When the Devil Gets the Last Laugh

When the Devil Gets the Last Laugh: An April Fool's Story

At approximately two o'clock in the morning on March 30th, a shriek was heard so loudly throughout

the Meadowbrook Apartment Complex that it even woke Mrs. Jones in 4B, who every night takes enough Ambien to kill a horse.

"What the fuck did you do!" Jenn screamed as she shot up in bed reaching to switch on the lamp sitting on the nightstand next to her. In the light, she could see her roommate laughing uncontrollably at the foot of her bed. As she began to get out of bed to go confront him, she noticed a small clump of bleached blonde hair on the floor. Tears already began to fill her eyes as she reached her right hand up to her scalp and began to pat around until she came across what felt like a small patch of felt on her head where hair should be. This caused a bolt of lightening to shoot through her body making her jump up and dash out the door. Her roommate was still laughing as he watched her run down the tiny hallway and into the bathroom where a few seconds later it happened.

"Whoa! Whoa!" Teddy said still laughing as he ran to catch up with her, "another scream like that and we'll have the cops busting down the door."

"I can't believe you did this, Teddy!" Jenn sobbed. "There's literally a huge bald spot on the side of my head!"

"Oh c'mon," Teddy retorted, "it's not that noticeable."

"Are you kidding? How the fuck am I supposed to go to work, Teddy?" She screamed back.

"Well good thing you sell software over the phone where nobody has to see you," Teddy said chortling.

"I still have to see my BOSS, you dumb ass, and everyone I work with." Jenn replied. "You can't do this shit to a girl. I'm not one of your 'frat bros' where shaving off a patch of their hair is no big deal. Do you know how fucking long this is going to take to grow back?"

"Okay, okay, I'm sorry, I'm sorry!" Teddy said still grinning while throwing his hands up in surrender.

Jenn looked her roommate up and down. There he was with his moppy light brown hair that poked out around the bottom of the backwards baseball cap he always wore, curling around his ears. He towered over her at six foot two so she had to tilt her head up to meet his light blue eyes on that face that looked like it belonged to the more sporty looking models you see in ads for athletic wear, but unlike them, Teddy always had a slightly mischievous look to him that indicated there was still a happy, slightly annoying, but loveable kid somewhere in the tall mountain of muscles that was Teddy's body which could never keep Jenn mad at him for long, but this time he went too far.

"Sorry isn't going to cut it this time, dude," Jenn replied. "There's literally a bald patch on the right side of my head. I have work in a few hours, and we are having friends over later."

"Okay, okay I'll buy you a hat or something," Teddy said as he walked out of the bathroom and back to his room, or the pit, as Jenn called it, because there were dirty clothes hanging off everything and empty beer and soda cans everywhere.

"Yea, that will fix it," Jenn said rolling her eyes as she crawled back into bed hoping she could manage to get a few more hours of sleep before she had to face the world looking like a failed Chia Pet.

Later that evening, when Jenn got home from work she ran straight to her room slamming the door and locking herself in. Even though, Jenn managed to comb her hair in such a way that the shaved patch on her head was less noticeable, people at work still gave her weird looks anyway, and it made her so upset she vowed that she wasn't going to leave her room until it grew back. But tonight was the night of the week that Christy and Mark, Jenn and Teddy's neighbors from down the hall, came over for pizza and beer. When she heard the muddled sounds of laughter coming from her friends, Jenn couldn't resist going out to hang with them. Plus, even though she was mad, she was bored, and Jenn looked forward to Wednesday nights all week. So she got up, and threw on an old trucker hat in her closet that she still had from high school when that kind of thing was cool. Before she stepped out she took a quick look in the mirror. She approved of her outfit: a simple black v-neck tee that hugged her slender body, and perky breasts, and a pair of low cut skinny jeans that she slipped on over her g-string panties. She thought it was cute how her pin straight blond hair (at least what was left of it) draped out from underneath the trucker hat framing her face perfectly.

When she emerged from the tiny hallway that connects the living room to their bedrooms, Christy immediately made eye contact with her and shot up from the couch where she was sitting with the two guys who gave a loud "Aye!" in unison when they saw Jenn walk in. They were watching some sporting event on TV, and the small coffee table in front of the couch was already covered in empty beer cans. The tantalizing scent of pizza hit Jenn's nose reminding her that she hadn't eaten since lunch and so she made a dash for the kitchen where Christy caught up with her.

