Literotica's "Peggy46" offered herself up as a subject of stories. I accepted the offer and sent her the first part of the one here. She approved it so here it is expanded. Chapter 2 coming soon!
***************************
Ouch!" I yelled as her hand slapped hard -- again -- across my naked ass. Then she stopped.
"Oh, did that hurt your little ass, Honey?" Peggy made her voice sound so insincere.
"Yes," I said.
"Well, maybe this will help," she said, picking up the leather strap. I knew exactly how that would feel. I winced as it whistled through the air and landed with a sharp 'Snap!' across both cheeks. I jumped with each successive stroke. Then it happened. This was the reason I submitted to this punishment -- well, the other reason than simply the act of submitting itself.
My endorphins kicked in and the pain became a kind of pleasure. I worked through the pain, as if it was happening to somebody else's ass. Peggy finally dropped the strap and put her lips close to my ear. "Do you want me to stop?" she asked.
"No," I whispered, my eyes closed tight.
"Then ask me to go on."
"Please, Honey. Paddle me some more. Paddle my ass red." It was a strange kind of pleasure, too, that came with asking to be spanked. I was not tied down. This was a completely free choice.
She took up the leather, spade-shaped paddle. She stroked it gently across my tortured butt. I trembled, knowing how hard she would bring it down. She reached between my thighs and took my cock and balls in hand. She squeezed them -- not hard enough to hurt, but firmly. I groaned. In the middle of my groan, she brought the paddle down with a crack! I jerked,making her grip on my genitals tighten. She began to rain my ass with strokes of the paddle. Each time, I pulled up a little bit. I was making my own dick and balls hurt as a counterpoint to the pain I felt on my ass. The pain did nothing to lessen the erection in Peggy's hand. In fact it made me harder yet.
She released my cock and brought her thumb against my anus. I wriggled in delight. She swatted me and began to insert her thumb into my oiled ass. By the time she had it all the way in, I was near the edge. The paddle fell and she pumped her thumb into me. The waves began to wash over me. She knew it, because my asshole contracted with each spasm of come jetting from my cock.
She dropped the paddle to the bed. She slipped her thumb out of my asshole and lay down next to me. I was drained and whimpering. I was not ashamed about the whimpering. It was not weakness, only a surfeit of pleasure and passion. She stroked my back and butt as she kissed the side of my neck.
I rolled to my side (I was too sore to lay on my back yet) and gathered this lovely, loving woman into my arms. Another day it would be Peggy's turn, but right now it was my turn to feel the love I have in my heart for her for allowing me this exquisite pleasure.
***********************************
The next morning the pain had lessened, but my ass was still sensitive. In the shower, under the hot spray, it felt like a slight sunburn. I recalled the feeling of being penetrated with pleasure.
My dick began to rise with the memory. I lazily stroked it while massaging my own anus with my other hand. I wasn't seriously masturbating however, just fondling. I had a job to go to and it was getting late.
At the office, I am a supervisor. Seven people work under me, four men and three women. Two of the women are married and in the forty to fifty year age range. The other is single, attractive, and in her early thirties. Mandy was promoted quickly to an associate's position in our company. She is very talented at her work and I have to admit she deserved the bump up. Her personality is ambitious and aggressive.
I had a staff meeting scheduled for that morning. As it happened, Mandy took the chair immediately to my right at the round conference table. As did several other of the associates, she had placed her attache case on the table before her. While Spencer, our foreign marketing associate, was relating a problem that had arisen out of the return of Hong Kong to China, I happened to glance down and to my right.
My hope was to possibly get a look at Mandy's long legs. What caught my eye, however, was the keychain that rested in one corner of her case. Several keys occupied the ring. The fob of the ring, however, was what really caught my eye. It appeared at first to be one of those fishing lures. The kind that looked kind of like a squid with its tentacles sticking out.