Cali's Revenge

Story Info
She blackmails the guy who gave her hell.
2.5k words
4.27
147k
42
0

Part 1 of the 2 part series

Updated 10/31/2022
Created 06/22/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Cali had just finished her sophomore year at college. She loved school and living on campus. Now that classes were done, she dreaded going back home. All throughout high school, Cali was a relatively quiet girl who got good grades. She had a few friends, and dated here and there, but nothing serious. She always wondered why she didn't have success in dating, and thanks to her neighbor Brian, she found out why.

She and Brian always got along when they were younger, but by the time high school came around they peacefully went their separate ways. That's why Cali had no idea what possessed Brian to be so mean to her just a few days shy of the senior prom. She was at her locker, about to head home when he walked up to her. He saw her putting her prom ticket in her bag.

"Ha! Somebody actually asked YOU to the prom?" Brian laughed. "Sucks for them, they don't get any titties to play with!" He walked off laughing. Cali broke into tears. She couldn't believe he said such a thing. Sure, she had small boobs, but she was a small person. Only five foot one and just barely over a hundred pounds, tits any bigger than her 34As would've looked out of place. Besides, she was still very pretty. Long, straight blonde hair fell halfway down her back and she had a pretty decent tan. She had gorgeous green eyes and a beautiful smile that could light up a room. She had no idea what possessed Brian to be so cruel.

So today, as she was unpacking her things from school, her phone rang. It was her neighbor, Brian's mom, asking if she could baby-sit overnight because Brian was going to be out and his parents have a six year old named Zach that needed to be looked after. In an instant, all those memories of Brian making fun of her to her face, and then to his friends until everyone at school knew about it, all that humiliation came rushing back. But since Brian wasn't going to be there, Cali agreed to baby-sit because she could use the money to save up for an off-campus apartment.

***

Babysitting was so easy. As soon as she got to Brian's house she ordered a pizza, and her and Zach watched a Disney movie. Soon after, he went to bed without a fuss and was out like a rock by nine. Cali, clad in a somewhat skimpy pair of purple pajama shorts and a white tank top with no bra (Cali rarely wore bras), sat on the couch and watched MTV until she dozed off.

Around ten thirty, Cali awoke with a start to the sound of the door opening. Brian stumbled in, slammed the door shut, and staggered upstairs. Cali was furious just seeing him again, and none to pleased about being scared at the sound of the door. After a few minutes of steaming to herself, she decided to march up to his room and tell him off.

When she got to his door she was disappointed to see he had already passed out. She was about to leave when Brian rolled over in bed, and his sheet slid off, revealing he was completely naked.

Cali stared at Brian's naked body. His brown hair was a mess, but he had a nice body. It appeared that he was working on a six-pack, and he must shave his chest. Then she realized he also shaved all of his pubic hair. And then she saw it. Brian's penis. It was by far, the single smallest cock she had ever seen. She suppressed a giggle, and then an idea came to her. Quietly, she stole down the steps and dug through her purse, and pulled out her digital camera. She tiptoed back upstairs and started snapping pictures of his little dick. For his sake, she really hoped it got bigger, a LOT bigger, when he was aroused. In its flaccid state, she estimated it was maybe an inch long. She giggled and took one more shot, but this time, the flash went off. Brian's eyes blinked and he started to wake up. Cali tore out of the room, but it was too late, he saw her.

Cali sat on the couch, biting her nails. She was so worried...and then she wasn't. An evil smile crept across her beautiful face. She had the camera. She had the power.

Moments later, Brian stamped into the living room wearing a pair of shorts, yelling at her, "What the fuck were you doing in my room?"

"Quiet, needle dick, no need to wake up your little brother."

"You titless whore, I'll..."

"Not another word. One more crack about my tits, or anything negative about me, and I'll be sure that the pictures of your pathetic penis are all over the internet."

"And what if I posted pictures of your non-existent tits?"

"Well, Brian, a girl with little titties can still pleasure someone. Unless that tiny tool of yours really grows into something special, you ain't pleasing anyone."

Brian's blue eyes widened with fear. Cali sensed for a moment that this could be better than she expected, so she continued.

"So how about it, Bri, does your little pee-pee grow?" She cooed.

