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!

Better sections in the CD/TV/TS dating page

How are you girls doing today? I’m finally getting settled back down after my move back to Florida. I wanted to tell you all about a change for the better I made in the transgender dating page in here. When I first made it, it was going to the crossdresser dating site. But of course we have many others here that are looking for others.

Some of us are looking for crossdressers or transvestites to date. But others here are looking for shemale dating, or want to date a transsexual. Still others would like to meet Asian ladyboys for dating. So I found out that this same dating service has a better section, made for all CD/TV/TS girls. This way you can find a crossdresser to date.

Or you can find a shemale dating girl. Others can find a hot Asian ladyboy for dating. So it appeals to all of the transgender girls that want to find others to date. Or even just to have some hot sex! Hell, nothing wrong with that right! So just go to the dating page here and click on the profiles to see the new format, or click on any up above to take you to it. Have fun dating!

Kinky sissy videos at the new Mistress Deedra’s sissy clips site!

Mistress Dedra's Sissy videos!

Check out the kinky sissy videos inside Mistress Deedra’s sissy clips site now!

Alrighty all my sissies and crossdresser girls, I’d like to showcase a sissy videos site I have been working on with my mistress Deedra! For those who know, I have been making sissy slave videos for the past 6 months or so.

Mistress Deedra is my mistress that I worship and do anything she ask. Deedra is a very sexy, tight body babe with the best perky ass you will ever see! Just check out that sweet ass in the picture below of her.

Mistress Dedra's Sissy videos!

Check out the kinky sissy videos inside Mistress Deedra’s sissy clips site now!

Mistress Deedra loves to tie her sissy up and do lots of kinky, humiliating and abusive things to her. She forces her sissy slave to eat condoms full of cum, whips her ass red, forces her to cum, shoves dildos up her ass and lots more.

It’s all hardcore sissy slave bondage porn, with your very own sissy as the slave! Mistress Deedra loves to tease too, showing off her petite body in thongs, sexy stockings, thigh high boots and other fetish wear.

Mistress Dedra's Sissy videos!

Check out the kinky sissy videos inside Mistress Deedra’s sissy clips site now!

I even get fondled and abused while wearing a kinky female mask and full body femskin suit! Needless to say I have a lot of fun letting my mistress tie me up and do hardcore, kinky things to me. It’s a sissies dream come true!

Mistress Dedra's Sissy videos!

Check out the kinky sissy videos inside Mistress Deedra’s sissy clips site now!

Well now you can buy each sissy video one at a time in Mistress Deedra’s new sissy clips site. By buying just the ones you want you save money while getting just the clips that turn you on the most.

Once you pay for a video your emailed your password and username with a link. You go to the link, enter your code and then download your video. You have 3 days to download the sissy videos.

Mistress Dedra's Sissy videos!

Check out the kinky sissy videos inside Mistress Deedra’s sissy clips site now!

Mistress Deedra will be adding more sissy videos each week, including some other sissy videos from partner sites! Soon she will be adding picture galleries you can buy also.

In time she will even open a full paysite so you can see all her sissy videos at any time. So check out the lovely Mistress Deedra today and buy a kinky sissy video you want to see, let me know what you think!

Mistress Dedra's Sissy videos!

Check out the kinky sissy videos inside Mistress Deedra’s sissy clips site now!

Poor sissies teased and abused by hot chicks!

sissy teasing at Humiliatrix!

Click to see the hot sissy teasing free tour inside Humiliatrix now!

Humiliatrix is the ultimate destination for all the sissies and pathetic men who need a real woman to tell them how worthless they are. This popular femdom site caters to those who fantasize about being completely dominated by unmerciful bitches.

Here you can watch sissy boys in extreme pain, as well as smoking hot mistresses who take full advantage of their poor slaves. They now have over 300 hot sissy movies plus much more!

sissy teasing at Humiliatrix!

Click to see the hot sissy teasing free tour inside Humiliatrix now!

The gorgeous chicks inside Humiliatrix are using poor sissy boys for their pleasure, torturing and abusing them in the cruelest possible manner. There are scenes of strapon fucking, sissy humiliation, extreme bondage, forced feminization, corporal punishment, small cock teasing, orgasm denial, trampling, spanking, whipping and cuckolding.

