My Relationship with Chastity

Ever since my first sexual encounter, I’ve been practicing tease and denial. I’d slip off into my best friend’s brother’s bedroom and we’d mess around at a ridiculously young age. He four years older than I was an just as inexperienced, which made everything pretty exciting for me. I remember how much fun it was having access to his body, getting to touch and lick and kiss. We kept at this for weeks, each week building up what we were doing. We started with kissing and then moved onto oral sex and then one night we were talking about having sex. I wasn’t ready, but he didn’t need to know that. Instead, we played a fun game of edging for the entire night until we fell asleep. Shortly after that experience, my family moved.

I’d fooled around enough to have some idea of what I was doing when I met my next serious boyfriend. Our relationship led right into sex and I found out rather quickly that my favorite position was on top. I could scratch my fingernails down his chest, pin his arms above his head while I rode him, but most importantly, it afforded me the ability to pour (the wrong kind of) candle wax on his chest while I took my orgasm. CFNM, tease and denial, forced masturbation, light pain, body worship, all of these things were things that were absolutely normal to me and I couldn’t have imagined sex any other way.

Years after we got together and a couple of years after I was married, I came across an erotic story that I’d read about a woman who wanted to keep her husband in chastity. The thought of it was incredibly appealing to me. I didn’t much care that my husband masturbated; I knew that he did and sometimes I’d ask about it because it turned me on. Sometimes he was even thinking about me, which I thought was sweet. I did like that I would get to control when we would have sex instead of being expected to put out whenever he wanted it. Mostly though, I just liked the idea of chastity. It was taking tease and denial to a whole new level. At that time, I didn’t even realize the level of frustration (or pain) that could come from wearing a device. Putting him in chastity made me want to play with him more, touch him more, tease him more, taste him more, and so naturally, like everything else I’d ever suggested to him, I brought it up. Without even hearing why I liked the idea of chastity so much, he not only declined to try, but told me that there would never be a man out there that would let me lock him up.

Our marriage was pretty open from the start. There were a few of my kinks that my husband didn’t care to participate in, namely anything having to do with control. He made allowances so that I could have a pet on the side that I could do all of my tease and denial and controlling and pet play with. Typically they were just internet things so they weren’t very obtrusive and they allowed me a lot of room for creativity. I had one sweet pet named Lin that would do puppy/kitty play with me on cam, that was often the victim of my tease and denial, and that would allow me the game of mental chastity, where he was never allowed to orgasm without my permission. Most of the time it was also required that I got to watch him on cam. I’ll never forget the way that he would squirm and bite his lip right before he would beg so sweetly, “Mistress, may I cum?”. Sometimes yes, sometimes no. All the time if he came he had to clean it up. I was fortunate enough to get to meet him in real life for a weekend and if I knew then what I know now, we could have had a lot more fun.

My next relationship was local but all of these elements remained the same. There was no impact play, there was only a matter of controlling him, tease and denial, and chastity. There was no device used here either, because I enjoyed getting to use his body. It wasn’t that I was ever using his cock, but I liked rubbing against it. More so, I really enjoyed having him on top and jerking him off against my clit so that when he begged and I granted him release, he would squirt right against my clit and then I would come as well. Not quite simultaneous orgasms but good enough for me. This one was precious to me because I was able to discover that I enjoyed oral sex a whole lot and he was always happy to give it. We’d get up in the mornings and he’d service me. He’d shower and I’d watch tv while he made breakfast and then he’d service me again. If I got horny in the middle of the day, I’d pull his face between my legs and get off again. And it was almost mandatory that I would receive oral before I fell asleep at night. Sometimes I’d push him down between my legs, cover his head with the covers, and hope he could get me off before it got too hot for him. Other times, I’d let him have an orgasm, but only if he could jerk himself off while giving me oral and cum by the time I did.

