1,509 results for sissy training

Open Wide For Daddy’s Size!

Sissy Girl Training

Pretty little princess sissy bitch, open your fucking mouth. I’m not going to play nicely with a slag like you, so unhinge your damn jaw! There you go sweetie, very nice. I need you to smear that nice, rose red lipstick I spotted onto your face all over his cock. I know it’s quite large, probably about thirty five centimeters long (that’s 14ish inches, for you American perverts!) and he’s quite thick, so I hope you’re ready to really choke darling.

There, stick out your tongue so he can drop that heavy chocolate onto it, and you can get your first real taste of an Alpha cock. This Bull has more semen swimming in his sac today than you’ve had in your entire life. And that’s why your little dicklette clit stick is locked away in a pretty cage. Only the real men get to play today! You’re a little lady who’s going to choke his big cock down.

You can’t? Then let me help! A fistful of that wig glued tight to your scalp should help. I’ll force your throat down over this dick again and again. Choke the fuck away, bitch. You should have done what Queen Presley said.

Humiliation Phone Sex

Your First Appointment

mistress phone sex

You called to set up an appointment, your first you said. Interested in a Mistress to train you. I like my newbie’s; they are fun and come to me not knowing what will happen to them. You walked in wearing a pair of khakis and a button down and loafers. A businessman I could already tell. Sometimes having all that power makes you yearn for complete domination in your deep dark private life. I knew this was going to be fun.

You still had a little authoritative attitude, and I was going to quickly squash that. You sat down and I told you to stand. Now that you are in my training you will not do anything without my permission first. Puzzled you were but you complied and asked. I told you no. I told you to follow me. For your first training we will be fitting you with a pair of panties and a small but mighty butt plug.

You quickly said no. I told you never to tell me know. As you stood, I unbuckled your pants and removed them. Took off your boxers and pulled out a pretty pink pair of panties. Your cock started flinching as I pulled them up. Now baby, bend over. You bent over the couch as I grabbed the lube. I pulled your panties down and pushed the tube up your tight little asshole. You shook, but not in terror, your little cock was overly excited. I took the butt plug and as I started pushing it in your asshole you clinched and let out a moan and exploded. What do you think I should make him do with his mess?

Be My ‘VIS’ Darling!

Femboy Training

My “VIS” meaning my Very Important Sissies pay extra to have a full day of shopping with their favorite trainer! I start the day with a bit of pampering, we go get our manicures and pedicures as well as some waxing and facials before getting a massage and going for a hair appointment. It is so fun to feel so well pampered before we go spend some serious money on our clothes and accessories. We go to the luxury boutiques and spend a small fortune on shoes, lingerie, corsets, nighties and robes before venturing over to buy some pretty ready-made dresses and outfits. Our last stop is a little couture boutique where we get fitted for a couple of gorgeous custom gowns because every sissy of mine needs to be pageant ready at a moment’s notice! Don’t you want to be my VIS Darling?

Time To Turn Tricks

mistress phone sex

Oh, what a lovely job my sweet sissy has been doing lately. We have been training hard and she is wonderful. Her sweet little clitty has adjusted perfectly to her little cock cage and her sweet pussy is always puckered and ready for whichever butt plug I pick out. She has been my cock sucking, cum sucking queen. So as a reward I told her to pick out the sluttiest outfit she could find because we were going out to have some fun.

She never disappoints. She came running from the changing room and twirled with excitement. The bitch was fine. She had on black fishnet thigh highs, stripper boots, crotchless black panties and matching bra and a short black skirt and crop top. I applied some hot glittery pink lip gloss, smacked her ass and off we went. She had no clue where we were headed.

I stopped the car and parked and told her to get out. She looked confused but I kissed her cheek and told her tonight she would be my whore and I would be pimping her sweet tight ass and pretty glossy mouth out to all the perverts. She practically jumped for joy as I stuck my hand under her skirt and felt her little clitty leaking. I laughed as the perverted men started pulling up. I held my hand out and took the cash, smacked her ass, and told her to make sure they had a good time. Should I trick you out too baby?

Nancy Nylons with Pics!

Sissy maid training

The following is a exchange about sissy maid training and more with a real sissy and real sissy pics!

Nancy nylons : Merciless….. thanks to You handcuffing my manicured hands to my red six inch high heels in order for me to be totally under his control.

Zoey: Yes completely handcuffed and willing to be our slave. You are going to be the perfect subject for other sissy whores. Glossy precum lips! Throat full, My strapon on you pretty pink puckered. sissy hole

Nancy nylons : Do You think that I should rub my lips with the precum oozing from my member right now? Just to tease us both right now and fulfill the sissy responsibilities of eating every bit for You?

Zoey: Yes you should baby you are the perfect whore run it all in right now that’s an order! Yes your sissy responsibilities are on you right now ! Do it baby wear you sissy panties proudly as you do! 

