This is a story that contains descriptions of gay sex and paddling/spanking between two men. If you are under 18 or otherwise prohibited to read this story, pease do not go any further.
Betting Your Ass
My college roommate and I discovered early in our first semester that we had a lot in common. It was the first time in our lives when we were away from our parents and our families. Billy was from Stonewall, Mississippi, near Meridian, and I was from Montgomery, Alabama. We had gone to a small liberal arts college in the Smokey Mountains of Tennessee and had been assigned a dorm room together. Alcohol was easy for freshmen to get especially when you pledged a fraternity like we did. One night during rush week we got very drunk stumbled back to our room and ended up having great sex. Neither of us considered ourselves gay, at least not at this point in our lives. But instead of acting like nothing happened, we talked about it and decided that we had never had that much fun having sex with anyone else, but also decided to keep our little sexual experimentation between us, especially if we were going to join a hyper-heterosexual fraternity.
The other thing that we learned after we joined the same fraternity was that we like getting our butts whacked with those frat paddles, during our initiation. They never paddled us much just a few whacks here and there. We shared with each other how we had enjoyed being paddled by the coaches at the private high schools that we had both attended. It was after our college experience when we were confident gay men that we got together for a little one-on-one paddling session.
We had separated for grad school, Billy to law school at the University of Alabama and me to the Auburn University for business school. We occasionally got together during that time, though we continued to have other boyfriends and paddling remained just between the two of us as part of our foreplay. It wasn't until we got out of grad school that we dreamed up a betting game for a private paddling party between us. The annual Auburn-Alabama game was the time of our party. Billy's parents had died during his time in law school, and he had returned to Stonewall to live in the old family mansion. The house was stone with columns in front and a large stone veranda in back with a barbecue pit and a jacuzzi, best of all it was in the country miles from anyone else. The house occupied only by Billy would be the meeting place for our party.
I always drove from Jackson, where I was currently living, to Billy's house. We always met each other with a passionate kiss and I would proceed to undress and walk out to the veranda. (Billy would already be in only a chef's apron, because he didn't want to burn any vital parts firing up the barbecue.) We both kept a baseball player's physique and played in softball leagues and went to the batting cages regularly to keep our swings of the paddle in top form. Out on the veranda we would cook steaks and drink beer waiting for the game to start. Billy had a large screen TV that rolled out on the veranda so we could watch the game there. The rules of the bet were simple: 1) When the opposing team scored, you got paddled that many licks. 2) If they scored a field goal first then you got three whacks fast and hard. If the first score was a touchdown you got a shot of tequila and then seven hard and fast. (The tequila really didn't do that much but it was a fun addition.) 3) After the first score, the paddling was cumulative and you were allowed a shot of tequila before each paddling started. 4) At the end of the game, the loser took the total number of points scored by both teams (this time without any fortification). 5) The paddling were always given hard but after the score began adding up, the speed of the paddling was slowed some for better effect. 6) After the game was over and the loser took his punishment, we would share a joint and then eat.
Those were the rules and this last game was the most fun we ever had. I arrived at Billy's and we got ready for the game to start, that is get naked, sit back, drink beer, and catch up on each other's lives. The game started with Alabama scoring a touchdown in the first minute and made the extra point kick. Billy picked up his paddle and began warm up swings. I opted not to take a shot of tequila to get the full impact and bent over ready for my punishment. Seven quick hard whacks on my naked ass, counting out each one. I took them well, but still had to lay on my stomach on the lounge chair in front of the TV, while a cool breezed cooled down my red hot ass. Billy slapped my ass and said, "Better luck next time," before he sat back down.
It took to the end of the quarter for Auburn to score a field goal and hopefully gain some momentum in the second quarter. Billy took his three licks like a champ and checked on the grill before sitting back down. I was able to sit at this point and just admire the perfect bubble butt of his with its bright red streak across him making it only sexier. I was getting horny at this point and it showed as my dick started to stir, but it soon subsided as the game started back up.
