After twenty minutes, Ally was satiated.  She sat there, her legs all spread out, her head back, with sweat dripping off her body. I focused on the drop of sweat that dripped off her right nipple. After enjoying her glow for about five minutes, she got off the couch and went to get us two beers from the frig. I was in my usual post-sex condition, my penis was throbbing and pounding against the end of the cage, my balls ached, and my body was trembling especially my hands. I sat on the floor slumped over both hands on top of the cage as if that would stop my penis from fighting the cage. Ally handed me a beer and I held it with both hands.

“Don’t spill it. Wow, I think your shaking after sex is getting worse. It seems like you would be getting used to it by now, but I guess not. Now that I have de-stressed a little with help from your magic tongue, I want to talk to you. I couldn’t think when I was lust-insane like you are right now.”

“Could you go put some clothes on? Some baggy sweat pants and a sweatshirt, please. I want to settle down so I can think straight. And the cage is too damn tight. Please, give me just a little break. My stomach muscles are so tight they feel like they are going to rupture.”

“Of course not. I am your keyholder. Get your shit together. You have to learn to function when you are messed up because that is your new normal. Your stomach muscles hurt because you were fucking the air too hard. Although I love it when I make you do that.”

“What do you want to talk about?”

“About the next phase of the game, we are playing.”

“What about it?”

She was standing in front of me, sipping her beer as I got up and sat bent over on the couch. I ignored that she was naked, or tried to. My eyes were first drawn to her pussy and then to her bare breasts. I pulled my eyes away and focused on the blank tv screen on the other side of her. I looked back at her face, and she had a silly grin from enjoying my hour-long struggle since she walked through the door.

“It is almost dark. Let’s go out on the back porch and let’s talk.  Help me get what we need to make some boilermakers.” I helped her carry an ice chest outside with two six-packs of beer and a large bottle of whiskey to some tables and chairs we have on our deck. It was still light enough that our neighbors could have looked out the back windows to see her bare ass, but Ally didn’t seem to care. We made our first boilermakers and Ally chugged hers. I sipped on mine slower waiting for what Ally had to say.  I was handicapped enough without getting buzzed. I watched her make her second and third boilermaker over the next thirty minutes. It was as if she was getting her nerve up to talk to me about something. Watching her walk around nude was the new normal, but I had not adjusted to it, yet. I wondered if I ever would as a tried to move the tight cage around where it was not so uncomfortable.  I was mentally exhausted trying not to think about fucking her.

“Do you like this game we are playing?”

“Yes. I assume you are going to let me fuck you at some point. I like most of the kinky stuff you are doing.  I wish you had done some of this kinky stuff before we started the chastity game. We could have been fucking each other’s brains out. But now in this cage, it just makes me insane. I don’t know how much longer I can keep it together without a release. What is this talk really about?”

“I really like you being locked up and horny. Knowing you are sitting there hard in your cage constantly wanting me is such an ego booster. I feel like I am the sexiest and most desirable woman in the world.  I am doing all this kinky stuff because you are in that cage. It makes me insane with lust.  I like feeling sexy and powerful. I like what I am doing to you. I don’t want it to end.”

In the interest of being open and honest, I’m having brunch with Teddy in a few minutes.

As you read this document, I know two things will happen: first, you will become jealous, which will be some mix of anger and fear. We have both committed to becoming poly for years, so here is your first test.  Second, you will become very turned on. Your cage will become very tight and uncomfortable. It will eventually become painful if you don’t get a grip on your jealousy.

Unlike previous erections you have experienced in your cage where you get aroused, the cage gets tight and uncomfortable, but it loosens up with the removal of the stimulus, usually my bare ass, this time the cage will stay tighter for much longer. Why? Because your jealousy is going to keep the images and events, that I describe in this log fresh and vivid in your mind. I hope I write clearly enough that you can see me in your mind’s eye sitting with my legs open and my pussy exposed. Teddy, I predict, will get aroused and come in his pants when he gets a taste of this wicked keyholder. He will be powerless, a mere pawn; and afterward, he will become obsessed with me, and I will mold into a toy. Perhaps I should make him into a chastity slave? What do you think?

You will get aroused and jealous. You will not be able to get off, instead, the tight cage will become increasingly uncomfortable or even painful. Your jealousy will cause you to keep replaying the images in your mind, keeping you aroused, and keeping the cage tight, to state the obvious. In addition, as you stay aroused, your prostate gland will keep making semen escalating your blue balls to another level.  Since you are already full and dribbling, I am interested in how you handle my new rules about dribbling. This is going to be a memorable and difficult challenge for you and your balls. If you just remember your status as a chastity slave, you will be okay. If you get confused and think you have some rights as a slave, this could turn into a real hell for you. Sorry, my love.

