The Big Tits Club: Chapter 33 (Patreon)

-- CHAPTER 33: Ailiseu --

****

A stray beam of sunlight woke me up. The curtains had been shut, but there was a half-inch of space between them, and at this very time on this very date, the sun’s rays came through at just the right angle to hit me right in the eyes.

The morning air was cold against my right cheek, the pillow reassuringly warm against my left. I snuggled deeper into the covers and their cocooning heat while pressing myself against my lover’s back, my bare chest separated from her skin by only a thin layer of cotton. As my senses came alive, the fingers of my right hand reflexively squeezed the large breast I was currently palming beneath her nightie. My left arm snaked beneath her pillow, with the hand dangling off the edge of the bed.

Breathing deeply, I let my head roll forward to push my nose into her strawberry-blonde hair, smelling her sweet fragrance. Reflexively, I ground my morning wood into her panty-covered ass. My banana-bent prick automatically nestled into her buttcrack, but as I started hot-dogging her buns, I became quite consciously aware of the hard, unyielding bump that impeded my shaft’s movement.

It’s a butt plug.

That information zapped my brain like a lightning bolt, and my eyes flew open. All of a sudden the events of last night came rushing to the forefront of my memory, and I started to wonder exactly how Belle had managed to magically appear in my bed.

The last time I saw her, she’d bolted through my bedroom door and slammed it shut behind her. I’d fallen asleep alone in my bed, exhausted from the day’s extensive sexual exertions, and expected to awaken similarly unaccompanied. Obviously, that did not turn out to be the case.

Part of me wanted to wake her up and demand an explanation for why she’d more or less picked a fight with me and then stormed out.

The greater part didn’t really give a shit. Girls could mystify me at times, especially when it came to their emotions, and rather than (A) wake her up sooner than she wanted or (B) say anything that would potentially upset her, I preferred to simply enjoy her familiar presence in my bed, continue fondling her bare breast, and enjoy the moment for as long as it lasted.

Besides, I still remembered “the plan”. Last night while dressed up as Morrigan Aensland from Darkstalkers, bat wings and all, the sexy little vixen had told me she wanted to sleep all night with the big butt plug in her teeny little asshole and then have me replace it with my cock in the morning.

And I really, really wanted to get into that ass.

Explanations could wait.

In the meantime, I had a scantily-clad teenage girl in my bed, and if experience in these anal matters had taught me anything, it was that the easiest way to loosen up a girl’s tight rectum was to give her an amazing orgasm first. And… well… I wanted to see how far I could titillate her body before she woke up… just because.

I slid myself away from her, and with my body no longer supporting her from behind, she automatically rolled a bit further onto her back so that she was about three-quarters of the way face up. Pulling my right hand out from beneath her nightie, I pivoted my wrist and ever so slowly slid it beneath the waistband of her panties instead, moving lower until my middle finger found her cleft.

Belle inhaled but did not wake when that middle finger penetrated her nether lips. I didn’t have to push very far to find moisture, and after coating my fingertip in her honey, I pulled back far enough to rub that moisture over her clit. She shivered just a little at the touch, but I had already stopped rubbing as I’d gone back to get more juice.

I repeated this motion twice more, and then finding her hard little clit slick enough, I stayed there and gently maneuvered it like a pointer stick in the middle of a laptop keyboard between the G, H, and B keys. She started breathing a little more deeply, her lips parting open a bit, but still she did not wake.

Every now and again, I had to go back to get more pussy juice to slather over her clit and keep going, but the longer I went the more her labia opened up, making it pretty easy. I smeared her liquid arousal everywhere and now bracketed her little nub with two fingers, rubbing more firmly. She moaned, turned her head away from me, and started gasping as her hips began to shake.

I didn’t let up.

Annabelle’s awakening was inevitable. It was only a matter of when, not if. I just wanted to pleasure her unconscious body as much as I could before that happened, so I started rubbing her harder and harder and harder.

Her eyes snapped open just before she came. Her head whipped around, pale green eyes brilliant in their luminance as she gasped, her mouth forming a perfect O-shape. Her eyes grew wide as saucers in surprise as well, and then suddenly her eyelids snapped shut as she clenched her eyes, clenched her teeth, and even clenched her legs together. But nothing would stop the climax that came crashing through her entire body as she jerked rather violently, just once, and then suddenly gaped her mouth open again in a silent scream as the explosion rippled out from her loins.

I quickly rolled onto my knees and yanked down on the sides of her panties, dragging them off her legs and tossing the flimsy fabric aside. Yanking her right leg out of the way, I dropped my face down to her crotch and began feasting on her succulent snatch immediately, driving my tongue deep into her soaking wet vaginal canal and licking up until I could fasten my lips around her protruding love button.

The second climax came much faster than the first. While I had been fingering her for what felt like ten minutes slowly building the sleeping beauty to blissful release, this time I just went full bore on her tight little pussy, eating her out with abandon and intent on giving her such a massive orgasm that it would nearly render her unconscious once more.

“Nnnngghhhh…” Belle groaned at the sensations, eyes clenched once again as she slowly waved her head side to side across my pillow.

I added two fingers, curling them to tickle her g-spot even as I felt the snug constriction of her little hole, the channel’s volume displaced by the silver butt plug in her colon topped with a blue crystal that glinted in the morning light just beneath my pumping hand.

