The Dating Game – Part 1 – by Mollie Blake

I am thrilled to introduce you to Mollie Blake, a wonderful writer from England’s west country. In this, her first piece for FionaDobson.com she’s going to lead you through a story telling the tantalizing crossdressing story of a date night to remember. You can find more of her stories at MollieBlake.com

The Dating Game – by Mollie Blake

Find all episodes of The Dating Game HERE.

“Professor Forbes, I’ve got a…er…Lucinda de Vilish on the phone for you.”

David glanced up to check his office door was closed. “Thanks, Edwina. Put her through.”

“Professor Forbes. This is Lucinda de Vilish.”

Before responding he waited for the “click” to make sure his inquisitive secretary had put her phone down. “Lucy. You’ve rung me at work! This had better be a matter of life or death.”

“Well, hi, David. How nice to hear from you! And it is a matter of life, and my future happiness.”

“So what’s that then?”

“I’ve set us up on a double date.”

“A double date?” The frown David had been wearing for most of the day so far, slowly morphed into a broad smile. He pressed his hand over the top of his dark grey trousers.

“Oh, come on! You know you want to. It’ll be fun. I met this guy and his friend in the bar last night. I said we’d see them tonight. At Don Antonio’s, your favourite Italian. You can pick me up at 7.30…and David, I’m relying on you. 7.30 okay?”

“What if I’ve got plans—”

The line had gone dead.

Who was he kidding anyway? Lucy knew he didn’t have plans. During semesters, the only thing he had going on was teaching a bunch of students about quantum technology. He focused on the report he had been writing with renewed zest—his day had just got better.

 



 

“For fuck’s sake!” Lucy stepped back from the door to her apartment.

David grinned. “What, honey?” He followed her into the small living room and did a three-sixty. “Do you like it?”

“You look bloody gorgeous,” she said, always surprised how David managed to look so feminine. While he was taller than most women, when he put on heels and the right clothes, he managed to exude a feminine mystique she found both tantalising and surprising.

“Ha! It takes balls to look this good,” he said, with a bravado that she knew was all show. He was as nervous as a teen on her first date.

“Very funny.” Lucy remarked, reaching up and slapping her hand across his shoulder before grabbing her coat. “We’re supposed to be finding my forever guy. Now, Diana, you’re going to distract every bloody sod in the restaurant!” She shot him a quick glance. “You’re okay with Diana, right?”

“Of course,” said David. “You look lovely too.”

He stared after her, wondering just where she got the leopard-skin miniskirt from, and why it seemed to be riding further and further towards her backside with every stride.

They arrived at the restaurant fifteen minutes early and sat in a quiet corner.

“You are glad to come, aren’t you?” Lucy asked, sipping her cocktail.

“We’ll see if that happens later, shall we?” He winked. “But, sure, of course I’m glad.” The nervousness in his voice betrayed his true anxiety. With the prospect of meeting a stranger, ‘Diana’ was a nervous little girl.

Lucy was about to tell him she planned to leave with her “date” for the evening, when a guy called out, “Hey, Lucy.”

The man was about five foot eight, with short brown hair and black rimmed glasses. David couldn’t help noticing how ordinary he looked. Even respectable. Not the dreary looking rock hippy she usually fell for. He smirked for a second, knowing how much Lucy hated his name-calling. But it never stopped him. As far as he was concerned all her hippy friends were as thick as pig shit. This guy, however, definitely looked different.

Standing next to Lucy’s date was a taller, blond-haired man, with large blue eyes. And he was staring right at David.

“Hi, Mitch, great to see you again!” said Lucy.

Hearing Lucy’s overly enthusiastic welcome for a guy she had only just met, put a momentary halt to his scrutiny. David watched her bounce up and tilt her cheek for a kiss.

What an odd couple, David thought, as the man’s neat brown hair came into contact with Lucy’s deliciously untameable mane of purple before Lucy’s next words grabbed his attention.

“And Luke, this is Diana.”

The tall man hesitated, his eyes fixed on David. The moment of silence was just long enough for David to thank God.

“Pleased to meet you, Diana.”

David realised Luke was as nervous about this as he was.

