Chapter 8: Annabelle

I’ll never forget for the rest of my life the first time I entered her. She was so freaking tight. At 5’1” with proportionally scaled-down hips, Belle was a small girl, and her vagina was similarly small. Add in the fact that she was a virgin who’d never stuffed a cucumber, hairbrush, or even a tampon into her pussy, and you’re setting up a recipe for peeling the skin off my dick upon entry. Seriously, the two fingers I’d stuffed into her tonight only to the second knuckles were the biggest things she’d ever felt inside her. Those muscles simply weren’t prepared to be stretched by something as thick as my dick, and I’m a little embarrassed to say her deflowering did not go very well.

Belle, too anxious to get fucked for the first time, was overly overconfident in her virgin pussy’s ability to accept my big dick without preparation. While I told her I wanted to go down on her first and get her warmed up, she insisted she was already wet and wanted to feel me INSIDE her. Like NOW. Before I second-guessed everything and went into vapor lock about thinking of her like my little sister again.

She had already stripped herself naked, so once we agreed that yes, we were doing this, she helped me get naked too.

“Do you still wanna be on top, or do you want me?” I asked.

“You.” She smiled up at me coyly. “I’d settled for the idea of impaling myself on you before you realized what was going on. But I’ve always dreamed of you holding me in your arms, looking down into my eyes, and cuddling me close while you push your thick cock into my little pussy to just... take ... me.”

Well that sounded pretty great to me, so I rolled Belle onto her back, climbed on top, and started kissing her like the apocalypse was imminent and the last things I wanted to feel on this earth before the meteor of doom hit were her lips pressing against mine.

I actually told her that while we were kissing, and she moaned and wrapped her legs around me. Our height difference was such that her pussy was more or less around my belly button while we kissed, so it wasn’t like I could grind my shaft against her clit, not without breaking our lip-lock. All of a sudden she was in a terrible hurry, whimpering, “In me, Matty. I need you in me. Please?”

How could I possibly say no to that? So I nodded my assent, crawled forward a bit so that my chin was at the crown of her head, and looked back down my body. She reached for my dick before I could, spreading her legs wide and aiming my mushroom head at her entrance. Her labia had been opened slightly by my fingers, so it wasn’t like her pussy was completely closed. She managed to notch me into place, and while keeping her tiny right hand circled around my shaft as a guide, she dug her heels into my ass, directing me to start pushing my way inside.

It hurt.

A lot.

I did a full push-up, locking my elbows so that I could get a good view of her face as she felt her first ever penis penetrating her pussy. She said she wanted me looking down into her eyes, and if she’d been looking back at me she would’ve seen the concern in my gaze. But her eyes were clenched shut as she grimaced and winced and generally looked to be in terrible discomfort, so I immediately stopped my forward momentum and started to retreat.

“No!” she cried, clamping onto me with her legs and gripping my dick tight in her right hand. “In me! In me!”

“You look like you’re in pain,” I reasoned.

“A girl’s first time always hurts; don’t you know that?”

“Uh, I mean I’ve heard stories, but--”

“Just fucking DO IT!” Hugging my torso, Belle yanked on me with both legs and arms, so I stopped resisting her and began to push my way forward again.

Belle was in agony. She screamed, and not in a good way, as my cockhead tried and failed to push through. Her labia weren’t separating, and it felt like I was pressed up against a brick wall. Tears were now running down her eyes, and after the way Sam had cried so much it made her waterproof mascara run, I was beginning to wonder if every sex encounter I ever had would begin with me making the girl cry.

“I don’t think it fits,” I groaned, feeling Belle’s insistent pressure for me to push down but literally feeling blocked by ... something. It was as if my dick was caught in a spider-web or some other kind of elastic sheet.

“It’ll fit!” Belle whimpered. “Everyone has always said it’ll fit. I’m a girl! A woman! My body was made for this!”

“It’s not fitting though. And I don’t think you’re really wet enough. Lemme go down on you. Give you a nice orgasm and get the fluids going. Stretch you with my fingers a bit, huh?”

“Just push it in, gawddammit!” The tears were flowing freely, and she looked absolutely terrible. “Maybe it’s my hymen, I dunno. Just DO IT! Tear that shit up! In me! Now, Matty! INNNNN-OOOOWWWWWWWW!!!!”

