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!

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

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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

Sexy feminization ebook out for kindle and tablets

Kinky sissy stories ebook out now!
Click here to see more about it and buy today!

Today I have something new for you! We all know more and more people are reading ebooks on Kindles, tablets and other types of readers. Sissy and crossdressing stories are getting very popular to read as ebooks as well.

So I am starting to make a line of sissy, cross dressing and feminization stories in ebook form! I am selling them on Amazon for a relatively cheap price each. In time when I get enough I’ll make some into bundles so you can buy several stories in one book.

You can read these sissy stories on your Kindle, tablet, other wireless readers, mobile phones and even on your computer. Basically any type of electronic reader device can be used to view these kinky stories.

This sissy story is called Training of a kept sissy! It’s about a cute sissy that gets caught sneaking a peek at a sexy mistress. Soon the poor sissy is brought to the estate of the mistress for proper sissy training.

Will our sissy be able to handle her kinky sissy training? Will she get in trouble? What naughty things will happen between her and her new sissy roommate? You’ll just have to find out inside the book!

It’s a short story, about 19 pages long. It does have explicit sissy and cross dressing sex content, just so you know. I hope this will be the start of many more sissy and cross dresser stories.

I also will make some femdom, gay and erotic stories that are more “normal” in style, so to speak. A bit of everything for all taste. So check out the new Training of a kept sissy ebook today and start reading great sissy stories!

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

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!

Sissy slave abuse videos at Femdom Empire!

Cross dressing porn feminization!
Check out the best sissy and cross dresser forced feminization videos today!

Femdom Empire caters to those who believe in female supremacy. This femdom site is run by dominant females with the help of male submissives.

The babes are very attractive and have beautiful bodies enhanced by tight latex corsets, knee high leather boots, catsuits, balconette bras, and fetish costumes. Femdom Empire features famous mistresses such as Cybill Troy, Nyx Blake, and Kendra James.

Cross dressing porn feminization!
Check out the best sissy and cross dresser forced feminization videos today!

This kinky femdom site showcases young, beautiful mistresses who use male slaves for their own pleasure. They force to poor sissy slaves to suck fake cocks, eat cum from the floor, and beg for mercy. Some movies feature forced milkings, bondage, trampling, verbal humiliation, sissy feminization, corporal punishment, and cuckolding.

These babes love to make their slaves feel pathetic and worthless. They fuck the poor slaves in the ass, slap and crop their tightly tied balls, and then spit on them. For a preview, visit Femdom Empire and check out the free tour now!

Cross dressing porn feminization!
Check out the best sissy and cross dresser forced feminization videos today!

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

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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

Sissy fucked video from Vintage Cross Dressing!

crossdressing porn with Lady Annabelle!
See lots more sissy ass fucking videos with Mistress Annabelle in the free tour now!

Wowza, just watch as Lady Annabelle strapon fucks this cute sissy up the ass with a giant dildo! After a good pounding she switches to an even thicker and longer one, will that sissy be able to take it!?

You’ll just have to take a peek at Vintage Cross Dressing to find out! This is the best cross dressing and sissy porn site out there for sure. It’s run by Lady Annabelle, the most beautiful mistress on the net.

Each Friday mistress Annabelle updates her site with new high quality cross dresser porn videos and picture sets. It’s like a movie production each time, with super high quality lighting and sets.

See several cute sissies get ass fucked, forced to suck cocks, get tied up in bondage and lots more by Lady Annabelle and her other dominatrix girls. Don’t wait, take the amazing free tour today at Vintage Cross Dressing now!

crossdressing porn with Lady Annabelle!
See lots more sissy ass fucking videos with Mistress Annabelle in the free tour now!

Cute sissyboy gets fucked at Gay Sissies

hot crossdresser porn from gay sissies

Hi everyone! I am very surprised about the amount of you sissyboys that seem to love the new crossdresser porn site, Gay Sissies. Frankly I thought the title of it would scare a lot of you off, as I know we hate to be called gay. But the fact is that’s it’s a great crossdresser porn site, so here’s another hot gallery for you. In this one a cute sissyboy in a red top and sexy jean shorts gets herself manhandled by her boyfriend.

Soon she’s sucking his cock before getting it shoved deep in her ass. This sissyboy gets the fucking of her life as she gets it every way. The sissies at Gay Sissies are a wide variety bunch. Some are maids that get forced fucked by their male bosses. Others are office sissys that get played with by the head honcho at work. Still others are cute sissies with boyfriends that seem to get fucked all day!

They also have crossdressing porn with other crossdressers too, as both dressed up girls have some fun with each other. The sissies have great lingerie and makeup, looking very hot and sexy. It’s a real crossdressing sissy porn site, not those others that seem fake and don’t know what they are doing. They have a lot of crossdresser porn movies and pictures now, and you still get a bonus crossdresser pantyhose site free when you join. So check out the tour for Gay Sissies here, or

Click here for the Gay Sissies crossdresser porn gallery!

hot crossdresser porn from gay sissies

Quality sissy maid outfits at The Sissy Store!

Cute sissy maid outfits at the sissy store!
See all the sissy outfits and accessories inside the sissy store!

If you’ve bought sissy maid outfits before, you know it’s very hard to find one that fits well. Us sissy boys are just not made the same way as a real female and it’s hard to get clothes made for them to fit us.

But there is one place, and only one place as far as I know, where you can buy a quality sissy maid outfit custom made just for you! It’s called The Sissy Store and they carry over 70 different sissy maid dresses.

Cute sissy maid outfits at the sissy store!
See all the sissy outfits and accessories inside the sissy store!

Each one is made of high quality satin with lots of lacy trim, bows and ruffles. You can choose from several different colors, not just plain old black. Baby blue, red, pink, yellow and more colors are options you have.

Once you find a sissy maid outfit you want, you give up to seven different measurements so they can cut it to fit you perfectly. You can even request long or short sleeves, long or short skirt and more.

Cute sissy maid outfits at the sissy store!
See all the sissy outfits and accessories inside the sissy store!

They also have many options to choose from. Like adding tiny sissy bells, matching hair ribbons and sissy cuffs, sissy handbags, garters and more. Plus they have a wide selection of sissy dresses, panties, stockings, petticoats and other sissy clothing.

It’s the biggest and best sissy outfits store you can find! So check out The Sissy Store today and get your dream sissy maid outfit custom cut to fit you perfectly with all the sissy options!

Cute sissy maid outfits at the sissy store!
See all the sissy outfits and accessories inside the sissy store!