It was a dark and stormy night. Or was it? I cannot recall it honestly.

Anyway, a voice said to me, "Dee? Sweetie Pie? Shouldn't you enslave the men of this world into the divine pleasures of femininity?"

That was awhile ago, and sure enough, it began to happen .. on Rachel's Haven. Then I started up this crappy blog in 2010. Enjoy!

Monday, May 14, 2012

The Position Has Been Filled!

Well, I ended up with many more replies than I thought I would get for the position of "Sissy Maid" especially since it started out slow with no replies the first night. Then I guess word got out, and people were mincing over here as fast as they could on their stiletto heels.

I decided that I should take them in order, since that was probably the fairest way to go. I will try to get one out to everyone, though it might take a bit of time to do so.

This one up above is for Chaosbeast, and completes the story I had in mind when I was looking for someone to be my subject. It touches a few points that I enjoy working into captions and I hope that I was able to steam some panties. I know there isn't much in the way of words BUT I hope that I have portrayed a vivid story, condensed into a pivotal moment in time.

This one was written about an hour ago. I did a Google image search for "sissy maid" and this picture set was one of the first to come up. I saw the pair of maids, and the idea pretty much formed right then and there. This photo worked the best, as I was able to clone tool out the model credits (Jessica Maid and Sweet Maid if you wish to know the models) and just imbed the speech right onto the picture.

This one was a tad bit harder to create because I don't know either of the people that replied. I guess that is one reason why 98 percent of my captions are made as trades .. its easier to craft something when you know what the recipient likes. I took a broad view of the situation, and made a decision that though they are usually on the same level as submissive sissy maids, that one would get to be the "honored" sissy and the other would be on the receiving end. I read both people's applications, and Jelena had "slut" in hers, she should be the ultimate sissy that night. If both Allison and Jelena would prefer to swap spots, I have no issue with reversing their roles.

I have quite a few people left to make captions for. As I mentioned above, I am going to do them in  some semblence of order in which I received them. If all goes well, I hope to do one per week. You might get a solo caption, or it might be a buddy caption. It all depends on what I find for source material and the ideas I get out of the photos.

DISCUSSION QUESTION: What things do you like to see in a Sissy Maid caption? Any scenario you haven't seen enough, or that keep you blushing in agony? Figured I'd ask since any ideas that come in the comments could influence what I write in the coming captions. Anything you can't stand to see? For those who haven't received a caption yet .. what floats your boat in Sissy Maid captions?

Since these won't be posted to the Haven, I would like to see comments on the actual caption as well. Feedback, especially from the recipients, would be much appreciated.


  1. Thank you so much Dee! It's such a tittilating caption. You've certainly communicated a lot while actually saying very little.

    What do I enjoy in sissy maid caps? Well, there is the whole sissy aspect of course. The wonderful contradiction with a man acting as feminine as possible. Then there's the maid portion. I truly do love to help people and thoughts of subservience really get me going, so I'm naturally drawn to maidhood. Plus maid outfits are always so cute and sexy.

    1. I'm so glad you really liked it. As one of the people that comments here most often, I was nervous with anticipation as to whether you'd be happy with it. I figured you would drool over the picture and I wanted to make a story that could match up with it and do it justice.

  2. Thank you for including me in one of your captions I always saw myself as more of a bimbo more then anything just the thought of becoming a blonde with big tits and shaking my tight ass always makes me so happy plus they always wear the cutest outfits and again thank you for including me

    1. Glad you liked it .. perhaps you have a full head of blonde hair pinned up underneath the wig. I wouldn't want you distracting the various other servants .. at least not while they are on duty!

  3. Very sexy caps Dee. The image used in Kyra's is hauntingly beautiful, and the story you wrote around it is the perfect piece of the tale (or maybe its just that Kyra is the perfect piece of tail!).

    Allison and Jelena's cap is very sexy too. I like the thought of the sissy maid's competing and getting to use the other if they 'win'.

    I think the thing I like to see the most in a sissy maid caption is the subservience. The loss of station. Really there doesn't seem to be any position lower than being made over into the maid. It's very similar to the 'secretary' position in an office. I also really like seeing the mixing of their duties. Dusting, Vacuuming, sucking, fucking. All the while though, they aren't the 'main attraction'. They are readying their women or men for someone else to enjoy.

