Tag: Sissy training

Put on those Silky Panties

best sissy trainer

Michelle tells me that I’m the best sissy trainer that she’s ever had. Michelle came to see me and he was dressed in blue jeans, a sweatshirt and work boots. I raised my eyebrow and told that girl to strip out of that crap right away. He had men’s white briefs on too. I cut them up in a bunch of tiny pieces. Then I put her in lavender silk panties and a white silk nightie. I made that girl put in a thick pink plug and stretch her pussy for later use. She whined but her clit was standing out all hard.
The next training that I gave to Michelle was cum eating. I didn’t want that sissy to embarrass me when she got cum from a real cock. I took a cum covered strap-on and fucked it into her lips. God, that lazy slut hadn’t even made her face up before she came over. I smeared the jizz all over her face with the strap-on and let it dry. That’s how I made her go out shopping. She had a tiny nightie, panties and dried up cum on her whore face. She’s almost ready for real dick now.

My Boss’s Transformation Continued

Sissy trainingOver the next few days, I would slip him a few more pairs of panties with instructions to be wearing a pair each day. Then I observed his behavior. He was happier, more relaxed having someone to share this secret with must have been a huge relief. Each night after work I would stay late (paid of over-time of course) and we would discuss my future plans for him. I took some measurements and we sat down and did some online shopping. I needed to make sure my slut had the proper attire for her debut weekend. Her sissy coming out party had been planned and now it was just getting her ready. First the outfit, we decided on an innocent look as we agreed it would be best given she was a sissy virgin. So white lace panties, garter, and thigh high stockings. A beautiful white satin chemise, with a gorgeous white sheer long flowing robe. The order was placed and set to arrive at my house the day before the party this upcoming Friday. So all that was left was practicing for the big day. I bring my strap-on to work and I’ve been teaching her how to suck cock, and I’ve provided other fun accessories to prepare her sissy pussy for her first time. Soon my new sissy who I’ve finally decided to bestow the name Lily will be more than ready for her big day!

Online Sissy Training

online sissy trainingOnline sissy training available here. I love dressing up sissies. I have a daughter, but a woman can never have enough sissies. I also have two sissy sons. I have been training sissies at home and on the phone for years. It is more than a hobby; it is a job. Occasionally, I get paid to make a sissy. I was paid $5,000 from an unlikely client recently. The client was a woman. She wanted me to turn her son into a sissy. She always wanted a daughter and she had this sixth sense that her son was not going to grow up to be a ladies’ man anyway. Mothers know. If you are a sissy, I bet your mother was the first to know, even before you did. When Sally arrived at my place Friday night, she had her son Trey with her. He thought they were at my place for English tutoring.  He was there for sissy training. He was unassuming for a young boy. He had a naturally feminine body. I didn’t think he would fight his feminization, but he did. I prefer to be sweet and nurturing, but if a sissy fights me, I fight back harder and win. I took that sissy bitch, tossed her over my lap and spanked her. Bare bottom spankings are something I can administer well. After I was done wailing on her ass, I shoved a butt plug in her ass. Her momma helped me duct tape the butt plug in her sissy ass. She helped me dress her too. She was better behaved with that butt plug in her back door pussy. In fact, it made her clitty hard. Once she had a hard clitty, she was easier to train. Sissies get pleasure too. They get twat teased and abused also, but almost every sissy I know loves to rub her clitty. Once we dressed her and pleasured her back door pussy, she transformed before our eyes. She didn’t even put up a fight when her mother and I put on strap-ons and tag teamed her new pussy. She welcomed it. Another sissy converted under my watch.

Cucksucking 101

Sissy Girl TrainingWatching a sissy suck cock can be so amusing. The cock hungry little whores just try to swallow the things which may make the guy cum but won’t necessarily be a mind-blowing blowjob. It lacks a key ingredient that linger with a man after he gets his dick sucked. That my sluts is the art of the tease. If you want to ever be considered among Arabelle’s darlings then you will listen to my advice and learn to utilize it. Any man can find a whore on a street corner to devour his cock for a quick 5 minute nut, but a real woman no matter how salacious have class. I can give a man a blowjob that will have his mind reeling because I know how to take my time. I know how to use my skills to tease every inch of his cock and balls. While still catering it to what he likes. You need to listen to the sounds he makes, test out his super sensitive areas and see how you can make him squirm beneath you for a change. That’s how you become the best cocksucker you can be.

