First day of "real" chastity! Hopefully many more to come.

I thought I'd start one of these journal threads so I have something a little more persistent than the posts over in The Tower. This will be a place for me to catalogue my thoughts, experiences, and fantasies in a community with like-minded people. It's going to be pretty free-form and I'll probably post in fairly random intervals. Please feel free to comment with thoughts, stories, or advice!

I've had a long journey getting a cage that's wearable for me. I just don't think my anatomy is very conducive to being locked up. I just had my Jailbird resized and although I don't think it's a perfect fit yet it's finally to the point that I felt genuinely comfortable in not having my own key on standby. The secret seemed to be going as short as possible. I'm currently in a cage that's 5/8" shorter than my shortest flaccid length. I think as time goes on I'll go shorter. I'd love to be in a cage that's a full inch shorter than my flaccid length. I love how my cock looks in its cage now. Before I always used to have a little room to go. Now when I'm totally flaccid I'm just barely touching every bit of the cage and at the first hint of an erection I'm already pressing firmly against the bars.

Today is the first day I've ever not had access to a key. My KH took them to work with her. There is one backup hidden somewhere in the house. Everything feels much more... real now. Before even though I wouldn't cheat, knowing I could unlock at any time made the whole concept of being in chastity seem very artificial. Now, knowing I can't, I am so excited. I've been getting random (attempted) erections all day, something which hasn't happened since my teens.

My current goal is to be able to be locked 24/7. I'm still working on being able to sleep in my device. For the time being my KH has agreed that she'll let me take off my cage to sleep. This is a little disappointing to me that I have to do it, but she's very encouraging and assures me that we'll work together until I get to the point that it doesn't need to come off.

If I'm being honest I really want her to force me to wear it, no matter what. I know this isn't realistic or healthy and it should remain a fantasy but if she came to me tonight and said that we're going to solder the cage shut I don't know that I'd be able to say no. I have a lot of conflicting feelings here. On one hand I want her to be an aggressive and malicious Domme. I want her to not care (and probably be turned on by) how much pain she's causing me. For her to go out and fuck other people without asking me then to come home and tell me about it. On the other hand I know that isn't sustainable and I want those things in a gentle and loving, yet firm way. To not be "her little bitch" but rather her submissive, so that we can explore ourselves and grow together.

We're both exploring what we want out of this relationship dynamic but I think so far we've been doing well. She's always been dominant over me. It caused some trouble early in our relationship and several times we almost broke up. After a year or so I had a very serious talk with her about what she was doing and how it was affecting me. She genuinely didn't realize the extent of her actions and backed off. We've been together another 7 years since that and we've since learned to introduce her dominance into our relationship in a healthy supportive way, instead of a manipulative and destructive one. We started dating in our late teens and have both grown a lot since then. I think she has an inherent need to dominate. This has made her very successful in her work. However it's been a challenge to channel it into a healthy relationship dynamic. I now know she cares deeply about me, and although we've had our ups and downs I think we're finally getting to a place where we're both happy and having our needs met. Frankly, sex has never been fantastic between us. I think we've only stuck together for so long because outside of the bedroom we're best friends. I couldn't ask for someone better to spend my life with. I feel like I often hear about people who have a bad relationship but great sex. We ended up on the opposite side of that but inserting a healthy D/s dynamic seems to be helping a lot.

In the short term, aside from 24 hour lockups, my biggest goal in being in chastity is to get back in shape. When we first started dating I was 17 or 18 and very trim. She used to enjoy dressing me in girls' clothes and it remains one of my biggest fetishes. However when college hit, it hit like a brick wall. Academics, quick & easy meals, and drinking readily pushed exercise to the wayside. I never became fat in a real sense but I certainly lost my trimness and with that her desire for me to crossdress. We're honest with each other, especially when it hurts, and she has a hard time being attracted to me when I'm not in good shape. I commend her for sticking it out for all of college with me promising every year to do something about it and then quitting after a month of intermittent gym visits. If I could lose about 10 pounds I'd be at a point that I'd consider to be good-looking again. 15 and I'd probably be pretty trim. I'm going to sound weak-willed but this is pretty difficult for me. I have a hard time eating a salad when I know as a cook I could instead whip up a whole batch of French beef-stew that people would pay $30 for as an entree. But that's life and at some point you have to accept you can't eat like you did when you were 18. I've at least started drinking significantly less.

