My most memorable spanking with Bob was our last. I had been spanking him about once a month for a year. I was moving and I told Bob that our last session would be one we would remember. The one thing that I wanted to do was to jerk him off. We are both married but had a spanking only relationship. I have always wanted to see another man cum, but I have no desire for any type of _s_e_x_ with him other than jerk off. The only way I knew that I would be able to pull it off was to extort him. Being married, we are both in the closet when it comes to spanking. As we always used his place, I had his address and I knew his wifes name. I was going to use this as a means to jerking him off.
Prior to meeting, I told him that to make this special, it was going to be a straight our discipline spanking. When he picked me up at our meeting place he was to remain silent to build it up. As soon as we entered the house, I grabbed him by the collar and started to spank him as we went to the living room. Once there, I started the one way interrogation.
"Bob, I am really dissapointed with you. Shoplifting is a serious crime. You are lucky that I know the manager of the store. I'm not even going to ask you why. You should already know that you are going to get the spanking of your life. Now, drop your pants and get over my knee."
He did and once I had him positioned, I commenced hand spanking him on his underwear, lecturing him as I went. After about 50 or 60 good licks, I stopped.
"Bob, you have been very naughty. You know how naughty boys are spanked, right? You will ask me, understand".
"Yes sir. Sir, please take my underwear down and spank my bare bottom."
I did. I slowly lowered his white briefs down. He was already a little pink. After some slow rubbing, I commenced to light up his ass. I continued to spank him for about 10 minutes. I then told him to get up and go get the ping pong paddle. He brought it to me and back over my knee he went. I peppered his ass with the paddle for another ten minutes until he was really moving and nearly in tears. When I thought he had enough, I asked him if was ever going to do it again.
Sniffling, "No sir".
"Well Bob, just to make sure, I going to finish this up with another hand spanking. When I'm through you will not forget this. Understand?"
"Yes, Sir".
I proceeded to spank him for another 15 minutes. His ass was a deep crimson red when I told him to go stand in the corner. While he was in the corner, I got some cooling hand lotion. After about 10 minutes in the corner, I told him to come back over to me.
"Bob, you have just had a very hard spanking. I expect you have learned you lesson. I have some lotion that I want to put on you to help out. Do you have a problem with this".
"No sir"
I then had him go back over my knee and started to massage the lotion in, slowly. I thought that I heard him moan quitly, and decided that this was the time to start my plan.
"Bob, you know this is our last session. We will probably never see each other again. I said I wanted to make this special. I'm not going to beat around the bush. I want to jack you off."
He immediatly stood up and put his underwear back on and went to the other sofa to sit down.
"No way. We made it clear there was no _s_e_x_ involved."
"Your right Bob. I don't want to have _s_e_x_. I just want to jerk you off and watch you cum. There isn't anything wrong with that".
"Yes it is. I'm not gay."
I'm not either Bob. I thought you would be apprehensive and didn't want to have to resort to this, but, if you don't I will send a letter with pictures to your wife."
"You wouldn't. This is extortion."
"Call it what you want. But if you don't want your wife to know, you had better get those underpants off and lay down on the sofa"
He sat there for a minute and just gave that I give up look. He got up, took off his underwear and layed down on the sofa.
I placed the chair next to him and started to slowly rub his _c_o_c_k_.
"Bob, please don't be mad. Jerking off is normal. Just lay back and enjoy it".
He didn't say anything, just looked up at the ceiling. I slowly rub his _c_o_c_k_ until he was completly hard then started to give him a hand job that I thought I would like. At first he just layed there, then he started to move around a little. I sensed that he was starting to enjoy it. Then he moaned and I knew that he was. After about another minute, his legs started to move quite a bit and his breathing was getting heavier, and I knew he was about to cum.
"Go ahead Bob. Shoot your load so I can see it".
"_s_h_i_t_ man, I going to cum" he groaned.
He then tensed up and his _c_o_c_k_ got even bigger and then he let loose one of the biggest loads I have ever seen. The first shot must have went 6 feet in the air. I think he continue to squirt out 5 or 6 more times before he finished.
"Jesus, that was good. I'm sorry that I even questioned you."
"Thats ok Bob. You should just listen to me more often".
"I know. If you don't mind, I would like to do the same for you".
"I was hoping you would say that".
I dropped my pants and we switched places. His hand job wasn't as good as my own, but I had a very powerful orgasm too. He got hard again while jerking me off, so I gave him one more. He came pretty quick, with almost the same intensity.
That was almost 2 years ago. I haven't been able to meet up with anyone since for spanking or jerking off. But, hopefully, someday I will meet someone that I can have the same type of relationship with.