Room 139--08

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Laura was intrigued by a guy who liked dressing as a woman.
1.8k words
4.41
24.9k
5

Part 8 of the 9 part series

Updated 10/31/2022
Created 05/16/2012
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Despite Laura's cross-examination, the dinner at the House of Pies wasn't a total disaster.

Like Wendy, Laura was intrigued by the idea of a guy who liked dressing as a woman, and the table reverberated with the pros and cons of having a cross dresser as a mate. The conversation continued in the parking lot, to the extent the six of us made tentative plans to meet later that night.

Jess and I exchanged phone numbers and promised to get together and shop the junior's department at Carson's over Christmas break. It was seven o'clock by the time we got back to room 139.

The four of us got dressed together. It was the best way to maximize the available space—not to mention the bathroom mirror. Besides, we had seen everything by that point. What was the point of a door? And with innumerable hooks and fasteners and zippers, many hands made for light work.

Our collective anticipation took over the room. Spirits were high.

Wendy was stunning as a magician's assistant in her black corset, sheer black stockings and black heels. Michelle was radiant in her strapless, floor-length sequined movie starlet gown. And Kelly was centerfold-sexy in her teeny yellow bikini.

Kelly finally declared "Ladies, we are ready!" Michelle reminded us of the rules: No guys, five drinks max and to meet at Burlson's if we got separated. Then she insisted we make sure each of us had the phone number to the motel.

"One more thing: Kelly has the motel key and the car keys. Don't lose her!"

Wendy had a final suggestion before we left. "Let's see if we can find someone to take our picture." There were snickers when she returned with an old guy in a CAT Diesel baseball cap and work boots.

"Hiya ladies. Fixin' to out tonight? I heard you all hootin' and hollerin' a minute ago and figured something was up. It's gonna be plenty crazy out there, I tell ya. Be careful."

Wendy set up the camera, showed him what button to push and it was done. He was a gentleman, and escorted us to the car.

"Goodnight ladies. And watch out for them fellers!" Wendy slid next to me in the backseat. "Too late" she said with a smile.

Kelly soon had the Pontiac headed towards campus.

Owing to the enormous crowds, we were forced to park several miles from downtown. On the plus side, it gave me time to practice walking in heels.

Wendy, Michelle and Kelly all shared their advice. But Michelle the drama student had the best, and even developed a character whose demure and unintentional sexuality fit the costume.

Too bad I was such an awful actress.

While my companions generated lust, I created curiosity. I danced with a SIU freshman dressed like a butler, and she was kind enough to volunteer the services of her feather duster. She was curious about how I had ended up in such a costume.

Michelle and Kelly were fascinated by the questions they got in the bathroom from women who were on to me. Unlike Wendy, they had never experienced it before. "Is he your boyfriend?" "How does he fit into a costume like that?" And Kelly's favorite, "Who did his nails?"

Michelle decided she was going to try the men's room. But between the groping and the come-ons and the dirty stalls she gave up almost immediately. "I'd wear a dress to get out of going in there too!" she said to me.

After a couple of hours, we began to run into familiar faces. Some of them I didn't want to see.

A girl dressed like a hooker was obsessed with seeing my lingerie, and kept asking to check it out in the bathroom. Every time I saw her she was drunker and more-persistent than the time before, and her dirt-bag boyfriend didn't help things by saying "Let her see, faggot."

I couldn't take them any longer and retreated to Burlson's. That was the only time the four of us were separated.

But even hanging out there was fun. Someone offered me a hundred dollars a week to clean their house, and another two-hundred to serve drinks and dinner at important social occasions. "Oh my God, an invitation to my house would be the hottest thing in town!"

I curtsied in appreciation but told them I was already employed.

A geisha girl asked me dance. And that's what I was doing when I saw Wendy scanning Burlson's for me. Luckily, I was able to catch up with her and let her know I was okay.

I explained about the hooker and the dirt-bag, and how I felt it best to avoid another confrontation even if it meant sending up an alarm to everyone. I apologized for worrying her.

"I'm just glad you're okay. My imagination was going into overdrive."

Wendy and I hadn't had much time alone, so we enjoyed the walk back to where Kelly and Michelle were waiting.

We both felt odd about the afternoon. Had we cheated on each other? Did we use Michelle and Kelly? Did they use us? We agreed we were having a great time, but the weekend's sexual dynamics were confusing.

"Just like our relationship" laughed Wendy.

"This weekend has been so great" I said. "Having everything out in the open has been unbelievable. I love it! It's dissolved all these boundaries. I feel so free. I feel like I've been hanging out with Kelly and Michelle forever!"

Wendy beamed at me. "I've never felt anything like this before! And they were saying the same thing! It's unreal. What's going on?"

Just then we heard two voices calling our names. It was Kelly and Michelle. They hurried down the sidewalk towards Wendy and me.

"Where were you? What happened?" Their faces were full of concern.

I again explained about the hooker and the dirt-bag, and waved it off. "I'm just sorry I worried you guys. I just wanted to get away from them."

