Misadventures in Chastity

(written by my beautiful and beloved sissy maid, Angela)

Since meeting my wonderful Mistress, I have been, by choice, locked in a chastity device. When I met her, I owned a CB-3000 chastity cage that I asked her to hold the keys for. She happily agreed, and thus began my chastity service to her.

Having worn the device myself on and off for a few years, there was very little difference now, except that I no longer had the ability to unlock myself when I desired. I would now have to deal with it on a 24/7 basis, as well as any problems that come along with it. Everything was going fine, and other than not being able to release myself, I didn’t have any problem with it.

(A little background here…I am a cross dresser, and Lady Julianna's sissy maid. I also have a snowplow business, and most times would wear panties, pantyhose and short skirt under my snow pants when out plowing. Anyways…)

It was the middle of January here in beautiful, snowy upstate NY, and I was out plowing early one snowy morning. I was wearing some very cute panties, tan pantyhose and a denim mini skirt under my snow pants, and of course, the CB-3000 securely locked in place. It was around 6 a.m., and I was shoveling the sidewalk at a church I plow for, when all of a sudden I felt a pinch on the bottom of my balls. I kind of didn’t think anything about it until I felt it again, only this time it was much, much worse. Obviously, something was wrong with my CB, but I couldn’t tell what. I turned to head back to the relative safety of my truck to check it out, and the pinching pain was unbelievable! Every step I tried to take only made it worse.

So here I am, standing on the sidewalk of a church, in the early morning darkness, it’s like 2 degrees out, snowing like crazy, and I’m afraid to even move because of the terrible pinching I am feeling on the bottom of my scrotum. I remember painfully chuckling to myself, and thinking “Oh, this is fucking great. Now what do I do?”

Being so early in the morning, no one was around so I unzipped my snow pants, reached under my skirt, hose, and panties to see if I could figure out what was wrong. As soon as I touched the ring of the CB that goes around my cock and balls, I felt a very severe pinch that almost put me on my knees. I put my fingers down to the area being pinched, and could feel that the hinge part had broken, and there was a chunk of very tender skin caught in between the broken pieces.

At this point, I am more concerned with my well being than anything else, but every time I tried to move it just pinched worse and worse. Now even though there was no one around, I still couldn’t just strip down on the sidewalk of a church wearing pantyhose and a skirt to inspect my chastity device. I would go to hell for sure for that! So, I reached into my panties with both hands, and pulled the broken ring apart slightly, which hurt like hell, but also instantly felt better. Now at least I could move without pain.

Holding the ring apart with both hands, I waddled…yes, waddled the 100 feet or so back to my truck, managed to get the door open, and climb in to the cab. After making sure the sensitive skin of my ball sac was no longer between the broken pieces, I pulled my snow pants down, pulled my skirt up, pantyhose and panties down, and finally able to see what the deal was.

The hinge part of the ring was indeed broken, and my only choice was to pull it apart enough to slip my balls out and remove the device. Fortunately, I only suffered a small cut on the bottom of my scrotum, but in that area, it felt like a 6 inch gash. I threw the CB on the floor of the truck in disgust, pulled my panties and hose up, my skirt down, and zipped up my snow pants, and went back to shoveling the sidewalk. Walking back to where I had dropped my shovel, I saw my foot prints from my waddle back to the truck…toes pointed out and shuffling in the snow, and burst out laughing to myself thinking of what that must have looked like, and being very thankful that it didn’t happen at 2 o’clock in the afternoon.

When I told Lady Julianna what happened, of course the first thing she wanted to know was if I was alright. After assuring her that I was, and telling her how I solved my little problem, we both had a pretty good laugh over it. She said she would have given anything to see me hunched over with both hands down the front of my pants, waddling back to my truck. Looking back on it now, I have to admit, it had to be a pretty fucking funny site.

A few weeks later, she got me a new CB-6000, which is a totally different and better design, and much more secure and comfortable to wear. We expect no similar problems with this device, and I am safely back in chastity for her.
contributed by cdangela315

Sissies and Massages and Fuck Pigs, Oh My!!!

I can hardly begin to describe the insanity that went down in my house this afternoon. I am kicking myself severely for not taking pics. I managed to snap two (bad) pics with my cellphone, which I will include.

