Chapter 61: First Night With Anna (R18)

-Warning-

-This chapter contains sexual content, reader discretion is advised-

Intentionally or not, Anna and I had set a good mood for ourselves. The lights were out, so the only light dimly illuminating the living room was coming from the TV.

Having a girl rest on my lap while caressing her hair would easily pass on as a cute romantic scene in such a setting.

Yet, when she made her offer, I refused, and even now, I'm frantically trying to hold Anna back from my son.

Anna: "Why though?"

She pouts and tries to struggle against my hands holding her in place.

Back then I never would've imagined myself refusing the advances of a girl like this, but...

Miwen: "I'm already in a relationship."

Anna: "With Licia, Claire, and Mia right? I already know that, so what's the problem with one more?"

She was wrong about Mia, but even if I accounted for that, her point would still stand as i couldn't deny doing it with the others...

The problem was that those two were pretty much a special case...

Miwen: "Those two had an agreement, I don't think it's fair to do it with someone else behind their backs."

Anna: "... It's fine, they won't mind it."

Miwen: "And how would you know?"

Without any further explanations, it felt like it was just wishful thinking on her part to me.

Anna: "All this time you've been fooling around with Mia though, and I've never seen them act with jealousy."

Miwen: "This and that are different though."

I might not be a genius, but even I can see how going from jokes to actually doing it with another girl is a huge jump.

If either Licia or Claire got mad at me for joking around with Mia, then I might've toned it down a bit and expected things to be alright with us.

I guess allowing me to do that does show a bit of a willing side to them, but again, there is a huge gap between accepting your partner to mess a bit with other girls and actually accepting that he lays with them.

Anna: "Sure, but even when you saw three other girls' naked bodies, they still kept mild. Even when Beatrice hugged you, they didn't show any care towards that, so I think they don't actually mind you being with other girls."

Again, all those situations had their own circumstances behind them, and her point isn't really strong since It's mostly her opinion of what she has been observing.

Which brings me to...

Miwen: "Since when have you been so observant?"

Anna: "Since always? It's a necessary trait for a heavy knight... but that's beside the point, so, can you take off your hand from me ?"

Miwen: "..."

Strange, I thought I had a good grasp on her...

Is it due to her attentiveness towards the others' actions that she's outperformed in the dungeon? Maybe I actually read her standing wrong...

Yet, the first time she said it, I thought it was just thanks to her drunkness kicking in, but her actions have been consistent towards her intention of getting on with me, and what's more, she seems uncharacteristically desperate for it.

Miwen: "...What's your reason for doing this? I haven't done it with anyone other than those two, and I provide the same for everyone. Furthermore, if there's something you really want, you can just ask me without doing this, like Beatrice."

In other words, I don't understand what is it that she expects to gain from this.

What would make her so desperate that she felt necessary to offer me sex instead of just asking for it normally?

Anna: "Do I need one?"

Miwen: "I won't lay a hand on you without a good reason."

And with this, I've brought an end to the whole situation. Much as it hurts me to deny her, I already have two cute girls by my side that I wouldn't want to risk losing without a reas-

Anna: "...There's something I've been keeping from you, it's not really a lie, more like an omission, but I couldn't tell you at the time, only now that I know you better do I feel safe sharing it..."

The way her act changed in an instant made two things clear in my head, first of all, this wasn't happening thanks to the alcohol flowing through her blood.

And second, it seemed like she was really serious.

It would still do me good to doubt, but I decided to play along and try to get a few more out of her since whatever she's hiding might impact our group.

Miwen: "I'd be glad to hear you out though, no need to go this far."

Anna: "I need to make up for keeping it from you first... Won't you let me?"

Haah... it's impossible for me to resist when she's almost begging for it like this.

Still, no matter what was at stake, I didn't want to sour my relationship with Licia and Claire, so I left the sofa and went back to my room without uttering a single word, which seemed to make Anna shocked with my iron will...

...And then, less than a minute later, I came back.

Miwen: "I got permission."

Truth be told, this was the easiest and safest way to resolve things aside from outright denying her.

Though I'd like to hold an actual conversation with Licia and Claire to understand their feelings on the matter better, this time they were a bit occupied so I had to ask them from outside the room and kept it to a simple "yes or no" question.

With this I now know how far they are willing to let me go with other girls... and I also get to know what Anna is hiding too.

Anna: "Eh? Did you ask them that? That's... shameless!"

Miwen: "Said the girl begging for cock..."

I thought my Gift behaved in the strangest way since it threw me in a wolves' den, almost as if trying to get me killed in a war, but hers making her fuck someone else is a serious contender... I can't help but laugh at the absurdity.

