Introduction:
Mindy had just finished giving me the best blow job I had ever had. I had come into some money and Mindy was going to be in deep shit if she didn’t get $30,000 (see part 1). After she got off her knees she said
“Are we done?”
“Sure, is there something you wanted to talk about?” I said jokingly
She started to move to get her cloths.
“No, just sit down. I think I like you naked”
She glared at me, sat down, and the said in a resigned tone.
“I’ll do it. I’ll sleep with you, if you give me the money?’
“You’ll do a hell of a lot more than that. I checked online and for about $200 I can get an hour’s worth of sex. $30,000 would let me cum 150 times over six days. Giving you the money for a one-timer would just be charity, and you wouldn’t learn a lesson, now would you?”
I didn’t much care if she really learned her lesson about gambling, but I thought an appeal to her conscience might get more cooperation and more enthusiasm.
“So what do you want? You want to fuck me 150 times?! she said a bit angrily
“First, you best keep that temper under control, or I will bend you back over the desk. Second, I was thinking that I wanted a sex slave. We are going to fly to Las Vegas and then you are going to do anything I want for the whole weekend.”
The church auditors were due on Monday. Today was Thursday. Mindy had waited until almost the last possible minute, trying to come up with a better way to get the money.
“What? Tomorrow? What do I tell, John? There isn’t time?”
“That sounds like your problem. When five o’ clock comes around, you best be packed and ready to go to the airport. Oh, and don’t pack any underwear, you won’t be needing it”
“No, there has to be some other way. I’ll let you fuck me anytime you want, please”
“You must think I’m dumb. Once you get the money, I have no power over you. As a matter of fact, I don’t like that you would even suggest that. Get your ass back over the desk.”
“Don’t. Please, it really hurts.”
“Yes, it does. And if it hurts enough, maybe you will figure out what you are supposed to say and do. Now move, before you earn double”
With that she got back into position. She put her hands on the edge of my desk, and bent over putting her head on her hands. Her tits dangling, and swaying slightly.
“Now, how many do you think you deserve?”
“One” she said flatly.
Wham! I hit her already red ass with a blow that had started with a four foot arc. It was much harder than the others, and it was meant to deliver a message. She grunted loudly and squirmed. But she did not stand. She was learning.
“How many?”
“Ten!” she said quickly “Please, don’t hit so hard. I will be good. I promise”
I almost felt sorry for her and let her off with one swat. Almost.
“Since you asked so nicely and promised to be good….”
The next two were less forceful and I took my time. I stood to the side to get a better view of her tits. With each blow, she would lurch forward to subconsciously escape the pain. With each blow her tits would jump and sway. By the third blow I was pausing to fondle the nearest boob. She did not protest, but I was starting to get a signal in my antenna. I didn’t know if I could even go again this fast. I’m not a kid anymore.
Whack! Whack! Whack! Swats four, five, and six, I did in quick succession. I think I actually got number six delivered before her ass had sprang back from number five. Mindy drew in a large breath of air and held it with those blows. They did hurt. Her tits were still doing that jump-sway thing and I had a raging hard on. This would not do.
“I have an idea” I said “Let’s have a test to see what you have learned. I can either give you the last four swats to your red, possibly bruised little ass, or I can fuck your pussy that is so prominently on display. Your choice”
Now if she was smart she would take the fucking. She was going to get plenty of it this weekend anyway. What would one more be? If she chose the spanking, she had to figure I was going to hit her harder because she knew I wanted to fuck her.”
“No more spanking, please. Just fuck me and get it over with”
Wham! I delivered another very smart blow to her ass. This time she did let out a small scream.
“Ask me nicely to fuck you”
“Please fuck me. Pretty please. I want you to fuck me” she said quickly through the residual pain
“That’s better”
I said as I took my pants down again. Her heels put her cunt at exactly the right spot and I slowly entered her. She has two kids so I didn’t expect her to be tight, but she was tighter than I expected and very wet. I started with a few slow thrusts and then I started faster. I had both hands guiding her hips back to meet my thrusts. It felt incredible. As I continued to plow her pussy, and she grunting softly each time my pelvis met her sore, red ass, I took one hand off her hip and put the thumb on her little rosebud, and pushed slightly. I got the reaction I expected and she tightened up, increasing the pressure on my cock. That did the trick and I felt my balls start to tighten and I knew I was going to come soon. Both hands now on her hips and I was slamming her for all I was worth. The desk was actually moving a bit with each thrust, and then I exploded deep inside her.
I pulled out and hobbled over to the front of my desk to get some Kleenex out of a drawer. Mindy stood up and asked
“Are you planning to do me in the butt?
“I’m planning to fuck that sweet ass of yours every chance I get. And every time I do, you are going to chant ‘Gambling isn’t worth it’ You’ve got it into your head the gambling gives you pleasure. I’m going to fix that”
Again, more bull. This might work or it might not. I just wanted her pliant and willing to do everything I wanted, and do it if not cheerfully, willingly.
