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.
I awkwardly knelt down, and the hood was removed from my head. I blinked at the bright light and looked around at my surroundings. I appeared to be in an unfinished basement, kneeling on a concrete floor. The room was filled with what looked like equipment from a medieval dungeon: there were various benches and racks with restraints on them, a couple of large cages, plus two tables full of paddles, crops, and other disciplinary devices, plus assorted other sex toys like dildos, plugs and several other things I could only guess at their uses.
"Do you like what you see?" Lindsay asked, with an evil little laugh. "Don't worry; you'll get to try out most everything you see in here. You're going to be our bitch, our slave, our plaything, for the next day or so. If you want to get through this with a minimum of pain, you will follow and obey these rules.
"You will not speak unless spoken to and, unless otherwise directed, the only acceptable answers are 'Yes, Mistress' and 'No, Mistress'. Failure to respond properly, or speaking out of turn, and you'll be punished.
"You will obey our instructions and commands completely and without hesitation. Failure to do so will result in punishment.
"If you resist in any way, you will be punished.
"If you try to escape, well, I think you know what will happen," she said, giving my groin a light kick. "Do you understand?"
I nodded my head and was immediately slapped across the face. "The correct response is 'Yes, Mistress'!" Lindsay yelled in my face. "Do you understand these rules?"
I tried to say "Yes, Mistress" through the ball gag, but it didn't sound anything like that. However, it must have been enough, as she said, "Good," loosened the ball gag, and removed it from my mouth so that it dangled around my neck. At the same time, Kathleen cut the restraints around my wrists.
"Here, take these," Lindsay said, handing me two blue pills and a small paper cup of water. "There's one more rule," she continued. "You are not to cum without our explicit permission - which we will probably never give. Your time here is all about our entertainment and pleasure - not yours. These are to keep it interesting," she said with a laugh. I had to assume they were Viagra, and I quickly swallowed them and finished the cup of water.
"Now stand up and take off all your clothes, slave. You won't need them while you're here." I quickly stood up and started undressing, placing my clothes in a pile on the floor. Lindsay came over to me and gave my flaccid penis a swat. "Such a tiny dick," she laughed. "No wonder you were alone at the bar. I hope it gets bigger when it's hard - not that we'll have much use for it."
Meanwhile, Kathleen had gathered up my clothes and put them in a trunk, removing my wallet first. She took out all the cash - about $150 - and also took out my driver's license and a business card. Noting the look of alarm on my face, Lindsay said, "Don't worry, you'll get your license back at the end. It's just a little insurance that you don't try to escape. Plus, we'll copy down your information, in case we're ever in Omaha and want to say 'hi.' The cash is for room and board because, well, you are going to be enjoying our hospitality for the next day and a half. That's only fair, right slave?"
I was totally screwed. There didn't seem anyway out of this but to get through this ordeal by doing what they said. I murmured, "Yes, Mistress" and looked down at the floor at my feet.
"Good," Lindsay said. "Now, get back down on your knees."
I knelt back down on the cold, hard concrete floor while Lindsay turned away from me, raised her skirt, slid her tiny black thong down to her feet, and tossed them and her shoes away from her. "Lick my ass, bitch," she commanded. "Your tongue is going to be very busy while you are here, so we'd better see what kind of training you'll need."
With that, she spread her cheeks with her hands and backed up towards my face. With only a slight hesitation I leaned forward and placed my hands on her legs to steady myself. "Hands behind your back, bitch!" she ordered. "Kathleen, cuff his hands. Now, start licking."
As Kathleen put handcuffs on me, I reached out with my tongue and started licking in a circular motion around her pungent rosebud. "Oooh... That feels really good," sighed Lindsay. "You're a good ass-kissing bitch. You must make up for your tiny dick with a talented tongue. That will make your time with us easier. The better you perform, the easier it is on you."
Meanwhile, Kathleen had knelt down next to me and started slowly stroking my cock. It had already started stiffening at the sight of Lindsay's naked, tanned ass, in spite of my humiliation. "Oh, that's much better," Kathleen said, as I got completely erect. I had I believe an average penis in length, just over six inches, but above average in girth. "Maybe your dick isn't completely useless. Remember the rule, though: no cumming without permission."
