Tag: Online sissy training

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.

The Beginning Of My Boss’s Transformation

Best Sissy TrainerI work in one of those standard boring offices with a nine to five gig. It fits me most of the time, however lately my boss has been a major buzz kill. He’s starting to complain the clothes I wear are no office appropriate. He went as far as to tell me that my skirts are to distracting for the males in the work place. I’m use to sexism but nothing has really changes until this last week, and I’ve been racking my mind as to why. And a thought occurred to me, last week in the break room I spilled some coffee on my blouse and since I was the only on in there I went ahead and did a quick change. But if that perv was watching the camera then he may have seen me in my pink bra looking through my bag for another top. However, it doesn’t explain his recently attitude toward the way I dress…unless he was jealous. I easily pick up on those kinds of things. So I tested my theory and waited for most of the office to clear out before requesting a meeting with him. I shut his door and pulled the blinds down while he gave me a puzzled look, and then I threw a pair of lace pick panties on to his desk. “Put them on”. He blushed and cleared his throat. “Excuse me?” he attempted to question me. I laughed at his attempted to cover up what I already knew. “I said get you sissy boy ass up and put on the panties, I was very careful to get a pair I was sure would fit you”. The room fell silent and for a minute I thought maybe I was wrong. Then he picked up the panties and started to feel them in his hands and smiled. “How did you know?” he asked. “Because all sissy sluts act jealous around me. I’m everything you want to be, and if you do exactly as instructed I can get you as close as possible to being just like me.”. The happy look in his eyes told me exactly all I needed to know. Now the fun part can begin.

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.

Sissy Slave Training at the Glory Hole

sissy slave trainingI had a busy weekend sissy slave training. I have this one sissy who is a work in process. I have been feminizing her the best I can, however, I don’t have much to work with. She looks more like a transvestite than a femboy. I have dressed her, done her make-up and given her a pretty blonde wig, but she doesn’t look feminine enough to be one of my sissies. I thought perhaps if she swallowed some cum, it would help feminize her more. I dressed her up in a pretty dress. I did my best to make her look pretty and I took her to the glory hole. On the weekend, the glory hole is hopping. My plan was two days of cock sucking and cum guzzling would make her more feminine. Friday night we spent 5 hours at the glory hole. She was such a good cock sucker. She blew 46 cocks. Can you believe that? That was Friday night. On Saturday, we spent almost 8 hours at the glory hole, and she guzzled another 52 cocks. I was keeping track. In two days, she sucked off almost 100 cocks. She swallowed almost 100 loads of man seed. Cum is transformative in sissies. It helps soften features. It helps grow breasts. It helps stop hair growth on the body and it feminizes a sissy. I was very proud of my not so feminine femboy. The cum helped, because she looked radiant today. Something about being such a good cum guzzler pushed her out of the transvestite category and more into the sissy girl category. If you need help becoming a better and prettier sissy, you need some phone domination from a sexy sissy trainer. I want to help you get cum too. I want to help you become a very pretty cock sucker.

phone domination

Sissy girl training

sissy girl training

Sissy girl training is my passion. I would love to strip you down, and redress you  like my little sissy slut fairy bitch. Bring your tiny little cockette over here so that I can look at it. I want to laugh as I put you in panties. You’ll wear them because that tiny excuse for a peepee is more of a clit and that’s what you will call it. I want you to rub your clittie for me through those silky panties and tell me how much you want me to fuck your sweet little pussy hole. I bend you over and spank your thick little ass until it’s red and stinging. I pull your cheeks apart and slide my big thick, studded cock right into your whore hole. You love the feel of my strap on. I’m going to hold you down and fuck your little fairy ass like the cum slut you are. You’re going to be my little fairy hoe and I will own you! I pull my cock out and make you suck it clean. I love watching you lick all of your he-pussy juices off of my strap on cock. You’re my sissy girl and I will fuck you when ever I want!

 

Mistress phone sex

Mistress phone sex“I want the world to know what a sissy I am Mistress.” I look down on him with adoring eyes. “Is that so?” I start to pet his head. “You need the world to know what you truly are. Trust me I know.” “You are not the first sissy to come to me with a confession like this.” And I know exactly how to handle your craving of being ‘The center of it all whore.’ I walk across the room in my thigh high stockings and four-inch black high heels. Twisting around I face you. With my finger, I call you over to me. You crawl over on all fours as good sissies will do. You kneel before me leaning down and kissing my heals. I point to the right of you and see that I have you on live internet feed in your girly pink lacy dress. “Tell the world your name.” He spurts out “um, um… my name is Tim Mistress.” “Very good I praise you with.” “Now tell the world where you are from.” ” He looks at the camera and again spurts out “Texas Mistress.” His face blushes his dick rock hard his dream comes true.

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.

 

Sissy Phone Sex Valentine’s Day with Dark Chocolate

sissy phone sex

I hope all my phone sissies had a happy Valentines Day. I took a break from sissy phone sex to give my sissy sons a chocolate treat. They are at that age where they have become fascinated with big black dicks. I am sure you understand the fascination. They are big, thick and beautiful. The Internet is full of them too. Anyone is only a keystroke away from interracial porn. I have a black lover named Jerome. He is all stud. He loves fucking this mommy with an audience. He also loves helping me with the training of sissies. I dolled them up for Valentine’s Day. They had on pink frilly dresses. Cute little white socks with Mary Jane shoes. I put bows in their hair and I even put on some pink lip gloss. They know how to suck cock. Every sissy should know how to suck dick. This was their first time sucking on anaconda meat. I am a BBC sissy trainer and it was Valentine’s Day. Not a holiday without love and chocolate, right? I fed my sissies their chocolate treat.. They did good slurping on chocolate cocks. They have a big sweet tooth for big black dicks. I am sure you understand. I do too. This sexy mommy wanted some chocolate too. My sissy boys watched their mommy take that chocolate fuck stick in every hole. They were right there to clean up the mess. It was a lovey Valentine’s sissy day.

Sissy Slave Training

sissy slave trainingI love sissy slave training my sissies. I have a few prized pupils. Some are married and must be very discreet with their sissy duties. Others are free to be the best sissy they can be. And a few are single but can only practice from the safety of their home because of stigma. They have jobs or parents that just wouldn’t understand. Breaks my heart when a sissy can’t be who she was born to be outside her home. I have two sissy boys. I knew when they were young what their true nature was. I didn’t guide them to be sissies. I let them explore their sexual identities. And those identities involved wearing mommy’s panties, playing with her make-up and sucking on her dildos. I’d buy them gender appropriate toys and they would play with their big sister’s old Barbie dolls instead. I stopped buying them boy things by the time they started school.  They are still in school, but they go to an arts school. Its LBGQT friendly. They can be themselves. The younger generation gets it. They don’t judge. For you older sissies, the best sissy trainer is a mommy who understands you can’t always be out sucking cock or going to stores and buying lingerie for yourself. I wish you could be like my sons, but I understand different generation and different situations. Regardless if you can go out and get cock and toys like my precious Bambi or you have to stay in the closet like Mickey, this sissy boy mommy wants to help you make the best of sissydom.