Auburn had indeed gotten some momentum and within three minutes of the game intercepted the ball and ran it back seventy yards for a TD, but they missed the extra point. Billy got up and handed me my paddle saying, "I'm going to take a shot of tequila for these six. Your swing has gotten better since last year." He walked near me and squeezed my biceps to prove his point and then he licked my cheek, threw back the tequila, and bit a lime. Billy bent over for his punishment, which I proceeded to gave him nine hard licks, slow at first and then gave the last three in rapid succession. My reprieve I had experienced from the beginning of the game soon ended as Alabama scored a few minutes later with another touchdown and now had fourteen points. This time I did take a shot of tequila, because truth be told Billy's swing had gotten remarkably better as well. If my ass had been a baseball, I would have been out of the ballpark. I bent over and took my fourteen, which he gave me hard and slow with time in between each of the hits to really feel the full force of each whack as the paddle cracked across my ass. As before I was unable to sit back down right away, so I laid on the lounge next to Billy, who had laid back down on his stomach, having taken off that apron and allowing me to see that big beautiful cock of his. Evidently he had just been putting on a brave front when he had sat back down before and the stinging was getting to him also, yet he was semi erect. Our paddling sessions had always been heavily erotic for both of us.
Halftime came without either team scoring again. I turned to Billy to see if he was having fun and the grin on his face told me all I needed to know. I leaned over to give him a quick kiss, but he rolled me off the lounge landing on top of me and giving me a deep passionate kiss. He looked into my eyes and said, "I really miss you. I've missed you since we've separated since college. Now I have this big house with you only a few hours away and wish you were here more than just once every couple of months."
"I've missed you too. The guys in Jackson aren't nearly as sexy as you are, nor do I share that much in common with any of them. I miss our talks most of all, I don't call as much as I should. Not to mention just being next to you."
We stopped talking and began kissing again and humping our bodies against one another. We were both hard, and our dicks just glided next to each other. However, the stone floor of the veranda was not only cold, but also very uncomfortable. We each got up still kissing and then walked over to get another beer. The game was about to start again. Billy slapped my ass and then pressed his body against mine with his hard cock wedged between my ass cheeks. He began kissing my neck and rubbing his cock between my ass cheeks like a wiener in a bun, but I reached back grabbing hold of his dick and said, "You know you have to wait until after dinner for that. I don't allow a man to fuck me before he has wined and dined me first."
Billy gave a I'm-horny-and-hurt-but-not-really-hurt look and said with a pout, "Well, the game is starting again anyway."
Alabama came out of the locker room with plenty of momentum from their lead and that last touchdown and quickly got the ball from Auburn and moved it down the field and scoring a touchdown within the first few minutes of the half. I took another shot of tequila, feeling a good buzz, and bent over for my twenty-one licks. Again he gave the licks with plenty of time to think between each hit, and he kept the licks as hard as they had been the first time. This time however, Auburn scored just as Billy administered the last whack. It came as such a shock to him, that he just bent over for seventeen whacks without any fortification (Auburn had gotten the two point conversion). He took the paddling like a pro, but was groaning a little on sixteen and seventeen. (I guess I had gotten a little better.) There was not much rest for Billy, because Auburn got the ball back after Alabama was able to only move up to the twenty-five yard line in there possession before they fumbled the ball. Auburn took the turnover and scored another TD, making the score 24-21, within the last minute of the third quarter. Billy took is twenty-four licks very well, considering I took pity on him and gave them fast and hard so he wouldn't feel the full effect of all twenty-four, considering this was forty-one whacks within 30 minutes. Billy took two shots of tequila to make up for the two he had not taken before the punishments he had just received.
