Wicked vs Good: The Wager

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Help me secure his wrists, Pamela. We can't have him touching himself and ruin things while he watches us play."

Billy finally found his voice. "Jesus Mom, what are you guys doing and, and who is that?" Billy pointed to Dre before he started to struggle against being secured to the bed.

"Shhh baby . . . let's do what Mommy's friend says OK. Now just relax."

"Yes, be a good boy and do as your mother tells you honey," Dre added before whispering some sweet magical words in his ear.

Raising back up, Dre smiled at Billy. He was under her spell now and was no longer struggling. They both took turns stroking his hair before giving him the gentlest of kisses on each of his cheeks--- before snapping the iron shackles around his wrists.

Grabbing Pamela by the hand Dre announced, "Now let's go in my closet and find you something nice to put on, Pamela."

They were inside for quite some time before emerging with Pam wearing a white satin robe while Dre was wearing an identical robe but only black. Both were showing off sexy high heels; Dre's being a pair of slutty looking six inch, black, open toe stilettos, while Pam's wore a more conservative silver pair of evening sandals with three inch heels.

Their heels clicked seductively on the polished stone floor as Dre led Pam over to the luxurious plush white rug spread out in front of the brick fireplace.

The two women, holding hands, sunk slowly down to their knees as they whispered and giggled happily to each other-- like a pair of school girls-- while totally ignoring Billy.

Billy's mind was a mess. He couldn't figure out where he was, how he got there, and why he was shackled to this bed. More importantly, just who was this woman, this sexy, curvaceous, raven haired beauty his mother was obviously very good friends with.

Billy stared at her, trying to figure things out, but her creamy white skin, glowing with unearthly beauty in the soft light cast by the flickering fire, distracted him. She looked altogether mature, like his mother, and, in fact, resembled her enough where she might have been an attractive older sister.

He tried to focus his thoughts on just exactly what was happening, but they kept breaking up-- maybe because he couldn't keep his eyes off Dre's heavenly body which the snug robe very much hinted at.

Then a small voice, and not just any small voice, but that of the raven haired chick with his mom, popped into his head. It was soothing and easy to listen to.

"Relax baby and focus your thoughts entirely on us. We are going to put on such a good show for you honey. Nothing else matters so now just lean forward a bit so you can hear what me and your mommy are whispering to each other."

Billy felt strangely compelled to listen to this woman's voice inside his head. He relaxed, heeding her advice, and even though leaning forward only brought him mere inches closer to them, he could now, somehow, hear them perfectly, even though they were speaking softly and were all the way across the room.

Pam stopped giggling when the previously doormat fireplace roared to life. Turning back to Dre she whispered, "Did you do that?"

"I did. I have a vast array of magical powers on this level, Pamy." Taking Pam's hands into her own, she added, "But just so you know, magic is not what I do best?'

"What do you do best, ahh . . ." Pam asked, "I don't even know your name I afraid."

"It's Drenanya," she whispered.

"Drenanya that is a pretty name. I like it. So tell me Ms. Drenanya . . . what do you do best?"

Dre reached out, stroking the side of Pam's face tenderly before dropping her voice to a sultry whisper, "Sex. Have you ever been kissed by another woman, Pamy?"

"No," she answered timidly.

"Then I guess it will be my supreme honor to be your first."

Billy stared at the scene. Hard. The twin figures of his mom and Dre, facing one another, their hands clasped together in front, were beautifully silhouetted against the dancing flames in the fireplace.

Both women turned toward Billy, greeting his wide staring eyes with soft smiles before they turned back to each other. With a light touch, Dre pulled Pam closer as their lips came slowly together.

Billy, simply unable to turn away, watched his mom and Drenanya engage in a series of ever increasing passionate kisses, causing his manhood to grow in leaps and bounds under the single sheet covering his naked body.

The soft smacking of their lips coming together, and then parting, over and over again, too numerous to count, caused Billy to let out a soft moan. Watching the scene, he fell into a daze of sorts, before the spell was finally broken when Dre pulled back slightly, whispering to his mother, just loud enough for Billy to hear, "Now let's get your pretty robe off of you huh."

Dre's hands slipped down to the robe's knot in front before she slowly untied it. Billy let out a sigh as he watched the robe slip off his mom's shoulders. Underneath Pam was wearing an innocent looking white bra with delicate lace trimming around the edges of the cup. Billy, having a bit of a bra fetish, thought his mother looked delicious in her white bra.

