1,510 results for sissy training

Transforming You Into the Perfect Sissy Slut

Sissy Training

Your sissy ass is eager for some big fat cocks, and I know just how to entice men to make them want to fuck you. I get you a sexy, tight red bodycon dress with a plunging neckline. I make sure you fill out that dress with gigantic, H-cup breast forms in a sexy, lace red bra. I put you in a nice red thong that give easy access to your ass. For the final touches, I do your makeup in a way that emphasizes your big, dick sucking lips and let you borrow my 6-inch red stilettos. Now, it is time for you to go out on your own, to a bar late at night where the women are few and then men are horny. Sashay inside and let them ogle your body, from your big, beautiful tits to your nice, round ass. Let them objectify you and see you as the sissy fuck toy you really are. Rub your ass on their cocks, push your tits on their chest and make their cocks rock hard. When one of them wants to fuck you, act like the sissy slut you are and follow them into the bathroom. Let him bend you over the sink, and fuck you in your big, fat ass. Take every inch of him like a good little slut until he squirts his cum inside of you.

Phone Dominatrix Coraline will Make You a Sissy Slave

phone dominatrixI am a phone dominatrix. What I say goes. Sissy slaves who do not follow my instructions will feel my wrath. I am dominant in my real life too. I consider myself a sensual dominatrix. I can be a bad ass bitch when I want. I have all sorts of strap ons, whips and restraints. I started as a professional dominatrix before I became a sissy trainer. I used to beat balls back and blue. Some days, I miss it. Training sissies is more sensual than cock and ball torture. I have this one unruly sissy. I have a few, but Ray is my most obstinate sissy. He hired me but then imposed all these rules on me. He was like I do not want to do gay shit and I do not want to dress up in women’s clothing. I was like what do you think sissy training is then, Ray. He told me he just wanted to eat my pussy and ass. That is is a submissive slave not a sissy. Since he wanted to be a slave and not a sissy, I gave him what he wanted. It was more than he bargained for. I did sit on his face and made him worship my cunt and ass. But I also pissed on him. He never said anything about golden showers being off limits. I pissed my golden nectar down his throat while pinching his nose to make sure he swallowed every drop. He did drink it all down like a good slave. I took it further. I thought about shitting on him, but it’s not really my thing. I did use my strap on on him, however. I tied him up and rammed his ass with a ten-inch dildo. I wanted him to realize that being a sissy is better than being a sex slave. At least it is less painful. By the time he was done being my slave, he was ready to be my sissy. He put on a pair of sissy panties after a good pegging and now, he is far more obedient. You are on a sissy site. Be prepared to dress up pretty and suck some cock.

The Best sissy trainer set and auction full of sissies in Sissy panties

Best sissy trainer

Since i am the Best sissy trainer I have so many sissy slave training to do i decided to auction them off to some BBC sissy trainer bulls I know. They all came with money and big black dicks for my Sissy sluts. I got them ready with some Phone domination and Sissy training audio tapes before they came. They knew to arrive wearing Sissy panties and heels, plus lipstick. I love watching that lipstick smear when they suck a big black cock. When the auction started, they all had to come out one by one showing off their favorite skill they acquired from sissy training. One sucked dick until his mouth was full of cum, another sissy used his magical hands to milk a BBC. the last one showed how quick his Sissy pussy can make a BBC cum and he even cleaned up his cock with his mouth. I knew he would bring me lots of money at this auction. One by one they took turns getting bid on. At the end of the night any BBC sissy trainer who won his bid paid me and claimed his winnings. 

Branding my sissy

forced feminization

One of my absolute favorite sissy sessions is the branding kind. I’m always looking forward to having a sissy agree to some gnarly forced feminization. The best feeling is making a sissy do whatever I want without hesitation. Sissy slut Maggie went to get branded ” Property of Goddess Alessandra!” Oh boy, did I love seeing that on her lower back? It was the perfect tramp stamp, and it made a statement to all the men that would use her ass pussy. They now know that this particular sissy has had the best training from me.

A series of sissy sessions that will have this sissy pleasing and doing whatever it takes to make that big hard cock jizz so fucking hard. I’m so into these sissies doing whatever I want from them.

Forced Feminization Makes Sexy Sissy Slaves

Forced feminization

My tested, tried and true forced feminization process can turn any lanky, long necked nerd into the fine sex goddess he’s always wanted to be.  Most men don’t have the guts to go after what they really want in their sex lives and just stick to the norms that are expected of them.  The geeky guys who come to me to have their unused asses turned into gaping gashes are obviously ready to go on a completely different sexual journey.  I’m more than happy to be their guide into girlhood, I’m really good at making all of my femboys look and feel fan-fucking-tastic!

