Anna from Across the Hallway Pt. 01

Note: This begins a long, many-part story which I've completed writing. I will be posting new parts frequently, as I complete the final edits on them. I hope you enjoy the read! -- Valory.

*****

I'd lived in my apartment building for maybe eight months before saying more than just hello to Anna from across the hallway.

I was able to move into my first apartment by myself when I graduated from community college and got a job as a UPS driver. Some people thought I had more promise than that, but all I wanted was a living wage, a chance to buy a fishing boat, and write the amateur poetry I never showed to anyone.

The apartment building had once been a corner grocery store, with the store on the bottom floor and living quarters on top. Now, the building had been converted into two apartments on the bottom floor and three on top. Every day as I returned from work, I'd climb the inner stairs to the top landing, and enter the leftmost door to my long and small apartment. The door in the middle seemed to belong to a young Hispanic woman, and the door on the right belonged to a nosy old lady.

I say nosy, because I'm a crossdresser who dresses as a woman most of the time when I'm home alone. My male name is Jerry, and when dressed as a woman, I'm Lisa. I belong to a crossdressing club, have been out in public as Lisa several times, and am even thinking of taking a CD cruise in the future. Imagine all the hanky panky, Love-Boat stuff that could happen there!

The nosy old woman (I never did get her name) -- I'd swear she figured out what I do in private. Like, we both had bay windows facing south, so we could both look a little into each other's apartments. I tried to keep the blinds in her direction closed, except when I left for the day. Maybe I forgot to close them one day and she spotted me "en femme"?

During the brief times I've spoken to her, with her unruly gray hair, she hinted in an around-about way she knew I was up to something. Ever since, I've been triple vigilant about keeping those blinds closed.

As for the young woman who goes in the middle door..... I'd seen about as much of her as I'd seen of the old lady. I mean, I guessed her to be 22-ish and had no idea what she did for a living (maybe a student?). She dressed "average" for her age and wasn't bad looking. I saw female friends of hers come to visit several times; all Hispanic -- I'm not sure if they were relatives or not.

One Saturday I was climbing the stairs with groceries for the upcoming week. When I reached my door and dug in my pocket for keys, her door opened and there she stood, wearing dark pants and a bold-striped T-shirt.

This was a bit of a surprise. Here I was, looking forward immensely to changing into into Lisa, when this very real woman suddenly materialized. I noted her long, black hair, reaching down over modest breasts, and her three-or-four-inch heels.

She spoke first. "You are Jerry, right?"

I was impressed she remembered my name. "Yes," I managed as I set the groceries down.

"You work for the post office, don't you?"

"Oh, no. I work for UPS." I had the feeling she wanted some kind of delivery favor, which would be hard since my route was in a different part of town.

She seemed upbeat, almost cheery. I loved her Spanish accent. She looked aside for a moment before continuing with, "Would you marry me?"

What? Was this some kind of joke? No, there was no hint she was kidding. She looked earnest, almost as though she'd asked what groceries I'd bought.

"Do I want to marry you?"

"Yes, would you marry me?"

My mind went into overdrive. Shit! What.....? Marry her? Jesus. Suddenly I remembered her name. "Anna, I don't even know you -- I can't marry you."

Now she stood in a more passive stance, holding her cute hands together in the traditional fig-leaf pose, looking downward as her countenance saddened a little.

"I'm really sorry, Anna, but I can't marry you."

She didn't say anything further -- just kept looking down.

I didn't think there was anything more I could say, so with embarrassment and detachment I unlocked my door and brought my groceries inside with a quick "Bye."

Once inside, in my own sphere of privacy, I was so unsettled it took me a half hour to get to the place where I wanted to feel sexy again as Lisa.

This amazing encounter with Anna, though, stuck in the back of my mind the rest of the day, and into the next as I breezed around the apartment cleaning, cooking, reading, watching TV, and yes, writing a bit of poetry.

As a matter of fact, I wrote this about the experience:

In drab mode, not Lisa

Real girl Anna taps my shoulder

Asking, asking, so innocently

Will I marry her?

