Henry and Kennedy

by Randy Rogue

14 Feb 2022 2282 readers Score 9.0 (19 votes) PDF Mobi ePub Txt


They’d met Reginald at a party in a hotel with an open bar which had everyone pretty sloshed. Reg was talking up Henry pretty good and Kennedy knew to stay away from the two so that Reg wouldn’t bolt. Henry and Kennedy had done this before. They were an ultra strange couple… with a twist.

Henry was an older top in his mid-fifties but had a voracious sexual appetite. With just a touch of gray at his temples and a good shaped body, he exuded the alpha male prototype that most bottoms gravitate toward. After Henry was sure that Reg was sufficiently into him he called over Kennedy and introduced her to Reg. Kennedy was a nearly 6 foot tall, red-headed beautiful woman with huge tits and a very slim figure. Reginald looked a little miffed but boldly said, “Well, I could never tell you were into woman, Henry. Nothing against you my love,“ He said looking at Kennedy, “but, can’t she hang at the bar so I have my way with you”? Reg finished, brow furrowed, looking at Henry.

Henry knew Reg was a caught fish so he just gaffed his comment off and drunkenly nuzzled up next to him and whispered in his ear, “It’s just a watching thing, surely you don’t mind if you’re being watched while having sex?” Reg looked down and smiled, “Oh, a bit of cuckolding thing, is it? I get it. Well, I’m sort of an exhibitionist, so yeah, I’m all in. Does that make me the unicorn?”

Henry nodded, ”I’m not sure but we’ll see, let's head upstairs then”.

As soon as they got to the suite, Reg sat on the bed and Henry turned to him and said, “you see Reginald, Kennedy isn’t going to watch me fuck you… she wants to fuck you while I watch”.

“But Henry, I’m not into women” Reg stammered, taken aback.

“Yeah, I know. Ya see you might not be into women, but this woman would be in you. Kennedy?”

Kennedy unzipped her evening gown and dropped it on the floor. She then pulled down her pink thong to reveal a slightly erect, thick uncut 7 and a half inch cock, dripping precum.  She was absolutely beautiful standing there in a pink bra with that nice-sized dick. Reg looked at Kennedy zeroing in on her uncut dick. “Well, she looks like… a bit of… fun”.

“Great, I’m glad you see it our way”.

“Sorry but I got to take this damn thing off”, Kennedy said as she undid her bra.

When Kennedy released her tits, even Reginald cleared his throat and said under his breath, “Nice”.

Henry had his hand on Kennedy’s hip and leaned down to grab her cock and lift it up showing it to Reginald. “So Reg, I bet you’d like to suck on this bad boy here? She’s a hell of a lot bigger than me.”

Reg got down on his knees in front of Kennedy and put her slightly hard cock up to his mouth. He began by pulling back the foreskin and swirling his tongue around the pinkish-red tip. This made Kennedy exhale deeply and her knees bent a bit. Reg put more of her cock in his mouth and began slowly going up and down on it stopping every once in a while to pull it out of his mouth and lick the head.

“Wow, Never sucked uncut dick before. I heard they were sometimes a bit grotty”.

“You know what Reginald? You talk too damn much. Henry told me sucking cock was your specialty, so… make me a believer.”

“Yeah she’s a little pushy, ain’t she Reg?” Henry said as he sat back into one of the chairs by the bed opening another bottle of wine and pouring himself a glass.

Reg went back to sucking on Kennedy’s cock, going up and down a bit faster pulling on it from the base to the middle with his right hand. Kennedy put her hands on the back of Reg’s head and began forcing her dick a bit more down his throat, slowly, face fucking him. At one point she let go and Reg took his hand away from her cock and he deep-throated it and held it deep down his throat for a while. Reg pulled back and spit flew out as he breathed in a gulp of air. He then jacked her dick up and down for a couple of thrusts making it a veiny angry red. Then he slapped the big wet weiner on the side of his face a couple of times.

“Wow, dude! You do suck good cock. Hey Henry, why don’t you help Reginald out of his clothes so we can get to the main event here”?

Reg stopped sucking Kennedys cock and stood up pulling his shirt, shoes, and socks off, while Henry helped him with his pants.

Kennedy stood with her hands on her hips looking Reginald up and down. “Nice undies Reginald! I like when men wear thongs. And not a bad little body either, I can’t wait to make you my bitch.”

Reg just shook his head and laughed a bit, “I’ve always been very versatile but I’ve never bottomed for a girl before”.

“First times, sometimes the best”, Kennedy said pointing at him with her index finger. “Don’t you worry I’ll be very gentle with your hinny. You might say I have the gentleness of a woman. Mm-hmm! Now, why don’t you kneel down over the edge of the bed so I can get you ready”?

Reginald did as Kennedy asked with his knees on the floor and his rear up, belly, and head on the bed. She pulled his thong down a bit and off to the side and started to squeeze and fondle his ass.

“God I wish more men would work on their rears. Obviously Reginald you work out at a gym and you don’t neglect your ass, such a nice hard butt.”

Kennedy planted a kiss on the right side of his ass cheek and then licked his ass crack up from his lower spine down to his taint before pushing her tongue into Reg’s hole. She pulled his semi-hard cock out from under him up, toward her.

“Oh Man”! Reg gasped.

“Yeah, nice and clean. Good for eating and great for fucking”. Kennedy growled.” Love a man that knows how to clean up and out before sex.”

Kennedy grabbed both sides of Reginald’s hips and pulled his ass cheeks apart then stuck her tongue as far up his hole as she could. She began pushing her tongue in and out, tongue fucking him getting him ready for the onslaught of her thick dick.

