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The Best Cuckold Stories

How I Became Chastized Cuckold, part 4

by Gizzard

  

  

 

It was a few days before she allowed me to use the rubber black cock on her again, saying she needed to recover from her first, real deep fucking. I did not take offense to her words because I knew they were true. The dildo I picked out could go deeper than I ever hoped to go. When the night came to break out the toy again, she decided to have a little fun with me.

 

"I think my new rubber lover needs a name, something to help reinforce to you that your place of fucking me in bed has been taken over by the cock you picked out," Jana said playfully to me, "I think we should make it a black guy's name since it fits the type of dildo you picked. I think Leroy will work. Hubby, go get Leroy so he can give me a good fucking tonight."

 

God if I didn't know any better I would have thought that she knew about my cuckold fantasies. Some of the things she said just seemed way over the top from her normal way of thinking, but then again it was probably paranoia. Nothing has really been the same since the day I started chastity and she surprised me with things all the time now. For all I knew, Mistress Sara could have told her allot of things while they talked that night and I know Jana had talked to her since. It would make sense that Sara would try to help Jana develop more dominate features.

 

I retrieved Leroy from the dresser drawer and returned to the bed where my wife was waiting for me with a blindfold.

 

"I want you to put this on and lie back on the bed. No matter what happens I do not want you to move your hands for any reason. Is that understood?" my wife said forcefully.

 

"I understand Mistress," I replied submissively, "I will not move my hands."

 

The world went black as I put on the black silk blindfold and lay back. I felt my wife moving around between my legs. Suddenly I heard the hasp of the padlock on my cage unsnap. Before I could think of what was happening, the dome of the cage was pulled off and replaced with the baggie of ice water. I flinched but true to my word, I did not move my hands. After about thirty seconds of freedom, the ice water was removed and I felt the cage being slipped back on but there was something ever so lightly poking into the top section of flesh near the base of my cock and suddenly, I heard the closing of the lock.

 

"Go ahead and remove the blindfold," Jana told me. "What I did was install something called points of intrigue, a gift from Mistress Sara. It seems your cock is trying excessively hard to get an erection inside your cage while Leroy has his way with me. This should help with that. Do you know what points of intrigue do?"

 

"Yes I do," I replied. "As I try to get hard, the dull points will dig deeper and deeper in my sensitive flesh causing discomfort and pain to help battle my body's attempt at a hard on."

 

"Good," my wife cheered, "Warm me up with your mouth and then Leroy can fuck me."

 

That is exactly what I did. I ate her pussy until she was nice and moist and then let Leroy finish the job with a nice deep fucking, all the while with the points digging deeper into my cock. Three orgasms later and the wife totally satisfied I was once again blindfolded and the points removed before going to sleep. Thank god she remembered to take them out or I might have been in for a very rude awakening.

 

Over the next month our usual routine continued. Most days I would lick her pussy until she was satisfied and on rare occasions she would have me use Leroy on her when she needed a good solid fucking. Leroy was never slow and loving when I dipped him into her pussy. He always pounded her like a sex object, the only goal to make her cum and cum by deep and quick strokes. I continued to maintain my hygiene under my wife's careful watching eyes and my free erections limited to zero.

 

As I crossed the one-month mark, I started to become concerned about the possibility of wet dreams, not because I did not want to have any but because it would be like cheating on my agreement to wait three months for an orgasm. I had previously experienced wet dreams in the past and knew they could be just as powerful as a natural orgasm but I didn't want to take away from Jana's enjoyment, plus I knew she would just restart the clock on my chastity period and I would constantly be fighting a losing battle, renewing my period of denial every time I came in my underwear at night and never again be able to get inside my wife, at least while we still played this game, and I wasn't done playing yet.

 

Reading all the information on cuckolding back when chastity was a mere imaginative fantasy, I often came across stories and articles on how prostate milking could be used to drain semen from the chastised male without the pleasure of an orgasm and help stave off nocturnal emissions. Although I never actually tried to milk myself, I knew it was something I was going to need to meet my goal of three months in chastity. I didn't know if Jana would find it repulsive or if she would even consider it but I felt we had grown enough in our comfortable relationship to express our need for something, no matter how strange it might be. Perhaps some nice dinner conversation I laughed to myself.

