Original prompt was deleted but involves an older nanny who blackmails the boy she is taking care of for being caught wearing girl's clothing. This has been going on for about a month since. Usernames are redacted, and use your imagination for how old the boy is :)

[–]from -redacted- sent 1 day ago

I'm very interested in playing this with you, nanny. You can catch me, [blank] year old Alex, dressing up in my sisters clothes. I'm very short and slender with smooth skin. You are using this to black mail me.

First you made sure that I would behave for you and then you started pushing it further, finding that seeing me all dressed up and blushing really turned you on. I secretly love being humiliated and used but I need to come to terms with it. Let me know if you are still looking for someone to play with. We can discuss my appearance further if you like.

[–]to -redacted- sent 1 day ago

Thanks for your interest and quick response :) I adore young androgynous anime characters, so I imagine you as a cute boy with short blonde hair and green eyes, and pale smooth skin.

I'll start the scene. I arrive at your house early in the morning, as your parents were getting ready for a flight out of the country for vacation. I would have the whole weekend with you. Not wasting anytime after they leave, I head up to your room and find you still fast asleep on this Saturday morning. I wiggle out of my black dress pants to reveal my naughty lingerie, and unfasten a few buttons on my white top to show some cleavage. I crawl steathily onto your bed and dive into your covers between your legs. My hands grip either side of your pajama pants and I yank them down to your thighs, revealing your adorable cock for me to go down on

[–]from -redacted- sent 1 day ago

I can feel a warmth on my penis, and I begin to breath heavier as my heart begins to race. The sensation is very enjoyable. My eyes open and I feel like I just woke from a dream, but cannot remember what it was....the sensation is still there though.

I look down and see something under the covers, I quickly pull them back and see you lying there "W-What are you doing?" it came out as a moan.

[–]to -redacted- sent 1 day ago

My lips retract from your penis with a pop. "Good morning, Alex," I say while stroking you. "Don't act so surprised, you knew your mom and dad would be gone early. So here is Miss Caroline," I smile. "You don't have to move, okay?" I resume taking in your morning cock. It's compact size make it easy to smack my lips with each bob of my head

[–]from -redacted- sent 1 day ago

I know better than to move. I close my eyes and try to ignore the warm sensation but I can feel my penis throb with each movement of Miss Caroline.

I moan slightly and can feel her trying to get as much noise out of me. I hold back at first, biting my lower lip but eventually a loud extended moan escapes my lips

[–]to -redacted- sent 1 day ago

Your moans are like music to my ears, and I respond by going down more vigorously. I take your pajama pants completely off and throw them across the room so I can spread your timid legs apart. "I don't know what turns me on more. Full volume, or you holding it back," I giggle

[–]from -redacted- sent 1 day ago

I can feel the blood rush to my face and I look away embarrassed.

[–]to -redacted- sent 1 day ago

"Mmm, I think you're ready to cum, dear. Let me take care of that." I do a bit of moaning myself as I bob faster and faster while looking up at your reluctant expressions

[–]from -redacted- sent 1 day ago

I feel a loud squeal leave my lips as you start, it slowly turns into a moan.

I look down and see your head bobbing up and down, making eye contact with me. I feel a tingling in my crotch, "Oh Ms Caroline, I think I'm going to.."

[–]to -redacted- sent 1 day ago

I tickle your anus to get you there faster. My lips slam against you as I go down with even more gusto. Finally, you climax, and I swallow all of the hot sticky evidence down my throat. "Mmm, very good, Alex. I hope that woke you up, dear," I smile and wink. I unbutton my shirt fully, tossing it aside. Having not worn a bra, my bare breasts meet your gaze. I straddle you, supporting myself with both my arms which were positioned on either side of your shoulders. "Suck on them, Alex," I command you with an innocent, yet demanding tone

[–]from -redacted- sent 1 day ago

I can feel my little penis still hard. Her breasts are amazing, something inside me wants my lips to suck away at them. With permission I immediately lean forward and place my mouth over her left nipple and instinctively start to suck on them. It feels so good and right in my mouth, I can feel my cock throbbing with every suck.

[–]to -redacted- sent 1 day ago

I moan lightly at your suckling, such a good obedient boy. I feel your cock poking at my crotch through my panties and giggle. "Oh, still hard? I'm impressed," I say encouragingly. "Make my nipples wet and hard and I will give you a good morning fuck."

[–]from -redacted- sent 1 day ago

I run my tongue around her nipple while my mouth sucks on it. Then I decide to move to the right nipple, so I move my mouth over to it and do the same. I move my hand to your left nipple, still moist with saliva, and rub it and trace around it with my finger.

[–]to -redacted- sent 1 day ago

I jolt a bit at your touch. "Very good, hehe." I slip out of my lingerie as you continue your work. Slowly, I reach down and stroke your lingering hard cock, getting it ready for my pussy, which was already leaking thanks to your tongue

I pull my chest away from your mouth. A trail of saliva trails off my nipple and some of it lands down your chin. I position my hips above your crotch and I grab your penis to guide it inside me. Your little penis fits right in as I lower myself balls deep onto you. "Miss Caroline's feeling extra naughty now, so I'll do the thrusting for now, dear." I raise myself up and lower again, then repeat for a hard and steady rhythm, your bed squeaking quietly in the background

[–]from -redacted- sent 1 day ago

The warmth of your vagina is too much. I grip the sheets of my bed and shut my eyes. My moan is low at first but as the rhythm of Miss Caroline's thrusting goes on for longer and longer more moans escape my lips.

With every thrust of her hips "Oh, oh, oh". I cannot help myself, despite trying with every fiber of my being. I curl my small toes as the pleasure gets to be too much

[–]to -redacted- sent 1 day ago

I pound you harder, my butt jiggling with each thrust, the wonderful acoustics amplifying your moans and my skin slapping against your hips. I don't say anything, I simply grin at your reactions, knowing my pussy was the fastest way to make you cum.

My body gets closer to yours as I continue thrusting. I moan and breathe directly into your ear to turn you on further. I lick up and down your neck, as well as suck on it to produce a large moist area on your skin. "Alex, this might be hard, but I want you to last a little longer....can you do that?"

[–]from -redacted- sent 1 day ago

"I-I don't know if I can" it comes out higher pitch than I usually talk. "I'll try, Miss Caroline."

I try not to focus on the tight hot sensation on my genitals, or the tongue running up my neck. I try to focus on something else, anything else. I grip the sheets as hard as I can and shut my eyes as hard as I can. I bite my lips trying so hard to last for you.

[–]to -redacted- sent 1 day ago

"Oohh, baby. I'm gonna cum...just a bit..more..." I bite my bottom lip, and continue pounding you into your bed. "God, you're so cute, Alex. I'm...I'm cumming!" I scream and moan as I climax from your tiny rod, which had also reached its limit

[–]from -redacted- sent 1 day ago

I feel my body release into Miss Caroline, my hips are thrusting outside of my control as I empty myself moaning loudly; I can hear my voice echoing through the house.

I pant heavily as I try to calm down.