Category Archive: Sissy maid stories

My Hot Sissy Maid Stories

sissy maid stories

My sissy maid stories are sensual and really naughty.  Billie was a man in his previous life. I mean he was born with a dick, “giggles” if you can call it that. He was drawn to my dominance and how I kept men begging at my feet. His tie and suit didn’t fool me one bit. For weeks I had pulled him in close and then gave him the cold shoulder. That’s the power of having a tight young body. When I was sure he was ripe I invited him up to my parents’ place for some hot roleplay fun.sissy maid training

I had him undressed and when I saw his tiny shriveled Penis, I couldn’t help but laugh. And now I had Made my Billie shy. He was so embarrassed his how body flushed pink. It was time for our sissy maid training! I put him in the frilliest and sluttiest maid outfit with all the frills that comes with it. And now it was time for him to serve me. I loved spanking his tight ass as I lifted his skirts! Any Mistakes were swiftly dealt with and his submissiveness made me so fucking wet.

Working a nice big black anal Plug up his ass, I had him kept in as he dusted the entire penthouse. My sissy maid would undress me with his sexy mouth and plant his face in my wet tight cunt until I was satisfied! Not To mention the cuckold shows I would give him with bull cocks sliding in and out of me!

I still remember the very first day that sissy maid Billie tasted another mans load out of my pussy. He wet his black lace panties! I knew then it was time to get him Cum directly from another man’s cock! Now where M sissy men at, Its time for you to be mine!

Making a Sissy Maid

Forced Feminization

I love when I get the chance to turn a man into just a little sissy who caters to my every whim. My newest plaything is just too adorable, we play dress up into the cutest little frilly dresses complete with stockings, panties and training bras! He said that he wanted to do anything to make me happy so today we are turning him into a little sissy maid for me to use! I found a cute and sexy little French maid outfit, short skirt and thigh high white stockings made him look perfect! I ordered him to draw me a nice hot bubble bath and he sat at the edge of the tub and washed my feet and legs, then my arms and back, since he was so good I let him wash my chest too. Then he carefully washed my hair, it felt so good to be catered upon! Since he did so good taking care of me that I even let him have some fun after I had dried off. I rubbed his little cock through the fabric of his panties until he came right in them!

They can watch

sexy chicks

Sexy chicks are always the freakiest ones. My friend and I had a double date. A little bit of alcohol makes us both horny sluts. My hot friend is a blonde bombshell. We both have a mutual attraction to each other. We weren’t feeling the guys much. We couldn’t keep our hands off each other. After dinner, we went back to my place. The guys assumed we were going to have some hot group sex together — no way in hell. I wanted my hot slutty friend, and she wanted me equally. We both got down and dirty and began to make out and scissor in front of our guys. We had no care in the world. I wanted to make her orgasm so bad. The guys kept trying to jump in, but we had it planned right. They could watch, but they can’t touch.

Sissy Maid Stories Are So Hot

sissy maid stories

Sissy Maid stories make my young pussy so hot. I love when I have a hot strong man come begging at my feet for some hot coed pussy. I told Mark that the only way he would be able to get my sweet pussy is if he put on his maid outfit and cleaned my Condo with 6 of my friends Present. ANd he had to keep his big black dildo clutched in his tight ass as he did so! I didn’t want a speck of dust left anywhere. My University Girls came over to drink wine which Mark had to tiptoe in his black heels not to spill one red wine drop on my white carpet. And to humiliate Mark and his small penis under his frilly maid outfit! All night he was serving us and the girls would take turns fondling his little package under his skirt, pinching and pulling that cute little boy dick that never belonged on a grown ass man. We were nice though and ordered some hot cock in the form of all-star football players to give us creampies so Mark the sissy Maid could lap us up like Icecream! 