Finally, after those relationships ended and I was back to just play partners, I met someone who had a device. I didn’t get to do much more with it than see it, see how it worked, hear about it, lock it on him for a day or two, before the play was over. It wasn’t going to work out long term anyhow. The device was a hindrance to him because he was a cross dresser, a beautiful one at that, and the device gave him away. I didn’t want that. I thought he was hot when he was ‘en femme’ and I wanted other people to think so as well. I wanted to take him out and have this beautiful girl on my arm and have no one think anything of it. It never really developed into anything other than a hunger to play with a real device.

Then I met him. When he told me that one of his main fetishes was chastity, I couldn’t figure out why. After all, all I ever heard from guys was complaints that they weren’t allowed to masturbate or they weren’t allowed to cum or the devices made them look weird or this or that or anything else. He liked the control of it, the ownership of it. Or at least he thought he did. The first night we met, I got his key. He did quite a few days in the device and magically, this world that I had always dreamed of opened up to me. On top of the chastity though, we were engaged in some serious mind fuck. No touching. No seeing. It was my cock, not his. I would do with it what I wanted. I would ignore it if I wanted to. He may never receive another blow job. He may never feel another hand touch my cock ever again. Best of all, he may never experience intercourse ever again because he gave me his cock and now that it was mine, I may never want it inside of anyone ever again.

All the while all I could think about was how much I wanted to unlock him after a week or two of chastity. I wanted to tie his hands behind the chair, make it so he couldn’t touch himself at all, kiss down his neck and chest and slide between his legs and slowly, carefully, unlock his device. I wanted to carefully remove those plastic pieces from around my cock. I wanted to take him in my hands and feel the blood flow deep into my cock, watch as it finally, after weeks of denial, got to grow to its full size. I wanted to see the way his eyes would roll back in his head as my fingers played up and down the shaft. I wanted to hear the groans and the whimpers when my tongue flicked the head. I wanted to see how fast and hard he would cum when I granted him an orgasm. I wanted him to know that his pleasure was because of me. Because I allowed him the pleasure. Because that cock sure was not his and without me, he wouldn’t know what it was to cum ever again.

Really, what is there to dislike about chastity? Especially from the Keyholder’s point of view.

An Experiment In Chastity

July 19, 5:30am: Good morning Akalashi. It was a very good thing I did not have the key. Last night I was cursing myself for leaving the key at work. Let’s just say you were constantly on my mind. At one point I thought the device was going to break! The torment was almost too much to take.

It’s a little embarrassing, quite humiliating but also a turn-on that someone could sneak a peek, so to speak, and maybe figure out that it’s not my cock bulging from my pants but a chastity device.

I am wiped out and tired! That blasted device has had me awake more than I thought. But it always has me thinking of you.

July 20, 5:30am*: Good morning! What a glorious day! Sleep has once again eluded me. You will be most pleased to hear that my inability to find release last night caused me such physical and mental pain and torture that I was almost reduced to tears. My pillow was once again a victim of attempted rape.

Last night was the most intense yet! You are at the forefront of my mind. I am not exaggerating when I say rape and crying. These are accurate adjectives to describe my night.

Remember, this is coming from a man that used to masturbate every day.

You have me in a perpetual frenzied state at the moment. I can’t think, breathe, or move without physical arousal happening. Which always brings me back to the fact that you possess the key.

I did not anticipate how much of me you would own by your possession of the key, now your key. Because not only do you own my cock, my orgasm, my pleasure, you own my sleep and thoughts as well. I cannot sleep because of your cock. My every thought turns to you because of your cock.

I may never come again. That is something I never even contemplated!

July 21, 5:30am: Good morning Master**! I am now even more sleep deprived than I was yesterday. I was able to manage a couple of hours. The pain in the scrotum has now become such that I cannot even think about touching. The testicles are swollen. They have turned purple and cold. Each night the torture becomes worse than the night before. I am coming to a point that sleep is something I have to avoid. If I can avoid the sleep maybe I can avoid the pain and torture. This is much more extreme than I have ever imagined. Please tell me what I must do that you will allow me some relief from this device. I am desperate!

