By Kendra Holliday | August 29, 2012
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!
She did the white glove test on the fan. It was spotless!
I ordered him to kick up one heel for this shot:
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!
Just look at his cute panties!
He even got down on his knees and wiped the baseboards.
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!