“Matttyyyy…” Belle hissed as her fingers scrabbled in my hair, her nails scratching my scalp as she fought for purchase. Her legs started moving, her knees and feet pumping up and down to the sides as if she were climbing stairs.

I didn’t let up, sucking powerfully on her clit while continuing to fingerbang the hell out of her.

And then she was there. At first, she inhaled while gasping, “Ahhh… Ahhh…” as if on the verge of a powerful sneeze. But instead of letting out a big “ACHOO”, instead she finished with “OHHHWWWAAAAAAAUUUUUGGGGGHHHH!!!”

Belle’s back arched, her hips thrust upwards, and she nearly snapped my neck. But I held on for the ride and kept tonguing her through her climax to maximize her pleasure, until she’d spasmed and jerked a dozen times before collapsing back down to the bed, utterly and completely limp.

Perfect.

In less than ten seconds, I reached into the nightstand, retrieved the bottle of lube, grabbed the silver disc with the blue crystal, and pulled back on the butt plug, which was a little harder to remove than I’d expected. But it swiftly came free, I squirted a bunch of lube all over and into the gaping black hole before me, and then I centered my purple throbbing cockhead at her open anus.

Then I pushed.

I didn’t actually watch the way my dick sank deeper and deeper into Belle’s butthole. Instead, I watched her face, watching the way her eyes got HUGE and her mouth once again formed that perfect O-shape.

She didn’t make a sound; she just lay there with her jaw flapping a bit like a fish out of water while inch after inch of Matty-dick burrowed all the way into her anal chute. And only when I was buried to the hilt and stopped pushing did she even start to breathe, suddenly gasping for oxygen like a deep-sea free diver finally returning to the surface.

Her eyes closed then, and she breathed shallowly with her forehead furrowed in concentration. After what felt like eons, she opened her eyes again and squeaked softly, “Did it all fit?”

I chuckled and pecked her forehead. I had to hunch my back in order to get low enough to kiss her lips, and I sighed, “Yes, it all fit. Does it hurt?” Traumatic memories of my little Annabelle screaming in pain or even just yelping, ‘Nope-nope-nope’ popped into my head.

But she shook her head in the negative and closed her eyes to concentrate on the sensations. “Doesn’t hurt. Just feels SO fucking FULL.”

I breathed a sigh of relief. “Thank goodness.”

“Feels good, actually.”

“Really?”

“Mmm-hmm… I think I get why Neevie wants this so much. You’re in my sacred core.”

The mention of Naimh’s nickname reminded me that not everything had been resolved nor would be washed away by this anal encounter, but I focused on the present and bent down to kiss my lover’s lips. “I’m in your sacred core,” I murmured warmly. “And it feels so fucking GOOD.”

She opened her eyes, a twinkle in those pale green irises. And in a somewhat proud tone she asked playfully, “Is my ass tight for you?”

“So fucking tight.”

“You feel so big inside me.”

“It’s a perfect fit.” I kissed her again. “You’re my perfect fit.”

Belle’s eyes shimmered, and then she grabbed my head and kissed me fiercely. We made out like the teenaged lovers we were for a few minutes, unmoving nor really needing to move. It was still early and it felt like we had all the time in the world. And after last night’s… whatever that was… I felt a desperate need to reassure my little Annabelle just how very much I loved her.

But eventually she broke the kiss and held my head to stare into my eyes with a curious look on her face. A moment later I found out why when she started clenching her ass muscles rather experimentally. Then it was MY turn for my eyes to get big as the incredible intensity of Belle’s butthole sent pulses of pleasure into my brain. Her legs were wrapped around my waist, and she flexed them experimentally while undulating her abdominals, fucking her own ass back and forth along my dick a few inches at a time.

Pre-stretching overnight with the silver plug and the copious amount of lube I’d used made it… well, it wasn’t easy but I’ll admit that it was a lot easier to slide my shaft in and out of her asshole. At first, I simply stood my ground, letting her fuck herself on me to let her give me this pleasure. But after a couple of minutes, I couldn’t help but get involved as well.

So I started pumping. Belle’s eyes got big again, the size of saucers, as she absorbed the new sensations. She stopped milking me and instead concentrated on the way I fucked her ass and skewered her skinny body to the core. Her chin extended upward toward the ceiling as her head lolled backward, and she started gasping like that fish out of water again while I steadily plundered her tight little rectum.

Belle groaned gutturally when her first anal orgasm snuck up on her. She flopped and twisted and her anal chute clenched up so tight I couldn’t move. She planted both hands atop her face and screamed into her palms. But rather than wipe her out, the climax energized her, and suddenly she was back to fucking me as much as I was fucking her.

Scooping my arms beneath her lower back, I heaved and hoisted Belle off the bed while falling back onto my own heels. She sat up straight, our faces lined up perfectly to start French kissing furiously while she continued to hump her ass up and down my dick. I pivoted and slipped off the bed while she kept her legs wrapped around my waist. And just because I could, I started walking around my bedroom while she clung to my chest like a Koala bear, the walking motion helping her bounce her tight little butt as we went. I certainly couldn’t do THAT with any of the other girls.

