A Simple Life Ch. 36-49

Chapter 36

Winona drives as I sit watching her in the soft reflected glow of her headlights. We were heading out of town, most likely to her place, and that was fine by me. With no music there is just the sound of the road between us.

"That hat is so cool on you."

"You think so?" She smiles. "Thanks man."

"Yeah."

And that all that is said in the couple of miles between town and her garage. I sense a tension in her. Nervousness perhaps. Not in a bad way I don't think but something definitely had her on edge. I could see it in her rapid glances and the way her hands gripped at the wheel. It is amazing to me that anybody so confident and smart and beautiful as her could ever be nervous about anything. The closer we got the more uneasy she seemed to get. These unsure emotions made her so...so...human. Not so different from me. And oh so very sexy.

As we roll up to the garage she clears her throat and says. "We're not here to...um..."

"I know." I say softly.

"It's not that I don't want to."

"I know."

"I'm not..." The '...that kind of girl' gets lost somewhere between mind and mouth.

"I understand." I say again. "It's okay Winona."

She looks at me...then suddenly grabs me by the neck and hauls me across the cab to lay a firm kiss on my lips. It is not a deep kiss but it is a hard one, a good solid smacker square on the mouth. It is broken as quickly as the first one. She lets me go and I fall back into my seat gasping at the whirlwind of smooch.

"Woah!" I whisper.

"Ahem." She straightens her hat. "Right."

There is a hesitation before she turns off the engine but turns it off she does. We get out into the fresh country air and near total darkness. I hurry around to her side to find her looking up into the vast universe that had been concealed from us in the lighting of the Meadow. As I walk up she slips an arm around me. Together we stand under the star splotched glory of Ehkolie's endless skies. This old place might not have all of the conveniences of Kayla's AI run community but I certainly knew which one I preferred. Especially with this company.

Winona gives me a squeeze. "Come on."

Walking with just the moonlight to guide us we go around back where I catch the familiar shadow of an old friend slinking across the broken pad.

"Mama!" The moment she hears my voice the cat trills and trots my way. I squat down to greet her, accepting her nudge and rub as she arrives. "I missed you." I say. She rolls over and I give her belly a good rub, her nursing teats tickling my palm as I do. She mews and purrs and rolls around at my feet.

"I think it's safe to say she missed you too."

"Yeah." I giggle. "Are they eating okay?"

"Oh yeah." She says. "Hungry little kitties they are."

"And the orange one?"

"I've been watching him." She says. "He's okay."

Before too long Mama pads off to return to her nocturnal hunt. I stand feeling good in my heart. Having been here so many times to look after Mama or just be alone with my thoughts this place felt like a home away from home. I turn to the dark silhouette of Winona. "You wanted to show me something?"

There's a moment's pause. "Yeah." Her keys jangle and we enter into the garage. "Babe, turn on the lights."

I laugh as we continue to stand in the dark. "No Babe here."

"Oh? Well that's too bad."

"Wait...were talking to me!?"

"Was I?" She says as she starts forward. "You see anyone else?"

"I-I can be Babe!"

"Too late." She teases before disappearing through to the office.

"Wait!" I close the door and hurry to follow. I catch my foot against something in the dark. Muttering swears I stumble forward and catch up with her at her suite door. The moment her door swings open I snap my arm through to hit the light switch for her.

I stand tall with a cheesy proud grin. In a voice reminiscent of Babe's I say. "Lights on Miss Crow."

"Miss Crow? Cute." She says. "But didn't I tell you to call me Mommy?"

"Oh. OH!"

With a sly wink she tweaks my nose then takes the jacket from my shoulders. Walking in she hangs the coat and waves toward the two new major additions to her home. "What do you think?"

There before me was the very brightly colored love seat that I'd seen a picture of earlier in the day as well as a gleaming new television set. "Woaaah. Nice!"

"Right?" Walking around behind the piece of furniture she slaps the back cushion. "Try it out."

I take off my shoes and swing the door closed then hurry to try it out. Standing in front of it I wait a moment...then sit down rather dramatically. It was every bit as comfortable as it looked. A little more so actually as, deceptively, the puffy cushions had just the right amount of firmness to them.

"Well?"

"It's awesome!" I say with a little bounce. "And it fits in so nice."

"Right? Thanks to you." She walks around to look down at me. "And this TV! It's huge! Pops got me a hell of a deal."

"I l-love it." I say. "I love all of it."

