Please see Stu999's story for the other side of this situation....
....and I heard my buddy Dan yell out "No, man, you got it all wrong, the groceries you caught Eric with were mine, you shouldn't be whippin' him, it should be me!"
I knew better than to take my nose out of the corner, Dad had impressed that on me more than once with more lashes of his belt on an already sore bottom but I wasn't told that I couldn't talk so I said, "Dan, you should have just left it alone, my strappin' was almost done!"
I could hear Dan pleading with the boss to let me get dressed and leave, Dan said that he'd drop his pants right now and get over the desk and take the lickin' and that it wasn't fair to whip my butt for something that I didn't do. I heard the buckle of Dan's leather belt that he always wore click as he started to undo the fly of his jeans in preparation to pull his pants down for the strap.
"Enough, you two," came the bosses' voice, "Eric, you stay in the corner, Dan stop taking your pants down, you forget who's in charge here."
I stood there with my dick still drooling, hard as anything, and very aware of my striped and hot bum glowing out into the office. The welts from that darn strop were just throbbing with pain, much worse than Dad's belt!
I heard Dan pleading with the boss, telling him how he was out of money and wouldn't have any more until the next payday and how he had promised to pay me back the money that I had lost from being suspended and how he'd do anything if the boss didn't fire him.
"Eric was going to get two dozen strokes of the strop for stealing," the boss said, "and that seems like a fair punishment to me so that's what you will get. In addition because you cost Eric so much money I think it will be fair if he's allowed to give you another dozen strokes as well. Right now, though, before we get going with the strop I'm going to give you a little boy spanking over my knees, you behaved just like a little boy when you didn't own up to your crime and let Eric take the rap for it" The boss sat in his chair and called Dan over to him. He told Dan to lay down over his knees and I heard the chair creaking as it took the extra weight.
I heard spanking sounds but they didn't sound right somehow, muffled kind of. About fifteen or twenty whacks sounded in the room and I heard the boss tell Dan to stand up. I heard a zipper going down and then a rustle of cloth, he was pulling Dan's jeans down from the sounds of it! I heard the chair creak again, must be Dan getting back over the bosses' knees and then spanking sounds started again, still muffled but not quite as soft a noise as before, I was guessing that the boss was spanking Dan on his boxers.
A couple of dozen smacks landed and Dan was starting to moan and then there was a slight pause and the spanks started again, fast and hard. Lots of spanks hit Dan's bum and then there was another pause and the spanking started again, this time it was a sound that I was very familiar with, the good old sound of bare hand hitting bare bottom skin. That was more like it, Dad never spanked me on anything but my bare backside and from the sounds of it Dan was starting to whimper and sob a bit.
"If you think this hurts, wait until you feel the strop!" said the boss as he continued to spank and spank Dan's bare backside.
Finally the spanking stopped and I heard the boss tell Dan to just take off his shoes, socks, pants and underwear which I knew would leave him dressed in a T-shirt. I was so aroused by the spanking my dick was bobbing up and down with my pulse and I still needed to pee really big time.
I heard the pad of Dan's bare feet move around to the front of the desk and heard the boss tell him to bend over the top of the desk and pictured him in my mind, his bum up and ready to whip, his cute boy-hole on display above his dangling nuts and dick. I was so concentrated on this mental image that when the strop hit the desk with a horrible cracking noise it scared me and a scalding squirt of pee came out of me to splash on the wall and puddle on the floor! Darn it all, this was the second time today that I leaked like that!
"Eric!" the boss yelled, "You should have been all done but now you've gone and wet on the floor like a baby so I'm going to spank you like one. I'll get to you in a minute or two, just stand there!"
I heard that darn strop come down across Dan's buns and his yell of pain and that first lash of the strap was quickly followed by a bunch more while Dan wailed and begged for the hiding to stop, he couldn't take any more. After a dozen searing strokes burned into Dan's behind he was let up off of the desk and guided over to the other corner in the room, Dan was still crying as he stood there.
"Eric, come here," said the boss.
