Category: Sissy maid stories

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?

Dirty Little Secret

Sissy humiliationI know all of your dirty secrets, things that would shock the people closest to you. I’ll keep your secrets if you’ll be a good boy and obey. My car note is due, and you’re going to make me some money. Put on this wig and makeup, I’m going to turn you into a beautiful sexy slut. Slip our sexy ass into these black lace panties and high heels, because I have a room full of big black dicks. Get down on your knees and crawl into the room, you’re a sex animal. Black dicks will surround you, do your best to take care of each one. Open your mouth and suck and lick each huge veiny cocks. Use your hands to stroke these long thick cocks until they’re nice and stiff. Make my money and no one has to know that you’re a cock sucking faggot. I can see that your cock is hard, you love black cock! I wonder what would your loved ones think if they found out about your dirty little secret.

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.

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.

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

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

Puppy penance

Sissy humiliation

What makes something humiliating is subjective to the person being humiliated. At least that is my take on it. My sissy hubby can’t even grill a steak right, so I’m the one that does the grilling. So I make him sit next to the patio door on all fours waiting for his meat like a good little pup.
Once the meat is done he gets so excited wagging his little pup butt and drooling. This time he tinkled all over the carpet in excitement, I was so pissed! I walked him over to the spot he soiled and made him lick the puddle up. He whimpered and cried, but I rolled up a newspaper and he knew exactly what that meant, a smack on his little pup dick.
Meal time he sits next to my chair waiting for me to cut him little scraps of meat. Sometimes I will toss it a little to make him run after it, which is pretty funny considering people aren’t meant to walk on all fours. Sometimes I will just toss it on the floor or let him take a piece from my fingers. Only if he’s a good boy does he get to get under the table and lick the pack leader’s pussy.  Definitely, don’t want crabby pack leader pussy.

Phone 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.