The Bet Ch. 03

We arrived in New York, and after gathering our luggage, we hailed a cab, and made our way into the city. Sarah had booked us a room at nice boutique hotel in mid-town. When we got into the room, Sarah ordered me to strip down to my panties. I stood in the middle of the room, in front of the king sized bed as she walked slowly around me, looking me over. She appraised me like I was just an object, running her fingers along my body lightly. Touching me here, then there.

"OK pantyboy, time to trade up again," she announced. Standing behind me, she wrapped her arms around me, sliding her hands into my panties and pushed them down. The panties fell to the floor around my ankles. My cock began to rise to attention. "Spread your legs, and lean on the dresser," Sarah directed. I did as she told me, and looked at myself in the mirror mounted on the wall above the dresser. I could see my cock stiffening, and Sarah reaching into her carry-on bag. As I expected, she pulled out a small bottle of lube and another black plug. This one looked even larger then the last. It looked like it might be 2 inches at its widest. I felt like my eyes were about as large as I stared at the monster.

Sarah saw me staring and smirked at me. "Don't worry pantyboy, this won't hurt a bit. You're all warmed up already, this is just a little larger than the one you're wearing now. This will get you ready for the main event tonight." This was the second time she had alluded to a something greater later tonight. I wasn't sure I could handle anything larger, but her words brought images of Sarah pulling a giant plug out of her large roller bag.

My attention was brought back to the now as I felt Sarah pulling on the plug in my ass. This time, it seemed to slide out rather easily. Maybe she was right, I was getting used to this now. It had been almost 4 hours since she had inserted the first plug back in the parking garage. I felt her adding more lube to my ass. I couldn't be sure, but I think she slid two or three fingers into me, spreading the lube. It felt wonderful, and I let out a moan before I realized that I was doing it.

"Ooh, you like this pantyboy?"

"Yes, Mistress. I didn't know that it could feel this good."

"This is just the beginning...just the beginning."

And with that, I felt the now familiar feeling of the plug pushing into me. This one was larger. Despite what she had said, it wasn't too painful, but it did stretch me wider than I thought possible. It took a little coaxing, but the plug was soon deep inside my ass. Sarah told me we were going to dinner and a show. Then, we'd return here for the "climax" of our evening. With that, she giggled just a bit, not a girlish giggle, but more a fiendish giggle that had me a bit concerned.

"Give me a moment to get out what you'll be wearing tonight, pantyboy," Sarah said as she unzipped her suitcase. She tossed onto the bed a small plastic wrapped package, another pair of panties, this time black with some lace, and a matching garter. Next came a black camisole, its silky fabric shimmered in the light as she held it up to show me. I picked up the package and saw that they were a pair of sheer black stockings with lace tops. I fumbled a bit with the package. My hands were not cooperating fully more out of excitement than fear I realized. I sat on the edge of the bed, and managed to get the stockings on. They had a stretchy rubber lining at the tops to hold them up without the garter, but I reached for it anyway. The garter took a little more time to figure out, but I found that it fit rather nicely around my hips. After I got them attached to the stockings, I looked up and saw myself in the mirror. My legs looked more feminine than I would have expected encased in the sheer black stockings. I stepped into the panties, and as I pulled them on, I felt the smoothness of the stockings on my legs.

"Good pantyboy. I'm glad you understood the garter went before the panties. That's important."

I looked up and realized that while I had been focused on the stockings and garter, Sarah had completely changed her clothing. She had on a short black dress that barely covered the tops of her own thigh high stockings. The neckline was a steep "V" that reached almost to her navel. It was obvious that she wore no bra.

"Don't just stand there, pantyboy. Keep getting dressed. We've got a reservation to make," she ordered sternly.

The camisole fell loosely over my chest. The silky fabric felt exquisite against my skin. I quickly stepped into my slacks, and then went to my bag to get a new shirt. I found what I was looking for — a dark blue oxford — plenty dark enough to hide the camisole. As we left the hotel, I could feel eyes following us through the lobby. I had to convince myself that they were following Sarah, her sexy dress and high heels accentuated her toned legs and perfect figure. I could feel the stockings and the camisole with every step I took. The plug was no less noticeable as I focused on walking as normally as I could.

We took a cab to the restaurant. Sarah had found a nice dimly lit restaurant that was actually below street level. You could see people's feet walking by through the small windows mounted high up on the walls. We were seated in a booth, away from the traffic of the wait staff. Sarah had clearly prepared for our arrival as the hostess handed her a menu, and ignored me completely. She scanned the menu quickly, then placed it on the corner of the table and waited for the waitress to arrive.

When she did arrive, Sarah ordered for both of us. Throughout dinner and later the show, Sarah continued to take charge as if it was totally normal. Her demeanor was one of control and confidence that had me feeling less and less her companion, and more and more her pet. She didn't order me to "heel" or "sit" like I was literally a dog, but the way in which she did direct my actions, she may as well have done so. I found myself looking to her for direction, and at the same time, trying to anticipate her needs and wants.

I was constantly reminded that our evening out was just the beginning of more to come. Each time I shifted in my seat, or had to walk anywhere, the plug reminded me that this was no normal night on the town. The silky feel of the stockings and camisole beneath my clothes along with the plug had me hard almost the entire time. I don't even remember much of the show, not that I ever really enjoyed them anyway. Throughout the show, Sarah had her hand resting in my lap, fingers teasing my inner thigh and sometimes tracing the outline of my hard cock.

After the show, we returned to the hotel. The cab ride was uneventful except for the fact that Sarah was whispering into my ear. "Are you ready for me, pantyboy? You've been good tonight, keep it up, and you'll earn a reward."