"Shut the fuck up."

"Now Brian, that's no way to talk to someone who is completely willing to broadcast your little dick to the world. I'm calling the shots tonight, asshole, and you owe me big time for ruining my prom."

He struggled with the thought and then answered. "So what? Everyone's dick is small when they're not hard. Everyone knows that."

"Oh really tough guy? Prove it."

"You wanna see some other dude's cock?"

"No dumbass. Get hard. Show me how big it gets."

"Fuck you."

"I swear one more negative comment in my direction and every inbox in my school and yours will have these shots within the hour."

Brian he could sense she wasn't fucking around. "Fine. What do I have to do to get those pictures?"

"Oh, don't worry about that just yet. I mean, I'm a very fair person, and it would be wrong to put pictures of your tiny pecker all over the internet without having pictures to compare it to. I mean, it was soft so why don't you make it hard, big boy, show me how big it gets."

"Why should I..."

"Shut the fuck up and do it!"

Brian didn't know what else to do. He pulled down his shorts and Cali laughed.

"Oh God, I didn't even notice how little your balls are too! That's so funny!" Cali snapped a few more pictures, and then began directing him. "Come on! Grab your cock, stroke it!"

"I...I can't." Brian needed to stall, he needed time to think.

"Why the hell not?"

"All my Hustlers are at school."

"Oh Jesus, you are making this so difficult. What do you want to see? You like panties?" With that she spread her legs so Brian could see her little green panties through the leg hole of her shorts. "Or maybe you're an ass man?" She turned and started to pull down her shorts, but stopped and whirled back around just as the top of her butt crack came into view. "Oh no, I remember, you like titties! Big, fat, juicy, round ones, right? Not like these!" She whipped off her tank top, exposing her tiny breasts, capped off by her light pink, slightly puffy nipples. She began caressing and squeezing her boobs in front of him. "So these don't do it for ya, do they?" She glanced down at his cock. It had grown. But not by much.

"Oh my god, is that hard?" She grabbed it. It was hard alright. Rock solid. "Holy crap! It is! You have the tiniest fucking cock I have ever seen! You dared to call me titless with a dick like that? Ha!"

Brian was humiliated and his face was a deep red. "I'm sorry," he mumbled. She just laughed.

"Oh no, not yet you're not!" With that she snapped a few pictures of his tiny little stiffie, giggling all the while. "Oh I am going to have some fun with you. You are going to do every little thing I say if you want this to stay our little secret. Now go find a ruler, I want to know how small it is!"

Brian sulked off and found a ruler. Cali held it next to his cock. "THREE INCHES!" She fell on the floor laughing. Once she regained her composure, she snapped a few shots of it next to the ruler. After that, she sat back down on the couch and smiled at him.

"Now, back to business. You have something to look at now. After all that crap about my tits they were all it took to turn you on. That's just great. But now, I want you to jerk it off."

"What? Are you kidding me?!"

"No. Jerk off right here, right now. I wanna see how much cum shoots outta that thing! Stand over here." Brian walked over and stood right in front of her so his cock was level with her chest. "I want you to stare at my boobs and beat off. I'll even record it!" With that she turned her camera onto it's video function and started recording. "Go!"

Brian was reluctant to start; he didn't want to suffer any more humiliation. "Aw, a little camera shy? Don't wanna jerk off to these cute little boobies?" She started using her free hand to rub her nipples. She could tell he was struggling not to touch himself. All of this sexual power she had was getting to her too. Cali felt her pussy moistening, and once again that evil smile crept over her face. "How's this for a little inspiration?" With that, she slid her hand down across her flat stomach, under her shorts, into her panties, and began rubbing her clit. Brian could hear her fingers moving through the wetness and he couldn't take it anymore. He grabbed his cock and began furiously jerking off. Within twelve seconds, the cum began spurting out of his tiny dick, hitting Cali in the chin and coating her left breast. He shot a second stream that landed on the arm that was halfway in her shorts and partially on her stomach. A third spurt also hit her stomach. He hung his head in shame.

"Holy shit! How fucking fast was that? Did you even touch it? Jesus!" She looked at the cum that was all over her. "And when did I say you could squirt all over me? Clean this shit up!"