 

"Honey," I said sitting down to dinner, "now that we are going for longer and longer periods of chastity, I am afraid I will not be able to complete the entire period of denial without experiencing wet dreams at night. The body will use wet dreams to expel old semen to allow new semen to be produced if the balls are not being drained on a regular basis. I am going to need your help if you want to keep them at bay and help me go the entire three months without orgasm."

 

"I see," my wife said putting down her fork and giving me her undivided attention, "I take it you have had one before. Have you had one since you have been locked in chastity?"

 

"No, I would have confessed to you if I did. It would have been like cheating on our game," I replied seriously.

 

"What does it feel like when you have a wet dream?" my wife asked.

 

"It feels almost as good as a natural orgasm. The muscles spasm just like normal making it feel really good, good enough to wake you up from deep sleep to experience your penis spurting semen into your underwear," I told her, not a hint of shame in my emotions.

 

"Well yes, that would be cheating on our arrangement," my wife stated quite sternly leaving no doubt that my suspicions were correct. "If it is pleasurable to you, like a normal orgasm, we must do what we can to avoid it happening. I take it that since you brought it up you have a solution to avoid it from happening?"

 

"Yes, I have read allot about it," I told her, "but you might find it a little strange and I am not sure you would be into it or enjoy doing it."

 

"Hubby," my wife said, her voice cold and calculating, "I have your dick locked in a chastity belt and deny you the ability to cum for months at a time. We have tried things that are strange and against the norm. I will be the judge of whether I will enjoy it or not. For that little indiscretion, two more weeks of chastity added to the end of your lock-up. Out with it...now!"

 

"Yes Mistress," I replied softly, my head bowed in shame, not because of what I was about to say but because I had challenged my wife's dominate position in our relationship. "I am sorry for anything that I implied and I understand the need for you to punish me. Please forgive me."

 

"I do forgive you hubby," my wife said sweetly, "but that doesn't mean I will retract the punishment. Now you better start talking before I make it another two weeks or perhaps a month."

 

Taking a deep breath I began, "The procedure I am talking about is called milking the prostate. Basically, it involves inserting a finger or other suitable object, such as a tool called a milking wand, into my anus and massaging the prostate gland for a period of time. Doing so causes semen to work its way out of the balls and flow out of the penis, more like a dribble than a spurt though. Doing it for long enough will drain all the semen from the testicles and remove the body's reason for having a wet dream."

 

"What does it feel like when it comes out?" my wife asked me.

 

"I can't say out of personal experience because I have never done it," I answered, "but all the stories and articles I have read describe as feeling similar to a slow urination. No pleasure, other that knowing your balls are being emptied, is experienced."

 

"Well I can't say I have ever heard of that," Jana confessed to me, "but I will do some research and see what I can come up with. So, do you really want me to stick something in your ass to help drain that stale cum out of you?"

 

With heartfelt dedication I looked into her hazel eyes, "I will do anything to make sure I can complete the tasks you lay before me. If having my prostate milked to prevent wet dreams is needed to meet the amount of time without orgasm that you ordered, I will happily do it."

 

Not much was said on the topic over the next few days and I didn't bring the subject up in fear of making her feel pressured. I did, however, begin to worry. With each day of frustrating denial, the pressure in my balls grew. I began to feel like a ticking time bomb, not knowing how long it would take before necessity overpowered chastity but I didn't want to find out and restart my clock.

 

On Saturday afternoon, about a week since we first discussed it, the subject of milking came up again. Jana sat me down on the couch and told me of her plan.

 

"I have been reading everything I can find on the subject of milking the prostate as well as talking with Lady Sara about it," she said, "and it seems you were telling the truth. As far as I can tell, it will not give you pleasurable release and something needs to be done to remove those poor cummies from your swollen balls, not only to keep you from involuntarily having an orgasm, but also for the benefit of your health. I didn't know that it was unhealthy to leave your sperm stagnant and cooped up. If I had, I would have addressed this much sooner."

