Room 139--01

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The road to Halloween has many curves.
1.5k words
4.29
43.3k
10

Part 1 of the 9 part series

Updated 10/31/2022
Created 05/16/2012
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Summer was coming to a close as Wendy prepared for her first semester at U of I. We had grown close, and I was feeling torn as her departure date neared.

I realized there was a very good chance she would disappear into the milieu of college life and that our relationship would fade. And I didn't want to stand in her way.

But my relationship with Wendy was liberating. A joy. She was unlike anyone I had ever met, and I wasn't ready for it to end.

Despite sleeping together on the first date, our thirst for each other remained unquenched. Even beyond the physical we were very much a couple, with much in common and just enough that wasn't to keep things interesting.

Wendy was funny, smart, tender, brazen, interested, good-natured and beautiful. It wasn't an exaggeration to say I was deeply in love with her.

When departure day came, I accompanied her family to Champaign. After helping Wendy get settled in her dorm, her family and I went out to dinner and then returned to campus for the dreaded goodbyes.

At last it was my turn. I had so much to tell her. I tried to tell her I loved her and only wanted what was best for her. That I wanted her to grow, to experience everything that university life had to offer. Yet for things between us to somehow stay the same.

It was a crazy wish.

She smiled through her tears and hugged me tight. We shared a salty kiss and separated. It was torture.

As September tipped towards fall, it was apparent my worries were groundless. Wendy and I phoned each other often; some calls hours-long and others only long-enough to tease each other. We wrote letters, sent mix tapes and managed to get together every couple of weeks.

It wasn't the same as impulsively dropping by each other's place for a summer night's walk or some ice cream, but it was better than separation.

Soon enough, it was October. And with October came Halloween—one of my favorite holidays. In a sense, every day is Halloween when you're a cross dresser. And yet on Halloween I was free to celebrate anonymously. For a day I would be just another guy in a costume.

Not surprisingly, Wendy had several suggestions: bride, cheerleader, cocktail waitress, disco chick, harem girl and her favorite, the French maid. She loved to tease me about the ruffled panties that came with it. Even more so when I blushed.

Which was the interesting aspect of my cross dressing and its effect on our relationship. It brought out a dominant streak in Wendy; she confessed she loved the control of dressing me up, and found my desire to do so arousing.

I was grateful for her acceptance after so many years of secret torment.

For me, it played on those early childhood experiences behind the garage with Leann. As long as it didn't affect other aspects of our relationship, I was happy to comply. Especially since it so often ended in toe-curling sex.

There was a phone call one morning.

"How do you feel about the French maid?" she asked.

"With you, fine. In public—I'm not so sure."

"You'd probably have to shave your legs."

"What?"

"You can't have hair on your legs with so much of them showing" she said. "Besides, you have nice legs. You should show them off!"

I protested, arguing that my modest body hair didn't require shaving, and that it would make me the object of ridicule when I played basketball.

"It'll grow back" she said. "And you could wear sweat pants until it does. Come on. It'll be fun."

I had no argument on that point. But going out in public in such an outrageous costume made me a little squeamish.

"I know!" she said in the voice that would solve everything. "I can shave you here. I have razors and the hair removal stuff. Kelly could probably do your nails. What do you think?"

"Do my nails?"

"Yeah! She is really, really good."

"No."

"She already pierced your ears. Oh my god! I have to leave for class. Think about it, okay? I love you."

Nails aside, the rest of Halloween was coming together perfectly. It fell on a Saturday, which meant Wendy and I could head to Southern Illinois University in Edwardsville and take part in the celebration there. And since my employer had agreed to give me Friday afternoon off, we'd be able to get an early start.

Two weeks before Halloween, I called Wendy.

"Hi! How are you?"

"I was thinking about the French maid costume" I said. I let a silence ensue.

"And?"

"Well, I was thinking that...I'll do it."

There was an excited squeal on the other end. "This is going to be great! I'll reserve it today. It's a twelve—that'll fit, right?"

"Yeah."

I lifted up my shirt to look at my waist. No potato chips until after Halloween.

"I wanted to ask you something."

I sank. When people say they want to ask you something, they're preparing you for something they're fairly sure you won't want to hear. I steeled myself.

"Sure. What's up?"

"What do you think of Michelle and Kelly coming with?"

I had met Michelle once, and already knew Kelly. I liked them, but wasn't sure I wanted to spend a weekend with them.

"I'd like it better if it was just you and me."

"I know, but Kelly just broke up with her boyfriend and doesn't have anything to do. Plus she'd love to do your nails. And Michelle can get you a really gorgeous wig from the drama department—she checked. We want to dress you up. It'd be just us girls."

This was followed by one of Wendy's patented giggles.

"Did you invite them yet?"

Wendy was put-off. "No."

"Wendy—I didn't want this to turn into a campus-wide event. I wanted it to be a weekend with just you."

"But you're going to be out in public with thousands of people!"

"Yeah, but they're strangers. Kelly and Michelle aren't. They know me. People talk, and they can get really nasty about stuff like this."

The opposing forces of Wendy's exuberance and my guarded nature sometimes created a battleground within our relationship. It appeared we were going to pay it a visit.

"You're more freaked-out about your cross dressing than anyone I know! Did I change how I feel about you after I found out? No. Did Kristin? No. Kelly just said it would be fun to make you up. And Michelle has seen guys play girls and girls play guys ever since she's been in drama. They don't think it's a big deal. It's not like we're going to put it in the newspaper."

"Wendy, I just want a little control over who knows, that's all."

"Well, you should know I told Sarah."

"You told your sister?"

"Yeah."

They were thisclose, and I should have figured what one knew, the other did also. The thought of going to Wendy's house and facing Sarah was humiliating.

I was fuming. "Anyone else?"

"You understand I've only told one person, right? Kristin found out the same way I did, and Michelle only knows I have a guy friend who might be dressing as a girl for Halloween. Kelly knows, but that's because she did your ears. I haven't told anyone else!"

There was silence.

I sighed.

"Wendy—it was just beginning to sound like everyone would know and I freaked-out. We're different about this. You love it and think it's cute and don't care who knows. I'm embarrassed and cautious. There are people out there who think I'm a pervert and should be locked up. That's why I get so defensive."

I paused. "I'm sorry I accused you of telling everyone."

"I love you Missy and wouldn't ever do anything to hurt you. I know people can get really mean. But I would never tell anyone if I thought they would use it to hurt you. Sarah loves you—you know that. She thinks it's cute."

Wendy sighed.

"I know you hate that word. But I don't know how else to describe it. Me and Sarah think guys are so weird about feminine stuff—like their dicks are going to fall off or something if they get close to it. We love how you are so into it. You're so curious!"

"Yeah I am. But I also just love the feel of lingerie."

Wendy laughed.

"Don't ever change. If you want it to be just us two that's fine. I'm always going at a hundred and ten, and Kelly and Michelle just seemed like a good fit. That's all."

I laughed. Wendy was usually speeding along at a hundred and ten, while I plodded along at sixty. The fact that it was she who asked me out was the defining component of our relationship.

But our differences served a purpose; I kept her from careening off the road, while she kept me from sinking to the bottom of the fish tank. I was her ballast—she my wings. It worked.

"Look. If you want to invite Michelle and Kelly, it's okay. Just make sure it won't traumatize them for life or anything, okay?"

"Yay! I love you Missy."

"I love you, too."

We hung-up before giving each other diabetes.

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AnonymousAnonymousalmost 12 years ago

More, keep going with the story

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