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Taking It for the Team Pt. 02
bydpingjessie©
If it's possible for a team to back into the playoffs, that's what my ice hockey team had been doing for the past couple weeks. With a berth in the postseason all but locked up, the team had now lost seven games in a row -- more losses in two weeks than we had in the previous two months! -- and the playoffs were suddenly no longer a sure thing.
The losing streak was obviously weighing heavy on the guys, especially my buddies Jack, Howard, Gus and Moe, who had been the ones to form the team to begin with and had been, until recently, largely contributing toward piling up the wins. With one game left in the regular season, morale had hit rock bottom. One more win was all we needed to clinch a spot, but with the downward spiral we were caught in, we honestly didn't believe we could pull out just one more measly game to get us that fresh start in the new season.
My team was on my mind almost all the time during this stretch, so it was hard to find much enjoyment in anything. Fortunately for me, my best friend, a hottie named Jessie, was making her annual visit home by herself. When she had come up last year, leaving the husband and son behind for a week, it led to some exceedingly ungodly fun, so I was hoping for a little more of the same this time and, thus, help take my mind off my anxieties.
Jessie was staying with her parents for the week, which wasn't all that close to my apartment, but the time of travel didn't prevent her from stopping by my apartment her first full day in town. It was always a pleasant sight when the 5'5" slender brunette was standing at my door. Even though she was in her late 20s, she looked at least a few years younger, and, from her tight frame, you'd never tell she had pushed out a k**. You also couldn't tell from her stunning smile or her innocent bright brown eyes that she had so eagerly participated in the raunchy, debauched activities of which I had had the immense pleasure of being a part over the past few years.
The look on Jessie's face said it all, but what the girl was wearing punctuated her point. After all, no one wears a tight top, short skirt and high heels underneath a long coat in the dead of winter when she's looking to just hang out. After very little catching up in the living room, we were both in my bed with the only clothing between the two of us still on being Jessie's high heels. The lady loved her shoes, and I loved how she would sometimes wear them during sex. Nothing looked hotter than Jessie wearing nothing but a pair of sexy heels.
For the next half hour or so, I fucked another man's wife hard on my bed like I had done to her several times before. Jessie and I had been best friends for more than 10 years now, and that relationship had often erred on the side of romance, even after Jessie got married. We didn't cross the line of sexuality entirely until one fateful night four years ago when we had sex in my apartment while Jessie was stranded during a snow storm while her husband was out of town. Since then, the sexual element of our friendship was a bit of a roller coaster. I still don't think her husband knew about it -- that is, except when he and I were fucking his wife together.
My fond friend of now 12 years was always the best sex I had, no matter how we were doing it. This time was no exception. I rarely saw Jessie since she moved out of state not long after that first time we slept together, and I even less seldom fucked her just to myself, so I cherished this moment. Like I said, I didn't know if her husband had any idea his wife screwed me when she was back in her hometown without him, but Jessie was so irresistible that I had long since dismissed those qualms.
I had actually just seen Jessie about a month ago when her family visited during the holidays. Her husband and I teamed up on her a few times during that span, but it didn't matter how much she satisfied me while she was around; I always longed for more as soon as she went back south. One simple month felt like ages, and the pounding I gave her as she wrapped her limbs around me while lying on her back in the bed demonstrated just how badly I had desired to vent my obsessive lust. At last, I brought my dear friend to a screaming orgasm, indicated also by her nails' sinking into my back, her heels poking my ass and her mouth letting out a cry of undeniable pleasure while her pussy convulsed around my thrusting cock. Her orgasm was almost always enough to beckon my own, and this time was one of those instances.
I told Jessie I was going to cum, so she relaxed just enough to allow me to push myself up and withdraw my cock from her pussy. As my lady friend's perfect B-cup boobs heaved up and down, recovering from the orgasm that had just rocked that sexy body, I jerked off and plastered her tits with a generous helping of semen, cursing and moaning in delight as I did.
I collapsed next to Jessie, both of us catching our breath now as both of our bodies glistened with sweat. As Jessie kicked her shoes off and got comfortable with me in the bed after cleaning the semen off her breasts, small talk ensued, and soon I was telling her about the woes of my hockey team and the big game we had on Saturday.
While Jessie had met my friends on the team only once, she was in one way very well acquainted with them. About a year and a half ago, I had talked Jessie into a five-man gangbang in which my hockey buddies and I each got to enjoy the full experience of Jessie's rocking body. Undoubtedly it was the memory of that incredible night that inspired Jessie to make the offer that she would make.
"I bet I could boost your team's morale," she said with that unmistakable grin.
"What, like a strip tease?" I asked, intrigued.
"There would be no teasing," she responded. "A tease wouldn't be good for your spirits."
"Another gangbang?" I said, now beyond excited. Jessie just nodded her head, still grinning. Then she noticed that, even though I had just emptied my load a few minutes ago, my cock was getting hard again. "Maybe you want to practice right now by sticking that in my ass," she offered.
After giving Jessie anal for the first time in non-group sex and depositing the meager load my balls could supply on such short notice, we finally got out of bed and went out for the night. During the night, Jessie picked out a photo for me to show to my teammates in the locker room after our practice tomorrow in order to see whom we could round up to gang fuck her. I imagined there would be plenty of guys who would sign up.
The next day, I ran the idea by my four friends, and, naturally, they were stoked on the idea. In fact, Jack was so excited that he was the one to announce it to the rest of the locker room. Of course, a lot of guys on our team were in committed relationships, so I knew it wouldn't be all 22 of them dominating my poor friend, but most of them still wanted to see the picture of Jessie, and they all agreed she was a knockout babe. I'm sure most of them thought it was a joke or some sort of scam, like the ones you find on Craigslist.
We did have four guys, though, who committed to be at the rink with us Saturday afternoon before the game to have what we were calling an "optional practice." Their names were Kyle, Ryan, Evan and Matt. I didn't know how many guys Jessie was expecting, but I assumed nine would be enough! Personally, the biggest gangbang I had been a part of consisted of eight people, and that number included the girl. It was going to be an interesting pregame, to say the least.
With puck-drop at 6:30 pm and the rest of the team arriving around 4:30, we arranged for the 10 of us to show up at the rink 2 pm the day of the game. We figured it would give us at least an hour and a half to enjoy Jessie, by the time we were all prepared, and still leave about a half hour to clean up and be ready before the rest of the team showed up.
Jessie and I traveled to the rink together after Jessie had showed up at my house to carpool. It took every ounce of self-control to not fuck her right there in my apartment after she showed me her outfit. It was her old cheerleader uniform from college, and I was really impressed that it still fit her so well. Like most cheerleader outfits, it was sleeveless and had a very short, pleated skirt. The colors were blue, white and red. Originally she was going to wear sneakers to match the outfit, but I talked her into sporting the black and white high heels she had also brought. In addition to showing a little more skin and making her ass look a little tighter, the open toes showed off her French tip toenails. I understand cheerleaders don't typically wear high heels, but Jessie's feet were too cute to obscure with sneakers.
Jessie and I arrived at the arena just before 2 pm. For now, that same large coat from earlier covered Jessie's outfit, except for the heels and, of course, her long brown hair, which she had curled for the event. She didn't often curl her hair in that manner, but the slight change of appearance was cute and went well with the cheerleader getup. Of course, she also made sure those pretty eyes and lips were popping with just the right amount of makeup.
When I got Jessie to the locker room upon which we had all agreed, I saw that the eight other men were already present, and that presence was made clearly known as the group erupted into cheers in order to warmly welcome the sexy guest of honor, who grinned and blushed quietly in the spotlight. I knew, though, that she would come out of her shell soon enough.
"Hot damn," Matt, our goalie, said, "she's even hotter than in the picture!" The other new recruits agreed, while the guys who had been with Jessie before just grinned as memories from a year and a half ago undoubtedly swam through their heads.
"Well, what are we waiting for?" Jack said excitedly. He then pushed the play button on his phone to begin his pump-up playlist, as he often did before games. We'd heard these songs in the locker room many times before, but there had never been a girl in the room.
We guys took our seats on the benches, at which point I noticed that one of my buddies had laid a mat out on the floor by the lone column in the middle of the room. It was a good idea, since this floor could get only so clean, and Jessie was already going to be getting dirty enough for us.
