Permission to Enter

“Make your tiny cock hard, and rub it against my clit. I want an orgasm,” my wife and Mistress said.

This would be as close as I’ve been to being inside her for over two months. The prospect of feeling her warm, soft pussy lips against my unlocked cock was going to be quite a treat for me. Just imagining how the moistness of her labia would feel against the head of my cock made me quickly get hard for her.

I guess being out of my chastity cage for a week (while it gets resized) has more benefits than I realized.

She pulled the bed covers down, revealing her unclothed bottom half. Slowly she bent her knees and separated them, revealing her genitals to me so seductively. As I moved into position, she pulled her glistening pussy lips apart, revealing her sensitive nub that apparently needed some attention.

I lowered myself and gently put my cock head against her opening. She startled – apparently my PA ring was cold. Damn. “I don’t want that ring there; slide up further,” she directed. I did so, and my cock head approached her belly button. My shaft pressed against her clit now, and she started enjoying the pressure.

She began to grind herself against me, and I realized that this position gave me basically no glans stimulation at all. So I redirected my attention to ensuring that her pleasure was uninterrupted. It didn’t take her long to climax, after which I snuggled in and just hugged her as she floated in that post-orgasmic state.

Eventually she opened her eyes, smiled, and asked “I suppose you’d like to go inside me?”. I responded “Of course,” fully expecting her to decline as part of her ongoing teasing. She said “Well, it’s probably going to be a hassle to remove that ring, you probably need some tool from downstairs…” She likes to leverage any excuse to deny me.

“Actually, Mistress, the tool happens to be right here on the dresser,” I said. I could tell by her smirk that she was amused that I had anticipated this possibility. Even so, I expected only to be taunted further. Just because I’m unlocked from chastity for a few days doesn’t mean she would allow me to have intercourse with her. I briefly fantasized about being allowed to just rub my cock head against her now very wet pussy lips for a minute or two, and then she’d roll over and go to sleep.

Which is why I was shocked when she said “Ok, take it [the ring] out.” I quickly removed the 8 gauge ring from my pierced cock and rejoined her on the bed. Just to be sure, I asked: “Mistress, please may I cum inside you?” I couldn’t believe it when she agreed. Despite his lack of use, tiny (her name for my cock) remained hard enough for me to slip inside her wonderful, warm, wet, snug, delicious pussy.

It had been well over two months since she had last permitted this. As a result, the intensity of the sensation was very high, and it didn’t take me long at all to orgasm. It’s good that she had hers first, because I I don’t think I could have lasted long enough to bring her over the edge. It was so incredible to feel her vagina hugging tiny again. I felt extremely grateful to have been allowed that pleasure.

As we chatted afterwards, I got the impression that she was going to want more intercourse going forward. She wanted that pleasure for herself. I’m not sure how that’s going to work when, probably early next week, I’ll be locked back into chastity. Taking my captive bead PA ring out is super easy. Removing the PA lock and the JailBird is nowhere near as quick. But I guess that’s my problem, not hers, right?

Of course I’m also assuming that she meant more intercourse with me. Although she teases me a lot and talks about sex with other men often, I don’t think she’s serious about actually doing it. Sometimes I think I must be crazy to want that and to be locked up for months myself, instead of having sex with her myself.

Having experienced a little serious chastity and denial, I find myself drawn deeper into it. During these days of being unlocked, I find myself a bit uncomfortable about having free access to my cock. I’ve even urinated standing up a few times, and it feels like I’m getting away with something. It’s as if something in me has switched over to chastity as the norm for me now.

In related news, I completed a modification to the PA lock. There was a part of the brass locking cylinder that stuck out. The corners of that little metal piece would poke into my scrotum providing wincing-level bad pain on occasion. It turned out to be quite easy to file down that piece and round the remaining edges. It doesn’t diminish the lock security in any way, and it should be much more comfortable.

