Category: Sissy maid training

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.

For more hot pics and stories to get your rocks off, visit us at https://wbmtphonesex.tumblr.com/

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?

The Therapist is IN.

phone sex therapy

He sat in front of me sobbing into his hands. I patted his leg, telling him that things were going to be ok.  I’m a phone sex therapist and I help men in need. “My cock is very small and I can’t get any pussy. My girlfriend left me.” I asked him to show me his problem and he unzipped his pants to reveal the ittiest, bittiest penis that I had ever seen on an adult man. I tried to stifle a giggle. “It’s a little bit small.” I admitted. “maybe you can compensate by learning to eat pussy?” “No, doc.” he stuttered. “I want to be a girl and I want you to teach me.” I was dumbfounded. How do you teach a man to be a girl? I began to question him. “Are you turned on by cock?” I asked. He smiled and nodded. “I want you to fuck me.” My pussy got a little moist as I pondered this thought. I reached into the bottom drawer of my desk and brought out a huge black cock left behind by a previous client. His face lit up and his tiny pecker began to swell. I put it on and stuck it in his face. He greedily gulped my dick like a pro. “Make it wet for your pussy.” I ordered. “Now turn around.” I poked my giant cock head right up against his man-twat. “Now push. Take my dick, you little faggot.” he whimpered as he impaled himself on my thick blacksnake. I hammered that ass good, making myself cum, as he blew his little dicklet all over my floor.

Are you in need of some special therapy, too? Bare that ass and get on your knees. The therapist is IN.

Let me be your naughty maid

I love dressing up in naughty outfits and surprising you at your office. Walking past your employees in a long coat with a skimpy maid outfit underneath. I get to your office and just drop the coat on the floor. Seeing your cock get hard in your slacks make me creamy in my tight black thong. My maid outfit is driving your cock crazy.

I push you on your desk and I pull that fucking cock out and sit right on it. My maid skirt coming up as I bounce my ass up and down on that cock! You grab my hair and pull me down on your shaft. You grab your tape off the desk and put a piece of my mouth so no one can hear you fucking my brains out. I am you dirty secretary please fuck me harder on you big desk. Wouldn’t you love to have a girlfriend like me? I can be tonight! Call me and I promise I will give you the complete girlfriend package. You won’t be disappointed baby!

Naughty maid phone sex

Sissy Humiliation with Farah

sissy humiliationSissy humiliation is so much fun. When I was younger, the Internet and smart phones didn’t exist. Phone sex came around in the 80s, however the women, were how should I put this nicely, not as pretty as they are today.  You had no way of seeing what they looked like, unlike today where you can see us first before you call. The original phone sex sluts worked in a warehouse in some cubicle with a headset on, not out of the comfort of their homes like today. A lot has changed since I was young, including sissy humiliation. The Internet has given birth to a new brand of sissies. Pathetic, cross dressing, cock sucking, shameful, pansy sissies who beg to be outed and publicly humiliated. Growing up, a boy got called a sissy for crying. Now you are a sissy when you have a limp tiny dick, enjoy public humiliation and forced feminization. And, when you suck dick wearing something pink and frilly. Now, the folks behind sissy humiliation are not the boys on the playground, they are hot sexy women like me. Bitches in charge who recognize the desperate plight of the modern sissy. Women like me who understand that some men just belong in panties and a frilly dress. Some boys aren’t really boys, just girls trapped inside a loser male body. Some women recognize the shameful nature of  these man girls trapped in the wrong body, trying to act like someone they are not. These individuals need sissy training to become who they were meant to be. Full fledged sissy maids waiting on goddesses like me to dress them, shame them, out them and put them to work for us. Sissy school is now in session thanks to the modern world and hot sexy MILFs like me. Think you can handle it sissy?

sissy humiliation

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