Chapter 30: Kipona Aloha

Lily sat up on the edge of Belle’s mattress, her heels perched on the bed frame with her elbows on her knees and her face in her hands as she sobbed in utterly abject misery.

I rushed to her, sat down beside her, and then gently drew her into my arms. My cute ku’uipo girlfriend immediately pressed her face against my chest and started sobbing even harder, but at least it felt like a cathartic release rather than my presence making her feel worse or anything like that. And I rubbed her back and shoulders and arms with both of my hands while pressing my cheek down against the top of her head and rocking us both back and forth a bit.

Eva’s head appeared in the open doorway to Belle’s bedroom, the movement drawing my attention to her. She merely peeked around the corner, her eyes wide with uncertainty. I expected her to draw back and disappear out of sight again, but instead she first took a single step into the room to reach for the doorknob before gently shutting the door to give us some privacy.

Gentle as Eva was, she still couldn’t shut the door with complete silence. The sounds of wood contacting wood and then the latch snicking shut made Lily pop her head up to look, and she started to slowly regain her composure as she sat back up, sniffled, and wiped her eyes with the backs of her hands.

Keeping my left arm wrapped around Lily’s waist, I grabbed a few tissues off the nightstand with my right hand and then handed them to her. She accepted them gratefully, blew her nose, and then balled up the tissues into a wad. I handed her several more tissues and let her keep wiping her eyes and blowing her nose until she’d made a bigger ball in her hands. And finally, she bowed her head with her hands in her lap, going silently despondent with no more tears left to give.

I gently pried the ball of tissues out of her hands and walked them over to the trash can by the desk before returning to a seated position beside her. Lily immediately wrapped her arms around me and buried her face into my chest once more. But at least she didn’t start crying again. And we remained like that, quietly embracing, for another minute or so.

Eventually, I spoke up first, intoning tenderly, “I’m so sorry about Belle.”

“Always saying ‘sorry’? The honorary Canadian has nothing to apologize for,” Lily mumbled into my chest before letting out a big sigh and then relaxing her grip, although she still kept her arms around me. Pulling back a bit, she shook her head slowly while staring at my chest with a melancholic expression, mumbling, “It’s not your fault that Belle’s not gay.”

I waggled my head and muttered, “Saying sorry was more of a sympathetic ‘I’m so sorry’ than an apology. As for Belle not being gay ... well ... It kinda is my fault, if you think about it.”

Lily knitted her eyebrows together for a moment, but then cracked a smile. And she pulled back far enough to lightly punch my belly. “You’re right. It’s you and your gorgeous cock’s fault that Matty’s Little Cumslut can’t imagine a life partnered up with a girl instead of a guy with a gorgeous cock producing all that yummy cum she craves so much.”

“Sorry...” I drawled.

Lily chuckled for a second. But a second after that, the smile on her face faded away along with the sound of her amusement. And she wound up sighing while shaking her head with that melancholic expression again. “If only it were as simple as craving Matty’s cum. I asked if she could be happy with me so long as you gave her regular doses. But it was never just about satisfying her cumslut urges. Belle wants a boyfriend. Belle wants a husband. She wants a Hallmark nuclear family: with a husband and kids all dressed in identical reindeer outfits on a Christmas card she can mail out to friends and the parents of her kids’ soccer teammates. And even if that husband doesn’t end up being you, it’ll still have to be some other ‘him’. Not a ‘her’ like me.”

“Aren’t we all a little young to be thinking about marriage?”

“That’s what -I- said!” Lily looked up at me with a world of confusion in her eyes. “We never even got together as a romantic couple or anything, so why in the hell did she feel the need to break up?”

I grimaced, took a deep breath, and asked, “Was there anything that triggered her today? Did you say anything that upset her?”

“What? Me? No. If anything it was that boorish asshole that must’ve upset her.”

A chill ran down my spine, and I suddenly stiffened as I growled protectively, “What boorish asshole?”

“Relax, relax,” Lily soothed before sighing. “We have no idea who the hell he is. Just some random lolo on the street. So Belle and I are skipping hand-in-hand down the sidewalk on the way home when this boorish asshole across the street yells some crap about there already being too many dykes in Berkeley. So Belle yells back that we like sucking dick just fine but that a greasy fuckwit like him can only dream of getting girls like us to ever suck his. Brah looked like he shit his pants, and we laughed about it the whole way home. Belle said she was gonna suck your dick as soon as she saw you, and I said only if I didn’t get my mouth on it first, and then as soon as we got home we came up here and started kissing and I thought everything was great but then all of a sudden she just rolled onto her back, stared at the ceiling, and muttered, ‘I’m not a lesbian’.”

