Cuckold Conundrum

Spring 1998

Nebraska

Please note: All characters are 18 years of age or older.

Please also note that the events in this story occur right before Lady Lazarus.

"Yo this is stupid!" Darterrius said crossing his arms. "It ain't funny, and I can get into some serious trouble!"

"Come on..." Charles said trying to sound cool with his large muscular African-American friend. "What's the worst that could happen?"

Darterrius frown at his smaller and much whiter friend as he spoke, "well what if Lisa don't like your little joke?"

"She's a prankster!" Charles exclaimed laughing, "check this out, one time she farted on my pillow, I saw her and then switch it with hers!"

Darterrius rolled his eyes, "come on man, what's a pillow got to do with this."

Charles gripped his stomach then fell over laughing, his muscled black friend stared in bewilderment.

Sitting back up Charles wiped his eyes then spoke, "you don't get it!"

"No man," Darterrius replied.

"She got pink eye and when she did she didn't stop laughing for hours!" Charles said falling over again.

Darterrius didn't get the joke, but the thought of Lisa's tight bare ass squating override the brain that should have been doing all thinking.

"Uh yeah..." he said fixing his trousers, "I'm in, but you gotta promise to speak the truth when the five-oh show up looking to arrest someone."

Sensing that the deal was made Charles spat into his hand and held it out.

Darterrius didn't blink, he was in! He too spat and took the smaller man's hand.

When their hands grasped Darterrius squeezed tight.

"Ah!" Charles whined, "you're squeezing too hard."

"I want your white ass to know that whatever happens is legit, and you got my back!"

Charles' face went red! His voice was more off key that usual as he spoke, "yes!"

"Yes what?" Darterrius said increasing the pressure and raising his voice.

"Yes!" Charles said in a firm yell, "I got your back... no matter what!"

Darterrius released his grasp, then gave a mock jab to Charles jaw. His white friend gave a fake smile and chirped out a weak laugh as the threat sunk in. Darterrius may have been on the football team, but boxing was the blackman's true passion in life.

"Now tell me again how this shit will go down." Darterrius said with a mischievous grin.

Two days later

"Your friend was so nice to let us use his room to study." Lisa said with her fingers up in air quotes to emphasize the study portion.

Charles set down his school bag and approached his petite girlfriend. She was slightly shorter than him and she wore her light brown hair in a pixie cut.

He gathered her into his arms and hugged her close. He felt that he should say something cool or witty, his brain was blank, all he could think was how Lisa was almost as dark as Darterrius.

She was Italian-American with strong Calabrez features, she tanned golden brown on sunny days when he cooked and was left red. Darterrius was obviously black, but he was more of a light brown, like a caramel.

"So..." Lisa said lifting his chin up to her face, "are you going to kiss me?"

As she chuckled Charles was startled!

'How did she read my mind!' He wondered as he did kiss her.

They stood in the middle of the room, halfway between the window and the two beds. Lisa seemed to be pulling him towards a bed, that snapped him completely back to reality! He had a plan!

"I have an idea." He said into her neck.

Goosebumps appeared as she purred.

"Tell me more..." Lisa moaned.

"How about I show you?" He said guiding her to the window.

"Oh!" She eeped as her ass touched the window sill.

Charles returned to kissing Lisa as his hands roamed all over her body, with his repeated attention going to her chest.

"Oh yes..." she said softly when he tried to pinch a nipple through a padded brassiere.

Charles moved his hand lower, across Lisa's stomach, then into her pants.

"Silly boy!" Lisa teased when Charles pulled his hand back out.

"How was I to know you're wearing panties?" He pleaded as he slid his hand back down.

Lisa laughed at her clumsy boyfriend right up until he touched her shaved pussy. She inhaled deeply when he discovered how wet she was.

Charles didn't have much experience with women, but what he lacked in skill he made up with enthusiasm. Lisa obviously enjoyed his efforts, she was digging her nails into his arm.

He pushed his middle finger between her lips and into the wet abyss that was her pussy. Despite dating for several months he was still learning his way.

"Yes!!!" Lisa groaned, "that's it!"

Clueless he did more of what he was already doing.

"Oh... that's good!" She said running her hands through his hair.

He grinned like an idiot as she mussed his dark brown hair. Her tussles soon turned into a gentle nudge on the top of his head.

Sighing Lisa spoke up, "eat my pussy and make me purr!"

Charles knew exactly what she desired as he pulled her pants down, then off her feet. He tried to remember the last time they had sex, Lisa the ever prankster had tricked him several times to eating his own creampie before he had remembered.