"Hey, I was wondering where you were," Christy said leaning up against the counter next to Jenn who was already half way through her first slice. "What's with the hat? Are you trying to resurrect 2005? Because as your friend, I strongly advise you to reconsider. Not that I wasn't a total victim of the trucker hat myself back then."

"No, no," Jenn began to answer as she finished swallowing her last bite of pizza. "It's not like that, I swear. I don't want to talk about it."

"What did he do now?" Christy asked accusingly as she crossed her arms and in front of Jenn.

"Nothing, nothing," Jenn replied as she tried to duck by Christy who had her pinned against the counter.

"Yea right, nothing. C'mon let me see," Christy said as she made a grab for Jenn's hat pulling it off her head.

Christy immediately covered her mouth with her hand in an effort to stifle the laugh that was about to erupt from her throat.

"Oh my god, fuck you," Jenn said, snatching the hat back from Christy and putting it back on.

"It doesn't look that bad," Christy replied, still trying to hold back her laughter.

"Yea, okay. I look like a fricken goon," Jenn countered, opening up the fridge where she proceeded to crack open a beer and chug half of it in one gulp.

"Let me guess, Teddy?"

"Yup."

"Well that's what you get for living with a guy. Especially a guy that you met on craigslist."

Jenn finished her beer and said, "He's a good guy, he just needs to grow up," before cracking open another and taking a big gulp.

"He's twenty-six," Christy retorted.

"Yea and I'm twenty-five, but I'm still going to get revenge on him big time," Jenn said taking a sip of her beer while staring down Ted whom she could see over the counter and into the adjacent living room where he was screaming something at the TV with Mark, completely oblivious to the conversation being had between the two woman just feet away.

"Why don't you just stop sleeping with him?" Christy suggested, knowing that even though Jenn and Teddy were platonic friends and roommates they would have the occasional romp. "That should miff him."

Jenn laughed. "I've been thinking about doing that anyway because lately he's been bugging me about having a threeso-" Just then an idea popped into Jenn's head. "Hey, do you still have that friend, you know, the one you told me about who's 'adventurous?'"

Christy narrowed her eyes at Jenn. "Yea, why?"

Jenn's wicked smile told Christy that Jenn had figured out what she was going to do.

Later that night after Christy and Mark went home, Jenn and Teddy sat on opposite ends of the couch staring at the TV that was turned to some late night talk show that neither was paying attention to.

"You want a beer?" Ted asked sheepishly, knowing that Jenn was still mad at him.

"No" Jenn countered, her eyes still glued to the screen. Not only did she reject it because she knew that this was Teddy's feeble attempt to make peace with her, but she was already pretty drunk from drinking steadily all night.

"Aw, c'mon, Jenny, I said I was sorry."

There was something about when Teddy called her Jenny that melted her insides a little, because he would only do it occasionally, like when he was telling an endearing story about her to a friend, or when she knew that he was truly and genuinely sorry.

Jenn turned to look at him, a true look of remorse had fallen over his boyish face. Jenn knew that if she continued to stare in those crystal blue eyes underneath that mop of hair that was being pushed down around his brow from that signature ball cap backwards on his head she was going to do something she would regret. Plus, she was drunk and horny because it had been a while since she last had sex, and just the thought of Teddy on her, in her, or anywhere near her was making her wet as she sat there on the couch trying to be mad.

Teddy could tell that she was trying to resist him so he crept closer to her and whispered, "let me make it up to you," right into her ear.

Just the heat of his breath on the sensitive skin of her ear made goosebumps shoot down Jenn's spine, filling her up with a lust so strong it gave her no choice but to close her eyes and let it take over the anger. Once Teddy pushed her hair aside so he could kiss the nape of her neck, the anger subsided completely, and she gave into him, releasing a heavy sigh as she turned her head to meet his lips with hers.

They kissed long and hard in only the light of the TV screen. Teddy started out soft and tender with his kisses, but one his lust took over he lost control of himself and started kissing Jenn like a starving puppy.

Teddy then pried apart Jenn's lips with his tongue so that he could slip it into Jenn's mouth, she took it in; wet and slick, when it met hers. She then breathed in heavily through her nose in order to take in Teddy's scent.

