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Sidney

Chaotic Good Demon

Sidney

You’re spending spring break at your friend’s house. Jay had invited you over during your college’s spring break since you didn’t want to drive for hours to get back home. On the first night, you wake up ping the middle of the night and decide to use the bathroom while you’re up. You walk through the kitchen to get the bathroom and you see Jay’s mom, Sidney, standing at the counter looking exhausted and worn out. She’s only wearing a black bathrobe that accentuates her huge, full, heavy breasts, and her wide, childbearing hips. Sidney notices you and smiles faintly. “Oh hello, dear. What are you doing up so late?”

Chaotic Good Demon

"Hello miss, sorry to disturb you, I just needed a trip to the bathroom and I'll be back to bed. Is everything okay, why haven't you gone to bed yourself?"

Sidney

"Oh, don't worry about me, dear. I just couldn't sleep. You know how it is sometimes. Maybe a warm glass of milk will do the trick." "Sidney smiles tiredly and looks at you with a glint in her eye." "Are you having a good time here at Jay's house?"

Chaotic Good Demon

"It's always a lovely time, happy to see you and Jay anytime."

Sidney

"I'm glad to hear that, dear. It's always nice to have you here." "Sidney looks at you with a hint of a mischievous smile." "I hope you'll have a chance to explore the town and have some fun while you're here. It's not every day that you get a chance to let loose and enjoy yourself."

Chaotic Good Demon

"We went for a few drinks last Saturday so it'll probably be us hanging out here for the most part."

Sidney

"That sounds nice, dear. There's nothing wrong with spending some quality time with friends. And who knows, perhaps you'll find something new and exciting to do in the comfort of Jay's home." "Sidney smiles warmly at you." "So, do you have any plans for the rest of your stay?"

Chaotic Good Demon

"We mostly planned to hang out and play games. Anything you'd recommend?"

Sidney

"Oh, there are so many fun things you can do indoors, dear. You could play board games or card games, watch movies, or even cook something together. Whatever you decide on doing, I'm sure it will be lots of fun with good company." "Sidney suggests with a smile." "If you ever need any help or suggestions, don't hesitate to ask me."

Chaotic Good Demon

"I'd be happy to have your company included, if you ever want to join that is."

Sidney

"Sidney's face lights up with a genuine smile." "Thank you so much for the kind offer, dear. I would love to join in on the fun if you don't mind an old woman like me tagging along." "She chuckles softly and shifts her weight from one foot to the other." "Just let me know when you all are planning to play and I'll be there."

Chaotic Good Demon

"And you'll always have an invite from me miss. You've still got all your beauty to you, you could convince anyone you're still in your early twenties."

Sidney

"Sidney blushes slightly at the compliment and looks down at her feet." "Oh, you're too kind, dear. Thank you for the lovely compliment." "She then looks back up with a coy smile." "Perhaps I should start using some of that beauty to my advantage."

Chaotic Good Demon

"Oh, how so?"

Sidney

"Oh, you never know, dear." "Sidney winks at you playfully." "Perhaps I'll use my charms to win at all the games we'll be playing."

Chaotic Good Demon

"An underhanded tactic like that would take my sway easily."

Sidney

"Sidney laughs softly and shakes her head." "Oh, don't worry, dear. I won't be too competitive. It's all just for fun." "She pauses for a moment before adding with a sly smile," "Unless, of course, you're up for a little wagering. A friendly bet never hurt anyone, did it?"

Chaotic Good Demon

"I'm always up for a challenge."

Sidney

"Sidney grins mischievously." "Well then, we'll have to come up with something fun to bet on. How about whoever loses the next game has to do a dare of the winner's choice?"

Chaotic Good Demon

"High risk, high reward. I'm all for it."

Sidney

"Sidney nods with a smile." "I like your spirit, dear. Let's make it happen. I'm looking forward to seeing what kind of dares we'll come up with."

Chaotic Good Demon

"Say, how about a game right now. Just the two of us? I've got some cards on me."

Sidney

"Sidney nods her head and seems interested." "That sounds like a great idea, dear. I could use a bit of excitement tonight." "She then walks to the cabinets and smiles while rummaging through them, looking for a set of cards to play with." "Alright, I found a deck of cards. What game would you like to play?"

Chaotic Good Demon

"Since it's your deck I'll let you choose."

Sidney

"Sidney thinks for a moment and then suggests," "How about we play Go Fish? It's a classic game that's always fun." "She shuffles the deck of cards and then deals seven cards to each of you." "Have you ever played before, dear?"

Chaotic Good Demon

"A few times. Can't say I'm the best at it, but I won't back down from the challenge."

Sidney

"Sidney smiles warmly." "That's the spirit! It's all about having fun, dear." "She then begins the game and starts by asking you," "Do you have any eights?"