The site features a wealth of content, from the hottest femdom movies and pictures to sissy cartoons, erotic stories, drawings, strapon femdom galleries and more. If you are ready for an exciting preview, take the free tour available at Humiliatrix today!

sissy teasing at Humiliatrix!

Click to see the hot sissy teasing free tour inside Humiliatrix now!

Orgasm denial free movie clips from Teasing-Video

sissyboy tease and denial porn movies

Well it’s time once again to show you a few hot free videos from the best tease and denial porn site on the net, Teasing-Video! This time I took some of the sexy free teasing porn movies they have on the tour and put them on here. Each one of the videos you see if you click on it shows a short free teasing and denial porn movie. So just what the heck is a teasing and denial porn site?

Click here to take the tour for the Teasing-Video porn site!

Well it’s a little bit of everything, from bondage, to femdoms, to mistress worship. At Teasing-Video they have well over 250 teasing videos of poor sissyboys getting tied up to beds, chairs, stripper bars and other fun bondage devices. Then the super hot chicks unlock the sissy’s chastity lock, tease their poor cock almost to the point of orgasm,,,,,, then stop!!!!

sissyboy tease and denial porn movies

It’s enough to drive you mad, but it’s also every sissyboys dream, to be in total control from a hot mistress, doing what they tell them to do, then get their cock teased and fondled. The femdoms stroke, suck and even rub their pussies over the sissy’s rock hard cock. Each time the poor sissy strains and thinks this time she will let him come,,,, but does she??

Click here to take the tour for the Teasing-Video porn site!

Well you never know, that’s the fun part! The chicks are super hot with big tits and tight slender bodies, not to mention their shaved pink pussies. Sometimes the sissyboys are played with by two or more femdoms, making it even more exciting. They even have lesbians playing while the poor sissy has to watch, all tied up and just out of reach,,, owww!!

sissyboy tease and denial porn movies

It’s the best tease and denial, orgasm denied, femdom bondage video site on the net. They even have some cuckold humiliation and other neat sissyboy abuse. All the teasing videos are made in high definition, with two sizes to choose from. So check out the samples in the 3 videos here, then

Click here to take the tour for the Teasing-Video porn site!

Cruel Girlfriends, sissy forced feminization porn!

Sissy humiliation porn at the new Cruel Girlfriends!Sissy humiliation porn at the new Cruel Girlfriends!
See lots more tight teen babes humiliating their sissys inside the free tour of Cruel Girlfriends today!

Every sissy wants to be humiliated by a good looking woman armed with kinky toys. The babes from Cruel Girlfriend definitely know how to make a guy feel like a looser.

These chicks force their boyfriends to wear girlish clothes while they are getting fucked by real men. They make fun of the poor sissies, telling them how pathetic they are.

Sissy humiliation porn at the new Cruel Girlfriends!Sissy humiliation porn at the new Cruel Girlfriends!
See lots more tight teen babes humiliating their sissys inside the free tour of Cruel Girlfriends today!

At Cruel Girlfriend, you will get humiliated, ridiculed, and abused by dominant babes. The poor sissies are forced to wear tutus, clean the floor with their tongues, and even work in the porn industry to pay for their girlfriends’ luxury vacation.

Some sissy boys get fucked by horny gay guys, while others are forced to watch their girlfriends having sex with real studs. From public humiliation and verbal abuse to cuckold, blowjobs, strapon fucking, sissy maid training, and forced feminization Cruel Girlfriend offers tons of movies and pictures for those who believe in female supremacy. Check out this site and take the free tour for a preview now!

Sissy humiliation porn at the new Cruel Girlfriends!Sissy humiliation porn at the new Cruel Girlfriends!
See lots more tight teen babes humiliating their sissys inside the free tour of Cruel Girlfriends today!

Hot chicks force feminize sissyboys and force bisex fuck

forced sissification and feminization at Mean Girls!

Every few weeks I try to find a hot new crossdresser porn site for you all to check out. Today I have another hot one for the sissyboys! It’s called Mean Girls, and it features very sexy chicks forcing sissyboys to do some very kinky forced feminization porn, as well as many other forced dominatrix sex. The things they make their sissies do will make you scream “please take me master”!

forced sissification and feminization at Mean Girls!