I made her do it

sissy phone sexMy newest little sissy bitch was reluctant to follow all of my rules so I had to punish her. And what better way to punish her than to make her do all the things she was reluctant to do in the first place right? So after she was all dressed up like a little slut I told her I was taking her out for a little surprise and boy did she get all excited. She was acting like she had been a good girl that deserved a treat or something and seriously nothing could be further from the truth. She was really a pain in my ass with all her complaining but that was gonna be changing real quick. I led her into this private club where I had all her clients all lined up and waiting for her. She was going to have to serve each and every one of them before we left there or she would no longer be my sissy. Well she cried about it but you know what? She sucked every fucking dick in the place! They fucked that tight lil pussy of hers too until she had cum running down her legs and she was too tired to stand up. Only then did I take her home and let her rest.

In Need of Sissy Girl Training

sissy girl trainingSome men need sissy girl training more than others. I think I found the biggest loser this weekend. I met him in an adult bookshop. I knew he wanted to go into the glory hole room, but he was too much of a pussy. He was trying to be nonchalant, but I knew he wanted to suck some cock. He didn’t look like he had much experience. I decided he needed a mistress. He was not going to ever be cock sucking faggot hesitating. I went up to him and told him that I knew he wanted to be a cum guzzling, cock sucking faggot. He was in shock. No one had ever said that to him. I told him I was sure anyone who knew him longer than a minute would know. I mean he was transparent. My guess was just no one in his life had called him out on it before. Women know. Some may not want to admit it to themselves that their husband or lover is a sword swallower or a butt pirate, but they know. I don’t turn a blind eye to a sissy or a faggot in need of cock. The world needs more cocksuckers. I led him to the glory hole room and blackmailed him into sucking dick. He just needed that push to do it. You can think about cock all day long, but how can you be a cock sucking sissy if you only think about doing it? You just need a phone dominatrix like me to take you from fantasy to reality.

Tammie gets a Treat

Sissy TrainingMy 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.

Foot Job Fetishes

Mistress Phone SexBesides being an excellent sissy trainer, I am also a mistress whom client’s employ to fulfill their fetishes. I have a client, Mark who has a tremendous foot fetish. He likes to schedule an appointment about once a month. To prepare for this appointment I go to have a pedicure. He likes my toenails to be a deep red and my feet to be extra smooth. He also likes them to be extra stinky, so I make sure that I wear my oldest running shoes without any socks and work out in them for an hour or so before his arrival. When he arrives, I am barefoot. I sit him on the couch and lay down with my feet facing him. He starts by rubbing them and then he starts licking and kissing them. Taking each of my toes completely in his mouth, running his tongue between each one. While he is licking one foot, I use my other foot to rub his cock over his pants until it is nice and hard. I then remove his pants and apply a nice slick oil all over his rock-hard dick. I take my feet and give him a foot job. He lays there and watches with big wide eyes. He doesn’t need to touch any other part of my body and never moves his eyes from his crotch, watching as my feet glide up and down on his hard shaft. I wrap my feet around it and move them up and down, grazing his balls with my feet as I go. When he is close, he lays back and I can see his eyes relax, that is my cue to start rubbing harder and faster, stroking him softly but firmly. Soon he is ready and grabs my feet around his cock and explodes, leaving his warm, thick cum running down my feet and in between my toes. Then he takes my feet and licks his cum from them, between my toes and even under my toenails before scheduling next months appointment.

You’ll Need A Professional

phone dominatrix

If you’re in search of a phone dominatrix then look no further. I’m very observant and I pay attention to the little details that could either make or break you as a sissy pet. If you want to be trained properly, then you better be willing to relinquish all control over to me. Your mistress. I’ve noticed that a common denominator with your sissy boys is that a lot of you hold positions of power or authority in your day to day lives and sometimes you just want an escape. A place to release that pent up pressure and tension if you will. It’s natural and finding a balance between your world and mine is where you’ll find physical bliss and harmony. Just be prepared to commit to this role. I want you to do as I instruct, say as I demand and wear what I desire. This will be the place you come to when you don’t want to have to be making any hard decisions in life. When you just need somebody else. Somebody stronger than you to dictate your next move. I hope you’re prepared to be humiliated and dominated by a true phone Domme Queen.

Sissy phone sex

sissy phone sex

Sissy phone sex is my most favorite thing to do. I love training my sissy girls over the phone and making them rub their little clitties for me. Making sure they’re wearing their pink frilly panties as they make sticky messes for me. When I have them all to myself, I make them dress up for me like the little sissy girls they are. Then I put them on their knees and bring in something they’re not used to seeing. I bring in a real man with a real cock. I make sure they take his huge thick cock deep in their little throats as I turn them into the perfect little cock sucking cum queens! I make sure they gag on him and deep throat him like good little bitches. I love getting fucked right in front of them and making them lick me clean after! Part of making them cum eating queens is making sure they can lick out every drop! My little sissy dolls are the perfect cum sluts.