How I Became a Chastized Cuckold Ch. 05

After ten minutes, I could not stand anymore and was at my breaking point. I was about to tell her I wanted to end our chastity agreement when she suddenly stopped and removed the bag. I wheezed as I tried to draw in breath, my stomach a series of tangled knots, and a severe urge to vomit that I quickly brought under control. With the painful stimulation dissipated, did I still want to end our agreement? The answer was no. I wanted to continue being chaste but I was sure that I would endeavor to make no more mistakes.

"Lesson learned!" she scolded me before giving me a deep kiss and leaving me in a dark room again.

It took two hours before my balls felt normal again, perhaps a bit swollen, but without the pain. Shortly after Angie locked my cock back up in the cage and released me, kissing each reddened piece of flesh where I was restrained. She rolled me over on my stomach and began to lovingly massage my back. I was sure that Madam Sara had put her up to this and she was feeling a bit sorry about doing it. I loved her so much that I would not allow this to bother her, even though what she did to me really hurt like hell.

"I am sorry for leaving my clothes on the floor," I began sincerely, "and I am sorry for making you punish me. I understand that you had to do it and I promise I will try to ensure that you don't have to do it again."

"Thank you," she said perking up immediately, "I am so happy that understand why I did it. I know it was intense. How much more do you think you could have taken?"

"A split second" I told her, "merely a heartbeat."

I rolled over and she melted into my arms as we made out like newlyweds before drifting off to sleep.

About a month and a half later, I was working on the computer in my office when Angie walked in wearing her naughty nurse's outfit. My fingers stopped pecking away at the keyboard as my mind went blank. Seems like a good night to have my balls drained. My sexy wife gave me the 'come here finger' and walked towards the bedroom with me in tow. When I entered the bedroom I was shocked to see Kelley sitting in the chair next to the bed, dressed only in a hot pink thong, her huge globes hanging freely and her nipples quickly hardening.

Angie had me assume the position on the milking table as they both began to attach cuffs and tie me down. As usual, my wife did a good job at limiting my mobility and Kelley, with a few helpful pointers from my wife, did equally as well. I strained to get hard in the cage knowing that Kelley would watch me get all my stagnant cum extracted by getting my prostate massaged. It also hit me that she would watch me lick up everything that streamed out of me. I figured that my wife told her about the progress we had made, but it was something else to know she would witness it.

"Wow, you were kidding Angie," Kelley gasped in amazement. "He eagerly hopped right up there."

"Of course he did Sis," my wife answered her proudly. "This is the only way he has available to get the cum out of his body and reduce the swelling in his tender balls."

"Oh you poor baby," she said with mock pouty lips. "How long has my evil sister kept your poor little dicklette locked in that cage without allowing you to have an orgasm?"

"It has been four and a half months since I last had an orgasm, and a mighty good orgasm it was," I replied with a smile on my face.

"He is actually proud that he has gone this long without cumming," she said to Angie.

"Of course he is," my wife told her calmly. "He is being a good little boy and achieving a goal I set before him, because I desire it and nothing else."

"Well I would feel sorry for you," Kelley said to me, "but since you brought this on yourself, you have no one to blame but yourself. Alright, let's get this party started."

Angie wasted no time snapping on her gloves and lubricating my arse before inserting the enema nozzle and letting it flow. After waiting for a time, followed by expelling the liquid, I was restrained again. She had Kelley remove my CB-6000 as she lubricated two fingers, inserted them into my ass, and started to massage my prostate gland. Kelley watched closely as my wife worked her magic. Thanks to having an audience, it took no time at all for precum to begin glistening at the tip of my raging hard prick. Angie removed her fingers, inserted the milking wand, and continued with the process. After a few minutes, my wife allowed her sister to try it and before I knew it, Kelley was working the wand, hitting all of the right places.

As the small amount of pressure began to build in my nuts, Angie took over working the wand and began a quick, rough stimulation of my prostate. I had learned to control my muscles expertly with all the practice I received over the past few months and kept them still as a pond as my saved up sperm and seminal fluid rapidly drained from my cock, landing in the tray below me.

