Empty Nest: Chapter 109

With me in nothing but panties, my tit still tingling from where Lily had sucked it, and her on top of me with lust in her eyes the pair of us stare at each other for a long moment as it truly dawns on us that this was about to happen. Whatever ‘this’ ended up being it was definitely gonna be something. There was some reluctance in her to ‘cross that line’ even now that it was clear we were crossing it. I’m not sure if it was because of who we used to be, because of her mom, because I was a dude, or because she felt she might be betraying her twin brother in some way but I sensed the mental hurdle in her even as it melted to the heat of the moment. Not wanting regret to be Lily’s lasting memory of today I keep things light and playful.

Keeping my voice soft and lilting I say with a wink. “How am I gonna tell if you got as nice of titties as me if you don’t show them?”

She laughs, my quip all that she needed to give in to the inevitable. “Well what are ya waiting for, pretty girl?”

“He he he!” I cannot contain my giggles as I thrust my hands up under her sweater. My first instinct is to go straight for her tits and grab them but, recalling what she’d told me earlier about touching her like a guy, I instead slow my advance to savor the warm flesh of her stomach. When I do reach the sleek fabric of her bra and the full, round tits beneath I run my thumbs across the front and feel her aroused nipples protruding slightly even through the fabric. After just a light brush I slide my hands around to the sides to give each breast a sensual caress.

“Mmmm.” She moans softly at my touch as I run my hands back down her sides again. “God, your hands feel good.”

“Not as good as you.”

She clearly wanted to enjoy this soft petting further but our time together was short and she had nut to bust before we got out of here. In a sort of slow, seductive dance with her upper body she pulls the sweater all the up her body and then her arms before letting it drop down behind her. Savoring the feel of my hands on her flesh she continues the dance as she reaches behind her to unfasten her bra. I lay my hands over her boobs, take a grip of her bra, then gently pull it away from her body.

Topless and smiling Lily was sexier than I’d ever imagined. Eight years ago I would have given up my left nut for even a glimpse of smokin hot Lily Hutton’s tits and seeing them now…it would have been worth it! If one was to search the term ‘perfect breasts’ Lily’s rack would have been at the very top of the results. Round, full, smooth, bigger than average but not actually huge, perky yet with just the right amount ‘pout’ to give that natural teardrop shape combined with circular pink areola with subtly jutting pink nipples hers was a pair that could bring a dead man’s cock to a full salute. Though I was MILF man now and wouldn’t trade Heather’s big ol’ jubblies for anything in this world I could recognize transcendent perfection when I saw it.

Cupping her titties and giving them a little squeeze I say. “See. I knew they’d be awesome.”

“Pff!” She laughs. Laying her hands over mine she brings them up to take a more fulsome hold on her soft breasts. After letting me fondle her for a time she looks down and quips. “Sooo…bigger tits top?”

“That’s hardly fair!”

“Heh! Bigger dick then?”

“You’re as bad as Julie.” I chuckle.

“GAH! I forgot you two fooled around already.” Her face scrunches. “This is so WEIRD!”

“Julie and Elliot fooled around.” I whisper. “Ellie is all yours, Lily.” Reaching up place a finger and a thumb over her eyes and close the lids. “Close your eyes.” I whisper. “Think about Ellie. She’s here. She’s right here. And she’s yours.”

Her pretty smile grows. Finding my head she strokes my hair then runs a hand along my neck then down the center of my chest. “You smell so good. You feel sooooo…good.”

“Ohhh, Lily.” Wrapping an arm around the small of her back I rise to sit up. As she runs her hands up and down my back I continue to explore her naked flesh with hands and mouth. “Mmm.” I give her a long, gently sucking kiss to the inside of her right breast while my hands follow the shape of her hourglass figure. On the way back down again I find the zipper of her skirt and slowly pull it down to loosen the waist. Her thoughts are a mirror of mine as she is already pulling the skirt up and off of her before I’d even finished the zipper. “Oh my God.”

“Yessss.” She squeezes my tits and begins to rock her hips. With each rock she shifts ever forward until her hard as steel cock is rubbing against my belly.

“Mmm.” I kiss her other breast as my hands sink into her firm yet soft ass. Again there is the pull and push of wanting to savor this sensual moment and knowing that we had to hurry. After a bit more petting I brush my hand along her penis then take a light grip of it to begin to stroke.

