Day 1 - New to This

I made this same post in the introduction thread but I felt it might be a good post for my first journal entry as well. If this is against the rules, my apologies.

I’m in a committed heterosexual relationship - going on a little over 1 year together. We have a VERY active sex life. I manage a couple hundred people in my line of work and am always in “boss mode”. On the exterior Im extremely masculine, covered in tattoos, ride a Harley, and train in the gym daily. My lady is in a male dominated career field where she owns her own business and is always in “boss mode”.

The dynamics: My lady is always having to be a tough woman at work and likes me to take charge in the bedroom and outside of work. We’ve recently explored light BDSM and she enjoys it when I take charge/lead.

The issue is that I’ve always fantasized about being in a FLR where I’m privately forced into feminization, teased, and locked. She doesn’t know the FLR or feminization aspect but Ive been hinting to wanting to try chasity and finally got my lady to say let’s get a cage. Last night she asked me to wear a plug to dinner (no cage) with friends and she even teased me before we left with making me taste her and a few other things before we left without me touching myself or her. I absolutely loved it!!

Her concern with chasity is that it’ll ruin our sex life because she loves penetration and me taking lead when exploring BDSM. She likes pain and I like sensualness. So there is a bit of a contradiction with it which is my struggle. She is also concerned that chasity will make me become less of a man outside the bedroom. She loves my rough exterior. We’ve talked about it but I don’t like having to tell her what I want her to do as my KH. I’d like her to just take lead…

Today, with my first experimental cage, I’m wearing it but she didn’t seem to excited about it. She looked at it on me, asked a few questions, and then walked off. She may be processing too, I don’t know. I locked it when she walked out of the room and am now wearing it at the gym. I can tell it’s there but it’s not bugging me or causing problems. I haven’t been aroused yet so I don’t know what that’ll be like but so far, this seems easy.

When we ordered this one, she said if WE like it, we can order a much more pricier custom made one.

Im here for advice, tips, and everything else. I’m excited to finally be apart of the chasity team - let’s just hope it gets better with my lady.

 

Still from day 1…

I got home from the gym, she asked questions about how it felt and then we had a very candid convo about the cage, what I hope comes of it, and her concerns. A couple hours go by and then she begins to play with me locked up (it was everything ). Still keeping it on, I wore it out to dinner/drinks and we had talked about it, this site, and what we wanted. BUT we ended the night in an argument, not cage related, so I unlocked it and went to bed.

Today she teased me without the cage on, which was fantastic. I love when she takes charge and ownership! Sadly, she never once mentioned the cage . She later asked about it from last night and I told her it was hers and hers to decide when I wear it again.

I’m leaving for a 1 month work trip next weekend and really hoping she asks me to wear it this week or at least bring it with me. It’s in a drawer so kinda outta site, outta mind kinda thing but I pray she asks me to wear it before I leave or while I’m gone. I’ll keep y’all posted…

 

How freaking excited am I!! This morning during sex we were having sort of sexy talk (nothing unusual for us) and I told her how much I enjoyed her teasing me and it made me cum more than normal.

Well… as she’s riding me, she starts saying how she’s really going to torture me today. SHE said she wants me to put on the cage when we’re done. Then she said since we’re both working from home today that she’s going to keep me locked up while she wears something incredibly sexy around the house and tease me throughout the entire day. Then she said she wants to use our toys on me, which she has before, but while I remain locked. She went on to say how she wants to make me dribble loads of cum while caged and beg for her pussy. Then while on top of me, she said she wanted me to cum. URGH, by this point I was so turned on about what she was saying & doing that I came right when she said it.

Now I’m locked and we’re about to shower together. Im so excited for the day of teasing and chasity!!

 

OMG - OMG - today was great!!

