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Conversations in Chastity: It’s Tough For Us Keyholders, Too!

Posted by JonMustWait on April 15, 2014
Posted in: Conversations, Male Chastity, Wife Led Marriage. Tagged: , , , , , , , , , , , , , , , , . 4 comments

Lady M: I can’t get enough of feeling your body, touching you all over.

cagedmonkey: I love the way you touch me.

LM: I want to touch you all over. I miss your cock.

cm: Yeah, about that… can I ask you something out-of-role?

LM: Sure, baby. What’s up?

cm: It seems like lately you’ve been really missing my cock… I’d say almost as much as I do, but that’s pretty much impossible. But I’m getting the vibe that it’s starting to take its toll on you too. Do you want my help with finishing the whole month you planned to have me locked 24/7? If you start to break down, do you want me to remind you?

LM: I’ll be okay. When I tell you that I miss you cock, I’m just expressing myself. I’m not going to pretend that I don’t miss it.

cm: Good, I don’t want you to pretend. I also kinda like it that you miss it.

LM: Right. See, I can’t play that “hard ass Domme” role like I don’t want your hard cock. This stuff is hard on me too, you know.

cm: I know, but I need to know how bad you want this. Because I obviously want out of the cage, and if you start getting weak I can’t guarantee what I’ll try to talk you into it. But if you REALLY want this to happen, I’ll try my best not to push it. We may need to work together when we try to stretch to new limits.

LM: I do want to make it. I will let you know if I need your help. It’s only a few weeks, I should be able to make it.

cm: You say “only a few weeks” as if it’s not that much time. To me, it’s “a few weeks!”

LM: Only a few weeks until I get to wrap my hand around that big fat cock of yours.

cm: Mmmmm, I love it when you describe it like that!

LM: Well, it is big and fat… but only when I allow it to be.  😉

The Man Without a Penis

Posted by JonMustWait on April 14, 2014
Posted in: Male Chastity. Tagged: , , , , , , , , , , , , , , , . 3 comments

A few nights ago, My Lady and I were laying on the couch together, and things started to get sexual… as they very often do nowadays. 🙂 We began kissing and touching each other; things started to get really hot, really quick. I rolled over on top of ML and began thrusting my hips towards her as I kissed her deeply. All of a sudden, both of us felt it at the same time: we flipped the “power switch.” All of a sudden, I felt very dominant and powerful over ML.

When I get dominant, I tend to talk dirty a lot. I rubbed up on her, and I started asking her if she wanted to get fucked. If she missed taking my hard cock deep inside her slutty wet pussy. ML was getting turned on, too, pushing back up against me as I pushed my hips down against her. I pounded my hips down on her, doing everything I would be doing if I was fucking her pussy as hard as I could… except for the fact that my cock was still locked in its steel cage, of course.

Afterwards, I started to get a little down. All of the simulating of the dominant, forceful sex kinda made me miss it a bit. I realized that I really do miss my cock. I miss being able to fuck My Lady hard and deep. I miss the way ML’s warm pussy feels when it’s squeezing my cock. I miss being able to fuck ML more than three thrusts at a time. Hell, right now I just miss my cock getting hard!!!

I didn’t expect these feelings to show up so strong and so soon into the 24/7 month. I’ve gone 24/7 longer than this, but not with the pretense that I would be waiting an entire month for my next full erection. It’s really getting to me this time around. I’m not really having second thoughts about all of this – chastity is still the most amazing thing that has happened to our sex life, and I wouldn’t change it a bit. But still, I can’t deny that right now a decent part of me truly feels like a prisoner locked away against his will. This is when chastity truly becomes “enforced chastity.”

Sentenced to the Jailbird

Posted by JonMustWait on April 8, 2014
Posted in: KeyHolder, Male Chastity, Wife Led Marriage. Tagged: , , , , , , , , , , , , , , , , , , , . 4 comments

So the HUGE piece of news I teased in my last post was already spoiled by ML in her last post, unbeknownst to me: My Lady has decided to keep me in the Jailbird 24/7 until the May 4th. No removing the cage. Not even a cursory release for my poor cock. I will be locked up for the next 26 days straight.