You are now my obsession. My physical body yearns for you, my every thought is of you, my only desire is to please you.

You reaching down between my legs and feeling nothing but the hard plastic device that caged your cock was a very humiliating turn-on.

I can’t sit, I can’t stand, I can’t think, I can’t sleep! But then I think about the pleasure my pain, anguish, and torture gives and it makes it worse! Because knowing the more pain, anguish, and torture I endure the more pleasure you receive.

My greatest fear is that you’ll keep me in chastity indefinitely. What would be so bad about that? To be free from the flesh between my legs. Didn’t that already happen when I gave you the key? I relinquished all rights of it to you. So why can’t I wash my hands of it and walk away?

Oh my god! I am never going to have intercourse again, am I? I hadn’t considered that possibility either!

How is it that I’ve gone from having intercourse multiple times a day to never having intercourse again?!

Absolutely every single feeling is pumping through me right now knowing that I might not ever have sex again. I may not even be allowed to masturbate much less cum. Hell, this damned device may never be coming off! I am feeling angry, mad, betrayed, hurt, sad, defeated, stupid, humiliated, aroused. What I imagined and what I negotiated are two very different things. That is my own fault! All of these feelings are directed at myself. It was my decision to move forward. I am also very scared. Scared of how sadistic you can and want to be. What else might you take from me and use against me?

I am being reduced to a membered eunuch.

July 22, 5:30am***: The pain from raw skin is beyond anything I have experienced! Sleep is something I now know I will never have again. One more thing to put on the list! Each day it seems there is something else you have taken from me. I am yours!

Last night was once again intense. Not sure how I cam going to make it through the day without sleep! I hurt and am too sore to continue a relationship of that nature with my pillow. Simply sitting is now a chore. I am now wondering if I will be able to continue like this. I am hoping that soon I will just become numb to it. I really do need out! But I know there is nothing that I can do or say that will make that happen. I am at a point where the actual physical pin is so great that I want out not to get off but to relieve the pain.

Right now I don’t even want to touch your cock! It is that sore! I apologize for not taking proper care of your cock. I just did not know how to.**** I would like to try to continue on to Monday.

Once you have your cock locked to the cage, not just in it, I will truly become your slave. Never to know an orgasm or freedom again. Am I correct? Your own personal torture toy. {In response to my informing him that since I own his cock, I could pierce it if I’d like.}

I’m tired. Falling asleep at my desk. I can’t think straight. I can barely work. I’m confused and scared. What have I done? How did I get here? I agreed to chastity. Having my cock controlled. But so much more has been taken. You have pointed out how stupid I am. I was thinking with my dick.

I am scared because you have used my sex to abduct me and I never saw it coming. I just happily handed it over to you.

* This is the first report after being given the key to his chastity device

** Dev was seeking an appropriate honorific to use to address me, as we are not in a D/s relationship, we are only Keyholder/victim at the moment. I commented that I was amused the key reads ‘Master’ on it and at first he rejected the idea of using such a term, because Master implies so much to me (and to him as well) but after much consideration, there is a distinct flavor of ownership to at least this one part of his body, enough that we agreed this would work. He also pointed out how nice it would be to have my name right on my key.

*** This was the first day that he was required to start sending pictures along with his morning report to help ensure that I can see what’s going on in order to make better, more informed decisions about whether or not continuing with wearing the device is in the best interest of his health.

**** Dev discovers lube is his friend and it helps to keep the cage from chaffing the skin.

Chastity. This is something that I’ve always wanted to try but I never had a boy that owned a device who wanted to play with me. I met someone on CollarMe that had some of the same interests as me. My initial draw to him was the fact that he spoke of submission and learning, not of fetishes and kinks. There were a few things that held me back from contacting him at first, but eventually I sent a letter. The person that I got to know was much more than I had expected from his profile, and he said the same about me. Of course that may be due to the fact that I have a rather generic profile.

