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I am truly lucky to be blessed with a KH that not only seems to be horny all the time, but is also highly orgasmic. Whether I’m licking her pussy, fingering her, or playing with toys, I absolutely LOVE giving My Lady an orgasm. And I am very thankful for the multitude of opportunities I get to make it happen!

Take today for example. My Lady came upstairs to tuck me into bed this morning, and we began kissing and cuddling as we normally do. I could feel her excitement growing as my hands touched her all over; her body was pushing closer to mine and her breathing had gottern more rapid and deeper. Instinctively, I slid my hand between her legs and into her panties; they were absolutley flooded with her pussy juice. I rolled ML onto her back and began to rub her slippery pussy lips and her throbbing clit. It didn’t take long for her to start thrusting her hips up towards my hand. Soon I felt her body tense as she came, struggling to keep her moans quiet to avoid alerting the children downstairs of our naughty fun.

Later on, after the kids went to bed, ML and I shared a shower together. We were both heavily turned on once again, ML pressing her wet naked body against me, my cock straining against steel. I took the opportunity of being in the shower to give ML a nice, good squirting orgasm (always a favorite in the shower because of the lack of clean up needed). My Lady had also brought Adam into the shower with us, and after a good hard cum she wanted to be fucked. I used Adam to fuck her doggy style, holding the rubber dick where mine would be if it weren’t confined by the cage. I fucked her from behind nice and hard, my hips slapping against her ass as I drove deep into her. With no need to be quiet, ML moaned louder and louder until she squealed as she came all over the fake cock. My cock twitched in its cage in jealousy as I felt her pussy squirt some more pussy juice down our legs.

Then, just before it was time for me to leave for work, I had the chance to make My Lady cum again. This time, she was laying on the couch when she called me over as I was in the middle of getting dressed. She pulled me down and forced me to kiss her before demanding I finger her pussy until the same. I gladly obliged! I stood over her, looking into her eyes as I slid two fingers deep into her horny wet pussy. She moaned deeply as she maintained eye contact; it was so fucking intense! I fingered her deeply and firmly, just the way she likes it, and she was close to orgasm within minutes. Her body was writhing and tensing as her orgasm approached. She reached up, grabbed the back of my head, and pulled me down until our foreheads were touching. Then, My Lady looked directly in my eyes as her orgasm hit her. I could almost feel her sharing her intense pleasure with me, and I couldn’t help but moan in unison with her as her orgasm continued to flow through us both. She stood up on shaky legs and I stood up with a painfully constricted penis.

It really is a joy for me to be able to give My Lady such wonderful pleasures. One reason is because she looks God damn fucking sexy when she is cumming, but it’s not only that. My Lady and I share an incredible bond, a bond that is emotional and spiritual as well as physical in nature. ML understands that I will not be experiencing the pleasure of my own orgasm for quite some time, so she is gracious enough to share her pleasure with me through this bond. When she looks at me like she did on the couch, her eyes locked with mine as she reaches that height of pleasure that I cannot reach, I truly feel her giving me that energy. It is a special gift that I chersh every time, and it makes me want to give it right back to her over and over.

And over.

And over…. and over…..   🙂

My Lady has been thoroughly enjoying teasing my cock over the past few days, knowing full well that my next orgasm will be many months from now. Today, she decided to continue her growing dominance over me by forcing my body to do her bidding.

I went upstairs to take a nap late in the morning to adjust my sleep schedule after the weekend, and ML followed me upstairs to tuck me in. Still looking to satisfy her bondage craving, she cuffed me to the bed and began stroking my cock as she kissed me; I was hard for her within a few seconds. ML then went and grabbed the wand vibrator from the side of the bed. She used an extra set of velco cuffs to secure the wand to the shaft of my cock. Then she hit the switch, sending powerful vibrations all over and through my cock. I moaned loudly and pushed my hips up into the air. It felt soooooo good.

ML petted my cock, her fingers feeling just as good, if not better than the vibrations from the wand. She leaned in close to me, and looked right into my eyes.

“I’m going downstairs. You better be a good boy and not spill your cum, otherwise I’m going to lock you up for a month and a half with absolutely NO time out.” Then she stood up and left the room. “See you in a while,” she said as she shut the door.

I knew right away that I was in trouble.

For starters, I already knew it was possible for the wand to force me into a ruined orgasm in this type of situation; it had happened before. It was only a matter of time before my body gave in to the incessant vibrations. I also knew by the look in ML’s eyes that she was dead serious; if I had an orgasm, I’d be in the cage until August most likely. Part of me wondered if ML set me up to fail, that she was using this as the opening to an extended 24/7 lockup we had discussed in the past. But, as always, I want to be a good boy for My Lady. So I tried to hold off. I took deep breaths, I let my mind wander to a number of different non-sexy subjects. And, miraculously, it seemed as though I was getting a handle on it. My cock was softening. I was going to make it!