I winced and gave Lily an apologetic look. “How did it make you feel when she said that?”

“I didn’t feel anything at first. I was just confused and didn’t know what was going on. But then she looked up at me with this sad look on her face and said, ‘I’m not being fair to you.’ And then I asked, ‘What are you talking about?’ And then she said, ‘You want to love me, but I’m never gonna be able to love you back the same way.’”

I nodded slowly and muttered, “I see.”

Lily pursed her lips. “I never asked her to like ... be my girlfriend or anything.”

“But it definitely seemed like you wanted her to be. At the very least, I know you thought of her as aikāne. I’ve heard you say to her, ‘Aloha au iā ʻoe, aikāne.’ You’ve said plainly, ‘I love you.’”

Lily looked ready to cry again. “I do love her.”

“Did she ever say it back to you?”

Fresh tears started rolling down my ku’uipo’s cheek. And in a quiet voice, Lily mumbled, “No. She didn’t.”

I took a deep breath and sighed. Lily started shuddering. The waterworks started flowing. I quickly bear-hugged her again. And the next thing I knew, I was rubbing her with both hands while pressing my cheek down against the top of her head and rocking us both back and forth once again.

What followed was a near-repeat of what we’d done before. It took a while, but Lily eventually cried herself out and started to regain her composure. She sat back up, sniffled, and started wiping her eyes with the backs of her hands. I held her with one arm while retrieving tissues with the other. And she spent some time wiping her eyes, blowing her nose, and bunching up the tissues into a big ball between her hands until she finally bowed her head with her hands in her lap, going silently despondent with no more tears left to give.

And then she kissed me.

Lily wailed in mournful agony while pressing her lips to mine. I felt her yearning need for comfort and held my ku’uipo girlfriend tenderly in my arms while kissing her back. And when she knelt atop the mattress to gain enough leverage to push me onto my back across the bed, I simply let myself fall back while cradling her smaller body against my side.

She started crying again while kissing me, and neither the crying nor the kissing stopped for a long, long time. There was nothing sexually passionate about our kisses; she needed comfort and love, not sex. And eventually she ran out of breath as well as tears, and she slumped against my body with her right leg thrown across mine with her face pushed into the crook of my neck while I stroked the back of her head.

At first, both of us panted for oxygen after such an extended makeout session. But as the seconds ticked by, Lily’s breathing slowed down and became deeper and deeper until I genuinely wondered if she’d fallen asleep on me. But when I turned my head fractionally to try and look down at her face, she tilted her head back to look up into my eyes. Her irises then sharpened. She propped herself up on one elbow. And then she lowered her lips down to mine once more.

This time there was a LOT more passion in Lily’s kiss. She crooned into my mouth with carnal need, and her tongue plunged into my mouth while her fingernails slid across my scalp. She attacked me with lustful fervor, moaning and groaning as she sat up, reached down for her sweater’s hem, and whipped the offending garment over her head. Her bra went next, baring her big, beautiful boobies to me. And a moment later, her magnificent melons crashed down onto my face when she draped her chest on top of me while reaching down with both hands to start wriggling out of her jeans.

When quite literally “faced” with such marvelous mammaries, I did what I always do: I grabbed on and started motorboating myself in them. I licked and I suckled while my horny Hawaiian hottie groaned and wriggled on top of me until she managed to slip off her jeans and panties. But then paradise was momentarily removed from view when she slithered down my body to start working at my jeans instead.

I didn’t ask any questions or try to dissuade Lily from her present course of action. I knew she was feeling lonely and rejected, and for me to do anything but welcome my girlfriend’s passionate lovemaking with anything less than eager anticipation would’ve been a cruel blow to her heart. She needed me in this moment - needed her boyfriend, her hoa kāne, to make her feel loved. So I merely ripped off my own shirt while she tugged my jeans and boxers down to my knees and then ducked her head to start feeding on me.

Had that boorish asshole been present he would’ve gotten first-hand proof that Lily liked sucking dick just fine, and she went a little loco with some of her most passionate, most aggressive fellatio ever. But her fervor didn’t last long - she was quickly consumed with a need to feel me deep inside her - and after ensuring that her hoa kāne’s “giant tree” was sprouting straight up to the sky, my cutie ku’uipo was quick to cram my cock all the way into her already-creaming cunt.

Lily fucked me with an unusually animalistic abandon. Oh, she’d always been an energetic lover: buoyantly bouncing up and down while waving her hands in the air like she just didn’t care, or screaming in joy while thrashing beneath me. But there were no exclamations of ‘Best! Day! Evar!’ or ‘WOOOO!!!’ this afternoon. She didn’t squeal ‘Yes! Yes! Yes!’ or cry out ‘Fuck me, Matty! Fuck me!’

