So it's been a while. Oops. Starting to take classes and feeling a little burned out with writing can do a number on how often you update. ^^() This chapter is dedicated to one of my favorite writers on here. I hope you enjoy it, my dear!

Ambrose and the Frustrated Spanko

Mondays are designated days off for my boys. Some of them are constantly booked up, so this makes sure that they have a day to rest. You know how tiring it can be to always be trying to make people happy. On Monday nights, I bring them to my favorite bar. Mondays are not a popular drinking night, generally, so the bartenders appreciate the extra business. In all honesty, we're usually the only ones there, except for a few regulars who always sit on the end of the bar closest to the door and never bother us.

I do it to make my boys happy and let them hang out together, but I also do it because I enjoy watching them with a little alcohol under their belt. Most of them are not bound by many inhibitions as it is, but they do get awfully giggly when tipsy and I find that remarkably cute.

So as this Monday night progressed, I had settled into my spot at the bar with my glass of brandy and was admiring my boys when I noticed the bartender on duty staring at them as well. Now don't get me wrong. I wasn't upset at her for looking at them. That would be absurd. I want everyone to look at my boys because everyone is a prospective client. No, what I found odd was that she had never really seemed to take notice of them before in all the times that we had been here.

She was a sweet girl. Annabel was her name. She had lovely raven colored hair and she looked mature for her age, a detail that was usually accompanied by an almost permanent scowl on her face.

"What's troubling you, sweetheart?" I asked.

She almost seemed startled that I was even speaking to her. I think she had gone into a bit of a trance while looking at my ridiculous boys laughing and throwing napkins at each other like a bunch of drunk children.

"Oh, sorry Mama. Did you want another brandy?"

"No, dear. I'm still nursing this one. I just noticed that you were staring at my boys," I laughed.

"Oh no! I'm sorry. That's not a very professional thing to do, is it?" She scratched the back of her head as she looked at me sheepishly.

"Bel, the staring was fine, you don't need to be ashamed. It's just that we're in here every week and you've never stared at them like that before. It was like you were in a trance and your mind was elsewhere, so I was wondering if something was troubling you."

"Ahh, it's just dumb guy stuff."

"What do you mean?"

"Well I've just never seemed to have much luck with men. I'll meet a guy I really like, but they just want to get in my pants. That wouldn't be so bad if they were upfront about it so I knew that it was just a sex fling, but even then, the guys never seem to be into what I'm into."

"And what would that be?"

"Spanking."

"Guys don't want to spank you?"

"Come on, Mama. You're in the business of sex, so you know what I mean. They don't ever seem to understand just how much I need to be spanked. It's like an instinctual inner desire for me or something. I just need to be disciplined. I can't quite explain it. Then, if the guy is willing to try, he just sort of taps my bottom and thinks that's a proper spanking. They're afraid to hurt me, but that's part of the whole experience."

"Hmm, I see what you mean."

"So I've casually dated a few guys and had one or two quick flings, but nothing has felt right. No one has been able to satiate this...thirst that I have. It's just really frustrating. Maybe I was subconsciously staring at the guys because I'm still pining for a proper spanking and they're there in front of me, being all handsome."

I laughed at her and she frowned.

"Sweetheart, it's entirely understandable to be sexually frustrated. A good chunk of my business comes from people with that issue. If you ever want to get rid of that frustration..."

"Oh geez. Mama, I don't think I could ever pay for sex. I can't afford it, for one thing, and I think I would hate myself. Like I would feel that I'm a failure for having to resort to that."

"You wouldn't be a failure, Bel. No one's a failure for not being able to find the person who best compliments them. Or for not being able to find a person who just 'gets them' sexually. It can be a challenge." I took one of my business cards from my purse and slid it toward her. "You can trust me, sugar. Whenever you feel ready, just give me a call."

"I don't think I'd ever be ready," she replied, although she picked up the card anyway and slipped it into the pocket of her jeans.

