Category: Humiliation phone sex

Sissy Girl Training 101

Sissy girl training

A good mistress knows, instinctively, how to train their sissy slut into the proper fucktoy. My sissy slut, Emily, is my greatest accomplishment. She came to me unsure of herself and in need of guidance and confirmation on everything. I made sure I taught her to recognize her place as a useless sissy slave worthy only of serving and pleasing her sexy seductress. I had to help her understand that her worthless, little clitty was no longer her own. It belongs to Mistress Heaven now. Sissy Emily learned her place beneath me, pretty quickly, but even she makes some mistakes and finds herself getting into trouble. When she’d misbehave or make me cross, I’d lock her little clitty up in a chastity cage and leave it there for days or weeks depending on how upset she made me. I’m not all about punishment and pain; although my tight, juicy mistress pussy does get wet when I make my slutty sissies suffer for my pleasure. I’m actually a very kind-hearted mistress that loves to take great care of all my sissy cum sluts in training. I simply demand the same in return. At the end of  each of our intense slutification training sessions you’ll be thanking me for whipping your little clittly into shape. Literally and figuratively. In the beginning of my sissy training, you will wear your precious pink chastity cage just like all the rest of my newbies. As you get better at your training, you’ll be outfitted with various cages and butt plugs. Each one color coded and sized for your individual level of sissy training. Pink cages and butt plugs size small adorn all my baby sissies. By the end of your training your little clitty won’t even need a cage. It’ll never get hard or leak any of your boy juices again. Not unless Mistress Heaven allows you to do so. You’re going to enjoy me forcing you to embarrass yourself by making you wear a red silky thong and tights to your job, then demanding random pictures to make sure you are obeying. I will get a good laugh while you whine to me about your sissy fears and embarrassment. I love hearing all about how your red panties were clearly visible at the company meeting. Then I’ll let you tongue kiss my tight pussy once I’m satisfied with your humiliation. Sure I may smack your eeny weeny clitty a few times for good measure. That’s just to remind you of why it’s important to keep that little clit locked up safely. Trust me when I say you’ll be on your sissy slut knees crying with pain, pleasure, and sincere appreciation for your heavenly mistress. 

Sissy training with Miss Remi

sissy training

Every half decent sissy training mistress knows that Christmas is perfect for finding little sluts shopping for panties and that’s exactly what I do! No one looks twice at a man browsing the silky, soft piles of women’s panties at a department store around this time of year. You might think they’re just shopping for their wives, but I know their kinky, little secret. I find secret sissy whores like that every year. I follow them to the fitting rooms and sneak in when no one is looking. A few clicks with my phone and I have pictures that can ruin them! I think they secretly love being blackmailed by a hot mistress and being forced to suck fat, hard dicks at the risk of being exposed by me! I don’t care either way, I just love turning them out!

 

Bend Over Sissy

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Aww look at you coming down from your bath. I have laid out your clothes for the day as we have an incredibly special time planned love. Your eyes brighten as you see a new pair of pink nylon panties and matching bra on the bed. You practically dance with excitement seeing your thick pink jeweled butt plug. Hurriedly you grab the fish net thigh highs and put them on, then your panties and bra and finally your short black slutty dress. You slip on your heels and come to me. You hand me the butt plug, bow your head, and say please.

I bend you over, pull down your panties. Your pussy is already pulsating and gaping with excitement. I smack your ass one time just for fun and then ram the butt plug deep inside. It is the special one, the one with the remote. The one that I have complete control of. I know you want me to push it, but I make you wait. I grab your cock cage. The extra small one and push your little clitty inside. The prongs touching your skin, just waiting to restrain you. I see you leaking and laugh. You really are my slut babe I tell you as I kiss you on the cheek. Now let’s get in the car, you are the star of my afternoon Mistresses’ club, to be used and abused. You just smile as I turn on the remote.

BBC Sissy Trainer For White Boy Faggots

BBC sissy trainer

Mommy Diana is a BBC sissy trainer. I will get you fucked by the hottest taboo fuck there is. That is big black cock is the best cock for a white faggot sissy. I will train you to please that big black cock like a good whore. You will suck black cock for Sissy mommy Diana.

You will cum riding that big black cock. Your clitty will squirt in those pretty panties. You will crave the big black dicks of mommy’s lovers. You will beg for those BBC cocks to cum in your sissy pussy. I promise you will be addicted to that black seed. There will be denying that your obsession will make you a total size queen for BBC.

 

Cream pie, Sissy Training

sissy trainingYou need the taste of your own cum, and this sissy training, sexy slut wants you hooked on it! I think the humiliating aspect of it with a beautiful, dominant woman like me forcing you to cum guzzle appeals to a fucked up perverted bitch like you! All you want is that warm cummies drank down for me! Your wife would be so shocked to know how much her husband enjoys tasting his own dick juice, wouldn’t she? Well, we all know she loves to drink other mens cum, and be fucked by them.

I mean, your cum load isn’t much by quantity is it now? Little dicks don’t spurt much, so it’s really like a tablespoon of clitty juice! I like her, would much rather be fucked by a large and in charge cock that gave me a nice coating down my throat or up my sweet tight little pussy! Your wife and girlfriend both enjoy your mouth on cum filled cunts and you pretend like you have no idea your eating a cream pie!

Maybe you can cream on top of a BBC and taste both cum loads mixed together for me! Get on your knees and suck it right from the source, big black dick, bull white boy cock it really doesn’t matter to me as long as you’re in the sissy bitch position and sucking a dick! Now put that mouth to good use and get your sissy slave training done for me!sissy slave training????