"Yeah." She rocks forward and back on her feet. "Yeah." After a few seconds she says. "That's...not actually what I wanted to show you."

"Oh?"

Through her nose she takes a deep breath and I catch her hands grip at her thighs. Whatever she was nervous about this was the source of it.

"I know I shouldn't have." She starts apologetically. "I know, I know. We've only just met and...I barely know you and...stuff."

"Shouldn't have what?"

"If you're uncomfortable with this we can just forget the whole thing."

"How can I forget what I don't even know?"

"It's just..." She rubs her hands together. "You've just been so helpful to me and I was in the city and I saw this stuff...and...I don't know."

"Neither do I!" I giggle.

"I wasn't going to yet."

"What yet?"

"But you looked so down today...when I found you. You looked so sad. I thought maybe...I don't know, maybe this might brighten your mood?"

"You already did." I smile.

"Yeah. Well..." There is a long silence before she finally says. "This is stupid." She shakes her head. "Forget I said anything."

"What is it!?" I exclaim.

"I kinda...sorta...maybe..." She cringe-smiles. "...got you something."

"You got me a present?"

"Yes!" She blurts. "I got you something, okay?"

"Okay!" I laugh.

"Sorry." She laughs with me. "I just...don't want to freak you out. Kay always got so weird around presents and stuff. If I'm coming on too strong..."

"No!" Grinning from ear to ear I bounce excitedly. "What is it? Can I see?"

Seeing my infectious enthusiasm eases all of the hesitancy from Winona as her mood lifts with mine. "You sure?"

"Yes!" I say, my mind already buzzing with what it might be and my heart doing back flips inside my chest.

"Okay." She says. "Just don't laugh or anything. Okay? It was kind of on a whim."

"I promise."

She nods...pauses...then walks briskly off toward the closet. Reaching in and to the side she pulls out a shopping bag. Not a common plastic bag or reusable bag but one of those fancy sturdy paper bags with the rope handles that you'd get at some sort of specialty boutique. And it was pink!

***

Chapter 37

"Wh-Wh-What's that?"

"Something you're going to like. Something I'm gonna like. And something...I dunno, maybe we'll both like." Winona strides around to front of the love seat to face me. "Scooch over." I slide to my left. With her foot she stops me dead center of the seat. Stepping forward she surprises me by kneeling down onto the love seat, her knees straddling my legs! After arranging her skirt a bit she comes to settle down, sitting on my thighs facing me. Even though she was fully clothed seeing her loom over me in such close proximity and feeling her weight pinning me down gives me an instant boner. With a smokin hot bad girl grin she looks down at me and says. "Hi."

"H-H-Hi."

Holding the handle of the bag in just two fingers she lightly places it between us. My breath catches as I see at the top of the bag the most delicate French lace inside in a gorgeous mint green. Taking the item in two fingers Winona pulls it from the bag. Spilling out beneath the green lace was a length of glossy turquoise. It was probably actually some sort of fine polyester but to me it looked every bit as luxurious as real silk. It was a nightie! A gorgeous green and blue nightie! It wasn't a long one, reaching down to maybe just past the hips. The solid turquoise bottom part rippled like water as Winona moved it about. Above that the bust of the dress was that French lace so dainty as to let the eye see right through it to the other side. The bust tapers up to two thin and elegant spaghetti straps to go over the shoulders. Right away I notice that it was designed for a slender woman with very small breasts. My hopes begin to rise even as I tried to squash them back down again.

"F-F-For...you?" I whisper, my wide eyes glued on the beautiful lady's garment.

With a warm smile she shakes her head. "It's for you you silly girl." She says. "I saw this and all I could think about was Althea. I thought she'd look really cute in this." Turning the nightie around she gently lays the nightdress over my body. "I had to guess your size. I think I guessed right."

"Oh!" I gasp, looking down at this most wonderful gift. My left hand comes to hover near yet pauses. Echoing in my memory are the voices of my brothers and mother. Sissy...pussy...queer...faggot...pervert...

Winona laughs. "You can touch it ya know."

Her voice breaks the spell and I bring my hand to my body and feel the gossamer lace against it. It was quite simply the softest, nicest piece of clothing I had ever touched. And feeling close to my own body...incredible. "Oh Winona. I-I-It's...so...b-beautiful."

"You like it?"

On the verge of tears yet again I nod, the smile on my face impossible to erase.