"Hold onto the ledge." He warned his woman as he parted her legs.

"I'll try..." she said trying to get comfortable.

Charles pushed his head in deep, then lifted a soft tanned leg up to his shoulder.

"Oh yes!" Lisa screamed as his tongue lapped away at where he assumed her clitoris was.

Charles could feel her body shaking in pure extascy as he jammed his tongue into her wet hole.

"Charles!" Lisa yelled pulling his head back from her sensitive spot.

He pushed his head deeper as he filled with pride that he had her shouting his name.

"Charles!" She yelled again, "I think people can see us!"

Freezing Charles spun his head in a 180 spin to look at the closet.

"No you fool," a half naked Lisa said, "outside! Anyone can look up and see me!"

Gulping air to starve off a potential panic attack, Charles got his wits about himself quickly.

"That's the plan!" He blurted out much too quickly.

"Tell me more..." Lisa said in alluring tone.

"Public sex!" Charles barked, then inhaling deeply he continued, "we can see them, and.."

"If they don't look up, they won't see us!" Lisa said finishing his sentence.

Charles' cock was aching with desire! Not only did he love her deeply, but he wanted to fuck her hard and fast as soon as possible!

Laughing he nodded in agreement. Lisa pulled off her top, and undoing her bra she flung it away. Charles stared open mouth at her dark brown nipples.

"Silly boy," Lisa said pushing he head back into place, "who told you to stop!"

Fifteen feet away inside the closet Darterrius was getting bored. He liked watching Charles groping up Lisa, but all that pussy eating was so very draining.

'If she wanted a wet pussy, he could just spit on it and move on!' Darterrius wondered to himself.

He was naked, hot and very bothered in the dark closet. He had on a rubber Halloween mask, but removed it when he could keep his eyes open from all the stinging sweat.

'Some plan this is...' Darterrius mused, 'at this rate I'm going to pass out from all this carpet munching!'

Darterrius did have to admit that when Lisa pulled off her top he went from turned off to turned on.

'She ain't busty, but what she does have is mighty fine!' He thought.

Lisa then started pinching her nipples and twisting them. Darterrius went from half chub towards hard. He wished that he could join in and not be a weird interruption.

He watched as Charles paused to pull off his shirt to reveal ribs and more pale skin.

'Dammit!' He almost shouted at the couple he was spying on when Charles went back in for more.

Darterrius debated jerking off, he was after all hidden, no one would see him and it appeared he had plenty of time to clean up before he was expected to step out.

'Fuck it!' He declared to himself as he slowly jerked off, 'this is lame, but she got good tits!"

Justified in his actions he stroked his black snake to life.

It felt weird jerking off to a guy who tutored him eating out his lady, but once he started there was no turning back.

'Finally!' Darterrius thought as Charles stood to switch spots with Lisa.

He watched Lisa get on her knees and undo Charles belt.

'Shit!' Darterrius almost said under his breath as he worried his nerdy pal might have a bigger cock then him.

'Whew!' He whispered to the heavens when it was obvious that he had several inches in girth and length over the white boy getting serviced by the window.

'Lisa has skills! Mad skills!' Admired to himself as he watched her gulp down ivory cock.

It was obvious that Lisa would suck, blow, then pause to prevent Charles from nutting early.

'Man she want that small dick bad!' Darterrius thought as Lisa stood up and turned around to face the window.

Charles was seen getting behind her and pushing his small dick in.

Darterrius was excited! He wanted to see some pussy plowing! Charles seemed to be wanting to deliver what he was expecting.

"Oh yes!!!" Lisa said loud enough for Darterrius to hear.

Darterrius didn't think he was a pervert, but he decided to jerk off in such a way that he'd cum when Charles came. In his mind it made sense, all the porno VHS he watched he always came when the dude came.

SLAP!!!

'I liked where this was going!' He commented to himself as he saw his tutor proceed to fuck and spank his woman.

Darterrius' sexual excitement started to wane as he realized all he saw was white ass... white man ass at that! Charles was doing a good job, but it all he could see was... ass!

'I wanna see that spicey Italian pussy!' Darterrius wanted to say. 'or maybe some side boob!'

He kept stroking himself, despite his waning interest. He was determined to nut at the appointed time.

"Oh yeah!!!" Charles yelled out.

"Yes! Yes! YES!!!" Lisa said over Charles yells.

"What the fuck?" Darterrius muttered under his breath as he slapped himself on the head. "He came too fast!"

At the window Charles huffed in satisfaction! He had pleased his woman good, and the first phase was complete!

