Welcome to Crossdresser Playground, one stop mega site for all things CD/TV/TS related!

This place is big, so use the navigation links to your left to pick
specific CD/TV/TS sections. Links in the top navigation bar lead
to main pages of interest to all. Hit the crossdresser home link to
get back here. Browse around, have fun and make yourself at home!
If you want to say hi, join the CD/TV/TS forum and chat or post a picture!

New CD/TV picture gallery in the picture page

Kims anal heaven tv porntransvestite Luci May!transvestite sex

Click pictures to see the full gallery!

What’s going on everyone! Are you getting tired of that Christmas music already? This is one of those times I’m happy that I’m 90% deaf, that can be a good thing sometimes! I wanted to let my regular readers, all 2 or so of them, know about something new I just made. I redid the picture gallery so that you have more crossdresser and transvestite porn gallery pictures and movies to see!

So now you not only have the other sections in the picture gallery page, but below those are a whole bunch of mixed crossdresser, sissy, transvestite, shemale and ladyboy galleries! Clicking on each picture takes you to the full gallery that picture was taken from so you can see all the hot porn details, neat huh!

I will TRY to update that page with new galleries each week, making it bigger and bigger. I know, I keep saying that about the other sections and never get around to it. But I try, and I added this right, so bare with me. It will be a big mix of different types of crossdresser, transvestite and shemale porn galleries. Right now there are 15 new ones, so go check it out!

Click here for the picture gallery page!

Now is best time for a Orlando Disney vacation!

Walt Disney World Orlando vacation

Huh? What the hell does Walt Disney World have to do with crossdressing? Well nothing I suppose, unless you count all those characters in those costumes. Having worked there myself for two years I can tell you that many of those Mickey Mouses has a pussy inside that suit, and some of those female Disney characters has a hard on!

In fact I once tried to date a little cute female midget who played an,,,,, ewok!! Yes, one of those furry things from Star Wars. No, she was not hairy and no, I did not get to go out with her ok! The reason I mention Disney is because I live here in Orlando and go by the theme parks all the time. In fact I’m making a Orlando tourist site, fun fun! Read more…

Sissy Captions, new sissy forced feminization porn site

forced feminization at Sissy Captions porn site

Well sissyboys, it’s time for another cool sissy porn site to look at! Damn, how many sissy forced feminization porn sites can there be out there! A lot I guess. This one is called Sissy Captions, and it’s made by the same great company that makes Teasing Videos. Sissy Captions has over 2,300 hot pictures of sexy mistresses making their sissyboys into the sweet slave they want them to be.

forced feminization at Sissy Captions porn site

They put captions on the pictures, just like you see here. Most of them are full hardcore, as you see the hot chicks strapon fucking their sissyboys up the ass, letting them lick their sweet pussies and so on. They also have some good short sissyboy videos and audio sissy tapes too. It’s great forced feminization, with a touch of femdom, bondage, strapon fucking and sissy humiliation.

Sissy Captions has dozens of hot chicks getting naked and abusing their sissyboy slaves. You see the sissys in cute maid outfits, cleaning the house, getting whipped and all those things we sissyboy love our mistresses to do! The captions are really hot and make a visual story to read. They even have pages of captions that make a short story.

So if forced feminization and sissification of little sissyboys turn you on, then Sissy Captions will please you. You see these sexy mistresses naked or teasing, just out of reach of their poor sissyboy slaves. So take the tour here and see what this great forced feminization sissy site is all about!

forced feminization at Sissy Captions porn site

New transvestite porn site, Kims Anal Heaven!

Transvestite porn at Kims Anal Heaven

Whenever a brand new transvestite porn site comes out, I figure it’s my job to tell you about it. Well, a spanking brand new one has just been made, and it’s a beauty!! This one is called Kims Anal Heaven, and it stars,,, who else but KIM, a kinky transvestite with the best legs and ass in the biz! That’s her to your right, the shorter one.

