Just one...

As Jeremy lined his cock up with the hole that he had found with his fingers Sandy stepped over to the side, "One last piece of advice, then I'll leave you two alone. When you enter, when you tear her hymen, stop, and let her direct you into her. Okay?"

"Sure thing. Sharon kind of said the same thing when she was...uhh...anyway. Yeah she was muttering about how even she'd have to take this thing in stages."

"That's a great way to put it. I think I'm going to have to meet this Sharon person." Sandy said. "Anyway, have fun you two. I'll leave the two of you to have your moment together, by yourselves."

With that Sandy walked to the door, and let herself out.

Jeremy looked to his love, and gave as confident a smile as he could to Courtney, "Are you ready?"

Courtney raised her head up and looked at the massive tool poised at her entrance. A flash of worry over the pain hit her mind, but at the same time she wanted it so bad. She let her head fall back onto the bed, "Yes, Jeremy. Please take me." She said, her voice full of need, and want and lust.

Jeremy took a breath and then with his fingers separated Courtney's Pussy lips. Gripped in his other hand he guided his lubed up cock into the lubed up slit. After it slipped up and out of her slit he tried a second time. While he hadn't meant to miss the target he did like the "Oh!" that came out of Courtney's mouth.

Courtney was breathing heavy, her hands trembled a bit as she watched Jeremy try and hold her pussy open slightly and guide his cock into her. The lube didn't help too much, and he missed a second time this time down to her ass, the head of his cock grazing her rosebud. "H-here...let me hold me open for you, okay?"

Jeremy nodded as he lined up his cock again, as Courtney reached down and spread herself open a little farther than he had been comfortable with for fear of hurting her. Another thing that Sharon had said popped into his mind, even as his cock head settled into the entrance of her pussy. "Women are stronger than we look, Jeremy." She had said, "I mean this whole area is where babies come from. And I know you may have a babies arm where a penis should be, but it's still not as big as an entire baby. We can take some poundings. With your size you may have to ease it in, but once we adjust, hoo boy, even you can go at it!"

With everything lined up Jeremy looked back up into Courtney's eyes, smiling to put her at ease.

Courtney saw him smile at her, and tried to return it, but his big cock head was very distracting to her. At the moment there was no pain, but the stretching sensation she felt wasn't exactly comfortable. Courtney wanted this part over with, the apprehension, the not knowing. The nervousness was really starting to get to her.

Jeremy saw a lot of this in Courtney's eyes and wanted nothing more than to reassure her more. He could tell that she wanted to get this part over with. He leaned forward, his hand holding his cock in place, neither moving further in, nor moving from the entrance of her slick slit.

As their lips met Jeremy took that opportunity to enter her. Her felt the resistance of her hymen almost immediately and pushed a littler harder. Courtney shrieked into his mouth loudly. Her eyes filled with tears as the tearing sensation ripped through her young body. She was aware that Jeremy had already stopped moving, entering no further for now.

After a moment the pain left Courtney. She moved her hands from opening herself and instead moved her arms to encircle Jeremy's body.

Jeremy felt her arms moving, and her legs too after her feet rested on his ass. Jeremy moved in a little further, stopping when he felt her tense up. He moved his cock out as they continued to kiss sweetly. Her relished the feeling of her pussy wrapped tightly around his cock, though of course it wasn't a painful tightness as the too small condom had been.

Jeremy wondered if her could bury himself to the hilt or if that was beyond what Courtney could take at the moment.

For Courtney's part she wanted to feel his balls on her ass, though she wasn't sure if she could take all of him at this time. She already felt like his cock was intruding into her intestines, and that she knew was physiologically impossible.