"Hey baby," he tried to say casually, "I'm going to turn on some music and then we can people watch until I'm ready again."

"Don't go!" Lisa pleaded with a hand behind her back holding him in place. "I don't want you to pull out."

Charles squeezed her breast, then slowly withdrew his white meat from her. He was still hard.

He stepped back and although initially he was worried about Lisa watching his ever move, she had forgot all about him. She was lost in staring out the window at the warm spring day.

They had fucked and watched people walk by, play hackysack, and chat. None of them aware that just above he had just pumped Lisa's pussy full of cum.

Charles turned on the music, then cranked it loud. Lisa stood with her legs spead apart facing away from him with a hand between her legs to keep the cum from oozing out.

Snickering he opened the closet.

"What the fuck?" He mouthed to Darterrius when he realized the giant blackman was naked with an erection. "That wasn't a part of the plan!"

Darterrius couldn't hear the words over the music, but he had the just of it. He could see Charles freaking out and with his hands waving about.

"Yo, what did you expect me to do?" Darterrius said when Charles pointed to his junk, "besides you came too quick!"

Charles cupped a hand to his ear, his didn't catch a word of it. He then started to dress.

"You boring!" Darterrius said when Charles pointed to the mask.

Darterrius picked it up and put it on, it was hideous Halloween mask they used to scare each other in residence. Then with a quick exchange of thumbs up, Charles opened the door and left.

'Move like a butterfly...' Darterrius said to himself as he glided silently across the floor.

"Now that's a fine white ass!" Darterrius said looking up at Lisa.

He knew the plan... stand behind Lisa and when Charles waved from below he'd tap her on the shoulder and scare her.

"This shit is too complex." Darterrius said once in position.

He was close enough that he could scare her good, and unfortunately close enough for her to slug him. Shrugging Darterrius started to will his boner down. He wanted to startle her without looking like an erection swinging sex predator.

Lisa seemed absolutely oblivious to it all. She leaned forward with a hand still between her legs, all while staring out at all the people.

Darterrius dick started to twitch; Lisa's fine ass and that side boob had him all fired up.

'Gotta clear my mind...' Darterrius thought as he looked out the window for inspiration.

'Damn fool!' Darterrius mumbled when he saw some clown on a skateboard trying to do some tricks.

Leaning forward to see if the clown fell over his giant black cock touched Lisa's ass leaving a tiny dot of pre-squirt.

'Oh fuck!' He thought as he realized there was no escape, the joke would be sprung too soon.

Lisa however did the unexpected, instead of looking over her shoulder she reached between her legs and grasped the thick black dick behind her!

"Oh fuck!" He muttered when she teased her hole with his cock head.

Darterrius couldn't see it, but he could feel Lisa coating his penis tip in the dripping creampie Charles had left earlier.

"Don't look back..." He mouthed as she lined him up and proceeded to sit on him. She pushed her pussy backwards to impale herself deeper.

"Oh!!!" Lisa cried out startling Darterrius, "so thick!"

Darterrius just shut his eyes, he didn't want eye contact with his tutors girlfriend. The last thing he desired was for her to look back to see she was getting fucked by a naked blackman in a mask.

Despite being pre-greased, Lisa made little progress in getting more dick in her vagina.

"What is this?" Lisa said over the music, "so thick..."

Darterrius dared not breath as Lisa pushed then tried a different angle to get more.

"Strap-on?" Lisa said between grunts.

She had gotten almost half in when she grunted loudly. Darterrius also leapt at the sound.

Deciding she won't get any more in her petite body, Lisa started fucking. No contact sex wasn't something new for Darterrius, he'd encountered several women too small to take it all in.

"Charles!" Lisa said, "this is sooo thick! I love it! It's like making love to some sort of beast or a black man!"

'You'll see how much of a beast I can be soon enough!' Darterrius promised.

"Oh yes!!!" Lisa cried out.

"Shit!" Darterrius said as Lisa came, the pussy pressure squeezed his dick powerfully!

"Oooohhhh!!!" Lisa cried out as her full lubricated pussy swallowed all of Darterrius ebony spear.

"Oh?" He remarked when he felt some sweet Italian ass press into his lap.

Darterrius was in ecstasy! Most white girls tended to be lazy in the sack, never on top and definitely not pumping away like this.

'Who was she?' Darterrius thought as he tried to figure out the name of the woman he knew back in Ohio who was easily a rival for Lisa.

"Charles!" Lisa yelled snapping Darterrius from his dreaming, "speak Canadian to me!"

"What kind of freaky shit is this?" Darterrius asked to no one in particular.