I ended up showering on my own, with the cage on, cause my lady got busy with work. I even asked her (only to see the response) if I should take it off to shower and she candidly responded, “no, I don’t think it’ll be an issue”. Afterwards I was slightly disappointed, did some work, and then went to the gym thinking nothing great was gonna happen but regardless, I was happy to be caged.

when I got home, OMG!!! She had her sexy harness on and latex shorts. I was immediately ready and she tugged my caged a lil. She made us lunch as I sat by the counter having deep relationship convos. - I got us cards for Christmas that have random deep thought relationship questions so we answered a few as she cooked and we both sipped on our drinks. After a late lunch I jumped in the shower. In the middle of my shower she peaked her head in and said, “I want you to be thorough, but not take all day”. WOW! That immediately turned me on!

I dried off, put on some gym shorts, and walked out to her sitting on the sofa with a few toys lined up next to her. She played with me caged for a while and I kept saying how badly I wanna cum. Well, the excitement got the best of her and she unlocked me and we have SEVERAL sessions of fun together.

Although it was extremely hot & fun, I am kinda upset she uncaged me. I mentioned how I thought her goal was to make me cum with the cage on but she said I sounded so wanting and my balls were swelling up. I think she just couldn’t handle it. I hoped she would locked me up after but nope but the night was sexually fantastic.

I’ll be standing by waiting for the next time I’m asked to wear it. Until then, it’s back in the nightstand….

 

I woke this morning to watching my lady get ready for work. Since I didn’t have any morning meetings, I got to stay in bed longer but watched as she got dressed. That’s something I’ve always enjoyed since we’ve been together. She looks incredibly sexy in her business attire - real boss lady vibes with matching sexy underwear, a silk blouse, pleated skirt, and knee high boots. After some quick teasing she left and I laid in bed horny. Not because she’d mind, but I was adamant about not masterbaiting. Well, that didn’t last long.

Now that I actually own a cage, it’s all I think about as it sits in the nightstand next to the bed. I grabbed a bag of frozen broccoli to calm my erection and put the cage on, even though my lady didn’t ask me to. The thought of a cage orgasim has also been racing through my mind lately and if it’s even possible. Well… I grabbed a prostate massager, some lube, and started stroking myself while it was in the cage. WOW - I just came so much while locked up! The rush/shooting feeling of explosion isn’t the same while wearing the cage and I’m left wanting more but WOW, it’s still intense and loads (pun intended) of fun. I’ll clean everything up and get ready for that, uncaged…

Side Note: How do I change the title of my entire thread? I don’t like that it says Day 1

 

I only wear sexy style underwear as well. I think that was my way of acknowledging my desire without moving to women’s panties. I told my lady that life is too short for boring underwear. Thankfully she feels the same way and appreciates me wearing men’s sexy underwear. I’ve always been into fitness/nutrition but have found myself concerned about skincare.

 

☺️☺️

So… as I was packing for my long work trip, my lady said I should pack my cage. Then she told me to bring a few toys and lube as well. I immediately raged with excitement when she nonchalantly mentioned it and I anxiously waited for her to bring it up again. She’s really good at calmly mentioning it but it makes me erotically anxious every time she does. In response, I said, “yes, I will but that’s your cage, not mine.” I made a personal rule to not bring up or talk about the cage topic unless my lady does first. After all, I want her to feel like it’s her penis and her cage both under her control, not mine. ️

Today, after a long stressful journey, I finally arrived to my final destination. My incredible lady surprised me with a text message while I was picking up groceries. She precisely told me once I get back to my room to clean up and put the cage on.

I excitedly replied, “yes, baby”. She told me to respond quicker and it’s not “yes, baby” but to reply with “yes, Mistress”. That comment took me for a surprise and I myself didn’t think I was even ready for that step. I’m still processing it but I absolutely loved the position of power she took by demanding me to respond in such a way. For me, I don’t want there to be a separation between our relationship and the cage. I fear using “Mistress” might make the action/feeling more clinical instead of intimate.

Either way, I was still rushed with extreme excitement and immediately rushed to finish up with the groceries and get back to my room! She continued to provide instructions till I got to my room. I was already fully erect/excited at this point from her direction! I was worried I wouldn’t even be able to get my… correction, HER cage on.