624 hours.

37,440 minutes.

2,246,400 second.

Not like I’m counting or anything.

My Lady and I have talked about trying this for quite some time. When we were discussing it, it really turned me on. How would I respond to not having an erection for an entire month? How will I feel after it’s been so long since I’ve seen my cock get hard? How will it feel when my cock is finally free of the steel and can swell to its full size?

Now that it’s happening, it’s a little bit overwhelming. Although ML has caved in the past and given me mercy during some of these “extended” times or denial or lockup, I have a feeling she’s not going to crack so easily this time. She’s very curious about the reactions she can coax out of me. If I start getting desperate, she may just grow to love it. Who knows? Maybe I won’t even be getting out until my next Maybe Day in June? No clue. No control over it.

Right now, I’m a little stunned. I know for a fact I’m really going to miss my hardon. I like it when my cock gets hard. It feels nice. I’ve come to enjoy the feeling of my cock pressing against the steel cage, but it doesn’t compare to the feeling of my cock getting nice and thick and big when I’m turned on. The longest we’ve ever done a 24/7 lockup stint is ten days I think, and I started to get a little antsy near the end of that time. I went into what ML likes to call “bargaining mode,” which is when I start to try to make a deal with her in order to get just the tiniest need filled. For example, near the end of that ten day period, I was literally begging ML to give me a ruined orgasm, just so she’d let me out and touch me. Again: I begged My Lady to give me an utterly frustrating ruined orgasm just because I needed to get hard and be touched. This was after ten days. I wonder what My Lady will have me doing by the end of this run.

Emotionally Sensitive

Posted by Michele on March 21, 2014
Posted in: KeyHolder, Male Chastity, Wife Led Marriage. Tagged: , , , , , , , , , , . Leave a Comment

I’m really tired of being sick, how is it possible that I feel worse this morning?!

That doesn’t really stop me for the most part. When I woke up this morning I wasn’t feeling particularly horny or anything because I felt like shit. However, cagedmonkey and I have a communication notebook and I was writing in it and got myself worked up anyway. I decided to pay him a visit upstairs while he was sleeping. I did just snuggle with him for a bit, until he put his knee between my legs and I started grinding on his thigh. I rubbed myself to a soft orgasm, it was nice, but it only made matters worse. I ended up sitting on his face and getting myself a good pussy licking. I love him being in the Jail Bird because I get to lick him and play with him while his face is shoved in my pussy. I came a few times and then another by my own hand before I headed back downstairs.

I don’t know if it’s me being sick, going to start my cycle or what but I’m emotionally sensitive today too. I feel like everything is a criticism. Maybe its just me because I’m sick, haven’t cleaned my house, folded the laundry or anything all week and I feel bad about it. Maybe I’m the one being over critical about myself so I’m putting it on others as them thinking that. I feel like I’ll never live up to expectations today. Like I’m not good enough for anything.

What a fantastic way for a Dominant woman & Keyholder to be, huh? Ugh!

I JUST WANT TO FEEL BETTER!

Dark Desires

Posted by JonMustWait on March 14, 2014
Posted in: Male Chastity, Tease/Orgasm Denial. Tagged: , , , , , , , , , , , , , , , , , , , , , , , , , , . Leave a Comment

As far as fetishes and kinks go, male chastity can be very diverse. Many things can be added to or augmented to chastity; no two experiences will be exactly the same. What I’ve found is that chastity has opened up many different areas of kink to My Lady and me. There are things we thought we’d never try that we found were a huge turn on for both of us.

Last night at work, ML and I were having one of our “remember when” discussions about  the time she fulfilled my rape fantasy. I was amazed at how incredible the experience was, and how much I enjoyed it… after the fact, of course! As we were talking, we began to brainstorm about how to take it to the next step. As we were considering a lengthier scene, ML writes me the following text:

“Not too tough with enough time to spread it out. Like being kidnapped, kept, and repeatedly raped, hehe.”

My jaw literally dropped.

And my cage immediately got tighter.

What a GREAT IDEA!!!!!