I actually am really looking forward to getting locked back into my resized JailBird. I sent it back to have the base ring enlarged. The problem was that when Mistress would get me seriously aroused, that base ring would get so tight I could barely stand it. Because the PA-lock prevents pull-out, a larger base ring isn’t a security concern.

I expect that the new base ring and increased lock comfort will allow me to wear the JailBird continuously for weeks or months. Whatever Mistress wants.

Sinking into Submission

Mistress just loves the look of the tea apron on my housedress. This picture isn’t me, but it shows what my formal housekeeping dress looks like with the white tea apron. I wore it all afternoon for all my housecleaning duties today. My wife sees me wearing it and smiles – so happy. She thinks it completes the outfit, making it utterly obvious as to my servant and submissive role. She says it helps me to look like the sissy she knows I am.

She went on to tell me that someday soon she’s going to invite one of her friends over, and that she will expect me to serve them both. This is another dominant woman, someone my wife knows both in the real world and in our kink community. My guess is she will wait until I’m back in the JailBird, so that she can humiliate me both as a crossdressed sissy and as a chaste wimp with a tiny cock.

Partway through my cleaning duties she got behind me and pushed me to the kitchen counter, leaned me over it, and kicked my legs apart. She lifted my dress and started spanking me. Then she bucked her hips into my ass like she was fucking me. She alternated these back and forth, switching to a wooden spoon for the spanking. It was a fun mini-scene, and I actually went into a headspace where I daydreamed that she was fucking my ass with a strap-on and spanking me. I wished it was real. The pain/pleasure mix was delightful. She is so wonderful.

This morning I had hopes that she would be interested in sex with me. I woke up with an erection – something my cage doesn’t normally permit. I held and caressed her in bed, physically trying to get my point across without being annoying. Eventually she asked “Did you want something?” I told her “Yes.” She asked what I wanted. I said “I can’t say. I’m not allowed.”

You may recall that she has forbidden me to ask her for intercourse. She said “Oh, I see. You’d like to be inside me?” I said that I did. She teased, “I see. You’d like to put tiny inside my warm, wet pussy, wouldn’t you?” I nodded. She was quiet for a while, and then simply got out of bed and went downstairs. I was a bit stunned, but then realized that she has to reinforce her rules.

At dinner last night we were talking about intense scenes. I wanted her to know that I was willing to go as far as she would like in pushing my pain boundaries. As an example, I suggested she could spank me until I cried. She replied “Oh, I know exactly what to do to make you cry. All I need to do is make you watch while another man fucks me.” She was smiling as she said this, and I know she meant it.

It’s probably true, I probably will cry. I honestly don’t know how I will react if she does cuckold me someday. I’ve always said the emotional piece would be the tricky one for me (as opposed to physical, moral, intellectual, etc). On one level, I realize it’s just sex. But there’s a (small) traditional part of me that honors her as my wife, my spouse, my soulmate. Very little of that will change, really, just because another man has sex with her. But it’s a line that gets crossed nonetheless, and can never be undone.

All those issues seem small to me, though, compared to two others. One is how erotic I think it would be to be forced into a scene like that. The wimpy husband watching his wife turn on and have sex with another man. The other is my very strong desire for her to be happy. I don’t know if cuckolding me will make her happy, but if it would, then I very much want that for her.

It occurs to me that perhaps she is taking things slow on purpose. If her goal is to have my chastity be long-term, then we have lots of time to develop into whatever new relationship she desires. She’s probably figuring out what she wants too, as we go along. It’s not reasonable for me to expect more at this stage. Reminder to self: let go, let go. She is in charge.

Actually, I feel so grateful to be loved so completely by her. She accepts me, even though she doesn’t mind locking away my tiny cock for who knows how long. She encourages and helps me flourish in my sissiness. It makes such a difference to have this level of trust with her. I’ve wanted that so much, to be able to put all of myself into my dominant’s hands and let her have her way with me. Am I living the submissive’s dream? Sometimes it feels like it. I am sincerely grateful. No wonder I love her so much.

