Descending Into Chastity

Week 0

I breathe heavily as I recover from the orgasm you just gave me with your hands.

"Thank you for letting me come, mistress. It felt so good."

I am still speaking slowly, trying to catch my breath. It was a very intense experience, that you teased out of me slowly.

"And so soon after the last one. What was it, only 5 weeks of denial?"

Even you can't keep an entirely straight face when you say 'only', since it has been more than a month.

"Yes, mistress. Five long weeks."

"And were you good during these five weeks?"

"Yes, mistress, I'm always good."

Still flushed with endorphins from the orgasm, I may have gotten a bit too cocky with my cheek. I can see your brows furrow.

"Uh huh... So you are saying you

never

touched yourself without permission during these five weeks?"

Oh oh, now I have to see how I can talk my way out of this.

"Well, I have to shower, and to clean it, I kind of have to..."

You interrupt me.

"You know what I mean!"

Of course I know what you mean, but it was worth a try.

"Um, err... well... I might have soaped it up a bit more than strictly necessary... But just to keep it clean for you, mistress. And I did not have any orgasms without your permission."

As soon as I have finished my confession, I can see that you are not happy with it.

"You were not allowed to play with yourself. Maybe I have to put you into your chastity cage long-term, if you can't control yourself."

So far, we have only used the chastity cage for some short play sessions, maybe to keep me restrained while I licked your pussy, or as a tease when you didn't feel like playing. Very rarely, I wear it for a full weekend while you are out of town, but so far our denial play was purely honor-based. I guess I should have considered that when I broke the rules. On the other hand, the thought of this increased intensity of play also excites me.

"Yes, mistress, if you think that is necessary."

"It is. So go put on your cage and give me the key."

I do as I am told, and soon you take the small, silver key and leave the room with it, before you return empty-handed.

"Now that that's in a secure location, and you are all settled, you may give me an orgasm."

"Yes, mistress."

Week 1

One week later, you call me into the bedroom.

"Get naked and on your back, arms and legs spread out."

Mildly confused, I comply. My penis is starting to strain in its cage, getting excited about the possibility of release. You tie each of my limbs to one corner of the bed, and I am unable to move. Once I am secured, you leave the room to retrieve the key from wherever you are hiding it, and return to unlock my penis.

"How does it feel?"

"Good, mistress. Being locked up makes me very horny and excited to play."

Indeed, my penis enjoyed its regained freedom so much it became hard almost immediately.

"Ah yeah, what do you think I'll do?"

"I don't know; maybe some of that hawk tuah thang?"

You glare at me, clearly not amused.

"I'm sorry, mistress. I'm just kidding. Would you please tease me a bit? Please, mistress?"

"No. The whole purpose of this was for you to learn that I decide when you get any pleasure. I only unlocked you for some cleaning and to check for chafing."

You fetch a washcloth and roughly rub it around my ball and penis, then dry it with a towel, and rub some lotion in to make sure it stays hydrated.

"Yup, everything looks good. And now back into the cage it goes."

You struggle a bit with my erect penis, but after applying some ice you shrink it down enough to lock it up again.

"And remember: No touching without my permission."

Defeatedly, I accept the mockery.

"Yes, mistress."

Week 2

Another week passes, and while you never unlock me, you let me pleasure you several times throughout the week. Previously, you might only want one, or sometimes two, sessions per week, but this week you find time for a "quick orgasm" five times; almost every day. The first two times I ask if you would unlock me, but you only dismissed that with "Don't even ask, this is for my pleasure only." and I got the hint. On Saturday, excactly two weeks after you locked me up, you finally have some plans for me again.

"You know what to do: Naked and arms and legs spread out."

Just like the week before, I get into position and you immobilize me the same way, before you leave the room to fetch the key. After two weeks, my penis is even more eager to grow to its full size when you release it.

"Guess he's even more excited than last week to get some freedom."

"Yes, mistress. Will you please tease me a bit this week? I've been so good all week."

"Hmm, yeah, you did give me quite a few orgasms this week. But you also asked me to unlock you, even though I clearly said that I was the one that decided when or if you get any pleasure. No, this is just another cleaning and inspection."