In these screen captures from a sample video, two hot babes force their sissies to dress up in maid outfits complete with makeup and wigs, with panties and pantyhose. After they do some work they decide to have fun with them, and bend one over and fuck his face with a strap-on while the other uses a drill to fuck his ass with a huge toy! Next they force the other sissy maid to fuck his ass with a strap-on wrapped around his face.

forced sissification and feminization at Mean Girls!

Finally at the end they force the two sissyboys to kiss and make out while they watch. They also force sissies to wear blindfolds, then make them suck dick without knowing they are. The beautiful babes also make them lick their assholes out, doing ass worship, feet worship, cuckold humiliation, slave milking, cum eating, strap-on fucking and lots more. It’s a sissies dream come true as these hot chicks make their sissy slaves do every degrading, teasing, sissy fucking act including bondage!

Check all the forced feminization sissy sex out today!

forced sissification and feminization at Mean Girls!

Gay Sissies, hot crossdresser porn!

crossdresser porn at gay sissies!crossdresser porn at gay sissies!
Hi everyone, how’s all the kinky Halloween parties going! Watch the kids, we don’t want to warp their minds by showing up in a naughty maid outfit before they get sent to bed! Well today’s post is a real treat. A lot of you seem to really like the brand new site crossdresser porn site, Gay Sissies! I STILL think the damn name is wrong, as we crossdressers do NOT want to be called gay!

But despite the name, it’s really a great new crossdresser porn site. So I have a total of 4 different crossdresser porn galleries for you to see from them. It has a bit of everything in it. Sissyboy maids getting man handled and fucked by their boss, crossdresser girls seducing straight guys and sucking cocks, office sissie girls getting banged by the boss over his desk!

Yes it has every kind of sissie crossdresser porn you could want to see and lots of it. These poor crossdresser sissies get hardcore fucked in every set, all by male bosses, friends or otherwise abused by studs with big dicks. With 4 sets to check out you really get a chance to see what it’s all about. Of course you can take the long tour here and see much more, or click on each picture to see each set.

crossdresser porn at gay sissies!

Once you join you also get access to a panyhose crossdresser site to, so you get a great deal. The movies are top quality too, they’ve been making crossdresser porn sites for years so they really know what you want and give it to you! So enjoy the crossdresser porn sets at Gay sissies, it’s a great site that only gets better!

crossdresser porn at gay sissies!

tease and humiliation femdom site

orgasm denial site

So how did everyone’s weekend go? Hope your doing ok despite the economy. Well to take your mind off things I’ll show you another new site. It’s a lot like the teasing video site I made a post about a few weeks ago. This one is called Indecisive Captions. It has a big mix of hot caption pictures, short picture stories, short videos and even audio. It’s all about super hot babes teasing and doing orgasm denial, chastity cock locks, cuckolding them and even femdom bondage.

They currently have over 6,000 caption pictures like the one above, over 200 videos and audio clips and lots of neat picture stories. The stories open like a book, you press to see the next page. The chicks are very sexy and yes you see them naked and in hardcore sex. They add over 150 new orgasm denial caption pictures and videos each month. It’s lots of fun to read the caption pictures and see what they say.

The short videos are also really hot, as busty chicks tease sissyboys cocks and stroke them, but stop before they can get off! The audio is hot also. With a big mix of chastity, orgasm denial, cock teasing, cuckold humiliation and femdom bondage there’s sure to be plenty of stuff you like. If your not into caption porn they also have a huge teasing video site with over 250 videos and 2 new ones added each week. Click the screen below to take a peek at the site.

orgasm denial site

So they pretty much have you covered for any type of tease and denial, orgasm ruined, cuckold humiliation and femdom mistress worship and bondage porn you may want. They update all the site often, and the sexy babes are damn hot! So check it all out by going to the Teasing Video site, or the Indecisive Captions site!

orgasm denial site

Sissys get ass fucked by Strapon Jane

crossdresser sex with Strapon Jane!

Check out the kinky free tour at Strapon Jane today!

Strapon Jane is an expert at using her monstrous rubber cocks on sissies, trannies, crossdressers, men and women. Known as “the most hardcore British strap-on Mistress around,” this babe has absolutely no limits when abusing her sissy slaves.

