Monday, a Man I'd serviced almost a year ago emailed and wanted to stop by. I had figured he was a one and done type, even though he'd emailed once or twice since trying to hook up. Monday it finally worked out and my demerit tally was now 136. That would be a fine total to stop at. Then Mr, Kisser emailed and I'm always eager to service him. As we were working things out I figured it'd be another 14 demerits. It wasn't though. It turned out to be 22! If I'd actually added it up beforehand I'd have known it was going to be more than 14. Maybe I would have made a different choice, but I didn't. E1 did email but the timing didn't work so luckily the demerit total stood at 158.
158! Holy cow. I was embarrassed to tell Sir Dennis, but I did. After all there's no point and no fun in not telling him. I was actually worried though about what he'd think when he realized what a cock whore I am.
Sir Dennis emailed me instructions as to how things would go and also reminded me to bring my paddles. I was simultaneously eager and dreading our next session. About an hour before I needed to get ready I laid down on my bed (on my stomach) and thought about how my ass was going to feel and how the demerit swats would hurt and sting. I got turned on but decided to hold off on jacking
At the appointed time I found the door to his office and announced my presence and waited for him. We were going to start off with a school boy sent to detention role play. After some suitable and appropriate chastisement I was bent over, hands on the edge of the desk and received 10 school swats, luckily with my jeans still in place. Oh man, what a way to start things off. No nice warm up. No easing into it. 10 stingers to my keister. Yeouch!
Then we moved to the other room where we'd played the first time. I showed him my paddles and then we laid down for some cuddling. I like how easy it is to lay down with him.
Then it was time to get down to the business of the demerits. I knelt between his legs and nuzzled his cock as he sat and reviewed my demerit log. He asked me about a few of the entries, the last one being 22 demerits with Mr. Kisser. He wanted details on how so many points had accumulated. I had to confess that 10 of the points were due to taking Mr. Kisser bare. We had a brief discussion about this and Sir decided that that would now cost 15 demerits. ugh. I like that Sir has changed the scoring but at the same time, fucking Mr. Kisser is going to get costly. Also, I'm not sure what I was expecting to happen with the demerit book. In the back of my mind I figured I might be asked about an entry or two. Maybe he'd remark on the number of entries. Giving details though was embarrassing and hot. To describe out loud to someone the ways in which I was a cock whore. To describe the activities and feel ashamed. Good hot fun!
Sir decided that the game we'd play today would involve rolling a die. Odds I keep my pants up. Evens the swats go to my bare ass. Great, hopefully the odds swats would be a tad easier. They weren't. I think he swung harder on those. The other challenge was that I had to keep track in my head of how many swats I'd taken. He wrote the numbers down and would periodically check my math. I came close to screwing up once but was able to backtrack to the right number. Phew! The dice made it all quite fun. When I got to 98 I rolled a 6. He gave me a choice of taking 2 and ending at 100 or taking all that I'd rolled. I think he liked that I chose to take all 6 and end the session with 104 swats (plus all the others that were just for Sir Dennis' amusement). He then marked my demerit book with the swats I'd received. I signed his special paddle and then we laid down for a bit more cuddling.
It was another great session with Sir Dennis. He makes it all interesting and fun... and painful. I'm a lucky boy.
Did you ever get paddled when in school? What was it like? Leave comments below.
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