Mature Phone Sex Women Like Big Dicks

mature phone sexMature phone sex fantasies are common. I get a lot of younger men calling me for milf fantasies. I excel at being that hot woman that offers release to younger men. Now, I am a cock size queen, so I don’t want my men too young. I’m in my forties, so those teen boys and college studs are perfect for me. They aren’t virgins, but they can still benefit from some tutelage to become a great lover. Men get personal satisfaction with two major things: providing financially for their women and families and providing sexually for their girls. Not every young stud I fuck can satisfy a woman with his dick, so I coach them on how to be a good cuckold. It is better to hear that you have a shrimp dick when you are younger. Carl is a handsome college boy. Smart and cute, but he was cursed with a 4-inch dick. That is not going to give a woman pleasure. It certainly wouldn’t please me. He was hoping to be the teacher’s pet, but he became the teacher’s sissy instead. I dressed him up in a sissy maid outfit and gave him tasks from cleaning my office to worshiping my ass. He did well with his tasks. He was just happy to be in the presence of a sexy babe. I was happy to have a new sissy assistant. Some men transition easily into sissies, some give quite a fight. Carl is a natural sissy and I am lucky to have a new sissy slave who doesn’t need a lot of training to except his position in my world.

Sissy Face Sitting

Femdom phone sex

I love having my pussy eaten by a submissive man. Especially when I’ve got a hot load of cum inside me from one of my BBC bulls. I like to sit on his face and take control. Having my pussy licked makes me cum so fast, but face sitting makes me feel powerful and dominant, like the sexy femdom Queen that I am. I want you to lay on the floor while I stand above you and then squat onto your face and put my pussy and ass right on your mouth. I’m in control of the situation now, and you can’t stand up until you’ve made me cum and let me squirt all over your face. Maybe if you’re lucky I’ll let you stroke your tiny cock while you lick my pussy and asshole. If you’re a really good little pussy pleaser for me, I’ll even fuck you with my strap on and jerk your cock from behind while I do it.

Naughty Maid Phone Sex For Cucky Hub

I’ve this cucky husband that just cannot help but watch me take different cocks and the best part about this is getting into the kinky roleplays we love and Naughty Maid Phone Sex is a real fun one. I love to twist things a little up and make it more exciting. This recent little idea of me dressing up as a naughty seductress maid type thing for a couple of male friends and my hubby would be in the sidelines watching us from a corner. Well we were getting pretty hot with me sucking off two cocks and having my breasts played with while the third guy fucked my pussy while i sat on my hubbys face. It came clear to the guys quickly that he needed to be servicing their cocks while all three of them fucked me. Dennis quickly became the maid of the night and he was quite the little slut with this sissy maid training. He was getting dressed up in the frilly panties I just took off that were covering a sopping wet cunt. We also dressed the little slut up in the frilly pink apron and I even let her wear my garter belt and stockings.

If it’s phone sex therapy sessions that are in the lines of being a Sissy or a cuckold we could have some hot fun together. I haven’t any taboos and the idea of being limited in how we play is obscene! The more obscene your fantasy is the more fun we can have with it I am certain. Our roleplay going from cuckolding his wife to being sissified and made a whore to big dick is a nice twist in the usual cuckold call, and I welcome that. If you wish for a very specific fantasy you are welcome to email me the details and set up that call with me so we can have some sexy fun.

Naughty maid phone sex

Naughty maid phone sex whore

Naughty maid phone sexSissy Boy called me up for some naughty maid phone sex. He has been such a dirty sissy cuckaholic and needs his whole entire house cleaned from top to bottom from all of his sexual antics. A bunch of his big black dick friends came over to play with his sissy pee pee all night last night and clearly they have made a huge ass mess that needs to be tended to. He’s such a horny sissy, his little cock is constantly twitching just dying to be played with! He called me up and begged me to come and help him clean up the mess. Of course I showed up all dressed up in my sexiest maid outfit. My tits were pushed up and looking phenomenal as usual. My ass was nice and big & juicy, when I bend over you have the perfect view of my slutty fuck holes. Even though i’m there to help Sissy Boy clean, I am also there to totally humiliate him and make fun of all the filthy, nasty things that i’m gonna make him do! I’m looking like a total fuckin goddess as I strut around in my sexy high heels. I drive Sissy Boy crazy. He has never been this close to a real life princess before. I may be a maid but I still own him and his pathetic little pee pee. In fact, I think i’m gonna invite those big black cocks back over to his house because I want to create a little bit more of a mess and have a little more fun with him before I get down & dirty and scrub his place clean. Sissy Boy is all dressed up in his prettiest lingerie and looks like a total little whore. I shove his panties to the side and plunge one of those huge anaconda cocks inside of his asshole while another goes into his mouth. He has one in each hand while he strokes them hard. I have to whip out my phone and take pictures so that I can always remember how fucked up Sissy Boy is, lol! Sissy maid stories sure are fun to tell and talk about, especially with this special Sissy Boy!

