How I Became a Chastized Cuckold Ch. 04

"The first thing I am going to do," she began instructing my wife, "is get our little chastity slave clean and prepped. This is not something you have to do if you are in a rush but I prefer to not get dirty while performing the milking."

I heard the sound of a latex glove being snapped on before feeling my ass cheeks being pulled apart and a cold wet substance being placed near my anal entrance. I began to feel pressure being applied against my virgin hole.

"Try to relax your muscles," Madam Sara taught me, "I will allow me to slide in much easier and apply the lubricant."

I fought the involuntary urge to keep my backdoor slammed shut and began to release the tense muscles, allowing the thin, gloved finger to slide inside, coating the entrance with slick lubricant. After a few seconds of working her finger in and out, she removed the gloved intruder before replacing it with something a little bigger. I looked back and saw the thin, clear tubing attached to the new invader. I knew immediately what it was.

"I am going to give your husband an enema," she told my wife. "The nozzle has a balloon on each side of his sphincter that I will inflate to ensure none of the solution will leak out. I like to start with one quart of warm water and allow it to cleanse for fifteen minutes before releasing the slave to expel it. There is always a possibility of cramping and the chance increases if you use cold or soapy water, but you can combat that by momentarily stopping the flow and massaging his lower stomach until it goes away."

She finished inserting the nozzle before using a large syringe to inflate both balloons, the pressure of them acting against the other, squeezing my sphincter between them. I saw her hand work something on the tubing and began to feel warm water flow inside my ass. It is tough to describe what it felt like, perhaps a little uncomfortable but not unpleasant either. As the water continued to flow, the pressure began to build and a cramp started to develop. I groaned and shifted as I worked through the discomfort. Madam Sara noticed my slight distress and stopped the flow of liquid, beginning to lightly massage my lower abdomen.

"You can tell by his body language that he is starting to cramp," she began telling my wife. "As you do it more often, the signs will become almost second nature. If he starts to cramp it is best to pause and deal with it right away or it will come back more often."

"Feeling better now?" she asked me.

"Yes Madam, thank you for being so attentive," I replied graciously.

She started the flow of water again and the pressure began to build slightly but without the cramping this time. After a few minutes the entire contents of the bag was inside my bowels as evidenced by the swelling in my abdomen and the urge to defecate. She put me on my side and curled my legs close to my body.

"Now that all the fluid is inside him, put him on his side with his legs pulled up to his belly and allow him to rest while the solution does its job to cleanse his insides. After fifteen minutes, you can allow him to expel the fluid or make him do some light exercise such as jumping jacks, moving the fluid around to help clean."

As I waited for fifteen minutes to tick off, Madam Sara passed the time teasing my bound wife. She ran her hands all over Angie's body, every surface exposed and available to her touch. I watched as she drug her latex covered tits up and down my wife's body. As she pulled away, I realized Madam Sara's nipples were so hard that the outline of her areolas were clearly visible through the rubber material and her hard nipples had stretched the body glove to the point of becoming thin and lighter in color. I never really thought about my wife with another woman in my cuckold fantasies but I had to say that watching this was hot. Finally, Madam Sara said my time was up and escorted me to the bathroom.

"I am going to deflate the balloons and remove the nozzle," Madam Sara advised me. "I want you to keep your muscles tight and try not to allow any fluid to escape. If you get any of it on me, I will be very angry and your balls will pay the price."

Her words alone were enough to tighten every muscle in my body. I had never really endured serious CBT before but I had no doubt she would be more than willing to introduce me. She deflated the balloons and removed the nozzle quickly. My back door slammed shut quickly like a screen door in hurricane winds. I didn't spill a drop. Madam Sara then left the room and allowed me to release the contents of my bowels. It felt so good as the fluid rushed out of me and the pressure in my swollen abdomen began to decrease. It took five minutes to work it all out of me and I cleaned myself up before leaving the bathroom where my captor awaited. She grabbed my wrists and led me back to the bench, helping me back into a position on all fours.