Temporary Freedom

My wife, Mistress and keyholder has approved a modification to my chastity cage. It is being mailed back to Mature Metal today. They offer base ring resizing for only $10, another great thing about them and their products.

At the moment, tiny (her name for my cock) is wearing only the PA-lock through my Prince Albert piercing (mine looks a lot like this photo). I’ll probably be switching back to the captive bead ring that came with my piercing, as I need to modify the PA-lock slightly. There’s a piece on it that has pointy corners that can poke into my scrotum at times. It’s caused wincing bad pain a few times just sitting at work, so it’s time to file those edges down.

Although I had only worn the JailBird for a week, I had gotten very used to it. It feels so strange to have it off. My genitals hang down loosely, all floppy and flaccid. I feel surprisingly vulnerable between my legs now. This makes me realize that the cage gave me a sense of safety, being locked into the constrictive cage.

I’m also struggling with temptation. I could masturbate. I know that would greatly displease my wife, so I shouldn’t. But there is a physical and psychological urge that is compelling and a challenge to keep contained. I’m not willing to lie to her, as that destroys the mutual trust that is core to who we are today. And for myself, I don’t want to be a liar, especially to her.

I told her about feeling tempted. She asked me straight out if I had masturbated, and I told her the truth (no). I said “I’m quite aware of how bad the consequences would be if I did.” Her response: “No, you really have no idea how bad it would be for you.” Ok, it’s pretty damn clear that I won’t be cheating just because I am sans-cage for a few days.

Last night we watched the South Park episode featuring the Shake Weight (season 14, disk 3). It was hilarious how they overlaid masturbation onto that exercise device. Afterwards my wife wanted to masturbate me. I wasn’t going to say no, since it had been a week since my last orgasm. We had to take the cage off anyway to ship it back for resizing.

In bed she jerked me off with her hand, the PA-lock still dangling off the end of tiny. I was so aroused by her touch that I came very quickly. I wasn’t even fully hard, and I lasted only a minute or so. It was a very intense and enjoyable orgasm. My wife commented quite a lot about how it didn’t take me very long.

She also mentioned that she was thinking about letting me fuck her, as long as I was out of the cage already. That didn’t happen last night, and she might just be teasing me. I’m a bit worried that I won’t be able to last very long, like last night. Pleasing her is important to both of us.

This makes me wonder: might chastity be turning me into a premature ejaculator? If so, that could be one more reason for my wife to seek out other men for sex. And another thing to use to humiliate me. I can’t help that I’m so sensitive after a period of denial. My wife probably won’t mind it, though, as she seems fine with forgetting about intercourse with me anyway.

She continues to notice and comment about black men. At dinner tonight a man with very dark skin was at a nearby table, and she spent quite a bit of time looking at him and talking about him. It’s such a mind-fuck for me, because I don’t know if she’s sincerely interested for herself (which is what she acts like), or if it’s just to make me feel inferior (which it does, probably also her goal). It may also just be a tease because she wants to watch a black man overpower me and fuck my ass (or so she says).

In other news, the tea aprons for my housekeeping dress finally arrived. Mistress wants me to do some work for her tomorrow morning, and then I’ll be her maid for the rest of the day. I expect to be cleaning floors, vacuuming, cleaning bathrooms, etc. At least I’ll be able to tuck tiny down under, and avoid the embarrassing bulge under my dress.

Punished

My wife, Mistress, and keyholder punished me yesterday for not following through on something I told her I would do. I failed to mail a letter for her. It sounds trivial, but I had explained to her how easy it would be for me to take care of it for her. Then I forgot.

I guess this is just a way for her to start enforcing the expectations she has for me. In fact, I’ve created a new page called Her Rules which will evolve as she clarifies the behaviors that she desires consistently from me.

When I got home from work yesterday she made clear that she would be punishing me. After dinner she told me to let her know when I had finished cleaning up and doing the dishes. It was clear to me then that she wasn’t going to waste any time getting to it.

