Madelyn Meets the Gang

** Contains male-on-male sex **

There was another knock at the door. I answered it. "Hey, Paul, what's up?"

"Justiiiinnn," he drawled, and my tall friend stepped into the suite.

"You know Craig, of course. This is James, he's bi. James, Paul is not. And this ... is Madelyn."

It was her idea, enthusiastically supported, then arranged, by me. Madelyn is a total exhibitionist. She loves her body and loves getting naked. And if anyone was to get off on that, she thought, well, that just made the world a better place. I had jerked off countless times to her dirty selfies and movies, and we masturbated often together on webcam and in person. The next thing to do, it seemed, was to share the love. Sure, she could circulate her pics and movies, but that risked losing control of distribution. And she really did enjoy the intimacy of men appreciating her in person rather than simply imagining that they were at some random time and some random place.

It was surprisingly easy to arrange. I had simply booked an upscale hotel room for a night and messaged some close friends who I suspected would have an interest. I had rearranged the suite that morning, pushing the chaise lounge into the middle of the room as a makeshift stage, surrounded on three sides by a sofa, a line of barstools, and the bed.

Madelyn sat on the chaise lounge, legs together and folded to one side beneath her. Her arms were straight, palms flat on the sofa either side of her knees. She had made a very special effort for the event. She wore a scarlet bra trimmed with black lace and a diaphanous baby-doll chemise. Her panties coordinated. Sheer black stockings were supported by a lace garter belt, and she wore black, open-toed mules with long, spike heels. Dark brown hair flowed to her shoulders, and her green eyes were heavily made up with shadow, liner, and mascara. "Hi, Paul," she smiled, with lips painted a dark red.

Paul grinned as he opened a beer bottle and propped himself against a barstool. "So this is really happening, is it?"

"That's why we're here," I replied. "And now that's all of us." I sat down on the bed next to James who was sitting cross-legged. "Alright, Maddy. Showtime."

"Well, okay, then," she responded. I could tell that she was a little nervous, even though she had wanted to do this for some time. Unfolding her legs, she placed her feet on the floor, knees wide apart. She slowly leaned forward and reached down to her ankles giving Craig, on the sofa opposite, an unobstructed view of her generous cleavage. Slowly, sensuously, Madelyn's fingertips glided over her stockinged calves and thighs. They continued over her hips and torso, playfully lifting the chemise, then letting it fall. Locking eyes with Craig, she lazily brought each hand to the points of her bra, her fingers making small circles around the nipples beneath the fabric. Her fingers trailed up her chest and shoulders, and behind her neck, gathering up her hair which she pushed up languidly, then let fall. Her arms continued until they were straight above her head, then she brought them down in a slow, expansive circle to her sides.

Craig was transfixed. The hand that had been resting on his knee was now at his crotch, massaging an obvious bulge in his jeans. Leaning against the stool, Paul too was fixated, one hand holding his beer, the other in his pocket as he shifted from foot to foot. I glanced across at James, who grinned.

Reaching behind her back with both hands, Madelyn unclipped her bra. It remained in place, sitting loosely on her shoulders. Crossing her arms in front of her chest, she slipped the straps down her arms until the bra fell beneath her breasts. Madelyn has a magnificent pair; heavy and firm, peaked by large, dark brown nipples that became incredibly erect when she was aroused, as she was now.

Reclining on one elbow, Madelyn raised a foot to the chaise, keeping her legs spread. Now facing Paul, she slowly pulled up her chemise, the lingerie now bunched at her curvy waist. Bringing her free hand to her mound, her middle finger trailed down the fabric to the wet patch that had formed between her legs, and she made small circles around it.

She returned her foot to the floor and, with feet together, she stood to face James and me on the bed. Holding me in a smoldering gaze, she bent at the waist, legs straight. Slipping her fingers into the band of her panties, she slowly lowered them until they fell around her shoes. Paul now had prime view, unable to take his eyes off Madelyn's curvaceous ass. Remaining in her pose, Madelyn took a step to the side, and brought a hand between her thighs. Sliding it back, she parted her slick labia with her fingers, and wantonly wiggled her hips side to side.

Paul succumbed. Freeing his cock from the confines of his jeans, he stroked it gently up and down. It was the only time I had seen my straight friend's dick. Like him, it was long and skinny; at least nine inches jutting from a tuft of thick, dark pubic hair. As hot as Madelyn's performance was, Paul's exposed cock turned me on just a little more.

