1,510 results for sissy training

The Best Sissy Trainer is Online

best sissy trainerDo you need the best sissy trainer? I think we are all good sissy trainers on this site. We just have different specialties and approaches. I am a nurturing trainer. That is because I am a mother with twin sissies whom I love very much. I enjoy helping them on their sissy journey. Just like I enjoy helping you on your journey too. I do not care if you are a recreational sissy or a lifestyle sissy, I want to accompany you on your journey. I have helped my sons go from panty wearing sissies to cock sucking faggots. They are still young teen boys, but they embrace their sissy nature. No closets for them expect for storing their pretty dresses and things. They have long hair. They wear make-up. They dress feminine. And they take cock in their sissy holes. I was teaching them to suck cock when they were still playing with dolls. I always had a lover who wanted nothing more than to let them learn how to suck cock using his dick. I realize not every boy has a mom like me and not every man has a sissy trainer in his world. That is the beauty of online sissy training. We never have to meet. I can help you on your sissy journey regardless if we meet. You just must put in the work. Are you ready to begin your sissy journey?

Sending You My Sissy Panties

Sissy trainingDressing my sexy men up is my favorite thing!

I love teaching them how to be slutty little princess sissies. We learn to dress pretty, do our hair, walk in high heals and of course, we learn to suck cock like a pro!

I had a little sissy in training who would always take pictures of himself in his wife’s panties before doing our call. He would send me pictures and tell me that he just did not feel pretty!

Well no wonder! You can’t be a sexy sissy princess in granny panties like those!

So the next day, I sent him the panties I was wearing. I literally mailed him the panties off my ass!

I told him to take a picture and send it to me and he looked so pretty wrapped up in my lace panties!

I could tell he was starting to feel like a real sissy princess because his cock was getting hard.

But that is a naughty little sissy! We keep our cocks under control by any means necessary!

We are not above pinching that meat or taping it down!

After all, sissy princesses can not walk around with big tents under their pretty frilly dresses!

Being a good girl means being a lady, wearing heals and learning to swallow like a good little slut! Ladies never spit!

 

 

Sissy Phone Sex Isn’t For Weak Bitches

Sissy Phone Sex

Even though we’ve been through several rounds of sissy phone sex training together, I know you aren’t ready to go to the royal ball or to worship the balls of royalty! I don’t trust that you could carry yourself with poise, little girl. I know you crave to be a little fem boy bitch, and that’s exactly what I’m going to make you. But you’re going to need lots of practice sucking cock before I even think about letting you step foot inside that Ballroom.

You need to learn how to deep throat it, fluff it up so it’s all nice and ready for the Queen to get her royal cunt fucked perfectly. Think about how it would look if I brought some under trained sissy out to suck the cocks and worship the balls of my guests. The kingdom would revolt, and then I would have to punish you. Oh I could flay you, or beat you, but my favorite thing to do is to edge you endlessly.

That’s right, if you displease me after I finished training you for this, you’re going to regret it for the rest of your life. The last time you came will be the last time you ever cum. I’ll keep you locked up, tight under key and shackle in my dungeon, and you’ll be stimulated everyday all day on that pathetic clit of yours. Why? Just to drive you crazy.

So, stand up straight, give me your best sissy girl smile, and get ready for the most dangerous thing you’ve ever had to do; please the Queen.

Online Sissy Training

Sissy Phone Sex Birthday Celebration with BBC

sissy phone sexIt was a sissy phone sex celebration this weekend. My sissy boys had a very special birthday. I wanted to celebrate in a way they would appreciate. Friday, it was a pampering day. I took them first to get their hair done. They have grown their hair over the years, and it is longer than mine now. They wanted some pink hair, so I splurged. They have pink hair with some curl. Our hairdresser put some layers in their hair to give it some bounce. That was followed by getting their nails and toes done. They love glitter polish. Saturday in the afternoon, we went shopping. They each got some pretty new clothes. I even took them to Victoria Secret to get some undergarments too. It really is the bra and panties that make the sissy. There was a reason I wanted to pamper them. At their party Saturday night, I invited a few black lovers to join the festivities. I am a great BBC sissy trainer because my sissy sons share their mommy’s love for big black cock. My black studs love fucking my sissy boys. I bet you would too. I played with my pussy as their little backdoor pussies got thick and long black dong. I had enough black lovers in attendance that my sissy boys could take black cock at both ends. It was a proud sissy mom moment.  My sissies loved their special birthday weekend. They got pampered and they got fucked. I was so impressed with them. I have been training them for years to be black cock sissies. I can train you too. One of the nice things about black men is that they will fuck any tight hole. They do not care if it is a sissy ass or a milf pussy. If I can make my sissy sons black cock  sissy fags, I can you too.

Service Sissy Slaves

Online Sissy TrainingDoing online sissy training is not as easy as it might look. And ruling this kingdom is its Queen is even harder. I have to entertain several guests, regularly. And trying to keep those men interested is so difficult. Sometimes they bring their wives, and every once in a while their offspring.

Last night, I had a full house. It was the perfect time to show off my little sissy bitches. I dressed them to the nines, even stuffing their bra since their hormones were only just starting to work on their tits. Their little clitties were stored away in chastity cages, hidden underneath frilly silky panties. They wore sweet flowing gowns, and their hair had grown out long and was done into beautiful braids. My perfect princesses.

In the middle of dinner, I could see several of the men start to get antsy. So one by one I sent my little sissy sluts under the table. They unzipped their pants, and went to town sucking on their hard cocks. Well, the women started to wonder what was going on, and when they looked under the table and saw my pretty princesses down there slurping on their husbands cocks, well they got pretty jealous. More of my princess girls crawl under the table, moving the ladies panties to the side so they could look at their sweet pussies. Even the young ones were starting to wonder, and so I sent the last of my girls underneath of that table to play with those young sweetlings, giving them a taste of my Royal hospitality.