Take a look at the bottom picture below. Is that the best transvestite ass you’ve ever seen or what! She has a deep tan, sexy legs and a rock hard body with blond hair. What her specialty is, is shoving huge toys up her tight ass! I mean 3 inch diameter kong dongs and things that would give a horse a hernia! She takes them all, along with real cocks too of course.

Kims Anal Heaven is made by the same people that bring you Zoe Fuck Puppet and Luci May, so you know the transvestite sex gets wild and crazy in here. That also means it’s a high quality site and honest with it’s members. It updates twice a week so you always have fresh transvestite porn and anal action to watch! Other transvestite porn stars make guest appearances too, like the two I mentioned.

It’s anal transvestite toying at the extreme level, with plenty of TV on TV sex, cock sucking and kinky porn action. The outfits Kim wears are so sexy and erotic, with lots of fetish wear and lingerie. The long tour gives you more free videos and pictures, so click here for Kims Anal Heaven tour, or

Click here for Kims Anal Heaven picture gallery!

Transvestite porn at Kims Anal Heaven

New Shemale Japan porn site review!

Shemale Japan porn site review

Well like I said in my last post, I’m starting to add more cool stuff in here. Today I added a new porn site review, and it’s a good one! This is for the new Shemale Japan porn site! The folks over there let me get inside the paysite and watch all the hot Japanese shemales having sex and getting nasty. Everything in my review is honest and true.

Japanese shemales are really beautiful, with petite and feminine bodies like a ladyboy, but with milky white skin and bouncy tits like a shemale. They have very smooth skin and often have red hair, I guess because of their pale white skin. Anyway I made a full and honest porn site review of it. It took me 2 hours, so you better read it! I have 6 different Japanese shemale galleries you can see in the review too. So,,,

Click here for the Shemale Japan porn site review!

Crossdresser stories and myspace

Do you want a “myspace” on here?

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Do you want a story page?

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Hi everyone, hope your week is going well. For a long time I have been just slapping up post after post of crossdresser porn sites and other porn related post. I did that because,,, well,,, most of you like looking at that of course! But also it’s faster to do that then write a real personal post,,, like this one. For months I have had lots of writing to do for others, that’s my main income.

So I never had time to really make some meaningful post on here, I always was in too much of a rush. Well I now am making more off my websites, I have about 8 of them. So that means I can cut back a bit on my writing. I now have a person that I write for who wants a long steady stream of post. So, I can do just those and have more time to work on this site, which is what I really want to do.

I am starting to add more fun things to this site. A few of them are a crossdresser story page and a “myspace” type of crossdresser place we girls can meet each other. Many of us love to read erotic crossdresser stories. They can be sissyboy stories, forced feminization, transformation, transvestite sex, fetish and so much more. I plan to have that page started within a week.

As for the crossdresser myspace, or whatever you want to call it, I need to look at what scripts are out there for it. I think that would be a big hit, as we girls love to talk to each other and meet other girls. I also have a few more things I will add. Some of it is adult, others are not. I’m going to add a chat room too, and a game section for online games.

So please take my poll above and let me know if you really are interested in seeing a crossdresser story page here, and if you’d like a myspace type of site on here for crossdressers. I’m going to make this a really kick-ass crossdresser site!! ;)

sexy Tgirl shows her tits at Frank’s Tgirl World

shemale porn

Alright everyone, once again I’m showing you a new gallery from a new sponsor. This one is from Frank’s Tgirl World, one of the biggest and best Tgirl and shemale porn sites on the net. The hottie Tgirl in this gallery is Brenda, a very sexy babe with nice big hooters. I’m not sure if she’s Latina or Brazilian, but I do know she’s hot! She strips out of her little pink top and shows those perky melons off for all to see.

Then she takes it all off and strokes her Tgirl cock to hardness, waving it around. Brenda has a damn hot Tgirl body, one I would love to kiss all over. She’s one of the many sexy Tgirls you can find inside Frank’s Tgirl World. Frank goes all over the world and films the hottest Tgirl babes he can find. He captures them on the beach, at clubs, at home, anywhere they are he goes.

