It's Fucked Up

'You are. This will be conversation only.'

.........

The bar was quiet for a Tuesday afternoon. Some days I would change from my business attire, put on jeans and wander over here as it wasn't as stuffy as the bar at the hotel. It's a great bar to get a drink, a burger and watch a game. Cheryl was one of the regular waitresses and always wanted to wait on me when I came in.

She's 29, covered in tattoos and has more piercings than I can count. When it's dead, she will sometimes sit with me and I'll buy her a beer and talk about life. I'm also a good tipper, so she makes sure I'm taken care of.

I asked her for something private as I was meeting a "friend". She smiled, knowing it was most likely a hook-up. It's funny how much bartenders and wait staff see and quickly pick up on what's going on. She led me to a corner booth in the back, one with a circular bench and as much privacy as any other seat in the bar. After I got settled, she brought me my usual, Johnny Walker Black, neat. I had just taken my first sip when I noticed her walk through the door. She looked nervous. And to be honest, I was nervous too. But I tried my best not to let it show.

She looked around the mostly empty place and made eye contact. I nodded as she made her way back to the table. The only guy sitting at the bar turned to stare at her ass as she walked by, but her focus was anywhere but him. She had on a floral printed dress, the top cut low to show off her ample cleavage. As she reached the table, I motioned for her to sit next to me. She nervously looked around and slowly moved her hair behind her ear as she looked back at me and smiled then sat.

I didn't say anything. Partly because I was nervous and didn't want to fuck this up. But also because I wanted her to speak first. I stared at her eyes as she looked down at the table. She reached up and began twirling her hair, looking for words to say. Cheryl walked by and asked for her drink order.

"She's not drinking tonight Cheryl." She looked at me then at Janet, who suddenly looked at me with a surprised reaction. Not pressing the situation, Cheryl turned and walked away.

At this point, our eyes were locked. I still hadn't spoken to her, only addressed Cheryl. I had taken control of the situation and felt the confidence I was looking for. Moments passed and she looked back down at the table as she continued nervously playing with her hair.

Finally, "Thank you for meeting me. Katie said you may be able to help me." She never made eye contact, only stared at my glass. She was nervous and I could feel the seat move from her legs shaking.

"Yes. Katie told me and I said I would meet with you. Do you prefer Janet or Jan?"

"My friends call me Jan." I already knew this from Katie.

"Okay. Why don't you tell me why you are here, Janet." She tensed at my disregard for calling her what her friends do. Her hands were shaking now and she looked back at me.

"May I order a drink? It will help calm my nerves." Despite being a middle-aged woman, she looked like a nervous schoolgirl in that moment.

"No. I want your mind clear for this conversation." She nodded, acknowledging that made sense.

"Tell me Janet, why are you here?"

I took a sip of scotch and then swirled my drink around as I waited for her response.

Taking a deep breath, "Didn't Katie already tell you? She told me about you and that maybe you could help me."

"Help you with what exactly? I want to hear it from you Janet." I kept swirling my scotch and her eyes were glued on it like someone being hypnotized with a swinging a pocket watch. A minute passed. Then two. I was beginning to think I had overplayed the situation.

"I". deep breath. "I- I want you to dominate me." She let out a long breath, relieved to finally get it out.

I took another sip and her eyes followed the glass. Setting it back on the table and swirling the light brown hypnotic liquid, I asked.

"And why do you want to be dominated Janet?"

Moments passed and then another deep breath. "Katie told me that you join them in bed and have them do things for you. I don't judge. In fact I would have loved if my ex-husband would have been as adventurous as Mike. She also told me how you take control in the bedroom and make her do things she normally wouldn't do. She goes on and on about how great the sex is and how it has opened up a new world for both of them.

After hearing about the details of all you've done with her, I found myself wanting the some of the same. Especially what you've started doing with her lately. I've never been with a man that has taken over and just had his way with me like you do with her. I was married for over 20 years and the sex was never great. Even when we tried to spice things up, it was never anything like what you do with them. I've dated men since my divorce but the sex isn't anything memorable. Dating at this age is hard and I have never been with anyone where I didn't have to play a role. I've even had one-night stands thinking it would be wild and free, but those aren't anything close to living up to the hype. I've known about you since the first night you met them at the bar in the Ritz."