I should have listened to my own advice, but she was so insistent I finally just slammed my hips forward. That elastic sheet suddenly ripped, and before I knew it, I had three inches of dick inside her. That was it. I’d torn Belle’s cherry. She wasn’t a virgin anymore.

I’ll never forget for the rest of my life the first time I entered her. And NOT in a good way.

I had three inches inside her, but I wasn’t getting any farther anytime soon. I may have gotten past the first obstacle, but more challenges still lay ahead. Now that I’d gotten past her entrance, I figured pushing in the rest of me should be fairly easy. But it wasn’t. She was SO. FUCKING. TIGHT.

I tried letting gravity drop my hips, but I didn’t budge. Actually, attempting to support all my weight on my dick just sorta made my dick start bending in a direction it wasn’t meant to, and that didn’t feel good at all. I tried digging my toes in and really mashing my hips downward, and that got me maybe another inch, but that’s all.

Meanwhile, Belle started sobbing, in a world of pain, and when I looked back down and saw her face, my resolve completely left me. I’d spent years convincing myself that my role was to protect Belle like my little sister, not to molest her, fantasize about her, objectify her, or in any other way consider her as a sexual being. I was the one getting high-fives from Belle’s dad for telling him I’d pound the face in of any boy who made her cry. And yet here I was, the molester who had painfully torn Belle’s precious maidenhead and quite literally made her cry.

I got my knees under me, pulled out, and that’s when I saw the blood on my dick. I didn’t know for sure if it was hymen blood or period blood, but let’s get real: seeing blood on your dick is NOT arousing in the slightest, and I started to soften immediately.

Belle didn’t seem much in a sexy mood, either. And as soon as I pulled out, she twisted her hips and curled up into a fetal position, hugging my pillow like a life preserver while she sobbed her little heart out.

I grabbed a few tissues and quickly cleaned up my shriveling penis. Then I dropped to the mattress and spooned behind Belle, holding her firmly in my arms. She shuddered and backed up into me, seeking comfort in my embrace, so that helped me not feel so bad about the molesting-destroyer-of-virginities feeling, and I shushed her gently, feeling a very weird sense of déjà vu having done basically the same thing just last night with Sam in this very same house.

“I’ve failed you,” Belle sobbed.

“No, no. It’s okay, it’s okay. This isn’t your fault.”

Seriously, I was NOT expecting to be in this position again so soon. Less than twenty-four hours ago I’d lost my virginity to one of my gorgeous friends, and now I’d taken the virginity of another of my gorgeous friends. Less than twenty-four hours ago, I’d had to comfort a despondent girl who was crying over her apparent failure to please me. And now here I was again.

“I wouldn’t have even been able to impale you by surprise if I wanted,” she moaned in abject misery. “I’m too small. It wouldn’t have fit.”

“I think we were just in too much of a hurry,” I reasoned. “I should’ve taken the time to stretch you out before we started. This is my fault. I should’ve slowed you down.”

“This is MY fault. I was the one who insisted you just hammer it in.”

“We’ll do better next time. There WILL be a next time. I’m not going to go into vapor lock and try to say you’re like a little sister to me anymore. I can’t hide behind that shield any longer, because it’s time I admitted the truth to myself. I LOVE you. I’ve always loved you. Fuck, I’ve been in love with you since I was twelve. You’re my Annabelle.”

She was still crying, but the sobbing slowed and eventually stopped, and her whole body went still for a second. Then, the petite strawberry-blonde in my arms started to turn around, looking back at my face through bleary eyes. “Wait, what did you say?”

“I love you. You’re my Annabelle,” I repeated.

“No, the other part. You’re in love with me?”

“What? No. I’ve always loved you, and I always WILL love you.”

“No, no. You specifically said you were IN love with me.”

I snorted and backed away from her a bit. “That’s just crazy, B. I think you misheard me.”

Belle frowned and furrowed her eyebrows as she completely turned around to face me. “You’re lying. You’re not a very good liar, and I can always tell.”

“Belle, seriously.”

“How long have you been in love with me?”

“I’m NOT. I’m not in love with ANY of the girls. That would totally ruin the BTC. We’ve had this conversation before.”

“Then why did you say it a minute ago?”

“I didn’t.”

