UMD Stories


Anna's First Time With Pies
Story by messyman88x
Posted 2/18/20     1352 views
*This story is 100% fiction. It is not based on any real person, although it is based on many different real situations. This may turn into a series, which is why I spend a lot of time providing backstory.*

Anna sat at her desk, looking out at the unseasonably cool late September day. It was her first semester away at college, and it was about a week past her 19th birthday. She was excited to finally be away on her own, as she came from a fairly sheltered household. She had dated a few guys briefly in high school, but none of them were very serious or lasted very long, and as a result she was still a virgin. Her lack of experience was not due to looks however: she was one of the prettiest girls from her school and could've had any guy she wanted, but she decided to avoid unnecessary drama and be picky with her relationships. Anna played a few different sports growing up but was never really great at any of them, but she enjoyed soccer and cross country the most. She had the body of a runner, fit and toned, curvy in the right places, with shoulder length golden dark blonde hair that more often than not was up in a ponytail. She ran every morning before class, and went to the gym a few times a week after class. Because she often worked out before and after class, she often wore athletic type clothes to classes: a loose fitting t shirt, Nike leggings, and one of her many pairs of running shoes were the norm, although she did have the same clothes typical 19 year old college girls wear as well.

Because of her looks, she had no problems making friends on campus. When she left for school, she only knew one other person, her roommate Katie. Katie was a friend from her hometown that found out they were both going to the same school and they decided to room together. Katie's boyfriend also went to their school so she didn't spend a whole lot of time in their dorm, especially on the weekends. Anna decided she needed to make an effort to find things to do on the weekend too, so she started exploring different clubs and groups. The row of sorority recruiting tables caught her eye one day when running through campus, and she decided to take that route. After talking with a few different groups of girls, she made her choice: Alpha Delta Pi, one of the bigger groups on campus.

Her chapter had meetings weekly, and every Sunday she would run the half mile to the sorority house and then either get a ride back to campus or run the half mile back. After her acceptance her regular t shirts were gradually replaced with shirts containing her letters, which became a source of pride. Her sorority sisters loved her outgoing bubbly personality, and even as a freshman she became a leader within the group. Nothing out of the ordinary or different happened however until mid October...

It was the second meeting in October, when the senior leadership of the group announced they were going to be holding a fundraiser later that week and were looking for volunteers. They gave no other details other than the date, time, and place to be. Excited to be an active part of the group, Anna signed up right away. Whatever it was would be so much fun! She only had one class on Friday, when it was going to take place, so she would go to class and get a run in before she needed to be there and would relax after it was over with and she got back to her dorm. Thursday night she got a group email from Hanna who was in charge of the fundraiser, restating the time and place on the quad to be, but no other details were given still. She did notice that the email was sent to 3 other freshmen besides her, who signed up, and 2 sophomores. The message also stated for the girls to not do their makeup very detailed and to wear a shirt or sweatshirt with their letters on it but otherwise dress casually. This stuck her as a little weird, but she didn't think too much about it.

Friday finally came. Anna got up and checked her email to find out her class was canceled for the day. "Awesome," she thought to herself, "I'll have even more time to get ready and get everything done ahead of time." She did some laundry, got some homework done, and decided it was time to start getting ready. She went to her closet and pulled out her favorite shirt with her letters on it, a nice light blue with white letters, it fit her perfectly and she loved how it looked on her. She put on her favorite black Nike Pro leggings, black ankle socks, and her favorite pair of blue Asics running shoes. They didn't quite match her shirt, but they were close enough. She went out for her late morning run, and ended up getting to their table on the quad a little early. The school had set up the table already but no one else was there yet, so she sat down and waited. About 5 minutes later Hanna walked up carrying a large duffel bag that looked fairly heavy and said "Hey! You're early!" "Yeah, I was on my run and ended up here and figured I'd just hang out!" She replied with an excited tone in her voice. "Well great, you want to help me bring some things from the car?" Hanna replied, pointing over to her car in the adjacent parking lot. Anna agreed, Hanna set down the bag she was carrying, and they both walked over to her car. "I had to go to the store to get everything, it cost quite a bit, but I think we should be good" Hanna said, which sent Anna's mind into overdrive. What were they about to do? They arrived at her backseat which contained 3 more large duffel bags, all appearing to be as full as the first. There was also a large posterboard which was angled at a way that Anna couldn't read it. "If you can take 2 I'll grab the other bag and the poster and lock up" Hanna said from the other side of the car, so Anna threw a bag over each shoulder and started heading over towards the table. "What is in here?" She kept thinking to herself. As she got to the table she put the bags down, and her curiosity got the best of her. She peeked open one of the bags, and inside saw what had to be at least 25 to 30 cans of whipped cream. She turned around and finally could read the sign, which read PIE A PI, $2. She couldn't believe it. She would've gone back and changed into some older jeans if she knew! But too late now.

