Meeting Sissy Maid

By Kendra Holliday | August 29, 2012

Sissy Maid in action

A close girlfriend of mine asked me if I would come over to her house one night and have cocktails with her while a man cleaned her house wearing a decked out French maid costume, right down to the high heels.

Of course I said yes.


I have to say that as fun as that fantasy sounds, the reality never matches up.

That’s because submissive men have a terrible track record with me.

I’ve dealt with many of them, and they CLAIM to be all about serving and worshiping women, but they act as though they’re more into serving and worshiping their dick.

They lack respect and don’t follow protocol. For instance:

They text you and ask if you’re available RIGHT NOW.

They arrive late.

They take liberties.

They impatiently and eagerly email you ten times in ten minutes.

They don’t do a good job cleaning.

They don’t follow instructions.

They make demands.

They don’t tribute you properly.

They say they want to be trained, but don’t ever manage to catch on to your way of doing things.

They say they want to serve you, but when you state your expectations, they counter with their own terms.

Um, excuse me?

They act like bratty little bitches, and it’s annoying as fuck.

I’ll hardly interact with a sub guy even on a paid basis at this point. They waste my time, and my time is extremely valuable. I am not a mere Mistress. I am a QUEEN. I am a GODDESS. Get with the program, assholes!

OK, I’m done ranting. I went into this situation skeptical, but the fact that my girlfriend has very good taste was encouraging.

It turns out she introduced me to one of the best sissy boys in the world!

She instructed him to arrive at 6:45 pm, not a moment before or after. He pulled up and parked at 6:43, and we were pleased to see him sit anxiously in the car until the right time.

When he walked in, he was wearing a black t-shirt, jeans, and boots. He was tall, muscular, and handsome. I was thrilled!

Here is how he describes his schtick:

“I dress in a french maid uniform and heels and clean your whole house. dishes, laundry, floors, bathroom etc. all in turn for you laughing at me and say humiliating things every once in a while during the process. yes im serious and yes im a kinky bastard. cleaning is all i want to do, then i pack up n go home. NO GUYS PRESENT PLEASE, IT MAKES ME NERVY. Of course make sure its ok with boyfriends and husbands and family pets first.”

We were about to put him to the test!

He shyly went upstairs to change into his costume. She and I were wearing matching polka dot dresses.

When he came back down, I was blown away by how tall Sissy Maid was in those heels! His costume was very elaborate – in addition to the French maid uniform, he wore jewelry, mascara, sheer stockings held up by a satiny pink garter belt, a pink polka dot petticoat, and frilly panties. He looked so ridiculous!

First, we had him pour us St. Germain cocktails. Then, she and I sat in the kitchen as he started cleaning. She had supplies laid out for him. As you can see from the photos, he didn’t need a step stool to clean the ceiling fan!

Do a good job, Sissy Maid. We’re watching you!

She did the white glove test on the fan. It was spotless!

I ordered him to kick up one heel for this shot:

Aw, he’s so pretty!

Her husband had written mocking taunts directed at Sissy Maid on the stovetop and microwave with bathtub crayons. He scrubbed those appliances until they shined!

Wipe it clean, Sissy Maid!

Just look at his cute panties!

I see London, I see France!

He even got down on his knees and wiped the baseboards.

That’s right – you belong on your knees!

He respectfully asked us if we would take some pics of him for his girlfriend (a vivacious burlesque performer) as well as another woman whose house he cleans. She likes when he sends her pics of him working on other houses.

Usually Sissy Maid is quiet and servile as he does his duties, but we couldn’t help ourselves. The three of us had instant chemistry and got along famously! We ended up chatting our heads off about all kinds of kinky things! He had a stellar personality.

He confessed to us that he had a cuckolding relationship with his girlfriend. “I haven’t had sex with her in two years!” he announced proudly. In fact, while he was cleaning away, she had a man over right now, which excited him tremendously. He said the guy was a good friend of theirs and had been tested, so they could incorporate some nasty cumplay in their activities. He said primly, “Sometimes, I get a gift.”

“You mean a CREAMPIE!” I crowed.

He blushed and said, “I love you! You guys are so great!”

“So are you gonna do that tonight?”

“I sure hope so!” he exclaimed, his hand flying up to his chest.

“Do you think she’ll get two loads out of him?” I wondered.

He squirmed with prickly pleasure.

At one point, he received a text from a woman. He asked to excuse himself for a moment and went to the bathroom. When he came out, he confessed, “My friend is having her period. She wants us on the same cycle, so every time she changes her tampon, she makes me follow suit.”

“You mean you’re wearing a tampon!”

He nodded bashfully.

“Did you use lube to get it in?!”

“No, just a little spit.”

So now he was cleaning while plugged! This was great!