Of course Dre, courtesy of her lord and master the Devil, knew all about Billy's little bra fetish so she had picked out the perfect outfit for Billy's viewing pleasure.

Billy fidgeted against the iron shackles holding him tight when they started to kiss again. Softy, sweetly, the new found friends kissed with the sound of the light smacking of their lips drifting across the room to his ears.

Watching his beautiful mother make out with another hot chick might have been the single most delicious sight Billy had ever witnessed in his brief life.

After slowly guiding Pam's hands to the front of her robe Dre whispered, "Now it's your turn Pamy. Go ahead take my robe off."

After patiently undoing the knotted tie holding Dre's robe tightly shut, Pam patiently slid her friend's robe down and off of her body. Like a laser, Billy's eyes had been focused on Dre's chest. He suspected she was rather well endowed as her dark satin robe was just tight enough around the chest to provide such a hint.

Under the robe, Dre was wearing an all-black ensemble consisting of thigh high stockings, complete with matching sheer black garter belt, and a delicious little thong. But most noticeably, and what really garnered Billy attention was Dre's ultra-sexy black bra leaving little doubt in Billy's mind Ms. Dre was hugely endowed.

Billy continued to watch, his cock growing painfully hard, when Dre brought her hands up and started to fondle his mom's boobs through her white bra.

His mother's only reaction to having this strange woman fondling her tits was one of total submission. She leaned back, closing her eyes, while resting her full weight on her extended arms as she thrust her chest out skyward.

"Hmm, your tits are nice and firm Pamy. Would you mind very much if I was to unhook your bra so me and that anxious young son of yours could get a good look at your boobies."

Pam opened her eyes as she turned toward Billy. "I wouldn't mind, but let's ask him. Honey, would it be OK if Mommy's new best friend unhooked her bra and maybe took it off her."

Billy swallowed hard and then nodded his head yes. He desperately wanted to see his mom's tits. Just as Dre promised it would be, Billy's earlier memories of seeing his mom's naked breasts, thanks to Dre's magic potion, had been wiped totally cleaned.

Dre slipped behind Pam before spinning her about so she was fully facing the bed and her son. Billy stared, with something akin to wide eyed disbelief, as Dre showered his mom's neck with dozens of light kisses while carefully unhooking her bra. Using both fingers, Dre delicately pulled the twin bra straps across Pam's shoulders slowly.

Billy desperately wanted to touch his rock hard cock under the sheet as he watched his mom's bra cling for a few precious seconds to the darkly tanned twin summits of her gorgeous tits before it slipped away-- revealing what to him was the most beautiful sight in the world-- his mother's big, naked tits.

His mom's nipples glistened with unearthly beauty in the soft glow from the fireplace. His cock jerked again as Dre carefully cupped his mom's tits in her hands, jiggly them up and down, before turning her around so she was facing her.

They kissed wildly this time while Dre continued to paw at his mom's breasts. The two women fell back onto the plush rug, mouths glued together, making poor Billy squirm even more. Dre took charge, maneuvering Pam onto her back before raising up. "You wanna see a bit of magic sweetheart?" she called out to Billy.

"Y-yes," he answered.

Dre snapped both her fingers in unison as she spoke some words in old Latin. Four blinding puffs of white smoke suddenly appeared on each corner of the white rug causing Pam to cough and blink her eyes.

When the smoke cleared seconds later Pam was in awe . . . and now quite nervous. At each of the four corners of the large square rug was a black cast iron plate bolted to the floor. Extending from each plate was a short iron chain, also black. Finally, and most ominously, attached to the end of each of the four black chains was a gleaming pair of round manacles.

"A-are those for me?"

Dre smiled whispering, "Who else would they be for Pamy?"

Pam smiled. "I thought maybe they might be for you?"

"Mmm, afraid not," Dre told her softly as she shook her head from side to side.

"Well, why not?"

"Tell me, Pam, sweetheart, what color was the robe you were just wearing?"

"White."

"Pure white yes . . . and what color is your bra and panties."

"White."

"Correct again, both white and both with delicate lace trimming. So sweet and innocent."

"Yes, but what is your point?" snapped impatiently.

"I'm getting there."

"Now what color was my robe?"

"Black."

"And what color is my stockings, along with my bra and panties."

"Black."

"OK and our respective shoes. Mine is both black and slutty, with their six inches heels, while yours are pretty, silver and a bit classier with their three inch heels."