Planting Belle against the wall, I started humping her the way I did sometimes in the shower. Freed from the effort of fucking me, she instead poured that energy into attacking my face and mouth. But eventually my legs started to tire, and some of the dizziness after-effects of Sam’s pill from last night gave me vertigo. So I staggered back to my bed and sat down before Belle pushed me onto my back.

Only now did she finally rip her nightie over her head, baring those sweet boobies to my intense gaze. She leaned back to grab my legs behind her and planted her feet flat on the bed to either side of me like she was doing a crab walk. This spread her entire crotch out wide as she crunched her abs to really hump her anus up and down my fuckstick. The view was incredible and I nearly came, but she got tired and eventually just sat down in my lap, panting for breath.

Meanwhile, the position had given me time to catch my breath, and by now I REALLY wanted to cum. So eager to finish us both off, I picked her up, pivoted us around, and put her back on her back in almost the same positions we’d started in. But this time I bent her legs backward so that her feet were flat against my chest as she held her own legs behind the knees.

Scooping her ass up in my hands, I knelt and leaned forward, really driving my dick all the way up her butt. Belle groaned initially, and then she groaned a helluva lot more as I started to lay down the lumber.

“Cum inside me, Matty,” Belle crooned, recognizing the strain on my face. “I wanna feel your sperm so deep in my virgin asshole. I wanna feel your essence spilling inside me where no one’s ever been before. I’m going to savor this moment forever. Because I’m making you this promise, you hear me? No matter what… no matter where our lives may take us… For the rest of my life, you are the only man I’m ever going to let into my sacred core like this. I don’t care if we end up marrying other people somewhere down the line. I promise, from now until eternity… This is only for you. My asshole. Forever yours. Because I love you. Because I’ll always love you.”

“I’ll always love you,” I grunted, feeling the strain of holding back my impending eruption. “My Annabelle… I love you… My Annabelle…”

My voice saying her name like that triggered her final climax. She had already been gasping on the edge while trying to express her promise, but now her mouth gaped open once again in that silent scream, she started muttering “Ahhh… Ahhh…” like she was about to sneeze, and then at last she howled, “OHHHWWWAAAAAAAUUUUUGGGGGHHHH!!!”

“AAAAANNNNNNNAAAAAABBBBBEEEEELLLLLLLEEEEE!!!” I howled right with her.

I came so hard I blacked out.

****

It was still a school day, so after cleaning up, we got dressed and headed downstairs. Mother was already up and had laid out breakfast for three on the table. Belle made polite chit-chat with Mother, and then she excused herself to head over to her own house to retrieve her backpack before returning so we could drive to school.

No sooner did she get out the door than Mother turned to me, arched an eyebrow, and asked rather tersely, “Did you put your massive dick inside that poor little girl’s asshole this morning?”

I blinked several times in surprise, not just twice. Did my mother just refer to my dick as "massive"?

Finally I muttered quite dumbly, “Uhhh… You can tell that?”

“Well that petite young woman isn’t walking with a hitch in her step on purpose.”

I winced, flashbacks to Belle’s initial deflowering coming to the forefront of my memory.

Mother sighed. “I have some topical analgesics. They’ll help numb some of the pain.” She left and headed upstairs to her bedroom.

Two minutes later, Belle returned and Mother explained what the cream was for. I got banished out to the minivan, despite arguing that I’d obviously already seen everything. I sat in the driver’s seat trying to not really picture my mother helping Belle apply the cream. And couple of minutes later, Belle joined me in the minivan, giving me a silently nonchalant shrug when I gave her a pointed look.

I shifted the minivan into reverse and backed out of the garage.

Alice was waiting for us at the parking lot and came over as soon as we stepped onto the curb. “You alright?” she immediately asked Belle. “You’re walking kinda funny.”

Belle exchanged a glance with me, grinned, and began, “Well… actually…”

****

The rest of the week flew by. Belle and I didn’t talk about what happened Valentine’s night, and I realized she’d deflected me once again. But while I was willing to go forward with our regular routine for now, I hadn’t completely forgotten.

Belle was only walking funny for a day or two and then everything was back to normal. And on Friday she was eager to show off her new trick, apparently wearing the silver butt plug all day to pre-stretch so that when the whole group got together they got to verify with their own eyes that she really could fit every last inch of Matty dick up her backdoor. Of course after watching pretty little Annabelle scream her pretty little head off, Naimh, Sam, and Mari were quick to line their asses up for me as well.

On Saturday morning, Alice came over to play video games with me, and mid-race out of the blue she asked, “So what’s with your recent fascination with anal sex?”

I glanced over at her, promptly crashed into a retaining wall, and belatedly returned my attention to the screen trying to get my car back on the road. “Umm, excuse me?”

“You and this new obsession with getting into everyone’s asshole.”

“I don’t think I’m obsessed with it. I mean, if you go back and do the math, I’m still having pussy sex a lot more often than I’m having anal sex.”

“Well, fair enough. But it definitely seems like we can’t have a sex session with the girls without you getting into at least one of their buttholes by the end of it.”

“That’s just because you hang out with Neevie and that girl can’t seem to go a day without at least one anal creampie. Have you asked HER about her anal obsession?”

“Of course I have, and I understand her explanation. So now I’m asking about yours.”

I sighed, leaned against the backrest, and set the controller down in my lap. Looking up at the ceiling so I could think instead of getting distracted by the game, I gathered my thoughts and ignored the fact that my car had stopped in the middle of the road.

