chastity, male chastity

All posts tagged chastity, male chastity

My Night Was Ruined

Posted by JonMustWait on July 22, 2014
Posted in: Male Chastity, Tease/Orgasm Denial. Tagged: , , , , , , , , . 2 comments

The current rhythm of chastity that My Lady and I have been using – in and out, whenever she desires – seems to be more intense than an extended lockup period. This way, I’m much more exposed to ML’s teasing, as it may come at any time whatsoever. I’m very glad that My Lady can trust me enough to have me unlocked when and for how long she wants… but I’ll admit it makes things a little tougher to know that I very well could jerk off, but I’m not allowed.

Yesterday I spent the day unlocked and constantly under threat of ML’s teasing touch. My cock was being teased and edged all day long, whenever ML was able to sneak away long enough from my kids trying to critically injure themselves. I was extremely horny by the time the kids’ bedtime came about, and ML and I went to bed shortly after.

After putting on a movie (to cover the sound, perhaps?), My Lady began toying with my cock, making sure to keep me aroused. After edging me four or five times, it was ML’s turn to have her rightful orgasm. She used her wand to give herself a body-shaking orgasm, and I joined in by using two fingers deep in her pussy, making her cum so hard she had to fight her hardest to stop herself from screaming and waking the kids. My favorite!

It was then her turn to torture me with my own desire. ML climbed up on me and straddled my cock, riding me slow enough to avoid making me cum. That ended up being not too fast at all – with her tits in my face and her warm wet pussy wrapped around my shaft, I felt ready to cum almost instantly. And when she spun around and faced the other way, the sight of that beautiful ass bouncing up and down almost drove me to orgasm even when she stayed still!

My Lady slid off of my cock and moved up towards my head. She clamped my arms next to my body with her legs and planted her pussy right on top of my face. She then fucked my face with her pussy, teasing and stroking my cock the entire time. I moaned loudly into her pussy as she pushed me to edge after edge. Adjusting her hips, she then pushed her asshole onto my face, forcing her tight hole down onto my tongue, fucking her ass with it. She spread her cheeks wide and she pushed down harder, grunting as my tongue pushed farther into her ass.

As I used my tongue to fuck her ass, she began to stroke my cock again. She edged me quickly, stroking me hard and fast and letting go quickly. Each time, my body nearly leapt off the bed, held down only by the weight of her ass on my face. She stroked me, and then she pushed me right to the edge and stopped.

I could feel myself teetering, hanging on the edge of orgasm. I tried to hold back, I didn’t want it to be ruined. But the whole situation was just too fucking hot – ML tease torturing my cock, edging me as she smothered my face and force fucked her ass with my tongue.

I couldn’t hold it. As my tongue pushed into her ass once again, I could feel the cum creep up the inside of my cock and leak out in a pathetic attempt at orgasm. I felt two or three drips of cum ooze out of my cock and onto my stomach. It was truly a ruined orgasm – it must have been a full three to five seconds between when ML stopped touching my cock and the cum dribbled out, and I got absolutely NO sexual relief from it! My Lady rode my face fit another minute or two, giggling at her handiwork as I moaned in frustration under her.

It was a very frustrating day for me in all – kept on edge for virtually the entire day, only to be slowly dragged over the edge with no pleasure granted to me whatsoever. However, I know how much my frustration pleases My Lady, so I can imagine how much fun she had creating the frustration. There’s always a positive to my sexual suffering.

What I’m Looking For (or, Why I Stare At My Lady When She Has An Orgasm)

Posted by JonMustWait on July 16, 2014
Posted in: Male Chastity. Tagged: , , , , , , . 27 comments

“What are you looking for when you do that?”

She said it with a breathy, trembling voice that can only be spoken by a woman in the moments between one orgasm and another. She didn’t get a chance to explain exactly what she meant by the question, as my tongue swirled over her clit and pushed her farther towards her next climax. I continued to gaze up at her from between her thighs as she came again, her pussy quivering under my lips and gushing wetness all over my chin.