I showered and successfully caged up. She then told me to send proof and then to lay out all my toys on the bed where she instructed me through an amazing caged orgasm! She was sending me demands, asking for picture proof, and having me respond with “yes, Mistress”! She teases me with punishments for being bad but hasn’t really done anything, but I’m definitely not pushing that issue because I’m afraid I’ll regret it once I bring it up.

We’ve also started getting to the point where I won’t cum unless she tells me to, even when I’m dominating her in the bedroom. So right before I exploded, I asked if I could cum. She let me, but said I must keep the cage on.

I’m still in ecstasy thinking about it like it was just a dream. Im only upset that she isn’t here with me. Afterwards, she instructed me to clean up but to keep the cage on. As much as I feel unsatisfied with my caged orgasm, I feel madly in love with my lady and wanting more! Now I sit her anxiously waiting for her next instructions. Until then, I’ll keep the cage on. ☺️

 

Monday was my first time in the cage for 24hrs. Surprisingly, I didn’t feel the intense need to masturbate or even want the cage off until the middle of the night. I read on here that the first couple of nights of sleeping are the most difficult and I learned why. When I’m not cuddling my lady I tend to sleep on my stomach. Since I’m alone in a hotel room, that was my go to position. This became difficult with the cage on but I managed to fall asleep till about 4am when I woke up with a burning feeling. At first I thought I was chaffing but then realized I had that super hard middle of the night wood. It was so bad though that I couldn’t get back to sleep and it was becoming slightly irritating.

I ended up taking the cage off and although very tempted to start playing with myself, even though it was 4am, I pushed the urge away and fell back asleep. I woke up, did some yoga, took a shower, and put the cage back on. My lady didn’t ask about it all day. I was hoping she’d ask me to take a picture while I was work for proof I had it on but she didn’t. After I got back to my hotel room she asked about it and I told her what happened. I was hoping for some sort of punishment but she said she was proud of me for not pleasuring myself. She then told me I could take it off after leaving the gym.

I was kinda disappointed. I only had the cage on for a little less than 24hrs and I also removed it during the middle of the night. With my gym pants on, the cage was slightly noticeable. I sent her a pic (also included in the post) and asked if I could remove it before I go to the gym. She immediately replied with “you should’ve picked better gym pants” which I found so hot and erotic. Although it would’ve been difficult to hide, I wanted that response. Imagine the disappointment when she followed up with another message saying I could take it off. Yes, I was relieved but I was also kinda disappointed. She did turn me on when she stated that even though the cage was off, I don’t have the green light to pleasure myself. She makes wearing the cage easy with no real challenge, but maybe after we and keep going she’ll get better at it.

Later that night we talked and she asked about wearing the cage to work. Then we talked about my cage orgasm. When she asked how the big O was, I told her it was less than dramatic climax, almost a disappointment. She replied with a sincere, “aww that’s not good” but I wanted her to be more happy about that. We ended the conversation with some light sex talk over the phone while she let me cum.

She did surprise me and say when I get back from this work trip that we can properly measure so that we can order a custom one! She also said she enjoys the cage too! So those are two great things!!! I just want her to be a little more cruel or demanding with me wearing it. I want to want to be out of the cage and want to feel the need to cum while not being allowed to but I haven’t felt that yet. I already think when she has me wear it that I’ll only have it on for a short period and then once it’s off she’ll let me cum.

IDK what the future holds. We’ll see…

Now it’s Wednesday, the cage has been off since yesterday evening. I will wait until she tells me to put it back on…

 

Before I left on this work trip, I asked my lady to read @longtallsally journal while I was gone. I felt like she does a good job of explaining chastity and control from a females perspective.

Yesterday, I got to my hotel room and my lady said she read it and said she thinks she’s been going about this cage thing totally wrong. She now realizes it’s about control, intimacy, and chastity from both a mental and physical spectrum for both of us, not just me. She goes on to tell me that she has a few ideas and questioned if she should have let me cum while wearing her cage on Monday. We talked some more about her in control, how she wants to handle things, and that she officially only wants me to masturbate if she directs on exactly how I will do it and when I do it. My first rule! Then she proceeded to give me directions on how to pleasure myself in which I eagerly did!