Alice simply paused the game and turned to look at me.

“I think that for me, at least,” I began, “making out and blowjobs are the appetizers to a full meal. Having regular sex is the main course, or courses depending on how many rounds we go. And at the very end, anal sex is the dessert. Now I don’t have dessert every meal, but it’s certainly a nice treat when I do. Does that make sense?”

“Is it better than regular sex?”

“Not better, just different. It’s comparatively newer, so there’s the novelty factor. And there’s also the sense that it’s the next level of physical intimacy. I mean, when all I got was kissing and dry humping, when Mari let me suck on her nipples and gave me a handjob until I came all over my own belly, I felt like I’d seen God. Then Belle started giving me blowjobs, and I wanted to stick my dick in her mouth all day every day. Then Sam took my virginity, and Belle, and thoughts of having sex consumed my every waking moment it seemed. And now it’s anal sex.”

“And then what, water sports and scat?”

I blinked. “Uhhh no.”

“Just checking.” Alice chuckled. With a sigh, she pursed her lips together and shook her head. “This is the escalation I was worried about in the beginning. The idea that once one girl crossed a line and took things to the next level, the rest of us would have to put out just to keep up.”

I frowned. “Please tell me you don’t still feel that way.”

She shrugged. “You, obviously, haven’t pressured me at all. I’m here, dolled up in makeup, this pretty skirt, and a skimpy tank top that shows off my boobs, and yet you haven’t made a single move on me.”

I blinked and frowned. “Did you WANT me to make a move on you?”

She shook her head in the negative immediately. “I don’t want you doing anything you don’t already want to do of your own initiative. If I have to tell you to do something, it defeats the whole purpose.”

“Okay…” I furrowed my eyebrows and thought about that.

“And no, I don’t feel any pressure from the girls, either. Even when I stormed out and left the BTC for a while, that was me putting pressure on myself. Once I realized my friends wouldn’t think any less of me for being a virgin and not ready to do the same sex things they were doing with you, I chilled out about the whole escalation thing.”

“I’m glad.”

“So back to the main topic. Is anal sex really so much better than regular sex?”

I frowned. “I never said it was better. Just different.”

“You said it was dessert. Doesn’t everybody love dessert more than regular food?”

I thought about that. “Well… it’s certainly sweeter. But at the same time, people can’t eat dessert all the time.”

“Because of all the sugar and calories and lack of nutritional benefits. That’s not the case with anal sex. I mean, you and Neevie certainly seem to be trying to have anal sex all the time.”

“Well if we’re going with this metaphor, maybe it’s less about the dietary consequences of having anal sex and more about the effort involved in getting there.”

“What do you mean?”

“I mean it’s not as easy to just line it up and shove it in. Well, most of the time it isn’t. But let’s take us for example right now. If you wanted to give me a blowjob, you could just park on your knees in front of me, pull down my shorts, and start bobbing away.”

“Sounds reasonable.” With that, the scantily-clad Asian beauty slipped to the floor in front of me and reached for my shorts.

“Whoa, whoa, I meant talking hypothetically. I wasn’t asking for a blowjob.”

“I know you weren’t. But you put the idea in my head and now I want to.”

I stared down at my best buddy in surprise as she went ahead and pulled down my shorts, took my mostly-limp dick into her mouth, and started sucking. It didn’t stay limp very long, and soon enough sprouted into a full-blown erection.

At that point, Alice popped off and gestured with one hand, saying, “Keep going with your explanation.”

“Uh, I forgot what I was saying.”

“You were saying how anal sex takes a lot more effort to get there.”

“Oh, right. Well… you just demonstrated how easy blowjobs are. And even regular sex, while it wouldn’t be easy for me to just flip up your skirt and shove myself in dry, it usually doesn’t take that long to get a girl wet enough for vaginal entry.”

Alice paused more than halfway down my dick, looked up at me with her warm, almond-shaped eyes, and then pulled off the top. “If that was a suggestion for me to hop on board and give you my virginity right now, the answer is, ‘No, not like this.’”

I chuckled and shook my head. “We’re still talking hypothetically. But the point is: we could if we wanted to right now. I already know you’re getting wet while going down on me.”

Alice conceded that with a silent shrug. She was also rubbing herself at the same time. And she went back to her blowjob.

“Anal sex, on the other hand… I mean, you know what Belle just went through. It took a month of gauging her asshole with successively bigger butt plugs, and even then she had to get a wider one from Sam in the end to make it work. The first few attempts were disastrous, and I sincerely doubt we’ll ever be able to do it without lube. So it’s not like we could just spontaneously decide to pop your anal cherry right now and slam it in. Even Neevie wouldn’t be able to do that without warming her up. And we haven’t even started talking about the inconvenient need to clean up afterwards.”

She pulled off again. “Then why do it if it’s so much work?”

I laughed. “Because it’s fucking amazing, that’s why.”

Alice frowned. “I thought you just said anal sex wasn’t any better than regular sex, just different.”

I sighed. “Just because I like pizza doesn’t mean I’m gonna stop eating burgers.”

“So it’s a variety thing.”

“I suppose.”

“Neevie seems to think pizza is better than burgers.”

