Category 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.

Sissy humiliation, let’s fill my fish bowl

Sissy humiliation

Sissy humiliation … what’s there to say really? It’s rather self-explanatory, but each person has their own idea of what it entails. What does it entail for you? I like to compile a list of things my sissy doesn’t like. I know it’s rather shitty for me to pick up on things in a normal everyday social commentary, but you have to get your info somehow!
What we will do once I am satisfied with the number of things you dislike that I have accumulated. I’m going to have you write each one down on a piece of paper and put it in a fish bowl. Anytime you do something that is out of line I will grab one of the pieces of paper and you will be punished with whatever happens to be written on it. I probably stacked the bowl with ones I like too. If you can think of 10 things you dislike, tell them to me and I can have some fun making sure you feel humiliated and more like a sissy than you did previously.

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.

The gym bull

Cuckold phone sex

He was handsome and ready to fuck. We invited him in, he seemed nervous, but when he saw I only had a silk robe and nothing else on his focus turned to his hardening cock. Hubby said, “Please take her and fuck her like I can’t.” The gym rat smiled and picked me up and said: “Where can I fuck you.” We made our way to the studio,  kissing and giggling. Instead of putting me down, he put my legs on his shoulders with my pussy right in front of his face and he started licking my pussy so expertly. Then he flipped me upside down, legs in the air and my mouth at his cock, we sucked and licked each other while the sissy sat in the corner in his usual panties and bra. Cock popping out the side I gave him permission to jerk off. Gym rat was hard as fuck and he sat down on a chair and set me on top of him. He didn’t just start fucking me hard; he teased and played and licked more, then teased me with the head of his cock driving me crazy. Finally, he let loose and was plunging into me balls deep. Skin smacking every time he would bury himself in my pussy, I begged to ride him. When I got on top his cock was so deep, he looked at the sissy hubby and told him to come over and play with my clit and be a real man. Fingers on my clit, cock deep inside me, rocking my hips back and forth I exploded all over him. Sissy was ordered to lick all the squirting juices and sperm off both of us.

Sissy humiliation

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.

Older posts «