14 years ago I posted a couple of stories from my first sexual experience, which…
Squash Club fucking
I am a member of a squash racquets club in London. I like to work out generally, keep myself fit and toned, and I spend a lot of time at the club and in the gym. I was at the club one day, looking for a squash playing partner. I approached a group of three men and asked if any of them would be willing to give me a game. Actually, the conversation went more like this:
“Hi, guys. Look, I am fairly new to this Club, and my partner has let me down. Would any of you like to play a round with me?” They looked at each other, and smirked suggestively. I realised that I had not phrased myself clearly, and given them a double meaning to my innocent question. I stammered out “Oh! Sorry. I meant would one of you care to play a round of squash with me”, and I laughed, blushing at my stupidity.
“Sure” one of them said. “We were playing a competition among ourselves. It’s what we usually do to make the game more interesting, but you can join in the competition, if you want.” “Fine” I said, relishing the thought of some keen motivation to improve my game. “Right” said the same man “our rules are simple. We play a Round Robin, which means we each play against the other three – three points for a win, none for a loss. Then at the end of the three games, the one with the most points is the winner.” “That’s okay by me” I said, “What are we playing for?”. I expected a pool of money, but the main man said “We each think of a forfeit that the loser must pay to the other three. These will be sealed in envelopes, and the winner gets to get his forfeit from the loser.”
“What about the second and third placed men?” I asked. “Ah!” he said “The forfeit must include them in the payment, so that no one is left out. Is that alright with you?”.
“Yes” I said, not really understanding. Then we each went to a bench to write down our respective forfeits. My own was that the loser should take the other three out for a slap up meal. Then we all put the envelopes into a locker and got changed. As I got into my kit, I couldn’t help glancing over at the opposition, to weigh them up as competitors. I didn’t get many clues, other than to see that they each were fit and healthy looking, with strong and slim physiques, powerful arms and legs, and tight firm stomachs. I also noticed that they were each well hung! Their cocks hung heavy between their legs, and their balls were firm and added to the obvious bulge they would undoubtedly show in their trousers when out on the town.
Their names, when introduced to me, were Kirk, James and Kenny. I played Kirk first. He was good, fast and strong around the Court, and It only took him 45 minutes to demolish me, beating me in 3 straight sets. I was breathless from running around the Court, and feeling shaky with exertion. We waited for about ten minutes for the other two to come from their game. I asked “What was your forfeit, then?” but he just smiled and said “Ah! It has to be kept a secret until the end. However, you must agree to abide by the full wishes of the winner, and actively take part in whatever the forfeit is. Agreed?”. “Oh yes!” I said, a little nervously “No problem there. I am a man of my word”.
My next game was against James. He came up looking fit, hardly broken into a sweat. I was amazed at how these guys must be, because although I had recovered a bit after the first match, I was still looking and feeling a bit weary. I went into the game with some trepidation, but also determination. I won the first set, but the effort I had to put in left me unready for the next two sets, which James won comfortably, although I did put up some decent opposition for a while. Clearly, I was not going to get my forfeit, as I had now lost two of the three games, so, while we waited for Kirk and Kenny to finish, I said “Well, I won’t be getting my forfeit, so I might as well tell you what it was. It was a slap up meal for the four of us, courtesy of the loser. What was your?” He said “Sorry, the rules are that it must be kept secret until the end. All I can say is that whoever wins, it should be a memorable evening for all the others!”. With this mysterious and useless hint, the conversation ended. When the others came up, neither of them looked particularly tired, and I marvelled at their stamina and endurance.
I went in to play Kenny, expecting to lose but determined to fight all the way. Again I won the first set, and was up five points in the second when he seemed to step up a gear and get his second wind. Then he dazzled me with some brilliant shots, leaving me flat footed and open mouthed with admiration for his skills. I lost the second set, and the third was just a formality. I lost it hands down with no answer for his play and talent. I congratulated him and we left the Court to wait for the others. “Have you done this before?” I asked, “I mean with an outside player like me, or is it just usually between the three of you?”. He smiled and, looking me directly in the eyes with his dark brown gaze, said softly, “Oh, no. You are the first. I hope you won’t be disappointed”. He held my gaze for some time, and, I felt the butterflies in my stomach as he seemed to peer deep into my soul.
