Alyssa (Babysitter’s Club 1)

Our mouths moved together, switching tongues from one to the next in a sensual dance. “I’m going to fuck you deeper now. I’ll try not to hurt you but I have to reach your pussy bottom. It’s the only way this will be complete.”

With my finger in her ass and my teeth clenched around a tit, I power fucked her with quick strokes of my hips until I felt her pussy give. “That’s it baby, open up and let me in.”

She was out of her mind with lust now, moving wildly beneath me, moaning for more cock. But because I was so attentive to her, I heard the little squeaks of pain mixed in with those moans of lust.

I kept up the same pace of in and out, three times hard, three times soft, one hard, one soft, and repeat, until I found the rhythm that she liked. I wanted to give her as much pleasure as I could her first time.

I don’t know much about virgins, only locker room talk that’s usually not exactly accurate. But I know that my cock could really hurt her if I’m not careful and that’s the last thing I want.

I also know that this virgin at least, was now owned by me. I’d gone from one end of the spectrum to the next. Never in my wildest dreams could I have imagined finding someone like her. Pure, untouched. “Mine!”

Gage

It took some time but I was finally in her to the hilt. I knew she was hurting from the silent tears that slid down her face, but my brave girl was doing her best to take all of me without complaint.

“I’m not going to stay in you too long this first time baby. That shit’ll hurt you.” Her eyes were glazed over, mouth slack as she nodded her understanding.

I didn’t need to tell her to squeeze her cunt around my pole, her pussy was doing that shit on its own. It was like getting my dick massages by a suction cup. Best fucking thing I ever felt.

She wrapped both legs around my ass and dug her nails into my back as she kissed me furiously. My finger went wild in her ass as my cock thumped and pounded away at her pussy.

Now the sounds she made were hoarse, guttural grunts. The bed beneath us was soaked with her juices and I was afraid blood as well. It couldn’t be helped. At least that much I know about virgins; they bleed!

“I’m not pulling out!” There’d been a slight chance that I might because of her age even though I didn’t want to. But her being a virgin changed everything.

“I’m going to cum inside you every time and you’re going to take it.” For some reason, the gentleman in me took a backseat and the man she made me feel like being took point.

I felt an insane intense need to possess her completely. To leave no room for mistakes. I know part of that had to do with my failed marriage but it was mostly about her.

This sweet little innocent who’d given herself to me. If she’d had plans on this being a summer fling she was in for a rude surprise. By the time I felt my balls draw up hard and the first volley of my cock cream shot off inside her, I’d already planned half her life.

“You’re not going anywhere, you’ll never leave me. I’ll kill you first.” I felt those words and meant them. Whatever plans she had for her life would have to change unless they involved me.

Maybe I had pussy fever, maybe I’d lost my mind, whatever the case, the things I felt and said in that moment came from a place inside me that I’d locked off never to reopen.

I felt a whole host of things as my cock dribbled its last bit of seed inside her. “You came!” I looked down at her in amazement. Even with all the pain I’d given her she still found pleasure in having me inside her.

I brought her down with soft nibbling kisses and sweet words of love and admiration whispered in her ear. Taking my time and being as careful and as gentle as I could, I eased my dick from where it was lodged at the mouth of her womb.

She hissed with pain and relief when I finally slid free. “Don’t move baby I’ll be right back.” I jumped off the bed and walked across the room to the en suite.

Once inside I turned on the hot water in the bath and looked around for something to soothe her with. As an athlete I have tons of shit that’s good for sore muscles, but nothing to ease a sore pussy.

I got an idea and while the tub was filling, ran down to the kitchen bare ass naked. I grabbed a tray of ice and ran back to her after grabbing a little hand towel.