I tossed her the Kleenex and told her
“5’o clock tomorrow until we touch down back home Sunday night, your ass, and everything else is mine to do with how I please. You deny me nothing. You do it willingly, without too much objection, I like a little begging, and you do what ever you can think of to increase my pleasure. In return you get $30,000 in cash and we each go our separate ways. Deal?’
“What cho..” she started. But her sore ass must have reminded her of her manners. “OK, Friday until Sunday, I’m yours, then I get the money.”
I thought about making her get dressed downstairs in the ladies room, forcing her to walk naked for about a hundred yards. But, after cuming twice I was in a good mood. I never enjoy watching women put their cloths back on. Watching the tits disappear into a bra always brings a bit of sadness. But, I buoyed my spirits with the thought that I would be getting all I wanted in 24 hours
Friday was a very long day. I took notice that Mindy was wearing a skirt today. She was wearing a bra, but I expected that. She cornered me around noon and said we would have to meet at the airport, as John was going to drop her off.
Quitting time came and I was at the airport ticketing area thirty minutes later watching for Mindy. I didn’t have long to wait, as true to her word John dropped her off, and was gone in a minute. She walked in, saw me and I put one arm around her pulled her in close for a kiss and grabbed her ass at the same time. She resisted for a split second, and then opened her mouth to accept my tongue.
“Good girl” I said “You’re learning”
She smiled a weak smile and then I said
“We might as well keep with the education. Follow me.”
I lead her to the elevators where we dropped down a level, and we walked towards to back of the garage.
“Where are we going?” Mindy asked.
“My car. It’s good spot for lesson number one.”
We were at my car in a minute. It was all the way in the back, with the passenger rear door facing a bare wall. I led her to that side and told her.
“Lose the bra and panties.”
“Here? Someone will see.”
“Shut up and get it done. You’re on my time now, and if I keep getting grief from you we can call it off, right now.”
Without another word she reached up underneath her skirt and pulled her panties down, swiveling her neck constantly looking to see if someone was watching.
“Can I take off my bra in the car, please?”
“Ok, it’s open”
And she opened the backdoor and pulled her top up and over her boobs. With that she unhooked it, and gave me a nice show as she took it off and readjusted her blouse.
“Good. Now bend over into the backseat so I can fuck your ass”
She had a look of sheer terror in her eyes. She was not expecting this so soon.
“Please. No. Someone will see. It will hurt”
“Maybe. Yes. And don’t forget to chant “Gambling isn’t worth it”
I grabbed her by the shoulders and spun her so she faced the backseat. She leaned over, and her skirt rode up a bit. Not nearly enough to see her pussy, but enough to get my cock to respond. I put one knee between her legs and gave her a bit of a nudge, as I leaned around her and yanked her top well above her tits. With those exposed, I kneaded them a few seconds, feeling the nipples harden.
Now it was time for the other side. I got behind her and slowly lifted her skirt above her hips exposing her cunt and the much tighter orifice I was about to violate.
“Please. Not dry. You’ll kill me”
“So you’ve done this before. Then you know to relax or it will hurt even worse.”
I wasn’t going to do her dry. It would hurt me too, and stretching her asshole would be painful enough. I reached into my pocked and pulled out a veterinary syringe I had filled with Astroglide, and after shooting a small amount on my finger to lube it up, I started working it into her ass.”
“What’s that!?” she exclaimed as she also tightened her ass.
Whack! I slapped her on the side of her ass with my hand and told her to relax. After a few in and out strokes of the syringe, I pushed the plunger and shot most of it into her anal canal. She felt the coldish liquid and started to quiver a bit, both from the chill and the anticipation of what was coming. I used the rest of the lube on my cock, which I had unsheathed moments earlier, and touched the head to her tight little hole. She instinctively tightened.
“Look it’s going up your ass. We can do it the easy way or the hard way. It’s your choice”
She relaxed and it pushed. I could feel the head begin to breech her hole. I kept a steady pressure and the head popped in. She jumped a bit and said
“It hurts. Please that’s enough for the first time, OK?”
“That is not what you are supposed to be saying” I said as I pushed a little deeper and feeling her tighten around me.
“Gambling is not worth it” she started
And I pushed all the way in. She gasped and sputtered to get the words out
“Oh, that hurts. Please. Gambling is not worth it”
I was buried will my balls resting on her cunt. So I pulled back and started to pump her ass slowly. She resisted at first, but then relaxed some. It was still so incredibly tight. There was no way I was going to last long. So I grabbed both hips and picked up the pace. I pulled almost out and slammed back in. I did this time and time again. With each thrust she would stifle a cry and turn it into a groan. I was getting close, so I reached under and grabbed one of her tits, found the nipple, and twisted it. She buried her head into the backseat and let out a scream as I drove my load into her ass.
This was going to be such a good weekend.

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