An Eventful Night: Part II – A Huge Mess

(Click here to read Part I of An Eventful Night)

My Lady had put me in an extremely submissive position. I felt broken down and defeated, completely at ML’s mercy that she was not willing to give. What she was willing to give me was tender aftercare, holding me as I lost control of my emotions. ML’s aftercare drove me further into my submission, which fed my growing urge to please my dominant lover.

Most often, when I hit this depth of submission, I find the urge to please My Lady’s pussy unbearable. This time was no different. I shoved my face into her pussy and found her soaking wet. She was flooded with pussy juices, obviously turned on by her extreme dominance over me. I didn’t even take the time to move between her legs; I was facing ML’s feet, angled off to her right slightly, licking her from clit to asshole and loving every minute of it.

As I was smearing her juices all over my face, I felt ML’s hands running over my ass cheeks. I moaned as her fingertips traced over my skin. Little did I know that she wasn’t just rubbing my ass, she was warming me up for something more.

I was surprised by the feeling of cold rubber pressing against my asshole. I moaned into ML’s pussy once more as the tip of the vibrating anal plug slipped into my ass. ML slid the plug in further until I felt it bumping up against my prostate. When she turned the vibration on, I nearly squealed in response.

I could feel the pressure building inside as the plug massaged my swollen prostate, backed up with more than a month’s worth of unreleased cum. It was hard to keep my concentration as my cock twitched inside its cage. My Lady refocused me by grabbing the back of my head and shoving my face back into her horny pussy.

I continued to please My Lady’s pussy, even as the sensations inside my ass became more intense. My moans got louder as I felt the pressure building and building. Then I felt ML’s fingers push upward underneath my balls. I groaned as I felt the pressure push past the breaking point…

The fluid gushed from my cock, in what felt like almost a constant stream. Luckily, ML had placed a towel underneath my dangling cock cage, so as not to soak the mattress… although she milked me so thoroughly, towel was totally soaked through! It was only the second time I had experienced this, and the first time with My Lady. It was amazing how much fluid ML was able to milk from me! The mattress was only slightly damp underneath the towel, so it wasn’t too uncomfortable when ML made me sleep in it. ūüôā

After the intensity of my emotional craziness earlier, the milking gave us both something to laugh and smile about before we went to sleep. Apparently, ML is not the only squirter in the household!

Three Days to Tease, Please & Deny pt 1

Today was just the beginning of three days with the kids at day camp. Hopefully you’ve read what happened first thing this morning, if not, you’ll just have to click here.

So we laid down together to nap and I really did try to nap, I promise. However, laying there in cagedmonkey’s arms was quite literally maddening. You see, we don’t often get to lay together sleeping in each other’s arms. Before I could even fall asleep I ended up having two spontaneous (is that what they are?) orgasms. I just laid there shaking, cumming in his arms. Omg, the feelings of love flowing through me were making it that much worse. I felt so connected to hubby, so safe, so wanted and desired.

I did last there for a little while trying hard to sleep. Cagedmonkey fell asleep right away since the poor man had been at work all night and still hadn’t been to bed yet this morning. I knew he had to get some sleep but, still I laid there, with thoughts of sex running through my head. I really couldn’t stop thinking of wanting to do things to cagedmonkey. Finally after spending time writing my earlier post, playing some games on my phone and wasting as much time as I could, I just needed to attack him.

I lifted the blanket to expose that gorgeous ass of his, I rubbed his cheeks, kissed it and then took my wand to his asshole. Haha I’m sure that was an interesting way to be woken up! Then I rolled him on to his back and sat right on his face. While he was busy licking my pussy, I played with his caged cock. I licked that sweet spot on the bottom side and felt him moan into my pussy. Btw, that is something that completely makes me gush. I kept teasing, licking and kissing his straining cock while he could do nothing but slurp up my sopping wet juices.

He continued to lick me as I got lost in the pleasure. It made me want to milk him for some reason. So I grabbed Pearl and gently pressed it into him. I took my wand and put it on the base of it and turned it in to a sort of vibrating dildo. The moaning in my crotch got much more intense and my pussy got that much wetter. I held it there, licking him through the bars of his cage while sending vibrations through him to his prostate. I, then, told him to get up on his knees (which we found was THE position) and continued to vibrate him and massage his balls in a 69 position while he was still licking my clit. It didn’t take long in that position to get that precum pouring out of him. I milked him a nice puddle on the bed… which also meant we had to strip the bed and wash the sheets. ūüôā

After all that I was well cummed out and he was emptied but extremely desperate for an orgasm, we came downstairs and took a shower together… then I made lunch!

Setting the Table (or “The Night When My Lady Tied Me Down, Pegged Me, and Sent Me Off To Work)

The bondage rope is quickly becoming one of My Lady’s favorite toys. Last night before I left for work, she chose to give me something to remember her all night long with. And it was VERY effective!