She went back to wiping down the bar and I returned to admiring my boys. I noticed that Jon had been watching me speak with Annabel. We made eye contact and then he glanced at her, then back at me. He raised his eyebrow and I nodded. I held up my hand, flat and with the fingers together, and flicked my wrist. He nodded back and smiled. This was why he was my favorite. We understood each other without saying a word.

Tonight, Annabel was going to get the release that she so craved.

I rounded up the boys and began to guide then outside. They were all drunk enough where they needed a little guidance, but not to the point of being obnoxious or a public nuisance. If any of them ever got that drunk, they got a rather aggressive talking to. You might laugh at the thought of me scolding these grown men like they were schoolboys, but trust me when I say that I can get pretty vicious when need be.

As I lured them out of the bar, Jon held back and strolled over to the bar where Annabel was getting ready to close up. He winked at me and I winked back as I let the door shut behind me.

He leaned against the bar, casually, yet with that aura of charisma that naturally drew people to him. He watched her for a moment, admiring her more superficial traits and smiling to himself. When she turned around, she jumped.

"I thought everyone had left!"

"They did," he shrugged. "I just decided to stick around for a while. If that's okay with you, of course." His mouth curled into the sort of grin that makes panties drop. It wasn't lost on Annabel.

She cleared her throat to try to somehow hide her flushed face. "No, uh, I don't mind. Any particular reason that you'd want to stay after closing? Do you want another beer?"

Dean shook his head. "Nope." He rested his head in his hand as he leaned against the bar and stared at her mischievously.

She shifted uncomfortably under his gaze. "Okay then…so…what do you want?"

"Nothing in particular. I've been keeping an eye on you all night."

"...really? Why?"

"Mmhmm...you just seemed a bit out of it today. You doing alright?"

"You're not going to charge me for this, are you?"

"Just to talk? Generally when someone is paying me, we're not talking," he said with a wink and a smile.

She frowned at him and looked away, her cheeks slowly becoming a light shade of rose.

"No, Bel. I'm not going to charge you. Don't be ridiculous. You're always so good to us, so this is me as a friend right now."

She sighed, accepting that he wasn't going to go away until she opened up to him. "I've been having a bit of guy trouble lately."

"Did some dude break up with you?"

"Not to go into specifics, but more or less. I just feel used and disappointed. I had opened myself up to him when I told myself I wouldn't and he took advantage of it. So that's been bugging me the last few days."

"I see. You should get back out there. Find someone to distract you for a little while, if you catch my drift."

"Dean, your drift is so obvious, I can see it from a mile away," she giggled, smiling for the first time that night.

"You should smile more. You're beautiful when you do."

By now Annabel's face was close to a shade of crimson. "Thank you, Dean." She shook her head and leaned against the bar. "I don't think that would help very much, going to find someone as a distraction. The kind of thing I'm looking for...it just doesn't seem like it's easy to find guys around my age who are into it. Every time I've tried dating sites online, I can only find older gents and I'm generally not very attracted to older men."

"What is it that you're looking for?" he asked, knowing full well what the answer was going to be.

"I need to be spanked."

"Well no one can ever say that you're not upfront about it," he said as he pushed the hair out of his eyes.

"I mean, if I was looking for someone to spend my life with, I'd include other criteria, but I'm only 22 and I just want to have some fun and spend time with someone casually. He doesn't need to be perfect..." she said, her voice drifting off. "He just needs to not stand me up and not spank me like a pussy," she mumbled under her breath.

"How do you want a guy to spank you, then?"

Annabel covered her mouth with her hand. "Fuck, you heard that?"

He laughed at her and placed his hand on his chest. "Hey man, you're talking to a fellow mumbler. I speak the language."

She shifted her weight back and forth on the balls of her feet. "I want it really hard. I want it to hurt. But I also want the guy to know what he's doing. Like, there's a method, a technique to a proper spanking that these guys don't seem to understand. It's just...frustrating. It's never as sexually fulfilling as I wish it was. As I feel it should be."

