Her Bright Future

There was no one in her class at Barrington Preparatory Academy was popular as Wendy Willery. Head Cheerleader (a close race, a narrow win over Cheryl Schwab), president of the debate club, presumptive homecoming queen, and definitely the highest rated GILF of her class. 3.9 GPA and an early acceptance to Stanford with a well-funded 529 account her parents had established to fund her full ride at college, Wendy was going into senior year at the top of the curve. She was the envy of every girl in her school. Her future was so bright, she had to wear shades.

Of course, her life wasn't perfect. There was the escalating animosity between her parents, the endless shouting and arguments. Wendy couldn't wait for senior year to be over and her escape to college.

And then there was the threat of embarrassment hanging over her head, a threat her mother seemed not to care about. Coming home from work early one day, Mom had found Daddy dressed up in her clothes, complete with wig and makeup. That started the endless shouting and recriminations.

And while so far no one at school had mentioned it, her mother had gotten drunk at the country club last night and lashed out at her father, announcing to the club that he was a nancy boy who had stretched out all her good underwear. Wendy's father had shouted the night before that he looked better in her clothes than she did, and her mother just couldn't let that go. So, she retaliated with the public humiliation.

Her father was strangely quiet when they came home, refusing to engage her mother in argument or in conversation. That went on for two weeks, and then Wendy's father disappeared.

At first, Mom said, good riddance, but when a week passed and the bank began calling about bouncing checks and an upcoming mortgage payment, worry set in. It turned out that Wendy's loving father had refinanced the house to the max and had emptied all their bank and investment accounts, before he disappeared. He'd even emptied Wendy's 529 account.

In a panic, Mom called their accountant, who promised to come by that evening, as a friend. He made it clear that the mother could no longer afford his professional services. When he came by that evening, he let Wendy and her mother know the full extent of their financial standing. All accounts had been emptied of all the money except $50 each, and further, if the husband couldn't be found, the wife was going to be responsible for the taxes on all the deferred accounts: the IRAs, the 529, and the other retirement accounts. Plus, their house was likely to be repossessed in the not-too-distant future unless the family could find the funds to bring the new mortgage up to date. Plus, the balances on their credit cards were also overdue and subject to almost 30% interest.

Wendy was crushed. No 529 meant no Stanford. Mom was crushed. How could they survive? She'd never had to work, never had a job. She'd gone from her Daddy taking care of her to her husband's care. Now both sets of Wendy's grandparents were gone and the inheritances they'd left had been in the investment accounts that were now empty.

In the end, their accountant friend made a deal with the bank -- in exchange for voluntarily vacating the property, saving the bank the time and expense of foreclosure, they would vacate the balances on the credit cards. That was the best he could do. He hinted that if Mom was a little friendlier, maybe he could help with some of the other bills. Mom declined.

The reality set in when Wendy's school contacted them about the second semester's tuition. They couldn't afford it, and they couldn't afford to live in the public school district she would have attended otherwise.

Her mother had lorded her position over their "friends" at the country club; "friends" in quotes as her mother's self-declared superiority had alienated those same "friends." No one stepped forward to help them in their distress, and humiliated, her mother refused to reach out. They relocated to the city in the next state to the east where Mom's cousin agreed to put them up while they looked for a place of their own.

That lasted less than two weeks. When her cousin (actually, stepcousin, as it was then pointed out) learned that they didn't have any money to contribute for groceries or rent, they were asked to leave. After three nights in their car (Wendy's five-year-old Toyota Camry -- all the other cars had been repossessed), they finally found a pair of beds in a homeless shelter. Their first night there, Wendy's shoes were stolen. The charity that ran the shelter was able to find an old pair of tennis shoes for her to wear, a well-worn and dirty pair. Wendy had stoically been holding back her tears at the sudden downturn in her life but having to wear filthy secondhand shoes was the last straw. She broke down and wept uncontrollably.

They'd been assigned a social worker, who helped Wendy register for the local public high school and apply for the local state college. She had less than a year to find the almost $18,000 per year that even the state college would cost, not including living expenses. It seemed impossible, but Wendy was determined to get a college degree. She'd find a job and earn the money.

