My Son the Gigolo

Book 2

Thanks to WAA01, Killerarmyguy, and Taco for the edits.

******

Chapter One

"Umm..." Drake Lucian, aka Dante Cole, his professional name, stood very confused as he stared at the rather attractive redhead at his door. It was his house (unofficially, his father's name was still on the loan as well as his mother's), ever since his father skipped out on fulfilling his agreements. Thinking he or his brothers would allow their mother to go into foreclosure. He hadn't spoken to his father since he walked out on them with his mother's sister and moved to somewhere in Asia. Not that he cared, he got the woman he had longed for forever since he was sixteen. What his father and his aunt did was their business. "I'm sorry, no, I don't," he apologized; he would have remembered someone as attractive as she was; then again, with all the whoring that he's done, that could have muddied his memories. Seeing the woman's face heat when Emma's moans began to filter down the stairs. "Sorry about that," Drake said, a little embarrassed as he stepped outside and closed the front door.

"It's... okay, I came unannounced; you had no way of knowing you'd have company," she said bashfully, remembering how hot he looked at the club that night while she was serving out drinks. Now, now that she was less than two feet away, she was drooling in her mind at how drop-dead gorgeous he was to her. "I'm Samantha Carter; by the way, we went to high school together," she introduced herself as she extended her hand to him.

"Wait, not Samantha Carter, the head varsity cheerleader?" Drake asked, trying to recall where he's heard that name before.

"The one and only," Samantha said with an alluring smile as she slyly eyed how his t-shirt hugged his chest. Detailing every muscle, remembering how he didn't have said body back in high school. Wondering just what he's been doing over the past few years. She couldn't help it as his cologne filled her nose, heat began to form between her legs. She had no idea how or when he got so attractive.

"So... why look me up after all this time?" Drake asked, noticing how her cheeks blushed and her blue eyes glanced down to her feet.

"Umm... can we like go somewhere to talk?" Samantha inquired, trying to ignore the sounds that were coming through his front door.

"Oh?! Yeah, they're probably going to be a while," looking around for her car, not seeing one, "did you drive?"

"No... I took the bus," Samantha said, a little embarrassed.

"Coffee good with you?" Drake asked with an arched eyebrow.

"Mmmhmm," Samantha hummed with a nod of her head.

"Okay, let me grab my keys," Drake responded as he reached for the handle of his front door.

"Sure," Samantha chirped. Mouthing the words 'Oh my God' as the front door closed behind him. Breathing out slowly, trying to calm herself down, she didn't think Drake would take too kindly to her coming on to him when she would be asking him for a favor. Turning her head as she heard his garage door lifting. Her jaw dropped as Drake's BMW 8 series backed out, watching how the roof lowered once he was out from beneath the door. She had no idea he had that kind of money to afford a car like that.

"Hop in; I know this nice little coffee shop close by where we can talk," Drake stated as he peered over at her. Keeping his smirk to himself, he noted how she was gawking at the interior as she slid into the passenger seat.

"Nice car," Samantha said, trying to control her voice.

"Thanks, just got it a couple of weeks ago," Drake replied as he backed out of the driveway.

"So... I heard you went off to New York," Samantha said over the wind.

"I did; I head back in early August. Did you head off on some wild adventure once high school was over?" Drake asked as he stopped at a stop sign, hearing his blinker ticking away, waiting for the cars to pass.

"I wish," Samantha sighed.

"What happened?"

"I didn't do so well in high school; I allowed myself to think I had it made. Stupid mistake," Samantha said sadly. "I wanted to go to some far-off college to expand my wings, to see what I was made of, you know?" Seeing him nodding in understanding, "But I partied too much, studied way too little; in the end I'm stuck here. What's New York like?"

"Crowded, very fucking crowded. Noisy. Expensive, but it has its merits," Drake answered, taking a left and heading towards the shop.

"Oh? Like what?" Samantha asked curiously.

"I don't think you want me to answer that," Drake responded with a sly grin on his lips.

"Oh, I see; got you some ladies up there, huh?" Samantha teased.

"Quite the few," Drake admitted. Wondering if he would be servicing the same women he had done before he had left for Italy.

"Don't take this the wrong way, yet I don't ever recall you being so well off with the opposite sex," Samantha said as she noted how the strands of his black hair moved through the wind as the late morning sun played along his face. Her heart fluttered as Drake laughed; she did like the sound of it which brought a smile to her lips.