The three of them regarded me with genuine empathy, and it struck me: which of them hadn't been in a similar situation at some point before?

Time was growing short, and I could feel Sunday approaching. I didn't want the weekend to end on such a somber note.

"Weren't there free jello shots at the Wild Hare after midnight?"

The three faces brightened. "Yes!"

We set off for the Wild Hare.

Not surprisingly, the club was packed. Free jello shots in a college town can do that. Wendy and Michelle somehow managed to get half a dozen, and brought them to Kelly and I. We hadn't even snagged one.

I eagerly grabbed a shot, toasted Wendy and Michelle and grabbed Wendy's hand. I had to dance. We tore into the Psychedelic Furs' 'Pretty in Pink'. Wendy's eyes shone, and it wasn't long before Kelly and Michelle joined us. The four of us danced until closing time.

Happy-drunk but eager to get out of our shoes, we made our way through the throng and out into the street. Remarkably, there was an empty bench on the other side. We made our way to it and collapsed.

"Ugh! I don't know about you guys, but next year I'm bringing a purse big-enough to stuff some gym shoes in" said Wendy. "We still have to walk another mile, right? Grrr!"

"I don't know how you guys do it" I said.

"We don't" said Michelle.

We massaged our aching feet for several minutes, watching the street life. Despite the way I was dressed, my metabolism had remained male. The salad and iced tea hadn't sustained me, and I was starving.

"Wasn't there an all-night taco place a couple of blocks down? Maybe we could give our feet a rest there and get something to eat."

The threesome looked at me hopefully.

"Really? I was too busy watching you walk in heels" teased Wendy. "I'm game if those two are."

"Michelle? Kelly? My treat."

"A couple of blocks, right? That means two" said Kelly.

We collected our shoes and staggered to Senior Ray's Taco Emporium. After the dim lights of the club, the orgy of florescence at Senior Ray's was blinding.

We paused to take in the menu board. I went up to the counter alone.

"May I take your order please, seniorita?"

I ignored the muffled giggles behind me.

"Four tacos, please."

"Do you wish any beans or rice? A sapodilla perhaps?"

"No thanks. The tacos will be fine."

"Anything to drink? Coffee?"

"Not tonight."

"Okay. Three dollars please."

I dug in my purse and extracted three crumpled dollar bills. I handed them to the cashier.

He nodded and carefully inserted the bills in the cash register drawer.

Suddenly he appeared as if seized by a brilliant idea.

"Some hot sauce, seniorita? Hot? Medium? Mild?"

I turned to check with my dining partners, but they were preoccupied with their snickering. I made a face and turned back to the cashier.

"Hot."

"Right away" he said.

After inserting four packets of sauce and some napkins, he handed me a plain white paper bag, neatly creased at the top.

"Gracias seniorita. Su luminosa belleza solo es igualada por su gracia incomparable." He smiled. His teeth were practically an alternate light source.

Wendy burst out laughing. I ignored her and smiled at him.

We grabbed a table near the front. Wendy would not stop laughing. She was near tears. She finally put her head down on the table to compose herself.

We were dying of curiosity. "Wendy, what's up? What's so funny?"

She wiped the tears from her eyes and began. "Um, Missy? He, um, he..." and that's as far as she got before collapsing into hysterics again. I looked at Michelle and Kelly. They didn't have a clue.

Wendy sat up. She raised her hands. "Okay. I'm cool. Okay." She wiped her eyes. And then she slipped again.

"Wen-dy!" I was starting to get annoyed.

"Okayokayokay. Missy? He said your luminous beauty was equaled only by your incomparable grace."

I put my head in my hands. Wendy, Michelle and Kelly exploded into prolonged laughter. One of them kicked me under the table. I sullenly ate my taco as the three of them relived the moment endlessly.

"I thought your feet hurt" I groused.

This provoked even more laughter.

They eventually settled down, and Wendy pressed herself against me. She put her hand on my cheek and drew my face towards hers.

"You know something? I agree with him."

She kissed me deeply.

Kelly and Michelle generously supplied gagging noises. And on that note we prepared to leave. My companions wanted to make one final visit to the bathroom before the trip home.

"Don't you need to go, Missy?"

"No" I said. "I'm fine."

Michelle regarded me with mock contempt. "She's only a girl on the outside, Wendy. Must be nice."

I went to look for an inconspicuous place to wait, not wanting to further arouse the passions of Senior Ray.

After leaving the restaurant we resumed our walk. The streets were empty. I found the click of our heels reassuring. A soft breeze caressed my legs through the stockings and lifted my dress.

I closed my eyes. I felt so feminine. So free.

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AnonymousAnonymousalmost 12 years ago
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please continue story i look forward to more very interesting

AnonymousAnonymousalmost 12 years ago

I sincerely hope that there is some truth in your story because becoming a girl is truly a freeing experience when ones most inner feelings become reality.

Molly

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Room Series Info

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