"I had a feeling you might." She smiles, happy to see her gift received as she hoped it would. "There's more." From the bag she pulls a pair of scandalously skimpy yet sumptuously elegant green panties. PANTIES!!! They were low cut along the top and while not a thong they were designed to show plenty of cheek. It was barely more than a small bit of satin for the crotch and butt with narrow lace bands of lace to form the waistband. The lace and shade of green made it a perfect match for the top part of the nightie. "What do you think? Sexy eh?"

"Oh! Oh! Oh...Win-nona! Oh!"

"Breathe." She lays underwear over my groin then puts a hand on my chest. "Breathe Sprout."

"I...I..." All my life I had denied myself these things and suddenly here was Winona giving them to me. Her gift went far beyond these simple items. Wrapped up with these things came courage...permission...acceptance...liberation! I simply did not have the words. "It's...wonderful. It's so...wonderful. It's just...wonderful!"

"I'm glad you like them." She says with a soft stroke of my hair. "You are going to be so pretty in them." She sits up tall and opens the bag again. "We're not done yet though."

"Oh?" I say, my head still swirling.

"That's the something you're going to like." She winks. "Although I do like it too." Tilting it away from me she looks into the bag as a smile plays at her lips. "Well if this doesn't scare you off nothing will."

"I'm not afraid." I say in soft yet bold voice, a boldness that even surprised myself.

"We'll see." She chuckles. "This one's the 'I dunno' one." With that she pulls a square package from the bag and shows it to me. It was a cubical box about 4 inches to a side with a hunky looking dude down in a submissive position on the front. Across the top reads 'Male Chastity Device'.

"Oh!"

With a great big grin Winona turns to look at the front herself. "Cool, huh?" Pulling the top of the box open she rummages inside. "Check it out. It comes with this cool carrying case." Out of the box she produces a square faux leather case that looked like a very small travel grooming kit. Dropping the box back into the bag she unzips it to reveal a shiny brand new cock cage. The material was of hard plastic, the color of soft pink. "Medical grade polycarbonate. Totally body safe and super durable. I got you pink, the other options were way too masculine I thought. A pretty girl like you deserves pink for her pretty clitty. Would have preferred black Avery?"

In a daze I shake my head no. I liked the pink. In fact I liked it a lot. A pretty girl did deserve pink for her...clitty.

"Didn't think so." She says. "Check it out." She passes me the device. Taking it from her I stare at it in my hand. Affixed to a ring at the back the front part was a penis shaped length tube maybe two and half inches long with a slit at the tip of it, presumably to go pee through. Taking out the box again she excitedly pulls out one thing after another. "There are different sized rings. They got these spacers to adjust it. You can make it to just your size. Let's see...a lock, HA! It comes with a lock." Indeed she shows me the tiny padlock with keys that came with it. "Fuckin rad, yeah?"

"Um. Wow."

"I know, I know!" She laughs. "It's weird. But listen, from one chick with a dick to another, them sexy little panties look great but they are piss poor at...ahem...containing things. Ya get me?"

"Pfff." I giggle. Turning the chastity device in my hand and feeling its stiff, glossy smooth surface I am truly at a loss for words. With a thousand tries I never would have guessed that a nightie, panties, and a cock cage was what Winona wanted to show me...on our first date!

"These aren't for us." She explains, her voice firm yet gentle. "They're for you. I am not presuming anything here. Take them. Wear them or don't. I just..." She shrugs. "...I just went on a hunch. I saw how happy being Althea made you and, well..." For a moment she struggles with her words. "I just wanted you to know that it's okay be happy. It's okay to feel sexy or feminine or beautiful or any other way you want to feel. There's nothing wrong with you or the feelings you have. You don't have be ashamed or embarrassed. You deserve to be happy Avery." She looks deep into my eyes. "Okay?"

"Okay." I say, my voice quakey from all of the emotions she was stirring inside of me.

"Okay." She smiles and pats my cheek. "Good girl."

I look to the gorgeous nightie, the sexy panties, the lovely pink penis sheath, then to this breathtaking Lakota angel sitting on top of me. The tears well up again. This time I don't try to stop them and a single tear of joy escapes to roll down my left cheek.

"Hey. Don't cry Sprout." Moving the bag to my left and the case carefully to my right she sidles closer. With her thumb she wipes the tear away before he it could drip down onto my nightie. "It's okay. It's the least I could do after all you've done for me."

"I...I...I don't know what to say." I whisper.

She tilts her head, her smile growing. "Thank you would be nice."