I will update this log when I have finished playing with Teddy. I will not make too many promises on what I won’t do because I am turned on out of my mind thinking about what is going to happen. I am going to be a naughty keyholder. I think it will be fun and difficult to stay in control of Teddy and my own desires. Do I feel guilty about what is going to happen to you? A little, perhaps. But, as your keyholder, it is my job is to tease and deny you. When you get hard and stay that way, it means I have done my job. When you beg to be released, and I don’t, it means I have done the second half of my job. Perhaps, a hot bath will help you to settle down? You’ve had more than a week to learn to control your lust while you are getting hornier every day. I suggest you get ahead of the curve if that is possible.

Ally buzzed through the living room and went upstairs. She just waved as she went by and then her running feet echoed up the stairs to our bedroom. My body said nothing; I was relieved. Ally came down the stairs ten minutes later. My mouth dropped open. “I am in a hurry, but I wanted your reaction to some changes I have made.”

She put on foot up on the coffee table unavoidably showing me between her legs. “You’ve shaved,” I noted.

“Yes, and how do you like my new skirt? I think it is even sexier than the one I wore for you last night.”

The skirt was incredibly short and tight. The shiny green material wrapped around her and was held together by a zip zagging golden chain that left a four-inch vertical strip of her skin above her leg visible.

“Look, my showing skin here, the guy will know that I do not have any underwear on. I have twisted the skirt so that the opening is less than a half-inch away from my pussy. And when I sit, any man in front of me is going to have an erection.”

“An inch of your butt cheeks are showing.”

“Yes, and if I bend forward you can see my pussy from behind. I have to stand up straight,” she said as she demonstrated it for me. I noted almost abstractly that the cage was painfully tight again.

“What do you think of the top?” [RO2] [RO3] I stared at the simple white halter top that tied in a single bow across her bareback and another one that tied behind her slender neck.

“I can see the darkness of the areola around your nipples, and I like that your nipples are erect. You don’t worry about being arrested in that outfit?”

“Women can get away with almost anything they are brave enough to wear as long as they can pretend it is normal. I just have to wear it brazenly. It is our privilege as the beautiful gender that controls the world.”

“I don’t know how to respond to that.”

Movie time turned out to be Ally sitting nude on the couch asking me to put a pizza in the oven, bring her a bowl of ice cream, and make her several fancy drinks. While eating the ice cream, she put her feet up on the couch and waved me over to go down on her. Yes, she had the ice cream before the pizza. It was all about her being the Princess. She reveled in and I tried my best to indulge her. I was dead tired and Happy was gradually becoming slower to respond to insanity. I was beginning to believe I would live to see a better day. Tomorrow,  I would think clearer and know how to respond to the crazy world I now lived in.

When not busy treating her as a Princess with food and sex, I tried to watch the two movies that she enjoyed. At bedtime around midnight, she got me wound up making out with me on the couch and then got up suddenly to go to bed leaving me sitting on the couch waiting for the discomfort of the cage to subside. In bed, she asked me to cuddle in behind her with the cage nestled in her butt.  She molded her soft body into mine perfectly. She made it a big deal, sticking out her butt and pressing it into my groin making the cage uncomfortable. When I tried to move back a little, she moved back again until my cage rested tightly up against her butt. I wondered if she could feel the throbbing she was causing.

My left arm went under her pillow and neck. My right arm wrapped around her and she pulled my hand onto her left breast and put two hands over mine. She fell asleep quickly. I lay there trying to calm down. I was aroused enough that the cage was tight and very uncomfortable. I tried to lie still and think about something else besides her nude body feeling soft and warm against mine, her boob in my hand, and her ass pressed up against my cage but I found it impossible. Tension filled my entire body and every so often my body would jerk and then tremble. I seem incapable of controlling my own body.

After about an hour, I woke her because my body was jerking too much and I was moaning in my half-awake, half-asleep erotic dreams. I was nearly dead, but Happy had got a second life and wanted this soft and delicious body that he pushed against. I couldn’t stand how much my body wanted her. When my shaking finally woke her up, she was annoyed.

“Oh honey, I love how much you want me and how messed up you are from trying to cuddle with me as I asked. But you keep having those little jerks and tremors go through you. I know you can’t help it, and I love that I am keeping you awake wanting me so much, but I need my sleep. Get up, sit here. I think I can set it up where you can keep jerking and I can get some sleep.”

At home, she pulled up in our driveway.  It was dark sometime between 8 and 9 pm.  She got out of the car and instead of going into our relatively private back yard, she walked around to the front porch motioning me to follow her.  I helped her pick up five boxes from Amazon.   I couldn’t help but watch her bare ass bend over to pick up the boxes then wiggle to the back door.  I smiled to myself knowing that she enjoyed how obsessed I had become with her.