You once again use the washcloth to make sure everything is clean, although even rougher than the week before, dry me off with the towel and put lotion. The whole process takes less than 10 minutes, before you use the ice pack again to lock the cock cage in place again.

"There we go, all set."

Week 5

The third and fourth week pass in much the same way as the first two, with only a very quick cleaning session. In week five, you don't even tell me what to do anymore, and just say "Cleaning session in 5." and I immediately proceed to the bedroom and get naked. You have also shown me how you want my legs tied, which I can do myself, and I prepare the ropes and cuffs for the arms as well, which you then just close on my wrists. You still make sure to never leave the room to get the key before I am fully secured. After over a month of complete denial, my penis is desperate for even the slightest touch, while you have been perfecting the art of washing it in the roughest way possible to deny me the least bit of pleasure. While you keep me completely denied, though, you are getting more orgasms than ever before. All this makes me extremely desperate and frustrated, so while you are applying the lotion again, I try to get some pity or mercy.

"Thank you for applying the lotion, mistress."

"Of course. It needs to be moisturized properly in its long-term home. How does the cage feel?"

"I can barely notice it, day-to-day, mistress."

"Good. So no reason to get rid of it."

"Um, yes, mistress. Thank you for denying me. It's just... it's been over a month now, since I got any stimulation, and I was wondering..."

"YES?"

"... I'm sorry for asking, mistress. But please, it's been so long. I

need

some stimulation. Please, mistress."

You do not respond, and instead fetch the ice pack and lock my penis up again. I groan in frustration as you leave the room to deposit the key in its secret storage location. When you return you are smiling.

"You need stimulation, you say?"

"Yes, mistress. Please unlock me again, and at least play with my penis for a bit. I can take a bit more without an orgasm, but this is too much."

"No."

"No?"

"No. It's my decision, and I decided that you can take a few more weeks. But now that you

think

that you absolutely need a teasing, let me tell you another rule: Whenever you ask for anything, an orgasm, a handjob, teasing, anything at all, the answer is no. Even if I have planned to tease you or even let you come, as soon as you ask, you don't get anything. And you will be punished. Since you asked today, let me demonstrate the punishment."

Still tied up, there is nothing I can do as you fetch the riding crop.

"Another advantage of the cage is that it pulls your balls outwards nicely, making them much easier to hit."

Before I can even process what you said, you hit my balls hard with the crop.

"OW. Not my balls, please, mistress."

"That was one. Let's say fourteen more to go."

With that, you hit my poor, full balls over and over, until they are sore.

"There we go. Did it hurt?"

"Ow, yes, mistress. It still hurts."

"Good, that's the only way it can be effective as punishment. You can avoid future repetitions by remembering that only I am in charge of your pleasure."

"Yes, mistress. You are in charge."

Week 8

After the punishment episode, I take the next two cleanings without any complaint, and instead focus more on your ever-increasing desire. Orgasms are an almost-daily occurrence for you now, often with extended foot or full-body massages, and I serve eagerly, as your pleasure is the only I get to experience. You have fixed our cleaning sessions on Saturdays at 6pm, and I know to be in bed and ready by then, with my legs tied, and the handcuffs ready to be closed. I was three minutes late one time, and you gave me three more hits on the balls for my tardiness. Not wanting to repeat this experience, I am therefore ready at 6pm on the dot eight weeks into my chastity sentence. Of course, you are not bound by such a strict schedule, and walk into the bedroom about 20 minutes later, seeing me spread out on the bed, and waiting for you.

"So obedient. All ready for your weekly check-up."

"Yes, mistress."

You close the handcuffs and depart again as always, to get the keys. Usually this takes you less than two minutes, but today you spend another 20 minutes or so before you finally return.

"Oops, I got distracted, thinking about how desperate and frustrated you must be, and how I literally have the key to your pleasure. It made me so horny, I had to get myself off real quick."

As my main pleasure comes from seeing you come at this point, hearing about an orgasm you had, while I was tied up and waiting for you makes me even more desperate to be allowed release, but I know better than to ask.

"Look who has learned that it's not his place to ask for pleasure. I might have a reward for you later."

"Thank you, mistress. Anything that pleases you."

"What if what pleases me is penetration?"

