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  1. Sissy Girl Training 101 — 2 comments
  2. Not For The Faint Hearted Sissy — 1 comment
  3. Heavenly Sissy Slut Training — 1 comment
  4. Punishing My Sissy Cum Slave — 1 comment
  5. Sissy Fun With 2 Mistresses — 1 comment

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Punishing My Sissy Cum Slave

Sissy pantiesMy sissy slut Cassidy pissed me off the other day. She disobeyed her mistress and removed her plug before I gave her permission. To make matters worse she didn’t even use her mouth to clean it like I like all my sissies to do. She was nervous her wife might find out about it. Just for that I locked her little clitty up in an extra small cock cage and made her wear her pink frilly sissy panties home to her wife. I also put my inflatable ass spreader in her and filled it all the way up. For good measure, I made her suck on a cum ice cube on the way home too. I want her breath to smell of fresh cum when she goes home to kiss her wife.  I hate it when I have to punish my cum sluts but this mistress doesn’t take kindly to disobedience. This little sissy will learn to understand that her wife is not the one she needs to be afraid of. 


BBC Sissy Trainer Heaven

BBC sissy trainer My little sissy cum sluts are trained to be the perfect BBC cum whores just like their sexy Mistress. I put my sissy on a leash and caged up his tiny clitty. Mistress Heaven has a surprise for this sissy slut. “I have a surprise for you that I know you’re gonna love my beautiful sissy,” I told her. Before she could ask any questions, I commanded that she open her big mouth nice and wide. I completed her slutty leather outfit with a new toy, a slave punishment mouth gag with nipple clamps. Her pretty red lips looked so plump and sexy in her new toy. “Assume the position” I instructed. My obedient sissy slut bent down and got on all fours. I pulled out my next surprise, a huge hollow tunnel butt plug. I inserted it into her tight sissy asshole. She whined and tensed up. “You better get used to the feeling of having your tight little man pussy stretched open babe. All good sissy pussies are always wide open and ready to be used at any given moment.” That’s when I brought in my final surprise a BBC friend of mine who just happens to love breaking in new sissy sluts. “You’re going to be the best sissy and lick my sweet pussy while my friend fucks your boy pussy with his giant black cock,” I smiled. I spread my legs for my sissy as my friend rammed his cock into my sissy’s hollow asshole. My pretty sissy obeyed my instructions while her tight ass got used and fucked. She sucked my wet pussy as my friend’s massive cock filled her juicy, stretched out man pussy with hot sticky BBC nut sauce. “Let my beautiful cum whore clean you all up, friend,” I told him. My friend nodded and pulled his hard, shiny cock from my sissy’s wet asshole. He removed the mouth gag and replaced it with his BBC. “I want that dick all cleaned up, sissy,” I directed. “You’re going to be a BBC pro by the time I’m all finished with you,” I smirked.

Sissy Fun With 2 Mistresses

Sissy girl training Mistress Gypsy and I always have so much fun playing with our beautiful sissy slut TJ. This Christmas we have something special planned for bringing in the new year. Mistress Gypsy got a brand new, purple, double-sided strap-on and we’re going to dress our sissy cum slut up real nice and pretty. Then we’re going to do a sexy homage to Sweet Gwendoline photo shoot starring our favorite girl! We also picked out a gorgeous deluxe pink chastity cage for her little clitty. It’s going to be so sexy watching Mistress Gypsy deepstroak sissy TJ’s tight man pussy while the other side of that purple strap-on pushes deeper inside her cunt. I’m going to love seeing our sissy slut with her pink lipstick all smeared from licking and scooping all the creampie out my slippery kitty while she takes that purple dong right in her fuckhole. We’ll fuck our sexy slut until her clitty leaks yummy cummy through her cage. Then we’ll make her clean that ten inch purple dong on both ends. She’s the perfect sissy cum eater to dress up real pretty and play with. We will train you to be an obedient, perfect, cum-guzzling sissy slut too.

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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. 

