Category: Sissy girl training

Humiliation Phone Sex With Jackie

humiliation phone sex

Oh. My. God. Look at that tiny little cock. Looks like you’re ready for some humiliation phone sex. I can’t believe you are even trying to pass that thing off as a dick. It’s more like a clit and trust me when I say that you’ll NEVER be making a woman cum with that ridiculous little nub. I’m sure you’ve tried, but it’s just not physically possible. The only thing you’ll ever make me or any other woman do with that thing is laugh. And I don’t give a fuck if me laughing at your little dick makes you sad or upset. You can even cry and it won’t affect me.
It would be so much fun to gather a group of my girlfriends and have you there as the maid. Serving drinks to us in your little outfit will make me smile. And I’m going to make you tell each and every one of them why you’re all dressed up in a maid outfit. Beware, though – once they find out what a tiny dicked loser you are, they’re probably gonna want to fuck you with a strap on to show you what a real cock would be like. Oh well. It just comes with the territory. Call me and find out the rest of the things you’ll be doing for me.

You Are A Cock Whore Sissy

Sissy Panties

Come here you little sissy boy. I have laid out some pretty pink satin panties for you to put on. There you go, look how pretty you look in them. Look at how you cannot even see your tiny cock through them. You cannot see your little balls either. I think these were made just for you. Turn all around and let me see how you look. I like how you have shaved your legs and waxed between your legs. You are preparing yourself aren’t you my little cock whore? You cannot wait to take those panties off and please a man with a big thick cock. I think I see a little spot on your panties. Are you getting wet just thinking about it? Now come here my sissy and help me get this big dick hard so I can slide it into my juicy wet pussy and ride that big thing while you sit and watch.

Sissy Girl Training With Mistress Jackie

sissy girl training

I see you’ve reported for duty for sissy girl training. I know you’ve wanted to for a long time but were just scared. You’re in the best hands with me because I love turning men into sissy sluts. We will go as slowly or as quickly as you want to, as long as we’re making forward progress. You can’t call me and keep putting off your feminization. Just trust me when I say that, although it’s scary, you’re going to be so happy with your sissy transformation. You have to let go of the control and let me help you with what you desire most in the world.
My favorite party of sissy training is getting the look down. You have to be willing to do the hard work – waxing, shaving, growing your hair, etc. You have to learn makeup, lashes, wigs. And I know you probably already have pretty panties and lingerie, don’t you? Can you walk in a pair of 4-inch heels? Men love women in heels and the same goes for sissy sluts like you. I’m gonna be here every step of the way for you. All you have to do is get on the phone and give me a call. I’ll be waiting for you.

BBC Sissy Trainer for You

bbc sissy trainerI love being a BBC sissy trainer. I love big black cocks and I love helping sissies know how to handle them. I acquired a new sissy over the weekend. He has long fantasized about being a cuckold, but his wife just would not cheat on him. I have no clue why. I mean that is like having your cake and eating it too. What woman would not want to stay married to a man financially taking care of her and have lovers whenever she wanted? You know damn well, men would jump at that chance. My new sissy is the soon to be ex-husband of a friend of mine. I had no idea he wanted to be a cuckold. I told him he should have confided in me long ago. Before the divorce was finalized, I would have helped my friend because that is what friends do. I want all my girlfriends to have big cocks in their cunts. If I could not help my girlfriend, I could help her ex-husband. I called over a few black men I know that will come over at the drop of a dime. They were knocking on my door before I had my BBC sissy dressed properly. Most of my sissies get online sissy training, but this sissy, I know. She lucked out because she was going to be a cuckold and black cock faggot sissy in one night. I made her fluff my black studs first. If she wanted to be cuckold, she had to fluff and guide those dicks inside me. She also had to clean up my messy pussy afterwards. And of course, cleaning those big black cocks up after my pussy juice coated them is part of being a cuckold. This is also part of being a black cock faggot. Cuckolds often become sissies. Once you suck a black cock you want more. Trust me, I know. I think my friend’s ex-husband is a natural black cock faggot. She is just lucky she knows me because I have lots of black cocks for her to hone her skills on.

Giving Daddy Sissy Maid Training

sissy maid training

Daddy Jim gets a special kind of sissy aid training from me. See he has to do as I say and put on his cute little maid outfit and hold his pee until I say he can. I make him wash the dishes with the water running full blast as he does his little pee-pee dance. Then I make him Piss on the clean dishes so he can wash them all over again! I am so mean right. Well I do take it easy on his little two-inch clitty and give him a big monster BBC to suck on like a lolly. He loves that shit; he will suck and gag until he has to pee again. I put him in his pretty little cock cage and make him piss with it on this time. I poke at his balls and little tiny dick until he can give me a little cum shot and then it is back to work for that sissy cum dump! All the while I am being fucked wherever he is cleaning by the big black bull cock! Bet you were wishing you were Daddy Jim now!

