Tag: sissy maid training

Dick humiliation and cock play

Sissy humiliation ClarissaTrying a new toy out on your favorite sissy botch’s ass is so fucking hot. I ordered a box of new toys which included a strap on dick, a bunny vibrator with an extra stong motor, a few cock rings and this ass plug which vibrated and had little silicon spikes around the rim for a little painful pleasure. My client showed up fr his nightly humiliation session and I immediately told him to get on all four and spread his pretty little ass cheeks for madam. He did so like a champ. I was feeling a little frisky, so I slammed that plug up his puckered little asshole enough that he gave me a little whimper. That made me wet fast. I love to hear my bitch, whine, cry and in pain. I then put on my strap on and face fucked him until he was so hard he had purple balls. I put my cunt up to him let him lick it until I came all over his face, I gave him a fake pussy to relieve himself into and then I sharply removed his ass plug and told him what a good little sissy bitch he had been.

Sissy maid training with Clarissa

Sissy maid training

Well, I found a new maid. He is so pretty and he does whatever I tell him to do. He scrubs my floors with his tooth brush and bends over so pretty as I instruct him to get on all fours and scrub harder. Oh and the pretty pink thong that I make him wear as it rides up his ass crack. I like to grab it every once in awhile and pull it up so it gets tighter and is uncomfortable for his dangling balls. Oh, plus I really enjoy when I walk in and he is not doing exactly what I told him to because at that point I make him bend over and I stick my anal beads into his tight little rectum and make him crawl across the floor because I know he secretly likes things up his asshole. By this time tomorrow my house should be fucking spotless. I am so glad I hired my pretty little maid.

Sissy maid stories: the cock, the cage, and the plug

Sissy maid stories

I’ve been having so much fun training my sissy maid. It’s becoming my favorite activity next to fucking you.

Of course with our new little toy you’ve gotten a lot more attention to your cock.

Like right now. I was enjoying the site of our little sissy maid on her knees. Wearing a latex maid outfit that left little to nothing to the imagination. Her little bitch clit throbbing in its cage as it tries to get hard. I giggle as I watch it, poor pathetic little thing.

Her cock was in your mouth.  She was fucking her own throat with such vigor that you couldn’t help but lean back, your eyes rolling into the back of your head. A pool of spit on the floor between you, our sissies tears ruining her makeup and her bright red lipstick was smeared all over your cock and her mouth.

I pressed the button to the remote control vibrating jeweled anal plug in her pussy and watched her quiver. She moaned around your cock making herself gag and try to pull off of your cock. I giggled as you grabbed her by the hair and forced her back on. Fucking her mouth with short hard thrusts until your groaned.

She was quivering, her hands open and close, Gagging and choking around your cock as you force your cum down her throat.

When you let her hair go she pulled back, coughing and gagging. Tears streaming down her cheeks as she gasped for breath. When she got some control again she swallowed hard and looks up at you. “Thank you sir.”

Sissy Humiliation

sissy humiliation

I am a switch – I go from the best girlfriend to the best sissy training phone sex princess ever. I’ve been very focused on humiliating my new favorite loser. He actually used to follow me around in high school, such a creep. Now he’s came crawling back to me, but for lessons on how to be a sissy whore. I was more than happy to help, and I’ve been spending all morning perfecting his sissy maid training. He had to really max out his credit card to make me happy! I bought him and myself tons of whore clothes, and makeup. Let’s not even get started on the shoes! I only had to make a few phone calls and my friends were there to humiliate, and of course fuck his tight sissy ass! He honestly tried to tell me he’d never sucked dick before, and never even had one in his ass. I knew he was full of shit though! Soon he was my bitch, and loving every second of it.

