It's Fucked Up

She was moaning now from the pleasure and lost in the moment. Abruptly, I pulled my finger out and added ten more swats to her ass, which was now turning a darker shade of pink. Just as she began whimpering from the pain, I shoved two fingers back into her pussy and found her spot again.

She was writhing on my lap and I could tell she was enjoying what I was doing. All of it. I reached back under with my left hand and pinched a nipple while I pulled my fingers out of her and added a few more swats. I then rubbed her cheeks again with both hands and made sure I kept spreading them, exposing her fully. I then took my left hand and inserted a finger into her ass.

She clenched her cheeks and I smacked them again with my right hand as I made sure she knew I was going to touch her wherever I wanted. I don't know if she had ever had done anal play before, but I felt warm liquid on my leg when my finger passed the first ring inside her ass.

With my left finger still inside her back passage, I smacked her ass a few more times and then put two fingers back inside her pussy. I could feel my fingers touching one another, separated by a thing membrane inside her. The rubbing was doing the trick and I wanted to get the most out of what time we had. The situation was much different than in the hotel room with Katie where I could take my time. In here, she was uncomfortably positioned on my lap and I wasn't sure how long she would be able to stay there without falling off.

Also, the palm of my hand was now stinging and I wished I had my leather strap. But this was just a warm-up for the next time we met. Pulled my finger out of her ass and rubbed her cheeks while I continued massing her g-spot. I was also thinking about how far I could take it with her and the next time we met.

Then a thought hit me.

Shit, this is fucked up.

I added a few more swats and pushed three fingers in this time as I put my left finger back inside her ass. She was moaning and I could tell from her movements she was on the brink of orgasm. And while I could drag this out for a while, I wanted her to love this experience and come back for more. Judging by the amount of girl-juice coating my fingers, she would be back. I pulled them out again and smacked her ass a few more times then re-inserted three fingers and found her spot again.

Just as I felt her approaching the inevitable, I rubbed her spot more vigorously and added pressure with my fingers on my right hand and then pulled my finger out of her ass and smacked her cheeks again with my left. While an odd angle and the swats not as hard, it was still enough to send her over the edge.

Fortunately, the music in the bar was always loud and this was no exception. She screamed, moaned and began crying as she orgasmed, her pussy clamping and contracting on my fingers throughout. It went on in several waves and lasted almost a minute.

Her tears weren't from the pain, but from her release. By the time she had calmed down, there was a pool of liquid on the concrete floor and my right leg was soaked.

She had squirted! I had never been with someone who squirted and that included Katie.

I looked over and Cheryl's eyes were glued on Janet's pussy and was apparently approaching her own orgasm. She began shaking, let out a moan and grabbed the desk as she came. Janet was still coming down from her high and oblivious to what was going on behind her.

My cock was poking up into my jeans and into Janet's stomach. I wanted relief but this was not the place and I now had other plans. I rubbed her ass with both hands, massaging the redness the best I could. Her ass was bright red now and more so than when I had spanked Katie.

Cheryl had come down from her quick rubbing and noticed the mess on the floor. She smiled and looked back at Janet's pussy as she buttoned her jeans. I spread her cheeks again giving her a better look of her violated pussy and ass. But I knew we had been in there long enough and I'm sure the bartender was beginning to wonder where she had disappeared.

I helped Janet off my lap so she could stand. I took her into my arms and held her. She continued sobbing, but I knew this was something she needed. It was then she looked and saw not only the mess on the floor, but Cheryl staring at her red ass.

"Thank you Cheryl. You mind giving us a moment? I'll clean this up before we leave."

"No. I'll clean it up. It was worth it to watch. Take as much time as you need." She smiled, turned and pulled the door to as she left.

I held Janet for what seemed like an hour but was really only a couple of minutes. I pulled back and took her face into my hands.

"Are you okay?"

She wiped the tears from her face and caught her breath, standing before me still naked.

"I've never had an orgasm like that in my life! You can do anything you want to me any time you want. I understand now why Katie and Mike like spending time with you so much.

When can I see you again?" She hugged me again, holding me tight.

I smiled and pulled away. I leaned over, picked up her dress and pulled it over her head. She looked down at her bra, but I shook my head 'no'.

"Let's let you get composed before we walk out of here." She shook her head and leaned against the desk, but quickly flinched as her ass was apparently on fire.

I chuckled, "Are you okay?"

She laughed. "Yes, I think so. It stings but it was SO worth it!" She wiped another tear from her cheek as she took a deep breath. She looked deeply into my eyes and asked again when we could see one another.

"I head back tomorrow but will be back next week. Let's plan on getting together next Tuesday evening and plan on spending the night. I'll text you instructions before you come to my hotel but plan on a long night." She nodded, almost giddy and said 'ok'.

Yes, Tuesdays are my night with Katie and that was about to change.

"I also want you to seriously think about any boundaries and hard no's. I'll expect you to send them to me before we meet so I'll know how far I can push you. Understood?"

