How I Became a Chastized Cuckold Ch. 04

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading.

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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," Angie 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 Angie had talked to her since. It would make sense that Sara would try to help Angie 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," Angie 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 baby, 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 Angie'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 Angie 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," Angie 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. Angie 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. Angie 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, Angie 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. Angie 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. Angie 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 Angie. 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 Angie, 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."

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

Angie 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 Angie," 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 Angie'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. Angie'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.