Taking It for the Team

"How many cocks can she take at once?" Jack asked.

"She's done three," I answered, though I knew his question was rhetorical. "But I bet she could do five." We were about to find out.

Without a word, Jessie hovered over her new friend and knelt down, her legs on either side of Jack's waist and her hands on his chest as she lowered her pussy directly onto Jack's cock. Not wanting to miss out on what would be the best seat in the house, I hurried up behind the two of them and set up at Jessie's butt. As I saw Jessie sink down Jack's cock until her taint made contact with Jack's balls, I stood over her ass and asked her to spread it for me.

Jessie looked over her shoulder, her hair flying as she grinned at me and complied by straightening her back and putting one hand on each asscheek, spreading them as wide as she could so that I could see straight into her bright red and ravished hole. Then I leaned forward, put one hand on Jessie's soft, slightly damp shoulder and stuck my prick into her ass.

Jack stayed still and silent, his cock still submerged in Jessie's cunt while I pushed my whole shaft into Jessie's ass with little resistance. It was still tight, especially with Jack underneath her, but it was slick and used now, so it readily accepted me. In just a few seconds, both Jack and I were balls-deep in the same bitch again.

Once I was inside her, Jessie cried out and fell forward, putting her hands on the floor, her tits hanging near Jack's face. Jack had her waist, and I held her hips as we immediately began to bang her in both holes. Jessie moaned between us as she prepared for three other guys who were surrounding us, waiting for a piece.

"She's got a mouth and two hands," I said between breaths to the other guys as I panted while fucking Jessie in the ass. "Don't be shy. She can take it." Whether or not she actually could take it had yet to be seen, but I couldn't wait to watch her try as it all unfolded in front of me.

Howard positioned himself in front of us, putting his cock in Jessie's face. She obediently took it in her mouth and sucked Howard off while Jack and I were still moving like pistons in and out of Jessie's other end. Then Moe and Gus stepped up on either side of us, and Jack and I had to help support Jessie's body as she picked her hands up off the floor so that she could stroke the two remaining cocks. After just a moment, Jessie was pleasuring five men at once, a feat about which I'd never even dared to dream.

"Now that," Jack panted amid the many bodies above him, "that's what we call an airtight ski-poling." No one else said a word for the remainder of the orgy, except for the occasional curse or exclamation. Otherwise, the only sounds were the slapping of flesh, the squishing of Jessie's holes and the moaning of deeply pleasured people.

Panting and sweating, I continued to hold Jessie firmly in place as I bottomed out in her ass again and again while my counterpart beneath me plugged her pussy. Meanwhile, Howard was railing Jessie's face, and Jessie was impressively jerking off Moe and Gus on either side of her. I knew all along that she could do it and, in a sick, shameful, depraved way, I was proud of her.

For the first several minutes, I was focused mostly on watching my cock pump into Jessie's shitter, but as the gangbang progressed, I remembered that I had the best position to watch the debauchery occurring right in front of me. I looked up to see Jessie expertly pleasure three men at once, one stroking in and out of her mouth while her head bobbed up and down as Howard held her hair. Somehow, even though she was already taking three other cocks, she managed to continue to slide her hands up and down Moe's and Gus's shafts with little encouragement from those boys. Meanwhile, Jack thrust into her from beneath while I took it all in and slammed into her asshole. Then my eyes scanned down Jessie's back and to her ass before, leaning backward, I finally caught of glimpse of Jessie's little taint and the thrusting cocks neighboring it.

A shifting mass of human flesh, we were all moaning loudly as we gangbanged the sexy whore. Everyone was dripping with sweat by now, as the close proximity of so many warm bodies coupled with the intense group sex made the room feel like 100 degrees. I felt kind of bad for Jack on the bottom, what with all this commotion happening on top of him, including Howard's standing right over his head. That said, no one was doing poorly in this situation tonight, not even Jessie, who, to my delight, seemed to be enjoying all the attention and the pleasure of all these cocks bouncing in and out all over her body, even if she did need a breath every now and then.

We five men dominated Jessie's helpless body in those positions for a couple more minutes before, in fairness to everyone, we decided to switch up. For at least the next hour, we all took turns in different holes and in different positions. Jessie was flipped onto her back, then again onto her hands and knees and so on. What remained constant was that no matter who was where, five dicks were each getting a piece of Jessie, deriving pleasure from the same female. We made sure each one of us guys got at least one turn in Jessie's pussy, ass, mouth and hand before it was over.

