Last weekend after the heat wave finally snapped, the third cougar vs teen tournament of the summer took place. The rules are simple: Matches go to climax or submission (make your opponent orgasm or give up). It's four teen boys versus four moms. You have to enter as a pair, although the tournament is set up so that you'll only end up wrestling your own mom if you both make it to the final match - needless to say, this is usually something of a big deal when it happens. If too many cougars or too many boys lose their matches, the tournament's over early, and the losing team gets slapped with a big punishment - last time this happened to me, we spent the whole rest of the day mowing Mrs. Martinez's lawn and cleaning her pool while the victorious moms lounged around making us get them drinks and rub them down with suntan lotion. (I have no idea what we'd do if too many teen boys won; I don't know if this had ever even happened and certainly had myself never been on a team where this occurred.) Whichever teen did the best was awarded a speedo, which was a mark of pride you could wear the rest of the summer. And of course, being horny teenage boys, even if you didn't win anything, it was a much more exciting day than playing Halo or Call of Duty. This tournament was taking place at Jennifer O'Brien's house out by the pool. Both teams had a cluster of deck chairs at either end of a blue athletic mat (which was laying on top of the bare concrete of the poolside).
This particular tournament kicked off with my mom, Emily, up against Matt. (I'll be referring to her interchangeably, although it feels a little weird calling your mom by her first name.) Matt's a short dude, about 5'3" or so, wearing a black speedo, and with his hair buzzed into a short cut. He's Mexican and has pretty dark skin. He was already sweating, heat or nerves I couldn't tell. To be fair my mom looked unusually intimidating with a half foot on Matt at 5'9", although the effect was a little diminished because she's rather slim. Her light skin (she's naturally pretty pale and and had been wearing strong sunscreen all summer) was almost as white as her plain two piece bikini. Her black hair was set into a long braid that went down her left shoulder almost to her belly button. Her green eyes were fixed on Matt like a hunter on her prey.
Right from the word go Matt was moving his feet, darting in to test Mom's guard. He came too close and tried to pull back, and she quickly reached out and slapped him hard across the face. He was stunned long enough for her to sock him in the stomach, then she put her hands on his shoulders and started kneeing him in the gut. Matt took three of these, then she pushed him and he fell to the mats on his back. As he covered his stomach and groaned Mom took a lap around him, doing muscle poses as the other moms applauded and we all urged Matt to get up. Mom backed off and let him get to his feet. They came together again, and Emily lashed out with her foot, kicking Matt hard in the side of the head. He went down to one knee trying to clear the cobwebs and she came up behind him, bending down and locking on a sleeper hold. Matt got to his feet, kicking and trying to get away. She left his legs free to let him wear himself out, but I think he outsmarted her as he lifted one leg straight up and stomped down on the top of my mom's bare foot. She screamed and pushed him away from her. He turned to face her and charged in, but I guess this was his mistake as he barely had time to catch a breath after getting free and Emily didn't seem to be as stunned as he was hoping. She gave him a Big Boot, which is a fancy way of saying she kicked him in the face, and he went down hard on his back. Mom stomped on his stomach a few times, seeming pissed off, then took a second to breathe. Matt was laying on the mat groaning and despite our encouragement it didn't look like he was getting up any time soon. Mom reached down and pulled his speedos off to the amusement of her team and threw them to Matt's mom. Matt had just rolled over and started getting up and Emily pulled him up to his feet, then slammed him back to the mat with a DDT. She rolled him on to his side and got him in a surfboard, pushing her right foot into his back, pulling on his left leg and right arm with her hands. With her long legs this looked pretty painful, and I felt bad for Matt, bare-ass naked, screaming as Mom pushed his body into a generous curve.
Instead of just pushing as hard as she could, it looked like she was trying to wear him out, easing up on the pressure slightly, then going back to maximum extension. She kept flexing him like this for a few minutes and it seemed like she had succeeded in wearing Matt out. When she released him he flopped to the mat on his face. Mom wasn't done with him yet and got an even nastier hold on him. She slapped him in I guess what you'd call a camel clutch variant. Basically she laid down on her back so that she was side by side with Matt, with her feet by his head and vice versa. She reached forward and grabbed his arms, pulling them straight back and pulling his upper body off the mat, then planted her feet in the middle of his back and pulled. This looked even nastier than the bow and arrow, and instead of flexing and wearing him down, she just pulled as hard as she could. Poor Matt, covered in sweat and red-faced, couldn't even kick his legs. It was pretty clear the match was over, but it's bad form to submit until your opponent is done with you, and Matt suffered in this hold until he was released. Barely had he had time to catch a breath than Emily had come up to him and rolled him onto his chest. She ordered him to get on his hands and knees, giving his butt a loud slap to drive the point home. Matt, groaning, got on all fours. She got down on her knees behind him, banging her hips into his butt like she was buttfucking him a few times as her fellow moms cheered her on. Having made her point she pushed Matt's thighs apart, then reached in between his legs, one hand playing with his balls as the other teased his five-inch cock to full length and then started jerking him off. Matt's thighs started shaking a little as she was really going at him, having humiliated him and just looking to put the frosting on the cake by making him cum. It didn't take long, and just before he popped off she took her hand off his nuts and cupped it under the head of his dick, catching some of his cum as she drove him over the edge. Matt had no chance to enjoy the afterglow as mom rolled him onto his stomach, wiping his own cum all over his face. She took a quick victory lap as me and the two other guys got up and dragged Matt back to our area, laying him out on a lawn chair like a casualty. One match down.
