Sissy Blog

Sissy blog about all things sissy: fashion, makeup, lifestyle, sissy training...

Smokey Eye Makeup for the Crossdressing Sissy

smokey eyes for the crossdressing sissySmokey eyes...No doubt the sexiest look for sultry eyes. Here's a graphic that shows step by step how to make your own smokey eyes.


Here's 7 Steps for Creating a Smokey eye look. My God, do they ever look exotic!





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Male Breast Implants

Male breast implants

Have you ever put on the prettiest skimpy, lacey bra and started w-i-s-h-i-n-g... for you know what?  (Breasts! silly)

Sexy lingerie feels just so wonderful!

But once you're in that sexy bra, don't you somtimes wish they were real breasts, not just stuffed with some fake filler?

There are lots of products out there that claim to be able to grow male breasts. You know, the natural estrogen. I don't know of any that really work. Leave comments if you have found something that works.

It's hard to get Premarin or prescription estrogen without a prescription. You're taking your chances if you find one of the sites that claim you can order without a prescription. Good luck.



Read about Male Breast Implants.

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Painted Toenails at the Men's Gym

I finally went to the gym, worried that my svelte figure was going to hell from lying around week after week. I had been sooo tired for sooo long. I just said f*** it, and packed my gym bag and drove to the gym.

It felt really good to be on the treadmill again. I don''t go to lift weights or any of that macho crap. I go to be slim and trim and a fit hardbody. I finished my workout and thought it would be very nice to finish the day with a long relaxing sauna. I showered, pulled my hair back, and slipped on my flip- flops. There's nuttin worse than foot fungus from public showers. I noticed I still had my toenail polish on-- oops. Oh well, I was the only one going into the sauna.

That's what I thought. I ladled some water to make steam and some young muscular guy came in. He sat at the other end of the bench I was on. It was embarrassingly silent and then he said, "Is that nail polish?"  I laughed and got nervous and right away started fumbling for a story. I was going to say my girlfriend was trying her new polish on me, but waited too long to make my excuse. He asked again, "Do you like wearing nail polish?"

I noticed his original question had changed. I felt like I couldn't answer. He was now facing me kind of in a crouched position, both on the toppermost bench where it's hottest. The heat had speeded up my heartbeat, but so was the nervousness. Or was it excitement?

 Many times I imagined getting caught doing my girlie stuff, now here I was, alone with a jock in a dimly lit sauna. He laughed and said, "That's alright, let me see." I felt like I was being let off the hook, so I turned enough to show my toes. "No. Let me see them. Put you feet up here." I lifted my legs onto the bench, swiveling my body to face the young stud. "Well, well, well, you shave your legs too! Relax I won''t hurt you. Lean back."

I leaned back against the hot cedar walls. That allowed me to be more comfortable. "I'm into feet," he grinned, massaging my feet, "especially pretty feet. Like yours." he massaged my feet and it was sooo relaxing. Once in a while his massage would go part way up my smooth calves. Then he did something shocking! He put my feet in between his legs, and I could feel an enormous erection!

He must've seen the shock on my face and he just laughed. Hey my massages are worth $60 an hour so now you have to start repaying me! He winked and took my feet and started rubbing them on the sides of his erection. Then I started doing it on my own, and as I got better at it, I even used my toes to tug his shorts down, then the real fun began. For him mostly. No I take that back, I think I was getting off on seeing my girlie toes pleasuring this fine stud.

footfuckWe tried to be sneaky cause there were a few people in the gym area, and when he finally came, it shot on my smooth silky legs and on my feet and pretty toes. "Let's see how much your stretching paid off," he smiled. He pushed my head all the way to my feet and made me lick his cum off my feet. He made me go back to the shower following behind him, where the cum on my face and legs and painted toenails brought looks of disgust, or surprise, or curiosity from the few guys getting dressed or undressed.

I watched my "friend" lean over and say something to one of the guys by a locker. They were both staring my direction. My stud came over to me, "you''re invited to work out with the 3 of us tomorrow." I would be there. Against my better judgement I knew I would.

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Christmas Again?