Sharing My Pet

Sissy maid training

First off, if you do not know Nicolette then allow me to introduce you to her.  She is one of the kinkiest friends that I have.  A few years ago I helped her with one of her sons.  Since that time her and I have become fast friends.  She is super hot.  I mean, look at her.  Her tits are simply amazing. Now onto the story part of this blog:

Nicolette was spending a couple days with me so we could catch up on things since it had been ages since we had spent any real time together.  Our conversation turned to sex.  For some reason it always does when the both of us are speaking together.  I told her about how I can afford to now pay people to have sex for me while I watch.  How I have a new play thing who was at his Parent’s home for the Holidays, and that I started learning about BDSM.  When I mentioned that she perked up quite a bit.

She asked me if I could get a hold of my pet who I play with now and then.  I told her I could most certainly try.  I texted him and being the good pet he is, he texted right back even though he was out for dinner with his wife.  I told him that I really didn’t care that he was there with her, I wanted him here, now!  He sent back a short reply of, ‘Yes Ma’am.” Then we waited.

Forced feminizationWhile we waited we went up to my closet to pick out some appropriate apparel for our fun.  The doorbell rang and I went to answer it.  He was there, kneeling by the door to request permission to enter.  I told him not yet and yelled for Nicolette to come down.  She came to the door and laughed.  I told him he could come in, he looked confused.  He wasn’t used to having anyone with us when we played.  I introduced them and we were on our way.

We made him put on a pair of panties all while informing him of what the night would hold for him.  He didn’t like wearing the panties, but tonight he was our little Sissy and he would be trained to be our Sissy Maid.  He stood there in those panties, it was almost comical, he was truly embarrassed.  Nicolette suggested that he be punished for not liking what his Domme had given him to wear.  I told her where the gear was and she brought out everything.  Her and I decided on the canes.  He bent over while her and I took turns reddening his Sissy ass.  With each swat he had to apologize.

We then moved onto some strap-on play.  I have to say, Nicolette was a beast with that thing.  I have never in my life seen someone get fucked so hard.  She was thrusting into him so hard that I thought for sure he would go shooting out the window onto my front lawn.  She then made him clean off that which had been so violently rammed into his ass.  I went behind him and continued to widen out his Sissy pussy.  By the time we were done he was in tears from the humiliation, and Nicolette and I were enjoying seeing those hot tears running down his cheeks as he thanked us both for the lesson.

Sissy humiliation

 

Sissy Maid Stories With Clarissa and I

 

sissy maid storiesSissy Maid Stories are so fucking pussy wetting! Clarissa is The best Mistress Trainer around. She holds my pussy to the highest standards. When I came for my session Clarissa Had her best sissy Nathan in a maids uniform that was so short you could see his little dick in its cock cage. My, My, was it straining and bulging out everywhere like playdough. I asked her where she got such a tiny cage to make his 3 inches sweet and bulging like that. Turns out Clarissa makes her own because she has had so many needle dicks and the industry can’t keep up with the shrinking cock department of humiliation. Clarissa was so sexy it made my Bisexual teen pussy ache so bad, I knew I shouldn’t dare but I came up behind her and reached around and grabbed her gorgeous tits. Clarissa grabbed my hand commanded me to my knees. ” A Good Mistress must always start as a sub and I will teach you to be my submissive bitch!” She pulled her panties to the side and made me lick and slurp that cunt and had her Sissy Maid Nathan bring her a glass of Merlot and Ky Lube. “Ass in the air slut!”  She was drinking her wine as She made Nathan Sissy bitch boy with the tiny cocklett bring her a huge black butt plug. : This Time I will Lube it, Learn your place or I will make you pay C.J.” My ass was reamed over and over until I was breathless. My pussy came on her command. I know we are some sexy hot women and I love being trained to be a good Mistress By Clarissa! We need sissy boys, come to play with us!

sexy hot women

Older posts «

Chat with Sissy-maid-stories
X

Please enter your name

Send a message to start conversation with Sissy-maid-stories
Send