Then, as my cock started to soften, the wand must have slipped just the tiniest fraction of an inch, sending sensations to a different area of my shaft… a much more sensitive area.

My cock was once again stiff in an instant. I could feel the vibrations flowing through my cock in waves. I tried as hard as I could to hold off, but I could feel the orgasm creeping up on me. Slowly, torturously it came nearer. I gave it one last effort, holding it back with all of my body. But it was no use.

I moaned loudly as my body gave in, my cock pouring cum out onto the bed sheets as it twitched against the wand. Much like the last time, the orgasm was by no means satisfying; I needed stroking on my shaft to give me a full orgasm. Instead, my cum-covered cock twitched helplessly against the wand, begging for more stimulation but receiving none. I moaned in frustration, knowing that not only would the ruined orgasm make my need to cum even worse, but that I also doomed myself to a month-plus of having no erections whatsoever.

My Lady came upstairs shortly after (she must have heard my moans). She acted as if she was disappointed in me – calling me a bad boy, disobeying his lady, getting messy when I shouldn’t.* Then she explained that she would uncuff me and I would immediately head downstairs, and put the cage on as I was taking a shower. “Make sure it’s comfortable,” she said, “because it’s not coming off for a LONG time!” I did as ordered, locking the Jailbird on my cock, wondering what it will feel like after a month and a half of not seeing or feeling my cock get fully hard. How frustrated will I be? How relieved will I be to get the cage off? Will I even survive it to find out the answers to these questions? I guess there’s nothing I can do but let time pass now.

*Note: My Lady did mention to me out-of-role later in the day that she meant for this to happen all along. She was most likely going to leave me up there until the wand ruined my orgasm no matter what. If I managed to hold off, thent he struggling I’d go through would be enough torture, but she REALLY wanted to lock me up 24/7 until our next vacation in August. I was very thankful she told me this. After all, I pride myself on being a good boy; knowing I was doomed from the start was somewhat comforting.  🙂

Today I had my last orgasm of 2014.

Well, actually, I had three of them, but that’s beside the point. The point is that I won’t have another one for the rest of the year.

Thankfully, I knew this going in, so I was able to get really nice mental pictures of all of them. My first cum of the day was in the morning – before I went to sleep, My Lady came upstairs to “tuck me in.” She cuffed my hands to the bed, climbed on top of me and rode my cock until I was just about ready to explode. Then the stroked me the rest of the way while sliding a finger in and out of my asshole.  It sure helped me get to sleep, I can tell you that!

My second and third orgasms were pretty much back to back. ML once again gave me some anal stimulation during my orgasm, only this time it was a little bit more than her finger; she used Pearl on me and she allowed me to stroke myself to orgasm. That was a REALLY nice one! It has been a while since I stroked my own cock to orgasm, so I don’t know if that made it so great, or if it was Pearl giving me a little extra sumthin’ sumthin’, but it was a really good cum. The third was right afterwards – ML continued to stroke me right after my orgasm, giving me a little bit of POT for good measure. She got me close and then allowed me to jerk myself off again… it was my birthday, after all, and is there a better present than allowing your chaste male to masturbate? I didn’t think so! I made myself cum a third time, and I was nearly drained by the end of it. I think this was ML’s goal, because she promptly had me lock up in the Jailbird before I headed to work.

And so begins my 6-month-plus period of orgasm denial (ML has said that I might get an orgasm for Christmas, or perhaps I’ll have to wait until 2015, she isn’t sure). This is going to be a difficult test for me. Not only will my denial be the longest I’ve ever gone through (by far!), My Lady and I have discussed trying some things during this chastity period that will also set new benchmarks. She wants to keep me in the Revenge  for longer than I’ve been before, locking my cock away where I can’t even see it let alone touch it. She is also interested in attempting a longer period of denying my any erections at all, locking me in the Jailbird 24/7 for a full month. With the discovery of ML’s new favorite toy, going that long will be easier than it has been in the past.

Well, easier on her at least. It doesn’t get any easier for me no matter what happens. And I know that ML will be taking every opportunity to make things even more difficult for me, teasing me whenever possible. I can already see the excitement in her eyes, and we’ve barely just begun. But I have to admit… I’m excited about this, too. I’m exicted to see just how far I can push myself, and how much farther ML can push me after I break down.  🙂

I’m not sure where I read it, but I remember a quote that goes like this:

The sun shines brightest on the man who just got out of prison.

Whoever said this is seriously spot on, I swear.

