Crossdressing Photography Basics

The basics in crossdressing photography are the same as the basics in all photography. Get creative, try different things and think outside the box. You should also wear a lot of makeup and huge breast forms.

As Robert Jordan once said: “There is one rule, above all others, for being a man. Whatever comes, face it on your feet.” Of course, sometimes a man has to face whatever comes while on his knees. Sometimes a man may even have to swallow his pride, among other things. Every picture tells a story so use a fast shutter speed.

Linda Zoe

Linda Zoe

Real Men Carry A Cute Purse

There are several advantages of carrying a smaller bag, but the main one is that its lighter. By the time you pack all your stuff into a large handbag it can weigh twenty pounds or more, which is tough on your whole body.

You don’t need to carry everything everywhere. Sure, its nice to pack extra makeup, pantyhose, condoms, tissues, books, binoculars, a full size camera and lenses, handguns, tasers, and even your Chihuahua, but its not necessary.

Marie Kondo wrote The Life-Changing Magic of Tidying Up, which has absolutely nothing to do with purses, clutches, shoulder bags, crossdressers, transvestites or sissies, but she’s making a fortune. Its about determining which items spark joy. So put the dog down, grab your purse, throw in your lipstick, condoms and tissues and go to town.

Britney Smith (possibly not his real name) really nails it with his little bag and is ready to do whatever it is he does.

Britney Smith

Britney Smith

The Male Secretary-Dress Code and Work Ethic

Working as a secretary can be a very rewarding job for a man if approached in the right way. Most if not all of your coworkers will be women, so you will have a ball talking about clothes, makeup, and cute guys. But there are certain things you have to consider, including occasionally doing some actual work.

Whether or not you can type 100 words per minute may not matter if you dress the part. First of all you need to follow the dress code. Office rules vary but matching lipstick and nail polish are almost always appreciated, especially as you will set an example for the other girls.

The always lovely Linda Zoe (possibly not his real name) demonstrates some of the essentials.

Dressed For Success

Dressed For Success

At some point you will have to stop browsing lingerie and porn sites and just do your job, they probably didn’t hire you just because you look great in a short dress. There are files to file, paperclips to sort and the always stressful taking dictation in shorthand (keep your legs crossed).

Lost in thought

Lost in thought

Now this may be your dream job and the pay can be fantastic, but its not all sitting pretty and reapplying your lipstick. Common secretary duties include answering telephones, greeting visitors, ordering supplies and providing various services to customers. You have to take your job very seriously and you have to be a team player.

Of course, most men have the attention span of a goldfish when work is not all that exciting, so there is one more skill to master. This may take practice but in the long run it will pay off every time. When your boss asks for the report you were supposed to have finished hours ago but completely forgot about, its time for the move.

Slowly stand up from your desk making sure the tops of your stockings are showing, smooth your dress and show him those gorgeous legs. Get close enough to him so that he can smell your perfume and look him right in the eye. Next is the tricky part and you may have to tailor your response to the man in charge.

Lick your lips and say: Oh Mister Manager, I’m so, so sorry, is there anything I can do to make this up to you? Anything? Nine out of ten men will find something for you to do but be discreet, its harder to sleep your way to the top when the other girls are doing the same thing.

The Move

The Move

Ironing Tips For Men

The first step in successfully ironing your clothes is making sure you have the right tools for the job. The right tools include an adorable dress, stockings and high heels. Lipstick, earrings and nail polish are optional but can help you channel your inner housewife.

Rachel Boomboom (possibly not his real name) demonstrates the proper stance, its all about balance and posture.

Rachel Boomboom

Rachel Boomboom

Harness Racing

So you want to wear a lace harness? This naughty number will stop him in his tracks (you may or may not want that). Its made with soft stretch lace, satin ribbon ties, and Venice lace accents. Stunning on its own but also beautiful as a layering piece.

This Etsy shop is called Naughty Naughty Lingerie and is owned by Terry Rebecca Gilchrist. Terry wakes up and gets ready to “be the girl who will be making your panties” and smiles…ready to change the world, one comfy sleep bra and skirted thong at a time.

Note: you can’t change the world until you change your panties.

Black Lace Harness

Black Lace Harness

Black Lace Harness by Naughty Naughty on Etsy

Base Layers

We went to the park this morning for a brisk walk, reveling in the beauty of January and breathing in the cool morning air. After about five minutes my friend announced that he’s freezing and is going back to the car.

The beauty of January

The beauty of January

Sure, it was 20 degrees, but I was dressed for the weather wearing several layers of tight, thin clothing commonly known as base layers. Most guys do not wear the right base layers to stay warm and comfortable.

