My early life, growing up, was, as I look back now, perfect! I was the only girl with two, much older brothers. My parents were upper working-class with good jobs and incomes. My mom was a mail carrier and my dad was a truck driver, both military. My mom was in the Army and my dad was a code-breaker in the Air Force. I was spoiled, but I was humble and shy. My dad bought me my first car when I turned sixteen, a baby blue 1981 Chevette; I loved that little car. Back then, driving to school every morning, I felt so happy.
After graduating high school, I went to college the following fall. I and my baby blue Chevette were away from home and in the big city of Grand Rapids, Michigan. I lived with three other young women in a campus apartment and we all got along beautifully. I was there to study hotel/restaurant management, with no boyfriend at the time. I was determined to make my parents proud of me.
My roommates had part-time jobs to help supplement their income. My parents deposited money, weekly, into my checking account for my expenses.
After the first semester, my roommate, Rose, started acting differently. Every Thursday through Sunday, she started carrying a beeper; that was the technology we used back in the day before cell phones were invented. I would watch her, and it would start around 4:30 in the afternoon. Her pager would beep, she would look at the number, smile, and then disappear into her bedroom with the cordless phone. A few minutes later, she would be heading to the shower. When she came, out she was very sexily dressed with her hair perfect, eyes smoky, and dark mascara on her lashes.
Usually, she was wearing a black mini skirt, black, thigh-high stockings, and a low-cut, revealing, blouse without a bra. She wouldn't look at me or any other roommate; she simply picked up her purse and car keys and walked out the door. She was my roommate, so I would wait up for her. I needed to make sure she got home before I could sleep.
I would be reading, a tiny light clipped to my headboard, illuminating my book. She would smile warmly at me as she gathered her night clothes and went into the bathroom. I would turn my light off and roll over and drift off to sleep.
This would be our routine for the next six months. Her clothes became more expensive; she traded her old Chevy Malibu for a shiny red Camaro. She dropped a few classes but maintained her grade point average to remain in campus housing. I started getting jealous.
That little green monster would forever change my life.
I was waiting up late, for her, one cold October night, and she was later than normal. I heard the door unlock as she finally walked into the dorm. I was sitting on the couch, with a blanket tucked around, me reading. The first thing I noticed was the sparkle around her neck. She was wearing a diamond choker and the light made every diamond twinkle in the dorm lighting.
My breath caught, as she stood there in silence. Our eyes locked and she put a finger to her lips, “shhh,” as she mouthed, “bedroom.” I followed her into our room and shut the door. We sat on her bottom bunk bed and I saw her tiny hands were shaking.
She looked at me, took a deep breath, and said, “Please, Wendy, don't judge me. My father lost his job and my scholarship was cut in half. I needed money if I was going to stay in school.”
I didn't say anything for the next hour. I simply held her hand as she poured her heart out to me.
She had answered an ad in the school newspaper for an assistant for a lawyer. She figured it would be running errands, picking up dry cleaning, and such. She went to the interview and the woman was in her early forties—tall, beautiful, every bit the professional that Rose had expected. She had explained that she needed an assistant to handle different duties while she would be busy with clients or in court. The pay was $400 a day, with extra compensation if she needed Rose at the last minute. Rose was offered the job and started that same week. The job was perfect for the first six months, and then she started getting asked to pick up clients from the airport or go to dinner with both male and female clients. She was given a clothing allowance, a credit card, and a beeper.
Her first “client” was a famous actor who was flying into town. Her boss, Geneva, obviously not her real name, needed Rose to pick him up and "make him happy;" she would be paid $1000 for the effort. Rose accepted the assignment, and she bought sexy black thong panties, a black push-up bra, black stilettos, and a low-cut little black dress.
The limo pulled up to the airport fifteen minutes ahead of schedule. Rose was in the back waiting, as she had no idea who she was picking up. At exactly 9:30, the driver got out and opened the door. Rose, felt her heart stop when she realized who the actor was; it was a soap opera star, and she recognized him immediately!
He was friendly and introduced himself. He said, “Call me, Jack.”
Rose felt nervous but comfortable. The driver drove down by the river walk, pulling up to the valet station of a high-rise Merritt hotel. The valets opened both doors, and Rose watched as Jack tipped the driver and both men. He took his bag and Rose followed him into the hotel. He checked in, took her hand, and took the elevator to the penthouse floor.
