Welcome to the Sissy Forced Feminization section of Crossdresser Playground!

Here you can find everything about being a sissyboy, sissy slut, sissy training, forced feminization and sissification. Use the links to your left
to get around the different sections, and the top navigation bar
above for the main site pages. Enjoy you sissy girl you!

Sexy femdoms verbally tease and humiliate sissies!

sissie and humiliation phone sex

It’s time for something different today! I wanted to share yet another new site I found for those sissies, humiliation and forced feminization lovers of us. It’s a place called Talk Sugar, and it’s a great place filled with sexy babes that specialize in hot phone sex with those into being a sissie, wanting to be humiliated or talking about being forced feminized.

sissie and humiliation phone sex

They have dozens of girls that are into everything from femdom, sexy mistresses that demand you to worship them, dominate bitches that will strap-on fuck you and much more. Kinky fetishes, baby talk girls, all kinds of things. Each picture you see is a screen shot I took of that mistress, clicking on the picture will take you right to her page.

sissie and humiliation phone sex

You can choose between just hearing a hot recording to actually talking to the mistress. Most of them even have a live cam so you can see them as your talking to them if you use your computer phone! These girls have been doing this for a long time so the know just what you want to hear and how to treat you. From motherly feminization talk, putting down your small cock, to all out femdom sissie and humiliation talk, they do it all.

So check it out and see what it’s all about. You can click a picture to go right to that mistresses page, or click below to go to the main page and list of all the mistresses. Have fun, and let these girls demean you, mother you, force feminize you and humiliate you!

Click here to go to the main list of mistresses!

sissie and humiliation phone sex

Tasty teen babes tease sissy slaves at Humiliatrix

Tight femdoms inside Humiliatrix!

Check out the long and sexy free tour at Humiliatrix and see these tight body babes humiliate and tease their sissies today!

If your a sissy and want to see the hottest teen mistresses around teasing you with their tight ass and bouncy tits, make sure you check out Humiliatrix! Inside here you can watch hundreds of hot point of view sissy teasing and humiliation movies.

They look like they are talking right to you, or strapon fucking you, whipping you and so on. They run around in tiny thongs and little tops, teasing you sissies with their hot bodies. The mistresses in here are super hot too, with tight fresh, tasty bodies, yum!

Tight femdoms inside Humiliatrix!

Check out the long and sexy free tour at Humiliatrix and see these tight body babes humiliate and tease their sissies today!

Humiliatrix has lots more than just sissy movies however. You also get to ready erotic sissy stories, see sissy cartoons and drawings, caption sissy pictures and picture stories, hear audio sissy assignments and more.

They update the site twice a week with more sissy teasing and denial movies that’s sure to get your sissy cock hard in your panties! See for yourself in the long and free tour inside Humiliatrix today and cream your pink panties!

Check out the long and sexy free tour at Humiliatrix and see these tight body babes humiliate and tease their sissies today!

Tight femdoms inside Humiliatrix!

Check out the long and sexy free tour at Humiliatrix and see these tight body babes humiliate and tease their sissies today!

Meet sissies in your area today for hot sex!

If you want to meet real crossdressers, sissies and trannies in your local area, there is no better place than Date A Crossdresser! On the web now for a few years, Date A Crossdresser is the most popular tgirls dating and contact site on the web.

In fact it’s the only real dating and contact site for crossdressers and tgirls that I know of. Many horny crossdressers want to find others around them. Or maybe your a sissy looking for a hot femdom to be a slave for.

Still others want to try a transsexual babe for the first time. Whatever your reason, you can find them all at Date A Crossdresser. It’s an honest and real dating site with real local crossdressers, sissies and tgirls.

You can join for free and look at all the members in your area before ever paying a dime. Only when you want to contact someone do you have to upgrade to a paying membership. So click a profile above and get your free account today at Date A Crossdresser!

Sissies strapon fucked by Mistress Annabelle!

Vintage Cross Dressing porn with Lady Annabelle!
Make sure you take the free tour at Vintage Cross Dressing with Mistress Annabelle today!

Vintage Cross Dressing opens a whole new world of possibilities to those who are passionate about cross dressing and femdom. This amazing new site is run by Mistress Annabelle, a dominant and beautiful woman with a deep attraction for vintage lingerie, silk corsets, nylon stockings, and pointed stiletto heels.

This unmerciful gal has a tiny 18 inch waist, big breasts, and long legs. She definitely is one of the hottest mistresses out there. Annabelle runs her site herself, so she gives it lots of loving attention.