“Yes you did,” she said seriously. “You said you’ve been in love with me since you were twelve.”

I sighed. “Yes, I had a crush on you when I was twelve. I’ve told you that already, back when you were infatuated with Taylor Guazelli.”

“And you’ve been in love with me all this time?”

“No, no, of course not. You’re blowing this whole thing out of proportion, B.”

“Am I?”

“I can’t be in love with you. You know that.”

“Why not? And don’t give me some bullshit about me being your little sister.”

“No, I told you I wasn’t going to hide behind that anymore.”

“Why were you hiding behind it in the first place?”

“I...” My voice trailed off, and I took a deep breath to try and collect myself.

“You’re not twelve anymore, Matty. You told me you mentally categorized me as ‘out of bounds’ so you wouldn’t be hurt by rejection, but that was a long time ago. There hasn’t been a Taylor Guazelli in my life for a long time, and the relationship we have now is nothing like it was back then.”

“It’s not,” I agreed. I took a deep breath, closed my eyes, and tried to relax my brain. I could feel the truth bubbling beneath the surface, the words trying to float into my brain if only I’d let them. Just like the words, ‘I’ve been in love with you since I was twelve’ had come into my brain and flown out of my mouth all on their own, a sentence I couldn’t deny I’d said any longer.

“I...” I began again, but stopped as I felt the old mental blocks coming back into my mind.

Belle was patient. She didn’t press me.

“I...” I began again, and once again stopped and closed my eyes.

Belle rubbed my shoulder and gave me a warm, inviting smile.

I started shaking my head, muttering, “I can’t. It’s ... I--”

“I love you, too, Matty,” Belle said softly. “I’ve been IN love with you a long time, too. Not since I was twelve, unfortunately. But ... I dunno. Fifteen? Before the BTC. I didn’t want to admit it to myself, but it’s certainly the reason why I never really dated anyone else.”

I blinked in shock. “Wait, what?”

Belle grinned. “That’s why I always knew you’d get my cherry. It could never have been anyone else.”

“But you’ve gone out of your way ... several times ... to state that you’re not IN love with me.”

Belle shrugged. “We all lie, even to ourselves, to avoid getting hurt. How could I tell you I was in love with you when you constantly held me at arm’s length with your whole ‘little sister’ schtick? You made out with everyone but never let ME kiss you. It would have broken my heart to admit I was in love with you only to have you fall in love with ... I dunno ... fall in love with Sam or something.”

“I’m not in love with Sam.”

“I know that, and I’m glad for it.”

“Shit, B. What are we gonna do? If I’m in love with you, and you’re in love with me ... what the HELL are we gonna tell the girls?”

Belle shook her head. “We’re not gonna tell them anything. Nothing changes, at least not for now. I may have tried to cover up just how strongly I felt for you, but I wasn’t lying about not breaking up the BTC for us. There will be time for us to figure out our feelings for each other. There will be time for us to figure out your feelings for the other girls, too. And yes, there will be time for us to make this sex thing work. Because I’ll be honest, if we don’t figure out how to make this sex thing work and it’s gonna be THAT fucking painful every time we try it, I am falling OUT of love with you as soon as fucking possible.”

I laughed at that and leaned in to kiss her. She met me with a tender brush of her lips, and I reached up to stroke her cheek.

When we pulled back, I stated sincerely, “I do love you, Annabelle.”

She glowed and replied back primly, “And I love you, Matthew.”

Belle giggled and shook her head. “It does feel a little weird, calling you by your full name. You’ve been Matty to me for as long as I can remember.”

I shook my head. “You used to call me Matthew all the time when we were little. Back then, I NEVER called you Belle. Your friends did, but not me. You had ALWAYS been my ... holy crap.”

Belle gave me an amused look. “I’d always been your ‘holy crap’?”

My eyes were wide and unseeing. The truth that I’d been trying to keep down had suddenly floated up into my brain while I’d been distracted. And I shook my head at the realization.

“What is it?” Belle asked.

“I just realized when ... and why ... I stopped calling you Annabelle and started using Belle instead.”

She snorted. “Because I kept ASKING you to call me ‘Belle’?”

I gave her a sad look and said, “I remember why you started insisting everyone call you ‘Belle’ instead.”

Her eyes flickered, and I saw her start to close up a bit.