I thought about that. “I’ll grant you that. But it’s different for everyone. If you ask Mari, I’m sure she’ll tell you that she gets much more pleasure from regular sex than anal sex. Belle, too.”

“And yet Belle is so driven now with getting you into her ass.”

“Well, maybe that’s BECAUSE she had to work so hard for it. You know what they say about the best things in life being the things you have to really earn.”

“I thought the best things in life are free?”

“Well, maybe ‘best things’ is the wrong phrase. More like… you get more personal satisfaction hiking four miles to get to an okay scenic vista than just pulling over to the side of the road and staring out across the Grand Canyon. The effort involved makes it more rewarding.”

“Okay that word ‘rewarding’, I get that, at least. Belle won’t shut up about how thrilled she is that you can finally assfuck her. She said it’s not as physically pleasurable for her as regular sex, but she said it’s so much more rewarding when she cums during anal sex because she knows how much pain and suffering she had to go through to get it.”

“Well there you are.”

“That’s also not a glowing recommendation that would inspire a girl to give up her anal cherry.”

“Yeah, well, it’s not so painful or difficult for most.”

“I hope not.”

I arched an eyebrow and looked down at her. “Were YOU thinking about having anal sex?”

She pursed her lips, made a face, and went back to giving me the blowjob. The immediate pleasure was such that I was in no hurry to make her answer the question, and in fact was completely ready to let it go.

But after a minute, she popped off again and answered, “I was thinking about it, yes. I wouldn’t go so far as to say I was considering it, but I am trying to understand what makes the other girls want to do it.”

“Have you tried asking them?”

“Of course.”

“And?”

She thought about that and looked away, rather absentmindedly continuing to stroke my dick. Without looking back at me, she muttered, “For Belle it’s a personal achievement; she’s insecure about her body and she needs to feel like she can please you the way others please you.”

I frowned at that pronouncement.

Alice kept going. “For Mari it’s dessert, or pizza, or… I think I lost the metaphor. It’s a change of pace, and while yes, she likes pussy sex better, she enjoys anal sex every now and again when she’s in the mood or when she’s sharing the experience with her friends, like yesterday.”

I nodded.

“Neevie’s the opposite. I genuinely think that girl loves your dick in her ass better than in her pussy, and if it weren’t for all the effort and cleanup stuff she’d have you up her ass all day every day. There’s a reason she’s the Anal Queen of the BTC. She also keeps going off about you touching her ‘sacred core’ and stuff like that.”

I chuckled at that.

“Sam confuses me. Sometimes it feels like she’s just trying to keep up with Neevie. Or at least, it felt like that in the beginning. I mean I wasn’t there, but the others said that she gave you her anal cherry literally the night after Neevie gave you hers. And it was horrible and painful and all that, but she insisted she had to do it.”

I grimaced. “Sam’s… complicated.”

“But it’s not like that anymore. It’s weird, like… Sam is always in control and she definitely enjoys being on top when she’s having regular sex with you. But then--”

“But then she has this other side to her where she likes surrendering that control and letting me have my way with her,” I finished for her. “She does it with face-fucking sometimes and the anal sex too. Like she just wants me to bend her over, pin her down, and violate her for my pleasure.”

“Yeah, that’s what it looked like to me,” Alice agreed. “It’s like there’s a submissive streak in her or something.”

I blinked. “I wouldn’t go so far as to call her a submissive.”

“Whatever. Maybe it’s just a trust and safety thing. She loves you, and she trusts you, and the idea of putting herself in your hands and getting all that pleasure…” Alice’s voice trailed off as her eyes unfocused a bit, but she squeezed my dick a little tighter in her hands.

“Want me to go down on you right now?” I asked quietly.

Blinking from her reverie, Alice looked up at me and blushed. “Yes… but uh, no not yet.”

“Well now that you mention it, I think there’s a certain level of intimacy Sam shares with me when we have anal sex. For all of the girls, actually, it’s so much more… personal… special… like Neevie’s bit about her sacred core. A girl letting me into her ass is like the ultimate representation of putting her trust in me, of expressing how safe she feels with me to let me do that to her, even if it’s not the most comfortable thing.”

“Yeah, it’s the discomfort part that worries me the most. I mean, I trust you Matty, and I feel safe with you. But it just looks so painful.”

I shrugged. “Don’t knock it ‘til you try it.”

“I have.”

My eyebrows popped. “You have?”

“Well, not with your dick, obviously. But Neevie’s played around with my butt a little bit. Pretty early on, actually, she was going down on me and I was super-close to orgasm and she popped a finger in my ass and started wiggling it. It stopped me from cumming and just freaked me out. She got all apologetic.”

I frowned. “Having Neevie surprise you with a finger is different from truly ‘trying it’. Honestly, Belle got me to put my thumb into Sam’s butthole one time and just like you, it freaked her out. But now, obviously, she’s much more into it.”

“I didn’t say that was the ONLY time I’ve tried it. After Neevie turned into the Anal Queen and wouldn’t shut up about it, I got around to having her try it again, this time with me at least expecting it. But honestly? It’s just sorta… weird.”

I held up my hands. “I’m not gonna argue with you. Neevie’s tried playing around with MY butt too while she was going down on me. It uh… I didn’t like it.”

