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"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.
Chapter Two
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.
