Homeless Prostitute to Million Dollar Playboy Bunny


The title says it all …

Fame. Fortune. Glamor.

Everything seems to be perfect. The perfect lifestyle. The perfect reputation. The perfection of being a beauty. But, I wasn’t like that before. Let me take you back seven years ago. The life I had as a homeless prostitute.

My name is Eleanor “Elena” Jacobson and I’m here to tell you my side of the story – on how I became a homeless person; but also a homeless prostitute. I will then tell you how my life changed and what made me become a Playboy Bunny.

(This story is suitable for 16+ only). If you are not 16+, you can read the other stories such as Bree's Special Encounter, Skylar Hanson: Sunset's Daughter (in construction) and If I Saw You In Heaven (in construction).

PS: This story is by far the darkest I've ever gone.


1. Rags to Riches

(As the author, if you get confused I may write Eleanor but everyone calls her Elena. Elena is Eleanor’s nickname).


It was Saturday morning. Sitting on my queen-sized bed with blue bed sheets with light pink flower print and matching pillows; feeling the warmth under the bed sheets felt soft and safe. Thinking about what I’ve done seven years ago, I felt sick in the stomach. Every day I wondered; not knowing what was going to happen to me, I let fate worsen by the minute. I didn’t appreciate on what I did for a living but it was the only way I could survive. Shaking the memory away, I got out of the bed and made the bed nicely. I then went into my automatic double wardrobe and picked out a glittering gold, short, ruffled skirt, a pink strapless corset, a pair of black stilettoes and a white diamond tiara. I added some gold and silver bling. One of the bling’s is my Playboy Bunny ring. I went into the bathroom and washed my face. I brushed my teeth. I put on black mascara, black eyeliner with wings on both eyes, and light purple with baby pink eye shadow, gold shimmer, a hint of light pink blush on my cheeks, light foundation powder and medium pink lipgloss. Combing my long, chocolate brown hair gently from root to tip, keeping my hair down untied. I looked at myself in the mirror and looked from head to toe. Noticing a huge different from the way I looked seven years ago to now.


I went to the living room and saw Adam Sawyer; who was standing near the living room door while holding a tray of drinks. Mariah Jenna who was talking to Melissa Halt about dreaming of being featured in a centrefold. Veronica May-Jaye Greyson was sitting on the sofa listening to heavy metal music. She’s like one of those Goth girls you call ‘emo’. Adam then noticed me and gave me a smile. I smiled back. Adam was pretty much my best friend. He helped me like no other person would have done for me. One time, one Valentine’s Day, from Adam, I received a boutique of red roses, a small stuffed teddy bear with a red heart on the middle which said ‘I love you’ and a Valentine’s Day card with a sweet poem. It was the sweetest thing that any guy has done for me. Then, there was Jake Hefner. Jake is the son of Playboy founder, Hugh Hefner. At 33, he still looks hot for his age. I’m surprised he hasn’t found a woman for himself. He flirted with me a couple of times but they never seemed to work because he comes too strong and he puts a huge amount of pressure on you to decide. Also, he uses the same flirtation strategy so that’s pretty much why it didn’t work. His charm does get the other girls to fall for him. Sometimes an hour or two and sometimes its just three whole minutes. He even had a try at the twins, Kristina and Karissa Shannon. The twins only took notice of Jake a few times when he tried but failed to do it for the 25th time, as they knew his antics would be the same. The twins are like the prize possessions of Hugh Hefner. Having twins is very rare at the Playboy Mansion so, in order for them to preserve their youthful skin and wow factor, they use lotion creams and eating a healthy diet.


Jake always planned good strategies onto get women he wants. He’s not my type and also the wrong age to be flirting with a girl 11 years younger. No matter how long he tries to flirt with me, he’ll never get my attention. I know it’s not cool to have a crush on someone that you can’t have. The one that I can’t have is Adam Sawyer. He’s so handsome. His short blonde hair, dreamy blue eyes and his amazing six-pack hiding underneath that white singlet top makes me feel good. Not in the way you think it is; but the way he looks. He’s so gorgeous. I know I said handsome before but, you know how it is, right?