How many times have you sat at your work desk and wished that your ass was being worked over by a big fat cock or, at the very least, a massive strap-on dildo?  I know, you daydream about being turned into a dainty little fuck toy and having your rim wrecked on a daily basis but you tell yourself that you don’t have the balls to do anything about it.  That’s not the problem, Pal.  Would it blow your mind if I told you that it’s not your lack of balls that’s the problem, it’s your overwhelming abundance of them?  Boom.

I’m gonna shrink that sack and turn it into a sexy slut-slit that sits right below your perfectly positioned, perpetually wet little clitty.  Your ass will be shaped and shined and prepped to take on any and everything that I want to throw at it.  You’ll love it!  I won’t neglect your tiny sissy titties and those sensitive, puffy nips of yours.  Having them sucked on while you have a finger or two boring into your butthole, feeling out the flexibility of your sphincter feels amazing!  It’ll have your clit head slinging so much drool, it’ll blow your mind.

Hitting on the girls at work isn’t in your stars, your man self doesn’t have the balls for it.  You have all the testicular fortitude you need to become one of the girls at work that the other guys hit on, though.  Sure, you’ll have to ditch the dweeby image and learn how to properly take a massive anal insertion without completely blowing out your butthole.  Take it from me, you don’t want that drama.  Follow my simple sissy slave training techniques and you’ll go from the unfuckable office dork to the sexy cream queen of the company that everyone, guys and girls alike, will be dying to get their hands on.

 

Best sissy trainer punishment tools have BBC and are ready

Best sissy trainerI’m like the Best sissy trainer, but you sissy boys were giving me a hard time so I called someone to teach you a lesson, but it wasn’t what you expected. You figured some small dicked guy would come and fuck your face, maybe give your ass a try, but I didn’t do that. I called a tranny to show you up. That’s right, a bitch who can suck dick better than you and fuck you until you’re a crying mess. I decided to utterly emasculate you by getting a woman who can do everything you do but better. She’s prettier, hotter, tougher, and has a bigger dick. She’s here to wreck you and teach you all about Forced feminization. When she’s done with your sorry, weepy ass pussies, I expect you’ll be a lot more compliant and obedient. She’s your punishment, and you’re her reward, so don’t think she’s going to go easy on you just because you cry or whine a little too much. She’ll just get rougher. She enjoys shit like that, she relishes in taking power from you and using that power to stretch out your asshole until it’s glaringly obvious you’ve been pounded within an inch of your life. A ten inch masterclass rod of might is here to show you what’s up and if you somehow manage to come out of this a stubborn bitch, she’ll be back next time ready to partake in the glorious prize I’ve afforded her, your Forced sissy training. So let’s get you dressed up all pretty and ready to have it torn off you and ruined. You’re paying for it, of course. Paying her too, enjoy your expenditure because it’s coming at you hot, ready, and harder than a stone monolith to all that we’re tearing down one dicking at a time.

Sissy Halloween Fuckfest

Domination phone sex

I took some of my sissy sluts to a domination phone sex Halloween party and, I don’t have to tell you, they were the hit of the evening!  All kinds of hot whores were there dressed in their slinkiest getups looking to be objectified and subjugated, but my beauties with balls were the cum covered belles of the costume ball.  You already know, I wouldn’t have had it any other way.

When we arrived, the party was already swinging.  There were dressed up dolls getting banged out all over the tables and whores bent over the bar so I decided to put my panty waist pussy boys up in some more compromising positions for pole pleasing.  It was a big club, I figured that we might as well utilize all of the space.  

I fastened my first femboy up the amps on stage and forced that he-bitch to get her butthole busted by every big bone that wanted a piece of ass while they enjoyed the music up close.  Of course the band got in on it and fucked my little clitty queen senseless like she was one of their groupies.

I posted a couple of sissy boys up in the bathrooms, handcuffed one to a toilet to be used as a human urinal for the men and tied the other up in one of the stalls for the women to do the same.  I don’t know if you’ve ever blown a piss filled load all over a golden shower loving fuckboy before, but the guys at the club seemed to love it.  The moans and groans coming out of the men’s restroom were crazy!  I’ve never heard louder male orgasms in my life.  Even the squeals and cackles coming out of the girl’s room couldn’t compare.

The photo booth needed a slut in it to jazz up everyone’s junk so I tied a sissy slave to the backdrop and told all of the party goers to do whatever they could to make her cry for their pictures.  There were some great shots and my prissy whore got tons of pictures of herself being hammered hard by tons of different characters, but my favorite was one of a couple dressed like Marge and Homer Simpson shoving a frightful rubber fist into my he-she’s ass.  It was hilarious!  

By the end of the night, everyone was saying how my sissy sluts really made the night.  We all had a blast, my gang of girly guys had several!  If they ever wondered whether or not the sissy slave training I put them through pays off, that Halloween party should’ve been all the proof they needed.

