––––––––
She looked distinctly uncomfortable standing in front of me, but I pretended I didn’t recognize her. I made a point of ignoring her as I read her résumé much slower than necessary, only occasionally glancing up and staring at her like she was a statue or something.
“You realize you’re signing up for a one year contract and won’t get a penny if you leave early, right?”
“Yes sir,” she replied.
“You also realize that we live in a certain lifestyle here that many consider to be kinky or depraved?”
“Yes sir.”
“I expect flawless service and instant obedience from everyone working here, and administer both immediate and weekly punishments for any shoddy work or intolerable actions. Do you have a problem with that?”
“No sir.”
“Do you have any questions?”
“Yes sir. Will I be forced to have sex with you or anyone?”
“No. I’m not a rapist and any sex around here needs to be a hundred percent consensual. Sex is very common in this household and you better get used to seeing it at any time or place, but there’s no need to participate unless you choose to. Any other questions before we begin?”
“No sir.”
“Then welcome to the team. You will refer to me as Master from now on. This is Mistress Silvia and Mistress Claire. Failure to address any of us in the proper manner will earn you an instant blow from this riding crop I carry around. Do you understand?”
“Yes Master.”
“Good. Claire, why don’t you give her the tour, explain her duties, and set her up in one of the unused bedrooms.”
“Follow me,” she said, rising and heading out the door.
I waited until they left and closed the door behind them before turning to Alfred.
“How did you find her, and how did you know about us?”
“Your father gave me the job of keeping an eye on you, so there wasn’t much you did that I didn’t eventually find out about. I knew this girl was a sore spot with you, so when Silvia asked if I knew of someone who’d be a real challenge, I tracked her down and made an offer she couldn’t refuse.”
“After the way she ran out on me before, I doubt she’ll last more than a day before she’s running full speed out the door.”
“Then it’s an appropriate challenge for you,” Silvia said. “Someone like Lily will already obey any command you give her... someone like Shelly needs to be carefully trained to think like that. If it was easy, then it wouldn’t be a worthwhile test.”
“I guess you’re right, but I’ll admit I’m a little adrift right now over this surprise situation.”
“You have three months to figure something out, but you’re a bright kid and I’m sure you’ll come up with something.”
I wished I had her confidence.
***
“Shelly,” I called. “Come with me, I have something to show you.”
“Yes Master.”
For her first week working for me, she was generally excluded from any punishments other than a blow from the crop if she failed to address me properly. I still wanted her in attendance for the regular Saturday night session in order to help her understand a few things.
I led her down to the playroom and told her that since she wouldn’t be receiving any punishments or rewards, she’d be serving everyone tonight. She’d been with us for five days now, and I thought it was time to introduce her to a bit of light bondage so she’d start getting used to it.
I made her change into the slutty latex French maid uniform and put on wrist and ankle cuffs. I told her it was a rule that any girl serving in the playroom had to be at least minimally restrained, so I connected her wrists with a twelve inch chain and her ankles with an eighteen inch one. Ok, I’ll admit I just made that rule up, but that’s a master’s prerogative.
I made her open her mouth so I could put in a small ball gag, and buckled it only slightly snug. Her eyes looked a little wild, but she eventually calmed down as I ignored her after telling her to pour me a scotch on the rocks.
As the other girls began making their way down to us, she got too busy to think too hard about her new predicament, and actually became somewhat professional in her duties. I kept a close eye on her, but made sure I never made direct eye contact. I wanted her to think of herself as just one of the household staff.
I deliberately gave out fewer punishments and more rewards than normal that night, since subtlety seemed to be the card I needed to play with her. Overall, she didn’t seem to react badly to the proceedings, and I even caught her staring in fascination every now and then at the girls I’d put into bondage.
I decided to try upping the restrictions I placed on the servants, gradually making corsets, ballet boots, and gags part of the everyday routine. I began spending more time in the playroom and made sure there was always at least one girl in bondage whenever Shelly was around.
Putting my creative taskmaster’s hat on, I also made sure that at least one girl got a harsh punishment every week, with another getting an extremely sensual reward. She was never one of the girls chosen, but was getting trained with the carrot and the stick technique nevertheless.