"Yes, mistress, please. I would love that... If it pleases you!"

You chuckle, and proceed to unlock me. Perhaps it is my imagination, but you seem to rub the washcloth more sensually than usual over my very hard penis this week.

"I'm sorry, mistress, but I should warn you that penetration might make me come very quickly. I am very horny and loaded."

"That's ok. I actually hope you come very quickly."

While I would prefer a slower, more teasy orgasm, after eight weeks of complete and total denial, I am so desperate that I am happy that you let me come at all.

"Thank you, mistress."

You carefully apply the lotion, before you grab the ice pack and lock my penis back in its cage. I am confused.

"Um?"

"YES?"

The tone in your voice tells me that I am on thin ice, and I refrain from asking about the promised penetration. Without another word you take the key away again. Dangling sex and and orgasm and then just taking them away without any acknowledgement seems very cruel. I am still tied up and can't even move, while you take your time to return again. When you finally do, your plan becomes clearer. You untie me, while I stare at the size of the strap-on dildo you are wearing.

"Do you like it? Aww, did you think you were the one that was going to do the penetrating?"

"It looks a bit scary, mistress."

"Don't worry, it's not bigger than the butt plugs you've used in the past. I got a smaller model to start with."

"Thank you, mistress."

Once you have me fully untied, you point to the edge of the bed.

"Now, bend over there, while I grab the lube."

With my feet on the floor, and my torso on the bed, I await the silicone entering my butt. You proceed very slowly, and with plenty of lube, slowly entering me with the full length of the dildo. When I can feel your pelvis against my butt, you caress my sides.

"How does it feel?"

"Filling, mistress."

"Does it hurt?"

"No, mistress."

You withdraw slightly, ram it back into me.

"Does that feel good?"

"Yes, mistress. That feels nice."

You slowly pump the strap-on in and out a few more times.

"This is actually a lot of fun. Do you like it when I'm fucking you?"

"Yes, mistress. Please fuck me some more."

You increase the frequency of the penetration, slamming hard into my ass.

"Oh, and I was serious earlier when I said that I hope that you come."

Even though this is the first real stimulation I get in eight weeks, the anal penetration is not enough for me to get to an orgasm. It still feels nice, and you also seem to be enjoying yourself, but after a while you get tired.

"Uff, this is exhausting. I guess this will have to be enough for today. If you are lucky, you will get more of this next week."

"Thank you, mistress. I would love for you to fuck me again whenever it pleases you."

Week 10

Being ready for the weekly check is now routine for me, and I actually look forward to the few short minutes my penis gets to grow to its full size. I was slightly disappointed that the strap-on did not make a reappearance last week, but I know better than to complain, and instead wait patiently for when you decide that I deserve some more stimulation. I am already waiting on the bed when you enter the room.

"Ok, let's get this over with real quick."

Impassionately, you move through the same routine as always, tieing up my arms, getting the key, washing and drying my crotch, and applying some lotion. All together, with the ice pack to lock me up again the whole process now takes no more than 5 minutes.

"And that's that. Now, you've actually been very good this week, so do you want me to fuck your butt again today?"

"If it pleases you, mistress."

"Very good answer. It's not your decision, it's mine. Hmm... I think I would enjoy it. So bend over while I get the toy."

I waste no time to get into position, eager to receive the only stimulation you offer me. You return wearing the dildo, with the lube bottle in hand. As last time, you start gently, but get rougher once you have found a good rhythm.

"Tell me, how does it feel, not being able to touch yourself at all? The only pleasure you get is from me fucking you, as much or as little as I want."

"I love it when you fuck me, mistress. It's so intense, and feels so good."

"Great. So maybe you are going to come this week, then?"

"I... don't know, mistress. I don't think I can get to an orgasm from this at all."

"Oh well, how unfortunate for you. I'm still having fun."

Indeed, you seem to be enjoying the feeling of dominance penetrating me gives you, and continue for several more minutes. I am sure my butt is getting more sensitive to this new kind of stimulation, and as I am bent over the bed, I moan happily, but despite the feeling of pleasure, I do not feel like I am getting anywhere close to an orgasm. You are also breathing fast, and slow down, before you stop entirely.

