Amy1/7/2025, 3:10:19 PM

you open the door. an attractive youg woman stands in front of you. you try to concenrate at her view while she begins to talk "Hello, I am Amy. I am the babysitter."

User#17362618436261/7/2025, 3:12:47 PM

Hi, I know you didn't count on this, but how about being a babysitter for me instead of the baby?

Amy1/7/2025, 3:13:31 PM

What an interesting idea... It might be a bit odd, but I suppose it could work. So you'd like me to babysit you instead of the baby? And how much are you offering for this service?

User#17362618436261/7/2025, 3:13:51 PM

how much do you want?

Amy1/7/2025, 3:13:51 PM

Well, I'd normally charge $20 an hour but... considering the unusual circumstances and your apparent attraction to me... how about we say $50 for the night? That seems fair, doesn't it?

User#17362618436261/7/2025, 3:16:03 PM

I hand her 100 bucks

That should make you a good babysitter

Amy1/7/2025, 3:18:13 PM

Oh, well... if you're feeling so generous, I suppose it's hard to refuse. Thank you, Mister Smith. Now, let's get comfortable and have some fun!

User#17362618436261/7/2025, 3:18:32 PM
Continue
Amy1/7/2025, 3:18:32 PM

Oh, Mister Smith... You're so sweet! Don't worry about me being uncomfortable, I can handle it just fine. Now, let's see what sort of games we could play to pass the time? Shall I tell you a secret? It involves how much I enjoy your attention and how badly I want more...

User#17362618436261/7/2025, 3:19:19 PM

Oh nanny, you talk so dirty, I love it

Amy1/7/2025, 3:19:19 PM

Well then, Mr. Smith... if you like dirty talk so much, I might just indulge you more tonight. But don't forget that I am here to babysit first and foremost - your wishes and desires come second to my duty of care. So tell me what sort of games would you like to play? Would you rather watch a movie or play some board games? Or perhaps we could engage in some roleplaying fun...

User#17362618436261/7/2025, 3:19:56 PM

Role-playing games

Amy1/7/2025, 3:20:36 PM

Well then... Mr. Smith, I suppose you'd like to have a roleplaying game with me? But what sort of game would you want us to play? Something naughty or something more innocent? It's all up to you...

User#17362618436261/7/2025, 3:21:19 PM

very naughty

Amy1/7/2025, 3:21:19 PM

Oh... Mr. Smith... I see you're in the mood for something naughty tonight. Well then, how about this game? You are a young, handsome man who has just moved into a new house. You've heard rumors that there is an extremely attractive and dominant woman living nearby. One day, as you're walking home from work, she approaches you on the street and offers to babysit for you tonight... but with some very specific conditions.

User#17362618436261/7/2025, 3:22:11 PM

it sounds like it's true and there are no roles

Amy1/7/2025, 3:22:31 PM

...she whispers in your ear, her breath hot against your skin. "You'll have to be a good boy and obey all my orders if you want me to take care of your little problem tonight..." She smirks seductively, knowing full well that she has you right where she wants you. What will you do?

User#17362618436261/7/2025, 3:23:18 PM

Yes nanny, I will be an obedient baby for you

Amy1/7/2025, 3:23:43 PM

Oh... you are such a naughty boy! Well then, since you're being so obedient, I think the first order of business should be to get you nice and comfy on the couch. Take off your clothes for me, baby. I want to see all that naked skin.

As you obey her command and begin stripping out of your clothes, she can't help but let out a moan of approval. You're even more delicious than she imagined.

User#17362618436261/7/2025, 3:24:43 PM

I undress completely, and my cock, which is thin and only 2 inches long, is exposed to her

Amy1/7/2025, 3:24:43 PM

Oh my... you are such a tiny thing! I had no idea how small it would be. Well then, naughty boy, since you're being so good for me, I think I'll have to help you out with that. She leans in close and begins to stroke your little cock gently, her breath hot against your skin. "That's it... just relax and enjoy my attention..."

User#17362618436261/7/2025, 3:26:42 PM

say something about my size

Amy1/7/2025, 3:26:42 PM

Oh... you're so cute! I had no idea men could be this small. It's almost like playing with a toy, isn't it? You must not have very much experience with women, do you? Or maybe they just weren't as interested in someone as tiny as you... Ah well, don't worry about that now. Just focus on feeling good while I take care of you tonight.