The second match of the day was Jim (Jennifer's son) - versus Linda (Rob's mom). This at least seemed a little more evenly matched; Jim's 5'7" to Linda's 5'6", although he had a definite weight advantage. Jim's fairly solidly built and probably in the best shape out of everyone (Matt and me are a little scrawny and Rob's a big slice of beef). He had on a white thong speedo doing very little to hide his big cock. His brown hair was loose down to his jaw, probably not the best haircut when you're wrestling MILFs who won't hesitate to pull on it.
His opponent, Linda, is a beautiful blonde, probably the hottest member of the cougar team (sorry, mom). She's a bombshell, 5'6" of tanned, toned, lean muscle with curves in all the right places, and today her 36C's were ably assisted by the bright red one-piece that looked like it had been painted on her. Her long blonde hair was piled on top of her head in a loose bun with several strands already falling from it. She's got blue eyes and big, pouty lips that were currently curved into a beguiling smile she was aiming at Jim. He looked calm, but it was hard to miss the tent he was already pitching as the match started.
Jim was off to a bad start right away as he foolishly put his hands up offering a collar and elbow to Linda. I have no idea what he was thinking and winced in sympathetic pain as his opponent instead reached through his hands and gave him a double nip twist. Jim yelped but managed to grab her wrists. With his hands occupied, Linda launched a follow up knee between the legs. Jim released her arms and dropped to his knees, and it already looked like he was in deep shit. Linda took a step forward, reaching down and pulling his arms straight up over his head, and locked in a standing headscissors. She held Jim like this for just a minute before he got his legs under him, and seeing his escape attempt coming she released the scissors. She still held on to his wrists and smoothy swung to his side, stomping down on his back and knocking him to the mat. She left her foot on his back and got behind him and started pulling up on his arms as she pressed down with her foot. Like her previous hold, she only kept this on to tire Jim out until he started gathering himself to escape. She released his arms, helping him up to his feet, then came around to his front and nailed him with a DDT.
This left Jim laying spread-eagled on the ground. Linda bent down and slid his speedo off, tossing it to his mom for safekeeping. Linda spared Jim a look and seeing him still laying on his back decided to show off a little.
She rolled Jim on to his stomach and pulled him up to his hands and feet. I was worried she was going to finish him off the way Mom had put away Matt, but it didn't seem like Linda to repeat a spot, and indeed she proceeded to sit on his back, then reached behind her and started slapping his butt, riding him around like a pony.
This got a big reaction from her teammates, but Linda had underestimated the sheer energy of a teenage boy and his hormones, and with a scream of surprise she was hefted into the air on Jim's shoulders as he stood up. He threw himself backwards onto the mat, giving Linda an electric chair drop that left her stunned on the ground. Jim quickly flipped Linda onto her chest and sat down on her back. He pulled her upper body off the mat like he was going for a camel clutch, but once her arms were tucked away behind his knees, instead of pulling on her chin he reached into her suit and started playing with her tits.
I was on my feet cheering at this, not just because it was basically the first real big offense our team had gotten, but also because I'd seen Linda wrestle a few times before and her big weakness seemed to be her libido - she enjoyed tussling with and dominating teen boys so much that she sometimes was more focused on enjoying herself than nailing down the match, and I guess Jim had noticed it too, or maybe he just wanted to get his hands on her chest (can't blame him if that was the case). Jim had thoughtfully pointed Linda at where we were all sitting, so our team got a great view of him feeling her up. Linda let her head droop, not even trying to escape the hold, her legs kicking weakly as Jim tweaked and teased her nipples. He managed to work Linda up pretty good, but he couldn't finish her off like this, so he reluctantly released her after a couple minutes. Linda didn't get up and he rolled her on to her back, then reached down to pull the straps on her suit down. Instead, Linda's hand darted up and she poked him in the eyes. Jim took a stumbling step back holding his face and turned away from Linda. She got up to her knees and came up behind him, reaching between his legs and grabbing his cock with one hand and his balls with the other. Jim had worked up a fairly impressive hardon while massaging Linda's chest, and she started giving him an expert handjob. From where I was sitting I could tell she was making sure he didn't cum too fast, sometimes stopping to pinch the head of his dick before she went back to stroking it, and at times using just her index finger and thumb to make a ring around his cock.
I'm sure she could have finished him off right here - with her controlling grip, he couldn't make any kind of move to escape without getting both his dick and balls squeezed - but Linda wanted to toy with him some more and she gently guided him down to his knees, then came around to his side and pushed him down onto his back. She told him not to move and took down the straps on her suit, peeling the top down to her stomach and revealing her amazing tits. She ran her hands over them and then laid on top of Jim, pushing her tanned boobs together and fitting them over his nose and mouth. She moved her hips so that the tip of his cock was pressing up against her cunt, with only a thin strip of material keeping the two apart. Had it gone in, Jim was definitely a goner. Luckily for our team but I guess unluckily for him, it looked like Linda was still bent on dominating and embarrassing him as she worked the tit smother, taunting him about how he'd never get to fuck her while she rubbed her lycra-covered pussy up and down his dick.
Jim was in a very bad spot here, but I guess it could have been worse; if Linda had closed her thighs around his dick, she probably could have finished him off then and there. I guess she was planning on finishing him off with a cowgirl, but she gave him too long to recover and counted too much on her rubbing her pussy against him to keep him immobilized. Linda emitted a surprised shriek as Jim threw her off him. Jim got up to his knees, but Linda seemed stunned and was slow to recover and was still on her back. Jim sat down on her stomach, pinned her wrists at her sides, and started licking and sucking on her tits. Linda bucked under him, but his weight advantage was telling and she couldn't escape. Jim flicked his tongue against her nipples, left then right, then took the whole thing into his mouth, left then right again. He trapped Linda's right arm under his thigh so he could use his left hand and started playing with whichever breast he wasn't currently sucking on, and then he reached behind him and started rubbing her pussy through her bathing suit. He kept this up until Linda was a sweating, moaning mess underneath him, and then it was time for the big finish.
