstrate for you.” Victor tried to speak through the gag, but only muffled noises came out. He had never had a session with anyone other than Alex, and honestly didn’t want to. Plus taking severe beatings on his ass was never a favorite for him. Out of the corner of his eye he saw Domina take a large paddle off the wall and disappear behind him. When the first blow landed he realized he can’t use his safeword with the gag in his mouth. Did she even know what it was? Does she even care? Panic began setting in as she continued raining blows against his helpless backside. He screamed through the gag and struggled to get free, but it was futile. No one was listening and he couldn’t break the bonds that held him in place. Domina was relentless as she continued paddling his ass. He wonders if she would have ever stopped if it wasn’t for Alex coming back into the room.

“Oh good, you guys have met.”

“Yes. Had to gag him, he was rude from the start and hasn’t shut up since.”

Alex walked in front of Victor and squatted down so they were eye level, “Sorry about that. He usually is very well behaved. I didn’t tell him you were coming so he’s probably just scared. Surprise!” Victor again tried to talk through the gag.

“See what I mean? This one’s a real chatterbox.”

“I don’t think he likes what you’re doing to him, do you?” He quickly shook his head side to side. “Would it help if I distracted you?” She moved closer so their faces were only inches apart then raised herself slightly and pushed his face into her cleavage. “Does this help?”

Domina laughed, “Looks like it. The little slut’s getting hard.” Victor was in heaven. For years he’s dreamed of just being able to see Alex’s breasts, and now they were literally in his face! Of course, the fact that he can barely breathe is a problem, but he was too busy enjoying the moment to care. The flogger crashing down on his backside made him quickly start caring again. While not as bad as the paddle in theory, he was already so sore that every fresh strike was agony. Between the gag and her breasts his screams were nonexistent to anyone but him. To make matters worse, the lack of oxygen was becoming an issue as he was getting light headed. However Domina never stopped and Alex never moved away, so he focused his energy on trying to breathe as best he could. As the hits continued he was losing the battle for air and was about to pass out. He barely noticed when Alex told Domina to stop and she released him from her cleavage. He only knew he could finally breathe again and was sucking in as much air as he could through his nose. A few seconds later the ball gag was removed and he could finally pull in all the air he needed. As his breathing slowed his body was limp on the bench.

“Jeez, did we break him?” asked Domina.

“I don’t think so, was just smothering him a bit too much. Let’s give him a rest, though.”

“That’s fine, I need to get going anyway. Thanks for the light workout, slave. Maybe next time we can get serious.” Victor did not think he wanted a next time, but for now he was happy to rest. Alex gave him a kiss on the forehead and walked out with Domina, closing the door behind them.

This time he did doze off, so had no idea how long he was alone when the door opened again, waking him. Another strange woman came in alone. She was a little taller with a very fit and toned body donned in only a sports bra and yoga pants. With brown hair and a very pretty face she looked like the girl next door. “You must be Victor. I’m Mistress Donna. I’m going to be working here too, so Alex thought I should come in and introduce myself.” She walked behind him, “Wow, looks like you’ve already had a few introductions today. Don’t worry, pain’s not really my thing, but I do like a nice ass.” She went over to the dresser and returned with a blindfold. After putting it in place, she said, “Don’t want to spoil the surprise.” She then put the ball gag back in his mouth and walked away. He could hear her going through the drawers again, and then some buckles clinking about. He had an idea of what was happening. When he felt something cold and wet touch his asshole his suspicions were confirmed. A moment later her hands were on his hips as she was slowly pushing a strap-on into his ass. Once she had it all the way in she explained, “I’m more about pleasure than pain. My pleasure, anyway. That’s why this strap-on is double-sided. Plus,” a second later he heard a click and suddenly the dildo inside of him came buzzing to life as they both moaned, “this one has an added feature. Jesus, that feels good. Now I’m going to fuck you until I’m satisfied. I’ve had a few guys cum from this too, and I’m told you’re pretty backed up, but I’d hold out if I were you. Alex will be pretty pissed if you cum without permission.”

That was the last coherent thing she said for a long time as she started fucking him. Slowly at first, giving him a chance to relax and accept what she was doing, but soon she was thrusting into him hard and fast. The vibrating dildos were making them both moan with pleasure. Donna was thrusting faster as she was getting closer to cumming. To Victor’s surprise, he felt like he was getting close as well. He had done this a few times with Alex before, and while he didn’t hate it, it was never something he was particularly into, and he had never had an orgasm from doing it. Of course he had never gone four months without cumming before either! Unfortunately for him, now was not the time to experience it. He wasn’t sure if it would work, but he tried the usual old tricks, thinking of completely unsexy things, hoping he could hold out. Lucky for him, a few minutes later Donna screamed out in pleasure and collapsed on his back with the strap-on still deep inside of him, buzzing away. It was enough to keep him hard and excited, but no longer in danger of cumming without permission.

