Gigolo

By Willie Cici
published June 10, 2019
Summary

Grayson’s pursuits find himself in troubled waters …

Grayson Baker dove into the pool of his sugar momma’s estate. He swam for almost half an hour enjoying the cool waters on the steamy hot July day. As he breaststroke from one end of the pool of the other, Grayson enjoyed the strong sun beat upon his face. He had the world by the balls and loved every minute of it. For the small price of seducing his sugar momma, Grayson earned the financial largesse of his lady friend. In addition to outright sums of money, Grayson’s lady friend showered him with gifts.

Grayson learned at an early age that he could garner more from his looks than from his brain. He hated school, but he loved the art of seduction. In high school, Grayson learned that he could barter with his sexual prowess. When he wanted new clothes, Grayson fucked the wealthiest girl in school. When he needed a passing grad, Grayson seduced his teachers. When he needed some spending money, Grayson convinced the milfs at his gym to pay him for ‘extra services’. Sex equaled money. It was a lesson that Grayson would master and then catapult into his career.

Grayson was a gigolo, not a street-walker. He studied his prey and their behavior. After two semesters at the local community college, Grayson secured a position at the country club’s health club, as a personal trainer. From there, Grayson targeted willing sex partners to finance his desired lifestyle.

Grayson watched his sugar momma strut out of the house towards the pool, sporting a Catalina swimsuit that accentuated all her curves. Grayson slowly hopped out of the pool, putting on a good show for his sexy milf.

“When does he get back, Eva?”, Grayson asked.

“Sunday night. He’s at some convention. He wanted me to go, but I refused.”, Eva said.

Grayson approached his milf and kissed her. “So, Eva, we have the house to ourselves for three more days?” Eva nodded ‘yes’. He lowered Eva’s bathing suit top and nibbled on her breasts. Eva smiled, as she took Grayson by the hand and led him into the house to pass the late afternoon, evening and twilight hours. Grayson calculated the eventual payday in his head with every orgasm he coaxed out of the sexy milf.


Two weeks later –

On a Friday afternoon, Grayson drove his car downtown towards the Staples Center. He parked his vehicle in the underground garage of one of the many tall, imposing skyscrapers in Los Angeles, and rode the elevator to the 12th floor. He shook his head in disgust. To avoid a criminal conviction, Grayson accepted an alternative trial disposition. Participation in Anger Management counseling was one of the conditions of his disposition. He was attending his first appointment with the psychologist, Doctor Barry Fitzsimmons. Grayson entered the reception area and took a seat. About 3:05, the door opened and a distinguished looking gentleman called out, “Grayson.” Grayson rose from his seat and walked into the doctor’s office. “Hi! I’m Doctor Fitzsimmons.”

Grayson extended his hand and said, “I’m Grayson Baker.”

“You work at Silver Hills Country Club.”, Doctor Fitzsimmons said.

“Yeah, I do. Are you a member?”, Grayson asked.

“Yes, I am. My wife and I are members. The wife practically lives there.”, Doctor Fitzsimmons bragged. Grayson took a seat in the office. “Can I get you something to drink? Bottle of water?”, he asked.

“Sure.”, Grayson replied. Doctor Fitzsimmons walked over to the small refrigerator in the corner of his office and retrieved a bottle of water. He twisted the cap and handed the bottle to Grayson. Grayson sipped the spring water and kept the cap on the bottle.

“So, what brings you here?”, Doctor Fitzsimmons asked.

“My court case.”, Grayson said. “Agg Assault.” Grayson took another sip and stared at Doctor Fitzsimmons.

“Do you remember what happened?”, Doctor Fitzsimmons asked.

“Not really. It’s a blur. I know that I beat some guy.”

“That’s … a thumbnail version. You sent him to the hospital.”, Doctor Fitzsimmons replied.

“He attacked me. I was defending myself.”, Grayson rationalized.

“No. He accused you of having sex with his wife. When he tried to strike you and landed a punch, you went …”

“I went red.”, Grayson admitted. He took another gulp of water and capped the bottle.

“Have you always overreacted to hostile situations?”, Doctor Fitzsimmons asked.

“I have a temper.”, Grayson replied.

“You can’t remember what happened?”, Doctor Fitzsimmons questioned.

“I don’t remember what I did. I know what I did, because I read the police reports.”

“You know … hypnotherapy can help with memory blocks.”, Doctor Fitzsimmons said.