I ran like that for a month before ensuring she earned one of the harsher punishments and I got my first turn at working her over. I had her bend over the spanking bar, which she reluctantly did. Her reluctance earned her a large ring gag and a strappado tie for her arms, but that was all to the good as far as I was concerned.
I gave her twenty medium strength lashes with the flogger and left her tied in place while I dealt with the other girls. I’ll admit I cheated for this part, since I’d told the girl I’d be rewarding what I wanted her to pick tonight.
Amber said she wanted to be tied spread eagle, naked, in the middle of the floor (where Shelly had a bird’s eye view, although an upside down one) and be brought to multiple orgasms any way I thought best.
Once she was naked and tied as requested, I informed all the girls that they were allowed to have fun both with her and with each other. I sat on a barstool next to Shelly so I could keep an eye on her reactions to this incredibly erotic Sapphic display of pure carnal lust.
Amber was brought to her first few orgasms by the tongues of the others, but as the night progressed it degenerated into a chaotic orgy. She was made to cum with a strap-on or vibrator almost constantly, while also being forced to eat a girl out. She’d be useless for service tomorrow and might even sleep for a week after this ‘reward’.
Several of the girls got tired of waiting for their turn and began masturbating with some of my custom-built toys (which were of an appropriate size these days since I’d bought better tools and equipment) or falling into a sixty-nine with someone.
I’d never seen so many orgasms happen in one night before... it was mesmerizing. It was also testing the strength of my pants, and I was surprised my dick hadn’t burst the seams with how hard I was.
I wasn’t the only one turned on by the display either. I saw Shelly was breathing deeply out of pure lust, and she couldn’t seem to tear her eyes away from the orgy. Her nipples were rock hard and I could see her grinding her hips slightly, as if she was imagining herself in Amber’s position. Most telling of all was the faint trail of moisture running from her pussy and down her leg.
Amber looked completely wasted by the time I was ready to let her go, and I had the girls move her out of the way of their orgy and put her on the couch where I joined her. I sat down and cushioned her head in my lap while I stroked her hair and let her relax as we continued to enjoy the show.
While exhausted, Amber was still willing to go the extra mile and after she’d rested a bit she begged me to allow her to show her thanks properly. It wasn’t part of the plan, but she begged so well and I was so incredibly horny, I relented and let her unzip my pants.
She worked my pecker out and slowly caressed it for a minute before plunging her mouth down over it. It felt like heaven, yet her technique was off after all the use her mouth had already been through with the girls. It meant it was the longest, slowest, and absolute best blowjob of my life.
Shelly began watching us and I could see a hungry look in her eyes. I regretted leaving her bound and gagged now, or she might’ve joined right in. It didn’t matter, though, since I could see she was hooked. Her rule of no sex wouldn’t last a week after this.
As the orgy began winding down, I told the girls to release her when they were finished, and have her clean up the mess. I went to my office and turned on the playroom video feed to see how she acted once left alone.
She began by quietly cleaning and putting the used toys in their proper spots, but once the last pair of girls left, she stopped disinfecting the ball gag she’d been working on and went over to the bar. She poured herself a stiff drink and downed it in a single gulp, looking lost in thought as she poured a second drink.
She sat in the recliner and absently toyed with the ball gag as she sipped her drink. As if reaching some sort of decision, she put the drink down and put the gag in her mouth, buckling it tightly behind her head.
One hand went to her chest where she began playing with her nipples and the second went between her legs. Furiously rubbing herself, she came after only a minute or so and fell slack into the chair once the orgasm passed.
She removed the ball gag after a couple of minutes, downed the rest of her drink, and quickly finished cleaning up. I almost turned off the video feed once the last item was put away, but I’m glad I didn’t or I would’ve missed what happened next.
She didn’t put all of the toys away properly. The ball gag, a realistic looking penis vibrator (molded from my cock if you want to know) and several leather belts went into a bag before she scurried from the room to go to bed. How interesting.
Shelly seemed to have a glow about her the next day, and it was hard for me to keep a straight face around her. I decided to have a little fun with her, and told her she’d be helping me in my workroom today while I prepared a new set of toys for the micro controllers I’d built.
