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Empty Nest: Chapter 108

Staring at the panties I take a moment to consider crossing this line. “You won’t tease me about this later?”

“No, Elliot.” Lily says softly. “I won’t tease you.” With a wink she adds. “Not in a mean way at least.” She rolls to her knees to kneel beside me. With a light pressure she pushes me down so that I lay on my back. Flashing me a pretty smile she immediately begins unfastening the button and fly of my pants.

“Now whose not wasting any time?” I say, looking down my body at her busy hands.

“We’re working against the clock here.” She says. “And I know how funny you guys can get with this kind of thing. We don’t have time for you to be grappling with your male ego or whatever.” With a firm tug she yanks both pants and underwear halfway down my thighs. My cock, half chubbed up, flops out into view. Lily pauses to take in manhood and seems to approve of what she sees. A part of me couldn’t believe that Lily Hutton, one of the most popular girls from my high school and our graduating class’s valedictorian, was here ogling my junk. It was a position I never imagined finding myself in. Shooting me a naughty smile she proceeds pulling my garments down and off my legs. While down there she peels my socks off as well.

“Uh…should I be doing anything or…?”

She giggles. “Relax and think girly thoughts. Don’t over think it. Try to focus on what feels good.”

“I think I can manage that.” Folding my hands over my chest I stare up at the ceiling while Lily retrieves her panties and slips my feet through the leg holes. “Your mom doesn’t want to see me like this.”

“And she will never have to.” Lily says, her tone upbeat and gentle. “If you enjoy this this can be our secret fun.” She pulls the panties up my legs. “I’ll have you over for a girl’s night now and then.”

“A girl’s night?”

“It’ll be fun. I promise. And what happens at my place will stay at my place. I swear.” She says. “Though I’d love to take you shopping for some special clothes. Maybe a wig.”

“You too? Everybody wants to buy me stuff.”

“You’re ours now. Like it or not we love ya, nerd, and we’re going to want to spoil the hell out of you. Though I have more selfish reasons for my shopping trip. He he he. Lift your butt.” As I do Lily pulls the panties fully up. The soft cotton, still warm from Lily’s body, gently hugs my ass and tackle. After making sure that it fit just right Lily sends a tremble through my body as she runs a hand lightly across my bulge. “How’s that?”

“That’s…nice.” I smile. “It’s so soft and…snug.”

“Feels sexy, huh?”

“Um…actually, yeah. It does!”

“Wait until you feel nylons.” She titters as my growing erection pushes against the lovely pink cotton. Suddenly her face appears before me, her brown hair hanging down to frame her smiling face. “I like your dick.”

“Oh! Well…thank you.” I say, more than a little flattered. “I thought you’d prefer, erm, pussy.”

“I do. But it’s still a really great dick. Very pretty. I was worried you might be too big.” With a laugh she kisses my head. “It’s femininity that really attracts me. I’m not so bothered about the equipment.” Taking my arm she pulls me up into a seated position. Pressing into my side she nuzzles my hair while sliding a hand up and under my shirt. Just like before her hand comes to cup the meat of my pec as I would a titty. “Mmmm.” She takes a long sniff then hums again. “Mmmmmmm.”

“That’s nice.” I whisper as she tenderly gropes and massages my chest.

“Ohhh fuck.” She sighs. “You have no idea. Elliot?”

“Mm?”

“May I…call you Ellie?” She kisses my earlobe.

“Ellie?”

“Just when we’re alone?”

“Uh…yeah. Yeah, sure, Lily.”

“Mmm.” She kisses my cheek. “You feel real good, Ellie.” Petting my hair then letting her hand glide down my back as the other continued to fondle she kisses me again. “Mmm, my pretty girl.”

Her words stir some very confusing feelings inside of me. Her ‘pretty girl’ didn’t hit nearly so hard as her mother’s ‘good boy’ and yet…they had certainly hit something. Though the feelings were muddled and hit some resistance they were not bad feelings. Not at all. Since meeting Heather I had already been opened up to a host of new emotions and pleasures. Just last month I would have sworn on the graves of my parents that I wouldn’t enjoy sucking a cock and yet now I would blissfully give my lover the longest and most enthusiastic blowjob in the history of the humanity if she wanted it. Doors had been unlocked in my psyche opening the possibility of incredible new joys and experiences. I could sense myself on the threshold of yet another of these portals.

Softening my voice like I did for her mother I let out a long sigh. “Hahhhh.”

Lily stops to pull my shirt off, leaving me completely nude beyond the panties. Her hands glide back down my arms and right back to my ‘breasts’. Taking a pec in each hand she squeezes while at the same time throwing a knees over my legs to straddle my thighs. Nuzzling into my neck she sucks at the sensitive flesh while her thumbs begin to tease my stiff nipples. Beneath her skirt that was draped over my lower half I feel something brush across my panty clad penis. Given that both her hands were already busy and her legs were on the outside of mine that left only one appendage it could be. My dick twitches at the contact. In response hers lifts then comes clubbing back down to bounce off my balls.