Upstairs she had me strip and put myself in our 4-point restraints on the bed, face-down. She tightened the last one herself, making me helpless before her. She proceeded to beat my ass for about 30 minutes using first a belt, then a leather paddle, a cane, and other implements. During this she quizzed me about what I did wrong, how that must have made her feel, and what I will be doing differently.

Once she was satisfied with the redness of my butt, she surprised me with something new. She applied some of that muscle ointment that heats up, right on my stinging ass. It took a while for it to work, so while she was waiting she poured some isopropyl alcohol on it as well. The alcohol really stung, and then my whole ass got really hot. I was thrashing around, straining my bonds and yelping. She seemed quite amused, and left me to suffer for a while.

A short while later I was laying next to her. I was still naked, she was still fully clothed. She took the opportunity to play with my nipples. She had no mercy as she tortured me for another 20 minutes. Those little erogenous zones drive me into a sexual frenzy. I was straining so hard against my cage, trying to get erect. She laughed at my futile attempts to get any genital stimulation, as I pumped my hips into the air. I can’t help my carnal reaction. It’s humiliating, and she loves it.

She said it made her wet, and that her pussy was warm and moist. She teased me that she was thinking about letting me fuck her, but after my behavior, there was no way. I’m quite sure she has no intention of letting tiny (her name for my cock) inside her anytime soon. But she loves to torture me with the fantasy. Just thinking about being inside her makes me strain my cage. I was exhaused after all the torment of the evening.

The previous night she used my hand to give herself two orgasms before bed. We were spooning, and the bits of my cock that were squeezing between the bars of my cage could just barely feel her soft behind. She pulled my wrist between her thighs, and without being told, my fingers found her clit. She brought herself to the first orgasm by grinding against me as I laid still beside her.

Then she reached between her legs and felt my forearm. “Oh, that reminds me of how thick my black lover’s cock is. He is soooo big – nine inches! Last time he laid behind me, just like you are. Except his incredible cock was inside me. I had four orgasms, and they were wonderful. He came three times, and each time I could feel his hot spray inside me. It felt so good.” Moments later she had a second orgasm. Then she went to sleep.

Today she surprised me with an email proposing that we attend an upcoming athletic event. She wrote “I was thinking I could perhaps meet a mandingo man” there, meaning a black lover. I honestly don’t know if she’s teasing or not. I suggested to her that she could try CraigsList, maybe searching for “cuckold”. A few weeks ago I saw two local ads. Today there were over 1/2 dozen, including one experienced black bull.

It feels a little insane for me to be encouraging, and even suggesting, ways for my wife to find other men to fuck. I still don’t know how it will affect me if that happens. But I do know that I feel very sad that my chastity denies her the intercourse we used to have together. I want so much for her to be happy and satisfied, including being sexually fulfilled. Even if that means another man’s cock is inside her.

I’ve also created a new page called My Stats. I won’t be impressing anyone with my chastity duration anytime soon. But I want to be tracking it. I plan to also track a few other significant things, like: intercourse denial, my last orgasm, milkings (eventually), and number other orgasms since I’ve been locked up. I’m open to other suggestions.

One last note for today: I think I may have discovered someone where I work who is also in chastity. I may be wrong, but I think he also has to sit to pee – why else would that be? I’m going to continue to observe and see if I ever see him at the urinal. What are the odds that another guy who works on my floor is locked up?

I feel more humiliated each day as I walk past real men who can pee standing, on my way to sit in a stall instead. Sitting there dribbling past the PA-lock and cage, I sound like a girl using the toilet. Looking down I see my satin and lace panties, with a pantyliner (for drips). Many times a day this routine reinforces what I have become: a chastised sissy.

As a bonus for today, here is a link to another story I enjoyed recently on Altarboy’s chastity site: Letter from Shana.

