When I was in college in the early 90s, I had a pen pal named Tami who I would write to about once a week—actual, physical letters. We’d been corresponding for a few years, and as we were a couple of awkward people who lived several states away from each other, we’d often flirt with each other. It started off in high school where we exchanged photos and I said she was beautiful. It later evolved into sharing innocent and not so innocent little fantasies and stories about each other: What would happen if we got stuck together in a cabin for a week? What if I dared you to go skinny dipping? What if we had to pass ourselves off as a married couple? Nothing explicit, just some fun escapism we both enjoyed, knowing we’d never have to face each other in real life.

The thing was, I’d always had a fantasy about being feminized by a beautiful woman. Letting a girl dress me up, make me over, and treat me as a female, allowing her take it as far as she was willing to go. The internet was in its infancy, so I had no one to share these fantasies with. It occurred to me that if I phrased this as a random thought, maybe Tami would take my writing prompt and run with it, writing out a story of her turning me into a girl. Maybe she’d even like the idea! Maybe this little fantasy would turn into an epic epistolary tale that we’d write together.

Eventually, I succumbed to temptation. Using her love of The Rocky Horror Picture Show, I suggested she write a story where she had to help me pass myself off as a woman. I played it like it was just a silly thought, but deep down I was hoping for her to send me a detailed description of how she’d feminize me, what I’d look like afterwards, and maybe even how she’d keep me that way.

For a week, I awaited her letter, terrified I’d admitted too much, and yet even more excited about her response.
Finally, her letter arrived.

After a page about what she’d been up to, I finally read her response to my request.

It was a half-page, lifeless ‘Mrs. Doubtfire’ knock off, the least exciting thing I’d ever read. God, I was disappointed. But clearly the idea didn’t interest her, so I moved on.

But that was the first time I ever let slip my desire to be feminized, and I wish it had been more exciting. So I present to you the letter exchange I wish had happened, all those years ago:

FEBRUARY 19, 1994: (FROM LEON)

…and that’s why I know e-mail will never replace good old fashioned letter writing. You’ll see.

So you go to this ‘Rocky Horror Picture Show’ every week? Sounds like you’re really into it. I was surprised to learn that you do everyone’s makeup, especially the guys’. I’m shocked so many men get into it that much. If I ever make it down to your state, I’ll have to let you give me a full makeover for the show.

Of course, I never really saw the draw of RHPS, so making me over as a woman might be a wasted effort. Unless of course we had another reason to get me into a dress.

There’s an idea. Say I had to pass myself off as a girl for some reason and came to you for help. I wonder how I’d end up looking after you got through with me. Are you skilled enough that no one would suspect? And what if I had to keep up the disguise for a long time? Do you think I could handle it?

Might make for an interesting story. What do you think?

At any rate, I have an early class tomorrow. Learning to program in BASIC and LOGO is hard, but I know it’ll be a valuable skill once I graduate.

Thinking of you,
Leon

FEBRUARY 24, 1994: (FROM TAMI)

You’d be surprised how many guys I make over, and not just for RHPS. Guys do it for costumes, for drag, or simply because they enjoy it. You’d be shocked how many perfectly normal guys like to put on a skirt and blouse at home.

So I’m going to give you a makeover, huh? Well, you have a cute face (though not a girly one!). Since you’re not into Rocky, I’ll have to think of another reason to make you feminine…

You know I mentioned how I was thinking of applying to work at a beauty salon? Well, you have to have some sort of project in order to get hired (at least for the sake of this story). Let’s say I ask you to help, and you agree, not knowing what I had in store.

Then, when I present my project to the bosses, I introduce them to a beautiful girl named Laura. Her legs are shaved, her toes and fingers painted, and she’s wearing rogue, eyeliner, and lipstick. Her hair is cut into a cute little bob, and she’s wearing big hoop earrings. She’s standing unsteadily on some spiky heels, and she’s wearing a sleeveless sweater (guess she’d have her armpits shaved too) and a short skirt. The judges love what I’ve done with her and go on and on about how cute and girly she is (though she looks rather upset and confused). Finally, as they’re about to make a decision, I drop the bomb. ‘Laura’ is actually my good friend Leon! I show them a before picture, and they are just amazed and what a complete transformation I’ve done on you. They keep saying how flawlessly you pass as a woman. I get the job, of course. And the best part is, they hire you too! They decide to keep you on as a model for the other beauticians to practice on! Sure, maybe that’s not what you had in mind when you said you’d give me a hand, but hey, it’s a living! I’ve taken the liberty of giving away your male clothes, so it looks like you’re in for an interesting year, Laura!

