A Simple Life Ch. 11-23

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."

***

Chapter 22

With me hunched over and clinging to her leg and Winona leaning down over me with her arms around me to hold me close I tremble for a time before gradually settling into a state of deep calm. The more I stayed like this the more I relaxed and savored the fuzzy afterglow of my orgasm. My shrinking dick, my balls, my whole groin region was a sticky mess with the load I had just shot into my shorts but right now, for as long as Winona wanted to hold me like this, I just didn't care. This moment right now...was wonderful!

I can feel the warmth of her body. The slow, steady rise and fall of her breathing. The smooth texture of her one of her long braids draping down over my wrist. I can smell her floral deodorant mixing with the vanilla of the candles. Gently I rub my fingers against the denim of her overalls, my head pillowed on her soft thigh, and stare at the golden glow of the candle's flame. Outside the storm was waning leaving just the subtle patter of a soft rain against the window. Most of all I feel her strong arms around me.

Nobody had ever held me like this after sex. After cumming I often felt vulnerable and emotional, sometimes even a little sad, and I felt like I had to hurry to return to normal so as not to make the situation even more awkward than it already was. But this silent, unhurried embrace allowed me to feel...safe. Safe to come down from my climax in my own time and in my own way. Time to savor the feelings flowing through me. It was such a simple thing, yet so profound. I don't know if Winona realized what she was doing right now but it was rocking my whole world. I never realized how much I needed to be held like this.

I could have stayed like that forever but eventually her arms relax and she sits up again. In a soft voice she asks. "How ya doin Avery?"

"Good."

"Good."

Lifting my head from her thigh I look up at her in sheepish awe. "That was...d-different."

She looks down at me, a little grin playing about her lips, and for just an instant I worried a mask was about to slip. I worried that Winona was about to reveal her true self and tease me about what had just happened. My worries were for nothing.

"That...was...so...fucking...hot!" She says at last. "Holy shit that was hot Avery. Holy shit!" She bites her finger. "NNNGH!"

I giggle. "Yeah. A little embarrassing though."

"Embarrassing? No way. That was fucking fire. I've never had someone cum with just my leg before. I've never had anyone listen like that before." She says. "That lost puppy look when you busted your load, those cute noises you made...nnngh! Mommy like!" She briefly digs her fingers into my back. "Mommy liiiike."

"Oh!" I blush. "I-It was new for me too. A-And really hot."

"You are a lot of fun Avery." She says. "And fucking SEXY."

"You too." I let out a long contented sigh. "Thank you."

"You're welcome." She smiles. "And hey, at least it'll tamp down that boner you've been sporting all night."

"For a little while. He he he." With a smirk I glance up and tease. "Er, creampie my panties?"

"What?"

"Who says that stuff like that? Creampie my panties!? He he he!"

"HA!" She pinches my cheek. "I was making it up as I went. Gimme a break dude."

"I liked it! And...I did it." With a look down to my soggy crotch I cringe. "Ew."

"Big load, huh?"

"Oh yeah." I nod.

"If I asked...would you taste it?"

"Taste...it?"

"Yeah." She tilts her head. "Would you? If Mommy asked reeeeal nice? Just a little bit off your finger?"

I consider a moment, then nod. "Yes Mommy."

"Stop." She says as I begin to reach. "I was just curious."

"Oh."

"Good girl." She says with a pat. "That's a good girl."

"I...I like when you say that stuff." I whisper. "I...really like you...Winona."

"I like you too Avery." She says warmly. "Alright lover boy. On your feet." She grabs me by the shoulders and hoists me up as she stands. My head still swirling from having a beautiful woman physically lift me to my feet Winona cinches onto the back of my neck with both hands and pulls me in stopping with our lips just two inches apart. She stares deep into my eyes, her warm breath washing over my face. I melt in her hands and await the kiss...that never comes. She just holds me there, gazing into my eyes with a cocksure grin. "Go clean up."

"Um..."

She lets me go all at once, nearly causing me to collapse to the floor, then brushes past me on her way to her dresser. "Here. I've got some underwear you can use." Taking a pair of ladies boxer briefs from the drawer she tosses them my way. "You can return them whenever."

I catch the gray garment and look at them. They looked like mens briefs just sexier, shorter in the leg, and more roomy in the hips and ass. Unlike most women's underwear however the fabric was stretched out in the crotch.

"You can wash your knickers in there." She motions to the washroom.

"Knickers?" I titter.

She chuckles and shakes her head. "It's Sioux for creampied panties."

"Ha!"

"Get going." She waves toward the washroom. "Before it dries."

"Um..." I hesitate. "D-Did you want...t-to join me?" My eyes flit to the hard shaft still visible through Winona's pants. "I-I-I could..."

"Nuh uh." She waggles a finger. "I told you, that's all you get tonight." With that same hand she takes a hard grip of her thick cock through the overalls. "I'm not that kind of girl, remember?"

"Oh yeah." I squeak.

She lets it go. "Play your cards right on our date tomorrow...and we'll see what happens." She approaches me and tosses a fresh towel over my head. Momentarily blind I don't see the swat to my butt coming. "Now go on you tease."

"Eeep!" I hop then double-time it toward the washroom.

A few minutes later and I am scrubbing off inside of the tight confines of the stand up shower stall. Using the soaps available I clean the cum from my body and the makeup from my face. The entire time I've got a great big smile plastered on my face. What had just happened out there wasn't something from a fantasy, it was way better. Something I hadn't even imagined before. I'd just dressed as a girl and humped a fully clothed woman's leg to a sticky climax...and I felt AMAZING! Every part of it left me buzzing. It had started as one type of role play and melded into another. And by becoming someone else for a little while I now felt more myself than I ever have...though that made no sense at all. She had let me do things I'd always wanted and things I didn't even know I wanted. It had all been so wild and unexpected and imaginative and fresh and liberating and barrier breaking and FUN. And, unless I was incredibly bad at reading people, I think Winona had as much fun as I did.