I took Lily with us and started by having her mix up the alginate molding powder while I soldered the last few wires to connect the motors to the circuit boards. I couldn’t wait to see the look on Shelly’s face when she realized the toy she borrowed last night was molded directly from my cock.
I’d previously gotten my best casting results when I lay face down over two tables with my groin in the empty space between them, so that’s what I did today. Once the alginate was ready, she poured it into a ten inch long by four inch wide tube and had Shelly start knocking it on the table to shake out any air pockets, while she stroked my penis and got it nice and hard.
A soon as the alginate was ready, she brought it between my legs and pushed it over my cock, making sure my tool was perfectly centered in it. I always found this to be a fun, yet trying procedure, and never had any difficulty in maintaining maximum erection. The hardest part for me was holding still for the eight minutes needed for that much alginate to properly set.
This was going to be a hard day for me since I wanted to make a dozen different models, each with a slight variation to the motor and controller configuration. Have you ever had your dick stuck in warm gooey tubes for two straight hours without getting any relief? You can try it sometime, but I doubt many of you have the needed self-control.
Once the first mold was set and she pulled it off me, I went to prepare the silicone needed for it; I wanted to make sure the controller worked properly before doing the full run of twelve. I picked a translucent blue silicone and carefully filled the mold with it before embedding the motor and controller inside, smoothing the overflow over the top so there’d be a flange around the base.
I normally let the silicone cure for a full day before breaking the mold, but knew it would be set enough to check the operation of my controller after a couple of hours. I got back up on the table so Lily could resume making the alginate molds.
Being someone who used the toys I created, Lily came up with a good idea to increase the pleasure they gave; a finger stub that could sit on the clit. Since she couldn’t hold the mold steady and use her own finger, she had Shelly reach between my legs and press a finger against the base of my prick and into the mold.
I couldn’t believe Shelly did it without question and with only a slight blush to her cheeks. I also couldn’t believe Lily came up with this idea out of the blue, and when I caught her eye she gave me a broad smile and a wink. I’d definitely owe her a favor for coming up with this.
After a few castings like that, Shelly came forward with a tentative suggestion. She offered to try making a mold of her tongue that could be used for the clit tickler portion. She thought it would be hot and so did I, so I gave her permission to try it at the end and we’d do a few castings with it tomorrow after everything cured. (It didn’t actually work very well, but was still a highly erotic idea.)
The last few castings were only half-length ones, and with more space to work with, Shelly was able to both cast my prick and her finger by herself. I had Lily start filling the finished molds with silicone and the components I’d already put out for them, while Shelly took over the rest of the alginate work.
She’d lost any embarrassment caused by fondling and holding my prick by this point, and I was seriously impressed by how far she’d come today. Once the last mold was complete I flopped down in an overstuffed armchair with a glass of cognac, feeling both drained and excited.
I was always overdue for some relief after a casting session and today was no different. Lily finished with the toy she was working on and came over to both clean me off, and finish me off. As her head bobbed between my legs, I caught a glimpse of Shelly out of the corner of my eye.
Her face was flushed and her nipples hard; I was willing to bet she’d swap places with Lily if I asked. I knew I was one step closer to winning, and could hardly wait for the next part of my plan to go into effect.
***
“Ok, ladies,” I said, calling everyone together around me. “Since tomorrow is a rest day for most of you, and you’ve all been working hard lately, I decided tonight should be a night of fun and relaxation for almost everyone. Sorry Jennifer, but you drew serving duty tonight and Kelly will be working breakfast tomorrow morning, so your fun will be limited.”
They both groaned at the thought of missing out, and had a pout on their faces, but they didn’t complain, knowing they’d get their chance next time. They’d also still get to have a bit of fun, just not as much as the rest of us.
“It’s not all fun and games, though, since one thing that needs to be done tonight is the testing and rating of my latest batch of toys. You all know the drill by now; every girl that tests a toy earns a bonus, but has to complete a full hour with the new program running. To enforce the rule, you’ll be bound for the duration.”