Alice started guffawing and she actually choked on her own spit for a second. At the same time, the discussion about my girlfriend sticking her fingers in my ass was not arousing in the slightest, and at some point Alice had stopped stroking my dick. I was deflating, and when she noticed, she pulled her hand away and gave me a thoughtful look.

“Maybe it would be different if you were the one playing around with my butt.”

I blinked in surprise. “Excuse me?”

Alice sighed. “Messing around with the girls has been… eye-opening. I mean, having anyone’s tongue wrapped around my clit, male or female, is pretty awesome. I don’t mind going down on them either because fair is fair and to hear a girl moaning from an orgasm -I- gave her is a bit of a rush. But at the end of the day, I’m pretty straight. And while Neevie is hot and all, I’m not super-attracted to her. So like I said: maybe it would be different if it was you.”

With that, Alice stood up and started tugging down her skirt and panties. I gawked at her, a bit of a deer-in-the-headlights expression on my face.

“Go down on me first. Get me warmed up,” she said matter-of-factly. “And then when the mood seems right, go ahead and start playing around back there. Just as long as you know that licking me and putting your fingers in is as far as you’re gonna get.”

I gave her a questioning look, one that asked if she was sure.

“What?” Alice smirked. “Hasn’t this basically been your role in the BTC for years already? Let us girls experiment with you, test our boundaries with a safe guy we know will never push us past what we’re comfortable with? This is the next step I want to explore, and I want to explore it with you.”

“Well when you put it that way…” I gave her a warm smile. But rather than slip off the couch and immediately start eating her out, I pulled the half-naked girl into my arms, abruptly dipped her over my lap, and sealed my lips over her mouth. She squealed in surprise but swooned when I started kissing her. I knew Alice would be perfectly happy to make out with me, and the adrenaline rush of feeling like she was falling for a second spiked that pleasure. Knowing that the end goal was to get her comfortable with me playing around with her ass, I knew I should have patience and take the time to really work her up to it.

So we made out for at least five minutes first. I couldn’t hold her in my lap forever though, and I wound up shifting Alice over a bit until her head was supported by a pillow propped against the armrest to my left. I slid my right hand up her torso, circled it around to her back, and flipped the clasp of the lacy black bra she’d worn in stark contrast to the peach-colored scoop-neck tank top that had been showing off her cleavage to me all morning. I paused to brush dark bangs back from her pretty face, obviously highlighted by her makeup to give her an even more exotically-beautiful appeal while at the same time remaining quintessentially “Alice”. And I smiled in obvious admiration to make sure she understood just how lovely she was to me before I bent down to capture her lips with mine once again.

I fondled her breasts and scraped my tongue against hers. I slid my fingers down her belly and through her neatly-trimmed pubic hair before gently caressing her protruding clit. She moaned into my mouth and then pulled her lips off mine to gasp against my neck when I penetrated her with two digits. I kissed my way down her neck, pulled the neckline of her tank top down and underneath her big boobs so that the peach fabric held the massive mounds up and together invitingly. I accepted that invitation and began to lick and slurp and suckle at her proffered pink teats. And she whimpered and shivered and finally squeaked an orgasm into my ear when my nipple-suckling combined with fingerbanging combined with my thumbing of her clit to bring her up and over a small peak.

Only then did I slip off the couch and orient her body upright. Tugging on her buttcheeks, I dragged her ass right to the edge of the couch so I would have unfettered access to her sweet snatch. I dove in and feasted, wrapping my tongue around her clit right away. And she moaned and grabbed my hair, pressing my face even deeper into her crotch before groaning gutturally, “Ah, fuck, Matty. Eat me! Eat me!”

I ate her. I ate her and I fingerbanged her. I ate her, fingerbanged her, and then I flipped her over onto her stomach. She wound up with her chest and torso atop the couch cushion but her knees on the floor while I licked her slit from behind. I then dragged my tongue along her happy trail, from pussy across the perineum and finally to her winking rosebud. I licked all around that pink little sphincter while re-introducing my fingers into her wet box. And while I fingerbanged her cunt with three digits, I stiffened my tongue and pushed it through her anus.

Alice’s head popped up and she groaned in obvious pleasure. She reached out with both arms, clasping at the backrest and the cushions to either side. She grabbed the same pillow against the armrest and pulled it to her face, smothering herself for a moment before she bared her teeth and bit down on the top of it.

By now I’d started stashing an extra bottle of lube underneath the couch since I’d started having so many anal encounters with the girls in the family room. Just yesterday, I’d used the bottle to show off Belle’s new butthole trick, so it only took a few seconds of blindly searching with my left hand to find it. And after popping open the cap, I stopped giving my best friend a rimjob and instead squirted out a healthy glob of the slippery stuff right atop her anus.

Alice shivered and looked back at me, asking, “What are you—OHHHHHH!!!”

Her question got cut off when I removed my fingers from her cunt and instead pushed first one and then a second finger through the glob of lube and into her tight asshole. She’d clenched up in surprise but then relaxed a second later. I then ducked my head back down to resume licking her clit, working hard to send pleasure signals into her brain while slowly pumping the two fingers in and out of her ass.

“Turn over again, Alice,” I said gently and went back to eating her out.

Her eyes were clenched shut and she moaned as I fingerbanged her little asshole, but she responded nonetheless by rolling first onto one side, and then all the way back around while I used my free hand to hoist her body back up to the couch.

