Five Nights with Madame Pearl

Continuation of House of the Rising Sun

Five Nights With Madame Pearl

Day One

       Mistress Sun had asked me to stay at her house for the week while she was out of town on business. I gladly accepted, knowing how happy it would make my mistress. My first mistake came on Monday morning while I was attending to my morning erection. I was in Mistress Sun’s bathroom, eyes closed and completely oblivious to anything other than pleasuring myself when I heard a distinctly feminine cough. I opened my eyes to find Madame Pearl wagging a finger at me and giving me the evilest of grins I could imagine. She told me that I was pretty much fucked if I finished or not, so I closed my eyes and quickly completed my business.

       Madame Pearl grabbed onto my cock and tugged me into Mistress Sun’s bedroom and then into her closet. She began throwing pieces of clothing at me and told me that I had three minutes to be ready. With a few seconds to spare, I was dressed in a skimpy latex maid’s uniform, four-inch posture collar, and three-inch high heeled fuck-me pumps. She completed the ensemble with a pair of handcuffs on my wrists and another pair of shackles on my ankles with about eighteen inches of chain. She told me that she expected the entire downstairs to be cleaned by five that night and I quickly shuffled down the stairs and got to my duties.

       Promptly at five, Madame Pearl sat down for dinner, which I had just finished preparing. Before beginning to eat, she ordered me into the basement, where I was to wait on my knees for her to begin administering my punishment for my earlier dalliance.

       After waiting for close to an hour my mind had wandered to just about every corner of every deviance of every punishment Madame Pearl could have in mind for me. I wasn’t even close to imagining what was to come. I heard the door open and a cascade of light preceded her down the stairs. She was wearing her thigh high leather boots and a leather bra made to look like flames cupping both of her breasts. She was absolutely stunning and my dick quickly stirred which she let out a small smile for.

       She had me strip down to nothing before she threw me a blindfold and a ballgag, which I quickly put on. I then heard her in pulling out the chest of hemp rope with which she began applying a very intricate rope harness. She secured my arms behind my back and against my chest, which also had the effect of limiting my breathing. She then had me sit on the floor so she could tie my ankles to my thighs. I heard her adjusting the pulley system on the ceiling and then I felt myself being hoisted in the air or at least my chest was. My knees were left on the ground and my torso was parallel to the ground, nothing too tough, and nothing I hadn’t been in before and survived. She then applied a pair of clover nipple clamps and chained those to the floor, limiting how much I would swing one way or the other without risking losing a nipple.

       I started to sweat when I heard the click of her heels circling me. As she tightened my gag another two notches she explained to me why I had been a very bad boy. She leaned in close and whispered into my ear in her best Asian-accented English “You should know by now, little boy, that you don’t have to fantasize about fucking me. You’re already living a fantasy, and if you want to get fucked by me, all you have to do is ask. I’d be real careful if I were you about struggling too much, because the more pressure you put on these clamps, the tighter they tend to get.”

       I heard her giggling as she wheeled something up behind me. I started to get an idea of what was going to happen when she began applying the Astroglide to my ass. I next felt a dildo pressing against my anus.

       “I’ll come back to check on you in an hour, just to see if you still want to fantasize about getting fucked by me. I’ll be watching you on the tele in the den, make sure you put on a good show for me.”

       With that she flicked the switch and walked out the door, leaving me to my torment. After a few minutes I began to get used to the slow, rhythmic, fucking of my ass and actually began to get quite turned on. After about fifteen minutes, my dick was so hard I was sure that I was going to explode. Then the machine doubled it’s speed and I heard Madame Pearl over the intercom “That’s right my little fuck-slut, you better keep wiggling that tight little ass of yours. And don’t think that I don’t see how hard that little cock of yours is either. I know that little slut ass of yours is loving this.”

       This continued, with her changing the speed every fifteen minutes or so for a couple of hours. My dick was still pulsing, maddeningly hard when I heard the door open.  Immediately I felt her small hand wrap around my cock and begin stroking. She whispered in my ear “You better enjoy this one, this is the last orgasm you’re getting this week. At least until Sun gets home.”

