An Unconventional Convention

Casey gave Kelly's pucker one last expanding twist, and then removed his thumb, and picked up the bottle of baby oil, again. He drooled some of the cool liquid on his throbbing cock, and spread it around his cock-head and down its length. He then set the bottle on the nightstand and picked up a couple tissues to wipe his hand.

Kelly raised her head and turned it so she could look around her closed legs at Casey's glistening cock as he crawled forward on his knees. She couldn't remember ever feeling so excited, so sexy, and also so nervous all at the same time.

Guiding his slippery cock with his fingertips, Casey placed his knob against her sphincter and made little circles with it against the wrinkled ring of flesh.

Although he had just been rubbing her asshole with his thumb, the softness of his cock-head felt completely different, and she let out another contented, "Oh!"

Casey then leaned in and began to apply pressure against Kelly's sphincter.

Reflexively, Kelly's body reacted to the imminent intrusion, and she tensed up, which included forcing her rectum as tightly closed as it could get.

Unfortunately, even on her back and craning her neck, she couldn't actually see Casey's fat knob pressing against her asshole. But looking at Casey's stiff cock, gleaming with baby oil and joining his naked body to her upturned ass fueled her ability and desire to push her body's natural protective reaction aside, and she willed herself to relax.

Suddenly, she felt a soft but firm presence in her tight little rectum, gently spreading the circular opening wider. In her mind's eye she could see that big squishy knob that she had sucked and washed with her tongue stretching and deforming over the stiff root of muscle that was Casey's hard cock as he pushed against her constricted opening.

More than anything in the world right then, she wanted to feel his cock-head inside her, and she forced her sphincter to stop trying to close.

All of a sudden, his deformed cock-head popped inside her and expanded on the other side of her sphincter, almost locking him in place.

As Kelly's rectum closed tightly around the neck of Casey's cock, he let out an, "Oh, fuck, yes!" and she moaned, "Oh, my God!" at the same time.

He held still, enjoying the grip of her ass on his cock-head, and letting her get used to the stretch.

She looked down at his cock, solidly connected to her ass, and said, "Jesus! It didn't feel that huge in my mouth! Did you make the frigging thing bigger in the last ten minutes?"

"If it's bigger, baby, it's all because of you! You've got me so fucking hot!" he replied. He then asked, "Are you okay? If it hurts, I'll take it out."

"Don't you dare!" she said. "Yes, it hurts and I've never felt anything hurt so good in my life! But I know from sucking that thing that it's going to get bigger as you shove it up my ass, and I can't wait to feel how good that hurts!"

He leaned in, and a millimeter at a time, his cock slid into her asshole. As the taut circle of flesh stretched, Kelly clenched her teeth and breathed deeply through her nose.

For Casey, the feeling was off the charts. He had tried to pretend to fuck an asshole by making a circle with his thumb and finger and gripping his cock as tightly as he could, but his mock-up anus didn't come anywhere near reality.

If Kelly had been on her knees with her face in the sheets she'd have sworn that Casey was shoving a baseball bat up her ass. But that she was watching its slow progression into her guts added to the wonderful pain/pleasure paradox.

She was at the very brink of pushing on his body to get him to stop when she felt the tiniest bit of relief as the fattest part of Casey's cock passed through her sphincter.

As his cock sank deeper the pain gradually tapered off to where the pleasure was the dominating feeling coming from her ass. Then suddenly, Casey's knob made contact with a soft, super-sensitive, walnut-like protrusion of flesh, and Kelly groaned, "Holy fuck!" as the bulge in her panties made an unexpected leap and spurt.

Casey froze with a few inches of cock still left to go, and repeated, "Are you okay? Do you want me to stop?"

"Fuck, no!" Kelly said. "Keep going! I want to feel every inch of your hard cock up my ass and then I want you to fuck me 'til both of us cum!"

Casey resumed leaning in until his thighs were pressed against Kelly's upturned ass-cheeks and his cock was buried as deep in her ass as it would go. As he had pushed ever deeper and his stiff cock rode across her walnut, Kelly had let out a continuous low moan.

He paused only a moment at full penetration, enjoying the snug grip around the root of his cock, and then began to retract almost as slowly as he went in. He continued his extraction until his cock-head popped free of her asshole, but he left the squishy, slippery knob pressing gently against the quickly-reclosed rosebud.