It''s time to give that little sissy inside you the gifts you've been withholding pleasures from.
We know.

You''ve secretly been trying not to allow that sissy inside you to get out.

Give yourself the gift of sissyness, you silly girl. You can''t fight it, you were born that way!
It starts with panties usually. Think back: did you raid your sister''s panties? Get them out of the laundry hamper?
Or was it bras? Stockings maybe? Your mommy's?
It starts with something. The first thing usually becomes your fetish item. Your secret wardrobe has likely grown. Maybe you have high heels by now, hopefully you do.

Maybe you''ve grown up a bit, and started using toys on yourself. If not, remember -- it''s Christmas!!!

Give yourself a fun playtoy that will help you advance in your sissy life. Maybe something really comfy to "fill you up": click heeeeere!
Another gift you can give that little sissy is some of the tapes that make sure you''re not denying yourself the pleasure to be who you are meant to be! 

sex toys for sissies

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A Happy New Year

So many sissy stories start with the wife or girlfriend or significant someone catching the sissy in the act. This one is not different.  It was New Year's Eve. Mitch had enough partying at the office, and said his goodbyes early. He never liked office parties, the women gravitated to certain guys but never to him. He didn't mind that too much. So he told himself. He did have one person who befriended him, but he suspected it was out of pity. She had heard others talk behind his back and often refer to him as Mitch the B*tch. Shilo would bring him coffee when she sensed Mitch was having a bad day. He loved smelling her Poison perfume, and admired the way she dressed, walked, and basically stayed different from the office gals. She was not intimidated, and dared to be different. Over the years, they became confidantes, and she often dragged Mitch along to her salon appointments. She would catch an odd look of longing in his eyes as he watched the manicurist shellac her nails and toenails in the wild colors she chose. Shilo was aware there was something different about Mitch, and that's probably why they clicked so well. He learned he could trust her and she would not betray him. From time to time, they would even sleep over at each others apartment, after visiting too late into the wee hours. That's why he eventually gave her his apartment key. This night that would be a grave mistake in judgement. Or would it? So the office party was a drag. Shilo watched Mitch becoming more withdrawn as the night wore on, and he was drinking one cocktail after another. She watched him say his goodbyes and exit. Was he going to be alright? She had friends who drank when they were depressed, and she never liked that combination. She always believed that you could confront that which was troubling you using your own inner strength. But she was innately strong. Some people weren't. Those were the ones that needed a guide.

Mitch arrived home, and plopped heavily into his armchair. His apartment only afforded a few pieces of furniture, and the living room served as his office, studio, and sometimes even his bedroom. Tonight it was going to serve as his bedroom. He was drunk. He knew he was drunk, and luckily he decided to come straight home. A drunk person wandering the streets alone on New Years was not safe in his neighborhood. He was on an upper floor, and he looked down on the city, imagining all the couples celebrating. Mitch began to wonder why he wasn't one of them. Am I so repulsive? Am I some kind of freak? In his alcoholic fog, he tried to make sense of his fate of being forever alone. He began to list all the things that might qualify him as a freak. Yes, it went even back to his childhood, when bullies called him a "sissy" and made fun of the way his mama dressed him. He didn't understand that his mother really wanted a girl, and she sent Mitch to school in very girly kinds of outfits, which he came to prefer, himself.

sissyboy pantyboi transvestite "THAT'S IT!!!" Mitch exclaimed out loud, "I'm a fucking sissy and everyone senses it!" He poured himself a gin and tonic and stood at the window again, this time a tear rolled out his eye. "I resolve to destroy the sissy in me!" Mitch said out loud, gripping his drink. For emphasis, he added, "I Mitch the B*tch do hereby resolve!" He ran to his crowded bedroom and tore the dresses down from the back of his closet where he hid them behind his suits. He pulled open his bottom drawer and flung the bras, panties, stockings, garters, and all the other feminine garments he could afford to have, as he lived alone and no one would ever disturb his dress-up evenings. That's what he did every night he returned from work, it just felt so relaxing to be himself for once. Now he was on a mission to destroy the sissy within.

