Adventures with the Boss Queen

A few days ago I moved from big city(ish) Texas to small town Oklahoma, moving in with my boss queen. It was a bit fast, but I didn't have a job or the money to get my own place and the earlier I get here the earlier I can look for a job here and we were certain we didn't want to be 400+ miles apart. After getting here and getting all my stuff in her house my boss queen, @Kitt , took the key I was given back on my return to Texas earlier and the keys from a different device I had tried before that happen to perfectly match this one too. Now I don't have the ability to circumvent the system which is nice (not that I did, but it's more fun when I can't).

Of course before going into current happenings it is tradition to go into the past. Months back before the relationship started I was a pretty reserved person about sexual stuff, but Kitt made me feel comfortable and kind of made it a game to get me to divulge my kinks. I think the last one I gave up was chastity, both being a more recent interest and something I'd never told anyone else.

Fast forward a little bit to we've got interest in each other but there's no relationship yet because want to meet face to face first. and a visit is coming up when suddenly I've got horrible migraines consecutively (a couple months previous I had em 16 days in a row). I notice that on days I felt good and wasn't worrying the migraine came when I masturbated. Kitt's response was "Isn't there something that can be done about that?" Of course she was referring to a chastity cage. The ones I had were cheap on amazon and didn't fit well and had horrible hygiene so she informed me that she was going to buy me a new one. We spent a night with me telling her my actual thoughts on chastity and not just "it's my kink," and then finding a cage together.

Eventually that cage arrives and it's something I can actually wear for extended periods of time comfortably. But it's not perfect, it's notably too big when flaccid and upon hearing of this Kitt decides to buy another cage, that one would be delivered to her and she'd give it to me when we met. Eventually that happens and the cage does fit better (and is what I use now but at some point in the future when we have the income we definitely should get a custom one). I had a good time visiting her, and somewhere in the middle we decided that a relationship was what we wanted.

From then until now it was mostly being away from each other and perhaps not interesting enough for a journal. So instead I'll get into some other things. I was upfront in telling her that I thought permanent chastity/denial was super hot to me. So far it seems like she might be into the idea (in a less fantasy, more realistic way) as it amuses her that I'm a virgin and she can keep me that way. Of course if she wants something else I will be glad to give her what she wants and she knows this. Our relationship so far isn't super FLR, as she seems very worried about what I want all the time but she knows that ultimately she's in charge.

Of course right now the first directive is: get a job.

 

It's been almost two weeks but ultimately not too much noteworthy has happened. On the days my boss queen is around we do things together, and on the days she's working I put some effort into finding a job. Of course right now we're right in the middle of a 6 day weekend for her.

To start off not long after the first post she was dissatisfied in my job search and "revoked titty privileges" for about 4 days. That's been most of the sexual intimacy these last two weeks and I was certainly sad that had happened, but mostly because I had disappointed her. Of course there's plenty of other intimacy like cuddling and foot/back rubs (which I'm sure she wished I'd do more but she's also expecting me to just decide to do it on my own and unfortunately the thought isn't crossing my mind always).

After that she's been more satisfied with my search but I still haven't even gotten an interview. This week was thanksgiving so we had thanksgiving with her mom. Speaking of her mom apparently my boss queen informed her that I'm caged so that's fun. There were also a few days where I had to go without the cage due to a bit of irritation.

While my boss queen normally resorts to light scratches across my stomach and nipples to excite me as we've found they do that, she's been going a bit further the last few days. Going for my butt or my crotch. Grabbing my balls and even the uncaged dick through my underwear a few times. It's been exciting but I've got a little bit of an aversion to high sensitivity touches like that so my initial reaction has been trying to fight it before i can calm down a bit and enjoy it.

However I am back in the cage now. We bought some alcohol yesterday that we plan to enjoy during this 6 day weekend. Her mom was over a bit ago and she had no problem letting slip that she grabbed my balls to her. A weird kind of open relationship with her to me as I never talked about sexual anything with my parents ever. There's also a sale on some Bad Dragon toys this black friday weekend and we managed to get an extra large one that I plan to use on her. I can't wait for that.