After that we continued chatting over the phone, I cleaned up, and then went to grab food and hit the gym. When I was laying in bed later that night talking with her about random things and missing each other. I did explain that I’m not sure I’m ready for the “Yes, Mistress” aspect though and she agreed. She explained that at that moment, she just wanted to ensure I knew how stern she was being via text. I’d like to respond with something more serious than “yes, baby” but not sure what. Anyways, our convo started to get hot and she directed me to pleasure myself again before falling asleep. We’ve always had a very active sex life but now with this cage and her taking control, I’m noticing our emotional intimacy is growing. I’m absolutely loving the deeper connection this is building. She said it doesn’t make her physically happy to have me caged but mentally she enjoys it.

After getting to my hotel from the office building today we chatted about usual life stuff and nothing erotic. Then when I got back from the gym we chatted and I told her I needed to shower. Unexpectedly, my lady told me she wanted me to cage up immediately after the shower through tomorrow. I explained that I was feeling slightly horny and she responded saying that I needed a little restriction after the two orgasms I had yesterday. Once I got out of the shower she even asked me to send her a pic in which she said I looked so sexy caged for her. ☺️ To have her tell me that made me so happy! It tells me she’s enjoying and embracing this new adventure. I’m starting to realize there is no turning back at this point but I think I’m ok with that. If she tells me I can take it off tomorrow for a release, I may tell her I don’t think I need one yet… IDK though, I’m nervous that could open Pandora’s Box. I secretly want her to tell me that’s she’s changed her mind and to keep it on until she says otherwise but we’ll see. Longest she’s had me wear it was slightly short of 24hrs. I do hope I can make it through the night without removing it though. I need to get use to sleeping through the night with it on, which the first time I couldn’t.

After that she brought up the custom cage I want. Can you believe that?! SHE brought it up! I sent her the Mature Metal link and mentioned the “Jail Bird” so I could still stroke my cock and cum if she wanted while caged. She really had to think about that one. Then she offered either the “Queens Keep” or “Spyder”. The “Spyder” will completely restrict my head, which is super sensitive. She decided on the “Queens Keep”. She said she liked “a bit more construction”. So now I need measuring advice and if I should go with an oval or round base ring.

But how exciting is this journey! I knew I loved her but wow - I’m absolutely melting in her arms right now and we’re geographically separated at the moment.

**Side Note: How can I rename the title to this?I’d like to remove “Day 1”

 

I want her to keep me locked longer than 1 day and for her to know that I’m ok with that. I’m not sure how without voicing it but I’ll take your advice. I’m hoping it gets to the point when I don’t know when she’ll unlock me so I’m constantly wondering. I’ve already made my own rule of not to mention the cage at all unless she brings it up first, regardless if I’m wearing it or not.

Thank you for the comment. I was beginning to question if anyone even reads my posts.

 

It’s Thursday night and I made it through an entire night caged up! I did wake up a couple times to discomfort from becoming erect and then a few times from just being uncomfortable with it on during my sleep but I never took it off. That’s a win for me!

I’ve gotten more comfortable with wearing it during the work day and at the gym. I’ve realized I can probably go with a slightly smaller one in length though. The more comfortable I am with it on, the less my cock wants to try forcing its way out. Mine right now is a hair over 3 inches. I’m going to look for a 2.8 inch one to test out before I order my custom one. I just wanna make sure I have the perfect sizes down before I spend so much money on a custom piece.

As predicted, I got back to my hotel room tonight and my lady asked me how it felt having the cage on while I was at dinner with my coworkers. I told her it didn’t bother me but felt like a secret between her and I. Then after that she instructed me to take it off and directed me on how to pleasure myself to full release since I had been good. It’s hard to be bad when I’m only being locked for 24hrs. Now I’m becoming frustrated in a totally opposite way than how I should be but I’m not sure if she even realizes that.

