Missy watched in fascination.  Pickles looked so stupid right now.  If she wasn’t so amused, she’d be embarrassed for him, or question what it was she saw in him.  She wished she could take a picture of this so he could see how ridiculous he looked, laying on the bed, his ass in the air, and his legs stretched above his head as his lips tried desperately to reach his own cock.

He had bragged about it.  Said he’d managed to do it before.  He was damn proud of it.  Missy had to admit, she was interested in seeing it in action.  She’d heard about it, or more specifically, heard about guys breaking their necks trying to do it.  She considered herself a connoisseur of the fucked up, and definitely wouldn’t pass up the opportunity to see some wild shit like this firsthand. The technicalities of it interested her the most.  His cock was fairly average in length.  Not the biggest she’d ever been with, but worth keeping around.  He was thin, but wasn’t a twig.  God knows his old ass wasn’t necessarily flexible either.  It didn’t make sense that he’d be able to do it all things considered, but damn was he making an effort.  She had to commend him on that.

Still, an effort wasn’t what she wanted to see.

“C’mon, Pickles,” she taunted.  “You said you could do it.  I don’t have all night.  You could be getting me off instead.”

“I…  I can do it…  Geez, I’m fuckin’ tryin’.”

He was getting frustrated now.  She convinced herself that he’d had enough this evening that he didn’t feel shame but it was seeming like the pressure of her watching was making this more difficult for him.  Regardless, she wasn’t going to let him talk to her like that.  She swatted his ass after he raised his voice, causing him to lose his balance and fall over onto his side.

“Oww!”  He lay on her side and shot her a dirty look, rubbing his ass cheek.  Seeing the bright red imprint of her hand on his pasty skin probably would have made her feel bad if she didn’t know he was into it.  “What the hell was that for?”

“For raising your voice at me,” she said.

“Well, sorry,” he mumbled.  “Goddammit…  I almost had it before you hit me.”

The smuggest smirk graced her lips.

“No, you didn’t.  C’mon.  Try harder, bitch.”

Pickles straightened out, stretching with a sigh.

“Gimme a minute,” he said, out of breath.  “I need a drink.”

Missy rolled her eyes. 

“Of course, you do.” 

She looked around the room, locating a half-empty bottle of liquor on his dresser.  She got up off the bed to swipe it, taking a swig for herself as she brought it back to him.

“Open wide, babe,” she said when she got back to the bed.

Pickles mouth fell open, and she poured a little bit inside.  He licked his lips after she was done pouring and grinned.

“Better.”

“That ought to loosen you up.”

Whether it did or not, he kicked his legs over his head again for another shot at it.  He looked like he was closer this time.  His knees were on either side of his face with his dick just out of reach.  It was painful to watch, but she couldn’t tear her eyes away.

He placed his hand on his back while the other gripped the sheets.  It looked like he was trying to push his lower half closer, but it was possible he was just holding it because it was starting to ache.

“Do you need a push?” she offered anyway.

“If ya want me breakin’ my back,” he said.  “… But gimme a little more booze.  ‘M almost there.”

She moved a little, positioning herself on the mattress so she could pour the liquor into his mouth from between his legs without his boner getting in the way.  She poured roughly a shot down his throat, which he swallowed before trying again.

Sometimes, she wondered if alcohol was to Pickles like spinach was to Popeye.  Whether the booze really did loosen him up or just made him drunk enough that he could no longer feel pain or know his limits, he craned his neck, leaning forward juuust enough to…

“Holy fucking shit!”

Missy couldn’t believe her eyes.  His lips made contact with the tip of his cock.  He wasn’t going to be deepthroating it any time soon, but he could suck the first inch or so.  Even with his own dick in his mouth, his smirk was evident.  He held that position for a moment before releasing it and falling back flat on the bed.

“Fuck.”

“I’m not even going to lie, that was kind of hot,” said Missy.  “Wow.”

“Yeah,” he said with a self-satisfied sigh.  He brought his arms behind his head and closed his eyes.  “A thing of beauty…”

She snorted, thinking about how ridiculous he looked in the process.

“I wouldn’t go that far,” she said.  “Want me to finish you off?”

“Please.  That was only enough to tease me.”