Mr. Hunter's Second Chance Academy Ch. 03

Chapter 3: Damned if You Do, Damned if You Don't.

I've enjoyed S&M sex since my earliest recollection. My very first memory of being aroused involved an old Piggy Hamhock cartoon (Pigs is Pigs, Merrie Melodies, 1937) where he was strapped into a chair and force-fed by an evil scientist. My reaction to those images was very strong and I instinctively knew that it wasn't typical. I was far too young to understand much about sex and that incident was largely forgotten. Many years later, I read a letter in a Penthouse magazine by a woman who was spanked and forced to wear a butt plug by her husband. I had the same reaction and the die was cast.

After that, I knew what turned me on and I sought out stories, letters, videos and magazines that catered to my predilections. By this time, I was sexually active and even convinced more than one girl to play some games with me. Some were more enthusiastic than others but all indulged me up to a point. Unfortunately, none of these relationships gave me exactly what I was looking for in either quality or quantity but I eventually found myself in a position to act out my most perverse fantasies.

Several years ago, I set out to document how this journey began and wrote a couple of stories about it. They are published here under the title, "Mr. Hunter's Second Chance Academy". I only made it through two episodes before life got complicated and I didn't have time to write anymore. One should really take a few moments to read the first two installments but the following story will stand alone, even if it is short on background.

Jennifer, Chloe and I finished our tour of the country without picking up any more participants. We met several and declined to offer them a position for one reason or another, though we did put a few through their paces. Perhaps, if time allows, I'll write about some of those adventures later. A few candidates failed to show up for the interview and one had the decency to cancel ahead of time. No matter. The girls I had selected proved to be everything I dreamed of and served me very well for the next four years. I enjoyed playing with them, training them and teaching them along the way. One particular evening stands out as an example of the kind of fun we had.

I love putting submissives in positions that will cause them to suffer but allows them some level of control, even if it only prolongs the inevitable. On this particular evening, I had decided to put both girls in just such a position.

Jennifer and Chloe were instructed to bathe, shave and present themselves to me precisely at eight o'clock. They must have been busy playing with each other in the tub because they bounded down the stairs in their fluffy, white bathrobes at 8:05. They were both gorgeous in their own way. Jennifer's perfect feet and long legs predicted the athletic form covered by her robe. Her dark skin and hair, set off by the white material, made her look like an exotic beauty. By contrast, Chloe's pale skin radiated pink vitality, partly from the hot water of their bath and partly from the blush, no doubt, brought on by their Sapphic play. They approached gingerly, knowing that they were in trouble.

I ordered them both to drop their robes and assume the position. The girls immediately dropped their garments, as well as their sheepish smiles and instantly took on the demeanor of penitent slaves.

I had Jennifer kneel in front of me with her hands behind her head as I unzipped my fly. Slowly, I withdrew my hardening member and let her pay homage to me. I like a slow, loving blowjob and that's how I trained my girls. Some women suck dick like they're trying to siphon gas out of their neighbor's gas tank. They suck too hard and there isn't anything sexy or erotic about it. Others stroke back and forth too fast, subscribing to the belief that faster is better. Still others are too dramatic and sloppy and they're just hoping you'll be done soon. I rarely like to come in a girl's mouth, preferring her to worship my cock for a few minutes then move on to bigger and better things.

I soon tired of her ministrations and moved both girls to the playroom. Our play space is quite well equipped with a bathroom, several cabinets full of all sorts of toys and a few pieces of dedicated furniture. For this exercise, I had Chloe climb up on a massage table and get on her elbows and knees. She dutifully lowered her shoulders and spread her knees as far apart as she could. By rotating her hips outward and pressing her ass back, she gave me full access to her glistening pink pussy and perfect rosebud. I grabbed each cheek and roughly spread them apart as I licked slowly and deliberately from the apex of her slit up to the introitus of her vagina. She tasted wonderfully clean and her skin was perfectly smooth, inside and out. Chloe moaned and wiggled just enough to show me how much she appreciated the attention. I then moved my tongue up to her ass and she pushed back to get my tongue inside.

"Greedy little slut!" I spoke playfully as I slapped her right cheek. The blow caused her to lurch forward and twist her hips even more. She loves to be spanked and have her ass played with but tonight we would push her limits. I pulled away and had Jennifer take my place laving Chloe's asshole while I located my first implement of punishment. I hadn't planned on whipping either girl tonight but their earlier tardiness needed to be addressed.

"Both of you will be punished for making me wait", I said as I drew back my arm.

"Count the strokes for your sister since she's got her tongue up your ass, Chloe."