"For the rest of the procedure I am going to secure you to the bench," Madam Sara advised me. "For a man, having an object stuck up your ass is unnatural. Without being restrained, you might try to defend your ass from being probed and it will be counterproductive to our objective here tonight. Will you be comfortable being tied down and immobile?"

"Normally I am comfortable being tied up Madam," I replied respectfully. "I may be a little nervous in anticipation of the unknown but I will not panic being restrained."

She started by securing my ankles to locking hooks on the back corners followed by my wrists to locking hooks on the front corners, making me extend my arms and once again rest my weight on my forearms. She then applied two more leather straps just above my knees, spreading my legs, and securing them to the side of the table. These restraints ensured that I would not be able to close my legs and kept my caged cock in a vulnerable position. The last thing she did was fasten a short length of chain to the ring on my collar, preventing me from being able to lift my upper body. If she had any ill intentions, I would find out very shortly.

Sara turned towards my wife, "I will need to remove his chastity belt to properly milk him. You can do it without removing it but it will help extract the semen if you have full access. Besides, you would have to remove it after for cleaning anyway."

Angie responded by pushing out her chest, extending her ample breasts towards the red haired beauty and offering the silver key hanging on the chain between them.

Sara removed the key from around Angie's neck and proceeded to unlock my cage and removing the cage and ring, freeing my restrained cock. The cool air surrounding my prick felt as good as always after being cooped up for so long.

Madam Sara instructed my wife, putting on another pair of latex gloves. "Milking the prostate can take anywhere from fifteen to forty-five minutes, or even longer depending on each individual and the experience and technique of the Dom. The entire milking can be done with the human finger but I find it easier to use a milking wand."

She held up a clear plastic cylindrical object that curved towards the end with a soft, ribbed, latex ball on the end, making a closed ring with her fingers and showing my wife how to insert it properly.

"Until you feel comfortable with the placement of the prostate," she continued, "I recommend using only your finger or fingers to complete the process of draining his balls through milking. It is possible to cause damage if you go too deep or put too much pressure in the wrong spot. It is also important to use generous amounts of lubricant to help avoid tearing the tender rectal tissue. If you have any finger nails, always use a glove to avoid injury, especially around the prostate."

She turned her attention back to me, coating her fingers with a gel lubricant. "I am going to lubricate your anus and loosen your sphincter a little. Keep your muscles relaxed. It will make things easier on me and be more enjoyable for you."

Madam Sara put a large glob of lubricant on my asshole and I relaxed as best I could, waiting to be penetrated. This time her gloved finger slid easily into my ass. She withdrew her finger to the tip and inserted another finger, adding another dollop of lube to my opening. She twisted her fingers around inside me and made sure all the surfaces were slick with the gel and then started to separate her fingers, gently spreading my cooperating anal muscles. A couple of times I caught myself tensing up and worked against instinct to relax. After a few minutes, she removed her fingers and announced I was prepped and ready to begin.

Sara had my wife stand on her toes as she undid the D-rings that secured her cuffs to the bar and led her closer to the table. She handed my wife a pair of gloves to put on while she placed a small tray beneath my semi-rigid dick, swaying in the breeze between my legs. She then handed Angie the tube of lubricant to prepare her gloved fingers.

"I am going to insert my finger," she began teaching again, "and curl my finger down until I find his prostate. I will watch his reaction and that combined with feel will tell me I found it. Once I do, I will massage it for a few minutes before letting you do it to see where it is located and what it feels like."

Madam Sara inserted her finger again, meeting very little resistance from the prepared hole. She curled her finger and immediately hit a spot that made me feel a sudden urge to urinate.

"That's the spot," she exclaimed. "As soon as I applied pressure to the gland I felt his muscles tighten up."

"It's alright to do that while your Mistress is learning the location of your prostate," Madam Sara corrected me, "but you need to control those muscles. Leaving them nice and relaxed helps to drain the cum without orgasm, but if you move those muscles at the wrong time it could interrupt the process or even inadvertently cause an orgasm. Your body will tell us if it did and you will be locked up, having to start all over again."

