Fundraising for the Band Trip

by Oscar Dante

Copyright© 2015 by Oscar Dante

Erotic Sex Story: Cassie Walters needs money for the summer band trip to Europe. She's not going to get there babysitting.

Caution: This Erotic Sex Story contains strong sexual content, including Ma/ft   ft/ft   Fa/ft   Teenagers   Consensual   Coercion   Lesbian   Heterosexual   Fiction   Incest   Sister   Father   Daughter   Safe Sex   Oral Sex   Squirting   Teacher/Student   Babysitter   Public Sex   Prostitution   .

Cassie Walters picked up her backpack and opened her laptop. She pulled up a spreadsheet were she entered the money she earned on her last babysitting job for her band trip to Europe.

The trip was in five weeks, and she only had half the $6,000 the trip cost. Last night she would get $40, to lower the total she needed to $2,960. It was depressing.

She spent every hour she could selling candy, washing cars, and other menial jobs to raise money. The trip meant everything to Cassie, she was an exceptional jazz saxophone player and this trip would look so good on a college resume.

Her older sister, Hillary had gone to Europe four years ago with her jazz band. How did she do it?

She clicked on Skype and paged her sister. Her sister accepted the call.

She was at Yale, on a music scholarship. "Hi, Cassie!" She said cheerily. "What's up?"

"Hill, I'm depressed over the fund raising for this band trip. I have five weeks and I'm $3,000 short."

"Yeah, I remember being really short to about a month out." She said.

"I'm babysitting, washing cars, mowing yards, and I just don't think I can make it. Did Mom and Dad help you?"

"N0, they'd made it clear that they couldn't. They told me that if I wanted to go, I had to raise the money on my own."

"So, how did you do it? I'm out of ideas." She said sadly.

"Are you alone?" Hillary asked her younger sister.

"Yeah. Mom and Dad are down stairs."

"Put in ear buds. What I tell you is a huge secret." She seriously told her sister.

Cassie picked up a pair on the desk and put them in. She plugged then into the laptop. "There's no sound."

Hillary leaned into the screen getting close to the microphone. "Linda Gaines and I ... well ... we ... let the fathers of kids we babysat know ... that we would fuck them for money."

"What? You and Linda used prostitution to make the money?" Cassie gasped speaking in a loud whisper.

"Yes, it was the only way we got to go on the trip. You can make a lot of money quickly if you sell pussy." Hillary said.

"But, I wouldn't know what to do. I've only been with two boys. I would be terrified to ask a grown man to have sex with me for money." She said nervously.

"It was the same with us, we had no more experience then than you do now. The men were very helpful. It was a real turn on to fuck a girl who wasn't very experienced. They showed us what to do. Later when we knew what to do, we kept pretending we didn't." Hillary informed her sister.

"This is crazy." She paused. "How much did you raise?" She asked.

"I made $2,000 more than I needed." Her sister smiled.

"If you raised the amount you needed, then why did you keep doing it?"

Hillary smiled, "Extra spending money. And after a bit, it got to be a real turn on. Being with grown men can be addicting. They are so much better in bed than boys your age."

"But, I don't think I could ever just ask a man to have sex for money." Cassie said sadly.

"Make some business cards. Get a burner phone, put the number on the card, and what you do and for how much. Business men love this." Hillary looked down and pulled out a desk drawer. "Like this." She said as he put a card in front of the camera: 724-436-8372. Darlene, Hand Jobs $25, Blow jobs $50, half-and-half $150, anal $300, girl/girl $500, and movie appearances negotiable.

"See it lays it all out there. And they will pass the cards around and business grows." Hillary said positively.

Cassie leaned in and examined the card. "Hill, why do you have a card still, and who's Darlene? Oh, God, are you still doing this? At Yale?"

"Yale is expensive, Cassie. There are a lot of older men here who are unhappy with their older wives. And Darlene is my stage name. Your clients will know you so you can use your real first name." Her sister advised.

"I don't believe this, my musician older sister is a hooker." Cassie said in shock.

"I'll leave you to pass judgment on me when the band is in Europe and you're not." Hillary said coldly.