“I don’t know.”, Grayson said. He felt a little tired, more sleepy than dizzy. He wanted to close his eyes, but knew he could not fall asleep in the middle of his therapy session. Grayson finished the bottle of water and stared at Doctor Fitzsimmons. “I … I’m not sure … about hypnosis …”, he said, unable to finish a thought.

“Close your eyes, Grayson, and listen to my voice.”, Doctor Fitzsimmons said. Grayson glared at the doctor. “Close your eyes. Just relax. You’re in good hands.”

Grayson closed his eyes. He listened to Doctor Fitzsimmons, guide him through deep breathing, relaxation drills, and then a fictitious walk up a flight of stairs to a higher place where his mind was open, calm and receptive. When he opened his eyes, Grayson stared at Doctor Fitzsimmons.

“Now Grayson, who attacked you?”, Doctor Fitzsimmons asked.

“George Masters.”

“And why?”

“He found out his wife was paying me to have sex with her.”, Grayson bragged.

“How much money did she pay you?”

“He figured it was about $5000.”, Grayson answered.

“And how much was it really?”

“More like $15000.”, Grayson replied.

“For how long were you having sex with his wife?”, Doctor Fitzsimmons asked.

“About six months.”

“Where did you meet his wife?”, Doctor Fitzsimmons asked.

“At the country club. That’s where I meet all my mommas.”

Doctor Fitzsimmons smiled. “Mommas. Is that what you call them?”

“Yes.”

“And how many mommas have you seduced?”

“Over a dozen.”, Grayson boasted.

“Anyone I know. Be honest with me. I’m here to protect you. You’re safe, relaxed and calm. Just open your mind.”

“Mrs. Hardy … Mrs. Browning … Mrs. Daniels. And my new favorite, Mrs. Connors.”

Doctor Fitzsimmons gasped at the last name. “Mrs. Connors?”

“Yeah. She’s hot. I really love having sex with her. She’s my favorite momma.”

“Does she pay you?”, Doctor Fitzsimmons asked angrily.

“Of course. They all pay.”

Doctor Fitzsimmons rose to his feet. His anger flooded his mind. “That fucking whore!”, he muttered. Poor Grayson did not realize that Mrs. Connors was really Mrs. Fitzsimmons. His wife, a devout feminist, insisted on keeping her maiden name, Connors. Fitzsimmons stared at Grayson. He understood the first impulse of George Masters, to attack the young stud, but then, he closed his eyes. “She’s paying him to have sex, because …”, he thought to himself. He did not finish the thought. He and his wife agreed to stay married, but to pursue their sexual interests independently without causing scandal. As he opened his eyes and stared at the young stud, Fitzsimmons licked his lips. “Take off your clothes.”

Grayson rose to his feet and undressed for the doctor. He stood in the office like the ‘David’, posing in the nude. Grayson impressed Fitzsimmons. His wife had good taste in men. He could not abide her reckless conduct. “Paying the personal trainer at the country club for sex.”, Fitzsimmons thought to himself, shaking his head in disbelief. “Get dressed, Grayson.” Grayson found his clothes and dressed. “Sit down.”, Fitzsimmons said when Grayson was fully clothed.

“Grayson, for the time being, keep working the mommas at the club. Make your money. You’re young, attractive and sexy. Have fun.” Grayson smiled. “Close your eyes and listen to my voice.” Grayson closed his eyes. “When you have sex with Mrs. Connors, make sure that you cum inside of her. Do what you have to do to cum inside her. Do you understand?”

“Yes, Doctor.”

“Good. Whenever you hear me say ‘angry stud’, you will return to this relaxed, calm, receptive state, deeper and deeper, calmer, more relaxed, more receptive. Do you understand?”

“Yes, Doctor.”

“Good. Now, on the count of 3, open your eyes. 1-2-3.”

Grayson opened his eyes. “Was I hypnotized?”

“Yes, you were. You did very well. Next time, we’ll explore what happened as I loosen some more memories. For now, we’re good. I’ll see you here next week. Same time.”

Doctor Fitzsimmons rose to his feet, shook Grayson’s hand and escorted him out of the office. When he returned to his desk, Fitzsimmons opened his desk and found the vial of liquid sedative he used to spike the spring water. He placed the vial in his pocket. “For later.”, he whispered to himself.


