Chastity Keyholder - Blog Posts

The following is an original work of fiction. All individuals described are consenting adults. All rights reserved by the author. If it is received positively I may consider extending this novella.

Carol left a note on the breakfast table. Good morning sleepyhead. I didn’t want to wake you up before my trip. I’ll be back in two weeks, love you!

Smiling I made juice and got ready for work, luckily my office had gone completely remote and all I had to do was walk the twenty feet to my home office. The idea of having the house to myself for a change was going to be a novelty.

I noticed another note from Carol on my computer. It said, sweetie I hid an emergency key just in case. I don’t even want you touching yourself down there without my permission.

My heart beat quicken and I could feel myself tightening in the cage. I unconsciously shifted in my chair. She went on to say “if there is an emergency contact me and I’ll let you know where it’s located.” I’d never had to use the emergency key, but it was smart to have one.

Her note went on to say since I’ll be gone so long can you take care of a few things for me? I want you to provide a few “favors” for David. My mouth went dry, David had become “our” boyfriend, at least that’s what she called him for the past two years.

He had become a dominant presence in both of our lives. I was hoping while Carol was away I could have a break from him, but it didn’t look as if that was going to happen.

I had been her actual cuckold since David came into our lives. It began when Carol met David at work, he was a manager in the office. He was tall, muscular and supremely confident.

In the beginning, being her cuck was simply a kinky role play game we indulged in.

Carol always enjoyed it greatly. She also introduced the idea of chastity and slowly escalated the duration from a few hours, to a few days, then weeks until it became semi-permanent.

Before David became a presence in our lives. I satisfied her with my mouth or large strap-on, which she surprised me with on my birthday. I said it looked as if my “birthday present” was really for her to which she smiled knowingly. It was about this time she began referring to me as “cucky” all the time, unless of course if family or others were present.

Whenever she said it the tension in my caged increased. When the chastity became 24/7 I began waking up with exquisitely painful blue balls.

One night she came into the bathroom and saw me sitting on the edge of the tub nursing the ache. She gave me a wry smile and asked what’s wrong, is your poor little locked up toy hurting?

She pulled me back to the bed and we had a long make out session. She proceeded to tell me what a pathetic little cucky loser I was and kiss me deeply. My genitals ached in a deliciously painful mix of frustration and submission to her.

I found the ache to be addictive.

Two years ago we had our anniversary dinner at home that I prepared. After finishing dinner, I started to get up to clear the table and she motioned for me to remain seated.

She took a deep breath and said I have something I want to discuss. She said she wanted to take our cuckold role play to the next level. I gulped and said how so?

Cucky you know I love you with all my heart yes? Of course I said, I had become more and more under her control daily. I could feel my face turning red. She smiled at my reaction and said remember David one of the senior managers at my work? Yes I said, I had met him at a Christmas party at a local restaurant the prior year. He was quite friendly and had a disarmingly confident attitude. He had the type of personality that was casual, yet dominant. This was the first time she mentioned David in more that a casual work related way.

I shared with him our… little role play. I blinked, oh my god really? This is our personal business I protested. Of course cucky, but I didn’t think you would mind. I shifted awkwardly in my seat.

The ache in my crotch was quickly becoming obvious to her. She observed me carefully and said it looks as if you don’t mind too much… do you? She said with a wry smile.

This is how it began. At first it was an occasional night out with him. I would sit in my room in a combination of frustration, arousal and humiliation. Experiencing the delicious ache between my legs. It was the most profound high of my life.

She would return home late in the evening and jump on me and push my face between her legs or demand the strap-on. The taste of her sex was overwhelming.

Previously she would occasionally reward me with a release, usually in the form of a hand job, but now she fiendishly delighted in my frustration.

After a few months Carol said that she wanted David and I to meet. I initially protested saying having to meet him would be too embarrassing, but she wore me down and I surrendered. The first meeting was awkward, at least for me, David was casual and completely confident. He didn’t try to overwhelm me and tried to assure me he understood the special relationship between my wife and I.

During our first meeting he mentioned that Carol has talked about me quite a lot and that he was happy to meet me. After that he openly began to come to the house to pick Carol up for their “dates” and made small talk with me. Eventually Carol told me David was going to spend the night and that they had a treat planned for me. Carol asked me to make a “special dinner” for the three of us. To say I was nervous would have been an understatement.

That night I was permitted to watch them have sex for the first time. I sat in a mixture of arousal, frustration and utter humiliation. David took notice of my predicament and smiled. Enjoy the show cucky? That was the first time he called me by that name causing my face to blush beet red.

During one of their play dates at our house Carol said she wanted me to join in the fun rather than simply be permitted to watch. I was hoping she would grant me a release, but she had other ideas.

Before David came over she told me “they had decided” that I needed to understand my place in the household by sucking David hard before they had sex.