"And all this means?" Pam asked again anxiously.

"It's simple really," Dre said as she took Pam's hands into hers. "Black is the color of power and domination, while white is the color of innocence and submissiveness . . . and who is wearing black?"

"You," she whispered as she felt herself being pushed back onto the rug.

"And who is wearing white?"

"Me," she answered meekly as Dre secured the first shackle around her wrist.

"Good girl," Dre said as she quickly maneuvered around securing Pam with all four of the iron shackles.

Billy's heart was absolutely pounding in his chest while watching this beautiful stranger maneuver his willing mother into place so she was laid out-- spread eagle--naked, expect for her panties and high heels, in the middle of the white rug with each of her four limbs chained securely by those evil looking manacles.

Dre moved slowly, like a cat stalking a mouse maybe, as she patiently climbed on top of his mother, straddling her by sitting lightly on her lower tummy.

The whole time she was carefully maneuvering herself into position she spoke softly to Billy. "Now Billy sweetheart, I want you to watch me and your mommy very closely hon, and if I look up and happen to catch you not staring at us . . . hmm, it will go badly, very badly for your mommy. Do you understand what I am saying?"

Billy swallowed hard before answering, "Yes, I understand."

"Good," Dre replied while giving him the slyest of smiles. "Because if you are a good little boy and watch me, oh so closely, as I play with your mommy I might feel, hmm, inclined to give you a nice reward when I'm done playing with her."

"What kind of reward?" Pam snapped, her jealousy over her son showing.

Dre frowned, fixing, Pam with a baleful glare before answering. "That is my secret Pamy, you don't need to worry your pretty little head off about such things. OK?"

"OK," Pam answered meekly. The look, the look of pure delicious sinfulness on Dre's pretty face, when she fixed her with that menacing frown totally cowed Pam. There was just something about Dre's manner which demanded total obedience. Pam had no doubts her son felt the same way as she finally realized her and Billy were here, wherever the hell here was, in this romantic medieval styled bedroom as nothing more than simple play things for Ms. Drenanya.

Reaching down, Dre lightly ran her hands all over Pam's tits before beginning to squeeze them delicately. Using her thumbs, she flickered them lightly across Pam's nipples making them snap instantly to attention as she let out a soft moan--while struggling against her shackles.

Leaning down, Dre whispered in Pam's ear, "Hmm, I think someone has a pair of highly sensitive nipples. Isn't that right, Pamy?"

"Yes . . . yes they are," Pam replied.

"Well let's find out just how sensitive they are . . . shall we," Dre told her before dropping her mouth to Pam's neck. Apparently, Ms. Dre knew all of Pam's weak points as she found the exact spot on her upper neck, a few inches below her hairline, and just behind the earlobe, and began to assault it with a series of light kisses and gentle nibbles, quickly causing Pam to start squirming all over the plush white carpet.

Pam wasn't the only one squirming though as poor, poor Billy, he too, was struggling something awful over on the bed shackled, just like his mother, and helpless.

His cock was a raging monster now as he watched his mom's beautiful tits bounce and jiggle as she writhed and thrashed about from Dre's teasing kisses on her neck.

And then things really got hot--for both mother and son--as Dre's kisses fell down, down to the soft dark valley of those delicious perfectly tanned tits of Pamela's.

Sprinkling them with the dozens of feather like kisses, Dre made it a point to avoid paying attention to Pam's fully erect nipples. After an inordinate amount of time, Dre finally lifted up to smile at Pam. "Would you like me to give them ripe, fully erect nipples of yours a little bit of attention, Pamy?"

"Oh God, yes . . . Please, Dre, suck on them."

"Hmm, since you said please, I guess I could do that."

Lowering her mouth, Dre let her wicked tongue loose on Pam's nipples making her twist and turn from the delicious assault. After flashing her tongue over each of Pam's nipples several times, Dre opened her mouth wide and began to suckle wildly on each of them in turn.

Watching his mother having those beautiful tits of hers sucked on by her gorgeous friend was hot beyond compare, causing his cock to jerk to new heights of hardness. Yeah, he thought nothing could compare to it, until . . .

Dre raised up, looking down at Pam she whispered, "So what do you think." Dre turned to Billy smiling. "Should we invite your son over to play with us?"

Pam wasted no time in nodding her head yes . . . rather eagerly.

"OK, I'll go ask him if he wants to come over and play with his mommy and her new best friend."