Today being the first day after being allowed to cum in nearly three months, I’ve been trying to soak up all of the relaxation the moment can afford me. That’s not to say that I’ve been totally “relaxed.”  🙂  I’ve also been taking advantage of the “denial break” that I’ve been granted by My Lady. Notice I didn’t say “chastity break” there; I’ve been wearing the Jailbird to work the past two nights. But that doesn’t bother me a bit when I have the opportunity to have wonderful spontaneous sex with my wife.

This change of situation has made me realize a few things. First, it’s obvious that I’m still horny for My Lady. The frantic edge of the want has been filed down, but the desire didn’t (and most likely will never) go away. I have noticed that my cock is a little bit slower at “standing to attention,” but I believe that’s a result of having so many orgasms after a period of having so few (a.k.a. none). If you haven’t run a mile in a year, you’ll probably start having a tough time after a few laps around the block. My cock just has to get its wind back, that’s all.  🙂

I have also noticed that, although I do like cumming in ML’s mouth twice a day (brag), I also enjoy how it feels when my horniness has hit a level so high it can only be reached through a lengthy denial. The conflicting feelings of being totally energized yet drained at the same time, the highs from pleasing ML and the lows of being denied my own pleasure… it’s one major mind trip. Nothing else can recreate it.

This experience has also allowed me to grow closer to My Lady, not only on a physical level, but on an emotional and spritiual level as well. The mutual orgasm we had as we made love last night was absolutely incredible. It was a wonderful moment for both of us to share. Having that moment with each other after waiting for so long accentuated just how powerful it was for both of us. It also showed us both that, no matter the length of denial My Lasy should choose, that connection of ours is so strong that it will never fade.

My Lady and I have been going through some pretty intense experiences over the past week. I think we could both sense Maybe Day approaching next week. It was exciting, but it was also taking its toll on both of us.

Granted, it was probably more difficult on me than on ML. I could feel my horniness growing deep inside my gut and spreading to the outer limbs of my body. I had gone well past my longest period of orgasm denial. My balls were constantly feeling swollen and the veritable “blue balls” veins had appeared weeks ago. Even after ML gave me a milking over the weekend, I still found no relief. The finish line was near, but I was barely dragging myself there.

The denial of my orgasm was also having a not-so-obvious effect on My Lady. As time ran on and the intensity grew and grew, she began to ramp up her dominant side. She was taking advantage of my more and more often, cornering me and rubbing her wet pussy all over my face whenever she could. We began to do more bondage games, pushing the intensity further. ML eventually reached a plateau; she was no longer feeling the fun of dominating me.

“It feels like work,” she said to me this morning, which is the LAST thing I want it to feel like. I want ML’s control over me to be natural, to flow from her effortlessly. I don’t want her to fulfill a role she thinks I want her to. I want her to be her. If she feels like teasing me in cute ways one day, then bring it on! If she isn’t in the mood for any teasing whatsoever, no problem! She was starting to feel obligated, and neither of us wanted that. So I asked ML if we could take it easy tonight and just lay with each other and make love. Those were apparently the exact words she wanted to hear, as she responded with an empahtic YES!

Before ML brought the kids upstairs to bed, she handed me the key to the Jailbird and whispered to me to unlock myself for when she came back downstairs. Eeeeeeeeeeeeeeeeee! I didn’t expect this kind of love making! I quickly whipped the cage off and waited for her to come downstairs. We sat with each other for a little while, kissing as we slowly undressed. Once we were fully naked, ML got up and got her phone and told me to get ready to shoot a video.

As I hit record, she took my cock in between her beautiful tits and started rubbing them up and down my shaft. Oh my God, it felt so good! I was almost ready to blow my load in seconds. In between breathy moans, I told ML that I was getting close to cumming. I expected her to slow down, but she continues the titty fucking. I told her again, this time in a semi-pleading tone. She responded by simply shhhh-ing me and moving her tits up and down even faster. She continued until I could feel my orgasm hurtling towards me. There was no stopping it now!

And then I was cumming! I was having my first orgasm in 80 days, and it was hitting me hard. I moaned and whimpered as it pulsed through my entire body. I looked down at my cock, spurting cum all over ML’s titties (I thought there’d be a lot more, but then I remembered the milking session on the weekend). It just barely registered in my mind that I was recording the whole thing. Somehow I ended up getting a great angle on the whole thing!