The way that Teddy smells never during sex never disappointed in igniting Jenn's primal need to be penetrated, and true enough, tonight, the cheap deodorant that he bought failed just enough to let the perfect amount of musk escape from the sweaty crevasses of his body, filling Jenn's nose and turning her into an animal in heat.

Teddy managed to take that lust to the next level when he put his hands on her. A man's large, rough hands on her soft skin never fails to open her up. Teddy's hands, in particular, do the trick quite well; square and rough with thick fingers that he moves strategically over her body stopping and fondling in all the right places, floods her with a potent arousal that builds up behind a wall somewhere deep within her loin.

When he slipped his hand into her pants he felt that her panties were already drenched. He slid he middle finger up and down her slit, getting it slick with her juices so that he could slide it in her effortlessly. Jenn couldn't help but moan a little through the kisses as Teddy finger fucked her, stopping for a moment to take her shirt and pants off.

He then began to kiss down her torso stopping right before the waistband of her panties. With his head between her legs he gave one last mischievous look to her, like a boy that was about to steal from the cookie jar, before sliding the underwear down her legs and completely off.

Teddy had worked her up so well that even just the cool air of the room hitting her swollen cunt felt good.

Teddy then hoisted each one of her legs onto one of his shoulders spreading her apart before diving in, using his tongue to lap all over her pussy before finding her clit. He worked her over and over, with each movement of his tongue building up the pressure behind the wall, causing Jenn to arch her back so hard that it appeared as if she was levitating. She used her hand to push Teddy's face harder and deeper into her gap. The force building up harder and harder within her, causing the wall to eventually come crumbling down, releasing a pleasure that consumed Jenn's entire body, making her completely forget about everything, even the bald spot on her head, in that one glorious moment of release.

Teddy came up and wiped his mouth and smiled at Jenn.

"How's that for an apology?" He asked as he tried to catch his breath.

"Not too bad." Jenn said thinking, "it won't grow my hair back though."

Jenn decided that the following Friday, with it being April Fool's Day, was the perfect day to enact her plan to get revenge on Teddy. Everything was arranged, all that was left to do was to text Teddy and get him to take the bait.

"Hey I was thinking, the other night was really hot, and I was hoping we could try something new out," Jenn typed on her phone.

Within seconds Teddy responded, making Jenn wish he was that quick to respond when she texts him that it's his turn to buy toilet paper.

"What did you have in mind?" he replied.

"Well you know that suggestion you made a couple weeks ago, about maybe inviting someone else over to come 'play' with us?"

"Of course!! Why? do you want to do it??"

"Yea I do, and I already found someone, a friend of Christy, and we will both be waiting for you in my room when you get home from work today."

"R U Kidding! That's so hot. Tell me more about the other chick."

"Well, her name is Casey, and she's on the taller side, brunette, and really hot"

"What?! She sounds so hot, I can't wait til 5:00"

"Yup! Me either..."

Jenn was grinning ear to ear. She knew that Teddy would be too excited to question it, or even realize the date.

At about half passed five, as if right on queue, Teddy came barreling through the front door and headed straight towards Jenn's room. When he got there, though, it was not what he expected.

"Who the hell are you?" Teddy asked sharply, for sitting on the bed was Jenn and some guy that Teddy had never seen before.

"Where's this girl you were telling me about, Jenn?"

Jenn got up and started walking towards Teddy. "Teddy, meet Casey," she began,"Casey is bi, and he's here to play with us,"she paused for a moment before coyly adding,"April Fools, Teddy." She then slipped between Teddy and the door closing and locking it.

"What the fuck is going on Jenn? There's no way in hell that I'm going to have a devil's three-way if that's what you think is happening here." Teddy said sternly. "You're crazy! Now move out of the way so I can get out of here." Teddy shouted, trying to move his way passed Jenn who wouldn't budge from the door.

"Now hold on, bud." Jenn began. "This has always been a fantasy of mine, and you owe me big time. If it makes you feel any better you won't have to touch each other," Jenn said as she moved in closer to Teddy slipping her hand down his pants stroking his flaccid cock. "Please," she whispered in his ear.

Jenn's hand did feel good on his dick.

Teddy looked down at the bald spot he had left on Jenn's head then over at the stranger sitting on her bed.

This Casey guy looked like any regular guy that Teddy might hang out with; brown hair, fit, wearing a collared shirt and blue jeans.

