My World to Free-use

149: GILF

The massive ass cheeks tried to close around my hands, and it was almost impossible to hold them with how soft they were.Regardless, I saw the prize deep inside the darkness of her massive ass and went forward without fear.

Her giant ass almost smothered me as I leaned in, crushing my face from both sides, but I managed to arrive at my destination.

[Cleanse]

A clean, shaven, untouched GILF pussy. I pressed my mouth against her virgin vagina and began to lick it slowly, and made sure to go over it thoroughly, sliding my tongue along her folds.

A soft moan escaped Valeria’s mouth, and I couldn’t help but feel all the more turned on. Not to mention, the torture of not being able to see her expression right now.

“Haaah…”

Another soft moan as my tongue once again explored her unexplored cavern.

“Describe what you feel right now, Valeria.” I heard the lady’s voice while I was still buried in Valeria’s ass.

Valeria, slightly breathless, but I could tell for sure her expression wouldn’t have changed much, and replied, “My lady… I can feel Jack’s tongue on… my vagina… It feels strange, but…”

“But?” The lady asked.

“For some reason it… it feels… pleasant.”

Valeria herself could not describe it properly, from the looks of it. Well, it wasn’t much of a problem if she couldn’t. She could tell it wasn’t anything bad, so she wouldn’t be going anywhere.

Motivated by her reply, I only licked deeper, while her massive ass cheeks pressed heavily against the sides of my face, almost crushing me between the soft, warm pillows of flesh.

Keeping them apart was an arduous task, but I had to, not only because I enjoyed it a lot, but also because it was the only way for me to breathe since my nose was buried in her ass, and it was blocking all sources of air for me.

I moved on to her clit, making her gasp out loud from above.

“What was that, Valeria? Did he hurt you?” The lady’s voice once again fell in my ears.

“Ahh… No… my lady… it just… I don’t know but… he seems to have touched some part of me… for some reason, my legs are trembling.” Valeria replied between heavy breaths. She could moan, but didn’t really know how to moan, so the moans she was letting out were out of instinct, not voluntary moans.

But her answer made me happy, genuinely. It meant that it was time to take the next step, and take the next step I did.

I was about to slip two fingers inside her tight vagina, but that meant letting one of her ass cheeks go.

“May I trouble the lady to hold her butt with her hands?” I asked.

“Y-yes. Which side?” Valeria asked.

Logical one, huh?

“Your left buttock,” I replied.

“Alright…” Valeria replied and held her left ass cheek in place while her other hand was still on the couch for balance.

Since her ass was now handled, I once again buried my face inside the darkness, even though I didn’t need to, since I would be replacing my fingers in her pussy, but it felt so good to be crushed by her ass that I couldn’t resist.

I traced her pussy with my finger, making her twitch a little, before I slowly and gently slid my forefinger inside her tight, virgin entrance, working her insides as gently as I could.

“Haaapp!!”

Valeria gasped even louder from above as my finger encountered a blockage. No doubt her hymen, but I didn’t push any further. I didn’t want to accidentally break it with my finger. That task was only my dick’s.

Still, her body was extremely tense after I inserted my finger to the limit her pussy allowed. She was gasping loudly, I could hear even from down here, and her body was not relaxed either.

“What is it now, Valeria? It seems like you’re in pain.” The lady once again asked Valeria while she gasped in discomfort.

“My lady… I… something… something just went inside my… my vagina… it stings…” Valeria replied.

“Are you hurting my servant, Jack?” The lady asked with a soft tone, but the crushing feeling of her question never faded away.

“Of course not, my lady.” I pulled my head out of heaven into the real world and replied, “It is just some initial discomfort that is involved. She will soon feel better.”

“Hmm…” The lady hummed in suspicion but didn’t pursue the matter.

I guess I should better add mana. I was hoping to keep things genuine, but it wasn’t the real world. While there were ups here, there were downs as well. If Valeria didn’t feel good from this act, there were chances the lady wouldn’t allow this to be done with her either.

So, I added mana to my finger, and instantly her pussy throbbed.

“Mmmmph!!” Valeria tensed even more, but this time was different. She was feeling good.

“Are you still in pain, Valeria?” The lady asked.

“N-no, my lady… I am no longer… in pain… it feels pleasant… warm…” Valeria replied while gasping and moaning, but it was still on the milder side since I had only supplied a little mana to her pussy.

Knowing that the problem was now over, I began to finger her properly. Slowly and patiently, I fingered her pussy while I also leaned in to play with her clit.

Her huge ass kept getting in the way, the massive cheeks pressing against my face and hands, and I constantly had to spread her wider. And I absolutely loved every second of it.

“Jack, I see Valeria’s butt is bothering you. Is it a negative aspect about her?” The lady’s voice interrupted my good time.

“Of course not, my lady. There is not one part about Lady Valeria that could be negative.”

Probably the most honest I’ve been since I came here.

“Hmmm… And you, Valeria? How do you feel when Jack touches your butt like this?” The lady asked Valeria.

“I do not… feel anything in particular… my lady,” Valeria replied.

“I didn’t ask if you were offended by it. I asked how do you feel?” The lady clarified.

Apparently, Valeria interpreted the earlier question as, ‘How do you feel when a commoner touches you?’

“I can feel my butt pressing against his face… unghh!!... it feels… it feels… warm… very warm…” Valeria laboriously replied. Her breath was rapid, and her body was beyond tense.

She was approaching her climax.

But not so fast. She wasn’t cumming with my fingers. Her first climax would be from my dick. I wanted her to know how good my dick could make her feel compared to anything else.

When Valeria was wet enough, and the pain had mostly faded thanks to my mana, I stood up.

I began to move forward so I could line up my dick against her pussy when the lady asked, “Are you about to begin? Insert your penis inside her, I mean.”

“Yes, my lady.” I had to stop and reply to the lady, which was annoying, but what could I do when she was the one calling the shots? Even now, if the lady called Valeria away, no matter how good I could make her feel, Valeria would walk away.

Anyway, back to the BBW GILF!

I tried to enter her from behind, but her enormous ass once again got in the way. The huge, soft cheeks pressed against my hips and cock, making alignment difficult.

I had to spread her ass with both hands myself, gripping the soft ass firmly, before I could make my way in. It was still difficult to put my dick in because I didn’t have a free hand, so I asked Valeria again.

“Please hold your left buttock firmly like this, my lady,” I asked Valeria, and she nodded, putting more power in her hand to pull harder.

Finally, I had enough space to move about an inch forward, but that still meant only about half, or a little more, of my cock would be going in. Not more than that.

Still, I pushed forward. Even half was enough. My dick was finally at the entrance of her virgin hole.

I slowly pushed in, inch by inch, very carefully. Valeria gasped sharply, even though I was applying mana to her pussy as her insides stretched around me for the first time.

Only when I was inside to the limit, about five inches of my nine-inch cock, did her gasping stop enough for…

“How do you feel right now, Valeria?”

The lady once again butted in. But I was too busy savoring the tight feeling around half of my dick to bother with her.

Valeria, however, wasn’t.

She was going through a tough time, I could tell from the way she was gasping and breathing in sharply.

I sent another wave of mana, making her gasp out loud.

“I asked you something, Valeria.”

~~

Two extra chapters, and two chapters of yesterday and today. I guess I'm going with schedule. 

Anyway, I've completely destroyed my other novel thanks to this one, and this one doesn't even pay. I would like it if you guys were a little bit thoughtful of that and support me in some way. Maybe visit my Patreon and all.

Another point is that while I had planned only ten chapters of smut before the story, unfortunately I had to change a lot in the novel and now there would be 20-30 chapters of smut before we move on to the story.