Hanna set the poster up against the table, taping it so it didn't fall over, and unloaded the bags. 50+ pie tins, 60 cans of whipped cream, 3 bottles of chocolate syrup. When asked about it, Hanna said "the chocolate is to make it taste good!" Everything was ready to open, except one thing: Anna was still the only girl there. Hanna was only there to run things, it was clear she was not supposed to be a target. Hanna and Anna sat at the table, waiting for classes that were currently going on to let out, and for the rush to begin. "Please, girls, don't let me be the only one here..." Anna pleaded in her head as she sat there with her legs crossed.

The top of the hour came, when classes let out. People started streaming out of the buildings surrounding the quad, and Anna's heart was racing. Finally, after about 5 minutes, she saw someone she knew. Todd, a guy from her English class, stopped by the table and said "Hey Anna! You're doing this kinda stuff now?" to which she smiled awkwardly and nervously. "Only $2 to pie her!" Hanna replied happily, and Todd thought for a minute and reached for his wallet. Anna's heart really started racing now. She couldn't back down now. She got up, put on the goggles that Hanna had given her, and walked over to the tarp set up on the grass. Todd smiled as Hanna filled up a pie tin with half a can of cream, and she added a sprinkle of chocolate syrup on top. Todd picked up the tin and walked over to her. "You ready?" he said, and Anna nodded nervously and braced. Todd counted down...3...2...1...

*SMACK*

Everything around her went dark, and she couldn't smell anything but cream and chocolate. She stood there in shock, not knowing what to do. Todd twisted the tin around a little to make sure everything came out, at which point the cream and chocolate began pouring out. Her face was covered, and her shirt was quickly following suit. She wiped the cream from her goggles and started licking up what was around her mouth ("Hanna was right, it does taste good" she thought to herself). As she got her goggles cleaned off, she saw what had become a small line at the table. "Oh no. Where are the other girls?" she thought in a panic, knowing if they didn't show up she was going to be pied by each and every one of them. She didn't know the guy, who walked up almost shyly, surveyed her face and *smack* the next pie came in, softer and gentler than the first. Most of the pie slid out the bottom of the tin, and she now had white streaks running down her leggings and pooling on her shoes. "These were over $100" she thought to herself, a little mad. The next guy walked up and smacked the next pie in her face. At this point her shirt was entirely covered, and she considered it a total loss. She could feel it soaking through to her sports bra underneath. But she also felt something else. "This is kinda...fun" she started to think. She started to egg on each participant, sticking her face out for them, playfully sticking her tongue out, and enjoying it. She even felt herself getting a little turned on by it. After about 10 pies, that turned into very turned on. She loved how the pie felt running down her face, covering her once-blue shirt, running down her leggings. Finally she heard the voice of one of the other girls, Trisha, running up to the table. "I'm sooooo sorry I'm late!" she told Hanna. Hanna looked at Anna, smiled, and said "Don't worry, Anna's holding her own over there!" Anna saw this as a chance to take a break, so she walked over to a chair and took her shoes - half stained with cream and chocolate - off. Trisha was wearing a different shirt, but was also wearing tight black Nike leggings and what looked like a new pair of light brown Ugg boots: clearly she didn't know what to expect either. Anna turned around and saw Todd again, with a big goofy grin on his face. "You have a friend finally?" he said. "Yeah!" She laughed. "Want to get both of us?" "No, but I think you've taken a beating and deserve to be the first to get her! Then I'll get you both." Todd replied, handing $6 to Hanna who pulled out 3 tins and started filling them. Anna grabbed Trisha's arm and they ran over to the tarp. Todd whispered something to Hanna, and then brought one of the tins over to Anna who took it and took aim at Trisha who looked like she was terrified. "It's really not that bad!" Anna assured her, and she pressed the overfilled pie tin hard into Trisha's face. Trisha let out a little shriek and started wiping cream off her face. Todd walked up holding 2 tins. "Squeeze together!" he said, and the girls got as close to each other as they could. He proceeded to sandwich them between the two pies. Anna was loving this by now, while she could tell Trisha was having second thoughts about signing up. A small line had formed by now to pie the new girl, and Anna made her way over to the table to help Hanna take money. On her way to the table she stepped in a large pile of chocolate and cream so she sat down and took her socks off. Grabbing her shoes, she slipped one on and immediately felt something squishy. Someone had filled them with what looked like a full can of cream and full bottle of chocolate, and the mess was now pouring out the top and through the once-blue mesh. She looked at Hanna, who shrugged and said "your friend gave us $20 to do it, how could I say no?" and Anna simply smiled and shrugged. She loved how it felt actually. She didn't even care that her $120 shoes were now stained and ruined inside and out. It felt so wrong, and she loved it. Over the next 40 minutes or so they kept taking money, the other girls showed up slowly, and they took pie after pie. They finally ran out of tins, and she sat down exhausted, covered, and happy.

