Debbie - The Man in the Shadows

"That's her." said the man in the shadows, as a gorgeous woman opened the door, exhaling a thick cloud of cigarette smoke before walking into the bar. "She usually comes in on Thursdays looking for a quick hookup."

"Damn, she's hot!" said the other man. He looked her over. Long curly red hair that went halfway down her back, and wearing a very revealing tight yellow t-shirt, with no bra on. Her tits weren't too big, nor too small. They looked perfect. She had on blue jean shorts that looked like they were painted on, and 3" black high heels. He looked back at the other man and asked "You sure you want me to go through with this? She might not even go for me." and turned back to look at her again as she found a stool at the bar, and sat.

The man in the shadows looked at him and said "I'm paying you well. You better make sure she goes for you. You're a good-looking man, but you need to make your move quick. She always finds someone, and never leaves alone. She usually comes in, and within minutes picks someone up and leaves. She can't go more than 15 minutes without a cigarette, so I know she won't be here long. I suggest you get over there now. When I see you leaving with her, I'll slip out the back, and meet you at the place."

The other man nodded, and made his way over to woman who just sat down at the bar.

He walked up to her and asked "May I buy you a drink?" She looked him up and down, and liked what she saw. He looked to be around 35. He stood about 5'11" with shoulder-length black hair. He had a short mustache and goatee, and piercing blue eyes. He was wearing a slightly too small black Harley-Davidson t-shirt, showing off his bulging muscles, and he had tattoos up and down both arms. Tight jeans with a pretty good sized bulge, and black motorcycle boots completed the ensemble. She gave him a big smile, and nodded her head yes. The man smiled back. He was gorgeous she thought. "My name's Ron. What can I get you?

"Hi Ron. I'm Debbie. It's nice to meet you" she said, and shook his hand. He had a firm grip, and she thought she'd love to feel those hands in her increasingly wet smooth pussy. She held on to his hand for a moment as she said "I'd like a Captain and Coke please." She then released her grip.

Ron leaned in to the bartender, ordered her drink, and a Coors draft for himself. He turned back to Debbie. "So, what brings you in all alone?" he asked her. "Meeting someone?"

The bartender gave them their drinks. She gave Ron a sexy smile, and replied "I think I just met him." He laughed a little as she took a sip of her drink. Her eyes never left his. They talked for a few minutes. The usual BS. Where are you from. What do you do. Blah blah blah.

Finally, after about 10 minutes, Debbie said "Let's cut to the chase." He raised his eyebrows as he took a swig of his second beer. "I'm looking to blow someone. If you're up to it." She looked a little harder at his jeans. Her eyes went a little wide as she saw the front of his pants start to stick out. She casually rubbed her hand lightly across the front of his jeans, and felt his cock jump a little. She smiled at him.

"Only blow?" he asked. "I was hoping for a little more." he said as he turned a little, and casually rubbed his hand along her firm tits. She gave a sharp inhale, and her nipples started jutting out.

A few seconds later after she caught her breath, she reluctantly replied "I'm supposed to meet my boyfriend shortly. There's a movie he's been wanting us to watch for quite a while now. I'm sorry, but I don't have a lot of time."

"Boyfriend huh? he asked with a laugh. She shrugged a little. "Does he know you fuck around?"

"I'm a slut, and he's proud of it." she replied with a sexy smile.

He grinned, and pulled her hand down to his cock again. He was hard as a rock, and huge from what she could tell. "Are you sure you don't want to go a little further?"

"Fuck!" she whispered loudly. "How big are you?!" she asked.

"Twelve inches." Ron casually replied, and finished his beer. "And I really want to feel your tight pussy wrapped around it." At this, Debbie's eyes went wide, and she started squirming on the bar stool.

"I've never had someone that big before. I guess I could be a little late." Deb replied after thinking for a moment. "He'll understand. The movie's not going anywhere." she said with a big smile. "Just let me text him to let him know I may be a few hours." She pulled out her phone, and typed quickly. She dropped her phone in her purse without waiting for a response. She looked back up into his sexy eyes "Ready when you are." she said with a smile.

Ron smiled back "Good. Let's go, and I'll drive." he said. He threw some bills on the bar, and nodded to the bartender. He stood, and offered his hand to Deb to help her up. She accepted with another smile. As they were heading out, he looked towards the back of the bar, and saw the rear door closing.