“Too painful?” I asked.

“Matty...”

“You had always been Annabelle to me. Your mom LOVED saying your full name, saying she chose it because it was so beautiful, like you. And every time I called you by your full name, I remembered the way your mom used to say it, too.”

“Matty,” Belle said a little more strongly, a touch of warning in her voice.

“She was as much a mom to me as she was to you, far more than my own mother, and once she was gone, I clung to you like a life preserver. After we lost her, I was terrified of losing you. I told you it was never a sexual thing back then. I hadn’t hit puberty and didn’t even have hormones. But I knew I wanted to spend every waking moment possible with you. I wanted to marry you, maybe not so much because I wanted to date you or anything like that, but because if we got married, we’d be together forever.”

Her expression softened. “I used to dream about that too. Still do, every now and again.”

I smiled. “Maybe we WILL be together forever. We’re still teenagers right now. Who knows what the future will hold?”

She looked hopeful. “Maybe.”

My smile faded. The truth had come into my mind, and it wasn’t leaving. “But I couldn’t have you back then. By the time I was twelve I was in love with you, but you wanted Taylor Guazelli. I realized I couldn’t have you, and yes, you did keep asking me to call you ‘Belle’ instead of ‘Annabelle’, especially around your friends.”

She gave me a curious look, a kind of realization dawning on her face even before I said it.

“The day I decided you were my ‘sister’ and that I’d never get to have you? That was the day I stopped calling you ‘Annabelle’, at least on a regular basis. From then on, you were just ‘Belle: my sister’. It was as if I could package up all the love I felt for you into the full name ‘Annabelle’ and tuck it away for safekeeping. It still comes out from time to time, in those special moments when it’s just me and you and I feel so happy inside I can’t help but think of you as ‘my Annabelle’ the way we were when we were kids. But so long as you were ‘Belle’ or even just ‘B’ to me, we’d never be more than friends.”

“Matty...” she caressed my cheek and said a little uncertainly, “Matthew...”

I arched an eyebrow at the way she physically chewed, as if tasting the way my full name felt in her mouth.

Shaking her head slowly, she grimaced and said, “I don’t think I can go there. It’s a nice enough name, but you’re still Matty to me.”

I laughed. “I never said you had to use MY full name. I’m good with ‘Matty’. Really, I am.”

She looked relieved. I leaned in and kissed her, and gave her a warm smile when we pulled apart.

“I’ll love you no matter what you call me. But for those times I do call you ‘Annabelle’--”

“I’ll hear you saying ‘I love you’ in my mind,” she finished for me.

I grinned. “Yeah, pretty much.”

“Works for me.”

I nodded, and she nodded, and a long silence fell over both of us. We smiled at each other, unsure of what to say. And after the silence started to become a little awkward, only then did we seem to remember our nudity.

“I did NOT expect to have this conversation today,” I finally said, a little embarrassed.

“Me neither. But...” She popped her eyebrows and gave me a hopeful smile. “I know this hasn’t been the most ‘uber sexy’ conversation, but would it be too weird for me to say I’d still like to take another shot at this sex thing?”

I raised my eyebrows. “You sure?”

“I don’t want to go to bed tonight still a ... Well I guess I’m not technically a virgin anymore, but I still don’t feel like I’ve earned my woman card.”

I smiled but held up a finger. “You’re letting me go down on you this time, no arguments.”

“Not arguing.”

“Maybe I shoulda bought some lube.” I suddenly grimaced and rubbed my temple as if I could physically scrub away the thought that had just popped into my mind.

“What?”

I sighed. “It occurred to me that Mother might actually have some in her bedroom. As much as I don’t want to think about it, she’s been a single woman who has kept herself in amazing shape ever since the divorce, and while she’s never brought a man here as far as I know, she definitely stays out pretty late at night.”

Belle could tell I really didn’t want to go snooping around Mother’s bedroom and she stroked my hair, saying, “Don’t worry about getting lube. We’ll make it work.”

Relieved, I nodded and repeated back to her, “We’ll make it work.”

We made it work.

We had both learned our lesson after that disastrous first attempt. We took our time, made sure she was plenty wet, and I pre-stretched her out as best I could.