A base layer should be tight fitting so it traps air next to the skin and insulates the body from the cold as demonstrated by this man. Don’t forget a warm, comfortable pair of gloves. Wig, lipstick and adorable necklace are optional but highly recommended.

Base Layers

Base Layers

Fall Fashion for Men that Dress like Women

Pinterest is a great place to go for fashion, makeup and clothing inspiration. Here is the beautiful Linda Zoe demonstrating fashion staples that never go out of style. Huge breasts, a very sexy blouse, black stockings, a short skirt, bright red lipstick, long nails, a wig, jewellery, and cute high heels. He has also mastered the classic couch pose and is sitting pretty.

Linda Zoe

Linda Zoe

Sissy Audio-Special Requests

I am recording again and will be adding to my Podcast very soon. If you have suggestions or special requests leave a comment below.

Sissy stories will be considered but must be less than 1000 words. A good example is Saragirl’s Sissy Confession (see my story page or Podcast). Do not send me anything without discussing it first, there are only 24 little hours in a day.

Topics can include forced feminization, sissy humiliation, transvestite bondage, sissy maids, or all of the above. But absolutely no more cheerleader fantasies, too many torn ligaments.

Cheers

Cheers

The Halloween Sissy

Its never too early to plan for Halloween. Make sure you have the right lingerie, stockings, garter belt, corset or bra, heels and dress. You’ll also need to do something with your hair, and for many of you that means a wig.

Makeup help is always available and is as close as your local beauty salon. Ideally you’ll stop in ahead of time and make an appointment, then come in that afternoon or evening fully dressed.

Make sure everything fits, practice walking in your high heels, and decide on the right jewelry and perfume. You’ll also need a cute purse or bag for lipstick, extra panties and of course condoms.

Just don’t bite off more than you can chew.

Head to toe

Head to toe

The Most Interesting Man In The World Is A Crossdresser

The most interesting man in the world, in my opinion, wears panties, bras, nightgowns, skirts, blouses, dresses, wigs and makeup. The most interesting man in the world is a 20 year old straight guy from the UK. His favorite hobby is crossdressing and taking pictures of himself every time he dresses up as Lucy.

The most interesting man in the world is one of very, very few men to post photos of himself in male mode when he’s not dressed up as a girl. His parents know about his hobby, I’m guessing a lot of his friends know, and he doesn’t seem to care.

THIS GUY HAS BALLS! (not shown).

Lucy-CD.tumblr

The Most Interesting Man in the World

The Most Interesting Man in the World

Feminized by Mom and Her Friend

Getting caught in the panty drawer and feminized as punishment is a favorite fantasy for all crossdressers, transvestites and sissies. Getting caught and feminized by your Mother, and getting caught and feminized by your Mother’s friend are two very different things though.

These are actually two separate stories about the same boy. In the first one, Mom calls her friend to see if she can help. Her friend has a lot of experience with boys that dress like girls, and tries a crossdressing intervention to see if he is really the sissy he seems to be. She has limited success but he has a ball. What now?

Mom decides to take the matter into her own hands. She encourages her son to dress like a girl until the thrill is gone. But that doesn’t happen right away. It takes him a tremendous amount of practice and hundreds of pairs of panties to come to his own conclusion about the whole thing.

Both are audio stories as well as written stories, listen to the previews or read the whole thing. These two recordings and 14 others are free with a one time video signup, you’ll see the link. Enjoy!

Feminized by Mom’s Friend

Feminized by Mom

Feminized by Mom and Her Friend

Feminized by Mom and Her Friend

Love Letters

You may be getting a tax refund in the near future and you should try to spend it sensibly, not on something frivolous like another babydoll nightie. Unless that babydoll is the Love Letters Babydoll from Dottie’s Delights.

Description: “This little darling is as sheer as it comes, available in either powder pink or black, made of the same authentic wispy nylon as the vintage nightgowns of the 1960’s. Very short, flirty length gathered from the neckline with a tiny satin ribbon and bow stitched at center.

Little cloud tuffs at the shoulder that can be made to stick upright or down depending on the look you desire. My favorite feature is the ruched circle pouch pocket at the hip, also adorned with the satin ribbon. The perfect size to store all of your naughty and nice items – from lipstick to cell phones to condoms.”

OK, lets recap: a beautiful sheer nightie, available in powder pink or black, made of wispy nylon like the ones you may have worn in the 60’s, and a pocket for your lipstick and cell phone. Well if that isn’t sensible I don’t know what is. Go for it!

Note: panties, manicure, pedicure, heels, false eyelashes, wig, lipstick, cell phone and condoms not included.