One of the topics that kept coming up between us was his desire to be owned and to experience a full D/s relationship. Anyone reading this journal knows full well that I am trying to avoid that kind of situation because there were a few other things that I’ve been wanting to experience, and this was one of them. Dev had mentioned that he wanted to try wearing his device. He’d only ever gone for 48 hours wearing one before and never any longer. He masturbated daily. His last kinky relationship pretty much had him being used as a sex toy, made to perform for his Mistress several times a day. To hear the stories from him personally, one would think he was kept on site for a porn shoot, never knowing when he was going to be pulled out to be fucked again and again. But it didn’t have all of the D/s elements he was looking for.

With some encouragement (what?) he decided late Saturday night to put the device on of his own accord. He let me know that he had and I told him that I was rooting for him. Throughout the weekend he gave me updates and told me how difficult it was for him to do this and how much easier it would be if he had a Keyholder. Sunday he told me that he was afraid he would just unlock himself and be done. I told him that if he was especially clever, he would take the key to work and leave it at his desk to avoid that temptation. He took my suggestion and did just that.

That evening, through reasons completely unrelated to his stint in chastity, we had agreed to meet. I enjoy meeting local people who have similar views to my own. I was hoping too that if we met, I might be able to encourage him to join one of the local communities, perhaps even attend a play party with him. He had mentioned that he may bring his key with and if things worked out exceptionally well, perhaps we could negotiate me being his Keyholder, and talked at length what that would mean to each of us.

The evening was spent going over hypothetical situations, expectations, hopes and desires of both kink and vanilla. Towards the end of the night, after negotiating, he offered me his key and I accepted. The negotiations that he offered lacked two things: an ending period and any kind of limit regarding release from device, orgasm, or intercourse. I was perfectly aware that he’d forgotten about these, but I figured rather than just merely mentioning them, I would show him what happens when he forgets to negotiate to the very last detail in hopes that he would never make the mistake again. (I think he’s learned his lesson.) The only other thing that he didn’t allow himself, which I strongly encourage in every other situation, is a safe word. His lack of a safe word means more responsibility for me, ensuring that I don’t push him further than I think he can go, because I’m the only person now that can stop where we’re headed.

His expected date of release is Monday, July 25th. I’m hoping to make this birthday one he remembers for a while at least.

I Can’t Promise You The World

This past week at work was a mess. One of my bosses decided to schedule me for a shift that I couldn’t possibly work without some outside help. Since the car accident, kitty’s been left without a car, so he uses mine to get to work. He works late; I work early. This works out! Thursday and Friday of last week, I had to work late. This didn’t work out! I had to arrange to get someone to drive 80 miles in one day to pick me up, take me to work, drop me off home, and then go back to where they lived, right next to work. I was not pleased. I don’t know why this person even agreed to help me out! But she did, and it was sweet of her. I bought her dinner and gave her gas money. She had to repeat the morning trip on Friday but Friday night I had covered.

Joey probably had no idea what he was getting himself into when I messaged him and asked if he’d be willing to pick me up from work, instead of meeting me at my house like usual. I explained that I worked a little ways out, but if he would do this for me, it would increase his rank in the Teh Bestest Pet Ever competition he didn’t previously know he was competing in. At first I think he was tentative. I guessed this because he asked me just how far out I worked. “Just follow the freeway you usually take to get to my house to the end.” To the end of what, I could hear him asking? “To the end of the freeway.” Joey is very, very expressive. Not always through words though. Usually just his deep, brown eyes. Via text, it comes out like this: O.O

“Best pet ever?” was what he asked in return and I knew he was hooked. It might have also had something to do with the fact that I mentioned pets that could offer service as well as their backside always got me revved up, and I wasn’t entirely lying about that either. Oh, and if he picked me up, we’d have to go get this flogger I was looking at. C’mon now, it was pay day.