"I see," he said, rubbing his chin.

"And to top off my downer mood lately, I feel like my professional life is in shambles. I have a degree and what do I have to show for it? I tend bar at this place. I wish I had a better job, but it's been so hard trying to find one around here."

"I'm glad you work here because I get to see you every week." His smile was enough to charm her into believing him.

"You're probably just saying that to make me feel better, but I'll take it."

"So your personal and professional lives are both feeling pretty shitty lately?"

"Extremely shitty, and the prospect of that changing doesn't look great."

"It sounds like you need a little structure...a little discipline in your life." He waved her over to him with his hand. "Come over here." He pulled out one of the wooden chairs and sat down facing her. She hadn't moved an inch. He shot her a disapproving look. "I mean it, Annabel, get over her now."

The hard look on his face and the sternness in his voice made her legs shake as she slowly came around the bar and walked forward. She stopped in front of him. Her hands fidgeted in front of her and she looked at the ground. She couldn't quite get herself to look him in the eyes right now.

"Annabel. Look at me."

She lifted her eyes, peeking at him through her lashes, but she didn't lift her head. She felt so embarrassed. He grabbed her chin firmly and pushed it up so that they were face to face. Her cheeks were turning from a pleasant pink to a bright red.

"I want you to lie down over my lap."

"Seriously?" she asked.

"Do I look like I'm joking?" His eyes were rigid and intense.

Gulping, Annabel shook her head. She slowly lowered herself across his thighs, but it was apparently too slow for Dean.

"Get down there," he said as he pushed down on her back and pulled her into the proper position. "This is what you want, right? That's what you said."

"Yes," she nodded. "Yes, please."

"Now tell me. Why do you deserve to be spanked?" he asked as he started to rub his hand along her jean-covered bottom.

"I can't quite seem to get my life together."

"I should smack your ass for being too general. Give me something specific to punish you for...or I'll punish you for failing to follow the rules."

"My life is unorganized. I need some structure. Some rules. Some guidance to make myself better and progress as an adult."

"That's a very mature answer. Good girl." He squeezed her ass playfully and she let out a squeak of surprise. "I might not be able to keep you in check all of the time, but I think I can help you get started."

He pressed his left hand down firmly onto her back and lifted his right hand. Annabel inhaled sharply, knowing what was about to happen. Dean brought his hand down hard onto her right cheek, then repeated the same action on the left one.

Annabel winced, but did not cry out. This wasn't her first rodeo, so she knew what to expect. She would have to admit, however, that his hands were larger and stronger than any of the guys she had been intimate with previously.

"Those were just two warning shots. Do you still want to go through with this?"

She took a deep breath and nodded. "Please god, yes."

He made a low noise that softly rumbled in his throat. Annabel wasn't quite sure what it was. A moan? A growl? Whatever it was, though, she knew she wanted to hear it again.

He gave her ass another gentle rub and then without much of a pause, he began to smack her bottom hard and at a steady, upbeat pace. Thwack. Thwack. Her body lurched forward a tiny bit every time his heavy hand made contact. Thwack. Thwack. Behind the pain, there was a deliciousness about it that she would never be able to put into words to try to explain to others. It was just something she felt deep inside. Her breath became heavy and right before he let up, she was about to crack and cry out.

"Get up and take your pants off," he ordered.

She awkwardly tried to pick herself up off of his lap, but he wouldn't help her. Once she was finally standing again, she noticed that he had been watching her very closely. She started to unfasten the button on her jeans, but her fingers couldn't quite get it with him staring at her. They had talked so easily and casually just moments before, yet now there was this different aura about him. He was really taking this dominant role to heart.

"Faster. Quit stalling, Annabel. You need to take your spanking like a good girl."

He was flexing the fingers of his right hand like he was warming them up. The sight of that alone made her feel a little dizzy and her pussy began to ache. She could still feel her bottom throbbing slightly. She bit her lip, anticipating what was to come next. She managed to finally remove her pants and she went to stand next to Dean.