“Ohhhhh, Elliiieee.” She sighs, her eyes still closed.

“Mouth or hand?” I whisper softly.

“Mmmmm.” Lily drags her nails across my shoulders. I knew she would have preferred my ‘pussy’ but we didn’t have time to build up to a proper love-making session, which wasn’t bad because I wasn’t allowed to bottom right now anyhow.

“Or if feet are your thing…?”

“Feet?” She lets out a laugh. “Kinky girl.” With a caress of my breast she says. “No more jokes, Ellie.”

“Okay.” I smile.

“Your hand is…ohhhhh…just fine.” She leans in to kiss my head and take in a sniff of my hair. Her already diamond hard dick flexes even hard in my stroking hand. “Fuuuuck.”

“Mmmm. Ohhhhh.” I let out little feminine coos and mewls as I stroke Lily’s member. “Tell me I’m pretty again?”

“Ohhh, Ellie.” She opens her eyes to look down into mine. In those hazy brown eyes I could almost see the ‘Ellie’ of her dreams. Stroking my face she whispers. “Ellie girl. You’re so beautiful!”

“Oooo!”

Trying my best not to shatter her fantasy I do what I can to move and hum and look at her in the sexiest but most feminine ways I knew how. This was so…different! I didn’t yet my true feelings about gender swapping for Lily but I did know that I was having fun and that it was kinda nice to be seen as ‘pretty’. More than that however what really strikes me was how happy I was to make her happy. Seeing that smile, hearing those sighs, feeling her passion throbbing in my hand made me feel more amazing and more…manly than I’d felt with any girl before Heather. It felt so fucking good to give good feelings to a woman. It meant a lot to me. I meant everything to me. I had yet to have even a drop of honey from Lily, these feelings ran deeper than that. In a flash it comes to me that the real rot that had set in between Blair and I was my inability to bring joy to her. Like me she was so deeply unhappy. Despite all the things she’d said to me I hoped that someday she could find her own Heather to complete her.

Pouring my attention to the sexy lady on top of me I continue my soft sounds and passionate gropes and steady strokes. Lily closes her eyes again to submerge fully back into her fantasy. Maybe next time, with the right clothes and other girly touches, I could truly be the pretty girl that she was dreaming about.

I worried that getting spoiled on honey might ruin regular sex for me but it wasn’t the case. I still enjoyed the feeling of soft flesh in my hand, the sensation of breasts against my face, and now the added pleasure of having a woman’s balls rubbing my boner through soft cotton panties. The highs weren’t as high and the lows weren’t erased but having fun while ‘sober’ felt every bit as good as it used to.

Pulling back to give me some space I start stroking Lily’s cock faster while gripping it a little tighter. I get immediate results as her dick surges and a big drizzle of precum sprouts out the crown. Letting a long stream of saliva drop from my lips I add my spit to her honey to really lube her up. With the sudden wetness my strokes could now glide smooth and slick up and down the top few inches of her erection.

“Hahhh! Fuuuck!” Lily thrusts in time with my strokes, her hot body bending in such a sexy way.

I stare down at her member as I focus on giving her the best handjob I could. As I stroke, adding more spit ever so often, I begin to end it with a bit of a twist at the elegant tapered knob. It sure felt good to feel another cock in my grip again. Nice and hard and big. I loved it! And Lily’s was so darn pretty too. Like the rest of her body Lily’s penis just exuded feminine allure. Though noticeably thinner and shorter than Mia she still made for a nice handful and she was long enough for a satisfying up and down motion. If I were to guess a number I’d say Lily was about eight inches, just a smidgen shorter than Julie though WAY thinner. After feeling my ladies in my grip my own pecker was going to feel like a toothpick by comparison. Of course, if Heather had her way I’d never have to stroke one out on my own ever again.

“Fuck!” Lily huffs. “Oh, baby. Ohhhhh!” Looping her hands around the back of my neck and humping into my hand faster and harder Lily’s perfect tits begin to bounce. “Yes! Yesss! Mmmm!”

“Ohhh! Ohhhh!” My femme voice rises as if I were on the verge of release myself. Her balls rubbing me through the panties felt really fucking good but not in the same strong, steady way as I full on handjob. I knew I probably wouldn’t get to cum and that was fine by me. I lick her titties, I suck her titties, I hold her tight around her back as I moan. “Yesss! Ohhh, yesss! Cum for me, baby!”