Friday night, he came to hang out with me at work for a while. He drove me to the store to buy the new flogger that we’d played with together the time before last when we went to buy new lube for him. This is a beautiful flogger that I almost missed in the dark of the dungeon. I’d found a whip, one without a handle, that was designed to look like barbed wire. This pushed all the right buttons for me because when I was a little younger, I used to have fantasies of tying up boys in rough rope and barbed wire, but I just couldn’t find a good way to get barbed wire into the place without breaking SSC. Now that they’d made a leather alternate, I was hooked. I lashed him with this and the way he jumped and swore had me sold. Oh, but there was no handle. However was I going to work this? Just then, peering down into the darkness, on the next shelf, which was home to floggers, I found it: a suede flogger with falls of leather barbed wire in them. I snatched that baby up and Joey barely had time to turn around to offer his back to me before it fell upon him. The same reaction! Glorious!

Well now that it was pay day, I had to have it. And have it I would!

After that, we made our way back to my house. I knew I wanted to use that on him. I also knew that I couldn’t use just that on him or we wouldn’t each have a wonderful time. Tonight we’d do a proper warm-up.

Usually when he comes over, I give him time to get in the door. I don’t kiss him right off, because it’s too much like a relationship he’s said (although I’m beginning to think he can see how this all fits together) so instead I just let him join me in the living room and we talk for a bit. The dog (the real dog) is always super excited to see him and I think it’s best that he gets some attention first, if we want him to leave us alone at all while we’re playing.

Then comes the magic moment, when the dog winds down a bit, and Joey looks at me, waiting to see what I want to do. “Strip!”. It’s said with some enthusiasm, usually. Sometimes deadpan, but with a smile. It’s so entertaining to me because he is still so shy. He watches me when he can, but otherwise looks around to everything else in the living room while he casually pulls off his shirt and lowers his pants. It’s always the hesitation at the waistband of his underwear that makes me smile. I reassure him that I’ve seen him naked before and he laughs nervously. It doesn’t make it any easier this time around.

Tonight was different though. For one, he was standing on the other side of the room. I’d ignored him up until then, trying to get some music started so the neighbors didn’t hear the sounds of floggers. When he looked at me, I went straight for him. A kiss. There was no collar around his neck yet — it wasn’t part of the scene — but it appeared to be okay. I kissed him and helped him undress. It was as smooth as I can be, which really means it wasn’t smooth at all. I’m used to him taking his socks and shoes off when he gets in the door, tucking them under the coffee table where his furry bff can’t thieve his socks away for a vacation while we’re playing. I got all of his clothes off his body, had my fingers curling around his hard cock, and then realized my mistake. Oh well. He wasn’t shy undressing that time, and that was all that mattered.

In a matter of seconds he’d finished the job that I’d started and climbed onto the couch, kneeling away from me. I started with the old flogger, Old Trusty. I can swing and fling and flap and hit and thwap with that all night long. I can really get into it too. Usually I’m pretty good with it but he’d tell you there’s been one or two strikes to the side, completely unintentional. I wasn’t quite lined up right when I let go — premature flogging, due to excitement. Each time that I bring it out, I try to hit him harder and harder. He admitted once that part of him really wants me to hit him as hard as I can and the sane part of him is glad that I don’t. We’ll get there. I know this because I can see how far we’ve gone in such a short amount of time.

Caning is another favorite and while I usually tend to keep like toys together, which would have meant the new flogger would have come second, I didn’t think he was ready to go from thuddy to super stingy. I have a very thick cane that’s very thuddy and bamboo canes that are very stingy. I’m positive that they both got used. I’m positive that he did not get such a warm up for the bamboo canes. I can attest to this because there was more time spent sitting upright, breathing, then hunched over with his ass pushed out ready to accept another strike. So little effort; so much pain. I love these canes.