Madelyn sat back down on the chaise. She brought her wet fingers to her lips before taking them into her mouth, making a lascivious show of savoring her juices. Reaching beneath the sofa, she retrieved a large, purple vibrator. She then reclined completely, bringing her spike heels up to the chaise, and spreading her legs wide. Placing the tip of her vibrator at her clit, she flicked it on. The buzz of the toy joined the jingling of Paul's loose belt buckle, and now Craig's, as he released his own cock. His was perhaps six inches long emerging from a thicket of dark blond hair. Craig was mesmerized by Madelyn's cunt, a bead of sweat at his brow as he gripped his shaft in a tight fist. A fat, purple head emerged from his thumb and forefinger as he stroked himself in short, vigorous movements.

Madelyn repositioned the vibrator, pointing it away from her, and then gently pushed it an inch or two. She held in there, twirling it in small circles. "Oh ... oh ... oh ...", she gently moaned with eyes closed. Then suddenly she plunged the toy into herself with a grunt, her now saturated pussy talking all of its eight inches. With lip curled and knuckles tensed, she began to fuck herself energetically, "Uh-uh-uh" with each powerful thrust.

James unbuttoned his few remaining shirt buttons, and pushed it back on his shoulders, exposing his smooth, lean torso. Then he too unzipped his trousers and took his erection in his hand. James had an almost perfect cock, one I was very familiar with. Eight inches long, cut, and hairless, it tapered to a pretty, heart-shaped head; a pair of weighty balls in a smooth round sac hung beneath. Holding his shaft vertically, he lay back flat on the bed, legs dangling over the edge. Closing his eyes, he slowly began to stroke himself.

The spectacle of my four friends masturbating to each another had tested my will for long enough. I stood and peeled off my long-sleeved t-shirt. Pushing my jeans off my hips, I let them fall to the floor, and I was now completely naked. With so many exposed, engorged dicks in the room, I had an overwhelming desire to blow one. I straddled James in a sixty-nine position, my elbows and knees on the bed. Taking his cock from his hand to mine, I lowered my mouth to his soft glans, craning my neck so that I could continue to watch Madelyn and my friends masturbate. James sighed audibly, then began to lick the underside of my shaft and sac with quick, gentle laps of his tongue. I took his cock further into my mouth, then released him before lowering my lips to his smooth scrotum, rolling his slickened shaft against my stubbled cheek.

"I knew you guys would do gay stuff," Craig rumbled from the sofa with barely concealed disdain, as he continued to vigorously pump his cock. I half-smiled at the irony and let it go without comment.

With a final thrust and a throaty "UHH", Madelyn allowed the vibrator to slide out of her soaking pussy and fall to the floor where it continued to hum. "Did you like watching me fuck myself, boys?" she teased.

She brought her legs together, then stood, carefully balancing on her high heels. Facing Paul, she knelt on the chaise, before dropping down to her hands. She beckoned him playfully with a polished fingernail. Paul stood and stepped towards her, his rude cock swaying obscenely in front of him. Taking his shaft in her hand, she lowered her lips to his mushroom head and her mouth engulfed him as Paul emitted a reflexive "OH!" Holding him in place with her lips, her hand slipped into his open fly, cupping and gently massaging his hirsute balls. Slowly, she inched her mouth further down his shaft, taking as much of him as she could. She gagged twice, and released him with a loud exhale, a thick string of saliva hanging from the tip of his cock to her lower lip. Then she enveloped him again, and began bobbing her head up and down his shaft, her lips forming a tight seal. Eyes closed, Paul threw his head back, and panted irregularly to her motions; "Ah ... AH-ah! ... ah ... ah ..." Not knowing what to do with his hands, he held them behind his back, awkwardly.

"Fuck this!" Craig from the sofa, wanting more. He stood, knelt behind Madelyn on the chaise, and effortlessly pushed his cock into her dripping cunt.

"MMMPH!" Madelyn's cry was muffled, but she did nothing to express her opposition. Craig fucked her ungently, hands gripping her hips, thrusting into her as intensely as he had been stroking himself minutes earlier; "MMmm-MMmm-MMmm-MMmm ..." she moaned, her mouth full. Madelyn's heavy breasts swayed wantonly beneath her with each of Craig's movements.