For Her Amusement

Mistress got upset at me yesterday. I had shared with her that I was just thinking about how nice it would be to be inside her, but made clear that I knew I wasn’t suppose to ask to have intercourse with her. You may recall that about a week ago she made clear that I am not allowed to ask to make love to her.

She felt that even bringing up having sex with her was not ok, even if it wasn’t a request. So she clarified that I am not allowed to even talk about penetrating her with tiny (her name for my cock), in any way whatsoever. She emphatically stated that it is entirely up to her “when, or perhaps more appropriately, if” I will ever be allowed inside her again. She said “At this rate, it’s looking like it will be about three years.”

I think that was an off-the-cuff remark. I hope it was. She hasn’t talked specifically about release times at all. We used to have sex several times a month, on average. But it’s been almost two months now that she’s denied me.

She has also talked recently about having me tattooed, although she’s still pondering what it would be. Her most recent suggestion is the word “Sissy” in large letters just above my ass.

I gave her a present after New Years that I haven’t written about here. Included was a card that let her know that, despite my aversion to needles, I was turning myself over fully to her, including needle play. She was looking at tiny in his cage recently, and remarked how she could just push some needles through my penis skin right between the bars of the cage.

Then she asked me if I would do that for her. I said “Of course, Mistress,” but my mind was reeling at the thought of putting needles through my own cock. It really is a tough limit for me to deal with. But I trust her so much now.

Last night she let me lick her clit until she had an orgasm. Tiny tried so hard to have an erection, with the smell and taste of her pussy right there in front of me.  I feel so fulfilled when she cums, her achievement of pleasure gives me the sense of being whole and complete. I crave for her to use me for her enjoyment. It’s nice to fall asleep with the smell of her on my face.

Yesterday she spanked my ass with a wooden spoon, just for fun. She made clear that I hadn’t done anything wrong. It’s just that she wanted to paddle my ass and see it get red. It arouses her to use me for her amusement like that. So to me it’s just another way I can please her.

Tonight she asked me to install something in our bedroom someday soon. She wants a chain hung from the ceiling that she can use for some purpose. Apparently she saw a video online today that gave her some ideas. I don’t know what she has in mind, but being naked and helpless before her sounds wonderful.

She’s waiting for me now in the bedroom, so I must not delay further tonight.

Piercing #12

I got quite a surprise on Saturday. My wife/Mistress/keyholder asked me to make an appointment to get my nipples pierced – that evening.

We did talk about it together, and I was fine with it. A bit surprised, but happy to let her make a decision like that about my body. I think it’s wonderful that she’s accepting my submission so fully. I want her to own me, and to make the decisions. This made it clear that she is quite happy to do so.

I’ve had my nipples pierced before. She loved the look of metal through my nipples, and I really liked them too. But they migrated and I had to remove them to minimize problems. That was about 6 years ago. Things healed well, although I have a little scar tissue.

Back then we wanted rings, so we got curved barbells when pierced. The piercing community has learned a bit since then, and for male nipples especially, straight barbells heal much better. So I now have 12 gauge metal through each nipple.

When they are healed in 6 months, Mistress wants to change them to stirrups. Like rings, they work well as bondage attachment points. She can’t wait for that.

You might be wondering about my other piercings, as 12 might seem like a lot. Here’s a run-down:

My first two were ears, which I still have and use (and love). Crossdressing just wouldn’t be the same without pierced earrings.

My next two were nipples, which didn’t last as mentioned above.

I then had a series of genital piercings: one dydoe, two hafadas, and two frenums which were the start of a ladder. The dydoe hurt the worst. And unfortunately they all grew out too. My best guess is that they had too much pressure and movement to stay healed.

The dydoe was particularly interesting because of our jewelry choice. On the back side was a captive bead, a short straight barbell through, then a bead with a ring on the other end. Like this but with a ring on only one end. The result was a handy attachment point for the head of my cock (e.g: leash). We thought it was really cool and fun.

