Each year we all take a wonderful vacation and everyone’s favorite Sissy helps make that come to fruition. She begs and pleads all year long for humiliation and shame just like she deserves and we all give her what she wants and then some. Being fairly new here I have yet to dish out any humiliation of my own, however, I have heard that it is Sissy’s fantasy to accompany us on vacation one year and be our Sissy maid. She longs to wait on us hand and foot, cooking and cleaning in her pretty pink maid uniform. She longs for the Sissy maid stories that she will come away with and be able to share with…with….with…come to think of it, there isn’t anyone she would be able to share these stories with because she hides the fact that she is a sissy from everyone but us and we will all know all about every Sissy maid story she will have to tell. That is almost as sad as the life she leads as a fake man in a court room surrounded by real men who would laugh at her and ridicule her if they ever found out the truth. Maybe one day our head bitch in charge, Levi will do the honors of introducing me to Sissy. Until then Sissy, let your pantie wearing flag fly high! Maybe some day you will get what you wish for….
Category: Sissy maid stories
She Dreams Of Sissy Maid Stories
- By Ginger in Best phone sex, Cuckold phone sex, Domination phone sex, Erotic roleplaying, Femdom phone sex, Forced crossdressing, Forced feminization, Hot sexy woman, Phone sex therapist, Sissy maid stories
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January 8, 2016
Let’s watch the Ball drop!
- By Felecia in Best phone sex, Cheapest phone sex, Cuckold phone sex, Domination phone sex, Forced crossdressing, Forced feminization, Sissy humiliation, Sissy maid stories, Sissy maid training, Small dick humiliation
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December 28, 2015
You are invited to my Ball Drop party!! I will have half naked whore’s walking around. We are all here to please you! Plus come make fun of our chubby sissy whore! Sissy will be my maid at this year’s party! I am so excited to see him dressed up as a “Sexy Bunny” but really he will just make you kinda sick! Come laugh with me and get drunk this New Year! Let’s have some fun with my fat little dick sissy whore!
She is supposed to show you her itty bitty tiny cock when you as her to see it! Sissy has to follow her orders! Make Sissy Fairy Fag your table! Make Sissy your foot rest for the night! Make her prance around in her tall heels! Make her shake her flat sissy ass! I know you want to ring in the New Year making fun of my fat fairy sissy and her small cock! Make her watch as you fuck someone right in-front of her! This fat sissy will beg for your cum all night long!
Felecia

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Sissy humiliation with Felecia
- By Felecia in Best phone sex, Cheapest phone sex, Domination porn, Fantasy phone sex, Female domination porn, Hot sexy woman, Phone chat lines, Phone humiliation, Sissy humiliation, Sissy maid stories
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August 22, 2015
Our Site Sissy Micheal needs to come clean my house! I just can not stop myself right now. I know he is going to be shocked when he see’s my floors. I keep fucking myself with my big red cock. I keep making myself squirt pussy juice every where!! I want our site sissy whore to watch as I make myself squirt even more. I want to make fun of him and his tiny worthless little cock. He will never make a woman cum as much as my red cock!
After I am done cumming my sissy fairy fag and his tiny cock is going to lick up all my yummy cum up off the floor. He has to lick it all up! Every drop off the floor and if he misses one spot I am going to call his wife tell her what a sissy whore he is and send her pictures of his tiny cock in a cage!! Let’s go sissy, get to work. Make me happy or Your wife will know EVERYTHING!
Felecia

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Good help is hard to find.
- By Clarissa in Domination phone sex, Femdom phone sex, Forced crossdressing, Phone humiliation, Sexy dominatrix, Sissy humiliation, Sissy maid stories, Sissy maid training, Small dick humiliation, Tease and denial phone sex
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August 16, 2015
I just love a good little Sissy. I have this one that I keep as my very own little sissy maid. I dress her up in the most frilly maid outfit and love watching her clean my place. I keep a lovely riding crop with me it keep my pretty wissy sissy in line. On her hands and knees she’ll scrub my floors with nothing but a toothbrush and her ass in the air to show off her pretty little panties. I love watching her blush with embarrassment as I get to see the way it rides up into the crack of her ass and how it holds in her balls and small dick.
It pleases me when she uses her manners and acts like the proper lady I taught her to be, otherwise I’m forced to make her bend over and get a swatting.
You wouldn’t be a bad little sissy maid would you? You’d do everything I’d ask you to do, wouldn’t you? Be a good little girl and you’ll get rewards, but be a little girl and you’ll get your bottom spanked.
Clarissa

