My Son the Gigolo Pt. 02

"That was so beautiful," Cybil sniffed, drying her eyes as she had silently listened in while in the bathroom, only seeing the last part of their discussion. "You two are truly meant for one another," she said in a happy sigh.

"We are, aren't we, honey?" Iliana cooed as she wrapped her arms around his neck, causing the sleeves of her dress to show off the toneness of her arms that Franklin and Aydin had helped her achieve.

"I would hope so. Otherwise, it's going to be awkward with the ring in my pocket," Drake teased, seeing his mother's eyes, along with Cybil's, widening as those words left his lips.

"Ass," Iliana uttered playfully, slapping his chest, seeing the funk her son was in fading from his eyes as Drake laughed. "Don't you dare, and I mean never, tease me about that! Unless you're really going to do it," she said, wagging her finger at him.

"That so, hmm, this changes things," Drake mused, wondering if he should contact the jeweler he uses back in Nashville.

"You're not joking, are you?" Iliana muttered; her heart leapt into her throat as she saw the seriousness in her son's eyes.

"Why would I joke about that, Iliana, I've always wanted you, and now that I have you, I want the world to know it," Drake stated in a firm tone. Watching how his mother's hands flew to her mouth, how her eyes quivered as she stared at him.

"Oh, baby?!" Iliana uttered, throwing her arms around him, hugging him tightly to her. "Yes, a thousand times yes," she whispered as she nuzzled his neck.

"But don't I have to ask first?" Drake teased.

"Don't spoil this!" Iliana hissed in his ear.

"I'm so happy for the two of you!" Cybil squealed before turning their hug into a group one.

"Now I think it's time for you to take your future wife out to dinner, don't you think?" Iliana asked coyly, her eyes shone brightly in the light as she spoke those words.

"Right, you are, the future Mrs. Cole," Drake said, wondering how his mother was going to take to being married to his alter ego. Seeing that loving smile and the mischievousness in her eyes as they shared their own private joke between the two of them as she looped her arm around his.

"You do know this means I'm so picking out the ring." Iliana's voice could be heard through the gap of the door as it closed behind the three of them as they left for the evening.

******

"Oh, God, I'm so fucking sore?!" Cybil moaned. She hissed as her pussy throbbed like mad from the pounding she and it had taken from the time they got back to the room at seven to the hour of midnight.

"I did tell you, you would be," Iliana stated as she got ready to head down for their last day of the conference.

"But it was so worth it!" Cybil sighed, falling back on the bed where she had taken another man on, still smelling her sex along with Drake's on the comforter after eight hours. Looking over at Iliana, recounting how she would fill her legs whenever Drake had come in her. Feeling her pussy growing moist at the thought of having her tongue inside of her again. "Iliana, why don't we cut out early? The thing is over at one anyway; no one's going to notice us missing and come back up here so you can get your own ride.

"Oh, did you think Dante was doing nothing when you passed out those few times?" Iliana asked, shooting her friend a coy smirk. "I know how to handle that beast of his, but you loved having my man between your legs, didn't you?" she purred as she slipped her hand into her friend's skirt, playing with Cybil's sore pussy through her panties.

Cybil looked up; towards the bed, they all had slept on due to how soiled the one they'd had sex on had gotten last night when Iliana had a smile on her face as she peered at it. A devilish grin appeared on her lips when Drake's cock filled her view. She didn't hesitate; she just opened her mouth, telling him she wanted it, no matter how sore she was. Which Drake didn't hesitate to fill her mouth with his hard rod. Switching out with Iliana, who lavished his pole in ways she never tried. Also, noting how Iliana was pulling her panties down as her hips shook as her skirt was bunched up at her waist.

"We don't have a lot of time, honey, but I want to feel your cum in me throughout the whole thing," Iliana stated, moving hurriedly to kneel at the side of the bed where Drake was standing, bending over, presenting her ass to her son. Breathing heavily into the mattress as she felt his hand moving along her ass while his other played with her hot mound before easing his cock into her eager folds. Her teeth tore at the comforter as Drake took her hard and fast; how she fucking loved it!

"What?!" Cybil's face heated when Iliana peered over at her as she mimicked her friend. "I might be sore, but there's no way I'm going to miss fucking that cock."

"Alright, but I get the creampie this time," Iliana said, flashing her friend a smile.