Cross dressed slaves

Best sissy trainer

His  reality – 40+ years later? More powerfully addicted to dressing in woman’s clothing than ever before. Just putting on  panties and stockings excites him more than it ever has. It never gets old or stale. It is impossible for him to stay out of girl’s clothes. Yes – He wants to look like a perfect girl. His lifestyle restricts him to only interact virtually while in his home. This includes never being dressed in public. At least in his outerwear. That’s just the way it is and will always be. Has he interacted with others over the phone? Yes – a waste of time and money.  He can put on a dress (and he has 100’s or even thousands of times) and cum like he always has to a fantasy. What he cannot experience, without somebody else, is being under their strict control. This is what compelled  him to contact me. There is something wildly erotic to him about being required to address me as Master. He wants me to be his Master. That’s right! – my rules are very clear. He must follow all of my commands. He begs me for the opportunity to submit to me, Master Brielle. From now on, he will be in my command at all times. Whatever I say GOES, it will not be up for discussion. Yes – disobedience needs to be punished via humiliations, whips, chains, BBC, and having his cock and sissy hole tortured. He needs these things done to him even when his behavior is perfect. Why? Because he is to be Master Brielle’s Sissy and a reminder of my power over him makes him even more powerful. He begs me Master Brielle to keep him under my control for as long as he wants. Once I start, he is never to be allowed to stop being trained by me. A Sissy? A cocksucker? Being fucked by another Sissy? Worse being fucked by a man? All things he has refused, denied or failed to accept. He describes himself and comes to me as a Lesbian slave-girl. But as his Master, he begs and pleads with me to turn him into any or all of the above. Our interactions may be limited to virtual, with constraints on public display, but that does not mean he will not be turned into my personal property and possession.

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not so forced sissy training on my new woman!

Best sissy trainer

“As a teenage boy, whose mother and older sister worked full-time, he had access to their clothes after school for several hours each day. During the summer? All day long. he dressed himself frequently. Head to toe. Panties, bra’s, stockings, pantyhose, full length body shaper, girdles, half-slips, full slips, blouses, mini-skirts, dresses, high heels and nightgowns. He even put on their makeup including polishing his nails. Did he cum when he was all dressed up? He tried not to but he did on several occasions. His most intense orgasms have always been when he is all dressed up. Didn’t they know? Of course they did. His sister caught him a few times and his mother absolutely knew. They ignored it. They pretended that it never happened. What did he truly deserve? Punishment to fit the crime. Because as powerful as his crossdressing desires are. His submissive desires are equally as powerful. (#1: You want to dress as a girl? Fine, you picked it. You made your choice.) But it will not be when you decide you are in the mood to dress this way. You will be required to dress in girls clothes quite often and will have no say in the matter. (#2: You want to cum dressed as a girl? Fine, you picked it. You made your choice.) But, you will only cum from now as a girl, A vibrator or dildo inside of you, with no touching of your cock. You are not going to just be dressed as a girl, you are going to get turned into a girl. You will have no say in the matter. Yes – he wants to look like a perfect girl just like his Master Brielle. What he cannot experience, without somebody else, is being under their strict control. This is what compelled him to contact me.”

He is the new sexy lady in town and I am his Master!!! 

Too be continued…..

Queen Presley Owns You

Best Sissy Trainer

I am the best sissy trainer, and I own your pathetic little soul. Sweet pretty girl, come play dress up with me and my girly friends! We don’t shave, we wax – every single part of our beautiful lady bodies. We always have to be ready to take some hot bull cock. Here, try on these panties! They’re so cute! All pink and lacey, and matching this bra! Here, put it on honey! We’ll get you hormones so you can grow your own tits and fill these bras out, but for now you have to be a cutie little A cup. Remind me again, what’s your name sweetie? Oh not that name! Your pretty girl name. Don’t you want to be a sexy bitch like me? You do, because I say you do. And Queen Presley owns you.

Cum Here Pet

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Aww here comes my little pet. On his knees crawling to me. Wearing a pair of pink nylon panties and pink vinyl collar. I pet your head before attaching the leash. Do you want to go on a walk boy? I attach the leash, kiss your forehead, and lead you to the playroom. You hang your head because you know that you have been naughty. I saw you on your phone watching shemale porn and rubbing your little push pop. Goodness that was a sight. I even had to zoom in to make sure you really were jerking your clitty as it is so tiny.

I tie the leash to the table, and you climb up and take the position. On all fours, chest down and man pussy up. I pull your pink panties down to make sure your clitty cage is nice and tight and then rub your ass. I grab the paddle and put it to your face. You instinctively lick it like you are licking a cock. You really are a little whore I say as I examine the cage and see little drops of pre-cum leaking. I hold my hand back and deliver the first spank against your creamy white ass. A bright red form starts to appear. You gasp and your knees are unsteady. My pussy soaking as I pull back for number two. How many times do you think I should paddle you pet?

New sissy trainer in the hut

Best sissy trainer

Welcome to sissy slut hut!! 

 

I just had the best sex ever! I am so surprised he let me fuck him with my strap-on! OMG it was amazing I never thought giving a man anal would turn me on this much. He even dressed up for me. He was wearing a very sexy flair royal blue dress. What he had underneath was a rose floral embroidered bra and panty set. The crouch was cut out so his massive cock hung. Uhhh I was so impressed by his choice of clothing. We got back to my place and we had the time of my life. I put a sexy black outfit on and attached my strap-on to my hps. He dropped down to his knees and sucked my cock so good he was drooling and slobbering all over the place. His ass started to get so wet he bent over and asked me to have no mercy! I sure didn’t! I fucked him deep in his nice round ass so good he was moaning so loudly. My pussy began to throb. I was dripping wet. He bent me over and showed me how much of a man he really was.

 

 

I had never been fucked so good in my life. My pussy is still tingling. I am playing with myself now!