So I have a few sacrifices to make but I think that's alright. Making these sacrifices will allow me to truly explore my submissive side. And oh how I want to explore it. I've shared some of these fantasies (and some more or less in parts) with my KH but I've had a lot, especially now that I'm locked again. I'd love to only have caged releases. Perhaps once a month I could put on my full sissy maid outfit and be bound to our bed and gagged. My KH would peg me and I'd have to signal to her if I felt I were close. If she was feeling generous she'd allow me to cum in my cage onto a little mirror, which I'd be made to lick clean after. These are just fantasies and I'm ranting now. Anyway I think I've said everything I wanted to for now and this was a helpful exercise in articulating some of my thoughts and feelings. If you read the entire thing, thank you for showing interest and taking the time out of your day to read about my experiences! Again, please feel free to reply with any feedback, encouragement, thoughts, advice, or just to say hello.

 

For context here we have 2 safewords: yellow and red. Yellow means you're near my limit but can keep going. Red means you just went past my limit, continue but don't continue with that intensity. Red Stop means you just went past my limit and I want to end our session.

We had our first D/s play session in a while last night. My KH dressed herself in her mistress' outfit and had me strip. She bound me and used various impact toys on my ass and thighs, all while I was caged. I'm still working on a good fit for a cage and it was very uncomfortable to wear it throughout the session but I managed. She went until I called out red at which point she decided I'd had enough and untied me to watch while she used the vibrator wand to bring herself to a very strong orgasm. I loved every second of it.

One thing I genuinely don't enjoy, though, is that she has the classic man's problem of getting tired after an orgasm. She'll occasionally have a second, but this is pretty rare. So after I'd been beaten with my cock straining for a half hour and watched her get herself off she's now basically only focused on falling asleep. She hands me my key and mumbles that I'm allowed to take my cage off now (we currently are still working toward overnight wear). So I do and come back to bed.

At this point what I really want is some aftercare and some teasing. Both of these feel like they're borne of selfish desires but at the same time they are things I really want. I've been caged for 10 days now but there hasn't really been any tease aspect. I don't expect to be given an orgasm but it's nice to have my cock paid attention to at least somewhat. However I don't think she understands the tease aspect that I want out of this dynamic. Yes my cock is in a cage and no I'm not allowed to have any orgasms but that doesn't mean you can just forget I have a penis. You have to take it out and use it every now and then. I'm very conflicted here as well because I want to please her and be denied myself but I also want to be teased and edged. I worry that I'm rushing things though and that I should introduce these things slowly not inundate her with "I want you to do X, Y, Z".

I'm lying in bed next to her at this point, involuntarily at full erection. I want her to tease me but I don't want to just tell her "Hey, stroke my cock until I almost come a few times and then tell me it's time to calm down and go to bed." So I said "I really need to have an orgasm." She asked what would happen if I didn't and I jokingly said I'd go insane or come on accident. So she offered to blow me.

I'm absolutely not going to turn that down in my current state. It's of course what I wanted in the immediate sense but I was also disappointed she gave in so easily. It was easily one of the best blowjobs I've ever had. I was extremely sensitive after not having my erect cock stimulated in any way whatsoever for 10 days. I came in less than a few minutes but she knows that's normal for me when I haven't come for a while. I loved having an orgasm but I was also kind of disappointed. The sexual high of denial was gone and replaced with a sort of fuzzy happiness which honestly just wasn't as good.

So, I don't know. We're heading in the right direction in our D/s relationship but I feel like we're drunkenly stumbling there, not walking smoothly. I can't tell if I'm being ungrateful or unreasonable. Or if I'm just being an impatient asshole. I know from all my reading about chastity that there's a classic trope (in relationships between a male and female, at least) of the male part wanting everything to change to his perfect fantasy overnight and the female part can get overwhelmed because she doesn't understand what's being asked of her or, even if she does, how to do it.

