I was in Chicago attending a week-long training for work. It ended Friday afternoon but, since I had to go to a conference in Denver that next Monday, I was staying in Chicago until Sunday afternoon. I didn't really know anyone in town, so I just ended up visiting a few different bars near my hotel Friday evening. I wasn't looking to meet anyone, so I kept to myself, sitting at the bar or alone at a table.
After probably a few too many, I decided to head back to my hotel. I stumbled out of the last bar and started slowly walking back. I wasn't really paying too close attention to my surroundings, so I must have jumped a bit when I heard a female voice behind me ask, "Excuse me, can you help us out?"
I turned around to see two young women behind me. One was probably 5'11", blonde hair, blue eyes, a golden tan with large breasts and a narrow waist. She was stunningly beautiful, perhaps one of the most beautiful women I had ever seen in person. The other was only about 5'4", brownish red hair, blue-green eyes, pale skin, very small tits and a skinny body. It was obvious she was very fit, probably a runner or cyclist. She was attractive in her own right, but was so overshadowed by her companion that it almost made her look plain. Both appeared to be in their mid-twenties, and were wearing tight cocktail dresses and stiletto heels, with light jackets tossed over their right arms so that their hands were not visible.
"Well? Can you?" asked the blonde, looking amused. She knew she was gorgeous and was clearly used to using her beauty to get what whatever she wanted.
My mouth must have dropped open when I turned around, as I shook my head to clear my thoughts and it snapped shut. "I, uh, I'm not from here," I stammered.
"Oh?" the blonde remarked, smiling slightly. "That's not really what I asked. Can you help us out?"
"I, uh, don't understand. What do you want?"
"Our car is just down this street, and we are having trouble starting it. Can you take a look at it?" She pointed down a darkened street right next to where they stopped me. Fifty yards or so down the street I could just make out a car.
"I don't really know much about cars. I don't think I'd be of much help," I replied.
"Please? It will just take a second." This time, it was the redhead that spoke.
"Um...okay," I said, not wanting to disappoint two beautiful women who were asking for my help. We started walking down the side street. They made some small talk with me, asking where I was from, why I was here, and how long I was staying. I answered them truthfully, not sensing any reason not to.
"We've got tools and a flashlight in the trunk," the redhead said. "It should be unlocked."
"Okay," I said and took a couple of steps ahead of them towards the trunk.
"That's far enough," said the blonde in a stern voice. I turned around to see both of them pointing Tasers at me that must have been concealed under their jackets.
"What? What is this? What are you doing?" I demanded.
"Quiet!" ordered the blonde. "If you make any more noise, I won't hesitate to shoot you. Kathleen," she said, turning to the redhead, "hand me your Taser, open the trunk, and get him ready."
After turning her Taser over to the blonde, Kathleen stepped forward, opened the trunk, and pulled a few things out of it. "Please," I said, "You don't have to do this."
Kathleen quickly spun around and in one fluid motion punched me in the groin. As I doubled over in pain she hissed, "What did she just say? Another word and you're done. Now, stand back up, face Lindsay, and put your hands behind your back."
After a moment, I regained my composure and complied, facing Lindsay. She still had both Tasers pointed at me, and had an evil-looking grin on her face. Clearly she was enjoying what was happening. I felt Kathleen grab my hands, hold them together, and tie them tightly using a zip tie.
"Put your feet together," she said, doing the same thing with my feet. "Open your mouth," she ordered, then shoved a ball-gag into my mouth and fastened it behind my head. "Get into the trunk," she ordered, turning me towards the trunk and giving me a shove. I sat down on the edge of the trunk, leaned down into it, and they lifted my legs and pushed them into the trunk. The trunk slammed shut, and I was in total darkness.
After driving for what seemed an eternity but was probably only about fifteen minutes, the car slowed to a stop after pulling into what sounded like a garage or some other enclosed space.
Shortly after the car was turned off and the garage's overhead door finished closing, the trunk opened and I was staring up at Lindsay, who was holding a black hood. She quickly shoved it over my head, and I was in darkness again.
"This is going to be a long, painful and humiliating time for you," Lindsay said, "But how painful depends largely on you. Follow our instructions and obey our orders, and you'll be released largely unharmed early Sunday morning in plenty of time to catch your flight. Disobey or disregard or orders, or resist or struggle in any way and you will be punished. Try to escape and, well, I hope you enjoyed having these," she said, giving my balls a squeeze through my slacks.
They helped me out of the trunk, cut the restraints around my legs, and led me through a door and down a set of stairs. "Get on your knees," Lindsay commanded.