Well, I hope you enjoyed the story and didn’t think it was too silly or mean. Personally, I’d like to know how you’d adjust to living as a female model, if you feel like continuing the story.

As always, I really look forward to your letters. Please write soon, dear friend.

Tami

MARCH 1, 1994: (FROM LEON)

…a modest inheritance. My parents are investing it for me in a company called ‘Enron.’ I’ve never heard of it, but they say it’s going to be huge. By 2005 it might be enough for me to retire!

So sounds like I’m really stuck in dresses for a while. If I didn’t enjoy being near you so much, I might just pack my panties and leave! But I guess there are worse fates than hanging out with you. Of course having my makeup and hair done several times a day might be stressful, not to mention your coworkers practicing their electrolysis on me! No more five o’clock shadow…ever. After all this stress, you better treat me to a girls’ day at the spa or a shopping spree. After all, I’ll need all new clothes.

I guess we’d have to live together. As Laura, I couldn’t live with another guy, and I certainly couldn’t surprise a female roommate coming out of the shower. I wonder if we’d share clothes (though I’d have to lose a bit of weight for that). When I said I got into Tami’s panties, I meant it literally.

Of course, it would be hard to come onto you after I’ve traded my sneakers for heels and my razor for a mascara brush. I’d be pretty jealous seeing guys flirting with you and not being able to stop it.

Even worse, what if they flirted with me?

A whole new angle you’re welcome to explore.

Write me soon, Tami.
Leon

MARCH 7, 1994: (FROM TAMI)

To be honest, you wouldn’t have to lose any weight if you wanted to try on my clothes. I know you pretend not to notice, or maybe you can’t tell from the photos I send, but I’m not exactly the world’s skinniest girl. It’s too bad you don’t really want to wear my clothes, because I think they’d fit you just fine.

And you can joke about other guys flirting with me, but trust me, that wouldn’t happen in real life. If you went out with me as Laura, you’d be the cute one.

But hey, this is just a story, right? We can pretend.

So maybe I agree to a double date with a guy, and promise to bring my roommate Laura along. You’re not especially happy about this, especially since I didn’t tell you we were going on a date until we got to the restaurant.

Maybe I get a little jealous of how both the guys are paying more attention to you, so when they suggest we go back to their place, I agree. And maybe you’re a little annoyed with me, so when my date tries to kiss him, I let him. And then when your date tries to kiss you…

Well, let’s just say both our dates wind up with a lot of lipstick on their faces. And we end up having to leave before your date realizes your boobs are fake. I think we’d both end up mad at each other. Are you mad that I tricked you into going on this date? Am I mad that you were the pretty one? Or are we a little jealous that we weren’t kissing the person we wanted to that night?

And don’t worry about your manhood. You were just experimenting. Besides, the massive amounts of estrogen I’ve been putting into your food probably affected your reaction.

Oh, didn’t I tell you? Well, the changes won’t just be mental.

Ain’t I a stinker?

Write soon,
Tami

Marh 15, 1994: (FROM LEON)

…which is why that political dynasty is over. You’ll never hear the name ‘George Bush’ again on the national stage.

Tami, I don’t like it when you insult yourself. We’ve known each other for four years, and I’ve always thought you were one of the prettiest women I know. I often wonder what our lives would be like if we didn’t live a thousand miles apart. I don’t know if all the guys around you are blind, but trust me, you’d be the best looking one in any crowd.

Of course, now that you’ve been feeding me estrogen for a year, I could give you a run for your money. It was embarrassing enough when I had to start borrowing your bras. It was even more embarrassing when I had to buy my own because yours were too small. Twenty years of obsessing about boobies and now I have my own pair. No more shaving, except for my legs, everything is smooth now. I’ve gone from a bass to a soprano. And the changes aren’t just physical.

Now that I’m living as Laura, it’s hard to remember that I’m not Laura. New name, new job, new gender, and if I don’t watch it, a new boyfriend. Look, maybe I wasn’t thinking when I asked you to buy me a pregnancy test, but he and I had been drinking and…

No matter. The sad thing is, I’d always kind of hoped I’d end up with you. Now it looks like the best I can hope for is to be maid of honor at your wedding. Can’t really be your boyfriend when we share clothes and makeup?

One night, I burst into tears (maybe it’s my time of the month). I tell you how confused I feel, and that when I look in the mirror all I see is my old face on a woman’s body and I don’t know what to do or where to go from here. You hug me and tell me our experiment has gone on long enough. You’ve made an appointment with a doctor who is going to make sure I no longer feel like a half man/half woman.