Billy watched, his eyes fixated on Dre's chest, loving the way her big boobs jiggled and bounced happily under the tight confines of her black bra as she strutted across the bedroom to him.

"Your Mommy wants you to come play with us, Billy. Would you like that?"

"Y-yes . . . I think I would like t-that," he replied in a voice that wasn't so steady.

"First I gotta see if you are ready."

Slipping a hand under the sheet, Dre found him to be more than ready.

"Oh my," Dre exclaimed as she turned to Pam, "I don't think I have ever felt a boy as big and as hard as your son is, Pamy."

Jumping to her feet, Dre pronounced a few words, once again in that language neither Pam nor Billy could ever hope to understand, and immediately the shackles securing his wrists to the upper bedposts snapped open with an audible clinking noise.

Leaning closer to him, Dre whispered in his ear, "Before you join us wrap the sheet around your body as I don't want your mommy to get a look at you, down there, just yet."

"OK," Billy responded.

Dre sank down, once again settling herself lightly on Pam's tummy. Turning to Billy, standing nearby with the bedsheet wrapped tightly around his naked body, she motioned for him to sit down behind her. He complied, straddling his mother, directly behind Dre.

Dre twisted herself around to face Billy. Reaching out with one hand, she stroked his face lightly. Leaning closer to him, she whispered, "You are such a handsome boy. I want you to kiss me now . . . like your very life depended on it. Your mommy won't mind . . ."

Almost immediately, the two of them began to share dozens of enthusiastic kisses as Pam could do nothing but watch, with no small amount of jealously. Her jealously only grew as she watched her son begin to paw at Dre's big tits through her sexy black bra.

"Here honey, let me take it off for you," Dre whispered while reaching behind her. Slowly, like she was about to reveal a great masterpiece, Dre unhooked her bra, and then just as deliberately, with both mother and son watching intently, she pulled the bra off and away from her body.

Billy's eyes got big. Dre tits were . . . yeah, pretty fucking big as they basically dwarfed his mom's 36 D's. He had just enough time to mutter a quiet, "Jesus, they are huge," before the action kicked into high gear.

Grabbing Billy's hands, Dre guided them around to her breasts. Billy responded eagerly as he kneaded them with boyish enthusiasm, leaving a distraught Pam to look on enviously.

They begin kissing again, ignoring Pam completely, when Dre rotated completely around to face Billy once more. Scooting back, Dre raised her hips up she was hovering just over Pam's face.

Pam closed her eyes as Dre lowered her pussy unto her face while reaching out and snaking a hand through Billy's long hair, pulling his face down to her chest.

She let out a long sigh as she felt Pam's first tentative licks at her pussy, while Billy's mouth attacked her bountiful breasts with youthful exuberance.

Quickly, Pam's first tentative licks at Dre's tasty pussy were replaced by a lively, eager tongue lashing. In a mere matter of seconds the dream goddess was quivering with anticipation, just as Billy's mouth latched onto one of her large nipples, sucking on it with keen enthusiasm at the exact same moment Pam's tongue found Dre's clit, assailing it with loving passion.

Rotating her face around, Pam applied a tender amount of long loving licks to Dre's delicious tasting pussy causing her to let out a long series of wild moans.

Thanks to the mother and son's combined attentions, Dre soon found herself approaching a mighty orgasm.

"Oh My Dark Lord, Satan . . ." Dre cried as she rocked up and down, "I am . . . I am coming . . . Oh Lucy thank you . . . thank you."

Dre slumped down, a quivering mass of flesh, as an all-powerful orgasm swept her away.

A minute later, the three of them, with Pam in the middle, still secured tightly by her shackles, were cuddling sweetly under a blanket Dre retrieved from her closet.

After about a short reprieve from the fun and games, Dre raised her head from where it had been resting on Pam's shoulder. "So who is next to be pleased . . . just like you two so deliciously just pleased me?"

"I think Billy needs some of our loving attention, Dre. I really imagine the poor boy is ready to erupt," Pam replied.

"Actually I think he could use a bit more teasing before he is ready to be pleased so . . ."

Slipping out from under the blanket, Dre hopped to her feet. "Come with me, Billy," she told him, extending a hand.

Billy was reluctant to leave his mother, but somehow, as he had been all night, felt totally compelled to follow the dream goddess orders. He climbed to his feet, after Dre reminded him to keep the sheet wrapped tightly around his lower body.