My Lady cleaned the cum off of her tits, and I immediately laid her down on the couch and climbed on top of her. I entered her, and we truly made love. It felt so amazing to not have to slow down, or worry about accidentally cumming. In fact, since I had just had an orgasm, I was hanging in there pretty well. Still, it didn’t take all that long until I was ready to cum again. I picked up my pace and thrusted a little deeper, and just as my orgasm started I felt ML’s body tighten underneath me. Oh God, we were having a mutual orgasm… fuuuuuuuck it was beyond awesome. I could feel the waves of pleasure flowing through both of our bodies as we shared an intense orgasm. What a wonderful night.  😀

So, in the end, we came up a week short of the intended Maybe Day, but that’s why we call it Maybe Day. ML has the right to give me an orgasm sooner or later, completely up to her discretion. And she needed that closeness today. We both did. I’m not sure if the fact that it was 80 days factored in to her decision or not; she does love round numbers after all.  😉

My Lady sent me to work tonight wearing the Jailbird again. I am thankful for two things. Actually, make that three, with my orgasm being one (hehehe). I’m glad that I don’t have any guilty/down feeling about cumming. I’m not disappointed about not being made to hold out longer. In fact, I’m happy that ML made a decision that she wanted instead of just blindly pushing to Maybe Day. I’m not sure how my moods will be in the next few days, but right now I’m feeling good. I’m also thankful that I’m not mopey about going back into the cage. It felt good to go back in at ML’s direction. I don’t find myself feeling cheated or wanting more time out.

And what about the plan for my next denial stint? Neither of us are really sure where it’s going to go. ML has mentioned a number of options. She has thought about locking and unlocking me multiple times and perhaps not even giving me a real denial time – allowing me to cum fairly often for a little while. She has also mentioned the possibility of locking me up 24/7 with no release time until my birthday and seeing where it goes from there. Honestly, anything she chooses will be perfect as long as she makes the choice freely and without pressure.

cagedmonkey: So…….. can I cum yet? 🙂

Lady: Uhhh, no love, it’s just not time for that. Especially when you’re at work.

cm: Of course. Why do I even ask? lol

Lady: Hoping one time I’ll actually say yes? 😉

cm: I guess so, although I have a hard time believing you will say yes. There have been times recently where you were so horny I thought you might cave in, but you didn’t. If you didn’t give in during those times, I doubt you’ll ever give in to me early.

Lady You’re right, I’ve become much stronger than in the beginning. At first I was still in the “need to please him” phase even if I didn’t think I was. Deep down I didn’t want to frustrate you, upset you, etc. It just caused me to be weak to your pleas.

cm: Now it seems like it’s the exact opposite – the more I beg and plead, the more you enjoy it and the harder you push me!

Lady It must be bittersweet that I’ve become so strong, huh?

cm: Honestly, I couldn’t be happier. I know that I can be honest with you about how I feel (sooooo frustrated!!!) and what I want (to cum sooooo bad!!!!), and not worry about influencing you or topping from the bottom. You truly are in full control, and I’m very lucky to serve a dominant with such a strong sense of what she wants.

Lady You are a lucky boy! Hehe 🙂 It wasn’t hard after awhile to embrace the frustration and let it entertain me. Once I was able to almost laugh at your situation, I began to really get enjoyment out of your frustration. I started enjoying the control of making you so incredibly horny for me. I just love getting you to that point where you HAVE to touch me just to feel my skin… because you’re THAT horny.

cm: And I definitely am that horny! Speaking of which…… can I cum now?

Lady No :)~

cm: Damn…..

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Yes, that’s correct… I’ve been out of my cock cage for pretty much the whole day today! Going back to last night, actually, it’s just about 24 hours now. I had an appointment earlier today, and My Lady actually allowed me out of the house and not in her company without being locked up. I had to ask her if she was sure, I was surprised! Obviously I didn’t have permission to cum, but this was the most freedom I’ve had since ML and I started practicing male chastity.

And I’m not going to lie… it feels good.

Last night and early this morning in bed with ML, it felt really nice to just roll over and slide into her pussy on a whim. The spontaneity of ML grabbing me, squeezing me, stroking me through my clothing is so exciting. I really do like being unlocked!!

But, let’s not get carried away. This situation is just as frustrating as wearing the cage is. Those unexpected touches from ML are driving me mad, shooting my desire into the stratosphere and making me incredibly horny! All of the sex ML and I have been having since she unlocked me is great… but I need to cum. And each sexual encounter makes me need to cum even worse. Even walking around the house, I can feel my cock brushing against my clothing. I’m so sensitive after over a month of denial, it’s like I’m being constantly teased! Seems like the cock cage was doing me a favor. 🙂

And just because I say that I’m enjoying my (most likely temporary) freedom, that doesn’t mean I want to end our chastity play. Far from it! I do enjoy my freedom, but it is this freedom that makes being locked in chastity so intense and wonderful. And THAT is why ML and I do this – we have an intense sexual connection through denying me regular sexual outlets, allowing her to control all aspects of my pleasure, and having me serve and provide her with as much pleasure as she desires. A day or two of going “free range” is never going to change that.

 

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.  😉

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.”

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.