Trained and Transformed

He’s ready now, you can pick him up anytime.

Trained and Transformed

Trained and Transformed

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

Seasonal Sissy Maid Jobs

So you wanna be a sissy maid but are having trouble finding work? Well next month there will be a huge demand for sissy maids, and all you have to do is take advantage of it.

Super Bowl 50 is coming up very, very soon, and this is a golden opportunity. Men that watch football need one important thing besides a large screen TV, beer and food. They need to be served more beer and more food every few minutes.

This year, instead of sitting there watching the game with your friends, make yourself useful and help everyone enjoy the event. Bring them beer and serve them the usual junk food, but serve it with a smile.

Tip 1: If you can make your own delicious snacks you will probably be invited back for other occasions, there is always a need for someone to cook, serve and clean.

Tip 2: Studies show that men prefer their sissy maids to wear bright colors, so don’t limit yourself to the usual black maids outfit. Same with stocking or tights and heels.

Tip 3: Bright red lipstick is traditional but feel free to wear other related colors, especially pink.

Tip 4: Don’t forget halftime. Most halftime shows are relatively boring, so with a little creative thinking you can make this Super Bowl one that the guys will never forget (consider knee pads).

Super Bowl Sissy Maid

Super Bowl Sissy Maid

Sissy Maid Tips

The most important tip is to stay out of her panty drawer. That’s how you got in trouble in the first place!

Trouble, trouble, trouble

Trouble, trouble, trouble

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

Lets dress him up as a girl!

How long have you wanted to hear those words? I’m guessing for a very long time. But how is it going to happen? Will you be kidnapped by a group of large breasted makeup artists and transformed into a beautiful girl? Drugged in a bar and driven to a mansion far, far away to be used as an experiment by an evil Dominatrix? Forced to become one of the cheerleaders at school and entertain the football team? I hate to tell you this, really I do, but there is a chance that this may not happen.

So how can you fulfill your fantasy of being caught in panties by women you know, blackmailed, and forced to become a feminine little plaything for their amusement? I have a plan…

THE FORCED FEMINIZATION GUIDE

The Forced Feminization Guide

The Forced Feminization Guide

How to Find a Woman to Feminize You

I think it was Nixon that said “Those who fail to plan, plan to fail.” Maybe it was my lawn guy, I don’t really remember. But if you want to find a woman to dress you up and play with you, a plan is needed. I have such a plan.

This will take some effort on your part, but it will be fun I promise. Its simple really, you are going to accidentally on purpose show a woman that you’re wearing panties. But you’re going to do it in a very classy, creative, and well orchestrated way.

The Plan: You wear a pair of panties under your jeans or shorts, then go shopping. Simple right? And to make it even easier, you’re shopping for food in a large supermarket. You’re just going to wear your panties instead of your regular underwear and talk to women who are shopping in the same isle.

The Setup: You have a shopping list in your pocket. Make it up, I suggest small things like soup, tomato sauce, and yogurt, things like that. You casually browse the store until you find a woman you’d like to meet. Then, you go over to where she’s shopping and ask a question about a product.

The Move: This is where it gets creative. As you and your new friend are talking about clam chowder, you pull out your shopping list to remind yourself of the brand you wanted, and oops-the list falls to the floor.

(You may want to practice this move at home. Make it look natural.)

Keep talking, bend over and pick up your shopping list. You’ll want to pull your panties up a bit higher before bending over. Not wedgie high, but just enough to make them visible as your shirt creeps up a little. That’s it! OK, that’s not it but if you get this far you’ve already achieved your goal. Now what?

You may be wondering if she actually saw your panties showing. Believe me she did. Women will look at a guy’s butt 9 out of 10 times just because that’s what we like to do. You’ll be able to tell from her face what to do next.

The Next Step: Do not go too excited just because a woman knows you’re wearing panties, many women will just chuckle and continue to help you find a the best soup with the lowest Sodium. Its all about her reaction.

Reaction 1: “Oh, you’re wearing women’s panties, isn’t that cute!”

Reaction 2: “Nice panties! What kind are those?”

Reaction 3: “Get away from me!”

Listen, no plan is perfect and you’ll probably get other reactions as well. Some women may ignore your panty clad butt completely much to your dismay, but it will help you with the next one.

