I answered a spanking ad about six months ago. The part of the ad that caught my attention was the way he wanted to give the spanking, in a 'caring way, letting you feel each sensation and experience the pleasure of spanking.'
We have been e-mailing each other off and on for all that time. I shared with him a few torso pics just so he could get some idea of what I look like and then I finally gave in last night and agreed to meet him.
He instructed me to show up at his door wearing only underwear and absolutely nothing else, not even shoes or car keys. Upon receipt of this directive, I was instantly erect and excited about what was in store. I decided to give him a little surprise and showed up in my little boy fire truck briefs, the ones that are super low rise and show just a little of my ass crack.
He answered the door and immediately assessed me from head to toe. He grinned as he laid eyes on my underwear. "Nice," he mumbled.
He was, I'm guessing, in his early sixties and still pretty fit. He wore gray trousers and a white, fitted polo shirt. His hair was cut really short and was beautiful silver like it had been colored professionally. It was actually so nice that it gave me great ideas about how I want to look when I go too gray to cover up.
"Come in young man," he instructed. I was really nervous, it was cold out side and I found myself shaking a little. He noticed and whispered, "It's going to be ok. You'll warm up soon enough."
I noticed a chair in the center of his living room and several spanking instruments lying on a table next to it. There was a wooden spoon, a ping-pong paddle, a belt and a thin frat looking paddle with holes in it. That last one made me made my heart race.
He led me over to the chair and sat down while still holding my hands. He was looking right at my growing cock. It was straining in my little underwear. I stood there looking at him, not really knowing what was next. I mean, I knew a spanking was coming but how exactly was it going to play out. I shivered again at the thought. The head of my penis was poking out of my underwear. "It is so sweet that you are nervous young Jared."
He turned me around and inspected my body. He touched my ass and rubbed his hands down my leg. He turned me around and ran his hands along my abs and then put both hands on my hips. "Do you know why you are here young man?" "Yes, I said timidly."
"Why are you here?" "Um," I responded. "Cause you're gonna spank my ass." "That's right."
He pulled me down and over his knee. It was a little awkward at first. He rubbed his hands over my ass and then began spanking it ever so lightly. My cock was pressed up against his legs. "Pay close attention to what you are feeling," he said. It was so light for me, so I really wasn't feeling anything. "Young Jared has been a very bad boy and Uncle Dave is going to teach him a valuable lesson." I was a little freaked out by what he said for a few seconds but my attention was pulled back when he picked up the pace intensity.
As the spanking grew stronger and stronger I began to squirm in his lap and beg him to stop. It stung, even through my underwear. I kept trying to grasp his hand to stop but he just pushed it away and continued to spank me.
As it was just beginning to become unbearable he stopped. "Stand up young one." I stood up, massaged my stinging ass and looked down toward my raging hard-on. Pre-cum had stained my underwear.
"Step toward me young man." He reached for the waistband of my underwear. "Now Jared remember, this is for your own good. You asked for this." With one quick motion of his hands I found myself standing naked and hard in front of him. Pre-cum accumulated at the tip of my cock and began the long drooling trip to the floor. I moved to catch it but he slapped my hands away. All I could do was stand there in embarrassment, looking down at my naked body and pre-cum pooling on the floor.
"Jared, I want you to pick an instrument from the table." I looked over at the collection and pointed at what I thought would be the least painful, the belt. He picked it up and threw it aside. "Great," he said. Now that we've eliminated the one we aren't going to use I want you to pick another." I picked up on the fact that he didn't say we were going to actually use what I picked. He just said the word another, so I picked the one I thought would be the most painful, the one with the holes. "Nice choice but don't you think that one will sting a little?" I looked over at him. "Well ok," he said. "Bend over my lap."
He spanked me again with his hand. Even though it was much lighter than the last one's he gave me, it still stung a lot more because he was spanking my naked flesh. I was a little further back on his lap and my cock kept brushing his pants over and over as it bobbed up and down. The spanking was just hard enough to be erotic. Jeez man I was really getting into it saying "Fuck yeah, fuck yeah."
Toward the end of this part of the spanking, he spread my cheeks with one hand and spanked my anus. It was driving me so fucking crazy I began humping his leg. "Fuck yeah," I screamed, "fuck yeah."
He stood up without warning and I fell to the floor. "Get up and bend over the chair." I braced myself on the seat of the chair as he retrieved the wooden paddle and began to spank my ass. Pain shot through my body immediately. It was not longer erotic. "Count to ten," he said as another swing landed on my ass. "One," I screamed.
We got to ten; he stopped and caressed my ass as if admiring his work. It was really hot, on fire, and I was sweating as the stinging sensations escaped my body.
He went to the couch and motioned for me to follow. "Lay over my lap Jared." Fuck, I thought, no more. I'm fucking done. "Come on. This is the last one." I lay over his lap face down. "Not that way," he said. "The other way." I turned over and he helped me scoot up where my ass right in his lap between his legs.
"Jared, I want you to masturbate before you go." I closed my eyes, grabbed my cock and began to stroke. He just watched as I pumped and pumped until I was cumming all over myself.
I stared right into his eyes as I licked the cum off my fingers.
The best part of the night for me was at the moment he opened the door for me to leave. I was still in only my little briefs and just barely out the door when his neighbor walked up the steps. I don't think she was amused at all. I said hey in the friendliest way and she just stared at me in judgment as I passed her.