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Fun New Sissy Games!
- By Amber in Phone humiliation, Sissy humiliation, Sissy maid stories, Sissy maid training, Small dick humiliation
-
July 31, 2015
What a delightful chat we had with Sissy Michael Fraze..e this evening. Apparently she has been BEGGING and whining nonstop so that all of us girlies know how much she enjoys being the jingly jangly pee-pee drinker for princess nectar. She has been begging Mistress Levi for days to be able to stroke her tiny winky and finally she got her chance. Of course this didn’t come free, as nothing ever does in this poor pathetic little piggy faggot world.
She kept begging and during that time we discovered that Piggy Michael is actually in the dictionary! We got our dictionaries out, looked up the word “queerness”, and here is what it showed:
QUEERNESS; NOUN: a contemptuous term used to refer to a person who does not conform to a normative sexual orientation or gender identity, such as the sissy fag pictured here.
What a fun surprise to know that our little fairy was famous enough to land her picture in the dictionary next to such a funny word!
So finally, after lots more begging, Mistress Levi decided it was time for a new game for Piggy Michael to learn. PPS. This is the always fun game of Pay-Per-Stroke of her tiny winky so that she can do her nasty little squirt. Since her winky is smaller than my thumb, the strokes were tiny that they added up quickly! Now she owes a fortune for playing the new game. At first her winky shriveled up, but the timer was already going so she had to start stroking. We laughed and laughed as she stuck her piggy nose into her humiliation and stroked away at that tiny little thing like crazy.
She ended up getting her little dingle balls drained, and we laughed so hard at her and how embarrassing it was in the end. I found this new little piggy winky cover for her to
wear so that her little tiny winky can’t shrivel up and hide anymore. It should keep it toasty warm and in easy reach of her little hands. Speaking of her hands, I found the perfect manicure she can get before her big sissy day out on the town next month. I think it will be super funny and just add to how pathetic and silly everyone will think she is! Jingle on down to the salon, Piggy, and get ready for your big day!
Amber

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A Jingly Jangly Sissy Potty!
- By Amber in Best phone sex, Sissy humiliation, Sissy maid stories, Sissy maid training
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July 28, 2015
I just love finding things are made for Princesses Only – and I made an awesome find today! Our little fairy faggot sissy, Michael, came jingling up to me and wanted to show off her newest way of pampering us princesses. And when I say JINGLE, I mean it – she has a new collar from Mistress Levi, along with cuffs for her wrists that have so many bells on them it sounds like Christmas has arrived when she walks by!
Her little fairy outfit was so skimpy – I think she will be in trouble for showing her pathetic little buttcheeks like that – I was surprised that more people weren’t stopping to take pictures. She led me over to a pink port-a-potty and I just cracked up. I asked her what in the world that was, and she told me that she sits in there in the hot weather, mouth open, and just waits for superior females to come by and pee down her throat!
Well, of course, I couldn’t believe the little whining piglet, so I had to see for myself. She climbed inside – down into the hole – and sat there and waited. I could hear her inside singing some new song about princess pottying and her bells were jingling so loud I could hear them with the door shut. Sure enough, a pretty girl walked up and heard the bells. I told her to go inside and that a jingly jangly sissy toilet was waiting.
She opened the door, and the little sissy lit up with a big smile and begged for her sweet female nectar. She gave it to her, and she drank it all down like the good little piggy she can be. I was proud of little piggy Michael today – she sure knows how to jingle those bells and make sure that all us princesses get treated well, even if its just when we have to pee!
Amber

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Best phone sex with Felecia
- By Felecia in Best phone sex, Forced crossdressing, Mature phone sex, Phone sex sites, Sexy dominatrix, Sexy phone chat, Sissy humiliation, Sissy maid stories, Sissy maid training, Small dick humiliation
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June 14, 2015
I had a sissy one time who was a nasty freak.
He was about 250 and 5’6. Short fat man who wanted to be made fun of.
I called him pig dick.
He was one of those guys who would just want to punch when ever he opens his mouth.
Lucky for me he had a pantie fetish.
I would wear the same panties for a few days, put them on right after sex.
I let those panties get crusty, smelly and ugh I hated wearing them. But the money he paid me to wear them was worth it.
He paid me money to make fun of him, to call him names, Tell him how tiny his cock really was.
But most of all he paid to clean my house.
He would walk in the door, wearing nothing but a thong, thigh highs, 5 inch heels a pig nose and nipple clamps.
The very first thing we would do is grab those nasty panties, shove them in his mouth and duck tape his mouth hole closed.
Then I would enjoy watching my little piggy clean my house.
Felecia

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Nose Ring Piggy Michael Oinks and Squeals!
- By Amber in Best phone sex, Phone chat lines, Sissy humiliation, Sissy maid stories, Sissy maid training, Small dick humiliation
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April 29, 2015
My favorite kind of little faggy piggy is one that sqeals when she is excited! Poor little Michael, all she seems to do is squeal and oink – so Mistress Levi made her wear her piggy nose ring so that the whole wide world knows how much she loves to be a little silly piggy! She walks around feeling just like a pink little faggy piggy and people just laugh and laugh. She loves all the attention and is so happy to show off her nose ring like she’s the prettiest little piggy ever! Nose ring Piggy Michael oinks and squeals!
This little piggy went poo poo
Then this little piggy oinked once
Then this little piggy oinked twice
And this little piggy had a teeny weeny winky
And this little piggy danced a jiggy
And squealed squealed squealed all night long!
She loves to wear her piggy nose ring so that everyone knows how ridiculous she is and how much she loves to be humiliated by superior females like myself and Levi. The other girlies and I have been laughing at the little piglet for so long and she just eats it up – snorts it up like the little squealing piglet she is! Poor poor little piglet, she just can’t get enough attention, so she has to be made fun of and made to do things that only sissy fairy fags do. That’s all she deserves though, and I look forward to every time Levi makes her SQUEAL!
Amber