 

The last post was in the middle of saturday, but that was a fun saturday. We did of course get a little drunk, and eventually ended up messing around. I was quickly informed that my fingernails were too long though. But I also deemed she was a little hairy for oral so we got out one of her toys. It's not as big as the one that's supposed to arrive today, but hey it's still some fun! I got to use that on her until she was satisfied and then we went to sleep.

Speaking of that extra large toy coming, it was something where the topic was initially I told her that I was thinking I really wanted to use a very large dildo in a strapon to feel a little power for brief moments even though I'm caged. She was excited by the idea too. She said "Since the toy is on the way, maybe you should look into strapon harnesses for it now." Honestly it's so big I fear I'll have to make my own but I guess we'll see. At least for now it can still be used without that!

As another bonus the sale continued with new things being added. We did another purchase from Bad Dragon with two bullet vibrators (one for her and one for me she said). And another toy, but this one smaller. This toy is for me, but it's notably bigger than anything I've gotten in before. But it's the one she wanted because it was the colors she liked. Of course she's not really into guy butt stuff so I explained to her "I'm not sure we'll ever get this in because this would have to be done on a regular basis so I could work my way up to it." Her solution was that all throughout January I can do butt stuff any time she isn't around (as normally i am disallowed as it's seen as a form of masturbation to her) and she will probably help get this big one in.

Sunday was an I dress up and be her maid day (as Sunday is the designated day for that). But all she really wanted was to relax and watch some TV most of the day. We did end up walking to the town park at night to see the Christmas setup, but the trolley wasn't running even though she'd seen that it would be and she really wanted to ride on it. We took a cab back and the driver said that they heard the trolley driver had quit this year and they never found a replacement so it won't be running. I also had to go back into my normal clothes for this trip, as my dressing up is "only for her." (or if her family just happens to come by which is a regular thing she doesn't mind if they see)

Monday was another mostly relaxing day. Although I got around to shaving her like I said I wanted to. Honestly I wasn't prepared for this since I personally haven't had to trim since the first time I did it 10 years ago and I didn't do a good job. We've bought a new trimmer and razor for next time which will hopefully go better. After that I got around to cutting my nails. "Not short enough," she said as I had to keep going back until it was like I had no fingernails. Most girls keep their fingernails longer than this!... Although maybe it's because since they themselves feel it they're much better at not scratching...

Come tuesday morning we started with a little messing around on waking up. With my non-existent fingernails and her much less hair the experience was going better, although she seemed a little unsatisfied. When I asked if I should get the toy she instead suggested that I get my whole hand into her like I had been trying (I honestly wasn't trying that). We worked towards it, and her ultimate goal was getting my fist in. Eventually I was able to get most of my hand in, but not shaped like a fist and she determined she was satisfied. Maybe some other day. Honestly my fist isn't that big and we might need to be able to fit it just to get that toy we bought in!

Yesterday was her first day back at work since Thanksgiving. Signalling the end of her 6 day weekend. I was also called for an interview on a position they wanted to fill that day, so I did that while she was at work. After she was home she had been distracted on her phone for awhile, so I joked "Are you sexting your friend?" and her reply was "I guess I should get on that huh." She also informed me that she'd sexted him before, and let me see that she brought it up to her friend. After that she went to other room and told me I wasn't allowed to read her conversation.

As a bit of background on this friend: He lives in England. She's known him for years, and early in this year visited him hoping for a relationship to sprout from that. It didn't, and after that she went out of her way to find people for a relationship which is how I met her.

A few hours later she let me see the conversation. She did in fact sext him for about 30 or so minutes. At the end of it he says "So are you two in an open relationship or am I becoming a home wrecker?"

She replies "No, we're in a monogamous relationship but he likes the idea of cuckolding."
I don't remember exactly what he said but it was along the lines of "Well if you ever want to try it out I'm open to it."
And her reply was "I have been wanting to go back to England again."