At any rate I think I'll try to communicate some of my feelings to her tonight. And I hope I can get input from her side, about what she wants and how she's feeling. I'll be reasonable and try not to overwhelm her with details and specifics. She and I are excellent communicators for every life aspect except sex, it seems. Anyway, back to day 1 orgasm-wise, now.

 

Wow I just reread these posts for the first time in a month. I have apparently changed a great deal in that time. They seem kind of selfish and conceited, now.

I've gotten into a much better exercise routine. The weight is coming off and being replaced with muscle. It took about a month to start noticing a difference but it's there, and she's commented as much. Like many things it seems like exercise is something you're initially resistant to, then do begrudgingly, then actually come to want. We've also been eating much better. I cook as my hobby and was preparing meals 3-4 times per week. Now we eat in almost every night. Sometimes it's leftover night but often it's prepared from scratch. I love preparing dinner for her and the money it saves can be spent on other things, saved, or used for less frequent, fancier nights out. Like my orgasms, quality over quantity. Neither of us are vegan but we have for health and environmental reasons started pretty serious meat/animal-product reductionism in our diets. It's now a large feature in our meals maybe only twice per week instead of almost every dinner, as before. This has forced me to be much more creative in my cooking. To learn to use more ingredients in different combinations to produce something that still tastes rich and wonderful all while being much more healthy.

As far as D/s and chastity is concerned we both feel as if we're making progress. We sit down once per week to discuss the previous week. We can talk about what we did or didn't like, both in a general and specific sense as well as what we'd like to do in the future. It's totally out of the context of our D/s and I won't be punished for anything I say during it.

She says she's feeling more confident as a Domme and keyholder. Before I felt much more in control of my chastity. If I asked to take the cage off for some reason she would say yes without any thought because she didn't want to cause me discomfort and was never sure when it was appropriate to say no. Recently we had this conversation:

"Hey I'm going to go shower. May I take off my cage so that I can shave?"
"No, I don't think so."
"Why? I can't shave without taking it off."
"That's fine, you can shave another time. I don't need a reason, I just feel like I want you to keep wearing it right now."
"Alright, Miss."

That used to a problem for us. She felt uncomfortable switching between vanilla and D/s, and didn't know when it was appropriate. I feel like she understands now that it's always appropriate and I will always appreciate being dominated, especially as I am almost always horny (or if I'm not that can change very easily). Now it's very easy to tell from her voice and mannerisms if my girlfriend is asking me to do something or my Domme is ordering me to do the same thing. We used to have very isolated play sessions in which she was my Domme. Now we kind of flow in and out of it in our daily lives and it feels very natural. She said recently that she feels we're closer and in a better place than we have been in years. Personally, I couldn't agree more.

One of the biggest lessons I've learned over the past weeks is to just shut up. When we first started and she was unsure of what to do I filled in that void with what I wanted. I know now that's not appropriate for a chastity D/s relationship. It's about what she wants and what she is comfortable with. I overloaded her with all my fantasies and desires which made her feel overwhelmed trying to meet my needs. If something is urgent I will bring it up right away. Otherwise I will wait until our weekly meetings and we will have a productive conversation about it. If I'm not overloading her constantly she has more time to naturally fall into her role. It also gives her time to gauge my reactions to things and experiment without worrying about being constantly micromanaged. And the more I let her explore and the less I push the more confident and engaged she becomes. And you know what? Something that I'm only mildly interested in, but that she came up with, is thousands of times better than my most involved fantasies, if she's only acting them out to please me. The less I ask for, the more I get, and the better it is. The more I submit, the more she leads, and the closer we become.

Speaking of pleasure, it's all about her now. Giving her a strong orgasm satisfies me in a way I never knew I could feel. She has told me that in the past she would sometimes not want sex not because she wasn't horny but because she didn't want to worry about getting me off as well. She likes doing that, don't get me wrong, but sometimes she wants to just have an orgasm and go to bed. No frills, whips, chains, or cocks involved. Occasionally in the past this might have lead to us masturbating together but more often than not it lead to a dead bedroom and some awkward tension. In one of our weekly meetings we talked at length about this. I strongly affirmed that especially now, in a chastity D/s context, as my Domme she never owes me any pleasure at all. Pleasing her is my main concern. And anything I receive in return is a gift to be given if and when she feels like it, and will always be received with the utmost gratitude. I think only very recently has she felt comfortable with this. Just tonight she turned in early and I came in to say goodnight.