My mouth dropped open, I’m not gay Carol I said. Carol smiled and said of course you’re not, you’re doing this as a sign of your devotion to me. I’m sure you’ll love it cucky, don’t worry.” Then she added, when we are finished you’ll clean his “cock” with your mouth and lick out my freshly fucked pussy to show your appreciation. She grinned and kissed me deeply knowing I couldn’t resist her.

That’s how it started, Carol began referring to David as “our” boyfriend when she mentioned him.

As it turned out, David really enjoyed being sucked off by me, much more so than Carol.

He would sometimes drop by just for that purpose. Carol enjoyed watching me pleasure “our” boyfriend.

Early on David insisted that I be hairless. He casually mentioned that he preferred me to have an adolescent boy appearance including outfits.

One day they announced it was decided I was to permanently move into a tiny undecorated room downstairs, while the adults occupied the master bedroom. At the time the reference about adults staying in the master bedroom failed to register. I was focused on being told I had to move into the windowless storage room.

The room I moved into consisted of only having room for a twin bed and cardboard boxes to store my clothes. David semi moved into the master bedroom with Carol. Even though he had his own place, he let it be known he will set the rules for the house.

Some of the rules consisted of having to ask permission to go out, having any outside friends approved by them and having a 8 o’clock curfew along with doing all cooking and grocery shopping. I was told that I could hold hands with Carol and cuddle and kiss but that anything else had to be approved by him and would be considered a privilege.

Once Carol caught me trying to listen when they had sex. I hadn’t earned the privilege to watch, or for that matter listen, that week due to not following some of the rules he introduced.

The following day I returned from grocery shopping to a surprise. Carol said, well cucky since you have difficulties following the house rules “we” have decided a way to help you remember.

She took me to my room, which was slightly larger than a closet, to show me my twin bed had been equipped with a four point harness with restraints for the wrist and ankles that attached around and under the mattress.

My mouth dropped open. Ahh..Carol, I’m sorry, I really didn’t mean to break the rules. I promise to obey them from now on. This looks frightening.

Well cucky, David decided you needed “alone time” to understand your place. I sat on the bed and got the second shock. The bed made a crinkling sound. What’s this I said? Its a water proof sheet to keep you from soiling your mattress silly. Your “alone time” could be for only a few hours, to a few days, perhaps much longer. It all depends on your transgression.

During that time you won’t be permitted to leave your bed. You’re going to be secured and left in the dark.

From then on when I was being disciplined, I would be bound to the bed for whatever duration David decided upon.

This didn’t initially seem too bad, but the first time I spent a few “days” of alone time it was humbling.

Carol allowed me to wear a diaper and fed me a simple meal twice a day. During one session when I could no longer hold my bowels I soiled the diaper. Carol noticed when she brought me a meal and reticuled me for messing myself. It was so humiliating. I quickly learned not to break the house rules.

Discipline was either “alone time” or a punishment spankings from “daddy” and kneeling in the corner for a set time. Carol and David kindly offered this as a alternative when they noticed my distress after being confined to the bed for several days.

Both punishments I learned to dread.

Around that time David and Carol sat me down one weekend and informed me that I was to call him “daddy” whenever I spoke to him and that every sentence was to begin or end with “yes daddy” or “no daddy,” My face was absolutely beet red the first few times I said this. Carol was turned on by my embarrassment. I knew she was aggressive, but didn’t realize the extent.

Daddy particularly enjoyed play time as he is physically larger than I and enjoys daddy-boy roll play.

Daddy and Carol had put me on a strict diet until my appearance was physically pleasing for daddy’s taste. Daddy said he preferred me to be thin and have longish hair.

Now we are back to the present, Carol was off for two weeks and she expected me to perform favors for David. My mouth was dry, I knew what was expected. Daddy enjoyed fellatio, long slow blowjobs, which he expected me to perform to his satisfaction. If I failed to perform as expected I would receive an utterly humiliating spanking. These usually resulted in me sobbing and begging “daddy” for forgiveness. As a daddy, David proved to be strict and wickedly imaginative.

As time progressed daddy had began to explore his sexual perversions with me.

He introduced me to pony rides, he would repeatedly bounce his “little boy” on his knee with my arms bound tightly behind my back in a box tie facing Carol who sat in a chair in front of me and sing.

“Ride a little horsey don’t break down. Ride a little horsey go to town. Better be careful so you don’t fall down!”

The song would repeat over and over as he bounced me helplessly up and down on his knee. I found this utterly humiliating. Carol absolutely loved watching as daddy bounced me up and down on his knee giving me pony rides and masterbated herself. She loved to see me humiliated. Eventually daddy would place me kneeling facing a corner and they would fuck. I didn’t dare turn my head nor make a sound.

On one occasion they fell asleep and left me there for hours. I didn’t dare move.

This is how our lives intertwined and how I willingly went from being an adult to a chaste submissive boy for daddy’s use and a humiliation slut for Carol’s erotic amusement.

I have money and a tiny cock, but no one to humiliate me and put me in a chastity cage 😒

Absolutely! That's because it's the only way to make me release my seed.

Literally my state right now 🙂