1,510 results for sissy training

Femboy training was best for him

Sometimes I tend to get a caller that needs a little coaching. This one needed Femboy training. It’s not surprising since I am a sissy mommy and a sissy slut hut site mistress.
This young man called me up in a complete mess of a situation. It seems his mother-in-law decided she was going to force him to wear pantyhose and a bra. But that was not all, he was forced to watch his wife get fucked by her daddy.

So when he called me he was in a dilemma. He couldn’t understand what was happening. One thing for sure though he was not getting that wife pussy anymore. He wasn’t even going to get a mother-in-law’s pussy to fuck either.

Situations like this is why I am here. I help train him to be the cucky  sissy serpent his wife needed.

Femboy training

Prissy Sissy Phone Sex For Faggots

Sissy Phone Sex
A little prissy, sissy phone sex for faggots is what you get. I’m tired of you misbehaving, so I’m going to put your ass in a pamper and you’ll thank me for it. I’ll spank you, and you’ll thank me for it. Sit with that diaper on, you tiny cock loser, and accept your fate.

If you’re lucky, I’ll dress you up in a cutesy little onesie and make you know the full wrath of my fury. We’ll find you a thick dick BBC Daddy to turn you into his little dress up doll fairy princess fuck toy.

Once that BBC Daddy buys you, it’s not online sissy training anymore; he owns the rights to you for life. And you will serve him as the perfect little sissy whore you are, won’t you? You’ll make sure big Daddy’s cock is sucked, that your little hole gets fucked, and filled, and even bred if that’s what he needs.

Daddy’s going to be greedy, little faggot, so get ready to really surrender everything and live the type of Alice in Wonderland fantasy life your pathetic, squirting clitty has only ever dreamed of. Everything you are is thanks to me, thanks to Daddy. I’m the very best of the BBC Sissy Trainer sluts around, and believe me when I say you’ll get yours, bitch.

Online Sissy Training

He Needed a BBC Sissy Trainer

I am a bbc sissy trainer and so is my daughter. She is 18 now and wants to be a sissy trainer and dominatrix like her sexy mommy. She has shared some of my BBC lovers with me over the years. And I have shared quite a few of her black boyfriends with her over the years. Last night, one of her black boyfriends was over when I was training a sissy. This sissy has never expressed interest in black cock or any cock. This sissy just wants to dress up and be my sissy maid. That all changed when my sissy went upstairs to use the bathroom and walked by my daughter’s room. She did not have the door completely shut and my sissy bitch saw her sucking on her boyfriend’s big black cock. My sissy came back downstairs and started drilling me about the guy upstairs. His clit stick was bulging in his nylon panties. I excused myself for a moment and came back with my black suction cup dildo. My daughter’s boyfriend is not into guys at all. But I know plenty of black men who think any port in a storm will do. I texted one of them that I had a sissy bitch who needed stuffed. While I introduced my sissy to my black dildo, she came alive. She was no longer interested in being a sissy maid. She wanted to be a black cock sissy. Well, she was in the best company because I am the best sissy trainer for BBC faggots. She sucked on my black dildo for awhile before she asked for the real thing. That was on its way. My black lover arrived 20 minutes later and broke in my sissy’s ass with the real thing. Nothing feels better than a real BBC in a sissy’s ass. Or my ass either. And just like that as sissy went from a maid to a bbc sissy faggot.

Mistress Phone Sex Cum Eating Training

Something I always wanted a guy to do for me was to eat his own cum. I love cum eating phone sex calls. Well, I am perverse to know that I could really make a guy eat his own seed. Like a straight guy. You will be all worked up and excited and I would force you to lick that semen up off your fingers before the feeling goes away. You will do it for me. You will be my submissive cum eater and I will be your Mistress. Lay back and listen to the sound of my voice. I will taunt and tease that jizz from your sexual member. You will have to instantly put your fingers to your mouth and eat that semen. This is how you prove to me that you are my slave. A good slave does what his Mistress wants. That is the power I have. I make you eat your cum. If you don’t follow through you will get two more chances. You fail all three and I am not going to be bothered with you anymore. So that is my first requirement for my slaves. I may request you buy a dildo or a cage and we will then carry on from there. But first things first. The cum eating initiation into servitude to me.