Well, maybe, if I be the bride

In ever-so-sexy backless gown

So she can deflower me

Gosh

Aside from that horny reverie, on the more practical side, I kept wondering why she asked. I had been so taken aback I hadn't been able to continue the conversation. I figured I should've.

I couldn't believe she was attracted to me. I'm not goodlooking; I'm not a chick magnet; I'm just a dull delivery driver. I have no girlfriend; drive a 10-year-old car; and the only bright parts of my life, to be honest, are writing poetry and becoming Lisa. Lisa (at least in my mind) is pretty, sexy, curvaceous, outgoing, generous and happy.

I decided I had to return and talk to Anna. But not that very day. No, I'd sit on it for a couple days. That stretched into a week, and I hadn't seen her. One night, after a dinner and beer, I somehow felt expansive and nervy enough to knock on her door. She wasn't home. I felt deflated.

I tried again the next night with no luck. Finally, on Friday, I thought I'd give it one more try before I gave up, and she answered the door. Again, she looked cheery and up. This time she was wearing an embroidered poncho over a long, white cotton dress. I loved her elaborate earrings.

"Hello Jerry."

"Hello."

"What......?" She really didn't seem to grasp why I would want to talk.

"Mind if I come in? I'd like to talk to you, talk with you."

"Oh, OK." She closed the door behind me. "So, maybe you changed your mind?"

"That's what I wanted to talk about."

She brightened a bit. We went into her living room. There was a little clutter and the smell of cooking in the air. Pleasant. We sat at opposite ends of her sofa.

"I mean, Anna, it was pretty unusual to ask a person who's almost a stranger to marry you, right? Why do you want to marry me?" It was unusual for me to be so direct.

"Well, you seemed like a nice man. You have a good job."

"You don't have a boyfriend?"

"Oh, I did have. He joined the Marines."

The story was beginning to take shape. "Did you want to marry him?"

"Oh, yes, especially after that last night we were together, before he went for training. He got me pregnant. After that, I told him I'd follow him to live off base. But he just ghosted me. Doesn't talk to me anymore."

"Does your family know?"

"Just my sister Esmeralda."

"I'm sorry, but what do you do for a living?"

"I work in a panaderia, you know, Mexican bakery. I'm like one of the managers. You like Mexican pastries?"

"I'm not familiar; sorry...... So, you need a papa for your baby? You thought maybe I'd be a papa?"

She looked to the side once again and wiped away a tear making its way down her cheek. "I know what I asked was stupid. I guess sometimes I hope for a miracle. That my luck will change."

"Grasping at straws?" I offered.

"I try to be positive. I know my life will be OK, I just know it. God will guide me and show me a way."

After just a few minutes, I felt much closer to this young woman, to which I both felt attracted to because of her looks and innocence, while sympathizing with her. All because I merely lived across the hall, had a decent job, was "nice," and was only a few years older than her.

As we talked, I hinted at ending the pregnancy, but she firmly said her religious upbringing would never allow that.

What evolved was me feeling more and more empathetic toward her, learning more about her, and visiting her several times. She was probably holding out hope I'd change my mind. Most of her family lived a hundred miles away, out in the farm country. Then there was her older sister Esmeralda, who lived in a nearby suburb, and was married with children.

I continued to want to help her find a solution for her fix. Meanwhile, that little Marine inside her that she'd been carrying for a month and a half was doing what embryos do -- ever so slowly growing.

One night she had me over for dinner. She was wearing thin, loose pants and a lace camisole. I asked if she needed any financial help, if she had medical coverage, and all that. She thanked me profusely, but said she was OK for now. Then, out of the blue (once again!), she asked, "Do you wear women's clothes?"

She'd been peeking through my keyhole? "What's this about women's clothes?" My face must have been as red as Santa's nose.

"The anciana, the old lady next door -- she told me she thinks you dress up as a woman."

I was immediately inclined to do a complete denial. Why the hell would that old woman want to burst the bubble of my lovely female side?

