Tag: Sissy Maid Stories

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.

Sexy Dominatrix Gwen

sexy dominatrixYou called and arrange a session with a sexy dominatrix. I told you to be here promptly at eleven o’clock in the morning. It is now twelve and I have not seen or heard from you. I am starting to think that you have chickened out. Then my phone rings and you start making excuses for being late. Which is totally unacceptable. You should have called me at the time of our appointment not thirty minutes later. By the time you finally arrive you have wasted over an hour of my time. I let you know that you will be paying me for my wasted time and this is no longer going to be a sexy domination session, but instead a sissy maid training session. You will be paying for your naughtiness. I have you take off all of your clothes and then put on a super slutty maid outfit with crotch less panties, stockings, sexy high heel shoes, and last but not least some red fuck me lipstick. Then I hand you a feather duster and tell you to start cleaning. Every time you bend over I give you a hard smack with the riding crop. Before long your ass is covered in pretty little red welts. The door bell rings and you go to hide. I tell you you had better get back to cleaning my coffee table if you know what is good for you. I open the door and one of my luscious dark chocolate friends is standing there. He notices you right away and says well Mistress Gwen what do we have here as he licks his lips. You’ll have to call me to find out what happens next.

sissy maid training

Sissy maid stories always crack me up!

sissy maid storiesSissy maid stories always crack me up so when a little sissy bitch named Matthew called me I knew that it was going to be a very entertaining call… for me anyway, he was going to be humiliated and shamed. This little bitch boy was all shaved and had long feminine hair, he was all dressed up and had a full face of makeup on, this was clearly not his first time dressing as a sissy. He asked me if I thought he was beautiful and I just had to laugh, I told him to look at me if he wanted to see beautiful, that he was just a pathetic wannabe! You are not a woman just because you shave and put on a dress! What you are is a silly little sissy boy that needs a good fucking to show you your place! That’s why I fucked that little sissy boy with my biggest strap on cock, by the time I was done he was much more aware of his place!

Women In Charge

Sissy Maid Stories

I am part of a highly exclusive club where things are a little turned around. Here, it’s the boys that drop to their knees at the command of a woman. The ladies get the VIP life, while the men are collared and leashed to serve the women. We keep a few of the buff bodied sissies up on the stripper poles, doing sexy little dances for some of the femdoms who are chatting with their friends, of course, using the men to sit on or as foot rests. Sitting at the bar to order a drink, one of the sissy boys dressed in a little maid’s uniform came up to talk to me, as was customary when a femdom walked in and was not already accompanied by one of the girly boys.

I kicked off my shoes. I had spent a long day on my feet, so I ordered him to massage my feet through my stockings. The bartender brought me a drink as I moaned from the tension slipping away from my body. Opening my legs, I signaled that he should now begin to please me in a different way. He kissed up my thighs before licking my clit. I pushed his face deeper into my pussy as I came on his face. After catching my breath, I dismissed him. I didn’t need him getting attached and trying to get me to take him home as my permanent pet.

Sissy cuck with PMS prissy man syndrome

Cuckold phone sex

I don’t really suppose cuckolding can be done with a dildo, but I’ll just do it anyway. My sissy hubby has been a super bitch lately. It seems like he is having PMS, prissy man syndrome, sullen, bitchy and no fun at all. When it was chores and panties time the other night he actually rolled his eyes at me and let out an exasperated sound at me. I wasn’t too happy about that, nothing in his sissy training has included giving me attitude. I do understand that his job is very demanding and stressful so I gave him a scolding and told him to keep his complaints to himself or I would have to dole out some punishment. He didn’t seem all that impressed either way and he went about his chores. A few hours later when he was done I told him I wanted to cum. He got onto the bed where I way lying naked stroking my pussy, he started licking my wet little fuck hole and clit without much enthusiasm. When I got tired of his half ass effort I told him to go sit in the corner and if he wasn’t going to do it right he could watch me every night for a month with someone else or a something else. That seemed to perk him up a lot and his cock got nice and hard. Finally the sissy I know is back….but I think with that behavior a punishment is in order.

Sissy Maid Training all night long

sissy maid trainingI never knew about sissy maid training until I met my husband. He’s much older than me and his cock is so small. Good thing his bank account is nice and fat.
He swept me off my feet with his charm. I couldn’t wait to feel his cock inside of me. When the time finally came and I slipped my hand into his pants, I was horrified. I smiled awkwardly and he burst into tears. That’s when he revealed his secret. He was looking for a wife like me because he needed sissy maid training and he knew I was just the woman for the job.
He bought me piles of sexy lingerie and spa treatments. Then he sent me out at night looking for the biggest cocks I could find.
My masculine businessman spouse turned into a cum craving slut!! He loved watching me get fucked. He could barely wait until you left so he could lap up the creamy leftovers and jerk his tiny weewee onto my big tits. As for me, I am loving it. I feel like the luckiest woman alive. I can barely wait until tonight when I go out searching again. Are you a cucky slut, too, who needs some training or are you the oversize cock that I’m searching for?