Amanda Cortland was going on eighteen when she and her cousin, Barbara, or Babsi, as she was called, were lounging in the family room watching TV and sharing local gossip.
“Congratulations, Amanda!” her cousin said with a hug.
“For what, Babsi?”
“You’ll turn eighteen in a month!”
“So what? Big deal.”
“You’ll be out of school in a few months. That means freedom, independence, and you’re in control. It’s so liberating. You’ll be an adult.
“It doesn’t feel liberating. Well, maybe it would if I had a car to drive.”
“Can’t you drive your mom’s car?”
“Nope. She said the insurance is too expensive, and she can’t afford it on her waitress salary. Even with tips, we’re just scraping by.”
“That sucks. A girl licensed to drive without a car is like a girl who’s a virgin. Maybe you need a job.”
“What job will pay three or four thousand a year for insurance? It won’t be working at McDonald's.”
“Yeah, I see your point, but let’s look at the bright side. You still have Darrel’s, um, what did you call it, his stick shift?”
Tears came to Amanda’s beautiful azure blue eyes. “We broke up. Emily is shifting his gears now.”
“You’re kidding! You are ten times more beautiful than Emily.”
“Thanks, but I can’t compete with those enormous boobs of hers.”
“Okay, but that’s because Emily is older. She graduated last year. In a year or two yours will develop. Actually, I think your petite boobies are sexy. A lot of guys like the perky schoolgirl look. They aren’t as intimidating as Emily’s. Anyway, you were with Darrel all last year, so she isn’t doing anything with him that you didn’t do, assuming you’re not a virgin, that is. Was he your first?”
“Well, yes and no. Yes, I’m not a virgin, but It wasn't with Darrel when I did it for the first time. I had just turned sixteen when Uncle Roy took me to his office to show off his golf trophies.
“He asked me if I had a boyfriend. I said no because I hadn’t hooked up with Darrel yet. Uncle Roy stroked his chin as if he was thinking, then said, ‘A girl shouldn’t leave high school a virgin.’ That’s when he showed me another of his trophies.”
Babsi let out a long laugh. “You mean his trophy cock.”
Surprised, Amanda said, “You were in the trophy room with him?”
“Yes, and I was no older than you when he rode me like his namesake.”
“Who’s that?”
“Roy Rogers? A cowboy in the movies. ‘Back in the saddle again,’ and I was the saddle.”
“Babsi, isn’t it taboo or something to have sex with a relative?”
“Maybe it is, maybe not. I don't see it that way. Uncle Roy is very kind and thoughtful. I loved the attention, and the sex wasn’t bad. Did you like it?”
“Well, not so much the first time, but the next time was better.”
“You let him fuck you again?” It was Babsi’s turn to be surprised.
“Yeah. We did it in his van on my dad’s fiftieth birthday.”
Babsi laughed. “Sounds like a fun birthday party. I guess once you’ve had sex, and the anxiety of the first time has passed, a girl just wants to try it again. That’s the way I felt. Now when I get horny, I’m not that choosy. Like a couple of days ago, I was so horny that I slept with Stephen.”
“But Stephen is your brother!” Amanda shrieked.
“Stepbrother, and he has a cock to die for.”
“So, you did it with him?”
“Yeah, but it wasn’t our first time. We started last summer before I left for college. I had already done it with Uncle Roy so why not with Stephen? I put on my mini bikini and seduced him by our pool. Stephen went nuts. It was amazing, Amanda, not just because he has an eight-inch dick but the excitement of doing something forbidden. You know, like you said, taboo.”
“Don’t you feel ashamed?”
“No, Amanda. Like they say. 'It’s all in the family.’”
“What do you mean that it’s all in the family?"
“Well, I promised not to tell, but you can keep a secret, right?
“Sure. What’s the secret?”
“Do you remember celebrating Grandma's seventieth birthday when she had a little too much wine?
“Yeah.”
“She said I was sexy and looked like Mom when she was my age. Then she whispered that she would tell me something if I promised to keep it a secret. Up until now, I haven't told anyone.”
“So, tell me the secret?”
“She caught my mom and your dad in bed together, and they weren’t playing hopscotch. Grams didn’t say her son and daughter were fucking each other but the way she said it and the look on her face made it clear that’s what happened. So, it got me thinking.”
“Thinking about fucking Stephen?”
“Right! So, that made it easy to let him screw me. I probably would have done it anyway.” Babsi chuckled, “He’s a stud, Amanda. You’d love having him fuck you. Maybe I can fix you up with him if you want.”
“I’ll have to think about it, Babsi. I guess that would make Stephen and me kissing cousins?” Amanda said with a giggle.
“But, Amanda, if you two hook up, make sure Stephen wears a condom. He likes to go bareback, which is OK if you are on birth control.”
“Mom said I was too young for birth control pills. She says it only encourages girls to have sex. Darrel never used one and always pulled out in time. Are you on the pill?” Amanda asked.
“No, I wear a diaphragm. The pull-out method is dangerous, Amanda. My friend’s mom is a nurse. She can fit you with a diaphragm if you want to be safe.”
