Breaking through the Barrier

You begin to gently move your hips, sliding the part of your cock that was inside her in and out. Anna's face contorted into a mixture of pleasure and discomfort as you try to find a rhythm that would please her. Sweat trickles down your forehead as you focus on not hurting her while also trying to give her as much pleasure as possible.

But as she continued to push more of her ass up towards your cock, you couldn't help but try to do the same. With a surge of determination, you grip her hips and thrust forward, eager to bury more of yourself inside of her. However, you soon realize that your efforts are in vain as your cock only goes in a little deeper before hitting the same barrier as before. Anna lets out a small yelp of pain, her face scrunching up at the unexpected intrusion.

"I'm sorry, I didn't mean to hurt you."

"No. No, it's fine..." she says, wincing past the pain. "Please, do it again."

You take a deep breath, trying to steady your grip on her hips as you slowly push forward once more. You can feel her body tensing up as you make contact with the barrier again, but this time she doesn't make a sound. Instead, she bites her lower lip and closes her eyes, bracing herself for the sensation.

You consider your options. Perhaps you could try going slower, allowing Anna's body to adjust to your size inch by inch. Or maybe you could try a different angle, or use some lubrication to reduce friction. You decide to try the first option, and begin to slowly push forward, giving Anna time to adjust to each new inch. She breathes deeply, her body tensing as you make progress.

With each millimeter gained, you can feel Anna's body relaxing a bit more, her muscles gradually loosening up around your shaft. You take your time, savoring the feeling of her warm, velvety walls enveloping you bit by bit. It's a slow and delicate process, but the look of relief and gratitude on Anna's face makes it all worth it.

Finally, after what felt like an eternity, you can feel the tip of your cock pressing against the barrier deep within Anna. You hold your breath, waiting for a response. After a moment, Anna moans softly, her body trembling slightly. "I'm going to try again, are you ready?" you asked, being on top of her your sweat matched with hers.

"Yeah..." she replied, her voice slightly shaky. "But please be gentle this time." You nodded, taking a deep breath to steady your nerves as well. You began to thrust slowly, carefully pushing yourself in deeper each time.

With one final thrust, you pushed past the barrier, causing Anna to orgasm for the first time. Her body arched as her tongue hung out from the impact alone.

As you slowly withdraw your cock from Anna's tight channel, you feel a sudden rush of liquid heat filling the space left behind. Her pussy had just squirted its first load, coating your throbbing cock with her arousal. "Did you just have an orgasm?" You asked in disbelief