Now in her original position once again, shoulders reclined against the backrest with her ass hanging off the edge, I was able to bend over and really wrap my lips around her clit while fingerbanging her butt below. The half-naked Korean babe reached out with both hands to either side, searching for something… anything… to grab onto. And in the end she came up with her video game controller.

After hitting a button, the TV blazed back to life as the racing game unpaused. Her eyes wavered, but Alice stared straight at the screen. She grasped the controller with both hands and started pushing buttons. From behind me, I could hear her start a new 1-player game. And I chuckled to myself before bearing down to really feast on my best friend’s pussy, and even added a third finger into her ass while she played her game.

We went on like that for about three minutes. Twice, it seemed like Alice was about to climax as her eyes rolled up into her head and her head lolled to the side. But both times she fought off the orgasm like a sleepy driver trying to stay alert behind the wheel. She sat up a little straighter, inhaled sharply and focused on her racing. But a few seconds later, the pleasure took over again, and her head started to nod once more.

I have no idea what place she got in the race. It doesn’t really matter. All that matters to me is that as soon as the race was over, she finally dropped the controller, let her head fall back, and she absolutely SCREAMED in ecstasy, “EEEEYYYYAAAAAAAUUUUUGGGHHH!!!”

Her butthole clenched around my invading fingers. Her legs snapped shut around my ears. Her pelvis bucked off the mattress and actually bumped my nose. And Alice vibrated and shuddered on the couch as the most powerful climax I’d ever seen her have exploded throughout her entire body.

“EEEEYYYYAAAAAAAUUUUUGGGHHH!!!” she screamed again.

“EEEEYYYYAAAAAAAUUUUUGGGHHH!!!” she screamed one final time.

And then she went limp.

I decided to keep licking her as she came down from her orgasm. Nothing super intense, just sort of lazily dragging my tongue up and down her soaking wet pussy while keeping three fingers buried in her asshole. I actually thought of introducing a fourth, since her orgasm had definitely loosened her up. But I resisted the urge and looked up at the beatific smile of heavenly bliss plastered all the way across her face.

Finally, I pulled my head up. “Enjoy that?”

“Put your cock in my ass, Matty,” she groaned, grimacing a little while helpless to even raise her head.

I blinked in surprise. “Umm, what?”

“Shove your fucking big dick into my fucking tight ass,” she grumbled in an annoyed tone.

I couldn’t be hearing her correctly. “We haven’t even had regular sex yet.”

“Is there a rulebook saying I have to lose my pussy cherry before I lose my anal cherry? Shut up and shove it in there before I change my mind.”

“Alice, maybe--”

“Dick. Ass. NOW!”

I was already rock hard from watching sexy half-naked Alice moaning from my mouth and fingers, watching her tank top propped up titties gyrating, and getting off on the mental high of fingerbanging her butt. Her asshole gaped open when I pulled out my lubed fingers, and it was a simple matter to get up on my knees and press my mushroom head into the black hole.

As soon as I was in position, Alice wrapped her legs around my torso and PULLED. The first three inches went straight into her colon. Her eyes popped open wide and her mouth gaped open just like Belle’s perfect O-shape. As the Korean girl dug her heels into my back, I leaned forward as well, and with surprising ease, I got fully buried to the hilt in my best friend’s butt.

“Fucking A you’re big,” Alice grunted once our bodies were pressed together as tightly as they would ever go. She reached down between us and started frigging her own clit. A moment later, she commanded, “Suck my titties and start fucking my ass.”

I blinked but started to do as ordered, withdrawing myself a few inches and then smoothly pushing back in. I bent over her body, wrapped both arms behind her upper back, and paused to kiss her lips first. Alice moaned into my mouth and clutched my head close for a few seconds. But then she broke our lip-lock and pushed my head down until I captured a pink nipple in my mouth and started suckling away.

It didn’t take us long. Alice turned into an animal, scratching my back with her fingernails, biting my neck, and really humping her entire body up at me. The more revved up she got, the more revved up -I- got. And after only two minutes I was pounding her into the couch cushions with utter abandon, as hard as I’d ever buttfucked any of the others.

She screamed like a banshee for the entire last minute. I’m a little surprised I didn’t go deaf. Her orgasm took me by complete surprise, as one moment she was just howling away while humping herself at me with all four limbs, the next she clamped up TIGHT and screamed, “EEEEYYYYAAAAAAAUUUUUGGGHHH!!!”

That clenching milked out my cum as well, a super-tight grip that produced incredible friction and yet did not stop me from being able to keep pumping my cock through her constricting canal. I joined her seconds later, roaring into her ear as I pumped three more times, unleashing the deluge at each thrust’s apex as I absolutely flooded the Korean babe’s rectum with what felt like gallons of cum.

When we were both done, I found myself collapsed atop Alice’s chest. We were both panting for breath and sweatier than I could have imagined, as if we’d had an intense cardio workout together (which, I suppose, we had). My arms were jello, and it took me three tries to push myself up off her chest. She stared up at me, and eventually gave me a goofy grin.

“Well THAT happened…”

I blinked and shook my head. “Didn’t you say that licking and fingers were as far as I was gonna get?”

She smirked at me. “I also said I was just like all the other BTC girls who wanted to test her boundaries with a guy she feels safe with. In the moment, I wanted to push that boundary a little.”