I’m relieved that I’m going to have my breasts removed and can start living as a man again. But not as relieved as I first thought. After all, I’d grown so close to Tami this year. I don’t want to give that up.

I lay in the hospital bed with the anesthesia lulling me to sleep, you holding my hand.

“Laura, I hope this is the right decision.”

I nod, sleepily, not sure at all. You take out a stack of photos.

“Now I’ve given the surgeon a general idea of what I want your new face to look like, but I guess you should have some input. Do you want a tiny nose, or a more narrow one? Think lips or fuller? Do you want to look more like Christy Brinkley or Rachel Hunter? Or would you rather be your own girl?”

As I fall under, I blearily tell Tami how I’d like to look.

So…what do you think? Write soon.
Leon

APRIL 2, 1994: (From Tami)

You know I always get excited when the mail comes, just on the chance there will be a letter from you. You don’t know how much you cheer me up. Ever since I’ve moved into my own apartment, I feel so lonely sometimes. It’s too bad you can’t stop by after classes and we could hang out together.

Silly, huh? Well, on with the story (I hope you don’t mind that I’m continuing it)

Now that I’ve rearranged your face, Leon has pretty much been replaced by Laura. You now look like a young Demi Moore, and everyone seems to notice my cute roommate. You now do your own makeup, buy your own clothes, and find your own dates. I know it’s only a matter of time before someone makes you into his bride (and don’t worry, that plastic surgeon made sure your future husband won’t get any nasty surprises on the honeymoon…though you were sure surprised when you first woke up after the operation!). And Tami will be alone again.
We walk down the street together as you turn everyone’s head. And I miss Leon. He was the only guy who ever treated me nice, the only one who ever called me pretty. And I don’t care that he’s Laura now. He’s still my best friend. I just wish I could hear him compliment me again, or enjoy the way he would always flirt with me. Oh well, I missed my chance. Always a bridesmaid…

APRIL 11, 1994: (FROM LEON)

I hope you realize that distance it the only reason I never tried harder to be with you. And I always kind of assumed that you had your own boyfriends down there, just as I’ve had my own dates up here. But none as pretty as you.

And we’re not going to end the story like that. Because if there was even a chance that Tami still liked Laura, she was not going to give up. And one night Laura gets down on one knee, slips a ring on Tami’s finger, and asks is she’ll do Laura the honor of becoming her wife.

The question is, would Tami accept Laura as a wife, or is she now too feminine for Tami’s taste?

I’m not sure how you’d really react. But in my story, Laura and Tami go down the aisle in matching wedding dresses. And that’s how Leon Smith ended up as Mrs. Laura Jones, wife of her best friend. And you know what? They lived happily ever after.

And I would consider that a happy ending. Take it how you will.

APRIL 16, 1994: (FROM TAMI)

Leon, there’s something I’ve been wanting to ask you all year, but I’ve been too afraid that you’ll say no. I’ve always been able to be open with you, because we’ve never met face to face. I can say whatever I want in my letters because I somehow always knew that we’d never be in the same room, and I’d never have to worry about you not feeling the same way.

But this last series of letters kind of made me realize that maybe I’m hiding behind the distance between us, and maybe you’re using the letters to be more open than you normally are. Maybe about more than one thing.

So I’d like to ask you if you’d like to move in with me for the summer. I have my own place, the rent is cheap, and you said that the programming work you do can be done remotely. It’s warm down here, and there’s a lot we can do. We can just be roommates, though I only have one bedroom. Make of that what you will.

And I want to make you and offer. I don’t have a lot of friends here. I’m very good at makeup. And I think my clothes wouldn’t actually be too tight of a fit on you.

So if maybe you’d like to try out life as Laura, now’s your chance. Maybe I’m reading too much into a silly story, and if that’s the case, I’ll never bring it up again. But I bet you anything, with new clothes, padding, makeup, and a wig, I could make you into a passable woman. So if you’d like to spend a few months experiencing the other side of life, I’d be glad to help dress you.

And then undress you.

I’m terrified to send this letter, but I know I’ll regret it forever if I don’t. Don’t feel guilty if you aren’t interested in my offer. But please don’t be afraid to say yes.

Eagerly awaiting your reply.

*

Sadly, none of this ever happened. But my frustration at her lack of interest in my feminization led to me write my first TG romance, a hobby I’ve enjoyed for over 20 years.