“What is in the boxes?”

“For one, there is another seven-inch mini-skirt.   What do you think?

“You have no reaction except that bent-over walking thing you are doing?  Where should I wear it?  Give me some suggestions. Okay, if you are not going to say anything then I will leave you alone for a while and let you get your shit together.  It seems you can’t handle this woman.”

Once inside, I tried to grab her ass in the living room and she took off up the stairs laughing and hollering.  I came up the stairs more slowly struggling with how uncomfortable I had become being hard in the cage for so long from all her teasing and craziness.

I found her on the bed with a dildo beside her.  “Stand right there and watch me, honey.”

She put the dildo inside of her and for the next twenty minutes fucked herself with it almost crying over and over,

“I so want your cock inside of me.  Imagine if I was fucking you right now, your cock hard inside of me, the pressure building in your balls, you trying to hold back coming too soon because I am so fucking hot.”

She kept repeating similar lines as I stood there bent over with my hands on my knees with my cock pulsating in the cage.  I stood there breathing hard my hips moving with hers silently fucking the air.  After she came, she motioned me to the bed, “please,  I want a little more.  Go down on me, Robert.”

I dove in like a madman and she started coming almost immediately.  She let me go for about ten minutes and then pushed my head away, “I’m exhausted, let’s take a break.”  I rolled over on my back not wanting to stop but trembling and shaking all over from what my madwoman had just put me through.  Five minutes later, I had started to settle down.  She rolled on top of me wrapping her legs around the outside of mine and burying her lips in my neck.  She slowly started fucking me and I arched my back to try to push the chastity cage into her pussy.

“We can’t let you off this easy, Robert. I want you to try to fuck me with your cage and see if you can handle it.”

We got thrown out of Kohl’s.  Ally made too much noise.  I guess the saleslady, who must have been at least twenty, could have called the police but she just told us that we made too much noise, that everyone in the store heard us.  I think that was an exaggeration, but she whispered a small caveat to me as Ally was putting herself back together that my grunts were like a bear in heat.  Her small knowing smile made me feel like she somehow approved.  We were lucky that she was cool.  I was a little rattled by how this young innocent-looking girl was standing close to me whispering about what we had just done while Happy was throbbing about her standing so close and talking about me sounding like a bear during the “act”.  In my fantasy filled brain, I imagined putting her hand on my cage to feel its prisoner thumbing on the bars trying to reach her.

Ally took my hand in that stairwell and led me back on the roof and across to the stairs on the opposite corner of the garage.  She led me down the stairs and through a hall into the mall.  I saw a bench and pulled Ally over to it.

“What’s wrong, babes.”

“My legs are mush.  I have to sit down.  My balls really hurt; I really need to come. It’s hard to walk; the cage is too tight.  It is so damn frustrating with my penis hard and pointing straight down.  And I can’t stand this wanting you so much; I want you so much I am about to cry.   Your teasing has got me so wound up I can’t handle it; all I can think about is fucking you.  You look so damn sexy in that short red dress, I can’t handle any more.  Please, I have had enough.”

“And as your keyholder my job is to push you, encourage you and most of all, not let you blow what may be a once in a lifetime experience.  So quit being a whim and suck it up.”

“This is really much harder than I expected.  You really don’t understand how messed up I am.  I’m in agony here.”

“I think you are being a little dramatic here.  But, I have learned something very practical with you.  If I want you to do something, I just get you more turned on than you already are, and like magic you are onboard.”

“I’m already turned on enough, I’m hard.”

“Okay, baby.  Look at my hemline, you can almost see my pussy.   Now see what is happening to you.  You are starting to breathe harder, you are fidgeting in your seat by just talking about my pussy.  The cage is going from hurting to you being so aroused you feel no pain.  The same basic thing happened to the welders, and as I turn you on, the same thing is going to happen to me by the way.  It is just how it works.”

“Look at your eyes, they keep going to my legs and trying to see my pussy.  Maybe there is an inch or two of my dress covering up my pussy.  Now I pull it up to where you can almost see it.  Now I open my legs a little so you can almost see it.  Look at your breathing. I open my legs a little more, and you are getting pulled toward me like a magnet.  After being in this cage a week, you are so damn easy.  You can’t control what is happening to you right now, but I can.  You somehow thought it would be great putting yourself in this situation.  I didn’t see the potential, but boy do I love it now.  This is your fantasy, but I enjoy it so much.  So, no you are not getting out.  I have lots more planned for us, my dear Robert.  I want to explore and develop my powers over you.  And, I am guessing all men have the same weaknesses.  Now ask yourself, how much will I pull up my skirt sitting here in the mall.  Growing my powers over you is so easy.  First, is my attitude.  I have to grow into being a wicked Princess and enjoy using my powers.  Second, I just have to keep you in the cage, keep you turned on, and let the horiness and frustration build day after day.  I own you, Robert, dear.”