When Rose is talking, she gets a faraway look into her eyes. She was reliving that first night as a paid escort.
The room had a view of the river. Jack moved her to the big window and stood behind her. He whispered, “You smell so tasty,” in her ear.
He felt her tremble as he caressed her arms, gliding down her hips. His cock pressed hard against her ass and she closed her eyes. In her mind, she was running through a field of daisies. He undressed her and the black dress slides to the floor.
Jack was an easy lover. He made her cum many times, but she was still running in the field of daisies. He called her a cab around midnight, then handed her $500 and thanked her. In the cab, she calculated her expenses for the next semester and decided to continue as an assistant to Geneva until she finished her degree.
We talked well into the morning hours. She told me that she was no longer an assistant as her contract had been bought out by a Sugar Daddy and that she now belonged to him, exclusively. He paid for her schooling, her expenses, and the diamond collar she now proudly wears around her neck. She mentioned that Geneva was looking for a new assistant since her contract had been purchased.
“Wendy, you would be perfect. You're a natural flirt, you love sex, and there's no commitment. I can set up the meeting for tomorrow. Say yes!”
My heart was pounding. The idea of not being financially dependent on my parents was so enticing. Plus, the euphoria of having sex with rich, powerful men was even more thrilling than the money I could make.
I shook my head up and down, and she hugged me tightly. “You won't regret this, Wendy.”
Famous last words!
I remember the meeting with Geneva like it was yesterday. My hands were shaking, my stomach was in knots. Rose had me wear one of her new dresses. It was lightweight, pink, had small rosebuds on it, and was low-cut. She made me wear a pink thong and a pink push-up bra. My breasts are big and the bra made them more glorious.
I was escorted to a corner office, where the receptionist knocked on the door, waited, and then pushed open the door. My heart practically stopped. The woman behind the desk was drop-dead gorgeous. She had this radiance about her, power, femininity, confidence. I'm not a lesbian, but I felt my panties getting damp, my pulse was racing, and my nipples grew hard.
Her green eyes never wavered as she smiled at me. She never stood up but just motioned with a slight tip of her head to the chair across from her desk. I sat down, legs together, trying to look calm and professional.
“Wendy, you are twenty-one, you just finished your associate's degree in management, and are now going for your bachelor's degree next, correct?”
My throat was suddenly bone dry, “Yes, ma'am, that's right.”
“Rose was my first assistant; she gave you a stellar recommendation.”
At this point, Geneva stood and walked around her huge desk. She walked to the door and locked it. She stepped back, sat on her desk, opened her legs, and showed me her perfectly bare pussy. She looked at me as she pulled her shirt up. I tried to look away.
Her voice was like a whip across the face. “Wendy, look at my pussy!” she said as she started to rub just inside the tan velvet lips.
I watched, transfixed, as she spread her cunt lips open. She was already moist inside, little beads of liquid caught the lights to glisten against her pink inner flesh.
“My assistant must be able to please both men and women, equally. A woman deserves the highest level of service as any man.”
She was rubbing her growing clit inches from my face, “Wendy, smell my pussy.”
I leaned in closer and inhaled her scent. My mouth started to water and I moaned out loud. I felt her hands in my hair. “Have you ever tasted pussy before, Wendy?”
I shook my head no. She looked at me and said, “Call me Madame.”
“No, Madame,” my voice was so soft.
“You will be my assistant, but first you will need training. Put your face in my pussy and lick it all over. Get me wet with your tongue.”
She pulled my head close and pushed her pelvis against my face. My tongue darted in and around her pussy as I found her clit and soaked it with my tongue. I tasted her liquid as she became more and more aroused. She was moaning when I sucked her clit deep into my mouth. She started face fucking me with her cunt, my head almost completely submerged inside her.
“Put three fingers in my cunt, now!” she ordered me.
I slid three in, never letting go of her cunt. In and out, I pumped inside her until she groaned, my fingers being squeezed by her pussy walls. She groaned and pushed my head in harder until I was swallowing her juices, squirt, squirt, down my throat. My face was wet, from her orgasm.
Her legs were shaking when she let me breathe. She smiled as she pulled me to her and French kissed me.
“Touch your pussy, Wendy. Rub your clit for me.”
