CrossdressingComplete

The Neighbor

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Many thanks to neuroparenthetical, Andreas_Kreuz and pamelacdnz, who edited this story.

THIS IS A TS/CD STORY. YOU HAVE BEEN WARNED.

When I was twenty, I had a serious fixation on one of my neighbors. She lived two blocks away, and I had been watching her for a long time. Our neighborhood consisted of spaced-out houses with plenty of room for tall, shade-giving trees, and there was almost no traffic. I saw her often walking by -- tall and slender, with short blonde, hair. She typically dressed in men's clothing -- most often a loose suit, which she nonetheless paired with high heels and a scarf. She knew my name, and we said hi to each other, but otherwise, we had no rapport.

My infatuation with her had a deep impact on me. I found her exquisitely beautiful; her poise and demeanor were striking. Every time I saw her, the memory of that chance encounter lingered in my mind long afterward. She was single -- or so the word on the street went. Why that was, I could not say. To my mind, she would have been followed by a long procession of suitors wherever she went, yet that was not the case. She was on the older side -- forty, maybe going on fifty -- but to my twenty-year-old self, that was a mark of allure, not a drawback.

Such was the power she had over my thoughts that it made me want to become a different man. I started dressing better in the hope she'd notice me. Gone were the sweatpants and graphic tees. I wore jeans and shirts, and even those eventually gave way to slacks and jackets.

With my confidence boosted, I tried to do more than simply greet her. On several occasions, I walked with her and made small talk. It wasn't taking off -- that much was obvious -- but I wasn't expecting it would. She and I had nothing in common, and I could not fathom a single reason why she'd be interested in me. Don't get me wrong; I was in no way uncertain about myself. I was young and good-looking, and felt I had a bright future ahead. And despite the lack of interest on her part, meeting her was never a downer; in fact, I found each of our brief encounters stimulating and uplifting.

One day, I saw her in a small park by the river, sitting at one of those chess tables, studying the pieces arranged on the board. She was alone. I approached and said hi.

"I didn't know you were interested in chess," I said after she returned my greeting.

"I'm not, really," she replied, looking up at me from the bench. "I barely know the rules." She smiled -- her intoxicating smile revealing her large, even teeth. "Can you play?"

"My father taught me," I said, "but I'm no chess master," I gestured toward the board. "Is that a chess problem you're trying to solve?"

"Oh, this? I just found the pieces like this."

I sensed an opening. "Would you like to play a game?"

"What if the players return?"

I glanced around. Nobody was in sight. "Seems unlikely. Probably just old-timers who forgot they were even playing."

We played a game. I won. Even though she said she was a beginner, I suspected she had let me win on purpose, so, in the rematch, I let her win. She seemed delighted, and I was happy. I didn't know who was playing whom -- whether it was me, or her again, letting me let her win.

That was it. After the second game, she said she needed to be somewhere else and left. No numbers were exchanged, nor any promise of another meeting.

Nevertheless, it emboldened me. I looked for her more intently every time I stepped outside. When I saw her, I ran after her, greeted her, and no longer tried to hide my big grin of excitement. I walked with her, whether or not I'd been invited.

Then came the moment I asked to take her hand. When she didn't reply, I reached out and took it anyway. My heart thumped wildly after that. Blood rushed to my head, making my ears ring and my temples pulse. She still said nothing. We walked in silence for a while under the trees lining the street, and it took me a long time to gather the courage to turn and look at her.

Other times, I asked her personal questions -- like, duh, how she could possibly be single? One day I asked her what she thought of me.

"I think you're a very promising young man," she said, smiling as she often did.

"You're only being polite," I countered.

"No, I really think so."

"Then go out with me."

She chuckled.

"So it's true," I said. "You don't actually like me."

"I do, I do," she said, amused, "but there's nothing bringing us together."

"I like you."

"We're not a match. Would you really want to be seen with me? What would your parents say?"

"Why does that matter? I'm an adult."

"It matters. I'm too old for you -- old enough to be your father."

Yes, she saidfather.Her pronouncement made me laugh. Shewouldhave been my father -- I knew that,everybody knew that.And in terms of age, she was about the same as my father.

"Are you gay?" I asked brusquely. I'd always assumed she must have been, but I was afraid in that moment that maybe she wasn't.

She frowned. "I've dated men, but you're not that kind of man."

"Oh no? What kind is that?"

She looked to the side and said nothing. I didn't think she had an answer, so I stepped in front of her and grabbed her arms below the shoulders. That forced her to look at me.

"I want you," I said firmly.

Her eyes widened, as if she was seeing me anew. "You do," she said, recognition rising in her voice. "You really do."

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