       It didn’t take long for me to climax and it was the best orgasm I’d ever experienced. Madame Pearl released me from the ceiling and untied my legs so she could lead me into her bedroom. She pushed me onto the bed and had me eat her pussy until she fell asleep after which I immediately passed out.

Day Two

       That morning, Madame Pearl had me dress up in the same uniform as the day before and had me clean the dungeon. I don’t know where I found the strength from the night before, but by five I had finished and had enough time to prepare dinner. She once again had me wait for her in the dungeon.

       She announced her presence the same as the night before, slowly strutting down the stairs in her thigh high boots and nothing else. She had me strip before she lead me into the red room, called so because of the red velvet that draped every wall and accented only by a St. Andrews cross in the middle of the room. She had me step onto the pedestals at the base and duct taped each of my arms to the cross, using an entire roll on each arm, taping from my armpit to the tips of my fingers. She repeated this with my legs and once again I knew I was in for a long night. Watching her work so expertly at immobilizing me, my dick was standing straight out. “I hope you weren’t expecting to use this tonight,” she taunted as she slapped it a few times.

       I had to open my stupid mouth and respond with some smartass answer. She just smirked and pulled out a pair of silk panties. She wrapped the panties around my dick and began to stroke me off when I opened my smartass mouth for the second and last time “I thought last night was my last chance to cum?”

       “I thought I’d be nice to you and let you have one more chance,” she replied while speeding up her hand. I came after a couple of minutes, right into her silk panties which she then quickly shoved into my mouth. She produced another roll of duct tape and quickly sealed the cum stained panties in my mouth. She then began sucking and tugging on my nipples, pinching and teasing them until my cock sprang back to life. She then left the room and returned with a bowl of ice which she used to vanquish my erection.

       The next item I saw in her hands was one that I had heard of and had always feared. A little chastity device called Kali’s teeth. It left no access to your penis and punished erections with a devious little ring of semi-sharp teeth. While she began fitting the device on me she taunted me “This should teach you to play with yourself in the way that I know you do. It should also teach you not to open your mouth without thinking about what you’re going to say.”

       Once the device was snugly on and locked into place she took my nipple into her mouth and began to suck on it while tweaking the other nipple, dragging her long finger nails against it, all the while I struggled to not let my cock get hard. It didn’t work, soon it was straining against the device. She laughed as she walked out of the room and returned with a DVD in her hand.

       “I hope you like this new video I picked up for you, the title is Lesbian Bondage Olympics, six hours of the sluttiest lesbians in the strictest bondage imaginable.”

       She threw it in the player and lowered the screen. She started the movie and before she left played with my nipples once again. “I’ll make sure to record this little session for Sun. Have a good night, slut-boy.”

       I watched her walk out of the room and I could only make the slightest noise from behind the gag. I didn’t think she would actually leave me like this for the night, but I didn’t see her again until the morning. She took one look at my cock and knew that I had had a very difficult evening. She extricated me from the cross and allowed me to take an extra long shower and a short nap before I put my maid’s uniform back on.

Day Three

       Today Madame Pearl had me outside doing yard work all day. She allowed me to do it bare foot instead of the heels, but she insisted that I wear the maid’s uniform, collar, and handcuffs. Mistress Sun lived in a very remote location, thank God, but I was still mightily embarrassed to be outside in that ridiculous getup. The biggest moment of humiliation came when the UPS man made a delivery and wouldn’t stop staring at me. Madame Pearl even asked him if he wanted to fuck me in the ass, but thankfully he said no. At the end of the day, she even allowed me another shower before that evenings activities.