Hanna asked if she wanted a ride back to her dorm, but Anna declined. She enjoyed being seen this way. It was exciting, fun, different. Anna said her goodbyes, gathered up her things, and rushed to her dorm. She needed to get herself off, NOW. Everyone staring at her as she ran back to her dorm only made matters worse. She was soaking wet inside of her skintight and cream soaked leggings. She rushed in the door, up the stairs, and into her room. Katie wasn't there, which was expected. She closed the blinds on the windows and laid down on her bed, soaking it in chocolate and cream in the process. Her hand immediately went down her leggings, inside her panties, and she began playing with herself. She looked down at her ruined shirt, leggings, and shoes, and couldn't take it anymore. She let out the strongest orgasm she had ever had, having to put her free hand in her mouth to keep herself from screaming. It wouldn't stop. Her fingers kept going, and she kept cumming. Suddenly she felt something new and wet running down her legs. "Did I just squirt???" She thought. Sure enough, she had. She collapsed onto her bed, now fully exhausted, with a bed in need of a wash as bad as her.

She laid there for about 10 minutes before she gathered herself and got up, took off all the clothes she had on, took the sheets off her bed, and threw them into a bag. Living on an all girls floor it wasn't too uncommon for the girls to walk around without clothes during the day if going to the bathroom or showers, so she threw on her Nike slide on sandals to take a quick shower. She washed her whole body, amazed at how much chocolate and cream her hair could hold. Afterwards she went back to her room, threw on a sorority sweatshirt and another pair of leggings, along with a white pair of ankle socks and her Birkenstock sandals. Grabbing the bag of clothes and bed sheets, she went and threw them into the washer. Sitting down on one of the couches in the laundry room, she pulled out her phone. Several of her friends had seen her and taken pictures of her and tagged her on social media, so she looked at them all and a few of her favorites she saved to her phone. An email came in. She opened her mail app, and it was from Hanna.

"Anna, thank you so much, we made more money today than we ever have doing Pie a Pi! Sorry about the other girls being so late, I'm not happy with them, but it really seemed like you enjoyed yourself! If you want to do something like that again, let me know, we can set something up!"

Anna looked in the full length mirror across from her and smiled, knowing what she looked like just 20 minutes beforehand. She hit the reply button on the email and typed,

"I enjoyed it more than you know. You doing anything tomorrow? Let's meet up and talk about it."
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Comments:
ChuckSM:
11/27/20
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great backstory to this series! Already love the character Anna and looking forward to what's in store for her!
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