Category: 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.

Tease and denial phone sex Felecia

My little sissy could not keep his hands off his tiny little clitty. No matter how many times I spanked him he just would not stop trying to rub it and get off! Can you believe how bad my sissy was being?! He needed to be punished. I dressed him up in a beautiful little frilly dress, I put a cock cage on his tiny clitty and some panties!

Tease and denial phone sex

We didn’t forget the make-up and wig! I sent him out to go get cucumbers, Bananas and some lube oh and condoms! He was so sad that I forced him to walk and take the bus to the store dressed up! He thought someone was going to take a picture of him and it be found on fb and then his wife would find out. Well if he wasn’t such a disobedient little sissy faggot then he wouldn’t be humiliated so badly! When he finally got back after an hour! He was in tears! Covered in spit, he even had this guy throw poop at him! He said it was the worst day of his life, but when I pulled up his frilly skirt I saw that his tiny clitty was rock hard and drooling!

Sissy humiliation

I knew he loved it! His punishment wasn’t over yet! I told him to tell me all the mean things that those mean people told him! I pulled out the bunch of bananas and started to fuck myself in front of him! He was begging me to let him taste me after he had such a bad day! I giggled and continued to fuck myself with that banana! Watching my little sissy cry and beg to cum! He shouldn’t have been such a bad sissy! I think I’ll keep the key to his cock cage and let him go home for the week not allowed to rub his clitty or even play with his own wife!

Domination phone sex

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 Bitch

Sissy maid stories

I was shopping today for a new maid uniform for one of my clients and it got me thinking that I need a new sissy bitch to lick my leather boots. They have not been cleaned in some time and are due for a good licking. I also got to thinking how much not only my boots need cleaned but so does my asshole. I really need my new bitch to have training in several areas. I started checking off what I wanted in my head and I decided I really want someone who can lick like their life depends on it, someone who is not a giant crybaby and wont be a little bitch when I slide my fake cock into their asshole, I want someone who can lick pussy without needing any air because I do not like giving breathing breaks. I want a little bitch who is going to obey my every command without question. And if they do disobey me I will make them wish they had not. I have many over-sized cocks to stick in your orifices as punishment.

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.”

The Best Phone Sex is Sissy Humiliation

best phone sexThe best phone sex for me is with sissies and cuckolds. Why? Because I get to be a mean bitch. Over the weekend, I met this man. We actually went to college together, but lost touch over the years.  Face Book reunited us. I agreed to meet him Saturday for drinks. Attractive man. Educated, articulate, nice and a wealthy.  Just not very masculine. I figured his more feminine voice and mannerisms were from low testosterone, which usually means small dick. I was right. He had a 2 inch willy at best. When I saw it, I burst out laughing. The gall of any man who thinks he can fuck me with a shrimp dick pisses me off. I gave him a healthy dose of sissy humiliation that began with putting him in a pair of my panties. Anything less than 5 inches belongs in panties because it will swim around lost in boxers. I am a sissy trainer. Sometimes guys come willingly to me for help on becoming a sissy, sometimes they need nudging like my college pal. He was an old friend. I couldn’t delude him into thinking he had anything that could please a woman.  That’s just setting a man up for failure. Sissies can become a very integral part of a woman’s life if they just get a little training and accept their fate. The sissy training began with panties and an honest conversation about cock size. We discussed ways he could still please a woman without actually fucking her since that would be no pleasure at all. During training, he couldn’t stop rubbing his nub. I smacked his hands away from his dick several times before I put him under lock and key. Sissies are here for a woman’s pleasure.  I only allow a sissy to touch his willy as a reward for something quite remarkable. My sissy in training can barely lick my pussy. Until further notice, he is under lock and key. I love being a sissy trainer. He will learn to worship my pussy eventually. At least if he ever wants to touch his dick again, he will.

sissy humiliation

Princess phone sex Darline

Princess phone sexWe got a new maid!

Not just any made but a young little sissy for me and Lorine to play with.

This young man was thin, pretty, and made such a pretty little maid.

She was so nervous as Lorine and I looked her over as if she was meat. Our fingers tracing over the shiny latex uniform, pulling on the cotton ribbons and apron.

She was practically shaking with nerves, so rather than try to make her feel feel better I told her. “You are ours. Your body… Skills… Mind… You are here to serve us. Understood?”

I saw her adam’s apple bob before she nodded. “Yes ma’am!”

I grinned, grabbing her by the hair and making her moan and her knees seemed weak. “I want you, as your first task to make my Lorine cum.” I pushed her down by the hair, her knees hitting the concrete hard making her gasp. The latex skirt tenting with her erection even as Lorine pulled up her skirt and revealed her wet hairy pussy. My hand pushing our little sissy’s face into that musky, beautiful, wet pussy. “Lick slut.” I commanded, knowing she followed it as Lorine shivered and moaned.

We were going to spend hours training, teasing, and fucking with this little sissy maid and I’m sure that we’ll have a long, fun, and loyal employee after this.

Latina phone sex

Sweet and slutty and ready to play.

GFE phone sex

Sometimes you need a sexy and friendly voice instead of a slutty one when you got something on your mind that is making your cock swell. And you want advice as well as release, why not try some GFE phone sex with a college educated phone sex therapist. I’m a sensual woman who knows how to please a man. I have quite the sexual appetite myself so I know how you feel when something is stuck in your head making you crazy. Share with me those wicked and naughty thoughts and fantasies. I’ll teach you new and creative ways to make that cock quiver. Tease and denial, edgeplay, guided masturbation and erotic hypnosis are just a few. I’d love to be your new internet girlfriend and someone you can share your dirtiest and most perverted thoughts with. Don’t mistake me for boring. I love to slide my hand in my panties and play along as we chat. I have a wicked sense of humor that will make our sessions anything but boring. Let me share vivid verbal pictures of my own needs. Nice girls have wet pussies too.

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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?