Karen offers her asshole to her future husband.

Today is the day I meet Karen. On the days when Karen serves me, I refrain from Lina's morning service and sex during lunch break, and head to our usual cafe, feeling the weight of my balls filled with semen. Lina had left work early because she had been asked to take care of some errands at home, and when I arrived at the cafe, the two of them were sitting in their usual seats, waiting for me.

Karen looked somewhat nervous as she placed a piece of paper on the table.

"Please, read this."

I took the paper and read it. Wow, I didn't expect it to go that far... This was a document signed by Karen's father, the Baron, giving permission to take Karen's anal virginity. I've never heard of anything like that before. The Baron must have had a headache having to sign a document giving permission to have anal sex with his daughter.

"Do you really want me to use your ass and hold you that badly?"

"There are still two more years until we can get married. I want Allen to take me and make me feel even more like his woman. And... I want to feel better too..."

Karen said as she took off her clothes. Then, completely naked, she got on all fours and spread her ass wide open. The anus above her virgin pussy twitched obscenely, insisting that I have sex with her.

"Please, I'm already prepared, so please take my first time."

"...I get it. Just stay still for a bit."

I squatted down at Karen's feet and ran my tongue over her anus. She certainly seemed to have been prepared, there was no smell. There was a slight taste, probably because she had used some lubricant.

"Eh, hey, don't lick there. It's dirty."

"Karen licks my ass too. I'm just returning the favor." [A/N: Gosh! Why am I writing this scene...]

Karen let out a panicked cry, but didn't resist. He used his tongue to loosen the entrance to her anus, and wet it with his saliva.

"Allen, no! You don't have to do that!"

But I thrust my tongue in and caressed the inside of her hole. Karen tried to escape by lifting her hips, but I held her down firmly and didn't let her get away.

"Ahh, something's strange... it's giving me goosebumps."

Sensing that Karen's reaction had softened considerably, I removed my mouth from her anus. Karen collapsed onto her back on the sofa, panting heavily.

"Allen, please... I want you to hurry up. Take my virginity... Lina, please watch."

Karen let out a sad voice. Lina, who was waiting quietly by the wall, nodded gravely. I took out my stiff penis from my trousers and placed the head of my penis against her anus. I really wanted her to suck it, but I'd hold back today.

"Okay then, I'll put it in. I'll take Karen's anal virginity."

When I put strength into my hips, the head of my penis sunk into her anus. Karen gritted her teeth and endured the sensation, which was new to her.

"Ngh, it hurts a little... but it feels good... I'm happy..."

My dick pushed aside the folds of her anus and entered inside. It was my first time having anal sex.

"Wow, it's so hot inside my ass... I can feel Allen's penis filling me up. This is what sex is..."

Karen had a dreamy look on her face. I too felt a different kind of pleasure from being wrapped in her warm flesh.

"Then... I'm going to make Karen's anal mine deep inside."

With those words, I slammed the rest of my dick into her rectum with a squishing sound.

"Ughhhhhnghh~!!"

"Woah, that's amazing..."

Lina couldn't help but speak up at Karen's reaction.

"Ahh, my butt feels... strange... ahhh!"

Karen gritted her teeth and drooled as she endured the sensations that were assaulting her ass, which could be described as both pain and pleasure. I kissed her and ran my tongue over her teeth.

"Nghhhh, aah."

"Open your mouth, Karen. I'll loosen you up."

Karen followed my instructions and opened her mouth wide. I entered her mouth and sucked her tongue.

"Hmmm... Ahh, ahh."

Karen's voice became sweeter as she felt a sensation different from the pain of her anus. I slowly started to thrust in and out, checking her reaction.

"Nghhh! Ahh, haaah."

Karen lets out a cry of pain mixed with pleasure every time her anal is dug. My dick is also about to be taken away by the sensations different from Lina's pussy. If I let my guard down, I might cum.

"Karen, are you okay? If it's too hard, let's take a break."

"Mm, haa! Ahh, Allen's dick is raging deep inside my ass... it feels so good... please, don't pull out. I want you to finish it all, all the way to the climax...Nghh~!"

"That's good. Then I'll move it around some more."

"Yeah, I'm Allen's sex slave, so don't worry about it. I only move to make Allen feel good."

I took her up on her offer and started to move my hips. The feeling of my penis being pulled by her intestines and being squeezed by her anal made me want to ejaculate.

"Ugh, Karen, I'm about to cum... Can I cum inside your ass?"

"Yes, cum inside me. I want you to dispose of Allen's semen inside my body."

"Got it, I'm cumming...!"

I cried out as I ejaculated deep into Karen's anal passage. I could feel the thick semen that had been building up all day spreading inside her intestines.

"Ahh, Allen's heat is spreading inside my stomach... I'm so happy that you came inside me..."

Karen has an ecstatic look on her face. I kiss her as a thank you, still inside her.

"Mmmm ♡ I was able to use my hole to satisfy Allen's sexual desire. I'm so happy... I'm so happy right now."

"Congratulations, Karen-sama."

"Thank you, Lina-sama. I'm sorry I offered my ass to Allen before you did."

"Karen, I'm not done yet. I'm going to violate your asshole to the max today."

My dick was still hard from the excitement of my first anal experience. Karen noticed and smiled happily, put her hands around my neck, and kissed my cheek. I started pumping my dick into her anus again, and we went into round two.

We continued fucking for the next hour, and by the time the 5pm bugle sounded we were completely exhausted.

I sat next to Karen, who was sleeping on the sofa, and Lina gave me a cleaning blow job.

"Mmmm, slurp, haa... Young master, thank you for allowing me to serve you with my mouth."

After saying that, Lina let go of my dick and bowed her head. I gently stroked her head.

"Yes, thank you. I was surprised when Karen offered her ass to me, but it seems Lina had been preparing for me all this time."

"Yes, in fact, I have been expanding her anal since this afternoon. At first it was so tight that I couldn't even fit a finger in, but Karen-sama put in the effort so that you, the young master, could use it."

"Well, it looks like I'm going to have some very good wives. Now I'll make sure to take Lina's asshole."

I kissed Karen on the cheek. Lina looked on as she smiled happily.

"Well, it's getting late, so I have to wake Karen up and see her off... It's going to be hard for the Baron and I to see each other off..."

However, I received a firm handshake and was greeted with, "Allen, please take good care of my daughter." Yes, but is that really okay, Papa...