Sticking feathers up your bum, doesn’t make you a chicken aka The end of Monica Maxwell aka The end of my life as a transvestite (potentially)

Yes, that is me.

I think this is going to be the end of Monica Maxwell aka my life as a transvestite.

Although, I wouldn’t believe it if I were you. I’ve been known to do this in the past and it’s never lasted.

I don’t write about Monica or my life as her. This will have been the first time. Odd that it could be the last time…

For those of you who barely know me, and for those of you who know me really well; there’s quite a bit none of you know about me that what you’re about to read may come off as a shock.

Why I dress up and what happens when I do:

I’m a 28 year old STRAIGHT transvestite. Basically what that means is I am a male who likes to wear women’s clothes. I wear women’s clothes purely for sexual reasons. I get off on it.

I started doing it in the sixth grade, and have been doing it ever since. Every year since then it’s gotten more and more elaborate. Initially it was just pantyhose, then it was lingerie, bras / panties, wigs, heels, make-up, dresses, etc etc until I needed a whole other closet solely for my drag clothes, jewelery, heels, wigs, fake eyes lashes and nails, and all my make-up, lotions, perfumes, sex toys, fake boobs and cigarettes.

What happens is, when I dress up, I get horny. And the better the illusion, the hornier I get. The closer I look to the women I find attractive the hornier I get and the better the orgasm. The orgasm doesn’t just apply to how I look. It’s also applies to how I act, what I do and where I am.

You’ll notice that a lot of my pictures are taken from cheap hotels, smoking, watching porn, doing lines of coke, and masturbating on camera.

I’m not ashamed to admit that women who look like this and have lifestyles like this, turn me on. (

HAVING SAID THAT, I’m not ONLY attracted to these kinds of women, I’m attracted to lots of different women. Who have different looks and different personalities. No, seriously. I fell in love with a church going gal, a paris hilton lookalike, a goth girl, a fetishist industrial girl, various trannies and your regular every day girl (albeit more beautiful than your average every day girl, but every day girl nonetheless).

But what I have found out, is that my identity as Monica is a substitute for that in which I do not have. Meaning, I dress as the type of girl I am looking for in absence when I don’t have her.

In the past I’ve noticed I stopped dressing when I found the girl who encapsulated all my desires.

For instance.

I dated a girl who liked getting dressed up where ever we went, friends houses, the movies, the video store, the convenient store, etc. (make-up, heels, fake eyes lashes, tanning, jewelery, etc). She was a girly girl. She partied, was hyper sexual, genuinely interested in me, she was also sweet and endearing, funny, loving, and also kinky.

It ended because she liked drugs better than me.

I suppose this is what you get when you date a girl like this.

que sera sera

I didn’t dress up when I was with her. Instead, my role as a man took over. I found myself letting my body hair grow out, being protective, buying her things, cooking her meals, (insert manlier traits here).

With mostly all other girls, I dressed up as Monica. Because for the most part they only partially fulfilled my attraction and interest. My attraction and interest in them didn’t fulfill me enough to not want to search for something or someone who could. (i.e. another girl or Monica).

There was however, two cases, of two legitimately attractive (inside and out) women who not only liked me as a man, they enjoyed me dressing as a woman. I got to live out my biggest sexual fantasy all the while continuing my life as a man.

They both ended because they were both bat-shit-crazy and there was no way I was able to tolerate their actions, emotions, moods, thoughts, opinions, etc. in order to get what I want.

Their bull shit just wasn’t worth everything else that was good.

So what, DO, I want?

Ultimately, I would love a girl who looks like this:

Is like this to me:

Willing to do things like this:

And is like this:

I understand that so much of what I like is based around fiction. That to want to have the model, romantic, kinky porn star, non-feminist, homemaker mother is never going to happen. A lot of people would say women like this don’t exist.

My only rebuttal is that I know they exist. I’ve been with them.

And that’s my issue. I’ve never been able to cope with not being able to have something I once had. I’ve never been able to go back from eating filet Mignon from the top restaurants in the world to eating a McRib or Big Mac. I just can’t bring myself to enjoy it. Nor do I want to. I’ve never settled for anything in my entire life. I’ve always allowed myself to get what I want. No matter how long it’s taken. Women are no different. Now that I’ve had women who were like and did the things like you seem in the images above, it’s impossible to go back.

I’ve made compromises along the way, like if the girl wasn’t a homemaker mother but she was a model, romantic, kinky porn star, non-feminist or if she wasn’t a kinky porn star or model but was a non-feminist, model, homemaker mother…I was able to compromise with myself with what I allowed myself to like about them.

I CAN compromise what I like. As long as their good qualities out weigh their bad.
I’m sorry if you think this makes me a superficial person, but you’re kidding yourself if you think you don’t do the same thing in lesser extremes. I’m just honest about it.

So what’s the problem?

If I know what I want, I should go and get it.

I am trying.