Anna: "Y-yeah... it's basically like that so..."

Miwen: "I get it, I get it. Turn around and point your ass this way..."

Though I was fine with ending things after I learned what she was hiding, given the new circumstances, I would feel bad for not accompanying her until the end, especially after seeing how hard it was for her to talk about it.

I also don't know if Licia and Claire have finished their business, so what's wrong with having a bit more fun?

Anna: "...Please be gentle..."

Miwen: "Got it."

She must've gotten the wrong impression of me since I was so assertive before, though it's true that I tend to give in to my instincts, I ain't that forceful when it comes to sex... I think...

Still, I went slowly with her and prayed her pussy open with as much delicacy as I could.

Every time I felt a little bit of resistance I'd stop and take it all back, which made her let out soft moans.

I could keep teasing her like this, but eventually, I would need to penetrate her wall, and when that moment came, like it or not, I started being a little more forceful.

Anna: "... you can move more..."

While I felt a bit challenged by that, I tried my best to control myself and kept exploring her cave, after all, I still hadn't put everything inside, and I doubt she'd be unsatisfied when I started moving seriously.

As if to answer me, when I poked at her deepest parts, her moaning became louder and more uncontrollable.

Anna: "...! Ahn... Aihn..."

Her pussy was pretty wet, and she managed to moisturize my dick pretty well. Thanks to that, I was able to start pistoning Anna at a good pace.

Though her walls were incredibly tight, every time I'd slap her butt, she would squeeze me really hard, which gave me a devilish idea...

Anna: "Aaaah... nhn... it's too good... I'm gonna cum."

Hearing her say that, I diminished the pace greatly, and even took my dick out of her.

Anna: "Uhnn...? Don't take it off... noo... I'm so close..."

She had teary eyes and started to wave her ass looking for my cock, but every time I would refuse to enter her pussy.

It didn't take a minute for her to start to beg me with a pleading face while using her hands to open her hole...

Anna: "... I wanna cum... please...put your dick back inside me..."

Miwen:" Oh, I'm gonna make you cum, just not with this hole."

Anna: "Eh? Awn... ahn.... n-not there... that place is... uhn..."

Though her pussy was great, ever since Claire denied me access to her asshole, I've only been thinking about fucking ass, and though Anna's not as great, it's not shabby at all, a bit less plump but appetizing nonetheless.

Furthermore, I might've gotten the perfect excuse...

But before I did her ass, I had to finger it, since it would be impossible to fit my thing in there the way it was.

With that purpose in mind, I also kept fingering her pussy to keep the supply of pussy juice going.

It seemed like there was a lot in there, and soon splash noises could be heard coming from it. A moment later and...

Anna: "Cumming... cumming! ...AAaaah... that's so good... ahh..."

She started squirting with no regard to the fact that I was there, and since it was way more juice than I needed, I decided to taste it for myself, and I gotta say, it was pretty good, a mix of salty and sweet that made me want to lick her clean.

I never forgot about her asshole though, so as soon as I finished taking drinking the reward for my good efforts, I started pressing my dick against her hole.

Anna: "You can't be serious... it's never gonna fit!"

Miwen: "It's your punishment for keeping a secret from me, so bear with it."

Anna: "Eh? But i... UNhn!"

I knew that if I wasn't fast enough she might dislike it enough to run away, so before she could, I entered her ass and started to pound it.

Her pussy was pretty tight, but this was on a whole other level, every time I put it in, I'd have to struggle against her walls from every direction, the pressure was insane and I thought that she might snap my dick off.

Still, I kept pounding her, slowly, then hard, until she had accepted all my dick inside her ass.

Anna: "Aaahhnn... It's too much... you're tearing me apart...haa..."

Miwen: "Let me ease your pain then..."

Though she was feeling good, I wanted it to be the best possible experience for her, so I leaned forward and started kissing her.

It was a bit hard to do since we were doing it doggy style, so my pace went down a bit during it, which might've alleviated things for her, if only for a while.

For the first time, I stopped holding her by the waist, and in that moment, I noticed that she was also liking it, as she kept bouncing back on my dick.

Still, I really wanted to hold her by the ass as I was about to nut inside her.

Her moaning was very loud now, if not for the girls being distracted, I'm sure they would be able to hear it.

Miwen: "I'm gonna cum... squeeze your ass..."

Anna: "Ahnnn.... Ahhh...."

My ejaculation seemed to have no end as she did her best at the end, I think I came buckets inside her.

And even though it was pretty good...

I still wasn't completely satisfied, and the night was pretty long, so we continued to make company for each other for a while...