 

"Now," she continued, "since I am still not positive how the whole process works, Lady Sara has agreed to teach me how to do it properly. She says she milks her husband once every two weeks and he has not had a wet dream since they started the chastity lifestyle. We are going over there tonight and you are going to experience your first unfulfilled testicle draining. You will be respectful and gracious for her efforts. Now, let's go get you in the shower. I want you clean and smooth for tonight."

 

"Yes Mistress," I replied submissively.

 

Well I guess we can cross that one off the uncompleted fantasy list, I laughed to myself.

 

After showering and shaving, being extra careful to remove every stray pubic hair, I dressed in normal street clothes since they would not be on very long anyway. Jana came down the stairs moments later dressed in a see through white silk bra and panties with matching garter and stockings. White six-inch heels rounded out the sexy get up. I could clearly see the thin strip of blonde hair through the transparent material. I started to wonder if she was going to walk out the door that way before she grabbed a long trench coat from the closet next to the door.

 

We sped off towards Mistress Sara's elegant adult store, both eager for what was coming. Despite it still being light out, Jana brazenly opened her coat and fingered herself throughout most of the short trip. I wondered if anyone got a clear look at what my sexy wife was doing in the passenger seat.

 

When we arrived at the store, we found a closed sign on the door. Jana told me to be respectful and I basically took that to mean submissive. To be on the safe side, I decided to really allow myself to drift into my role. Jana knocked on the door and Mistress Sara soon appeared dressed in a full-length black latex gown, the tight material stretched over every curve of her body. That red dress she wore on the night we all met did her figure no justice. She was absolutely stunning to say the least.

 

"Won't you please come in," Sara invited us.

 

"Thank you," my wife smiled, removing her coat before she was inside the door.

 

"Well don't you look good enough to eat," Sara complimented my wife, licking her lips.

 

"And I think I must meet your tailor," my wife returned the compliment. "That dress is breathtaking, not to mention the body it encases."

 

With a look from my wife, I undressed quickly, once again folding my clothes in a neat pile and handing them to her. As I stood naked in the doorway, Mistress Sara got down to business.

 

"I am very happy that you came to me for guidance," Mistress Sara began. "I am sure this procedure will prove to be rewarding for both of you. As a gesture of my gratitude, I will not charge you for my services; However, I do ask three things of you and they are non-negotiable. First, I ask that you reimburse me for any supplies I use. I use a few things that I will not use on anyone else. Those items you can take with you at the end of the night. Second, I expect nothing but total obedience from our little toy in chastity. If I tell you to do something, you will not delay, you will act immediately and deliberately."

 

"I understand," I replied bowing. "May I ask a question?"

 

"Tonight is meant to teach both you and your Mistress," Sara replied. "You may speak as often as necessary as long as you do so respectfully. Insolence in my chamber is often punished severely."

 

I believed her.

 

I asked my question, "I wish to address you with respect while not disrespecting my Mistress. Is there a form of address that would be acceptable to you, reserving the title Mistress for my beautiful wife?"

 

Sara stared at me with soft eyes, "Oh how I adore dedication and loyalty to one's owner. You have done well with this one Lady Jana. You may address me as Madam Sara. I assume that is acceptable to everyone?"

 

We both nodded.

 

"Very well," Sara consented, "the last thing I request, and I am sorry I have not mentioned this before, seeing the effort you put into looking delicious tonight. I am the only Dom permitted in my chamber and as such, am the only one permitted to wear clothing or be unrestrained while within the confines of my chamber. I do not ask this to disrespect you Lady Jana, but I ask it out of respect to me. Is this acceptable?"

 

"Quite acceptable Lady Sara," my wife replied bowing her head, "and I do very much appreciate you taking time to instruct me and my toy."

 

Jana turned to me, "Hubby, remove my clothing for Madam Sara, fold them, and give them to our host along with your clothing. She will decide when we get them back."

 

"Yes Mistress," I replied

 

I unclasped her bra and let it slide off her shoulders, floating to the floor like a white feather. Her firm tits stood at attention as her nipples hardened into ice picks. I slowly unbuckled each high heel shoe and kissed the tops of her stocking encased feet. Next, I unclipped her garter from her stockings before rolling each one down her leg, my tongue tasting each inch of newly exposed flesh, before sliding the garter down her legs. I spun her to face Madam Sara before gripping the thin waistband of her wet panties and lowering them seductively down her legs, allowing her to step out of them and stand completely exposed before our host. Madam Sara looked Jana up and down like a hungry dog eyeing up a T-bone. I had a bone myself, well at least as much as the chastity belt would allow.

