Category: Online sissy training

A Hot Shemale For Tammie

mistress phone sexMy sweet little Tammie has been such a good girl lately. Doing everything that was asked of her. She had been our little cum whore at my last penis party and even licked up my creampie pussy without even being asked. She stayed on her little knees and sucked every man and shemale that came to her so that they were nice and hard and ready to go. She politely lifted her sweet ass and let them take turns ramming their dicks or dildos deep inside her. She cleaned everyone up too, leaving not a drop. So, to show her how wonderful I though she had been I got her a special present. Laid on the bed was the prettiest pink dress and matching garters, a pair of silky hose, black heels, toe rings and a beautiful new cock cage. Her eyes lit up when she saw them, and I told her to put them all on. I had her twirl round and round as she showed her new outfit off. Finally, I told her to lay down on the bed because her best present was yet to come. I could see the liquid dripping from her sweet cock cage from excitement as Sandy, the biggest, blackest, most beautiful shemale entered the room. I handed Sandy the key and told her that Tammie was ready to play as I winked at her and closed the door.

Dick Training 101

Humiliation Phone Sex
So you want to be one of my sissy girls? How well can you handle thick, throbbing dick? If the answer isn’t “like a fucking pro” then sit the fuck down and shut the fuck up. If you want to be a real girl honey, you have to be able to ride with the big bitches and roll with the cum shots. That means being able to swallow a cock as if you’ve never even heard of breathing.

Can you get face fucked for hours on end like a proper whore? Of course we’ll allow for sips of water; have to keep that mouth pussy lubricated so those bull cocks can use you properly. That’s what you’ll be meant for, little girl. At least in the beginning of your residency in the Halls of Sissy Slutdom, your main job will be fluffing the nutter if you know what I mean.

That mouth and those sweet, manicured hands will need to be precise in keeping those Kingly cocks hard for the professional sluts; the real women. Our cunts will be used to milk delicious creamy cum out of those swollen mushroom tips. You’re going to help us keep them hard on our water breaks.

In return, maybe I’ll let you use that nasty girly tongue of yours to scoop the remnants of our fuck fest from our swollen pussy holes.
Sissy Training

I’m a Size Queen

Humiliation phone sexI am a size queen. When I was a young girl, my mom listened to Motley Crue. She was stuck in the 80s decades later! When I saw the infamous sex tape Tommy Lee and Pam Anderson made, I told myself I only wanted cock if it was big enough to steer a boat. How many guys can steer a boat with their cocks? Not many. Hell, I have met a few who could not drive a Matchbox car with their dicks, LOL. Tommy Lee has ruined me for men like you. Once a woman knows there are much bigger cocks in the world, she is not going to waste her time with small dicks. Sure, I have to date some losers like Max. Notice I said date, not fuck. Once I realize they either lied about their cock size or I assumed wrongly, I split. Max lied. He told me he had 9-inches of hard meat. My foot was longer than his cock and I have a size 6 shoe. I laughed at his cock and he called me a cunt. He wanted to play games; I was ready for him. I kicked him in the balls and administered some much needed cock and ball torture. No matter how big or small a set of balls are, men always fall to their knees when kicked between the legs. Maybe Max will remember the next time honesty is the best policy.

I Love Cuckold Phone Sex

sissy phone sexI love cuckold phone sex. I am a size queen and if you call me thinking I will fuck you and you have a small dick; well, you are shit out of luck. This dude called me last night bragging about how he could satisfy me. He said I needed him. He talked himself up so much, I smelled bullshit. He thought that a five-inch cock was what I needed. I am a hot babe. I make men pay thousands of dollars to have sex with me. I have had some of the biggest cocks around and this asshole thought 5-inches would blow my mind. It did, but not in the way he had hoped. Small dick humiliation was the best he could hope for with a pathetic appendage between his legs. At first, he was calling me names and telling me a phone whore should do whatever the paying caller wants. I had to school him on the difference between me and other phone sluts. I am not a submissive whore. I am a sexy gfe size queen. You need a big dick and a big wallet to please me. My loser caller finally accepted his fate as my little slave. I managed to get some pussy and ass worship out of it and a promise that he will never try to dominate a woman again with a sub par cock. The nerve of some men.

Sissy Phone Sex Brings Mommy Joy

sissy phone sexSissy phone sex is so much fun. So is training sissies. Honestly, it is almost criminal that I make the kind of money I do this way. I have a real time sissy who I have been training since he was in high school. I am like a bonus mom to him. He is a friend of my daughter. He is a couple years older than her. One day when he was still a young schoolboy, I caught him in my bedroom trying on my pretty things. For his age, he had a great understanding of what pairs well. I mean he had on a black garter belt, with black stockings, matching black and red bra and panty set. He had them all on correctly too. His young hairless body was perfect for the look. I put a little lipstick on him and got a pair of my daughter’s heels and a sissy was born. His father would have disowned him if he ever found out that his son liked to wear panties and lady’s lingerie. I became a second mom to him. I was his sissy mom. I still am. He is 20 now and still in the closet to his family. I have been sissy training him for 7 years now. He is like one of my own sissy boys. He likes to wear women’s clothes and suck cock. And guess what? So do lots of men and there is nothing wrong with that. Fuck anyone who tries to ridicule or shame you for wearing a pretty pair of panties or wanting to suck a big fat cock, even a big fat black one. Just like I nurtured my boys and my bonus sissy son, I will nurture you too. I love being a sissy mom to my boys. And I will love being your sissy mom too. You can have discreet sissy girl training with me, honey.