“You pushed that boundary all the way.”

She popped her eyebrows. “The mood was right.” She clenched her ass around me for emphasis.

I gave her a curious look. “So when is the mood gonna be right for me to finally take your other virginity?”

Alice snorted and shook her head. “You’re such an idiot, you know that? The mood has already been right a half-dozen times. You were just too dense to realize it.”

****

“Wait, what?”

So there I was, balls-deep up my best friend’s butt having just blown a massive wad into the depths of her bowels, and the more her words sank in the more confused I got. I stared at her dumbly, trying to work out her meaning.

“So…” I began, “are you saying that if I had recognized the mood when it was happening, you would’ve been fine with me just slamming it into you?”

Alice rolled her eyes and pushed at my chest. “You’re heavy. Get me some tissues or I’m gonna leak out all over your couch.”

I took me an extra beat before I sprang into action. I pulled out of Alice’s distended anus and quickly hunted down the tissue box while she curled her knees up to her chest like an armadillo to let gravity help keep my cum in her ass. Not for the first time, I wished Belle were here because then cleanup would be easy and obvious.

I got Alice the tissues and she rather uncomfortably shoved three of them into her gaping butthole. Then standing up and clenching her cheeks, she waddled into the bathroom to sit down and release. The sounds of liquids dribbling out of her and plopping into the toilet soon followed.

Alice called out the door, “I see what you mean about this being an inconvenient ‘dessert’ thing.”

“Yeah, it’s unavoidable,” I called back. “Well, unless Belle’s around.” I started to clean myself up too. I kept a package of baby wipes under the couch next to the lube.

Eventually, Alice flushed, returned to the room, and announced, “I think a proper shower is in order.” She gathered her clothes and started heading out of the room.

I grabbed my clothes as well and followed after. “You still haven’t explained what you meant about recognizing the mood.”

Alice rolled her eyes. “If I have to tell you to do something, it defeats the whole purpose.”

“C’mon, you’ve always been straight with me.”

“I AM being straight with you.”

“Then give me a straight answer to this question: When ARE we going to have pussy sex?”

“When the mood is RIGHT.”

“And how do I know when the mood is right?” We hit the stairs and started ascending. “On the one hand, I’m waiting for you to tell me you’re ready. I’ve spent years not pressuring any of you girls into doing anything you’re not ready for, and I swore to myself I’d never do anything you didn’t give me explicit permission to do.”

“Yes, and I’ve loved that about you.”

“And then we talked about this way back during winter break. You said that it would happen when the mood was right. Maybe we’d be gaming and you’d toss the controllers aside and order me to slam it into you, the way we did just now when you told me to put my dick in your ass.”

Alice snorted. “Yeah, that was kind of a spur-of-the-moment thing. I didn’t plan that.”

“But you don’t regret it either, do you?”

“Not at all. That was AMAZING.” Alice stopped at the top of the stairs and reached out a fist. “Seriously, dude. Amazing.”

I chuckled at the absurdity of it all, but I fist-bumped her anyway. She then continued on to the bathroom, adding, “I NEVER thought I’d be into anal sex. And I get that it’s not gonna be a regular ‘main course’ sort of thing. But if we’re both in the mood for dessert, you may very well get a repeat sooner or later.” She tossed her clothes onto the counter, reached in to the shower, and started turning on the hot water.

“So anyways,” I continued, “you then said maybe you’d show up in a nice dress and ask me sweetly to take your virginity. The point is: I’m waiting for your cue.”

“I know you are.”

“But then there was that video game girls thing on Valentine’s. When you parked yourself next to Mari and Naimh, it certainly felt like an implied invitation to push myself into you. Was it? Was that a cue?”

Alice looked thoughtful. “What did you think?”

“Straight answers here.”

Taking a deep breath, my best friend exhaled slowly. She focused on the water temperature, holding her hand in the shower spray waiting for it to heat up. “Let’s just say… if you HAD pushed yourself into me and taken my virginity then and there… I wouldn’t have regretted it.”

I furrowed my eyebrows. “So I DON’T have to wait for explicit permission?”

Alice turned to me, her eyes sharp. “I’m not giving you carte blanche to just ram it into me whenever you want. Let’s be clear about that.”

“No, no, of course not.” I held my hands up defensively.

Alice stepped into the shower, ducked her head into the spray, and stood up straight while using both hands one at a time to push the water back from her forehead and through her scalp. She looked incredible.

“What I’m saying is,” she stated slowly, “if I have to tell you, it defeats the whole purpose.”

I still didn’t completely understand. Sighing and shaking her head, Alice gave me a look. “You coming in or not?”

I got into the shower.

Smirking and brushing my hair back from my face, Alice hugged me, kissed me, and sighed. “I love you, Matty. Not romantically, but I love you. You’re still gonna be my first everything. But I need you to figure this one out on your own, alright?”

I took a deep breath and nodded. Meanwhile, Alice put soap into my hands, helped me lather them up, and then placed my palms on her big tits. We didn’t start up another sex session in the shower, but we definitely had fun getting clean. And in the end, Alice told me she was driving over to Naimh’s house to hang out for the afternoon.

Me? I drove out to pick up fast food for lunch. And right when the drive-thru attendant asked me through the speaker box for my order…

… THEN I finally got it.

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