Strapon Jane is one of the most attractive and cruel mistresses you will ever meet. This smoking hot chick makes a memorable impression that will never forget.

crossdresser sex with Strapon Jane!

Check out the kinky free tour at Strapon Jane today!

One of the things I like the most about Strapon Jane is that she has a kinky porn site packed with female domination videos and pictures. You get a nice big shot of her, plus images depicting scenes of forced feminization, bondage, strapon fucking, trampling, spanking, sissy humiliation and lesbian porn.

Updates are weekly, and revolve around her big fat rubber cock and the way she humiliates poor sissies like you. For an exciting preview, be sure to check the free tour available at Strapon Jane!

Check out the kinky free tour at Strapon Jane today!

crossdresser sex with Strapon Jane!

Check out the kinky free tour at Strapon Jane today!

Sissyboy crossdressers get fucked by males

sissy crossdresser fucked by cop

Weeee, looks like this sissyboy crossdresser has her ass covered huh, lol! I thought I’d share another gallery with you from the new site called Gay Sissies. Now, I really don’t like the name of it, I mean most of us don’t want to be called gay, because we are not! BUT, if you can get past the name it actually is a really cool sissie crossdresser site.

What’s nice about it is it has feminine sissies all dressed up and having jobs as maids and stuff like that. Then they get sexually harassed and fucked by their male boss, co worker or other type of Kinky situation. They also have crossdressers having sex with each other in full dresses, pantyhose and other lingerie fetish wear. What could be better than getting felt up and banged by a horny guy while your dressed as a maid!

The dresses, stockings, panties and other lingerie are all very nice, not that crap you see in cheap sites. They even have the sissies getting deep kissed, something you don’t see in other sissie sites. So it’s a nice big mix of crossdressers having sex, ass toying and crossdressing sissies getting chased and ass fucked by studs, yes!

The gallery today has the sissyboy in a green top and skirt with stockings and high heels. A cop is there, and soon it’s the sissie that gets stuck up by his big cock! This slender sissie really gets her ass split wide while she wears her frilly panties. When you join now you also get a crossdresser pantyhose site for free. So check out the gallery below, or take the long free tour with hot videos here.

Click here for the gallery!

sissy crossdresser fucked by cop

Sexy feminization & humiliation mistresses phone sex

sissie and humiliation phone sex

Well I hope your all having a nice weekend. 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 girls. 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

Sexy mistresses humiliate sissies at Humiliatrix

sissy humiliation and cuckold teasing

Hi everyone, TGIF! One more time we get to relax and have some fun over the weekend. So, I wanted to share this great sissy site with you. I already made a post about it, but I don’t think I did a good job explaining just what it’s about. It’s called Humiliatrix, and it’s a very large site filled with hot dominate babes that love to have fun with you sissyboys.

Or rather, they have fun mocking you, putting you down, laughing at your small cock, force feminizing you and just plain having their way with you. They have over a dozen very beautiful mistresses, each one specializing in her own form of sissy control. Some do the whole sissification and force feminization thing, dressing up their sissy slaves and having them do the housework.

sissy humiliation and cuckold teasing

Then for a reward they get a big strap-on dildo up the ass! Others love to laugh at your little cock, calling her girlfriends over to see how small your wee wee is, playing with it, then locking it up in a cock lock while teasing you with their big tits and tight asses. They love having you sissies lick their boots and suck their toes as they lay back with just their thongs and bikini tops on.

sissy humiliation and cuckold teasing

Humiliatrix has lots of hot videos of all the babes, as they dominate and abuse their sissy slaves. Lots of strap-on fucking, cock teasing, bondage and more, all with hard body chicks that are wearing next to nothing, but not letting you quite see anything! Well, maybe a little here and there, when their slaves have been good!

They also have sissy stories, sissy cartoons, sissy audio recordings, public sissie humiliation assignments and more. Some of the chicks are even into cuckold teasing and humiliation, as they get fucked with big black cocks as you are forced to watch. It’s one big site filled with all the sissy humiliation, cock teasing you could want, all run by beautiful, half naked mistresses. Take the big long tour today!

Click here for the tour!

sissy humiliation and cuckold teasing