After reading all this I was feeling very excited. While in the past we've discussed this, as evidenced by her stating I like the idea of it, it's always come down to it seems unlikely it would happen. She would only do it with someone she has an emotional attachment to. And here it looks like an opportunity may have arisen. We'll see though. I later asked if I would be allowed to read the previous sexting conversations to which she replied "Maybe." I then asked if she'd continue sexting her friend, and the reply to that was "You don't get to know that!"

Now it's another morning where she's at work and I'm here alone. I called to ask about the job to find I didn't get it. The first directive is still unmet, so I guess it's time to go back to working on that.

 

That toy we ordered came! it is large. It is too large. I was too caught up in the moment and the excitement and not really understanding what the numbers meant. The head of it is much bigger than my fist! Accepting that though we do want to use it eventually, it'll be a long time, we'd like to sell it and get one that is smaller and more appealing to us anyways. In the interim since it'll be awhile before we use the one we got for me, we can use it on my boss queen. It's gotta be separated like that because she doesn't want anything that enters a butt to ever go into her vagina afterwards.

Starting on friday after mentioning I saw it in another journal my boss queen decided to have me write things every day. X thing 100 times, and with "pretty" handwriting. The first thing was "I will overcome." Yesterday's was "My Boss Queen Blesses me," and today's is "I will set reminders for myself." That last one because I forgot to call back a place yesterday.

With that second order though came the bullet vibes. Yesterday my boss queen decided to use one on me and while I'm not entirely sure whether she was just trying to edge me or go all the way (as the day before I explained that I was feeling very antsy for one after so long), I had my first orgasm since I've been here; of course with the cage still on. Afterwards she said "Well let's hope this doesn't change your attitude too much or you might not get this again!" Later in the night we decided to use the other one on her. I was in control of it and I had a hard time getting it to be enjoyable for her.

Eventually I asked if it was time for the promised masturbation session I get to watch. My boss queen said yes, and had me get her the toothbrush she got for this. Despite that she bought this just last week I found it already opened and modified for the purpose. I asked "Did you use this already?" and got the response "What did you think the door was closed for yesterday?" She demonstrated to me that it was much stronger than that bullet vibrator and got to work. I got to watch for about 8ish minutes after which she had me turn around and simply listen so she could look at porn while masturbating. Outside of special occasions I'm not allowed to look at porn and this was the reason I was given for not being allowed to look. Of course I still enjoyed listening. I think it would've been better if I hadn't orgasmed earlier in the day, and the cat hadn't come in to lie against me and be distracting but it was still good for me.

Today's another dressup day. I've been assigned my first maid task: clean the bathrooms every week. There's a few other things I could do, but I got something in my foot that we didn't manage to get out until today so my boss queen's been lenient about the fact that standing up is hard for me right now. Although I have promised her a back massage and foot massage with the massage oil today and I'm definitely gonna have to get around to those. Also as I was writing this journal she came over and saw it and went "I was gonna let you smack my ass but I see you're busy!"

As a final note my boss queen's been torturing me with tweezers. I've got lots of acne everywhere, and she's gotta pop them all. And while she's doing it she tells me it's gross. Of course it's gross..!

A job is still not acquired though.

 

I've fought back on the tweezing. It hurts, it leaves whatever itchy, and there's always as much to do every day so it's not like it's having the effect my boss queen keeps telling me it'll have. At the same time I guess it's one of few things she actually seems to take charge about so I'm still debating if I should be fighting back on it.

She's started intermittently playing with my nipples or even using a bullet vibrator on me while I'm playing videogames, which I do almost exclusively while on voicechat with my friends. She seems to enjoy teasing me in very small bursts and often while I'm doing something or we're out in public.

Speaking of that last one, she's now told one of her coworkers about the cage. Apparently she shared that I gave her a back massage and the coworker was all "ooh that's code," and she had to correct that coworker. And it wasn't just a "no, he just did it because he could," my boss queen had to go "no, he's caged," and show that coworker a picture of a chastity cage when it was questioned.