She paused, searching for what to say next. I was also taken aback that Katie was that close with her to tell her everything, even the stuff with Mike. They were closer than what Katie had let on.

"I'm not even sure how this works, but I know I can't stop thinking about it. I want to be able to give up control with someone and let them use me however they want. To be able to fully experience something so raw and primitive yet be safe. I even fantasize about being degraded and humiliated to an extent. I know that sounds depraved but I can't stop thinking about it. It turns me on in a way I can't explain and as a woman that's dangerous, but Katie trusts you. And since she trusts you, I trust you."

She looked as though a huge weight had been lifted from her shoulders. And all of a sudden, I felt that weight on me.

Who was this woman?

Katie said she had a close friend she wanted me to meet. She said she was single and sexually frustrated and wanted to be dominated some, but I wasn't expecting her to be so open and vulnerable about it like she was.

We sat in silence for a few moments as I pondered what to do next.

"So? I put myself out there for you. Will you do it?" She looked even more nervous now than before.

"Do you understand what you are asking?"

"Yes. I think so?"

"You need to be sure Janet. If I do this, I will need 100% obedience when we are together. Because I will punish you if you aren't obedient." She gasped but her nervous look changed. It was now a look of desire and she saw me pick up on it and quickly looked away.

"You want to be punished, don't you?" She looked down again and her face began to blush.

"Have you ever been spanked before Janet?"

"No"

"Do you want to be spanked?" She paused again, looking back at the swirling liquid.

"Y-y-yes. I have fantasized about being spanked for a long time." Another exhale of relief. I quickly learned she was not only wanting to be submissive, she wanted to confess her desires.

"Have you ever told anyone else of your desires?"

"Katie knows. We tell each other everything. We always have. That's why she said you could help. She trusts you. She said you started spanking her a while back. She told me about your spanking her last week and how much she orgasmed from it. She even showed me her butt the next day and how red it still was!"

I took another sip, hoping the glass would hide the surprise in my expression. I wasn't expecting any of this. Katie said she was a close friend. But as I looked at Janet more closely, the pieces quickly fell into place and I figured it out.

This was fucked up!

Janet wasn't a friend.

Janet is Katie's sister!

How did I not pick up on it before? They look just alike! I took another sip as I processed this information. It didn't really change anything. Actually, it did. Katie, Mike and I had become friends. For her to share what we do and also recommend me to her sister meant something. I also felt a strong sense of responsibility as I sat beside Janet. She had exposed her deepest desires to me and wants me to help her live them out.

As I processed the tremendous responsibility laid before me, my thoughts were interrupted.

"Well? I just laid it all out there. You could at least respond." Her demeanor changed and she started scooting out of the booth deflated.

"I didn't tell you to leave. Sit down Janet." She did. As she started to speak,

"You don't talk unless I ask you a question. Do you understand?" She nodded.

"The answer is 'Yes', Janet."

"Yes, master." She was anxious.

`

"I didn't say 'master', Janet. Only yes."

"I'm sorry, I was only trying to please you."

"When we are together, you will have no choice but to please me. But I'm not into this master/slave nonsense. If that's what you want then I'm not your guy. But if you want me to help you with your fantasies and desires, I'll do so. But I'll need to understand your limits."

She thought for a moment. "I don't think I have any."

I laughed. "We all have limits, Janet. If I told you to strip naked right now and go blow that guy over there at the bar, would you?" She looked at the bar and then back at me.

"Oh, I see your point." She sat in silence, thinking.

"I would never do that to you Janet, but did want to show you that you need to think before you so willingly agree to something." She nodded.

"Do you really want from me what you've said?" She thought again for a minute.

"My heart stopped when you said that about the guy at the bar just now. But it also turns me on. Katie is right, there is something about you. I don't know what it is, but I feel like I can trust you. So, yes. This is what I want." Our eyes locked again and she seemed to be set in her decision and had the most confidence I had seen from her yet. I now had to figure out what to do next.