As they stepped out, Debbie paused and pulled out her cigarettes. "I need a smoke before we leave, if that's ok?" she said as she put the Marlboro Red 100 in the right corner of her mouth and lit up. She sucked it hard, and inhaled deeply. She waited a few seconds before exhaling a thick stream of creamy smoke. He watched her and liked what he saw.

He pulled out his own and said "You can smoke in the car if you want." as he lit up his Marlboro Red short.

She smiled at him, and took another huge drag as he opened the door of his '69 Mustang for her. She thanked him and exhaled into his face slowly, and then kissed him passionately. He returned the kiss, grabbed her ass, and pulled her in tight. He rubbed his huge 12" cock against her, and she moaned audibly.

Debbie reluctantly pulled away from him, took yet another deep drag, and said "Let's get going! The sooner I feel that cock in me, the better!" and he laughed a little as she exhaled.

The ride to his place took about 15 minutes. He lived in a shady part of town, that Debbie normally would have avoided. A lot of bars, rundown houses, and hookers on every other corner. She was becoming a little nervous.

"So... why were you at Pete's Place?" she asked, as she took a huge drag off another cigarette. "I've never seen you there before, and believe me, I would have noticed." She exhaled, and flicked her butt out the window. "I mean, there are plenty of bars in this neighborhood.".

Ron sure as hell didn't want to tell her that he was hired to pick her up, and take her back to his place for a little fun for himself, and a lot of pain and punishment for her. He thought quickly, and replied "Have you seen these bars?" and laughed. "Just because I live around here doesn't mean I want to socialize with the locals. Ya know?" she nodded in understanding. Whew, that was close he said to himself.

A minute later they pulled up in front of what looked like a small rundown warehouse. There was a sign out front that said 'Ron's Motorcycle Repair'. She looked at him again. "Believe it or not, it's a lot nicer inside." he said with a chuckle. "I own the building. Repair shop down here, and I live on the second floor. Come on. I'll give you the grand tour." he said as he exited his car. He ran around and opened the door for Debbie, and helped her out.

She smiled again at him. "Such a gentleman." Debbie said to him with a sexy smile. If she only knew...

"I have an entrance to my place on the side, but we'll go through the shop. There's an entrance there as well. That way you can see most everything, and we'll end at my apartment." he said with a wink.

"Most everything?" Deb asked.

"Well, I don't wanna bore you." he said, and laughed. He walked up to the front door of the repair shop, and unlocked it. He ushered her in, and showed her around the shop. There was a sales department as well as the repair shop. It was a fairly tidy place. Not as nice as a Harley showroom, but it looked like it served its purpose.

He led her up the steps to his apartment. He unlocked the door, and waited for her to go in. It was like walking into a whole new world. Nice furniture and carpeting. Very well decorated, and not at all gaudy. Oil paintings on the walls, and a beautiful brick fireplace. Very clean and tidy. She stood in awe.

"This is gorgeous!" she said. "You weren't kidding when you said it was nicer on the inside!" she said as she whirled around, looking at the room. He laughed a little, and lit up another cigarette. She followed his lead, and lit up one as well. She walked around the living room looking at the paintings, and taking deep drag after drag. "Show me the rest of the apartment!" she said excitedly after a moment.

He showed her around. After the living room, he showed her the kitchen (not even a dirty dish in the sink), and then the dining room. He took her down the hall, and showed her the guest bathroom. Next to the bathroom was the laundry room. Across the hall there was the guest bedroom, that was as nicely decorated as the rest of the apartment. Another spare bedroom next to that was set up as a music studio. Guitars, drums, keyboards etc... All of the rooms were of a pretty good size. Last but not least, he led her into the master bedroom. There was a king-sized bed that looked very comfortable. Debbie smiled at Ron. He didn't smile back, but instead studied her face for a moment.

There were two separate sets of doors. The first set had two doors, and she opened them to reveal a walk-in closet. Debbie turned quickly, and said "I would kill to have something like this!" and she laughed a little. She walked back out, and closed the doors. She saw an ashtray by the bed, and went over to it to put out her cigarette.

She then walked over to next door, and tried to open it, but it was locked. "What's in here?" she asked with a smile. He didn't answer, but continued to stare st her. Her smile faltered a little. "If you don't want to tell me, it's fine."

