Category: Femboy training

Celebrate Your Independence Now

Now that the 4th of July has passed, you can do some of your own personal celebrating with the best sissy trainer Diana. I love my Sissy sluts and want to be a part of their celebrating of their own identity independence. Accepting your true feminine selves is a big step and once you feel the freedom it offers to be so accepting you can celebrate You! I am here to offer some guidance and a friendly ear for you to get some of the stress or tension off that comes with wanting to be different that what others expect of you. I am the nurturing mommy that can be here for you and I accept you as you are and I will help you be the best little cock sucker you can be and the best little sissy you desire to be.

Best sissy trainer

I blackmailed him

sissy phone sexThis little sissy slut was coming to me for training but for whatever reason he was very resistant. He even threw away all of his girlie clothes and panties and all that, can you believe that nonsense?? Well I was tired of his bad behavior so I went to his house and made him dress up with all the clothes I brought with me. Then I took a whole bunch of pictures and told him that if he eve disobeyed me again that I would publish them all and make sure that everyone he knew saw them. Oh boy he was definitely ready to obey me then! He was freaking out and crying and begging me to keep the pictures a secret, it was hysterical! I just laughed at him and told him that I would do whatever I felt like doing so he better keep me happy or else. Well, he handed me a wad of cash, took me shopping and promised that he would keep me happy so for now I will keep those pics to myself. I wonder how long he will last before he pisses me off…

Do You Need Sissy Slave Training?

sissy slave trainingSissy slave training is what many of you need. I get guys all the time that tell me they are good sissies or good subs, but they are a far cry from “good.” They need a sissy trainer like me. I met Mark on a sissy fetish site. He sold be a bunch of bull crap. He was just a pretend sissy. When he arrived, he was dressed like a man. He didn’t even have a sissy bag to change into. He didn’t suck cock. He didn’t wear panties. He didn’t eat creampies. Like what the fuck? How do you call yourself a sissy like that? I decided to ease him into the sissy life. The real sissy life. He said he wanted to worship me like a Goddess. I am good with that, but a sissy does so much more. I had him eat my pussy. I waited until after I squirted on his face, however, to tell him I had another man’s cum in my cunt. I had a lot of spunk inside me too. He licked it all up unbeknownst to him.  He was not happy when he found out he ate a man’s cum from my cunt. I told him I am the best sissy trainer around and if he wants to be a sissy he better get with the program. Sissies take orders. They never give them. Every sissy trainer is different, but if you are my sissy, you will clean up cum in my cunt. You may suck cock too. You may even get dick in your back door pussy. You will definitely dress the part. I will feminize you head to toe. So, don’t call me for sissy boy fun unless you can take orders like a good sissy boy! There is no such thing as dominant sissy.

Glory hole punishment

Taboo phone chat

One of my sissies needed a little lesson on obeying orders and listening to his mistress. He also needed to be punished and humiliated too. I had the perfect punishment for him! I took him to the nastiest and seediest sex club downtown dressed in fully sissy panties, makeup, and heels. He had to walk through the parking lot and the front of the club in nothing but panties, makeup, and 4″ slut heels. I lead him through the club to the grimy dirty bathroom stall and made him get down on his knees on the filth covered floor and wait by a hole in the disgusting wall for a big cock to poke through. A really dirty looking uncut cock slid through the hole and my little sissy started to gag when his face got near it. I gave him a sharp smack across his ass and told him if he didn’t start sucking, I’d put his ass up against the hole and let them fuck him. He hesitantly obeyed and sucked the nasty dick like a good little sissy bitch and even swallowed when his mouth was filled with cum. That was just the first dick too, I had him on his knees for hours sucking any dick that came along, no matter how filthy or dirty they were. This is what happens when sissies don’t obey their mistress. They need to be taught a lesson and punished. You have to remind them who’s in charge. I love humiliating a sissy and most of the time they love it too, even if they don’t want to admit that they love sucking big black cocks, but even sissies have their limits and don’t want to suck nasty dirty cocks from a filthy glory hole bathroom for hours. He should have thought of that before disobeying me though.

Become Your True Self w/ Femboy Training

He was so confused and really needed my Femboy training sessions. It was something Jamie was really uneasy about and felt he needed to hide it, but the urges and desires to be the Ladyboi he truly was could no longer be denied. He contacted me and after our first session was already feeling more accepted and excited about his ability to come out about his Sissy needs. He would hole himself up in a Hotel room outside of his town and bring he secret suitcase of all his pretty Sissy clothes, toys and accessories to be himself finally. He lied and said he was going out of town for work. He was really going out of town to be the sissy faggot he really wanted to be and wanted the nerve to really suck cock and hook up with a sexy tranny hooker. He always failed to get the nerve and just spent his time being a sissy online in the crossdresser kink sites where he would talk with others and share pictures. When he found me, he was finally able to gain the assurance and my training and strap-on play really brought the inner Sissy faggot out. If this sounds remotely like you, I would love to assist, I am always open to first timers and experienced Sissy’s alike. The humiliation and forced cocksucking is very exciting for me and I love making you my sissy submissive.