"Before you go to sleep, I was hoping I could make you feel good."
"I don't know. I'm not really horny or Dommey or anything and sex seems like a lot of work right now."
"That's completely okay if you're not into it. I just want you to know I don't expect anything in return and you never have to make this a big event or anything. It can always just be casual."
"Hm. Well, okay. That sounds really nice actually, get the vibrator."
(after, I have my head on her chest listening to her breath and her heartbeats slow)
"And it's okay that I don't want to unlock you now or anything?"
"Yes, absolutely."

And honestly? I didn't even want her to unlock me at that point. I felt so happy to have given this beautiful woman a wonderful orgasm that having one myself seemed irrelevant. If this is what true submission feels like I might be happy never asking for an orgasm again. Then again, I had a full one a week ago and a ruined a few nights ago so I might simply not be desperate enough yet.

Finally, it's getting late here and I should be getting to bed soon. I will have to wake her briefly so she can unlock me. I hate to disturb her sleep but we've agreed it's a necessary evil until I get a perfect fit. I do believe I'm very close here. I still suffer with burning on the back of my scrotum during erections as well as the ball-crushing feeling I'm sure many who've worn a chastity cage know. Every adjustment I've made has lessened this to varying degrees but nocturnal wear and wear during extended teasing remains impossible. Tonight I was maybe 60% of the way to needing to ask for it to come off. I'm very pleased I didn't but if she'd wanted another orgasm I don't know that I could have strained for that much longer. The cage goes back for a gap increase (on the seasoned advice of Mature Metal) after the Thanksgiving holiday. Here's to hoping it fits well enough for more wear so that I can focus more fully on her pleasure and that we can become that much closer in our journey together.

 

Yes I hope this is the case! We just need to find what works for us.

We're still working on this a bit but I did have a night where I was rather upset and now she's always asked about how I feel after.

I'm really getting into the mind games here. I do really want to come a lot but at the same time I don't want the ride to end.

I've found that if she wants to hear about them, she'll ask.

Yeah I can see this starting already. My orgasms are rapidly becoming less of a priority. Both scared and excited.

I use baby oil gel on the back of the ring, always. I don't think I could wear it without. I can see the skin has already toughened a bit because any burning I get is muted compared to what used to happen. I can't seem to get rid of the ball crushing feeling, though. I could deal with the burning but the ball pain is much deeper and intense and tells me that if I don't take the cage off for it I might be causing some damage.

Thanks for reading!

 

It's always been this way, whether it's day 1 or 3 weeks. Personally I'm not a huge fan of the finger test, some people have pudgy fingers and others have bony ones, you know? But I have pretty "average" sized fingers and yeah I do pass it.

I tried going up a size but holy moly was that bad. The device was falling down all the time and the ring had so much room to move it chafed me raw after only a few hours. With my current device I can wear all day. I pretty often forget that it's even on. The only time I have problems is during erections. Mature Metal seems to think it's a gap issue, so it's going back next week. Hopefully my KH will have real 24/7 control soon.

 

My cage is currently out for a gap increase as per Mature Metal's advice.

I do not have a spare cage and the past few days have been... difficult to say the least. It's even harder than I remember to abstain from masturbating. I had to leave the house today and go somewhere public. I was starting to convince myself that I could just edge a little and watch some porn but I know without a doubt if I get to that point I won't be able to stop.

We had a really awesome tease session last night. I was allowed to penetrate her after she'd had an orgasm (and while the numbing cream she'd told me to put all over my cock was doing its work). We're still working on our PIV and she got sore fairly quickly. She told me I was allowed to come all over her if I could despite the numbing cream. It was a lot of work and she was luckily feeling talkative and indulging my fantasies so I was able to get very close. I told her I was close and she told me to slow down.

"What if I decide I don't want you to come anymore?"

She made me beg for it and I was very honest and confessed how desperate I was and that I didn't know if I could keep being good without the cage. She thanked me for my honesty and gave me permission to finish. It was nice and did help with my libido levels but the numbing cream had really done its work well and it ended up feeling like a very mediocre orgasm. When I told her as much she responded with something like

"Good, you can have a better one when you've earned it."