Finally, we had the slut on her back one more time. Moe was in her ass, and Jack, Gus and Howard surrounded her upper body as she sucked Jack off the best she could with her head turned to her right and beat off the other two men. I was right where I could spend eternity, kneeling between Jessie's legs, which were stretched out and held high in the air, those high heels reaching toward the ceiling as I clung to her thighs and pounded her pussy, slapping my balls against her taint just a centimeter from Moe's sack, which was all the space I needed. Jessie's body was slipping and dripping with sweat, a mixture of hers and five other people. The room was rank with the scent of that sweat and sex while all I could hear was flesh on flesh and those wet holes accompanied by our moaning and shouting.

Jessie's holes squelched as my flesh slapped against hers. Her hair and boobs bounced wildly as she took the fucking from all directions. I couldn't take any more. Frankly, it was a miracle that we'd all been gangbanging Jessie for more than two hours now and we'd all held off our orgasms. It was now past 4 am, though, and I needed to cum, so, as we were still all pleasuring and being pleasured by Jessie in unison, I suggested we each take one more turn individually with her before closing out the party.

The guys agreed, and we all pulled out of and away from Jessie, leaving the spent, exhausted skank on the floor, her holes suddenly empty after being filled to the brim with cocks just a moment before. My sympathy went out for her, and I asked if she was all right, hoping we hadn't given her too much.

"Is that all you got?" she said, lifting her head and grinning. I knew she was most likely just playing along, but holy shit, I'd been sitting on a goldmine for 10 years while being just friends with this girl! She just took a five-man pounding and was still conscious - and we weren't done with her yet. I couldn't imagine all the fun I could have had with her all these years.

We mercifully allowed Jessie to lie on the floor as we finished her off. She still had stamina, though, and wasn't one to just lie there. As Jack went first and slid himself between Jessie's legs, Jessie wrapped her legs around his hips and propped herself up to watch him stick his cock in her pussy one final time. As he railed her, Jessie continued to hold herself with her hands on the floor and thrust back into him, matching his efforts as she moaned and shouted while her glistening boobs jiggled and sweat-soaked hair shifted with her movement. How she still had it in her was beyond me.

Moe, Gus and Howard, respectively, all took similar runs with Jessie as well. The point was to work ourselves up to an orgasm and pull out just before it in preparation for a grand finale. At last, it was my turn to culminate the magical night. I lifted both of Jessie's ankles onto my shoulders and then shoved my cock into her twat before leaning over and grabbing her boobs. Jessie got very vocal, yelling all kinds of expletives as I started to slam into her.

"Oh yes, fuck your bitch!" she said, obviously very turned on still despite the intense treatment she had undergone over the past couple hours. "Fuck the shit out of me - come on!" I rocked her as hard as I ever had while she shifted her weight and thrust into me as well, causing my cock to go as deep as possible in her and making my balls slap steadily against her taint. Meanwhile, her legs bounced against my shoulders and her tits sprung up and down as she took the last fucking she'd receive in a long night of sex.

I could barely catch my breath as I fucked my best friend. She too was heaving by now, unable to shout any more obscenities. I was sweating as much as I had all night while we rocked back and forth into each other as the rest of the men watched. Jessie's matted hair and slick body shone in the living room light as the smells and sounds of sex filled every inch of air. Then, just before I was to pull out, Jessie's twat tightened around me, and she shuddered violently. She was cumming, and, at the risk of making me cum just a moment too soon, I pulled out barely in time and ordered her to her knees, preparing to jizz on her right away if I needed to. However, by the time Jessie assumed the position, I had successfully held off. Being the one who brought the meat tonight, I really wanted to be the last one to finish.

Jessie demanded that we cum on her, panting as she tried to catch her breath one more time. Her body was already soaked with sweat from head to toe, but the five of us surrounded her, beating off vigorously as we prepared to cover her with another fluid.

