When Larry Met Ashley (Crossdressing Story)

Thank you Cynthia for letting me help with this first part of Ashley's and Larry's Story :)

When Larry Met Ashely

It was a quiet car ride in the back of a taxi going through the noisy evening traffic.  Two people in the back seats were looking into each other's eyes trying to find words.  One individual with a red bob haircut just blushed and averted their eyes towards their purple dress.

Their peer, with short brunette hair and wearing a suit, was giving a comforting smile.  They cleared his throat to break the silence.  The one in the purple dress peered nervously at them.

“Ashley, thank you so much for joining me.  I was worried that this reservation would have been in vain since my issue happened.”  Ashley started to become calm hearing him say this.

“You’re welcome, Larry.  It’s a great opportunity to get to experience a fancy restaurant.  I can’t even think of the last time I’ve dressed this fancy.”  Ashly thinks for a moment how women’s clothes aren't their normal attire at all.

“I usually prefer tank tops and jeans.” Continued Ashly thought.

Ashly shifts nervously around for a moment. Being born male, she wonders if Larry can tell she’s not really a woman. She didn’t want to lead Larry up the garden path, but things just kinda happened and now it was too late to back out.

“I have to say, you’re just as beautiful as I told,” Larry says with a smile, causing Ashley to blush and smile back

“Thanks,” Ash replies. “Makes me happy to be informed that you were looking for a partner for this meal.”  Ashley then blushes, realizing they used the term ‘partner’.  #

Larry was confused by Ashley’s embarrassment.

“I appreciate the sentiment, hopefully, we don’t find this too awkward!”  Larry says giving a reassuring smile.

At that moment, Ashly let out a sigh of relief.

Larry was much more of a gentleman than she’d expected.

Crossdressers are used to men only wanting one thing! Especially crossdressers as passable as her, so it was refreshing. She couldn’t help but smile back at him.

The taxi driver interrupted their moment, surprising them both.

“Ok, we’re here!”  Declared the driver. Without moments, the cold night air was rushing up Ashly’s leg as Larry paid the driver. Crossing her arms, she waited patiently as Larry tipped the driver.

A smirk runs across her face as even more evidence of Larry being a good man appears in front of her eyes.

Getting into line, awkwardly next to each other, they notice other couples holding hands. Quickly glancing at each other, they quickly realize that they look out of place by not doing so.

As they became alerted that the line was moving again, without thinking about it, Ashley grabbed Larry’s hand as they advanced.  Once she realized what she did, she became nervous, and blood rushed to her cheeks.

“Thank goodness my hands are soft.”  She thought to herself as Larry remained quiet. His silence, however, only helped to deepen her worries. Why wasn’t he acknowledging her advances? Did he know? Had he sussed her secret!?

After the line advanced again, he surprised her by leaning over and whispering gently into her ear.

“Good idea, we don’t want to stick out,” he comments, as the warmth of his breath tickles her neck. Ashly couldn’t help by feel a little excited. She’d never experienced such a roller coaster of emotions.

“Thanks for not pulling away,” whispered Ashley, as she leaned her head against his shoulder.

As they made their way up the line, still holding hands, they both smiled like naughty schoolchildren.

Once they’d spoken to the waiter, they continued to hold hands as they are shown to their table.

“Any drinks?” The waiter asks as Ashly attempts to cover her chest with what little material her dress could offer.

“Yes,” Larry said confidently. “I will have a beer and the lady will have the house red.”

As the waiter nodded and scurried away, Ashly couldn’t help but feel a little impressed by Larry’s confidence. She’d never been on a date with a guy, so it was nice being looked after like that. It made her feel so very feminine.

“This place is amazing. I didn’t expect it to be this grandiose from the outside.” Stated Ashley admiring the interior.

“Yes, this is an amazing place! So happy you’re moving into the area.” Responded Larry.

“Speaking of which, what motivated you to move to town and use Allen’s apartment?”  Asked Larry.

Feeling the heat of embarrassment on her cheeks once more, Ashly seemed to struggle with coming up with an answer. Lucky for her the waiter came back and interrupted the conversation.

After ordering something she felt was fitting for a lady, Ashly had given it some thought and felt confident in answering his question without garnering any suspicion.