Brian went to leave the room.

"Where the hell are you going?"

"To get a towel."

"I don't think so, needle dick, you're going to lick up every last drop of it. You can start here."

She thrust out her arm and he reluctantly leaned in and licked the cum off of it. She pointed to her stomach, and began licking her.

"Ya know, it's kinda hot watching you lick your own cum off of me..." she cooed teasingly. With that, she slid her hand back into her panties and continued fingering her pussy. She rubbed her fingers all over her clit, working it good and getting faster and faster and wetter and wetter.

"I didn't say stop licking!" He tore his eyes away from her crotch, wishing she was naked, and continued licking. He lapped up all the cum from her stomach and moved up to her breast. He swirled his tongue all over her nipple, getting the semen off and thoroughly enjoying the sensation of her tit in his mouth. She began panting heavily and squirming around.

"Oh...oh god, I'm gonna cum, I'm gonna cum." She pushed his head down until he was on her knees in front of him. "Take my...oohh...my shorts off, quick...holy shit...panties, take them too..." Brian tore off her purple shorts and her little green panties and he saw her beautiful pussy, with a few tiny wisps of light blonde hairs on her pound and her fingers furiously rubbing away at her clit. "Fuck! I'm cumming! I'm cumming!"

Brian was not prepared for that. Cali came, and came hard. She shot her girl cum in a steady stream into his face. She shot stream after stream as her body violently spasmed and she moaned uncontrollably. Brian's brown hair dripped with her cum and his face and chest were soaked. Cali laid on the couch in a heap. "Holy shit..."

After a few moments, she regained her thoughts.

"Go upstairs; prepare me a nice warm bubble bath. When it's ready, come back down. Go."

As Brian walked away, Cali laid there in amazement. She had never cum so hard in her life. This control thing was really turning her on. Brian came back down.

"The bath is ready."

"Good. Oh look, you're little pee-pee is hard again! Come here for a minute." Brian walked over and stood in front of her. "I wonder if I would even feel that if it was in my pussy!" She saw Brian's eyes widen. She laughed at him. "Go ahead needle dick, stick it in me! I bet you won't even be able to pop my little cherry!"

Brian got closer to her, and she felt his pelvis against hers. She felt his tiny little prick poke at her clit, sending shockwaves through her body, and she felt him slide down, and then in. She could just barely feel his little cock inside the walls of her twat.

"I can hardly feel it! Thrust it in there! I wanna really feel a cock inside my pussy!" Brian thrust forward, and she could barely tell he moved. She looked at his face, and saw a look of pure ecstasy mixed with embarrassment. "Oh no you don't, you're not cumming inside of me or on me again. Pull it out and lay down."

Brian did as she said; she dropped to the floor and grabbed his ankles. She pulled his legs up until his feet were at either side of his head. She reached out and grabbed his dick in between her thumb and index finger and began to tug at it.

"How's that feel, Brian? How does it feel to have someone else play with your teensy little stiffie?"

He squirmed, determined not to cum, as his dick was aimed directly at his face. She saw his determination, and knew just how to break him.

"Just think of all the action you got, you little stud! Licking my tiny titties, cumming on me, me cumming on you, you even got to put your pathetic cock inside my tight, hot, wet pussy..."

That was all it took as Brian ejaculated, shooting a load onto his forehead and eyes. As he moaned, he shot a second stream of pearly white cum into his mouth, and finally a third onto his cheek. Cali grabbed her camera, and took pictures from between his legs, showing his tiny little dick pointing at his cum-covered face. She smiled.

"Now, bath time. Carry me upstairs and give me a bath. We have a long night ahead of us..."

Please rate this story
The author would appreciate your feedback.
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Smaller than Average Guy learns he is smaller than average.in Fetish
Penis Shrinking Cream A new product that can shrink the penis is on the market.in BDSM
Small Penis Humiliation Of Husband Empowered by SPH, wife goes further than ever.in Fetish
Matters of Size Ch. 01 He finally scores with his longtime female friend.in Fetish
Her Revenge Was Sweet Wife shrinks her "cocky" cheating husband's manhood.in Fetish
More Stories