She simply fucked ME with overwhelming madness, gripping my shoulders and humping herself on me harder and harder and HARDER until I was almost afraid her hips would bruise. She dug her fingernails into my skin, not quite scratching me with Eva’s Wolverine claws but still tightly enough to leave red marks by the time she was done. And there was an unsettling wildness in her eyes - almost desperation - as she stared down at me the entire time.

Her first orgasm came quickly, almost as soon as we’d gotten started.

Her second orgasm rapidly followed, even before her climactic cries from the first had died out. She lost the rhythm during that second climax, her spine arching and her hips spazzing. And when her body went limp atop mine, I planted my feet flat while palming her ass so I could take over with powerful upward thrusts into her pliant, pleasant pussy.

“Hngh! Hngh! Hngh!” I grunted while she went limp like a rag doll on top of me.

“Put it ... in my ass...” Lily groaned into my ear, her eyes a bit wobbly and her voice weak. “I need ... I need you ... Please ... Matty ... Put it in my ass...”

I stopped my heaving for a second, caught off-guard by her request, but after turning my face to hers, I managed to mutter, “You’re not prepped.”

“I’m prepped ... enough...” she wheezed, her eyes still wild despite her weariness. “Those orgasms ... wiped me out. I love you... hoa kāne ... I’ve wanted it ... since the weekend ... Please, Matty ... Please ... Roll me over ... and let me feel you...”

Lily was on the verge of tears again, and for that reason alone I figured I should tell her this wasn’t the right time. But there was also such desperation in her expression that I feared rejecting her request would be even worse. I took a deep breath, resolving to at least try. But at the same time, I knew that if she showed any of the same kind of discomfort or pain she’d shown Saturday night, I’d call the whole thing off immediately.

I started by laying Lily flat on her back with her legs thrown over my shoulders so I could eat her out while simultaneously lubricating her backdoor entrance with Astroglide-covered fingers, first one and then a second. She crooned to the ceiling while manhandling her own boobs, and when I bore down on her clitty as a distraction at the same time I started shoving in a third digit, she clapped my ears with her thighs and cried out as she came. And then her body went absolutely limp before me.

Recognizing that there would be no better time for me to attempt insertion than the moments of utter relaxation following such an orgasm, I wiped my hands clean and then laid Lily down on her left side with her legs stretched out, her body in a capital “L” shape. Standing next to the bed, I fingered her clit with my right hand while guiding my mushroom head into position against her anal star with my left, expecting to force myself past significant resistance. But she merely exhaled slowly and opened up for me at my first push, accepting the first few inches of my turgid tool straight up her tailpipe without any trouble whatsoever.

And THEN she clamped up like crazy.

“HOLY OKOLE!!!” Lily exclaimed as her entire body tensed and she suddenly reached back with her right hand to plant her palm against my midsection and prevent me from entering her ass any further. She clenched her teeth and muttered several more words in broken pidgin that I wouldn’t have understood even if I’d heard it all clearly.

The expression on her face at this moment was identical to the expression she’d worn on Saturday night when I’d called off her anal attempt while face-down/ass-up in a row with Naimh, Sam, and Belle. So I was very much prepared to call it off again.

But Lily reached up to grab my forearm, tugging me towards her instead of pushing me away. “No, don’t pull back. Please ... Don’t give up on me.”

“I’m not giving up on you,” I reassured her. “I just don’t think you’re ready for this yet.”

“I AM ready!” Lily insisted, tugging on my forearm again. “Please! I want to do this. I need to do this!”

“You don’t need to do this for me.”

“I don’t need to do this for YOU. I need to do this for ME!”

“Lily, this isn’t the right--”

“Matty, please. Please!” she wailed. Tugging on my arm again. “You’re already halfway in! Don’t give up on me now!”

Taking a deep breath, I nodded my acquiescence. Lily gave me a small smile and then exhaled slowly, forcing herself to relax. And as I felt the tension in her body start to bleed away, I leaned forward to ease myself a little further in.

Lily’s entire body clamped up again, including her colon. Her fingernails dug into my forearm, not quite hard enough to draw blood but enough to leave a mark. Several tears leaked out from her eyes to run down her cheeks. And I stopped my forward progress once more while she gritted her teeth against the pain.

Again, she relaxed and then tugged on my forearm again to get me to resume pushing.

Again, she clamped up after I pushed in another inch.

And then another inch.

And then another inch.