"Very nice," he smiled when he saw the panties she was wearing that night. He pointed to his lap and his smile turned stern. "Get down here, now."

She obeyed him immediately and he praised her for it. His hand returned to her ass, gliding along the thin fabric of her panties.

"This feels so nice," he said. "You over my knees. My hand teaching you a lesson." He began to spank her again as he said the word "lesson".

Without the thick covering of her jeans, Annabel could feel the sting of his hand much more. She didn't want to make any noise, but she just couldn't help it after the first few smacks. It started off as a soft whimper, barely audible. It soon grew into a muffled whine. She was clearly feeling the rawness in her skin, but she kept her lips tightly pressed together. She didn't like crying during a spanking, and she refused to do so now.

"It's okay, you can cry. I know it hurts." She shook her head defiantly. He paused for a moment to turn her head up towards him and he leaned down and looked in her eyes. "I want you to cry, Annabel. That's the only way I'll know that this is working. This is how the message will get through." She shook her head again.

"Fine, if you want it that way…" He let go of her face and brought both hands to her hips. Grabbing the top of her panties, he forced them down until they were sitting around the middle of her thighs. Her flesh was already a pleasant baby pink color, but he wanted to see red. "I will make you cry."

He pushed down firmly on the middle of her back and began to unleash a flurry of heavy slaps to her bare ass. Annabel had never had such a hard spanking before. She had always wished that a guy would go as hard as Dean was at that moment, but now that she was getting her wish, she wasn't really sure if it was what she wanted. Right now, everything just felt like it was too intense. It was too much.

It took her a few seconds to realize that she was crying. It wasn't a hysterical sobbing sort of cry, but it was immensely cathartic and exactly what she needed right now. She watched as her tears dripped off of her face and hit the wooden floor below her. A few wails managed to escape from her mouth and she heard him whisper, "That's my girl."

After a few more smacks, Dean let up, taking his right hand and lightly placing it on her lower back. He rubbed his hands gently along her back, trying his best to help her come down from this experience. He leaned down and wrapped his arms around her as best he could. It was an awkward sort of position, but he didn't want to sit her on his knee right now, as her bottom was hypersensitive.

"You did very well, Bel. I'm very proud of you." He lifted her head up and kissed the top of it. Despite some tears still welled in her eyes, she smiled.

"Thank you for that," she whispered.

"It was my pleasure."

He glided a hand up her inner thigh until he reached her bare pussy. Her outer lips were already slick with wetness. He could only imagine how wet she must be inside.

"Damn, you weren't lying when you said you craved a spanking." He traced a finger between her lips, eliciting a soft moan from her throat. He parted her legs slightly so he could have easier access to her entrance. He slid two fingers in with ease as she wriggled on his lap.

"You are so wet and open right now." He felt himself quickly harden underneath her. He had been a little hard during the spanking, but seeing just how aroused she was right now was a huge turn on.

He picked her up off of his lap and helped her onto her feet. He stood up and pressed his lips against hers while he fumbled with his pants.

She broke away from the kiss with a gasp. "I so badly want to fuck you, but I told you I can't afford it."

"That spanking was me helping out a friend," he panted. "This right here is me about to fuck you because I want to. Now take your shirt off and let me see those tits."

She wasn't about to let embarrassment stop her from giving him what he asked for. She pulled her top up and over her head, tossing it over to where her jeans had landed earlier. She also decided it was time to fully take off her panties, which quickly joined the rest of her clothes.

He had finally managed to unhook the button of his pants and pull down the zipper. He was attempting to pull out his cock when Annabel grabbed the waist of his pants and pulled then down to his ankles.

"If I'm getting to have this moment, I'm going to get the whole view."

He laughed at her sudden boldness as he kicked his pants behind him. "I suppose my shirt has to go too then, yeah?"

