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All posts for the month October, 2017

In my last post, I wondered aloud whether or not my long lockup period had already begun without my knowledge. ML’s response to this was, “I don’t know, maybe it has! I hadn’t really thought about it too much yet…”

It’s a little startling to realize how easy it has become for My Lady to keep me locked in my chastity cage for a week straight, but that is where four years of chastity has brought us to.

It turns out that did get at least one more chance to feel ML’s pussy before my cock is locked away for more than a month. ML and I had date night last night, and afterwards we attended a “play party” with some friends. We couldn’t stay long so we didn’t have a chance to play ourselves, but we came home pretty turned on. Lucky for me, My Lady was in the mood for sex, and she didn’t want a toy; she wanted the real thing.

ML used my cock along with her wand to give herself a few good orgasms before bed (none for me, of course). She was nice enough to allow me to sleep uncaged, which was a nice surprise. In the morning, she took the opportunity to give me a little bit of a tease to start my day.

She’s left me uncaged for the day today so far, which makes me wonder if she’ll be teasing me tonight or throughout the day… or both. It’s actually a tough day for me, because I’m seeing all of the things I’m going to miss when I’m locked up next week.

The extended lockup period that ML and I have been planning is looming on the horizon. Next Friday is our chastity anniversary, at which point My Lady plans to keep my cock locked in chastity 24/7 for the next six weeks at least. Although, at this point, I can’t really even be sure if it hasn’t already begun – my chastity cage hasn’t come off since my last post at the beginning of the month. Perhaps ML has been planning a true Locktober Plus this whole time and didn’t tell me.

She is certainly capable of such levels of deviousness.

Preparing for the long lockup has already begun: this morning, ML had me locate Adam from our toy storage so he will be at the ready when she needs him. She needs to reacquaint herself with his size and feel before she will be ready to use him during my time in chastity.

I was hoping to have one last feel of ML’s pussy on my cock before being locked in chastity for the long haul, but Adam’s presence makes me wonder if I’ve already had my last chance for a while and I didn’t even know it.

Your fingertips tickle the bottom of my cock as it bobs in the air, searching for any type of sensation that will bring it over the edge. But you are fully in control, and you won’t give my cock the touches that it so desperately needs.

I am kneeling on the floor at the corner of the bed. You have tied my ankles together behind the foot of the bed and my wrists to the post above my head. You have also secured my chest to the post, and in my position I am unable to move or thrust my hips in any meaningful way. I am totally at your mercy, and you have spent the last hour or so enjoying it by relentlessly teasing me and edging me. Each time you touch my cock, my body shudders in anticipation and hope that you will finally make me cum. I have been dangling on the edge of orgasm for too long, and I only wish that there was something I could do to bring this torture to an end.

Every touch is a surprise due to the blindfold you have put over my eyes, keeping my senses in complete darkness. Your teasing fingers on my nipples make me gasp and my cock surges even harder, perhaps jealous of the attention my sensitive nipples are receiving. You have been kissing and licking my entire body, and I moan loudly each time your soft warm tongue touches my skin.

Your hands and lips leave my body, and quiet descends upon the room. Did you leave me here to stew in my own horniness? It wouldn’t be the first time you’ve done that. I didn’t hear you walk away, but I was breathing so heavy it would have been easy to miss.

Moments pass as my cock continues to throb in time with my heartbeat. Your teasing was so intense this time, barely giving me a moment in between edges for almost the entire time I’ve been tied here. Even in this moment of peace, I feel the incredible desire for an orgasm burning inside me.

I hear your footsteps as you walk back into the room. I feel you move in front of me, and suddenly your warm wet mouth surrounds my cock, sucking in the head with your tongue swirling around. I moan and I try to thrust forward, but the ropes hold me back. Your lips tighten around my shaft as you slowly pull your mouth back to the tip of my cock and slide forward again. As my cock sinks deeper into your mouth, I hear you whisper in my ear, “How does that feel, darling?”

“Wonderful, ma’am,” I reply, as…… wait…. what???

How are you whispering in my ear when my cock is in your mouth?!?!?!?

