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Do you wear girls underwear?
🕑 Added 2022-06-09 17:00:00 +0000 UTC"Do you wear girl's underwear?"
The question caught me off guard. Wendy and I were headed to Champaign, where she was attending an orientation at the University of Illinois. She had invited me, and since I had an enormous crush on her, I accepted.
I looked at her. Her head was cocked in expectation.
I felt my face flush as I tried to maintain my lane. The sound of the tires passing over the expansion joints on I-57 counted off the moments of my mounting embarrassment. Tha-wump. Tha-wump. Tha-wump.
"I was just wondering, that's all."
More seconds passed. "How do you know?"
She straightened up in her seat. "It's okay. I don't mind."
"But how did you find out?"
"Well, one day at work I could kind of see the outline through your pants. And that day you helped Kristin move you crouched down to pick up a box and we could see your underwear."
"Oh my god."
I leaned my head against the window and considered the fallout. I wanted my cross dressing to be a secret. I wanted absolute control over who found out—and when.
"So which pair are you wearing today?"
I turned again to look at Wendy. A smile had spread across her face. Her brown eyes twinkled mischievously. I hesitated. This wasn't the reaction I was expecting.
"Polka dot."
"What colors are they?"
"Pink and green."
"Are they bikinis?"
"Yeah."
"Am I going to see them?"
I blushed. She giggled.
I wasn't a case of never been kissed, but close. Being shy, I needed the context of work or school to approach a girl. Luckily, I worked with Wendy, and to my amazement an easy going rapport had developed between us. Soon we were flirting and teasing each other endlessly.
I was in heaven.
But despite the obvious attraction, I still couldn't work up the nerve to ask her out. So when I wasn't in heaven, I was in self-inflicted torment. Which is why I was so relieved when she asked me out.
Long car trips are a great opportunity to get to know someone, and Wendy and I certainly were.
After the two-hour drive through the prairies of central Illinois, we finally arrived in Champaign. Wendy's orientation didn't begin until seven-thirty the next morning, so we had the night to ourselves. But first we had to get a room.
Because she was nineteen and I but twenty-four, it might appear suspicious if both of us appeared at the registration desk. We decided that as the eldest in our party, it would be best if I reserved the room. Besides, I had an actual credit card.
Despite the flirting and the frank conversation, the bed question loomed large as we approached the motel.
"Would you mind if we got separate beds?"
"It's going to look kind of strange if I'm the only one checking in."
"I'd just feel better if we did. We can split it."
I really liked Wendy. She had fought with her parents to go on this overnight, and I had to admit that if it wasn't for her asking me out, I wouldn't be here. It wasn't the time to push.
"No—that's fine."
"Are you sure?"
"Yeah."
The room was standard-issue motel, with low maintenance carpeting, synthetic bedspreads and the requisite walnut furniture. Champaign in July isn't exactly a tourist mecca, so it was a bit stuffy. I lay across one of the beds and stretched. I was starving.
Dinner was at a fast food joint. Afterwards, Wendy announced she had forgotten to pack something, and needed to stop at a TJ Maxx.
"It'll be quick, I promise."
I waited in the car while she went inside. Wendy returned with a fairly large bag, which she carefully set in the back seat.
"What'd you get?" I asked.
Wendy smiled. "Oh nothing—just some girl stuff." The look on Wendy's face didn't do much to convince me that she had just completed a routine errand.
Confirmation came when she changed the subject.
"You want to go out for a drink or two?" (In addition to a national speed limit of 55 MPH, these were also the days when nineteen-year-olds could legally obtain beer and wine.)
I did, and so we headed downtown. There, we found blocks of bars catering to students. Wendy took my hand, and we strolled up and down the street, savoring the summer dusk and the unhurried pace of a half-empty college town.
Music drifted out of the bars, and we paused outside each one to ascertain the likely clientele. The Oak Ridge Boys and Diana Ross were cues to move on. As was Van Halen.
Eventually, we heard Muddy Waters. Perfect.
We went inside and ordered beer. There was a nice, quiet booth in back where we drank and talked. The newness of her company was exciting. Conversation flowed effortlessly. I wanted to freeze the moment and keep it forever.
When we left the street was quiet, illuminated only by the soft glow of colorful neon. We took our time walking back to the car.
"How do you feel?" asked Wendy.
I looked at her. Her dark-brown hair cascaded like water over her the creamy skin of her shoulders, which were exposed by an airy sundress that hinted at the supple, lithe form beneath.
Her eyes searched my face for an answer.
"Never better" I said.
After returning to the motel, Wendy took a change of clothes and disappeared into the bathroom.
I sat on the bed and puzzled out how best to kiss her. If I didn't, I was going to spontaneously combust.
She emerged dressed in a t-shirt and running shorts. I smiled at her.
"Come here" I said.
Halfway across the room, she stopped and removed her shorts. She lifted up her t-shirt to better show her underwear. "You've seen mine. Now I want to see yours."
This was followed by a lascivious laugh.
This was my reckoning. My moment of truth.
I stood up and reluctantly pulled off my t-shirt. Then my shorts. And there I stood, naked save for a pair of polka-dotted panties.
Wendy giggled. "I love them!"
She approached me and we shared a hot, lingering kiss. It was like putting a match to gasoline.
We fell into a passionate exchange of kisses and caresses. The touch of her wandering hands through the silky fabric of my underwear was incredible. As I kissed my way down her neck and drew my hands across her back, I realized she wasn't wearing a bra.
Before long we were on the bed, doing what lovers all over the world do. We lay in the afterglow for some time.
When I began to feel a chill and reached for the covers, Wendy asked if I was cold.
"A little" I said.
"Don't you have anything to wear?"
"No—I don't wear pajamas" I said.
"Maybe I can help" she said, and retrieved the bag from her shopping trip.
"Here. This is for you." She sat on the edge of the bed and waited for me to open it.
Inside was something I didn't quite recognize. It felt structured yet soft. As I opened the bag and removed the contents, I realized it was a corset. Also inside were panties and stockings. I blushed furiously.
Wendy crawled up on the bed and kneeled next to me. "Do you like it?"
Any resolve I had about downplaying my cross dressing dissolved in the face of Wendy's present. It was beautiful, and I am only a little ashamed to admit I couldn't wait to try it on.
"You got this at TJ Maxx?"
"Yeah. Pretty sexy, huh?"
"I love it. Thank you." Wendy's face glowed as she leaned in for a kiss.
"Try it on. I'll help you."
I had never worn a corset before. It was a little snug, but Wendy was able to fasten it and helped me with the stockings and garters.
"Woo hoo! Hey there, hot stuff!" Wendy held out her hand.
I approached, trying to process a combination of feelings unknown to me. It was embarrassment, mixed with lust.
"You are sooo cute. I'm so glad you came with me."
I looked down. "I'm so glad you asked."
"Well, I figured one of us had to."
The frustration of my inability to ask her out welled up in my throat. "Wendy..."
She wrapped her arms around me. "It's okay. It doesn't matter. We're here, right?"
We lapsed into more smoldering kisses and another round of sex. Afterwards we fell asleep, deeply contented.
The next morning, her orientation went off as scheduled, and Wendy and I enjoyed a leisurely trip back to Chicago. The flat, featureless land sat underneath a brilliant blue sky. It looked far more beautiful than it had on the trip down.
Which was probably because I was falling in love.