Dottie’s Delights

Love Letters Babydoll

Love Letters Babydoll

The Halloween Sissy

You’ve been planning this night all year, and you’re finally ready to go out into the world dressed as an adorable, sexy girl. Your outfit has been carefully chosen, you found someone to do your hair and makeup, your lingerie fits like a second skin, and you know exactly where you want to go and what you want to do.

I have a few quick suggestions to help you make this a memorable night.

1: Carry a medium to large purse. Not only will you need a place to stash your makeup, phone, and wallet, a full purse makes a great weapon if needed.

2: Bring extra panties, pantyhose and condoms. You may not need any of those, but just knowing they’re there will let you concentrate on having a great time.

3: Remember, you may be dressed like a slut but you’re not a prostitute, probably.

The Halloween Sissy

The Halloween Sissy

Crossdressing-out of the closet and into the living room

In the old days, most crossdressers would simply put on a pair of panties and prance around the house. Then maybe, just maybe, they would get very brave and add stockings or pantyhose, a bra and a dress.

On a few occasions they might even put on a cute wig, makeup and nail polish, maybe even high heels, but rarely did they take pictures of themselves and share them with the world. Though the times they are a changin, and now you can easily find thousands of photos of pretty boys and men in panties all over the web.

I’ve put together a select group of my favorite crossdressers from Pinterest in two new boards: Pretty Boys and Men in Panties. I think this will give you a better perspective of just how many men like to dress up as girls. You might even want to begin taking some photos of yourself and spread them around.

Note: these two boards are repinned from the manly men of Pinterest, so some of these “girls” might even be actual girls, or maybe they became girls, its very hard to tell sometimes.

Update: I found out that this photo is Shemale Pornstar Nicole Ribeiro, so not quite your average pretty boy.

Pretty Boys on Pinterest

Pretty Boys on Pinterest

Pretty Boys on Pinterest

Just Another Forced Feminization Audio Story

You see sweetheart, your mother told me you’ve been dressing up in her clothes when she’s not home. And this has been going on for a while now.

You see, she wasn’t sure at first about your dressing up, and asked me what I thought. So I suggested that she keep an eye on your favorite things for a few weeks, to see if they’ve actually been worn.

Apparently these are a few of your favorite things.

It’s just like the song! Do you know that song sweetie? It goes like this:

Girls in white dresses with blue satin sashes, snowflakes that stay on my nose and eye lashes. Silver white winters that melt into spring, these are a few of my favorite things. La-la, la-la-la, la-la, la-la-la. La-la, la-la-la, la-la, la-la-la…

Listen To Favorite Things Here

Favorite Things

Favorite Things

James and the Giant Lipstick

I’d like to tell you a true story about my friend James. This is not a fairy tale but James is indeed a fairy.

He sent me a picture of a dress he found online with the model holding what looks like a giant lipstick, and asked if I had any idea where to buy it. A quick search showed that its not actually giant but it is a rather large red lipstick purse from Pinup Girl. I’ll give you the link at the end of the post.

Red Lipstick Purse

Red Lipstick Purse

This is not really my style, but if you like attention getting accessories it may just be the perfect purse for you. Now I’d like to show you the dress which is also not really my style but very, very cute.

Cartoon Print Dress

Cartoon Print Dress

Be aware that this dress will probably not fit most men. Even though it comes in Large and Extra Large you have to be very trim and not too tall. The Extra Large is designed for a 33 inch waist and a 38 bust. So if that’s you and you like this I say go for it. Butt wait-It also comes in black.

If you buy this dress, and its a great deal at less than $50, you have to ask yourself one question. And its not do you feel lucky, although you might very well get lucky if you rock this outfit. You have to ask yourself if you’re prepared for all the attention you’re going to get from the guys.

So you may want to learn this model’s pose and have a line ready when they ask you out. Look straight at the guy, tilt your sunglasses, and say: “You talkin’ to me?” Don’t get all De Niro on him but say it in your sexiest voice, then wait for a response. You should probably practice this at home.

Cartoon Print Dress in Black

Cartoon Print Dress in Black

Cartoon Print Dress: us.shein.com

Red Lipstick Purse: www.pinupgirlclothing.com

Alternatives to Petticoat Punishment-Audio Story

Hi there honey, I’m Teresa. Thank you for coming over on such short notice. Now wave goodbye to your Mother, she’ll be back for you later.

Come in, come in, we have a lot to do today. Come on, don’t be shy. I see you brought a package for me. Do you know what’s inside? No? Well I’ll bet you love surprises as much as I do, and this is gonna be a big one!

Follow me into my bedroom and we’ll both take a look at the same time. I really think you’re going to enjoy yourself today. Your Mother and I have been friends for a long time, and I told her I think I can help her out. Well, actually I want to help you out.