You chuckle; pretty much reading my mind, you say, “That’s right, darling, that’s someone else’s mouth on your cock right now. Once the shock settles in, I’m sure you’ll start wondering just who it could be….”

Of course, you are right – who could this possibly be? It’s hard to keep my thoughts straight as the tongue teases my poor defenseless cockhead. I try to wiggle free of the tickling, but I cannot.

“Hmmmm, who could possibly be sucking your big fat cock for me right now?”

It’s obviously someone we know, you wouldn’t allow this with anyone you didn’t fully trust. And it seems as though it’s someone who is well aware of my denial state, as they are trying to avoid pushing me too close to cumming.

“Here’s the fun part, darling – I am not going to give you any hints at all. I want you to be completely clueless as to who this is right now. As far as I’m concerned, it’s just a mouth – a mouth that I am using to tease the fuck out of you and blow your mind.”

Well, it’s definitely working. My mind is being pulled in what feels like fifteen different directions, but I very quickly start to associate the blowjob with the fact that this is YOU doing this to me. It may be another person physically touching me, but this is your plan, your teasing. The blowjob is just a conduit for you to tease me in ways I would almost never expect, and it’s making the tease even worse than it was before.

“So, here’s what I want,” you say. “I want to see just how bad my earlier teasing was for you to endure. I want to see just how badly you need to cum. In order to do that, I’m going to allow you to cum right now… but only if you want to.”

Ummm, why wouldn’t I want to?

“I want to see if I’ve made you so desperate to cum that you are willing to cum in a stranger’s mouth without even knowing who it is.”

Oh God…. my chest gets tight and I can’t breathe for a moment. What am I supposed to do?

“And don’t worry about me being upset. I put you in this position on purpose, this is what I want. If you want to cum that badly, I won’t be angry. In fact, it’s really MY fault for making you that desperate in the first place.”

Fuck, I can’t breathe.

“Think about it, though….  you must be so badly teased and needy and desperate to even be considering cumming in someone’s mouth without knowing a thing about them. Who they are, what they look like… you don’t have a clue, and this person is going to find out what your cum tastes like.”

You’re right…. after all of these surprises, now I honestly have no clue who it could be.

“It could be someone from the neighborhood, it could be someone you know from work…….”

Do I really need to cum this badly?

“Hell, I never even said it was a woman….”

WHAT????????????????????

“That’s right, darling…. I think I’ve made it clear – you don’t know a thing about this person. Like I said, it’s just a mouth. A warm, wet mouth that is willing to accept your load of cum. Are you that horribly desperate that you are willing to cum like this, in what is pretty much just a hole? You’d have to be almost dying of need to say yes to that….”

You’re right, I would…. “someone” is going to make me cum with their mouth. Am I that desperate to not care about who it is, or even what it is, just that I’m going to cum? Is that the only detail that matters to me at this moment?

“I’ll tell you one thing, though, this person is very good at following instructions; I can tell that they have been keeping you close to the edge this whole time without making you cum…. isn’t that right?”

You are driving me insane with the level of control you have over me right now.

“Such a slutty little cocksucker, too, ass is all pointed up in the air… so naughty.” I hear a smack and the mouth on my cock lurches forward. The person sucking my cock moans from your spank, and it vibrates my cock. I can’t help but shudder in response to the added stimulation.

“You really should see this… Oh, sorry darling, you can’t. You’ll just have to imagine it…”

Godddddddd, what the fuck do I do????

“Remember, darling, I wouldn’t put you in any position I wouldn’t want you in. I want this. I want you to be so bad off that you are willing to do this, because that means I made you that way. I teased you so badly that you just need to fucking cum and you don’t care how. So, what will it be darling? Do you want to cum for me?”

To say yes, it would mean than an orgasm is the most important thing in the world to me right now. I have want to cum so badly that I am willing to put aside anything else – no cares about who, what, when, where or how, and just cum. I’m scared to admit it….

“Yes,” I whimper.

“What was that?”

“Yes, ma’am.”

“So just to be clear: I’ve turned you into such a cum-needy slut that you are willing to cum in this stranger’s mouth right here, regardless of who it could be? Have I tortured you that badly and made you THAT fucking horny?”