Girls I like are few and are far between and regardless of how many girls are bi or curious about a straight male who dresses in drag they still want a man.

Not a man who shaves all his body hair and not a man who doesn’t have money to spend on them but rather has money to spend money on his tranny persona, not a man who will write emotional stuff all over his blog and Facebook, a man with confidence, a man with some mystery…(insert manlier trait you find attractive that I guarantee I don’t have).

I just don’t think I can keep up with two lives anymore.

Not just because of trying to attract and keep the women I AM attracted to, to stick around. But because of a few other reasons

1) Age
2) Money
3) Privacy
4) Mentally


I remember me and a friend went to Provincetown in Massachusetts, (a big gay community if you didn’t know), and I remember walking down the street during their gay pride parade. And I saw this old old old old OLD man with a walker next to a building getting make-up applied to his face by some hott chick. And I’m somewhat ashamed to say, it disgusted me. I don’t want to be one of the old trannies that just clearly doesn’t look good in drag at 40, 50, 60, 70 etc. As it is, my prime is slipping away. I sit all day for work and am starting to get love handles. No matter how much I work out or watch what I eat, those will be there. I can’t wear my tube tops and belly shirts anymore. I can barely wear others things of mine. 

An unfortunate truth, is that I am not a hott chick. Sure I may look great. But that takes a lot of time, effort and money and a lot of sacrifice as a guy to look as good as I do. Which is beginning to take a toll on me. Because women are no longer finding me attractive as a male anymore and that’s obviously a huge problem.

I am not a hott chick. But I can be. And honestly I want to be. It just takes a lot of time and effort and money. All of which would be worth sacrificing if my pay off were better.


Depending on what it is I’m doing the price of being a part-time passable tranny is expensive. And this is technically only the second year living away from my parents. So I’m still getting used to having to pay rent and other such living costs.

Make-up, wigs, hair accessories, jewelery, handbags, outfits (jeans, tops, coats, underwear, etc.), heels, temporary tattoos, tanning, sex toys, cigarettes, hotel room, condoms, boobs, cab fare, club cover, drinks, nail tips and other beauty / fun accessories. These aren’t things I need to buy all the time but my point is, in order to do this right, in order to look as good as I do, let other people see how good I look, try and find someone to have sex with me, to get experience and confidence going out dressed up and the ability to act like a woman as well; costs sometimes just as much as my rent. Which I just don’t have the finances to cover this stuff anymore.


For a long time I lived with my parents which was good in the sense…I had more money, but in order to dress up I had to rent hotel rooms. Which was fine because when I lived there I had the money to be able to. I finally moved away but in a way I’ve sacrificed more now. Not only do I not have money to pay for Monica. But I’ve also sacrificed privacy. I live in a very small one bedroom apartment that I share with a friend of mine. She knows about Monica and loves me dressing up, but, it’s difficult to have an erotic photo shoot when she’s home for the obvious reason that she may like me dressing up but, I’m sure she doesn’t want to come home and see me sticking a giant butt plug up my ass in the bathroom or kitchen while someone takes pictures of me.

Plus, I just have no room for my clothes anymore. I’ve accumulated a lot of clothes and accessories over the years and it’s getting harder and harder to explain why I have “Carmen Electra’s Strip Aerobics” DVD by my DVD player, or why I have a mannequin head wig holder under my bed, or why there are feathers strew about occasionally throughout my room, or why I have traces of mascara and eye liner around my eye from the night before, or why I trim/shave my arm and leg hair.

Also, in terms of the digital world…I am really throwing myself out there these days. On OkCupid, a dating website, I actually have a photo that shows Monica and my boy side, side by side in a photo to try and attract women who might be interested in having a part-time transvestite as a boyfriend. I’m putting myself out there like this because I am not meeting the people I want to be meeting. I’m not really meeting many people at all, in fact.

So I’m beginning to sacrifice my privacy in order to find someone who I like and who likes me. Which could have disastrous results.


I either need to be a full blown transsexual or a guy. Why? Because drag queens and transsexuals aren’t attracted to Monica, I’m not attracted to men, Straight girls obviously don’t want me as Monica, or as a boy (apparently). I just can’t find an attractive woman inside and out who will like me for who I am.

A while ago, a constant supporter and helper of my life as Monica and I got into a discussion about what was my ultimate goal with Monica. And during the conversation he said to me, “sticking feathers up your butt doesn’t make you a chicken,” the context is lost on me as to why he said that. But, regardless, I think about it daily. Because partially he’s right.

It angered me that he said this, for sure. To this day it still angers me. You just don’t remind a man who dresses like a girl that he’s not a girl. You just shouldn’t do it. I both think he’s right and he’s wrong. On one hand, just because I slap some fake boobs, make-up, and heels on me doesn’t make me a woman. Technically he’s right. But also, he’s wrong, sticking feathers up your butt and slapping some make-up, boobs and heels on me does make me chicken or woman. Because it brings me that much closer to at the very least appearing like one. Which is the whole point. I know I will never be a TRUE woman. But if I can at least live as much as my life appearing as one? Then that’s sufficient. Especially since humanity looks at things based on appearance anyway. If it walks like a woman, acts like a women, talks like woman…well, it must be a woman. And sometimes that sufficient enough.