"I'm sorry, this is just such a shock. I need to think about his." Cassie said.

"Let me know what you think. Maybe you can come up this weekend, I have a client you could help me with, and it would give you some idea of what happens." Hillary said.

"I'll think about it. Wow, this has been a bit shocking. See you later."

"Bye Sis." Cassie broke the connection.

She closed the laptop. This was totally unexpected, but she could see that she could make the trip with the money Hillary said it was possible to earn.

She texted her bff: need to see you ASAP. About band trip money.

She quickly got a reply: im home. Where are u?

She sent back: am home too. Can you come?

The return message was quick: yep. Parents said ok. Be right there.

Cassie sat on her bed leaning against the wall thinking. She heard Allison greet her parents and come up the stairs.

When she came into Cassie's room she smiled, but Cassie just said, "Shut the door."

"What's up?" She said as she came over to the bed and sat by her friend.

"It's about money for the band trip. How much have you got?"

"About $2,200. I'm not going to make it. I thought my grandma would come through, but she had to say no. So I'm fucked."

Cassie paused for effect. "You may not be. I have an idea."

"So how do we raise that much money that quickly? Do we become hookers?"

Cassie said nothing, but just smiled. A look of comprehension spread over Allison's face. "NO! You have to be kidding."

"I'm not. I just got off Skyping with Hillary, and she told me that was how she paid for the trip when she was in high school."

"NO! You're not serious. My Mom would kill me if I went down to Howard Street and started selling my ass." She shivered.

"Oh, Allie, we don't go down to Howard Street. We print up cards and give them to the Dads we babysit for. They're our customers."

"No, shit? You're serious about this, aren't you?" Allison was recovering from her initial shock.

"I am, Hillary said she made $2,000 more than she needed for the trip. And she said it got to be fun, having sex with all the older men. She said older men really know what they're doing." Cassie was selling hard.

"This is crazy, we can't do this." Allison said firmly.

"I'm still open to the idea. I'm going to New Haven this weekend to talk to Hillary about it. When I get back I'll let you know how it was." She said.

"Okay, but don't think that I'm going to sell my pussy to go to Europe." She said.

"Girls, supper in fifteen minutes, are you staying Allison?" Cassie's other called from downstairs.

"No, Mrs. Davis. I have to get home soon." Allison shouted.

"Well, you know you are welcome." She called back.

"I know, and thank you." She yelled back.

Cassie said reaching out to twirl a lock of Allison's blond hair around her finger. "So, we have fifteen minutes."

Allison saw the hunger in her friend's eyes, and a heat flowed through her body.

Cassie leaned over and softly kissed Allison. They played lip games, then tongue games. Cassie's hand brushed Allison's breast, then firmly took it in hand. She could feel the hard nipple through her shirt and bra. "Let me get you off." Cassie whispered and let her hand fall to the tanned thigh of her bff.

"Oh, God." Allison moaned as she deeply kissed Cassie. The fingers on her thigh moved up under the hem of the miniskirt and her index finger rubbed across the front of Allison's wet panties.

As they kissed Cassie's finger ignited Allison's fires. Her wrist flicked and her fingers were inside her friend's panties touching the wet lips, massaging them, pulling them apart and tickling her clit.

"Oh you are so good at this." Allison moaned. "I love it when you finger me." Allison put a hand under her top and pushed up her bra to tug on her nipple.

"Show me your boobies." Cassis hissed. Allison pulled up her shirt to expose her tiny brown nipples. Cassis locked her lips on it and sucked as she fingered Allison's clit.

Cassie saw she was running out of time and bit Allison's nipple and toyed with it with her tongue as she pressed on her sensitive clit.

Allison bucked off the bed, whispering, "Cumming ... cumming..." and writhing under the force of the orgasm. She pushed Cassie's fingers away. "I'm done." She said softly.

Cassie offered her bff a taste of her fingers, which Allison accepted licking her juices from them.

"Dinner!" She heard from downstairs.

Allison adjusted her panties. "You always do that to me. I want to return the favor sometime." She said quietly.

"Maybe next time." Cassie said.

The train was running late and when Cassie got off at New Haven and saw her sister waving.