After a few seconds he said "It's my... workout room. Would you like to see it?"

"Sure! The only workouts I do though are sexual." she said and laughed again.

"We can have sex in there. And more." Ron said with a bit of a dark grin. "Besides weights, a treadmill, and all the other usual stuff, I have one or two other things that make working out... fun."

Debbie smiled, and said "Well now you have my curiosity aroused. Along with a few other parts of me."

He stood still for about five seconds, before pulling out his keys. He went over and unlocked the door, and ushered her in. It was pretty dark, so she couldn't see a whole lot. He shut the door behind him, and locked it again with his key. It was pitch black, but Deb heard the key. She got nervous again. "Can you turn on the lights?" she asked.

"In a moment." he replied. "The switch by the door needs to be fixed. There's another one on the far wall." He grabbed her arm not too gently, and pulled her to the far side of the room.

"Hey, not so hard!" Deb said. He gave no answer.

When they got to the other side of the room, he flipped on the light. The room had wood paneling and unfinished floors. Debbie was standing next a wall that had shackles hanging from the ceiling. They hung about six feet from the floor, and were slowly swaying back and forth. She stared at them for a moment, and then looked down to the floor below the cuffs. There were two shackles attached to the wall about three feet apart, and about six inches from the floor. She looked slowly around the room, and saw the weight bench, the treadmill and what looked like a very uncomfortable waist-high bench with a stockade attached. At the bottom of the bench were more shackles. There was also a table with a few more shackles attached to that as well. There were ropes with hooks on the end hanging from the ceiling over the table. She looked at another wall, and saw a few different sized whips hanging, along with some very large dildos, a couple of magic wands, and a riding crop. There were a few other toys sitting on a shelf. Hanging a few feet away was what looked like a sex swing. And in the corner, a toilet, a hand sink, and a refrigerator.

"What the hell is all this?!" she asked very nervously. She reached in her bag and pulled out her cigarettes. She lit up, and took a few double and triple pumps.

"It's my workout room" he replied in a serious tone.

"Not sure this is the kind of workout I want." said Debbie with a nervous laugh, and took another double pump drag.

"I don't really give a fuck what you want." said Ron, and got an awful grin on his face. Deb got scared, and ran towards the door, forgetting that it was locked. Ron walked over, and grabbed her. She shoved her lit cigarette into his arm, and he yelled out in pain. "You Bitch!" he screamed and slapped her so hard, that she fell to the floor. She laid there in a daze. He crushed out her dropped cigarette with his foot, leaned down, picked her up, and took her back across the room. He laid her down not very gently, pulled her shirt off, and then her pants. He left her 3" heels on. He thought it would be hot watching her chained to the wall wearing only those.

Ron picked her back up, and put her against the wall. He lifted one hand, and attached one shackle to her wrist, and then the other shackle to the other wrist. He spread her legs apart as she was coming out of her daze. She started kicking and screaming as loud as she could. He slapped her other cheek. Not quite as hard, but it shut her up.

"No one will hear you. Trust me on that. These walls are soundproof. Don't fight me again, or it's gonna be a lot worse than it's already going to be." he said as he smiled at her. He grabbed her leg, and pulled it to the side, so he could attach the first shackle. Then he did the same for the other leg.

"Could I have a cigarette? I think I really need one." Debbie asked. Ron laughed at her.

"After that little stunt? I don't think so. It's going to be quite awhile until you have another smoke." He replied. That scared her almost as much as not knowing what he was about to do. She looked around nervously. "Smoking is the last thing you'll be thinking about in a few minutes." he said. "Or maybe not." he said after thinking for a moment. He grinned, pulled out his cigarettes, and lit up. Then he exhaled a thick cloud slowly in her face. She was not at all happy.

"Why are you doing this?" she asked. "What did I do to you?" she was almost crying at this point.

Ron answered "Me? Nothing. I never saw you before today. But a friend of mine knows you, and he wanted me to do some payback for him. He paid me well to see that I do. He'll be here shortly. Along with a few other surprises." At that, he started laughing.

"Who is it?" Debbie asked. "Who would want to do this to me?" and tears started rolling down her face.

"You'll find out soon enough." Ron said, and headed for the wall where the toys were hanging. He grabbed a magic wand, and came back over to Deb. "You ever squirted before?" he asked her.

