The Vacation Pt. 05

You surprised me. I know you love Shirley and would do anything she asked, or should I say told you to do. I'm Jealous of her." She added.

"Wow," I replied. "Was it a real bet or just rhetorical? I guess what I mean is what did the winner get?"

"Yes it was a real bet." Barbara said. "Whoever won the bet would get to paddle the loser. We had decided that the loser would receive as many strokes as you did the weekend. Unfortunately, we lost count since so many other players got involved. We estimated you received about 500 strokes so that is how many Shirley is going to give me. You are welcome to watch if you like."

Shirley got up and gave me a hug and a long and passionate kiss. She whispered in my ear to get my bag of toys from the bedroom. I returned a few minutes later with my bag.

Shirley told Barbara to stand still as she put wrist and ankle cuffs on her. She told Barbara to kneel and then attached a three foot spreader bar between her ankles.

Barbara was cooperating. She had lost the bet and now had to deal with the consequences. Shirley coupled her wrist straps together and then attached a strap to them. She bent Barbara over and attached a strap from her wrists to the spreader bar; passing it between her legs. As she tighten the strap, Barbara's arms were pulled back between her legs, forcing her head to the floor and her Ass into the air.

"This wasn't part of the deal." Barbara said. "The deal was..."

I put an end to her protests by pushing a ball gag into her mouth and securing it there. She tried to fight but it was too late. She was tied securely with her legs spread wide and totally exposed.

Shirley started the paddling. She was squirming from the first stroke. By twenty her ass had turned a bright shade of pink. Tears were forming in her eyes. By forty she was crying real tears. The squirming had stopped and she was simply enduring the pain like someone in subspace. When Shirley reached 100 she handed the paddle to me. She said she needed a break but told me to continue.

Barbara shook her head back and forth. My first stroke of the paddle was harder than any Shirley had administered. Barbara was again squirming. I delivered five more strokes in rapid succession. I concentrated on her left butt cheek for the next twenty strokes then switched to the right. After another 100 strokes I let Barbara rest. I rubbed her ass to feel how hot it had become. It was dark red with some bruising but I hadn't broken skin and I didn't see any blistering.

I put on a pair of gloves and started running my finger over her asshole. After a few minutes I stopped. I pushed against it, trying to penetrate her. I'm sure it was uncomfortable for her as I hadn't provided any lubrication. I asked her if she wanted me to continue. She shook her head no.

"I guess I'll resume the paddling then." I said.

I let up a little during the next set of 100. It was partly because my arm was tired and partly because her ass looked like it was starting to blister. When I finished the set I returned to playing with her asshole. This time when I asked her if she wanted me to continue she shook her head yes. I knew she would do anything to give herself some time to recover.

I dabbed my finger in the lubricant then pushed against her hole. It penetrated her to the first knuckle. When I felt I had lubricated her well enough, I added a second and then a third finger. I was working her hole in and out in a steady rhythm.

She loosened up quite a bit so I put a condom on before stepping up behind her and shoving my cock in her back door.

"Dean" Shirley yelled. "That wasn't part of the bet. Pull out. Pull out now."

Barbara was shaking her head no. She was moaning through the gag. I could see her body shake a little. Her juices were dripping from her cunt. She was enjoying this.

I kept sodomizing her until I filled her rectum with my cum. When I finished I withdrew and threw the condom away.

I concentrated on paddling her thighs during the fourth and fifth set. I remembered how much it hurt when she did it to me so I figured turnabout is fair play. When I administered the last stroke she seemed to collapse. I loosened the strap and unfastened the wrist restraints.

It took her some time to get circulation back. She was stiff and barely able to move. She was lying on her tummy. I bent over and kissed her ass. I rolled her over and buried my face in her pussy. She wrapped her legs around my head and squeezed. She didn't let up until she had two more orgasms.

It was time for bed. Barbara and Shirley had to get up early the next day to go back to work. I had an appointment with Ellen.

Barbara was heading up to her room as I sat cuddling with Shirley.

"We'll finish this at the beach." She said. "You better rest up because it's going to be a long week for you."

Chapter 7: The Vacation begins (Coming soon)