I was really hoping to be locked up for longer than 1 day. My prediction is that she’ll have me cage back up for another 24hrs on Sunday, but we’ll see. Following my rule, I won’t mention the cage at all. I’m leaving it solely to her without any input from me. Until then, I anxiously wait to be locked up again under her direction…

 

You’re absolutely right.

So… I can tell my lady is enjoying this cause today she sent me some pictures of a few toys she was shopping for instead of working and they mostly involve her being in control of me. I told her I was worried they were too intense and in a matter of a fact like tone told me that I will enjoy them.

Let’s fast forward to me getting off work early and back to the hotel: My lady messages me some sexy pics and asks if I want to play. She starts to instruct me on how to pleasure myself but this time I could only use a prostate massager. She kept messaging me details about it and how I should be feeling or asking what I’m thinking/feeling. Then after a while she finally lets me start stroking until I’m about to cum. When I tell her I’m close, she immediately tells me to stop and to only tease my head, which is sensitive but I need strokes to really cum. Well after a minute I came but it wasn’t a massive big O type cum. It felt like a teaser shot leaving me wanting to desperately start stroking so I could really shoot a good load. She instructed me to stop, clean up, and then put my cage on and go to the gym. Ummm, I definitely wasn’t expecting that!

To test her, I asked if I could put the cage on after the gym. She first playfully responded “are we negotiating now?” Then she said, “restraint and obedience” followed by “Follow the instructions so your next orgasm will make your head spin”. WOW!!! ❤️❤️❤️

It took forever to get my dick to calm down enough to put the cage on so I could actually go workout. I then asked her how long she’s going to have me wear the cage this time. She said “till tonight. Or maybe Saturday morning. I might wait till Sunday. Have a good workout”.

Now I am frustrated and so excited about it! Wow, this was totally unexpected in such a good way. As much I want to cum a real load, I really hope she makes me wait till Monday but she usually always gives in without me even saying anything so we’ll see. But wow!! I’m so blissfully happy about her taking on this role and actually enjoying it! ❤️ Im melting as this weak man in her grips and extremely blissful about it.

 

Well… things got sour.

Friday night I had no issues with the cage. I even slept in it with zero issues. That’s another win for me!

Fast forward to Saturday mid afternoon. I went the gym and while there, my lady started teasing me with sexy texts during my workout. She said when I get back to my hotel room we’re definitely playing and I was craving it. I finally get back to my room and she tells me to keep the cage on but get out my anal toys. We did that for a while and I had never seen myself precum so much before. It was also the longest I had been locked up. She finally lets me uncage and wow did I cum! Then she tells me to continue stroking even after I’ve already cam a ton. My lady talked me through another release so if you can imagine, I was covered in cum, exhausted, and weak. I loved it!! After that there was no more mention of the cage or any dom/sub convos.

It’s now Sunday night and she’s getting ready for bed. My lady is telling me how much she misses me and show her that I’m wearing her company’s sweater out to the bar. Remember, she owns her own business so I feel like I’m being her with me. I tell her this and she said it’d be better if it was a pair of her panties. That triggers me to get excited so I push more saying I couldn’t imagine walking around with her panties in my back pocket as a hanky. She replied that it’d be better if I packed her silk panties in my underwear around my dick while caged. So now I’m aroused assuming the convo is going in a fun sexy direction.

I wasn’t lying but I confessed that I masturbated early that morning. When I told her I expected her to go into dom controlling mode but the complete opposite happened. It was her 1 rule that I don’t masturbate or cum without her instruction. I was excitedly expecting to be punished. Instead she told me she was emotionally hurt and very disappointed. She was upset that I didn’t ask her or invite her. I could tell it genuinely upset her but not in a fun dom/sub way but in an emotional heartfelt way. After I apologize several times and listen to her being upset, she said she would cage me but “that seems more like a reward for bad behavior”. I asked why and she responded with, “ Because being caged is a stage in arousal and the anticipation for an intense release.”