Grayson entered the reception area of Doctor Fitzsimmons’ office. He greeted the receptionist and waited for his afternoon appointment. Doctor Fitzsimmons opened the door of his office and greeted his client. “Grayson, come in.”

Grayson rose from his seat. He extended his hand and said, “How are you, Doctor?”

“I’m doing well.”, Doctor Fitzsimmons said, as he shook Grayson’s hand. The two walked into the office and took their places. “Can I get you some water?”, he asked.

“Sure.”, Grayson replied. Doctor Fitzsimmons walked over to the small refrigerator in the corner of his office and retrieved a bottle of water. As he did the prior week, he handed the pre-opened, spiked bottle to Grayson. Grayson finished half of the bottle of water and capped the bottle. “I must be thirsty.”

“Last week, we started to unlock those memories in your subconscious. Are you ready to delve a little deeper?”, Doctor Fitzsimmons asked.

“I don’t think the hypnosis worked.”, Grayson said, as he sipped his bottled spring water.

“Angry stud.”, Doctor Fitzsimmons said. Grayson’s body fell limp. He looked bewildered and dazed. “Can you hear me, angry stud?”

“Yes.”, Grayson replied.

“Good. Did you have sex with Mrs. Connors?”, Fitzsimmons asked.

“Yes. I fucked her and shot my load in her every time we had sex. She told me not to use a condom.”, Grayson replied.

Doctor Fitzsimmons smiled. “Make sure you fuck her at least three to four times a week. She’ll pay. Don’t worry.”

Doctor Fitzsimmons made sure that his wife was on the same page. He entranced his wife with his signature mix of sedatives and hypnosis. His wife, who did not want children, would soon find herself pregnant with Grayson’s help. The doctor ordered his wife to stop taking ‘the pill’ and to allow Grayson to climax inside of her. Young, dumb and full of cum, Grayson would impregnate the wife for certain.

“Grayson, Mrs. Connors wants you to live at her home. You will agree to her request. Do you understand?”

“Yes.”, Grayson replied.

“And from now on, whenever you hear my voice, whatever I say, you will obey. Do you understand?”

“Yes.”

“Whose voice will you obey?”, Doctor Fitzsimmons asked.

“Your voice.”, Grayson replied.

“Good. Now, angry stud, get on your knees, crawl over to me and suck my dick.”

Grayson fell to his knees, crawled from his seat to the leather chair where Fitzsimmons was seated and unbuttoned his trousers. He pulled out the doctor’s member and suckled upon his throbbing cock. The doctor was semi-hard after all this talk of sex. As Grayson sucked his cock, Doctor Fitzsimmons spoke to Grayson. “You’re going to learn how to suck cock properly so you can make even more money at the country club.”


Nine months have passed —

Grayson opened his eyes. The sun filled his spacious apartment, atop the garage of the sprawling California estate. He hopped out of bed, found his bathing trunks and descended the stairs of his apartment and headed for the pool. When he reached the pool, Grayson dove into the deep end and enjoyed the cool waters on a sizzling hot California morning. He swam as he did every morning, 50 laps, both ways. The water cardio did wonders for his physique. The studly gigolo sported a fine physique prior to his moving on to the grounds of the estate, but in the last six months, his body transformed into an absolute wonder. Taut, lean, sculpted and beautiful: Grayson was the epitome of the blonde California stud.

Barry smiled as he watched his boy toy swim his morning laps. When he finished his laps, Grayson would enter the house, have sex with the wife, and then head to the country club, where he continued to work as the resident male whore for the country club milfs. At night, when he returned home, Grayson would spend the evening in Barry’s bed, and later, return to his apartment on the estate, and sleep the night away. Even with Eva in her sixth month, Barry made sure that Grayson continued to have relations with his wife. Eva continued to pay Grayson for his daily sex sessions. Within a couple of months, Eva would pay the ultimate price by giving birth to the child she never wanted. She would be the perfect mother. Barry would make sure that his wife honored her motherly obligations.

Grayson finished his laps and readied to jump out of the pool. (To see Grayson, click here). He found a towel, wiped the excess water from his body and walked into the house. He climbed the stairs and headed for Eva’s bedroom. He found Eva reclined upon her bed, waiting for her gigolo. Barry stood at the threshold of the bedroom, watching his wife and her young stud perform to his specific commands. He smiled. “Best money I ever spent.”, Barry said to himself. “Best money.”

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