Belle’s bright idea was to have our very first two-person shower to get cleaned up first. I was in heaven soaping up her petite, naked body, running my hands all over every inch of her silky-smooth skin. After years of fighting my own conscience every time I touched her in a semi-intimate way, it was SUCH a relief to simply enjoy myself grabbing her ass, fondling her tits, and kissing her lips beneath the shower spray.

We dried off and returned to my bedroom completely naked. We kissed and laughed and fell onto my bed to kiss some more. But eventually I started kissing my way down her body, pausing of course to luxuriate in her boobs. She would never have the massive melons Sam or Mari sported – globes that big would’ve looked ridiculous on Belle’s tiny frame – but she was so skinny and small that she ended up looking pretty top-heavy anyway, which to me meant they were perfect. I liked my girls pretty top-heavy, you know?

I devoured her breasts while Belle giggled and stroked my hair. But rather than linger, I quickly kissed my way down the rest of her body, tickling her ribs and briefly sticking my tongue into her belly button before reaching the juncture of her thighs.

By now I’d eaten Belle’s pussy many times, so it was with no hesitation that I wrapped my lips around her clit and shoved my tongue up into her twat. Desperate to make up for the pain I’d caused during her deflowering, I sought to soothe her strained muscles while paradoxically doing my level best to make them clench up in climax. At first, I succeeded more at the latter when I ate her to an orgasm, but in the end still got the former because she went limp and got super-relaxed after cumming. That’s when I slithered first one and then a second finger into her narrow channel, pumping slowly, intent on stretching her out while I languidly licked at her pleasure button to keep her distracted.

“Squeeze...” I intoned softly. “Imagine my cock is inside you. Squeeze ... and release ... Yeah ... like that ... Clench tight ... and relax ... Holy shit, B, you’re gonna feel so good when I’m inside you. Release ... yesss...”

My little lover was moaning and on her way to another orgasm when I pushed in a third finger. But once I had three fingers sliding in and out pretty well, I figured she’d been stretched out enough and switched gears to concentrate on getting her another oral orgasm.

Sam had taught me a few tricks, and I’d practiced them on the girls during Friday’s naked in heels bootcamp as well. But Belle had been on her period and I’d been unable to go down on her, so I was eager to explore and see how she reacted. Rotating my wrist and reducing down to two fingers again, I curled my digits up in search of her g-spot. I could tell I’d found it when Belle shivered and suddenly couldn’t keep her hips still. I bore down with my lips and did my best to keep her pinned beneath me. Eating a moving target isn’t easy, as I’m sure any African predator will tell you. But it didn’t take long before I made her cry out in ecstasy, and once again, my little Annabelle went limp beneath me.

It was time.

Wiping my face with the back of my forearm, I didn’t waste a moment before sliding up her body and notching myself into place. Her puffy pink labia were now wide-open and inviting instead of closed up tighter than a clamshell, and with only a little bit of pressure I felt my mushroom head pop in.

Belle gasped, her eyes fluttering open as she felt that first penetration, and she immediately clenched up.

“Release ... release...” I soothed. Stroking her forehead, I added sincerely, “I love you, Annabelle ... I love you, Annabelle ... I love you, Annabelle...”

She cooed into my ear as her body visibly relaxed beneath me, and with a little more pressure I steadily burrowed inch after inch into her tiny body.

She was still exquisitely tight, tighter than anything I’d ever felt in my life, not that I had a whole lot of sexual experience. Even Mari’s deep-throat couldn’t compare, and when I finally had every last inch of myself inside her, I had to stop and just savor the experience.

Belle was like minded, breathing shallowly with her eyes closed and her forehead furrowed in concentration. It took more than a minute to get myself fully seated, and now that she realized I’d stopped, she opened her eyes 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.”

Barely. She was a perfect fit for me, her pussy tailor-made like a glove that matched my cock to its exact specifications without a millimeter to spare. The feeling of being inside her was exquisite, even without any thrusting. My heart was filled with love for the girl I’d adored since I first realized the human species came in two different sexes. And for the next several minutes, we were both happy to remain as we were, making out for the first time while joined together so completely.

But after a while, Belle broke away to breathe, looked up at me through heavily lidded eyes, and murmured, “Fuck me, Matty. I wanna feel it.”

