Half asleep, cuddled up like nested spoons, Alex gently presses her ass into my groin. I drop my hand onto her hip, fingers curling around the front of her pubic bone, fingertips just brushing below the waistband of her underwear. Nearby, a TV chatters away, ignored.

Alex and I can’t lay touching without building up sexual tension, and tonight is no exception. We’re cuddled close, and before long she is grinding her ass into my cock, making quietly breathless “Mmm” sounds as she moves against me. I’m hard quickly, and grinding right back against her ass with determined strokes.

At this point, it’s very late, and we’re tired. I’m expecting to either come all over her ass and thighs, or maybe have Alex change positions at the last second and swallow my load (Alex is a big fan of warm semen), followed by a peaceful night’s sleep. It’s at this moment that I notice how Alex’s breath catches each time the tip of my cock slides against her asshole. Fatigue falls away, replaced by excitement!

Alex has been practicing to have anal sex for the last few weeks. She’s progressed to the point where she can take in a medium-large plug (or a few fingers at a time) and enjoy the sensation. Tonight, she’s clearly enjoying the feeling of my tip pressing against her as we play. I decide to take her to the next level.

I reach for the bottle of lube that lives on our headboard and quickly make my cock, Alex’s entire ass and at least three of my fingers totally slick. I roll her slightly off her hip, onto her stomach, and begin teasing open her asshole. Alex relaxes slightly, and I pop into her with a finger, and then two more. She moans, and presses into my hand. I gently massage her anus, spreading her open until she’s drawn in the entire length of my fingers. She starts to come.

I gently withdraw my hand and move in behind her. Very slowly (the secret to happy anal sex is to do everything slowly), I press the tip of my penis against Alex’s asshole until I slide it into her. A second later, I’m halfway down the length of my shaft, urgently fucking Alex in the ass. She comes almost immediately, shuddering out a moaned “My God!” as her pussy clamps down over and over again, and her anus squeezes me tightly.

We lay on our sides and fuck for at least an hour. Eventually, I let go and filled Alex’s ass with a huge load of cum. She came over and over for nearly the entire time. When we’re finally done, we’re both excited: Alex’s first anal sex! We do a quick inventory, and she’s not just unhurt, she’s already begging for more.

It’s going to be an excellent weekend…