Nobody seemed to mind since they’d begun to equate bondage with pleasure by now. Every girl immediately volunteered to be a guinea pig and wanted to go first. The last time I’d held a testing night it was only one girl, and her almost non-stop cries of delight were the envy of everyone.
I picked Donna first and let her randomly her select a toy from the pile. Only I knew what each one was programmed to do, and some of them had the latest version of my orgasm denial program built into them. I’d bought a dozen new laptops for tonight’s test so each toy could be monitored, and even controlled by the program Jerry helped me to write.
She slid the toy home, used a leather thong to hold it in place, electing to use the bondage chair as her method of restraint tonight. I had her start strapping herself in place while I set up a laptop next to her and pulled up the program.
If it worked right, this one should very slowly bring her to orgasm and use that as the baseline for the rest of the session. I hoped for her sake she didn’t cum too soon since each orgasm that followed would happen in half the time of the previous one, and she’d probably be cumming continuously near the end.
Amber was next and had the bad luck to draw one of the orgasm denial models. She’d probably cum once at the beginning while the program was learning her vitals, but the rest of her session would be a complete world of suck. I had Kelly strap her to the St. Andrew’s cross while I hurried to the next girl.
Jade was a bit of a masochist and picked the hanging board for her session. Most girls found the pressure of the board against their pussies unbearable after only ten minutes or so, but Jade seemed to love it.
I bound her arms behind her back and pulled them into a strappado, spread her legs wide and tied them off to floor rings, and stuffed an inflatable gag into her mouth since she was extremely vocal when it came to her orgasms. Her program was completely random and variable, and I wondered how many orgasms it would let her have.
Barb wanted to be tied in a large armchair with her legs spread wide, and had a variant of the denial model. Her toy should bring her closer and closer to orgasm each time it cycled, and finish off with maximum stimulation for the last ten minutes. She was a squirter, so I packed towels under and around her to help minimize the mess.
Julie wanted to be tied in a conventional spread eagle and had already put on cuffs and put the ropes in place. Her toy was a ‘rollercoaster’ model and would slowly go from zero to full power and back down again for each cycle. I had no idea how she’d react to this program but thought it would be quite the ride.
Silvia tied Claire and Lily together in a sixty-nine and had the girls hold each other’s toys in place with their faces. I gave her computer control of the programs for both girls and let her either torment or please as she saw fit.
I’d deliberately saved Shelly for last and simply raised an eyebrow as a way of asking her if she wanted to join in. She held up her hands to show me the cuffs she’d already placed on her wrists and went over to the spanking bar.
Since she hadn’t selected a toy for herself, I picked a red one I knew was my most advanced orgasm denial model, and handed it to her along with a chastity belt. The moans and screams of delight from the other girls had been echoing through the room for some time by now, and Shelly was well primed to accept the large toy.
She slid it in with no problem and quickly locked the chastity belt around her waist before she could change her mind. I spread her legs extra wide and had her stand on her tiptoes before I tied her ankle cuffs to the side posts.
When she bent over the bar I made sure the waist belt was extra secure before I went to the other side and pulled her arms taut and fastened them to the same rings I’d used for her ankles. It was the tightest I’d ever restrained her since hiring her, and my dick was reacting accordingly.
I started the program and let it bring her to the edge, but I watched closely and held my finger over the stop button in case the program didn’t react fast enough. Luckily, it worked perfectly. It cut off just before I was ready to intervene, leaving her gasping, (and swearing) at the sudden loss of sensations.
I still had several toys left on the table, so I let Jennifer and Kelly have a bit of fun by running them in manual mode on each other. Silvia picked one for herself to use while she played with Lily and Claire, and I was the only one left out now... I guess I didn’t plan tonight as well as I thought.
I interrupted Jennifer’s fun long enough for her to bring me some champagne, and wandered around the room to see how the girls were reacting. Donna was oblivious to everything but the buzzing toy ripping orgasms out of her flesh, as was Jade.
Amber called me an evil bastard and begged for some relief, earning her a bit gag and a set of clover clamps on her nipples. I knew she didn’t really hate me when she called me a bastard, but a Master has to maintain his image, right?