Was that back massage code? I thought about it a bit after I heard that and I don't really think it is. My boss queen loves footrubs and backrubs and for the most part I give them to her because I remember that. Unfortunately it's not always on my mind and she seems to just expect me to do it of my own volition instead of asking! So most of the time she complains about a pain and I'm like "oh yeah, I know how to fix that." I wish she would every now and then demand I do it because I kind of enjoy it when she acts like she's in charge.

As a final note: This morning there was a bit of fun times. I got my fist in her vagina, step 1 to getting a nice super large dildo in there. Unfortunately the one we got is too large to work towards from just that, so we're working on trading it for a smaller one (albeit still fairly big). but after doing that for a bit, we changed out to the dildo that will later be used for my butt and the bullet vibe for her. Went at that until my arm got tired and we cuddled in bed for another 2 hours before I got up to make her breakfast. Her ruling on the bullet vibe is it just doesn't seem to do much for her after she's been so spoiled with her toothbrush vibrators.

I got another interview, but still no job. Still applying to places. All I know for sure right now is that one place will probably be hiring in about a month, but also worrying I may be out of luck in the short term as I think the hiring time for seasonal is probably up and places are gonna be going down in employees in a few weeks.

 

I've found out that this bragging about me and sharing of the fact that I'm caged is apparently rather common...

She even showed me a conversation with one of her friends who was saying she wanted a guy to wear a cage, although it may have just been about the aesthetically interesting cage...

 

So typically I put my cold hands on my boss queen (mostly face/neck/back) because I'm cold and she's hot. At some point after a joke she went "oh now you aren't allowed!" but I wrestled with her and got my hands on her face. After that I was punished with a few days of no cage. Oh no. Eventually it was back on, but it was not to last.

A few days after it was back on I had a very nasty and painful pimple on my dick which necessitated the cage coming off. Expecting nothing to happen because no cage, I was proven wrong on Christmas Eve. My boss queen teased me a bunch. It was seriously just a little bit of brief touching, or a little nipple play, but eventually she edged me. After I said "I can't believe I didn't orgasm," she went right back into it. And this time she didn't stop until I did orgasm. Then she told me to clean up and go to sleep. I think it was more about amusement than horniness for her...

Anyways the cage remains off as the pimple has not healed completely yet. I miss it. However I've finally gotten a temp agency to tell me that there's a job lined up for me. Starting some time in january, it's actually at the same place my boss queen works. First directive met kind of?

 

A couple days ago I'd asked and gotten permission to look at all the porn I've been restricted from. "You can do it for 2 hours, but no touching and no making a mess." Unfortunately 10 minutes into it I saw something that particularly excited me and caused me to "make a mess." I definitely struggle to understand my limits. It just feels like I can go from just a little horny to too late to stop with nothing inbetween some days. The punishment for that was simply forfeiting the remainder of my 2 hours, as my boss queen is lenient.

Last night the cage was put back on. Earlier we had traded that way too big dildo for a still pretty big, but actually doable one and I was hoping for a chance to use it last night. But I was informed quite plainly nothing was gonna happen, while we were hanging out with my boss queen's mom of course. It was still a good night though.

Today we went over to hang out with her mom again. Playing yahtzee and card games. I took a break in the middle to make our dinner as I usually do. Of course at some point her mom wanted to fill her cup with soda and my boss queen had me get it for her. And the second I was going over to put the soda back in the fridge I got the message "You can totally put in your CM journal that I made you serve my mom!" which I think is code for her telling me to mention that. So I guess that happened.

So her mom knows I'm caged, that I do what my boss queen says, and maybe that I've never gotten to penetrate her with my penis. I believe she's implied that it doesn't happen, but not said it outright. Feels just a little embarrassing. Mostly weird that they're so open about it since I grew up in a house where there was absolutely zero mention of anything sexual until half a year ago when my mom found out I was visiting a girl and had to go "do I need to teach you how to use a condom?"

 

It's january, that means I get to put stuff in my butt while my boss queen is gone (something I haven't been allowed to do since before I came here because she's weirded out by it). Yesterday I got a little too into it and ended up orgasming because holy fuck I don't get how all you guys don't orgasm from whatever. Is it my cage, is it just not good enough at preventing that? That being said it's also the first time I've ever orgasmed from purely anal stimulation, something I could never achieve back in the days when I just masturbated every day. Exciting. Anyways my boss queen decided to have me write down this and any future transgressions of the month and will determine an amount of time the cage must be off next month based on that.