I lifted my drink and swallowed the last of it. As I set it back on the table, I looked back at Janet.

"You understand what this means?"

"Yes"

"I told Katie that I would meet with you today and that this would be conversation only, no sex."

"That's what she told me too."

"I'm not going to change that agreement. I'm a man of my word. However, in light of what you've told me, I AM going to punish you." Her eyes widened and her look was one of shock and want.

"You were disrespectful and acted like a spoiled child when you started to leave a moment ago. You also didn't follow a simple command and answer me the way I told you to." Her mouth was open in surprise, but her look told me everything. She wanted this alright.

She needed this.

"Are you wet right now?"

"Yes."

"You want to be punished, don't you?"

"Yes."

"Tell me Janet. Tell me you want to be punished."

"I want to be punished."

"How do you want me to punish you." She paused. She was shaking.

"I-I-I want you to spank me like you did Katie." She let out another breath as she confessed her desire.

"I only give a spanking on a bare ass." Her mouth was open again but I could tell her pussy was leaking now.

"Take off your panties and hand them to me." Her eyes widened as she looked at the palm of my hand on the top of the table then glanced around the room. But she also didn't hesitate. She reached beneath her dress and began sliding her panties off while sitting in the booth.

Just as she began to hand them to me, Cheryl had dutifully noted my empty glass and walked up to see if I needed another drink. Janet blushed as Cheryl had walked up just as she handed me her panties. There was a dark wet spot clearly visible in the pink silk and Cheryl most certainly took note. Janet tried to pull them back under the table, but I held them tight.

I pulled my hand from beneath Janet's and held her panties up, examining the wet spot and then showing it to Cheryl. She grinned at my display.

"We are doing great Cheryl." Cheryl looked back down at Janet whose face was now beet red. I know Cheryl well enough to know this was tame for her. She's told me she is pansexual and currently has a girlfriend named Beth, but they both share a boyfriend named Seth. Her other job is at a sex toy shop down the road and is whom I bought the leather strap and restraints from I used on Katie.

Janet however didn't know this information and was thoroughly embarrassed. She couldn't make eye contact with Cheryl and looked down and away from her.

"Actually Cheryl, I need to ask you a favor." Janet looked at me not sure what I was doing.

"Mr. Davis.." I interrupted her.

"Cheryl, you know to call me Scott"

"Sorry. Scott, you come in here enough and always leave the most generous tips. What can I help you with?" She looked back at Janet and almost laughed as she seemed to be enjoying the scene as it played out.

"As you can see, Janet is quite turned on at the moment but she has also disobeyed me and needs to be punished. And by punished, I mean a bare-bottom spanking. This is something I would like to address immediately. Is there a private room somewhere we could use for a few minutes?" Janet's eyes opened wide in disbelief.

Cheryl looked back at the bar and then around the room. She made eye contact with the bartender, made a gesture then looked back at me with a grin. "We have a stockroom in the back you can use. It would be perfect for that purpose. Follow me."

Janet froze, but I nudged her along and out of the booth. I grabbed her hand as we followed Cheryl to the back past the restrooms. She opened a door and turned on a light to a large closet lined with shelves of beer, wine and liquor. There was also a small office desk for taking inventory. Janet walked a few feet into the closet and turned around looking at me still in shock. I pulled the chair from behind the desk and sat down.

"I'll leave you two alone for a while. Just turn the light off when you are done." Cheryl smiled again and started to close the door behind her.

"Cheryl?"

"Yes Miste..I mean, Scott?"

"If you don't have to be back at the moment, you are welcome to stay and watch. That is if my spanking Janet won't offend you." She looked at Janet, smiled and closed the door. Janet now looked horrified and I needed to make sure I didn't run her off.

"Janet, you said this is what you wanted. You said you wanted to lose control of the situation. To be spanked and even humiliated to a point. Well, here we are. This has all the elements of what you wanted. I'm going to spank you on your bare bottom in front of Cheryl. Or, you can walk out of here now and we will never see one another again." She stood, frozen. She couldn't make eye contact and began shaking. But she also didn't head for the door.