"Deal, but would you mind if he gave me one before we got back to Nashville so I can go home with another man's cum in my cunt to show that dumbass what he'll be missing if he doesn't straighten up his... oh shit... slow Dante, take it slow," Cybil panted, having lost her train of thought when he slid his cock into her sore cunt. "God, I'm going to miss this so much," she sighed before squealing when Drake poured on the speed.

"Well, tell you what, you don't tell anyone who you fucked, name wise, the pictures you have don't have his face in them, so that won't matter, and if your husband leaves, we'll make this like a weekly thing," Iliana stated, really getting into her cuckquean role. Being with Emma was nice, yet they had done nearly all the positions with each other, and Iliana didn't want this to get stale for her son.

"Y-y-you really mean that?!" Cybil stammered in shock. She had thought this would be a one-time thing. Something that she would only have memories to look back on.

"Mm... fuck me! Yes, baby fuck me!" Iliana howled when Drake slipped his cock back into her. "That's it, right fucking there!" Screaming into the mattress as she came hard on her son's cock like it should always be. "Or how about we make him into a cuckold? Only fitting life for a cheating bastard, don't you think?"

"That's totally wicked, Iliana," Cybil giggled evilly before she gasped loudly as Drake buried himself back into her cunt. Her eyes rolled back into her head as her body was his to do with as her pussy would never let him go as she just came as hard as the first time she had his cock deep inside of her.

"Yeah, give it to her baby, make the bitch howl like the devil as she cums on your cock," Iliana egged Drake on, shooting Cybil a smile before he did just that.

"I want to taste me on your cock," she stated, something she didn't get the chance to due to how Iliana had always sucked him clean. Moaning around his shaft, loving how her sex tasted on his skin. "Now put that hard cock back in this horny bitch," Cybil spoke as she spread Iliana's ass cheeks apart. "Now, let me taste her on you; I have to know what she's like, after all the times she cleaned my cream from your cock. Yeah, feed me that cock," she purred as Drake placed his hand on top of her head as he slid his slick phallus into her mouth.

"Thank you, baby, that's exactly what I needed; now I know I'll get through the rest of the conference with your cum soiling my panties," Iliana purred lustfully as she lightly kissed Drake as he laid down to recoup his strength. "You get some sleep; you made me proud last night. Maybe you'll be up for some five hours with me one night," she said, allowing her innuendo to hang in the air.

******

"Yeah, you like that tight pussy wrapped around your cock don't you, Dante?" Cybil huffed as she was riding Drake hard in the back seat as they crossed into the city of Nashville. She didn't care who saw her fucking the man in her friend's backseat. Not after the exceptional orgasms, the man had given her. She lost count after her twenty-fifth one. "Yeah, that's it, fuck that pussy like you own it!" she moaned like a harlot in lust as Drake hammered his cock into her wet, sore hole. Knowing it was going to be days before she would be able to have her husband between her legs. She had said she wanted it hard and rough, and she got what she asked for, not that she was complaining; she loved every minute of it. Leaning forward, lifting up her shirt and bra over her breasts. "Give me your mark, Dante," Cybil stated, seeing the confusion on his face. "You're love bite, so he will see I've been taken by you.

"Fuck?!" Drake grunted as Cybil's pussy tightened on his sore cock as he gently bit the side of her left breast.

"That's it, Dante, give me that hot fucking cum!" Cybil cried out as she came alongside him.

"Good timing since we're nearly there," Iliana stated, watching how Cybil straightened out her clothes in the rearview mirror. "Well, seems the car got fixed," she said as they neared their home.

"Good, no telling what they did to my car while we were away," Drake spoke, peering around the passenger headrest.

"Who are you talking about?" Cybil asked, looking at Drake.

"My boys," Iliana answered. "The fuel pump went out on the car Saturday, and Dante here paid to get it fixed and allowed them to use his car to go to school while we were gone."

"Awe, that's really sweet of you," Cybil said, flashing him a smile. All the while, she was pondering if she should take Iliana up on her offer. Now that she's had something so large, felt how it made her fucking cum like a waterfall, she didn't want to give it up. "Iliana?"

"Hmm?"

"Does that offer still stand?"

"About making your husband into a cuckold?" Iliana asked curiously.

"Mmmhmm," Cybil hummed as she nodded.

"Of course it does; why? Are you interested in joining our little group sessions?"

"I am, but only if you and Dante are okay with it," Cybil said, looking between the two. "I don't want to put any pressure on the two of you."