ML started off by using the rope to tie me down to the coffee table in our living room; she cuffed my wrists together, and then used the rope to attach the cuffs to my thighs, running the rope around my cock cage for good measure. Now, if I tried to move my hands upwards the rope would tug on my cage and pull on my balls. ML let out a tiny giggle as I tested her ropework for her; she was obviously enjoying herself already, and we were only at the beginning.

Once I was secured to the table, My Lady grabbed her prized butterfly paddle and began to spank my ass. As she whacked my ass harder and harder with each swat, I began to whimper after each hit. My reactions began to fuel her desire, and she spanked me harder and faster until it seriously started to sting. She sat across my back to hold me down and paddled me more. I could feel my ass starting to turn red as each blow stung my ass cheeks. I could tell by ML’s breathing that she was getting very turned on, and when she gets very turned on she starts to lose herself in the moment. When this happens, there’s no telling what’s in store for me next!

What was in store for me, apparently, was a very rough pegging!

My Lady first started working Pearl into my ass. Pearl is a small-to-average size dildo, so it wasn’t too terrible. ML began fucking my ass with it fast and forcefully; I could feel it rapidly filling me up and exiting me, only to fill me up once again. I began to moan uncontrollably; ML’s response to this was to simply fuck my ass even harder. After a few minutes of this, she removed Pearl from my ass and reached for something much, much bigger.

The dildo she chose next was the large bronze one she has used on me before. This thing just looks painful – it’s longer than I am, and the head is extremely thick at the base. The shaft thins out to give a little bit of relief, however it is ribbed which¬†rubs against¬†my asshole over and over as it thrusts into me. She pressed the head of the dildo against my asshole. I wasn’t sure if it was going to go in at first! I felt my asshole trying to stretch around the bulbous head, and it didn’t seem to quite be getting there. No need to worry, though… ML shoved it in hard, forcing my ass to open up and accept the intruder. I grunted loudly as she shoved it in farther. God, it hurt SO FUCKING BAD. It felt like the dildo was pulling apart my insides.

My Lady began to fuck my ass with the huge dildo, roughly and without mercy. It didn’t take long for me to start sobbing and whimpering. I couldn’t take it anymore; I begged her to stop. I pleaded. And how did My Lady respond to my pleas? She leaned over and cupped her hand over my mouth and told me to be quite while she fucked my ass like a good little slut so I didn’t wake the kids (omgggggggg).

It was at that moment I started to break down. I didn’t just want her to stop. I needed her to stop. My Lady had never done anything this intense with me while the kids were in the house.¬†I couldn’t stay quiet. I physically could not. Yet My Lady was forcing me to. I needed to scream. I needed to cry out in tortured agony. But I couldn’t I wasn’t allowed. So instead, I simply broke down and began to cry¬†into her hand.

My Lady did it. She broke me. But did she stop? Oh no. She wasn’t finished with me yet.

ML pushed the dildo further into my ass; instead of screaming in pain I simply flopped down on the table like a rag doll. She pushed in as far as she could, thrusting deeper into me as I let out what would be best described as a long deep groan. I’ve never made that sound before. Then again, I’d never had a huge dildo pushing so far into my asshole I could feel it all the way up to my hips inside. My Lady held in in place deep inside me. My whole body shuddered as I struggled to keep my screams in my chest. I felt precum pouring out of my cock as I was¬†harshly milked, I honestly didn’t care. All I cared about was surviving being impaled by the bronze monster My Lady was assaulting me with.

Just as I was contemplating whether I should safeword or not, My Lady pulled the dildo out of my ass. She untied me from the table, but I couldn’t get up. I laid on the table, as limp as a ragdoll. When I was able to lift my head, I saw ML motioning me to lay on the floor, face up. I slowly moved over to where she wanted me. She stood over me and removed her soaked-through panties. Facing my feet, she squatted over my face and shoved her dripping wet pussy into my face. For the next ten minutes, My Lady alternated between rubbing her pussy all over my face and pushing her asshole down onto my tongue. I fucked her ass with my tongue as a good sub should, and I sucked on her clit when she moved it within my reach. After she rode my face to two orgasms, she laid back on the couch and waved me over again. “You have a mess to clean up,” My Lady said. I crawled over and licked her pussy to a massive orgasm that seemed to last about 5 minutes. Even after all of the pain I was put through, I smiled proudly at my ability to make My Lady cum so hard with my mouth.

After we took time for our aftercare (always important after a scene like this!!!), My Lady sent me off to work with a sore throbbing asshole. And the weird thing is that I was horny all fucking night long. I still am, about 12 hours after everything happened. I think this the worst horny I’ve ever felt!