After resting for a moment, she said, “I should have turned off the vibrator, it’s turning me on again. Ready for round two?” Victor shook his head and yelled no through the gag, but he was still helpless, “Tough shit.” Once again she started slowly thrusting into him and fucked just like before. Knowing how close it made him before, right from the start he tried to distract his thoughts and was able to keep himself under control as Donna again came with a loud scream. This time she remembered to switch the vibrator off as she rested on his back. Victor prayed there would not be a round three, not only was he afraid he wouldn’t be able to keep from cumming any longer, but his ass was pretty damn sore! Mercifully, he felt the strap-on slowly exit him. “Well that was fun! It was great meeting you!” Just like that she was gone, leaving him alone, blind, and still strapped to the spanking bench.

Several minutes later he heard the door open again, then the blindfold and gag were removed. After his eyes adjusted to the light, he saw Alex squatting in front of him at eye level. She had a glass of water with a straw and put it up to his mouth. He gratefully sucked down the entire glass. “How are you holding up?”

Victor was close to done, “Please Mistress Alexandra, please no more!”

She looked a little surprised, “Weren’t you the one always telling me you wish we could do longer sessions? Isn’t this exactly what you had in mind? Besides, if we stopped now you won’t be allowed to cum, and I know you must be desperate.” She was right about everything, of course.

“I’m sorry. I wasn’t expecting all this or the other mistresses you found. How many are there?”

“I know, I wanted to make today special and surprise you. Looks like I did a good job. Tell you what, how about we give you a little break and take you to the bedroom?” Victor couldn’t help but notice she ignored his question, but a break in bed sounded perfect so he agreed. She first led him to the bathroom so he could take care of any business, but insisted he sit down and she watched to ensure he was “a good boy.” It was a little humiliating and took him longer than usual but eventually he was able to relieve himself. The bed they bought was pretty impressive. King size, solid oak, four post, with plenty of eye hooks and other features installed to allow immobilizing someone anyway you’d like. What Alex liked right now was to lay him down on his back and spread his limbs out as much as she could, attaching each one to a corner with rope. She also wrapped some around his waist, chest, elbows, and thighs, to ensure he could barely move.

Once satisfied with her handy work she laid on the bed next to him, “That should hold you for our next guest.” As if on cue another beautiful woman walked in the room. This one was a short redhead. She couldn’t have been more than 5’2” with a slender body, but still had large breasts. Victor guessed they were fake. He could tell all this because she was wearing a very tight fitting leotard, like something a gymnast might wear.. She was all smiles as she approached the bed. “Victor, this is Goddess Christina. She’s going to be seeing clients here too. Her style is a little different than most other dommes I know, but I think you’ll like her.”

“Most boys do.” Christina crawled onto the bed between his legs and immediately grabbed his half hard cock, getting it back to fully erect almost instantly. “Everyone has silly rules about not touching cocks, guess they don’t want to be confused as prostitutes and get into trouble. But I absolutely love playing with a nice, hard cock. I could literally spend all day touching and teasing this thing. Besides, if I never let it cum is it really considered a handjob?”

That caused Alex to laugh, “I guess not. Never really considered it. Mind if I hang out for a while to see your handy work?”

This time it was Christina laughing, “Sure, as long as you’re not bothered by a boy begging and crying for an orgasm.”

They both laughed hard at that one, “I think I can manage.” She rested her head on his chest to get a good view of the action. While Alex could read his signs and knew when to back off, Christina made her look like an amateur. She not only was able to easily bring him to the very brink of orgasm but hold him there for as long as she wanted. It wasn’t long before Victor was constantly begging to cum, just like Christina predicted. She was relentless. After watching silently for some time, Alex sat up and said, “Victor you need to be quiet for a bit, I want to talk with Christina.”

But he couldn’t, “Please, Alex, please make her stop and let me cum, I’ll do anything, please!”

She became more stern, “Stop it, you’re embarrassing me. Don’t make me gag you again.” That managed to get him to stop begging, but he continued moaning and whimpering. “So Christina, how long do you usually do this to your clients?”