She nodded and crouched down in front of him to work on removing his boxers. When his cock sprung out from behind the fabric, she leaned back and took in the view.

"You like what you see?" He laughed.

"It's even better than I imagined. Ever since you guys started coming here once a week, I've honestly always wondered what it would be like to fuck you. I…sometimes stare at you when you're not looking." Her whole body had been flushed for a while, but he could still tell that she was blushing from admitting that.

"I've actually thought about what it'd be like to bang you, too. Sometimes you absentmindedly suck on cherries when it's slow in the bar, and goddamn woman, it looks like you could do some amazing things with that mouth of yours."

"I flattered, but if you want to try that out, it'll have to be another time because I need your dick in my pussy right now."

"Yes, ma'am," he laughed.

He quickly grabbed a condom from his pants and returned to her as he rolled it on with ease.

"You're quite good at that," she said.

"I hope I'd be with how often I put them on," he chuckled. He sat back down in the chair and crooked his finger at her. "Now get that fine ass of yours over here so I can look at my handiwork."

He reached his hand out to her and she took it, stumbling a bit as his tugged her toward him. He turned her around and traced his finger along the red raised welts that were in the vague shape of his hand. She shuddered at the slight touch. Her nerves were still on high alert and her skin was tender and sore.

He spread his legs slightly, placed his hands on her hips and pulled her down like she was going to sit in his lap. He held her around her waist for a moment while he lined up his cock to her waiting hole, then he let her weight sink herself down around him.

His dick felt amazing, filling her completely. She could feel him throbbing, even through the condom. She let out a long moan as her circled his hips while he was balls deep within her. He held her low around her waist and she feared for a moment that her weight would give and she would fall, hurting herself and seriously hurting Dean. After a moment, though, she felt confident that she was safe in his strong arms and let herself go.

He rocked her back and forth so that her hips slid up and down his cock. Slow and deep, it felt great, but it was also like a great tease to Annabel, who was used to being fucked fast and furious. She covered her breasts with her hands and began to massage them at the same speed that their bodies were rocking together.

He looked down over her shoulder and watched her with a smirk on his face. "One of my favorite things in the world is watching a woman pleasure herself," he whispered in her ear. She let her head roll back against his shoulder so he could have a better look.

After a while, he straightened her up and stood up himself. He gently pushed her so that she started walking toward the bar. She got the hint, bent over slightly, and leaned against the bar. He dug his fingers into her hips and slid back inside of her, thrusting at a furious pace. He cupped a hand on one of her breasts and the other hand slipped between her legs. His pelvis slapped against her ass with each thrust, sending shivers of pain and pleasure through Annabel's body.

She felt the tension building between her legs as he rubbed his fingertips against her clit and roughly pinched her nipple between his fingers. She finally released around his cock when he bit down on her earlobe. The cries of her orgasm sounded vaguely similar to the cries she made during the spanking.

"Mmm," he moaned. "You sound fucking wonderful when you come."

He gave a few more thrusts before his body went rigid and he thrust in deep, spilling his cum into the condom. They stood there for a few minutes, his arms still wrapped around her, as they came down from their high.

Once they had cleaned up a bit in the bathroom and got dressed again, a painful reality hit Annabel in the face.

"Fuck. I still haven't cleaned the bar yet." She hit her head with the palm of her hand and then went to grab the cleaning supplies.

"Let me help you so you can get out of here," he offered.

"That would be wonderful."

With the two of them working together, it only took about a half an hour to clean up the small bar. The two of them stood outside as she locked up.

"Hey," he mentioned. "Would you like me to walk you home? It's late and I wouldn't feel right leaving you alone, especially after we fucked and everything."

"You make it sound so romantic. Yes, thank you. I would really appreciate that."

"Alright then, let's go." He gave her a smack on her ass as he strutted past her. She glared at him with a big smile on her face and rubbed her sore butt as they headed into the night.

As always, feel free to message me on here or say hi on tumblr (I'm there under the same name). Thank you for reading!