She ran over with her backpack and gave her a big hug.

"I'm so nervous." Cassie said.

Hillary held her out an arm's length and looked her over. "You look fine. Don't worry." Her sister wore a similar black dress that showed deep cleavage.

"We need to get to the hotel. It's just a few blocks from here." Hillary walked Cassie to a waiting limo.

A driver opened the door for the women and they settled into the plush back seat.

Hillary poured vodka into two crystal glasses. "Drink this, it will calm your nerves."

Cassie downed the burning liquid. "So I'm just going to watch?"

"Yes, unless you feel like joining in, that will be up to you." Hillary reassured her.

"How old is this guy?" Cassie asked.

"He's forty-five. He's good looking, and he's very rich." Hillary said.

"How long will we be there?" Cassie kept up the questions.

"He gets one-hour. That's pretty standard." Hillary watched the traffic.

"So what are you going to do with him?"

"I'll undress him, he'll undress me, and I'll suck his dick, and then fuck him." She said casually.

"That takes an hour?" She asked.

"Usually, I time it pretty closely. If it doesn't we can talk about other things." Hillary said.

"Other things?" Cassie looked nervous again.

"Don't worry. You'll be fine."

The limo pulled up in front of the Hilton, and the driver let the girls out. Hillary led the way inside and took the elevator to the 11th floor.

At room 1121 she stopped, "Do I look okay?" She asked her little sister. "Oh, don't tell him we're related. It would make it rather kinky then. You're just working with me."

Hillary looked over her sister and didn't see anything wrong and knocked on the door.

It opened and a man in a robe opened the door. "Darlene." He said and kissed her on the cheek. He turned to Cassie, "and who is this lovely young creature?"

"This is Cassie. She's new and wants to watch. Cassie this is Armand." Hillary said.

Cassie smiled at him.

"Just watch?" He looked over Cassie, "How much extra if she doesn't watch?"

Hillary said, "Let's just say if she joins in it's on the house. But it's her decision."

Armand nodded in agreement. He led the women into the bedroom of his suite. He opened his robe.

Cassie's eyes bulged at the cock hanging from between his legs. She'd never seen one that big. Her boyfriend was so much smaller. Hillary walked over to him and ran her hand along his long, limp dick. "Let's get this guy ready. My cunt's hot for a good fucking." She said.

Cassie stood by the door watching as her sister sank to her knees and took the big dick in her hand. She felt a stirring in her loins and watched Hillary take the head in her mouth and suck. Hillary glanced over at her sister and winked. Cassie smiled and realized she wasn't that nervous anymore. She leaned against the doorway and watched her first experience as a prostitute take shape.

It didn't take long for Hillary to get Armand hard. His eight inch cock grew in thickness as Hillary was sucking about half of it into her mouth.

Arman pulled her to her feet and lifted her dress over her head. Hillary was naked and Arman fondled her perfect breasts. He leaned down to kiss one then suck the nipple in his mouth. Cassie was getting wet watching as he laid her sister over the edge of the bed and went down on her.

"Yeah, eat me Armand, lick my pussy." Hillary moaned. Cassie wondered if the moans were real or acting, but Armand didn't seem to care. He worked her pussy with his tongue and fingers. When one finger went into her sister's ass, Cassie saw Hillary humping on his finger and looking like she was going to cum.

Being this close to a couple having sex had Cassie's pussy itching, she lifted her dress and scratched her itch. Her finger rubbed her clit as she watched her sister climax.

Armand looked over at her and smiled. "Why don't you come over and put my dick in your friend?" He said.

Cassie hesitated then moved next to him and his cock just short of her sister's pussy. Taking his big dick in her hand she rubbed it up and down her sister's pussy. Then watched as Armand thrust it into her.

As she watched she felt Armand's hand under her dress and rubbing her bare ass. She let him fondle her as she watched him fuck her sister.

His fingers slipped between her cheeks and fingered her pussy from the back. She bent over the bed to give him more room. Her breathing was coming in short pants as he worked her up.

"Take off your dress, Cassie. Let me see you naked." He ordered.

Cassie complied and tossed the dress to the floor. She saw her sister looking at her naked body as Armand's long fingers rubbed her clit.