“I Think I Accidentally Milked Myself!”


This morning, My Lady came upstairs to tuck me into bed, and soon things took a turn for the frisky. I could feel her dominant streak starting to grow. It wasn’t long before she was telling me the things she was going to do to me, the ways she was going to use me.

It was time for her to go out and run some errands, and leave me at home to sleep. But she decided to make things just a little more difficult for me Рwe have a vibrating butt plug that has works on a number of different speeds and patterns with the push of a button. She got the plug from our toybox in the closet and began to rub it up and down her pussy lips. Then, using only her pussy juices as lube (OMG fucking hot!), she slid the plug into my ass and turned on the vibration.

Immediately I began moaning and squirming on the bed. She told me to keep my phone handy because she’d be texting me during the morning when she wanted me press the button to change the pattern. And off she went, leaving me with a vibrating ass,¬†unable to lie still.
I laid in my bed over the next couple of hours, softly moaning as the plug vibrated my ass, ML texting me every so often to change the pattern. Every once in a while, my entire body would jerk and spasm in response to the unyielding vibration. I began to feel a building pressure in my balls, a pressure I had felt before. It felt like…
It felt like I needed to pee.
I get this feeling usually when ML is toying with my ass, but the strongest I’ve ever felt this sensation was when My Lady milked me for the first time. Was this what was happening to me? Or was I about to piss all over the bed? I had no idea! I frantically texted ML, begging for permission to turn the plug off, because I was unsure what might happen next due to the sensations I was having.
Her text message response:
Nah, little slutty boys who like their asses played with get to sleep in their own mess ūüėČ
I then asked if I could at least put a towel down, but she refused. She told me to just let it happen, if I ended up peeing the bed it wouldn’t hurt or kill me. Then she told me she would be in a store for the next twenty minutes and not to bother her until she texted me back.
I tried like hell to hold it in, but the vibrations would not let up. I felt the pressure building and building inside me, until it was nearly unbearable. I was feeling as if I was about ready to burst, causing me to moan out loud once again. Then I heard My Lady’s words in my head… let it happen
So I did. I lifted my hips from the mattress, my ass in the air, and tried my hardest to relax my muscles.
Two seconds later, I heard the sound of something dripping on the sheet.
I looked down between my legs, and clear liquid was literally POURING out of my cock from inside the cage. “Oh God, please no,” I moaned. Still dripping, I reached down, afraid to smell urine on my hand, but I didn’t.¬†The fluid was clear and had no scent to it. Thankfully, it wasn’t pee. The vibrating butt plug milked me, and VERY effectively at that!
After a few more seconds and¬†I was fully drained, I reached down once again to survey the damage. Holy fuck… there was a 4-5 in wide puddle on the mattress, completely soaked through! My balls must have been completely emptied, without any orgasmic¬†feelings for me. It was equal parts humiliating and exciting. I always liked the idea of being milked by ML, my cum being drained from my body without giving me pleasure. It involves such a deep level of control that she can extract my cum yet still control my orgasm. But this was something else; ML somehow managed to milk me without even being in the house! What the fuck?!?!?!?
I sent ML about six frantic texts about how I think I accidentally milked myself, that the bed was a soaked mess, what should I do, but she didn’t respond. So I put my phone down on the nightstand… now what? Once again, I heard the words of My Lady in my head… slutty boys who like their asses played with get to sleep in their own mess…. I knew what i had to do.
The puddle was cold and slightly sticky by the time I laid back down. God, how embarassing, sleeping in a puddle of my own cum that I didn’t even get an orgasm with. It was once again difficult to lie still, this time because my cock was SCREAMING for attention. I really wanted/NEEDED¬†to hump the mattress and cum, but couldn’t obviously because of the cage. I eventually did end up falling asleep, only waking up when ML came into the bedroom when she returned home. After checking out the sheets for herself, she hugged me and told me how amazing it was that I listened to her and just “let it happen.”
And you know what? It felt good for her to say that. It was not easy to allow that to happen to me, but I trusted her and went along with it. I put myself through some pretty embarassing and uncomfortable stuff, simply because she demanded it. It felt great to be controlled like that. But the best part was that I could tell she appreciated the fact that I followed through on her desires. That is the essence of submission, I think – allowing yourself to be controlled by your dominant, and experiencing the appreciation that s/he has for your submission.
Now, of course, I can’t wait until ML milks me again in person. I want to hear her talk dirty to me while she does it, call me a dirty boy for making a mess. I want to hear her reaction when my cum starts pouring out. I think she will really enjoy it, and that humiliation/excitement feeling will go off the charts for me!

I’ve Got Big Balls!

Sorry, ACDC, but you have nothing to complain about here. Call me when you’ve been locked in a chastity cage and denied orgasm for over two weeks.