Your goal is to find the right woman for you, just like in any relationship. You want to look into her eyes and see fire. She likes the idea of a man in panties, you can tell by her smile. There will be no need to explain that you want to be transformed into a feminine little plaything for her amusement, she already knows. You’ll buy that clam chowder and start a new life with her. After dinner you’ll look over and whisper: Feminize Me, and it will happen…

At the Supermarket

At the Supermarket

A Story of Feminisation: Pippa’s Story

(Originally posted April 15th, 2013. The song remains the same.)

I was just entering my prearranged destination. It was 11 pm and just before I paid the admittance fee, I stopped to look at myself in the mirrored walls. Reflected before me was a sexy, if a little sluttish looking woman in her thirties.

The only discrepancy being that I was actually a 37-year-old man, happily married, here at the precise instruction of the woman I loved and was married to. She had returned home a day early from a trip to her sister’s place in the country.

What she found as she walked in was her husband wearing her underwear and fully made up to boot. She insisted that if I wanted to remain married to her, I would agree to dress up for her whenever and wherever she instructed me to.

I was flabbergasted and truly lost for words. I did not want to lose her, but I knew she could be a vindictive cow when she wanted. I agreed meekly to this arrangement.

This is why I am here. I am about to enter a transvestite club on the Earls Court Road, being fully ‘transformed’ into my female persona… Pippa.

In my hand I hold a sheet of paper, and have instructions that I must show it to anyone that I speak to once inside the club.

READ MORE HERE

A Story of Feminisation: Pippa's Story

A Story of Feminisation: Pippa’s Story

They Made Him A Girl!

Oh, hi honey. You’re waking up, welcome to your new home. Oh, no sweetie, don’t try and move too much, you see, you’ve been restrained very firmly, and will not be getting out of this bed until I think you’re ready to be good.

Do you like your pink satin sheets-they’re slippery huh? Especially when you’re wearing a pink nightie and matching panties like you are.

Why are your legs, armpits and face so soft and smooth and hairless?

Why do you have long, red fingernails and painted toes? Well…we’ll get to that in good time sweetie.

And that bandage around your chest? We’ll get to that too….

READ MORE HERE

Making Marissa-They Made Him A Girl!

Making Marissa-They Made Him A Girl!

Mommy’s Boy to Mommy’s Sissy Girl-Free MP3 Download

You know sweetheart, you shouldn’t feel so bad, I’ve always wanted a daughter. And since you simply INSIST on sneaking into Mommy’s room and dressing up in my clothes, I think you can be that daughter.

Oh darling, don’t look so horrified, you can be my precious little girl, dress up in Mommy’s pretty things, keep me company, and help me around the house-all the things girls do with their Mothers. I just wish you’d told me sooner that you liked being a little girl so we could have more time together.

You know sweetie, I’ll even let you wear those pretty things I caught you in today when I got home. You must like them, not that I blame you. I know I always feel so pretty and feminine wearing that pretty pink bra and panty set and that satin slip. You know, that set has a matching garter belt so you can wear stockings too, just like Mommy, just like a real girl.

Now, now, don’t bother to argue. I think we both know this is what you want, to be Mommy’s little sissy girl. To have Mommy buy you a whole set of pretty, feminine lingerie to wear under adorable blouses, skirts and dresses.

I’ll give you some of my makeup and teach you how to use it, won’t that be fun? Sitting with me at my dressing table learning to put on makeup just like a girl, just like Mommy.

And you know, sweetie, once you get comfortable with your new role as my little girl, we can go shopping for high heels and everything else you’ll need to be a pretty girl.

Oh, and I just thought of this…I’ll get to teach you all about boys, and how to get yourself a cute boyfriend. Because that’s a big part of being a girl. Now, now, it’s okay to be nervous about boys, sweetie, all young girls are when they’re virgins. The trick is to learn how to make boys happy without going too far-God knows a pretty girl like you will have boys begging to get to you.

Now, now, there’s no need to blush honey, of course Mommy wants you to tell them no—proper girls wait for that special man. Some of them will be quite insistent though, but there’s ways to make a young man happy with your hands or your mouth…but I’m getting ahead of myself, aren’t I?

For now, you’ll become Mommy’s little girl and you’ll love it.

This is what you really want honey, to be Mommy’s little girl. And this is what I really want too.

We’re going to have a ball together; you’ll see…you’ll see…

DOWNLOAD THIS MP3 HERE

Mommy’s Girl-Free MP3 Download

Mommy’s Girl-Free MP3 Download

A Story of Feminisation

I was just entering my prearranged destination. It was 11 pm and just before I paid the admittance fee, I stopped to look at myself in the mirrored walls. Reflected before me was a sexy, if a little sluttish looking woman in her thirties.

