Incest/Taboo My Son the Gigolo

"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.

"Y-yes," Drake stuttered, watching how her cheeks sunk in, the way her brown eyes peered up at him as she sucked him off like a pro.

"Good, I was hoping you would say that. Because tomorrow, you will arrive at my home and not leave it until I'm satisfied you know what you're doing with this fat thing you call a cock," Winters directed before beating his crown against her tongue.

"Shit?! I'm..." Drake's legs trembled as he blasted his load into his Madam's mouth. His eyes rolled into the back of his head as he groaned in pleasure at the sensation of her swallowing down his cum.

"Hmm... lasted longer than I thought you would," Winters mumbled as she rolled her tongue around, smacking her lips at the taste of his come. Pushing him back just a bit as she rose from her spot. "Relax, if you're nervous, the women will be too, take a breath and steady yourself. These aren't going anywhere," she said, shaking her 34DDs with her hands at him when she ordered him to undress her. "Look the woman in the eyes when you're taking off her clothes; always maintain eye contact." Teaching him how to act in the bedroom as Drake's fingers worked quickly to unbutton her blouse until she took hold of his hands. "Speed is important, but too much you appear too eager, too rushed, it makes the woman think you'll be the same in the bed. Too slow, and you'll appear disinterested. You need to find that balance," she stated in a teacherly voice as she showed him, then re-buttoned her shirt and had him unbutton it once again until she was satisfied.

"What do you think of my ass, Drake?" Winters asked from over her shoulder as her skirt fell to the floor as she stood in only her bra and crotchless panties.

"C-Can I touch it?" Drake asked, trying to sound confident like Francis had told him to be.

"Of course you can?" Winters purred; she did love virgins. They were so eager and always so ecstatic to simply touch any part of a woman's body. "So..."

"You sure you're fifty-five?" Drake asked as he rolled his Madam's ass cheeks in his hands. "This sure doesn't feel like a woman who's that old."

"Oh? Go on, tell me, why do you say that?" Winters mused, peering back at him, seeing how he was enjoying the view.

"It feels too firm, too kissable; I wonder if they do butt transplants; feels like a twenty-year-old's ass in my hand," Drake flirted.

"Why, thank you, Drake; you should always compliment your clients. If they feel good, you'll feel good, and ensure that there will be a next time," Winter stated, nevertheless, she was happy to hear his praise. She did work hard to maintain her figure, which wasn't easy given her age. "No, no, do it again, Drake, this time be faster about it," she directed as she re-clasped her bra. Making him do so another three times until she was sure he could take one off with ease. She knew the more he went on 'dates' the better he would get. "Now, Drake, remember the client's needs always come first. The blow job I gave you was so you didn't blow your load too quickly, so don't expect that to happen if the client pays for sex. Understand?" Winters stated as she positioned herself on the bed so she could teach him how to eat a woman's pussy. Smiling at him when all Drake could do was gaze down at her pretty little cunt as she spread her labia open.

Her wails gradually grew as she forced him to start over and over whenever he made a mistake when he was eating her out. By the end of the hour-long lesson, Winters was writhing on the bed, holding Drake's face against her pussy. Grinding her hips along his face as his tongue danced along her vulva. Her back arched; her breasts jostled at how he was toying with her clit with that tongue of his. So glad she didn't have to unteach him that stupid alphabet trick she's seen on the net and felt on her pussy a few times. It was too inconsistent, and women, when you're eating them out, likes consistency, especially when you have them on the ropes of an orgasm just like she was at that moment. "Oh fuck me!" Winters screamed out as her torrent of juices flooded her channel as she came hard on Drake's face. "Stop, stop, give me a minute," she panted, pushing Drake away from her oversensitive pussy. Her thighs quaked, her muscles spasmed, her fingers and toes twitched as her aftershocks racked her body. How she fucking loved it. She also loved seeing her juices covering a man's face like she noted they were clinging to Drake's skin.

"Now you just lay there and enjoy the ride; tomorrow, we'll work on your technique," Winters said; the slapping of his cock on her wet pussy was loud in the room. "You hear that, Drake? That's the sound of your virginity leaving," she purred before sinking down onto Drake's hard pole.

"So what changed? If you don't mind me asking," Samantha said, bringing Drake back to the present.

"Met a woman, taught me a lot of things," Drake said offhandedly.