I’ve talked in the past about how much I love to watch My Lady have an orgasm. Lately, I’ve started to watch ML more intently as she cums… so much so that ML might have thought something strange was going on, hence her mid-cunnilingus question. I answered (afterwards, of course… you don’t stop licking pussy to answer a question when your woman has her legs wrapped around your head and is humping your face like a dog humps your best friend’s leg) that I just love the way she looks when she is cumming. She is so beautiful, I swear. This look of pure pleasure and complete bliss comes across her face; she gets this tiny smile before her mouth drops open and she begins to moan. She closes her eyes and her eyebrows furrow, as if the pleasure is almost too much to bear. And her hands pull me towards her, as if to say there is nothing else that can make the moment more perfect other than being closer to me.

I love to watch her at the moment when her orgasm starts to get extremely intense. The past two nights, after licking her pussy for a while, ML and I have “cooperated” to give her very strong and very long orgasms – she rubs her clit while I finger her deeply with two fingers, my fingertips end up rubbing the inner wall against her fingers; in essence, we both rub her clit from opposite ends until she cums like a mad woman. Looking at her face when the orgasm begins to hit a new level and take on a life of its own is simply magical; I can see in her eyes when it begins to run away from her. She looks at me with surprise and concern, with just a tiny hint of fear, perhaps? It’s amazing. I know just when to say, “it’s okay, I’m right here baby… go as high as you want to.” That usually pushes her further as she knows she can truly let loose and be safe with me. The aftermath is wonderful, too – the shellshocked look on her face, somewhat unaware of what exactly just happened to her… just tonight, I had to point out to her that she was still rubbing her clit minutes after she had cummed herself out, as if her hand were on masturbation autopilot. That’s pretty hot, in my opinion.

So that’s what I’m looking for when My Lady has an orgasm – the moment where she loses herself and turns herself over completely to the pleasure that I am providing for her. It proves to both ML and myself how well I perform my subby duties for her. Because that is my ultimate goal – to submit to her sexually and give her anything and everything she could ever want or need.

 

Temporary Release

Posted by JonMustWait on July 2, 2014
Posted in: Male Chastity, Tease/Orgasm Denial. Tagged: , , , , , , , . Leave a Comment

Since I was home Monday night, ML and I decided to watch a movie and have a few drinks together. In the past, alcohol has not agreed with ML’s chastity and denial plans very well. This time, things were slightly different.

My Lady had been talking for a while about how much she truly misses my cock. After nearly three weeks of being caged every moment of the day, she was beginning to long for my hardness inside her. She stayed strong for so long, but the alcohol whittled her willpower down just enough to want me out of the cage for just one night.

She made it clear to me that she wanted me inside her, but I was not allowed to cum. Fine by me! After being held back by the cage for so long, I was willing to take whatever I could get. She unlocked me and pulled the cage off of my shaft, and I immediately let out a long, slow moan. It felt so damn good to be free of the steel. But that was only the beginning.

ML wasted no time in pulling me up on top of her. She spread her legs wide and showed me her sopping wet pussy. I was ready in no time. I slid my throbbing cock into her tight pussy; it felt AMAZING. I really did miss feeling her soft wetness wrapped around my shaft. I thrusted into her a few times, but my orgasm was quickly approaching; the drinking had a minimal effect on my staying power, unfortunately. ML began to rub her clit in order to cum on my cock, and I did my best to thrust into her as much as I could. It wasn’t long before I felt the walls of her pussy squeezing my cock as she came hard. I looked into her eyes as her orgasm continued, and I couldn’t handle it anymore. I quickly pulled out, trying to avoid cumming on accident. I only half-succeeded – cum dripped from the tip of my cock as my orgasm was ruined all over the blanket beneath us.

ML laughed and pulled me on top of her once again; she wanted more. And this time, with my orgasm ruined, I was able to handle a little bit more. This time, I thrusted into her slowly and deeply, looking deep into her passionate eyes as I made love to her. Her body began to convulse as she came hard once again, and all of a sudden I realized that I was nearly there, too! Once again, I pulled out as quick as I could, and once again cum dripped out of my cock – my second ruined o of the night!