We had SUCH a nice time that we’ve scheduled a private Sissy Maid tea party for next month and have invited a few of our girlfriends to enjoy the Sissy Maid experience.

PS: I asked Sissy Maid about what happened when he got home from his cleaning gig. This is what he told me!

“I came home and turned off the light to the computer room signaling to my girlfriend i was home. The computer room is right outside to bedroom door. I listened for a few minutes and didn’t hear much, but after a bit i could hear her moaning. The slight slap of him fucking her became audible there after. It became louder and louder and i heard her say “Fuck! your dick feels so good its so much bigger than his.” I had to keep myself from from masturbating at this point…i knew id cum to fast so I just listened, slowly rubbing myself through my panties as I stood there in my maid’s uniform. She told him to tell her when he was about to cum and the fuck noises became louder and louder there after. She began to yell and say FUCK FUCK FUCK over and over again. Then i heard him grunt and i knew he had came in her. I walked downstairs and waited on the couch. I heard her open the door and saw her walking down the stairs wearing red platform heels and nothing else.
She walked over to me and told me to take out my little dick and smell what a real man smells like. So i put my face down by her pussy and drew in long hard breaths. i could immediately smell his cum. She told me to jerk off and lick it clean. So I laid down on the couch and she faced away from me and sat on my face rubbing back and forth and around in circles. Then i felt her loosen up and let his cum run out into my mouth. I came right then and swallowed it all. She got up and told me to stay right there because she’d be back with more. About 45 mins later she came back down and began to kiss me….passing more of his cum from her mouth to mine. I started jerking my little dick again, she walked away laughing. PERFECT!”

In this case, it turns out the reality was hotter than the fantasy!

TO ALL YOU SISSY BOYS OUT THERE WHO WANT TO EXPERIENCE SOMETHING LIKE THIS: Unless you pay for it, you can’t just dial it in. You have to bring something to the table and honestly respect women. You have to earn your place in the community. You have to prove your merit. You need to do a good job and have a good reputation. So get out there and start attending events and meeting like-minded people. Make friends with people who enjoy your company and are happy to oblige your fantasies. Developing relationships and scenarios takes time and effort, but it’s SOO worth it!


Capn Marrrrk 2012-08-29 07:51:03

What a great story! I was thinking about Sissy yesterday after he posted a text conversation on FB. I saw him at a party Saturday night dressed up and serving ALL the women at the party, like simultaneously. He was fetching drinks, rubbing feet, cleaning shit up. He was in motion! What I was thinking was: “Man, how lucky he is that he’s surrounded by women who Love AND Respect him. They order him around, they call him names, but it’s good natured, it’s not mean. These women are EMPOWERED! It’s really something to behold. And you know what makes it work? Sissy is a really nice guy and not a creep. He also exudes both a genuine desire to do a good job and serve. Period. (Pun not intended, but there it is). It’s great to get to meet him, and learn more about who he is beyond just the frilly skirt. So he likes Cuckolding and Creampies…BFD. He’s an awesome dude for letting you tell his story.


Gary LaBrot 2012-08-29 14:20:22

You made me tear up! What an amazing turn to have found Alessandra, Mark and Kendra! Thank you for the compliments you’ve given me and for giving me a chance! I truly don’t know what to say! The article made me giddy! The very first things I mention when telling my cleaning experience is how divine Alessandra and Kendra looked. Dressed classy and wearing white gloves! As soon as I saw the gloves I knew what I was In for! YES! And then of course the the messages left by Mark written in crayon soap! Thanks for making things very special. Mark also commented on the wonderful women I’m surrounded by. I could never express how much I love and appreciate them! And remember Mark, the husbands and boyfriends who trust and understand me are a crucial part of everything! Thank you my friend! *bright eyed sigh with a big smile* Sincerely,Sissy Maid.


Kathi 2012-08-29 17:47:25

I’m a good friend of Sissy Maids. We have been friends for about 8 years now. Long ago I had him behave as a slave/servant at a all girls PJ Party. He was the best! He came in a nighty and heals with frilly undies as I asked him to. He did everything the ladies desired, made drinks, walked the trash out to the dumpster, reapplied make-up to one of the guest, gave full body massage to me. He did not speak unless spoken to, he did not sit unless he was told to, and he was an overall amazing servant! We all had a great time with him serving us. Many of our guy friends wanted in on these girl night (they wanted to serve too) but after Sissy Maid I knew no one could do it better than him!!! I have heard many stories of his and nothing phases me. Learning the new information through your blog just made me love him even more!!! He is one of the best people I know!!!


    Gary LaBrot 2012-08-29 18:33:04



Danimal 2012-08-29 20:08:18

I’ve said it before, and I’ll say it again. Gary is my hero. Great job Sissy, way to do us all proud! I can only hope to be as awesome as you one day. ๐Ÿ™‚


Bianca 2012-08-29 21:48:16

As usual Kendra, what a great article. It describes Sissy really well. I would write more here, but i’m still pretty buzzed from pain killers. You guys are great!


davidwraith 2012-08-30 02:48:17

Wow! What a great post!