 

"Your body looks even more exquisite when fully exposed Lady Jana," Madam Sara gleamed.

 

My wife blushed at the compliment, "You are most kind Madam Sara."

 

I folded her tiny garments, placing them on top of my own as Madam Sara continued to revel in the sights of my wife's naked body before handing them to our latex adorned teacher. She took them from me and left the room before returning with a think leather collar with a heavy gauge chrome ring in the front and two sets of leather wrist and ankle restraints.

 

"Lady Jana," Sara said handing the collar and one set of restraints to her, "would you please place these on your husband?"

 

Jana nodded, taking the black leather cuffs. She started by placing the two inch wide collar around my neck and tightly buckling the back hasp. I presented my hands to her and she wrapped each wrist in a padded cuff, the steel ring jingling as I brought my arms to the side. She then dropped to her knees and did the same with each ankle. Before rising, she gave each of my testicles a tender kiss and as she rose, grabbed my CB-6000s and gave it a strong tug causing a sudden cramp in the bottom of my stomach.

 

Madam Sara then used five shinny golden padlocks to secure each of the buckles. I realized there was no way I would be able to remove them. Once I was secured, I would be at her mercy. She brought my arms behind my back and fastened the two rings together with some sort of clip or D-ring. What a rush!

 

Madam Sara then began fastening the red leather wrist and ankle restraints against my wife's pale skin, again securing them with bright golden padlocks. I watched her smell the aroma of my wife's sex as she stood up.

 

"Now that we are all dressed we can proceed into my private chamber. Please follow me," Madam Sara instructed us.

 

As we followed the woman of the house, only the soft squeaking of stretching latex broke the still silence. As we exited the shop through a door along the back wall, we found ourselves in what I would describe as a medieval dungeon. The floor and walls were constructed of rock cobblestone and the fifteen-foot high ceiling loomed ominously overhead making the room appear immense and overpowering. The room, lighted by flaming torches fastened the walls with blacksmithing iron brackets, contained all types of equipment, benches and tables for securing a helpless man or woman as well as thick chains hanging from the ceiling in various places. If she wanted to keep us here forever, I had no doubt she would be able to but for some reason I trusted this woman.

 

"Lady Jana," Sara addressed my wife, "do you wish to be restrained sitting or standing?"

 

"I am at your disposal," my wife answered.

 

"Very well," Sara said softly, taking my wife by the wrists and leading her toward a set of chains hanging from a three-foot wide metal bar hanging from the ceiling next to a bench constructed of black walnut with a plush cushion on top encased in the softest black leather. Madam Sara secured each one of her wrist restraints to the chains with twist lock D-rings before walking towards a winch mounted on the wall. As she turned the crank, the bar restraining my wife's wrists was pulled toward the ceiling causing Jana's arms to stretch out and limit her mobility. Madam Sara went back to inspect her work, running her hands up my wife's arms, inspecting the placement of the cuffs, and running the tips of her fingers back down her arms and across her helpless tits before grabbing both rock-hard nipples and giving them a quick hard squeeze. Jana's eyes squinted shut and she let out a quick scream in response to the stimulus.

 

"I apologize," Madam Sara told my wife sarcastically, "I just couldn't resist."

 

My wife answered back with a grin that said 'Do it again'.

 

"Slave, come here," Madam Sara commanded me, her tone changed from playful to aggressive, "Up on the table and kneel."

 

I ran to her side quickly, the weight of the cage pulling on my balls with every bouncing stride. I crawled up on to the tables and nested my knees in the soft leather. Madam Sara released my hands from behind my back and ordered me to get on all fours and stick my ass up in the air. I lowered my face to the padded surface, resting my upper body weight on my forearms.

 

"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 Jana'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."

 

Jana 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 Jana'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 Jana 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 Jana to take her spot.

 

"Stick one finger in nice and slowly," she counseled Jana 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."

 

Jana 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?" Jana 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."

 

Jana 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."

