Go Ask Teresa – Analogy

E: Do you ever feel like everything you’ve ever wanted was wrong? That you’re completely lost and have no idea where to go? Its as if you just woke up after decades, and forgot who you were. Nothing seems to really matter anymore and nothing makes any sense. You don’t feel bad but you don’t feel good. You wonder why you should even get out of bed and continue to put one foot in front of another. Do you have any idea what I’m trying to say?

Me: Sometimes I feel like I’m in a car driving down a very smooth road. Its a good, solid car, and its mine. Its familiar. I seem to know where I want to go and everything is alright. There is no traffic, and I’m not in a hurry. I don’t really have a destination in mind so I’m just driving. It doesn’t matter what time of day it is, or what season, or anything. My mind isn’t racing with other thoughts of what I want to do later, or tomorrow, or what I should have done the day, week, or year before. I’m just driving.

Other times its as if I’m in a large pickup truck. Not a new, state of the art model, but an older, slightly rusted and dented one, with old sugar packets and napkins on the floor. Its not my truck but I can drive it, so its not too bad at first. Little by little it gets worse. Traffic is crazy and the road is bumpy and I feel like I want the ride to be over. The engine starts making a funny noise and some smoke is coming from the engine. Just a little but it seems like a bad sign. I can feel the tension in my arms and body as I hold on and try to drive normally. The other drivers seem angry and in a hurry, as if it is somehow my fault. I’m getting more and more stressed out by the second and start to panic. Then the steering wheel seems to be coming loose and I really freak out. It will come right off in my hands if I don’t hold it in place with all my strength and I’ll be completely out of control. It takes everything I have just to stay focused and try to get through this, but I have no idea where I’m going and how long it will take to get there.

Then, there are times that I feel I’m on the perfect ride. Its a motorcycle. The day is warm and there is no noise at all. No one else seems to be around. The bike starts right up and purrs like a cat. A tiger. A large, strong, very confident tiger with no fear of anything. I am no longer a rider on a machine but simply riding. I can go anywhere I want at any speed without a care in the world.

I pull onto the highway and see its been completely redone. The road is perfect and there is only one line freshly painted down the middle. The road is mine. I smile. This is what my whole life has been about-getting to this point. I have the road, the bike, the world to myself and there is no way any of it could possibly be better. I just want to ride.

I find myself going very fast and look up to see I’m doing 100. Its as if I’m flying an inch or two off the ground and I want to go faster. 125-150-180…

How long will it last. How long will the ride be this flawless and complete? It doesn’t seem to matter at all.

Go Ask Teresa-Crossdressing advice, help and insight

Go Ask Teresa-Crossdressing advice, help and insight

How to drop a hint about your forced feminization fantasy

You’d love to tell your partner about your forced feminization fantasies, but are just not sure how to do it. “If only she knew,” you think to yourself. “If only she would dress me up in pretty panties, do my makeup and nails, take me lingerie shopping, and parade me around in front of her girlfriends.”

Remember, many women don’t want to take the time to do this, and to be honest most are completely freaked out by the whole thing. So how to drop a hint?

I was reading the newspaper this morning and saw what just might be the answer. In itself its just a tape dispenser, but it has the potential to be your ticket to ride! (Or get ridden)

This particular tape dispenser is shaped like a high heel shoe. I’ve seen it in bright red and black, and its selling at OfficeMax for $11.99.

A tape dispenser shaped like a high heel? Yes, but this is where you put on your thinking cap.

You pick up one of these beauties on your way home from work and put it on your desk near your computer. Don’t say anything, just let her notice it herself. If necessary call her in to look at a travel site and let her find it on her own.

“Whats that honey, a high heel tape dispenser? Isn’t that cute” she says while rubbing your neck in anticipation of a vacation in France.

Now the seed is planted. “I never knew he liked high heels, cool!” she thinks to herself while making your favorite dinner.

The next step is to add other items to your new desktop collection like a hairstyle magazine. (You found it in a shopping cart in the supermarket parking lot, maybe she would enjoy it)

One of those free lingerie catalogs you ordered. (Something special for her)

A perfume sample. (Another gift-you’re so thoughtful)

And later on a gift wrapped box from Fredericks of Hollywood containing an Ultimate Satin Corset, in your size. (Oops!)

See how things go and be patient. At some point she may just put it all together and ask you about your sudden (sudden?) interest in feminine clothing, shoes, hairstyles and perfume. If she asks you if you ever thought about dressing up as a girl, think before you answer.

You don’t want to scream out: “YES-OH GOD YES! I THINK ABOUT IT EVERY 5 MINUTES!”

You might say something like: “Oh I don’t know, that’s really kind of kinky isn’t it? But if you think it would be fun I’m willing to try it, just because I love you.”

