Author's note:
Although the idea is clearly inspired by a certain Disney Channel sitcom, I've never cared much for the show (or its star). But I've always been intrigued by the idea of someone having to keep a secret identity (probably from all the superhero comics I read as a kid), and by the question of just how far—sexually—someone could go and still retain their wholesomeness and innocence.
Those of you wanting to get right to the sex, there is masturbation in chapter 3 and the actual sex is in chapter 5. Otherwise, please enjoy the character background and story development in the other chapters.
Although I have been a Literotica fan for years, this is my first submission. Constructive criticism is welcome.
Standard disclaimer: All sexual activity depicted in this story is performed by consenting adults.
Finally, this story is dedicated to the memory of my grandfather. About twenty-five years ago, in his seventies—with help from the pastor at his church—he came to realize that his favorite phrase of "God doesn't make mistakes" applies to people who were born lesbian, gay and bisexual.
Enjoy.
*
Chapter 1 -- Riley
Riley May was miserable.
Back in the early 1990's, her father Bobby May had recorded a song that became the number one country hit in America. In those days, the only way people could listen to the song at any time they wanted was to buy the album, so that's what lots of people did. The recognition he gained from his one hit song was enough for him to be offered roles in several TV movies and eventually a series. And the money he made from CD sales was enough for him to buy a mansion in the Hollywood Hills with cash. He installed a recording studio in the basement so his acting duties wouldn't conflict with making music.
Years later, Bobby was struggling to find another hit. He had one of Nashville's biggest producers in the basement studio and they were working on a tune by one of the most talented songwriters on Music Row. But it just wasn't clicking. Between takes, his nine-year-old daughter Riley asked if she could try singing it once. Bobby and the producer were feeling generous that day, so they let her, and she belted it out like a pro.
And that's when they knew they had a star on their hands. Bobby quit singing to become Riley's manager. However, he was also a protective father, so he insisted that Riley still attend regular school, only record on weekends, and only tour during the summer break. He also insisted that she use a fake name and wear a disguise onstage so that even her friends wouldn't know it was her. Through his TV contacts, Bobby knew people who could make a blond wig for his auburn-haired child that looked just like real hair, even close up. And together, Bobby and Riley came up with the name "Anna Louisiana" after Bobby's native state.
Over the next nine years, "Anna" became a superstar among elementary and middle-school-aged girls. She was never without a song on the charts for more than a couple of months at a time. Her formula was simple: catchy pop tunes with G-rated lyrics that made Taylor Swift's early material sound sleazy, along with music videos showing her wearing pretty clothes.
Riley never cared for the restrictions that were placed on her. She wished she could record under her own name and let her friends know who she was, but she understood. Growing up in Hollywood, she saw too many teen stars unable to make the transition to adulthood without succumbing to dangerous temptations. And when Michael Jackson died, her father told her all about how Michael had never had a real childhood because he was touring all the time, which led to addiction and bizarre behavior during his adulthood and his premature death at fifty years old.
But this was not why she was miserable. She was miserable because she was a lesbian and had to hide it. Although her father was not a fundamentalist by any means, he was a devout Christian and believed that homosexuality was a perversion and a sin against God's order. Plus, her best friend Jillian came from a strict fundamentalist household, and if Jillian's parents ever found out about Riley's sexual preference, she would never be allowed to visit her again.
What made it worse was—as she was nearing her eighteenth birthday—she was developing a crush on Jillian.
Chapter 2 -- Jillian
Jillian Prescott was miserable.
Her parents Ben and Heidi had met at Berkley when both of them were radical leftist atheists. They had two main goals in life: to rid the world of capitalism, government and religion; and to have children who would continue their work after they were gone. They moved to L.A. to be near what they saw as the nexus of the evil capitalist media empire, and immediately worked on having kids. But after years of trying, their doctor told them Heidi was infertile.
Rather than giving up, they channeled their anger and frustration into their political work. But they were so strident that they wound up alienating many of their fellow leftists.
And then, one day something amazing happened: Heidi got pregnant. And the only explanation anyone could give was that this was a miracle. Since Ben and Heidi's rigid ideology did not allow for the existence of miracles, they began to rethink their positions on all sorts of issues. Rather than come to the sensible conclusion that no ideology can be made to conform to how the world actually works, they instead adopted a diametrically opposed dogma: Not only does God exist, but the Bible must be interpreted as a literal document. Instead of radical leftists, they were now extremely conservative Republicans who wanted to take America back to a time when God reigned supreme, women submitted to men, and sex was not talked about in public. They immediately got married and Ben decided to study business and started his own company. At first, they wanted to move away from L.A., but couldn't afford to do so. Then, as Ben's business became more successful, he stayed in L.A. to keep his customer base.
They raised Jillian under very strict supervision. During her elementary school years, they couldn't find a religious school they could afford, so Jillian was homeschooled. By the sixth grade, she had become so advanced in math that her mother couldn't teach her anymore, so they relented and let her attend a fancy private school with lots of other rich kids, but only on the condition that she never go to her friends' houses unless they went with her. Well into high school, she was still not allowed to watch TV by herself or choose what clothes she wore. When she showed an aptitude for math, her father told her "You will make a great helpmate to some lucky man when he decides to go into business." When she asked why she couldn't go into business for herself, her dad said "That's not God's plan for women."