 

Femboy training with you is always so damn cute!

 Femboy trainingIn that frilly dress you bought for yourself for Femboy training at my beck and call, I can’t help but let the words “pretty” escape my mouth. It looks good on you, it’s so shiny in the midday light and the way it covers your shaven legs juuuust enough to tempt me but not enough to be boring, really highlights the entire look. Those heels look good on you, and the bow I picked out contrasts so nicely that I find myself realizing I’m really looking at a girl. We’ve done it, you’re a girl now, at least for right now. I casually adjust the bow a little atop your head, shifting it every so slightly to the side in an effort to really bring out your Sissy girl training. I brush your hair just right so that the part covers your eyes ever so slightly, and the rest frames your cute face. That little blush of yours feels so good to look at, a little added makeup doesn’t hurt though so I’m sure to go at you just a little. You don’t need that much, you’re a natural, and looking at you makes me feel really good. I did it, I made a girl today. I ask you to spin around for me and show me the back, and when you do I grab your shoulders and hold you still. “Just like this.” I giggle, lifting that skirt of yours, and revealing those pretty pink Sissy panties I had you buy. They’re so cuuuute! It’s a shame to slide them down your ass, but I do, because the real reason I had you turn your back is revealed a moment later when I slip a nice dildo into your asshole. You cry out at first, but I whisper soothing promises into your ear. Reminders like “pretty girls don’t complain” and “you’ll love it soon enough.”

Oop, that’s all the time we have. You’ll call me and hear the rest, right? You cutie slut.

Femboy Training with Me Takes You From Man to Girl

femoboy trainingI love femboy training. It is getting colder weather, so I cannot dress my sissies in as revealing clothes, but I can make them look perfect for sweater weather season. I have this one sissy who wants to be a trans girl like my twin sons. I have been working with her all summer. Her hair is now long and thick. She has some little boobies budding. Her body is softer and curvier. I waxed all the hair from her body too, even waxed her cockette. And with me doing her makeup and clothes, she was ready for her big debut as a trans girl. She wanted to see if she could pass in a normal setting, so we went to a Pumpkin Patch first. I had her in tight jeans, and a cute sweater. Put her in an old padded bra of mine to give her more curves. We just mingled with people at the pumpkin patch. My boys were with us. They were dressed too in their cute fall outfits.  The pumpkin patch was fun, but not how we wanted to end the night. I took my boys back home, and my trans sissy gurl and I went to a glory hole to practice her cock sucking skills. I am the best sissy trainer for trans girls. I can not only help them look like a girl, but I can also help them fuck like a girl. This glory hole I frequent is perfect for sissies to get some cock sucking experience. After she swallowed a bout a gallon of jizz, she wanted to pop her pussy cherry. Her sweet little backdoor cherry was ready too. I knocked on the wall, and over came a big burly man. He put my sissy on all fours, yanked her jeans off and fucked her from behind. I do not think he had any clue he was fucking a pretty sissy bitch. My client moaned, but she took that huge cock and huge load like a champion. My sissy training time with her is not over yet, but she is ready to live her life as a girl now under my continued tutelage.

Sissy-Bath Time is The Best!

Femboy training

 

Sissy-bath time is one of the most fun parts of my phenomenal femboy training!  Helping my girly guys get their little clitties all cleaned up and showing them how to properly take care of their dainty downstairs is super fun for both of us!  It fills my heart with pride knowing that I’m purifying those horny he-bitches and helping them get ready to take all the BBC that swings in their direction.

I don’t have any crotch goblins of my own, so I treat all of my sissy sluts as though I shot each one of them out of my pussy.  Since my little ones are full grown adults, though, sometimes getting them to submit to being an enslaved sissy and fully embody a perfect little priss is labor intensive.  Imagine trying to give birth when you’re 1600 weeks along.  It can get rough.  Attitudes abound, let me tell you.

Hot and steamy sissy bubble baths calm all of us down, though.  We climb in the tub, play around in the suds and let a bath bomb tickle us as it swirls around the top of the water.  I have a revitalizing shampoo that’s great for getting any sweat, spunk or spit out of their hair and I use a sea sponge loofah to help clean off any old cum that might be stuck to their skin.  When I clean off their ladyboy junk I use my soft fingers to get into all of the folds of their pussy-pricks and give those loose assholes they all have a special two fingered tickle-massage of a cleaning.  The soapy water lets my digits slide in and out of their dungers with little to no resistance.

When we’re done, I dry them off, give their butthole and wussy-puss the sniff and lick test then help them pick out the perfect pair of sissy panties and most outrageous outfit for the evening.  It’s like helping some street rat that I adopted get ready for their first date, only, unlike most parents, I hope that my little man-girl gets her ass plowed and pummeled by the end of the night.  It makes me all misty eyed just thinking about it.