Chapter 33: Dessert

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 chest no longer supporting Belle 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 upon 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. My baby Belle started breathing a little more deeply, her lips parting open ever so slightly, 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 continued the more her labia opened up, making access pretty easy. I smeared her liquid arousal all over the place 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 as 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 jerked 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 cute little clit, 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 pushed two fingers into her steaming wet box, curling them to tickle her g-spot. From within, I felt the snug constriction of her little hole, the channel’s volume displaced by the silver butt plug in her colon, it’s blue crystal glinting in the morning light just beneath my pumping hand.

“Matttyyyy...” Belle hissed through clenched teeth as her fingers scrabbled at 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 “AHHHWWWAAAAAAAUUUUUGGGGGHHHH!!!”

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 throughout 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 eventually 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 teeny 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 backdoor chute. And only after I was buried to the hilt and had 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, Belle opened her eyes again and squeaked softly, “Did it all fit?”

I chuckled and pecked her forehead. I then 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 special nickname for her asshole reminded me that not everything had been resolved nor would be washed away by this one 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 tried out flexing them 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 raided her tight little rectum.

Belle groaned gutturally when her first anal orgasm snuck up on her. She flopped and twisted and her colon momentarily clenched up so tight I couldn’t move. As the ecstasy exploded in her mind, 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 went 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 furiously French kissing 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 sometimes did 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 dizzy 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 shins 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 just from the sight of it, 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 position she’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 exquisitely tight 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, “AHHHWWWAAAAAAAUUUUUGGGGGHHHH!!!”

“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 together.

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. And in my experience, that comes from the soreness of either riding a horse, riding a bike, or riding a man. You tell me which of those she was doing in your room this morning.”

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 (and failing) 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 with my big dick pumping in and out of her tight teenage asshole, Naimh, Sam, and Mari were quick to line up their asses 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 group sex session 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 you 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 necessarily. 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, in the days when all I got was some kissing and dry-humping, Mari letting me suck on her nipples and giving me a handjob until I came all over my own belly made me feel 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 it seemed like thoughts of having sex consumed my every waking moment. 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 did say 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.”

“I’m not trying to inspire you. You asked, so I’m just giving you my opinion about why the others do what they do. And well, I really don’t think it’s 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, Alice 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. The BJ Queen of the BTC probably enjoys showing off her Body Built For Sex.”

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 selfish pleasure.”

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