All these things made her unhappy, but what really made her miserable was that she was a lesbian and her parents were deeply homophobic.
It started out when she was nine and Anna Louisiana first burst on the scene. Most of her friends wanted to be just like Anna. Jillian did too, but it went deeper: She wanted to someday marry Anna and have babies with her. But she had never heard of a girl marrying another girl. So, one day she asked her father "Daddy, can two women marry each other?" And her father went ballistic, ranting on and on about the sodomites and how they would all be cast into Hell. Jillian knew if she asked further, she would get a beating with the belt, so she never brought it up again.
By high school—despite the fact that she was exempted from sex education classes—she had figured out what lesbians were and that she was one. But there was nothing she could do about it. By that time, she was basically only allowed one friend at school: Riley May. And that was because Riley's family was the only other family at that school who attended church regularly. Granted it was not the same church as the Prescott family (and Jillian's parents secretly thought the May family were doomed to Hell, just not as bad of a level as the rest of the kids at school). Because Riley's dad also disapproved of homosexuality, Jillian knew not to bring it up with Riley either.
And that really hurt because Jillian was having feelings for Riley beyond friendship.
Chapter 3 -- The Party
One week before her senior year in high school began, Riley turned eighteen. She and her father decided to host a pool party in their backyard. Bobby said Riley could invite anyone she wanted, but the stipulations were no alcohol, tobacco or guys; or—as the invitations read— "no booze, no butts, and no boys". Riley was excited as the last Anna Louisiana tour was really grueling. She needed an excuse to hang out with her friends and be a normal teenager again, if only for a few hours.
Riley invited all her friends but was worried about Jillian. The other girls teased Jillian mercilessly for all the rigid rules her parents made her follow and for the fact that in many ways, Jillian had never grown up. While most of the other girls in school were into R&B or hardcore hip-hop, Jillian still listened to Anna Louisiana. And Jillian was not allowed to drink, smoke, use drugs, swear, talk about sex, go on dates, or watch movies not rated G or PG.
Riley also didn't drink, smoke or do drugs. And—not wanting to date boys—she also made the excuse that her dad didn't let her go on dates (not quite true, but he did say Riley needed a chaperone). But because Riley was pretty, outgoing and popular, she was able to get away with "quirks" that Jillian wasn't. And when people did tease her, Riley had a loving supportive family structure, unlike Jillian. Therefore, the insults didn't really hurt her self-esteem.
The party had been going on for an hour when Jillian finally showed up. While Riley and all the other guests were wearing bikinis, Jillian was wearing an old-fashioned one-piece swimsuit with a high neckline and a skirt around the waist. Still, that was much more revealing than what she was normally allowed to wear. Her parents were determined to keep Jillian a virgin until her wedding day, so they insisted that she wear conservative clothing at all times. Tops had to be loose and could not expose her collarbone or shoulders. Sleeves had to be at least half-way down her biceps, and she had to wear either loose slacks or dresses with skirts that ended below the knee.
Seeing Riley's well-toned arms and legs was a shock to everyone there—especially Riley, who couldn't help thinking that this was the most beautiful creature she had ever seen. She thought back to what this reminded her of, and she remembered an old movie she had seen on TV with her dad—something called "Vertigo"—where a beautiful young woman wakes up naked in Jimmy Stewart's bed. And Riley thought that right now, Jillian looked just like Kim Novak in that movie, but with her straight blond hair grown out just long enough to cover her ears instead of twisted into an old-fashioned bun.
Jillian didn't feel beautiful. She felt naked. She was surrounded by girls who made it plain they had no use for her. And just before she had left home, her father grabbed her by the elbow, pinned her against the wall, pointed an angry finger in her face and said to her "You *will* be home before sundown. I don't care that the law says you and Riley are legally adults. Under God's law, you're still my property until you marry a man I approve of. Do you understand?" If she didn't love Riley so much, she would never have come.
At 6:30 p.m., there was pizza and cake. Riley blew out the candles and started opening presents. Most of the gifts were cute clothes or various YA romance books and Blu-Rays. But Jillian's present stood out in Riley's mind. It was a bracelet: a simple pewter chain with a heart-shaped charm with the inscription "JP + RM = BFF". When Riley read the inscription, tears welled in her eyes. Right then, Jillian gave her a big hug and whispered in her ear "I love you."
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Hours later, after the party had broken up, Riley was lying awake in bed, the embrace still on her mind. Although it was completely chaste, it was still the most erotic thing that had ever happened between herself and another person.
Without thinking, she started rubbing her breasts. The whole time, she pretended that it was Jillian massaging her chest. Then she stuck her fingers in her mouth until they were covered with her saliva. She lifted up the loose tank top that she slept in and started rubbing her nipples, pretending her warm wet fingers were Jillian's tongue. That made her even more aroused, so she pulled down her panties and slowly started rubbing her clit, all the while still pretending it was Jillian's tongue working its magic. Eventually, it got to be too much, so she threw off the tank top and panties, played with her nipples using her right hand and sticking two, then three fingers in her vagina with her left. And the whole time, she kept fantasizing that it was Jillian licking her breasts and fingering her pussy. After a few minutes, she came. And at the point of climax, she swore she could literally hear Jillian whisper "I love you" in her ear.