Femboy training

Sissy phone sex with the best

sissy phone sexSissy phone sex with the best bitches on the block, that is what you will find here, so when little bitchy faggots call me with an attitude I need to slap them right down to size. This little whore thought she could talk shit to me, as if I would bow down to a sissy can you believe that shit? I am a Goddess I bow to no one least of all some little sissy dick sucker! She needed to be taken down a peg so I called several of my friends over and we used that sissy slut until she learned that her place was at our feet. Sissy had to dress up and then get on her knees and suck all the dicks there. That included big black cocks, smaller white cocks and huge rubber strap on cocks that we were wearing. We really opened up that little whore’s pussy too, I bet that bitch won’t be sitting down for a week after last night! By the time we were thru with her she was begging us to stop and she promised to be a good girl in the future. We shall see tho, I think sissy enjoyed her punishment and will be back for more real soon!

Total Feminization

Domination phone sex

Nothing makes me happier than feminizing a little sissy. I love exerting my power over a man and reminding him that’s he’s nothing more than a pathetic little bitch in women’s panties. I feel so powerful and sexy when men submit to me and make me their mistress. I had a little panty boy who needed to be feminized, so I took him shopping with my friends and we dressed him in full lingerie underneath his clothes. We had him model different dresses for us and strut around in heels and a wig in the women’s dressing room. My friends and I were having drinks and laughing at him trying on the different dresses and trying to balance wearing hooker heels. Once we had him in the most outrageous and over the top slutty dress we could find for him, I took him to a bar and had him on his knees servicing horny men in the bathroom. He was a very good little cum slut and just loved being on his knees and sucking cock like a whore.

BBC Sissy Trainer Whore On Deck

BBC Sissy Trainer

I love all things black. Maybe that’s why I am a BBC sissy trainer! Your hot Catholic schoolgirl rebel who always cut class to fuck the black cocks knows all about your love for huge black cock. Lay back and close your BBC loving sissy eyes. Drift off into my black cock world as your cocklette aches to be my subslut!  My creamy white ass getting pounded by 10 inches of ebony steel. Jealous? I know you want that to be your pretty white sissy ass getting pounded right now. That Black cock porn you got playing has nothing on the real thing. I want to dress you up in the slinkiest black dress with black thigh highs and take you to a pool hall on the darkest (Hehe) side of town. Think of all the black cock we will get being the only two white bitches there! Now baby I really hope you have been doing that but plug training. Otherwise you ass is going to be so raw and I am going to love making you pay for not wearing your anal plug. 15 black cocks in your ass as you are bent over that pool table! ANd then you get to come home to me and be in chastity as you clean BBC cum from my tight teen pussy!

Sissy Phone Sex

sissy phone sexI am having so much fun as a sissy phone sex slut. So are my sissy sons. They love hearing about other sissies. The like knowing that they are not the only sissies in the world. There are a lot of sissies in the world. I talk to them daily! They overheard me talking about glory holes to one of my callers. They were full of questions. They didn’t understand what a glory hole was because I had not taken them to one yet because of their age. I wouldn’t be able to get them into the adult bookstore. But my caller told me he goes to the ones in public park restrooms. That made me do some reconnaissance of my local parks.

sissy trainingSure enough I spotted a glory at the “homo” park. It is just a park with a reputation for where gay closeted men go after dark. I dressed my sissy boys up like the pretty girls they can be and took them after dark to the glory hole to suck cock. I told them it was part of their sissy training.  I explained that this was a gay glory hole. They enjoyed that more because they are cock sucking faggot boys. I watched my pretty sissies in a dirty public park bathroom sucking strangers’ cocks and I was so proud of them. Super proud. They made so many horny queers cum. I am sure the fags on the other side thought it was an old fag sucking them off. Nope just my young sissy boy twins. They have the best mommy sissy trainer. I have taught them to suck cock so well that you would think their middle names are Hoover. With their bellies full of cum, we went home and talked about the hot encounter. The next part of their training is going to be big cocks in their back door pussies. This mommy trainer is all about sissy slave training.

sissy slave training

Mistress Phone Sex For Pansy Princesses

Your a pathetic excuse for a male as your just a Pansy Princess in need of Mistress phone sex, and I am just what your sweet ass needs. I don’t care if your ass is pink, red, brown or blue it is mine to own and I will have full ownership of you, slave. I’m the one to bring the pansy panty wearing princess faggot out that has been kept in the closet for too long. I want you to shop for pretty panties and make sure the clerk knows they are for you. You will ask her if they are your color or if she thinks the style is good for you. I will want you to wear pretty silkt panties under your man suit and go about the daily grind of being a useless male, only knowing secretly how much of a sissy you crave to be. I want to help you my pansy princess.

Mistress phone sex