A Pleasant Sort of Torture, Part 17


Baseball. Football. Basketball. The quadratic equation. Anything I could focus on rather than Rose’s hand on my cock.  She stroked it, played with the tips, and dragged her nails over my glands. She knew that making me cum in that moment was not a problem; a quick series of strokes and I would have filled her hand with goo, but I think she wanted to stretch it out, give me some hope that I could last, and take it away as the end came in sight.

“Such a serious look on your face,” Rose said as she swirled her thumb around my tip. “Whatever could you be thinking about.”

“Just focusing on the road,” I said through gritted teeth. I wanted her to push me. i wanted to cum in her hands. Fuck losing the bet; after a day of restraint, I needed to let loose.

Rose smiled and pulled her hand out of my shorts. Her fingers were covered with pre-cum. “That is probably a good thing,” she whispered. “I wouldn’t want you to crash.” She licked the fluid from her fingers and sucked her fingers into her mouth. Every slurp made me wish I had not included a no oral stipulation in our little bet. She stuck her hand back up my shorts and grabbed my shaft. Her hand was wet with saliva and slick as her mouth as she stroked me from tip to base.

E=mc². The Gettysburg Address. The Declaration of Independence. Football.

“I don’t think you’re going to make it,” she said before unbuckling her safety belt. “In fast I think you are almost begging for it now, aren’t you?” She kissed my earlobe and whispered. “If you beg me, I’ll let you cum right now and I’ll let you sleep with my cum soaked panties tonight.” She bit my earlobe and pulled.  “What do you say?”

I wanted to say yes. Oh God how I wanted to say it, but I could not do it. Part of me wanted the reward for winning, but I think I did not want to lose more than anything else.

“Tempting, but I am not ready to give up just yet,” I said as I accelerated a little more.

“Suit yourself, but you’re not going to win this one,” she whispered. She stroked me with a slow, steady stroke, but backed off the moment she felt me getting close. She had me riding on the edge and I was starting to drool with the strain.

I turned onto my street. I could see my house at the end. All I had to do was hold out for another minute and I would win.

Rose knew where we were and said, “Time to win this.” She tightened her grip and stroked me hard and fast, making sure she took my tip onto her fist each time.

I tried to hold out. I clenched every muscle I could, but I had been on the edge for too long and fell short of victory within sight of the finish line.

“Fuck,” I said in a throaty growl as my cock jerked and filled her hand with cum.

Rose cooed and continued to stroke until we were in my driveway. “Nice one,” she said. “I might not have been able too swallow all of that down.” She pulled her hand out of my shorts and licked the cum from her fingers. Once she was done she said, “Let’s get the boys to bed and we can talk about tomorrow.”

I nodded and tried to get my breathing under control while she hopped out. Fuck. Fuck. Fuck. What the hell was it with this girl?

I got out of the SUV and pulled out one of the boys. We walked upstairs, undressed them and put them to bed. When I got back downstairs I found Rose in the kitchen.

She held out an open bottle of beer and said, “You’re a good sport, and my boss, so if you want to back out of our bet…” She let the words hang in the air, but she knew what I would say. She thought she had me figured out.

I was afraid she did.

“No. A bet is a bet and I’ll live up to my end,” I said.

Rose smiled and said, “Good. I am going to sleep in a bit tomorrow, so I’ll be here at noon for lunch okay?”

“Sounds good,” I said.

She finished her beer and walked over to me. “Make sure you get some rest,” she said. “It’s going to be a busy day tomorrow.” She threw her arms around my neck and kissed me, but let go and left before I could grab her and try to convince her to stay.

I sighed and finished my beer before heading up to bed. I fished my phone from my pocket and noticed I had a couple dozen text messages waiting for me. I took a look while I was getting undressed.

The first couple were from Susan, thanking me for the good time and the investment. There were a couple more from friends, but the bulk of them were from Cindy.

The first text said, “I did as you said, but I couldn’t wait until Monday to share.” The messages that followed were filled with pictures of Cindy having sex with her husband. Pictures of his dick in her mouth, her riding him, his mouth on her tit, and him fucking her from behind. The pictures were arousing and I loved the way she looked at the camera. I knew she was thinking of me.

I took a long, hot shower and thought about Cindy fucking her husband and wishing it was me. I lathered up good and shaved below the waste until everything was nice and smooth once more. I soap ed up once more and stroked my cock to the thought of Cindy’s husband watching me fuck his wife on their dining room table.

Once my load was flowing down the drain, I rinsed off, dried off, and climbed into bed. I tried to imagine what Rose would have me do the next day, and each scenario I conjured up left me harder than the last. I tried to banish the thoughts from my head, but even once I managed to go to sleep, there was Rose, haunting my dreams with possibilities.


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