Armand pulled his hand out and smacked her bottom, hard. She jerked and looked back at him. He grinned at her and said, "Suck her tits." Nodding toward Hillary.

Cassie looked down at her sister. Hillary gave her the faintest of nods and cupped at tit to bring the nipple to her sister's mouth. Cassie sucked her tit as Armand fucked Hillary.

Armand smacked her ass again. "Kiss her." He said.

Cassie moved up and pressed her lips to her sister's and the girls shared a deep lesbian kiss as Armand kept pounding Hillary's cunt.

The kiss lingered on and they could hear Armand's breathing grow faster. He smacked Cassie again and said, "Sit on her face."

Cassie didn't hesitate. She moved up and sat on Hillary's mouth. Her sister's tongue went to work on Cassie's clit and Cassie realized that she'd gone from observer to participant without knowing where she crossed the line.

"Oh God." She moaned as her sister licked her pussy.

"Turn around, Cassie." Armand ordered and she spun around and sat back down on Hillary's face.

Arman leaned forward and pulled Cassie into a hot kiss. Cassie grew dizzy at kissing a man thirty years older than herself. His gentle hands fondled her boobs as her sister kept up the lingual assault on her clit.

Armand groaned. He pulled out of Hillary and stood up. His cock right in front of Cassie's face. "Suck it!" He demanded and Cassie pulled the big dick into her mouth and bobbed her head as she sucked his cock.

He gripped her head and growled and a stream of cum flowed into Cassie's mouth. She swallowed it, but it kept coming. Splash after splash as quickly as she could swallow.

Then Cassie came on Hillary's face. Her orgasm catching her by surprise as she sucked the last drops from Armand's cock.

Cassie fell off Hillary's face and lay on the bed trying t catch her breath. Hillary sat up and looked at her sister. Cassie smiled at her to reassure her that she was fine.

Armand got a cigarette and lit it. He looked at the girls on his bed. He took an envelope from the dresser and dropped it on the bed. "Leave. I have work to do." He picked up his robe and put it on then left the room.

The girls picked up their dresses and put them on. Hillary took the envelope and they left Armand's suite.

They rode down the elevator in silence. The limo pulled up as they stepped onto the side walk.

After getting in the car, Cassie smiled at her sister, "I can do this." She said.

Allison went into Cassie's room and sat down on the bed. "Are you ready?" She asked.

"All set. I've got the business cards and the burner phones." Cassie took two stacks of cards out of the box. "One set for men, the other set for women."

"You actually think, we'll get women customers?" Allison asked doubtfully.

"Hillary says that women are using hookers more. You just have to treat them differently." Cassie explained.

"So, I just give one of these cards to the Dad tonight when I babysit?"

"Yeah, and don't give it to him when his wife can see. Try to get him to take you home, and then give it to him when you're alone with him in the car."

"What if he wants to do it right then?" Allison asked with some worry.

"Then get the money first and do him in the car."

"What if he wants the girl/girl thing?"

"Then you have to call me and we have to set up an appointment." Cassie said. "Now stop worrying. I'm leaving in a bit to babysit at the McGuire's'."

"Call me when you get home and tell me how it went. I have a babysitting job tomorrow night at the Carson's."

"Okay. I'll give you a call."

The night of babysitting was uneventful. The kids were good and Mrs. McGuire gave me $40, and I got her to let Mr. McGuire drive me home.

He was slow to get talking, but I told him about the band trip and how much money it cost. He seemed sympathetic. Then I said, "I've been earning money in a different way, in addition to babysitting." I handed him the card at a light and waited nervously as he read it.

He looked up at me. "You're serious?" He said.

"Yes. It's a lot of money to earn and this is the only way I'm going to make it." I said confidently.

He looked at the card. "$50 for a blow job."

"Yes, that's right."

"If I give you $50 can I see your tits while you blow me?"

I grinned, "Sure."

He suddenly turned down a quiet country road and then into the entrance of a park. He stopped and turned off the car.

He pulled out his wallet and handed me a $50 bill. "That's what you want?" He said.

