Category Archives: crossdressing

Phone Sex Sissy Gets Pimped By Mommy Anna


It’s time to put on your little panties and come with Mommy Anna. Are you scared? You should be. First, let’s tape back that worthless little dick of yours because you are mommy’s little girly tonight. You will dress like the slutty whore you are. Now I’ve arranged for some men to meet us in the woods. Continue reading Phone Sex Sissy Gets Pimped By Mommy Anna

Cunt Hole Violation Phone Sex


My little sissy slut has been so good that he deserved some special attention from his sexy but mean mistress.  I got him a pink, baby doll night gown with matching pink lace panties so he could dress up nice for me. He went all out for me too.  He got his nails done and his hair done and  all he wanted to do was be my little sissy slut and I could have my way with him.

He whimpered a little when he saw the size of my strap on.

Suck my cock.” I commanded. He sucked it and took it all in as his eyes got wide. He was so turned on, but scared at the same time. He knew what I was going to want next.

I had him get on all fours.

Spread those pretty little ass cheeks apart, Bitch.” I said.  He took his manicured hand and pulled his panties to the side, shaking in anticipation. “Time for you to really become my little bitch.”

Are You a Jealous Phone Sex Sissy?

Mistress Marilyn 866-513-0615

Look at those tits. Aren’t they beautiful.So perfect. I know a little sissy like you is jealous. You should be. They are what you can never have, what you can never be. Real Tits. A pathetic thing like you, a sissy locked inside the body of a pathetically weak man, doesn’t even deserve to look at something so incredible. You are unworthy. Disgusting. A vile fake creature, neither man nor woman. A thing.

Continue reading Are You a Jealous Phone Sex Sissy?

Time For Lessons Phonesex

844-332-2639 ext 257

We need to have a bit of a conversation about how you’re going to be impressing me. I want you to make sure that you have everything that you’re going to need.

So the two of us are going to sit down and have a conversation about what you’re going to need for all of your lessons. Don’t be nervous.

Continue reading Time For Lessons Phonesex

Pussy Loving Sissy Boy Phonesex

1-844-33-CANDY  ext 229

Believe it or not, not all sissy bois are faggot little cocksuckers.  I know there are a whole ass ton of them out there that are but every rule has an exception and this one does too.

Like there is this one yummy little sissy boi that I love to play with. He loves his pantyhose and panties and super cute skirts and he loves pussy! Not that he really gets any but he still loves it! He is so freaking cute in his sissy clothes though it would be so much fun to go out with him and do some hardcore cock teasing. Continue reading Pussy Loving Sissy Boy Phonesex

First Time For My Pretty Girl Phonesex

844-332-2639 ext 257

I know you’re getting anxious. You’ve been pacing this house for the last few hours, but I promise that everything is going to go just fine.

All you need to do is exactly what we have practiced. You need to listen to me, because I will be here every step of the way.

Continue reading First Time For My Pretty Girl Phonesex

You Naughty Sissy Bitch Phone Sex!!!

1-844-332-2639 Extension 209

Don’t think I don’t know that you keep looking at my profiles, and tumblr!!! Just to see what I have been up to! I am a busy girl, and you envy the amazing times we used to have together! How I used to use your information against you, threatening to expose you for the bitch you really are!
You are now and forever my sissy! You need exactly what I can give you so come get it!!!

Continue reading You Naughty Sissy Bitch Phone Sex!!!

Sucking That First Cock Phone Sex


Now that you serve me on a regular basis, there is no turning back. The tasks I’ve had you complete have been part of my master plan and each task builds from the last one.  First, I got you addicted to our sessions so you would only be able to cum under my direction. (As if your wife cares…..she’s fucking around anyway lol) Then I made you wear panties every time you wanted to masturbate. They started out, pretty but not too feminine.

Now they are always pink with a lot of lace and you have to wear them all the time…..even to work.  Soon, you were wearing a butt plug every time you stroked and I sent you on humiliating shopping sprees to buy penis enlargement devices, tampons, and even some women’s magazines. I got you addicted to the Cosmo sex quizzes!

Long story, short (no, not your cock, lol), I got you addicted to me and now I have you addicted to cock.  You never thought I’d make you cross so many boundaries and today you wanted to know if you could just go back to wearing panties. Well, you tell me. Can you un-ring a bell? Can you un-suck that first cock?


Cute, Tight, Little Ass Phonesex

844-332-2639 ext 257

I’m an ass girl. Always have been. So when you brought your ass in here, in those cute little panties, begging me to use your boy pussy, there was no way I could resist.

I know you haven’t had a lot of training, other than the pathetic stuff you do at home along, so I will do my best to make sure that you get treated right.

Continue reading Cute, Tight, Little Ass Phonesex

It Is Called GIRLS Night Out Phonesex


1-844-332-2639 ext. 222

Jill’s boyfriend decided that he was going to invade the sanctity of our ladies night out.  She didn’t have the nerve to say no to him when he insisted that we could have just as much fun with him there. The other girls and I were not happy about this turn of events and developed our own plan of how to deal with his intrusion.

We made sure that we started our beverage intake much sooner than normal but what he didn’t know was ours was tea while his was something a bit stiffer. When time to leave came he was already shall we say judgmentally compromised. We convinced him that it would be fun to let us dress him for the evening out. His outfit went from a casual polo shirt and jeans to a slutty club dress and stockings enough make up to make a him look like a trashy hooker and a pair of lovely sandals. Continue reading It Is Called GIRLS Night Out Phonesex

sissy phonesex, sissy slut training, sissy chatroom, feminization phone sex, domination phone sex, sissy maid phone sex