I continued licking around Lindsay's asshole, starting to flick my tongue across her tight hole. Lindsay moaned, removed one hand from her ass, and started slowly rubbing and fingering her pussy. "Oh, God, yes! You're such a good ass-licker, bitch," she sighed.
After no more than a couple of minutes of that, Lindsay said, "Now tongue-fuck my ass, bitch! Get your tongue in there as deep as you can." I started, but with now only one hand spreading her cheeks, I couldn't get all that deep.
"Kathleen, come spread my cheeks. I want to feel our bitch's tongue deep inside my ass." Kathleen stopped stroking my dick - thank God, as I didn't know how much more I could take - and came over to spread Lindsay's cheeks apart. Lindsay bent over even more, bracing herself with her other hand on her thigh and pushed back against my face as I thrust my tongue in and out of her asshole. She was rubbing herself furiously now and moaning loudly. In less than a minute of this, I felt her body stiffen, she let out a cry, and then pulled away.
"Wow, that was good!" She exclaimed. "It's been far too long. Kathleen, un-cuff our little bitch and take him over to the bench, restrain him, and put his gag back in."
Kathleen led me over to a narrow, padded bench, pushed me over it, and fastened my hands and feet to it. She also fastened a belt across my back, limiting my ability to move much at all. My legs were spread wide and my still hard cock hung down below the edge of the bench. My head hung over the other edge. Kathleen placed the ball gag back in my mouth and tightened it back up.
Lindsay had now taken off her dress and put on a leather corset that highlighted her curves and pushed her breasts up and together, making them look even bigger than they were. She came around to where my head is. I could see that her pussy was completely bald, and glistened from her orgasm.
"I bet you're wondering why we're doing this," Lindsay asked rhetorically. "Obviously, I can get any man I want any way I want - and that was fun, for a while. I could turn even the hardest, most masculine man into my slave for a chance to fuck my pussy. The problem is, they were willing slaves. I just didn't get the same thrill as I do now when I kidnap a man and rape him. Besides, with the willing ones, there were always expectations. I couldn't stand hearing them whine about fulfilling their needs. With bitches like you, you just want to get out of here in one piece and are willing to do just about anything to ensure that. I don't give a shit about what you want, and you're never going to ask for it.
"Kathleen, here, well, we've been friends forever. She used to marvel at how I would take men and bend them to my will. After a while, I let her join in. It was only natural that she'd become part of it when I took it to the next level.
"Now, next you need to learn what punishment is like so you understand why you want to avoid it. Remember, you'll be punished if you don't follow our rules, if you disobey or are slow to follow orders, or even if we just feel like it. Besides, I still need to punish you for not saying 'Yes, Mistress' when I asked if you understood our rules."
With that, she walked around and gave me a hard slap on the ass with her hand. "I'm going to warm you up, and ease you into your punishment," she said with another smack. "You won't get this kindness with future punishments."
She continued to smack my bare ass with her hand, alternating cheeks, for a good 20 or so slaps. While they stung, they certainly weren't unbearable. "Kathleen, it's time for the paddle," the blonde amazon said. "Show it to him first."
Kathleen had now taken off her dress and was completely nude. Unlike Lindsay, she had a trimmed, fire-red pussy. In her right hand she had a black, wood paddle shaped like a Ping-Pong paddle, but with holes in it. She waved it around in front of my face with a big grin on her face for few seconds, before handing it to Lindsay.
"This is going to hurt a bit more," Lindsay said, as she swung it hard against my backside. I jumped and grunted with pain, but after a few more I started getting used to it. That caused her to start swinging harder, sending shockwaves of pain through my ass.
"It looks like he's getting soft," Lindsay remarked between strikes. "You'd better get down there and get him hard again. I'd hate to think he's not enjoying his time here." Kathleen crawled under the bench and started slowly stoking my cock again, quickly getting me hard.
Lindsay stopped for a minute, and then walked in front of me holding a riding crop. "This is your next experience, slave. I hope you enjoy it as much as I will."