So you get the most diversified Tgirl babes on the net, with black, Latina, Brazilian, white, Asian and whatever else there is out there for Tgirl babes! Frank’s Tgirl World has over 2,015 different Tgirl models, over 340,000 Tgirl porn pictures and over 1,208 full Tgirl porn movies. Try watching all that and running out! They update every week with lots more too. From solo to full hardcore and gang bangs, you see it all in here for hot Tgirl porn. So check out the long free tour of Frank’s Tgirl World here, or

Click here for Tgirl porn chick Brenda’s gallery!

youtube crossdresser rubber doll fetish video


What’s up everyone! I have had a BAD day, I’m tired and not in the mood for a long post. Sooooo, I thought I’d show you all a youtube video of rubber dolls. No not kids dolls, but full grown dolls. It’s kinky and cool, and it’s a rubber doll fetish video, what’s not to like huh! So check it out and I’ll have a better post tomorrow, ok!!

Sissyboy fucked by strapon by sexy mistresses

sissyboy fucked by strapon at mean girls club

Hi everyone, hope your Sunday is going well. I made a post last week about a new forced feminization and humiliation site called Mean Girl’s Club. A lot of you seem to like it, so I found some picture galleries to share. This one today features a sissyboy that gets caught by the girls sniffing their footwear, ewww! You just know this bad sissyboy is going to get punished by the hot mistresses!

First they strip him naked, then strap a feather duster to his face and force him to clean up their footwear closet. They spank and tease him as he works, then decide he needs much more punishment then that. So they put the old strapon dildos on and force him to lick and suck them a bit before getting him on all fours and banging him. Yes this fucked sissyboy by strapons really gets his ass split!

The Mean Girls Club features a dozen or so very sexy mistresses that enjoy humiliating, force feminization, sissification, sissy training, cuckolding, slave milking and even forced cock sucking! They sit on their faces, make them lick their feet, dress them up as sissyboy maids and humiliate them in every way. The sissyboy porn videos are fantastic and high quality.

The free tour is very long and has lots of sissyboy movies so you really see what the site is about. The girls are hot, with big bouncy tits and tight asses, weeee! They do lots of sissyboy strapon fucking and much more. So go to the long tour with videos at Mean Girls Club here!

sissyboy fucked by strapon at mean girls club

High heel stockings & lingerie fetish site Stiletto Girl

high heel stockings pantyhose and lingerie fetish porn site

All right all you high heel, stockings, pantyhose and lingerie fetish lovers, I’ve got a brand new porn site that will make your panties wet! Hell, if your a crossdresser then you must be a high heel and stocking fetish lover, right? Well this brand new site was made just for you crossdresser lingerie fetish, stocking fetish, high heel fetish and pantyhose fetish lovers.

high heel stockings pantyhose and lingerie fetish porn site

It’s called Stiletto Girl, and it has very sexy, leggy women posing and walking around in the most “to die for” high heels and stockings, along with pantyhose, garter belts and frilly lace lingerie and panties. It’s a crossdressers high heel and stockings fetish lovers dream come true! It’s not really fair to call it a porn site, because the truth is they show no nudity at all. It’s a true shoe fetish lovers site, along with all the other stockings and lingerie fetish.

They now have around 40 very beautiful girls, in over 18,000 high resolution pictures and over 300 high heel shoe fetish videos! I’ve seen the tour, and it’s a high class act all the way. Sexy women showing off the best stilettos, high heels, pumps and many more hot shoe fetish styles. All while wearing the sexiest stockings, garters, pantyhose, lingerie and panty fetish styles.

The only trouble with this site will be you want to know where the hell they got all those hot shoes and stockings! They have a very large tour so you really see what they have, and boy they have a lot! They really know what high heel shoe fetish lovers want, as well as stockings, pantyhose and lingerie fetish lovers. So go here and click the tour link to see the great big tour, or click on any picture to see that gallery.

Click here for the high heel and stockings fetish tour of Stiletto Girl!

high heel stockings pantyhose and lingerie fetish porn site