I've always loved my girlfriend for our entire relationship but, wow, I don't think I've ever felt this attracted to her. It's just this raw lust that I don't even know how to describe.

Honestly, though, if I hadn't had that release last night I think I might have slipped up today. I just can't do this without a cage. I'm desperately hoping MM gets it back by the end of the week. I think I'm going to try to spend any time she's not in the house out with friends or in a public place so I can't get off but I might have to beg her for more release soon.

 

I told her as much last night and she allowed me to come again. She did make it clear, in no uncertain terms, that I was only allowed to come 2 days in a row because my cage is out and she understands it's difficult for me. I know she wants to deny me but I think she also knows that I'll masturbate eventually and figures she'd rather have me masturbate with/for her, instead of alone. I agree.

I'm still fairly pent up (especially since 3 months ago I was masturbating once or twice per day) but I can see myself lasting through the week now, at least.

 

Frustrated.

It looks like it's going to be at least another week until my cage is back. It's really making me realize how much I would rather be wearing it. I have still abstained from masturbating but it's becoming more and more difficult. If I'm caged I can deal with it. I'll focus that energy on something else because I can't get off (or at least not easily/well) Without it I'm tempted to pull my cock out and JO every time my keyholder isn't around. She's currently not and teased me about something later tonight. I'm waiting, of course, but I feel like I'm kind of going crazy by abstaining right now. Hats off to anyone who successfully does honor system chastity, I know now I never could.

The other issue here is that I don't want to constantly proposition her for sex, which is just making me more pent up. I don't want to come off as annoying and needy. Her libido isn't quite as high as mine and whereas she only needs to have a 3-5 orgasms per week, I strongly feel the need to have one every day. Without my cage we both know that sex gets initiated because I am interested in coming but it should be about making her feel good. My orgasm is an optional treat.

She's been very understanding but I may have to talk to her about how pent up I am. The difference between caged and uncaged chastity really is like night and day. When I'm caged I want to stay that way and sometimes, even when I'm released, I don't want to come. I'd rather stay horny and please her. Now it's the total opposite, my sex drive is rampant and focused entirely on getting myself off. No wonder we had a dead bedroom before reintroducing D/s and chastity. She's graciously allowed me to come 3 times already since the cage went back but as I'm not masturbating it hasn't felt like enough, it's like I'm totally insatiable about my orgasms.

The upside is that if I was ever concerned that she was just catering to me, I don't think that's the case. She asks about the cage coming back a lot and has said that she misses it being around. I've additionally been told that when it comes back I'll be made to try sleeping in it more frequently. So yeah I don't know. I'm happier with our relationship than I have been for years but at this point I'm just frustratingly impatient about wanting to lock my cock back up so that we can go back to truly focusing on her pleasure.

 

Yeah it was really amazing how much my perspective changed over that month. I occasionally read those first 2 posts to remind myself of what not to be like and they kind of make me cringe. I almost want to have them go away but I think they're an important indicator of my progress.

 

Last night I was very honest with her about the issues with my libido. This was post sex where I was again very graciously allowed an orgasm. I explained to her that just abstinence rather than an enforced chastity was not having the same effects psychologically for me. I was actually finding it unpleasant to not be caged for various reasons the strongest of which is the guilt I experience about so quickly returning to focusing on myself. They're the same feelings I had when I first started out, but I am experiencing them in a new context. I feel guilty about feeling that way rather than resentful toward her for "not meeting my needs".

At one point she stopped me and asked if I hadn't been masturbating. I said (honestly) no, of course not. She seemed genuinely surprised. Since we never explicitly addressed the topic, she wasn't sure if I'd been getting off on the sly. I told her I don't want to masturbate but I often feel like I'm not going to be able to help myself. I want my orgasms to be with her, when she allows it. She smiled and told me how happy that made her and that since I had genuinely been abstaining, that she felt like she had more power than she previously realized. Since it was on topic she addressed it specifically and said I am indeed not allowed to masturbate on my own. She told me she knows it's difficult and to be honest if I do, and outlined how she'd dole out punishment for it. I'll not lie to her as a relationship built on lies is not healthy so I would have to tell her at some point and the punishment for masturbation sounded like one I genuinely want to avoid. So I can think of that, too, next time I'm tempted to touch myself. Otherwise she said she understands what I'm going through and will continue to allow reasonable release until the cage is back. I love her so much for caring and thinking about me like that, I don't even have words for it.