He was panting and sobbing as he felt like he was losing a best friend. He sat on the bed sobbing, and unconsciously he began to caress the soft satin for the comforting feeling it gave him. Forgetting his mission, Mitch began to desire the women''s clothing more and more. He couldn't stand it. He'd read about the futility of "purging" your clothing and he felt defeated. Yes, defeated. He could not stop being a sissy. He loved it too much. It went too deep. It was part of who he was, and to hell with his coworkers. He slipped into the feminine clothing, lovingly slipping on each item. When he finished, he looked into the mirror and liked what he saw. He went to the bathroom and washed his tears away, and sat down at the vanity to apply his makeup ever so professionally. He had become quite good at it. He learned to imitate the "look" of his friend Shilo. If she could only see him now, he smiled. "Hey, I'm smiling all of a sudden!" he thought, and decided to have a toast to smiling.  He clickity-clicked into the small kitchen and mixed a drink. Then he went to his computer and began browsing the sissy sites he bookmarked.

First, he went to look at clothing he could get cheap, usually giving him an excuse to rotate his wardrobe and keep the dress-up nights exciting. He decided not to read any more about the hopelessness of his being a sissy, but instead began reading on how to enjoy being a sissy. After another drink, he toasted out loud, "I Mitch the B*tch do hereby resolve to be the best damn sissy this city has seen!" Then he proceeded to order recordings that would help him train his mind into being the best sissy. After all, it was a resolution. Feeling very smug now, and very drunk, Mitch realized he was turning a point, where he would come off the fence. He was relieved. He wanted to do things that he read other sissies did, so he started his spending spree. Never shop when you're drunk was rule #1 he had learned, but here he was breaking his cardinal rule. He found what he was looking for. Deprived of a partner, he always go SO worked up and excited, but also frustrated. This next order would help satisfy that craving. What the hell, it's New Years. It would take up space in his apartment, yes, but it looked like some kind of sexual workout machine too.

He just clicked the "Purchase" button when he heard a noise behind him. As he swung around, his huge "Shilo" earrings swung too, and his made up eyes grew twice as huge. It was Shilo!! "What the F**K!!!" he shouted. But Shilo pushed Mitch back down by his shoulders. "Well, well well. I thought you looked a little too eager when I took you shopping with me, or to the salon. So THIS is your secret desire. How sweet. Now I have a sissy boy."
Fucking Machine"I am NOT a sissy boy!" Mitch blurted, before realizing the absurdity of his retort.
"Well, lets see what you''ve been study so hard that you didn''t even hear a concerned friend at the door." She began to check Mitch''s browsing history. "um hmmm. um humm. I see. Okay. um humm." She went through his week of browsing and decided not to spend too much time confirming what she already had found out.

"Well, Mitch, what do we do now? This changes things a bit between you and me. I mean you can stop pretending now. I'll be coming over more often, maybe even every night. I am certainly curious about how your "exercise machine" is going to work. Maybe I''ll give it a spin myself!" She was certainly making Mitch blush. He had not uttered a single thing. Instead he began drinking straight from the bottle of gin. Shilo grabbed it away from him, and slapped him hard, "THAT IS NOT AN ANSWER!" she began sobbing, and said again more quietly, "That is not an answer, dear Michelle." She put her hand in his, and noticed that there was a bulge in his lap. Oh well, maybe he needs a firm hand too, as well as a gentle guide.

The story would go on, and Mitch would become Michelle, ever so gradually. It started with some physical changes. She knew he wanted it. Or should we say "she"? It was going to be a Happy New Year. And a very KINKY one! ;-)

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Shoe Fetish

Gotta admit, a foot fetish easily lends itself to another fetish in shoes! Your first pair of girlie shoes depends usually on what kind of sissy you see yourself as (or are being trained as).

There is something emphatic about slipping into a pair of shoes, don''t you agree? Of course, choosing the right shoe is important. If you have large calfs like men sometimes do, you''d probably be more interested in women''s boots that cover the calf. On the other hand, some of you are blessed with very sexy legs that should be shown off and highlighted with shoes that bring attention to the legs and feet.