I left the corner and went over to where he was standing, my hard dick leading the way dribbling a little pee and pre-cum fluid. The boss handed me a roll of paper towels and told me to mop up my puddle and then to come back over to where he had sat down in the chair again. I mopped up and tossed the wet towels in the trash can and went back to where he was sitting. He made me lay down over his knees with my woody between his spread legs, I hadn't been in this position for years, Dad had started to whip my butt with the belt while I was standing up when I was around eleven or so. It was so embarrassing to be like this and it got worse when the boss spread my legs wide, propping them open with his right knee, so my crack was spread wide. He picked up this wooden ruler from his desk and began spanking me with it, it stung pretty good but nothing like the strop but then he started to spank my protruding boy-hole with it and man, didn't that sting! It hurt enough that I just had to yip every time he smacked me that and he smacked me a whole lot with that little ruler, it felt like he had stuffed a hot coal up inside of me!
I had tears in my eyes when he finally let me get up, more from getting my boy-hole spanked than anything, not only does it hurt like crazy but it's so humiliating to be spanked there, I mean that's a pretty private spot on a guy's body! I don't share it with just anyone. He told Dan to come back and lean over the desk again to take the second part of his whipping and Dan begged and cried but it did him no good, the boss firmly told him to do as he was told. I heard the crack of the strop biting into the tenderized hide of Dan's ass and his howl of pain.
"Eric, come over here and hold his arms behind his back so he can take his medicine," said the boss. I walked over and got on the other side of the desk and the boss made Dan put his arms behind his back and I leaned forward and took a firm grip on his wrists with both hand, my weenie sticking out over his head.
The boss started laying the leather across Dan's butt cheeks again and he was howling and screaming almost and darn it all, my weenie leaked pee again, right on Dan's head! It wasn't all that much, just a little dribble, but Dan yelled that I was pissing on him. The boss just looked at me and shook his head as he continued to land stroke after searing, blazing stroke of the strop across Dan's fiery ass cheeks. Boy, didn't his bum look sore!
Finally the boss laid all twelve strokes on Dan's bottom and led him back to the corner, crying loudly. I glanced over and saw him standing there with his bum looking like a truck had run it over and did a burn out, it was so raw and sore looking and glowing like a stoplight in stark contrast to the paler skin of the rest of his body.
"Eric," the boss said, "we need to do something about this unfortunate leaking habit of yours."
"I'm sorry, I just can't help it," I said, "seeing someone getting their ass strapped like that is scary."
"Take off your shirt," the boss said, "I need to spank you some more and I don't want any part of you to overheat but your bum."
I did as he told me and went back and laid over his knees again in the same position only this time instead of leaving his legs spread wide he clamped my stiff weenie in between his thighs. He started spanking me with that ruler again, all over my sore bum and paying a lot of attention again to my sore boy-hole and as I jerked under the sting of that ruler back there I was rubbing my woody between his legs. Six stinging spanks in a row landed on my pucker and then it happened, I shot my load between his legs! He continued to spank my poop chute while I was cumming and it just seemed to drive the cum right out of me, long, hard squirts that seemed to go on forever. Even after I stopped cumming he was still spanking me there and boy, don't that hurt! There is nothing to match a spanking right after a guy's come off and that area is extra special sensitive anyway and it hurt like hell with each spank. Finally he let me up and ordered Dan back over the desk for the twelve lashes with the strop that I was to give him.
Dan was crying loudly again as he followed orders and got over the desk. The boss handed me the strop and held Dan's hands behind his back. I looked at Dan's bottom and it looked awful but I drew back the strop anyway and landed a fiery stroke across both his cheeks right over his butthole that was winking at me between his fiery red cheeks. Dan absolutely screamed and struggled against the bosses' grip and I saw him suck his boy-hole in tight only to have it protrude out again.
"That's enough," I said, laying the strop on the desk, "I'm satisfied that he's had enough of the strop, his bum can't take any more of that thing!"
"Okay," said the boss, "you don't have to spank him if you don't want to but you need to get some satisfaction from him. I don't care what you do but it has to take place in front of me in the office."
"Anything, man, I'll do anything!" Dan sobbed. "Just don't whip me any more."
Anything, huh? I smiled. This could be interesting. I could still see his boy-hole winking at me as he tightened it and then let it relax and felt myself getting hard again. Maybe I should....
Nope, not yet.
"On your knees, dude," I said to Dan.