Mistress Phone sex

The Best Sissy Trainer for Christmas

best sissy trainerGive yourself the best sissy trainer for Christmas. The holidays are right around the corner, and you deserve something for yourself right? It can even be our secret. I have plenty of closeted sissy boys. Most of my sissy callers and clients are married with respectable jobs where imagine is important. What happens with us during our time together, stays between us. Unless you piss me off of course. I have a private sissy client I see in real-time. I have known him for over a decade. He was my divorce attorney. One of the best in the industry. I saw something in him. He knew what I did. At that time in my life, I was not doing sissy phone sex yet. I was a dominatrix. My ex-husband was trying to blackmail me into getting custody of our offspring. I knew if he got custody, he would send our sissy boys to some alternative conditioning school where they could not be themselves, so I hired the best lawyer. He became one of my first sissies. We have had a decade relationship, but he recently tried to black mail me into free training. Like that shit is going to fly. He had no power over me. Being a sissy trainer is not illegal. My sons are trans, and young teen boys, no one can take them away from me. He was trying to black mail the wrong woman. I have nothing to lose, but he has everything to lose. I sent him an email of him in frilly pink dresses and bonnets getting spanked and sucking cock. Over 10 years together, I had a ton of photos. I told him one push of a button and I would send them to his firm, the American Bar association and his wife. I am severing my relationship with him too. I mean you cannot blackmail woman who is providing you with sissy training and not expect her not to fight back. I am a nurturing and sweet sissy trainer, until you cross a line. Then you will pray you had never met me.

Sissy Fun With 2 Mistresses

Sissy girl training Mistress Gypsy and I always have so much fun playing with our beautiful sissy slut TJ. This Christmas we have something special planned for bringing in the new year. Mistress Gypsy got a brand new, purple, double-sided strap-on and we’re going to dress our sissy cum slut up real nice and pretty. Then we’re going to do a sexy homage to Sweet Gwendoline photo shoot starring our favorite girl! We also picked out a gorgeous deluxe pink chastity cage for her little clitty. It’s going to be so sexy watching Mistress Gypsy deepstroak sissy TJ’s tight man pussy while the other side of that purple strap-on pushes deeper inside her cunt. I’m going to love seeing our sissy slut with her pink lipstick all smeared from licking and scooping all the creampie out my slippery kitty while she takes that purple dong right in her fuckhole. We’ll fuck our sexy slut until her clitty leaks yummy cummy through her cage. Then we’ll make her clean that ten inch purple dong on both ends. She’s the perfect sissy cum eater to dress up real pretty and play with. We will train you to be an obedient, perfect, cum-guzzling sissy slut too.

Taboo phone chat

 

I’m Your Sissy Slut Fairy Godmother!

Femboy Training

When I train my little sissies I always tell them to suck cock and get fucked as if I were there cheering them on! All my little sluts know that it’s better to bite off more than you can chew than be a cowardly sissy who can’t take a cock! I instruct with the intention to make my sissies the best cock fucking and sucking little whores around. My sissies are the prettiest, smartest and most slutty little cum dumps any man can have in their beds! I’m so proud of my little baby dolls when they tell me they hang out at glory holes and truck stops waiting for their opportunity to be used and get drenched in cum. If you are a blooming little sissy who needs the guidance of a real whore, call me! Miss Raine always satisfies!

