Go with his plan

You hear him out, and figure that he is trustworthy enough to try his plan. "Alright, you can put it in for a little bit without a condom," you concede. You grab one of the condoms and hold it in your hand, ready to give to Alex as soon as he needs to put it on. "Just... go slow."

"Alright," he responds, pointing his dick toward your opening. He slides the head of it up your slit and rubs it over your clit a few times, causing your body to twitch from the pleasure. After doing this a few times, he lines himself up for the main course and pushes in slightly. You feel yourself stretching and can't help but clench your teeth and shut your eyes tight at the stinging pain of him straining against your hymen. "Wait; are you a virgin?" He asks, incredulous. He pulls back slightly so that his tip is no longer nudging into you. You open your eyes and nod at him, not sure you're ready for what is about to happen. "Man, I'm going to enjoy this!" he says, putting his dick back at your opening.

He presses in slowly but very firmly, stretching your hymen in an excruciatingly slow manner. Finally, it gives way, and he pushes himself deep inside of you as he sighs out his pleasure. You feel his hips come to rest against yours and know that he is as deep as he'll ever be in your cunt. He starts to pull out for his next thrust, but you wrap your legs around him and hold him inside of you. "Hold still for a little while," you say, "just until it doesn't hurt anymore."

Rather than listen, he just pulls back against your legs and thrusts forward, starting to fuck your stinging, sore pussy. "Fuck that; I want to enjoy you as much as I possibly can before you make me put that stupid condom on." This pisses you off slightly, but there's not much you can do about it. He continues to thrust into you, but at least he's not moving too quickly. Just enough for him to be able to savor the feeling.

After a short while, you feel like your pussy is becoming accustomed to the thick intruder, and it starts to tingle with pleasure. You don't want to admit it, but getting fucked -- once you got past that whole hymen thing -- is actually better than anything you'd ever felt. This was better, even, than what you expected sex as a man to feel like. This was not just pleasure for your crotch, but it was feeling good all over your body. You felt tingling, almost like a pleasant pins-and-needles, all over your skin. The feeling was, however, focused around your crotch.

The warmth coming from the dick inside of you was exquisite, as was the silky smooth texture of the skin on your innermost depths. You could feel the texture of it; every vein and every ridge felt like a perfect tool meant to scratch every itch you had. You admit to yourself that it probably wouldn't feel nearly as good if that cock was encased in a condom, but it should probably happen sooner or later.