I just don’t know if I can go about my life with a dual identity anymore. Having my cake and eating it too is great in theory but it’s also making me crazy and kind of destroying both sides of my lives.

If I felt as though I had some friends, girlfriends, etc. who could be a mentor to me, who would go out with me, who would have sex with me, who would play out my fantasies, I think it would be easier…but I am not meeting many if any at all worth while people to hang out with.

And that’s the pay-off that I mentioned earlier.

In order to feel as though all this is worth it, all this money, time and effort I put in to looking like a hott chick…there needs to be a pay-off.

So what’s the pay-off?

It could be many things.

But I dress solely to get off.

So ultimately I need to have sex or masturbate whenever I dress up.

So if I dress solely to get off why not just dress up then masturbate and then be done?

That’s a lot of time effort and money for a quick wank. Dontchathink?

Plus, masturbation is only fun sometimes. There’s nothing like the unpredictability of another person and what they’re going to do to you.

Also, The point of why I dress may be to get off. But, it’s also for exposure. To show the world how great I look. And right now, I have no one to take pictures or video of me posing glamorously and provocatively and erotically and pornographically. Which I NEED IN ORDER TO KEEP DRESSING. Otherwise I dress up, walk around and smoke, wank, then I’m done. It’s pointless without either going out, getting pictures or video taken of me, or getting fucked.

So what IS my ultimate goal with Monica?

That’s a 3 answer question.

To either:

1) Get surgery and become a full-blown transsexual

2) Continue to be a part-time transvestite

3) To stop being a transvestite all together

Become a full-blown transsexual:

A part of me doesn’t feel like this is even remotely an option. Since I would lose everyone in my life if I did this because almost no one would understand. But then a part of me thinks this exactly what I want. It’s clear I am not a “guy” that is attractive to the kind of women I’m attracted to. And so much of what I think of ALL THE TIME is fashion, sex appeal, make-up, being a home maker, and how much of a guy I am not. It makes a lot of sense.

Continuing to be a part-time transvestite:

The only way this can happen is 1) if I can make more money to support another personality 2) Find a girlfriend who wants me to dress as Monica almost as much as I want to 3) Find friends who will introduce me to other passable trans type people vestites or sexuals or queens to be able to have a support system who are on the same level as me (attraction wise) 4) Move to a geographic location where there is a larger community of people who have my lifestyle and look (because Boston and Providence doesn’t) 5) Being able to have someone to play out all my sexual fantasies with.

Stop being a transvestite all together:

The only way this will happen is I need to find a girl who 1) I am both physically and mentally attracted to (which is harder than you’d think) AND 2) Find someone who is kinky as fuck (Also harder than you’d think)

So, there you have it.

In summation:

I either:

Need to get surgery to be a full-blown transsexual.


Obtain money and a support system to continue living both genders.


Find a girlfriend who will replace Monica.


If you’re a girl or tranny and you’re reading this and STILL are interested in dating me, you have to some things:

I like insane rough sex. What does that mean?

I want to write on each other in lipstick “Rape my cum dumpster mouth.”

I want us to perform anal on each other.

I want us to slap, spit, gag, choke and deep throat each others faces.

I want to tie each other up and leave one another in a cage while the other goes to work.

I want to make each other clean the house and perform chores dressed to the nines.

I want us to smoke while we make love.

I want to have threesomes with other men and women.

I want us to eat each others cum.

I want you to look at every picture, video, etc. on this blog and know that I want to do and be a part of and act like every one of those images.

If I can’t have any of that, I just NEED someone who will replace Monica and all the feelings she / it / I gives me.

So, that’s how this ends. Not with a bang, or even a whimper, (even though that’s how this REALLY should’ve ended)…it just ends.


All this was really supposed to be was a good bye letter, but as I started writing it I realized I had a lot more to say and owed my fans, friends and lovers a reason why Monica will be no more. Plus, this will ONE OF my last ditch efforts to try and wrangle up a support system, mentor, fuck buddy and girlfriend.

If one of you can find me multiple mentors, photographers, videographers, dates, sex buddys, friends, etc…then Monica has a purpose. Otherwise, she’s just an old tranny collecting dust so I’m pulling the plug on this bitch. If you want to write you have a few options:

My Facebook:

My Myspace:

My Tumblr ask box:

My Yahoo email (I hardly ever check this one):

Until then Monica Maxwell will be waiting for her Sin-derella

For the haters:

For the lovers:

To my father:

You know what I’m writing in lipstick there? “It’s not a phase dad!”

I love you all, kisses xoxo

I’m out!