ML still was not finished with me – she wanted my cock in her ass. She turned over on to her stomach and ordered me to fuck her tight asshole. Being the good sub that I am, of course I obeyed. My cock slid easily into her ass, lubed by the slick juices of her horny pussy. My Lady grunted deeply each time I finished one of my long, slow strokes. Then I leaned down and pushed my cock deep into her ass, and she growled with animalistic heat. I felt her moving so she could sneak a hand underneath her body, and she began rubbing her clit furiously. I held still in her ass, hoping her orgasm wouldn’t cause me to ruin a third orgasm. Luckily, I was still in good shape when I felt her body tense up and her asshole grip my cock as her orgasm hit. She moaned loudly and bucked her ass back against me, taking my cock even further inside her. I love playing a part in those super strong cums that ML has. It makes me feel so good that I can do that for her.

ML was finally satisfied with the thorough fucking she receieved. We went to bed shortly after, and I was allowed to sleep uncaged, snuggling up to her naked backside.

In the morning, we discovered an interesting development – I was feeling some skin soreness on the shaft of my cock. ML and I took a look and found the source of the pain – there was a small spot of irritation on the shaft of my cock, and it kind of looked like the way skin cracks when it gets really dry. We believe this is happened because my skin lost some of it’s stretchiness during the extended 24/7 lockup, and when I got hard after being unlocked the skin to stretch too much too fast, which caused the “injury.” Thankfully, it was only slightly uncomfortable, and only when touched. It didn’t prevent me from wearing the cage, which ML demanded shortly after I woke up.

ML plans to keep me locked for the entire month of July with no release time – “plan” being the operative word. Seriously, though, I think she means it this time. The irritation was a little red this morning, but there were no signs of infection or anything like that. I’m going to keep an eye on it. I’ve also decided to use some skin lotion on my entire cock and balls (instead of just using it for lubrication around the ring, as I had been doing). Hopefully this will keep the skin cracking issue from happening again when my next release date comes along.

Conversations in Chastity: The Frustration Grows

Posted by JonMustWait on June 30, 2014
Posted in: Conversations, Male Chastity. Tagged: , , , , , , , , . 3 comments

(The following is an excerpt from a text message conversation between Lady M and cagedmonkey the morning after an intense teasing session, which included multiple edges and a ruined orgasm inside the Jailbird!)

Lady M: Sleeping good, my love?

cagedmonkey: Yeah, pretty good… except for the fact that I want to hump the mattress, or you, or something… I’m fucking horny!!!

Lady: Oh, God that’s hot! I’d love for you to hump me!

cm: It’s actually beyond horny… my need for sex is almost painful, it’s so bad. And is it possible that my balls are even more swollen than they’ve been lately?

Lady: Maybe. I was rubbing them really good. I wanna feel them right now…

cm: I’m not even sure “horny” is the right word for it, anyway. “Horny” would indicate that I’m turned on or whatever. I sorta am, but that’s beside the point. Right now, I just need to fuck.

Lady: Hehe. 🙂

cm: I just filled up the cage in like three seconds… I’m twitching and throbbing now for no reason other than I’m talking to you.

Lady: Omfg, that turns me on so much!

cm: It’s so fucking intense right now. I was DYING before! I wanted to cum so badly, for real! I didn’t want you to deny me any more, I just wanted to cum and I didn’t care how.

Lady: I loved every second of it.

cm: It was so hard to get myself to “cum” and it totally wasn’t worth it… fucking sucked that you ruined my o while I was still in the cage. So fucking frustrating, I nearly wanted to cry.

Lady: Awwww, my poor sweet boy.

cm: I can’t imagine making it another 6 months. I don’t even want to wait another day to get out of this cage!

Lady: I wish I could help you with that. 😉

cm: Which part? lol

Lady: Any of it. 🙂 Hehe

cm: Yeah, but you’re cumming as much as you want, you can fuck my cock when you want apparently, and you can get a big thick (albeit fake) cock in your pussy… all without unlocking me! So I don’t think your desire to help me is as pressing as my need to get out of this fucking cage and empty my balls with a good hard cum is. 🙂

Lady: Yeah, I guess you’re right. 🙂 Speaking of cumming as much as I want, I’ll be upstairs as soon as lunch is done. You better be ready for me to grind my pussy on your face until I cum nice and hard…

cm: Yes, ma’am.

Two Can Play at That Game!

Posted by JonMustWait on June 26, 2014
Posted in: Male Chastity, Tease/Orgasm Denial. Tagged: , , , , , , , . 15 comments

There has been an interesting development in our T&D games this week.