Since I suggested Sissy Maid to your girlfriend weeks ago (as a replacement for that other servant who didn’t work out), I’m going to go ahead and take credit for this. ๐Ÿ™‚

This post made me really nostalgic. I miss being a service sub, but I’d probably have a better chance of hitting the lottery than finding a Dom that I click with who would put up with my schedule.


    Kendra Holliday 2012-08-30 12:19:40

    Thank you for doing your part in bringing kinky kindred spirits together!


      Gary LaBrot 2012-08-31 01:11:20

      Yes! THANK YOU DAVID!!!!


    Loney 2019-09-24 17:14:00

    I looking for a mistress to keep me for sissy maid 24/7 and make me do all thing she told me to do and she rent out to man andwomanto do housework and fun to do


The Nerd 2012-08-30 11:55:18

Wow, what a fantastic story! I’m glad these people get to live their fantasies.


Servant 2012-09-03 15:17:23

What an awesome story from the beginning to the end. Especially the last paragraph. It takes time to find the right Queen to honor you and do these things for you, but once you have one they need to be treated with the honor they deserve because they are precious.


Loney 2012-12-22 13:00:28

i looking for a MISTRESS and MASTER to keep me as a sissy male maid and they can have fun with me and they can tie me up ti and rent me iout


gdm 2013-01-13 08:16:01

yes my gf did that to i was hire out as a sissy maid to all her male and female friends to clean house one lady told me you are here for one thing i ask he what was that to be my bitch since i sell lingre i need you to try on some panties bras dresses well i did as told i was put into many thing once we were done now bitchi what you to wear this it was a pink lace push up bra with matching pantiesthen came a short black dress and a white see thought blouse that show my bra now when you come to work you will wear that but your breast need to grow so here that these pills it help make them grow well i did it toke thre month and i had breast my gf told me yes i love your tits she turn you into a sissy girl well soon i was back at her place the lady open my blouse and said your tits are nice how do you like them i told her i love my tits and i what men to see them do you feel like a girl itold he a bit but i want to feel more girlshe ask me how i told her i want a man to suck my tits and make me his bitch she told me yes just then she ripe my bra off and suck my breast i soon was geting hot then she said are you my bitch and do anything i ask i told her yes i your slave and bitch for you and friend


robert hathaway 2013-01-14 11:00:30

im a male maid and stay at home in a french maids out fit and high heels and do all the house work whille my wife go to work and i love it


Renee Wilson 2013-01-26 22:33:58

Ms Holliday, enjoyed the article but I’m not like those wannabes you describe. I would love to prove it to you. Live in Kansas but can travel and would relocate for hr right situation. Maid Renee


    Kendra Holliday 2013-01-27 12:41:48

    Ooh sissy cat fight! Rrrow!


    Gary LaBrot 2013-01-27 16:09:38

    (tongue in cheek) I’m not sure if you are including me as a wannabe Renne. But, if so It sounds like someone WANTSTABE in my position. So that makes you the wannabe. If you were as good as you claim you’d have your own goddesses to serve, and you wouldn’t WANNABE sticking your high heel in my door. CAT FIGHT!


      Matthew 2013-01-28 23:31:29

      Hahahahahaha!!! GETSOME!!!


Latex sissy maid 2013-02-10 15:01:15

Very nice story!


    Latex sissy maid 2013-02-10 15:20:12



maidsylvie 2013-03-21 17:19:33

I am sorry for your bad experiences however not all of us are this way . I get praise wherever I go for my respectful attitude and level of servitude . Of course sissy has needs but to me he Woman is always first


Mistress Lilyana 2013-04-18 14:09:04

If there were more guys like this in the scene, male subs wouldn’t have such a bad reputation for being flakes and fakes. Thanks for sharing!


Bear Knotright 2013-04-18 16:11:59

I have only known of sissy for a few years and it’s been nothing more then a polite Hi as we passed each other, but reading this gives me a much greater respect for him. Sounds as if he is on the path a very dear friend,that sadly I have lost touch with, has blazed. A tip of the hat to you sissy may you enjoy your journey that has chosen you in this life.


Danni 2014-03-10 15:47:32

I was lucky my found me and recognized I was a sissy who just needed a woman to ssrve. I have never been happier.


wild-rose 2014-07-03 23:26:25

This is an amazing post. It seriously warmed my heart! So nice to know that there are kindred spirits, and open minded people out there ๐Ÿ™‚


Butch 2017-08-09 14:09:48

I looking keep me as they female maid 24/7and make door all things they told me to do and keep me tie tp


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