Her words said “fuck me”, but I was seized by a sense of wrongness in that, not so different from the wrongness I used to feel about molesting my “little sister”. I wasn’t going into vapor lock or anything, but I suddenly remembered something Belle had said earlier. She didn’t want to hear my bullshit about how I’d never promised I’d “fuck her”; she’d specifically used the phrase “make love” to her. And THAT somehow felt so much more ... right ... to me.

So I told her, “I’m not gonna fuck you.”

Belle blinked and looked up at me in surprise, not understanding.

I smiled and said, “I’m going to make love to you.” And then I kissed her.

I did make love to her. Not that there’s anything wrong with fucking. I’d fucked the shit out of Sam last night and she’d loved every second of it. Someday soon I’d fuck the shit out of Belle and I knew she’d love it too. But tonight, Belle and I made love.

I slowly retracted a few inches and then smoothly pushed my way in. I took up a gentle rhythm, not too hard and not too fast. Belle’s pussy was still too constricting to build up much speed anyway. She was copiously wet, but the friction was still incredible. Even my leisurely pace was enough to generate a world of sensation for both of us, evidenced by the fireworks in my brain and the whimpers and moans of Belle beneath me.

“You’re so big inside me,” she whined, arching her back and wincing at the edge of pain but not quite. “I feel so full...”

“You feel so good around me,” I hummed right back. “Your pussy’s amazing, Annabelle.”

“So deep ... So big ... So ... OOOH!” Belle’s eyes suddenly flew open. “Ohmigawd what was that?”

I blinked in surprise myself. I’d started to retract a few more inches, until I was almost out, before sliding back in. The extra inches and extra push let me get about another centimeter or two of depth on the downstroke, and when I hit bottom it felt like my cockhead had bounced off a spongy wall.

“I think I hit your cervix,” I muttered in wonder.

“Do it again!” she breathed. “It set off a little sparkle in my brain.”

As ordered, I pulled back and thrust all the way in again, but somehow didn’t quite get deep enough. I didn’t feel the bump, neither did she, and Belle looked a little disappointed.

“Hang on a sec,” I told her and scooped my arms beneath her legs, spreading them out to the sides until my elbows hooked under her knees.

This time, when I pulled back and thrust in, I felt that little bump at the end, and Belle’s eyes fluttered as she cooed, “Oooh, yeah ... That was it. Do it again.”

So I did. Again and again and again.

“Ungh, ungh, ungh,” Belle started groaning every time I hit that spot.

“Hmph, hmph, hmph,” I was grunting every time I put that much extra energy into my thrusts.

“Fuck, fuck, fuck,” she started chanting, her pussy squeezing me as I powered my way through her narrow channel. I still wasn’t up to true “fucking” speed; she was still too tight for that. But I was definitely thrusting harder than I had in the beginning.

“I love it,” Belle whined. “I love this. I love you! Why the fuck didn’t we start doing this sooner?”

It was a rhetorical question, one I couldn’t answer right away. I was too focused on getting her off, sensing just how close she was getting to cumming. Her eyes were shut as she concentrated on the sensations I was giving her. My eyes were laser focused on her face, watching her reactions and reveling in the sense that -I- was the one giving her such pleasure. And all of a sudden, her eyes flew open as she announced, “I’m gonna cum! I’m gonna cum! OHHHWWWAAAAAAAUUUUUGGGGGHHHH!!!”

Belle’s back arched, her hips thrust upwards, and she met my next thrust so that my dickhead made one big hammer blow against her cervix. She screamed even louder when that happened, going into what looked like epileptic convulsions at first glance. I tried to keep fucking through that orgasm, but her cunt clenched down, constraining my cock and keeping it captured in her clutches. With my dick completely surrounded, her muscles milked me from all sides until I couldn’t take it anymore. And a second later, I felt my own ejaculation begin to FLOW.

“ANNABELLLLLLLE!” I yelled, feeling my mushroom head open up like a firehose and begin spraying gallons of creamy cum straight into her cervix. Over and over again I poured my seed into Belle’s snatch, my hips twitching as I filled her up to the brim.

And then I collapsed, gasping for breath. I braced my elbows on the mattress lest I crush her beneath my weight. Our height difference was such that my head was above hers, so she pressed her lips against my chest and nibbled a little on my collarbone.

“Ohhh, Matty...” she crooned, her voice filled with rapturous ecstasy.