My Lady has expressed some (tentative) interest in experiencing the locked side of chastity – she is willing to explore female chastity with me…. sometime in the unspecified future, according to her. 🙂 The thought of me in a dominating role with her is intriguing, she admits, but even more interesting would be how absolutely insane batshit crazy horny we would be for each other if we were both locked and holding each others’ keys. ML would never be interested in a long term version of this, and neither would I; she will always be the ultimate keyholder for me. Even in a mutual chastity setting, if she really REALLY wanted out, I’d allow it. She’s the boss, after all.

After approximately two weeks of total 24/7 chastity, ML is beginning to long for her much desired PIV. Sure, she’s gotten plenty orgasms (either from my tongue, my fingers, or her magic wand),  but she is really missing my cock. Rather than cave with over a month away from her goal of pushing me to August, she decided to challenge herself a little. She decided to test herself to see just how much denial she could handle – two days ago, she enacted a self-imposed ban on orgasms and penetration of any kind!

And I will admit this right now… I’m having a lot of fun with it.  🙂

First off, I’ll say that it hasn’t really been about me dominating her, really. It’s more like ML is using me as a tool to tease herself and to see how much she can take. It’s less “YOU’LL CUM WHEN I ALLOW IT, YOU LITTLE SLUT” and more “Am I teasing you well, ma’am?” It may seem like a strange dynamic, but it’s working and we are having lots of fun so far.

Pleasing ML so often in so many ways has put me in tune with her body and her responses to stimulation. Up until now, I’ve used this info in order to please her as best I can. Now, I’m using the knowledge of her responses to keep her from cumming. She may be an expert at edging me, but I can do the exact same thing to her. To be honest, it’s actually a little more difficult considering that ML can literally think herself to an orgasm (if only I could do that!!!). I have to be a little bit more careful in pushing her close to the edge, and I also have to rely on her not to deliberately make herself cum with only her mind. But she’s been playing the game the right way, and her pussy has almost been constantly wet since we started.

Edging ML sure is fun, but I might be enjoying teasing her with penetration even more. Before I left for work tonight, I was rubbing my fingers in between her pussy lips, spreading her wetness around. She was breathing heavy pretty quickly, and I could feel her hips pushing towards my hand. I pressed my fingers just the slightest bit more, almost pushing past her tight inner lips and into her pussy but juuuuuust not quite. ML began to whimper and moan, which is something I thought only I did when I was being teased.  🙂  Even hotter was what her pussy was doing – I could feel her pussy lips sort of grabbing at my finger and trying to pull me in! I could tell she was desperate to have anything inside her. I gave one last push with my hand before removing it from her pussy. ML growled in frustration and her body shuddered as she struggled to fight off one of her famous spontaneous cums.

I totally respect My Lady for trying this out and seeing what she is capable of. I know for a fact that she will never be able to last as long as I do without an orgasm; she just loves cumming too much! That’s a good thing, too, because I love making her cum. To be honest, I don’t know if she is going to make it to her goal of getting to the weekend without any cumming or penetration, but the fact that she is giving it a try is impressive enough for me.

Alternate Pleasure Centers – Activated!

Posted by JonMustWait on June 21, 2014
Posted in: Male Chastity, Tease/Orgasm Denial. Tagged: , , , , , , , . 1 comment

She looks up at me, that sexy confident look in her eyes. She knows exactly what she is doing to me as her tongue snakes out and tickles my sensitive flesh. I whimper softly as she teases me with her tongue, smiling as my body begins to shudder. I moan loudly as she sucks me into her mouth, pulling gently with her lips.

I could easily be describing what it’s like getting a blowjob from My Lady, only this time I’m not. With my cock locked up 24/7 until the end of July, it will be quite a while before I feel ML’s wonderful mouth on my cock. What I described above is ML’s new favorite form of oral sex – licking and sucking my nipples.

Lately, I’ve been finding that, since my cock is unavailable to receieve the sexual pleasure sensations that my body craves, other areas have stepped up to provide these sensations. In layman’s terms… my nipples are hella fucking sensitive all of a sudden. It seems as if they are almost constantly hard, and I can feel them rub against my clothing. Sometimes at work, when I go to put a pen in my pocket, I accidentally graze my nipple through my shirt and it gives me a small full-body shudder. And it’s not just my nipples; my balls are also extremely tender from being so full and being stretched so often when the cage pulls on them.