Kirk and James joined us after fifteen minutes and we all returned to the changing rooms for a shower, and to find the result. I knew that I had lost to all three, so it was only a matter of finding out what the forfeit was for the winner. It transpired that Kirk was the winner, and this was no surprise to me, nor to James and Kenny, as it happened. “Right” said Kirk, “my forfeit!” He held the envelope in his hand and, without opening it, he looked me straight in the eyes and said “The loser must do exactly as I demand. You will firstly take Kenny, naked, and give him the most tremendous blow job he has ever had. I warn you, he has had many, so you must be at your most erotic, sexy and sensual. Make sure that when he comes, you swallow all of it, don’t spill a drop. When that is over, I will tell you the second task with James.”
My heart stopped, my stomach lurched and my mouth went instantly dry as I realised what I was being ordered to do. I remembered the sight of their bodies, particularly their love tackle, from earlier, and got quite excited at the prospect of what lay ahead. We all stripped off, and me and Kenny stepped into the shower. We washed the sweat off, but I made Kenny do nothing while I soaped him down and washed his entire body clean. I soaped up my hands and slowly ran them over his shoulders, his chest, his legs and between his cheeks to touch, ever so lightly, his anus. He gasped as I did so, and I saw his cock spasm as it started to get harder and bigger. When all the soap was gone, he stood there with the water running down his body. I gulped as I took in the view of his strong chest and shoulder muscles, the six pack of his abs, and the strong leg muscles. His body was beautiful, and smooth, with little body hair. I leaned forward and started to kiss and lick his chest, moving slowly from one side to the other, licking and flicking each nipple, lightly biting each one to make it stand out hard, while my hands ran down his sides, kneading the muscles and then moving round to the back to squeeze and caress his firm buttocks. I could now feel his cock, standing out hard and erect, as it pushed against my stomach, and I could tell that I was giving him some real erotic pleasure with my efforts. I ran my tongue down his stomach, stopping at his navel to probe with my tongue into the small depression there, while I continued to run my hands over his buttocks, parting them and scraping my fingers between the crevice to touch his anal opening before taking my hand between his legs and stroking his balls. As I held them in one hand, I took my other hand and touched, for the first time, his stiff cock on the shaft at the base near the pubic hair, being careful not to touch the swollen end. I was saving that for my moist and hot mouth! I gripped his meat firmly, running my hand up and down its length while finger
ing his balls, and tugging at his pubi
c hair with my teeth. I felt his shaft throb in my hand with tension, and I slowly moved my tongue down his left upper leg, touching the soft skin of the inner thigh, then softly taking one of his balls in my mouth and gently sucking on it. I then ran my tongue along the entire length of the underside of his cock, until I reached the swollen tip, and I then opened my mouth to take his cock head into my mouth and I started to suck and bob my head onto it, taking his knob deep into my mouth near to the entrance to my throat. I sucked him like this for only a couple of minutes, and I then traced my tongue again down the shaft until I could suck his other ball, and stroke the soft skin of his buttocks near to the anal opening. I heard him gasp so I returned my mouth along his shaft until I again took his swollen purple cock into my mouth. He lunged and thrust his hips forward, pushing himself deeper into my mouth, and I sucked hard on him, bringing him, with mouth and hand, closer to his inevitable climax. He held my head in both hands and started to groan, and I could taste that he was ready to come inside my mouth. I sucked harder, pinching his shaft with my lips and he finally released his long stream of hot salty cum onto my tongue and down my throat. I continued sucking hard, draining him and swallowing all of it. I could feel the thickness of his cock getting softer and smaller as I drained of the last drops of juice. When he was finally spent, he slowly eased his cock out of my mouth, and fell, exhausted, against the shower wall.