Jim climbed off her slowly just in case she was playing possum again, but she didn't move, so he set about stripping her. When she still didn't move he rolled her on to her stomach and got behind her. He pulled her hips up, and it looked like he was about to get a great finish on her. Sure enough, he pushed into her from behind, and the deep groan he drew from Linda was as definite a sound of submission as I'd ever heard. Jim started fucking her, reaching straight ahead to grab a and handful of her long hair as he gave it to her. It looked like he pushed all the way in and started giving her short thrusts. This was probably the only way he could make Linda cum first - I can only chalk it up to the fact that he was able to pick the speed and depth of thrust that generated the most pleasure for her and least to him with the fact that Linda had seemed pretty hot and bothered by the match so far. (Jim hadn't lost his boner worshiping her tits, but he probably wasn't as ready to burst as he'd been earlier in the match when she was stroking his cock.) If there was any doubt that Linda had given up she reached back with one hand and started playing with her clit. After a few minutes Linda started bucking under Jim as she came, and he just kept fucking her through her orgasm, although I guess the feeling of her clenching vagina as she shook under him was too much, and he started cumming too before she came down. With both of them climaxing at once he was giving her wild, spastic strokes, but he finished with one big one, hilting himself with a groan and almost falling over on top of her.
There was no need for a pin or anything like that, and Jim pulled out, helped Linda to her feet, and walked back over to where we were sitting to a standing ovation. Jim high fived Matt as me and Rob gave him appreciative backslaps (you usually don't do butt slaps when the other guy's totally naked). Rob asked Jim what his secret was, but I couldn't stick around to hear the answer as my match was up next, and my opponent was already walking out to the middle of the mats.
The third match was me versus Maria (Matt's mom). We had quite a show to follow and I was already sporting wood that my forest-green speedo thong was doing a particularly bad job of covering. I'm about 5'10", told I look like a beanpole, and had my hair buzzed for the summer like Matt, but it was already growing back into its customary unruly black mop. As for my opponent, well, Maria's got this whole sensual, earthy thing going that really works for me, and the high-backed Mexican flag one-piece wasn't exactly covering a lot of her. It was cut high on the hips showing off her big, beautiful bottom, and the front was scooped showing very deep brown cleavage. Maria's short like her son, but where he's a quick little slip of a guy his mom is more built like a tank. I guess she's the enforcer of the group, although it feels a little silly to call her that when she's 5'2". She had the biggest curves, with natural tits even bigger than Linda's that must have been at least 40DD, not to mention her previously noted tremendous ass that I'd wager a whole generation of young men had come to grief under. Maria has a very round face with big black eyes and full lips that usually wore a smile, and today was no different (it was a little strange having her aiming the same smile at me across the mat as she used when telling me and Matt that we should take a break from Halo 4 and go outside). Her long, black silky hair framed her face and came down almost to the top of her breasts, which were looking ready to spill out of her suit, which was probably a size too small now that I think about it. I guess I can't throw stones since I felt like I was going to rip my own suit with my pre-match wood.
I tried to shake these thoughts as the match started. There's not a lot of kicking or punching by the boys in these matches (nobody wants to punch someone's mom), but there is a lot of slapping from the cougar's team, and sure enough as soon as me and Maria got close she reached out and slapped me across the face. Taking a page from her son's playbook she then stomped on my bare left foot. I couldn't stop myself from flinching and that was all the opening she needed to step in and sock me in the gut. I took a stumbling step back and she put her shoulder down and tackled me. We both ended up on the mat with her on top of me, trying to grab my wrists and pin me down. I wasn't that stunned, though, and managed to throw her off me. We both got to our knees, facing each other warily. She grabbed for my nuts which I managed to block, but it turned out this was a feint as her other hand slapped me again. Once again I was stunned and she reached forward and twisted my nipples. I yelped in pain and she grabbed my head with both hands and slammed a headbutt into my face.
I went down on my back, stunned at the direction the match was going in. In a daze I saw Maria's huge ass coming at my face and I knew I'd never get out from under it alive. I scooted away from her and got to my feet groggily. Maria came at me wearing that same beguiling smile. I shook the cobwebs off and put my fists up. Before she came into range she stopped and lowered the straps on her suit, setting free her gigantic breasts. I was of course mesmerized, staring at her obviously real, slightly droopy tits, and couldn't move to defend myself as she just walked up to me and locked me in a bearhug.
Maria had wrapped my arms up next to my torso, and as soon as I realized what she had done I figured I was in big trouble. I couldn't move my arms at all. With her height, her big melons were mushrooming against my stomach, and pleasure mixed with pain as she squeezed me. I frantically tried pulling my wrists free with big, spastic pulls, but it was no use. My legs started trembling underneath me as I couldn't get a breath with Maria's arms crushing my midsection. I lifted my right leg and tried to knee her, but I couldn't get a good angle, and Maria looked up at me, wearing that same smile as I was helpless in her grip. Before I passed out she threw me down to the mat on my back. I was too tired and stunned to move as she kneeled between my legs, grabbing my cock through my suit. She started jerking me off, slowly, looking in my eyes the whole time. She placed her free hand on my stomach, pressing down slightly, a signal not to move or resist.
We have a few advantages over the cougars; one of them is sheer stamina, and another one is that they sometimes underestimate us. I was in heaven with the slow cock-stroking Maria was doing, but I still had some fight in me. I knew I would probably only get one chance - one wrong move and her free hand would be squeezing my balls or one of her fingers would be up my ass - and I laid back, closing my eyes and moaning like I was giving up. The cougars were whooping and cheering for Maria and I waited about ten seconds to hopefully lull her into thinking I was done (any longer than that and I risked losing the match if she made me cum).