Jessie needed only a minute to calm her nerves, and the boys were very patient with her as she took off her coat, a little timidly at first. Once we all got to see the cheerleader outfit, the group roared with praise and approval. The affirmation seemed to bring Jessie to full composure, and that confident, sure, wicked grin spread across her face as she strutted over to the mat.
We cheered louder and louder as the hot brunette milf took center stage and swayed to the beat of the music. Without hesitation, she pulled off her shirt, tossing it behind her and revealing a white bra with red polka dots. We all continued to voice our approval, getting more excited as Jessie continued her strip tease.
"Take the bra off!" shouted Howard. Jessie smiled and shook her head, instead reaching under that short skirt and pulling a red thong down her slender, slightly tanned legs.
"That'll work too!" said Moe, nudging Howard. Jessie pushed the garment down to her knees, slowly in a teasing fashion, until it got to her knees, at which point she let it simply fall to her ankles. Then, pushing her curled hair behind her ears, Jessie carefully pulled her high-heel-clad feet out of the thong, stepping out of it and kicking it disdainfully to the side amid the constant cheers of her fans.
"Skirt on or off?" Jessie asked flirtatiously.
"On!" we all agreed.
"Heels?"
"On!"
"Bra?"
"Off!" Jessie laughed and reached behind her back, unhooking the brassiere and throwing it right at me to the tune of the music and eight other guys' hoots and hollers. Those cheers got as loud as they had been all afternoon once Jessie's smallish but perfect boobs were on display as the woman stood before us wearing only shoes and a very short pleated cheerleader skirt.
Jessie cupped her boobs for a second and then lifted up the skirt, giving all of us a full view of her shaved pussy and eliciting another strong reaction from her audience. Then, her hair flinging around as she did, Jessie turned around and leaned against that column behind her and stuck her ass out.
"Who's first?" she asked.
"Not so fast!" I said, jumping up and beckoning Jack and Gus to join me. Looking over her shoulder, Jessie grinned, not too sure what I was doing just yet until I stepped up to her and playfully turned her back around and pushed her to her knees. In seconds, Jack, Gus and I had our pants undone, cocks out, hard and ready. By the time we three guys had our pants around our ankles, the other six guys in the room were disrobing as well.
From her knees, Jessie took Gus's cock in her right hand, Jack in her left and lucky me in her pretty mouth. Our teammates all surrounded her then, and for the next 15 minutes or so, Jessie made her rounds. As nine men circled her, Jessie turned every 30 seconds or so to take a different cock in her mouth and in each of her two hands, expertly stroking them as she wonderfully sucked on another.
Even when my dick wasn't in Jessie's hand or mouth, I at least had quite the sight to see as my best friend rotated around and pleasured all of my teammates who were in that locker room. Those gorgeous eyes beamed as her head bobbed back and forth slowly while her hair shifted as well. Whoever Jessie pleasured would moan with satisfaction, and all of us, no matter whom Jessie was attending to at the time, affirmed and praised the sex goddess as she showed off her ability around multiple cocks.
Once everyone had gotten at least one turn in one of the pretty brunette's hands and at least one turn in the mouth, Jessie was helped up to her feet, at which point she went back to leaning against the column and sticking out her ass. As the captain of the team, not to mention the best friend of the entertainment and the one who brought her, I was given the opportunity to take the first ride. My teammates took a step back and cheered me on, and Jessie peered over her shoulder at me, just the corner of that amazing smile visible as I stepped up behind the knockout brunette.
I put one hand on Jessie's waist while the other guided my engorged prick into the girl's pussy. My tip was greeted with the wonderfully wet folds of Jessie's vagina and had no trouble working its way in. Once I had the head in, I put both of my hands on Jessie's waist, holding my friend in place as I sank forward into her. Jessie and I moaned in unison while our fans cheered us on, my cock sinking deeper and deeper into Jessie until my balls were touching her clit.
Jessie moaned louder and slapped the column while I briefly ground against her. Then, to the admiration of the onlookers, I started to thrust in and out of my dear friend, slowly to begin as my dick got coated in her sweet juices. Jessie looked straight ahead, her fingers pressed hard against the stone in front of her as she moaned and took my steady pushes into her lovely body.
"I can already feel the morale going up," I said as I increased my pace, thrusting faster and harder into my married lover, my hips now slapping against her ass cheeks. My teammates encouraged me to continue and give the sexy brunette the pounding she needed. They hadn't seen anything yet, I thought.
After a few minutes of taking a solo run with Jessie, I pulled out, and the train really began. One by one, all nine of us had Jessie the same way, bent over against that stone column, steadily fucking her from behind. Some fucked her slowly and deliberately, and others screwed her hard and fast. Some held onto her waist, others her ass or tits, and a couple even pulled her hair. No matter what, Jessie moaned as her lover grunted and groaned behind her. Ryan even got her to cum, which was hot to watch, seeing Jessie tense up and cry out as a perfect stranger nailed her twat.
Kyle acted as the caboose of this train, being the last one in line to make Jessie moan. After he finished his run of hard thrusts into the woman, he pulled out and allowed Jessie to stand up straight. Now it was time to decide how to proceed.
The team again looked to me. I asked for a volunteer, of which I had plenty. Moe was the closest, so he joined me with Jessie on the mat as the beautiful brunette grinned. I think she knew what was coming and readily allowed us to pick her up, I in front of her and Moe behind. The crowd, especially the new guys, really started to voice their excitement as Jessie spread her legs and d****d one arm over each of us, her right arm over my left shoulder and her left arm over Moe's right shoulder. With Jessie suspended in the air, Moe and I went to work fixing the girl on our pricks.
Jessie cooed as my cock slipped effortlessly back in her pussy but then gasped a bit as Moe's cock poked her asshole. I knew she would be OK, though, as she had done this same thing several times before. Once Moe was able to ease the head of his penis into Jessie's ass, he and I lowered the girl until we were both balls deep inside her.
The hoots and hollers were almost deafening as seven other men watched Jessie take two cocks. Kyle, Matt, Ryan and Evan were especially in awe, having never seen such a sight in real life before. The rest of us, of course, were entirely aware of Jessie's capabilities, and the newbies were about to see much more.
Once she was settled on our cocks, her feet dangling over the floor, Jessie cried out with excitement, her face beaming. Moe and I solidified our grip on the babe and then began to lift her up and lower her back down, sliding her up and down our shafts, which went in and out of her, mine in her cunt and Moe's in her ass. Before long, we were shifting her faster and faster, causing her hair and boobs to rock up and down as she took us deep and hard into both her holes.
Amid the raucous cheering of our onlookers, Jessie enjoyed a standing double penetration as her legs bounced with her body, which remained suspended in the air for a couple minutes. It was quite the workout for us guys, so much so that we actually lowered her a little bit at one point so that she could put one heel on the floor while she lifted the other one up over my arm. Jessie smiled at me as she now stood still and let Moe and me take turns going inside her ass and pussy. Her fabulous cunt felt even better now that it needed to compensate for her stuffed asshole as two cocks rocked in and out of her, separated by just a thin membrane.
Moe and I were sweating pretty good, and Jessie had some beads dripping down her flesh as well by the time we guys passed her off to the next group. Stepping up next were Jack and Matt, who gave Jessie a standing DP as well for a few minutes, the whole time allowing her to plant one foot in the ground as they sawed in and out of her tight, hot body.
Once Jack and Matt had their turn, Kyle and Evan stepped up, choosing to split-roast Jessie rather double-penetrate her. Kyle took her from behind and bent her over so Evan could stick his cock in that gorgeous mouth, and the two immediately began to thrust in and out of either end of her. Jessie's cries were muffled by that cock, but Evan's and Kyle's moans were clearly heard as each man fucked his respective end of their new fuck toy.
After a minute or so, they stopped thrusting and stood still, instead sliding Jessie back and forth between them like a slinky. By now, as the cheering was losing some steam, we could all hear the wet smacking of Jessie's pussy as Kyle pounded the hot girl. Jessie held onto Evan's hips as his cock plunged in and out of her mouth while she submitted to their lust, slamming each end into them over and over again.
