“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 déja 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.