Vintage Cross Dressing porn with Lady Annabelle!
Make sure you take the free tour at Vintage Cross Dressing with Mistress Annabelle today!

This beautiful gal loves to use her big strapon on sissy slaves and indulge them in some puppy play. She dresses her slaves in old fashioned lingerie and vintage dresses, and then she orders them to prepare her a cup of tea or clean the floor.

Her cross dresser porn site features high quality videos and picture galleries showcasing highly erotic images. You also can read sissy stories, get a weekly letter from Annabelle and more.

Vintage Cross Dressing porn with Lady Annabelle!
Make sure you take the free tour at Vintage Cross Dressing with Mistress Annabelle today!

The quality of Vintage Cross Dressing is the best I have ever seen and it makes a big difference. Lady Annabelle is always wearing the best fetish lingerie, satin dresses, seamed stockings and kinky outfits.

The sets are like a movie production studio, with the best props, bondage devices and more. Mistress Annabelle is a real working mistress, so you can even contact her for a personal sissy slut training!

Vintage Cross Dressing porn with Lady Annabelle!
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The cross dresser sex is hot too, with some kinky threesomes showing real cross dressers fucking each other and sucking cocks while lady Annabelle plays with them all.

Lady Annabelle is passionate about sissy slut training, bondage, spanking, trampling, forced bi, pony play and other fetishes. The content is updated every Friday with no exception. For a preview, take the kinky free tour at Vintage Cross Dressing today and see it all!

Vintage Cross Dressing porn with Lady Annabelle!
Make sure you take the free tour at Vintage Cross Dressing with Mistress Annabelle today!

New kinky femdom sex at Strapon Helga

crossdressers fucked inside Strapon Helga!

See the hot kinky free tour at the new femdom site Strapon Helga for sexy crossdresser fucking action today!

Here’s a new crossdressing porn site run by Strapon Helga. This sexy mistress is new in town and she looks incredibly hot. As you see, she has a slender body, beautiful tits, and round ass.

More than that, Strapon Helga loves playing roles while wearing fetish outfits, latex costumes, high heels, and more. The best is that she has a huge collection of thick strapons that she uses to punish crossdressers and sissies.

crossdressers fucked inside Strapon Helga!

See the hot kinky free tour at the new femdom site Strapon Helga for sexy crossdresser fucking action today!

Strapon Helga loves fucking her slaves in the ass with a giant cock. This babe can be cruel and dominant, as well as sweet and sensual. Most times she ties up her slaves in bondage, forcing them to suck her monster cock.

There’s forced feminization, sissification, ass whipping and spanking, and even lesbian sex. New crossdressing movies and pictures are added once or twice a week, so there’s always something new to watch. For an exciting preview, take the free tour at Strapon Helga now!

See the hot kinky free tour at the new femdom site Strapon Helga for sexy crossdresser fucking action today!

crossdressers fucked inside Strapon Helga!

See the hot kinky free tour at the new femdom site Strapon Helga for sexy crossdresser fucking action today!

Kinky sissy training with sexy femdoms

Sissy Slut Training!

See the long kinky sissy tour inside Sissy Slut Training now!

I have recently found a new crossdresser site addressed to all those who want to be completely dominated by women. Sissy Slut Training is all about cruel mistresses who are looking to torment their sissy slaves.

The poor sissies get a good ass fucking by a strapon wearing slut, being whipped into submission. If being a sissy slave turns you on, then you should visit this kinky site and take some lessons from other crossdressers like you.

Sissy Slut Training!

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The best thing about Sissy Slut Training is that it covers lots of aspects of female domination, from spanking and trampling to forced feminization, sissification, whipping, bondage, nipple torment, and more.

The babes are experts in slave training and inflicting pain on their sissies. They abuse and torture their slaves in the most sadistic ways for their own pleasure. If this idea sounds good to you, take the free tour and share your experience with other sissies!

See the long kinky sissy tour inside Sissy Slut Training now!

Sissy Slut Training!

See the long kinky sissy tour inside Sissy Slut Training now!

Pretty sissies get trained to suck cocks inside Mrs Lovings

loving sissy training at Mrs Lovings Sissy Feminization

Find out how good feminization can be in the free tour at Mrs Lovings sissy feminization today!

If you want to experience something new, check out Mrs Lovings Sissy Feminization. This kinky site is truly different, as it features mature women who are slave training their sissies in a gentle manner.

Mrs Loving is a nice lady who teaches sissies like you to behave and listen to her commands. The best is that she shows them what to wear in order to look like some real girls.

loving sissy training at Mrs Lovings Sissy Feminization

Find out how good feminization can be in the free tour at Mrs Lovings sissy feminization today!