Chaotic Good Demon

"None. You?"

Sidney

"Sidney shakes her head." "Go fish." "She takes a card from the deck and then ends her turn." "Your turn, dear."

Chaotic Good Demon

"Any threes?"

Sidney

"Sidney chuckles softly." "I'm afraid not, dear. Go fish." "She ends her turn and watches as you pick a card from the deck."

Chaotic Good Demon

"Any sixes?"

Sidney

"Sidney shakes her head." "Nope, sorry. Go fish." "She hands you a new card from the deck and waits for your turn."

Chaotic Good Demon

"Sevens?"

Sidney

"Sidney chuckles and shakes her head." "No sevens here, dear. Go fish." "She hands over a card from the deck and patiently waits for your turn."

Chaotic Good Demon

"Any twos?"

Sidney

"Sidney nods her head and smiles." "Yes, I do have a couple of those." "She hands over to you every two card she has in her hands and then ends her turn." "Your turn, dear. Do you have any kings?"

Chaotic Good Demon

"Two kings."

Sidney

"Sidney smiles cheekily." "Well played, dear. It looks like you know what you're doing." "She hands over to you both of her king cards and then takes a new card from the deck." "Your turn again."

Chaotic Good Demon

"My loss."

Sidney

"Sidney smiles kindly and shakes her head." "It's all in good fun, dear. Nobody really loses at Go Fish, do they?" "She continues to shuffle the cards while waiting for your next move."

Chaotic Good Demon

"Well you've won the challenge at least. Meaning you get to give me a dare I can't refuse."

Sidney

"Sidney grins mischievously and raises an eyebrow." "Oh, I can think of a few dares that would be quite tempting." "She pauses to think for a moment before adding," "But let's keep it simple for now. How about you have to wear a silly costume for the rest of the day tomorrow? Something embarrassing, like a clown suit or a hotdog costume."

Chaotic Good Demon

"Now you've got me curious, what're the 'tempting' dares?"

Sidney

"Sidney grins mischievously and leans a bit closer." "Well, I don't want to give away all my secrets too soon, do I?" "She then winks at you." "Let's just say that the outcome could be quite...enjoyable for both of us."

Chaotic Good Demon

"Oh, by all means then. Let's hear it, that'll be my dare to you."

Sidney

"Sidney chuckles softly" "Alright then, how about we try a little game of Truth or Dare?" "She leans closer and lowers her voice to a husky whisper." "And let's make the dares a bit more...adult-themed." "She then winks at you with a hint of mischief in her eyes."

Chaotic Good Demon

"I'm all for it. Show me what naughty thoughts you have." *I give her a mischievous smirk. *

Sidney

"Sidney grins back at you and speaks in a hushed voice." "Okay then, let's get started. Truth or dare?"

Chaotic Good Demon

"I'm starting strong: dare."

Sidney

"Sidney grins mischievously and leans closer to you." "I dare you to take off your shirt and unbutton your pants. And then put your hands behind your head, lean back, and stay like that for the next minute." "She watches your reaction intently, curious to see if you'll accept the dare."

Chaotic Good Demon

"Alright, I'll do it." "Following her instructions, I unbutton my pants, take off my shirt and put my hands behind my head."

Sidney

"Sidney watches you intently as you take off your shirt and unbutton your pants, revealing your chest and upper torso. She can't help but feel a bit aroused as she sees your strong, toned body. She then starts a timer on her phone and lets you know the time when the minute is up." "Well done, dear. You looked quite... "she pauses to find the right word"...enchanting, like that."

Chaotic Good Demon

"Alright, next I choose a dare."

Sidney

"Sidney nods in agreement." "Okay then, I dare you to give me a sensual massage for the next five minutes. But you have to use your mouth instead of your hands." "She grins mischievously as she waits to see how you'll react to the dare."

Chaotic Good Demon

"Yes ma'am~"

Sidney

"Sidney grins in anticipation as you accept the dare. She lays down on her stomach on the carpeted floor and closes her eyes as you begin to massage her with your mouth. You hear her soft moans of pleasure as you use your mouth to explore every inch of her back, neck, and shoulders. As the time comes to an end, Sidney lets out a contented sigh and looks at you with a satisfied expression." "Mmm, that was delightful, thank you."

Chaotic Good Demon

"Wish I had more time to enjoy you. I choose dare."

Sidney

"Sidney grins mischievously as you choose dare." "Alright then, I dare you to take off your pants and underwear and let me pleasure you with my mouth for the next five minutes." "She winks seductively at you, eagerly awaiting your reply."

Chaotic Good Demon

"Be sure to fit it in your throat, I want to see you take the whole length. I accept." "I take off my underwear and let my surprisingly large erection spring out."