“Oh, I usually like to mix it up and not edge them constantly like this. Learned that the hard way. Scared a few boys away early on and others tapped out during. I still do longer sessions, but there’s plenty of breaks during so they can catch their breath. But you said you wanted this to be special, and I was serious when I said I could do this all day, especially knowing he hasn’t cum in months! Fuck, I’m getting wet just thinking about that!”

Alex looked back to him, “You hear that? You’re getting the special treatment today. But you can take it, right? You won’t wimp out like those other boys. You’re going to make me proud, aren’t you?”

He didn’t want to. He was ready to end this now, if they’ll let him. But the way Alex was looking and talking to him. It made him want to do anything to please her. So instead of yelling “Red!” like he wanted to, instead he replied, “Yes Mistress. I can take it for you.”

She smiled wide, “Awww, that’s my sweet slave. Would you like the gag again so you can’t change your mind?”

No, that was crazy! Even Christina agreed, “You sure you want to do that after everything I just told you?”

Alex never looked away from Victor, her smile widening, “That’s exactly why I want to gag him. Don’t you agree, slave?”

He gulped, “Yes please. Thank you, Mistress.”

“See?” With a giggle she hopped out of bed to grab the gag and returned to secure it back on his head.

“Ok, but I’ll ease up a bit…”

“Oh no way. Like I said this is a special day for him and also consider it a welcome aboard gift for you. Do your worst and have fun!” To his horror, Alex got up and left them alone in the room.

It was Christina’s turn to smile at him, “Guess it’s just you and me. Why don’t you relax and enjoy the ride.” He could only moan as he set his head back and endured her teasings. He had no idea how long she worked him over, but she did change her technique periodically. After keeping him constantly on the edge she abruptly got up and left the room without a word. Victor was thankful and couldn’t wait for Alex to come back in and rescue him. His heart sank when Christina returned alone five minutes later drinking a glass of water. She hopped onto the bed and straddled his stomach facing his crotch. She grabbed hold of him again and began stroking him firmly and quickly, taking him to the edge in less than a minute. Of course, she stopped just in time. After pausing for around thirty seconds she did it again. Over and over she did this until it got to the point where only a stroke or two would put him back on edge. She had a sick sixth sense for knowing exactly when to stop and apparently she never made a mistake. The only reason she stopped this game when she did was because he got to the point where just a mere touch would have set him off. Again she left the room without a word, but this time Victor had no illusions that his ordeal was over.

Sure enough she came back several minutes later holding a handful of stockings. “We sure have a nice selection of pantyhose here. This is a fun game I call pantyhose pulling. Have you ever had someone rub something silky over your cockhead over and over again?” Victor slowly shook his head, fearful of what was to come. “I think you’ll like it at first, but then you’ll get so sensitive and it will just go on and on. It should really drive you crazy. Best of all it won’t make you cum! Ready?” It didn’t matter as she once again positioned herself between his legs. Taking one of the legs of a pair of hose she rolled it up and placed it over his cock, after she gave it a few strokes to get it fully hard again, of course. With one hand she held the base of his cock steady, and the other grabbed the toes of the hose. She then slowly pulled it towards her, causing the hose to rub right over his head. She was right, it felt nice at first but very quickly became unbearable. He was already sensitive after the hours of teasing he’s had to endure today and she made sure he felt every inch of the hose as she slowly pulled it along, giggling with delight hearing the noises he made and watching him thrash in the ropes but unable to get away.

Once she got to the end Victor laid there breathing heavily through his nose, trying to relax, grateful it was over. What he didn’t realize was Christina was rolling up the other leg getting ready to put him through hell again, which she did. She went through half a dozen pairs. By the end he could only sob silently. “Fuck, I’ve always wanted to do that. So what did you think?”

She crawled up the bed and removed the gag, “Please no more, red, red, red, please, mercy, please stop, please...”

“Looks like I broke you. I warned you guys. Hang tight, I’ll be right back.” Christina left the room and a moment later returned with Alex.

“Boy, you weren’t kidding. Poor Victor, was she too much for you?”

“Hey, you were the one bragging about how tough he is and said to do my worst. Be glad I only gave him around 75% of my worst.”

Alex chuckled as Victor began begging again, “Please no more! Red, Mistress, red! Please!”

She made shushing sounds, “Take it easy. Let me untie you and we’ll take a break.”

“How long have you guys been playing today?”

“Let’s see. I teased and busted him for about an hour. Amethyst was here and beat his ass for just a half hour while I smothered him. Then Donna fucked him for at least an hour. And finally you had your fun for two. What’s that add up to?”

Christina quipped, “For him? An eternity!” They both laughed as a now free Victor stretched his limbs a bit before curling up into a ball on the bed. Alex, dressed in her casual clothes, climbed in and spooned him from behind, trying to soothe him. “Well, I should probably get going.”