We knew we had to get ready for an exciting fourth quarter. With only three points separating the two teams, anything could happen in an Auburn-Alabama game. Sure enough Alabama ran the ball into field goal range and tied the game. I had enough good sense to take my tequila shot before I bent over. I also knew that Billy was horny and ready for revenge, which experience told me that this was going to hurt like a motherfuck. Sure enough he walked near the grill and got, not his usual frat paddle, but one with holes in it that was already warmed up from being near the fire. He told me to count all twenty-four whacks off and count to three in between each one. I though this meant he would wait until I had finished counting before he hit but he surprised me and varied his speed hitting on either one, two, or three. The paddle was already warm adding to the sting and the holes made the paddle travel through the air much quicker. Billy took no sympathy, but while my ass was stinging like never before at the end, I was hard as a rock. I almost wished for three more whacks because I was really close to cumming just from the momentum he had built up with the paddle. I had actually let a few drops of pre-cum hit the floor. When he was done, he bent down kissing each ass cheek as to say "No harm, no foul." The game stayed tied until the last three minute of the game when Alabama faked a field goal and ran in for a touchdown. I bent over to take a quick thirty-one with his standard frat paddle, nothing fancy this time, as the game was getting exciting. Auburn was running the ball backed down the field and looked like they would tie the game again. Billy finished my thirty-one with Auburn on the five yard line, no time outs left, and twenty seconds on the clock. Auburn went for it to tie the game and the quarterback threw a pass and the receiver missed it with Alabama intercepting the ball, and began running it back down the field but was stopped on the twenty yard line to end the game.
With the game over and Alabama winning 31-24, it meant that I had to bend over and take fifty-five hard licks. Billy picked up the paddle with the drilled holes but luckily it was not still warm from the fire or from the beating it gave my ass. I braced myself on the wall of the veranda ready for the beating of my life. The score had never cumulated to more than thirty-five since we had begun the bet, the most licks I had ever taken from a paddle in one session was thirty-one just a few minutes before. I was still horny as hell and my dick was already getting hard again, never fully recovering from the hot ass beating a few minutes before when Billy had used the holed paddle. The first five went relatively easy, but the next five hits were harder and faster. By the time he reached forty-five, I was extremely turned on and when he reached number fifty-four I was on the verge of cumming again. Billy paused for a brief second before he delivered his hardest hit yet, and I lost it. I came on my chest, the wall, and finally on the floor. It was by far my most intense orgasms ever, but I knew that the best part of the evening was yet to come.
We were both panting and laughing when we were done. Billy walked over to the table and retrieved a box, which I knew contained some of the best marijuana available. (Billy was a criminal lawyer and defended drug dealers across the south. He was rich, did not believe in drug laws, and only took weed from his best clients, as well as their money of course. He was one of those lawyers who believed everyone should get a good defense, but really only did his best the with marijuana dealers and let the rest go to jail. At least, that's what he tells me.) Billy lounged in his chair, and with my ass still sore coming down off my orgasmic high, I laid on top of him as he readied his pipe with weed. We got really stoned and neither of us was in pain anymore. So we began to cook dinner. We were both hungry, considering we were stoned. Now, its not the greatest idea to cook while stoned, but we had always cooked together, since college, either stoned or drunk, so for us it was just normal. We ate dinner, and smoked more weed and drank more beer and tequila (we always regretted this the next morning, but it was always a good time had by all).
After dinner we began to kiss and get more intimate. We took a walk, still naked, down to the pond behind the house. Billy pushed me up against a tree and began kissing me while running his hands up and down my body. When he grazed his hand across my ass I tensed, but soon relaxed into his arms. I leaned in to kiss him deeper, but he lost his balanced and we tumbled into the pond. While we were in their we decided to take a swim and wash the mud off of us. I helped Billy out of the water, and we fell laughing and giggling into the grass. We rolled around until I was on top of Billy and began kissing his chest, savoring his nipples, and then trailing down his body, kissing his stomach and finding the trail of hair that ran to his most impressive part. Considering the whole package was pretty damn impressive, his massive 8 1/2 inch cock was amazing. I began licking the top of his beautiful prick and then down the shaft to his heavy balls. I made my way back to the top of his dick and took as much of it as I could in my mouth. I was able to take a fair amount, being used to his cock, but I still gagged a little taking in more and more until we were in a good rhythm. He motioned me to move my body up towards him and he took my 7 1/2 inch cock in his mouth, mine was thick but not nearly as thick as his. He had always loved the size of my dick and quickly began deep-throating me as we continued in a sixty-nine position. After cumming together, we walked back up to the veranda and being a little chilly from the pond and the wet grass, we got into the jacuzzi.