"Look at all that nasty jizz just flow out of him!" Kelley exclaimed. "You are right. It doesn't spurt at all. It just runs out like a leaky faucet. Oh my god this is making me wet!"

She wasn't lying. The crotch of her panties was so wet that it appeared they would begin to drip like my cock at any second.

Angie kept at it for another ten minutes as they witnessed a random drop escape and hit the pan here and there. With a final down stroke of my cock, freeing the last remnants of my balls, Angie turned to her sister.

"Wait until you see this," Angie said confidently. "If that made you wet, watching him eat it will open the flood gates."

Kelley picked up the try and placed it below my face. "Here is your dinner Chasty. Be a good boy and show me how you swallow all of your cum. Lick it and eat it!"

I no longer hesitated in completing this task. It was like second nature to me. I quickly licked up large globs of my man goo, bringing it inside my mouth and letting it slide down the back of my throat. I watched Kelley as I continued to consume my mess and she couldn't keep her fingers out of her panties. I finished licking every drop as both the sexy women complimented my performance.

"Thank you for not disappointing me hubby," my wife said cutely.

"You did that like you enjoyed it Chasty. Nicely done." Kelley said laughing.

My wife cleaned my cock and balls with a damp rag before teaching Kelley how to install the cage. They untied my bonds and freed me from the table. Kelley threw herself on the bed and pleaded with my wife.

"Please let me use him tonight. After watching him eat his own cummies, I really need to get off. It's time I collect some payment for wearing this," she said holding up the silver key on the chain around her neck.

"Be my guest Sis," Angie said in a carefree manner , locking my wrists behind my back and walking out the door. "Feel free to use him as long as you wish, just don't break my toy."

Even though my balls had just been drained, knowing I was about to go down on my wife's sister made my cock snap to attention. I watched her lying on the bed, tweaking her own nipples as she stared me directly in the eyes.

"Make sure you have swallowed all of that cum," Kelley ordered me. "I don't want to get pregnant from any leftover sperm that might be swimming around in your mouth."

I swirled my tongue around my mouth ensuring that all my jizz had been swallowed before crawling between her legs, immediately smelling her excited juices. I used my teeth to grab hold of her cotton panties and peeling them down her legs. As my tongue traced its way back up the inside of her thigh, I began to feel the massive amount of heat radiating from her pussy. Seeing her sex for only the second time, I saw that she had shaved most of her pubic hair, leaving a thin strip similar to way my wife groomed her curlies.

As I slowly inched closer to her sodden cunt, she suddenly jammed it right into my face, taking me by surprise and jeering my neck. Regaining my senses, I immediately shoved my tongue between her slit and up her slippery hole, straining myself as deep as I could go. With just one lick she started to moan in ecstasy. I pulled my tongue out and bit her clit, using my tongue to push the portion inside my mouth against the back of my teeth. She screamed and bucked causing me to tug on her clit even harder.

"Holy fuck!" she screamed out loud. "I can't believe I am cumming all over my sister's husband's face. Oh my god, Oh fuck, Oh FUCK!"

Her voice trailed off into illegible sounds before she came down from her monster orgasm. As she tried to pull away, I held her clitoris tightly between my teeth, causing her to rebound from the jolt through her, now extra sensitive, button. She tried again and I held fast before she gave up. Once she settled I began to run my tongue up and down her moist slit before flicking it against her clit. As she tried to draw away again, I simply followed her up onto the bed, slithering my way like a snake due to not having the use of my hands.

"Oh my god," she said giggling, "you have to stop. I don't know if I can take anymore. Every time I try to pull away your tongue just follows me and hits the right spots all over again."

"Stop moving or I will tie you down Sis," my wife surprised us from the doorway. "I will tie you to the bed with your legs spread and inviting like a slut and make him pleasure you all night long."

I wonder if she watched the entire time. Oh well, who cares. Kelley finally stop trying to escape me and I began to focus my talents. I continued for the next forty-five minutes as she melted to mush below me, enjoying two more orgasms before I had to stop, my jaw throbbing and my tongue swollen.