A schoolgirl sissy will naturally gravitate toward Mary Janes, right? Can''t you visualize yourself wearing a pair with a skimply plaid skirt, and frilly socks?

high heels with padlockA nasty sissy would probably go for the spikey heels, really high ones. Maybe if being trained as aslut, would like to be PADLOCKED into their high heels. If this is you, then you should definitely check out Fetish Shoes from the pulldown menu under the "All Categories" block.

Whatever kind of sissy you are, there is a shoe for you! And don''t deprive yourself. Always have lots of things to choose from. That's the most rewarding thing: dressing up. is our favorite. Got shoes? No?

You might also want to get some "Sissy Training" if you''re still not really comfortable in your mind about being a sissy. There''s recordings here too about many other aspects of sissy training. Good girl.

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Plus Size Lingerie

Sexy Plus Size Lingerie

Plus size lingerie for sissies It's a fact that men are built differently than women. If you are not of the petite sort (which some sissies are lucky to have been born that way), you may have trouble finding women's lingerie that fits comfortably.

If you are overweight and if you are working on becoming more feminine, you may want to try some sissification mp3 recordings that have a subliminal effect on you.

Nowadays it's easy to shop online for anything the sissy crossdresser needs to complete her wardrobe. Work on that figure, practice your femininity, no matter what your size. See How to Lose Weight AND How to Get an Hourglass Figure on FemmeSecrets


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Toenail Art

ToenailsFirst of all do a Google Search for Toenail Art Images. You can also look at

After you study them, and look for one that appeals to you, learn how to do your own creative toenail art.

When you're done, and you are happy with your result, why not show them off? Do so here, where you can upload your toenail photo.

Need to train your sissy mind for Makeup Training mp3? Then by all means, do it!

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Makeup and Beauty

I want to tell you now, that if you do not know how to put on makeup you will look very obvious in public. If you're really bad at it, you may even look carnival-ish. It is important to study and practice practice practice.

A good way to do that is to get together with another sissy and have a day of fun. How do you manage to find someone like this? Of course, the very best way is through Adult Friend Finder (AFF).

Be diligent about setting aside entire days for your dressing up.
Believe me, makeup takes a while to put on, much less to learn secrets of application. In order to get your mind devoted to this, we recommend the Sissy Affirmations, and the Sissy Makeup Training mind training at

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There is so much information on the internet, it''s just a matter of sifting through it all. We like to find video turorials, learning best by watching, although plenty of sites have step-by-step instructions with images. You can also get all your makeup online too. Don''t worry. Everyone starts their sissy journey somewhere. Below is one of the examples of a video how-to

How to Natural Beauty

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Shapely Sissy

thumb 2007041722120629 2Yes, you CAN be shapely!
You get yourself all dressed up, painstakingly applied makeup and savoring the dress up time, and when you''re finished you excitedly look in the mirror. Is your response one of satisfaction and thrill, or one of disappointment and dismay?

There are the details that can help you be more feminine looking, if you are struggling with that. Men''s hips aren''t shaped the same as women''s, and neither are our butts. You will be happy to learn that there are PADDED PANTIES that will help you achieve that look.

Another thing: men''s physical frames are somewhat larger than men, but again -- fear not. Many places cater to large size women. One that you should be especially pleased with is called Hips and Curves. One item you should call your attention to is the Waist Cincher. It is a cross between a Corset and a garter belt. And we know how you love the garter belts just because they are sexy and feminine. But the waist cincer will draw in your waist and make you more shapely.

Do those 2 things to start. If you REALLY want to work on shape. Use a CORSET to start drawing it as tight as possible, until you can finally cinch it to get a real hourglass shape. But this is for the more serious minded sissy. You may grow into it, we hope.

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Gender Test and Body Image

Have you ever wondered what makes you who you are?
Why do you sometimes feel more feminine than masculine? Or more like a woman than a man?
It can be a little more than just a penchant for dressing up. It could have to do with your personality, your brain, your genetics, your testosterone. Lots of things. There are a few online Gender Tests we''ve mentioned before, but never replace real counseling or therapy with online questionaires. Just take them to see where you fit.