Sissy arrived early, which is unlike her. She is usually on time to the minute. I put her to work scrubbing down the walls in her ruffled uniform and 5 inch heels while Bacon worked in the kitchen. I took my time getting ready, having fun doing my makeup and playing with my hair, and when I was finished I just sat and looked pretty while the slaves finished their chores.

I brought the boys downstairs and made them strip. Sissy down to her sequined red panties and stockings, and Bacon down to the flesh. I bent them over side by side, four perfect asscheeks to spank, all in a row. What fun! I paddled them both soundly, until their asses were a nice cherry red. When I felt their poor tushies had had enough, I moved on to more interesting things.

I ordered them to stand back to back, with their heels touching, and wrapped their ankles in several layers of cellophane. Teetery things, they were. I wrapped them together from the shoulders to the hips, to their cocks were free for me to play with and their hands were tightly wrapped flat at their sides.

 "Now, dance." I told them and delighted in their silly hopping and wiggling. When I got bored, I sat on the low stool in front of Sissy and engaged in a little cock and ball torture, wrapping her cock in rope and swatting at her balls, making her jump.

"Don't fall down, if you fall down you are in trouble. Now turn around."

They pivoted and moved their feet until Bacon was now facing me for his turn, but he got a different kind of torture. He's such a big baby about chastity and constantly whining about how bad he wants to cum, I thought I might have fun edging him. I pressed up against him, breathing in his ear and stroking his cock. It wasn't long before he started to whine. When I felt his cock begin to throb, I let go and smiled evilly. "I bet you want to cum REALLY bad," I whispered, and walked away.

Rummaging around in Sissy's toybag I found a smaller roll of wrap, about 5 inches wide, and sat back down on the low stool, with Sissy's cock and balls at eye level, all bound with ropes and swollen. Holding the balls against the cock, I wrapped it very tightly with layer upon layer of cellophane, and followed suit with Bacon. Then I garnished each one with a pretty bow, just for fun.

"Chastity cage doesn't seem so painful anymore, does it?" I asked them, and gave their "packages" a firm smack.
"No, Mistress," the Sissy replied.
I looked at Bacon. "What about you? Not so bad, eh?" and smacked his package again.
"No, Ma'am."
"Good," I smiled and whacked their chests and legs with my bamboo rod, then a wooden paddle. They are both very sensitive to nipple impact, so it was nice for me to be able to strike a little harder than normal. The cellophane offered some protection. I slapped their pretty packages every so often to keep their attention, and eventually got bored and cut them loose.

I ordered Bacon to the corner to kneel on the concrete and stroke his cock, but not to cum.
Sissy I had other plans for. I ordered her face-down to the floor for a good spanking. I spanked her over and over with the kayak oar, and when I struck hard, she would tend to jump or try to roll over. I bound her ankles quickly but tightly with my quick ties, sat on her legs, and spanked her even harder. I explained to her that she must learn to accept what is given to her. If it was too much, she could call her safeword, but otherwise, she MUST accept her spankings with grace and dignity. I spanked and spanked until her ass was a shade of red that satisfied me, and then I crawled down next to her and held her close. Sending Bacon to fetch lotions for my massage, I had some quiet cool-down time with my pretty sissy maid, drying her tears, kissing her, telling her she is a good girl, and that she was very brave.

When Bacon returned and Sissy had pulled herself together, it was time for my massage and worship. I stripped down to my panties while Bacon fetched the long table. I laid face down and enjoyed their strong hands rubbing me down with fresh, summery-smelling lotion. Their four hands traveled over my body firmly but gently, relaxing and arousing me at the same time. They rubbed every part of me, every inch, and I rolled over so they could continue their magic. When I was nice and relaxed, I sat up and they immediately positioned themselves at my feet like good slaves, and we took a little time to talk and hang out.