We spent the next two hours, tossing around ideas for how to draw it out, including but not limited to: sending the kids to a multi-day camp, so she could abuse me over the course of days; cuffing me in various positions in various places around the house; blindfolding me, and using a variety of toys on me without warning; fucking my ass with the strap on, or toys of her choosing as I lick her pussy; leaving me restrained while she goes to rest, returning later to continue her assault; riding my cock while shoving a dildo up my ass; keeping the tease up while the kids are home, sneaking into the kitchen when I’m alone and roughly fingering my ass, giving me no place to hide; and so on.

Needless to say, my cock was trying its best to get hard. In vain, of course, pushing against the walls of the Revenge. But DAMN, was it hot. It was turning us both on! I have a feeling this will happen sometime in the future. 

It really is amazing that My Lady and I can discuss these dark desires with each other, without worrying about how the other will react. We made a promise to each other when we started this to be honest and open about any fantasies we have, no matter how out there they may seem. How else would we know if we liked something or not without trying it first?

I know all you guys out there always say that I’m the luckiest guy in the world, and I really am…. but not for the reasons you think. It’s not because My Lady locks up my cock for weeks on end, denying me orgasm until I’m insane with need, teasing me mad until I’m about to explode. It’s because I have a partner who loves me, respects me, and cares for me enough to allow me to trust her with anything and everything that is inside me without fear. And she has the same thing in me. THAT is why I’m so lucky.

Ok, I won’t deny it… I’m pretty lucky for those other reasons, too. 🙂

The Art of Eating Pussy

Posted by JonMustWait on February 22, 2014
Posted in: Advice, Wife Led Marriage. Tagged: , , , , , , , , , , , , , , , , , , , . 4 comments

I usually don’t work in absolutes, but I’m going to drop one on you right now only because it’s 100% true: every man should learn how to eat pussy. Period. Chastity or not, it’s one of the greatest and most generous things you can do for your lover. I always enjoyed it, way before the FLR/chastity lifestyle with My Lady began to form. For me, it’s such a turn on to know I can satisfy my wife with just my tongue (or fingers, should the desire arise). And now that I am in chastity, my pussy eating skills are all that more important!

It is very easy to enjoy licking My Lady’s pussy, simply because her pussy is DELICIOUS. Her taste and smell turn me on so much that I cannot get enough of it. I can (and have) eaten her pussy for as long as she will let me… 15 minutes, 30 minutes, an hour… it’s like an all you can eat buffet for me! I love the way she reacts to my tongue, gradually moaning more and more, louder and louder, until I push her over the edge of orgasm and she explodes. I don’t mind getting her gooey pussy juices all over my chin, or even the occasion squirt on my face… I wear it like a badge of honor. 🙂

I was always pretty good at oral sex; I have a strong, agile tongue that can handle lots of work. I’m also very dedicated to pleasing ML. But the most important aspect of my pussy eating prowess is the fact that I LOVE doing it! Naturally, you are going to be better at doing something you like. Speaking of: to those guys out there who don’t like eating pussy… what the fuck is wrong with you? REAL MEN EAT PUSSY. Give up your hang ups and just do it. Otherwise, some guy who likes doing it is going to do it better than you and steal your woman. Don’t say I didn’t warn you! 😉

So, as I was saying… I’m pretty good at eating ML’s pussy. But just like anything else, there is always room for improvement. So I ended up reading through She Comes First: The Thinking Man’s Guide to Pleasuring a Woman to see if I could learn a few tricks. And learn a few tricks, I did! I learned how to control the amount of pleasure I give My Lady, holding back at times to build tension: for example – pressing my tongue firmly on her clit and holding still; after a few seconds, she very often starts asking (begging?) me to make her cum. That’s when I unleash on her to release that stored up tension, flicking her clit quickly with my tongue until she cums good and hard. Using this rhythm, I can draw out the pussy licking over a much longer amount of time, pleasing ML almost endlessly, instead of just going right for it, making her cum hard, and draining her of energy.