The COGIATI (COmbined Gender Identity And Transsexuality Inventory), Gender Aptitude Test,The Empathy Quotient (EQ) Test, and The Systemizing Quotient (EQ) Test are 4 tests you can take at Gender DynamiX

It''s been our position, that if you feel like a sissy, you ARE a sissy. If you are beginning to have doubts, then listen to some Sissy Affirmations. The hypnosis recordings will train your sissy mind.

Some secretly desire to be a REAL TRANSEXUAL. That''s your own business. To thine own self be true. Like the porn sites? If you fantasize about being a she-male, you probably like watching too.

If you just want to keep it at a fantasty or online level, there are hundreds of thousands of people out there waiting to do the same. You can mingle with them on sites like Adult Friend Finder. Or you can set up a real meet! Crossdresser, Transgender, Transexual --- it''s a wide wide world.

Finally, we want to tell you about Transfemme. Have you ever wanted boobs?

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Just Can't Help It

You are a sissy. Face it. It''s in your blood. You've tried abstinence. You've purged your wardrobe only to restock. You are who you are, my dear: a sweet little sissyboy. Accepting that, you will learn to be very happy being who/what you are.

Gender Tests for trangender and sissy boysMany look to others to help resolve a perceived conflict, framing it in the context of a problem to be solved, as opposed to an endearing facet of personality. One "problem-resolution" method has included gender tests or "mental sex" tests.

The Transexual Roadmap website has a good article on the dangers of these different tests, concluding that the tests should be used only for entertainment purposes. Confirmation about gender issues should come from introspection and discussion of your feelings with others who understand.

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Sissy Stories Train Your Mind

Feminization heels with lock - sissificationOne of the best things a sissy should do with her time is to read stories about how sissies need to learn and to be kept in their places. This helps do a couple things: it makes you come up with more creative things to experiment with, it gets your mind into a sissy frame of mind, and it keeps your fantasies on the front burner, baby!

The best story sites for SISSY and FEMINIZATION STORIES:

Crystal''s Story Site -- this is one of the older sites that has a searchable index of stories. You will find yourself mesmerized for hours!

Literotica -- they have also been around a while, thousands of stories searchable by tags (this link uses tag "sissy husband"

Satin Submissions -- Forced Feminization & Femdom stories for your naughty reading pleasure.

A Submissive Sissy -- Sissy & Femdom stories -- Feminization Fantasies for Sissy Girls & Panty Slaves

Other ways to train your sissy mind: Sissyme

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Digital Sissy

Online websites for sissy boysIn this day of social networking, it's pretty normal to have an online sissy persona complete with your nicest photos or videos. There are plenty of free online photo storage sites, and ways to share with your best  girlfriends.

Just remember that there are codes of conduct / terms of service and you don''t want to upload tons of photos and get your account closed because you didn''t read the terms of service.

A sissy should also join an adult site that lets you upload your naughty and sexy photos, if you get a thrill out of sharing your photos. Also, adult sites allow you to meet others with your own kinky interests, and even meet in real life if that''s your fancy.

One thing we are finding out, is that it is so convenient (*and cool) to travel with a tablet or smartphone rather than a big laptop. That, plus you can download all the social apps to upload to your sissy account and stay in touch with your sissy girlfriends. even has mobile apps so you can log in to your account from your iPhone/iPad/iPod or from your Android device.  What are you waiting for? It''s cool to be a social sissy!

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Short Shorts

Have you had a chance to show off your sissy tootsies and pink toenail polish -- or slutty red? And be sure to look at some ideas in the video below for short shorts looks. We know you want to!

 If you think you don't have the nerve to do something like this, you may need some sissy mind training. We find that using the subliminal voice suggestion here to be effective in training a sissy to develop the mind of a sissy, desire and all. You know you want to!

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Inner Sissy

Beginner Kit sex toys for sissy crossdressers     It's hard to resist the temptation to dress in sexy women's clothing. If you have even DREAMT about what it would feel like to be in a dress, or in high heels, or sexy stockings, the odds are you went ahead and tried it. You can not resist the impulse. It probably started by trying on your sister's panties when no one was home, right? Mmm hmm.

