1,509 results for sissy training

Sissy Phone Sex Fun

sissy phone sexSissy phone sex is the most fun a woman like me can have! I am amazed still that I have a job like this. I am a real-life sissy mom. I love turning men into the sissies they were meant to be. I also like talking to real sissies. I find it enjoyable to hear how other sissies have been raised and their experiences. Some sissies are for daddies and some are just for mommies! My two sissy boys are for both. I have raised them to take care of me sexually. They eat mommy’s pussy and ass. They take care of their sister too. They do the housework and help with our beauty. By that I mean they give us pedicures and manicures, even do our hair and make-up on date nights. My sissy boys also make money for my daughter and me. I pimp out their sissy holes to rich daddies who like young sissies. At a certain age you can’t tell the difference between boys and girls. A tight backdoor pussy feels the same as a front door one!  My pretty angels entertained a super wealthy daddy last night. He wanted them both and paid well for them both. Their sweet young holes got fucked for hours. They still have cum inside of them. Today, however, is about me and my daughter. My sissy boys are prepping to watch us get some big black cock. Sissies are so versatile. Are you a good sissy or do you need sissy training?

Sissy Tranny Bitch

Mistress phone sexI met a cute sissy tranny through another one of my sissy slut trainers. Donna had been training her for a few months and she wanted to test her sissy tranny with another strong Dominant. Arriving at Donna’s her sissy tranny was already in restraints with a very red ass. Donna had beat her ass for twenty minutes. Giggles that is exactly how many minutes I was late. Suzi had tears in her eyes and I felt my pussy tingle looking at her bright red ass. Donna had her thank me for being late and Suzi whimpered out the words. I patted her head as I walked past her. Donna and I were laughing at the worthless tranny before us. Donna got out her dildoes and toys and the fun began. Suzi took every strike we gave her across her flesh. Her ass opened up wide when we shoved the 13 thick inch blue dildo in. She took the whole thing. We lowered her restraints making her level with our soaking wet pussies. We both sprayed her with our cum and left her in her restraints while Donna and I were fucking each other.

Dickless Sissy with A Charged Up Ass Hole

online sissy trainingPatrick loves to be my dirty dick taking charged loads up his ass… My sissy loves positively charged cum loads in his ass. My pretty panty wearing crack smoking sissy la la. with a girlfriend who brings him hot fresh cum loads. I meant he can’t help but be a dirty dick lover.  A real BUG juice cum lover. He sliced two inches off his cock for me last night. He is the real fucking deal. His girlfriend only lets him lap cum from her sweet pussy. I don’t blame her. He is a dick mutilating cock sucker fag cock taker.  I just want to bend him over and have a 50 man gang bang his ass until he is a gaping bloody pulp.

Coraline is a BBC Sissy Trainer

bbc sissy trainerMy sissy boys love that I am a bbc sissy trainer. One of my twins told me last night that since black cocks are the biggest cocks around, it is best to suck big black cock before any other cocks. I have a black lover with a cock bigger than either of my sissy sons can handle. Bigger than any of my other sissies can handle too. My hung lover spent some time in prison. He said you either learn to get fucked or you take the fucking. He learned to fuck asses and mouths so he would be King of cell block 8. Now, that prison mentality is ingrained in him. He especially loves fucking white asses and mouths. He doesn’t care about age either which is why he is my perfect sissy training helper. My sons were happy to see him last night. When Trevor walked into my home, he kissed me on the lips then walked over to my pretty little sissies who were dressed up for him. He unzipped his pants and his vine started swinging. My pretty little sissy sluts started grabbing at his big black cock. Once they got it, they kissed it calling him daddy. I told my boys they will never fuck girls. They will only fuck daddies. They have clitty sticks not fuck sticks. I rubbed my pussy and praised myself for being the best sissy trainer. If my boys can worship and satisfy big black cocks, they can make any Daddy happy. Now, it is time to train you to be a good sissy boy too.

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

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

Best Sissy Trainer Coraline

best sissy trainerI am a sissy trainer. The best sissy trainer. I love being one too. I can look at you and see your true essence. I have this neighborhood boy who thinks he has a girlfriend. He thinks he is masculine and just like other boys. He needed some sissy therapy. He needed me. I had him come over for a friendly talk. I planned on feminizing him, but I needed him to first acknowledge that he is not like the other boys at school. First, I had to explain to him that him and his girlfriend weren’t dating. I was 100% sure she thinks of him as a gay best friend or something, but not a lover. Their “dates” include shopping at the mall and getting a drink at Starbucks. He is always home by like 7 or 8pm from a “date.” And, the kicker, they have not even French kissed let alone fuck. I had him strip down naked so I could see his cock. He didn’t have one, which was no surprise to me. He had a clit stick. I put him in some panties while I gave him some sissy hypno training. I mixed images to show him that what is hanging between his legs was nothing like what was dangling between the legs of the high school jocks in the locker room. I also got him to realize that his schoolgirl friend is fucking other men and that he is permanently in the friend zone. It can be a tough wake up call, but not all boys are created equal. Some have small dicks. Some have feminine bodies. Some are never liked sexually by girls. Some are meant to get fucked not fuck. My neighbor boy is one of those boys. We have a lot more sissy training to do, but I got him to the first step which is realizing he will never be the romantic lead in any girl’s life.

I humiliated my sissy

bbc sissy trainingMy sissy is reluctant to go out in public, she just wants to be humiliated at home just me and her all alone doesn’t that sound boring as fuck? Why would I want to sit home with a silly little sissy bitch? It’s not like I would ever fuck this bitch, all she has is a tiny little clitty and that shit is unsuitable for fucking. Well I made her think that we would be having another boring ass night at home so she went and got dressed up and while she did I called my big black stud Leroy over. I made sissy fluff him up and watching her choke on that huge black dick made me so happy. It was so funny! Then I made sissy watch me fuck my stud, she was so jealous that I took that huge black dick all for myself and wouldn’t share at all. My stud doesn’t like sissy pussy only real pussy like mine but sometimes he can be persuaded to fuck one of my bitches. If this sissy really wants my stud tho she will have to go out all dressed up for public humiliation if she doesn’t she will only be watching this cock not fucking it!

Sissy Phone Sex

sissy phone sexI love sissy phone sex calls. I am a real-life sissy trainer. I have turned my twin sons into sissies, and I will turn you into one too. I have this friend, Adam. He has never been very masculine, nor has he had much luck with the ladies. He came to me this week for some advice. I had to know what I was working with, so I told him to strip naked for me. I almost spit out my tea when I saw how small his dick was. It was a mico penis. It looked like just a helmet. It was like all head and no dick. I laughed. I told him his problem was his lack of cock. He had a few options. He could be alone with no female companionship with his hand as his best friend. He could be a cuckold and suck cock and eat cream pies or he could be a sissy. He told me he has long thought about being a sissy but needed sissy slave training. He was in the right company. I took him to my sissy closet. I have a huge closet of sissy clothes, wigs, make-up and accessories. He looked in my closet with awe.  I picked out a pink lacey outfit for him to wear. I put him in panties and told him he will only wear panties from now on. Even in a pair of pink silk panties, you couldn’t see a hint of dick. Pathetic, right? Not every guy is meant to be a man. Some are much better suited for the sissy word. Adam needs a lot more training to be a perfect sissy, but I am ready to train him. A sissy is a girl’s best friend. Are you ready to be a good sissy too? You need the best sissy trainer if you are.