Heavenly Sissy Slut Training

Best sissy trainer Even the manliest men can be cum guzzling sissy sluts under my guidance. I teach them how to dress like a sexy sissy skank and how to take BBC like a good sissy whore does. I never have a problem making my sissy sluts do exactly as I say. That’s because this sexy sissy trainer has a zero tolerance policy for disobedience. Spare the rod, spoil the slut is my motto and I never spare my hot rod. He’s a massive 13 inch black strap-on and I don’t hesitate to bend my sissy’s over and fuck them into compliance. When they finally accept their place as my obedient sissy slut, I am loving and generous. I reward my best-behaved sissies with pretty dresses, heels, and the sexiest lingerie. Occasionally, I treat my well-behaved sissies to a buffet of giant, heavy cocks to indulge in anyway they like. Balance and consistency is how I get the very best out of my sissy whores in training. You will see for yourself when I turn you into the queen sissy slut you always dreamed of becoming. 

Not For The Faint Hearted Sissy

best sissy trainer

 I am very intense with my style of sissy training. I want to push your limits. I expect you to put on a French maid outfit. You will get down on your hands and knees and scrub the floors until the boys arrive. When they come in you will be introduced as the submissive maid slut. The three men with the big cocks will take turns shoving their cocks down your throat. The are huge dicks. No smaller than 9 inches each. I will get the strap on and tell them your going to need your holes loosened up a bit so they can pound you good. Keep in mind all three will be fucking you in your ass tonight. What more could a sissy ask for. All the attention is on you and your the star of the show. But it will be intense having them run a train on you. Your hole will be good and sore when their done fucking your boy pussy.

Heaven Is Your Mistress

Best sissy trainer Hey are you ready to begin sissy training. These courses are not for the faint of heart. You will need to be able to handle intense sissy training. We begin with giving you a crash course in cuckolding. As your master I will put you to work and make sure that my team of hot guys with big dicks abuses all your holes. Can you handle all these guys and their big ten inch cocks. I hope you can handle all the pressure of taking it in the ass while sucking cock at the same time. Can you keep up with what I’m going to put you through. If not need not apply. This intense sissy training will include humiliation and bondage. So don’t be a wimp when I give you your lessons. We have slot of work to do let’s get started. I want to be your ultimate sissy boss. I will get off on you being fucked in the ass.

Let’s Indulge In Fantasy

Best sissy trainer I am ready to invite some new Sissy boys over so we can have wild threesomes. Who doesn’t like a little naughty fun. All my guy freinds are very handsome and they all said they wanted to meet my newest little boy toy. I told them you suck cock better than anyone I’ve trained and they just had to experience you. When you came over you were wearing a sexy tight skirt and lingerie underneath. You stripped down to nothing but you thing and put your panties to the side. One by one you let them fuck you in the ass and you were moaning like a female. I am going to get the strap on and see if you can take a little pegging. You like when I humiliate you in front of a group of guys. You get so hard when I call you a cunt. Or my little bitch. So excited that you choose to be dominated tonight.

Heavenly Temptation

Best sissy trainer I am ready to give you your training. You said you want to learn how to be more feminine and seduce men in the bedroom. Well I can do that for you. You will enjoy sucking the large cocks of the the men I bring to you. You will feel so sexy in a bra and panties while being fucked from behind. I know many handsome men with large cocks that can make you there little sissy servant. Is it your dream to be the center of attention in a room full of hot guys. Well if I bring over three hung gentleman. And tell them you are the hot tranny they want to fuck. Can you handle the dick there giving to you. You will have maybe one or two cocks on your ass at the same time while your gagging on some huge throbbing dick. Sound like something your interested in? Well I can’t wait to get started.

Hot Sex Is Heaven

best sissy trainer I know you can’t stop thinking about cock. Do you wish a sexy dominatrix would dress you up feminine and humiliate you? I’m the girl to call. I have lots of gay men that trust me to give them the advice they need to become confident tranny’s. I will introduce you to my friends with big cocks. And yes some of them even have big black cocks. I will make sure you get some action tonight. It turns me on to picture you in your sexy lingerie that I helped pick out for you. I’ll have you waiting on the bed while I invite them in. You will be already bent over with a ball gag in your mouth. You will be a good little slut and take it in the ass. I love to watch gay men fucking. It’s so sexy to see you gagging on that large cock. I have a strap on to fuck you in the ass with while you suck his cock. ????