It felt like it took forever, and if her asshole wasn’t so tight and so hot, I’m sure I would’ve lost my erection halfway. But eventually I made it all the way inside, and Lily was sweating like crazy by the time my short and curlies pressed up tight against her buttcheeks.

Throughout the process she’d worn a perpetual grimace of pain with rivers of tears flowing down her cheeks, and I swore to myself up and down that I would NEVER do this to her ever again. Honestly, I didn’t want to be doing it to her NOW. The first time with some of the other girls had been rough or required some gritting their teeth and bearing it, but not anywhere near as bad as this. It was the least erotic bout of anal sex I’d ever had in my life, feeling more like a test of endurance and torture than an act meant to bring pleasure to both parties.

But Lily had kept tugging on my arm, kept insisting that I continue, and I didn’t have the heart to turn her down. She was feeling dejected and rejected already. And even though I thought she was doing this for the wrong reasons - even though the phrase “not in the right frame of mind” didn’t even begin to describe it - I couldn’t let her fail.

I couldn’t give up on her.

And at last she’d succeeded.

Or so I’d thought.

“You did it,” I told her proudly while leaning over her body to give her a tender kiss. She was still in that capital “L” shape with her legs out to the side, but our height differential was such that I could easily lean forward to rub my lips against hers. And I repeated with a smile, “You did it.”

Lily hooked her arm around the back of my neck and stared up at me with fiery eyes. “Not yet, I haven’t,” she countered. “You still have to cum in me.”

I pursed my lips. “I don’t wanna hurt you any more than I already have.”

“You haven’t hurt me. Hurting me would be quitting before finishing the job,” she insisted, panting deeply for breath as if she’d gotten the wind knocked out of her. “I won’t lie: this isn’t comfortable ... I don’t think I can cum this way ... But I CAN say ... that I fit my boyfriend’s big dick ... all the way up my tight virgin asshole ... And I WANT to say ... that my tight virgin asshole ... made him cum.”

Lily’s eyes were intensely serious. I knew there was no quit in her. For me NOT to cum would be the greatest failure now, and I nodded my acquiescence before withdrawing only two inches and then slowly burrowing those two inches back in.

Well ... I tried to. She clamped right back up, and her palm instinctively shot out to my midsection, holding me at bay. And I grimaced, shaking my head slowly as fresh tears rolled down Lily’s cheeks.

“I really don’t want to hurt you,” I insisted.

“You gotta cum, Matty...” she pleaded, pulling her hand off my midsection and tugging on my arm again. “You gotta cum.”

She forced herself to relax. I recaptured the lost inches. And I reached my right hand between her legs to strum her clit and give her some distracting stimulation while simultaneously wishing I’d thought to give Lily a vibrator so she could give herself some mechanical assistance the way Zofi had done for her very first anal.

It helped. With a little manual manipulation, she was able to endure a little more. Lily stopped clamping up on me, and I was able to make short thrusts two or three inches in and out. It was still slow-going though, and I knew I’d never get enough stimulation to cum this way. But the longer we kept going, the further and faster I was able to go.

At first, Lily stretched her right leg forward to give my hand a little more room to rub her. But after a few minutes, she kicked her right leg up and across my chest while rolling herself flat on her back. Raising both knees, she planted her feet flat against my chest to push back at me and help control the depth. When her feet relaxed, I pushed forward. And when she pushed her heels into my pectorals, I came to a halt.

At the same time, she furiously rubbed her own clit while closing her eyes and grimacing. Her tears had dried up and she very rarely clamped up on me anymore, so I figured her anal chute was finally stretching out to accommodate my monster. But the single best thing I enjoyed about making love with Lily was the way she looked up at me like I was the sexiest, most incredible, most desirable man on Planet Earth.

And she couldn’t do that while her eyes were closed.

“Look at me, Lil,” I encouraged while getting a better handhold on her hips with my fingers tucked under to feel her meaty bottom. I leaned forward against her feet, folding her in half so that she curled up like an armadillo with her knees pressed into the mattress to either side of her head but with her feet still braced against my shoulders. “Look into my eyes, ku’uipo.”

She opened her eyes, still grimacing and still furiously rubbing her clit. I could see the clear discomfort in her eyes, but I could also see her clear determination to finish her task.

“Aloha au iā ʻoe, ku’uipo,” I told her plainly. “I love you.”

Lily’s lips fractionally parted as she stared up at me in wonder.

“Mahalo makana ... uh... makamae,” I said in broken pidgin, knowing I’d screwed something up but hoping that she appreciated the effort. “Thank you for this special gift.”

Lily’s face brightened, her asshole relaxed, and suddenly I was able to take full lunges.