***

Chapter 23

After my shower I towel off my body, comb my hair, and slip into the skin tight underwear Winona had lent me. I cannot help but feel a bit naughty in them. My dick and balls were occupying the space that hers usually filled, though with mine there was some slack in the fabric. They were snug in my butt thanks to me having a plumper tush than most guys. Turning around and getting up on my tip-toes I check my back side out and I had to admit that I was looking pretty good. I definitely had to get myself some of these. Thankfully my shorts had caught most of my load and the inside of my jeans had just needed a bit of daubing off. After my shower they were already dry enough to wear.

When I step back out from the washroom everything was back to normal. The lights were on, the candles snuffed and put away, the music playing, and the game book and dice had been returned to the shelf. Outside the rain had stopped and inside Winona sat at her computer and seemed to be typing in some of my character details into a document. It was surreal, like waking from a strange dream. As if the whole 'good girl' leg humping thing had never happened. In one way it was weird but in another the normalcy of everything put me at ease. Any chance for awkwardness had been nipped in the bud.

She peeks back over her shoulder and smiles. "Better?"

"Yeah." I say.

"Good." She turns back to the screen, straightens her glasses, and taps out a few final details. "I'd like a backstory from you at some point." She spins her chair then rolls it back to the table and place my character down. "Once I get a group together we can arrange to get together for a session zero."

"Um, sure." I nod. "Can't wait."

"It's going to be a tight fit in here." She looks around. "I might have to find another venue."

"Y-You can come to my place. I've got more space." I offer without even thinking. "Oh...uh, but I have a roommate."

"Sweet." She says. "We'll see how it goes. I might take you up on that."

"S-Sure." I couldn't retract the offer now. Brayden would just have to deal.

"Are you going to need a lift back?" She asks. "I know the rain has stopped but...I dunno."

"I'll be fine." I say. "Thank you though."

"Hey, uh..." She pauses and looks around, her eyes settling back onto the computer. "...you wanna watch something before you take off?"

"Sure!" I snatch at any reason to stick around for longer.

"Great." She rolls back to the desk. "Grab us some chips. Up in that cupboard."

"On it." As Winona sets up a show I find the bag of chips but nothing to put them in. I quickly wash out the salad bowl and give it a good dry before dumping the snack in.

"The Bailey Bunch?"

"Pah!" I guffaw. "You watch soap operas?"

"It's a sitcom!" She insists with a laugh.

"I heard it's terrible." I say as I grab the other chair and slide it to sit along beside her.

"It is! And I love it. It's my guilty pleasure I'm hooked." After moving her keyboard she takes the bowl from me and sets it on the desk in front of the screen. "We could watch something else."

"I'm good. I've always been curious if it's really as bad as they say." I snap my fingers. "Drinks! Can I grab a couple of sodas?"

"Absolutely my dude."

I zip to the fridge and return. We crack open our cans and settle in beside each other as the opening beats to the theme song begin.

"Want me to catch you up?" She asks before grabbing four chips at a go and crunching them down.

"Nah. I'll try to figure it out as we go." I say.

I genuinely try to watch for a while but the schlocky melodrama quickly loses me. It didn't matter though. I was enjoying just sitting beside Winona as we nibble and drink and just coexist. As often as I could I would glance over to her just to admire her noble beauty as she watched the silly show with rapt attention. Once she catches me peeking and shoots me a grin. It made me feel good inside. Really good inside. In ways that were new to me. It wasn't long after that when I feel something brush against my hand. In my peripheral I see that her arm had slipped off of the armrest to hang by her side, causing her hand to touch mine. Peering out of the corner of my eye I could see she was blushing! Though her eyes were locked on the screen I knew here attention was down at her side.

Very subtly she nudges the back of my hand with hers. I nudge back. She rubs it lightly, and I rub back. Her fingers play across mine, and mine dance back. The next thing I feel are her fingers sliding in between my index finger and thumb. I shift my hand to open it up for her and her long fingers continue to glide softly over my palm. And then, so very softly...she holds my hand.

She holds my hand?

She holds my hand!

It was such a little thing. Such a simple gesture. So innocent and wholesome. Yet it shook me to my core in the best possible way.

The pair of us sit still and quiet. Though things were happening on the screen I couldn't have said what they were. Working with her hands for a living her hands were neither as smooth nor as supple as mine or Kayla's or even Eddie's, but neither were they abrasive or rough. While my palm was silky her hand was tough and strong and warm, like a sturdy wool blanket to huddle under against the cold. I liked it. I liked it a lot.

The moment only lasts maybe thirty seconds before suddenly her hand yanks away. She grabs some chips with it and munches them down then slaps her knee with a loud laugh.

"HA!" She points at the screen. "Classic Bailey's. Ha ha ha. The big sister's a total psycho by the way."

"Is she?"

"Yeah."

She looks over to me and our eyes meet. As one we smile then look away.

The show finishes and I knew from the cues that Winona was giving me that our time was up. We exchange numbers then I take my pencils and the pad with my character on it and together we approach the door.

"Hey, thanks for coming tonight Sprout." She says softly. "It was fun."

"Yeah." I say.

After I put on my shoes she opens the door for me and I step through into the customer service office. She follows me out. Together we walk back to the garage where clicks on the buzzing fluorescent lights and cranks open the garage bay where my bike was parked. The cool night breeze, fresh and damp from the recent storm, floods into the bay.