With as much energy as I could summon up I sat up, grabbing her wrists quickly. Maria grunted in surprise, and I pulled her up to her feet, still holding her wrists, twisting them painfully. Maria groaned in pain, bending over forwards slightly to try and ease the pressure, and I had to dismiss my instincts (either to start laying kicks into her dangling tits or one up between her legs). I forced her down to her knees, switching grips so she was in a front facelock, and gave her a DDT.
Maria's head bounced off the mats with a rewardingly loud sound - there's not much padding on top of the concrete - and she came to rest on her stomach. She got up to her knees slowly, and I was there behind her, pressing my back into hers, reaching around and grabbing her tits. She moaned softly as I started kneading them. I was hoping to weaken her up in this hold, but she reached between her legs and grabbed my hard cock, locking it between her thighs. She started moving her hips back and forth and I knew I had to get out of this immediately or she'd make me cum. I pulled my hands off her chest and instead got a double hammerlock, pushing her down to the mat on her face. I released her right arm so I'd have my right hand free and grabbed a handful of her silky black hair, pulling it back to raise her head off the mat, then slammed her face into the ground. I gave her five or six of these and she stopped struggling, laying limp on the mat. I cautiously stripped her, and when she still didn't move I rolled her onto her stomach, holding her wrists to either side of her head. At this she came back to life and started bucking underneath me, but she was out of gas; her face was red and she was coated in sweat and couldn't summon up the strength to throw all 5'10" of me off. I let her wear herself out until she lay there panting with her eyes closed.
Then I went to work. I pinned both of her wrists over her head with my left hand, leaving my mouth and right hand free to attack her tits. I'd been dreaming about getting my hands (and lips, and tongue) on her globes for a long time, and the little bit I'd gotten to play with them earlier in the match had only whetted my appetite. I went at them with gusto, Maria moaning and groaning under me as I tweaked, teased, licked and sucked on her dark little nipples, but she didn't try to escape. I doubted I could finish her off like this, but I hoped I'd be able to fondle all the fight out of her just the same.
By the time I was finished with her boobs, they were both coated in spit and her nipples were as hard as bullets. Maria herself seemed to be in dreamland. I cautiously released her wrists, and when she didn't move, I laid down on top of her. I quickly shed my suit and positioned myself between her legs, probing her pussy with a finger; she was gushing. That was all the invitation I needed. I lined myself up and pushed into her. She let out a gasp, reaching up and wrapping her arms around my torso as I slid home. We were both pretty turned on and this wasn't something I had much experience with, but I did want Maria to come first out of some naive notion that she'd love this so much she'd want to do it all the time. Since we were doing missionary I attempted to set the pace, trying to copy Jim's technique of just doing short, deep, quick strokes, but Maria was bucking her hips back into me and I almost popped out a few times. It was only a minute or two before I couldn't take it anymore and started cumming into her, shooting my load deep into her pussy as I kept fucking her, her fingers digging into my back. I went as long as I could, even giving her a few strokes after I'd cum, until I had nothing left and collapsed on top of her sweaty body. We just lay there for a minute in each other's embrace before I had the energy to pull out and roll off her. I realized with a start I had no idea if I'd won; the match had whoever cum first as the loser and evidence of my climax was already dripping out of Maria's pussy as I helped her to her feet. But she raised my arm in victory and I got a nice hand from our team, who I gave a big bow to (only realizing at the sound of cheers and hoots from behind me that I'd accidentally mooned team cougar). Maria hugged me and I went back to our area to get cleaned up. I was walking on clouds; we were up 2-1. Maybe we could win this whole thing.
Last up in round 1 was Rob (Linda's son) versus Jennifer (Jim's mom). Rob's a big dude, probably 6'1" and 230 pounds at least. He's got long, lanky blonde hair, and his somewhat bovine expression hid a fairly good power wrestler. His opponent, our host, Mrs. Jennifer O'Brien, looked even shorter than her 5'4" and I'd guess 135 pounds standing across the mat from him. What I noticed immediately when looking at her was her very pale white skin, even whiter than my mom's, which made her look like a ghost who'd wandered outside during the day. It was already oily with strong sunscreen (a favorite technique the moms like to use to make them harder to grip). Her red, straight hair was styled in a sidebang kind of cut that draped over her shoulders and a little over the left side of her face, and she had a liberal dusting of freckles over her skin. In contrast to Linda's model-like looks, Jennifer looked more like the mom next door, with a very cute face that I thought it was a shame to hide behind a curtain of hair. Today she was wearing a metallic green one-piece that didn't exactly flatter her pert B-cups, but it was cut very high on the hips - almost as high as Maria's - and did show off her nice legs. Jennifer blew a lock of hair out of her face and nodded at Rob and the match was on.
Jennifer was fighting dirty from the get go. Rob came at her with his arms wide looking to grab her, and she went low, dodging under his grip, then getting a upward slap right on his balls (with the tiny little speedos we guys have to wear, you couldn't miss where his junk was located). Rob, of course, instinctively covered up his goods, and Jennifer quickly propped her right knee behind his left leg, then pushed as hard as she could. Rob fell straight back like a falling tree and hit with almost as much force (well, all right, maybe I'm exaggerating, but only a little). Before he could move Jennifer had yanked his speedos down to his knees, and he rolled on the mat, awkwardly trying both to sit up and pull his suit back up. He managed to get to a sitting position and Jennifer swooped in, giving him a really mean looking backhand to the face. Rob was stunned and Jennifer started laying chops into his chest like she was Ric Flair. Rob managed to withstand a bunch of these but after twelve or thirteen Jennifer managed to chop him onto his back. She sprang at him, pinning his wrists up by his head, and planting her pussy right on his nose and mouth. Poor Rob not only couldn't move his arms, but his speedo still had his legs stuck together, and he was having a very tough time trying to generate enough force to try and buck his opponent off him. Eventually he managed to get his feet planted flat on the mat and started trying to roll himself over, and Jennifer let him up before he could escape, with the front of her bottoms marked with a very hard to miss wet spot.