*
A week after Amanda was fitted for her "cup," as she called it, she took Babsi’s suggestion and made a date with her stepbrother, Stephen. She had no boyfriend, was protected, and was horny, so the timing was perfect to find out if he was as good as his sister claimed.
Stephen was twenty and muscular and never shy about showing off his abs. Babsi was right, he had a large, thick cock, but in truth, he only wanted to get himself off and didn’t care about Amanda.
But Stephen wasn’t only pleasuring himself with Amanda. He had contacts.
While Stephen was recuperating and preparing for a second round, Amanda babbled on and on about not having a car to drive. She complained that her mom couldn’t afford the insurance.
“Get a job and pay for it yourself,” he told her.
“Yeah, that’s what your sister said. What job will pay a few thousand a year? It won't be at McDonald's, the only place that hires teens.”
“Maybe I can help,” he told her.
“How?”
“I have friends with money.”
“So, how is that going to help me?”
“Well, if you don’t mind horny guys a little older than you, they will help you.”
“You mean turning me into a whore.”
“No, Amanda, it’s not like that.”
“How is it like, Stephen?”
“It’s like they are your sugar daddy.”
“I still don’t get it other than you want me to fuck them.”
“It’s pretty simple, Amanda. You go on a date with a man. He might take you to dinner at a nice restaurant. If you like him and he suggests the two of you go to a motel, it is your choice. If he likes what you do at the motel, he helps you with your insurance problem.”
"So, you’re like a pimp, right?”
“No, Amanda. That’s not fair. The men I’m talking about are nice guys. They’re my friends. Most of them are married and unhappy at home. They just need an attractive girl like you to show them some affection and listen to their unpleasant lives. You're young, and with your cute puffy tits and tight cunt, my friends would be thrilled and very generous with a girl like you. You help them, and they help you. As long as you received no harm, there is no harm done.”
As a way of encouraging Amanda, Stephen added, “Look, Babsi has been with a few of my buddies, and they helped her pay for college. Talk to her. She'll tell you if it is good, bad, or indifferent. It really doesn't matter. It's the money that counts,"
“I’ll think about it.”
"Now let's check out your back door," he said and reached for a tube of Glide. "Bend over so I can lube your butthole."
"You're going to fuck my ass?"
"What? You make it sound like you're an anal virgin."
"Yes, I am."
"If you haven't tried it, you haven't lived."
"Please be gentle," she begged.
After lathering up his cock and her ass, Stephen squeezed in her tight hole and was gentle at first, pushing in slowly, an inch at a time. It wasn’t an easy fit, but the Glide helped. Eventually, he plunged in balls deep and began thrusting with deep strokes, then faster, harder strokes.
Amanda’s shrieks of hysteria weren't of pain or joy because she was feeling both, sometimes at the same time. She cried out, “Oh, oh, oh. Fuck, fuck, fuck. I think I’m cumming!”
“Ahh, ahh, ahh, ahh,” he growled as he unleashed a fountain of hot cum deep in her bowels. He didn’t pull out at first, enjoying the warmth inside her while they lay together exhausted. Stephen asked, "Well, did you like it?"
"It wasn't bad or good. It was just different, and I won’t be able to sit down for a week."
Later that week, Amanda began thinking seriously about Stephen's suggestion to fuck his buddies, especially after listening to Babsi's sugaring stories. It sounded okay. Babsi said her sugar daddies were considerate and fun. Some were a good fuck, better than the guys at college, and the money was good. "After all,” she told Amanda, "you had sex with our Uncle Roy, and you didn't complain."
"I guess not, even though it hurt a little for my first time."
*
Stephen set Amanda up with George, her first sugar daddy encounter. George was about forty-five and must have been handsome fifteen years earlier. They went for dinner at a supper club, talking about their personal lives. He said he was never married, then added, “I have to tell Steven how much I appreciate him getting us together. You are a princess, cute and sexy."
She thanked him for the compliment and explained her situation. Amanda used Babsi's college ruse of needing money for college. Amanda explained that her mom was a waitress and college was more than they could afford. She thought it was a subtle way to hint that she expected to be paid.
After helping each other out of their clothes, George said, "You seem kind of shy. Are you afraid of being with someone older?"
"No, I'm not afraid. I'm just a little nervous. This is my first time," she said.
"You've never had sex?" he asked.
"Of course I have, but it's just that I've never had sex with a sugar daddy."
"Is that what I am? Well, let's just pretend that we are lovers indulging in unrestricted fun. OK?"
"OK."
George lay on the bed with his hard cock standing straight up, throbbing in anticipation. Putting her delicate fingers around his cock, she thought of Goldilocks and the Three Bears. His cock wasn’t too big, and it wasn’t too small. It was just right! She even thought his cock was handsome, if cocks can be handsome.

Taking his rigid dick in her mouth, she seemed to be tentative, so he asked her if she could put it in further. She did the best she could, trying not to gag.
George turned her on her back and tongue-fucked her pussy. “Oh, you are delicious,” he whispered. Smothering oil on her body, he kneaded her breasts, occasionally pinching her nipples, sending waves of pleasure all through her young body. Then he rubbed oil on her shaved pussy, penetrating her slit with one and then two fingers, making her hips buck and sway.