Once Evan and Kyle finished their turn, Ryan, Gus and Howard were all up, a trio this time instead of a pair, since we didn't have an even number. Gus grabbed Jessie and pulled her down with him, he lying on his back on the mat and Jessie facing down on top of him as the two worked together to get Gus's cock inside Jessie's vagina. They sighed together with pleasure as Jessie sank down to Gus's balls just in time for Howard to kneel behind Jessie and proceed to impale the lady's sweet ass. Jessie and Howard grunted as Howard forced himself into Jessie's backdoor, which was certainly very tight, since her pussy was already stuffed to capacity, his dick going deeper and deeper until both he and Gus were balls deep in the same female again. All the while, Ryan was waiting his turn to take the only hole that was left.
"We call this a Jessie sandwich," I said to the rest of the guys as they stood back with me and watched Howard and Gus begin to saw in and out of the hot wife whose husband almost certainly had no idea what she was doing right now. Once Howard and Gus had their rhythm down and were thrusting steadily in and out of Jessie as she was smushed between them, Ryan stepped forward, cock in hand, and topped Jessie off, making her airtight.
With all three holes stuffed, Jessie never had fewer than three cocks in her for at least the next hour of this wonderful, amazing, ungodly gangbang. From that point on, there were still cheers and Jack's playlist was still on a loop, but whoever was looking on seemed to be in an awed silence as the beautiful woman in her late 20s took multiple cocks in all her holes like a champ, sinking deeper and deeper into depravity with the rest of us.
"Call me crazy," Matt said to me, "but I think we're going to win our game tonight." I have to say, all the tension caused by our losing streak seemed like a distant memory as I watched my best friend get pounded in all three of her holes simultaneously. The best part was, the main event was only getting underway.
The guys fucking Jessie were, understandably, getting carried away, hammering Jessie hard and for some time. I needed to intervene and tell them their time was up, reminding them that it was still too early for the guys to climax. Of course, Jessie could climax as much as she wanted, but she wouldn't be able to if we were too rough with her. The boys complied and pulled out of her, allowing the next set of three to take the mat: Jack, Moe and me.
Jack lay down on the mat as Jessie staggered to the side for now, her hair already a mess and her body gleaming with the sweat of herself and two or three other men. Once Jack was in place, I helped Jessie step over him and then sit down on his cock, her face and boobs facing out as she squatted and allowed Jack to poke his phallus into Jessie's sufficiently broken-in shitter. Jessie barely cried as she took the rod in her ass and just simply lay her back on Jack's chest before lifting and spreading her legs for me, which alone would have been enough to make me completely hard if I hadn't been already.
With the sight of Jessie's tight ass stuffed with my buddy's cock and the girl's sexy legs spread, inviting me to sandwich her, my heart was pounding and my dick was ready to go. I hurried in between those sets of legs and leaned forward, pushing my cock into Jessie's vagina, which was still nice and wet. Even with the constriction caused by Jack's cock in Jessie's ass, my penis slipped right in so that both of us guys were to the hilt inside my best friend.
Once inside Jessie, I lay down on top of her, sandwiching the lovely lady between Jack and me. We got right to fucking her holes, pumping back and forth into her, taking turns in our respective hole like we were pistons. As we double-penetrated Jessie, Moe stood to the side and lifted Jessie's head up so he could stick his cock in her mouth and make her airtight again.
Our three cocks bounced in and out of the sexy brunette, who was trapped helplessly among these three teammates. We worked her over good so that Jessie was enjoying it as much as we were. The evidence of Jessie's joy came when we got her to cum for the second time that afternoon, which was clear by her screaming around Moe's cock as her pussy convulsed around my thrusting dick.
Moe pulled out shortly after Jessie started screaming in climax, but Jack and I sawed in and out of her just a little longer until we too pulled out and allowed Jessie to lie on the mat while Matt, Evan and Kyle, the final trifecta, were ready to go immediately.
Wasting no time, these three arranged themselves a little differently, lying Jessie on her side and lifting her right leg straight up so that the heel of her shoe pointed to the ceiling. Then Evan lay parallel behind her and quickly stuck his dick in Jessie's ass, followed immediately by Matt, who knelt over in front of Jessie, slipping under the outstretched leg and inserting himself perpendicular into Jessie while Evan was already fucking her ass. Meanwhile, Kyle got to his knees in front of Jessie's head, and Jessie obediently took Kyle's cock in her hand and stroked it fast before working it into her mouth.
Now this sight was something new, as I had never seen Jessie take a double penetration in this position. I don't know how comfortable it was for her, but it looked really hot, especially with her leg poking out up into the air out of that writhing mass of flesh. Jessie was doing an especially noteworthy job of sucking Kyle's cock as the two other players sawed in and out of her other end.
Seeing Jessie take all these cocks in all these different ways gave me at least one more idea to carry out with her. Once the last three men took their run at Jessie, I suggested we still hold off on culminating this morale-boosting, team-building event for just a little longer and work Jessie over some more, if she was OK with it.
Kyle, Matt and Evan finished up just short of a climax, knowing there was still some time left for more fun. They stepped away and left Jessie to lie on the mat, her body vacant and shining with sweat. Her hair was a wild, matted jumble, and her tits heaved up and down as she tried to catch her breath. She looked like an exhausted mess, so much so that I even asked her if she was in good shape to go on.
"I didn't tell you bitches to stop, did I?" she playfully said while rolling to her side, still looking no less exhausted.
"Oh, you asked for it now!" I played right back before making my move. "Let's see how many cocks we can put in her at one time!" I said to my buddies.
Undeterred, Jessie sat up, her eyes getting brighter again and that confident, seductive smile creeping across her face. I stepped up to her first, getting down with her on the mat, which was now slick with the sweat of 10 different people as well as the vaginal juices of one particularly sexy female. I then lay on my back and pulled Jessie on top of me, securing her wet pussy with ease on my cock as blissful feelings overtook my senses. No matter what the circumstances, sinking my manhood into my best friend was always an experience I didn't take for granted.
Jessie and I moaned in unison as our bodies were joined again. She smiled down at me as she started to ride my cock the instant my balls touched her taint, her piercing brown eyes meeting mine. She worked herself up to a pretty good pace within a few seconds, but it wasn't long at all until Jack stepped up behind her and pressed his prick against her used asshole.
After Jack was in position, Kyle stepped up and grabbed Jessie's chin, pulling her head toward his cock so he could stick it in her mouth. Then Evan and Gus stood at either side of Jessie, each taking hold of one of her wrists and coaxing her to stroke them off while she took a cock in each of her sex holes. In a minute, Jack, Kyle and I were successfully thrusting in and out of the same gorgeous female while she managed to stroke off two other men, completing the airtight ski-poling that only a sex goddess like Jessie could pull off.
"Five, wow!" exclaimed Matt as he, Moe, Howard and Ryan watched on. "Can't really take more than that."
"I beg to differ," interjected Moe, who then joined Kyle over me and in front of Jessie's head. "That pretty mouth looks big enough for two."
"And while we're at it," added Howard as he shuffled behind Jessie while Jack and I double-penetrated her pussy and ass.
"Now that's more like it," I panted, admittedly a little overwhelmed with all the commotion going on around me. However, it was nothing like what Jessie was coping with, and it was hot as hell to be in the middle of this raunchy, wicked gangbang. In my experience, I knew one girl who had pulled off triple penetration, and even that girl didn't do it that well, but if anyone else could, it was Jessie. I had to see her try, at least.
"Holy shit," Jessie exclaimed as Kyle temporarily removed his cock to allow Moe to try to wedge his in there. "Fucking gadamnit!"
"That's right, baby," Moe said, "You got this," and the proceeded to begin cramming his dick into Jessie's mouth beside Kyle's. Meanwhile, Jack had shifted up Jessie's back, still pounding her ass to make room for Howard, who scooted in behind Jack and pushed the tip of his long cock against the base of mine while I was still thrusting into Jessie's pussy. I had to pull back a bit and come to a stop to allow Howard to do his thing, but I didn't mind. I had done double-vaginal on a couple of different girls before, actually, and one of them was Jessie, so I had long since gotten over any qualms with incidental male-on-male contact.