I Must Punish You

Mistress Phone SexI hear you have been a bad little sissy. Playing with your little clitty without permission? And riding your big fat dildo with your man pussy? I am so disappointed in you. We have talked about this and I have given you a few chances, but you continue to disobey. Now you know what happens don’t you. You must be punished. So, put on your sissy panties and grab your paddle. I want you to rub that little clitty until that small thing is as big as it can get. Now you take that paddle and swat it. Like that. I know it hurts but you cannot play with things that don’t belong to you. You know that clitty is mine. Now swat it again. Harder. And Again. Are those tears running down your face? Now swat it five more times and hard. Ouch that looks like it hurts. Incredibly good. You can stop now. Let me see it. Oh, look how red and swollen it is. Now since you like it so much you keep rubbing it, don’t stop until I tell you. Are you still crying? Look at that pre-cum leaking out onto your raw clitty. Bet that stings don’t it? Now you keep stroking that clitty until you have cum twice. I will know if you lie. Then pull up those sissy panties and rub your warm goo all over that raw clitty of yours and sit in those panties the rest of the day. Maybe next time you think about playing with yourself you will remember this. Next time I will do the swatting.

He Loved Being a BBC Slut

This sexy fiend of mine came to me wanting to watch me take cock. He didn’t want to watch me take just any cock either. He wanted to see a nice juicy big black cock penetrate my trashy Milf pussy. He knew I was a BBC sissy trainer but wouldn’t let that known to me. He was shy about it at first. I let him watch me as long as he wore my panties while doing so. I made him come close and get a good view of that black snake sliding it’s whole 10 inches inside of my wet mommy pussy. He was rubbing his little peepee and creaming those panties with his little nub almost instantly. Just a few thrusts of that BBC in my cunt and it glistening with my pussy juices was driving him mad. He eagerly took it into his mouth when told. I commanded that he pull it from my cunt and start sucking it. He is now a total sissy slut to BBC.

BBC Sissy Trainer

I made him my bitch

best sissy trainerI took a strong, successful man and made him my bitch. I broke him like a horse, slowly, carefully until he was completely incapable of doing anything without asking me for permission first. We met on a blind date and while he was handsome and clearly wealthy, there was just something about him that was off. He had a weakness in him that I could sense so I went about exploiting that weakness right away. That first night I had him on his knees begging me to fuck him with my giant strap on cock even though he had never attempted anything like that before. By the following week I had him dressed in women’s clothing sucking my lover’s cocks like a faggot. And just yesterday he went on his first out call appointment as a whore. I took that strong man and made him my bitch and that just proves that I can break anyone.

BBC Sissy Training My Husband

BBC Sissy TrainerOne thing high on the sissy lust list is a BBC. But you have to know how to handle the BBC. It is a big beautiful black beast. Not for an untrained sissy. Therefore, I have made a fortune from women wanting me to train their husbands to be BBC sissies or men who want to be BBC sissies. I will use my sorry ass husband as an example of exactly how this BBC sissy training works. I love to dress him in frilly sissy panties and have him sit right beside me. Then I have that gorgeous man with that monstrous snake come over to me. I show him how to stroke that big dick. It is so large you must use both hands. He did so good, stroking up and down in perfect rhythm. I show him how to gently touch the ball sack to, causing that beautiful man to start to moan. Next, and this takes lots of practice, I show him how to lick that massive thing. From the base to that big head. Going slowly and firmly, licking in long even strokes. I can see my husbands tiny dick through the panties, and he is starting to leak more and more as the gorgeous man moans louder. My husband gets so excited he starts to put it in his mouth. That is when I must stop him. He is not worthy of putting it in his mouth, he is simply there to get it nice and hard for me. I then make my husband get on the bottom of the bed while he watches me satisfy that BBC with my mouth, my juicy wet pussy and even my nice round ass. As that BBC is fucking me, I laugh at my husband rubbing his little dick, getting off on watching this big cock go in and out of his wife, making me moan in ecstasy.

Pegging you

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Tonight I am going to fuck you with this strap on cock.  It’s fat thick and hard ready for you.  I want to see you on your knees sucking my cock. I wanna watch you gag and plead for me to stop fucking that sissy little whore face of yours. I am gonna take this fat cock and ram it in your little virgin asshole.  I wanna spit on that brown eye and tease your needy hole and push that thick cock head in your boy pussy.  I’m gonna wrap my hand around your cock and stroke it while i pound your fucking asshole. I love hearing you cry out in pleasure and pain.  it makes my little slutty cunt dripping wet. i just can’t wait to fuck you and have you begging for more!