"That's right." I tucked it into my jeans pocket and reached for the hem of my tee shirt and pulled it over my head. I reached behind and unfastened my bra and laid it on my backpack.

"Christ, you have nice tits." He said as he unzipped his pants. He pulled out a half-hard cock. He wasn't as big as Armand, but it was bigger than my boyfriend.

I reached into his lap and took hold of it and then leaned down and took him in my mouth. He tasted a little salty, but he was fine. I kept my lips tight around it and bobbed my head in his lap. Playing with his balls while I blew him soon had him huffing and puffing as I sucked his dick.

"Fuck, Cassie, I never dreamed you would be this good at cocksucking. Suck it, you hot little slut."

His dirty talk soon had me hot. I wished he'd popped for the fuck as my pussy was on fire.

He thrust up and my mouth was full of his semen. I swallowed it and kept swallowing until it was all in my mouth. I sat up and wiped my mouth.

He tucked his dick back in his pants. "That was one good blow job. Do I have to wait until you babysit next to get more?"

"No, just call the number on the card, and we can meet somewhere secluded." Cassie told him as she put on her bra and tee shirt.

"Next time, I want to fuck." He said smiling. "How does this girl/girl thing work?"

"I have a friend. She joins me and you can watch us make out and eat pussy and then then fuck one or both of us."

"Sounds awesome." He said.

As he pulled up to her house he said, "I'll call you I don't want to wait for you to babysit for us again."

Cassie giggled, "Cool, just call the number on the card."

He waved the card at her. "Will do."

Allison was greatly encourage about this endeavor with Cassie's success at her first try. She had a job tomorrow.

Cassie said she had one at the Hamilton's.

Late the next tight Carl Hamilton was driving Cassie home when she handed him her card. He was shocked, but when he recovered, he told her he wanted to fuck her. He wanted the half-and-half for $150. He found an isolated spot behind a dumpster down and alley and got out of the car in the dimly lit alley.

Carl stood between the car and the dumpster and unzipped his pants. "Suck it, you little slut!" He said to Cassie who squatted in the alley and took his dick in her mouth. "Get e hard!" He said shortly.

Cassie sucked his dick thanking about what a change this was from the Hilton. He got hard and she gave him her best blow job.

"Bend over the hood of the car and pull off your panties."

Cassie did as he asked and pulled the condom from her miniskirt dress pocket. She took hold of his dick and rolled it down the length, then leaned over the warm hood of the car. She pulled her miniskirt up over her ass. Carl moved up behind her and quickly had his prick buried in her pussy and was giving her a good fucking.

"Fuck me, you hot little bitch. God, you have a tight pussy. Squeeze me! Oh, fuck yes."

Cassie was moaning genuinely as Carl banged her tight little teenaged cunt. "God, Carl. I love your big dick. Pound me with it. Fuck your hot little teenaged whore, Carl. Fuck me!"

It took Carl about ten minutes before he was flooding the condom with his seed. Cassie came hard about a minute before Carl did. She pulled off of him and stripped off the condom and tossed it in the dumpster.

Carl told her we would be calling her and asked for several of her business cards to hand to clients who came into town and were looking for a little extramarital sex from a hot teenager. She willingly gave him a half-dozen.

Later than night Cassie talked to Allison and found her date had went well. The man paid her $100 for a fuck, then another hundred for another round. She was thrilled.

Inside a week the girls each made close to $2,000. On Friday Cassie did four clients in one evening, and Allison did three. Business was booming. On Saturday night the girls got hired to be the entertainment at a party for a half-dozen out of town business men.

When the girls showed up to the large hotel room, a guy named Ralph gave them a thousand dollars. "This should cover the girl/girl show, and any blow jobs or fucks you hand out afterward."

The girls showed up wearing their normal high school clothes, miniskirts, tank tops, thigh-high stockings and thong underwear. Cassie pulled Allison to the king-sized bed and laid her down and started kissing her. The guys loved it. They rolled around the bed feeling each other up for a few minutes before they began stripping. They sucked on each other's tits and fingered their pussies through their underwear and then under the thongs.

Soon Allison was naked and lying back on the bed with Cassie going down on her. The men were taking pictures with their phones and a few had hard ons in their pants.