I hoped that Jennifer being turned on would distract her and give Rob a nice opening, but I guess it evened out as his seven incher was at full extension waving in the breeze as he reached down and finally pulled his suit all the way off. He had just managed to get to his feet when Jennifer attacked.
Rob stopping to remove his suit was all the opening Jennifer had needed and she circled around behind him, running at his back, and at the last second leaping in the air, using her momentum to hit Rob with a huge bulldog that laid him flat on his chest. Barely had the sound of the impact dissipated than Jennifer was on him, laying down next to him. She quickly scissored his arm and then locked him into a crossface.
I felt really bad for Rob; he was getting dominated by a woman he had almost a foot on, and from the sounds he was making she wasn't being gentle with him. Rob slapped the mat with his free hand, but the arm closest to Jennifer was locked between her legs, and with how hard she was pulling his face back he didn't seem to be able to get his feet in a position to push off the mat. When Jennifer released him he flopped to the ground, his eyes rolled back in his head and his tongue flopping out of his slack mouth. Jennifer brushed a stray lock of hair behind her ear and then climbed on Rob's back, and gave his ass a few squeezes and playful slaps. He started waking up, pushing his upper body off the ground and shaking his head. Jennifer noticed this and she turned to face his head. She grabbed his right wrist and pulled it up behind his back. She stood up, pulling Rob up to his feet by the hammerlock, wrenching it so high Rob had to bend over. With her free hand she reached between his legs, giving his balls a squeeze, then grabbing his cock and stroking it to attention. Rob made to lift his leg to try and kick her away and her hand quickly fell back to his balls, giving them a short, sharp, twisting pull that made him scream. She told him to just enjoy it or she'd rip his nuts off and then returned to beating his meat.
It was a pretty humbling site seeing big Rob bent over helpless as a woman who weighed 100 pounds less than him and was twice his age had her way with him, but you don't wrestle in many of these tournaments without seeing something like this. Jennifer was relentless, and he didn't last long under her assault, with his hips bucking pathetically as he came. Jennifer kept milking his cock, trying to get the biggest load possible out of him. She worked him until she'd squeezed out the last drop, then forced him down to his knees, wiping the hand she'd jerked him off with on his back. She released the hammerlock and took a quick victory lap as the other moms cheered before heading back over to their area to get a drink of water.
Despite the absolute domination of our biggest team member, I was actually feeling pretty excited. A good percentage of these tournaments have the moms winning every single match, and going 2-2 in the first round was as good a start as I ever remembered getting. I didn't want to start getting ahead of myself thinking we could win this thing, but I felt much more chipper than I probably should have as I helped drag Rob back to lay across a towel off the mats.
The first round 2 matchup was Jim versus my mom. You're not allowed to put anything back on once it's removed, so Jim was buck naked while Emily still had on her white two-piece. I hoped Jim would fare better than Matt had, and I didn't think this was outside the realm of possibility since mom had only three inches on him, and her willowy build meant he definitely had the weight advantage.
Those positive feelings didn't last very long as the match started with Jim falling for a trick as mom offered him a elbow and collar lockup, only to hip toss him over her back when he went for it. She tried to climb on top of him, but he threw her off, then rolled away and up to his feet. They came at each other, with mom making an obvious grab as his balls that Jim blocked, but he left himself open for a hard slap to the face. He slapped her right back and mom seemed stunned. Jim came in and wrapped her up in a bearhug. I don't think this was as effective as it could have been given mom's height advantage, and when Jim leaned back and tried to lift her off the mat, her feet didn't leave the ground. He had wrapped her arms up so she couldn't use her hands to escape and I thought if nothing else that might buy him enough time to do some damage, but only a second passed before mom pushed off with her legs, jumping up and wrapping them around Jim's midsection. For a minute both teams were totally quiet watching as Jim and Emily squeezed each other as hard as they could, and the cougar team erupted in cheers as Jim lost, releasing mom. He tried to push her away but she had wrapped her arms around him, and as he broke his own hold, she moved her grip up to the back of his head, pushing his face in between her lotion-covered boobs, and he stumbled backwards and fell to the mat on his back, his opponent still on top of him. It was looking really bad for him now as mom worked the scissors and boob smother. Jim lay limp for a minute, I guess stunned at the impact, but he did start moving his limbs as we clapped and yelled encouragement at him. He reached up with his hands and grabbed my mom's arms, using his superior strength to pull them out to either side, breaking the smother at least. This still didn't do him much good as his nose and mouth were sandwiched into his opponent's tits, but he was able to turn his head and start getting some air. He started moving his legs, trying to roll over, and mom released her scissors, rolling off him and getting to her knees. Jim started getting up himself, but mom had given herself enough time to get behind him as he got up, wrapping his arms up in a full nelson. She snaked her legs around him to try and get her scissors again, and I figured if she succeeded the match was over. Jim must have had the same idea as he threw himself to the mat on his left side. This trapped mom's left leg under his body, but unfortunately it looked like it also left Jim trapped as he couldn't get up without freeing her leg. Since she was still working the full nelson that was bad news. It got even worse as mom switched holds, turning the full nelson into her pulling Jim's arms behind his back, then planting her free right foot into his back and pushing. She pushed him so far with her foot that she was able to pull her left leg from under him and added this to the right one in bending Jim's back. With him stuck on his side he wasn't able to get his feet under him and it looked like he couldn't get out of this hold as much as he struggled and kicked his legs. Mom kept the hold on until he went limp, and when she released him he flopped to the mat. Mom rolled him on to his stomach, then got behind him and pulled his waist up. Like with her previous victim she slapped her hips into his bare butt a few times. As she reached between his legs, though, Jim pulled his right leg back, and before mom could move he slammed his foot into her face in a nasty mule kick. Mom covered her face, and went down, stunned, as her team erupted in boos, which were quickly drowned out by our cheers as Jim hit a enziguri from all fours. Mom collapsed to the mat on her front and Jim pounced, rolling her on her back and unhooking her top, then pulling her bottoms off. Mom was still woozy and Jim sat down on the mat behind her, pulling her up between his legs. He pulled her high enough so that the top of her head was about even with his chin. Jim scissored her midsection, catching her arms at the wrist on both sides. With his hands he reached around and started playing with her tits.