Next I knew I felt a *crack* across my ass. I jumped and screamed as much as I could through the gag. I had never felt pain like this before and tears started streaming down my face. Despite the pain and humiliation, I was getting closer and closer to cumming. Kathleen must have sensed this, as she slowed down for a while.
After 20 or more strokes, Lindsay finally stopped and came around and faced me. She bent over and in a low voice said, "This is just a taste of what your punishment can be, bitch. I still have floggers, whips and canes we can try out. Do you understand, bitch?"
I nodded and tried to say "Yes, Mistress," through the gag and through my tears.
"Are you ready for me to take this gag out - remembering the instructions we gave you earlier?"
"Yes, Mistress," was my muffled reply.
"Good. We're ready to have some fun with you. If we have to interrupt our fun and punish you again, I promise it will be much worse," she says as she removes the gag.
As the gag comes out, Kathleen comes around to the front of me. She was now wearing a strap-on dildo about the size and girth of my own cock. "I picked this one out just for you," she giggled. "You had better start sucking and lubing this up, as that's the only lubricant you're going to get before this goes up your ass."
I start frantically sucking and licking her strap-on trying to get as much spit on it as possible. After a short while she starts thrusting in and out of my mouth, grabbing the back of my head and forcing it down on her cock more and more so I almost gag on it.
Satisfied that it's ready, she pulls away and moves around behind me. Thankfully, she started preparing me with lubricant, sliding a finger coated in lube in and around in my ass - despite the earlier threat. Lindsay is now in front of me, wearing a still larger dildo than the one Kathleen had on. "Here's how fun time is going to work tonight," she says. "We're going to take turns fucking you in the ass. While you are getting fucked, you will be worshiping our asses and pussies. The better you are, the sooner we'll be satisfied, and the sooner you'll be done for the night."
With that, Kathleen started slowly sliding her cock into my ass. I gasped in pain and humiliation, at which point Lindsay grabbed my head and thrust the tip of her cock into my mouth and said, "Suck it, bitch!"
Kathleen kept slowly easing her fake dick in while I sucked on the head of Lindsay's prick. When she only had an inch or more left, she gave one quick thrust and she was all the way in. At the same time, Lindsay pushed my head down hard on her cock, causing me to gag. My ass was still on fire from the beating and now it felt like it was being split in two, while Lindsay was shoving my head up and down on her big, black dick.
Kathleen slowly started rocking her cock in and out of my ass, gradually picking up tempo, while Lindsay matched the tempo with my head. "Do you like my dick in your tight ass, little boy?" Kathleen asked. "This is what it felt like for any women you've fucked in the ass. I bet you'll never do that again!"
This continued for five or so minutes, with Kathleen occasionally adding to my pain by smacking my ass with what felt like a wooden spoon. Lindsay then said, "It's my turn!" and pulled her cock out of my mouth.
Kathleen also stopped, removed her strap-on, and came around to the front. "You haven't proven yourself to me yet," she said, "so you're going to worship my ass first. She turned away from me, bent over, spread her lily-white cheeks, and backed her ass into my face. I quickly started licking in and around her hole, while she removed one hand from her cheeks and started rubbing her pussy.
Lindsay, meanwhile, had lubed up her strap-on, applied more lube to me, and started slowly working her dick into me. I thought Kathleen's was bad! I felt like I was being ripped apart as she guided it in and out of my ass. "How do you like *my* dick, bitch?" Lindsay exclaimed, slowing thrusting faster and faster.
Kathleen started moaning louder and louder as she pushed her ass against my face and I darted my tongue in and out of her asshole. Finally, she let out a scream and pulled away. Lindsay slowed down and stopped as well, taking off her strap-on and coming around to the front to have her pussy worshiped, while Kathleen put her strap-on back on and started fucking me with it.
I lost track of how many times they switched, as my whole world was now their pussies and asses and my own bruised and battered ass. Each time it seemed like it took longer for them to climax. Finally, they both had enough and collapsed into chairs. We were all sweaty, exhausted piles of flesh at that point.
"Well, slave, I think that's enough for tonight," Lindsay said as she unfastened my hands and cuffed them behind my back. "We all need some sleep so we can get started in good time tomorrow!"