School was a nightmare. The classes were disruptive, the teachers either incompetent or uninterested in their students, and in the heavily diverse student body, the spoiled white girl faced daily bullying. She was pushed and shoved, cornered, then groped and pinched almost constantly, both in the hallways and in class. She was pressed between two brutes while they talked about her possible rape. Girls appropriated her sweaters and jackets. The teachers didn't seem to care.

Her grades immediately suffered. Her books were almost unreadable, covered with obscene graffiti and filthy limericks, bad penile drawings, and graphic suggestions. In those classes where the teachers did attempt to instruct, she was constantly distracted by attacks on her person. In despair, Wendy dropped out of school and applied for a GED, which she had no trouble acquiring. The move also gave Wendy the ability to work full-time, to earn the money for her college fund.

The only job she could find near the shelter was at a fast-food joint, taking orders in the drive-thru, for minimum wage. Even working full-time, after taxes, she was barely bringing home $500 per week, half of which she had to give to her mother to help with food and clothing costs, as they looked for an apartment of their own. Then, she had to pay her car insurance and gas costs. Her tires were worn and soon she'd have to pay to replace them. At the rate she was going, her college fund would take at least two years to fully fund one year's tuition.

But then Mom met Mitch and after several dates, he offered them a room in his apartment. Wendy and her mother had to share a bed, but it was rent free, so her mother was able to allow her to put more of her take-home pay into her college fund. Wendy didn't like Mitch; he was far too smarmy with his soul patch and pastel jackets that were reminiscent of the old Miami Vice show. He thought himself way too cool, and Wendy thought he was too young for his mother. He was at least 10 years younger than her mother's 39 years. He was almost closer to Wendy's age than her mother's.

But within two weeks of their moving in, Wendy found that she had the bed to herself. Her mother was now spending each night with Mitch.

Within a month, Wendy's mom had quit the retail job she had. She explained to Wendy that she was helping Mitch with his business. Wendy asked what his business was, but her mother responded vaguely that he was in the entertainment business. She acted as his hostess when he had to wine and dine clients who came to town. Her mom told her that Mitch was paying her a wonderful salary, as well as continuing to cover their rent and expenses.

Wendy couldn't afford college when the semester started. She needed to put it off another year, while she worked in misery at the fast-food restaurant. She felt like she was moving backwards. Just over a year ago, she was starting her senior year with a bright future. Now her foreseeable future was, "Do you want fries with that?" Her 18th birthday had come and gone, unnoticed by her mother and the world at large.

Feeling dirty from the job, her hair stringy with the greasy air from the cooking burgers, her skin threatening to break out from that same grease, Wendy hated her job. But with her mother relieved by Mitch of the day-to-day expenses of living, and earning enough money for herself, Wendy was finally able to put more of her money into her college fund. But doing the math, even at a state college, she was going to miss more than a year before she could start, and then she wondered how she could afford the succeeding years.

She was sitting on her bed, adding up her deposits and teary eyed as she projected the total she could expect when tuition was due. As she threw herself on her bed with a sob, Mitch stopped at her open door.

"What's wrong, kid?" he asked, leaning on the door jamb.

Something about the way Mitch filled the doorway made Wendy uncomfortable. She sat up. "Where's my mom?" she asked.

"She's out entertaining clients." Mitch replied with a smile.

That didn't sound right. "Alone?" Wendy quizzed.

Mitch smirked. "Sometimes it works out better that way. So, what's wrong."

Wendy decided the quickest way to get rid of Mitch was to answer his question. "I don't think I can earn enough money to cover my first year at college, let alone four years."

"I could help." Mitch smiled at her. "You could work for me, instead of flipping burgers."

"I don't flip burgers," Wendy quibbled. "I man the order station."

"Well, excuseeeee me!" Mitch performed a Steve Martin impression. "Still doesn't make you enough for college, does it?"

Wendy shook her head. She asked, "What is it you do? Exactly?"

Mitch shrugged. "Mommy didn't tell you? You don't know what she's doing for me?"

"She said you were in the entertainment business, that she's your hostess when clients come to town." Wendy could tell by Mitch's expression that he thought that was funny.