I swung with a moderate amount of force and the suede flogger impacted Jennifer's ass across both cheeks, leaving multiple pink stripes. If the whipping had been solely for pleasure, I would have started slower and lighter but this wasn't about sub-space, it was about getting their attention and preventing further abuses of my benevolence.

"One, Master!", Chloe said as she heard the blow and felt her partner sharply inhale. I kept up a steady rhythm until I had delivered twenty strokes. Despite my intentions, Jennifer was more aroused than ever. Instead of crying out with each blow, she was moaning and eating Chloe's ass with ever increasing enthusiasm. Chloe, meanwhile, was mewling and clawing the table in an effort not to come without permission.

I decided that it was time for a punishment enema for my little pain pig, Jennifer. A punishment enema is different than a cleansing enema in many ways. For instance, it might be delivered in a difficult position such as standing or on hands and knees. It might include an ingredient to irritate the bowels and might be hotter or colder than normal. A sub might also be forced to take a larger volume than usual or retain it longer. On this night, Jennifer would have to deal with all of the above. To make matter's worse, she would be a party to her own torture.

While I was arranging Jennifer into position, I had Chloe get down off her table and make up the enema which consisted of two-liters of very warm, very sudsy water in a bag connected to a double-balloon nozzle. I had Jennifer kneel on the floor in the same position that Chloe had assumed on the table and soaped up her ass. The soap would lubricate her anus to allow the insertion of the inner balloon and produce a nice burning sensation. I inserted my index finger as far as I could and twisted it to distribute the soap. Jennifer whined and tapped her toes on the floor, a sure sign that the soap was doing its job. I couldn't resist inserting another finger and fucking her ass with them while Chloe finished her task. When both girls were ready, I inserted the nozzle into Jennifer's ass slowly but firmly. Once the first balloon was in, I inflated it with a few gentle squeezes of the pump.

"Oh, God!" was all she could say between gasps for breath. All this drama and the real punishment hadn't even begun. I tugged on the tubing to be sure that it wasn't going to slip out and, when I was satisfied, inflated the outer balloon. Her sphincter was effectively sandwiched between two balloons and her rectum was full. She would have to take and hold all two-liters of the solution whether she wanted to, or not.

Now came the fun part. I had her stand up and connected the enema bag to the end of a rope in front of her. The rope went up and over a pulley and back down to a ten pound weight. The weight also had a shorter rope attached to it and that one went to a handle much like a water skier would hold. The object is this: the slave must hold her arms out straight in front of her so that they are parallel to the floor. This will hold the weight up and allow the enema bag to be nearly at waist level. Little or no water will enter her body with the bag this low. As her arms tire, the weight will get lower, pulling the bag higher and causing the water to flow faster. In addition, the full bag acts as a counter balance making it easier to hold the weight off the floor. As the bag empties, more weight transfers to the arms, making the task progressively harder, just as her arms are weakening. If she drops the weight entirely, the bag will be at eye level and her colon will fill quickly, and perhaps, painfully.

A smart, or experienced, submissive will realize that they are eventually going to take the entire enema either way. They will purposely lower the weight and use their limited strength and endurance to control the flow. To prevent this from happening, I also attached nipple clamps to each of Jennifer's tits. She hissed through her teeth as each one bit down on her tender flesh and hers eyes flashed up to meet mine. The clamps were attached to a chain which was then looped around the ski rope. Prematurely lowering the weight would cause painful stretching of her nipples and would likely be avoided as long as possible. I opened the valve on the enema tube and turned my attention to Chloe.

The focus on Chloe's asshole earlier may have primed her for things to come but I doubt she imagined the full measure. I liberally greased her up and took the opportunity to insert two fingers roughly into her rectum. She only moaned and threw her head back, hoping I would kiss her. I obliged by grasping her throat firmly in my left hand and kissing her open mouth passionately. I growled in her ear that there was much more where that came from as I let my lips trail across the nape of her neck and her knees buckled.

For her torment, I had my victim stand about eighteen inches away from the wall and lean back until her shoulders touched it. Then I had her slide down until her back was flat against the wall, her thighs parallel with the floor and her shins and thighs made a 90 degree angle. Working quickly, I placed a very small chair under her and positioned a very fat dildo against her anus. As her thighs weakened, she would have no choice but to be impaled on the phallus. Chloe loves to have her ass filled but this dildo was as big around as a beer can, much larger than anything she had taken to date and it held a nasty surprise. To prevent her from standing up, a short strap was placed over her thighs and secured to the chair. Since her nipples were pierced, it was difficult to clamp them. Instead, I looped a small noose around each nipple behind the barbell. The string was then connected by a break-away thread to a ring on the wall above her head. As she sank down on the dildo, her nipples would be pulled painfully upward but the thread would break if too much force was applied.