"But if you really want to live out this fantasy, remove your dress."

I had not anticipated any of this, but the situation seemed to play out perfectly. Janet nervously looked at Cheryl then back at me. I almost thought she was going to pass out from embarrassment when she lifted her dress over her head.

"Drop it to the floor." She did.

Standing in front of me and Cheryl wearing only a bra, Janet was exposed. We both were quickly drawn to her full bush, something I'd not seen in a long time.

I let her stand, shaking, for a few moments when I told her to remove her bra. She reached back, unclasped it and let it fall to the floor on top of her dress. Her tits were larger than Katie's. But then again, so was she. While not obese by any stretch, she was full-figured and had the pear-shaped curves of a true woman.

She looked over at Cheryl and then began to cover her tits with her hand.

"Hands by your side." She did.

I stood and walked the couple of steps to her. She was visibly shaking as I eyed her exposed body up and down. I walked around her taking her in completely. She had a small heart shaped tattoo on her left ass cheek just below her panty line. When I touched it she jumped.

"Spread your legs for me." She widened her stance, still not making eye contact with me.

I ran my fingers through her pubic hair, which looked like she hadn't trimmed in some time. When my finger found her wet slit, she began shaking almost uncontrollably. I made it to the entrance of her pussy and scooped up the thick, syrupy secretion with my finger tip. As I pulled my finger up, a long stringy trail was still connected to her pussy.

Holding my coated finger inches from her eyes, "What is this?"

"It-it-it's me."

"More specific."

"It's my juices."

"From where?"

"My pussy"

"Why is your pussy wet Janet? Why are we here?"

"B-b-because I want to be spanked." Her shaking was now almost uncontrollable. I looked over at Cheryl who's eyes were focused on her pussy.

I stepped back and walked over to the chair I had placed in front of the desk.

"Come over here and lay over my lap." She didn't hesitate and it seemed she wanted to get it started. I did too, as I was afraid she may pass out and I sure as hell didn't want her to get hurt from falling.

She started to lean over my lap from the left side and I corrected her and had her come in from the other way. As she settled in, her tits were hanging just over my left leg and her legs were stretched out behind her with her toes touching the ground. Her fingers barely touched the floor, but enough to steady herself for when I started.

Cheryl was standing in front of her and I made a motion for her to stand on the other side, behind her. Janet noted the movement and looked around to see where she was going.

"I told her to stand over there. I want her to see how red your ass gets after I get started. I also want her to see how wet your pussy is while you are being spanked for the first time."

I'd never been in a situation like this before but knew I had to maintain control of the situation and be confident in my decisions. With my left hand, I reached under and began grabbing her tits. I tweaked a nipple and she gasped. I didn't want to hurt her but I also wanted her to know I was going to do whatever I wanted to her body. I then did the same to the other. I cupped her tit in my hand and felt the weight, much larger than Katie and my wife.

I also started rubbing her ass and had her spread her legs. Cheryl had the best view standing only a couple of feet behind her and seemed to be enjoying the show. I also noted she had unbuttoned her jeans and had a hand shamelessly inside her panties diddling her clit. She saw that I saw what she was doing and it didn't bother her one bit.

What have I gotten myself into? Damn!

Smack! Smack! Smack!

The blows came quick and hard. Janet winced from the smacks and almost slid off my lap from the suddenness of the spanking. I re-adjusted her and added six more swats. I heard a verbal 'OW' but added another ten swats in quick succession. She wasn't crying at this point but I certainly had her attention.

I rubbed her ass which had begun turning pink from the smacks. With both hands, I pulled her ass cheeks apart and made sure she was completely exposed. I wanted her to know we were both looking at her most intimate area. Looking up at Cheryl, her finger was rubbing vigorously on her nub as she stepped forward to get a better look.

Janet's hair was matted from the juices freely flowing form her pussy and her lips were swollen and red. Her pucker was also glistening from where the juices had leaked down from her pussy. Like the first time I had met her sister a year ago, I inserted my finger into her snatch and began feeling around. She was swollen, very wet and ready for sex. I quickly found her engorged g-spot and pressed down, beginning to rub it in small circles.