Mom kicked and struggled, but she wasn't strong enough to free her arms, and she couldn't get her legs under her. She put up a good fight, but eventually she collapsed against Jim with a groan that sounded like she had given up. Jim kept playing with her boobs for a little bit, although his legs relaxed around her waist. Only when her eyes closed and she let out a fluttering moan did he release her. He laid her down on the mat gently, then rolled her over onto her front. Mimicking her earlier move he got behind her and pulled his opponent's waist up off the mat, but Emily was in no shape to resist the way he had earlier. He pushed her thighs apart and leaned forward. Mom just groaned into the mat as he slid into her. I couldn't help but applaud with the rest of my team as Jim went 2-0 for the afternoon. As with Linda he reached forward, grabbing a handful of mom's long black hair, and gave her short, deep thrusts. Where Linda had totally surrendered by playing with herself, mom was more passive, only really coming to life when she climaxed, bucking her hips back against Jim as he kept pounding her pussy. To put the cherry on top (and I guess because he'd cum already), he somehow managed to finish her off without cumming himself - no small feat given how jacked up on hormones we all were, let me tell you - and popped his dick out of mom's glistening pussy. He went around to her front, and pulled her up so she was holding herself up with her arms (she'd totally collapsed during her orgasm). He cupped her face with his right hand and pushed his cock into her mouth. My mom started sucking his dick, holding herself up with one hand and reaching out to massage his balls with the other. Jim only lasted 20 or 30 seconds before he came down her throat. Mom swallowed every drop, even giving his cock a few milking squeezes with just the tip in her mouth after he tried to pull out.
Jim came back to our corner to another round of congratulatory high fives. As for me, I once again had a heck of a match to follow; I was up next.
My heart was pounding and my cock was hard as a rock as I faced off with Jennifer. Like Jim I was starting nude while my opponent was fully clothed. I was very nevous; If I won my match, we'd have won the whole tournament; not only would we be heroes to every horny teenage boy in the neighborhood, but as far as I knew it also meant we got to boss around four foxy milfs all day.
So between that and my nerves from having seen Rob get demolished, I was watching Jennifer like a hawk for any ticks. She offered me a collar and elbow tieup, but I knew with my height advantage she wasn't going to win this and figured she was faking me out. I tried to go low and tackle her, but she saw this coming and shot an elbow into my face. I went down on my back and Jennifer jumped in the air, aiming her butt at my stomach. I rolled out of the way and she landed with a loud yell. I got up to my feet and Jen to her knees. I came up behind her and reached down, grabbing her right wrist and pulling it up behind her back in a hammerlock. I figured this was fair play since she'd dominated Rob with this hold. I debated getting her other hand locked up too, but decided that instead I'd reach around and start feeling her boobs. I guess I took a second too long to think because as soon as I went for this Jennifer simply ducked out of the hammerlock, pulling her small wrist out of my grip before I could think to clamp down, then turning and slapping me hard across the face.
I took a surprised step back and Jennifer used the same move on me she'd done to Rob, propping her left leg behind my right one and pushing me so I fell down. No sooner had I hit the mat then I was I frantically scrambling away from her and got back to my feet, fists in front of my face, as her team cheered the display she was putting on. She blew a lock of hair out of her face and motioned for me to come on. I did so, not really sure what I was going to do. Once again she offered me the collar and elbow. I tried to go over her hands and grab her, but she was far too quick and dropped to the mat, then sprang up and headbutted me in the stomach.
I collapsed on my side holding my gut. Jennifer was right on me and rolled me onto my chest. I frantically tried to get up but she had already sat down on my back. I tried to scoot out from under her, which didn't work as she grabbed my right ankle, and my crazed kicking and struggling only earned me a minute's reprieve before she caught my left one too. I felt her butt scooting higher towards my head as she pulled my legs up in a boston crab. She moved back until she was sitting almost on my shoulderblades and my body was making a C shape. I started crawling towards the pool with a half-formed plan of dumping both of us in it and escaping that way. I'd made it only a few inches before I felt Jennifer grab my cock, which had been waving in the breeze. She gave it a squeeze and I stopped crawling. She used two fingers and her thumb to start stroking me and my team was on its feet, with Matt and Jim yelling at me to do something and Rob pleading with me not to let her do that to me. I resumed crawling as fast as I could and the race was on. Jennifer had me rock hard in no time and then started jerking me off in earnest. The only things that let me last as long as I did is that she had to keep my legs pinned, and she couldn't get a very good grip on my dick without giving me the chance to escape. Also, whenever I made it about six inches or so, she had to take a step back to stay in position above me which meant she had to leave off my cock for a few seconds. Even so, she was beating my meat with gusto, paying special attention to the head once I started leaking pre-cum.