I highly recommend this book, for beginners or for so-called “experts.” Everyone can get something out of it. Thanks to this book, I can now make My Lady buck and bounce all over the bed while I’m eating her pussy. I sometimes have to hold her down just so she doesn’t push me off of her with her hips. And the noises she makes… let’s just say I need to be really careful about when I lick her pussy, so I don’t end up waking up the kids, or any of the neighbors! 😉

Eating pussy is an excellent tool for a man to please his woman, and I feel that every man should learn how to do it well. It’s wonderful foreplay, a great way to turn your partner on. And for those of us in chastity – where foreplay is pretty much the only sex we are allowed to have – it is an essential skill for pleasing your keyholder.

Taking a Chance

Posted by JonMustWait on January 17, 2014
Posted in: Male Chastity, Tease/Orgasm Denial. Tagged: , , , , , , , , , , , , , . 3 comments

roulette_lg

To celebrate our anniversary this weekend, My Lady and I are taking a trip to a local casino for some gambling & drinking fun. She even set us up with a babysitter for the day so we can go and enjoy ourselves without the kids in tow. What a wonderful anniversary gift for BOTH of us!

Until, of course, I open my big mouth.

You see, part of our agreement is that I tell ML about any and all fantasies or ideas that I get that involve our sex life. ML has been struggling with the decision on whether or not to let me cum on our anniversary – she REALLY wants me to fill her up with a nice hot load of cum, but she also REALLY wants to push me further. She couldn’t decide. That’s when my kinky, creative brain kicked in and came up with an idea that she seems to like a helluva lot more than I probably will.

Here’s my idea – we are going to find the roulette table in the casino and choose one spin to dictate a number. That number will determine how many extra days will be added to my current stint of orgasm denial. Thanks to the zero and double zero spaces, I actually have a 1/19 (~5%) chance to cum that night. However, I also risk the possibility of having to go another thirty six days without an orgasm. Considering I am already approaching three weeks without an orgasm, the longest time since we’ve started our chastity lifestyle without cumming, adding another month-plus on the back end is going to be torture. I know what I’m rooting for. What My Lady is hoping for is a mystery to me…

Wish me luck!

I Can Do It One Handed

Posted by Michele on January 13, 2014
Posted in: KeyHolder, Male Chastity, Tease/Orgasm Denial, Wife Led Marriage. Tagged: , , , , , , . Leave a Comment

I may have had shoulder surgery but that’s not exactly stopping me from A. Cumming or B. My WLM/Dominating. I will say that cagedmonkey is doing a fantastic job picking up my slack and doing the things I can’t. It started off rough and he didn’t think he could do it but I think he relaxed a bit and found that things don’t have to be perfect or exactly my way. When I ask that things get done, I just want them done. He’s been great about taking care of the kids and getting them to their activities. He’s been cooking most of the meals and even helps me bathe and get dressed. Like I said, he’s basically being my Super subby hubby! 🙂 I couldn’t be more proud of him, pleased with his service, his dedication and how hard he is working! Love this guy!

With all that said, I did mention that it sure isn’t stopping me from getting my orgasms and certainly isn’t getting him any. He had a little “free” time last week but has been back in his jail Bird and his next unlocking won’t be until January 18th. It’s not a definite orgasm day for him but I might give him a chance to cum at least. 😉

Today has been quite the subby day for him. He’s begging to do anything I ask of him. He is craving my direction and awaiting my orders. Aside from his chores, he was required to wear the njoy for a few hours today as well as service me right when I ask. I went upstairs to put away some clothes and had to call him up to help… he asked what I needed help with and I simply said “my pussy needs to be licked.” He immediately got on his knees and made me cum twice – and, to praise him, he even dealt with our daughters homeschool questions while doing it! 🙂 Awesome!

Is that service or what?

Tonight we have some celebrating to do in the midst of a very Dom/sub kinda day. We will be having some drinks tonight and having a while lot of kinky fun! 🙂

Mail Chastity – Questions from our inbox

Posted by Michele on January 10, 2014
Posted in: Mail Chastity, Male Chastity, Wife Led Marriage. Tagged: , , , , , , . Leave a Comment

A gentlemen contacted us to ask some questions about our WLM & chastity and I thought I’d share incase others had similar questions.