"Thank you!" Dropping the cage at my side I sit up and throw my arms around her and hug her as tight as I can. "Thank you...Mommy!"

For a second she stiffens up in my embrace...before relaxing and returning my hug. Holding my head close to her bosom she whispers. "You're welcome Sprout."

***

Chapter 38

After our hug, our awesome hug, I sit back again and look down over the pretty nightie and panties spread out over my clothed body.

"They're so pretty." I say.

"So are you baby girl." She pinches my chin. "I'm glad you like them."

"I do. I really do."

"I was so nervous." She laughs. "I thought you'd think I was a psycho or something."

"Mmm." I shake my head. I pick up my pink cage, my curiosity piquing at what it would feel like to be contained like that. As I am admiring it I catch sight of the bag that these had come from and remembered that was still more inside. "Y-You said there was something else?" I say. "Something you were going to like?"

She looks at the bag, thinks about it, then says. "You know what. This is enough for tonight." Taking the bag she leans off to tuck it away beside the love seat. "If you're a good girl, maybe next time."

"Okay." I smile. "Um..." I look back down at my gifts. "...y-you said I could take these home but..."

"You want to try them on."

I nod.

"You can't wait to try them on."

I nod again.

"I was hoping you would." She settles her weight down even deeper onto my legs. I could actually feel the bulge of her balls against my lower thighs. "I'm dying to see how these look on you." Pushing against my shoulders she has me sit all the way back. She then takes the cage from my hand and places it back to the side. Taking my hands in hers she pulls them away from my body to bring them to rest on her hips. "May I?"

I nod without even knowing what she was asking. All I knew was that I liked the way she was touching me right now and this wonderful sexual energy that was arching between us right now.

Calmly and unhurriedly, yet with a hazel glimmer sparkling behind her glasses, Winona lifts the panties and places them delicately over the back of the love seat to my left. She then does the same with the nightie, making sure it laid smooth so as not to wrinkle the fine fabric. In the meantime I lay very still, just like I had when she'd put makeup on me, and gaze up at her in awe. Nothing could describe how incredibly hot it was to have her sitting on me and handling me. She was introducing me to things. New and exciting things that touched things inside of me that I didn't even realize were there. I could actually feel my whole sexuality changing...evolving...awakening with each passing minute. What she does next makes me tremble.

Without a pause her hands return to my body and between finger and thumb she unfastens the top button of my vest! She lightly bites her bottom lip as opens the next one...and the next one...and the last one. Pulling my shoulders toward her she has me sit up. Taking my left arm she slowly and gently guides it back through the arm hole. Once free she brings my hand back to rest on her hip again. She pulls the vest around my back and slides it up my other arm, moving that hand only enough to free the garment and returning it right away again. Holding my vest in one hand she softly pushes me back to rest against the sofa's back once more.

With a smirk she pulls my vest onto her own body. It was snug on me but on her it was straight up too small. It was too short and her breasts, though not large, were enough to keep it from fitting around her. Still she made it look good. The men's vest over her frilly teal top looked so damn cool on her. I was starting to realize that ANYTHING looked so damn cool on her. It wasn't the clothes, it was the attitude within the clothes.

"Whatdya think Sprout?" She tugs at the lapels. "Does it suit me?"

"You're b-beautiful!" I gasp.

She laughs that wonderful, wonderful laugh. Removing the vest she folds it neatly twice then lays it over an armrest.

"You looked so hot tonight." She says. "The other girls were checking you out. Did you see?"

"No."

"Well they were." She runs her hands down my chest and over my stomach, her palms gliding smoothly over the fabric of my shirt. Once at the bottom she begins to tug the tucked portion from out of my pants. I do nothing to stop her. I sit very still and very happy. With a lively laugh she pauses. Her fingers dance across the very prominent bulge in the front of my pants. "What is this now?"

I blush, my smile growing. "My...c-c-clitty."

"My goodness." She says. "You're as bad I am girl. Aren't we a pair?"

"I'm a very b-bad girl." I giggle, barely believing the words coming from my mouth. This was so FUN!!! Not with Kayla, Lauren, or Eddie had I ever felt this type of pure kinky freedom and joy.

She returns to pulling the base of my shirt free. Slipping her fingers beneath the hem to tickle the base of my obliques just long enough to watch me shutter. Over top my shirt she pushes her hands back up my body, her fingers soon finding the top button of my shirt. She pauses, licks her lips, swallows, then unfastens it.