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A Simple Life: Chapter 21
🕑 Added 2023-03-17 20:29:40 +0000 UTC“Daddy.” I whisper.
“You want me?” Winona says. “You say you want me?”
I nod.
Though she tries to disguise it a host of emotions were flitting across her regal features. Playfulness, stern control, arousal, and a dash of doubt reveal themselves in tiny glimpses along with who knows what other feelings. I could see that she didn’t quite know what to do with me, but she was going to do something.
“D-Do you want me?” I ask, keeping my voice soft.
“Of course I do!” She laughs. “Sexy kitten like you. Who wouldn’t?”
“He he he.” She called me a sexy kitten!
“The real question is, do you deserve me?” She says. “Well. Do you?”
I shake my head no. “No Daddy.”
“Oh? Why not?”
“I-I’m a silly person.” I say. “And you’re…you’re perfect.”
Her brows raise. “Perfect?”
I nod. “I don’t deserve someone as good as you Winona.”
“Oh geez. Don’t say that Avery.” Leaning forward she reaches out, hesitates, then strokes my hair softly. “You deserve someone good. Everybody does.”
“Sorry.”
“Here. Say this instead. Say, ‘I do deserve you, but good girls need to earn their rewards.’” She pats my head then sits back and resumes her kingly posture. “And show me that pretty smile.”
I do smile, simply from the compliment.
“I do deserve you.” I say. “But good girls need to earn Daddy’s rewards.”
“Mmm. Very true.” She replies. “And have you been a good girl?”
I nod. “Yes Ma’am.”
“Tell me.”
“Um…”
“It’s okay, take your time.”
“Um…” I think. “I…I came up here…even though I was really scared.”
“Oh. That is good! Keep going.”
“I-I asked you on a date.”
“I quite liked that. Go on.”
“I-I m-made a salad, a good one, and I stayed real still to get my makeup on.”
“You did baby girl.” She concurs. “What else?”
“I made a character a-and I think I played her really well.”
“You sure did.” She says. “Anything else?”
“I-I’ve…been listening to Daddy Winona. A-And doing what she tells me.”
“Yes, you have.” She grins. “You like listening to Daddy?”
“Oh yes. Yes I do.” I bow my head even lower. “I like it very much.”
She tilts her head, looking down at me and pondering what to say next. When I dare to glance up I could see in her eyes that she was having every bit as much fun with this as I was.
“You have been a good girl. I cannot deny it.” She says. “And good behavior deserves good rewards.”
A tremble of excitement runs through me.
“Ha ha ha!” Winona suddenly laughs. I look up to see her grinning from ear to ear. “Sorry! I suck at this. HA!” She rubs her cheeks and tries to wipe the smile from her face to reassert her hard, dominant expression. “Gah!”
I giggle. “You’re doing great.”
“Thanks Sprout.” She takes a breath. “Alright. Daddy. Daddy. I got this.”
I cover my face and laugh some more. “He he he he.” She was as new to this stuff as I was! Neither of us had a damned clue as to what we were doing. It only made the shared exploration that much funner. “You got this Daddy. He he he.”
“Pfff! Quit laughing! Ha ha ha ha!”
“Sorry!” I snort and titter.
“Okay, okay. Serious.”
“Serious. Tee hee hee.”
“Totally serious.” She huffs. “Okay…I think…”
“PFFF.”
“GAH! You laugh and I swear to God I’ll spank that lily white ass!”
“Ooo!” I squeal, about to laugh again.
“Don’t!” She points a stern finger.
I pout playfully. “Yes Daddy.”
After a minute we both tamp down the giggles and start again.
“You have been a good girl.” She says. “I suppose you deserve a little something.”
“Thank you.”
With the fingers of her right hand she makes a beckoning motion. “Come here baby girl.”
I crawl toward her.
“That’s it. Good girl.” I crawl to just in front of her and stop. “Come on now. A bit more. Closer.” Confused I look up at her. Any closer and I would be crawling up on the chair. Maybe that’s what she wanted. I scooch even closer then suddenly stop as her foot slides forward between me legs so that the toes were pushing along the crack of my ass. “Right there.” Pressing her shin tight against my groin she says. “There you go.”
“Um.” I look up in need of direction. “What…?”
She peers down on me. Her candlelit face full of the quiet confidence of Lady Ara. “That is what you get. Take it or leave it.”
“Take it…or leave it?”
She gives a single nod. “I told you. I’m not like other girls. I don’t just jump into bed with somebody the moment I see a pretty face.” Carefully she pulls the hair band from my hair and flings off to the side. Her fingers begin to pinch and tease at the hair beside my ear. “Tonight the clothes stay on.”
“Oh. Um…what am I…supposed to do?”
She smiles. “You wanted me. You got me. A part of me at least.” Her smile grows. “Why don’t you just…start rubbing that hot pussy.” She grinds her shin into my cock. “And let’s see what happens.” Tenderly she runs her fingers through my hair. “Take my leg.” Slowly I wrap my hands around the back of her calf. “That’s it. Good girl. Hold on tight. Now lay your head down.” Cupping her hand around the back of my head she guides it down so that I rested my cheek against her thigh like a pillow. Against my forehead was the bulge her own hard cock. Her warm tone lowers to whisper. “Show me how much you want me Avery.”