Moe shot off first, blasting Jessie's right cheek, her chin and neck with several hard spurts. Before Moe was finished, Gus pushed to the front and sent two ropes at Jessie's forehead before unloading the rest on her chin and mouth, which she kept sealed shut along with her eyes to keep all the cum on her skin. Once Moe and Gus finished, Jack came on Jessie's boobs while a laugh came from Jessie's throat through her pursed lips. The laugh continued as Howard and I stepped up to finish the night while Jack hung back, now spent.

Howard and I jerked off, he pointing his cock at Jessie's rack, while I almost always went for the face. I looked on with unbridled lust as cum dripped down Jessie's nose and the right side of her face, which persuaded me to position myself for kind of the left-center of her face. Semen trickled down her neck and tits too, which also helped get me off.

Howard and I almost simultaneously exploded all over the nearly 30-year-old brunette in a grand climax to end the night, which had turned into early morning. Howard jizzed entirely on Jessie's boobs, which already had cum streaming down them, and I erupted on her left cheek, mouth, forehead and left eyelid - almost everywhere, really. I moved my cock up and down as I came so as to cover as much of Jessie's face as I could. After two-plus solid hours of arousal, all of us had plenty of semen to share with Jessie, and I was no exception as I doused her face with my man juice. I came so much that Howard was finished several seconds before I had completed my masterpiece on that pretty face.

There Jessie kneeled, in the middle of an apartment of a guy who was to her a perfect stranger before tonight, with her eyes shut as she laughed while cum covered her face and boobs and streamed down toward her neck and stomach. My knees essentially gave out after my orgasm, so I quickly collapsed on the couch right next to where Gus already was. I didn't pay attention to where any of the other guys went or had gone to. Instead, I just admired my lovely friend who had just been the centerpiece of a five-man gangbang, covered in the evidence and wearing nothing else but red high heels and jewelry.

In the ensuing moments, we cleaned up and got dressed. Jack offered for us to stay afterward and get some rest, seeing as it was early now, not late anymore. I assured him, however, that I'd take Jessie home. The boys heartily thanked me but especially Jessie for giving them the night of their lives. Gus suggested she consider a career as a pornstar, and I liked the sound of that idea. I guess if there was any need for me to prove myself to the guys, I had done it, even though it wasn't the girl about whom I'd bragged. I'm sure the guys didn't mind. After all, Jessie was officially at the level of sex goddess, something I couldn't say about any other girl with whom I'd slept.

A little delirious, Jessie, who was forced to go commando thanks to her torn thong, responded to the warm good-bye with just a smile and a small wave. By the time we got to the car, it was almost 5 am. We'd gangbanged Jessie for well over two hours, easily. On the ride home, Jessie, growing a little more talkative the more she recovered, insisted she'd had the time of her life and was shameless enough to do it again if I wanted to. Of course, she needed to figure things out in her personal life; after all, she was married, for now, at least, and she had the whole issue with her parents' watching her kid in hope of her getting her life together. I can't even imagine what they would think if they knew the shameful acts Jessie had just performed.

It wasn't until I was getting ready for bed and Jessie was in the shower that I realized that, while I'd told the guys that Jessie had given birth, I'd never told them that she was married. It just hit me that my four buddies had no idea that the five of us had just shamelessly gangbanged another man's wife. A few months ago, I would have felt guilty. Now, though, it was hot.

The sun was shining through the window by the time Jessie got into bed with me. We were both exhausted and spent, so we certainly weren't preparing for another round of sex like we'd been doing before sleeping. As she got under the covers, Jessie told me that one of the guys was talking to her when we were cleaning up in Jack's apartment and had told her about Abby and how Abby was originally going to be the centerpiece before Jessie fortuitously arrived in her place. I thought in some hypocritical way she was going to be mad at me for sleeping with other girls, but her point was something entirely different.

"I thought you were going to tell me when you had fun without me!" Jessie scolded me. It was true, actually. After the last time Jessie and I had sex, we decided it wasn't a good idea to continue, but Jessie did anything but discourage me from seeking out kinky episodes with other girls. I guess I didn't take her all that seriously. I awkwardly apologized, unsure of what to say, exactly, as I started to drift off to sleep. I wasn't even sure I correctly heard what she said next.

"That's OK," Jessie responded, curling up next to me. "Just invite her next time. It's been a long time since I've had sex with a girl."

Did I say "holy shit" already?