Don’t think ML hasn’t noticed this. She now takes any opportunity to tease me with these newfound sensitive areas. She has already taken a liking to flicking them with her fingernails or pinching them through my shirt whever she gets the chance. And when she gets me alone (and shirtless), she loves using her mouth on them – licking, sucking, and even biting them – and watching my uncontrollable reactions. The intense sensations shoot down my chest and build right behind my throbbing cock, increasing my desperate need for release.

My Lady knows that teasing these areas of my body have a strong effect on my horniness. And when I say she takes any opportunity, I mean she takes any opportunity. This morning, ML went out for some errands while I slept. I woke up while she was still out; I checked my phone and found a text message from her waiting to be read:

When you get this, I want you to pinch your nipple with one hand and roll it between your fingers, massage your balls with the other. You’re going to do that for 7 mins… because that’s my favorite number!

I love it when she teases me from afar. 🙂

It only took a few minutes before I was moaning and writhing in the bed. I took a moment to text her that I was awake and how it felt; she responded:

Love it!!! Since you stopped in the middle, now you have to start over. Hehe 🙂

Serves me right for not following My Lady’s instructions to the letter!

 

The Joy of My Lady’s Orgasm

Posted by JonMustWait on June 14, 2014
Posted in: Male Chastity, Tease/Orgasm Denial, Wife Led Marriage. Tagged: , , , , , , , , , , , , , , , , , , , , . 3 comments

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…..   🙂

In For The Long Haul (or How a Forced Ruined Orgasm Got Me Locked Up 24/7 For Over a Month)

Posted by JonMustWait on June 10, 2014
Posted in: KeyHolder, Male Chastity, Tease/Orgasm Denial, Wife Led Marriage. Tagged: , , , , , , , , , , , , , , , , , , , . 2 comments

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.  🙂

Moment Savored

Posted by JonMustWait on June 5, 2014
Posted in: Male Chastity. Tagged: , , , , , , , , , , , , , , , , , , , , , , , , , . 2 comments

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.  🙂

Keyholder Thoughts: Orgasm Denial and Chastity

Posted by Michele on June 2, 2014
Posted in: KeyHolder, Male Chastity, Tease/Orgasm Denial. Tagged: , , , , , , , , , , , . 5 comments

Cagedmonkey and I just finished up an almost 3 month period of denial, 80 days to be exact. It really pushed the limits for both of us because it was the longest we had taken the denial with some pretty intense teasing along the way. Since putting cagedmonkey back in his Jail Bird, I’ve been trying to decide how to handle his next denial period. I figured it might be a good idea to come to the blog and get out my Keyholder thoughts. Perhaps some of you have thoughts or ideas you’d like to mention.

Since we’ve done a bunch of different periods of denial already I don’t see denying him until Christmas or New Year’s (6 months) being a real issue. So I’m leaning on that being the actual denial period but along the way I love to throw in some intense teases, hardcore frustration and those lovely things to endure. I’ve thought about certain time periods of complete 24/7 wear with zero time out for even an erection. It would have to be a month or longer for this to be a challenge for him. I was also thinking that part of that, or another period itself, could be him wearing the Revenge and doing a “no look, no touch” thing for a couple weeks to a month.

I am loving the idea of a progression thing that goes along with the 12 Days of Christmas. Ideas are anything from just stroking him each day for longer and longer to actually doing a new, added thing each day. Like, a butt plug the first day and then the second day would be two nipple clamps and a butt plug and third day could be 3 stokes, 2 nipple clamps and a butt plug… etc but that would be twelve ideas I’d have to come up with! I could do a new thing added up to five and then from there could be spankings… hmmm.

Ok anyway, you see my thought process here. You know I love to keep things interesting so I’m kinds curious what others think of this. Would you like your Keyholder to do something like this? Something different, what? Something more? Something less? Would you like to see me put cagedmonkey through something in particular that I have or maybe haven’t done already? Let me know!

I hope to hear you’re thoughts!