“Um.”
“Shhhh.” She strokes my head like I were a cat resting on her lap as her leg begins to push and ease against my penis, her big toe prodding between my butt cheeks. “Don’t be shy. Don’t think even about it. Just…feel the good feelings.”
Gripping her calf…I begin to slowly thrust forward and back.
“Good girl. There you go. Good girl.”
I grind my cock against her leg. Through layers of clothes I stimulate myself. Through underwear, jeans, bathrobe, overalls, and possibly even socks I rub against her shin in slow, steady thrusts.
“Feel good?”
“Mmm.” I nod.
“Good.” She croons. Gazing down on me she brings her other hand to my shoulder while the other combs through my hair in long, even strokes. “That’s it. Rub your pussy. Work that clitty. Show Daddy how much you want her.”
“Mmmmm.” I moan a soft womanly moan. My undulating body soon finds a natural rhythm. My cock grinds, grinds, grinds, grinds against the layers of cloth.
“I bet you’re so wet down there.” She caresses my cheek with the backs of her fingers. “Are your panties for me baby girl?”
“Mmmm.” I nod truthfully. I’d been so aroused for so long that this stimulation had my dick burbling slick precum as fast as it could.
“I bet you are.”
Somewhere in the back mind I am cognizant of what was happening here. This woman I barely knew had dressed me as a girl and now had me humping her leg like some dog in heat. By almost any standard this was a moment of humiliation. But…the way she looked at me…the soft warmth I could see in her hazel eyes…the gentle joy I could see on her beautiful face…this wasn’t meant to be demeaning. There was no cruel humor that I could see in that swaddling gaze, only happiness. If anything…I think she respected me more!
Her warm left hand lays across the side of my slender neck. The fingers of her right hand stroke softly through my hair. Against my forehead her thick cock flexes hard and against her soft, fleshy thigh my head nestles. Bringing my hands to behind her knee I pull it hard to my chest, desperate as I was to have as much bodily contact as I could with her. Down below her shin continued to grind, grind, grind, grind.
“Ohhh, you are doing so good baby girl.” Winona says, her face as serene as a mountain lake. “So good.”
This was so different. So new. Kayla and I had never done anything even close to something like this. I dry hump Winona’s leg, rubbing my shaft along the left for awhile before switching to rub along the right. There was no penetration. Besides my underwear my dick had remained completely untouched. And except for occasionally bunting my head against her cock Winona had yet to receive any sexual pleasure from me at all. Yet, somehow, this was easily…EASILY…the hottest thing ever to happen to me.
“Ohhh. Ohhhhhh.” I moan as I grind against Winona’s leg with growing passion. Fucking her leg with all of the focus and energy I would have given her pussy. “Ohhhhhh.”
“Feeling good baby girl?”
“Mmmmmm!” I nod.
“Good. Good. Keep going.” She runs fingers down my temple and along my jaw. “Daddy wants to see you cream those panties.”
“Ohhhhh!” My lilting voice rises.
“Can you creampie your panties for me?”
“Mmmmm!’ I nod.
“There’s a good girl.” She brings two fingers to touch my eyelids. “Close your eyes. Just like that.” Her fingers glide down my nose and over my lips. “Let me see you smile. Good girl.”
“Ohhh. Ohhhhhh. Ohhhhh Daddy.” I mewl, my grinding now a desperate pumping. “Uh! Uh! Uh! I’m gonna cum.”
“Don’t hold back baby girl.” She whispers. “Show Daddy how good you can bust for her.”
Holding her leg firm and still I huff and hump frantically against it.
“Oh! Oh! OHHH!” My lids flare open and the last thing I see are two hazel eyes gazing down into me before… “GNNNNGHHHH!!!” My lithe body bucks and jerks hard as a flood of hot cum fills my shorts. “Ohhhhhhhhh!”
Winona’s eyes widen and her smile brightens as she studies my face through the course of my intense orgasm. All the while she continues to stroke and pet and whisper softly. “Good girl. Good girl.”
“Hahhhh!” I groan in a high, wavering voice as the hard pulses of my pumping cock slowly ebbs away.
When my climax was complete and I am left trembling and clutching to her leg Winona lowers her foot away from my junk. Winona and I hadn’t yet kissed. We’d not even held hands! And here I had just nutted in my pants right in front of her. Post-nut clarity hitting me I suddenly realize how ridiculous I must look. I swallow and go to rise but Winona holds me in place.
“Shhhh.” She smiles that warm, comforting smile. “Just relax. Be still. Enjoy the moment Sprout.”
“I-I…I made a mess.” I whisper.
“Shhhh. Don’t even think about that.” She rubs my back. “Take a deep breath Avery. Relax. Enjoy. Calm.”
Taking a long deep breath I slowly let it out and let my tense body go loose. Settling back against her thigh I rest hunched against her legs, softly petting her calf as I let the hazy afterglow take me.
“There you go.” She bends over and puts her arms around me, holding me exactly like I so needed to be held right now. “Good girl.”