I obeyed without hesitation. I reached down between my legs and moved my wet panties to the side. I touched my hard, swollen clit, as she watched me.
“That's right, little one, rub it faster. Don’t close your eyes, look at me.”
She opened my dress and took out my heavy breasts. She started pulling my nipples hard, twisting them.
“Before you cum, you must ask my permission. Do you understand me?”
She pulled my tits hard again and I moaned, “Madame, can I cum, please! I'm begging you!”
“No, not yet. You have to earn it!”
She pushed me to the floor, got between my legs, and started rubbing my clit with her thumb as she finger-fucked me. She was laughing each time I begged her to let me cum. It felt like an hour that she fucked and played inside my wet cunt.
“Ask me again, little one,” she whispered.
“Madame, can I cum? Please, please!”
“Yes, squirt!”
She put her mouth on my mound as I let loose. She swallowed every drop. I couldn't move; I couldn't think. I felt like I was on an amusement ride spinning and spinning.
She stood and fixed her appearance. Then, she reached into her desk and took out a bar of dark chocolate. She then turned and took a bottle of water from her mini-fridge. She knelt next to me and helped me sit up.
“Here, eat this and drink this after. Your first client will be tomorrow. Leave your email with my secretary.”
She handed me a cell phone. “This has a tracking device in it, in case of emergency, I will email you the itinerary. You will be paid in cash before the assignment. A messenger will hand-deliver you a package with your rate and any last-minute changes.”
“You can freshen up in the bathroom. Every Monday you will come to my office for a meeting. If I'm too busy, you will come to my house, or we will meet at a hotel. You are still in training, but this client you are seeing tomorrow wants an escort to a doctor's conference dinner.”
I did as I was instructed, left the office, and drove back to college. Have you ever driven somewhere but don't remember doing it? That's how I felt; it was a blur. The only thing I knew was that I had less than fifteen hours to figure out how to be an escort.
I had very little sexual experience. Of course, I wasn't a virgin, but I hadn't been with many men either. The “web” wasn't available yet, there wasn't any Google to use for research. I had the college library, and that was it. I pulled some old magazine articles but they didn't offer much help. So, I walked back to my dorm.
The messenger arrived at 12:30 pm with my itinerary. Inside it was a stack of twenties, rubber-banded together, and a computer-printed letter with all the information on it. My date that night was thirty-eight, a trauma physician, and his name was Dr. Anwar Raguliti.
I was to drive to the car-share parking lot on Baker Street. There, a car would pick me up at six-thirty, dinner was at seven. He had paid extra for sexual favors after dinner and he expected me to stay with him in his hotel suite until after breakfast.
I went shopping at the local mall and picked up a sexy bra and panty set. I was going to borrow a little, black, sexy dress from Rose. I got a bikini wax and had a pedicure. I felt sexy and excited. This young girl of twenty-one had confidence and a sexy, hot body. She was ready to take on this new world and milk it for all it was worth. It was about financial freedom and sex—no love, no commitments, no problem.
I was dressed to kill in a black silk push-up bra, silk French cut panties, silky smooth legs, a little black dress, and sling-back heels, with my red-painted toes peeking out. My thick, dark, brown hair was loose down my back, and I had red lipstick, with a splash of perfume in all the right places.
I parked my car in the lot and waited. At six-thirty, a long, black limo pulled into the parking lot, and it pulled right next to me. The limo driver got out, opened my car door, took my hand, and reached for my overnight bag. He opened the limo door helping me inside.
Once inside the limo, all my senses took over. The smell of his cologne, the size of his feet, his hair, how big his hands were, and finally, his eyes, hazel with a touch of gray assailed me. He greeted me by name, as he had been filled in as to who he had spent his money on. He touched my leg and his voice was deep, powerful, and very sexy. He motioned for me to scoot closer to him.
“Thank you, Wendy, for being my date tonight. I usually find a way to get out of these formal dinners, but tonight is about hospital politics and trying to secure money for a new surgery suite. You look very beautiful tonight,” he caressed my thigh softly.
He kept talking, I think he was more nervous than me.
“There is a cocktail hour before dinner. I will be holding your hand and keeping you close to me. You are my girlfriend from out of town, going to college for her bachelor's degree. Just be engaging and polite, and it will be a mostly painless night,” he winked at me. He continued, “I assume you're on birth control.”