"Oh, my god," I said. "She told you that? Like it's gossip."

"She said she saw you through the window one day. Or maybe that was someone else, like your sister?"

I was prepared to begin fabricating such a person. God knows a poet is always prepared to create something! But I put the brakes on that. She'd been honest with me.....

"OK, Anna. I will tell you. But only you. This is my secret."

"You dress up?"

"Yes, I do. It's very private. I have not shared this with anyone, not even my friends, except some others who dress too. It began when I was in middle school and began to try on some of my mother's things. I loved to spend time dressed, and then when I could finally live alone, I could become Lisa."

"That is so interesting. I never in a million years would've guessed. So..... I've heard of drag queens, but you're not a drag queen, are you?"

I laughed. "No, no. I just love shopping for women's things, and putting makeup up on, and trying to appear as a woman. This all must shock you -- do you come from a religious family?"

Now it was her time to laugh. "Oh, you'd be surprised at all the characters in my extended family. No secrets among us! A gay guy, lesbians, everything. But believe it or not, we're all still very religious. Somehow it all fits together."

"Any cross-dressers?"

"I heard about one from another family. He was supposed to love to perform as a woman but not like a drag queen. Our Latin version, I suppose. Jose to Josefa."

Anna looked me over intently. "I'm trying to see you changed to a woman. God, now I see you in a whole new way. Who'd think that the UPS man has this secret life as a woman? I hope you can show me a photo of you dressed."

So I brought over a photo, which she liked. I was becoming concerned that now the tables had been turned and the emphasis was on me and not on her pregnancy.

She did say she'd carry the baby to birth and would be a single mom. Somehow I wanted to help her in that journey. Me, a crossdresser coming to the aid of a young and pregnant Hispanic woman.

I wrote:

Anna of the earth

Am I the sunlight

Prompting her sprout to emerge

And spread its leaves?

*****

It wasn't long before Anna and I had dinner regularly (once a week) at either my place or hers, with me (yes!) dressed as Lisa. She was so supportive and comfortable with this, even giving me makeup tips and telling me where I could buy things to add to my clothing and lingerie collection. As Lisa, I felt so much more connected to her, like we were sisters or something. I also began to feel more sexual about her.

One day there came a new question, perhaps because we were friends: "Since you don't have a girlfriend, what do you do for sex? I mean, is being Lisa some sort of sex thing for you? Pardon my asking, I'm always so curious, but curiosity killed the cat, didn't it?"

"Now you're getting into something that I haven't ever talked with anyone about, not even my crossdressing friends. Just in my poetry."

"Oh, you write poetry?"

There it was, out in the open. My most private, personal thing, and I'd opened my soul to someone, and it was both threatening and beautiful.

After I explained my poetry writing, and she said she absolutely said she had to read some of it, the subject that hung in the air was returned to.

"You do sex as Lisa?" she wondered.

"Like, I make love to myself?" I laughed a little. "If I tell you some things, you must absolutely keep them to yourself. If you tell your sister or whatever, I wouldn't forgive you. I think you're impulsive, but this you must absolutely keep to yourself. No gossiping to the lady next door either."

We both laughed. "Yes, OK."

"OK. OK. Women's clothing and things, they make me feel very sexual. They call it a fetish. Like women's things are magic; that's the best word I can think of. I can remember the first time I wore panties, or a bra, or pantyhose. The thrill was out of this world."

I was saying this while actually wearing all these things: my bra, my faux tits, my pantyhose.

I realized I'd began talking more like a woman, like..... Lisa.

"So," she asked, trying to put two and two together, "are you a virgin, Jerry? Have you had a girlfriend?"

"Not a virgin! I had a girlfriend while I was going to college. We went all the way. She never knew about my crossdressing."

"So then, now, you... "

"Yes, I have sex with myself, or with Lisa, or however you might want to see it."

We both laughed a little nervously.

And then, as Anna was want to do, she walked over and gave me a kiss. We had hugged goodbye a couple times, but this was an honest-to-god kiss, Anna to Lisa.