Allison had a screaming orgasm and pushed Cassie on her back and went down on her. Ralph took off his pants and boxers and rolled a condom down on his cock and moved behind Allison and began to fuck her while she was eating out Cassie.

A guy named Bob stripped off his pants and put his dick in Cassie's mouth so she could suck him off while Allison ate her pussy.

Ralph didn't last too long, and a guy named Don moved into Allison's pussy with a rather sizable dick. He pounded Allison hard until Cassie came. Bob turned her over and mounted her from behind and fucked her until he came in her pussy.

Over the next hour the girls fucked all the guys and they went down on each other again at the end. When they came everyone applauded and tossed money on the bed for them. They gathered it all up and dressed. After counting it in the car, they found they had $1,600. Allison split it with Cassie and they both went home for a long deserved rest.

With ten days to go Cassie got a call from a woman on her burner phone. She said her name was Melinda McCann and she wanted an hour of Cassie's time for sex. They made an appointment for four o'clock at the local Motel 6. Ms. McCann would text her the room number when she checked in. Four o'clock was good as Cassie could get home just as her parents did.

Cassie was excited when the text showed up at 3:45. She parked in the Motel 6 lot and found room 117. When the door opened she immediately recognized the woman in the robe. It was her English teacher of last year, Jessica Shoemaker. Without giving Mrs. Shoemaker time to react to seeing a student, Cassie stepped into the room and shut the door.

"Cassie!" Mrs. Shoemaker said in shock. "What are you doing here?" She was freshly showered and her hair still wet.

"I think you know, Melinda McCann." She smiled. Cassie removed her jacket and revealed a thin tank top with no bra under it. Her breasts were clearly displayed by the thin silk. Her nipples were points in the shiny cloth.

"But you can't be..." Mrs. Shoemaker's eyes darted to Cassie's sexy attire.

" ... a hooker, ... a prostitute." Cassie finished her sentence smiling.

"Yes." Cassie moved close to Mrs. Shoemaker who backed up. Cassie drew close again and her client backed up. One more step and she would be against the door. Cassie stepped closer. Mrs. Shoemaker felt the door against her ass.

"I am trying to raise money for the band trip. I have to come up with $6,000, and I'm almost there. The $200 you're going to pay me for our little session will get me closer to my goal. This is important to me. Important enough for me to turn to prostitution to get what I want, and I get what I want, Mrs. Shoemaker."

"But you're a student. I'll get fired, they'll take away my license. I might even go to jail." She was terrified.

Cassie put her hands against the door at Mrs. Shoemaker's hips, trapping her in place. She and Cassie were the same size and Cassie's eyes were level with hers.

"Mrs. Shoemaker, or may I call you, uh ... Jennifer?" Cassie said coldly. The frightened woman nodded. "Jennifer, there are two ways this can play out. First, I can call the police. Now, normally, calling the police is not what a hooker does when with a John or Johanna, but in this case, with the Johanna a teacher and the hooker a student, this could cause problems for both. Me? I've never been arrested. I would get a fine and, at most, some probation. You on the other hand, as a public school teacher, would lose your livelihood, have your face in the news, and perhaps get some jail time, even though this would be your first offense. Do you see my logic here? One phone call to 911, and you have to explain to your family why you're hiring students to service your lesbian desires. Or, you can pay me, I'll give you the best sex you've ever had, I'll turn you inside out and back. I'll then do it again. You will never experience what I can do for you. I keep quiet, you keep quiet and we're all happy. Now, I'm not even going to give you a chance to think about it or make a decision. I'm going to make this decision for you." Cassie pressed her lips softly to Jennifer's. She softly pulled at the teacher's lips. Cassie could feel her warm breath on her face as the teacher was panting. Cassie opened her mouth and pressed her tongue to Jennifer's lips. The woman gently rubbed the tip of her tongue on Cassie's.

Cassie pulled on the belt of the terrycloth robe. The tie dropped and Cassie opened the robe. Her hands caressed the teacher's flanks, slowly moving up and down. Jennifer gave off a moan and her kiss became more impassioned. Cassie knew she had won.

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