Cynthia looked into the mirror before leaving her home, adjusted her hat, and added just a touch more lipstick. She knew she looked good, classic even. She adored the more traditional styles, feeling both feminine and powerful when wearing clothing that made her feel sexy yet modest as well. She particularly preferred an updated version of the 1950s. Gloves, hat, stockings held in place with a garter belt, pumps, girdles, bullet bras.

Luckily, Mr. Fender also preferred this style. He himself treated her with the utmost respect and manners at all times, even when she was willingly draped over his lap. Today, she was meeting him for coffee before their trip to the coast via a private room on the train.

Yes, taking a train took longer, but the world, in her opinion, already moved too quickly. The longer trip and the private room allowed for all kinds of wonderful activities that a plane or car would prevent.

Walking out to the awaiting car, she felt a snap. She lifted the hem of her dress and re-attached her silk stocking to it’s holder. Her Lyft driver, she noticed, saw this when he got out to open the door for her.

“Ma’am,” he said politely.

“Thank you,” she responded.

Silence ensued on the drive to the coffee shop, for which she was grateful. She had no interest in anyone safe Mr. Fender, although she did appreciate good manners. The driver safely delivered her to her destination, again opened her door for her, and wished her good afternoon.

“Any difficulty?” Mr. Fender enquired as he stood upon her arrival.

“None at all. The driver noticed a slight faux pas on my part when I adjusted my stocking, but he behaved like a gentleman should. He deserves a tip, I’d say,” she responded.

Mr. Fender chuckled, pulled out his phone, and gave the driver a healthy tip. Cynthia ordered two plain black coffees. Fancy really wasn’t their style.

“So, shall we go over the groundwork for the trip?” Mr. Fender asked.

“Certainly,” Cynthia responded once she’s swallowed her sip of rich coffee. “Last time we traveled, you required I keep my legs covered at all times unless we were at the beach or pool. Would you like to reinstate that?”

“I would.”

Cynthia retrieved a leather bound notebook from her purse and wrote down the requirement.

“Right. Underpants?”

“Certainly not.”

She scribbled again then took another sip of coffee.

“I also believe that your outer clothing is best suited for just that – outings.”

“Yes, Mr. Fender.”

He glanced at his watch and signaled the server. It was time to go to the train station.

Once they boarded, their luggage stowed, and the porter had shown them to their private room, Mr. Fender ordered dinner to be served in their room that evening.

“Time enough to be social tomorrow,” he stated as he sat on one of the bench seats that would later be converted into their queen sized bed. He watched as Cynthia removed her dress and hug it up on a hood on the back of the door. She sat across from him, wearing her bra, girdle, stockings, and pumps.

“You are beautiful,” he complimented.

“Even at my age?” she asked playfully.

“Especially at your age,” he answered. “Play with yourself.”

Cynthia spread her legs and obeyed, leaning her head back and closing her eyes.

“No. Keep your eyes on me.”

She snapped her head upright and her eyes open. Soon, she was panting. She opened her mouth, sighed “Ooooohhhhh” and came, her body trembling, her fingers dripping with her own honey.

Mr. Fender smiled at her, and said, “Absolutely stunning, Cynthia. Too bad you didn’t wait for permission. You also allowed the driver to see more of your legs than I would approve of, didn’t you?”

She bit her lip while he rummaged through his luggage. He turned around, handed her two round discs, and sat back down. Sighing, she placed the discs inside her bra cups, wincing as the rounded spikes pressed into her skin.

“Uncomfortable?”

“Very, Sir.”

“Painful?”

“Not at all.”

Just then, the porter knocked on the door announcing their dinner had arrived. Cynthia sat still, dutifully watching the passing scenery as the porter arranged their food on the small table, popped open a bottle of wine, and wished them both a good evening.

“Does it excite you, Cynthia, to be in your underclothes when others are around?” Mr. Fender asked as he cut through his medium rare steak?”

“It does, Mr. Fender. It also humiliates me, which is exactly what you want, isn’t it?”

He pointed his fork at her and said, “You know me well, Cynthia.”

They finished their meal then rang for the porter to come take the dinner things away, bring them each a glass of cognac, and to arrange the bench seats into the bed. Once that was accomplished, Cynthia helped Mr. Fender undress before he did the same for her.

“Oh my,” he tusked, “those little spikes certainly did leave a mark, didn’t they?”

“Yes,” she answered breathily, lying back on the bed.

Gently, Mr. Fender kissed the entirety of each of her breasts, soothing the discomfort, before suckling each nipple and fingering her wet pussy.

“Please,” she murmured.

He lifted his head and said, “Yes. But be silent.”

She bit her lip and trembled, falling into her orgasm as his fingers worked their magic. Before her pleasure ended, he was on top of her, his cock replacing his strong fingers. She scratched his back with her pointed, red nails, leaving welts but not breaking the skin. Her legs wrapped around his waist, her soul traveling faster than the train they rode. When he allowed himself the ultimate pleasure, releasing his cum inside of her, she let out a long breath, and moaned quietly.

He collapsed onto his side, pulling her close to his body.

“Mr. Fender, I do believe this trip is going to be one to remember,” she murmured

“I believe you’re correct. Here, enjoy your cognac and view. It will help you sleep. I have plans for tomorrow, and you will need your rest.”

“Excellent,” she responded then sipped her drink, reclining in his arms, watching the world go my, and imagining what tomorrow would bring.

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