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!

Gay Sissies movie galleries for your holiday cheer!

Gay Sissies porn movies gallery

So how the hell are your holidays going huh? Staying out of trouble,,,, yeah right! Well, I don’t have much way to give my readers anything, except maybe some free Gay Sissies porn movies! The porn site called Gay Sissies has been the most popular gay, or I should say bisexual, crossdresser porn site I have featured on here.

Lots of you like it, and I must admit the sissyboys in it are slender and hot, with tight asses that get fucked by big long dicks. It features crossdressing sissies in lots of different settings. Bosses fucking the sissie office boy, sissy maids in their outfits and stockings getting banged by the horny man of the house and so much more.

It also has crossdressers fucking other crossdressers with both their dicks and big toys. The pantyhose, stockings and dresses are really sexy, and they do a good job with their makeup too! So today I have a total of four Gay Sissies porn movies for you. Clicking on the top picture takes you to the gay sissies movie gallery with three different movies.

The bottom picture will take you to another Gay Sissies movie gallery that has 6 different short movie clips of the same sissy maid getting her hot ass hammered hard in her maid outfit and black stockings with high heels! So enjoy the free movie clips, and if you really like what you see click the tour link to see the whole tour with more movie clips. They still offer a bonus pantyhose porn site if you join right now. Sooooo, click here for the Gay Sissies porn site tour, or

Click here for the gay sissie maid movie gallery, or the top one for three!

Gay Sissies porn movies gallery

Sissy forced feminization and cock abuse

sissyboy foot worship and milking

Now that Christmas is over, it’s time to buy the presents you REALLY want for yourself. That means joining a hot sissy porn site, like Mean Girls Club. I’ve got a cool sissy picture gallery today from them, it’s two sexy girls abusing a sissyboy with chastity cock locks, foot worship and some forced milking.

They drop this sissys pants and reveal his cock locked up tight in a plastic chastity lock. They tease his cock, making it swell and hurt inside the lock. After sticking their tight ass and pussy in his face they put him on the floor and rub their feet over his abused dick. Finally they take the lock off and use some toys to milk him off.

Mean Girls Club touches on every cool sissy porn subject, like forced feminization, sissy humiliation, tease and denial, foot and ass worship, face sitting, sissy strap-on fucking, sissy training, forced slave milking, even forced bisexual banging! It’s a sissyboy’s dream porn site as a dozen or so sexy mistresses abuse their sissyboy slaves.

The girls are super hot looking, and they get naked and even fucked, but only after they dress their sissies up in cute maid outfits, make them clean the bathroom and suck on the pizza guy’s dick! If you never joined a sissy porn site before but always wanted to, this one has a bit of every sissy sissification sex you would want. Take the long free tour with hot videos here, or

Click here for the foot worship and forced sissy milking gallery!

sissyboy foot worship and milking

Humiliatrix, sissy femdom humiliation porn site review

Humiliatrix porn site movieHumiliatrix porn site movie

These are low quality sample movies, the ones inside site are much better

Humiliatrix tease picturesHumiliatrix tease picturesHumiliatrix tease picturesHumiliatrix tease pictures

CLICK TO PLAY MOVIES AND SEE PICTURES

Well today’s post will brighten up your Monday, at least if your a sissyboy! I’ve been able to go inside and make a review of what may be the best sissy porn site yet, Humiliatrix! I never knew just what there was inside, or how much there was. I had an idea, but it’s just not the same as going in and really seeing for yourself.

I was very pleased with what I found inside. Not only do they have great sissyboy humiliation and forced feminization movies, but they also have many audio humiliation clips, stories, cartoons, drawings, pictures and caption picture stories! There are a dozen or two super sexy mistresses that tease and humiliate sissyboys like you.

Every sissy subject is hit on, including cockold humiliation, sissyboy slaves, sissyboy maids, forced feminization, ass worship, foot worship, foot licking, sissy strap-on fucking, pantie humiliation, tease and denial, face sitting, kinky sissy bondage, small cock teasing, chastity cock locks, even forced cock sucking and cum eating. It’s a sissyboy dream come true!

Everything is done so that it’s from your point of view. So the hot mistresses are talking to YOU when they tell you to whip out your cock and beat it, or get ready for a strap-on fucking, weeeee! The verbal abuse and put downs are very good, hell all of it is! Just go and read the full review below, or go right to the tour link and see for yourself how good it is. I highly recommend this sissyboy site!

Click here for the Humiliatrix porn site review

CLICK FOR HUMILIATRIX PORN SITE TOUR!

CLICK FOR SAMPLE MOVIES

These are low quality samples, movies in site are much better
Humiliatrix porn site movieHumiliatrix porn site movie

Dealing with the sissy holiday blues

Holiday blues

I hope everyone is having a good holiday season. But the truth is, many don’t look forward to the whole Christmas season. It’s not because of the actual reason for Christmas, it’s because of all the other stuff that gets shoved in your face during this time of year. Many travel to family for the Hoidays, and for some that’s reason enough to get the blues!

For those in big family’s, you get the whole “so are we going to your parents house or mine Christmas day” fight. Then when you get there you have to pretend you really look forward to cousin Larry and his darling 4 kids, or try to remember all the distant relatives who say hi and you don’t have a clue who they are.