"Like?!" Her face grew red hot when Drake gave her a rather sinful smile that had a number of his clients melting in their panties. "Oh?!" Samantha uttered, dropping her gaze, wondering why she was being so bashful. It wasn't like she hadn't had sex before, hadn't had guys coming on to her left and right since her breasts came in. "So, did you go anywhere on your Spring Break?" she asked, trying to direct her mind away from the thoughts that were running around in her head.

"No, I was studying abroad last year, plus I didn't really need to go anywhere."

"Why?" Samantha asked curiously.

"The house I was staying at was sitting on the edge of a nude beach in Italy, so I didn't see the point of traveling anywhere," Drake said with a coy smirk on his lips.

"No?!" Samantha gasped; she couldn't help it. Her eyes did run down Drake's body, picturing what he would look like nude. "How long were you in Italy?!" she asked, eager to hear his adventures since she doubted she would ever travel outside her own state in her lifetime.

"About a year and a half," Drake admitted.

"How was it? I always wondered what Italy would be like given what I've seen on TV."

"It wasn't too bad, although the tourists during their Spring Break were kind of obnoxious," Drake said truthfully.

"But I bet some of those women were following you back to your place," Samantha teased, feeling her nipples starting to harden.

"Guilty," Drake chuckled as he slowed his car down and turned into the coffee shop's parking lot.

"Was the Mediterranean as beautiful as I've imagined it would be?" Samantha asked as she walked around his car, hearing his 'Mmmhmm.' Looking down at his pocket when his cellphone went off.

"Sorry, have to take this; the boss is calling," Drake said apologetically when he saw his Madam's avatar in the caller ID. Seeing her nod in understanding before moving off to give him privacy. "Hey, I was about to call you since I haven't heard from you yet."

"I know; I planned it that way."

"Oh?"

"You're three years with me is almost up, Drake. Do you still want to be in this life?"

"Yes, ma'am."

"Excellent; I was hoping you would say that." Feeling himself smiling at her warm tone, he's come to know so well. "When can you come in?"

"Say in two hours?"

"Make it 2:45. I have a meeting at two, don't know how long it will go."

"2:45 it is then," Drake nodded against his phone.

"Good, good, I know some ladies will be happy to hear you're still on my rolls," Winters said, her sweet, sultry voice filling his ear.

"I can imagine," Drake responded, smiling into his phone.

"Well, Drake, I'll see you then, don't be late."

"Never, ma'am, otherwise I'll have to kiss that beautiful backside of yours, although I might like that," Drake teased.

"I might make you do it anyway," Winters flirted.

"Well then, I best go get me the best Chapstick, so my lips are supple enough for that fine derriere. Would hate for Brian to question all those red marks along that silky skin of yours."

"I see your charm has grown since your time in Italy. I might just have to have a taste, just to update my files, you understand."

"Sure, sure, I get that. Is this for your personal file or HR's?" Drake asked with a devilish grin on his lips.

"Mine, of course." Drake felt his cock responding in that tone he hadn't heard since the night she had him fucking her all night long.

"Look forward to it."

"Oh, I know you will, Drake, I know you will. I'll see you this afternoon."

"Everything okay?" Samantha asked in a friendly tone, trying not to notice the bulge in Drake's pants. "Fuck, that thing has to be huge?!" she muttered to herself.

"Yeah, just have to head into the office later," Drake uttered as he pocketed his phone. "Shall we?" he asked, gesturing to the shop's entrance. Noting how Samantha brushed her red hair behind her ear, her cheeks heated to a soft red hue as she turned towards the door and walked in.

Samantha felt every woman's eyes on her as she stood next to Drake as they waited in line. It felt like to her she was standing beside a movie star with the way he was garnering the attention of the women in the shop. Her body heated when she felt his light touch on the small of her back, gesturing for her to order first. Her gaze lifted when she was digging out enough cash to pay for her coffee from her purse when Drake lightly placed a hand over hers.

"My treat," Drake spoke with an alluring smile on his lips.

Mentally smacking herself to snap herself out of the trance she felt herself falling into as she stared into those eyes of his. Wondering where he learned to be so alluring and so charming that it made her mind go blank. It wasn't the first time she's met someone as captivating as Drake was or close to it, yet they quickly slipped out of it the moment they got down to what they wanted from her -- her pussy and nothing more. However, with Drake, she hadn't seen him slip out of that demeanor once. A new wave of heat flooded her mound as his fingertips lightly brushed along the back of her hand.