 

Well, the universe is pretty ironic.

My cage came back today. I'd be super stoked but my girlfriend and I are both battling nasty colds and sex is basically the last thing on our minds. She had me wear it for a few hours today but let me take it off early since she didn't want me to be more uncomfortable than I already am. It might sit in the dresser for a few days until we're feeling better. Or at least until my head doesn't feel like an over-inflated balloon.

 

Finally locked again.

Between my cage being out, both getting sick (staggered one after the other), and holiday business we have really fallen out of our chastity play and D/s dynamic. Yesterday she asked me to put it on again. After 3 weeks I'd almost forgotten what I liked so much about chastity. I'm not fully back to the mindset yet but I'm hoping a few days locked up will help with that.

I'm really hoping this is the final adjustment I'll need for a while. It seems very comfortable for day wear but it still hasn't been "stress tested". I'll be taking some time off around Christmas and I'm really hoping that might afford me some time to try overnight wear again.

 

Wow took a really long break there.

To make a long story short and overly simplified my partner told me she simply wasn't in the right place to be a keyholder or Domme. We took a step back, and worked on some other parts of our relationship. We had no sex for a while, then a lot of vanilla sex, and then eventually rediscovered kink. It was a nice "reset" for us.

We've ended up in a similar place to before but I think we both feel it has a more solid foundation, now. She has communicated some needs and desires for our sex life and I have reciprocated by being open with mine.

One major difference is that we've taken a focus away from her having orgasms and my not having them, instead focusing on intimacy. For her, personally, orgasm is difficult to achieve and can be quite exhausting at times. Before she felt pressured to have one in the context of my denial. If she didn't she would feel bad and I, in turn, would feel like a bad lover. She explained that she does not always need or even want an orgasm to feel sexually satisfied. We've also done away with focusing on going long stretches between orgasm for me. She did not like having an arbitrary minimum/maximum lockup time and would rather simply let me come when she feels like it. Whether that's every day, every week, or once a month. Or any combination of those without any set pattern. We just both try to communicate how we're feeling on a regular basis and that helps us to stay in touch in a D/s context.

I have quite a lot more to write about but I think I'll save it for another day or when the fancy strikes me. For the meantime I'm simply happy to express we're back at it and both having a lot of fun.

 

We addressed some things recently that we'd both been dancing around for some time, and it went pretty well!

When we first started dating my partner used to enjoy having me crossdress. We fell out of it after a while and never came back to it for years. I missed it but never had the confidence to bring it up again. Well over the past couple months I've been much better about exercise and eating well and it's showing quite a bit. I think that gave me the confidence to talk to her about it.

Perhaps 2 months ago I asked if she'd mind if I painted my toenails. Her response was mixed but I went ahead anyway. After I was done I knew immediately I loved them that way and wanted to keep them like that.

She did not react well to it upon seeing.

For a bit of background... (I did not know this at the time and it's more in the context of recent conversations) she'd not only fallen out of a Domme-headspace. She confessed that for a long time she'd felt largely non-sexual. I suppose I always knew it but it was awkward and we avoided the conversation. We both convinced ourselves it hadn't happened.

Anyone who's been in a relationship for more than a few months knows that things which go unsaid will fester until they come to the surface in terrible and violent displays. It doesn't take a genius to know that avoiding the issue was terrible for our relationship.

I'd rather not go into details about it here but we had some very long and difficult conversations. We're okay (actually great) now but the road here was very unpleasant.

I was also honest with her about some feelings I'd had for a while and not expressed. Outwardly, to our friends, family, coworkers, and the public I want to stay the same person. In the bedroom, though? I'm a complete and total sissy.

At first I could tell she was apprehensive but trying to be supportive, which I really appreciated. I told her I really needed to explore this side of myself.