“We’ll probably grab dinner in a few minutes, wanna join us?”

“Sure, why not? Let me go change.” Christina walked out, leaving them alone where they laid in silence for a while.

Once his breathing slowed to normal, Alex broke the silence, “So how are you feeling?”

He paused, gathering his thoughts, “I’m okay. That was just so intense! I’ve only ever had a session with you and you’ve never pushed me that hard or for that long. I wasn’t expecting any of this today.”

“Yeah, but did you like it?” He was afraid to admit that he did...a lot! Even though during he desperately wanted it to stop, he was glad they pushed him. Even now he was getting hard again just thinking about what they put him through today, which also made him wince since his cockhead is amazingly sensitive and sore after that pantyhose pulling. He explains all of this to her as best as he could, which oddly enough helps him relax and feel normal again. Alex was smiling again, “So I guess if I offered to let you cum right now you’d say no since you’re so sensitive?”

He moaned, “That’s so not fair.” Her hand slid down and grabbed his shaft, squeezing, causing him to moan again as his body jumped. She steadily squeezed him, forcing him back to a full erection, and soon close to cumming. Continuing the pace, he felt just moments from an orgasm and knew better than to do so without permission, “Mistress, may I please cum?” Instead of a reply her hand slid up and rubbed his head, causing him to thrash about to escape the overly sensitive torture. He wound up rolling away, off the bed and onto the floor, much to her amusement once she knew he didn’t hurt himself.

“Come on, let’s grab some food. Afterwards, we’ll see if you’re a little less sensitive down there and maybe I’ll allow an orgasm.” She helped him up off the floor and they left the room to find Christina. As Victor went to find his clothes, Alex stopped him, “Oh, you won’t need those. I thought we’d order in. I’ll call Donna and Amy and see if they want to join us.” Victor was a little frightened at the thought of being naked in front of four beautiful dommes like that, but his cock twitched in excitement despite himself. The other ladies and the food arrived around the same time, so they all went to the kitchenette to eat. The table was small and only sat four, so Victor was forced to sit on the floor while they ate. He was much hungrier than he realized as he wolfed down his meal in just a few minutes then sat there as he listened to the four Mistresses above him discuss their plans for the new dungeon.

Domina Amethyst was first to notice him, “Is he just going to stare at us all night? It’s a little creepy. Can’t we put him to use?”

Alex responded, “He’s earned a little break. Someone made his cock too sensitive to play with.”

Christina replied with mock hurt, “Not my fault. Someone insisted, and I quote, ‘Do your worst!’”

They all laughed at his discomfort, but Domina wasn’t satisfied, “Surely he could be put to other uses. For example, my feet are sore and could use a massage.”

Alex thought for a second, “You’re right. Slave, crawl under the table and massage our feet. Start with Amy and work your way around the table.”

“Ugh, don't call me that in front of a slave!”

“Fine. Start with Domina Amethyst then. Happy? You’re so formal.”

Victor didn’t pay any mind to the bickering as he started crawling. Once there he gently removed Domina’s shoes and socks and began massaging her feet. After a few minutes he moved on and did the same for each of them in turn. Meanwhile, they were having a cryptic conversation above the table. “So what do you guys think?” Alex asked.

Domina was first to answer, “I still don’t think it necessary, but can see the advantages.”

“I’m good either way,” said Donna.

Christina sounded ecstatic, “Oh I’m totally on board. Most definitely.”

“Easy there. You’ll still need to share and have limits. Okay, sounds like it’s settled. Shall we?” The ladies all got up from the table, “Victor, go to the dungeon room and wait for us, we’ll be there in a few minutes.” He did as he was told, wondering what they could possibly have in store for him next. He was both scared and excited. Surely she wasn’t going to have them all play with him at once? Once in the room he wasn’t sure what to do with himself, so he decided to kneel in the middle facing the door. Several minutes later it opened and he was treated to an amazing sight. All four of them must have made a quick stop to the dressing room since they all looked like they stepped out of his dreams. Amethyst was the perfect stereotype of a dominatrix donned completely in black leather. Christina wore a full body stocking, but unfortunately for Victor, it still managed to obstruct her breasts from his view. Donna’s was similar to before with a sports bra, but this time very short, tight workout shorts showing off a hint of her ass cheeks. Of course, Alex outdid them all walking in as if she were on the runway for Victoria’s Secret. It was a much softer look than earlier but just as sexy. He wonders for a moment what he did to get so lucky as his cock began to rise again at the sight.