"Yeah, that didn't start till the last few months of my senior year," Drake replied with a charming smile on his lips. His mind flashed back to the day he first met his Madam.

******

Two years and a few months ago...

Drake stared nervously up at what appeared to be a simple ordinary office building. With its plain brick façade, its neatly spaced windows were the only breaks in the sea of red and brown. Hearing the noise of the city at his back, wondering if he could truly do this. If he had what it took to be a gigolo. Pondering if any woman would want to be seen with a skinny, virgin, eighteen-year-old high school kid. Blowing out a breath that he had been holding. Knowing he was there for a purpose, he just prayed that this would work out. He so wanted to get back at his mother for what she said to him. Hoping he could learn the skills he needed to make his mother lust after him like he knew she did with his older brothers. To make her yearn to have him like he's wanted her for so long before she said those hurtful words. Walking into the building, heading towards the elevator bank, he already knew where to go. The woman he spoke to informed him where their office was located. Her stern voice filled his mind as he looked at his phone, noting the time. Recounting what she had told him, if he couldn't be on time, don't bother showing up.

Swallowing hard when the elevator doors rolled open. Drake was expecting to step out into a hallway, not right into the middle of the heart of Winters Escort Services. Noting how the woman and man sitting behind the receptionist desk were staring oddly at him as Drake just stood unmoving. Feeling his heart hammering in his chest as their eyes bored into him. Clenching his fist, he came this far; he wasn't going to chicken out now!

"You lost?" asked a man with an Italian accent as his hand held the elevator doors open. Seeing the nervousness in Drake's eyes as the two of them gazed at one another. Arching an eyebrow when he noted how Drake's cheeks were heating. "Or are you here for a job?"

"J-job," Drake managed to say in a low whisper.

"First time in a place like this? Come on, the name's Simon," he greeted with a warm smile when he saw Drake's weak nod.

"Drake," he replied, taking the man's hand.

"Word of advice, in this line of work, women expect confidence," Simon stated, lifting Drake's chin up. He could tell Drake had been hurt and was seeking validation from someone or anyone that would give it to him. "Hey, Nancy," he cooed, putting on the charm he earned from his time in Italy, where he had first worked for the Madam of the branch there. "When you going to leave that big ol' lug of yours and let me have a taste, hmm?" Drake watched how his newfound friend didn't waste any time and how red the woman's face was getting.

"Simon, you know the rules; while I'm flattered, you would find this old woman alluring enough to line your arm for a night. Yet my heart belongs to that 'lug' as you call him," Nancy replied with a good-natured smile.

"Shame, and here I was wondering what you would look like spread out on my bed," Simon sighed, seeing how his new friend was studying him.

"Well, that's one thing you'll never find out," Nancy stated, yet that didn't stop her mound from heating. While she knew Simon was a harmless flirt around the office, he knew that was as far as it would ever go unless he left the agency. Even then, she wouldn't stray from her husband no matter how suave, and alluring Simon could be, and she knew Simon respected that boundary. "So, who's your new friend, Simon?" she asked, peering over at Drake.

"Ah, this here is Drake; he's here to see the boss," Simon stated, placing a hand on Drake's left shoulder.

"Oh? That so?" Nancy asked, looking over at Drake, who nodded.

"Yes, ma'am," Drake spoke when Simon gave him a look.

"Good, good, if you will just fill these out, I'll let Madam Winter know you're here," Nancy said, getting to her feet and handing Drake a clipboard with an employment application clipped to it along with a pen. "If you'll just have a seat there," she stated, nodding to the chairs. "So... what's up with the kid?" Nancy whispered, knowing teenagers didn't normally show up at their company's doorstep. If she had to guess, he looked close to her daughter's age.

"No idea, but he looks like someone hurt him or something like that," Simon uttered low.

"You going to mentor him once the boss gets done with him?"

"Think so," Simon nodded. Looking down when Nancy lightly placed her hand on his right forearm.

"You're a good man, Simon," Nancy said in a sweet tone.

"I was like him once back in the old country; I know how nerve-racking the first time can be."

"I'll keep an eye on him as well," Nancy said in a motherly tone. She had no idea what drove Drake to look for work as an escort so young; normally, it was the college girls that sought them out to pay off their tuition.