My balls are really starting to swell up HUGE. My Lady has kept me in the Jailbird for¬†over two weeks now with minimal time out and absolutely no orgasms. I have spent plenty of time pleasing her and she has spent plenty of time teasing me. And now my balls are significantly larger than I’ve noticed in the past. I actually have to make sure I’m not peeing on them when it’s time to urinate!

I’m not sure of the specific cause of this. Part of it is almost certainly being denied orgasms or draining of any cum whatsoever, as ML has not milked me at all during this latest stretch. I’m pretty much leaking precum constantly at this point, but that is nowhere near achieving the draining I need so badly. I am sure that when (if?) ML lets me cum on Christmas, it is going to be an extremely heavy load. ūüôā

I’m also wondering if my balls are looking bigger because my scrotum is being¬†pulled by the cage. When ML teases me, my attempted erection pushes the cage up pretty far on “the equipment” down there, giving the skin around my balls a pretty good stretch. I feel a lot less discomfort with the JB than I did in the Birdcage, but the pull is still pretty strong. During these times, my balls feel large and extremely full, and they turn a deep shade of red. All is well as far as circulation goes – ML has taken a liking to massaging them in this state to make sure blood flow is acceptable (at least that’s her excuse).

My gigantic balls are probably a result of both factors – storing up a large load of cum waiting to be released, and the tight squeezing from the cage every time the cock tries to assert itself. One thing is for sure – they are very sensitive in this state, and I often find it impossible to hold back my moans when ML rubs them. She takes quite delight in that!

He Said, She Said – Milking the Prostate

(In this post, Lady and cagedmonkey tandem post on the same subject. These are not conversations, per se, simply viewpoints from the female and male perspective.)

Lady:¬†Cagedmonkey has been denied orgasm for a couple of weeks now so I thought it might be fun to milk him. I haven’t ever milked him properly with an internal prostate massage so it was my mission to get it done! I have milked him a little bit with an external massage before but it wasn’t anything to write home about.

The other night I cuffed my boy to the coffee table on his belly. I got out the bottle of lube and the anal-t vibrating prostate massager. Since I really had no idea what I was doing, specifically, I played around a bit with angle and depth and that sort of thing. So with one hand I was adjusting the massager and the other I used to massage and push on his perineum so his prostate got as much stimulation as possible. At times I could tell I was hitting something just right because he would let out a pretty good moan. I did this for about 45 mins and while he was dripping precum pretty well I wasn’t getting that good amount of fluid that I wanted and have heard so much about!

That’s when, with the massager against the palm of one hand, I pushed up on his perineum with my fingers of the same hand and grabbed his cock and stroked a little with my other hand. I only stroked a few times (medium speed) and he only spasmed once and out came a huge squirt of what looked like milky water! Then of course I had to do it again so I stroked him another couple times and he dripped out a few more big drops of the milky fluid. Oh, not to mention, the very loud moan each time as well. I know he didn’t orgasm, he lacked the spasms for that and what came out was not thick like cum usually is. It really was just a thin milky colored, water-like fluid. It was hard to even show him how much after since it just made the towel wet.

It was a pretty neat experience but can be discouraging when it takes so long. I bet if we do it more and hubby is able to relax a bit more it can happen faster. I guess we’ll just have to practice more! ūüôā

cagedmonkey: I will admit, the idea of being milked by My Lady is very exciting. The possibility of her extracting the cum from my full swollen balls without allowing me the pleasure of a full orgasm involves a level of control that is off the charts. And to be honest, I want to be controlled like that.

ML has attempted to milk me in the past, with varying degrees of success; most of these attempts resulted in either a ruined or minimized orgasm. This was probably her most successful go at it. ML had me strapped down and unable to resist, and she used my helplessness to her advantage by taking her time and being patient.

ML has learned how to use the prostate massager very well. She was hitting all of the right spots; I was feeling flash after flash of pressure overload sensations, the signal that my milking was imminent. It was a little difficult for me to relax and let go because I was afraid I might end up peeing, but I think if she had continued with stimulating those sensitive spots I wouldn’t have been able to hold back any more.

After who knows how much time I spent on strapped to the table, my ass being penetrated and my prostate massaged, throat hoarse from near-constant moaning, ML began to stroke the cock in rhythm with her thrusting. I got closer and closer to orgasm until just at the last moment she stopped her stroking…. and I felt the “cum” shoot out from me! I could feel soft spasming in both my cock and asshole; I wasn’t quite sure if I had cum at first. But afterwards – when I was still horny and wanting to cum – it was obvious that I hadn’t. Some of the building pressure in my balls was relieved, but the need to cum was still there.

I’m not sure if we accomplished the classic definition of “milking,” but whatever we ended up doing was pretty intense! Overall, it was fun and something I am definitely interested in trying again!