With Chloe positioned for her torture, I was free to see how Jennifer was doing. As I suspected, she was struggling to hold the weight up but was managing to keep it about ten inches off the floor. Her nipples were stretched beautifully and the enema bag was near shoulder level and still mostly full. Her entire body shone with perspiration and her face reflected her growing agony and exertion. She had been whipped earlier but I was about to add some new welts to her reddened cheeks and maybe elsewhere.

I selected a riding crop from the implement cabinet and landed the first blow on her left haunch, reminding her to keep the weight up. She struggled but succeeded in lifting it a few inches. She did a good job keeping it up as I landed ten blows on each cheek and then turned my attention to her breasts. Five sharp licks connected with the skin above each nipple, causing the clamps to shake violently and torment her tits even further. I grasped a handful of hair and roughly pulled her head back.

"Will you ever make me wait for you again?", I virtually spat into her face through gritted teeth. "No, Master!", she said desperately. With that, her arms collapsed and the weight hit the floor. The clamps were brutally pulled from her nipples and she began to dance on her toes as the hot, soapy water rushed into her bowels.

Chloe wasn't doing much better. She had taken about two inches of the dildo but was still not at the widest part and her nipples were distended upward. She had reached that point where one's inner sphincters refuse to allow further penetration. I traded the crop for a small pussy whip made of leather boot laces and the fear was evident in her expression when she saw it.

Since this was supposed to be punishment, I didn't hold back much as I swung the tails through an arc that landed them on the tender flesh beneath her left nipple. Twelve raised welts appeared where the strands landed. I repeated the act until each tiny breast had sustained ten lashes and the welts overlapped so much that it was impossible to distinguish one from another. Each blow caused her tits to bounce and be painfully teased by the strings. In addition, her bouncing caused the dildo to inch relentlessly into her core. Ten underhand lashes directly to her slit and her punishment would be almost complete. She was sobbing but held her thighs apart as each blow landed, feeling like a dozen bee stings. With the last one, her thighs gave out and she sank down into a squat, forcing the dildo deep into her rectum. It's a bitter-sweet moment when the inner muscles give way. It feels incredibly good when the body finally submits and several inches are absorbed all at once but the sudden feeling of fullness can be overwhelming.

Chloe groaned as her asshole stretched to new dimensions and I reached down to strum her ravaged clit. She instantly came in my hand and fell forward onto her knees, breaking the thread holding her nipples hostage. I left her to catch her breath and turned back to my other captive.

Jennifer was standing there utterly defeated. Her hair was wet with perspiration, her belly slightly distended from the large volume enema and she had angry red welts on her tits and ass. Her breath was coming in short gasps as she tried to deal with waves of cramps as the bag hung empty. The final humiliation was to have her stand with her feet apart and spread her pussy lips as wide as she could with her fingertips. I lashed her open cunt with the pussy whip, each blow causing her to whip her hair back and forth and cry out. True to her training, she never let go of her lips or tried to shield herself. With the tenth blow, she came violently; shivering, shaking and groaning. When she had calmed down and I finally felt that she had learned her lesson, I disconnect the enema bag and let her go to the restroom and clean up.

Chloe was still impaled on the huge dildo and was ready to be released as well. Little did she realize that the object up her ass was inflatable and was capable of getting much bigger. Before I let her go, I gave the pump a few quick squeezes and the rubber swelled in her asshole. Her eyes bulged and she squealed but smiled up at me. She was rewarded by being allowed to suck me off. I had been rock-hard for at least an hour and steadily leaking pre-come so I knew it wouldn't take long. While she sucked, she bounced up and down, fucking her tormented asshole on the enormous dildo. The thought of my wanton slut jamming her sore ass down on that tool was more than I could handle and I gushed rope after rope down her delicate throat. She had won my favor and I slowly helped her up and allowed her to join Jennifer in the bathroom.

When the girls returned, they were carrying the balloon nozzle and dildo menacingly. They had decided that I should be subjected to the enema and dildo so that I could appreciate some of what I had put them through. I like to get as good as I give so I was game for it and we retired to the bedroom. I ate Chloe's pussy and Jennifer rode my dick while I took my enema and then I ate Jennifer's messy pussy while Chloe fucked my ass with the inflatable. The evening finally wound down with Jennifer fisting my ass while I fucked Chloe. As I stroked backward, Jennifer shoved her fist into me. As I stroked forward into Chloe's velvety pussy, Jennifer withdrew. The intensity of the double-team thrusting quickly brought me to another orgasm. Chloe wrapped her legs around me and screamed as she came with me. Jennifer did her part by licking us both clean and this led to the girls eating each other to many more orgasms. In fact, they were still going when I fell asleep! Overall, it was a very memorable evening and only one of many. When time allows, I'll try to write about some of them.