The rollercoaster program was highly successful, teasing Julie and slowly stoking the fires until she finally came after about fifteen minutes. Her orgasms looked mind-blowing after such a long, slow buildup, and I knew that program would be a big seller if I ever put it on the market.
The smell of sex was thick in the room by now, and I felt almost drunk from the power I held over these girls. I was also horny as all hell and thought about having one of the girls give me a little relief. I forced myself to wait, but it wasn’t easy.
I’d deliberately ignored Shelly while making my rounds, but her cries of ‘please, please’ had been growing steadily more insistent. I refilled my glass and went over to her, lying on the floor so we were face to face and giving her the chance to convince me why I should stop such an important test.
“Please Master,” she begged. “I’ll do anything you want if you’ll please just let me cum. I can’t take it anymore... please let me cum before I lose my mind.”
“I don’t know,” I said, taking a casual sip of champagne. “It’s important to let the test run without any interruptions, or the data will be faulty.”
“Please, Master, I beg of you to please let me cum. Take the evil thing away and fuck me instead. I’d give anything to feel you inside me right now.”
“That’s a very generous offer, but it would ruin the test. You still have fifteen minutes left to go.”
“Please, Master, can’t we end the test a little early? I don’t think I can last fifteen more minutes without going mad. I’ll suck your dick and give you the best blowjob you’ve ever had if you just end it early and let me cum!”
“That sounds like a reasonable request, but if you want to do it then I need to cum first.”
“Yes, Master, of course. Thank you, Master. I promise I’ll make you cum real fast and I’ll work extra hard from now on to be the best servant in the place.”
“Very well,” I said, sliding my pants down to my ankles.
I had Kelly toss me a few pillows so I could put my groin at a better height, and wiggled into position. She lashed out almost like a striking cobra in her haste to get my cock in her mouth, and began bobbing her head to the limit her bondage allowed.
It wasn’t the best angle of attack, but I’m a guy and it was a blowjob, so of course I enjoyed it. Wanting it to last, I began thinking about what variations of the program I could come up with next. It was just enough of a distraction that I was able to last the full twelve minutes remaining on her timer, and I switched her toy onto full power just as I began shooting my load.
She came almost instantly, choking slightly as I spurted into a mouth gone tense from her massive release. She had enough presence of mind left to finish sucking me off, milking the last few drops out of me and cleaning my prick as my erection slowly subsided.
She came again just as my prick popped out of her mouth, and I began caressing her tits, making her orgasm even stronger and longer. I let her have one more blistering orgasm before shutting down the program and letting her recover. She was panting heavily from the highly energetic release and I couldn’t take my eyes off her heaving chest.
“Thank you, Master, thank you,” she whispered repeatedly in between breaths.
I was enjoying myself where I was, so I had Jennifer and Kelly release the other girls from their binds. Most of them stretched languishingly after being released, and congregated in a circle on the floor, telling each other how the toy’s they’d gotten felt.
Amber was the only exception; she grabbed her vibrator as soon as she was free and pounded herself with it until she came... twice. As I relaxed and listened to their stories, I felt a set of lips brush against my penis. I stared at Shelly until I caught her eye.
“A good slave knows to thank her master properly when the opportunity presents itself,” she explained, before lowering her head again and taking me in her mouth.
She took her time with this blowjob, the frantic pace of her earlier lust forgotten. She even had the temerity to tease me by bringing me close before slowing her action and delaying the inevitable. It was a wonderful technique, and I wouldn’t change a thing.
She kept me going for close to a half hour before finally finishing me off, holding me as deep as she could while I came down her throat. My release was exquisite in more ways than one; I knew she was now mine.
***
Her training progressed quickly after that, and she even took to spending her free time with either Claire or Silvia in order to pick up extra tricks and lessons. She voluntarily changed her wardrobe to include a tight, heavily boned, quarter cup corset to give a little support to her C-cup globes.
She upgraded the standard five-inch heels the others wore into seven inch ballet heels, and locked ankle and wrist cuffs in place each morning after she took her shower. When her duties permitted, she would wear a hobble chain or wrist chain, and was rarely without a gag in her mouth.