Ally texted me to meet her on the 4th floor, the roof of the parking garage.  After three nights in the cage, I was horny but okay.  I was still glad Ally agreed to play the game, although I had questioned my sanity a few times when I awoke in the nighttime with a hard-on that would not go away.

There were a lot of parking spots on the lower floors as my car climbed to the top.   Ally was sitting on the hood of her car, the only car besides mine now on the roof.  Her bare, lightly tanned legs were stretched out in front of her; she was in a red billowy dress that was very short.  Her hands were on her dress to keep the strong breeze from lifting her skirt.  She slid off the car as I drove up and the wind picked up her dress exposing her bare ass.  Her hair was done up on her head and she had bright red lipstick on.  She looked great and had an evil smile on her face.  She had some evil plans that caused some movement in the cage.  I smiled back sheepishly.

I got out of my car and she planted a big kiss on me.  She then announced to me,

“I want this date to be just like in your fantasies, but even better.  You’ve always wanted me to do kinky things with you, I think after this week I am brave enough to try almost anything.”

FOR MEN ONLY

Let's take a short break from the Chastity Journal and learn about a game for a keyholder to play with her chastity slave.

One More Dice

M O E (Multiple Orgasmic Experience) An M O E is defined as the Princess Keyholder having three or more orgasms during the first hour, typically the first twenty minutes, of a guy going down on me.

CS is a chastity slave with no access to sex.

CCS is a Chosen Chastity Slave with select opportunities to give the Keyholder Princess oral sex and/or Fuck Her with a strap on dildo

For each round, the Chastity Slave meets me already in his Chastity Cage at a local pub.    He hands over the keys to his cage (which comes from my supplier) and we roll the dice (Round 1, one dice, Round 2, two dice, etc.)

Past Performance:

65% of guys owe me more MOE’s at the end of the month than at the beginning.

25% of the CCS quit after the first month.  80% of the CCS’s quit after two months.

One CCS has made it into the third round.

When I woke up about an hour late for work, I deduced Ally had woken up and got herself to work somehow.  If she was around, I would have been asking to get out of the cage; I was not having fun.   I got up and hustled into work. Ally had left me one small note in our log:

Robert, I hope you are starting to get horny so I can have some fun with you. Ally

Three nights in the cage had left me more aggravated I thought than horny.  But apparently, that was not completely true. [sPause sec=1 ePause]

The team secretary, Sally, came into my cubicle to bring me a copy of the handouts from a meeting that I had missed.  My cubicle is small so it was a little crowded when she pulled a chair into the cubicle to go over some things that had been assigned to me during the meeting.

I had books on the floor in front of her feet so she had to struggle with where to put her feet. My space is a disaster.

It was the first time I had seen her in a dress and it was short by her standards.  The dress was about mid-thigh with her sitting down and for the first time ever I noticed she had well-shaped legs and a good body even if perhaps with a few more curves than I normally lusted after.

From my new perspective inside of a cage, she had good curves, great curves actually.  In trying to sort where to put her feet, she had one on my one-foot-high stack of books and her other one on the floor; at that moment where she struggled with where to put her second foot, I caught a glimpse of her pink underwear.  She pushed her flowing floral pattern dress in between her legs and held it there with one hand to cut off my view. She knew that I had seen and I knew she knew, etc.  Apparently, my face was filled with satisfaction and she gave me a very cute half-smile. “Was she flirting,” my brain screamed?

My caged friend slammed into the end of his tube; my face must have registered how discombobulated and surprised I felt. My body did not feel like it was my own.  My body felt more than hypersensitive to anything female, it felt as if it was acting independently of me.  No matter how many times it had happened, I could never get used to it.  There was that very brief feeling when the blood rushing into the penis felt good and I welcomed it because my primitive brain knew something good was going to happen.

I could almost feel the flood of good hormones into my body.  And for that five seconds of bliss, I forgot that something bad was going to happen. Then in my case, the blue tube seemed to tighten around my penis stopping it from going any further down the tube, at least easily.  My penis felt suddenly like it was pushing into an every tightening vise both from the side and then my penis was being pushed back into my groin.  The greater the level of arousal the more it felt like a fat stick was being plunged back inside of my groin.

“Are you okay?” she asked me. It was a simple enough question but I couldn’t talk.

In my normal world I would have enjoyed a flash of underwear and her smile, but it would have passed without much to-do.  But in the new reality of the game where I had been teased and turned on dozens of times without release and my emotional well-being was now tied to my denied orgasms, I was so turned on I could not see straight.  I was breathing hard and I seemed unable to stop escalating arousal.