"I really wouldn't have to touch him?" Teddy asked.

"Nope." Jenn said shaking her head.

"Okay, if it's what you want, I'll do it."

Jenn lead Teddy over to the bed where Casey was waiting for them. Jenn slipped between the two of them to create a barrier with her body so that Teddy would feel protected from the other male.

Jenn didn't waste any time, she was horny and really excited over what was about to occur. She dove in on Teddy and started making out with him fiercely. Teddy reached for her breasts and began to play with them over her shirt. Meanwhile, Casey enjoyed watching them as he shoved his hand down his pants to play with himself.

Jenn could tell that Teddy was extremely nervous because his body was stiff and his dick wasn't. So Jenn did the one thing that she knew would get him to relax. She shuffled herself down the bed and go between Teddy's legs and pulled his pants off. Out came Teddy's fat cock flopping over soft and squishy underneath a thick curly patch of chestnut brown hair.

Casey was full mast now. The sight of Teddy's bare pelvic area was too hot for him to handle. Casey was a man who was able to appreciate the male body in all its glory and Teddy's was certainly glorious. His cock wasn't that long but it was fat, full of pulsing veins, and topped off with a huge cap. His balls were heavy and round, and hung low against his taint that lead down to that sweet place that Casey knew he unfortunately wasn't going to be able to go to today. Casey also admired Teddy's huge thighs. Teddy was muscular, but all that beer and junk food left a layer of fat over them, making Teddy appear even larger and more forceful to Casey.

As Casey watched Jenn take Teddy's soft dick into her mouth, he slipped off his pants letting his own manhood swing out and into the open. Just watching Teddy's cock get harder and harder with every bob, up and down, of Jenn's head, slick and wet with her saliva, made a droplet of precum ooze out of his own slit. He used his forefinger to rub the goo around his cock head making it gleam, and began to jerk himself off.

Teddy's eyes were shut in pleasure, but he opened them when he heard a flapping sound, but quickly shut them when he caught sight of Casey's naked body realizing the sound was Casey's nutsac slapping against his own body while he jerked off watching Jenn go down on him.

Casey couldn't take it anymore and had to join in, so he figured he'd go right for it. He went up behind Jenn and took her pants off. When she realized what he was doing she came up from Teddy's dick, and let him slip her shirt off so she was completely naked.

Casey rubbed his tip over Jenn's swollen slit that stuck out from underneath her ass as she was bent over in front of him continuing to go down on Teddy. After he got himself nice and wet from the natural juices leaking from her pussy, Casey glided his cock into her, relishing in the moist warmth of her cunt that effortlessly took him in.

A shot of pure pleasure shot through Jenn's body, starting in her pussy as Casey shoved in, and traveling outward through her extremities. Jenn was lost in ecstasy, having a cock penetrating both ends of her body.

"I want to take both of you," she moaned breathlessly.

This prompted Teddy to get up which compelled Casey to pull his dick out of Jenn and lay down on the bed on his back. Jenn got on top of him sliding his cock back inside of her.

Teddy began to push the tip of his dick into Jenn's asshole.

"No, not there," she protested.

"Then where?" Teddy asked.

"You know where."

Jenn looked over her shoulder locking her eyes with Teddy's. "C'mon"

Teddy looked down to see Casey's cock being swallowed by Jenn's gash, leaving just his balls hanging out underneath, taught and ready to burst.

Letting out a sigh, Teddy said, "fine," as he began to push his way into Jenn's pussy, stretching it open, making her moan out in gratifying anguish.

The two men began to pump in unison, slowly at first, but then harder and harder as Jenn's slimy cunt opened up more and more with each thrust making Jenn squeal like a pig as she bounced up and down on the two men inside her.

Casey was lost in a fantasy come true. He was in the best of both worlds. Not only was his cock deep inside a hot chick right now but it was smashed up and gyrating against the fat oozing pole of a hot guy at the same time.

Taken over by the pleasure he moaned, "kiss me." Jenn leaned in and began to kiss him, but when she pulled back, he managed to spit out, "no, him."

"No," Teddy shot back instantly, still pumping away.

"Do it," Jenn commanded.

"No"

"Yes!"

"No!"

"YES!"

"FINE!"

And like a shot, Teddy smashed his mouth into Casey's. Casey began to suck and kiss Teddy's face with the ferociousness of an animal in heat.