She shook her head no. "Not that I haven't tried. I just never seem to be able to get to that point."

"You're will today. It may kill you, but you will." He smiled, and plugged in the wand. He took another drag, and slowly exhaled it into her face. She was very nervous, and was starting to have serious withdrawals. He turned the wand on low, and put it up against her clit. She started bucking almost immediately. He held it for about 15 seconds before pulling it away. She was breathing heavily. He repeated the process again and again. She started cumming after a few minutes, and she begged him to stop. He was relentless though, and just kept doing it over and over. She came again. She just wanted to collapse but the chains and shackles prevented that. He finally stopped after about 10 minutes.

"Please I need a cigarette!" she was begging. Ron just started laughing again.

"No, but thanks for reminding me that I need one." was his reply. She started sobbing. "Aww you poor thing." he said mocking her. He lit up, inhaled deeply, and blew it in her face. He did it a few more times.

As he was finishing up, his cell phone rang. "Yeah... Where are you?... No, I said left at the light. Not right... Yeah, 1391 is the address... Yes we're here, and I've already started... No I haven't done too much... I left the front door unlocked. Just knock on the door when you get into the bedroom. I'll let you in." he said and hung up.

"Your friend is on his way." he said to Debbie with a smile. "Seems he took a wrong turn, but he should be here in just a few minutes. I'll give you a break until then." He lit up another cigarette, and kept exhaling slowly into her face over and over. This was becoming pure torture for her.

Right as he put his cigarette out, there was a knock. Ron smiled at Debbie, and walked over to unlock the door. When he opened it, Deb's jaw dropped.

"Al?! What the fuck?! You're behind all of this?! Why?!" she was practically screaming at him. He smiled at her.

"Payback is a bitch... Slut." he said calmly. He pulled out a pack of cigarettes, and lit one up. He stepped up to her "You pretty much fucked up my life with that little stunt last weekend, when your friend Brenda came to visit. Making me fuck Bob in his ass, and forcing me to become a smoker?! What the actual fuck were you thinking?!" he screamed in her face. He took a drag and exhaled it quickly.

"I... I'm sorry! I lost control! Once I started, I couldn't stop! Please believe me, I am so sorry!" she was crying hard at this point.

Al continued his tirade "Linda came home earlier than expected Sunday. The house reeked of cigarettes, and she found me jacking off to gay porn. She threw me out on my ass! I couldn't tell her what happened though! She filed for divorce two days ago. I have nothing now thanks to you! Except a 2 pack a day smoking habit, and I can't stop thinking about fucking guys in their ass! So, thanks for that!"

Debbie didn't know what to say at this point. She looked at him for a minute. "I'm sorry. I really am." was all she could come up with.

"Not good enough Slut." said Al calmly. "You're going to pay for what you've done." He looked at Ron. "Please continue." he said to him. Deb looked at him in horror.

Ron smiled, and turned back on the wand. He set it on the highest setting this time, and put it against her clit again. She was bucking harder than before. He pulled it off just before she was about to cum again. He waited until she stopped squirming, and did it again. And again. And again. Al watched her, and smiled while he smoked. After 15 minutes, Ron finally let her cum. She screamed in pleasure and agony, and was convulsing. She was soaking wet, but still hadn't squirted. Ron took a 10-minute break, and grabbed a cold beer for Al and himself from the refrigerator he had in the corner. He grabbed a towel, went over to Debbie, and wiped her face and breasts. She was shaking and sweating profusely. She needed a cigarette badly.

Ron said "Let's try something different." and undid the shackles at her feet. She drooped as far as she could go, but her wrist shackles wouldn't let her drop all the way to the floor. He let her hang there for a few minutes before holding her up, and releasing her wrists. She tried to drop, but he easily held her, picked her up, and carried her over to the table. He laid her down on her back, and attached her wrists to the shackles at the top of the table. He pulled her knees up, and hogtied each leg with rope, so she couldn't put them back down. She looked like she was ready to do sit ups. He then pulled her legs up so her feet were in the air, and attached the ropes on her legs to the hooks on the ropes hanging from the ceiling. Her legs were spread wide, and she couldn't pull them together. Her pussy and ass were easily accessible. He removed her heels, and threw them over where her clothes were laying. Deb felt a bit of relief when he took them off. In a moment, she was going to wish they were still on.