Homeless Prostitute to Million Dollar Playboy Bunny

Prologue:

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.

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2. Back In Time

We decided to go out on the deck to talk about my life, likes and dislikes. The deck featured a large in-ground pool, a big hot tub, barbeque area and an entertainment area. We sat on chairs under the sun-roof and drank some fruity drinks. “It’s kind of a long story to tell” I said. “Don’t worry Elena, I’m not going anywhere” Adam said, smiling. “It all started seven years ago. I was 15 years old at the time. Living in New York was a dream, busy streets as always. But, living the dream in New York was far from what was going on at home. My parents always fought; fighting about the littlest things which seemed to hurt me even more. I was abused by my father – not just physically but mentally as well; only my mother cared about me. She told me everything was going to be alright and that we’ll be free from him. Every day, I thought about what my life would be if I hadn’t been found sooner. I was upset and never happy. I hated myself for not fighting back. I was depressed and didn’t want any help from anyone. I ran away from home with a few bags. One of the bags had spare clothes, bathroom utensils, food and bottles of water, entertainment things and a blanket and pillow. I also carried a medium-sized bag with detachable straps. Inside the bag was my wallet with some money, my phone, a small pepper spray bottle, breath mints and a bag of make-up. When I ran away, I was wearing dark blue skinny jeans, short-sleeved t-shirt with a cross print at the front, a pair of black leather boots and a long, black cardigan”. Eleanor took a sip of her drink and continued.

 

“So, what did you do when you ran away?” Adam asked. “I found an empty building with opened doors and furniture in them. I went into one of the rooms and the one I went into had a computer for registry for a room and own bathroom. The cost for a room was $3.50 per week ($17. 50 total). I took out my wallet and checked the amount of money I had. I had about $756.85. This is because I saved up my money for something special like a pair of new shoes or a new electronic in the future, but since I ran away from home, I had to use the money to survive. I decided to stay in one of the rooms for 5 weeks. In the room I chose was No.7 was a single bed, a wooden desk with a chair, a bookcase and a large, round light on the ceiling. I separated the money to organize the plan I was making: $25-$30 on food and water, $250 for emergency, $150-$200 for transport and the list goes on. After 5 weeks in the building, I packed my bags and paid the stay then left the building in search for a place to stay again. A month went by and I found a couple of places to stay for a cheap price not over $5. I then found a flyer for prostitution to earn money (approximately $350-$500 three times a week). I knew doing this wasn’t a good idea but I was running out of options. I went into the empty alley and began changing into my mini strapless sundress and a pair of ballet flats.

 

My first customer was a man in his 20’s and he gave me $25 for 10 minutes. He came back for more for another few years and told me that he’ll tell his co-workers about it. He told me I was really good; even though I was 15 years old. When I told him my age, he was really excited. I guess that’s what he was looking for … I then started getting a lot of customers since after my first. The customers had escalated, so did the money and the pressure I was on’.

 

“So, you started prostitution?” Adam asked who was a bit confused sipping his drink. “Yeah” I said, looking down. “Hey, it’s okay. No need to worry. I have a few friends who had rough patches in their lives and I’m totally fine with that” Adam said, smiling. Eleanor smiled a bit. “So, how did Hef found you?” Adam asked. “Well, after being a prostitute for the next two years and five months, earning hundreds and hundreds of dollars as I continued, I went to the local bank called Rolland’s Bank and deposited the money. I knew with the money, when I finished prostitution, I would buy a house and live a normal life again. When I was in the alley of afternoon and eating some food and drinking some water, a long, black, stretch hummer parked in front of the alley. A man in his 70’s stepped out of the stretch hummer and looked around until he saw me. He was smiling. Kind and a warm looking face. He walked up to me and said ‘I could give you a lifetime opportunity to live with me in the Playboy Mansion. You can introduce yourself to the girls in the mansion as we turn you from Homeless to a Bunny’. I thought about it for a moment and accepted his offer. I gathered my things and went into the car. Everything was so shiny.

 

The next thing I knew, my things were placed into my room and I was hauled into another room with three girls. They were Kendra Wilkinson, Melissa ‘Mel’ Halt and Lucy-Anne Peterson. They began doing my make-up, hair, outfit, you name it. They made me look pretty on the outside as well as on the inside. They taught me how to apply my make-up, do my hair, what item of clothing matches; it was like a cycle of long words. The new look gave me confidence and I’ve lived here in the Playboy Mansion ever since. Since then, I’ve been featured in one of the Playboy magazines as the New Face in the Mansion, It Girl and Sweet as Pie”. “That’s a great story. My parents never got along either, so I know how you feel” Adam said. Eleanor nodded. “We should get back” Adam said. “Yeah” I said. We turned back and walked off smiling.

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