This year is even more trying for most, as the economy crunch has really cut into people’s lives. Many who thought they were going to be celebrating Christmas in their new home are now crammed in a tiny apt. and looking for work. Never mind who’s at fault, the point is it can really get you down. Everyone wants to give their kids what they want for Christmas. Read more…

Forced feminization sissyboys get abused by sexy mistresses

Sissyboy humiliation porn

Damn, look at the size of that strap-on dildo that girl on the right has! I hope she knows what she’s doing! This picture and the one below are from hot sissyboy humiliation movies from Mean Girls Club. They are fairly new, and they seem to really have a good grasp of just what a good sissyboy humiliation porn site should be.

Sexy, hot chicks that love to tease, humiliate and play with their sissyboy slaves, that’s what a good sissy site is about. They have about a dozen super hot chicks that get naked and drive their sissyboys nuts. They cover everything too; mistress ass worship, foot licking, cockold humiliation, sissy training, forced feminization, sissy slave milking, forced cock sucking and more fun stuff!

The two mean girls above fuck this poor sissyboy both ways, getting his ass stretched wide with those strap-on dildos. Meanwhile the slender hot chick below gets some face sitting in as she puts her ass right on her sissyboys nose before letting him lick her pussy out. They even force their sissys to suck real cocks; these cruel mistresses know no limits to sissyboy abuse! Check out the long free tour to Mean Girls Club today and see all the action!

Sissyboy humiliation porn

Poor sissyboys fucked hard by guys at Gay Sissies

sissyboy fucked by guy at Gay Sissies

Ouch, that looks a bit painful! Yes I have another hot gallery for all you sissyboys and transvestite lovers. It’s another sissyboy fucked gallery from Gay Sissies. I’ve been amazed at how many of you like this site, I’ve had more of you girls join this than any other site. But then again I can see why, you love watching these sissyboys get hardcore fucked by studs!

This gallery has a cute sissyboy in a flower print dress getting a big cock shoved down his throat, sucking it hard. Then this sissy gets put on his back and spread wide as his tight ass gets split and fucked by that long cock. He gets hammered several different ways before it’s all over, his ass a bit sore and walking funny! Gay Sissies has a mix of crossdressers and sissyboys dressed in frilly panties and dresses, along with stockings and high heels.

They are maids who get fondled by the boss, office girls who get bend over the desk and fucked, sissyboys who get taken advantage of. They even have crossdressers having sex with other crossdressers. They still throw in a second paysite, Men In Pantyhose, if you join up now. So take their big long free tour and see the videos and pictures to find out what it’s all about, or

Click here for the Gay Sissies gallery!

sissyboy fucked by guy at Gay Sissies

Forced feminization sissyboy banged by shemale and female

hot shemale and female fuck a sissyboy

Wow, have I got a hot shemale sissyboy gallery for you today! See, that shemales stroking his dick so fast its on fire! Ok, so maybe I put that there, I try not to show too much on my site. But rest assured you see that and much more in the gallery. And what a good one it is, as this poor sissyboy gets a good forced feminization makeover by both a sexy shemale AND a hot female!

It’s from that great porn site, Shemale Sissification. In this movie a shemale and female friend have some fun with their sissyboy pal. Stripping him down they tie him up, then do his face over with pretty makeup and a wig. They complete it with stockings, panties and a kinky red outfit. Seeing their new girl all done up gets them horny, and soon they get naked.

The shemale shoves her cock in his mouth as the female puts on a strapon and rams it up his ass. Then they switch and he gets a shemale dick up his tight ass as he get a wet pussy thrust in his face to lick on. Wow, every sissyboys dream huh, a dick in the ass and a pussy in the face! They hardcore fuck this sissyboy silly.

Shemale Sissification is the only porn site with sexy shemales fucking sissyboys that have been forced feminization made up into pretty girls. They have hot females that get in on the action too. A lot of sets have two shemales fucking their poor sissyboy on each end, fun fun! If you’ve never seen the tour, then take it now and see the hot free videos at Shemale Sissification, or

Click here for the sissyboy fucked by shemale and female gallery!

Sissyboy gets ass spanked by Nylon Jane

sexy Nylon Jane fucked by sissyboy

Well once again I’m showing a new site here for all you crossdressing perverts, Nylon Jane! Actually her kinky porn site is not new, but I never knew just what she does in her site. I thought she did pantyhose, stocking type of sex with other females or guys. Well, she does, and lots of it. But she also has some very hot and kinky sex with crossdressers and sissyboys!

THAT I did not know until I watched a set, or two,, or three! ;) Yes Nylon Jane is the same sexy strapon queen from Strap-on Jane the fetish queen. She also has her other porn site, Nylon Jane. In this site she always wears kinky fetish stockings, pantyhose, lingerie and other cool fetish clothing. Then she has hot sex with females and males as well as transvestites and sissyboys!

Like in this gallery here in the picture above. That’s a sissyboy in those pink panties and frilly outfit with stockings. This sissy gets her ass slapped hard and pushed around a bit by Nylon Jane. Then she rewards him by sucking his sissy dick and letting him fuck her doggie style, hot damn! Nylon Jane has a sexy body with huge knockers and a firm round ass.

She does every type of kinky fetish femdom sex with females, males, transvestite and crossdressers, as well as plenty of sissyboys. The outfits are fantastic and hot, with lots of pantyhose play, stockings, lingerie and some leather and vinyl wear. So it’s well worth checking out if you have a clothing fetish. Click here to take the long free tour with videos, or

Click here for the Nylon Jane sissyboy sex gallery!

New crossdresser porn galleries in the picture section

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!

Sissy Captions, new sissification sissyboy 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