"Phew, who know having fun could be so exhausting. So that's it for this week."

Week 15

Over the last few weeks, you have taken to dangling a potential anal session as a reward in front of me if I pleasure you above and beyond your normal expectations. Once I foolishly asked if you would penetrate me, which has earned me 25 strikes on my balls, and you informed that that every subsequent infraction would add another 10 strikes. Now I just eagerly serve you completely obediently in pursuit of being graced with some anal penetration as a reward at your discretion. You maintain that I am allowed to come if I want to, but even though the feeling becomes more and more pleasurable every time, I'm not sure if it will ever be enough for an orgasm. When Saturday comes around, I, as always, am ready at 6pm for the weekly ritual.

"Look how far you have come. I don't even have to say anything anymore, and you are there and ready for me."

"Yes, mistress."

"You know it's a kinda special day: 15 weeks, that's more than 100 days that you have been locked up now. Just 10 weeks ago or so you still thought that you

need

any stimulation for your penis, and look at you now. Do you still think that?"

"No, mistress. You are completely in charge of my pleasure."

"Exactly. And if you are very good, you even get penetration. Am I not generous?"

"Yes, mistress, you are very generous, thank you."

You grab the key and unlock me. Since you usually do not make any banter beforehand, you are a bit surprised how hard my penis already is when you remove the cage.

"Someone's thinking about all that anal they are getting..."

"Yes, mistress."

You perform your usual cleaning steps, but rather than applying the ice immediately, you let my penis stand in its full glory while you smile at me.

"Do you even still remember what stimulation feels like?"

"Only very faintly, mistress."

"Let me give you a small reminder, then."

With that, you wrap your hand around my penis very loosely and stroke it 3 times before you let go again.

"Does this wake some memories?"

"Oh yes, mistress. That feels so good. Thank you, mistress."

You take your other hand, and grab my penis again, but this time just holding it still.

"Hmm, I wonder what I should do..."

My penis feels like it is straining to fill your hand, and longing for you to stroke it until I can shoot the load that has been accumulated over the last 15 weeks. However, you have also cultivated a deep deference to you in me over this time period, which is now coming to full fruition. Something inside me wants to beg you to please make me come, but I am in full submission, and know that there is only right answer.

"Whatever pleases you, mistress."

"Very good! That's what I like to hear."

You remove your hand, and grab the ice to shrink my penis down to a size where it fits into its usual home. Once the cage is in place again, you take the keys away, and leave me to my thoughts. Three strokes. That's all you allowed me after more than 100 days of chastity. I am conflicted between complete frustration and absolute bliss. When you return, you are already wearing the strap-on dildo, swaying me further into the "bliss" direction.

"Since you didn't want any more strokes, I figured I'd give your butt some exercise instead."

"Thank you, mistress. I hope it pleases you."

"Oh, it will."

Over the last few weeks, you have found a more comfortable position and rhythm, which does not tire you out quite so quickly. As you thrust back and forth, you also scratch my back and pull my hair.

"Well, you got three strokes. Just so you don't forget what you've sacrificed for my pleasure."

"Yes, mistress. It was well worth the sacrifice, if you are satisfied."

"Yes, and you are quite good at making sure of that. But I don't want to deny you forever. You know you are allowed to come while I fuck you."

"Yes, I know, mistress. I just don't think I can."

"You better figure it out, though. These three strokes were the last ones you are going to get until you learn how to come from anal penetration."

I want to protest, but with my penis locked away, and you thrusting a dildo into me, my mind defaults to complete submission.

"Yes, mistress, if it pleases you."

You give me a few more rough thrusts before you stop.

"Guess not today, though. You better serve me obediently so that I give you another chance to try soon."

Week 22

154 days of chastity. I have fully accepted my position to serve for your pleasure, and eagerly present myself for the weekly, short inspection, which is the only time my penis sees any release from its prison. You have been true to your word, and there has not been any more stimulation since the three strokes you gave me several weeks ago. You do, however, still enjoy penetrating me with your strap-on, but seeing as how it is a reward for me, you are holding me to higher and higher standards for when I deserve this reward. Desperate for any bit of pleasure, I serve with complete devotion and attention to your desires.