Meanwhile elsewhere in the building Charles felt like Ferris Bueller as he jumped over, under, then dodged multiple people in the hallway.

Unlike the fellow in the movie, he had to move still sporting an erection.

"Charles!" Said a sweaty chubby classmate blocking his way. "What are you up to tonight?"

"Not now Tommy!" Charles said squeezing by.

"We're playing DND tonight!" Tommy yelled.

"Oh yeah?" Charles said as he stopped and for a moment forgot everything.

"Yeah!" Tommy said enthusiastically, "the new rulebook is out, everyone is going to crack it open and try it!"

Charles loved the game, but remembering what he had to do he turned and ran off without responding.

"Charles!" Tommy yelled to his quickly vanishing friend.

Once outside Charles wiped the sweat from his brow. Before he started 'officially' dating Lisa he did a lot of running, but nothing like this.

Catching his breath, Charles was glad that he wasn't sprouting a boner anymore. He looked up to see Lisa staring off.

"She is such an angel!" He said admiring her face, "I wonder what she's looking at?"

Glancing about he saw someone on a skateboard trying some advanced trick. When the fellow fell horribly, he chuckled then looked back Lisa

"She must be disgusted?" He remarked as he saw her face all scrunched up.

He stood there in pure adoration, watching her naked body sway back and forth.

"What?" He said confused.

"Charles!" Tommy yelled out from the doorway, "the new realm is amazing! Let me tell you!!!"

"Not now dude!" Charles said worried that the joke would be ruined.

"Why?" Tommy said, "you don't look busy?"

"I am..."Charles said unable to dream up a lie.

"Look at this this!" Tommy said handing him a sweat covered flyer. "A whole new realm!"

"Hmmm, it does look good." Charles said trying to placate his fat friend.

Above him he could hear Lisa moaning his name.

'Does she see me?' He thought followed by, 'is Darterrius in position?'

He dared not look up, least Tommy look up as well!

"Right..." he said in a British accent, "off you go."

"What?" Tommy said confused.

Charles cleared his throat and spoke normally, "I gotta pray, so scat!"

"Pray?" Tommy asked.

"Uh, yeah." He said, "it's a Canadian thing."

"I've been to Canada, they don't pray out in public!" Tommy whined.

"Well where I'm from they do, now scoot!" Charles snap.

"Whatever!" Tommy said moving off, "we play tonight!"

Charles started doing stretches and hoped they looked like mystic movements. He dared not look up. Lisa kept saying his name.

"Charles!" He heard her say, "speak Canadian to me!"

Feeling safe he looked up and saw what looked like Lisa's sex face!

"What!!!" He yelled out.

She didn't look down at him, her eyes were closed. He jumped and waved at her.

"Lisa!!!" He yelled. "Lisa!!!"

He could see sweat on her brow, her face was ruddy, it looked like she was....

"Masturbating?" He asked himself. "If she is, then what is Darterrius doing?"

"Charles?" Lisa said looking at him. "If you're down here?"

He leapt in the air in joy! The trap was sprung!

"Gotcha!!!" He yelled up to his grilfriend.

He saw her turn her head over her shoulder, her breasts swinging with her. He was hard in an instant!

"Got you!" He yelled.

"Aaaahhhh!!!" Lisa shrieked!

Charles laughed as he danced about, he had tricked her good!

He could see Darterrius over her shoulder wearing the mask.

"You bastard!!!" Lisa called down to him followed by, "oooooohhhh yes!!!"

"You got pranked!" He said.

Charles laughed so hard, but he sensed something wasn't right. Darterrius pulled off the mask and his sweat covered face was scrunched up just like Lisa's.

Upstairs Darterrius couldn't laugh. Lisa was still fucking him!!! He pulled off the mask when she screamed.

"You guys are cruel!" Lisa said grinding her ass into him.

"Uh..." Darterrius grunted, "you wanna take a break?"

"No!" Lisa barked out as he pussy squeeze his I have a lesson to teach you both!"

"Uh... ok?" Darterrius said liking this kind of lesson.

"You guys are trying to trick me?" Darterrius heard Charles say.

Darterrius grabbed one of Lisa's tits and squeezed hard! It may have been smaller than he liked, he wasn't going to complain.

"Oh yes!" Lisa said moaning in a fake tone.

Darterrius decided to take the driver's seat, he liked her moves, but he also wanted to close this deal before someone changed their mind.

"Hold on!" He said grabbing Lisa's hips with both hands.

He liked her curves! His fingers sank into her flesh, she'd have hand marks.