Noting the time, I sent Sissy upstairs to clean her chastity device thoroughly for a few more weeks of lockup, and to change out of her sissy clothes and back into her guy clothes. During that time, I ordered Bacon into spanking position, and took out a little aggression on his ass with my trusty bamboo cane. I told him to keep a better eye on my drinks in the future, to not let my glass get empty, to take better care with cleaning behind the toilet. His poor cock was now purple and raging, and I told him what a horny little pig he is.
"Now off! Go fetch your pig uniform and do it fast!" He scurried away and came back a moment later with his pig snout, ears and tail. He put on the nose and ears, and offered his ass to me to insert the tail. What a good boy. He looks so fucking cute in his pig outfit. I inserted the tail into his ass, and he moaned like a horny little fuckboy.I rammed it in and out a few times, getting him good and worked up.
"Are you a little fuckpig?"
"Yes, Ma'am"
"Yes, my dirty little fuckpig, aren't you?"
"YES, MA'AM"
"Now look for truffles, piggy!"
He took off on his hands and knees, snout to the floor, snorting and snuffling like a little pig should. I smacked him with the bamboo cane, telling him he is a naughty pig, he snorted and snuffled and WHEEEEE'ed when I struck him. He came to my feet where he planted kisses upon them, all the while continuing to snort like a piggy. He kissed up my legs and thighs and I grabbed his hair, driving his pig snout into my panties, holding it there, and throwing him back to the floor.
"TRUFFLES!"
Off he went again, nose to the floor, snorting and rooting and waggling his piggy tail. The cane stripes on his ass raised into red welts. He looked fantastic. His ass in the air, his snout to the floor, his swollen purple cock hanging between his legs.
"Enough now!"
I ordered him to kneel and edge his cock yet again, and Sissy returned to the dungeon for me to lock her device. Our session time was up. I looked at Bacon.
"Up!"
He stood.
"Clean up this mess"
I took Sissy upstairs to see her out, and Bacon emerged shortly thereafter.
I rubbed up against him.
"You were a good pig today."
He beamed. "Thank you, Ma'am."
I grabbed his cock. "I bet you would like to cum, wouldn't you? It's been WEEKS, hasn't it?"
"Yes, Ma'am"
I patted his cheek and smiled. "Not today, my piggy. Not today." And I locked him back up.
I love them both so very much.
What a wonderful day.

Chastity Games

One of my kinky friends was delighted to hear I was keeping my slaves chaste. She clapped her hands in a giddy sort of way and grinned like a Cheshire Cat.

"What kind of chastity games do you play?" 

I stared at her blankly. "Games?"

"You know! Do you roll the dice and see how many days he stays locked up? Or do you draw a card? Or put marbles in a bag?"

I almost fainted. Leave My power in the hands of chance? NEVER! Sure it sounds fun but that's not what I use it for.

Chastity is NOT a game... at least,  not to Me. It is NOT to add "spice and fun" to my life. It is a symbol of true ownership. As keyholder, I choose when they get to release. Not the roll of a die or the draw of a card or marble.

Mama taught me "If it's not yours, don't touch it."

Their cocks and orgasms belong to ME, not them. 

"If it's not yours, don't touch it"

^Bacon's cock locked away where it belongs^

Chastity and Orgasm Denial

The rule has always been that they don't masturbate unsupervised and without permission. It's in the contract. I have been having a situation with the slave getting a bit of an attitude because he was "hurting" and his "balls ache" from not being able to masturbate and frankly, I am sick of him walking around with an erection all the time. slaves can't think straight when they are thinking with their cocks. Enter the CB-6000. The CB has always been renowned for being the most secure chastity device on the market and the most comfortable for long-term use. Their new model, the 6000, debuted several months ago. I ordered two, one shipped to my sissy maid in the next county over, and one shipped here to my house for my live-in slave. Sissy's arrived first. He looks forward to his chastity, he has always been a fan. I had him locked in a pretty old CB-3000 for several months before the hinge broke and it had to be cut off. We expect no such problems with the new (improved) model. Sissy is all locked up and ready to go, with a tamper-evident tag with a serial number on it. When he comes for a session next week, we will put the permanent lock on it and I will keep the only keys with me. My houseboy, on the other hand, has no idea what's coming for him. I told him I had ordered him something online, and he was to deposit the money in my bank to pay for the item. He did. He is excited. He won't be excited when he finds out that there will no longer be a way to cheat on the "no masturbation" rule. His body, his cock, his orgasms.... they all belong to me. I choose when he is allowed to cum and I choose when he is allowed to touch and I choose when he eats, pees, showers, shits, works, sleeps and plays. When I unlock him for play, when I give him the privilege of cumming, he will then learn to appreciate it. It will enforce his devotion to me and not himself. Plus, not having a choice may make it easier for him than the honor system.

Chastity is an exquisite torture, and it puts me in full control of the most intimate part of my D/s relationships. I can't wait to begin this delicious torture on my subs.

Update 3/15/11 the other CB arrived today, both subs are now officially locked down.