You probably began sneaking panties or other items after that first experience. How exciting it felt! You may have tried over the years to quit dressing, and maybe even felt guilty or bad like something was wrong with you. These periods of quitting were probably never successful. Once a sissy, always a sissy! Rather than live in shame, why not accept it? You should just come to terms with it. Get some of the sissy recordings we like to promote.

Go shopping for some nice things to wear. And for gosh sakes, do NOT PURGE them because you will only find yourself re-stocking your wardrobe later. We like to shop at auction sites where you can receive your pretty things in the mail and not have the mailman raise his eyebrows. That is, unless you really don''t mind packages labeled "Victoria''s Secret."

Another thing: Don''t shy away from treating yourself to the other feminine desires. Dressing up is only part of the experience. You will, of course, want to have some fun once you like what you see in the mirror. Treat your sissy bod to some of the pleasures your feeling. Stock up on toys while you''re at it. (click on the image above and look for some Beginners Kit. You will not regret it, sissy.

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How to Apply Nailpolish Professionally

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If you like nail polish (or the toenail polish you can get away with) you will love Laquerous


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Don't Spit, Swallow

One of the subjects true sissies eventually get around to is being very good on their knees, if you know what I mean -- I.e. Swallowing Semen.

While cum-swallowing won't provide all the nutrition you need for the day (unless you''re gobbling up massive amounts *wink* *wink* one ejaculation producing about a teaspoon does have some nutritional value.

Indeed, someone with a penchant for cum has even produced a book of recipes that call for this delicious wonderfully textured ingredient!

If you think you have trouble picturing yourself in the subservient "on your knees" position being of service, you need more mind training.

If you are ready and willing to be of service, you''ll enjoy this web site Don't Spit, Swallow


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The Sissy in You

You know you didn't end up on the Sissyboy site by accident. Uh uh. You''ve probably been Googling sissy searches all day, right? There is a sissy inside you aching to get out. The more you browse and read and look at beautiful crossdressers and trannies the more desperately you want to indulge.

That''s part of the conundrum of being a sissy, that deep dark desire to join the world of sissies, yet at the same time a hidden fear that maybe you shouldn't: either there''s something wrong or bad about it, or you may get discovered. Come on, even your flimsy excuses for abstaining can''t help you to control the urges, right? Isn''t part of the excitement itself from the possibility of getting caught?

Everyone wants to belong to a group, that''s PSYCH 101. The Internet makes indulging your inner sissy so much easier than the sissy of 20 years ago. You can participate in all the online groups, photo sharing, chat, even meet sissy admirers.

So fear not dear sissy. Join the wonderful, secret, exotic, crazy, indulgent, beautiful, sexy, naughty life of sissyness. You want to belong. When you join the many sissy sites you not only are making a statement that you belong in the world of sissies, you give yourself the access to some fairly risqué stuff. So have at it. Let your inner sissy free.

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Once a Sissy Always a Sissy

There's quite a lot written about the subject of "purging". You may have gone through this yourself. It's a waste of time and money.

Purging is when you throw out all your wardrobe, jewelry, makeup, shoes, you know... you decide it's time to quit this silliness and make an attempt at joining mainstream society and be a MAN! 

So many crossdressers, transvestites, sissies -- whatever name you want to go by -- end up simply going back to restocking all the beautiful, sexy, feminine things they enjoy so much in the first place. And all that money!

Why do you do it? A number of reasons, mostly confused emotions: guilt, anxiety, fear, or shame.

We'll tell you a secret: there's nothing to be ashamed of! This is part of who you are, for whatever reason it gives you relief to be feminine.

sissyboy, transvestite, crossdresser secret

So there! Be a sissy! We're telling you now, if you want to be a GOOD sissy, get your mind right with these Sissy Training mp3 recordings.


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Latest Blogs

10 February 2017
Makeup Tips
Smokey eyes...No doubt the sexiest look for sultry eyes. Here's a graphic t...
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10 February 2017
Have you ever put on the prettiest skimpy, lacey bra and started w-i-s-h-i...
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Fetish Toys for the Sissy