The Project Pt. 01

Dee's bedroom lit with a dim blue glow from her smart phone. Her nailed finger swept up the screen as she scrolled the strictly platonic listings.

"Boring, boring, spam, fake. Can anybody complete a sentence on here!?" she thought.

She was just about to give up when she read the headline, "Mess around with gender roles..." As she read the post, she smirked, "Ah, a project." Dee pushed reply-to-ad, and quickly composed an email. Her heart was thumping with anticipation as she pushed send. Then she turned off her phone, laying in on the night stand and laid her head on her pillow.

She remained awake for several minutes thinking about what she read, and the possibilities, oh the possibilities! Closing her eyes she drifted off with her thoughts.

Dee woke with a start, her pillow damp with cold sweat. She glanced at the clock. 3am, ugh, was she awakened from such a pleasant dream. Her mind quickly returned to the ad she responded to, and she checked her phone for a responses. The message light was flashing, and she opened her phone.

"Another damn breast enlargement spam. Don't they know my tits are big enough? Delete." She slammed the phone down and rolled over, trying to return to her dream.

Buzz, Buzz, Buzz! The alarm sounded like a hammer slamming against her head. Dee rolled over and hit the clock, silencing the grating, angry noise. Out of habit she picked up her phone and checked for messages, but there was nothing. Glancing at the clock, she realized she was late for work, and she quickly dressed, made up her face and rushed down the steps forgetting her phone on the edge of her night stand.

Work was busy as usual, but Dee had trouble concentrating as her mind drifted back to the ad. She patted her pockets during a down moment to check her phone, when she realized she had forgotten it. This was going to be a really long day!

Chris had just gotten to work and sat down at his desk to start his day. He retrieved his phone from his pocket, as was his routine, to check his messages before he could even think about working. Expecting to see his inbox empty, he logged on to his secret account, and there highlighted in bold was an response to his ad "re: Mess around with gender roles..." Anxiously he opened the email and read it intently. He sat back in his chair, intrigued by what he read, and quickly drafted a response. After pushing send he would spend the next 8 hours unable to concentrate on his work. Instead he maniacally checked his email hoping for a response. Meanwhile at 8:15am, Dee's phone vibrated with an incoming message on her nightstand.

Dee slid her key into the lock to her apartment and trudged through the door. It had been a long day and she just wanted to crawl into bed. She threw down her coat and face-planted into her pillow.

Peering towards her night stand she saw the blinking lights on her phone. Quickly she grabbed it and sat up on the bed, eager to see if there was a response to her message.

Dee scrolled through the endless spam and finally came across the response Chris had typed 12 hours ago. She quickly read the email, her heart thumping into her throat, and her brain began devising a plan. She penned a reply, returned her phone to the night stand and rummaged through the night stand drawer for her vibrator.

The vibrator buzzed to life with a flock of the switch. Dee slid it down her still clothed body between her heaving breasts across her stomach, and then traced the outline of her thighs, stopping between her legs. Slipping a thumb inside the waist band of her pants and underwear she pulled them out and ran the vibrator against her skin and into her sex. The buzzing muffled as she plunged the vibrator into her pants. She released her waistband and crumple her pillow as the vibe did its job releasing her tension from the day.

Chris sat down in front of the tv to eat his dinner, alone, all but giving up on the promise of the email he received earlier. He then decided not to check his phone anymore this evening. He flipped through the channels and finally landed on 'Ru Paul's Drag Race,' one of his favorites. He watched intently soaking in techniques that he could employ in his next dress up session. Chris was so enamoured by the show he didn't hear the chime of an incoming message on his phone.

At 10pm Chris decided to call it a night and turned off the TV. Out of habit, he reached for his phone noticing the blinking light. Opening his email, he saw Dee's response. His mouth got dry and he gulped in his throat while reading the email. He realized that Dee was the one he had been looking for to share his desire. No sooner had he penned a response, and his phone dinged with an incoming message from Dee. It contained her messenger name and an invite to open a private chat session. Chris hesitated over the link, having been burned in the past, but he had to quell his curiosity, so he clicked on the link.

A message window opened on Dee's phone. Dee quickly accepted the invite, knowing that she was one step closer to reeling Chris in, she just had to bait a bit more.

Chris and Dee messaged back and forth for hours. Chris explaining his desire to crossdress and interest in going out in drag one night. Dee took in what he said and offered support, showing interest in his lifestyle. She was genuinely interested in trans people, some might say obsessed, but her end game was more involved than Chris knew. As they chatted she reassured him, with a smirk, that this was all strictly platonic. Chris, comforted by her reassurance that she was serious agreed to meet her the next day for coffee.