He slipped off of the desk and knelt in front of me and needed no coaxing, it was not like he'd never done this before. It didn't take long for his talented tongue and mouth to get me hard as a rock again and then I pulled out and lifted him to his feet, turned him around and bent him back over the desk. I aimed my slippery dick right where he was winking at me and put some pressure on and heard Dan yelp a little as I opened his back door and stepped inside. I ignored his begging and yipping, that's just part of the game he plays when we do this kind of thing, he likes to pretend that he's being ripped apart but I know better.
"Man, you're killing me!" Dan howled.
"Would you like me to whoop your sorry ass instead?" I asked.
"No, no, man!" he sobbed, "anything but that!"
I've got this wonderful thing I can do and it used to be the envy of all my buddies when a bit younger, you see I have almost no down time after cumming, I shoot off, I go limp and get hard again in a matter of a minute or so and can cum again almost immediately. I was always the last man standing during a circle jerk competition. Normally I'm not all that quick on the trigger but the circumstances of getting my ass whipped and seeing Dan get his whipped as well had me really aroused and it wasn't long before I shot off again, starting inside of his bum and yanking out to finish squirting my man juice on his welted and very sore bum. Then I stepped back a bit and watched my dick shrink down again.
The boss brushed by me and lifted Dan to his feet and then to my surprize turned him around and sat his ass on the edge of the desk and started working on his erect dick with his mouth and seeming as getting your ass tanned tends to make a guy horny it wasn't long before I saw Dan gasping as he shot off a load of his own, filling the bosses' mouth for sure, Dan comes a lot. I was putting my pants back on, figuring that all was finished up here now.
"Not so fast, Eric," the boss said, "we aren't quite finished here yet."
He had me take my pants back off and take Dan's place on the desk, I figured if he wanted to suck me off as well, why not? Instead he pushed me down so I was laying on my back on the desk and lifted my legs and put them on his shoulders.
"Hey, man, what you doing?" I asked.
"Finishing off your punishment," the boss said as he started working over my pucker with his finger. Now I like getting it up the chute as much as I like reaming some other guy out but felt that I had to protest and complained as he opened me up by sticking in two and then three fingers, three fingers being the magic number, if a guy can fit that many up another guy's bum his dick will fit with ease.
I heard the bosses' zipper go down and felt his dick replace his fingers and pretended to yell in agony as he thrust into my hole, heck, I'd felt bigger up there but why not pretend that he was the biggest I ever felt? As he started to ream me out suddenly Dan bent over my head and started to suck on my once more erect dick, giving me a most interesting view of his balls and crack. I couldn't help myself and started to nibble on Dan's low hanging nuts and licking his hole and the skin between the two, I knew that drove Dan crazy. It didn't take very long for that most marvelous of all things to happen, all three of us came off at once, me inside of Dan's mouth, Dan all over my chest and the boss deep inside my bottom. All you could hear in the room was the sound of heavy breathing as we all recovered from our ordeals.
The boss pulled out of me, Dan got up from over my head and I slowly got to my feet.
"You boys can get dressed now," the boss said.
Pulling on my underpants over my hot behind wasn't much fun and I heard Dan hiss in pain as he got dressed himself, his bum had to be hurting big time after feeling that stupid strop lash his naked hide 25 times. That's okay, we can take care of each other a little later for sure. The boss wiped himself off with a paper towel and put it away and zipped his pants.
"You two can head out for home," the boss said, "but I expect you both here bright and early in the morning."
As we headed to the door I heard him say, "You better not misbehave again for now you see what you are going to get if you do."
"I still owe you, man," Dan said as we walked out of the store.
"Darn right you do!" I said, "I didn't mind the hiding with the strop all that much, it wasn't a lot worse than what my old man used to do to me with his belt but you owe me big time for me getting my butthole spanked like that and I fully intend to collect payment in full!"
Dan looked at me. "You'd spank me there?" he asked.
"Darn right!" I said, putting an arm over his shoulder, "But don't worry, I won't use a ruler like the boss did to me, my hand will work just fine. Just consider it a little warm up for what is going to happen to it afterwards."
We walked to the parking lot and as we got into our cars I said, "See you at my place."
"Sure thing," Dan answered, "be right behind you."
I fired up the car and took off out of the lot, seeing Dan in my rearview mirror. I had better get home pretty darn quick, I gotta pee big time.