Tag: Sissy Maid Stories

Sissy Maid stories to live by

sissy maid stories The bubbles lapped my skin as the water swooshed back and forth. I had been reading some new sissy maid stories and was lost in the thought of my newest sissy. My body was alive at the thought of my sissy Sucking the UPS driver’s cock as a tip. We had been making good progress, and the outfits He bought to dress up in had become more sissified every weekend. He had taken my strap once and had taken three weeks to come back and see me. I was sure that would be the last session we had. But this morning I received a sissy novel on my doorstep and A bottle of wine and a Bath set. We had a “date” soon, and I was crafting a plan to keep him in my care for a long time.
I had fired my part time housekeeper and the house looked like a single busy business woman, lived alone. I stepped over discarded hose and panties, over towels and lotion bottles; giggling to myself. I had added to the mess with Hiding sissies butt plug under a pile of jackets and leaving a note beside it. Sissy was going to clean my house and sissy was going to either Present herself fully, or find another Mistress, My boots and black leather outfit With the crotch cut out would set the scene. It was Sissie’s favorite outfit. A leather loving sissy who would orgasm if he was allowed to click my boots too long.
The note read: Things you need, Your butt plug. (lube or no lube) The shopping bag in the closet behind My favorite Boots and Paddles.
If you wish to submit fully to me, and give me control to lead you into true sissydom, You know what to do. If you wish to end your contract you may gather your things and walk out the back door to hide your shame, No refunds on my Mistress tributes.

It took him 15 minutes. I waited dressed with my legs propped up on the couch. Sissy came crawling with her ass in the air, one pair of panties on and a pink leather paddle in his mouth. Sissy whined at my feet like a good puppy sissy.

We would begin his sissy maid training fresh. I had new ideas from his book.

Sissy Maid Training With Goddess Gwen

 

Sissy Maid Training

Sweet man did you not realize you needed my sissy maid training. You came to me for a little sissy play. You have been a cuck for your wife for a couple of years now. But the more you look at those big dicks going in and out of her sweet whore holes, the more you begin to want that cock in your mouth! It is now your realize that you need something more. One day you looked in the mirror and saw that clit sticking up to the sky. You were thinking about her, taking that dick in her pussy and you daydreamed that you were her in pretty lace and ruffles. You had your skirt flipped up and was taking the dick in your “womb” and ass hole. It was just a dream, you had been reading too many erotic sissy maid stories lately and you had envisioned being a slut in frills and pearls. 

This is where your Goddess Gwen Comes in. Offering to make you into the extract thing you want to be. I French Maid sissy slut!

sissy maid stories

You arrive at my place and I am in the sexiest maid outfit with my feather duster in my hand. I promptly hand it to you in exchange for the tribute you have for your mistress. A big fat wad of cash! If you need to be a full on sissy whore, you need to pay up piggy! We start with full exfoliation and hair removal. Your sissy maid outfit is read for you. Dressing you up in soft feminine colors and tights and even heels. The sexiest thing is your panties and bra under your ruffled skirts. I have a few girlfriends who know how to treat a sweet dumb whore like you. My pussy gets licked in front of you as We dangle a cock cage. You are ordered into a series of timed events. Dusting with a huge butt plug in your ass. I enjoy ordering you back to the fireplace leg as I check it. Uh oh! Someone gets the little dick cage!

sissy humiliation

 

Now for you sissy humiliation training. You kneel at my feet and kiss my heels begging for release, but I had other plans for you as my best friends and I invited our big dicked boyfriends over! You are going to learn to serve a big fat cock and suffer at the hands of hot Goddess!

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!

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! 

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

Sissy Boys Love Sucking Cock

Sissy humiliationI need a sissy boy.Can I dress you up in pretty lace panties? I’ll give your mouth something new to do. Let’s makes some money together. You could be my new girlfriend. Guys really like it when there’s two of us. I know exactly who to call, Raheem, has is a big spender. We could get on our knees and share his big black cock. Run your tongue up and down his chocolate sex stick. We’ll have to take turns deep throating. We have to remember to keep our eyes up because guys really like eye contact. When we have Raheem’s cock has hard as a log, we’ll bend over and give up some pussy. I’ll lick your boy pussy and leave it sloppy wet and Raheem’s cock will slide in a lot easier. I’ll hold your ass cheeks apart and help guide his cock into your tight hole. You’ll need to be a good sissy boy and moan like a porn star as he pounds your boy pussy. You and I are going to make a ton of money. Are you a sissy boy?

Sissy Boy

Sissy humiliationYou look so beautiful in that dress. And that wig and makeup have turned you into a gorgeous woman. Put on these heels and become my sissy boy. I have special guests coming over and you’re the entertainment. When we hear the doorbell ring, I want you to answer the door and pull them into my home by their cocks. Tell them you’re here to serve and please. Drop to our knees and suck those cocks like a good sissy boy. It was a really good idea putting red lipstick on your lips because they look so good wrapped around that big black cock. Get those cocks nice and hard because you’re going to give them your boy pussy. Get down on your hands and knees, put your ass in the air, face down onto the floor, and offer your tight asshole to my special guests. You are my sissy boy and I pull your strings like a puppet.