The only discrepancy being that I was actually a 37-year-old man, happily married, here at the precise instruction of the woman I loved, and was married to. She had returned home a day early, from a trip to her sister’s place, in the country.

What she found as she walked in was her husband wearing her underwear and, fully made up to boot. She insisted that, if I wanted to remain married to her, I would agree to dress up for her, whenever and wherever she instructed me to.

I was flabbergasted and truly lost for words. I did not want to lose her but I knew she could be a vindictive cow, when she wanted. I agreed meekly to this arrangement.

This is why I am here. I am about to enter a transvestite club on the Earls Court Road, being fully ‘transformed’ into my female persona… Pippa.

In my hand, I hold a sheet of paper and, have instructions that I must show it to anyone that I speak to, once inside the club.

READ MORE HERE

A Story of Feminisation: Pippa's Story

A Story of Feminisation: Pippa’s Story

Bedtime Feminization II-Feminization Hypnosis

Make yourself comfortable.

Lie back on the bed, and gently allow your eyelids to close.

Just begin to allow yourself to relax. Letting all your cares and worries go.

At this moment in time nothing matters.

As you switch off your thoughts you allow this time for yourself, so that you can unwind completely.

You begin to feel more and more relaxed, letting go of any worries or problems that may have been on your mind lately.

There is no need to fight any negative thoughts, as they will soon drift out of your mind again, just as easily as they came…

I would like you to take a couple of deep breaths, slowly filling your lungs with fresh air.

And as you exhale you will relax more and more.

As you gently slow your breathing down, you begin to feel more and more relaxed, more and more comfortable.

You will feel your whole body sinking into the bed and you will notice how relaxed you have become.

From the top of you head to the tips of your toes.

Your eyelids have become very heavy. All the muscles in your jaw and the back of your throat have become limp and relaxed.

READ MORE HERE

Feminization Hypnosis at www.strappedinsilk.com

Feminization Hypnosis at http://www.strappedinsilk.com

In The Bedroom-A Sissy Story

Hi, honey. Whatcha staring at? You always look so happy when you’re watching me getting dressed.

You know, I’ve noticed that about you. You always watch me so closely, while I’m dressing.

Are you wondering what I’m going to wear? Or do you just like seeing me dressing?

Do you like seeing me pull on my panties?

Do you like watching as I roll up my pantyhose, slip my toes into the ends of the feet and gently tug the soft nylon up my legs?

Ha ha ha. I think you do. I do. I think you’re just a little bit more interested in your wife’s clothes than a man ought to be.

You’re always buying me clothes, aren’t you? I love that.

Most men never think to buy clothes for their wives but you do.

Most men would think it a bit odd to take such an interest in their wife’s wardrobe.

What’s funny though, is that while you buy me dresses and skirts and blouses and jackets, and oh, everything – you never buy me the one type of clothing that most men do buy their wives – lingerie!

READ MORE HERE

Bedtime Feminization II

I want you to Say this mantra with me, and when you hear the word girl, remember that you are a petite skinny submissive.

I am a woman.

A beautiful woman.

My male ego is gone. Totally and completely gone.

All my problems and cares have left with my male ego.

My only thought or care is how I become more feminine.

I have let it go.

It is OK to be feminine.

It is OK if people think I am a girl.

I am girlish because I am a girl.

I want people to know that I am a girl.

I am totally and completely a girl.

Because I am a girl, I can act like a girl.

It is so absolutely wonderful to be a girl.

I am not doing anything wrong.

Being feminine makes me happy.

MY Breasts and nipples are a vital part of my sexuality.

It is OK to dress like a girl, because I am a girl.

You will memorize this mantra and repeat to yourself daily.

I want you to dream about this mantra.

I want you to believe with all your heart and all your soul, every single word.

I want you to live it.

Listen Here

Bedtime Feminization II at www.strappedinsilk.com

Bedtime Feminization II at http://www.strappedinsilk.com

Does Feminization Hypnosis work?

Laura peered in through the half open door. It had opened almost as soon as she had knocked, but no one was visible in the dark entrance to the flat.

“Mike?” she called, standing on the threshold. “I came as soon as I got your message. What’s happened? You sounded strange? Are you hiding behind the door?”

There was a little unhappy sound from behind the door and a face appeared shyly from behind it.

“Mike?” Laura exclaimed.