Kirk and James stood there, just outside the shower, clapping and cheering at my performance. “Well done. That will take some beating” said Kirk. “Now the next part of your forfeit is to suck my cock, with as much enthusiasm as you just did, while James here fucks your arse”. My eyes widened with a mixture of fear and excitement. “Don’t forget” said Kirk, “you must fulfil all of the forfeit. James will lie on the floor, and you will lower yourself onto his cock. When he is in, you can start to suck my cock. If, by the time he has come, I still haven’t, then I will finish off by fucking you myself. I might even have myself a little diversion to make it more interesting for me – but that will be my little secret!”. Then James lay on a towel on the floor, holding his cock erect in one hand and calling me over to him. Kirk then reached into his bag and brought out a large tube of lubricating cream, and smeared it on and around my anus. As he applied the cream, he occasionally slid a finger inside, and I felt by sphincter grip his finger, but he probed a little deeper. Then he slid two fingers inside me, with more cream, and stretched my muscles by opening his fingers slightly, and then pumping his hand in and out of my anus. When he had finished putting even more cream on, he guided my hips over James’ cock, and I slowly lowered myself onto the swollen end. As his knob touched my anal opening, I felt a slight tightening of the muscles, before I relaxed them, and his cock slid easily inside me. I lowered myself further, and I felt his thick cock started to plunder deeper into my bowels. When I felt the hair of his groin tickle my ass, I knew that he was fully inside me. I started to raise myself and lower myself onto him, but after a minute or so I found my leg muscles could not keep this up. As I rested my weight on him, he started to thrust upwards, raising me off the ground and he then started to fuck me in this position. He plunged in and out of me, his cock drawing its muscular length along the tender flesh of my insides, and I could feel each uneven bump and contour of his cock as he thrashed it in and out of my hole. While he was seeing to business at that end, Kirk pushed his hard and swollen cock into my mouth, and I concentrated my efforts on giving him the best head I could manage. I sucked him deep into my mouth, and then dragged my teeth back along the shaft of his prick, flicking my tongue on his knob, and squeezing my lips tight onto his rod. I moved my head down so that I could lick his balls, and take each one into my mouth to suck each in turn, and then returned my mouth to his stiff cock. I could feel the pounding meat banging away at my anus, as I squatted there, feet and legs apart, sitting on his rigid rod. I wrapped my arms around Kirk’s hips to steady myself, as I didn’t want to fall over and lose the hard cock that was up my ass, and also so that I could knead Kirk’s buttocks while I sucked him deep into my throat. Kirk held my head in his hands as he started to push his hips forward and enter my mouth as deeply as he could, fucking my face while James continued fucking my ass.
When I got some strength back in my legs, I lifted myself slightly and then pressed down with my anus, making the fucking I was getting more pleasurable for both James and me, and after about ten minutes of frenzied fucking, in which I could feel my rectum getting more relaxed, and my insides receiving a fabulous pounding from his cock, I suddenly and unexpectedly felt the hot rush of his cum inside me. He pushed up, making sure I received all of his juice, while Kirk was still running his hard cock in and out over my lips and tongue. Eventually, James’ cock softened and he was spent. Kirk pulled his cock out of my mouth and lifted me up so that James’s cock slid out of my well used hole. Then Kirk said “Right, now it’s the winner’s prize!” and he led me over to a bench in the middle of the changing room. He laid out several towels on the bench and placed me, face down, over them, with my legs hanging down free and my upper body flat on the bench. “Hold him!” he commanded, and I felt the other two grab hold of my arms and hold me firmly down on the bench. “Before I fuck you, I think a sound spanking is in order. Do you agree?”. The question was aimed at James and Kenny, who both said “Yes, indeed”, but I thought he was talking to me, and I was so sexually aroused and carried away by the moment that I said “Oh! Yes please Kirk, punish me for losing!”. There was a short silence, as if they couldn’t believe what they had heard, then Kirk said “Okay, fifty strokes it is!”. He then picked up a training shoe, with a heavy rubber sole, and positioned himself behind my exposed and totally vulnerable backside. Whack!! The first one landed across both buttocks, and I almost jumped up with the shock and pain of the first blow, but James and Kenny held me fast. Crack!! The second one landed on a different spot, making me shout out in ecstatic pain. It was followed by Whack! Whack! Whack! three more hard blows, and I felt the burning pain as my cheeks turned to a blushing pink glow from the punishing smacks. He continued up to ten, each blow as hard as the former, and then he stopped. I lay there, writhing but enjoying this new adventure, while he rested and spoke to me. “Your punishment will not be over too soon, boy, and I want both you and me to savour the joy of giving and receiving pain”. As he rested, I reflected on how fit and strong he had looked when I saw him in the shower and on the squash court. I knew I was in for a severe spanking, and probably and devastating arse fucking too!
