Tommy had been seeing me for almost two months now. I was growing quite fond of him. We had reached a point in this relationship where I needed to know if he was a keeper. I believed that he was, but I just needed to know for sure. I needed real proof.
I put on my best black lingerie and slipped on a nice dress. I called him and told him to clean him self up and hurry over. I could tell this excited him. He was over in a few minutes ringing the bell. As soon as he came in the door, I could tell he was really wound up. It had been almost three days since he was last serviced, and the tension had built up in him. I instructed him to take his clothes off, and he did as he was told. I liked to look at him standing there all excited with his erect throbbing penis so hard. His body was lean and his skin soft and smooth. He was lovely a man, made all the more delicious by his innocent submission. Tonight we were going to have a very special encounter. I let him stand there for a few minutes, with his heart pumping. I stood just close enough to him so he could smell me and be aware of my presence.
I took a minute to place my palms on his chest and feel the warm strength under his skin. He was going to need all his strength tonight. I made sure to stand in such a way as to not give his cock any place to rub against. His penis just had to stand erect, with no attention being paid to it. I could see it aching for attention.
I grabbed him by the ear, and gently lead him over to the large chair and told him to get down on his knees. His reactions were swift to my commands. I made him lock his fingers above his head, a position he already knew. How precious he looked all submissive and kneeling there before me. I went back to the bedroom dresser and got out my leather belt and my cane. He could not see what I was doing, but he could hear me. He knew already this was going to be more than a simple spanking. As I approached him, his back arched a bit and his little butt cheeks tightened. I stood behind and above him and enjoyed the view of his completely naked body and his throbbing cock. I could see a little bit of a shinny fluid at the top of his pink head. His balls were filling up and his body was making semen. I had already trained him on how to control himself, so I was not worried about an accident. I ran my fingers through his hair and enjoyed this sweet moment. Then I started.
I raised the belt and brought it sharply down across his little ass. SMACK! SMACK! SMACK! His poor unprotected butt quivered with each lick. He started to rock his weight from one side to other to try to avoid the stinging blows. SMACK! SMACK! and SMACK! again. The belt did its work on his ass. His finger knuckles grew white from the tension of having to keep has hands locked. After fifteen blows, I told him to stand up. This was already the worst whipping he had been given, and yet so much more was to come. I turned him around to look at his erection. He was hard as a steel rod and I so liked to look at him standing there with his eyes closed and his breathing quick with anticipation. I pinched each of small nipples a couple of times, causing him to make a slight gasping sound.
Normally I would have given him a few strokes, but tonight was different. I had other plans. There were things I needed to find out. I told him to open his eyes, and I took off my dress in front of him. He was really hot and bothered seeing me there with my black outfit on holding that cane. I lead him by the ear over to the middle of the room and made him stand still. Again he was told to lock his fingers on top of his head.
“Spread you legs,” I ordered. “I am going to whip your little dick.” He shivered as he spread his legs.
I reached my hands in between his legs to get a good grip on his testicles, and then I whipped his hard penis with the cane. “How much could he take”, I wondered. Each little whack would cause his dick to jerk and rotate about. It was a such a sweet pleasure to see him jump and wiggle each time the cane landed on him. This was the first time I had ever addressed him this way. The blows were short stinging little whacks. I worked the cane up and down both sides of his shaft.
He stood there taking it and saying nothing. His eyes were firmly closed and he did his best to hold up the punishment. I could feel his full balls moving around in my hand.
After as many whacks as I thought he needed, I went back behind him and started to use the cane on his red and white ass. WHACK! WHACK! WHACK! the blows rained down until I finally heard the sound I was waiting for. After that last blow, he had made a barely auditable soft little whimper. I stopped the whipping and went around in front of him. His eyes where shut, but I could see small tears forming and starting to come down his cheek. As I stood in front of him, he started to break down, the little whimpers turning into a quite little cry. He held his hands above his head and stood ready for whatever might come next. This was the moment I was waiting to see. As he stood there whipped and hurting but still waiting to take whatever I dished out, I knew the answer to my question. I put down the cane and quickly took off my bra. I put one hand behind his neck and with the other I reached down to hold his hot penis. He was only about half hard now as he was fighting to keep back his little tears.
“Okay,” I said, “Okay” His little whimpers started to fade and I pressed forward so he could feel the warmth of my breasts on his chest. As I rubbed his now half soft cock, I told him he could put his hands down. I let him put his arms around me and his head fell down on my shoulder as he slowly pulled himself back together.
After a few minutes of him feeling the warmth of my body on him, he started to come out of it.
‘I love you,” he whispered. “Oh god, I love you so much.”
His cock slowly filled back up and his eyes began to dry. As I stroked him, his breathe shortened and his muscles tightened. After a while, I could feel him getting close, and after a few more quick warm strokes, his whipped and hot penis went into a spasm and I felt the warm bust of his semen all over my stomach. Over and over again his cock jerked involuntarily as it produced one load of white fluid after another. His knees buckled and he let out a soft groan. He completely flooded me. After he was fully spent, I gently held his penis and lead him over to the front of the bed. I sat down and he knelt in front of me. All the while I kept him in my hand. He sat down on his knees and put his hands on his thighs, just as he had learned. When he was seated, I told him to open his eyes. I looked deep into him, then I pressed my lips to his and kissed him fully. He responded with such openness and he totally gave himself all up to me. After a long probing kiss, I gently bowed his head onto my breasts and slowly stroked his hair. My other hand still maintained the hold I had on his genitals.
As I sat there, holding him, I knew I had found out what I needed to know. He was mine, and that would never change.
“I do love you, ” he quietly said.
“I know,” I said as I held him there in my arms. I knew I had to take good care of this boy.
More Bill Ward art.
Originally posted 2014-04-28 20:31:27.