"Chris! Skinny mocha, no whip!" the barista called.

Chris walked over for his coffee and found a table near the window. He and Dee were supposed to meet at 12, but he was early. He sat nervously sipping his coffee, his stomach churning in anticipation.

Chris pulled out his phone and checked his messages. A message from Dee popped up. Dee was running late and wanted to know what he was wearing. Chris responded, telling her he was seated by the windows, and continued checking his mail.

Seconds passed but they seemed like hours, as he anxiously waited. The barista continued shouting names as he completed orders. Chris was wondering if Dee would order coffee. If so perhaps he could get a glimpse of her before she found him. The crowd around the delivery area was getting crowded. Chris couldn't even see the counter through all the people.

"Vivian, Chad, Delilah!" the barista shouted.

Chris glanced out the window.

"Hello. Chris?" a smooth feminine voice queried over the hum of the other patrons.

Chris looked up and clumsily stood up to greet her.

"Dee?" he asked.

"Dee is short for Delilah. It's nice to meet you!" she answered as she leaned in for a hug.

Chris reciprocated and felt her ample chest press against his. His heart was beating a mile a minute. He'd never met anyone in person that knew his secret. She squeezed his arm as she sat down.

"Don't be nervous. I don't bite, unless you ask." she chuckled.

Chris sat and again nervously sipping his coffee while he have Delilah a quick up and down. She was dressed fashionably in business attire with a silky maroon blouse that minimized her chest, even though Chris knew otherwise. A pair of black fitted suit pants hugged her curvaceous hips, and ended dusting the arch of her modestly platformed, high-heeled ankle booties. Her black hair flowed in large soft curls and landed on the shoulders of her fitted suit jacket. She was quite attractive.

"I seem to be underdressed," Chris stated looking down at his khakis and button down.

"Not at all!" she replied, "I just had a meeting. I work from home mostly, and usually I'm not wearing pants."

Chris was amused by her ice breaking quips, and began to relax.

"So," Delilah leaned in over the table, "tell me why you decided to place your ad."

Chris could feel his palms begin to sweat.

"Cutting right to the chase huh?" Chris joked.

"I'm already interested, and you didn't run away, so why waste time?" she reasoned.

He took a deep breath and a sip of coffee and recanted his fascination with gender bending and the feelings he got when he dressed. He also explained his desires to look as convincing as possible, and the great pains he had taken to learn makeup techniques and ways to give him the perfect feminine form.

Chris paused contemplating revealing his ultimate crossdressing fantasy, but decided not to scare Delilah away just yet.

"I'm impressed with your enthusiasm toward perfecting your look, but what is your end game? I think your holding out on me. Tell me what you really want, don't waste my time Chris," Delilah pushed, sensing he was holding back.

Delilah wasn't sure if maybe she had been too assertive until after the words came out of her mouth, but she was already sure Chris would be the perfect subject for her plans. She watched his face to gauge his reaction.

"Well, uh, you see, uh, I kind of have this fantasy, uh, um, that I would like to go out in public dressed, with a biological female." Chris stammered softly, uncomfortable with Delilah's bluntness.

Chris waited for Delilah to dismiss his "fantasy" as only a half truth, which was what it was, and dismiss herself from the table. He felt she could see right through him. Instead, knowing he was softening his fantasy, Delilah leaned in, masking her excitement.

"I think I can help you with that, under two conditions. Let's make a date today, and you let me help you get ready."

Chris was stunned.

"I'll be in touch Chris, but right now I need to get to my next appointment." Delilah said as she stood up straightening her jacket and smoothing her pants, "it was nice meeting you! Email me a date by the end of the day."

She looped her purse strap over her shoulder and strutted out the door, her heels clicking rhythmically on the tiled floor. Delilah closed the door to her car and dialed her phone.

"Hi, it's Dee, I have a new project. How's your schedule looking?...Good, I'll be in touch with the date and time."

Chris returned to his cubical still in a daze from his lunch date with Delilah. It was almost time to leave work and he hadn't looked at his schedule.

His phone pinged. It was Delilah asking if he'd thought of a date yet, and apologizing for seeming to straightforward. She also expressed her support to help him. Chris quickly checked his schedule and messaged back. He immediately received a message back from Dee, she had reserved room 429 on Saturday at Hotel Rue. He was to be there by 6pm with everything he needed to get ready. She closed the email with 'XO'.

Chris gulped, it was real now, and there was a plan.