The face nodded, and looking more embarrassed than ever, ushered her quickly into the flat. Once she was in the hallway Laura turned to see what had happened to Mike.

He stood there, a bleached blonde cascade of hair surrounding his prettily made up and very feminine face. The hair curled casually over a tiny pink and white crop top that barely contained an enormous pair of breasts heaving with his nervous, quick breaths.

A few tendrils of blonde reached as far as the tight and very short denim skirt he was wearing. Below it, smoothly hairless legs ended in pink heeled shoes.

Mike’s hands fluttered in embarrassment – hands that Laura couldn’t help notice had long pink nails. He looked panic stricken and confused, trying to hide himself and at the same time show her the dramatic transformation. He even had a large pair of hoop earrings swinging from his ears.

Laura stood there in shock, finally just repeating herself, “Mike!”

Favorite Things is now available

Your Mother and I have been talking about you dressing up in her clothes, and we feel that an intervention is needed. This is the perfect time to try out a new technique to help you come clean…

A short preview is here

The written story is here

Favorite Things-a crossdressing intervention

Favorite Things MP3 at http://www.strappedinsilk.com

Back to School

Being the only boy at an all girl school, Michael was teased unmercifully. Everyone knew he was a sissy, and they spent each day tormenting him in various ways.

He was called Michelle by the entire school including the teachers.

They made him wear high, open toe heels, and insisted his toenails were painted bright red to match his lipstick.

At lunch they played with his hair and experimented with different types of makeup.

They looked at women’s magazines together and made him pick the hottest guys, and confess how he would like to have sex with each one.

When he came to school in the morning, he had to walk across the cafeteria in his tight blouse, short skirt, and heels, listening to the catcalls of the entire class.

He was humiliated, embarrassed, and feminized. And he loved every second of it!

Crossdressing Digest Back to School Issue

Crossdressing Digest Back to School Issue

Go to the mirror boy!

The height of many crossdressing and forced feminization fantasies is the makeup.

Although you’ve probably been wearing all types of clothing for years, its not likely that you’ve been wearing makeup. For one thing its not an easy process and you may not have the time or skill to perfect it. For another, its not easy to quickly remove in the case of an unexpected visitor, wife, girlfriend, or vacuum cleaner salesman.

Having your makeup carefully and lovingly applied by a woman can be a very sensual and erotic experience. This is what I like to do.

Regardless of the outfit I’ve chosen for you, I have you wear only panties and a nightgown. Lets say a pair of black, lace, boy shorts and a very feminine, baby doll nightie.

You sit in a chair opposite me and I slowly and meticulously go through every step of the makeup process, explaining each one in detail.

THERE IS NO MIRROR AND NO PEEKING UNTIL I’M FINISHED!

You watch intensely as I take out each item, you feel the makeup on your skin, you want to squeal with delight as you see me finally opening the lipstick.

Blotting your lips with a tissue, you look at it in disbelief. Its really happening, you’re being transformed into a beautiful women, and your makeup is perfect.

But we’re not there yet.

Now its time for your wig. A change of hairstyle is always dramatic, and in your case the long, blonde, wig is going to complete the transformation.

Brushing it out I see your eyes light up like a child at Christmas.

“How do you feel?” I’ll ask. “Do you feel pretty?”

Most of the time all you’ll be able to do is giggle or stutter and smile, and I know its time.

I lead you to the full length mirror, holding your trembling hand.

As you finally see yourself, you feel a bit dizzy. Is it you? Is this person in the mirror with the long eyelashes, blush, lipstick, and long, blonde, hair really you?

Well, is it?

Crossdressing Fantasies

Crossdressing Fantasies

Free Audio Story Contest #3 (ENDED)

To celebrate the summer I’m having another story contest. It can be about anything, and up to ten minutes long (The time varies depending on the way its written, so figure about 1900 words). The winner will get a free audio version of their story narrated by yours truly.  It will be yours to use however you like and I’ll also add it to my website for everyone to enjoy.

All submissions will be kept strictly confidential and the deadline is July 4th.

There are no real guidelines, but I think it would be fun if it has something to do with summer. Maybe a pool party. Or a camping adventure. Or a shopping trip. Or shopping for a pool party at a campsite.

Whatever floats your boat. As long as its not about a 3 hour tour, a 3-hour-tour…

Strapped In Silk Sissy Story Contest

Strapped In Silk Sissy Story Contest

Transformation Magazine volume 1

Transformation Magazine volume 1

Transformation Magazine volume 1