The Dating Game – Part 2 – By Mollie Blake.

In the second part of Mollie’s story we continue to follow David, or ‘Diana’ and Lucy. Part 1 can be found here.

Wax Lyrical

David ripped the last length of wax from his leg, wincing only slightly and pressing his hand against the newly smoothed skin to relieve the sting.

A broad smile smile stretched across his face as he remembered his first encounter with a spatula of wax and strip of tape.


David shot bolt upright on the makeshift massage table. “Fucking hell! That hurt!”

There was no compassion from the sadist already applying another strip of hot wax—was Lucy sure it had to be this hot?—to the next stretch of hair on his leg.

Waxing makes all the difference.

This was a bad idea. Why didn’t he just stick to the black leggings? They felt good on him, beneath the grey chiffon dress.

“Come on, don’t be a wuss. Are you gonna’ man up to be the woman of your dreams?”

“Argh!” Wince, wince. Maybe he’d just have one leg done today, the other next week?

But Lucy’s torture was relentless. “Keep still, or I’ll have to go over that bit again.”

David could hear the taunting in her voice. For a petite five foot nothing slip of a lass she was a formidable character. It would make her day to keep him here all afternoon, subjected to burning pain, followed by everlasting smarting.

“My razor was just fine,” he yelled as he flung himself back on the table, closed his eyes and focused on the touch of the silk chemise against his skin. More importantly he tried to imagine what a nylon stocking would feel like on his super-smooth leg.

“I told you, this is the best way to get all the hairs out. You won’t get any regrowth for weeks and when you do, they’ll be a lot finer. Just think of this as ‘sex in the bank’ for the next three weeks.”

“I’m only going on one date,” he moaned, gritting his teeth ready for the next strip of hair to be ripped from his body. “Fuck! This had better be worth it.”

“Okay, that’s the fronts. Turnover.”

Half an hour later Lucy coated his freshly bare skin with a soothing cool gel. “Why don’t you go and put your stockings on while I make some mint tea. Then you can tell me how they feel.”

Finally he smiled. “Okay.”

Alone in his bedroom, David opened his favourite drawer. There was a neat array of lingerie with panties on one side and neatly folded cami tops on the other. A pair of brand new, fine nylon stockings lay at the front edge of the drawer next to a cream garter belt.

He stepped out of his joggers and fastened the belt over his black thong. The belt hugged his hips perfectly. Then came the part he had been waiting for. He withdrew the sheer nude stockings and unravelled them. Slowly curling them around his palm, he breathed deeply and was filled with a calmness which often eluded him.

“Right,” he said out loud, “let’s do this.”

Sitting on the edge of the bed, he stretched his leg out before him, toes pointed, as he began to ease the nylon over his foot. He stared as the smooth skin of his leg became encased in the feminine pantyhose. This felt so right. Keeping his eyes focused on the stocking he stood up and began to attach the top to his garter belt. There was no room for questions and self accusations of shame and guilt. The pleasure was too much. He glanced in the mirror. Wow, he thought, staring at his reflection. Yes, his feminine side was ready—ready for Diana’s first date with a woman.

It was early evening when he covered the short distance to the restaurant, and he was glad he had practiced walking in his kitten heels.

But when the waiter approached to ask if he had a reservation, David was panic stricken. Yet there was no stare, no pitiful look, and no sneer. The waiter simply said he would show her to the table, and announced that the other guest was already seated.

David started to breathe again, thanking God Diana didn’t stand out, and she wasn’t going to be stood up. But wait a minute—was he late?

He spotted Gwen on the far side of the restaurant and immediately called out, “Hi. Am I late?”

Suddenly all the diners turned to look at him. David turned crimson. But as they quickly resumed focus on their own culinary delights, he soon realised it was the number of decibels with which he had asked Gwen if he was late, that had attracted the attention of the other guests. Not the fact he was a man dressed as a woman. By the time he reached their table, he was trembling like a schoolgirl about to be reprimanded for wearing the wrong-coloured gym shorts.

“No, not at all,” said Gwen, her eyes shining, her voice quieter. “I was early. Your dress is beautiful, by the way. I love it.”

David stared at the older woman.

Gwen nodded to the chair beside her. “Why don’t you sit down. And you look like you need a drink.” She waved for the waiter’s attention.


Every cell in his body was beginning to regret coming on the date. But within minutes he remembered why he had agreed to meet Gwen for dinner. She was eloquent and confident, and had ordered a bottle of Sancerre, his favourite French white wine. Before long, David was feeding off her energy as he fed her enquiring mind with his theories for the thesis he was working on for his PhD. He pressed a hand against his thigh—just knowing the stocking was tight against his skin sent tingles up his spine.

But the real fireworks sparked a little later when it was Gwen’s hand touching his thigh, lingering as it rested on top of the garter. His eyes must have been like saucers.

David had given pleasure to several young women during his twenty-five years but Diana had always shied away. She was a private person. Just for David. After all, he had only known her a couple of years. During that time, the person Diana was most grateful to, was Lucy. From the moment David met her, Lucy never judged him. As their friendship deepened Lucy became Diana’s best friend too.

“Shall we go back to my place?” Gwen asked at the end of a very enjoyable meal.

Before David knew it, he was being led into her bedroom.