“Is it just an at home lifestyle? Did is happen right away or did it build to a FLM?”
Our WLM is an everyday, all day thing… our relationship has always been one where I took care of everything – financially, phone calls, Dr appts, anything with the kids, etc. We do make big decisions together, where to live, buying a car and that kind of thing. Usually I have the final say in most things though.

“Is it D/s?”
Just so you know wlm & D/s don’t need to go together but yes part of our relationship is D/s. Our sexual relationship is fully D/s and it will only trickle into daily life if we talked about it specifically where my Dominance will be an entire day thing. Hope that makes sense.

“Did chastity come first? and did it contribute to this decision?”
Chastity most definitely didn’t come first. We’ve been flr since we met – I’m a control freak hehe. We had gotten to a bad place in our relationship, we worked hard to repair it and in the repairing made a promise to be honest and share every fantasy. Hubby brought up the chastity thing and, at first, I wasn’t into it. Part of our promise was to be open minded about fantasies so I started to research and found, after about 4 months, that I really loved the idea and that’s how the whole chastity thing began. 

“How did you get it to work?….. We tried it before and it only lasted a month. It seemed rushed and not natural”
Some people are not naturally dominant so to have a wlm they do need to work at it, take it slow, step by step. Once we realized what our relationship was and that chastity was to be a part of it we created an agreement. That’s been a huge help in getting things to go smoother and “work.” It’s still a work in progress and probably always will be. We will continue to go over our agreement to change things. We have added things, adjusted things and taken things out. It’s not a perfect science, there is no one way to do things… it’s what works for a particular couple and no two relationships will look the same.

Thanks for your questions and please feel free to email and ask anything you like. Most things are not too personal and we love the interaction.

How to hear from you!

I’m a Good Boy

Posted by JonMustWait on January 9, 2014
Posted in: Male Chastity, Wife Led Marriage. Tagged: , , , , , , , , , , , , , , , , . Leave a Comment

As you may have read in an earlier post, My Lady recently had shoulder surgery that has left her with pretty much only one functional arm for the next few weeks. I’ve been waiting on her hand and foot (and toes!) for a couple of days now; it has been rough working so hard for her, but thing are settling into a groove. She is starting to feel better, as well as slowly returning to her “insatiably horny and wet all day every day” status. 🙂

Over the past few days, I have realized that I truly am at peace when I am serving ML. Sexual service is obviously more exciting, however serving her in non-sexual ways also gives me an energy from within. Most importantly,  I thrive on her feedback; it was rough going when she was in pain and feeling terrible, but it is getting better as her mood is improving. I live to hear those words “such a good boy” escape those sexy lips.

I have spent most of the past week unlocked, however I have still been denied an orgasm (still cum-less in 2014!). As ML’s physical comfort has allowed, I have been pleasing her with my tongue, hands, and also with my cock. She has mentioned on quite a few occasions that I feel exceptionally large this week. While I’m not the type to figure out exactly why I’m receiving these AWESOME comments – what guy doesn’t want to hear they have a huge cock? – it may be due to the fact that the frequency of penetrative sex has been less leading up to now. All bragging aside, I have somehow managed to hold myself off from cumming during this time. I can’t count how many times I’ve WANTED to shoot my load of cum deep in her wet warm pussy, but so far I’ve been that “good boy” that I strive to be.

What exactly makes some of us sub males so dedicated to our keyholders that we are willing to be SO committed to our chastity and orgasm denial? Why do some men need anti-pullout features on their chastity devices, while others can fuck their KH without going over the edge?

I can’t speak for everyone, but for me it’s that I am fully focused on My Lady’s pleasure. She gets off on the control she has over me, and I get off on her controlling me. I know that she would be extremely disappointed if I were to cum without permission (unless she forced me to, but that’s a different story). For me, it’s about giving My Lady what she desires. And what she desires is a man who will allow himself to be denied indefinitely until she wants to please him, and who will serve her every need until that moment occurs.

She wants a good boy. And I want that to be me. 🙂