She rubbed her fingers over the entire gland, varying speed and pressure as she worked the vessels to free the trapped semen. She continued for five minutes, removing and reinserting her finger to lubricate every so often. She almost seemed to be in a rhythm with the way she worked her finger around the gland. Once I was able to gain some semblance of control over my muscles, the stimulation felt good, even pleasurable in a way. It would take some time before I would have total muscular control. Madam Sara removed her finger and gestured to Angie to take her spot.

"Stick one finger in nice and slowly," she counseled Angie as she inserted her index finger. "Now curl it down slightly towards his ball sack until you find a gland slightly elevated from the rest of the canal. Pay attention to what his body is telling you and you will know when you hit the bulls-eye."

Angie fished around for a few seconds before I felt the familiar sensation again. I quickly tensed my muscles to let her know she found it.

"I just found it didn't I?" she asked Madam Sara.

"Yes, my dear," Sara encouraged her. "Now move your finger around with different motions and pressures. Move around the entire gland for a minute and then pull your finger out, lubricate and try to find it again."

My wife removed her finger, added a dab of lube, and reinserted her finger, finding the spot much quicker. I once again gave her a quick buck of my hips to let her know she was on target. She began swirling her finger around the gland covering the entire surface with light taps and small relaxing circles, every now and then hitting the prostate with a quick stab of more forceful pressure. Each time she removed her finger to lubricate, she found the correct spot more rapidly. After about five minutes of working her novice finger inside my ass, I felt something begin to travel down my urethra. A drip of fluid appeared at my piss slit of my erect cock, pointing at the tray below me.

"Is that what I think it is?" Angie asked her instructor.

"That is the first drops of precum leading the way for all of his friends," Madam Sara corrected her. "Now, take your other hand and wrap it tightly around the base of his hard cock and slowly stroke it downward to help free the fluid from his urethra. Stroke downward, as if you were milking a cow, and only give him one or two pumps. We don't want him to stimulate him so much that his muscles take over and he spurts his load in full orgasm."

Angie grabbed hold at the base of my dick and squeezed very tightly before she began to drag her gripped hand down the cock. As she did so, two drops of cloudy fluid dripped from the head of my cock and landed on the tray below me. She removed her stroking hand and Madam Sara had her remove her finger from inside me.

"Now that you know what the prostate gland feels like and you have seen how to remove tiny amounts of precum from him, I am going to teach you how to use the wand," Sara said producing the milking wand and beginning to lubricate it with generous amounts of gel. "I will permit you to use it for a few minutes and get the hang of it before I chain you up again and finally finish off his milking."

Madam Sara handed my wife the clear plastic piece of equipment and allowed her to insert the latex head into my anus. The expanded edge was three times the size of my wife's finger and I took a deep breath as my hole stretched a bit before the head slipped in and the hole closed around the smaller shaft.

"The trick," Sara stated, "is to visualize where the prostate is in relation to the wand and learn to recognize his body movements when you make contact. That is why I recommend only using your fingers for the first few times. You can even use two fingers or more if you like, if he can tolerate multiple intruders. As time goes on he will be able to control those movements but by then you will be an expert at pleasurable sperm extraction without orgasm."

Angie moved the wand around for ten seconds, like a blind man feeling his way through the world, and when she hit the right spot, I bucked to let her know she was where she needed to be. Madam Sara had her remove the wand and locate the spot a few more times before allowing her to continue massaging my prostate for the next five minutes. During that time, I began to feel more fluid draining through my urethra and drops of precum continuing to appear at the head of my stiff cock. Each time she used her gloved hand to coax the fluid out of me and into the tray where a small puddle began to form.

"OK, my dear," Sara said to my wife, "Time to get you hooked back up so I can finish draining him."

Angie left the wand sticking inside me and removed her latex glove before offering her wrists up to our host. Sara led her back to the chains and hooked the D-rings back to each wrist. She then retrieved a three-foot spreader bar from the wall and forced Angie's legs apart before bending down and installing the bar between her ankles. With the bar in place, she could not close her legs and her moist slit was left unguarded and vulnerable. Madam Sara traced her hands up my wife's legs, up the inner thigh, and with one finger, brushed between her pussy lips and across her clit.