"Sweetheart, I run an 'escort' service." He chuckled. "Your mom's one of my escorts. Some guys like an older lady with a little class. Your mother has that in spades." His eyes roamed over Wendy's figure. "So do you, honey. You could really make some dough."

"My mom's an, Mom's an, huh, escort?" Wendy said, unbelieving, but with a niggle in her brain that thought it explained a lot. "Does she, uh, uh, have sex?"

Mitch laughed. "Well, you already know that she's screwing me for the rent, right?" He shook his head at Wendy's shocked expression. "What did you think? That I'm just a generous guy?"

Bewildered, Wendy mumbled, "Mom's a whore?"

Mitch said, "Well, as far as I'm concerned, she's an escort. What the ladies do with the clients beyond that is none of my business. But she's getting a lot of repeat business, and not just from out-of-towners."

Wendy's brain was flying around at a thousand miles per hour. She couldn't get a thought to form, her mind racing away from the thought of her mother, prostituting herself. Not her mom!

When Mitch repeated his offer to Wendy to go to work for him, she jumped off the bed and pushed him into the hallway, closing and locking her door. Then she fell across her bed and wept for her mother, cursing her father for leaving them in this predicament.

It was two in the morning when Wendy was awoken by a tapping on her door. "It's me, honey." Her mother tapped on the door again. "Can we talk? Please?"

When Wendy opened the door, her mother was dressed for an evening out. She looked elegant in an evening dress that Wendy had never seen before, and which she knew hadn't accompanied them when they had moved into the homeless shelter. Her mom saw her looking at the dress and stood back and posed. "Like it? Mitch bought it for me?" Her smile faltered when she saw Wendy's look of disgust.

She rushed forward and gathered Wendy into her arms. "I'm sorry, honey, but I had to get you out of that shelter. It broke my heart when they stole your shoes. We had to have a better place to live, a better life, where you could go to college and have the life you were meant to have.

"This was the only way. I don't have any marketable skills, and as Mitch pointed out, as far as your father was concerned, I was just a whore he paid to have sex with and to cover his perversions." She wiped her eyes with the back of her hand. "If he'd felt any other way, he would never have left us, never have left us with nothing."

"But, Mom, a..." Wendy couldn't bring herself to say whore or prostitute, "an escort? You're an escort."

Her mother laughed as she wiped her eyes again and smiled ruefully at her daughter. "It's not that bad, sweetheart. Most of the guys are nice and clean, and," she hesitated for a moment, "I never realized what a terrible lover your father was."

Shockingly, Wendy began laughing. Her mother looked surprised, then joined in. "Look, sweetheart, maybe I'll meet someone who'll take us away from this. I was never going to meet anyone at the grocery store, so at least I can hope." She hugged Wendy. "And hopefully I'm earning enough to send you to a college you deserve to go to. I don't know if my ass is enough to get you to Stanford, but I'm trying, sweetie."

Wendy sobbed and pulled her mother into a fierce hug. Her mother was whoring herself for her. Did that make it right? The love her mother had to have for her to do the unthinkable must be overwhelming.

The two women hugged for a while, when her mother disengaged herself, saying, "I've got to go. Mitch is waiting for me." She kissed Wendy's forehead and exited the room.

That night Wendy stayed awake, assessing the situation she found herself in. She couldn't fault her mother -- she wouldn't fault her mother. But she couldn't let her mother carry the burden by herself. She would help. With two of them, Wendy thought selfishly, maybe Stanford wasn't an impossible dream.

The next day, Wendy approached Mitch while her mother was shopping. "What would I have to do, Mitch? What would it pay?"

Mitch smugly smiled. "You'll get a $400 per date, plus any 'tips' the client might pay for additional, um, 'services.' If you do as well as I think you will, you'll soon be in demand, and you could double that fee fairly soon. What do you think?"

"I think if my mother's willing to do this for me, I should be helping her. Between us, maybe we could afford Stanford. When can I start?" Wendy was determined to move forward. Getting out of the fast-food industry would be the icing on the cake.

"Whoa, hold the horses. First, we must see how well you can perform." Mitch's eyes swept slowly over her body. "Your mother's got an overnight client tomorrow. You can spend the night with me. Think of it as an audition."

"But," Wendy said in a rush, "I thought you said that your girls didn't have to have sex. I thought I could just be an escort, without being a whore."