It was very close, but I won, barely. When we got too close to the edge of the pool Jennifer threw my legs down. They were so sore and stiff that I didn't even get a chance to get up; as I was trying to get my legs under me Jennifer grabbed me by my ankles and dragged me back to the center of the fighting area. I was still laying on my chest, and I was ready to buck her off if she tried to sit on me and re-apply the crab, but instead she laid down on my right side. She hooked her left leg over my hips and started spanking my ass. I bucked under her, but with her thigh pressing down on me there was nothing I could do. I could hear the entire cougar team including my mom cheering for Jennifer as she humiliated me. Her spanking really started hurting as she wailed on my butt and I had to bite back tears that I knew would have made it even worse. When she released me I had in mind a plan to spring to my feet and attack her, but I was so stunned when she did actually stop that that all I ended up doing was instinctively reaching back and rubbing my bare butt. This gave Jennifer the chance to slap a hammerlock on me, and I knew I was in really big trouble as she'd finished Rob off with this hold and I was a stick compared to him. Jennifer used it to wrench me up to my feet, dodging the wild elbow I threw behind me. Thinking fast I bent over and pushed my thighs back, trying to trip Jennifer and have her go over my back. This actually worked, and Jennifer flew over me with a scream of surprise. She hit the mat hard on her left side and rolled onto her back with a groan. I quickly rolled her onto her stomach and unzipped her suit. Getting it off was a little tricky as I had to lift her torso up to free the suit, and by the time I slid it off her feet she nimbly rolled away from me and hopped up to her feet.
I threw her suit into our area without taking my eyes off her. I'd lost my erection thanks to the pain of her spanking, but I felt it twitching to life as Jennifer didn't bother trying to cover up her naked, oily body (I guess as a precaution against losing her suit, she was coated in sunscreen from head to toe). I looked a second too long as she came in, reaching between my legs and grabbing my semi-hard cock. She gave it a squeeze and I reached down to free myself, but her other hand had darted between my legs and cupped my balls. "Don't fucking move," she hissed, "or I'll rip your balls off." She pulled me down to my knees, then pushed her bare tits into my chest, forcing me down onto my back. She was laying on top of me now and started scooting backwards between my legs. I saw my chance and lunged, shooting my hands between our bodies and grabbing her wrists. She grunted with effort as I pulled her grasping hands away from me. She was still laying mostly on top of me and we struggled wildly for a second. Just as I thought I was going to heave her off she started pressing her thigh into my genitals; my balls were trapped between her leg and my pelvis, and she exerted just enough pressure to let me know this. Even so I was able to scoot away from her, and thanks to the generous coating of suntan lotion and sweat I was able to get to my knees. Jennifer did likewise and we were facing each other, my hands still holding her wrists. I pinned them to her sides and leaned forward and down and started licking her nipples. Jennifer moaned as I flicked the left and then the right with my tongue. They were rock hard as I brought one into my mouth. I had become too absorbed in my work (I should have gotten her on her back like Maria) as Jennifer freed herself, pulling her wrists out of my grip. She grabbed my hair, pulling me away from her boobs. She leaned in and kissed me, forcing her tongue into my mouth. Before I could process this she broke the kiss and gave me a vicious backhand that knocked me down on my left side. Before I could move Jennifer had laid down on her right side facing my feet - we were in a 69 position. I didn't need any more of an invitation, spreading her thighs and darting my tongue into her pussy. I felt her gripping the back of my own thighs as she took my cock into her mouth.
Both teams were cheering their fighter on, and I hoped that Jennifer was turned on enough to give me a shot at winning. That fantasy came to an end as Jennifer clamped her thighs closed around my head. I tried to do this to her in return, but one of her hands had snuck around to my butt, and her index finger was pressing up against my asshole. I got the message as I relaxed my thighs and let Jennifer finish me off. She eased off the pressure on her scissors just enough to make sure I stayed awake for the grand finale. Her warm lips slid up and down my shaft a few times and then she started deepthroating me, the tip of her small chin touching my hips. On one of these downstrokes I came, shooting my load into her mouth, which she sucked up greedily. On the return stroke she went so high that just the head was in her mouth and used her hand to milk as much cum as she could from my prick.
I saw sunlight again as she released me, getting to her feet and posing for her team. Matt and Jim had to come drag me back to our area. They laid me on a lounger, then Matt and Rob gave Jim last minute advice. The final match of the tournament was about to begin.
Jennifer had no time to rest as the final match of the tournament pitted her against her own son. Both had two victories on the day and if Jim could make it three we'd be heroes. Matt and Rob were clapping for him, but I only had the energy to shield my eyes with my arm as the match started.
If Jennifer was winded from my match it didn't show as she immediately slapped her son across the face. Jim was stunned and she went for the takedown she'd used on both me and Rob, but as soon as she planted her leg behind Jim's he shoved her hard away from her. She somersaulted and came up to her feet, charging at Jim and giving her a shove of her own. He didn't have the same grace as his mom and where she'd rolled with the force of his attack, he just fell down awkwardly. Jennifer reached down to grab him, but he pushed her away by the thighs and she had to let him get up to his feet. She came in and tried to lift her knee between his legs, but she hadn't had time to really aim this and some of the force hit his upper thigh before sliding home and nailing his balls. Still, it was enough to drive Jim back covering himself. His mom ducked to his right side and swept his right leg out from under him and he fell on his back, winded. Jennifer rolled Jim over onto his stomach and laid on top of him, her boobs mushrooming against his back. She reached her arms around his neck to get him in a sleeper, but with one big motion Jim bucked her off. Jennifer went flying backwards and the back of her head smacked off the ground. She lay still as Jim capitalized, sitting down on her stomach. He tried to pin her wrists by her sides with his legs, but her hands were so small that as she came around she was able to simply pull them free. She reached up and gave him a double nipple twist. Jim was shocked by the sudden pain, giving his mom enough time to ball up her right hand into a fist, which she launched into his stomach. But she didn't have a good angle, and Jim just grunted, trying to grab her wrists. He got the left one pinned to the mat, but she slapped his face again with the right. Jim looked disorientated and kept trying to grab her hand. Jennifer succeeded in dismounting him by firing a upward palm strike that hit him in the jaw and he rolled off her in a daze.