Today's also my birthday. A whole 27 years old. My boss queen told me that had it not been for yesterday she would've allowed me to cum today. But I'll have to try my best not to, since I'll be starting work on tuesday the 8th and thus have very few opportunities left where I'll be home alone in January to put dildos in my butt. I don't want to miss out on that.

As an added note my boss queen's suddenly demanding I address her as boss queen more frequently, including after every time I say thank you. Which I must say for a lot of things. Another thing is she's promised to make me a cake (a change from me doing all the cooking around here), and has agreed to my request for 27 candles. Whooo

As a quick edit due to stated misrepresentations: When I orgasmed this time I thought it might've been possible to stop in time and cool down but was very curious if it would actually happen given I've never done it from anal stimulation before. And the other is that my request for candles was more like "I want 27 candles. No I don't want a 2 and a 7, I want 27 candles and another candle every year." and that this was a demand.

I have left the original journal as was to show my mistake. And an added note that this too is going down on a notecard for next month.

 

Yesterday was my first day of orientation at my job, and today is gonna be the second day, then I get to work a whole bunch, with the shift after my boss queen so this is gonna take some adjustment. Besides that yesterday I ended up having an orgasm while doing butt stuff, which was of course unauthorized and thus goes on another notecard for punishment to be added up at the end of the month. This one I don't get though. I thought I had it figured out, but I went from soft to orgasm in 12 seconds. It was trying to force the knot on this dildo in, felt like I kind of forced out the orgasm, but I'd gotten the knot in many times before without doing so and it wasn't completely devoid of the orgasm feeling. It left me feeling upset all night though, so I guess arguably an improvement over past mistakes.

But also at some point throughout the night while talking about some other thread, my boss queen said "Dildos and the natural thing feel different." After questioning the differences she eventually told me that despite the advantages of a normal penis like its warmth and texture dildos could be up to 20x better. Then I of course asked "So you have no problem keeping me caged forever?" and she replied "Yep." She's also in the past told me that she doesn't really like blowjobs and she dislikes the taste of penises. I may be a virgin forever.

 

My job had a lot of physical labor that's taking time to adjust so I couldn't get around to doing that butt stuff I had free this month, leaving me with no outlet. Then of course I'm working the opposite shift of my boss queen so there's not a lot of time to spend together. After over a month of no sexual stuff together she ended up masturbating on her own, which will satisfy her for another month or so. This combined with other things made me feel resentment at being denied that chance and most other outlets.

I asked to end the chastity or at least remove the restrictions on what I can do, and my boss queen agreed. I definitely love her but I feel like this might be needed to avoid a situation where I feel resentment again. I guess we'll find out what the future holds.

 

Over the weekend Kitt decided to end the relationship. That means the adventures are definitely over and ultimately pretty short lived.

Ultimately I feel like I was put into an impossible situation and unfairly attacked over it. There were definitely problems but I was trying to fix them, but apparently trying to fix them was itself a problem. She also made little to no effort to get what she wanted because despite the short time being together I should've known what she wanted when she wanted and acted on it on my own and she had no responsibility for it.

But the most frustrating thing has to be that rather than address these issues and say they needed to be improved, her decision was to wait and see if they would get better with zero communication, then break up with me when they didn't. Then she got mad at me when I decided I didn't want to try reconciling it, which just makes me guess that for some reason that was what she hoped to get out of it. I'm not here to be abused and jerked around like that.

 

As it turns out, her wants towards sex were "none at all." I knew from the beginning she could be okay with that because she said it. However everything else she said up until she decided to break up with me did not hint at that being what she wanted or needed. She was the one who encouraged me to talk more about my interests. She told me to find a site for chastity and register here. She would suggest I update this journal. She got involved and excited at buying the new dildo after agreeing when I said it was something I wanted to do. On one thread here I saw someone mention that he went 54 days with zero sexual contact with his wife and told her I hoped she wouldn't do that with me because that's too long and she said "don't worry, that won't happen."