"No pressure, honey; I was the one that suggested it after all. Dante, will you be okay with this?" Iliana asked, peering at him in the mirror.

"As long as it isn't like last night, I think you two drained two weeks' worth of cum out of me," Drake groaned.

"But it was fun, wasn't it?" Cybil asked, flashing Drake a sultry smile.

"True, it was."

"I promise it will only be an hour," Cybil said, reaching over and resting her hand over his. "It will have to be on Sundays since my mother takes the kids to church with her, and he's normally passed out drunk from the night before to notice me gone. Will that work for the two of you?"

"Sure, Sunday sounds fine with me," Iliana spoke as she pulled into their driveway, with Drake nodding along.

"Hello? Oh, hey, what's up?" Drake asked after answering his phone once he got out of the car. "No, we just pulled in; when? Extra? Really, wow, she must be desperate for that. Yeah..."

"Who's that?" Cybil asked low as Drake walked off to give himself some privacy.

"His boss," Iliana stated as she popped the trunk.

"Thank you so much for sharing him with me," Cybil whispered as she hugged her friend. "I'll never forget this."

"You be safe going home, alright?" Iliana stated in a friendly tone as she rubbed her friend's back.

"I will, and don't you wear his cock out too much," Cybil said sinfully as she placed her bag into the trunk of her own car.

"Oh, I had planned on it," Iliana mused, getting a chuckle out of her friend.

"See you at work tomorrow, bye Dante; thank you for the lovely time and the amazing sex," Cybil said low so as not to be overheard by the person on the other end of his phone call. Feeling her cheeks heat as he waved to her. Knowing her Sunday mornings would be spent praying to her new god, the mighty hammer he has swinging between his legs.

"Hey boys, did you behave yourselves?" Iliana asked in a motherly tone as she got a hug and a kiss on the cheek from Franklin and Aydin. Ever since she and Drake officially became a couple, she forbade them from kissing her on her lips, at least when they weren't having sex. Outside of that act, she thought that should strictly be something only she and Drake should be doing, given their new relationship.

"Yes," Franklin mumbled. "Let me help you with those, Mom," he said, taking the bags from her.

"How's the car running now?"

"Like it's brand new," Aydin answered with a smile. "So, who is Drake talking to?"

"His boss." Seeing Drake snapping his fingers for the keys to his car.

"Drake, I'll pull it out for you," Aydin stated, eager to get one more minute behind the wheel of it since Franklin had hogged driving it. Grinning at his brother as Franklin reluctantly handed over the keys to him.

"You two weren't fighting over it, were you?" Iliana asked in a motherly tone as she walked beside Franklin towards the front door.

"No," Franklin lied. Hearing the Fusion starting and the garage door opening as Aydin backed the car into the street and pulled it along the curb. Shooting daggers at his brother as he walked arrogantly towards the garage. How he loved driving his brother's car, it was in another world compared to driving the Fusion. Even Aydin said it was slightly better than driving the Audi; he would have to take his brother's word for that since he's yet to drive it. Escorting his mother into the house when Drake finally got off the phone with whomever he was speaking to.

"See, Drake, not a scratch on it," Aydin boasted as Drake walked around the car. Seeing how his eyes moved along it, studying everything, hearing the car door opening as Drake made sure they didn't tear up the inside of his car.

"Aydin?!" Drake's voice filled the interior of it.

"What?" Aydin spoke with a bit of worry in his voice.

"What did I say about people in my car?"

"I swear no..." Aydin's voice died away when Drake held up a pair of panties between his fingers.

"You were saying?"

"Drake, I swear, we wouldn't allow anyone in your car; she must have thrown them into the back to cause trouble," Aydin pleaded with his brother to believe him.

"I think you and Frank need to detail my car," Drake said, wondering if he could get away with his prank.

"Ah, come... you're fucking with me, God, you're an asshole," Aydin bemoaned, crossing his arms along his chest when he finally caught on. "So, who's panties are those? I know they aren't Mom's... wait, you didn't, not with that petite blonde?!" Groaning as he tossed his head back, wondering how was it that his brother was getting more pussy than either he or Franklin was ever getting. He was the jock, and until two years ago, Drake was the scrawny, nerdy kid. It felt as if the universe had indeed been overturned. "Is that why you kind of look like death warmed over?" Aydin asked with an arched eyebrow as Drake shut the car door. Hearing the alarm chirping when Drake locked up his car.