“Oh, Ellie! Mmmm!” Stronger and faster she humps away, her glistening cock poking through my tight grip again and again. FUCK I wanted to suck her to a finish but it was too late now to switch things up. “Ohhh! Mmmmm!”

Faster I stroke, my hand now a blur as it pumps her big eight incher. Her soft body begins to tighten and tremble and I knew she was just seconds away. Though my forearm was tiring I grit through it and jerk Lily through to the end.

“HAH!” Her eyes flare open. Falling back she grabs my shins to arch her body back, her tits thrusting high in the air. “HAHHHHHH!!!” With a great gasp her cock throbs mightily in my hand and an instant later a long creamy white rope of cum soars! It arcs over her stomach to come splattering down straight between her tits.

“Yes! Fuckin cum for me, baby! Yes!” I pump hard and fast. I could feel her balls pulsing over my cock as I milk wad after hot wad of her jizz out onto her naked flesh.

“Hahhh! Hnngh! Fuuuuck!” She moans like a woman who hadn’t had it in WAY too long.

After a good minute of humping and humming I am squeezing out the last drops to pool in her belly button. I took a herculean effort for me not to lean down and start lapping up her creamy jelly but I had practice soon and I didn’t want to be all giddy and loopy on cum.

Her nut bust Lily topples over to land with a bounce on the mattress. Rolling onto her back she lets out a most satisfied whimper. “Ooohhh.”

“Heh.” I give her spent cock and balls a gentle pat. “How was that?”

“Ohhh, Elliot! Ohhhhh! Holy SHIT!” Her arms flop out beside her. “I don’t think I’ve ever cum that hard!”

“He he he! I’ve heard honey boys just hit different.” When she looks down at me I wink. “Or honey girls.”

She sighs, her face all flushed in afterglow, then whispers. “Thank you, Elliot.”

“Hey.” I crawl up beside her and kiss her shoulder. “The pleasure was all mine.”

“Ohhh, I don’t know about that.” Reaching down she strokes my cock through the panties. “You wanna squirt for me, pretty girl?”

“Mmmm.” I hum as I enjoy the feeling for a few strokes. Then, with a shake of my head, I say. “Nope.”

“No!?”

“Ellie expects to be treated right before she gives it up.” Taking her wrist I pull her hand away.

“You’re joking!”

“Mm mm.” I shake my head with a smile. “Ellie’s not that kind of girl.”

“You…you…you tease!”

“Heh!” I roll out of bed and slip out of her panties. Noticing the little wet spot caused by my precum I say. “Sorry about that.” Then lay them on the bed beside her.

“You’re seriously leaving!?”

“My lady’s been taken care of.” Hands on my hips in nothing but a smile I peruse Lily’s cum splattered body with the pride of a job well done. “My work here is done.”

She stares at me for a stunned moment…then bursts into laughter. “You…nerd! Ha ha ha ha!”

“He he he!”

“Ohhhh, Elliot.” She says, her belly laughs making her jiggle oh so nicely. “You are taking to this WAY too well.”

I blow her a kiss. “I’m glad you had fun, Lily. I know I sure did!”

“You really did?”

“Yeah.” I say warmly. “It was different but…yeah, I liked it.”

“Oh! Um…” She props herself up onto her elbow as she watches me pull on my underwear. The laughter fading, her voice softening, she asks. “When can I see her again?”

“Ellie?”

She nods.

“Well…that girl’s night thing sounded kinda fun.”

“It did!? Really?”

“Yeah. It did.”

“It’s a date!” She smiles. “I’ll treat her right, Elliot. You’ll see.”

Grabbing my crotch I give it a squeeze. “If you want this pussy, you better!”

“Ha ha ha!” She starts laughing all over again. Waving her hands at me she says. “Get outta here you little cock tease!”

“He he he!” I spin around, thrust my ass her way and give it a slap. “See ya in a few.”

“TEASE!”

I laugh as I duck the wadded up panties as they come hurtling by my head. Gathering up the rest of my clothes I bundle them to my body and hurry for the door. I would have gotten fully dressed but since I was just going to dash straight from this room to Heather’s I figured that there was no point. I still had a raging boner and a few more minutes to spare, I just prayed my Mistress was still in the room and still in the mood.

Chapter 110