As soon as you visit Mrs Lovings Sissy Feminization, you’ll get to watch mature women taking good care of their sissies. They train them to wear lacy dresses, high heels, wigs, stockings, petticoats, and makeup.

The final lesson has the role to teach them to suck real cocks while getting their sissy asses fucked. As you see, Mrs Lovings Sissy Feminization presents a series of movies and pictures designed to turn sissies in realistic girls who listen to their mistress. For a free lesson, take the free tour right now!

Find out how good feminization can be in the free tour at Mrs Lovings sissy feminization today!

loving sissy training at Mrs Lovings Sissy Feminization

Find out how good feminization can be in the free tour at Mrs Lovings sissy feminization today!

Kinky femdom sex with Strapon Helga

Sexy femdom porn babe Strapon Helga!

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It’s always exciting to write about a new crossdresser and sissy femdom porn site, so today I’m happy to present to you Strapon Helga! This sexy femdom babe is petite with a tight body, sweet ass and perky tits.

Strapon Helga loves to fuck sissys and crossdressers up the ass with her many big strapon dildos! She fucks hot females too in every hole, after getting her own pink pussy licked good.

Sexy femdom porn babe Strapon Helga!

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Strapon Helga has fantastic femdom sissy movies, showing sexy crossdressers and sissys in pretty panties, stockings, full makeup and dresses. After teasing them she often ties them up in kinky bondage.

Then she has her fun, whipping and spanking them till their ass is red, Forcing them to suck each others cocks, fucking their pretty mouths with her strapon before ramming it deep in their sissy ass and fucking them silly!

Sexy femdom porn babe Strapon Helga!

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Helga gets naked too, having her pussy licked by her crossdresser sissies or sitting on their faces. She pops her pale pink tits out often while wearing kinky corsets, stockings and other fetish wear like thigh high boots.

Strapon Helga is a great porn site for sissy humiliation, forced bi cock sucking, strapon fucking, ass whipping and spanking, forced feminization and even hot lesbian sex. It’s a wild kinky orgy that often involves three or more people getting fucked.

Sexy femdom porn babe Strapon Helga!

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Helga already has thousands of femdom pictures and hours of high definition femdom sissy movies. Plus she adds a fresh update once or twice a week. It’s the best newest femdom site for crossdresser and sissy porn!

If you love seeing crossdressing sissies getting forced to suck cocks and strapons before getting tied up in bondage and fucked hardcore up their tight asses, with sexy females having fun too, then check out the free kinky tour at Strapon Helga right now!

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Sexy femdom porn babe Strapon Helga!

Click here to see the new kinky free crossdresser sissy femdom porn tour at Strapon Helga right now!

Cruel Girlfriend, kinky sissy humiliation porn site!

Sissy humiliation porn at the new Cruel Girlfriends!Sissy humiliation porn at the new Cruel Girlfriends!
Check out the kinky free tour inside the new Cruel Girlfriends sissy humiliation porn site now!

It’s time to showcase yet another new sissy humiliation porn site! This one is called Cruel Girlfriends, and it features tight, hard body teen babes that tease and humiliate their sissy boyfriends.

Being completely humiliated by a cruel, sexy woman is a unique experience. The heartless chicks from Cruel Girlfriend love to humiliate losers like you. These babes are dominant, hot and sadistic.

They kick their boyfriends with spiked heel boots, fuck them in the ass with fake cocks, and dress them up like sissy ballerina girls. These chicks have no mercy for the guys in their lives.

Sissy humiliation porn at the new Cruel Girlfriends!Sissy humiliation porn at the new Cruel Girlfriends!
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The brutal gals from Cruel Girlfriend love to have wild sex while being watched by their sissy boyfriends. They torment and tease their sissy slaves, spend all their money on designer shoes, and hit them with heartless verbal insults.

The babes are smoking hot and look like real porn stars. They have perfect bodies, big tits, and great asses. You can watch how they force their boyfriends to wear chastity devices and then they fuck their real-man lovers all night.

The site is updated every week with sissy humiliation videos, sissy caption pictures and sexy MP3 sissy verbal abuse audio tapes. For a preview, check out the free tour from Cruel Girlfriend today and see how kinky sissy humiliation can be!

Sissy humiliation porn at the new Cruel Girlfriends!Sissy humiliation porn at the new Cruel Girlfriends!
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Forced Crossdresser Fantasies, kinky sissy cartoons

Crossdresser stories and cartoons

Click here for the kinky crossdresser cartoons and crossdresser stories tour inside Forced Crossdresser Fantasies!