She nodded. A long pause and then,

"I'll do it." That should have been a 'yes' answer, what did she mean by that? I cocked my head with a questioning look.

"I'll do it if that's what you want." My look didn't change. I didn't understand her answer.

"I'll go back in there and blow that guy if that pleases you. Nobody has ever made me feel like this before and I'll do whatever you want me to do if you can make me feel like this again."

I was stunned and know my reaction showed. There was no way I would make her do that and maybe she had regained her senses and was now testing me? Whatever the case, I now had other plans for her. I would be pounding her hairy pussy soon enough, but tonight I was going to get my relief another way.

"No, that's not what I want from you Janet. But there is something I want you to do."

Man, this is fucked up and beyond the line, but really this line was never discussed. Can I really go through with it?

I sent a text and received a reply within a minute. The answer just as I had anticipated.

We walked out of the stockroom about 20 minutes later. She had composed herself to the point she could walk back through the bar without people staring.

On the way out, I pulled a $100 bill from my wallet and handed it to Cheryl.

"You don't owe me anything Mist, I mean, Scott." She smiled at Janet and then at me.

"No, take it. And sorry for the mess." I winked at her as I walked Janet out of the bar and down the street towards my hotel.

I pulled my phone out and sent another text to a different number,

'10 min'

It was read immediately and I was given a 'thumb up' reply

..........

I opened the door to my room and Katie was standing just inside waiting for me. She was naked, just she always is now on Tuesday night when I get to my room.

"Well? How did the meeting with Jan go?" She started walking towards me to give me a hug when Janet appeared behind me.

Katie was caught off-guard as the door closed behind Janet. Instinctively, she started to cover her breasts but a quick stare from me and she put her hands back to her side.

"Why are you trying to cover yourself? She's your sister!

That's something you failed to mention last week. But she has seen you naked before. She said you tell one another everything and even showed her your backside after we met last week."

Katie was now blushing. In all the time we had spent together and all the wild sex we had, I'd never seen her in a more compromising position than standing before me and her sister, naked. She knew I would easily find out but she obviously wasn't expecting me to bring Janet back to the room with me.

"But to answer your question." I turned to Janet and nodded. She pulled her dress up over her head and stood in the small hallway just as naked as Katie, as we had discussed. She then turned around.

"Oh my god Jan, are you ok?" Katie started to walk over to Janet, but I held up my hand.

"She's fine Katie. I kept my word and didn't fuck her. This time. But I learned she not only likes to be submissive like her sister, she also likes to be punished like you too. So, I gave her a spanking and an orgasm that rivaled yours last week." Katie bit her lower lip. She knew I would find out Janet was her sister and that would give me an excuse to punish her after we met.

But what she hadn't figured was that I was going to give Janet a front row seat to her punishment.

"You left out that little detail on purpose." She smiled coyly, already accepting the fact that she was going to be watched. There was a lot more to her than I thought.

"Let's go over to the bed and get started, there's no sense delaying the inevitable." She walked over to the bed and turned, taking off my shirt. She then sat on the edge of the bed and unbuckled my belt. Then my jeans and pulled them to the floor. My cock popped straight out and she took it in to her mouth, deepthroating me like I had taught her.

Janet sat next to Katie and watched as my cock was firmly in the back of her sister's throat. She started gagging, but she liked it when I made her do that. Yes, Katie was a good little submissive who liked to be used. And I was going to make sure I used her tonight. All of her.

I pulled my cock out of her mouth and looked over at Janet. Her eyes were focused on me and looked as though she was ready to take me into her mouth just as Katie had.

"Turn over, it's time for the strap." Katie acknowledged me and briefly looked at Janet. I picked up the leather strap from the nightstand, just where I had told her to place it. I also tossed the other thing on the bed for later.

Smack! Smack! Smack! I used more force than I ever had before. It wasn't because I was angry. No. It was because I knew that's what she really wanted. I was going to be visiting Cheryl tomorrow and buying a different strap, one designed to deliver more of a sting. I know Katie well enough to know when I get close to crossing a line and I was going to make sure I went all the way to that line tonight.

I added another dozen swats and her ass was already beginning to turn pink. Several more smacks and I not only had her attention, but she was beginning to squirm from the stinging. My swats were not spaced out like usual and the successive nature were bringing her close to the point of tears. I stopped and shoved my cock into her pussy. No warm-up because she didn't need it. She is always wet with anticipation when I walk through the door and tonight was no exception.

I fucked her hard and fast. I had been ready to explode since Janet and I first sat down. Now I was going to get my relief, but was going to make sure I delayed my first load as long as I could.

Her tits were swinging as I plowed her from behind and Janet was right there, watching. She began playing with her nipple with one hand and another hand was creeping through the forest to her saturated pussy.

I pulled out and added another ten swats of the strap, bringing her to the point of tears again. I rubbed her ass with one hand and reached under and found her clit with the other. I diddled her swollen nub as I massaged her pink ass and knew I could bring her to a clitoral orgasm soon. I know her body well enough to know when she is getting close and just as she was about to cum, I put two into her pussy and captured as much of her juices as I could.