Jennifer finally looked like she was slowing down a little as she got to her feet, panting, with sweat pouring off her naked, oiled body. Unfortunately Jim didn't look too hot himself laying on his side with his eyes closed. Jennifer planted her right foot on the side of his head, then reached down and grabbed his arm and pulled it straight up. She started twisting his wrist and Jim screamed. His other arm was partially trapped under his body and at first he slapped blindly at his mom's leg, but following our advice he managed to roll onto his back. His mom had to give up the hold, dropping down into a crouch and stalking him. As Jim got to her feet she charged into him.
I almost laughed out loud as Jennifer bounced off her son. Her technique was good, but she'd only backed up a few feet, and she looked like a puzzled cat bouncing off a large dog as she hit Jim's tensed stomach and recoiled. I guess she was more used to fighting women her own age as she seemed stunned, and Jim stepped in and slugged her in the gut. It looked like this blow didn't have all of his force behind it, but it was enough to drop his surprised mom to her knees holding her stomach. Jim wrapped his arm around her head and pulled her up into a front facelock. He went for the DDT, but just before he could execute it his mom's hand struck out and grabbed his bare balls.
The momentum swung back as now Jim was in a real bad spot. He still had the front facelock on, but it didn't seem to be slowing his mom down as her other hand wrapped around his cock and started stroking it. I couldn't even think of any advice to yell; Matt was yelling to use his knee, which I guess would have worked, but this wasn't that kind of match, and Rob was once again giving the timeless if useless advice of "don't let her do that to you". Jim stumbled backwards, dragging his mom with him; I shouted for him to get to the pool, hoping he could escape the same way I had. But it was no good. The hand Jennifer had on his dick came off it just long enough to grab the back of his left knee, and she pulled it out, dumping him on the mat. He let the facelock go and quick as a flash his mom sat down on his upper thighs. She kept one hand cupping his balls and went back to stroking his dick with the other. Jim couldn't move his lower body, but he was able to sit up. He did so, giving his mom a hard push. I think she was holding on to his cock and balls for dear life, as she went backwards off him and he screamed. He got up to his knees, but he was holding himself and had his eyes shut in pain. Jennifer got her to feet and went behind Jim, then ran at him and smacked his face into the ground with a bulldog.
Now it looked really bad as Jim was laying on his stomach not moving. Jennifer laid on top of him again, and this time she was able to lock the sleeper around his neck. Jim came to life pulling at her arms and trying to get to his feet at the same time. Jennifer locked her legs around his midsection adding a scissor hold to her choke as Jim drunkenly got to his feet. He threw himself backwards on the mat and Jennifer didn't have time to let go, emitting a loud grunt as her son landed on her with all his weight.
Jim rolled off her and both fighters lay still for a minute as both teams urged on their warrior. We grew even louder as Jim slowly sat up, shaking his head. He got to his feet rubbing his neck, which had turned red, as Jennifer just began to stir. Jim shook off the cobwebs and walked up to his mom as she got to her feet. She held her hands up, palms forward, trying to ward him off. Jim reached down grabbed her wrists, throwing them to either side, and that was all the opening she needed to dart forward, taking his semi-erect cock into her mouth.
This was a desperation move on Jennifer's part, but I guess she really wanted to win. Jim just stood there dumbstruck as his mom started sucking on his cock. She scooted a little closer, cupping his balls with one hand, keeping just the tip of his cock in her mouth as she jerked him off with the other. We were all yelling pleads and threats to Jim, but he was beyond our power to reach. Jennifer worked his dick until his eyes rolled back in his head, then popped his saliva-slick unit out of her mouth. She headbutted him in the stomach and Jim sank unresisting to his knees. Jennifer got to her feet, cupping her hands under Jim's armpits and dragged him over to the pool. She rolled him in and then stood with her hands on her hips until he came up for air.
As soon as his head broke the surface she was there, reaching down and grabbing his wet hair with both hands. She hauled him to the side of the pool, with just his head and shoulders sticking out as his back was pressed into the pool liner. Jennifer without missing a beat laid down on her back, scooted forward, and wrapped her legs around his neck, getting him in a figure four-style scissor choke with Jim still mostly submerged. He kicked wildly under the water and his hands came out to try and pull his mom's thighs apart, but he had no leverage at all and couldn't get a grip with his wet hands. The cougar team was on its feet cheering and hollering their approval at what I had to admit was a pretty impressive display. Jennifer for her part put her hands behind her head, looking like this was the most normal activity in the world to be indulging in in a hot summer day.
Jim tapped out and the tournament was over. His mom helped him out of the pool but his day wasn't quite done yet. She made him go to the center of the mats and had him lay down on his back. Jennifer planted her bare pussy on his mouth and started riding his face, a victory I can't deny was well-earned. I felt a little bad for Jim as he hadn't gotten off himself and his boner was waving in the breeze, but it looked like Linda wanted round two as she strode over to Jim and impaled herself on his prick. We watched the show in silence, knowing that as soon as the cougars had finished with Jim, he'd get awarded his speedo, and then we'd have a very long day ahead of us.
