Ashlyn--My "to do" list

Back to the blog.

I’ve been a busy girl the last two weeks. Once I “decided” (like I really had a choice) that I am going to stay Ashlyn for the rest of my life, I really threw myself into improving my situation.

Well, that’s not entirely true. First I went through a bottle of Jack Daniels, puked my guts out, and slept off a hangover. Eventually I got up, took a shower, and took a long look at myself in the mirror. I was no longer pretending. This was me from now on. Ashlyn with the big boobs and red hair.

And for like the third time since I woke up as Ashlyn, I cried. I was glad my roommates weren’t home to hear me sobbing in the bathroom—although I guess I don’t have to be ashamed of crying anymore—girls are allowed to cry, right?

More than anything, I think I was mourning the loss of a life that I had aspired to have one day. I worked all the time, and had a terrible personal life, but I hoped someday to find the right woman, get married and raise some kids.

Now I know I’ll never be a husband or a father—and that makes me very sad.

The cliché is true. I did feel better after a good cry. So after a brief “mourning period” I decided that if this going to be my life from now on I was going to make the best of it.

I made a mental list of things I needed to do and goals for my life. My first official act, claiming this life as my own: Calling the IRS.

The previous Ashlyn left me in a bad financial situation and I’ve decided to face the problem straight on. At first I was real angry with the original Ashlyn for leaving me with such a financial mess—the girl had no sense of financial responsibility, and seemed to spend money like more would just magically appear whenever she needed it. After a while I realized that everyone has things in their lives that they are fucking up on a daily basis. I’m sure Stephen didn’t care for the 30 pounds overweight he inherited from me…or the trip to the dentist I had been putting off for the longest time. I hope that trip to the dentist was painful “Jake”. Yeah, I’m a little bitter.

The IRS situation went better than I could have hoped. I talked to a local agent, a Mr. G (I’m leaving his name out on purpose) about my problems by phone, but I suggested I we meet at his office and discuss things in person. Very business-like, he kept saying we could do all this over the phone—and I said I would feel more comfortable meeting him in person. What I really wanted was to see how much sway my boobs could have over the IRS. Yes, I know this is wrong—but hey, this is the IRS. I needed all the help I could get. I was just praying the guy wasn’t gay.

He wasn’t. I know this is vain, but one of the joys about being attractive is watching guys trip all over themselves when they meet me. I was so average looking before I was transformed into Ashlyn, I practically faded into the background—it’s fun to stand out, even if it is the wrong gender.

I walk up to his cubicle wearing way to little clothing for how cold it has been lately. He stands up quickly, eyes a little wide with surprise, and warmly sticks his hand out for a handshake.

I’ve learned to shake hands like a girl—one of the millions of little differences between men and women is the way we shake hands. When men shake hands it’s like a show of strength: firm grip, hearty shake of the arm. When a woman shakes a man’s hand, it’s a softer, gentle exchange. I made the mistake a couple of times, early after my transformation, trying to shake hands like a man. It always made the greeting awkward.

Mr. G the IRS agent was sooooooo helpful. Yes, I am a little bit evil.

Mr. G set me up with a payment plan that I could afford monthly and got the tax lien removed. My situation wasn’t as bad as I imagined, I keep forgetting how young I am now—Ashlyn hadn’t been a wage earning adult long enough to truly get into unrecoverable tax woes. Now if I could pay down some of my credit cards I could start rebuilding my credit.

I let a day or two go before I revisited my mental list of goals/things to do. Second on my list was to pick a college to go to for summer courses. The Boston area is the perfect place to be—there must be a hundred colleges in the area. People remember the heavy hitters—MIT, Harvard—but there is a wealth of colleges that I can get to by taking the “T”. I spend hours online researching schools and making appointments for visits.

Eventually I suffer information overload, and can’t do anymore research. I shut off the computer and fall into bed, but my brain won’t shut off. I looked at the clock. It was late, but not too late, to make a phone call and cross number three off my mental list.

I call Jean-Michel. I get his voice mail. I attempt to put a little something sultry into the way I talk. “Hello baby, this is Ashlyn. Would you please call me? I’ll be up for a while. Bye.”

He calls me about an hour later. I was a little nervous when the phone rang. I had slept with Jean-Michel during my visit to Canada—and when I think back to the things we did together I felt a little turned on. It was distracting.

“Hi.” He says.

“Hi back. Is it alright to talk?” I ask.

“It is, but I can’t talk for long.”
“No problem.” I say. “It’s just that I wanted you to know—“I was having difficulty saying the words. “I just wanted you to know I am planning to stay as Ashlyn. I wanted to give you one last chance to change your mind about having your old life back. After today there is no going back—I’m going to make this life my own.”

He didn’t hesitate. “I’m staying as Jean-Michel. I’m glad you decided to stay, I like you. It’s nice to know my old life is in good hands.”

“Thanks, that’s nice to hear.” I pause, collecting my words. “I still don’t understand how you can so easily give up this life. This is a fantastic body, and your parents are really wonderful.”

There was a long pause; I began to wonder if he got cut off.

“I was at a point in my life where my biggest aspiration was to be some rich man’s trophy wife—and I didn’t see anything wrong with that. When I was younger, I wanted to be somebody; I had plans and dreams of making something of my life. As I got older I realized that I could get by with a smile and a little cleavage. It became a crutch.” He said it very quickly.

“As Jean-Michel, I am who I am because of what I do, not because I have killer body and beautiful green eyes.” The statement came out as a compliment. I laughed lightly—hell, I giggled, it’s the same thing, right?

“That’s a little narcistic, isn’t it?”

“Maybe. But I remember how you were in front of the mirror. I think we both might have narcistic issues.” He says.

We talk for half an hour. It was nice.

“Have you tried sex with anyone else yet?” He asked suddenly.

“Um—no.”

“Why?”

“I don’t know—I’m still surprised we had sex.” I was slightly flustered.

“You shouldn’t be. You’re 23 and incredibly attractive, you should enjoy yourself. You’re only young once.”

“Wrong. Some of us are young twice.” I say back to him smugly. “But don’t worry. Having sex again is the fourth item on my list.”

“What does that mean?” He asked confused.
“Don’t worry about it.” I was tired, we said goodnight.

--Ashlyn