That’s a total of 9. My recent Prince Albert was 10, and the nipples for a second time make 12.

We also have matching tattoos. She enjoyed getting hers. I nearly screamed and cried through mine.

And she’s talking more seriously about getting me tattooed again. I’m not sure what it will be yet. Stay tuned.

First 24

My first full day of true chastity has gone pretty well. Being locked up like this isn’t too physically different, but mentally it is.

I never had any intention of defeating my chastity devices. With both the plain JailBird and the CB-3000, pull-out was always an option. I guess I did pull out once of the plastic unit, but I didn’t masturbate, I just put myself back in. Now I cannot pull out due to the lock that goes through my PA piercing and the end of the JailBird cage. True chastity.

Physically the cage feels about the same. But mentally I know that I am truly trapped in it now. No escape. She has hidden her set of keys. And she said today she’ll be checking the emergency key box weekly to ensure that it isn’t tempered with. Without access to the keys, my cock is trapped in this cage for real, 24 hours a day. No erections, no masturbating, sitting to pee, and my cock is always less than 3 inches long at all times. And the craziest part? I helped make it happen.

The PA lock is very secure, but it offers a little more discomfort than the simple captive-bead ring that I got when I had the Prince Albert piercing installed. I’ll go into more detail about all the pieces and parts in a few weeks. I’m pondering a product review posting for Altarboy’s chastity site.

My wife seems serious about having this chastity experience be real. By that I mean under her control. I was a little surprised when last night she told me we’d have to get good at this “milking thing”. I didn’t even know she knew what prostate milking was, so that indicates she’s been doing some reading about chastity on her own. That’s a good thing, but it was a surprise to me.

She said she didn’t know much about milking. I reminded her that we have an Aneros unit that should make it easy (we haven’t used it). She said that’s fine, but she didn’t know how, so maybe she’d just have me do it. That sounds pretty humiliating. To not be permitted orgasms, and then to have to penetrate myself anally to force my built-up cum to dribble out. Well, she gets to decide that.

I also realized that milking isn’t usually necessary unless the time between orgasms is long – typically over a month. So that suggests that she’s planning for some long-term lockup. She did ask me what my longest time being locked up was, but I honestly didn’t remember.

After she locked me up yesterday I expressed a little disappointment that I hadn’t gotten to be inside her first. I had held out just a little hope that she might let me fuck her one last time. She was pretty annoyed at me even bringing it up. And she said I was not to mention it again unless I wanted my lockup time seriously extended. Her reaction both surprised and aroused me. She is serious about being in control.

I sincerely was kind of bummed, though. The last time she permitted intercourse was Thanksgiving, about two months ago. Fortunately I can remember it vividly. She’s allowed me some orgasms since then, by either her hand or mine. But I’ve been begging and longing so much to feel my cock inside her again. However, I understand now that sex with me is clearly not on her to-do list.

She continues to talk about her fantasies of black men and their nice big cocks. She teases me about how nice it would be to have one inside her, and how she’d like to make me watch as she fucks men with real cocks. I’m still not sure how serious she is. I do wonder if it’s more likely now that she intends for my cock to be locked up for a long time.

There was a black man she found on-line who lives nearby. She contacted him, but he hasn’t responded. It could be that he’s abandoned that profile. Or who knows, my wife could be talking to him by phone tomorrow. Or maybe she’s looking elsewhere.

Last night she allowed me to lick her pussy until she orgasmed. I find that so fulfilling lately. Her smell and taste really arouse me, so it’s a bit painful to try to get hard with the chastity cage. But that doesn’t matter, she’s using me to pleasure herself, and that means a lot to me. I feel very gratified, it’s a meaningful experience for me. I find her pussy beautiful and fascinating, and I will worship it whenever she asks.

I’m suspecting that my chastity experience will transition into a more long-term journey now. I may post less frequently, depending on what events occur. I’m aware of wanting to keep the interesting-to-mundane ratio high in this blog.