Tiff Ruins Anon's Summer

“Jesus, Anon, how about you check your fucking phone?”

Tiff's voice startles you awake – damn, you hadn't realized how tired you were. She's leaning in through the passenger window of your crappy Cherokee, angerly waving your own phone at you. Brat must grabbed it off the seat.

“Sup, Tiff. Good to see you again.” And it is good to see her, especially the way the door presses up her breasts as she leans in. You gesture towards the bags filling the back -“Look, I've already got the hootch for the party – no problems, and you're welcome. You make a grab for your phone, and manage to slide it from her hand.

Tiff hops back after you recover the phone. “Yeah, I saw it. Too bad your dumb ass' stuck with it for a week.” She hits the unlock button from the inside, and climbs into the seat besides yours.

“Uhhh-” A brief scan of your many new texts tells you that the end-of-senior-year high school party got bumped unexpectedly, and Tiff was trying to tell you to pull around to discuss what to do next. “-why can't you take it?”

“We got two problems – first, the jock who's hosting is out of town this weekend. Training camp or somethin'. An' second, the stuff can't come back with me, since my parents are still real suspicious from spring break.”

Ah, Spring Break at the Crusts'. You hadn't known them that well then, but had received some fame for a few successful late-night beer runs for Tiff and her friends. It turned out that having an unscrupulous cousin at a liquor store was sufficient to put you on good terms with her, and she had been in contact for many occasions since then.

“OK, well, I'll take it back home and smuggle it into my closet somehow. No problem. Did you really need to come out here and tell me that?” Tiff had contorted herself around to rummage through the bags in back, leaving her butt wedged at eye level between the front seats.

“Figured I'd also check what you got, and pay up...what's this?” She pulled back and reseated herself with a beer in hand.

“That? It's called Wild Blue. It's like a blueberry beer, I figured you and Tiff might like to try it since you ask for all the fruity wines and such.”

Tiff nodded and looked at you. “Oh cool. We get the beers for the guys, usually, but thanks.”

To your surprise, she then cracked the beer, flicking the cap out the window. She took a swig, settling back with a quizzical expression. “Tastes like blueberry soda. This stuff's real dangerous.”

“Uh, alright then! Drinking warm beer in the school parking lot. Classy.” You decide to join, grabbing a bottle of Rolling Rock for yourself. It's a good thing it's well after 4 on a late spring Friday, and the closest cars are a hundred feet away, nearer to the baseball diamonds.

To your knowledge, you've actually never spent even this much time alone with Tiff before. You've been invited to quite a few parties and pre-games this semester, but your meetings alone have always been quick hand-offs to transfer booze to her and Brit. Otherwise, there always was someone around.

Tiff texts for a bit, then throws her phone on the dash. “Yeah, I know. Brit's at some college prep thing she joined AFTER the party got moved, leaving me stuck here to wait. Pshh.” She kicks off her sandals and sticks her legs out of the window on an angle, resting her beer on the sill.

She looks uncomfortably hot, judging by the sweat beading on her forehead. The sweat running down her neck, between her breasts –

BUZZZZZZZ

Tiff's phone startles both of you. Tiff, lunging for the phone with her left hand, comes up short and falls left awkwardly as she tries to right herself. “Fuck!” Her head comes to a rest for an instant on your crotch. You hear the beer bottle clack loudly on the ground outside, but fail to shatter.

You helpfully move to assist, grabbing under her armpits and righting her in a tasteful way while also maintaining contact with the tube top she has on that day.

Tiff scans her phone. “Cool. Brit's out early, so do you think you can drop me off at the east entrance?” She fixes her top – shit, did she notice?

“Yeah.” At the school, she takes a swig from your water bottle and hops from your car into Brit's, leaving payment and promises to text you if anything was happening this weekend.


The following Monday morning, You're seated in front of the Assistant Dean, with the bottle of Wild Blue in a plastic bag on his desk. He briefly goes over the evidence, including some blurry frames from a surveillance camera that note your car in and driving away from your parking spot. Nothing from the east entrance, however.  Luckily, you've been preparing for this nightmare for months.