"Okay," Samantha said weakly. Groaning in her head at how she sounded like a girl who's never been around a man before. Then again, as she slyly looked at Drake as he placed his order, she wondered if that statement didn't hold a candle of truth to it. "Thank you," she uttered in a soft tone as he held her chair for her.

"My pleasure, so you wanted to talk," Drake spoke as he lowered himself down into his seat. It wasn't hard for him to note the eyes that were on him. Yet he had mastered the art of keeping his attention focused on the woman he was with, regardless if it was a date or not, still that didn't mean he didn't notice the looks. "What about?"

"Well," bashfully looking down at her hands as they waited for their order to arrive, "I'm not doing so well in my math classes, and I remembered how you excelled in them back in high school when I saw you at the club that night," wondering why that rose his eyebrows, "I was hoping that maybe you could tutor me. I'll pay you, of course, for your time," Samantha quickly said, reaching out and lightly touching his hands.

"You free in the mornings? That's about all the time I have free in the day since I work nights," Drake stated after some thought. Peering up, thanking the woman as she set his coffee down before him as well as slipping a piece of paper with her number into his left hand, urging him to call her.

"Would nine o'clock be a good time for you?" Samantha asked into her cup before taking a sip of her coffee.

"An hour for tutoring, yeah, that should work," Drake mused after a moment, knowing that would at least give him a few hours to nap if he had a 'date' that evening. "And you don't have to pay me."

"But I'll feel like I'm taking advantage of you," Samantha stated, setting her drink down.

"Maybe I want to be taken advantage of," Drake flirted, seeing how that took her by surprise for a moment and how red her face was getting as he leaned back in his seat.

"Drake?! Amico mio?! (My friend?!)," Drake looked around; a smile appeared on his lips at the sight of his old mentor and friend as Simon (Francis), his professional gigolo name, called out with his arms outstretched.

"Ciao, Simon, vedo che sei fuori o ti stai preparando per la sera? (Hello, Simon, I see that you are out or you are preparing for the evening?)" Drake responded in Italian, seeing his friend's smile widen at the sound of his homeland.

"In a few hours, and who's this lovely beauty that you have with you?" Simon asked, switching to English as he laid on the charm.

"Samantha, I like you to meet my friend Simon; Simon, this is Samantha; we used to go to high school together," Drake introduced the two, seeing how Samantha was stammering her words as Simon laid on his charm. Smirking into his cup as Samantha's eyes glanced at him when she had no idea what his friend had just said.

"Drake, tu, io, raddoppia, una notte, cosa dici? (Drake, you, me, doubles, one night, what do you say?)" Simon asked, switching to his professional voice.

"Ottieni l'approvazione di Madam Winters, ti sei procurato un uomo ala (Get Madam Winters' approval, you got yourself a wingman)," Drake whispered as he embraced Simon in a one arm hug.

"Eccellente?! I'll let the two of you get back to your conversation; please do forgive my intrusion," Simon uttered in a suave tone as he peered down at Samantha. "Ciao Drake," he spoke as he waved to his protégé.

"Who was that, and what did he say to me?!" Samantha whispered as she leaned over the table.

"That was my mentor; he's taught me a lot since I started working for my boss a few years ago. Are you sure you want to know what he said?" Drake asked with a coy smirk on his lips as Samantha vehemently nodded her head. "I'll have to whisper it in your ear then; it's not suitable for me to speak so lewdly in public," he said sinfully as he slid into the chair beside her. Listening to her increased breathing as he whispered the sensuous words his mentor had spoken to her.

"Please, excuse me for a moment," Samantha spoke, quickly getting up from her seat and hurriedly walking towards the store's female bathroom. Her chest heaved, her body quaked, and her nipples pressed hard against her bra as she eased two fingers into her mound as she sat in the bathroom stall. Toying with her wet, aroused pussy thinking what those two could do to her if she had them together. Imagining they each held her aloft as they thrusted their cocks into her. Her wails filling her mind, just thinking of what it would feel like being stuffed by the two of them as they drove her crazy with lust as she came over and over again on their hard cocks. Her hand flew to her mouth, her body convulsed as she came on her fingers. Feeling her clit twitching, wishing Drake's lips were wrapped around it as she relaxed, rubbing that little bud as she came down from her euphoric high. Blowing out a breath, she's never done that before; she's always been able to hold off until she got to the privacy of her home. Yet, with Drake and his friend Simon she just wanted to burst right there in front of everyone in the store.

