Tag Archive: sissy maid training

Erotic Roleplaying and Sex Therapy With Gwen

erotic roleplayingGwen likes to do sex therapy sessions with you. She wants to hear all about your sexual desires and what kind of erotic roleplaying makes your big thick cock get rock hard. Nothing is ever off limits or taboo with Gwen. You are always free to share with her your dirtiest, kinkiest, and wildest sexual fantasies. I will never judge you. The truth be told I am a very kinky girl and your dirty little sexual secrets make my pussy soaking wet with desire. If you dream of fucking sisters Gwen wants to hear about it. If you want to be a sissy slut tell Gwen all about it. If you have a foot fetish or want to role play share it with Gwen. Gwen wants to help you live out all of your wildest kinkiest sexual fantasies, but you do have to tell her what they are before she can help you.

Cuckold Phone Sex: Shaming Losers

cuckold phone sexDo you enjoy cuckold phone sex? You must be a loser if you said yes. I love losers. I won’t fuck a loser. I married two losers so no more losers in my life. I mean no more losers in my pussy. I have no problem turning a loser into a cuckold or a clean up bitch. I also have no issues with shaming a loser. This guy I know loves to be publicly shamed for his little dick. He pays me for it too. Poor bastard. I had him over last night for girls’ night. Talk about fun. Me and 10 other hot babe size queens into small dick humiliation. We had him stand in front of us. We spent a good half hour ridiculing his little pinky dick. We wrote Loser and other such things in red lipstick on his body. The fun really happened when we dressed him up like a sissy. We even did his hair and make up. We put her in a sissy maid outfit I have for such occasions and took pictures for public shaming. We made him up load the pictures to his Face Book page so his family and friends could see what a shameful sissy loser he had become with our help. I broke out the bag of tricks so we could all fuck his little boy pussy. He cried and pleaded with us. Even claimed we had gone too far, but I knew he wanted a good ass fucking. All cucks and sissies love their asses played with, don’t they? You know what I am saying is true because if you are still reading this, you are enjoying what I have to say. Your little clitty is throbbing. Put on some panties, get out a toy and let’s have some fun.

Sissy Maid Training with Gwen

sissy maid trainingI have so much fun with sissy maid training. I always keep your little cocks in a cock ring because after all once I make the transformation of turning you into little sissy girls you no longer have a cock. You have a pussy instead. Sometimes I like to dress you up in a maids outfit and shove a feather duster up your tight little puckered assholes. I tell you that you had better do a good job dusting and laugh as you are wiggling your ass trying to dust the coffee table. You knocked a lamp off of the end table and that just won’t do. So I have you bend over and place your hands on the coffee table. I have found that my riding crop always helps you to remember to be more careful. After a dozen of well-placed smacks on that ass. I start fucking your ass with the feather duster. You are begging me to release your cock ring and allow you to cum. But I don’t. Instead, I tell you to go do the dishes and leave that feather duster up your ass. Maybe if you do a really good job cleaning I will allow you to come…..only time will tell.

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

Pretty Sissy

Forced feminizationI’m a madam, a female pimp, and I need a sissy that willing to do anything to get money for me. I’ll make you so beautiful that you’ll be able to attract any man. I’ll teach you how to do your makeup and hair. And put you in the finest clothes, because my hoes are high-class. The next step will be your sexual education, I’ll teach you how to suck cock, and how to accept huge cocks into your boy-pussy. We’ll make so much money you’ll be able to quit your day job. It’s going to be hard work. Sometimes you’ll entertain up to twenty men a day. You’ll get so much action your lips and asshole will be sore. The only rule that I have is that you must always remember that I’m the boss and I run the show. Any attitude or back talk from you means automatic punishment. Be a good hoe and we won’t have any problems.

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?

Maid Wanted

Small dick humiliationPull down your pants, let me see what you’re packing. Oh my God! Is that it? LOL! Seriously, you have the cock of a two-year old. There’s no way you could please me with something that small. You look like a female with a huge clit. I think you should be a female, and you should be my personal french maid. Put this French maid uniform, it’s your perfect size. Let’s put red lipstick on your lips and this blonde wig on your head. Look in the mirror you look like a real bitch. Now start cleaning, I want my house spotless. I need you to vacuum, dust, wash dishes.  Don’t act like a dumb bitch you know how to clean from top to bottom. And when you’re done cleaning I’m having male guests coming over and it’s your job to make them feel welcomed and comfortable. I want you on your knees with one of their cocks in your mouth at all times. If my guests want to fuck you…you bend over and give them some boy pussy. That’s a good bitch. Don’t let me down.

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