“I told you it would be fun,” Lucy whispered. Even though he was a real geek and too intelligent and self-opinionated for his own good, he was still Lucy’s best friend. Tonight he could be the professor of whatever the hell he wanted, but it didn’t change the fact he was a frightened little girl. And wasn’t this just the most divine she had ever seen him look?

Diana stood up just as the waiter came over to say their table was ready. Luke’s eyes roamed all over Diana’s body and he licked his lips in excitement.

“Pleased to meet you too, Luke,” said David, warming to his task.

There was no kiss, but ‘Diana’ didn’t mind. ‘She’ was expecting a lot more before tonight was over. I hope Lucy’s got plans to leave with Mitch tonight, he thought.

With titillating mutual consent, everyone just ate a main course and only drank one alcoholic drink. During the meal the guys announced they were construction workers working away from home.

“So how long are you staying in the area?” Diana asked, gazing at Luke.

“I leave tomorrow.”

Luke’s smouldering eyes were killing him. Together with his husky, deep voice, it was all too much to resist. The fact the guy would be nowhere to be seen tomorrow was just perfect too.

“Right, you two—” Lucy’s words stopped Diana’s lusting. “—we’re heading back to my place. I guess that’s okay with you?” She glanced at Diana before swivelling to get her bag from the back of the chair.

You know it’s great with me, thought Diana but she said, without conviction, “I thought we were going to hit a club or something.”

“Oh, we’ll be hitting something,” Lucy exclaimed, her eyes shining as she slapped Mitch’s lap, “but it won’t be a club. Let’s get the bill.”

Diana drained the last of the white wine in the glass, eyes fixed on Luke. She’d done this a hundred times in front of a mirror, and knew her rich brown eyes would be temptation personified under her long black lashes. Her velvet red nails strummed the table with seductive impatience before she delivered her piéce de resistance. With a growing confidence, she slipped her foot from her black kitten heel and lifted her long leg to rest on Luke’s lap.

“You wanna come back to my hotel?” Luke gasped, his eyes wide and his hand moving under the table to stroke Diana’s leg.

 



 

As soon as the door was closed, Diana began to peel Luke’s shirt off.

“Gotta get you out of this…big boy,” she warned him as her hand squeezed a very solid bicep. Oh, yes. The prospects for an exciting evening had well and truly dispelled all nerves.

Luke was helping her to tear his shirt off, ignoring the ping of a button whizzing across the dressing table. “So you’re a physicist?” Gasp! Pant! The jeans were already half way down to his ankles, and he prayed he wouldn’t fall arse over tit!

“Yeah,” Diana groaned, “You like a smart CD?”

“Fucking love it.” Luke was totally naked now, and hard as steel.

Diana grabbed his shaft. “This for me?”

“Any way you want it, babes.” Luke reached out and stroked her cheek. “Your skin’s so soft.”

“Wax, honey,” Diana moved her hand up and down the velvety shaft. She was hard too and weighing up her options. It was only one night so she wanted to make the most of it. Then she clenched her buttocks. Okay, now she knew what she wanted. “You quick to get it up again?” she asked, giving him a squeeze.

“When you’re this hot—” Luke smoothed his hands down the sides of Diana’s black satin dress. Her torso was slim and Luke’s fingers lingered when they reached the straps to her suspender belt. “—yeah, I’m quick.”

Diana kicked her kitten heels off and began to go down on her knees. But Luke pulled her up.

“Can I see you first?”

She gazed at him from beneath her long lashes and smiled. He was about to help remove her dress, but she wanted to do it alone. She was adept at unzipping, and the feel of the silky black fabric parting down her spine always left Diana feeling empowered. Besides, her fingers would brush over the lace of her cami top and panties, an added bonus. He’d better not be disappointed when I leave these on.

With her dress pooled at her feet, she gracefully stepped to the side and placed her hands on her hips, fingering the suspender belt with a tantalising enjoyment.

Luke stepped forward. His strong arms held Diana’s and he brushed her lips with his.

He tasted masculine and clean. She opened to welcome his tongue, letting it dance inside her mouth. Their bodies aligned perfectly, and the feel of his strong thighs pressing against the silk stockings hugging her skin left Diana heady with pleasure.