 

Jana 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."

 

Jana 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 Jana'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 Jana'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 Jana," 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. Jana 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 Jana.

 

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!"

 

Again, I hesitated. "Please don't make me eat it Mistress," I begged.

 

"I am not making you do it," my wife replied innocently, "Madam Sara is and you will not disrespect her in her own chamber. Make it two more months of chastity!"

 

Madam Sara held up her hand and my wife immediately shut up. "While I agree with the punishment you handed down and I hope you hold true to it, I do not need any help with the issue," she admonished my wife.

 

"Slave!" Madam Sara barked at me, "I have ways of making you do what I want. I can apply a vise to your now drained testicles and squeeze them until you do it. The bottom line is that I will not release you until you clean up every drop. Now do you need further encouragement?"

 

"No Madam Sara," replied a broken man, "I will do as you say."

 

With all the effort I can muster, I extended my tongue until it dipped into the tray full of my cum.

I tasted it right away, a mixture of bitter and salty flavor. I scooped a small amount onto my tongue and brought it back into my mouth. The taste filled my mouth as I struggled to swallow but finally the first bit of semen slid down my throat.

 

Now that the first lick was out of the way, I was able to resign myself to cleaning up the rest. Perhaps if I had a little time to prepare I would have been able to react immediately, but instead I now had to endure five and a half months since my last orgasm. That was a far cry from the one month I just finished.

 

I began licking my gooey load with purpose, shoveling large amounts of my ejaculate with each swiping pass of my tongue and quickly swallowing before I had a chance to have a second thought about what I was doing. Soon enough I was licking the last remnants of my most sacred fluid from the bottom of the tray, the taste lingering in my mouth.

 

"Very good," Madam Sara complimented me, "That wasn't so hard now was it? If you had just complied with my order, there would have been no need for punishment. Always clean up your own mess slave."

 

I felt Madam Sara messing with my now shriveled cock but before it had a chance to try to grow again, she roughly pulled my balls and sack through the chastity belt ring, causing me to wince from the pain. She then finished installing the cage before closing the lock and giving my ass one last hard slap.

 

Madam Sara unrestrained me and helped me off the table, steadying my shaking legs and forcing me to kneel before my restrained wife.

 

"Thank your wife with an orgasm for letting you empty your balls tonight!" Sara sternly said to me.

 

I dove in. To my amazement she was soaking wet, so wet that my entire face was covered in her juices by the time I got my tongue inside her slit. She was already primed from the night's events. After only thirty seconds of eating her and playing with her clit, she exploded in an intense orgasm, holding nothing back as she thrashed in her chains. I continued to grind my face in her pussy as pleasure rocked her entire body for almost a minute. Sara finally pulled me away and Jana collapsed, her chained wrists supporting her weight.

 

Madam Sara led me to a set of stocks and placed my head and hands on the notches before lowering the top half and securing the lock. She then hooked my ankle restraints to eye bolts in the floor.

 

"Your wife and I have to conduct some business," Sara informed me. "She will be in the same room with you but you will not be able to see or hear her."

 

She placed foam plugs into my ears before slipping a leather hood over my head, locking it to my collar and zippering the mouth closed. The only hole in the mask was for my nose and allowed me to breathe. Without warning, I once again felt pressure on my back door as something large was being inserted. Still being well lubricated, the item slipped in easily, filling my insides before my sphincter closed around the object. I was sure that a butt plug was just inserted. Oh well, nothing I can do about it now, I resigned myself.

 

For what seemed like hours, I stood there in dark silence, my imagination running wild about what was happening. Were they just talking or was it something more? Suddenly I was released from the stock and the hood and earplugs removed, the light of the torches like burning daggers in my eyes. As my sight adjusted, I was lead out of the room where my wife was dressed in a new outfit, latex just like Madam Sara's outfit. I was handed my clothes and got dressed quickly, leaving the butt plug in, before expressing my gratitude to Madam Sara and leaving her store. Jana did not bother to put her coat on.

 

We drove home in silence but Jana had a satisfied smile on her face. I didn't ask her what happened once I was hooded and to this day, I never found out.

 

  

  

  

next:  How I Became Chastized Cuckold, part 5

  

  

  

  

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