"Your wife is really enjoying this," Madam Sara said to me, showing me my wife's pussy juice on her extended finger.

"Once I am done with you, a well deserved thank you will be in order, or perhaps I could do that myself," she said again, eyeing up Angie's restrained body and laughing.

She walked back to me and took control of the wand still sticking out of my ass. Immediately she found the spot and began to work the wand like a master of her trade. I continued to fight against my muscles to keep them relaxed as the rubbing continued, the ribbed surface of the wand sending waves of stimulation through my reproductive tract.

For the next twenty minutes, drops of fluid continued to appear from my penis. Sometimes she would let them develop until they were big enough to drop on their own and join those already in the pan. Other times she would milk my cock with a tight down stroke as if I was livestock. As I continued to conquer my own muscle twitches, the feeling of being milked became more and more pleasurable, nowhere near that of an orgasm but enjoyable as a sense of relief.

After another five minutes I began to feel like I was getting ready to urinate, but not from my bladder. It was a very strange feeling. A very slight amount of pressure was building in my testicles, enough to be noticed but nothing like the buildup you get before an orgasm. Instinct took over and my muscles tensed, clenching the wand inside my ass. I received two very hard slaps across my bare ass cheeks and I had to grit my teeth in response to the pain.

"Do not tense up your muscles!" Sara admonished me. "You are very close to draining your balls and it needs to drain freely. If you continue to tense up I will continue to slap your ass until it is black and blue."

"Keep watching Lady Angie," Sara said to my wife. "Any moment now we will see his load fall into the tray. When it does, it will flow out nice and steady. If it spurts like a normal orgasm, it means he is cheating with his muscles and close to, if not actually having an orgasm. He is fighting against his body but over time he will learn, especially with enough positive reinforcement, as in positively smacking his ass."

I felt like I was fighting a losing battle against my own body. My ass cheeks were on fire from a few more, well placed smacks and I soon got them under some semblance of control. Suddenly I felt a large amount of fluid travel through my urethra. I looked back as I saw a stream of thick white sperm and seminal fluid drain from my cock and into the tray. As Madam Sara continued to work the wand, each pulse of pressure resulted in another steady stream of my cum landing in the tray. Angie was fixated on my cock, watching in wonder as I was drained without the aid of orgasm.

For the next two minutes, my load continued to be milked out of my body. I watched with amazement as the puddle in the tray continued to grow. I had no idea I was capable of producing that much semen. Finally the flow slowed to a stop but Madam Sara continued to move the wand as drips of my most precious fluid dripped from my very hard cock and stringing down into the tray.

"I always continue for five minutes or so to ensure I have gotten it all out. I like to leave my slave's balls completely empty and ready to build up more for me. There have been times were I have gotten twice as much discharge by going for five or ten minutes after the last stream leaked out."

After five minutes, Madam Sara removed the wand from my ass with a loud pop and used her hand to drag the last drops of cum out of my cock. My ass felt sore and wrecked but my balls felt shriveled and empty. My breathing was quickened and I felt a little dizzy. After a moment, I calmed down and regained my senses. Madam Sara removed the tray of my cum from under my cock and placed it under my head.

"A slave must always consume what he produces," Madam Sara said to Angie.

What? I asked myself. Surely, I have read about cuckold husbands eating their own ejaculate but I had no idea I would be told to do it tonight. I looked over at my wife and her jaw was dropped in surprise but that gaping mouth quickly turned into an evil smirk almost daring me to do it. I was not ready to taste my own cum.

"Come on now," Madam Sara said to me as I stared at the sheer amount of my semen pooled just inches from my face. "No more stalling. Lick up your cum like a good little chastity boy."

I continued to stare, unable to move muscle from being in shock.

"Madam Sara gave you an order," my Mistress scolded me, "and you remember the agreement. Total obedience and follow orders immediately. Since you have failed to do so, you can add another month to your time in the belt. Now clean up that cum right this second!"