    1. Your reply gave me a bit of an idea that I might use when making the next batch of sissy maid captions.

      I tend to like the first one a bit better because its more vague. You don't really know how serious the CEO's daughter is in her threats. Is it a playful tease, or a serious admonishment?

  4. May have gone mad with my response, sorry!

    tl;dr version: Love your captions, both of them for different reasons. Sissy maids are pretty and don't have to think much. Sex is less important than bondage.

    Now, the full horror:

    I always enjoy your work and particularly the fact that you remain very 'real' with things - literal too. The first one is a good example of the 'real' coupled with a very nice image. It fits, and the comments by the speaker are open ended enough to be harsh or with a hint of playfulness - given the eyes in the image we can assume the playful nature of them. And I like that ambiguity.

    Second cap is a good use of the image. Don't take this the wrong way, you can tell it was not as planned as the first. Still a really good caption and still bearing your hallmarks of quality but not the same as your first one. Does that make it less good? No. It makes it different, and I like different. I prefer your first, but that's because of the situation and the plot rather than the planned or unplanned nature of it.

    What is it about sissy maid captions for me? Given your laser-like perception of language and your ability to deliver exactly what people ask for, I fear my answer will be analysed well - I'll have to be careful! ;)

    Part of it is the submissiveness of the role. The fact that a maid carries out the orders of other people, a specific set of tasks in a given time frame and these must be completed to a given standard. There's no proactivity expected on the part of the maid and failure to complete any of the above will result in correction - that fear of direct punishment is certainly part of it. Also, there's a certain liberation in all of it - an abdication of personal responsibility and a trust in the whim of someone else. In my mind the person in charge is a mistress, something about societal expectations of female and male domains I suppose, rather than a master. I never really see the maid position as being a sexual one but a domestic one.

    Part of my attraction to the role is based on the fact that there's no real male equivalent - I mean, there were squires of old but that has sort of died out and in more modern times, within my own living memory, such positions of domestic servitude were female. Granted, there were butlers, but these were more public positions. They were also more 'batman' like (in the sense of being like the First World War rather than the superhero) in that they tended toward dressing and drinks. Also advice. Like a sergeant in the military to a Lieutenant - one was experienced but knew his place the other was superior but, if he was worth anything, would listen to the sergeant. A maid, now, did not have experience and was not expected to advise. It is that to which I am attracted, I suppose.

    What do I like about the sissy maid in particular? I like the bondage aspect of it - the feeling of being powerless and trapped and subject to the whim of a superior. The subject, that would be the operative part of it. I also just like the clothing associated with the role in the popular imagination - it tends to create nice co-ordination and imagery, it's pretty without being ostentatious; chaste without being prudish and constricting without being restrictive. With no male equivalent a sissy is the only way a male can fulfil the role.

    Okay, sorry, mammoth post.

    1. Oh sweetie .. don't EVER be sorry to write multiple paragraphs here. I LOVE when the comments get specific and wordy. Feedback is essential, and the fact that this is a blog exclusive .. this is the only place I'll be able to find out what people think of it.

      Plus, I haven't done many sissy captions in the past, so I need to figure out ways to make them better .. especially since in general, I've always looked at sexuality from a dominant standpoint. The submissive part intrigues me, and as mentioned in previous posts, the idea of not being in control can be liberating.

      "laser-like perception of language" - THANK YOU! I've always been a "lets get to the main point!" type of person, but over time I've learned to play around with words, especially when you are trying to generate a report that looks hearty but essentially says nothing. The hard part is striking a balance between the two, where you can be flowery with your words but still be direct. I think that since I was always the lyricist in the bands I've been in, it really helped when I started making captions. You truly have to boil down the story into a small amount of verbiage AND convey the story or ideas you want to project in a tidy amount of syllables.

      "I always enjoy your work and particularly the fact that you remain very 'real' with things," I have sort of touched upon that in a previous post, but its something I strive for, even though I'm known more for "magical" captions than the ones I uploaded in this blog post. Mostly, I want it to feel real, even if the means of transformation is hard to believe .. I want the people to act like they would IF that magic WAS real.

      Your answers to the whole "Sissy Maid" questions does help me out, and with the other postings, gives me some ideas and thoughts to ponder for when I make some more over the next couple weeks!