After that came the paddle. My paddle is beautiful. Thick, wooden, covered in sandpaper. It was frightening enough that pup, the construction worker, felt the need to point out the quality of the sandpaper and assure me that that was the real deal, this wasn’t fine grain to help save skin. Thanks pup! To anyone less experienced with sandpaper, it just hurts. I made sure that it hurt Friday night too.

Once I was done with the paddle, there was a crop. The crop is lovely because it makes the best smacking sounds ever when it connects with an ass. Especially a lovely ass that’s made to accommodate the size of the heart at the end. He’d jump when I hit him hard. He’d jump when he thought I was going to hit him hard. Friday night was all about pushing him and making him hurt. He’d mentioned that he thought I might make him bleed that night. I told him I hoped I would.

One major difference in the way we played Friday night was that I paid some special attention to his nipples, primarily by thwacking them with the bamboo cane and ensuring that they were rubbed by sandpaper. I remember him specifically pointing out later on that his nipples hurt while the rest of his body was mostly just a dull ache.

Finally we got to it: the new flogger. I tried to go light, I really did. It’s much heavier than Old Trusty though. I wasn’t quite used to the feel of it. I tried to swing it around behind him before I made contact but I was aroused. The first fall hurt him more than I was expecting but he put on his brave face for me. We have this agreement going that the less he says ‘fuck’ in normal circumstances, the happier I am. When I’m beating him, he can say ‘fuck’ all he wants and I don’t care. I think it’s hot, actually. Well, when this flogger came out to play, that was all I heard. Thwack, fuck, thwack, fuck. Amazing.

Afraid that he might not be able to handle it, I crawled up on the couch behind him, I pressed the handle of the flogger against his collared neck and pulled him back against my body. I told him ‘This is your one chance to get out of this if you want. You can ask me to stop right now, and I’ll put the flogger away.’ He swallowed, breathed for a second, and asked, ‘What do you want?’. I was thrilled. I was so turned on. ‘I want you to take more for me.’ So he nodded, I let him go, and I hit him more. To ensure that we didn’t go too far though, I made him answer in numbers. One a scale from one to five, one being my light strikes with Old Trusty and 5 being oh god, stop please, he was to let me know where he was at all times. I got a three, a four, and a lot of fucks. Never a five. We didn’t go for much longer though — I was too turned on.

I put the toys to rest. I had him climb down off the couch and kneel in front of me. I pet him for a moment, but then I remembered that my favorite toy was out to play. Reaching down, I began to stroke his cock. He knelt nicely, letting me play. He let me know when he was getting close. He’s never allowed to orgasm without permission. One of my favorite things about him is how sensitive the head of his cock is. Just touching it is an amazing experience for me. So I dragged my fingers over it, masturbating just that part of him, and watched with delight when he actually pulled his entire self away from me to get a moment’s reprise. When he was getting too close, we stopped.

Here’s where things go a little soft, a little vanilla. Picture some kissing, some rubbing, and a boy wearing a collar for me working to get me off in a new and exciting way for him that would probably elicit some yawns from the rest of us. Not that it mattered to me — I orgasmed.

After that, I pushed him back, had him sit at the corner of the couch, and told him to jerk off. In a matter of minutes he was riding the edge, fighting between doing what I told him to now (masturbate) and doing what I told him to always (don’t come until I tell him to). This is always an exciting game for me. He asked. He begged. I gave in way too easily, but he’d done me proud with all the pain he took. He came and I told him I loved the smell of it — like fresh rain.

After that, I took the boy out to eat so he wouldn’t starve to death. Waffles at midnight are a godsend. He made a bet, as we were both yawning, the he couldn’t stay up until 4am. What? Why would either of us agree to that? Because he shook my hand for so long that we were holding hands over the table in the middle of IHOP while not in a “relationship”, that’s why. I knew as soon as he got home and had constant stimulation he’d be able to make it. The wager? $10.

Needless to say, I lost the bet. Tonight I pay up. I have my own creative way of feeling better for losing though, which ties into service, which ties into “I Can’t Promise You the  World”. Tune in later!