Crossdresser cartoons, drawings and crossdressing stories are very popular with us crossdressing girls and sissies. However it’s very hard to find sites like that, or at least quality ones that have a lot.

Forced Crossdresser Fantasies is a crossdresser website that has been around for a few years. The owner is herself a crossdresser with a passion for crossdresser stories and cartoons.

Crossdresser stories and cartoons

Click here for the kinky crossdresser cartoons and crossdresser stories tour inside Forced Crossdresser Fantasies!

You can find over 2,000 kinky crossdresser and sissy dawings and cartoons in here of all kinds. There are sissy humiliation, forced feminization, sissy bondage, sexy femdoms, forced bi cock sucking and much more.

All the crossdresser and sissy cartoons and drawings are unique, made from different artist for lots of different styles to see. You can even find comic style crossdresser cartoons with a story line.

Crossdresser stories and cartoons

Click here for the kinky crossdresser cartoons and crossdresser stories tour inside Forced Crossdresser Fantasies!

Speaking of stories, you can also find hundreds of great crossdresser stories to read. Some are very long, with a long plot and even different chapters that continue to the next week.

However there are plenty of short crossdresser story pages to read also. Many of the crossdresser stories come with kinky crossdressing cartoons and drawings to enhance the story.

Crossdresser stories and cartoons

Click here for the kinky crossdresser cartoons and crossdresser stories tour inside Forced Crossdresser Fantasies!

Forced Crossdresser Fantasies has several different sections inside filled with hot and sexy crossdresser stories and cartoons. From sissy wimps that get forced to suck and take big cocks to feminized crossdressers, you can find it all in here.

The site is updated several times a week, and the join price is lower than most other crossdresser porn sites. So if you want to see kinky crossdresser and sissy cartoons plus read lots of hot crossdresser stories, check out Forced Crossdresser Fantasies free tour today!

Click here for the kinky crossdresser cartoons and crossdresser stories tour inside Forced Crossdresser Fantasies!

Crossdresser stories and cartoons

Click here for the kinky crossdresser cartoons and crossdresser stories tour inside Forced Crossdresser Fantasies!

Watch hundreds of sissy movies at Humiliatrix!

Teased sissys inside Humiliatrix!

Check out the free kinky sissy tour at Humiliatrix now!

I’m sure you have heard about Humiliatrix, the place where sissy boys like you are turned into submissive slaves by young and beautiful girls. These evil bitches deliver total humiliation as they penetrate the guys with their large rubber cocks, abusing them in every hole.

These ladies love to tease sissies while humiliating them about the size of their cocks. There is verbal humiliation, orgasm denial, cock and balls torture, whipping, trampling, ass worship, foot worship, kinky sissy bondage, spanking, and much more!

Teased sissys inside Humiliatrix!

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These real evil women are really dominant and cruel and they live to humiliate their slaves. As they strapon their rubber dildos, they make the sissies take the fake cock in their asses.

The content quality is very high because of its uniqueness. Humiliatrix features the most exciting audio humiliation clips, kinky cartoons, movies, pictures, and stories about guys who get their sissy asses fucked by horny bitches. So if you want to get a preview and see these babes in action, check out the free tour from Humiliatrix!

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Teased sissys inside Humiliatrix!

Check out the free kinky sissy tour at Humiliatrix now!

Girlfriends fuck their sissy boyfriends silly

Sissy movies at My Sissy Boyfriend!

Check out the hot free tour inside My Sissy Boyfriend!

If you dream of wearing girlish clothes while getting fucked in the ass by your girlfriend, then you really should visit My Sissy Boyfriend. The babes featured here carry out exciting domination performances, forcing the guys to become bitches when they take off their panties.

You’ll find anal fisting, sissy abuse, strapon fucking, and forced feminization, so get ready for some real action. This is a mixture of fetishes that you really don’t see too often, featuring the best of both worlds.

Sissy movies at My Sissy Boyfriend!

Check out the hot free tour inside My Sissy Boyfriend!

Once you get inside My Sissy Boyfriend, you’ll be able to watch sissy boys like you engaging in hardcore sex with some beautiful women with strapons. The guys are wearing their girlfriends’ skin-tight clothes and try to behave and look feminine.

They get fucked in the ass and abused by their girlfriends and they seem to enjoy the whole thing. The babes get naked too and get their pink pussies played with. For the hottest movies and pictures at My Sissy Boyfriend, take the free tour as soon as you can!

Check out the hot free tour inside My Sissy Boyfriend!

Sissy movies at My Sissy Boyfriend!

Check out the hot free tour inside My Sissy Boyfriend!