I know that this was your favorite lesson, being a service slave to me. I know that you still crave it to this day. To be used simply to pleasure my dinner guests, of course it can be done if that’s what I want. I’m in charge baby, and you’re forced feminization is all that I care about.

Humiliation Phone Sex

A Little Bit About the Best Sissy Trainer

best sissy trainerAre you looking for the best sissy trainer? You are in the right place. Not just with me either. All the sissy trainers at this company rock. Let me tell you a little bit about who I am as sissy trainer. I am a mature woman and a cock size queen. I have been a size queen since I was in high school. I date a lot of black men and that ruins you for white dicks. I married a white man, however. That was a mistake. I divorced a white man too. He did give me a hot teen slut daughter and two sissy boys. I raised them to be sissies because it was their destiny. They were cursed with small willies. They are what you would call gender fluid. They identify as both sexes. While I was raising them, I supplemented my support from my ex-husband with sissy training adult men. I did some BDSM work too. Now I am a phone trainer and take all my knowledge and experience to help you become the best sissy you were made to be. I am a nurturing mommy. That does not mean I will not punish you, because I am big on discipline. I just prefer to encourage your growth as a sissy and use humiliation when called for. Sissy calls are not all I do either. When you are a sissy trainer, cuckold husbands and adult babies call you too. I am a dominant woman, so I can handle all variations of a sissy. I am a fair sissy trainer, but not easy. I require dedication and you will do assignments like suck cock at glory holes for me. When you disappoint me, you see my bad ass bitch side. So, do you think I am the sissy trainer for you?

Owning a Sissy Slave

I’m always up to gaining a new sissy and my Sissy Slave Training sessions are great to explore your naughty desires. I love that you will call me while already wearing your pretty panties like a good sissy. I enjoy how excited you are to tell me about yourself and what you desire to accomplish with our sessions. It’s my desire that you get around to worshiping and sucking big cocks for me and I love to hear every detail.

Meanwhile as we work you up to that I expect you to have a large penis dildo to service with your sissy lips. You will find the suction cup ones to be the best. These realistic penises are great for making your own glory holes to service cock and slide up and down on once we get that sissy cunt trained. I look forward to playing soon Sissy.

Sissy slave training

Royally Humiliated During Sissy Phone Sex

sissy phone sex
Welcome to the Humiliation chamber, my favorite place to be during sissy phone sex. Our lesson today involves one bad sissy girl, the one you see hanging from the ceiling just there. He’s naked, and his tiny cock has been released from it’s chastity cage. His arms are bound above him as he swings from the ceiling. I see how excited you are; you won’t be after you see what I do to him.
I circle him, riding crop in my hand as my black stiletto boots click click click on the floor as I pace. His body is rigid, terrified. The blindfold does it’s job, and the ball gag in his mouth prevents begging. I’ve been force feeding him watered down wine for hours. I love online sissy training. See the bulge in his belly? That’s his terribly full little bladder. I stroke his cock with the riding crop, and his wiggles and moans, trying to get as much contact as he can before I ghost away, leaving his balls full and his poor cock dripping.
I lay a few blows on his ass, but then start to beat where his agonized bursting bladder is. He knows he is forbidden from pissing until Queen Presley says it’s okay. I make three other of my sissy girls go, and stroke and fondle his cock and balls. The third one in my sissy training plays in his asshole. They edge him, getting him as close to the line as I dare let him. He’s begging, so I remove the ball gag. “Do you want to piss or cum?” I know if he cums, he’ll lose control. The poor sissy slut chooses to pee, but I make him watch as he has a huge accident in front of the whole court.
Of course we all laugh. What was his transgression, you ask? Oh, he couldn’t make me cum in under five minutes during his forced sissy training. I stare at the rest of my sissies, and grin maliciously. “Who’s next?”

Online Sissy Training

Domination Phone Sex Sissy Mommy

Domination phone sex Sissy Mommy is who I am and I am here to assist in your sissy desires. My pampering mommy side is always a good side to help a sissy out of her shell. The dominating side is the best guidance most sissy girls require to get them trained to be good little cock whores. I am multi-faceted and experienced in all kinds of domination and sissy girl training. I find it exciting to help you in your journey into woman hood and encourage you all the way through the process. The Quarantine gave many time to reflect on their life and to explore some of the things they never got to prior to such. Many have been lucky in keeping busy with work, like myself. I know that you work hard and in the down time you couldn’t enjoy the usual life you led if it was based on socializing. Things have been difficult and those that have recently discovered their feminine side and started to embrace it should know that I am here for them. Whenever you just need to talk or get off some of the manhood stress and let out the side of you that you long to be. I’m here for you my beautiful Sissy Girl.

Domination phone sex

Sissy phone chat with Miss Remi

sissy phone chat

Everyone knows me as the ultimate sissy phone chat princess! I love to make my sissy sluts dress like little whores and tease lots of fat cocks! My pets stroke and tease the biggest cocks and make them cum all over my sexy little feet. I make my sluts get on their knees and suck my little toes to clean all of the cum off! If I see a wet spot in the front of their frilly little panties, it really turns me on! I keep my sissy pet, Candy right beside me at all times. Her silky panites are always sticky with pre-cum when she’s with me. She’s been trained to be my cum cleanup slut. Watching Miss Remi get fucked makes her clittie hard and she begs to lick the cum from my pussy. Of course I make her take a fat, hard bull cock in her little pussy as she’s licking my kitty clean. We’re always looking for new sluts to train. We’re not going to turn you into anything that wasn’t already deep inside of you, waiting to be set free. When you’re ready to begin your training, I’ll be here waiting for you!