If she still doesn’t get the hint you may have to make it somewhat more obvious. Go to a Forced Feminization website, maybe Strapped In Silk, and find your favorite story or picture. Leave it on the screen and ask her if she can help you fix your new tape dispenser, its suddenly jammed.

If she still doesn’t get it, politely excuse yourself, put on the corset and perfume, and sashay around the living room singing I Feel Pretty. Some people really need the full picture.

Lets ask someone who’s done it

Billy has been going out dressed as a girl on Halloween since he was 12. I thought a word of encouragement might help the secret sissies. The shy boys. The ones that say:  If only I was brave enough.

“So Billy, whats it like for you going out every year all dressed up?”


“Thank you Billy!”

Experienced Crossdresser

Experienced Crossdresser


Does this picture bring back any memories? Maybe you used to dress up in your Sisters or your Mothers clothes, and were filled with guilt about it, but just couldn’t stop. Maybe you couldn’t get the lingerie back in the drawer exactly where it was, and it drove you crazy with fear! Maybe you were petrified that a friend, neighbor, or family member would come home and catch you, but continued to dress up every day as you glanced out the windows like an escaped prisoner.

Its OK now. You aren’t that person anymore and things have changed. You have to realize that you’re not doing anything wrong, and if something as simple as dressing up gives you pleasure, then enjoy it.

Life is short-wear heels!



OK, so you’ve accepted your fetish and are having a ball. Just remember one thing: STYLE COUNTS!

Its all about style...

Its all about style…

Go Ask Teresa – Fear!

B: I really, really want to order your Beauty School CD Miss Teresa, but I cant risk having it sent to my house! I am so afraid of my wife finding out! I only go to your website when she’s not home, and then I clear all the history! Now she’s been asking me why I’m doing this! I have to have it-its my complete fantasy! What can I do?

Me: GET A GRIP! What are ya, a sissy? Oh yea. How old are ya kid?

B: I’ll be 47 next month.

Me: Listen kid, I have a plan. Now shut up and pay attention. First of all its a download, not an actual CD that would be sent to your house. I send it to your email, see?

B: Oh, I didn’t realize that. But my wife!


Now the first thing ya wanna do is download Firefox. You can have it clear your history every time you sign off, it even asks ya?

B: But…


Now you’re gonna get an email in another name see? They’re all free, just pick a name and remember it. If ya want, ya can write the name and password in a book that nobody reads, get it?

B: Yes Miss Teresa.

Me: You can use a credit card, or if you’re still yeller, an e-check. No traces. Then I send the file to this email that nobody knows about, see?

B: Wow you’re really good at this.

Me: Yea, I been around.

B: But what about downloading and saving the file? How can I hide it?

Me: Here’s what you’re gonna do. Ya download it when no ones around, and save it in a folder. Ya name the folder like another one, but add a letter. Then you put that folder in a different folder that never gets used, see?

B: But what if she finds it and listens?

Me: Ok, lets play it safe. Ya burn it onto a blank CD and stash it somewhere. Drive out to the dessert, get comfy and play it in your car.

B: Not bad, you’re very sneaky.

Me: Thanks kid, but I’m only helpin ya cause this stuff is harmless. So ya like to wear panties and prance around like Cinderella? Who gives a flyin rats ass?

B: My wife actually.

Me: YER A SISSY! Oh yea, that’s what this is about huh? Well, there ya go kid. Now ya can have a party in your pants. Play some pocket pool, adjust the antenna, baste the ham, badger the witness, buff the banana, cuff the carrot, flog the dolphin, milk the moose, oil the glove, rope the pony, yank the yo-yo, knock yourself out.

Just one more thing. Yer not gonna do anything illegal are ya? Anything strange or sick?

B: Oh Lord no Miss Teresa, I just want to wear pretty things and act like a beautiful girl.

Me: That’s what I figured. This conversation never took place, ya hear? Now go grow a pair.

B: Thank you Miss Teresa, but I don’t want to grow a pair because…


Go Ask Teresa: Crossdressing advice, help and insight

Go Ask Teresa: Crossdressing advice, help and insight

Disclaimer: I do not normally talk like this. I am in no way encouraging anyone to do anything illegal or immoral. Its just that in my experience many crossdressers do not want their friends and family discovering their little fetish. Right Mr. Madoff?

Go Ask Teresa: Crossdressing advice, help and insight

I’ve decided to help you girls with any issues you might be having. Mental anguish, guilt, fetishes, shopping tips, whatever. Just ask!

Feel free to contact me here, and just like Jeopardy, it must be in the form of a question. NO real names will be used.


Go Ask Teresa: Crossdressing advice, help and insight

Go Ask Teresa: Crossdressing advice, help and insight