“Oh my god, that feels terrific”, Reg gasped pushing back against Kennedy’s face. Kennedy came up for air and said, “Yeah, Wait for Mommy’s big cock, you little bitch. You ain’t felt nothing yet”.

Kennedy went back to eating Reg’s ass making him pant for something bigger than her tongue. Finally, she leaned back and Henry gave her some silicone lube, she covered her engorged hard prick in the slimy stuff, then pushed her cock up and down Reg’s crack waiting to zero in on his hole.

Kennedy found Reg’s tight anus and pulled her foreskin back all the way, she started to force her cockhead into the tiny opening.

“Hold still babycakes, this will only sting for a bit, then you’ll open up nicely for Mummy and it’ll feel great”.

Kennedy knew as any seasoned top knows, you have to go slow while entering a bottom, unless all you’re doing is raping ‘em. The Kama Sutra tells us that sex is for both partners. Male-Female, Male-Male, or Female-Female. And if you want to bring sex to the best level, both partners have to be enjoying it. It is… pretty obvious, but most people are not smart enough to know what’s obvious.

“Yeah, You’ve got my cock right up to your inner ring. Just relax and let Mummy push a bit more up into you”

“Oh, Crikey, You’re fucking huge! God damn, who would know a girl’s cock could be so thick”, Reg gasped.

Ohhh! There we go” Kennedy exclaimed. “Now I’m in you.” She could feel her cock slide past Reginald’s inner ring and up into his man pussy.

“Hold on wait… wait,” Reg said. Kennedy stopped the assault on his hindquarters and just let the man get used to the feel of her thick cock in his ass.

“Oh, OK, yeah, fuck yeah” Reginald breathed, pushing back against the cock that was half-buried in his hindquarters.

Kennedy took this as the go-ahead to start ramming more of her thick, hard sausage up into Reg. She was still pushing in and out slowly but with more pressure going into him. At one point she drizzled more silicon onto her dick and pushed harder up into Reg’s ass. Finally, he loosened up and she bottomed out with her balls up against his butt.

 “Oh, that’s it, Reginald. Nice! You like my cock, Right? I knew you would.”

Reg just grunted.

Kennedy leaned over Reg a bit more and placed her hands on his shoulders and then started really pushing into him hard. The slapping of their skin when they hit and the sloppy sound of the lube as Kennedy humped Reg’s ass was music to Henry’s ears.

Henry still sitting in the chair, pulled his cock out of his trousers, spit in his hand, and began jacking off. Reginald would grunt every time Kennedy would pull out and drive her cock up into his ass. This went on for fifteen minutes or more then, Kennedy stopped her assault on Reg’s ass and pulled back, standing up.

“Get on the bed my little bitch” She spat at Reg.

Kennedy wiped the sweat off of her brow and waited for Reg to get up onto the bed.

Reginald got up and jumped all the way on the bed, laying on his back. Kennedy got on top of him and flipped him onto his side. This chick was strong. She grabbed one of his legs and put it over her shoulder with Reg’s other leg still lying on the bed; Kennedy found his hole, entered him, and pushed all the way up into him in one forceful thrust. Reg yelped out a bit. She moved her left leg over his, trying to get closer so she could get more dick in him, and pushed into him again, deeply, Grabbing his cock and balls in her left hand and shook ‘em like they were asleep, trying to wake ‘em up, then started to move at a constant quick rate, sawing in and out of him again, her tits flopping up and down every time she nailed Reginald.

“Aw,ww,ww,ww Fuck” Reginald groaned as his body moved back and forth to Kennedy’s constant hard humping motions.

Just then Henry appeared by Reg’s side and said” I’m going to cum”. He was jacking his cock off and trying to get his cock close enough to put it in Reginald’s mouth. The first stream missed and flew over Reg’s head and soaked his left ear and the bedsheet. The next rope of cum hit Reginald in the face before he had a chance to open up his mouth to catch everything else. Henry grabbed Reginald’s head and pushed his cock into his mouth. Kennedy could see Reg was gulping down Henry’s load while she felt the cum rising up from her balls.

Fuck yeah, you little bitch, I’m going to fill your ass up”, Kennedy groaned. “Yeah, Oh shit, Yeah.”

And then she came deep into Reg’s ass while Henry was finishing up giving Reginald the last of his cum in his mouth.

 “Damn, that feels great”! Fu-u-uck yeah”, Kennedy yelled out as she came inside Reginal’s ass. Slowing down her thrusts to unload into his ass.

It was quite a sight, Kennedy filling Reg’s ass up as Henry was doing the same to his mouth.

But it wasn’t completely over. Kennedy got off the bed and fell down collapsing in a chair, her cock leaking cum everywhere. Henry, ever the cum eater, got down and started eating Kennedy’s cum out of Reg’s ass while jacking Reg’s cock up and down. After only a minute or two, Reg groaned and Henry was all over Reginald’s six-inch hard cock. He stuck Reginald's dick in his mouth and continued stroking him to get every last bit of man milk.

“Oh, Fuck Yeah”, Reginald said. Henry with Reg’s cock in his mouth pushed up from the base to the tip on the underside of his dick to push out all of his cum. For good measure Henry stuck his middle finger up Reginald’s ass and wiggled it around in all the Kennedy cum still leaking out, forcing out all the cum from Reggie’s cock, into his mouth.

Afterward, Reginald and Henry lay upon the bed with Kennedy still flopped out in the chair.

After a bit, Reg said,” Wow, I never knew I’d be into women so much”.

by Randy Rogue

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