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Small Dick Humiliation with Maggie: Are You a Prancing Panty Wearing Fag?
- By Maggie in Best phone sex, Domination phone sex, Forced crossdressing, Forced feminization, Phone humiliation, Sexy dominatrix, Sissy humiliation, Sissy maid stories, Sissy maid training, Small dick humiliation
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April 14, 2015
I enjoy small dick humiliation. Personally, I think any guy with less than 4 inches should be publicly shamed. How can you call yourself a man with such small inadequate equipment? You can’t. A few months ago, I had a party at my place for my department. Fellow grad students and professors were invited. This old crotchety professor of mine actually came. His invite was perfunctory; I didn’t think he would show. He made quite an impression too. At one point in the evening, I realized he was MIA. So I went looking for him. The bastard was in my bedroom trying on my panties! An Art History scholar was prancing around my bedroom in my red panties.
“What the fuck do you think you are doing, Fag,” I yelled loudly? I got his attention though. He stopped prancing dead in his tracks. I demanded he take off my panties pronto. And that’s when it hit me. He was NO man. I laughed hysterically. “Excuse me, but I guess you need to be wearing panties. That little thing will get lost in boxers,” I giggled. He had nothing but a clit stick. Well this explained why he had been divorced 3 times and was always cranky. No way any hot chick was fucking him, brains or no brains. Girls want something they can feel. Squinting, I still could not see it. I pulled out my cell phone and snapped several pictures to best capture his short comings. He pleaded with me not to expose him. “You outed yourself fag the moment you helped yourself to my panty drawer,” I retorted.
I ordered him to prance around like the silly fairy he was. His face turned red from embarrassment. He had yet to experience true shame. I made him put on lipstick and eye makeup, even a pair of my heels. I sent him back to the party. “You are no longer a guest, but my sissy maid,” I quipped at him. “Now go serve my guests whatever they want.” I knew when he reached the party because I could hear the laughter even from the other side of the house. I returned to my guests. That was when the party really got started. No one liked this professor, so no one had an issue with humiliating him. Well humiliating her. My clit was bigger than his dick, making me twice the man lol.
We now had a private department sissy maid. That party was just the beginning. I own that prancing fairy fag. At the party, she had to serve the drink and food in nothing but my heels. She had to pull up everyone’s car. Even had to suck some cock so she could understand what real dick looked like. She blubbered like a baby; pleaded for mercy; begged for forgiveness. But, pay back is a bitch. Now at every grad student party or department function or when any of is feeling cruel, we make her prance around in panties or naked and recite humiliating little ditties while waiting on us hand and foot. Oh yeah, and we all get As in her classes.
My time is precious. So it is nice to have a sissy maid to do my laundry, clean my house, and take care of my guests’ every whim. A sexy girl like me should spend all her free time fucking and having fun anyway. Don’t for a moment mistake my girl next door look and think I’m some sort of innocent door mat. I am smart, sexy and always in charge, especially if you are a prancing sissy fairy fag with a clitty stick.
Maggie

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Surprise in Sissy’s Purse!
- By Amber in Best phone sex, Sissy humiliation, Sissy maid stories, Sissy maid training, Small dick humiliation
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April 12, 2015
Poor little sissy fairy faggot Michael… she has a BIG day coming up and she knows that to celebrate her big Sissy Day, she has to dress up in her Miss Piggy dress and nose and go everywhere Mistress Levi tells her to. All you girlies will be so excited to hear what the pathetic little sissy has to do to out herself! We all know how she loves to carry her little faggy purses around and put things inside them so she feels pretty and pretends to be a pretty little girlie like we are.
Well, besides her lip gloss and her tampons – in case her little bum starts to leak from excitement – she is going to have her new business cards! She will be handing them out to all the real men who are laughing and pointing at her. She will smile really big and even sing songs as she passes them out to everyone she sees. The cards will have her real name and phone number and website on them. Everyone who gets one will be able to log on and see what a truly pathetic little faggot fairy she really is.
She is getting them ready now, and learning her new piggy song that one of the other girlies got her started on. Such a sad humiliated little fairy she is going to be while she hands out the cards to all the people laughing at her. In the meantime, I am sending all her info to everyone I know, even in the Phoenix area, so that they can be sure to find her when she is out and about doing everything Mistress Levi tells her to. I am laughing so hard right now after listening to her try to play with her itsy bitsy limp winky and cry about how scared she is. Soooo pathetic. She better do a good job and then thank Mistress Levi for letting her be humiliated, or things will only get tougher on the poor little faggy piggy….
Amber

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