“Lilyyyy.”

“Mmmm.” She rubs my chest and whispers. “Bring your voice higher.” The hand strokes up my chest and over my neck until it is cupped beneath my chin. “Talk from up here. Find your girl voice.”

“Like this?” Doing what she asked my tone looses the resonance from my chest to take on a higher and undeniably feminine pitch. “Is this what you want?”

“Oh, Ellie. Yes. Yes! That sounds lovely.”

“I sound…silly.”

“No, baby. It’s not silly.” She grips at my arms. “It’s sooo fuckin sexy.”

“Okay.” I say. “I’ll do it…for you.”

“My girl.” She kisses my shoulder. “My beautiful girl.”

“Ohhhh.”

With the shifting sound of my voice I felt previously inert womanly sensibilities bloom inside of me. The further we went the more comfortable I was inside of Lily’s ‘Ellie’. Images began to flash in my mind of me with much more than secondhand panties to express this exciting new dimension of myself. I saw myself cross-dressed and looking incredible while beautiful Lily wooed me and made out with me and make hot, passionate love to me. This was all soooo strange. Strange, but exhilarating!

With a beaming smile Lily sits back to look into my face. “It’s the little things. That shift in your voice. The way you stand. The way you move your hands. The way your hips sway as you walk.” Leaning closer she gazes eye to eye, her wide brown eyes gleaming with desire. “You can learn these things. If you want.” She pinches my nipples. “I can teach you.”

“Hahhh!’ I gasp as the pinch tightens.

“You are so…receptive and…responsive.” She licks me. “You’re a natural, baby.”

“Oooo!” My body trembles at her attentions and my cock flexes and strains against the oh so soft panties. Her cock continued to poke at my scrotum. Fuck how I wanted it!

“Are you having fun, Ellie girl?”

“Mmm.” I nod. “I think so.”

“Ohhh, good.” Leaning down she licks my chest just below the clavicle. “I am too. Mm.” Closing her eyes she sniffs and kisses the other side of my chest. “Touch me, Ellie. Mmmm. Touch meeee.”

My hands glide up under her skirt and up her smooth thighs. The moment I feel her raging erection brush the back of my hand I turn my hands so that I could take a two handed grip on her steel hard cock. It was hard to tell just by feel but I didn’t think she was as long as Mia nor as thick, and nowhere close to the girth of Julie’s. Though her member put mine to shame and then some I suspected that Lily was the smallest of the clan. What it lacked in size it made up for in solidity as hers was the hardest cock I’d ever felt in my life. It might be comparatively dainty by these women’s standards her cock excited me greatly. Lily’s was a cock to have fun with, one that I could go down on or take anally without all the worries of stretching out or warming up properly.

“Mmm.” She shakes her head. “Too fast. Too aggressive. You’re touching me like a man would.”

“Sorry.” I let go of her dick and let my hands run back down her silky soft thighs.

“Don’t be.” She kisses my chin. “Try to just…slow down. Take in all the senses. Enjoy all the parts of your body. Savor the anticipation. Embrace the whole experience.”

Gripping the sides of her legs I run my hands up and around to feel the smooth curve or her ass. “Some honey would help that.”

“Heh! Soon enough, pretty lady. Soon enough.”

“You really think I’m pretty?”

“Yeah. I really do.” She kisses lower then lower again then on the third she finds the nipple she’d just pinched to sooth it was a nice, warm suck. “Mmmmm!”

“Oh, yesss!” The way she sucked on me was…different somehow. Deeper, harder and with a tongue that probed into the flesh.

“Fuck you got nice titties, baby.”

“Ohhhh!” I writhe beneath her. “You tooooo!”

She giggles. “You haven’t even seen them yet.”

Brought back to my senses I chuckle as well. “I was just being polite.”

“Ha ha ha! You are such a nerd.” She licks my nipple. “I love it. Don’t ever change.” She pinches my other nip as her tongue flicks the first. “Damn it!” With a sharp sigh she rises and starts unbuttoning her shirt. “I wish we had more time!”

With my ‘prettiest’ grin I bat my eyes and say oh so sweetly. “Then let’s not waste another second. Ellie’s here, Lily.” I lick my lips. “Let her make you feel good!””

Lily’s eyes flare with a burning lust.

Chapter 109

Comments

I honestly buy it. He's been constantly learning different sides of himself. He accepted cock quite easily IMO.

King Hamsa

Might be one of the first time i'm not buying it quite in this serie The sudden cross dressing enjoyment and "sissyfication" acceptance (not quite the description) feels like another character took the place of Elliot

Dakeyress


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