About 2 weeks ago I shaved my legs and painted my toenails blue. It was like another magical moment, looking down and seeing my locked cock, smooth legs, and adorable nails. I felt like "me" in my body for the first time in ages. I don't think I identify as another other than male and I have no question that I might be trans. I think I'm just a boy that really enjoys pretending to be a girl a lot of the time.

I went to goodwill and got several outfits worth of girls' clothes for only $50 or so. It was absolutely nerve-wracking but also a huge confidence boost after I'd done it. I told my partner I wanted to share it with her and that this was important to my sexual identity. I didn't force her into a corner and give her ultimatums but we did mutually agree that if we find our sexual desires are severely mismatched the best thing to do for both our sanity is to have an amicable split.

I drew myself a bath and poured myself a glass of wine. I'd been keeping up with shaving but I wanted to be at my best so I went over everything. I made up a cute outfit and put on full makeup for the 3rd time in my life. I have a short crew-cut so I also had purchased a nice wig with shoulder-length hair, matching my natural hair color.

As could easily be imagined I was terribly nervous to show her. When I finally did though she couldn't stop smiling. It was insane, the waves of catharsis. We had a lovely night and talked a lot about how being honest really helped both of us.

So that's where we are now. It's been fantastic to look forward to this all day. I go to work then get to come home and spend the evening as a girl. I don't currently have the time or energy to do the entire getup but we agree I look pretty cute for now in panties/a bra with some cotton stockings. It's made her feel much more dominant and much more sexual. We'll see where it all goes I suppose but it's been a good couple weeks.

So I guess the takeaway from this post if nothing else is to be honest to yourself and to your partner. Anything else is going to lead you down a bad path sooner or later.

 

Just a quick update.

We had our best D/s session ever last night and I'm reeling still.

I got to spend the entire night in full sissy mode and cook dinner. Miss was apprehensive about the sissy thing before but if I had any doubts about it they're gone now. At one point when I had a break in cooking she had me come into the bedroom and orally service her. I've never given her an orgasm that quickly in my life. After we had a lovely little spanking session and I was caged the entire time.

She does not orgasm during PIV but thoroughly enjoys it anyway. She was very worried she wouldn't want me to penetrate her while I was dressed. This also apparently turned out to be completely false. She was so aroused she actually didn't even request I use lube which never happens.

The entire situation was very exciting for both of us and I admit I lost control for a moment. I pulled out just a second too late and orgasmed without permission. Given I did not stimulate myself at all during (especially since I was desperately trying to stop it from happening) and it was not very pleasurable. An unauthorized orgasm, nonetheless.

She laughed and had be bring her the riding crop. She knows I hate the feeling and reserves its use for punishments. I've never seen her quite like this, though. She completely broke me with it and seemed to love every second. I had to apologize, explain what I did wrong, and how I'll correct it in the future between strokes. After she held me and told me how much she loved me, and how proud she was.

I've never had an experience like this before and we've been messaging all day about it. I'm really looking forward to where our relationship is going.

 

I have decided I am done asking for release.

In the past chastity has been sort of an elaborate game for me. Build the tension, tease the release, deny the release, repeat. Finally have the release with a shaking, mind-blowing orgasm. And don't get me wrong, I still love this aspect of chastity but I'm trying to fixate less on the end and more on the ride.

I love being horny, all the time. It gives me energy (both sexual and in real life) like I cannot have when I'm able to masturbate. I'd rather rub her feet than have an erection. I'd rather give her a screaming twisting orgasm while safely caged than risk the possibility of throwing away all my energy and libido for 20 seconds of pleasure.

I like to serve. I love hosting people, I love doing nice favors for friends, and I love to make my partner happy. And I think all the same applies sexually as well. My gratification is tied into others. If I'm not getting someone off or somehow pleasing them it's just not attractive to me. That can be mutual, of course, but I'm okay with it being completely one-sided. I like it, in fact.

So whatever has happened lately as our relationship progresses had made me realize I don't want to focus on or even think about my own orgasm. I will inevitably yearn for them, I'm sure, but I don't think I'll be voicing that concern. I don't want to ask to be unlocked and I don't want to ask for release. I'm trusting her completely to make that decision for me. I just want to submit.