she loses her anal virginity

"Okay, here it comes. Slowly does it."

You push your finger into Cassie's butthole as she holds her face down and ass up in front of you. For both of you, it is your first experience of any anal play. The internet had suggested warming up to anal sex with a beginner butt plug, but you don't have one and you've been instructed to start today. At least you have lube.

"Ah! I can feel it! It feels weird and kind of wrong. But not awful..." Cassie reflects.

"Okay, I'm going to pull it out slowly, and then we'll try two."

You let her get used to two fingers, and then three. After that, it's time.

"I'm going to put it in now. Tell me if you want me to stop."

"I won't. I mean, I will tell you if I need you to stop, but I won't need to."

Bloody hell, she's really determined to please you.

You position the tip of your lubed-up dick against her sphincter and begin to add more and more pressure, until the gates open and the tip moves in. So tight! The outer ring of her asshole feels incredible as it moves down your cockhead. She squeaks but doesn't resist you at all.

"Does it hurt?"

"A little, but I can take it."

"Should I keep going?"

"This is what you want right? This is your fantasy?"

You hesitate for a moment.

"Yes, this is what I want."

"Then it's what I want too. So please, push it in more!"

I do not deserve her. She is too wonderful for me.

A weird thought to be having as you sodomize your fiancée, to be sure, but also a fleeting one, as the pleasure from feeling your dick slowly sink deeper and deeper into Cassie's asshole captures your focus.

"Shit..." She mutters under her breath.

That makes you freeze still. Cassie never swears.

"Do you want to stop?"

"I want you to stop asking that! Just keep going, okay!"

You push one inch in, and then another, and then suddenly it actually becomes easier rather than harder, the rest of your length sliding into her with little resistance. That's it, your first time properly penetrating another human, and it's an asshole. You can never take that back.

"Oh god oh god WOW!" Cassie sounds on the brink of being completely overwhelmed.

"Are you okay?"

"Yeah... it was painful at first, but now that you're all the way in, it actually feels kind of okay. Like, all cosy and snug, and... full. Like, maybe I could get used to this. Try moving it in and out."

You don't need to wait for her to ask twice. You start to slowly thrust back and forth, deep inside her ass.

"Hoo... okay, that's pretty intense... Haaaah..."

"In a good way?"

"In an I'm not sure way."

"We should stop."

"This is me fulfilling your fantasy, knucklehead. Don't you dare pull out before you cum. Do me!"

It's so endearing to hear your innocent little flower trying to find the words to sound dirty, and it's apparently what your member needs to hear too to go from rather hard to rock hard, and twitch inside her. You can do this! You slowly but surely ramp up your thrusting until you reach a decent 'normal sex' pace. To tell the truth, it feels amazing. You knew sex would feel good, but this is out of this world. Cassie's asshole is so tight! She is squeaking away, but you can't tell if it's pleasure, pain, or somewhere in the middle. She mumbles something but you can't hear her over the sound of your thighs slapping her butt cheeks.

"What?"

"...Harder. Go harder!"

Drunk with pleasure, you double your tempo before she's even finished speaking. Her squeaks turn to yelps, and you start grunting as you feel your orgasm building. You warn her of the incoming load of semen.

"I'm gonna cum. I'm gonna cum!"

"Do it! Cum in my ass!"

You bottom out with a feral growl and empty yourself inside her innards.

"I can feel it... Wow, I can feel your cum..."

After you come down from your high, you pull out as slowly as you can. It feels like it takes forever, but eventually you are free.

"Are you okay?" You ask hesitantly.

"I... I think so. But I definitely need to go to the toilet now."

You sit there, dazed, as the love of your life rushes to the bathroom to deal with the load of warm spunk you just shot up her backdoor. A few hours ago you had no interest in anal sex at all. Now you have to admit to yourself, you may have not known what you were missing.

What a day.