“Yes, ma’am!”

“Okay, then…. make him cum.”

I swear I can hear a devious smile in your voice, but I am quickly distracted by the increasing pace of the mouth moving up and down my cock. God, can I really do this? Can I really cum into the mouth of a stranger? The mouth is so warm and wet, and I need an orgasm so badly. Should I stop this? Am I having second thoughts?

No…. I want this. Actually, I’m beyond want… I need this. You’ve driven me insane and all I care about is cumming right now….

A few milliseconds before my mind blowing orgasm begins, the mouth releases my cock removes all sensation. I cry out in frustration as I hang on the edge of cumming. Seconds pass as I fight the impending ruined orgasm, which I know will be even more frustrating than all of the edges before it. I try and try to hold back, squeezing and grinding my teeth, trying as hard as I can to hold onto the orgasm I so badly want to experience in full….

I can only hold back for so long, and I’m beginning to lose my grip…

Just before I feel like I might have a handle on it, the tongue gives the undershaft of my cock one quick lick from base to tip. That does it – I lose my focus and I topple roughly over the edge. My cock pulses and throbs in the air, experiencing a ruined orgasm so frustrating that it’s almost painful. I’m nearly crying as I feel the pleasure of the orgasm slipping away.

“See?” you say, laughing. “Like I said – VERY good at following instructions.”

I can feel the cum dribbling out of my cock and down the shaft of my cock, almost like tears of frustration in defeat.

“I did say that they were going to taste your cum, though….”

Suddenly, the mouth is back on my cock, sucking hard and vacuuming the cum out from inside of me. It’s almost like post-orgasm torture, and I cry out as I try to escape with absolutely no success. I just have to endure it until you allow it to stop.

Thankfully, the post-orgasm torture only lasts for a few seconds before the mouth leaves my cock. I hear the two of you moving and getting ready to leave the room, but first you whisper in my ear, “That’s my good boy.” I can’t help but smile.

As you move to the door, I call out to you, “Ma’am? Who was it?”

“You’ll never know.”

October is a popular month among chastity enthusiasts for celebrating their fetish. We didn’t exactly plan it out that way, but ML and I will be doing something special during October, also. It won’t be a full “Locktober” for me, as I will get about a two week stay on my sentence, but I will definitely make up that time on the back end and more.

ML and I have been considering trying another extended 24/7 chastity period, and we are going to give it another try. We’ve found it difficult to get past the month-ish mark in the past, but we really want to push it this time around.

Starting on October 13th (our “chastity anniversary”), I will wear my cock cage 24/7, day and night, all the time until Thanksgiving at the earliest. Yes… “at the earliest.” At Thanksgiving, we will take stock of things and see if we want to try to make it to Christmas at that point. So, very soon I will be going without a full erection from somewhere between 6 and 10 weeks.

Writing that it actually makes me realize just how insane I must be for wanting this.

We always run into two problems when we try to do extended 24/7 lockups: 

  1. I start to feel a little disconnected with my cock locked away for so long, I start needing more sexual attention.
  2. ML starts to miss the feeling of having her pussy filled up by my big fat cock… Those are her words, not mine, but who am I to argue?

So we’ve worked out a plan to address these problems as well as we can.

First, we are going to use toys more often in order to satisfy ML’s need for penetration; “Adam” is more than capable of filling in for my cock in that capacity. And for those times that ML wants to feel me between her legs as I fuck her, we either the Rode-Oh underwear or the strap on harness that I can use.

As far as my needs go, it’s not so easy to get me the sexual attention I need with my cock locked away in steel… but not impossible. We just need to do it in other ways. And, by process of elimination, a lot of that will involve doing various things to my ass.

I’m interested to see how intense my submissive feelings get when the only sex I can have involves my ass. When my cock is taken out of the equation and the only sexual pleasure I receive is through plugging/milking/pegging/etc., how deep will my acceptance of my role go? Will I begin to look forward to it, ask for it, beg for it, even want it? I’m honestly don’t know.

I really hope we can go the distance this time. I’m not really sure whether I mean I want to make it to Christmas when I say that, but I guess we will find it when we are at that point.