With my finger on my other hand still flicking away on her engorged clit, I put my coated fingers at her pucker and slowly pushed them in. I'd only put my thumb in there before and she responded favorably. She pushed back against my fingers invading her ass and I knew she was mine.

I moved my fingers around inside and started fucking her with them. Between that and my finger on her clit, I could tell she had reached the point of no return and the first wave began rolling. Her ass is much tighter than her pussy and when she began contracting from her orgasm, I thought she was going to break my fingers.

I pulled my hand away from her clit but kept fucking her ass with my fingers. She looked back as I grabbed the strap and smacked her ass more, but not nearly as hard. She moaned and writhed and knew what was coming next.

I put the strap down and positioned my cock at her pussy again, putting it in just far enough to give me needed lubrication. I looked over and Janet was diddling away at her own clit and then another wicked thought went through my mind.

"Janet, lay down in front of Katie." Her look was that of shock but she started moving over without question. Katie turned around and shook her head no.

I smacked her ass again. This time with force.

"You are the one who brought your sister in to this equation. I told her I wasn't going to fuck her tonight and I'm keeping my word. But she needs release too and you are lick her hairy pussy while I fuck your ass. You don't seem to have a problem with your husband sucking on a cock, so you should be okay licking a pussy. Even if that pussy is your sisters." I smacked her ass again and shoved my two fingers back into her has far as they would go.

"You can't. We agreed no anal. Mike isn't even here!" I laughed.

"If you don't want it, tell me to stop."

Silence

"But Mike!"

"I texted him earlier and told him what I was going to do. He agreed it was time. He has always wanted to fuck you back here you know, but you never would. Well, tonight you are losing your anal virginity." Katie wanted it. She knew I knew she wanted it. Her game of no anal had gone on long enough. She had always wanted me to take her back there and it took being with Janet for me to figure it out.

Janet was already laying on her back in front of Katie, her legs spread and pussy waiting. Sisters or not, both these women were worked up and could have easily taken on the Panthers if they were lined down the hall. I pulled my fingers out of Katie's ass and positioned my cock at her tight pucker. I also reached over and grabbed the other thing I had thrown on the bed.

I pushed her head down between Janet's legs and she stared at her sister's wet, hairy pussy only inches from her face. Without giving her much time to think, I began pressing into her ass. Just the force of my body pushed her forward and her mouth into Janet's snatch.

Janet moaned immediately as her sister's tongue met her pussy. I continued my pressure and managed to get my cock all the way in to her ass. She was moaning and I know it was uncomfortable, but she wasn't complaining. She couldn't. She had her sister's pussy in her mouth while my cock was now fully buried inside her ass.

I held still for a moment, allowing her to adjust to the fullness. All the while she was lapping away on Jan's pussy. Finally, I began slowly pumping and knew I wouldn't last long. I looked over Katie's shoulder and saw the look on Janet's face I'd seen earlier. She began moaning and her body began shaking as her sister licked her to orgasm.

I was ready to blow my load and Katie's ass started spasming on my cock.

She's having an orgasm?!

Sure enough, her body started shaking and her ass kept clamping on and off my cock in rapid succession as the wave blasted through her. It was too much and I had reached the point of no return as I felt the tingling sensation flow from my balls and into my cock. I'm not typically vocal when I orgasm, but I was so in the moment I know I was screaming as I came and I couldn't control it.

The three of us lay in bed for almost ten minutes before anyone moved or said anything. The situation, the sex, the intensity led to the best orgasm of my life. The three of us hit the large walk-in shower and while there was some awkwardness between the sisters initially, it quickly went away when I started making out with both girls in the shower.

We made it back to the bed and while Katie was sucking my cock to get me hard for round two, I hit send. I had grabbed my iPhone when I was ready to penetrate her ass and recorded it for Mike. That was his ask when I texted him my intent. While he was not able to be there in person, he now had video to play and replay over and over of his wife not only losing her anal virginity, but also her first time with a woman. Her sister no less.

And I did keep my word. I did not fuck Jan that evening. We made out and played with one another for hours. After the second time with Katie I was hard again and Jan was on all fours, in position, begging me to fuck her. But I didn't. Despite being on my knees behind her and my cock rock hard and inches from her dripping pussy, I just couldn't do it . I'm a man of my word.

I waited 30 more seconds until the clock ticked to 12:00 a.m. Wednesday morning and then sank my rod into her hairy and very, very wet pussy in a hard thrust. The first of many times I would have both sisters at the same time, as this was going to be the new Tuesday routine.

Wednesdays would still involve Mike, but I'll need to think about how to involve him going forward. Maybe I pick up a chastity cage along with the new strap? That way he won't be able to play with his cock during playtime and be completely focused on using his mouth to clean up the mess we all make. Who knows? But I still have six months left on my contract, so I will have plenty of time to figure it out.