Turns out she waited until after breaking up with me to tell me that what she actually wanted was no sex. She was satisfied with vibrators on her own, and she wouldn't be interested in sex until that no longer was the case. She of course also told me in the past that she could also be satisfied with just toys forever, which at the time excited me because before that she also said "but if you're around i'd make you do it because why do it myself if you're there."

She kept telling me things that didn't line up with what she really wanted, then breaking up with me because I couldn't figure them out. Of course there was a lot of non sexual stuff too, though this is perhaps her absolute biggest communications failure.

 

I guess if you really want people here to know the whole story it might help to clarify that "enough money to stay in a hotel for a week and go to the doctor" is apparently an uninsured $300. Who knew.

You want people to realize how bad I was. You want to bring up that you got pissed off over a joke I had with a friend which spiraled into you kicking me out of the house the very next day because you are so stuck up on one specific word that you can't even understand that the context of it isn't serious despite that being exactly the same way it was used when you first asked me not to use it with you. Oh yeah and the fact that it was explicitly used outside of your presence but despite having broken up with me and wanting me gone you still felt the need to read my personal conversations.

I didn't get much housework done in that last week. I was sleeping 70% of every day, and trying to deal with the fact that I was in pain both physically and emotionally the rest of it. And I certainly didn't ignore you until the day you were kicking me out after I had packed everything and informed you what was gonna happen if you expected me out of the house. Which was you helping get me and my stuff to a hotel where it would actually be at least remotely practical to do so. At that point I was too drained and pissed off to deal with a conversation which would've been completely unproductive so I chose not to say anything. Which is how you were informed I dealt with my breakdowns.

As for emotionally manipulating I can guess that you mean when I said it made me feel a little rejected if I was of course, always rejected. I didn't intend for that to make you suddenly give in, I was simply airing how I felt. Something you apparently have had no problems doing since after breaking up with me, but were apparently completely incapable of doing so before then. At any rate I stopped trying to initiate after that because if I waited until you decided to do something then I wouldn't have to worry about it. The end result was you put me in a situation you promised wouldn't happen. I was upset. I wasn't going to let it ruin the relationship, I wanted to find a way I could deal with it. You didn't seem to feel the same.

I did want to quit the job. I did decide on that rather early. But it was never about the fact that I couldn't handle or didn't like the job. It was about the fact that the job was clearly putting a strain on our relationship. It was about the fact that I needed to quit so I could get back to spending time with you and giving you what you want so you wouldn't feel like you needed to break up with me. I started applying to different jobs, which I admittedly may not have mentioned but I felt like it was a given. Had I gotten another one fast enough it would've been nice, but the job had to go whether or not I did. Planning to have enough money to survive in case it took awhile to find a replacement job felt like the compromise that had to happen to make sure the relationship didn't fall apart.

It doesn't matter though. The second I got that job it was over. The job itself was always going to ruin the relationship. Quitting it no matter how I did it was always going to ruin the relationship. I got put into a position where the end result was the end of the relationship no matter what I did because there was a problem, and the solution was also apparently a problem. Making any complaints about the job was a problem because rather than relate or understand, you had to take it as "you make me feel like shit because you somehow think you don't deserve to deal with this but I also have a job and have to deal with this how could you think you're better than me." Which once again you never said anything about until informing me that we were breaking up.

And for my final failure I suppose I'll mention that I chose not to go to school paid for by my mom. This one really gets to me. This is literally what was going on with my life when we met and first talked. I told you that my mom had intended to pay for my schooling, and that given past experiences and knowledge of myself I believed it a bad decision and had no intention of wasting her money. But because she had to bring it up again while I was over there, it's like you suddenly forgot all that. You were too busy being jealous of the fact that I wasn't poor and shunned by my parents the same you were. Too busy being mad that you felt like I was choosing to not do something that you wanted for yourself but never had. You couldn't understand, and you certainly never tried to understand, simply choosing to cite it as a reason for why we had to breakup instead of ever talking about it.