She also offered herself to me on a daily basis, although I declined anything other than the occasional blowjob. She’d also stopped taking a toy to bed with her, and had one of the girls tie her arms and legs to the bedposts so she wouldn’t be tempted to play with herself.
On the day Silvia’s contract with me was about to expire, I called her down to the playroom to witness what I had in mind for my final test. I had Shelly serve us champagne and then it was show time.
“Shelly, remove your uniform and gag, and then present yourself to Silvia,” I ordered, tossing her my key ring.
She quickly moved to comply, stripping the latex top and skirt off in mere seconds, although she fumbled with the lock behind her head and couldn’t seem to get the key right. I had Claire finish removing it, and lock her wrists together in front of her as well.
“Sylvia will be leaving us today, and I think you should show her your appreciation for all the hard work she’s done. Diddle yourself while you thank her, and you may neither stop masturbating, nor cum, until otherwise instructed.”
Shelly immediately dove in between Silvia’s legs and started licking, her own hands busy between her legs. Silvia seemed surprised but pleased, and accepted her ‘thanks’ with aplomb. Once she came, Shelly leaned back and resumed her kneeling presentation pose, still rubbing herself of course.
“Claire also contributed a lot to your training, did she not?” I hinted.
Shelly immediately shuffled over to Claire, who spread her legs wide and wrapped them around Shelly’s head. Claire had a bit of an evil streak to her sometimes, and today was no exception. Rather than letting Shelly eat her out at her own pace, she began forcing the issue, sometimes smothering Shelly’s face with her pussy until she was close to passing out.
Claire’s orgasm, when it finally came, was almost enough to make me jealous. She was screaming at the top of her lungs for over a minute and I thought she might pass out from the sheer intensity of it.
She went limp when it finally subsided, although her body occasionally twitched from an aftershock. She slowly pulled her legs back and used her toe to push Shelly back into her presentation pose.
“That was well done,” I complimented her. “Do you have anything to say?”
“Yes Master, thank you for giving me the chance to thank Mistress Silvia and Mistress Grey. May I please thank you now as well?”
“You may.”
She shuffled her way over to me but was presented with a quandary. I hadn’t given her permission to stop playing with herself, yet I made no move to pull my pecker out for her. She tried using her teeth to get my zipper down, but didn’t have much success.
What finally worked was when she straddled my lap and was able to get one hand to grab hold and pull my zipper down. It actually hurt a bit when she pulled my pecker out since my hard-on extended past the level of the waist button, but I didn’t complain since she’d figured it out so fast.
She went back down to her knees and took me in her mouth, no preliminaries needed since I was already rock hard. It felt amazing and I was tempted to let her finish, but I still had other plans for tonight.
“Stop,” I commanded.
She pulled away and looked up at me, confused about what she could’ve done wrong.
“Silvia gave me a present which I’d like to open. It’s on the desk in my office and I’d like you to fetch it for me. You have five minutes to get it and return.”
It was awkward for her to get to her feet in her current predicament, but she managed and scurried off as fast as her hobbled high heels would allow. Her hands were still between her legs and made it twice as hard to move properly, but she never complained.
“I’m impressed,” Silvia said, once Shelly was gone.
“Thanks,” I said, raising my glass in a toast.
“While we wait, I’d like to talk to you about something.”
“Go ahead... it’ll take her at least ten minutes to return.”
“Your two friends, Brandon and Jerry, have hired me to train them in the same manner I’ve trained you. I’ll admit I’ve grown rather fond of living here in the lap of luxury, and since you have a better equipped dungeon than I do, I was wondering if I could stay here and pay you rent while I fulfill their contracts.”
“Silvia,” I said. “You’ve helped me make my life complete. You, Claire, and Lily can stay here as long as you like, but under one condition.”
“What’s that?” she asked, looking wary.
“Never insult me by offering to pay rent again. I’d like to think we’re friends now, and as far as I’m concerned, what’s mine is yours. Not only that, but I’m sure there’s still lots I can learn from you, and I love the idea of doing it on Brandon’s dime.”
She actually laughed out loud at that one.
“I’ll be willing to help out around here in any way I can. Lily will be staying on, of course, but her submissive training is pretty much at an end and it’s time I taught her the dominant role. Will that mess up your plans in any way?”