 Nancy nylons : I’m coating my lipstick for you now and spooning it with my fingers onto my tongue! I’m so happy that You agree with all of the women who have participated with Nancy in crossdressing over the years- every one of them took it upon themselves to be up front and inform me that if boys like me wanted to dress like a slut, Nancy would be always required to eat up all the mess that Mistress allowed her to make. You are All so hot for that- I feel so small when I partake in cum eating while Women watch me! I’m sorry but I’m completely covered in my mess and must clean it up. Thank you so much and maybe we can Skype next so you can watch it and make fun of me. Perhaps You could tell me exactly how to eat it for you to enjoy the show the most— I think I could cum on my patent leather stilettos if you want to record it!!!

Adult Phone Chat Lines

Adult Phone Chat Lines

Adult phone chat lines are an excellent way to get out all of your sissy boy frustrations. Mistress Genesis knows how much you enjoy being told what to do. You need commands and discipline. Be a good boy for me and put on a pair of those satin panties I bought for you. I love to see you dress up for me and prance around like a good sissy boy needing domination. I’ve always been a woman that lives for control and you need a firm hand. Be an obedient boy for Mistress Genesis and dress up the way that I want you to. We will begin your training with a few spankings for not listening to me. I want you to bend over the sofa and take your whippings for me. Humiliation is the only proper way to train you. I will laugh while you pull out your puny, pencil-sized cock. You think you’re enough to please a woman? Think again, Sissy. You’ll need a few more training sessions.

Mistress Phone Sex

Mistress Phone Sex
Mistress phone sex is what I provide for my army of sissy slaves. If you’re lucky, I can add you to my collection of sexual pets. I am a powerful, dominating woman who knows what she wants in life. Sexual satisfaction at all times. Sissies like you don’t know how to satisfy a woman and that’s why you come to me. Be a good boy for Mistress Genesis and put on a pair of those satin panties while you watch me fuck my newest slave, Ella. As much as I love training sissies, there isn’t anything like the feel of a dripping, young pussy. Breaking her in was easy. She loved the feel of my strap-on pumping her twat. Tying her to the bedposts and torturing her with the vibrator was my favorite part of our training session. Teasing her close to climax and then removing the vibrator… I did this over and over until she was begging for release. Do you wish to be added to my army of sexual servants?

Phone Dominatrix

Phone Dominatrix

My name is Genesis but you will call me Mistress. I’m skilled at my art as a phone dominatrix. I am a very dominant woman who knows what she wants. You want to be fucking used and I am here to treat you like the worthless trash that you are. We will begin our session by training you on how to correctly worship me. You are here at my disposal. You will be forced to submit to me and lick every inch of my body. That’s it, sissy. You don’t know how to please a woman, but if you’re lucky I may let you practice. Don’t be discouraged when I laugh at how pathetic your attempts are. You’re like my subservient dog who will lick up any scraps that I have to offer. You will be trained on how to please me, on how to worship me. Let’s not beat around the bush. I’m going to use you and train you like the little sissy bitch everybody knows you are. You should be so lucky that I would spare a minute for you.

Fierce Mistress Phone Sex

mistress phone sex

So, you’re online looking for a Mistress phone sex goddess to call. I don’t know if you have stopped to think about what that might mean for you, but maybe you should. When I answer the phone and you say “Hello Mistress” that automatically will change the dynamic between us. I am no longer going to be the sweet, loving sissy trainer that you might have gotten otherwise. I will order you to do more than just put on a pair of lacy panties. This is going to go far beyond that kind of training, so I hope that you’re ready for it.

I get calls from so many wannabe sissies who don’t want to get fucked. I’m sorry to tell you, but you’re not really a true sissy until you’ve bent over to have your pussy fucked by a big fat cock. You don’t have to do it all of the time, but you WILL do it if you’re going to be my sissy slut. Are you ready to submit to me and do what I tell you do to? I’m not really for the faint of heart, so you’d better make sure you can handle me before you call.

Taboo phone chat with Miss Remi

taboo phone chat

I’m Miss Remi and taboo phone chat calls are my favorite way to tease slutty, little sissy whores like you! I get so turned on when I’m rubbing my hot cunnie and talking them into doing what I want them to do. Telling a sissy bitch to dress up for me or to get on his knees and open his slutty mouth for my fat strap-on, makes my perfect, pink pussy so wet! I can’t help but to get a little carried away when I’m training a new bitch. I make my sluts gag on my thick fuck rod before I bend them over and let them show me how well they can take it. I love making my whores pull their pretty panties to the side and beg me to take that pussy hole. I always make them moan for me while I pound my 11 inch dildo into their sweet cunnies. If you’re looking for a new mistress who will put you in your place and train you to be a proper sissy bitch, let me know. I have plenty of time to train more little sluts!