Femboy Training with Tamika


femboy trainingMy favorite calls are femboy training sessions that leave my pussy dripping. I love showing men how inferior they are to women like me. My favorite way to keep my little boy toys in line is through humiliation; I’ll humiliate my small cock boys especially. I love little dick teasing. I know exactly how to put these bratty subby boys in their place. No man under seven inches could possibly please my perfect princess pussy. You things get put right into chastity cages, and I throw away the key! I dress you up for sissy maid training. You need to learn how to get bent over and have your anal fuck hole destroyed while balancing in pretty stiletto heels. Then, you’ll need some cock training. It’s a fine art, sucking cock and getting throat fucked. It takes a certain elegance and grace. You crave a woman like me to force you to your knees and hold your mouth open while I make you eat hot load after creamy load of Alpha Cock cum. Best learn to love the taste, that cum is the majority of your diet now/ My wet pussy is dripping. Get up here and eat my bush, make me scream and cum, and maybe I’ll reward you. I’ll ass fuck you with your pretty pony butt plug. Don’t test my FemDom temper. I will consume you.

Marissa Your Sissy Mistress

sissy slave trainingHave you been a good slutty sissy boy playing with your faggot man cunt for me? I’ve been preparing your man pussy for this moment and you better be ready for it! I’m bringing in all eight black alpha cocks to tear into your trained sissy hole. If you don’t think that’s enough for your sissy cunt then we’ll just bring in eight more. Don’t forget to be wearing your sparkly pink slut panties and matching tights. I’ve been training you to be such a good cock sucking slut while you’re grabbed by your little pussy boy ball sack! We’ll have to get rid of that for being such a girly sissy slut, don’t forget to clean up all the cum that’s shot out at your sissy face and sissy boy pussy! I wanna watch as your sissy slut hole is violently fucked by those black cocks spreading you all out and making their huge loads of massive cum spilling out and covering you all up in it! Don’t miss a drop of that hot white juice, be a good sissy boy for us!

Sissy Maid Training Goddess

sissy maid training

Oh, you poor thing. You are in desperate need of some sissy maid training, aren’t you? You tried – I’ll give you that. But if you want to be a perfect sissy maid, you need to do a little better. You didn’t even shave your legs. Do you think any man is going to want you in his house to clean for him and then service him looking like that? I don’t think so. But don’t worry. I’ll send you to have your legs waxed and then you’ll look like a million bucks.

Of course, there are women who might also hire you to do their cleaning. I was thinking that it would be fun to have parties where all my girlfriends come over and you could serve us drinks and snacks and then while we enjoy them, you’ll get down on the floor and clean it with a toothbrush. Oh, there will be so many giggles and I’m sure your little clitty will be so excited. If you’re a really good sissy maid at the party, I’ll fuck you at the end of the night. I know that sounds like fun to you, so why are you not on the phone yet? I’m waiting.

Mistresses femboy training

femboy trainingWho’s my favorite little sissy boy? I had so much fun last week playing with you! Didn’t you love wearing those sexy tight stockings for me? I hope you’re ready for your next session with your favorite mistress Marissa.  I’m sorry if I seem a little harsh or forceful but how else do I take over my shy sissy. I love to make you squirm and prepare your sweet tight asshole to take this large alpha black cock I have waiting for you. I know how much you love alpha anaconda cock deep inside your tight femboy hole. I so excited to play with my tight pretty pussy while I watch you get your tight faggot pussy stretched out and get covered and full of a big fucking load of hot big black cock cum! Let me teach you how to be such a good sissy bitch boy for me and all of my big black cocks for you! I love playing with my sissy boy, humiliation and teaching you to be a good sissy faggot is what makes me wet! Put on your pretty panties and hurry up!

Let Me Push It In For You

Today was a fun day. I had picked out the sexiest pair of black thongs and matching lace bra for my favorite sissy. He is a muscular good-looking guy who I have taken great pride in breaking. He came in wearing some tight jeans and tight white t-shirt. Showing off his muscles and well-defined ass. I laughed as he came in asking if I thought he looked good. No, I do not, now get undressed and meet me in my room love. He came in and, on the bed, I had those black thongs and the lace bra. He smiled as I handed them to him. As he went to put on the panties, I stopped him. Not yet I told him as I reached under my bed and handed him a gift bag. He opened it and pulled out a big thick jeweled butt plug and a cock cage to match. He tried to tell me no but that just got him a paddling. Over my knee he went and out came my wooden spoon. I spanked him until his ass was nice and red. Then I spit on the butt plug and made him stick it up his tiny little tight pussy. He was going slow, so I put my hand over his and rammed it all the way in. He jumped as if in pain but the little droplets on his clitty told another story. I pulled him in front of me and caged him. Now put on your panties and bra and then put your clothes over them. The outline of his black bra showed through his white shirt nicely. Now it is time to head to the mall baby, let’s go.