With the sexy babe still pressed against my chest, I could clearly hear the muffled screams coming from her throat, her mouth now filled to the brim with two cocks. The screams sounded only more desperate as Howard pushed himself harder and harder into Jessie, forcing his cock deeper and deeper alongside mine in her pussy. Jack even pulled out so that only his tip was in Jessie's ass so that Howard and I could get our manhood sufficiently wedged inside my lovely friend's tight cunt.
Jessie calmed down after a minute, and we took another moment to adjust to the extreme conditions. Soon, Jessie, albeit weakly, began to stroke off Ryan and Evan, just as Jack, Howard and I slowly but surely found a rhythm and started to pump our three cocks in and out Jessie's two holes like a well-oiled machine. Meanwhile, Kyle and Moe were essentially taking turns fucking Jessie's mouth, occasionally stuffing both pricks past those lovely lips.
Jessie squirmed and moaned as much as she could as five men fucked her sexy body while she did her best to stroke two more off. From then on, I could hardly tell what was going on as this mass of thrusting, writhing flesh moved above me while I continued to pump hard into that sexy pussy I was sharing with another dick. I was kind of stuck where I was, but I could see the other guys shifting around and taking turns with different parts of the female's hot body while they all cursed from excitement and praised their wicked sex goddess. At one point, I felt Howard pull out of Jessie's pussy followed by another cock's replacing it, joining me in my favorite twat. I'd find out that it was Matt who had taken Howard's place in the triple penetration.
Sweat was pouring out all over my body and mingling with that of my best friend as she was mercilessly pounded in all her holes beyond capacity with nine men who all took their turns with the team's new cheerleader. While Jack's playlist continued, the hooting had subsided for the most part as we all grunted and moaned while we all enjoyed the center of attention. The slapping of flesh and the squelching of Jessie's holes added to the soundtrack as I held the girl tightly and pushed hard into her pussy, competing with Matt's cock for room in there while Ryan, who had switch with Jack, caused Jessie's love canal to be even more constricted as he railed the lady's asshole.
The gangbang went on in that manner for a little while longer as most of the eight other men rotated and took turns in different parts of Jessie while she and I remained pinned in place amid the bodies and the intensely hot air that surrounded us. I had to pace myself, as I'm sure we all did, so as to hold off an orgasm until the very end, though cumming in Jessie's pussy wouldn't have been the worst way to end it. I honestly didn't mind not having the ability to switch holes. If I could stay put in any one place in the world all day, it would be Jessie's pussy.
At one point, I heard Matt say, "Let's put two in her ass," followed by his withdrawal from Jessie's pussy, leaving only my cock in there. I enjoyed having the hole to myself, but space got pretty cramped again once Matt started to push his cock into Jessie's ass, which was already occupied by Kyle. I couldn't really see what was going on, but I heard some grunts and Jessie's muffled whining while I felt another cock pushing along on the other side of Jessie's pussy wall. "Fuck!" Matt finally cried. "There we go!"
Kyle and Matt double-fucked Jessie's ass while I continued to pump in and out of her twat. At this point, Gus and Evan were both fucking Jessie's mouth, and I could hardly tell who else was fucking what on our shared cheerleader. The intensity of the gangbang hit a fever pitch until, at last, a couple people started to pull away in preparation for the grand finale.
Eventually, it was just Matt and me double-penetrating Jessie, who could finally breathe now that her mouth was vacant. My female friend collapsed on my chest, her hands on my shoulders, face buried in my neck as Matt and I continued to saw in and out of her. I asked her if she wanted us to stop, to which she lifted her head, revealing the sparkle in her eyes and that still-sure smile before she told me to sandwich her just a bit more.
I consented, but my body was a little stiff from having been on the bottom for so long, so the three of us all rolled over, Matt and I keeping our cocks lodged deep inside Jessie as we shifted. Then, with Matt on the bottom and Jessie facing up as she was still sandwiched between us, Jessie lifted her legs straight in the air, stretching them, her high heels pointing toward the ceiling, and gave us two boys full access to drill her two holes for one last round of hard fucking.
Matt and I double-stuffed Jessie like men possessed, pumping in and out her sweet ass and pussy hard and fast, over and over again with the rhythm of seasoned pornstars. Jessie, who had been screaming and whining throughout the latter portion of this group sex, was now literally giggling as the team's goalie and captain smushed her between them, going deep into her cunt and shitter over and over again. As much fun as it was to brutally group fuck this goddess, nothing was purely hotter than sawing into her with another guy while watching her smile and laugh as she expertly took the double penetration.
For the next few minutes, Matt and I enjoyed our delicious Jessie sandwich while I kissed her and squeezed her boobs, which were coated in sweat. At last, we succeeded in making Jessie cum for the third time that afternoon, her body rocking, legs shaking as her orgasm ripped through her body. Matt and I continued to double-team her straight through her hat trick orgasm, but it was just a little longer before I couldn't possibly hold out any more. Quickly pulling out of Jessie's pussy just as my friend finished her final climax, I announced, "Everybody cum on her face!" My instructions were met with loud cheers from my teammates.
Jessie was directed to her knees as she hopped off Matt's cock. I had been ready to go first but managed to hold out just a little longer to watch on for the first few cumshots instead. Kyle stepped up first, almost immediately firing off at that pretty face, landing it on her forehead and in her hair. Before Kyle was even finished, Matt stepped up and caught Jessie's left eye and cheek, sealing that eye shut for now. Kyle stepped back while Matt finished up, and then Jack and Moe stood up beside each other and, though Jack got off first by a second or two, simultaneously launched hard spurts of seman all over Jessie's gorgeous, grinning face.
As those two boys' cumshots tapered off, Jessie's shoulders were bouncing up and down, which, along with that big smile, indicated that she was giggling as one load after another covered her beautiful face. At this point in the bukakke, I couldn't wait another second, so I jerked off and stepped up in front of my best friend. I was quickly joined by Gus and Howard before I even got off, and, in one of the hottest spectacles I've ever witnessed, the three of us came on her face at almost the exact same time, I dousing Jessie's nose, forehead and between her eyes while Howard showered her chin and right cheek, and Gus launched all over the goddess's forehead and brown hair.
Ryan stepped up next and blasted Jessie's face with yet another load of cum while I joined my teammates on the bench and watched on as I inhaled deeply to try to catch my breath following such a satisfying afternoon. Jessie's face had so much cum on it that Ryan was just adding to it and causing it to flow down her face and onto her neck. Once he was done, Evan deposited his load as well, Jessie's face now completely covered with an incredible nine loads of man juice that was now dripping down her to her boobs.
Evan joined us on the bench, and Jessie remained on her knees, eyes forced shut, as white cream covered her face and streamed down her neck and tits, dribbling down to her stomach. When her lips parted to smile, cum seeped into her mouth, and she giggled some more. Staggering, she started to stand, at which point Jack stood up and clapped for our biggest fan. The rest of us joined in, giving the beautiful woman a standing ovation after the performance of a lifetime.
Lucky for Jessie, there was a shower right across the hall, so Jack and I got dressed quickly and helped her over there to get cleaned up, getting her out of her skirt and heels while we were at it. As the rest of the guys cleaned up and got things ready for game time, I guarded the shower and made sure the coast was clear. Once Jessie emerged from the shower, I handed her the change of clothes she had brought and helped her get dressed quickly in the hallway. We made out a little bit too, as not only was I not deterred by the fact she had just been banged by nine guys, I totally admired her for it.
When we got back into the locker room, the boys inundated Jessie with praises. With our game now just a couple hours away, I could sense that the tension that had plagued us lately seemed to have lifted. Jessie's morale-boosting stunt had done the trick, and we all felt a lot looser and more relaxed as we prepared to play.
Jessie stuck around to watch us not only snap our losing streak but dominate one of the best teams in our division by a final score of 6-0. Not one goal was scored by anyone who hadn't participated in the gangbang, I scoring two myself. It was unanimous that Jessie needed to be our new mascot, but, unfortunately, she had a husband and c***d more than 500 miles away and would be going home in a couple days.