Casey remained in that position for a few seconds to let Kelly catch her breath, but she surprised him, though, by locking eyes with him and commanding, "Don't make me tell you again, Casey! Fuck my ass! Stretch my tight little asshole with your fat cock and make me cum like a goddamned slut!"

Casey grinned at her tough, nasty talk, but then did as he was told and leaned in, forcing his cock through her constricted little sphincter and all the way up her ass in no more than two seconds.

Kelly threw her head back, her mouth gaped open, and her eyes went wide. The searing pain of the quick stretch of her rectum--that felt so amazingly good!--was followed by the electric jolt of Casey's cock-head jabbing and sliding over her walnut. The combination took her breath away.

With his dick buried balls deep in Kelly's ass, he supported himself over her on outstretched arms, and looked down at her. He playfully mocked, "What's the matter, slut? Is my fat cock too much for your prissy little ass?"

"Fuck you!" she growled back at him, unexpectedly enjoying the role of aggressive slut. "My ass is the best fuck you've ever had, and you know it!"

"And my cock is the biggest thing you've ever had shoved up your guts, isn't it?" Casey snarled as he pulled his dick all the way out of Kelly's ass. He leaned back a little to give himself some room, and then brought his hand down with a stinging slap on one of Kelly's naked ass-cheeks.

She jumped and yelped, and growled, "Bastard!"

He slapped her other cheek, and responded, "Cunt!" He then lined up and jabbed his cock up her ass in one quick thrust, going balls deep and holding it there as he looked down at her defiant face. He grinned, and said, "But you're right, baby; you are one hell of a good fuck!" He then began rocking his hips and fucking her ass with long, deep thrusts intermixed with short, quick jabs, and occasional tip-pokes in and out of her now-fully-relaxed asshole.

As Casey repeated a series of jabs that just had his cock-head poking her walnut, Kelly moaned, "Oh! Right there! Fuck me right there! I'm gonna fucking cum!"

Casey set up a quick rhythm of fucking, and Kelly gripped the sheets to force her hands to stay away from the bulge in her panties. Half a minute later, her orgasm ripped loose all on its own and quickly had the light fabric drenched as Casey's repeated walnut pokes produced squirt after glorious squirt of cum.

Very quickly, Kelly's walnut became overly sensitive, and she had to push on his hips to get him to stop fucking her. She looked up at him, and said, "Jerk off on me baby! Blow your hot fucking cum on my tits!" As she spoke she began unbuttoning her blouse as rapidly as she could.

With his slippery cock in his fist, Casey moved to the side so Kelly could put her legs back down, and then straddled her hips on his knees. Her bunched, cum-soaked panties were right below his dangling balls.

Kelly pulled her blouse wide open, exposing her lacy black bra and naked tits, and stared at Casey's cock-head as it slid in and out of view behind his flying fist.

It didn't take long for Casey to start breathing hard and then moaning as his second orgasm of the night churned up from his balls. He leaned over and directed his cock at one of Kelly's stiff nipples, and after landing a shot of stingy cum across it, he turned quickly to the other one, giving it a shot, as well. He then beat off the rest of his surprisingly big load between her tits onto her chest where he was sure the heat of his cum would be most appreciated.

When Casey's balls were finally drained, he straightened up and took a few deep recuperating breaths as he milked the last drops of his jism from his wilting dick to drop into the mess that Kelly had made in her panties.

With his breathing back under control, he smiled down at Kelly, and said, "That is--by far!--the most unusual and interesting date I have ever been on. And God's honest truth, Kelly, I enjoyed every minute more than I could ever have imagined. Thank you!"

"Me, too, Casey," Kelly replied. "When I was getting dressed to go out to the mall, I could never has guessed that the night would end up here, like this. You've added a dimension to my little hobby that I never even considered exploring. Thank you!"

***

The next morning, Casey was already in the hotel dining room at a table with a couple of other convention attendees when Rich came in. He waved him over, and motioned at the empty chair, inviting him to join them.

A waitress came over and took his order, and when she left, Casey said, "You look well-rested this morning, Rich. You must have had a relaxing night, huh?"

Rich grinned at him, and replied, "Actually, I had the most interesting and liberating dream last night. If I could have kept it going, I'd probably still be in bed."

"Is this a recurring dream?" one of the others asked. "My mother always said that was a premonition."

"First time I've ever had it," Rich replied. "It was kind of intense, so I don't think I'd want to have it every night, but reliving it once in a while might be nice."

End