Jun 18, 2009

Cacklin' Rosie

"...And he said, 'If you think it's scary now, imagine how I'll feel when I walk back alone!'," she said, allowing the punch line to sink in a second before howling at her joke. The guys laughed too, though not as loud as Rosie. It's doubtful that anyone could equal her boisterous laugh. Her friends back home often called her "Cacklin' Rosie" to which she'd always answer, "Get on board!"

She held court with five younger men. At 65, most of the men at the resort were younger than she was, though they'd be hard-pressed to accurately guess her age. Rosie had the body of a woman half her age. Only the laugh lines around her eyes and her vast experience could belie her years. She was immensely proud of her flat stomach and tight ass, loving the way it looked in her "itsy bitsy" yellow bikini -- the color set off her deep tan, just like her blonde, shoulder-length hair.

They had been gathered around her lounge chair all afternoon, sharing the glazed look of too much sun and way too much alcohol. Occasionally they'd excuse themselves to replenish their drinks, always bringing her a fresh Mai Tai like a tribute to their queen.

The guys, five of them, ranged from acceptable to hunks. Four of them were obviously college kids out for some beer and strange (in that order) while the fifth was a little older, a little paunchier, whose mischevous smile made Rosie a little wet every time she looked at him.

They hung on her every word as she entertained a vast array of topics, speaking to each in her gruff Brenda Vaccaro voice, and all of them thick with double entendres.

As the sun lowered over the gulf and the shadows lengthened around the pool, Rosie finally made her move. Standing up and stretching, showcasing every inch of her luxurious body, she announced, "I'm going to go back up to my room, does anyone care to join me?"

Of course they did.

The only thing less subtle would have been Rosie leading them back to her room with leashes tied around their dicks.

Following her shapely ass through the corridors of the upscale hotel, the guys were practically tripping over their tongues. They nearly bowled her over when she stopped outside of her door, turning to them and saying with an unexpected seriousness, "Things may get a little too kinky in here. If you feel uncomfortable and want to leave, I won't think less of you."

There were a couple of laughs that died quickly in the face of Rosie's serious reproach. She turned and slid the key card through the door handle, opening a new world to the four frat boys. The other man didn't seem taken aback at all at the sight of the naked man, bound with limbs akimbo to the room's second double bed.

Once they were all in Rosie's room she announced, "This is my husband. He's going to watch us. And, if any of you just can't wait to fuck me... he's got two perfectly good holes you can use in the meantime." His eyes got wide with panic but, at the same time, his already turgid cock twitched.

"I dunno, dude," said one of the frat boys. "This is too freaky for me." He couldn't take his eyes from Rosie's husband as he slowly backed away to the door, reaching back and flailing for the knob as if worried he'd be attacked from behind if he turned around.

No one said a word until the door clicked closed. "Anyone else?" Rosie asked, securing the deadbolt and chain. In answer, the four remaining guys started to strip, inelegantly tripping out of their clothes as men are prone to do.

Rosie kicked back on the free double bed, watching the exposure of manflesh, scowling a bit at the overabundance of tattoos that one college boy proudly displayed. "I wonder what he'll look like when he's Gerald's age?" she thought to herself, looking from the boy to her husband and seeing him eye the parade of hunky young bodies. Her mouth turned to a smile, seeing her husband smile behind his gag.

"Will someone help me with my suit?" she asked innocently. Quickly she had three sets of hands working at the three knots that held her bikini in place. The remaining college boys were overeager. The other man looked on, appraising her taut and fully-tanned body as it was freed. "Ahhh, that's better," she said, lying back and playfully tracing the muscular abdomens of the boys on either side of her, tickling down the trails of hair from their belly buttons.

With them all standing around, Rosie knew that she was going to play ringleader until (if) they got more comfortable. She crooked her finger at the third frat boy, beckoning to him before pointing to her bare pussy. It didn't take more than that for him to dive between her legs. He found the nub of her clitoris and attacked it with his tongue. "Shit," she thought, wrapping her thighs around him and pulling him back slightly to slow down his assault. He got the idea and slowed it down, giving her the ability to concentrate on the two boys on either side of her. She took one of their cocks in her hand while pulling the other closer to her waiting mouth.

Just as overeager as his buddy, he put his hands behind Rosie's head, his fingers slipping over her hair, and tried to fuck her mouth. Unable to find a rhythm, she helped him by wrapping her arm around his ass and pulling him into her, working against him until he worked with her.

She could hear the slapping of flesh on flesh as the boy on her right masturbated while one of his buddies used her mouth and the other licked her pussy. She wondered for a second where the fourth man might be but didn't really care. The pressure in her pussy was building to a delightful release.

She moaned around the cock in her mouth as she was pushed over the edge by the tongue in her pussy. She had to push the boy's head away from her after she came, suddenly over sensitized. He moved away and, before she could suggest changing positions, he was between her legs, sliding his cock into her pussy while she continued sucking.

Her legs now hoisted up over her shoulders, the boy was fucking her like a jack rabbit. It took everything she had to keep her lips around the cock in her mouth. It didn't take long, however, for him to whimper and cry out as he came.

Within moments she tasted warm, salty cum filling her mouth. "Oh, shit!" he cried, pulling her head closer into him.

She swallowed and, licking her lips, she turned to the third boy and said, "You've been so patient, hon. How do you want to cum?"

He leaned over and whispered in her ear. She nodded, rolling over and getting up onto her hands and knees.

She looked over at Gerald and smiled at what she saw. The fourth man had taken advantage of her offer. He had Gerald's bound legs up over a shoulder, his cock buried deep in Gerald's ass. Her eyes met Gerald's and she saw the joy there. She was sure the look on her face would be the same shortly as she felt the patient boy spreading lube on her tight rosebud. He groaned as he entered her superb behind.

Her eyes went wide before narrowing to slits of pleasure as she rocked back into him, meeting every thrust of his sex into her forbidden passage. She could hear him grunting behind her, animal sounds. She felt his sweat drip from his forehead, comingling in the pool at the small of her back. He gripped her shoulder with one hand, the other entering her hair to take hold of her long, golden locks. She began bucking harder against him so he might user her hair to guide her, to tame her.

The man in Gerald was about to burst. He pulled out of Gerald's behind and took both of their cocks in his hand, stroking them, their purple heads together. He worked them as one.

Rosie looked to see what the other boys were doing. They had begun to dress themselves but now stood in rapt attention of the sight of the two cocks being jerked at once. Perhaps even the boy plowing her back forty was doing the same. It felt that everything centered on their two cocks being worked, the two heads against one another, the one hand stroking them.

Gerald's groans raised and changed to a low, mewling cry. As if to harmonize with him, the man manipulating Gerald joined the cry with his own. And, as if they'd been practicing this maneuver for years, the two men climaxed at once, their seed mixing as it landed on Gerald's chest and stomach, clotting amongst the graying hairs of this chest.

Now a third voice joined the dying chorus; the boy inside Rosie. She felt him pumping his orgasm deep within her, filling her bowels with warm satisfaction.

Feeling him soften, she slid off of him to rest on the bed. The frat boy quickly joined his companions, dressing, before awkwardly excusing themselves. The fourth man, however, made no move to leave. Rosie nodded at him, knowingly. The boys could go, but the man would stay and continue to play with Rosie and Gerald.

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