"Did you see that guy?!" Samantha perked up at the sounds of the two women that had just walked into the bathroom.

"Which one?"

"The younger one, God, I just want to take a bite out of that taut ass?!"

"I know what you mean; just think about how those muscles would feel when you're riding him?! The older one was just as tasty!"

"Mmmhmm." Samantha heard the lust in the woman's hum. Jumping in startlement as a knock came on her stall door. "You almost done in there?"

"Just a second," Samantha squeaked out, quickly wiping her pussy dry. Her cheeks heated when she noted the wet spot on her panties before she eased them up her thighs. Flushing the toilet as her button was fastened, "Sorry for the wait," she said shyly as she eased past the older woman. Feeling her face heat as the woman's giggle followed her out after washing and drying her hands. "Sorry about that, Drake," Samantha apologized once she returned to her seat.

"Not a problem," Drake uttered, keeping the fact that she seemed flustered to himself. "So, what kind of math are you having problems with?"

"Algebra 2," Samantha said, a little ashamed of that fact.

"Ah, yeah, I can help you with that; it shouldn't take too long to get you caught up," Drake stated, knowing he had aced that course in his freshman year. "Do you need a lift home?" he asked once they left the coffee shop.

"If you don't mind, if I'm not going to be making you late for anything," Samantha said in a shy tone.

"Nah, got plenty of time," Drake replied, escorting her back to his car.

"Thanks, Drake; I really appreciate this," Samantha spoke as they sat in front of her parents' home.

"You're welcome." He was a little taken aback when she leaned over the console and placed a kiss on his cheek.

"I mean it, you're really helping me out here; I'll see you tomorrow at nine?"

"I'll be here," Drake nodded, waving to her before pulling away.

Not seeing Samantha rushing into her home. Locking the door so no one would surprise her before racing to her bedroom and slamming the door behind her. Her clothes went flying. Her soaked panties peeled away from her mound as her legs pointed to the ceiling. Her sex filled the air; her dew glinted in the sunlight that danced along her wet mound as she yanked open the drawer of her nightstand. Hissing in pleasure as her dildo slid into her soaked pussy. Her whimpers filled her room as her hand thrusted that rubber phallus deep into her molten core as she daydreamed about Drake.

Hours earlier...

Iliana stared lazily at her computer screen as the cursor blinked on the screen as it waited for her to input the data that was before her. However, her mind just couldn't let go of the events of this morning. Feeling her mound quivering as she remembered how Drake's tongue felt on her hot little peach. The way her nails dragged along his scalp as she writhed on his bed, howling in pleasure. Recounting how her 36D breasts jostled as she came on that experienced tongue of his. Her pleas to her son of don't stop, to make her pussy yearn for his touch. To make it so fucking wet that she would drown in her own juices. Giggling like a schoolgirl as she raced to her bathroom to shower before heading to work that morning. Hearing her son following after her in his powerful strides.

Yelping in surprise as Drake took her by her hips, spun her around, and forced her to her knees. Her eyes peered up at her son as he held onto the hair on the back of her head. Her tongue darted out as he teased her with that cock of his. Pulling away at the last second, causing her to whine before he fed her that fat rod of his. How she loved hearing his moans, the moans of the man she had fallen in love with as she pleasured that fat pole of his. So very happy that he gave her the chance to redeem herself for the horrible things she said to him over two years ago. Remembering how close she lost her mind in her sorrow for pushing away the man that had shown her through his actions that he truly loved her.

Feeling her nipples harden as her moans filled her bathroom, played out in her mind. Loving how that thick root of his stretched out her pussy like no one before him, not his brothers, not his father, nor any of the men she's been with before Mario. Hearing the wet slaps of her ass as her son pounded that hard tool into her eager pussy. Making it cream his cock like it has done ever since she finally made him hers. Feeling her folds clenching as she sat at her desk remembering the sensations of his cum erupting within her hot cunt. The way he would always gently fondle her breasts as she savored the orgasm he had given her.

A loving smile formed on her lips as her mind replayed how Drake held her in the shower. Holding her like she was the only woman in his life when she knew now that her son was a gigolo. Not something she was happy to learn about, yet when Mario abandoned them and ran off with her sister Idin to south Asia, and how Drake stepped up not only giving her the money to afford a new water heater but also enough to save the home she loved. After all, it was the home she raised her three sweet boys in. The home she knew her love, her son, her man would always come home to. No matter who the woman he was with on any given evening, she knew he would come home to her, his cuckquean.​