“So you say this was all for you, Anon? I find that very hard to believe.”

Your posture is humble, your grin somewhat shit-eating. “I'm sorry. I'll be the first to admit I have a problem, and right now I need help, not punishment. This was that cry for help.”

He doesn't react to that well. Over the course of nearly an hour, he attempts to connect dozens of incidents of underage drinking to your purchases.

“This wasn't all for you, was it? The footage shows that someone else was in your car, and we're working on getting into your phone to go though the text messages. You're a middleman.”

“I wish that were true. Maybe then I'd have some friends ;_;”  Your acting isn't awful, and you've been careful to only accept Brit's texts after she installed the encrypted chat program you picked out. In the end, you walk out sans phone and with many weekends of community service and therapy to attend, but with nothing connecting you to Brit or vice versa.


You've got earbuds in while running the industrial vacuum cleaner after school that Friday, so the tap on the shoulder takes you jump. “Who-oh. Hey.” It's Tiff, and the quickly hands you a note indicating where to meet her once you're done.

You've been thinking about Tiff all week, and how evasive she's been. She was quick to apologize online, but she hasn't spoken to you in person all week.

Shortly thereafter, you're in a section of the locker room generally reserved for the wrestling team, and which hasn't been regularly used in months. Still, you're thankful some other poor schmuck like yourself has been cleaning up in here, and the smell isn't bad at all. Tiff is sitting on a bench in the far corner. As you approach, you notice a duffel bag at her feet. “Hey. Want a  beer?”

“Are you insane? I've been grounded for months. I have to be home by 5 everyday, or else my parents will call the cops. I'm avoiding being suspended by a fucking thread. Also, I'm in counseling for made-up alcoholism, which I'm having to improvise on by watching fucking Always Sunny and remembering friends' drunken stories from YOUR parties. So, no.”

Tiff listens, avoiding your gaze, then begins to speak. “I know I fucked up. I just...fuck!” She pauses for a moment, then hops over the bench to stand in front of you. She's standing very close, and you can see the beginnings of tears in her eyes. Her perfume is faint, but overpowers the smell of the room. You really want to hug her for some reason. She's waiting for you to do something.

You hug her, and feel her hot tears sink into your t-shirt. She must feel how fast your heart is beating, either from anger, lust, or whatever. “Tiff...god damn it. Look...I...uh.” This is not going according to plan. Where the hell did this come from?

After what seems like hours, you both sit down on the bench next to one another. You've managed to keep an arm around her this whole time.

“I'm a fucking idiot, Anon.” Tiff's eyeliner has come off on your shirt. Fuck. Her tears are carrying more of it down her face. “This was supposed [*sniff*] to be a, a, a fun summer party to end the year, and I just ruined your whole summer.”

“Hey, hey hey. It's OK.” You move your hand up and down her shoulder, the classic consolation move. “I don't know why they decided to go after that bottle, after all there's probably a dozen new cans every morning from other Seniors boozing it up every morning.”

This seems to calm her down quite a bit. She straightens up on the bench, but you keep your arm loosely around her waist, just above her hips. “I just wanted to have a drink with you last week, that's why I went out there. Truth is, the party got moved a while ago. An' I thought...well, this was my chance to finally get some time with you.”

“What do you mean?”
“Well, you know...so we could carry on like at Spring Break.”

“Uh...” Spring Break? Lots of gaps in your memory. Beer runs. Parties. More parties? Talking to Tiff, texting her...gaps. Flirting, always flirting with the girls. Tiff's giant ass hidden only by a bikini, my GOD you can see every- “Wait. Did we...hook up? I'm missing a few nights from back then.”

Tiff giggles. “No, no, but I knew YOU really wanted to! An' I'm like, who the fuck is this guy? And of course, Brit's making fun 'a me 'cause I keep inviting you anyway...” Tiff's laughing now, stifling it in the empty room. “...an' Brit's like, 'Anon's way too shy to say this sober, but he means it,' you know? He really like you... And 'Tiff, you're too romantic, you want Anon to make the first move...'”