"Tell you what," Jessie said, that mesmerizing, seductive grin on her face. "Make it to the championship game, and maybe I'll make a quick trip back up."
bydpingjessie©
If it's possible for a team to back into the playoffs, that's what my ice hockey team had been doing for the past couple weeks. With a berth in the postseason all but locked up, the team had now lost seven games in a row -- more losses in two weeks than we had in the previous two months! -- and the playoffs were suddenly no longer a sure thing.
The losing streak was obviously weighing heavy on the guys, especially my buddies Jack, Howard, Gus and Moe, who had been the ones to form the team to begin with and had been, until recently, largely contributing toward piling up the wins. With one game left in the regular season, morale had hit rock bottom. One more win was all we needed to clinch a spot, but with the downward spiral we were caught in, we honestly didn't believe we could pull out just one more measly game to get us that fresh start in the new season.
My team was on my mind almost all the time during this stretch, so it was hard to find much enjoyment in anything. Fortunately for me, my best friend, a hottie named Jessie, was making her annual visit home by herself. When she had come up last year, leaving the husband and son behind for a week, it led to some exceedingly ungodly fun, so I was hoping for a little more of the same this time and, thus, help take my mind off my anxieties.
Jessie was staying with her parents for the week, which wasn't all that close to my apartment, but the time of travel didn't prevent her from stopping by my apartment her first full day in town. It was always a pleasant sight when the 5'5" slender brunette was standing at my door. Even though she was in her late 20s, she looked at least a few years younger, and, from her tight frame, you'd never tell she had pushed out a k**. You also couldn't tell from her stunning smile or her innocent bright brown eyes that she had so eagerly participated in the raunchy, debauched activities of which I had had the immense pleasure of being a part over the past few years.
The look on Jessie's face said it all, but what the girl was wearing punctuated her point. After all, no one wears a tight top, short skirt and high heels underneath a long coat in the dead of winter when she's looking to just hang out. After very little catching up in the living room, we were both in my bed with the only clothing between the two of us still on being Jessie's high heels. The lady loved her shoes, and I loved how she would sometimes wear them during sex. Nothing looked hotter than Jessie wearing nothing but a pair of sexy heels.
For the next half hour or so, I fucked another man's wife hard on my bed like I had done to her several times before. Jessie and I had been best friends for more than 10 years now, and that relationship had often erred on the side of romance, even after Jessie got married. We didn't cross the line of sexuality entirely until one fateful night four years ago when we had sex in my apartment while Jessie was stranded during a snow storm while her husband was out of town. Since then, the sexual element of our friendship was a bit of a roller coaster. I still don't think her husband knew about it -- that is, except when he and I were fucking his wife together.
My fond friend of now 12 years was always the best sex I had, no matter how we were doing it. This time was no exception. I rarely saw Jessie since she moved out of state not long after that first time we slept together, and I even less seldom fucked her just to myself, so I cherished this moment. Like I said, I didn't know if her husband had any idea his wife screwed me when she was back in her hometown without him, but Jessie was so irresistible that I had long since dismissed those qualms.
I had actually just seen Jessie about a month ago when her family visited during the holidays. Her husband and I teamed up on her a few times during that span, but it didn't matter how much she satisfied me while she was around; I always longed for more as soon as she went back south. One simple month felt like ages, and the pounding I gave her as she wrapped her limbs around me while lying on her back in the bed demonstrated just how badly I had desired to vent my obsessive lust. At last, I brought my dear friend to a screaming orgasm, indicated also by her nails' sinking into my back, her heels poking my ass and her mouth letting out a cry of undeniable pleasure while her pussy convulsed around my thrusting cock. Her orgasm was almost always enough to beckon my own, and this time was one of those instances.
I told Jessie I was going to cum, so she relaxed just enough to allow me to push myself up and withdraw my cock from her pussy. As my lady friend's perfect B-cup boobs heaved up and down, recovering from the orgasm that had just rocked that sexy body, I jerked off and plastered her tits with a generous helping of semen, cursing and moaning in delight as I did.
I collapsed next to Jessie, both of us catching our breath now as both of our bodies glistened with sweat. As Jessie kicked her shoes off and got comfortable with me in the bed after cleaning the semen off her breasts, small talk ensued, and soon I was telling her about the woes of my hockey team and the big game we had on Saturday.
While Jessie had met my friends on the team only once, she was in one way very well acquainted with them. About a year and a half ago, I had talked Jessie into a five-man gangbang in which my hockey buddies and I each got to enjoy the full experience of Jessie's rocking body. Undoubtedly it was the memory of that incredible night that inspired Jessie to make the offer that she would make.
"I bet I could boost your team's morale," she said with that unmistakable grin.
"What, like a strip tease?" I asked, intrigued.
"There would be no teasing," she responded. "A tease wouldn't be good for your spirits."
"Another gangbang?" I said, now beyond excited. Jessie just nodded her head, still grinning. Then she noticed that, even though I had just emptied my load a few minutes ago, my cock was getting hard again. "Maybe you want to practice right now by sticking that in my ass," she offered.
After giving Jessie anal for the first time in non-group sex and depositing the meager load my balls could supply on such short notice, we finally got out of bed and went out for the night. During the night, Jessie picked out a photo for me to show to my teammates in the locker room after our practice tomorrow in order to see whom we could round up to gang fuck her. I imagined there would be plenty of guys who would sign up.
The next day, I ran the idea by my four friends, and, naturally, they were stoked on the idea. In fact, Jack was so excited that he was the one to announce it to the rest of the locker room. Of course, a lot of guys on our team were in committed relationships, so I knew it wouldn't be all 22 of them dominating my poor friend, but most of them still wanted to see the picture of Jessie, and they all agreed she was a knockout babe. I'm sure most of them thought it was a joke or some sort of scam, like the ones you find on Craigslist.
We did have four guys, though, who committed to be at the rink with us Saturday afternoon before the game to have what we were calling an "optional practice." Their names were Kyle, Ryan, Evan and Matt. I didn't know how many guys Jessie was expecting, but I assumed nine would be enough! Personally, the biggest gangbang I had been a part of consisted of eight people, and that number included the girl. It was going to be an interesting pregame, to say the least.
With puck-drop at 6:30 pm and the rest of the team arriving around 4:30, we arranged for the 10 of us to show up at the rink 2 pm the day of the game. We figured it would give us at least an hour and a half to enjoy Jessie, by the time we were all prepared, and still leave about a half hour to clean up and be ready before the rest of the team showed up.
Jessie and I traveled to the rink together after Jessie had showed up at my house to carpool. It took every ounce of self-control to not fuck her right there in my apartment after she showed me her outfit. It was her old cheerleader uniform from college, and I was really impressed that it still fit her so well. Like most cheerleader outfits, it was sleeveless and had a very short, pleated skirt. The colors were blue, white and red. Originally she was going to wear sneakers to match the outfit, but I talked her into sporting the black and white high heels she had also brought. In addition to showing a little more skin and making her ass look a little tighter, the open toes showed off her French tip toenails. I understand cheerleaders don't typically wear high heels, but Jessie's feet were too cute to obscure with sneakers.
Jessie and I arrived at the arena just before 2 pm. For now, that same large coat from earlier covered Jessie's outfit, except for the heels and, of course, her long brown hair, which she had curled for the event. She didn't often curl her hair in that manner, but the slight change of appearance was cute and went well with the cheerleader getup. Of course, she also made sure those pretty eyes and lips were popping with just the right amount of makeup.
When I got Jessie to the locker room upon which we had all agreed, I saw that the eight other men were already present, and that presence was made clearly known as the group erupted into cheers in order to warmly welcome the sexy guest of honor, who grinned and blushed quietly in the spotlight. I knew, though, that she would come out of her shell soon enough.
"Hot damn," Matt, our goalie, said, "she's even hotter than in the picture!" The other new recruits agreed, while the guys who had been with Jessie before just grinned as memories from a year and a half ago undoubtedly swam through their heads.
"Well, what are we waiting for?" Jack said excitedly. He then pushed the play button on his phone to begin his pump-up playlist, as he often did before games. We'd heard these songs in the locker room many times before, but there had never been a girl in the room.
We guys took our seats on the benches, at which point I noticed that one of my buddies had laid a mat out on the floor by the lone column in the middle of the room. It was a good idea, since this floor could get only so clean, and Jessie was already going to be getting dirty enough for us.