       She told me that she missed me the night before and she planned on making up for this evening. Madame Pearl trapped my arms into an armbinder and led me into the theatre room. There she tied my ankles to my thighs, locked a collar around my neck and locked the end of the armbinder to the vicious little chastity device still on my dick. She told me that she had never seen Lord of the Rings before and she thought it would be nice to watch it tonight. I wasn’t the most comfortable the way I was tied, but I’d been through worse. She just giggled and said to me “Oh, you silly little slut, you don’t get to watch it, you get to eat my pussy for the entire movie. If you aren’t satisfactory in your efforts, I’ll watch the whole goddamn trilogy tonight.”

       With that she positioned herself in front of me on the couch and pulled my head into her crotch. She must have installed a d-ring underneath one of the cushions because she locked my collar to it and I was stuck at the perfect level to eat her out. This wasn’t too bad of a punishment for me, much more of a reward because Madame Pearl has the most fantastic pussy, besides Mistress Sun, that I have ever been allowed to taste. Her first orgasm came quickly, and many more followed, I lost count after six, but by the end of the movie she said that it was satisfactory. She also said she might have to make this a regular Wednesday activity. She untied my legs and removed the armbinder before leading me to her bedroom. I really knew she was sated when she chained my collar to her bedpost and had me sleep on the floor instead of me continuing to perform oral sex on her in bed.

Day Four

       While I was dressing into my maid’s uniform that morning, Madame Pearl informed me that she would be having a small cocktail party that evening and that I was to prepare the house for that evening. I spent the day scouring the first floor, not wanting to embarrass Madame Pearl or Mistress Sun by having a dirty house. An hour before the guests were to arrive, Madame Pearl informed me of my duties for the evening. I assumed that I would be dressed in some slutty little dress and serve drinks for the evening but she had something much more devious in mind.

       “Since Mistress Sun does not have a bidet installed in the bathroom yet, I think you should serve as a live bidet for my guests tonight. I have some of the most powerful women in the area coming over tonight, and it just wouldn’t do to disappoint them. I can hire any fool to serve drinks at this thing, hell most guys would beg to do it and do it for free considering who’s going to be here, but it takes a special kind of slut to do what I’m asking. And if you don’t want me to tell Sun about your dalliance earlier this week, you probably shouldn’t complain about your duties for the evening.”

       Reluctantly I followed Madame Pearl into the bathroom. She had me strip naked and sit on the floor, drawing my knees into my chest. She first used rope to get me into as tight of a ball as she could, squeezing my legs into my chest with hundreds of yards of hemp rope. She then tied my wrists and elbows together behind my back. She then took a piece of rope and tied it to the rope wrapping my chest and attached it to a pulley on the ceiling. She tipped me back, so I was at about a forty-five degree angle to the floor, and so my head was at approximately the same level as the toilet. I was once again absolutely helpless to the whims of this mad, mad woman, and all she could do was giggle. She squatted on the toilet for a quick piss and then quickly stood over my head and lowered her pussy onto my mouth. I knew what to do then, I quickly cleaned her pussy for her, cringing at the small tastes of urine I’d be forced to deal with for the rest of the night.

       Before she left me in the bathroom she showed me two things that would help explain my presence for the evening; a sign that read: “Please use my little piss slut in the same manner as you would a bidet.” She also placed a little jar next to me that read “TIPS for the sluts lipstick.”

       Wanting to add one, finishing touch to me before she left, she took out her hot pink lipstick and painted my lips up to look like a hooker. She giggled at me one more time and then shut the light off and closed the door. Within a few minutes the first guests arrived, and after a half hour the first woman came in the bathroom. She was pretty shocked at my being there, but after using my mouth to clean her up she left with a smile. The next woman through the door was Madame Pearl with my blindfold, explaining that some of the women didn’t want me to know who they were.

       My evening was pretty busy, as the more the women drank, the more they were in the bathroom pissing and using me to clean them up. Quite a few of the women actually demanded that I go down on them and I had no choice but to oblige. By the end of the evening I was feeling like the filthy little piss slut that Madame Pearl had set out to make me. She allowed me to shower before I went to sleep at the foot of her bed, but she would not release me from her special little chastity device.