Finally, she slid to her knees and the aroma of his sex hit her full on. Her oral skills were on a par with her scientific ones. She knew what a man liked and she knew how to give great head. She was going to rock his universe when she released all his little “particles.” But no swallowing this time. Not a construction worker she would never see again.

After teasing his slit with her well-trained tongue, Diana steadily devoured him, inch by inch, cupping his balls when he groaned in ecstasy. With one last suck, she pulled off and his white stream shot over her chest, catching her bra strap.

“Oh, what a mess,” she scolded, teasing the man who was trying to stay on his feet. She ran her finger over the sticky trail. Then she placed her finger in his mouth and watched with erotic fascination as he licked it clean.

“That’s better,” she breathed, inhaling to accentuate the swelling of her chest.

“Wow,” sighed Luke. “I bet you’re a fucking good teacher.”

“Professor, actually.” She shot him a fervent look. “And I’m good at everything. I’ll just clean up here. Then I hope you’re ready to go again.”

His cry, “Oh, wow,” was only just audible as she made her way to the bathroom.

She studied her reflection for a few minutes while she washed her hands and indulged in coating them in slippery moisturiser. With an air of confidence, she sauntered back into the bedroom.

Luke turned to gaze at the ‘woman’ he had wanted to meet since Lucy had told him and Mitch about her very special friend last night. He never tried to hide his bisexuality and counted himself lucky to have been with a couple of men who cross-dressed. It added a whole different dimension to the bedroom and Luke got a huge kick when he was able to share erotic sex during these encounters. He had to admit, Diana was one of the most beautiful cross-dressers he had met. Her body was toned, not too muscular, and he remembered her soft skin. Her dark hair was short and flicked back, giving her a Kristen Stewart look. And those hypnotic eyes? Hell, he had to concentrate not to melt when they drilled into him.

“You look amazing.”

Diana gazed down and ran her fingers over the dark blue lace of her cami top. “I feel it, honey. Get covered up and come and find out for yourself.”

There was something wonderful about that first breach as the man entered her body. Luke eased her panties to the side to lubricate her sensitive anus, and already ripples of pleasure were running through her. She began to relax, waiting for those skilful fingers to be replaced by that hard, silky cock.

“Yes,” she gasped, as he inched inside her.

They rocked together, Luke’s hands pulling her hips to reach deep inside. He was big and she luxuriated in the fullness. Then came her scream as he nudged her prostate. Diana leaned back, moved her hand down and shot her seed all over the towel on the bed.

Luke tensed and she knew she had got him. His chest warmed her back and she waited a moment before pulling away. Lucy had been right. It had been fun.

 



 

Lucy entered David’s loft-house apartment at midnight.

“What a fab night,” she declared, throwing her jacket over the nearest chair before heading over to the huge sofa.

“Yes, honey, it was great.” David glanced over his shoulder with a girlish smirk and poured neat scotch into two tumblers.

Lucy took the glass and plopped herself down, careful not to spill her drink.

“You got what you wanted?” David asked, noticing there was a trace of lipstick on his glass as he sipped the drink.

“Yep. And I can tell you did.” Lucy’s eyes trailed down from David’s sexy lace top in pale violet, to his soft gray lounge pants. He looked satisfied. She curled her legs under her. “So, you got your man. Did he do manly things to you.”

David sat next to her. They both glanced down to his erection.

“What do you think? Were you happy with your bit of rough?” He reached behind and eased her sweater upward to reveal faint lines criss-crossing her back.

“He gave me just what I needed. He was delectable really.”

“Really? You’re pretty delectable yourself, Lucinda de Vilish.” He leaned in and kissed her.

“Okay. So we both got what we needed.” She twisted the lace of his cami top through her fingers. “How about we go get girly in your room. You can leave this on.”

David grabbed her hand and pulled her off the sofa. “Sounds like another good plan.”

They headed to the bedroom.

“Thanks for setting it up tonight. My turn to pick next time. What do you think about trying to find ourselves a couple of bankers…”

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Part 2 of this story can be found here! (Released two or three days after this one).

Find more episodes of The Dating Game HERE.

You can read more of Mollies wonderful stories here  .Be sure to comment on the story if you enjoyed it!  We hope to feature more of her writing in the near future.  FD.