Jessie needed only a minute to calm her nerves, and the boys were very patient with her as she took off her coat, a little timidly at first. Once we all got to see the cheerleader outfit, the group roared with praise and approval. The affirmation seemed to bring Jessie to full composure, and that confident, sure, wicked grin spread across her face as she strutted over to the mat.
We cheered louder and louder as the hot brunette milf took center stage and swayed to the beat of the music. Without hesitation, she pulled off her shirt, tossing it behind her and revealing a white bra with red polka dots. We all continued to voice our approval, getting more excited as Jessie continued her strip tease.
"Take the bra off!" shouted Howard. Jessie smiled and shook her head, instead reaching under that short skirt and pulling a red thong down her slender, slightly tanned legs.
"That'll work too!" said Moe, nudging Howard. Jessie pushed the garment down to her knees, slowly in a teasing fashion, until it got to her knees, at which point she let it simply fall to her ankles. Then, pushing her curled hair behind her ears, Jessie carefully pulled her high-heel-clad feet out of the thong, stepping out of it and kicking it disdainfully to the side amid the constant cheers of her fans.
"Skirt on or off?" Jessie asked flirtatiously.
"On!" we all agreed.
"Heels?"
"On!"
"Bra?"
"Off!" Jessie laughed and reached behind her back, unhooking the brassiere and throwing it right at me to the tune of the music and eight other guys' hoots and hollers. Those cheers got as loud as they had been all afternoon once Jessie's smallish but perfect boobs were on display as the woman stood before us wearing only shoes and a very short pleated cheerleader skirt.
Jessie cupped her boobs for a second and then lifted up the skirt, giving all of us a full view of her shaved pussy and eliciting another strong reaction from her audience. Then, her hair flinging around as she did, Jessie turned around and leaned against that column behind her and stuck her ass out.
"Who's first?" she asked.
"Not so fast!" I said, jumping up and beckoning Jack and Gus to join me. Looking over her shoulder, Jessie grinned, not too sure what I was doing just yet until I stepped up to her and playfully turned her back around and pushed her to her knees. In seconds, Jack, Gus and I had our pants undone, cocks out, hard and ready. By the time we three guys had our pants around our ankles, the other six guys in the room were disrobing as well.
From her knees, Jessie took Gus's cock in her right hand, Jack in her left and lucky me in her pretty mouth. Our teammates all surrounded her then, and for the next 15 minutes or so, Jessie made her rounds. As nine men circled her, Jessie turned every 30 seconds or so to take a different cock in her mouth and in each of her two hands, expertly stroking them as she wonderfully sucked on another.
Even when my dick wasn't in Jessie's hand or mouth, I at least had quite the sight to see as my best friend rotated around and pleasured all of my teammates who were in that locker room. Those gorgeous eyes beamed as her head bobbed back and forth slowly while her hair shifted as well. Whoever Jessie pleasured would moan with satisfaction, and all of us, no matter whom Jessie was attending to at the time, affirmed and praised the sex goddess as she showed off her ability around multiple cocks.
Once everyone had gotten at least one turn in one of the pretty brunette's hands and at least one turn in the mouth, Jessie was helped up to her feet, at which point she went back to leaning against the column and sticking out her ass. As the captain of the team, not to mention the best friend of the entertainment and the one who brought her, I was given the opportunity to take the first ride. My teammates took a step back and cheered me on, and Jessie peered over her shoulder at me, just the corner of that amazing smile visible as I stepped up behind the knockout brunette.
I put one hand on Jessie's waist while the other guided my engorged prick into the girl's pussy. My tip was greeted with the wonderfully wet folds of Jessie's vagina and had no trouble working its way in. Once I had the head in, I put both of my hands on Jessie's waist, holding my friend in place as I sank forward into her. Jessie and I moaned in unison while our fans cheered us on, my cock sinking deeper and deeper into Jessie until my balls were touching her clit.
Jessie moaned louder and slapped the column while I briefly ground against her. Then, to the admiration of the onlookers, I started to thrust in and out of my dear friend, slowly to begin as my dick got coated in her sweet juices. Jessie looked straight ahead, her fingers pressed hard against the stone in front of her as she moaned and took my steady pushes into her lovely body.
"I can already feel the morale going up," I said as I increased my pace, thrusting faster and harder into my married lover, my hips now slapping against her ass cheeks. My teammates encouraged me to continue and give the sexy brunette the pounding she needed. They hadn't seen anything yet, I thought.
After a few minutes of taking a solo run with Jessie, I pulled out, and the train really began. One by one, all nine of us had Jessie the same way, bent over against that stone column, steadily fucking her from behind. Some fucked her slowly and deliberately, and others screwed her hard and fast. Some held onto her waist, others her ass or tits, and a couple even pulled her hair. No matter what, Jessie moaned as her lover grunted and groaned behind her. Ryan even got her to cum, which was hot to watch, seeing Jessie tense up and cry out as a perfect stranger nailed her twat.
Kyle acted as the caboose of this train, being the last one in line to make Jessie moan. After he finished his run of hard thrusts into the woman, he pulled out and allowed Jessie to stand up straight. Now it was time to decide how to proceed.
The team again looked to me. I asked for a volunteer, of which I had plenty. Moe was the closest, so he joined me with Jessie on the mat as the beautiful brunette grinned. I think she knew what was coming and readily allowed us to pick her up, I in front of her and Moe behind. The crowd, especially the new guys, really started to voice their excitement as Jessie spread her legs and d****d one arm over each of us, her right arm over my left shoulder and her left arm over Moe's right shoulder. With Jessie suspended in the air, Moe and I went to work fixing the girl on our pricks.
Jessie cooed as my cock slipped effortlessly back in her pussy but then gasped a bit as Moe's cock poked her asshole. I knew she would be OK, though, as she had done this same thing several times before. Once Moe was able to ease the head of his penis into Jessie's ass, he and I lowered the girl until we were both balls deep inside her.
The hoots and hollers were almost deafening as seven other men watched Jessie take two cocks. Kyle, Matt, Ryan and Evan were especially in awe, having never seen such a sight in real life before. The rest of us, of course, were entirely aware of Jessie's capabilities, and the newbies were about to see much more.
Once she was settled on our cocks, her feet dangling over the floor, Jessie cried out with excitement, her face beaming. Moe and I solidified our grip on the babe and then began to lift her up and lower her back down, sliding her up and down our shafts, which went in and out of her, mine in her cunt and Moe's in her ass. Before long, we were shifting her faster and faster, causing her hair and boobs to rock up and down as she took us deep and hard into both her holes.
Amid the raucous cheering of our onlookers, Jessie enjoyed a standing double penetration as her legs bounced with her body, which remained suspended in the air for a couple minutes. It was quite the workout for us guys, so much so that we actually lowered her a little bit at one point so that she could put one heel on the floor while she lifted the other one up over my arm. Jessie smiled at me as she now stood still and let Moe and me take turns going inside her ass and pussy. Her fabulous cunt felt even better now that it needed to compensate for her stuffed asshole as two cocks rocked in and out of her, separated by just a thin membrane.
Moe and I were sweating pretty good, and Jessie had some beads dripping down her flesh as well by the time we guys passed her off to the next group. Stepping up next were Jack and Matt, who gave Jessie a standing DP as well for a few minutes, the whole time allowing her to plant one foot in the ground as they sawed in and out of her tight, hot body.
Once Jack and Matt had their turn, Kyle and Evan stepped up, choosing to split-roast Jessie rather double-penetrate her. Kyle took her from behind and bent her over so Evan could stick his cock in that gorgeous mouth, and the two immediately began to thrust in and out of either end of her. Jessie's cries were muffled by that cock, but Evan's and Kyle's moans were clearly heard as each man fucked his respective end of their new fuck toy.
After a minute or so, they stopped thrusting and stood still, instead sliding Jessie back and forth between them like a slinky. By now, as the cheering was losing some steam, we could all hear the wet smacking of Jessie's pussy as Kyle pounded the hot girl. Jessie held onto Evan's hips as his cock plunged in and out of her mouth while she submitted to their lust, slamming each end into them over and over again.