Domina was first to notice, “Poor fool thinks this is exciting.”

Alex admonished her, “C’mon, look at us? We’re fucking hot! Also, he’s such a good boy kneeling and waiting for us. I thought you’d appreciate that?” She grudgingly agreed as she went to the dresser with Donna. Alex stood him up and distracted him by standing close and caressing his chest and stomach, telling him what a good boy he’d been all day. Christina joined her to help by slowly stroking him again, not trying to edge him, just gentle touches to keep him rock hard. What he didn’t see were the ankle and wrist cuffs and spreader bar the other women were gathering. He barely noticed as they put them on him, attaching his ankles to the bar and his wrists above his head to the dangling chains also attached to a bar. Each bar was around three feet in length. It wasn’t until Domina started to raise him that he realized what was going on. She had him high enough so that his feet were just barely on the ground. He was completely exposed, front and back, and helpless. He forced himself to become more aware of what they were doing and he watched Donna and Domina each grab a flogger and walk behind him. The fear and excitement he was feeling was so intoxicating he thought he might pass out, but there was no way he was going to miss out on this.

Alex gave Christina a go-ahead and stepped back. Suddenly she was working him to the edge again as she did earlier, using her uncanny abilities to keep him there for as long as she desired. She then nodded to the women behind him and soon he felt floggers strike across his ass and back every few seconds. “Victor, I have a little confession to make. When I released my other clients from their orgasm restrictions, I didn’t forget to tell you. I wanted to see if you’d be a good boy for me or not. Think of it as a test, and you definitely passed! And today was a bit of a continuation. The ladies and I were talking and we think it would be good to have a permanent slave for the dungeon. Someone who could help out, cleaning, setup, fixing things, and of course someone to serve all of us if and when we needed it. I immediately thought of you so we made today a test run to see how you held up and if everyone liked you. So what do you think?”

Thought was extremely difficult. What she was offering was a dream come true, though he always hoped to serve one woman he actually had a relationship with. Add in the fact he was still riding the edge and being whipped, and his mind was a mess. “I, uh, I don’t know. Sounds good.”

“Well before you answer, you should know if you say yes then you won’t be cumming today. Who knows when you’ll cum again, but I know orgasms will be less frequent than when you were just seeing me. You’ll need to please all four of us, and any other dommes who might join in the future, in order to earn your releases. But if you say no, Christina here will make you explode in probably the greatest orgasm of your life and we can just go back to sessioning once a week with just me like before.”

He moaned, “Oh god, please no. I need to cum so bad!”

“I know, you’ve never gone this long before, and today you were teased so much. You must be going crazy! I couldn’t even imagine. But admit it, today was the best experience of your life, wasn’t it?” Grudgingly, he nodded. “Imagine that being your life full time, not just once a week for a few hours.” She leaned in close to him and whispered in his ear, “Plus since I’m head Mistress, I expect you to be my personal slave. That means you get to tend to my more intimate needs. So what will it be? Do you want to cum or be our slave?”

His mind was on the verge of shutting down. He was completely torn. His body was screaming not only for an orgasm, but to stop the pain being inflicted on his backside. Deep down, however, this is exactly what he wants and being more intimate with Alex, whatever that may mean, is too good to pass up. He softly said, “Slave. I want to be your slave.”

She smiled, “Beg us not to let you cum. Convince us that’s what you really want.” For a moment he paused, but then he did what she wanted and begged them all to not let him cum, to keep teasing and tormenting him, to use them in any way they wanted. She let Victor go on for a long while before finally stopping him, “Okay ladies, I’m convinced. How about you?” Everyone agreed and they all stopped what they were doing, leaving Victor to hang there, body shaking as he tried to catch his breath.

The room was quiet until Domina Amethyst said, “Now that it’s settled, I should go. It’s getting late.” She walked to the front of Victor and roughly grabbed his balls, pulling them down and squeezing hard, “These had better stay full. I went easy on you today, you don’t want to see what real punishment from me is like.” She then bit him hard on the neck, said goodbye to the others, and left. Donna agreed it was late and left as well, but not before giving Victor a slap on the ass.

Christina hesitated for a moment, “I should probably leave you guys too. I’m still pretty wound up from teasing him all day, though.”

“So stay. I’m sure Victor won’t mind, do you, slave?”

Still helplessly hanging from the ceiling, he had little choice, “Of course not, Mistress.”

“See? Let’s take him to the bedroom and put our new slave to good use.”

As they lowered him from the ceiling, Victor was again reminded that he is a very lucky man.