“So...you never told me because...”

Tiff smirks. “Well I gave ya plenty of chances! Invited you to every damn party I threw, but you never got that drunk again. Still, I had these feelings...”

“Oh...so.” The awkwardness is intense, but Tiff never takes her eyes off you. She's looking up, her breathing audible. You bend down to kiss her, and she takes the opportunity to pivot onto your lap. Her wide hips straddle yours as she drapes her arms around your neck. You're both giggling now, kissing quickly and gently grinding against one another. You had changed into some dingy sweatpants before work, so your erection is quickly noticeable as it presses into the front of her shorts. “Woah! Easy, boy.”

“Hey, it's only cause there's a cute girl in my lap, whoops.”

Tiff's breath is warm on your face. “Just hold on for a second. When do you have to be back home?” Up until now Tiff was kneeling on the wooden bench as she straddles you, and she takes the opportunity to re-adjust and put her legs over the bench. You both inhale as you realize her legs won't reach the ground in this position, leaving her full weight on your crotch.

“Uh, around 5. It's only 4:28 now...”

“So we gotta make this quick. Can ya do that?”

Tiff smirks as she leans leans back, pivoting back over to sit next to you. In an instant, you shove down your pants and underwear, freeing your erection. Likewise, Tiff pulls her shorts down around her ankles.

“Bend over, Tiff.”

You stand up behind Tiff as she kneels on the bench, and push her panties aside to finger her pussy gently.  “Jesus, Anon...you're nastier than I thought!” Tiff braces herself on the lockers as you slide your fingers around inside her, your erection rubbing her backside.

“Ok...I'm ready”. Tiff reaches back between her legs, and you buck your hips forward as she guides you inside her. “Jesus!” An unmistakable clapping sound begins as you thrust inside her, her ample ass cushioning the blows.  Despite the amount of ass in the way, Tiff's at the perfect height to present her pussy, and she takes you to the hilt.

“F-Fuck! Oh God!” Tiff is panting, already thrusting herself back onto you. She's incredibly wet, and her shaking ass massages your cock from every angle.

“Shit, Tiff...Ah! You were already hard from when Tiff was grinding into your lap earlier, and you can tell you're not going to last long. Tiff is more than bent double now, and you reach over to brace yourself as well, pounding down into her pussy. Despite her wide hips, her pussy is tight and is gripping you as you pull out.  “Tiff...I...I'm gonna cum!”

“Anon...f-uck...you can come...I want you inside!” As she says this, you can feel both your orgasms are close. She's thrusting back hard, and you can feel her pussy begin to spasm around you.

“I'm-” You grunt and shove one last time, spurting hot cum deep inside her. Tiff moans, and you feel her pussy begin to relentlessly spasm around you. “Fucking fill me! Fuck me!” You climax again, pumping even more cum inside as both of you moan and grind against one another. Eventually, your groans subside as your orgasms relent. You stay together for a moment longer, feeling a wonderful warmth as you fill Tiff's pussy with seed.

You lean back, weak-kneed. As your cock pops out, cum spatters the bench and Tiff's shorts. “Whoops.”

“Uh, help?” Tiff's arms are too shaky to raise herself out of the position you pounded her into, and you end up holding her hand to help her up. “Wow, you needed that. God. My shorts are ruined.” A mix of Tiff's juices and cum spatters the bench, and her shorts are indeed ruined.

You walk carefully over to a supply closet, finding some paper towels and fishing out a pair of exercise shorts from an old box. “Think these'll work?”

“Hand 'em over, then you should probably head out, huh?” You check the time – 4:37, just enough time to make it back with a red light or two. As you hand over the shorts, you pull her into another kiss.

Tiff kicks off her shorts and wiggles into the new pair, amusingly short on her wide frame. “Message me when you get home, ok? Maybe I can chuck a burner through your window so we can talk at night.”

“One of these for the road, then I'm off.” You paw through the duffel bag, finding a mix of leftover beers from previous parties.

You each take one, pound it, and set about living the rest of your summer.