“It’s okay to be nervous. I’m a little nervous too,” Gwen confessed.

“I just feel a little…I don’t know…like I want this too much,” he muttered.

“Ha, no pressure then.”

David watched Gwen’s broad smile brighten her face. She looked serene and sensual. His nerves left him feeling agitated and clumsy. He’d already stumbled on his heels as they walked to Gwen’s house, and he had been grateful that Gwen pretended she hadn’t noticed. Then, when he’d gone to the bathroom he’d run his fingers inside the stocking to touch his still-ultra-smooth skin after Lucy’s brutal waxing. And hadn’t he nearly snagged the nylon on his watch strap? All he needed was a bloody ladder up his leg to look like a right slut! Calm the fuck down or you’re gonna’ ruin it!

Remembering his near mishaps, David giggled.

“That’s better,” said Gwen, “looks like you’re relaxing now. Tell me what’s tickled you.”

“I just thought what a slut I’d look if I laddered my stocking.”

“Ha, ha.” Gwen laughed with him. “The challenges of being a woman. Clothing, make-up, looking after our skin. Welcome to the dark side.”

“The dark side?”

“There’s always a dark side. But I guess you know by now, femininity can be worth working for.”

Gwen was standing so close to him, he could smell her perfume. It was sweet with an undertone of orange blossom. Hadn’t he read somewhere that that was an aphrodisiac? He inhaled, savouring the tempting fragrance.

“I really like you, Diana.”

For the briefest of moments, he froze. Gwen hadn’t called him Diana all evening. Something had changed. Was he really ready for this?

When he felt her hand pull at the back of the dress and begin to lower the zip, he just knew he had to be. The little girl in him wasn’t going to run and hide. She was going to let the woman in him take over.

Gwen’s warm hands scorched his spine as her fingers worked their way down before pulling the straps to his dress over his shoulders. He wiggled a little to let the dress fall to the floor.

“You have good taste,” Gwen gasped, ghosting her hands over his deep purple laced top.

David thanked Lucy for helping him to choose his lingerie for this date. When Gwen rested her head on his chest and moaned, his anxiety was cast aside. They both needed this.

The information he had gathered from the internet on cross-dressing and learning to accept and be accepted, hadn’t been full of bullshit when it informed him some women loved to be with cross-dressers. And Lucy hadn’t lied to him when she said it was true.

Gwen was the evidence he needed. He died and went to heaven when her hand moved lower, taking hold of its goal encased in a large purple thong.

“Love this,” she whispered.

The feel of her touching his hard shaft left him gasping for breath and eager to move to the next level. But there was something he was forgetting. For the first time that evening he took charge when he held her chin up and leaned down for a long kiss.

But when it came to the sex, he was happy for Gwen to lead. Or rather Diana was—this was her first time.

Pushed onto the bed, he watched as Gwen revealed her body. She was giving herself to the virgin inside him. David couldn’t take his eyes off her. His anxiety had become eager anticipation. He wallowed in the feel of the garter tightening around his hips, and the soft nylon hugging his legs.

Then Gwen was climbing on to the bed next to him, in all her naked glory. She slid her hand under the strap of Diana’s cami-top. “Do you want to leave these on?”

“Yes, please.” His voice was hushed. He wanted to move to the next level but he wanted this moment to last forever. Her touch was like warm oil, her fingers leaving a trace of their heat over every part of him. He was dreamy and excited at the same time.

Gwen leaned over him, gently easing him on to his back. Her lips began to cover his, her hands roaming over lace and skin indiscriminately. It was slow and divine. When she began to lick the flesh between his top and the thong, he thought he was going to explode. But he didn’t need to panic.

He bucked his hips as soft hands eased the thong off before encasing his penis, sliding up and down. Gwen’s ministrations continued as her lips sought his once more. He invited her tongue in to explore and share tastes. Pleasure began to well up from deep inside him. Gwen’s soft moans soared around his head, encouraging him to release, sensing it would empower her. All he wanted to do in that moment was please her, because she was fucking causing a cosmic explosion of erotic delight in him.

His seed coated her hand and he watched, mesmerised, as she lapped it from her fingers, before placing them in his mouth to take up the last remaining drops.

When he fell back to earth, his hands roamed her breasts, luxuriating in their fullness. His tongue teased her nipples before making its way down her body. As he raised her knees, he heard her soft cry.

“Oh yes, Diana.”

He gazed at her feminine mound. The smell of her sex combined with the closeness of the stockings to his skin, ignited his desire to taste her and bring her to orgasm. His tongue was light and patient, her clitoris delicious.

All too soon it would be over for both of them, and David was determined to burn this memory into Diana’s mind forever, to encapsulate it for his enjoyment when it would only be a memory and his search for another Gwen would prove futile…


That memory was from a long time ago, and he had been lucky to find other “Gwens.”

“Right, that’s me done,” David declared as he cast the wax strip into the rubbish bin. He glanced at his watch. Diana was going to be late for her date with Amanda if she didn’t get a move on.

Part 3 can be found HERE.

You can find more of Mollie’s stories at

One Reply to “The Dating Game – Part 2 – By Mollie Blake.”

  1. Another beautifully written piece. I find myself reading every chance I can. Diana is the one many of us only dream of being. Can’t wait any longer, part 3 awaits.

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