"Yeah, she was a little minx in the sack," Drake said, rubbing the back of his neck.

"So, how was it, being away with just you and Mom, minus that woman," Aydin spoke as he and Drake walked towards the house. Seeing that smile on his brother's lips, knowing they must have had a good time together. "Glad you and Mom are getting along," he said in a warm brotherly voice as he rested his arm along Drake's shoulders.

"What do you mean you and Drake are going ring shopping Saturday?" Franklin's voice could be heard coming from the kitchen.

"Where do you think you're going?" Aydin stated, grabbing the back of Drake's shirt when he tried to escape back out the front door. "Oh, you so aren't going to be getting out of this so easily," he said, dragging Drake towards the kitchen. "So, what's this about a ring?" Aydin asked, keeping a firm hold on Drake's right arm.

"Your brother asked me to marry him," Iliana said in a dreamy voice as she gazed at her son. "And I said yes. So we're going ring shopping Saturday," she stated with a wide, happy smile on her face.

"I see, and you thought to do around about on us, huh?" Aydin spoke, staring his brother down in a teasing light.

"Not that I need either of your approval, but yes, yes, I did," Drake said, ripping his arm out of Aydin's grip.

"Listen here, pipsqueak," Franklin spoke in a stern tone as he loomed over his brother. "You hurt Mom, and you'll have to answer to us, we clear on that?" he asked, poking his brother in his chest.

"Like I would ever, just look at her, she's perfect," Drake said, not backing down. Noticing how his mother's face lit up when he said that, and her loving look deepened as a smile formed on her face.

"Good, as long as you remember that," Franklin uttered; a brotherly smile appeared on his lips as he hugged his brother. "I'm happy for the both of you," he said, lightly patting Drake on his back before he engulfed his mother in that same warm hug.

******

"So, where are you going tonight?" Iliana asked, sitting on their bed, propping herself on her arms while her right leg sat on top of her left knee, her foot lightly kicking in the air.

"Some club that just opened up," Drake said, getting ready to head to Garden Hills to pick Brie up.

"Is that why you're not wearing one of your suits?" Iliana inquired; she loved seeing him in one of them. More so when she was the one peeling it off of him.

"Yeah, she wanted the boyfriend experience, paid double to get me to come out on my day off," Drake stated as he rolled up the cuffs of his slim, casual fit, white dress shirt that molded around his chest to his elbows to show off the delicate paisley printing that lined the cuff and collar; it's red and blue buttons match the printing's color that he had bought when he was in Italy. Seeing the hungry look in his mother's eyes when they ran down his chest.

"Does that still mean you're working tomorrow?" Iliana asked, wondering if she would get another night alone with him.

"No, she pushed it up to tonight, so unless my Madam calls me before noon tomorrow, I'm off. Why, want me all to yourself?" Drake asked with a taunting grin.

"You know I do," Iliana said sweetly. Her body heated as Drake neared. Her lips pulled at his, her fingers feathered out along his cheeks. Loving how his lips felt so perfect on hers as she savored the man she loved. "I'm never going to leave you, Drake, not now, not ever; I knew you were worried about it Monday night. A mother knows these things," she cooed as she stared into her son's eyes. "My place will always be here, Drake, in your heart and by your side. Even if we can only live as a common-law couple, no matter if Tennessee doesn't recognize it. I will always be your wife and your mother. But I expect a grand honeymoon, you hear?"

"Oh, whatever shall we do on it," Drake mused as he leaned forward, causing his mother's back to find its home on their bed.

"This and that," Iliana stated, lightly rubbing her right thigh along his hip as her hips rocked as his fingers teased her mound. Biting her lip, loving how her body responded to her son's touch. Feeling her heat rising as they made out on the bed. Groaning loudly when Drake's alarm went off, telling them it was time for him to leave for the night.

"Love you, always have," Drake said in a loving tone as he stared down at his mother.

"And I love you more than you will ever know," Iliana responded in a breathless whisper before they shared a passionate kiss. Feeling the heat flooding her cheeks as she gazed bashfully at her son as Drake stood in the doorway of their bedroom. Feeling like she was twenty years old again as those eyes of his gazed at her. Her heart fluttered as Drake blew her a kiss before he turned and left down the hallway.

"Aydin!"

"Yeah?"

"Take care of Mom for me; I got her all worked up, but work calls."