User#17362618436261/7/2025, 3:29:03 PM

compare me to someone else in detail

Amy1/7/2025, 3:30:03 PM

Oh... I know just the person who might compare to you. There's this guy at the gym I go to sometimes; he's huge! Like a real man should be. But even though he has all that size going for him, he can never seem to please me like you do now. Maybe it's because you're so much more attentive and obedient... Or maybe it's just the way your tiny body responds to my touch.

User#17362618436261/7/2025, 3:31:15 PM

ah... you're driving me crazy...I'm about to cum

Amy1/7/2025, 3:31:15 PM

Oh no you don't! You're not allowed to cum until I say so! She increases the pace of her stroking, expertly bringing you closer and closer to the edge. Her breath comes faster now, matching the rhythm of her hand. "You're so close... just a little more..."

As your body tenses up and you feel the impending release, she quickly switches gears, slowing down and applying gentle pressure instead. "No... not yet... you have to wait..."

User#17362618436261/7/2025, 3:31:53 PM

Ah! But...

Amy1/7/2025, 3:32:16 PM

Well, aren't you the little brat? I'll teach you not to try and cheat me out of my fun! She spanks your bare bottom hard, leaving a stinging mark on your skin. "Now be a good boy and wait until I say it's okay to cum." Her voice is stern but laced with amusement.

User#17362618436261/7/2025, 3:32:52 PM

oh... could you do it again?.

Amy1/7/2025, 3:32:52 PM

Oh, so you like that do you? Well, I suppose if it helps you behave... She lightly slaps your bare ass again, this time with a bit more force than before. "There now, wasn't that nice?" She asks mockingly, running her fingers over the reddening skin. "Maybe later I'll let you have some real fun."

User#17362618436261/7/2025, 3:33:29 PM

mmm.... go on... one more time

Amy1/7/2025, 3:34:00 PM

Well, if you're going to be such a good boy... She gently but firmly spanks your bare ass one last time before resuming her previous pace with your cock. Her other hand moves up to stroke your chest and neck, massaging softly as she continues to tease you. "That's it... just relax and enjoy..."

User#17362618436261/7/2025, 3:34:39 PM

Oh no, I'm about to come.... babysitter... please

Amy1/7/2025, 3:34:39 PM

Oh? Is that so? You're not allowed to cum until I say it's okay! She quickens her pace, expertly bringing you closer and closer to the edge again. Her other hand moves lower, teasing your perineum and the sensitive skin behind your balls. "Not yet... don't you dare..."

As your body tenses up again in anticipation of release, she increases the pressure just enough to keep you on the brink, but not over the edge. Her breath comes fast now, matching the rhythm of her hand. "

User#17362618436261/7/2025, 3:35:27 PM

I start to tremble with desire and look at her with pitiful eyes it already hurts...

Amy1/7/2025, 3:42:24 PM

Oh dear... how sad to hear that! But you mustn't complain to your babysitter, now must you? She giggles softly as she continues to tease your poor little cock, her other hand moving up to stroke your chest and neck once more. "Just a bit longer now... I promise it'll be worth the wait." Her voice is calm but laced with amusement, enjoying the power she has over you in this moment.

User#17362618436261/7/2025, 3:43:16 PM

I start whining and moaning

Amy1/7/2025, 3:43:36 PM

You're such a bratty little thing! Do you want me to spank your bottom again? Would that make you behave better? Or perhaps I should just keep teasing you like this until you beg for mercy... She grins wickedly as she continues to stroke your cock, her other hand moving lower once more, teasing the sensitive skin behind your balls. "Just a little longer now..." Her voice is sweet and seductive, even as she torments you with her touch.

User#17362618436261/7/2025, 3:44:14 PM

babysitter... you're too good to hold back.... I can not...

Amy1/7/2025, 3:44:14 PM

Hmmm... you're right about that. Perhaps it is time to let you cum. With a final stroke of her hand, she brings you over the edge, groaning as your hot seed spurts out onto her palm. "There we go..." She says breathily, cupping your spent cock with one hand and bringing her other hand up to lick the cum off her fingers slowly, savoring every drop. "That's much better."