Kelley lay there regaining her breath and five minutes later she was asleep. My wife removed my restraints and had me remove her nurse's outfit before we crawled into bed, joining her. That night I slept between, and cuddled with, two very sexy women. I know I have cuckold fantasies, but I don't care who you are, being sandwiched between two naked women is hot.

Over the next two weeks, Kelley visited more often, mostly to help my wife tease me mercilessly, but often times to collect additional payments for holding onto one of two keys to my belt. Even though I wasn't able to achieve orgasm, I was having the time of my life, satisfying two women at their whim.

One evening, shortly after I reached the five month mark since my last orgasm, Angie came down the stairs in a gorgeous red evening gown with a slit up the side then went all the way up to her hip, her usual straight blonde hair done up elegantly in waves and curls, and her make-up meticulously applied.

"Go put on a nice suit baby," she told me sweetly. "It is time for us to go on a date. I made reservations at your favorite restaurant and dolled myself up for you."

"You look amazing Bella. I won't even ask what the special occasion is. You dressing up like that is good enough for me. Give me ten minutes and I will be ready," I told her with a kiss.

We enjoyed a nice dinner in each other's company and happily spent the next few hours dancing as we did many years ago before our lives became so busy.

After we got home I put on some music and opened a bottle of wine so we could continue the romantic evening in the house we had made a home together. I realized that for the first time in months, I was wearing clothes inside the house. I suddenly got nervous that I was going to be punished for doing so.

"Oh my god, baby," I apologized, "I am so sorry for not removing my suit when we got home. I was so mesmerized by you and this wonderful evening that I simply forgot I was wearing a chastity belt. Please allow me to correct that error right now."

"It is ok Hubby. Tonight was a night for us, but perhaps we both should get a little more comfortable," she said as she undid the tie behind her neck and her dress effortlessly floated to the ground, revealing and equally elegant thin red silk bra and panty set.

I quickly removed all my clothing before retrieving our clothes and taking them upstairs and hanging them in the closet. When I returned to the living room, Angie was sitting on the couch and tapping the seat next to her, inviting me to join her. I sat down and wrapped my arms around her.

"Do you still enjoy being in that chastity belt?" she asked me nervously.

"Yes, I still enjoy being locked up and focusing my efforts on you," I said after a moment's pause. "There are times when it is really tough, when I want to just tear the cage off and ravish you, but the way you kiss me and hold me close to you reminds me that you love me, and my little bit of suffering does not go unnoticed. Do you still enjoy our game?"

"You have no idea how much I enjoy our lifestyle," she confessed, "perhaps even more than when we first started. I love the fact that you will do anything I tell you to do. Do you realize we haven't had an argument since we started?"

"Wow!" I exclaimed. "I haven't thought about it, but you are right. Maybe we found the secret to marriage," I laughed.

"Well I am not sure most men would agree with you," she giggled. "Do you miss having sex and having orgasms?"

"Of course I do baby," I answered her. "Any man would miss being able to orgasm when he wanted and any man would miss making love to you, but I realize that it takes more than me having sex to give you what you deserve. It really sounds like you want it to end though."

"I don't want it to end," she told me grabbing my caged cock, "but that is also part of the problem."

"I don't understand baby," I answered confused.

"Well hubby, the problem is that I am so god damn horny for a good fucking, and I don't mean you eating me or a romp with Leroy. Those just won't scratch the itch. I want to fuck a real living cock, to feel it pulse as it shoots off inside me. I had no idea I would miss it so much and I know it sounds selfish, as I at least get to cum on a nightly basis. Not only do you miss out on the sex but you don't have the privilege of orgasms either," she confessed, her voice cracking.

"The way I see it," she continued, "I can either unlock you early and have my way with you, which I really don't want to do, or I can leave you locked up and go without the one thing that I truly need right now, a good solid fucking. Either way I have to give up something that I want."

The thought of her cuckolding me rocketed through my head. Did I want her to try it? If so, this was the perfect time to breach the subject. She already had all the cards lying out on the table. All I had to do was make the suggestion and see if she went for it. So many 'what ifs' had my mind spinning in circles, but in honesty, the only way they would ever be answered was if I grew a pair and broached the subject of my most secretly guarded fantasy. It was now or never, I decided.

