Imagine you inherit a fortune from a family friend you never even knew. But what if there were conditions on your inheritance? And what if the other beneficiaries insisted you fulfill them? How far would you be willing to go to collect? Another brilliant story from Briana Vermont! Ten illustrations.
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For some boys, looking like a girl would be a blessing. For eighteen-year-old Sam Kent, however, it’s a curse. Already shy with girls, Sam can’t see how his girly looks can get him a date with his best friend Heather, on whom he’s had a crush for years. Heather sees potential in Sammy’s soft features, though, when her father’s country club announces an upcoming costume party. She’s sure that Sammy, dressed up as a beautiful bride, will win the $2000 Grand Prize.
A monkey wrench is thrown into Heather’s plans, though, when her brother Billy decides to blackmail his sister and her beautiful “girlfriend” into going on a date with and performing sex on him and his friend Alex. If they don’t comply, Billy will publish photos of Sammy at his feminine best to the Internet and ruin his reputation. Reluctantly, Sammy complies, not realizing that Billy has no intention of letting his sexual extortion end after one night.
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Jack’s stepmother tells him that she can’t afford to pay for his college tuition. He’ll have to go see his father, from whom she is divorced, to get the money. Jack isn’t comfortable with the fact that as his eye doctor father is now living as a beautiful woman. Having no other way to pay for college, Jack reluctantly agrees to visit his feminized Dad. The young man makes it perfectly clear that he thinks his father’s lifestyle is repellent. Jennifer, as Jack’s father is now known, is hurt by his nasty comments until she comes up with an idea. Perhaps Jack might begin to understand her attraction to femininity if he had the guts to spend a day as a young woman. Jack is persuaded to go along with this crazy idea, convinced that it will get his mother/father off his back and give him his tuition money. He discovers, however, that experiencing what a pretty young woman feels is a powerful drug, especially when people are complimenting you on your beauty and trying to convince you to become a fashion model. Strange new sensations overwhelm Jack when he kisses a man for the first time.
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In The Rack, Jean is assaulted and tied up by an unknown assailant. Dick takes the opportunity to ogle her helpless form instead of releasing her from her bondage. When she is freed, Jean vows to get even with both her attacker and Dick. Through guile and persuasion, she turns Dick into Dolly and recruits “her” to help her find the person who humiliated her. They form an unusual partnership and find an even more unusual love.
In Lovely Leading Lady, when Jack loses his job, he and his wife, June, worry about what will happen to their comfortable life. After some thought, June proposes that Jack allow himself to be transformed into Jill so that he can temporarily replace the girl who left her job at June’s government office. No one, including the reader, could ever guess where that simple if bizarre suggestion would take the two of them. One thing leads to another until June and Jill, still technically a heterosexual married couple, become national celebrities and Jill is a fantasy figure for many straight men.
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Poor Harry. He didn’t mean to cause an accident and kill the driver of the car he hit. Now the police are looking for him. Where can he hide on this tiny resort island? Harry thinks he is saved when the lovely and sexy Margaret offers to help him elude the authorities. Unfortunately, her “help” consists of disguising him as one of her maids, traditional uniform and all. Harry is trained in the feminine arts, including how to use his mouth to please Margaret and her co-conspirators, Norma and Clara. So convincing is his disguise that even his own sister doesn’t recognize him, but is it convincing enough to fool the wily police Inspector bent on finding and arresting him and the organized crime-involved family of the girl he killed?
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From the pages of history to today, a journey of passion and unleashed femininity….
“As I unbuckled the straps on my red plastic stilettos she cleared off the bed. My lingerie soon joined my dress and shoes on the floor. I lost track of time. When you are in heaven you don’t need a watch. Or in love either I guess. It was after midnight when we got up. I took off the wig and removed my makeup then I joined her in the shower. There was no conversation as we dried off and got dressed. After an experience like that nothing was left to be said.”
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“Do you remember when one of those jerks said I made him look bad? Well, it was because he realized he was mistaken about me; mistaken like you are now. Sure, I’m pretty and I’ve always been very girlish but I’m a boy, at least officially. Oh, I know I look like a girl but legally I’m a boy.”
That explained that strange sense of foreboding, that feeling that I shouldn’t be getting turned on by Teddy. Despite the prevailing values of the fifties I wasn’t about to bolt which surprised me. Maybe, on some level I realized that Teddy had, judging by the lines showing through his slacks, a penis in his panties. I should have been panicked but I still wasn’t going to run away from Teddy especially not since I noticed the tears in his eyes.
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A curious young boy. A beautiful and mysterious neighbor. When the neighbor takes the boy under her wings, she introduces him to the pleasures of the feminine life. Before long, his body responds to his new lifestyle and he begins to grow breasts, as if urging him to continue to pursue his new “hobby.” When the female half of a young couple becomes fatally ill, the boy is pressed into service as their baby’s wet nurse. Before she dies, she expresses the hope that the boy, who has maintained his female disguise, will take her place as her husband’s lover. Not realizing the boy’s true gender, Jim, the husband, starts to fall in love with the beautiful “woman” who has come into his life.
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“You’re a guy,” said Sean Unger as I sat on the end of my bed in my late mother’s rustling, blue, cocktail dress and slipped the blue high heels over my stocking feet, crossing my nylons as I did so. My brunette, pageboy hair flowed about my face and my earrings jiggled against my neck as I fitted the woman’s shoes to me. I could barely look at Sean, so afraid and nervous was I, as he studied my femininely made-up face. His eyes gleamed as he looked at the red lipstick I had chosen to wear instead of my usual, muted plum color.
“I won’t tell anyone,” I repeated to the boy who had kissed me so many times in the movie theater and told me that he had been waiting years to do that since he had seen me as a Good Fairy at his house on Halloween. “I won’t tell anyone if you don’t.”
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Bob blushed deeply once more and tried to hide it by bringing his cup of coffee to his mouth, feeling that Jennifer could read him like an open book. He managed to regain control and said in a rather meek voice, “But what am I supposed to do?”
“It is very simple really, you are going to assume all house responsibilities, cleaning, cooking, ironing, shopping like any housewife would do and both Anita and I intend to help you in the beginning. All you need is common sense and practicality and I know you have them both, after all you are an engineer,” Jennifer said quickly.
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