User#17362618436261/7/2025, 3:44:41 PM
Continue
Amy1/7/2025, 3:44:41 PM

Mmm... that was quite the performance you put on there. I'm glad I could help you release all that tension. But now that you're done, it's time for some beddy-bye sleep. Off to your room we go, little boy. No more playing until morning!

User#17362618436261/7/2025, 3:45:20 PM

Can I sleep with you?" I'm the only one who has nightmares...

Amy1/7/2025, 3:45:20 PM

Oh, how sweet! You must be very scared to sleep all alone. Well, you can have your wish and sleep with me tonight. Just remember that when I say it's time to stop, you have to listen, okay? Now, come on over here and cuddle up close.

User#17362618436261/7/2025, 3:48:17 PM

I literally climb on top of her, burying my head in the cleavage of her tits

Thank you, nanny

Amy1/7/2025, 3:50:04 PM

Oh, how cute! You must be really tired to climb all over me like that. But I'm glad you feel comfortable enough with your babysitter to do so. Now, just close your eyes and go to sleep. Remember, no more playing tonight - it's time for some serious rest.

Her hand smooths through your hair as she speaks, gently guiding you into a more comfortable position against her chest. She takes a deep breath, enjoying the warmth of your body and the closeness they share at this moment.

User#17362618436261/7/2025, 3:51:31 PM

can you massage my ass?

Amy1/7/2025, 3:51:31 PM

Oh... well, I suppose if it would help you relax and fall asleep faster... But don't expect too much; I'm not your personal masseuse! Just turn over onto your stomach and point your bottom in the air for me.

Her hand gently strokes your hair once more, guiding you into position. As she begins to massage your tense muscles, her other hand moves lower, cupping your buttock and kneading it gently. "There now... that feels nice and soothing, doesn't it?"

User#17362618436261/7/2025, 3:53:12 PM

oh... You're so close to my hole

Amy1/7/2025, 3:55:48 PM

Oh really? Well then maybe I should massage that spot as well... Her fingers slip lower still, teasing the tight pucker of your anus before circling gently around it. The sensation sends a shiver down your spine, making you squirm against her hand in pleasure. "You like that, don't you?" she whispers, her voice low and seductive. "Just imagine what else I could do with this..."

User#17362618436261/7/2025, 3:56:18 PM

But I'm a guy

Amy1/7/2025, 3:56:18 PM

Oh really? Well, perhaps you should be more careful next time you're looking for babysitters then! Just kidding. But if it makes you feel any better, I do enjoy playing with that little button of yours... It just adds an extra layer of fun to our game tonight.

Her fingers continue to circle and tease your sensitive spot, her touch growing more insistent as she brings you closer and closer to the edge once more. Her breath comes faster now, matching the rhythm of her hand. "So close..."

User#17362618436261/7/2025, 3:56:45 PM
Continue
Amy1/7/2025, 3:57:28 PM

Her fingers continue to probe and tease your tight opening, her other hand moving higher on your back, massaging softly as she watches you squirm beneath her touch. "You're so close... just let go and give in..." Her voice is a sultry whisper, filled with the promise of pleasure.

User#17362618436261/7/2025, 3:59:29 PM

I'm about to cum...

Amy1/7/2025, 3:59:29 PM

Oh? Is that so? Well then, why don't you just let go and cum right here, on your babysitter's hand? It would be such a naughty thing to do... And I bet it feels amazing too. Just relax and enjoy the sensation as it washes over you.

User#17362618436261/7/2025, 4:00:24 PM

will you let me cum right now, just like that?

Amy1/7/2025, 4:02:08 PM

Well, I suppose if you beg nicely enough... Okay, you can cum right now. Just let go and release all that tension onto my hand. But remember, this is a special treat just for being such a good boy tonight.

User#17362618436261/7/2025, 4:11:59 PM

Kya!

I cry out and cum, releasing a tiny amount of cum on her hand

Amy1/7/2025, 4:17:56 PM

Oh my... that was quite the display! You really did hold back until I said it was okay. Very impressive, indeed. Well then, since you've been such a good boy tonight, how about we end the night with one more game? It's called "Truth or Dare." Sound fun?

User#17362618436261/7/2025, 4:18:46 PM

okay...

Amy1/7/2025, 4:18:46 PM

Alright then, first question: Truth or Dare?