"Tell your husband thanks for inviting me to the party last weekend; I don't get a lot of time just to unwind," Simon spoke with a friendly smile before moving off towards Drake. "How's it going?"

"I don't know, never had a job before, so don't know what most of this means," Drake responded, scratching his head.

"Here, I'll help you out," Simon stated as he lowered himself down into the chair beside Drake.

"Why are you being so nice to me?" Drake whispered when they were halfway through his application.

"We all started somewhere, me; I started about your age when I used to live in Italy. I was like you, scared, and hurt, wanting to prove something to someone. Then I met a man who took me under his wing and showed me the ropes. How to act. How to speak. What words to avoid, and what words to use to get the client aroused. How to dress, what clothes to wear, cologne, what car to drive, etc. etc. I would like to help you, too, like my mentor helped me when I was just starting out in this business. My real name is Francis, by the way, here I'm, Simon. You should think of a professional name so no one will recognize you."

"Does everyone do that?" Drake asked low, to which Francis nodded.

"Madam Winters insists upon it. She doesn't want trouble from any family members if it gets out if one of us is an escort. Here's my card," writing down his cell phone number on the back of it, "call me any time; if I don't answer, just leave a message, and I'll get back to you as fast as I can," Francis said, holding it out to him. "It's okay to be nervous; it happens to all of us our first time out. Just takes time to get the hang of things," he said, lightly patting Drake on his shoulder when he saw Nancy motioning Drake to the desk.

Drake nodded as Nancy showed him how to find Madam Winters's office, as she unclipped his application and handed it back to him. Thanking her, hearing her soft encouraging words as he set out to start his life as a gigolo. Rubbing his hands along his pant legs to dry the sweat he felt on his palms as he neared the woman who held sway over his employment.

"Enter." Taking a dry swallow as his hand slowly turned the knob. Drake's heart was in his throat as the door continued to inch open. Drake kept his surprise from his face as he was greeted by a very alluring black woman. He had been under the assumption he would be dealing with a woman in her late sixties or seventies. Not this gorgeous, vivacious woman who appeared to him to be no older than her mid-thirties. "I take it you're the young man who contacted me the other day. Am I correct in that assumption?" Madam Winters asked with an alluring smile upon her lips. Her eyes ran down Drake's body before returning to his face. Noting the boy had potential, she just had to polish her gem to get him to shine.

"Yes, ma'am," Drake answered, trying to keep his nervousness in check.

"Please, have a seat," Winters offered, gesturing to the chair before her. "So, tell me, how did you hear about my agency?" she asked, taking his application from him.

"Saw your ad in a paper," Drake said truthfully.

"And why do you want to work for me... let me rephrase, why do you want to become an escort?" Winters inquired with a questioning look.

"Well, I need the money, plus I have no work experience, as you can see..."

"Yes, I saw; you know this isn't some fast-food joint where you can just quit at the drop of a hat. This isn't some whorehouse where you can fuck whomever you want, whenever you want. Can you keep that in your pants?" Winters asked with a pointed look.

"Yes, ma'am," Drake nodded.

"Good. I don't supply hookers to clients; my people are only there to escort their clients to whichever function they have been hired to attend. Sex, if there is to be any sex is off the clock, am I understood?" Winters spoke in a firm tone. Keeping her interest hidden at how red Drake got when she mentioned the word sex.

"Yes, ma'am."

"As I have said, I don't supply hookers to my clients. What I do offer is sophisticated, charming, wholesome escorts who help ease our clients in their hectic lives," Winters said, getting up from her seat. "Now our clients are very busy, very influential people. If I hire you, I want your best at all times when you're with a client. If I hear one word about how you were rude, disrespectful, or forceful with a client, I will end your contract with me in a heartbeat. Am I clear?"

"Yes, Madam Winters," Drake answered, trying not to notice how good her ass looked when she sat on the edge of her desk.

"Now, I must ask this, so please forgive the personal nature of it; I don't intend to be rude or nosy, okay? Have you ever been with a woman or man, if you swing like that, ever before?"

"No," Drake uttered in a shy tone as he looked down at his lap. Feeling her fingertips lifting his chin to peer at her once again.

"What do you mean no? Are you telling me you've never had any kind of sexual relationship with anyone before?" Winters asked, quite shocked, to say the least, as he gave her a weak nod. She was sure that most teenagers these days weren't virgins any longer. "Can I ask why?"