"Well honey," I began nervously, my hands starting to shake, "it seems you may have missed an option that would allow you get everything you want."

"I'm listening," she said curiously, her eyes perking up.

"Well," I said, clearing my throat, "you could always get fucked by another man."

"What?" she said loudly as she jumped out of my arms, her mouth wide open.

"The only way for you to get fucked and still keep me locked up is to find another man to fuck you with his cock." I told her truthfully.

"You mean to tell me that you would let me to cheat on you and allow some other man to put his cock in my pussy, the pussy that I have kept for only you since we married, just so I can keep you in chastity? You will let another man fuck me while you sit at home, locked away, not even able to jerk off?" she asked me looking like she was in shock.

"Bear with me for a few moments and please don't be mad at me. Let me tell you the whole truth about my feelings on it," I begged, getting her attention. "I am devoted to giving you everything I can to keep you happy. If that means sexual satisfaction by another man, I can live with that. Besides, it isn't cheating if you do it with my permission. It has long been a fantasy of mine to watch you with another man and I have known since we locked my cock in chastity that there was always a possibility you would want more than I can give."

"I don't know if I could do that to you hubby," she told me, shying her eyes away from mine. "What if you resented me for sharing myself with someone else? What if taking another man into my bed ruined our marriage? I don't know if I could ever make that gamble. You mean far too much to me."

"The only fear I share is losing you. I could not resent you for getting laid if I am the one that told you to do it. I can guarantee that it will not ruin our marriage as long as you grant me a few conditions," I reassured her.

"As long as one of them doesn't involve you fucking another woman, I am listening," she said giving me all her attention.

"No baby," I said calmingly, "None of them involve me having sex outside our marriage. If I am not allowed to orgasm with you, then I don't need to with anyone else. If you are interested, do it once and tell me all about it in great detail. See how I react before you do it again. Once again, I will lay no blame at your feet, but if I don't enjoy it, I ask that you don't do it again. I think I have that right as your husband."

Angie stroked her hand down my cheek, "Of course you have that right. I love you darling and I don't want to do anything that you don't enjoy in some way. I have to say that you have me interested but I am still afraid something could go wrong. What if I inadvertently fell in love with the guy I was fucking?"

"If you stuck with the same guy, you would have to view him as someone that just fucks you, uses your body for his pleasure and you use his cock to get off. Either that or constantly have new lovers. You would have to make me a promise. If you started to have feelings for the man fucking you, you have to break it off right then and there. No exceptions. No waiting to see where it might lead. That is the only possible way you could betray me with this arrangement," I told her being very serious.

"I easily agree with that baby," she said, once again being able to look me in the eye. "I hope you are sure about this because I am willing to try it. Here is what I want you to do. Every morning you will encourage me to go out and find someone to shove his cock in me and treat me like a slut. If you can convince me that you really want me to do it, I will go out on Friday night dressed like a woman looking to get laid and see what I can pull. Now, all this talk has me so god damn hot. Lay down on the floor so I can sit on your face and you can get me off."

I lay down on the carpet as she finished removing her bra and panties. She straddled my face and sunk down to her knees, placing her wet pussy over my waiting lips. As I ate her ferociously, she played with my caged cock and balls, licking my scrotum and taking my plastic encased penis into her mouth. She enjoyed her pleasure as I enjoyed my torment until we were both exhausted and my cock was leaking precum.

The next morning she joined me for breakfast and as she enjoyed her coffee, I followed her instructions, given the night before.

"Honey, I really hope you feel up to going out on Friday night. If you do, I want you to go out and pick up the hottest guy in the bar and follow him back to his place. I will be so happy if he tears off your clothes and gives you the rough fucking you have been missing for the past five months. I bet he can give you at least four orgasms before he sends you home to your waiting husband." I told her smiling. "Not a bad start hubby," she told me before she kissed me and headed off to work.

I said similar things to her over the next four days and soon enough Friday morning had arrived. I had planned what I was going to say for the past few days and I hoped it would drive her over the top.