“Not really. Although I’ll admit I have a hard time buying it when I mentally say the title ‘Mistress Lily’. It sounds like something from a bad Japanese anime flick.”
“She’ll be using her real name once she’s on the other side of the whip, and ‘Mistress Lilith’ has a much better ring to it.”
“I concur. I’ll also have rooms made ready for the boys since it’ll make everything easier if they move in with us.”
“Thank you, Edward. I foresee many long, pleasurable nights ahead of us.”
“I’ll drink to that,” I said, putting action to words.
I heard the clink of Shelley’s hobble chain coming down the hall and put my glass to the side. She was out of breath when she stumbled around the corner and made her way in front of me with the requested package.
I took it from her and opened the box to reveal the silver chased riding crop I’d been using for the last year and a shiny new single tail whip.
“The crop looks good on you, so I thought you should have it,” Silvia explained. “I also noticed you lacked a good whip, so I had Brandon fashion one to the exact specifications I thought would suit you best.”
“I thank you from the bottom of my heart,” I said, and I really, really meant it. “Since I’ve never had a chance to use a proper whip, and since Shelly was so tardy in returning with it, I think she may want to volunteer to help me test it out.”
“Yes, Master, I would love to help you break it in for the first time.”
“Go stand in front of the cross. You may stop diddling yourself now as well.”
“Yes Master. Thank you Master.”
She hobbled over to the St. Andrew’s cross and backed into place. With the three of us, it didn’t take long before she was tightly bound in place and I stepped back to take a few practice swings with the whip.
It was a real pleasure to crack a properly made, high quality whip for the first time. The ones in my collection that I’d ordered off the internet were ok, but nothing like this. I stepped up to Shelly and started with long, slow swipes across her chest, knowing I needed to work carefully with this new whip or I’d easily draw blood.
Starting slow also let Shelley’s endorphin level climb so it wouldn’t be a complete torture for her. The biggest mistakes I’d seen have been due to someone inexperienced start off with full strength blows, causing the maximum amount of pain they could.
That was wrong.
Punishment in a BDSM relationship wasn’t about torture, it was about combining pleasure with pain and intertwining them so deeply that it became impossible to distinguish between the two.
I slowly picked up the pace and strength of my blows until each lash was leaving a nice long red mark in its wake. To her credit, Shelly neither complained nor even cried out, even after her entire chest was a mass of painful looking red lines. I lowered the whip and took a moment to catch my breath.
“Release her,” I said, tossing back the rest of my champagne and flopping down on the couch.
Once she was free, she took the initiative and refilled all of our glasses before presenting herself in front of me.
“Thank you for allowing me to help you test your new gift. What else may I do to please you, Master?”
“Go select some wardrobe accessories that you think might amuse me and then return with them.”
She hobbled off to the toy wall and selected nipple clamps, posture collar, armbinder, butt plug, and the biggest ball gag in my collection. She laid it all out in front of me and waited for my approval. Damn, she sure had it right... I was truly impressed.
I wanted to keep eye contact with her during this phase, so asked for some help from the girls. They removed her wrist cuffs first and slid her arms into the supple single glove, slowly tightening the laces and drawing her forearms together until the elbows touched.
Once her chest was thrust out nicely from the restrictive armbinder, I pulled her nipples out in turn and let the clamp snap into place. She squealed with the force of the snap like I knew she would, and I gestured for the gag.
I began to doubt her ability to accept the mammoth ball in her mouth without either breaking some teeth or dislocating her jaw, but it popped behind her teeth a second before I was about to call it quits. Claire pulled the strap a lot tighter than I would’ve and the way the straps dug into the corners of her mouth looked rather painful.
The posture collar was next, and Silvia tightened it a little on the extreme side, but nothing that would cause any extreme breathing distress. Claire had her plant her face on the floor and thrust her ass up high for the final item.
She removed the ankle hobble and kicked her knees wide apart before squatting behind her and opening the jar of lube. She scooped out a generous handful and slathered it across her rosebud before slowly working it in.