"She didn't want me," Drake uttered; the pain his mother had inflicted was still raw in his eyes.

"Dry your eyes," Winters said softly, handing Drake a tissue. "Come with me," she said, rising off the edge of her desk and holding her hand out to him. Feeling the warmth of his hand as his fingers curled around her own. "If you're going to work for me, I need to know what you're working with. So, I can place you with the right kind of client. I hope you understand," Winters stated as she led Drake towards the side door of her office that opened up to a windowless, soundproof room with a lone bed that rested at the other end of the room, where she tested out new hires; male and female alike. "Please undress to your underwear so I can take a few photos for your profile; it's what our... are you straight, gay..."

"Straight," Drake stammered.

"No need to be nervous, Drake; I'm here to help you to become the best escort you can be," Winters spoke with a warm smile as she stood beside the camera sitting on its tripod and was pointed at the whitewashed wall.

"Wait... I got the job?!" Drake uttered in surprise.

"You wouldn't be in this room if you hadn't; you'll still need to sign a contract with me..."

"For how long?" Drake cut in.

"Three years, your pay will be 75% of the client's price, the rest goes to the house, and don't you dare think of going behind my back. If I learn that you have, I will blackball you so fast it will make your head spin?! We clear?" Winters asked with a stern look.

"Yes, Madam Winters."

"Good," Winters replied, returning to her happy demeanor. "Now, please, if you would," she waved to his attire. Arching an eyebrow when she noted how loose his jeans were as he slid them down his legs. Equally intrigued by the lump she saw in his boxers before his hands covered his manhood once his shirt joined his pants on the floor. "Is something wrong, Drake? Are you uncomfortable?" Winters asked, wondering why his face was getting so red.

"N-no," Drake uttered, embarrassed that he had a hard-on in front of his new boss. However, this was the first time he's ever been in that state of undress in front of a woman before.

"You know it's okay if you've gotten aroused; no shame in that," Winters stated, flashing Drake a smile to ease his jitters. "I'm going to see it soon," she cooed; an alluring smile she had mastered from her years in the business appeared on her lips. She thought it was rather cute how he was blushing as he moved his hands away from his groin. "

No, that can't be

?!" Winters thought to herself as she gazed at the rather large and, from what she could discern, thick bulge. "

What woman wouldn't want that?! Was that woman crazy

?!" She kept herself from gawking when she told him to lose his boxers. She's seen some thick cocks in her life and long ones as well in her years in the industry. Yet she's never seen a cock as thick as Drake's as it stood pointing at her.

"Don't worry, Drake, as your Madam, it's my responsibility to see that you know everything there is to know about sex and how to give pleasure to a woman's body," Winters said sweetly as she walked out from behind her camera. "So, there's no need to be nervous. I know it's natural for your first time. It was the same with me when I was younger than you. I'm not sending you out there until I know you got the basics down pat. I might be an old bird..."� � � � � � � � � � � � �

"You're not old; you can't be anywhere over thirty-five," Drake cut in.

"Why, thank you, young man, but I will have you know I'm fifty-five-years young," Winters spoke, flashing him a smile as she led him towards the bed. She wouldn't deny that his compliment did boost her ego. Lowering herself down onto the edge of the bed and moving Drake to stand between her legs. Normally she wouldn't have done this, not until their blood work came back. Yet she saw the truth in his eyes that he had indeed never been with a woman before; no, she would have made the men wear condoms while she blew them. "It's okay if you don't last long, Drake; just warn me before you erupt, so I don't choke," she cooed up at him before her lush lips wrapped around the head of his rod. Feeling her jaw inching wider and wider as she sank down his length. Her dew began to gather rapidly as the fattest cock she's ever had in her mouth slid along her tongue. "Feels good, doesn't it?" Winters inquired as her hand stroked him off. Watching his elation play along his face as she sucked on his right nut to give her jaw time to relax.

"Mmmhmm."

"You know my husband likes watching me fuck," feeling his cock swell at her sultry words, "he likes watching me cream another man's cock. Would you like to make this pussy of mine all nice and creamy?" Winters asked, spreading her legs; her skirt rode up, revealing her light chocolate labia; the lights glinted off the dew that hung on her lips. Her neatly trimmed landing strip waited for Drake to run his nose through it as he tasted her sweet pussy.