Sissy Phone Chat for the Holidays

sissy phone chatTis the season for sissy phone chat. Give yourself the gift of a sissy trainer this holiday season. My sissy sons love Christmas. They have some extra sexy little outfits this season to wear. I had them fitted for red velvet sissy dresses with matching bows. They look like sissy twins. The are identical twins anyway, but each has a little different style which helps folks tell them apart. One prefers the classic sissy looks: frilly dresses, fluffer panties, Mary Jane shoes and white ankle socks. My other sissy boy is more dramatic. She is a glam sissy. She likes bright colors, bold patterns, big hair, bold makeup. She loves my 80s clothes and has adapted and repurposed most of the things I have given her. They wanted pretty Christmas outfits for their school holiday dance. It is a formal dance, so I knew red velvet was the way to go. I love dressing them for school dances. They go to an arts school, so lots of LGBTQ boys and girls just like them. Last night, I was finishing the touches on their dresses. I had to make a few altercations. One of my lovers was over. We were fucking, drinking wine and he was helping me with some holiday decorations. His dick came back to life when he saw my sissy twins in their pretty red dresses. He knows they are sissy girls. Some of my lovers do not mind fucking my little twin cock sucking sissies. This guy, however, has remained adamant that he is only about pussy. He changed his tune after seeing how pretty they looked. How femme they looked. I am a great at femboy training. My sissy twins bent over, flipped up their skirts and pulled their ruffled panties down around their ankles. They spread their sissy cheeks. My lover spanked their bare asses, before fucking their sissy holes. After they got fucked like good sissy sluts, I needed to clean the cum off their pretty new school dance outfits. I can get cum out of anything. We had a nice evening. I got to share my big dick lover with my sissy girls. They may have out shined me momentarily. I am never out shined for long, however. I know how to take care of big cocks, which is why I am so good at sissy training.

Sissification Contest With My Perfect Sissy

Today I had the most fun with my Sissy Tj she was used for a good Sissification contest. I dressed her up in a pink chiffon rob with pink feather trimming her chastity belt, pink knee-high stocking and white heels. I wanted to show how well of a Sissy training TJ has had so I made her clean my nut filled cunt and I made her lick it all clean. While she licked and scooped the nut out of me with her tongue,

Sissy slave training

I had my BBC friend stick his throbbing in her tight little man pussy to show how well she can multitask and take cock. Oh boy! My sissy Tj did not let me down she cleaned me so well and fucked that Big Black cock like a good Cum Dump. We didn’t stop until we both came hard, and my sissy was all filed up and dripping with lots of cum. I know I won because sissy Tj is perfectly trained.  

Femboy Training in the Morning

femboy training

One of my sissy supremes called today for more femboy training. I love my sissies, but Margo is a sissy supreme. She is the sissy standard that I hold all my other sissies to. She likes to do marathon training. She also likes to make her sissy mom money. That is just one of my favorite things about Margo. She dresses frilly, does some candy and bends over for all the cock that has gathered around to fuck her sissy hole. I am a benevolent sissy trainer too. I am sticking some money away so Margo can get big bimbo boobs. You can be a great cock sucker. You can dress like a pretty sissy. You can act like a pretty sissy too. But without some boobs, and a wig, and makeup tutorials, you are just a dude getting fucked by another dude. Margo is pretty because I have helped her with her sissy training. She looks and acts the part of a sissy slut. Soon she will have the boobs to complete the look. This morning, she wanted an early session before anyone else was awake. I was off today but made some arrangements to accommodate my sissy supreme. I called all my sissy loving bulls. Big black bulls, some hung white married men and some sexy shemales. No one had less than a 9-inch dick. I knew Margo was up for the challenge. If anyone could service all those hung studs, it was her. One after another they drilled her tight sissy hole. No one cared about getting sloppy seconds either. For some sissy shaming, I had her walk across the barn with her skirt up and cum oozing out her hole. It was leaving a trail behind her. I decided that was a waste of precious seed, so I captured it in a mason jar for Margo to drink. One of the reasons I am the best sissy trainer for femboy faggots is that I know that guzzling cum helps your body get feminized.