Watching my two friends double-team Maddy, I needed more than James' expert tongue on my cock. Climbing off him, I stood, and led him to the other side of the bed. I gently pushed him to his knees and bent him over, his chest flat against the mattress. Pulling his trousers down to his thighs, I knelt behind him, between his parted knees. Spreading his firm buttocks, I exposed his puckered asshole, and growled, "I'm going to fuck you James."

"Oh, yesss," he whispered in reply.

I lowered my tongue to his stretched hole and rimmed him, making small circles around his sphincter, savoring his musky, dirty taste. Over the cleft of his ass, I could still observe the Craig-Madelyn-Paul show on the other side of the bed, Craig's broad hips smack-smack-smacking against Maddy's curvy ass. My lips formed a seal against James' buttocks, and my tongue snaked as far as it could into his asshole. He moaned, half-muffled by the comforter.

I reached for the ever-present bottle of lube I kept on the bedside table, poured a quantity on to James' cleft, and watch it drip down his anus, now wet with my saliva. I rolled two fingertips around the circumference of his hole, coating them in lube, before gently easing them into him, knuckle by knuckle, until they could go no further. I slowly pulled them out again, briefly taking my eyes from the threesome across the bed to admire James' gaping asshole. Lifting myself above his ass, I gripped his neck with my left hand, forcing his head down against the mattress. With my right, I guided the shaft of my cock between James' buttocks, and slowly rocked my hips, letting it slide up and down, over his greased hole. I pulled my hips back and pushed my cock down so that the tip sat snugly against his willing asshole. Then I pushed forward.

"UUUNNNNGGGHHH!" James cried, as I penetrated an inch or two into him. "Fuck! Justin!"

I waited impatiently for him to adjust, then pushed a little further. A couple more inches was deep enough. With my left hand still holding him down on the bed, I reached beneath his hip with my right, and softly cradled his now soft penis. I gently stroked it as I fucked him. "Ngh ... ngh ... ngh ...", James grunted, muffled against the comforter. I began to feel him getting harder and harder in my hand. Good. We'd need that.

By now, Paul had placed his hands gently on Madelyn's head, guiding her movements up and down his shaft. "I'm gonna cum!" he cried.

Releasing Paul and pulling free of Craig, Madelyn swung her feet to the floor, then knelt beneath Paul. Looking up at him, she placed her fingers beneath each ample breast and lewdly jiggled them. "Come on my tits, Paul. You too, Craig."

Craig stepped next to Paul and resumed his frenetic masturbation, almost squeezing rather than stroking his cock. Paul obligingly lowered his shaft to Madelyn's chest and barely touched it before spurting a milky rope of ejaculate over her pale breasts. "Aaahhhhhh!" he rasped.

"Nice, Paul!" Madelyn encouraged. He jerked himself a second, then third and final time, each upstroke shooting a smaller stream. Maddy's chest and breasts and her rock-hard nipples were now well-covered, her jiggling ensuring an even distribution.

I slid out of James' asshole, released him from my grip, and walked across the suite to stand next to Craig. I began vigorously stroking my shaft to hasten my orgasm. James joined me on my other side and followed in kind.

Maddy now had four men just inches away masturbating over, and she loved it. This was what she wanted. She loved expressing her exhibitionism like this. She loved to watch all these men stroke themselves. Most of all, she loved how deliciously bad and dirty this made her feel, and that no one who passed her on the street would ever guess that she was this kind of girl.

Sucking in his breath between his teeth, Craig stopped his movement, his hand freezing on an upstroke. White fluid pooled within the thumb and forefinger grasping his cock. He grunted, then smeared the stickiness across Madelyn's cleavage.

Madelyn shifted to face me and James. "Do it!" she hissed. "Come all over me, you dirty little cocksuckers!" Her filthy words and come-soaked tits were all the encouragement either of us needed. We exploded almost simultaneously, our loads arcing before spattering in translucent white strings over her cheeks, lips, and chest. "Mmmmmm," she moaned, licking our blended seed from her lips. "Oh, fuck, yes." She laid back on the floor, exhausted, a blissful look on her now sticky face.

Paul and Craig seemed in a hurry to zip up and leave. "Well, that was fucking hot," said Paul, stating the obvious.

"Yeah," Craig agreed, somewhat in a daze. "Yeah."

"Nice to meet you!" cooed Madelyn from the floor as they pair left the suite. James pulled up his trousers and I reached for a towel to wrap around my waist.

"Don't get too comfortable, boys," said Madelyn. "You have some cleaning up to do."