We rested and cuddled together in the warm water, while we caught our breaths from the romp down by the pond. Relaxing and talking about the fun we've had in the past, how much we missed each other, and how much we wished we saw each other more. Just as the romance part of the evening was picking up, Billy reached over to a small cooler next to the jacuzzi and got out a bottle of champagne and two flutes. Opening the champagne he poured us two glasses. Everything seemed perfect. We finished off the champagne, kissing and running our hands over each others bodies. We then got out of the jacuzzi, dried each other off and went inside and upstairs to Billy's bedroom. He kissed me as he laid me down on the bed. He then kissed down my body and rolled me over onto my stomach. Kissing my still smarting bum, he ever so tenderly parted my cheeks and began to lick my hole, darting his tongue in and out. I was moaning with pleasure as he paid such special attention to my rear. He licked between my hole and my balls and then licking my balls, taking long lapse with his tongue between my legs before returning to my tight little hole that was twitching in anticipation of that massive cock. He then reached over to the bedside table and got out a tube of lube and a condom. My ass twitched with anticipation once more. He lubed up his finger and began working one then two then three fingers into my ass. When he felt that I was loosened up enough, he moved up my body and began to enter ever so smoothly and gently. (Now this was an unsaid rule of the bet, but the bottom was always the loser of the bet. It had never been stated aloud, but it always happened that the winner was more aggressive and confident.) I moaned as he pushed all 8 1/2 inches into me. With that cock, it always hurt like hell when he entered and he always entered and withdrew two or three times before my ass could take him completely, but then he was able to push all the way in and slowly sped up. He then turned me over, lifting my legs over his shoulders, and re-entering me. He fucked me slowly at first and then began to fuck me harder. With both of us in the throws of passion the began to jerk me off while fucking me. We were in such ecstacy that our orgasms came only seconds apart. First, I came across his and my chest as we kissed deeply and passionately. Then he came while I was still in the throws of orgasm. Him cumming inside me started me again. I had thought the earlier orgasm had been the best of my life, but in Billy's bed and cumming with such passion that it felt like an eternity in heaven, I felt as if I would never experience such pleasure again.
We fell asleep in each others arms, awaking in the morning with only slight hangovers and fairly sore asses, mine inside and out. I got up first and went to take a shower. As I was entering the bathroom, I saw Billy get out of bed still naked and walk out of the bedroom, presumably to put on some coffee. I started the shower and quickly brushed my teeth. I got into the shower just before Billy walked into the bathroom. Soon he got into the shower and as he kissed me I could tell by his minty fresh breath that he had also brushed his teeth.
"Is there coffee on?" I asked.
"Yeah, it will be ready and waiting when we get out."
As we lathered each other up he looked down at my ass, which had a slight blue tent to it. He ran a sponge over my ass and said, "I'm sorry if I got a little carried away last night. I hope you will be able to sit down."
"Don't worry about it. Last night was the best game night we have ever had. And every time I sit, I will just remember this night fondly without any regrets. Maybe except for this hangover I have. How's your ass?" I then took a quick look and answered my own question, "It looks perfect as ever."
"Yet it is still sore. I may not be as bruised as you but you hit pretty hard last night, not that I'm complaining."
We laughed and kissed washing each others bodies. Then got out of the shower and drying each other off. We put on robes and followed the aroma of freshly brewed coffee downstairs to the kitchen. We walked out into the garden room where two very soft and comfortable armchairs were waiting for us. The soft fabric and plush cushions felt good on my ass. I lit a cigarette and enjoyed my coffee. Today would be a day of lounging before I went back to Jackson. I promised to visit more often and likewise did Billy. Then Billy said that he had a surprise for me. I looked at him quizzically, and he handed me a business card. The business card was his, but something was different. The address wasn't a Stonewall or Meridian address where he had his offices, his other offices across the south had junior staff working in them. Billy had come a long way in a short time in east Mississippi, mainly because of name recognition. The address on the card was a Jackson address.
"I'm opening a branch in Jackson. I've got clients there in federal and state courts, and I will be renting an apartment and will have to be in Jackson every other week working cases, sometimes more when I'm in court."
"This is wonderful. It means we will be seeing much more of each other." I reached over and kissed him. This was a more wonderful weekend than I had imagined it would be when I left Jackson Saturday morning.
If you liked this story and would like to contact the author please send any e-mails to paddleme77@yahoo.com.