After about a minute, where I felt the burning of my flesh spreading throughout my loins and the pain subside slightly, he started again, with equal fervour and power and singular accuracy, each time finding a fresh spot to deliver the stinging whacks to, until a further ten blows had landed. Then he came over and lightly stroked the sore and swollen meat of my buttocks. “Your backside was just made for two things – spanking the glorious mounds to a purple hue, and then fucking the hole between them!” He waiting another minute for the pain to ease, ensuring that the next ten blows would feel as fresh, and a painful, as the first had, and they did! I writhed in fresh spasms of pain and pleasure, unable to move more than a little, moving my hips from side to side in a vain effort to get some relief from the heat and agony I could feel. After another minute or two of rest, he delivered the fourth set of te
n whacks, an
d this time they felt and sounded much different. Then I realised that he had thrown the training shoe away, and was now using his leather belt. The more focussed straps of pain made me scream out with the pain, but I had to just lie there while James and Kenny made sure I would not move until the punishment was complete. The ten strikes from the belt made a criss-cross of red lines over my already bruised and battered backside, and burned like branding irons into my flesh. I felt tears of pain and humiliation running down my face, and when the final rest came prior to the final ten blows, I prayed for mercy, knowing that none would come. I lay there gasping and panting, knowing that after the next ten, I was still in for a good fucking from Kirk. He actually came round to my head, and showed me his magnificent, erect and very hard cock. “Kiss this,” he said, “because it will soon be buried deep inside your ass, taking you and me to a new plane of sexual ecstasy”. I lifted my head and planted a wet kiss on the swollen end of his cock, and thought of the promise he had just made as a means of getting me through the final stage of my spanking.
As I lay there, waiting for the kiss of pain, I reflected on what had happened to me so far, and while I was lost in this state of reverie, the first of the final ten blows landed, hard and hurtful, bringing me swiftly back to the present. I managed to stand the final ten cracks of the belt without crying out for him to stop, and when he had finished, I heard the belt buckle hit the floor, and almost instantly I felt his hands parting my buttocks and his hard cock being pushed against my unresisting anus. He slid inside me easily, and started to fuck me, pushing in slowly, drawing back fast, sometimes coming completely out before returning his ramrod stiff cock deep into my ass. He fucked me hard, then slowed down to make his fucking tender, then speeded up again, reaming in and out of me in different tempos, making me feel like I was being fucked by so many different men. He would draw his cock out fast, then return it slow, then change to drawing it out slowly and then ramming it back home with one powerful thrust. He would draw his cock out totally, then fuck me with quick insertions of just the swollen end, in and out quickly, then pushing himself deep inside and leaving his throbbing cock inside me, flexing and relaxing his cock muscles while it lay inside my guts. He was so good, keeping total control of his cock, extending his own, and my pleasure for about twenty minutes or more. As he fucked me, he would occasionally slap my arse with one of his free hands, and continue fucking me while the stinging made me wriggle on the end of his cock.
Finally, I felt him speed up and his rapid plundering of his cock became rhythmic, indicating that he was ready to come inside me. He gripped my hips as he pumped in and out of me, his cock throbbing with the cream he was waiting to shoot into me. I could hear the slap, slap, slapping of his firm stomach and thighs against my buttocks as he fucked me with vigour and wanton energy. He slapped my buttocks with his hands as his climax approached, and finally, he released a huge wave of hot creamy sperm into my waiting anus. I felt my own climax quickly approaching, and I heardthe loud splat as my cum juice hit the tiled floor under the bench on which I was lying, being fucked to a standstill. He pressed himself into me, so that my bowels could receive all of his juice, and when he finally finished, his cock shrank and he pulled out of me, leaving me gasping for breath. He then joined the other two on another bench, and the three of them sat there looking at me, naked, sweating and exhausted from a tremendous sexual experience, cum juice running out of my open anus and dribbling down my legs. I did not move, luxuriating in the afterglow of some great sex, and I saw them smiling at each other, with some pride and triumph on their faces.
After some minutes of silence, I said “Wow! That was some competition. When will the next one be?!” They just smiled at me, and said “Any time you like. Next time, we might make the number of competitors a bit bigger, to make it more interesting. What do you think?” Well, dear reader, what do you think?