“You don’t mind if I cum inside you, I mean, you’re OK with a creampie,” he said as he shoved his cock all the way in as deep as he could go. She wasn’t in the mood to object. Anyway, she loved the warm, thick fluid that poured into her.
His vigorous thrusting had lasted only a minute or two, blasting her cunt with shot after shot of hot creamy cum that began to dribble out of her cunt as soon as he pulled out. Scooping it up with his fingers, he slipped it in her mouth. She had learned to like the taste over several months with her boyfriend, Darrel.
When he caught his breath, George said, "Oh, that was great, Amelia. How about you?"
"Well, George, it was fun while it lasted. By the way, my name is Amanda. Amelia was the famous pilot."
"Yeah, right. Look, maybe we can get together again."
"Sure," she said, "and maybe you can last longer the next time."
George didn't ask how much she charged. He said he had never paid for sex, but he wanted to give her a present. He said he would call her again after getting back from an out-of-town sales meeting.
George drove Amanda home with two hundred dollars in her purse. The next day, she deposited the money in a new savings account. It was a start, and it wasn’t the first and only time she fucked George. They met off and on over the next several months. She called him her fuck buddy. He called her his Barbie doll.
*
Salvatore, or Sal, as he liked to be called, met her at school at lunchtime. Her afternoon was free because of a teachers' meeting. He was gruff and only wanted to brag about how many girls he screwed. She told him to fuck off, and she wasn’t interested in being added to his fuck list.
"Don't get uppity with me, Doll," he told her. "I don't know what you call yourself, a sugar baby or a gold digger, but whatever it is, they’re all euphemisms for a whore."
She started to cry.
"Look," taking his wallet out. "I'll make it worth your while, slut" and showed her five hundred dollars. "I'll give you two hundred for the first fuck and three more if there's a second one. And that ain't nothin' to cry about."
Sal took her to the Duck Inn, not far from town. The Inn had a well-known reputation, known by the kids at school as the Fuck Inn. Sal had a cock as hard as a steel pipe and balls the size of two ripe plums. There was no foreplay with Sal. He plowed into her, changing positions every few minutes. He just wanted to bang her fast and furiously. After finishing the first time, Sal said she was a good fuck and he hadn't gotten laid for a while.
"Why is that, Sal? You told me about all those girls you fucked."
"Well, that was before they put me in the can."
"The can?"
"You know, the slammer, the pokey."
"What for, Sal?"
"Armed robbery."
That's when it dawned on Amanda that she might be getting paid with hot money.
The second time, Sal didn't slow down. He was roughly fucking her like before.
Sal dropped her off back at school with cum trickling down her thighs. It wasn't a great experience, but she had five hundred dollars to deposit in the bank.
*
Her third sugar daddy, Philip Williamson, was a criminal lawyer. It was a longer-term relationship. They first met at his law office for a test drive. She gave him a blowjob for what he called a retainer. They met the next week for dinner, then he took her to a private dock helping her step into his yacht. They shared a bottle of Champagne before going below deck to the bedroom. The lights were dim, and soft romantic music played in the background that put Amanda at ease. It wasn’t until they were naked side by side that Amanda began to feel a surge of excitement.
Philip knew how to use his hands and fingers. He was an expert pussy eater. “I see you are not a virgin,” Philip said after licking her into an orgasm.
“Is that a problem? she cooed.
He laughed. “Look, I like young girls with experience.” Pausing, he then added, “But not too much experience.“
They both laughed at his implicit remark.
“My first girlfriend was a virgin, and all she did was cry the first time. Then there was Patricia, who showed me the stuff that dreams are made of.”
“Humphrey Bogart, right?”
“Ah, you saw the movie.”
Her anticipation was intense as she opened up her legs for him. His thick manhood made her squeal as it stretched her tight, wet fuck hole. Philip took his time and moved carefully filling her slippery cunt as far as he could go. At some point, she felt an urge for more. She cried out, “Fuck me, Philip! Fuck me hard. Deeper, deeper, fuck me with every inch of that fat cock.”
He didn’t need to be asked twice.
Philip pulled back as if he was pulling out, then forcefully plunged back in, pounding her into repeated orgasms. She was sure they were literally rocking the boat.
Amanda’s affair with Philip lasted for a month. He gave her an allowance of three hundred dollars for each of the four times they met. Adding the twelve hundred dollars to her savings account was enough to buy insurance.
After Philip, Stephen had no sugar daddy friends left, but suggested she go online to the Sugarbaby.com site, where she could be selective. The downside was that many of the potential clients lived out of town, although now she could borrow her mom’s car. Refining her search based on location, she found local men who added to her bank account. Now she was saving to buy a car.
Charlie was her second online sugar daddy. The first guy from Surgarbaby.com was a total loser. There was no dinner, not even a motel. He fucked her in the back seat of his car like a couple of teenagers. He was cheap, too. He gave her $150 and a hickey.
Anyway, Charlie was a lot of fun. She borrowed her mom’s car, and they met at a motel in the suburbs twenty miles from the city. It...