Claire obviously knew what she was doing, as she used one hand to rub her pussy while the second began finger fucking her asshole and slowly getting her to relax the sphincter. By the time she actually grabbed the butt plug and started sliding it in place, it almost seemed like Shelly’s asshole sucked it into place.
I was seriously impressed by Claire’s technique, since as far as I knew, it was the first time anything had ever been up her rear passage. They helped her to her feet where she spread her legs wide and posed for me.
Holy shit, did she ever look good. It was almost too good, and I wondered if this was all some sort of fucked-up dream. Either way, I wasn’t about to mess with either a grade-A dream or an A-1 fantasy come to life.
“It appears that you’ve chosen an outfit that pleases me greatly,” I said, choosing my words carefully. “Now... how do you intend to thank me with that rather obnoxious looking gag filling your mouth?”
She replied in the only way she could; she shuffled forward until she could climb on her knees over my lap and lowered herself on my prick. It was a beautiful gesture, but highly impractical given the current state of her bondage.
Partly out of pity for her predicament and partly because I was ready to explode, I helped guide my prick into her folds. Holy fucking shit... I’d fucked many women in the past, but I swear nothing compared to the feeling I had when she slowly settled down on me and I filled her completely.
She wasn’t able to get a lot of leverage to lift herself fully, but I didn’t care; I swear it was the best sex I’d ever had, and looking back at it over twenty years of experience, nothing else ever did either. Barely able to move two inches at a time, she slowly rode me for the next ten minutes and finally made me cum so hard I thought my toenails would get sucked out through my prick.
Sometime during that session Claire and Silvia had left the room, leaving Shelly helplessly impaled on my prick. I never fully lost my hard-on, and after a few minutes of cuddling and fondling her tits, I found myself rising to the occasion again.
Rather than being distressed by the situation, I detected a triumphant gleam in her eyes. She rode me to another glorious orgasm, made memorable by her cumming at the same time and making it the absolute perfect finish to the night.
My dick was still trapped inside her, but I didn’t think I could survive another round like that. I keyed on the intercom and had the girls on duty come down to help her off of me, and release her from her stringent bondage.
Once she was free and the other girls gone, she went to the bathroom and cleaned herself up. She returned and detoured to the bar, asking me if I wanted anything. I had her bring me a glass of my best cognac and one of my finest Cuban cigars, saying she could help herself to anything she wished.
After bringing me my selection and guzzling a glass of water, she poured herself a snifter of my favorite cognac and rejoined me on the couch, snuggling against me like we were long time lovers.
“May I please speak freely, Master?” she timidly asked.
“Of course,” I answered.
“Thank you, Master, for finally allowing me to gain fulfillment,” she said. “I’ve dreamt of this moment for years, ever since our first time together.”
“Say what?” I replied, stunned.
“You probably don’t remember me,” she continued. “But one night when I was a young girl in college, we hooked up and you tied me up for sex for the first time. I’d never forgotten that night, or how it made me feel.”
“I have a pretty good idea how it made you feel, since you never returned any of my phone calls ever again!” I replied hotly. “You broke my fucking heart!”
“You don’t understand, Master. I didn’t... I couldn’t return your calls because I was afraid. I was afraid of what you’d woken inside of me, and I knew if I allowed myself to submit to you again there’d be no turning back. Ever... and I was right.”
“What do you mean?”
“I love you, Master,” she said, pressing her head against my chest. “I think I’ve always loved you, but didn’t have the courage to come forward and say it before now. Keep your wages and hang the rules... I want to stay with you forever if you’ll allow it.”
For the first time in my life I was speechless. I’d been trying to find a way to win her over, and she’d been trying the same thing. God, we sure were dumb about it, and I briefly wondered how the human race even survived with the sheer amount of stupidity present in modern day affairs.
“Would you like to share my bed tonight?” I asked.
“You’d have to tie me up to keep me away,” she giggled.
“I may tie you up, but not away from the bed,” I replied, rising and carrying her out in my arms. “We’ve got a lot of catching up to do, and there’s no time like the present to get things started.”
I don’t think we got more than a few hours of sleep over the next few days, but neither of us minded. She was now mine, but I was just as much hers... just don’t tell Silvia, ok?
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The Edward Laste and Lilith Chance Collection