"Yeah, well, no." Mitch shrugged his shoulders. "You don't have to, but I must make sure you're able to, you know, represent my brand in the appropriate manner, if it comes to that."

Wendy looked down in despair. "But I can't. I never have. I couldn't"

Mitch's eyebrows flew up his forehead. "What? You're a virgin? But your mother said you were a cheerleader, a really popular girl? Who are you kidding here?"

"No one. I'm not kidding." Wendy slumped down. "I've never had sex. I did give a couple of guys blowjobs, and a few handjobs. Other than that, I never gave it up. I wanted to save it for marriage."

Mitch laughed. "What a waste. You gonna save it like your mother did? Waste it on some guy you think you love?" He laughed again. Then he stopped.

"Hey, you want to make your first year's tuition in one night?" Mitch looked thoughtful. "If you're willing, we could auction off your hymen. It's fucking amazing what some guys will pay for that."

Wendy rushed back to her room and locked her door. She should have known that sex was what it was all about. Mitch was just a pimp, no matter what he said.

Wendy heard her mother return from shopping and heard her and Mitch whispering. Soon, her mother was tapping on her door. When she opened the door, her mother drew her into her arms. "I'm so proud of you, Wendy. I can't believe that you're still a virgin."

Wendy buried her head in her mother's breast and nodded. Her mother hugged her and then held her at arm's length. "Mitch says you want to earn enough for Stanford?"

Wendy laid her head back on her mother's bosom and nodded again. "But I don't want to lose my virginity." She raised her head and looked into her mother's eyes. "I really don't want to become a whore my first time. I always dreamed it would be with someone I really loved; my husband!"

Wendy felt her mother's hand on her head, pulling her back to her chest. They quietly hugged for a moment. Then her mother spoke.

"But honey, Mitch thinks you could get more than $10,000 for your first time, maybe more." She paused. "It'd really help us get you the tuition you need. And he thinks we could sell it a couple of times, if we do it right.

"Of course, Mitch would take his 20%."

"20%? But Mitch said he had nothing to do with what went on between the girls and the clients." Wendy exclaimed.

"Don't you believe it. The only thing Mitch doesn't get a percentage of is any tips the client leaves. All the other fees go through his escort service, and he gets his 20% off the top." Mom sat on the bed and pulled Wendy down next to her. "This could really help us get your tuition. Maybe not enough for Stanford, but we could get you into a much better school than that state college."

The next day, Mitch greeted Wendy in the morning. "Well, what do you think? You want to get to Stanford or not?"

"Okay," Wendy replied without enthusiasm. "I'll sell my virginity." She felt like weeping when she said it. But she held it in, determined to do whatever it took. As her mother was doing, for her. "So, what do we do now?"

"Well, first you'll call in and quit that shitty job you have." Mitch smiled, "Then, since your mother's going to be gone tonight, you'll spend the night with me."

"But," she protested, "I thought we were selling my virginity."

"Just your vaginal virginity." Mitch smirked. "You'll give me your other virginity tonight. That one we can sell again later. The client won't know the difference. We could probably do it a few times, if you can act at all." He laughed. "It doesn't take much to fool these guys."

"Why? Why do I have to sleep with you?" Wendy teared up in frustration.

"Because, sweetheart, if I'm going to put together an auction, I have to be sure you're going to deliver the goods when they're sold. And the only way I can be sure of that is to have you deliver the other goods to me, tonight." He stood up and kissed her on her forehead. "I'll take you to dinner at 6:00 o'clock, and then we'll come home to the main event. Be ready at 5:45." He stopped at the door and looked at her. "You might ask your mom for some lube. If she doesn't have any, you might want to buy some. I think you'll regret it if you don't. Oh, and get a couple of prepackaged enemas. I'll give you a complete course in anal intercourse after dinner. Ta-ta!" He went out the front door, still laughing triumphantly.

Her mom not only provided both the lube and the enemas, but gave Wendy some important pointers, along with a medium sized dildo. She recommended that Wendy spend some time during the day lubing her rectum and the dildo, practicing with it. She should stretch herself out some and become acquainted with what approaches and angles were most comfortable for her.