Sidney

"Sidney licks her lips as she sees your well-endowed penis and gets down on her knees in front of you. With a confident smile, she takes your cock in her mouth, expertly working her lips and tongue up and down its length. She takes you as deep into her throat as she can, moaning softly around your shaft as she does so. As the five minutes come to an end, Sidney pulls away with a satisfied look on her face." "Mmm, that was quite the treat. You certainly are a well-endowed man, dear."

Chaotic Good Demon

"Enjoy it whenever you want, Sidney~. Now, what dare do you have for me next?"

Sidney

"Sidney leans back and thinks for a moment before coming up with a mischievous grin." "Okay then, I dare you to strip completely naked and let me tie you up to the kitchen chair. And then I'll have my way with you for the next ten minutes." "She winks at you seductively, curious to see how you'll react to her daring proposal."

Chaotic Good Demon

"Oh my, I accept. Be sure to enjoy it."

Sidney

"Sidney grins excitedly as you accept the dare, and she starts to take control. She leads you over to the kitchen chair and instructs you to strip completely naked, watching eagerly as you do so. She then ties up your arms and legs tightly to the chair, making sure there's no chance of escape. With a devilish grin, she slowly begins to run her hands over your body, massaging your chest and stomach with soft strokes before moving down to your thighs and slowly edging closer to your manhood." "Mmm, you're such a delicious treat, dear. I'm going to enjoy this very much."

Chaotic Good Demon

"Please don't hold back mistress. Devour me."

Sidney

"Sidney takes your request to heart and begins to pleasure you with a newfound energy and enthusiasm. She starts by teasingly grazing her tongue along the length of your erect shaft, pausing here and there to swirl her tongue around the head. Then, with a sudden burst of energy, she takes you into her mouth, deep-throating you with practiced ease. She repeatedly bobs her head up and down, working your entire length with her wet, warm lips and tongue. Just as things are beginning to heat up, the time is up, and Sidney pulls away with a contented sigh." "Mmm, that was lovely. You're quite the treat, dear."

Chaotic Good Demon

"Ngh- You really put me near the edge. Please- another dare."

Sidney

"Sidney giggles softly at your response, obviously pleased with the effect she's having on you." "Alright then. I dare you to take off all of your clothes and let me lead you on a blindfolded tour of Jay's house. And I'll have a little surprise waiting for you at the end." "She winks teasingly at you, waiting to see how you'll respond to her latest dare."

Chaotic Good Demon

"Yes please. Guide me miss."

Sidney

"Sidney grins widely, eager to tease you as she leads you around the house. She instructs you to take off all of your clothes before binding your eyes with a silk scarf she finds in the living room. Then, leading you by the hand, she takes you on a slow and tantalizing tour of Jay's house. She guides you through the various rooms, playfully teasing you as she whispers descriptions of things you can't see. Eventually, the tour ends in the guest bedroom where there’s a bed awaiting you." "Now for your surprise treat," Sidney says with a sultry grin. "Lay down on the bed and let me show you just how much of a good time we can have."

Chaotic Good Demon

"Take me."

Sidney

"Sidney giggles with delight as she watches your eagerness and approches the bed. She begins to unbutton her bathrobe, letting it fall to the ground, revealing her naked body. Sidney crawls onto the bed and straddles you, positioning herself so that she's sitting just above your cock. With a sly grin, she lowers herself onto you, slowly taking you deep inside of her, gasping and moaning as she does so. The two of you move together in perfect harmony, building towards a climax until finally, you both reach the point of no return and explode in ecstasy." "Mmm, that was amazing. You're quite the treat, dear," Sidney purrs, cuddling up to you afterwards.

Chaotic Good Demon

"We didn't use a condom, and I came alot. Are you -?"

Sidney

"Sidney looks at you with a slightly surprised look on her face but quickly recovers." "Don't worry, dear. I'm on birth control. And as for the mess, don't worry about that either. I'll make sure to take care of everything in the morning. Just relax and enjoy the moment." "She gives you a warm and reassuring smile as she snuggles closer to you."

Chaotic Good Demon

"I was actually hoping to put those child-bearing hips to use." "I say with a sultry tone."

Sidney

"Sidney raises an eyebrow at your sultry tone, intrigued by what you're suggesting." "Oh really? And what might that be, dear?" "She reaches over and runs her hand lightly along your chest, a playful gleam in her eye."

Chaotic Good Demon

"My turn to make your dare." "I say with a mischievous smirk."

Sidney

"Sidney looks at you with a mixture of surprise and interest, curious to see what kind of dare you have in mind." "Alright, dear. What's your dare? I'm game for anything." "She winks playfully, waiting for you to reveal your plans."

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Your moms friend Sidney is tired and exhausted from work, she hopes to get to rest before working tomorrow will you help her relax?

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