I went into the kitchen to make some breakfast; making a wholegrain piece of toast with a spread of honey, some chopped banana in a small bowl and a glass of orange juice. I picked up a medium-sized tray out of the tray rack and placed the things on the tray. I took out a knife, fork and a napkin and placed those of the tray. I picked up the tray and took it to the dining area, putting down the tray of the white marble table and siting down on the comfy chair. I began slicing the toast with the knife and fork into two pieces. Wiping the fork on one side of the napkin for the chopped bananas and placing the fork on the tray. Picking up a slice of the toast and taking a bite out of the toast. It was a satisfying taste. Adam then came into the dining area and sat down with the tray of drink. He sighed. “Hey Adam, what’s wrong?” I said. “Miss Eleanor Jacobson. I’m very well, thank you” Adam said. “Adam, how many times do I have to tell you? You can call me Eleanor or Elena” I said, with a smile. Adam smiled. “Of course, Miss Elena” he said. “No, just Elena” I said. “Elena?” He said. “That’s better” I said, with a bigger smile. I took another bite of the toast and drank some of the juice. “Now, tell me what’s really going on or I’ll go get Jake for help” I said, about to get off the chair. Adam waved his and to me “No, no, no need for that. I’ll tell you, as long as you don’t bring ‘Mr Fancy Pants’ here” Adam said. “Don’t worry and I won’t tell him you said that” I said. Colette Lily walked past Adam and Eleanor with a large bowl of assorted candy. “Hey guys” Colette said, picking up a red snake and nibbling its tail. “Hey Colette” Adam and Eleanor said, together. “Bye guys” Colette said, waving and walking away. “Bye Colette” Adam and Eleanor said, together.


“Start talking” I said, drinking some orange juice. “I … Like you” he mumbled. “I like you too!” I said, blushing. “No, you don’t understand. I really like you” he said. “Yeah, I know” I said. “And, I really like you too, Adam!” Adam smiled. “But, I don’t know much about you. I don’t know about your life before the Playboy Mansion, what your likes and dislikes and such” He said. “Well, I could ask Hef if we could spend the day together getting to know each other. He’ll understand” I said. “Are you sure?” he said. “Of course, I’ll go ask him now” I said. Finished the last bit of my breakfast, wiping my mouth and hands with another napkin and walked up the stairs to Hef’s room.


Walking in were Kendra Wilkinson and Carmen ‘Red-Hot’ Hudson in the bed with Hef. Carmen looked at Eleanor with a fierce face and Kendra smiled at Eleanor. “Hey Eleanor, come to join with the girls, sweetheart?” Hef said. “Not exactly, Hef. I was wondering if I could get to know the butler, Adam Sawyer. I know I couldn’t continue unless I asked for your permission. You know rules first” I said. “Hmmm, alright sweetheart. It is time for you to get to know the other girls in the mansion and Mr Swayer too. He can have the day off. My son, Jake can fill in his job for the day” Hef said, with a smile. “Thank you Hef” I said, with a smile walking down the stairs as Hef said goodbye.


Adam picked up a drink from the tray and began to drink some of the mix. The drink tasted like lemon, orange and a hint of mango with a small splash of vodka and ice. He saw Eleanor coming down from the stairs and looked at her. “Well, what did he say?” he asked. “Hef said you can take the day off and spend the whole day with me” I said. “That’s good news” he said, with a smile on his face. “And, Jake is going to be taking your place as butler for the day” I said. “Even better news!” he said and an even bigger smile appeared on his face. I laughed. “Yeah, good news for you, rookie” Jake said, walking pass us. “Well hello …” “Save it, Jake. Not going to happen. Ever” I said, cutting him off. “One day sweetheart, one day I will have you” Jake said, winked at Eleanor and walked off holding the tray. “He’s annoying” I said, frowning. “Everyone in the mansion knows” he said. We both laughed.

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