Once Evan and Kyle finished their turn, Ryan, Gus and Howard were all up, a trio this time instead of a pair, since we didn't have an even number. Gus grabbed Jessie and pulled her down with him, he lying on his back on the mat and Jessie facing down on top of him as the two worked together to get Gus's cock inside Jessie's vagina. They sighed together with pleasure as Jessie sank down to Gus's balls just in time for Howard to kneel behind Jessie and proceed to impale the lady's sweet ass. Jessie and Howard grunted as Howard forced himself into Jessie's backdoor, which was certainly very tight, since her pussy was already stuffed to capacity, his dick going deeper and deeper until both he and Gus were balls deep in the same female again. All the while, Ryan was waiting his turn to take the only hole that was left.
"We call this a Jessie sandwich," I said to the rest of the guys as they stood back with me and watched Howard and Gus begin to saw in and out of the hot wife whose husband almost certainly had no idea what she was doing right now. Once Howard and Gus had their rhythm down and were thrusting steadily in and out of Jessie as she was smushed between them, Ryan stepped forward, cock in hand, and topped Jessie off, making her airtight.
With all three holes stuffed, Jessie never had fewer than three cocks in her for at least the next hour of this wonderful, amazing, ungodly gangbang. From that point on, there were still cheers and Jack's playlist was still on a loop, but whoever was looking on seemed to be in an awed silence as the beautiful woman in her late 20s took multiple cocks in all her holes like a champ, sinking deeper and deeper into depravity with the rest of us.
"Call me crazy," Matt said to me, "but I think we're going to win our game tonight." I have to say, all the tension caused by our losing streak seemed like a distant memory as I watched my best friend get pounded in all three of her holes simultaneously. The best part was, the main event was only getting underway.
The guys fucking Jessie were, understandably, getting carried away, hammering Jessie hard and for some time. I needed to intervene and tell them their time was up, reminding them that it was still too early for the guys to climax. Of course, Jessie could climax as much as she wanted, but she wouldn't be able to if we were too rough with her. The boys complied and pulled out of her, allowing the next set of three to take the mat: Jack, Moe and me.
Jack lay down on the mat as Jessie staggered to the side for now, her hair already a mess and her body gleaming with the sweat of herself and two or three other men. Once Jack was in place, I helped Jessie step over him and then sit down on his cock, her face and boobs facing out as she squatted and allowed Jack to poke his phallus into Jessie's sufficiently broken-in shitter. Jessie barely cried as she took the rod in her ass and just simply lay her back on Jack's chest before lifting and spreading her legs for me, which alone would have been enough to make me completely hard if I hadn't been already.
With the sight of Jessie's tight ass stuffed with my buddy's cock and the girl's sexy legs spread, inviting me to sandwich her, my heart was pounding and my dick was ready to go. I hurried in between those sets of legs and leaned forward, pushing my cock into Jessie's vagina, which was still nice and wet. Even with the constriction caused by Jack's cock in Jessie's ass, my penis slipped right in so that both of us guys were to the hilt inside my best friend.
Once inside Jessie, I lay down on top of her, sandwiching the lovely lady between Jack and me. We got right to fucking her holes, pumping back and forth into her, taking turns in our respective hole like we were pistons. As we double-penetrated Jessie, Moe stood to the side and lifted Jessie's head up so he could stick his cock in her mouth and make her airtight again.
Our three cocks bounced in and out of the sexy brunette, who was trapped helplessly among these three teammates. We worked her over good so that Jessie was enjoying it as much as we were. The evidence of Jessie's joy came when we got her to cum for the second time that afternoon, which was clear by her screaming around Moe's cock as her pussy convulsed around my thrusting dick.
Moe pulled out shortly after Jessie started screaming in climax, but Jack and I sawed in and out of her just a little longer until we too pulled out and allowed Jessie to lie on the mat while Matt, Evan and Kyle, the final trifecta, were ready to go immediately.
Wasting no time, these three arranged themselves a little differently, lying Jessie on her side and lifting her right leg straight up so that the heel of her shoe pointed to the ceiling. Then Evan lay parallel behind her and quickly stuck his dick in Jessie's ass, followed immediately by Matt, who knelt over in front of Jessie, slipping under the outstretched leg and inserting himself perpendicular into Jessie while Evan was already fucking her ass. Meanwhile, Kyle got to his knees in front of Jessie's head, and Jessie obediently took Kyle's cock in her hand and stroked it fast before working it into her mouth.
Now this sight was something new, as I had never seen Jessie take a double penetration in this position. I don't know how comfortable it was for her, but it looked really hot, especially with her leg poking out up into the air out of that writhing mass of flesh. Jessie was doing an especially noteworthy job of sucking Kyle's cock as the two other players sawed in and out of her other end.
Seeing Jessie take all these cocks in all these different ways gave me at least one more idea to carry out with her. Once the last three men took their run at Jessie, I suggested we still hold off on culminating this morale-boosting, team-building event for just a little longer and work Jessie over some more, if she was OK with it.
Kyle, Matt and Evan finished up just short of a climax, knowing there was still some time left for more fun. They stepped away and left Jessie to lie on the mat, her body vacant and shining with sweat. Her hair was a wild, matted jumble, and her tits heaved up and down as she tried to catch her breath. She looked like an exhausted mess, so much so that I even asked her if she was in good shape to go on.
"I didn't tell you bitches to stop, did I?" she playfully said while rolling to her side, still looking no less exhausted.
"Oh, you asked for it now!" I played right back before making my move. "Let's see how many cocks we can put in her at one time!" I said to my buddies.
Undeterred, Jessie sat up, her eyes getting brighter again and that confident, seductive smile creeping across her face. I stepped up to her first, getting down with her on the mat, which was now slick with the sweat of 10 different people as well as the vaginal juices of one particularly sexy female. I then lay on my back and pulled Jessie on top of me, securing her wet pussy with ease on my cock as blissful feelings overtook my senses. No matter what the circumstances, sinking my manhood into my best friend was always an experience I didn't take for granted.
Jessie and I moaned in unison as our bodies were joined again. She smiled down at me as she started to ride my cock the instant my balls touched her taint, her piercing brown eyes meeting mine. She worked herself up to a pretty good pace within a few seconds, but it wasn't long at all until Jack stepped up behind her and pressed his prick against her used asshole.
After Jack was in position, Kyle stepped up and grabbed Jessie's chin, pulling her head toward his cock so he could stick it in her mouth. Then Evan and Gus stood at either side of Jessie, each taking hold of one of her wrists and coaxing her to stroke them off while she took a cock in each of her sex holes. In a minute, Jack, Kyle and I were successfully thrusting in and out of the same gorgeous female while she managed to stroke off two other men, completing the airtight ski-poling that only a sex goddess like Jessie could pull off.
"Five, wow!" exclaimed Matt as he, Moe, Howard and Ryan watched on. "Can't really take more than that."
"I beg to differ," interjected Moe, who then joined Kyle over me and in front of Jessie's head. "That pretty mouth looks big enough for two."
"And while we're at it," added Howard as he shuffled behind Jessie while Jack and I double-penetrated her pussy and ass.
"Now that's more like it," I panted, admittedly a little overwhelmed with all the commotion going on around me. However, it was nothing like what Jessie was coping with, and it was hot as hell to be in the middle of this raunchy, wicked gangbang. In my experience, I knew one girl who had pulled off triple penetration, and even that girl didn't do it that well, but if anyone else could, it was Jessie. I had to see her try, at least.
"Holy shit," Jessie exclaimed as Kyle temporarily removed his cock to allow Moe to try to wedge his in there. "Fucking gadamnit!"
"That's right, baby," Moe said, "You got this," and the proceeded to begin cramming his dick into Jessie's mouth beside Kyle's. Meanwhile, Jack had shifted up Jessie's back, still pounding her ass to make room for Howard, who scooted in behind Jack and pushed the tip of his long cock against the base of mine while I was still thrusting into Jessie's pussy. I had to pull back a bit and come to a stop to allow Howard to do his thing, but I didn't mind. I had done double-vaginal on a couple of different girls before, actually, and one of them was Jessie, so I had long since gotten over any qualms with incidental male-on-male contact.