“Well, my brother is desiring to take his virtual job abroad and I took the opportunity to finally move out of my parent's place.”  Responded Ashley, as she ran her finger up and down the neck of her wine glass “It’s a lovely city, I just don’t know anyone here.”

“Makes sense,” Larry answers after taking a sip of his beer. “Speaking of Allen, did he show you around town before he left?  If not, I can show you around town sometime.”

Ashley averted her eyes for a moment then turned back to him then smiled and nodded.

“Is this your way of asking me out on another date?” Countered Ashley, smirking.

Larry responded with a grin.

“That obvious…am I?” Larry replies, with his grin getting wider. “I don’t know if this sounds crazy, but I feel like I’ve known you for years!”

Ashley giggled in response before leaning towards him.  “If only you knew the truth,” she thought, before wondering how to respond back.

She opened her mouth to start to say something but got interrupted by the waiter once more.

They ate quietly for a few minutes, with them both enjoying the culinary excellence placed in front of them.  Larry glanced over at Ashley gleefully eating, with the same lust in his eyes like a teenage boy sitting with his sweetheart.

After he finished his meal, he cleans his lips and patiently waits for Ashley to finish eating.

They exchange small talk while waiting for the bill.

Ashley was very curious and tried to peek at the total for their meals, but Larry hid the total.  He just gave a look of surprise, before using his debit card.

Once he left the table Larry looked around then got up and offered Ashley his assistance. Out stretching his arm, he offers his hand to her.

“Fancy going for a nighttime stroll my dear?” he asks, as Ashly looks up at him and smiles.

“Oh yeah,” declared Larry, as they exit the restaurant.  “You were about to say something as they brought out the food.  Do you remember what that was?”

Walking down the street with her hair blowing gently in the wind, Ashley had to think for a moment, then answered.

“I think you may have been asking me out on another date,” Ashley blushed, as she tucked her hair behind one ear. “I was hoping you’d bring that up again.”

“Oh yeah!” Larry responds with excitement, as they both walked up the block, holding hands. “Do you think we could?”

“I think you’ve earned it,” Ashly giggles as she playfully bumps into him, causing him to have to regain his balance.”

Larry laughs and chuckles to himself, as he brings his body back next to hers.

“What is it?” Ashly asks with curiosity, as he continues laughing. “What’s so funny?”

“Oh nothing…,” Larry smirks. “It’s just… I’d never thought someone like you would be interested in a guy like me.”

Ashly raises an eyebrow and leans in towards him

“Someone like me?” she asks

Larry coughs nervously before turning to her and smiling.

“Yeah,” he replies. “I know you’re not a normal woman and I love that about you.”

“Sorry!?” Ashly replies and swiftly pulls her hand away leaving Larry a little stunned.

They stop still in the street, staring at each other as other people walk around them. The night's air gently wafts Ashley’s hair and dress.

“Don’t worry Ashley,” Larry smiles, bringing his body closer to warm her shaking body. “I’m just saying I think you very a very special person!.”

Ashly’s face goes bright red as Larry embraces her with his larger warm body.

“Oh…..,” Ashley politely mutters, as a certain friend of Larry’s, pokes her stomach. “Thank you.”

“Do you want to head home?” Larry asks, stroking her red hair. “You look rather cold.”

“Please…..,” Ashley replies, looking up at Larry from the safety of his chest.

Reaching for his cell phone, Larry quickly calls an Uber. Handing Ashley his jacket, they wait patiently for the car to arrive.

Nerves had started getting to Ashley, as Larry puts his arms around her shoulders. She knew she should tell him the truth!

“L-Larry,” Ash anxiously mumbles. “I s-should really t-tell you something.”

Larry looks down at the worry on Ashley’s face. His heart rate increases as he worries about what she might have to say.

“Yes, my dear….?” He responds.

Just as Ashley builds up the courage to tell him the truth, the car arrives in front of them.

Swiftly taking Ashley’s hand, Larry takes no time in helping to get her shivering body into the car.

Having lost her nerve, Ashley slumps in her car seat and looks nervously out of the window. She really did like him and was now terrified to admit the truth.