Now I feel like shit because what I thought would lead to a fun punishment did the complete opposite. I actually hurt her. It took the fun away but led to her genuinely being upset that I masturbated without her when I didn’t realize it was so deep. Now I genuinely hurt and upset my lady and I’m not even there to help. With this being my first trip away for so long, I never wanted something like this to happen…

 

I wish I could edit the post above this one. I was slightly intoxicated when I posted it and the grammar issues are horrific! My apologies to anyone reading it - that is IF anyone is actually reading my journal entries.

Anyways, I didn’t wake up to a good morning text from my lady, which I usually always do. Instead, I woke up to a cold “cage up this morning” message. I of course acknowledged. After apologizing again she said she didn’t want to hear it. She wanted to see that I was sorry. Then my lady reminded me that although I am gone on a work trip with full possession of my key, she still controls the use of that key. She then told me that it’s her key, her cage, and her cock. After agreeing with her she said was glad that I understood. I’m learning those words of affirmations make me feel good.

I do hate that I let her down and upset her. I didn’t think me pleasuring myself without her permission would affect her in such a hurt kind of way like it did. Is it selfish to wish that she would punish me though? How great would it be if she made go buy some panties and wear them or something crazy like that? I would be slightly humiliated but at the same time, I feel like it’s deserved. I could only imagine how uncomfortably awkward it would be to tell the person working that I was shopping for myself.

However, my lady did say she wants to make me ache a little bit. I had already left my hotel today but she said if I was still there she was going to make me wear a plug while I ran errands, knowing that wearing always makes me dribble cum and gets me extremely horny.

It’s now Monday and I’m locked with no idea on how long it’ll be. Longest so far has been a little over 24hrs.

 

You’re right and I like how you labeled it as a “fun-isment” and not necessarily a punishment. I think a part of me wants to be rebellious so I can be punished. I’m also curious what her idea of punishment actually is or where she intends to take this but I know the cage and her having control of my orgasms are staying. I can just feel it from her. BUT, I do really hate that I actually hurt her which is the last thing I ever want to do.

Today my lady has been teasing me a lot with pictures. She made the comment of wanting me to ache because of what I did. So maybe this is her way of punishing me. She hasn’t kept me locked up for longer than 28hrs. I told her I could probably go longer but she said we’ll work our way up to that. I think I’m just very eager and she’s still figuring things out from her perspective.

I also made note of what you mentioned about letting go of control which is something I think I probably will struggle with if she locks me up longer or when our dom/sub lifestyle evolves. I’m very interested in testing that but it’s her rules and she’ll decide when that is.

Thank you for the feedback. I really appreciate it, especially with me being so new to this. It’s also nice knowing that at least one person is reading my journal. Cheers mate!

 

My lady and I had a nice convo on Monday night. She said she never wants to look at the cage as a genuine form of punishment like she did Monday morning when she coldly told me to cage up. She was angry and wanted the cage to be a prison for me which, according to her, ruins the fun. She wants chastity to remain a fun frustration builder with fun-ishments (thank you @Stephplayswithyou for the term) instead of legit punishments. We agreed that the cage will only be used for sexual aspects. Example: I’m not going to be threatened with the cage if I don’t take out the garbage. - However, I want both fun-ishments and punishments but it’s more important to me that she enjoys it & wants it.

After our convo she really laid it on me with teasing me. She sent me hot text, photos, & pics! Then she instructed me to stay locked and I was only allowed to precum, which I definitely did. She wanted me to ache and crave release for masturbating without permission.

I told her that I wanted her to really lock me up, tease me, and torture me. I explained that she can keep me locked longer & ask much more of me but I honestly don’t think she has it in her. She is so much of a giver that she struggles making me suffer. She really enjoys knowing that she’s getting me off. We’re geographically separated and she can’t keep me locked up for longer than a day or two. I really hope this is one area she grows in. I’d also really like to be punished with fun-ishment exercises but we’ll see.

I stayed locked up until this morning (Wednesday - which makes my longest locked period thus far, 2 days) when she instructed me through one caged release and immediately after, another release. Later today she asked how I feel being free and I told her I kinda miss being caged, explaining that I love her having complete control over my penis. She said enjoys that very same aspect and is debating if she’ll cage me tonight or tomorrow morning.