Day Five

       Friday morning finally arrived, and Mistress Sun was due back that evening, so I figured I could take whatever devious little punishment Madame Pearl would dream up. But the day started off just like any other, she had me clean the house up quickly for Sun’s return, but she said she wanted me in the dungeon by three. I took my time getting my cleaning done and when I arrived in the basement, Madame Pearl was already there getting things set up.

       “I heard such great things about you from the party last night, so I thought I’d give you a little end of the week reward. Come over here so I can take off that nasty thing on your cock.”

       I sprinted to her so I could finally feel normal again. She unlocked the Kali’s teeth and my cock immediately sprang to life. She giggled as she traced her fingernails against the head of my cock, enjoying how it bounced for her. In the middle of the room, she had set up a small, leather bound table that was about the size of a mattress. It had tall poles at each corner with d-rings hanging every few inches.

       She had me sit on the edge of the table while she wrapped my hands with duct tape, keeping them in tight fists. She then put leather mittens over the tape, and locked them on with padlocks. She had me lay flat on the table so she could lock my hands to the poles. Leather ankles cuffs followed, and they were locked to the same poles as my hands, forcing my body to bend uncomfortably. It also gave me a pretty good view of my own dick. A blindfold soon followed, leaving me unable to see the very strict dental gag she carefully placed in my mouth. She ratcheted it up as much as it would go, leaving my jaw stretched to its maximum and leaving my mouth completely vulnerable.

       I felt a cool sensation on my ass as she applied some lube and then she shoved in a moderately sized butt plug. I heard her fiddling with a few other things and try as I might, I could not expel the plug on my own. A pair of clover clamps was quickly applied to my nipples and then fastened to the gag, forcing my head up. She was nice enough to put a pillow behind my head so I wouldn’t strain my neck too much. She then explained my predicament to me while she slowly stroked my cock “I thought I would leave Sun a nice present for her return, and she should be home in a couple of hours. It’s not just a butt plug that you’ve got in your ass right now, it’s attached to a fairly large enema bag, full of hot, soapy water. It’s probably too hot right now for you, but the longer you can wait, the more comfortable it’ll get.”

       It was at this point that I made as loud a noise as possible, even though she couldn’t understand it.

       “I was getting to that part, anyways, there’s a clamp on the hose right now with a string holding it there. I’m going to tie the string to the tip of your penis. You’re pretty hard right now so here’s the deal, as soon as you get soft enough that the string gets too much slack in it, the clamp comes off the hose, you get an enema. If Sun gets home before you get soft, you don’t get an enema. That seems pretty simple. I’ll leave you be now, I want to make sure you’re nice and ready for her.”

       She soon left the room, leaving me to my misery. I tried every trick I had ever learned to stay hard, concentrating deeply on every fantasy I had ever had and even deeper on some of the kinkiest situations I had never been in, but I could only hold out for an hour. I felt the string begin to slip and finally fall off completely. A few seconds later I felt the rush of warm water. After an eternity, the water stopped flowing and I was left with a very full feeling. Another hour passed until I heard the door open. It was not the voice I was expecting “I just got off the phone with Sun and she’s stuck in Minneapolis for the night, something about mechanical problems with the plane. I hope you can make it until tomorrow morning.”

       And then I heard the worst sound I’ve ever heard, the door closing and Madame Pearl walking back up the stairs. There was absolutely no way I was going to last until morning, I wouldn’t last another hour. I was sweating buckets, struggling with every ounce of strength to get out when the door re-opened. I felt Madame Pearl’s hand grip my cock and begin to slowly stroke it. Soon she had me on the brink of orgasm and it was then I realized why she used the dental gag. Before I could think to move, I came, straight into my mouth. A few drops missed, but Madame Pearl was kind enough to clean them up with her fingers and wipe them on my tongue. As she began unlocking me from the bench, she began to tell me about all of the fun we’d be having tomorrow until Sun came home. All I knew was that I had just finished another night with Madame Pearl and for some reason I had the same taste in my mouth that I usually had. I could not wait for Mistress Sun to return, but I also couldn’t wait for her to go on another business trip.