You look so nervous sweetheart, just relax. I want to be your friend, OK? Now come over here and sit on my bed next to me. Come on, sit right here. Awww, you’re so shy aren’t you? Don’t you want to sit next to me?

Are you afraid of girls? Because I think a big part of this is that you are afraid of girls.

Now move over here. You can get closer to me you know; I’m not going to bite you. Alright, I think its time to explain why you’re here, and exactly what is in that mysterious package. You see sweetheart, your Mother told me you’ve been dressing up in her clothes when she’s not home. And this has been going on for a while now.

No? Are you telling me that you haven’t been dressing up in her clothes? Are you sure? Because your Mother seems to be pretty sure that you have. OK, tell you what, let’s take a look inside this package and see if there’s anything in there that can help us figure this out.

Now I want you to know that whatever happens here today is just between me and you. And of course your Mother. But really sweetie, she only wants what’s best for you. You have to believe that.

Ready? OK, here we go. Well look what we have here, panties, pantyhose, and a dress. Do these look familiar at all? No? OK, then let me tell you about the discussion your Mother and I have been having.

You see, she wasn’t sure at first about your dressing up, and asked me what I thought. So I suggested that she keep an eye on your favorite things for a few weeks to see if they’ve actually been worn. Apparently these are a few of your favorite things.

It’s just like the song!

This recording is 40 minutes and is now a free download.

Preview Favorite Things Here

Favorite Things

Favorite Things

Experiments in Feminization Hypnosis

John woke up with a slight headache as he usually did after Nina had been trying her hypnosis on him. It never seemed to do much (she said she was building up her skills), but she seemed to enjoy doing it, and it had been a good way to diffuse the argument they’d had. He frowned at the thought of her being so pissed off with him. Usually she’d find some way to get her own back – he just hoped she wouldn’t do anything too embarrassing.

He slipped out of bed and started to run the bath, putting in some scented oils. For some reason he seemed to have woken ridiculously early for work, so it seemed a nice idea to take his time getting ready. Nina would be there when he got to the office and she’d appreciate him smelling clean. As the bath ran, he stood in front of the mirror and idly plucked his eyebrows until they were thin, high arches.

Getting in the bath he hoped Nina would be in a better mood today. He’d not done anything wrong last night, but she had been so irritable. He knew that if she remained tense like that she tended to snap and take it out on someone – usually him. Thankfully she’d seemed to have calmed down by the time she’d left, so the chances her doing something cruel were slim. As he lay in the bath he carefully shaved his body until only his pubic hair remained below his neck. Finally, he trimmed that hair into a neat heart shape before getting out of the bath…

READ MORE HERE

Experiments in Feminization Hypnosis

Experiments in Feminization Hypnosis

You’re a girl now sweetheart, you’re a girl now

Bob had been dressing up a lot more since being laid off from his job at the factory. He still woke up each morning at 6, then remembered that he had no job and nowhere to go. His girlfriend Julie was out of town on business, and her closet full of beautiful dresses, blouses and skirts, her dresser filled with soft, silky lingerie, and her collection of high heels was irresistible to him.

He would get up and shower, then put on the TV and have coffee, promising himself that he would stay out of her clothes. But within an hour he was standing in front of the full length mirror, admiring himself in her fabulous pink satin tulle baby doll, and matching panties.

Despite the anxiety, the worry about her discovering his secret, and the guilt he felt, there was no way he could stop. The layers of soft, cool, silk and satin on his skin, and the way he felt as he slipped on her nightgown was incredible. It was like a drug that he had to have…

READ MORE HERE

Queen for a day

Queen for a day

Mom Has Crossdressing Intervention

The truth of these crossdressing interventions must be told and this is based on actual events. It began as a simple favor…

“You look so nervous sweetheart, just relax. I want to be your friend, OK? Now come over here and sit on my bed next to me. Come on, sit right here.

Awww, you’re so shy aren’t you? Don’t you want to sit next to me? Are you afraid of girls? Because I think a big part of this is that you are afraid of girls. Now move over here. You can get closer to me you know; I’m not going to bite you.

Alright, I think its time to explain why you’re here, and exactly what is in that mysterious package. You see sweetheart, your mother told me you’ve been dressing up in her clothes when she’s not home. And this has been going on for a while now.

No? Are you telling me that you haven’t been dressing up in her clothes? Are you sure? Because your mother seems to be pretty sure that you have.

OK, tell you what, let’s take a look inside this package and see if there’s anything in there that can help us figure this out…”

LISTEN TO FAVORITE THINGS HERE

READ FAVORITE THINGS HERE

Favorite Things

Favorite Things