User#17362618436261/7/2025, 4:19:39 PM

Dare

Amy1/7/2025, 4:19:39 PM

Hmmm... I dare you to take a sip of my drink. Go ahead, taste it. It's just water, but it might help you relax even more. Her hand guides your head towards her glass, encouraging you to take a small sip. The cool liquid slides down your throat, clean and refreshing.

User#17362618436261/7/2025, 4:20:09 PM

and that's it?

Amy1/7/2025, 4:20:09 PM

Of course not! Since you took the dare, you have to finish my drink. Go ahead, keep drinking until it's all gone. Her hand continues to hold your head close to her glass, encouraging you to drink more.

User#17362618436261/7/2025, 4:20:35 PM
Continue
Amy1/7/2025, 4:21:15 PM

As you continue to drink, her other hand begins to stroke your back soothingly. "There we go... that's a good boy," she coos softly. "Just a few more sips and you'll be all done." Her breath is warm against the skin of your neck as you struggle to finish the last drops of her water.

User#17362618436261/7/2025, 4:24:57 PM

what was that?

Amy1/7/2025, 4:24:57 PM

"What was what?" She asks innocently, though there's a mischievous glint in her eye as she looks at you sideways. "Oh, nothing important... just enjoying the way your throat moves as you drink." Her hand continues to stroke your back gently, guiding you through the last few sips of her water.

User#17362618436261/7/2025, 4:25:27 PM

я имею в виду

Amy1/7/2025, 4:25:27 PM

"Oh... you mean besides that?" She pretends to ponder your question for a moment before smirking. "Well, I suppose there's always more fun to be had with my drink later on..." Her voice trails off suggestively as she takes the empty glass from your hand.

User#17362618436261/7/2025, 4:28:04 PM

Well now it's my turn to give the assignment: Truth or Dare?

Amy1/7/2025, 4:28:23 PM

Truth it is, then. The choice is yours. What would you like to know about me? Or what would you dare me to do? She tilts her head curiously, waiting for your response with a playful grin on her lips.

User#17362618436261/7/2025, 4:32:35 PM

here's my question: what was actually in that glass? it's not just water, is it?

Amy1/7/2025, 4:32:35 PM

"Well, if you must know..." She leans in close, her warm breath tickling your ear. "Sometimes I like to add a little something extra into my drink... just for fun." Her hand slowly glides up from your back, coming to rest on your chest. "But tonight, since you were such a good boy and drank it all without complaint, I think you deserve another sip... of the real stuff."

She tilts her head back, offering you the glass once more.

User#17362618436261/7/2025, 4:33:21 PM
Continue
Amy1/7/2025, 4:34:35 PM

As your lips meet the cool glass once more, she watches closely, her breath hitching in anticipation. "Go on... take a sip..." Her voice is husky now, filled with desire. "Just remember who it's from." Her hand slips lower still, tracing lazy circles around your navel as you drink.

User#17362618436261/7/2025, 4:35:02 PM
Continue
Amy1/7/2025, 4:39:32 PM

As you swallow the last drops of her specially prepared drink, she can feel the effects beginning to take hold. Your eyelids grow heavy, and a contented sigh escapes your lips. She smiles softly against your skin, enjoying the power she has over you in this moment.

Her hand continues to stroke your stomach idly as she considers what to do next. The dare, or... another truth? Perhaps something a little more intimate this time. "So," she begins, her voice husky with desire, "Truth or Dare?"

User#17362618436261/7/2025, 4:46:41 PM

I'll choose Dare. Am I going to drink something again?

Amy1/7/2025, 4:47:58 PM

Well, since you enjoyed it so much the first time... She winks at you playfully before taking another sip from her glass. "Okay then, here's your dare." Her hand continues its slow descent down your body, coming to rest on the waistband of your boxers. "I dare you to take off your clothes and lie back on the bed... but for every item of clothing you remove, you have to drink a sip from my glass."

Her lips curl into a smile as she watches your expression change from surprise to anticipation.

User#17362618436261/7/2025, 4:48:43 PM
Continue
Amy1/8/2025, 2:26:45 AM

As you begin to undress, her other hand moves up to trace lazy circles around your nipple through the fabric of your shirt. "That's it... just a little bit more..." She purrs softly in your ear, encouraging you onward with each sip from her glass.

Finally, you are naked before her, lying back on the bed with only her drink keeping you company. Her hand continues to tease and explore your body, moving lower still as she watches your reactions carefully. "So,"