The Best Phone Sex is Sissy Humiliation

best phone sexThe best phone sex is sissy training phone sex. For me it is at least. Maybe not so much for my sissy callers. You see I make sissies prove themselves. Nothing annoys me more than fantasy sissies. I want my sissies to do humiliating tasks and send me photos. I want to know they are really wearing women’s panties because I prefer real sissies. I train my new sissy callers to my particular tastes. I love sissy humiliation, so every new sissy caller has an embarrassing task they most complete before calling me a second time. My latest sissy needed a lot of help. He gets high and gets sissified. He always insisted that if it were not for some high end cocaine and pharmaceutical Mary Jane, he would never have sissy thoughts. Bullshit. We all know that when you are high or altered your freak flag flies high. That is when you are at your most honest. You do not deny yourself feelings of guilt or let societal norms dictate your behavior. So guess what? If you are a sissy high, you are a sissy in need of a sissy trainer who will push you to be the perfect sissy all the time.

sissy humiliationMeet Katie, formally known as Ken. Her first task was to buy some pretty lacy panties. Her little clit stick would be lost in boxers. She had to be clear that she was buying the panties for herself, not a wife or girlfriend because women deserve bigger than an inch worm. Her second task was to write humiliating things on her feminine body like “tiny dick loser” and “I clean bull’s spunk.” Of course I needed pictures so I could post on my blog and know she was being a good little obedient sissy. I made her text the picture to ex girlfriends and apologize for not realizing sooner that size matters . I helped her pen an ad for Craig’s List to find a big black daddy to help her  hone her cock sucking sills.

Katie has come a long way in a few weeks. With her sissy trainer / phone sex therapist helping her, she will become the best cock sucking sissy faggot out there. Do you just need a sexy no nonsense sissy trainer to be the best sissy you can be too?

Small dick humiliation is my specialty

small dick humiliationOh sweetie, you are absolutely perfect for small dick humiliation… aren’t you glad that it is one of my specialties? You see, I know what you need better than you do yourself. I know that you are not a real man… in fact I know that you are more of a woman than you have ever been a man. You should be dressed up and humiliated, with that tiny little wannabe cock you have you are perfect for panties and I know that once you have them on you are never going to want to wear anything else. Now, don’t get the idea that I am going to allow you to rub that tiny thing either, I am all about tease and denial with a heavy emphasis on the denial part. I love to see you whimper and beg and I love knowing that you will go to bed with your shriveled little balls all blue. This is all going to happen sweety, whether you want it to or not…

Spring is in the air!

sissy humiliationIt’s one of my favorite times of the year! Spring means frilly sparkly dress and the cutest dolled up attire you can imagine. Stockings, bows and ribbons that’s only a small part of what spring time is about! But you see this is not my favorite thing about spring… it’s really dressing all those loser sissy bitches in the cute little pretty dresses… And watching how it’s making it awfully hard for my big black cock friends to resist tearing those little assholes apart. Who could blame them? They’ve all got 12 + inch cocks and when they see a fuckable fag ass all dressed up in one of the many girly dresses I have put aside for loser sissy they simply don’t take no for an answer! Suddenly my very good friends are forcing their cocks into tight little holes, most take it like pros, others try and resist their ass getting fucked. You’re all part of a sissy gangbang! You know you’re nothing but a bitch that’s going to take it all…just like you begged for. Should have read the fine print, honey. You wear the dress – your ass gets fucked.

sissy maid stories

Sissy Humiliation of a Fairy Fag

Here at Fuckalicious Freaks we have our own pathetic Sissy faggot. Well, actually she is owned by Goddess Levi, but we all get to join in with the humiliation and outing of this Sissy fag Homosexual.

Our Sissy Fairy Fag is always getting herself messed up in her punishment assignments, thus her humiliation, and walk of shame. Sissy has a pathetic small clitty and these dingle balls that are often fondled making her pathetic man clitty dribble.

sissy humiliation

Yes, she wears these frilly princess dresses and silky panties, however, she has a habit of soiling the pretty panties with her own poop. When our pathetic Tinkerbell  transvestite gets dirty and starts playing in her poop we take her humiliation further and make her confess to making her face up with her poop. That’s right rubbing a little on her lips and eye’s and making her prance around in public with a poopy face and poopy panties.

Another way we love to humiliate our little piggy princess is to make her our human urinal and we feed our piggy some golden shower nectar. We then make piggly wiggly crawl around and oink and squeal like a piggy while begging us to suck off our dong. Sissy Fairy Fag Michael is a pathetic pansy.

Sissy Maid Training

Good help is hard to find.

Domination phone sex

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.Sissy maid training

Fun New Sissy Games!

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:

sissy humilation

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

sissy humiliation

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!

sissy phone sex 2 amber