With the sexy babe still pressed against my chest, I could clearly hear the muffled screams coming from her throat, her mouth now filled to the brim with two cocks. The screams sounded only more desperate as Howard pushed himself harder and harder into Jessie, forcing his cock deeper and deeper alongside mine in her pussy. Jack even pulled out so that only his tip was in Jessie's ass so that Howard and I could get our manhood sufficiently wedged inside my lovely friend's tight cunt.
Jessie calmed down after a minute, and we took another moment to adjust to the extreme conditions. Soon, Jessie, albeit weakly, began to stroke off Ryan and Evan, just as Jack, Howard and I slowly but surely found a rhythm and started to pump our three cocks in and out Jessie's two holes like a well-oiled machine. Meanwhile, Kyle and Moe were essentially taking turns fucking Jessie's mouth, occasionally stuffing both pricks past those lovely lips.
Jessie squirmed and moaned as much as she could as five men fucked her sexy body while she did her best to stroke two more off. From then on, I could hardly tell what was going on as this mass of thrusting, writhing flesh moved above me while I continued to pump hard into that sexy pussy I was sharing with another dick. I was kind of stuck where I was, but I could see the other guys shifting around and taking turns with different parts of the female's hot body while they all cursed from excitement and praised their wicked sex goddess. At one point, I felt Howard pull out of Jessie's pussy followed by another cock's replacing it, joining me in my favorite twat. I'd find out that it was Matt who had taken Howard's place in the triple penetration.
Sweat was pouring out all over my body and mingling with that of my best friend as she was mercilessly pounded in all her holes beyond capacity with nine men who all took their turns with the team's new cheerleader. While Jack's playlist continued, the hooting had subsided for the most part as we all grunted and moaned while we all enjoyed the center of attention. The slapping of flesh and the squelching of Jessie's holes added to the soundtrack as I held the girl tightly and pushed hard into her pussy, competing with Matt's cock for room in there while Ryan, who had switch with Jack, caused Jessie's love canal to be even more constricted as he railed the lady's asshole.
The gangbang went on in that manner for a little while longer as most of the eight other men rotated and took turns in different parts of Jessie while she and I remained pinned in place amid the bodies and the intensely hot air that surrounded us. I had to pace myself, as I'm sure we all did, so as to hold off an orgasm until the very end, though cumming in Jessie's pussy wouldn't have been the worst way to end it. I honestly didn't mind not having the ability to switch holes. If I could stay put in any one place in the world all day, it would be Jessie's pussy.
At one point, I heard Matt say, "Let's put two in her ass," followed by his withdrawal from Jessie's pussy, leaving only my cock in there. I enjoyed having the hole to myself, but space got pretty cramped again once Matt started to push his cock into Jessie's ass, which was already occupied by Kyle. I couldn't really see what was going on, but I heard some grunts and Jessie's muffled whining while I felt another cock pushing along on the other side of Jessie's pussy wall. "Fuck!" Matt finally cried. "There we go!"
Kyle and Matt double-fucked Jessie's ass while I continued to pump in and out of her twat. At this point, Gus and Evan were both fucking Jessie's mouth, and I could hardly tell who else was fucking what on our shared cheerleader. The intensity of the gangbang hit a fever pitch until, at last, a couple people started to pull away in preparation for the grand finale.
Eventually, it was just Matt and me double-penetrating Jessie, who could finally breathe now that her mouth was vacant. My female friend collapsed on my chest, her hands on my shoulders, face buried in my neck as Matt and I continued to saw in and out of her. I asked her if she wanted us to stop, to which she lifted her head, revealing the sparkle in her eyes and that still-sure smile before she told me to sandwich her just a bit more.
I consented, but my body was a little stiff from having been on the bottom for so long, so the three of us all rolled over, Matt and I keeping our cocks lodged deep inside Jessie as we shifted. Then, with Matt on the bottom and Jessie facing up as she was still sandwiched between us, Jessie lifted her legs straight in the air, stretching them, her high heels pointing toward the ceiling, and gave us two boys full access to drill her two holes for one last round of hard fucking.
Matt and I double-stuffed Jessie like men possessed, pumping in and out her sweet ass and pussy hard and fast, over and over again with the rhythm of seasoned pornstars. Jessie, who had been screaming and whining throughout the latter portion of this group sex, was now literally giggling as the team's goalie and captain smushed her between them, going deep into her cunt and shitter over and over again. As much fun as it was to brutally group fuck this goddess, nothing was purely hotter than sawing into her with another guy while watching her smile and laugh as she expertly took the double penetration.
For the next few minutes, Matt and I enjoyed our delicious Jessie sandwich while I kissed her and squeezed her boobs, which were coated in sweat. At last, we succeeded in making Jessie cum for the third time that afternoon, her body rocking, legs shaking as her orgasm ripped through her body. Matt and I continued to double-team her straight through her hat trick orgasm, but it was just a little longer before I couldn't possibly hold out any more. Quickly pulling out of Jessie's pussy just as my friend finished her final climax, I announced, "Everybody cum on her face!" My instructions were met with loud cheers from my teammates.
Jessie was directed to her knees as she hopped off Matt's cock. I had been ready to go first but managed to hold out just a little longer to watch on for the first few cumshots instead. Kyle stepped up first, almost immediately firing off at that pretty face, landing it on her forehead and in her hair. Before Kyle was even finished, Matt stepped up and caught Jessie's left eye and cheek, sealing that eye shut for now. Kyle stepped back while Matt finished up, and then Jack and Moe stood up beside each other and, though Jack got off first by a second or two, simultaneously launched hard spurts of seman all over Jessie's gorgeous, grinning face.
As those two boys' cumshots tapered off, Jessie's shoulders were bouncing up and down, which, along with that big smile, indicated that she was giggling as one load after another covered her beautiful face. At this point in the bukakke, I couldn't wait another second, so I jerked off and stepped up in front of my best friend. I was quickly joined by Gus and Howard before I even got off, and, in one of the hottest spectacles I've ever witnessed, the three of us came on her face at almost the exact same time, I dousing Jessie's nose, forehead and between her eyes while Howard showered her chin and right cheek, and Gus launched all over the goddess's forehead and brown hair.
Ryan stepped up next and blasted Jessie's face with yet another load of cum while I joined my teammates on the bench and watched on as I inhaled deeply to try to catch my breath following such a satisfying afternoon. Jessie's face had so much cum on it that Ryan was just adding to it and causing it to flow down her face and onto her neck. Once he was done, Evan deposited his load as well, Jessie's face now completely covered with an incredible nine loads of man juice that was now dripping down her to her boobs.
Evan joined us on the bench, and Jessie remained on her knees, eyes forced shut, as white cream covered her face and streamed down her neck and tits, dribbling down to her stomach. When her lips parted to smile, cum seeped into her mouth, and she giggled some more. Staggering, she started to stand, at which point Jack stood up and clapped for our biggest fan. The rest of us joined in, giving the beautiful woman a standing ovation after the performance of a lifetime.
Lucky for Jessie, there was a shower right across the hall, so Jack and I got dressed quickly and helped her over there to get cleaned up, getting her out of her skirt and heels while we were at it. As the rest of the guys cleaned up and got things ready for game time, I guarded the shower and made sure the coast was clear. Once Jessie emerged from the shower, I handed her the change of clothes she had brought and helped her get dressed quickly in the hallway. We made out a little bit too, as not only was I not deterred by the fact she had just been banged by nine guys, I totally admired her for it.
When we got back into the locker room, the boys inundated Jessie with praises. With our game now just a couple hours away, I could sense that the tension that had plagued us lately seemed to have lifted. Jessie's morale-boosting stunt had done the trick, and we all felt a lot looser and more relaxed as we prepared to play.
Jessie stuck around to watch us not only snap our losing streak but dominate one of the best teams in our division by a final score of 6-0. Not one goal was scored by anyone who hadn't participated in the gangbang, I scoring two myself. It was unanimous that Jessie needed to be our new mascot, but, unfortunately, she had a husband and c***d more than 500 miles away and would be going home in a couple days.
"Tell you what," Jessie said, that mesmerizing, seductive grin on her face. "Make it to the championship game, and maybe I'll make a quick trip back up."
Jayla
- 02.12.2021
- 15
- 0
