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GILF Hunter

Chapter 139 Feisty Bitch Is Weak in Her Anal · Nov 14, 2026

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Chapter List (547)

Page number / 11

101 Chapter 101 Taming Older Women 2026-11-14
102 Chapter 102 The Safe Word for SM Play is ’I Love You’ 2026-11-14
103 Chapter 103 Turning Her into a Masochistic Sow 2026-11-14
104 Chapter 104 Training Morgan 2026-11-14
105 Chapter 105 The Horned Beauty’s 2026-11-14
106 Chapter 106 My elf 2026-11-14
107 Chapter 107 Returning Sex Partner 2026-11-14
108 Chapter 108 Declaring Herself to Her Husband in Front of the Camera 2026-11-14
109 Chapter 109 Filling the Womb of a Married Woman 2026-11-14
110 Chapter 110 The smell of a male after sex is insane… 2026-11-14
111 Chapter 111 Too Many Pussies Around 2026-11-14
112 Chapter 112 Nothing Beats Fucking While Working 2026-11-14
113 Chapter 113 Fucking an Office Lady in Just Pantyhose 2026-11-14
114 Chapter 114 I Love My Husband’s Cock More Than the Responsibility of Leading the Village 2026-11-14
115 Chapter 115 Nothing Brings a Man and Woman Closer Than Sex 2026-11-14
116 Chapter 116 Neglect Play 2026-11-14
117 Chapter 117 Leaving Her with a Rotor and Going to Fuck a Married Elf 2026-11-14
118 Chapter 118 Cum in My Womb... I’ll Let My Husband Raise It... 2026-11-14
119 Chapter 119 Cumming from Fingering Without Even Realizing It 2026-11-14
120 Chapter 120 Waiting for Him So Desperately 2026-11-14
121 Chapter 121 Pussy Torture with a Massager 2026-11-14
122 Chapter 122 Fellatio Service 2026-11-14
123 Chapter 123 Unloading in dragon 2026-11-14
124 Chapter 124 Rough Sex with My Newly Acquired Fucktoy 2026-11-14
125 Chapter 125 Getting a Morning Blowjob 2026-11-14
126 Chapter 126 Going on a Date with My Wife 2026-11-14
127 Chapter 127 High School Girl (Wife) 2026-11-14
128 Chapter 128 Hot School Uniform Play with My Wife 2026-11-14
129 Chapter 129 Bliss of nut-glow with my wife 2026-11-14
130 Chapter 130 Pounding Her in the Classroom 2026-11-14
131 Chapter 131 Thrill of Breaking Her Convictions 2026-11-14
132 Chapter 132 Take her virginity? 2026-11-14
133 Chapter 133 Pseudo-Sex with My Adopted Daughter 2026-11-14
134 Chapter 134 Pleasure Without Even Penetrating 2026-11-14
135 Chapter 135 Time to move to the next step. 2026-11-14
136 Chapter 136 Why I Love an Adulterous Married Woman 2026-11-14
137 Chapter 137 The Pleasure of Taming a Prideful Elf 2026-11-14
138 Chapter 138 Please let me go to the bathroom...! 2026-11-14
139 Chapter 139 Feisty Bitch Is Weak in Her Anal 2026-11-14
140 Chapter 140 The Finest Anal Pussy Developed by Master 2026-11-14
141 Chapter 141 Fine Ass of an Elf 2026-11-14
142 Chapter 142 Shall We Enjoy Some Sex 2026-11-14
143 Chapter 143 Threesome Sex 2026-11-14
144 Chapter 144 When’s my turn? 2026-11-14
145 Chapter 145 Doggy style sex is the best…! 2026-11-14
146 Chapter 146 Taking the Cock-Sleeve to the Forest 2026-11-14
147 Chapter 147 Breast Milk of a Busty Beauty Taste Like? 2026-11-14
148 Chapter 148 It Feels So Good to Spray Milk from My Breasts... 2026-11-14
149 Chapter 149 The lactation experiment 2026-11-14
150 Chapter 150 Ready to Accept a Man 2026-11-14

Chapter 139: 139 Feisty Bitch Is Weak in Her Anal

”Back already?”

”U-Uh, yeah.”

Diana nodded with an awkward expression.

She seemed to have mixed feelings about her first time with this kind of play.

”...Anal sex, huh. How do you even come up with such perverted play?”

”In my hometown, this isn’t exactly common, but it’s not considered weird either.”

”Do all humans live like that?”

”Well, it depends on the culture, I guess?”

Even in this era, if you dig around the continent, you’d find some people doing it...

But there’s probably no one as dedicated to developing a woman’s anus as me. I’m an anal connoisseur by heart.

”Anyway, come here, get on all fours, and stick out your ass.”

”...Got it.”

Diana’s face flushed as she got on all fours on the floor.

In that position, she slightly pushed her ass back, looking enticing.

”As expected of an elf, so flexible. That waist and ass line are pure art.”

”D-Don’t tease me, just do it already if you’re going to.”

Was it the unfamiliar experience of anal training?

Diana seemed especially tense today.

”But you’re suddenly talking casually again?”

”You took off the collar.”

”So you only treat me as Master when the collar’s on? That’s disappointing.”

”Hmph! If you get it, then make this bitch slave feel good already.”

Seeing Diana act all tsundere made me chuckle.

Maybe it’s her petty revenge for making her hold it to her limit earlier.

Chalaak.

I put the collar back on Diana’s neck.

”So, am I Master now?”

”...E-Even with this on, I’m not treating you like Master.”

”Pfft! So prideful. Guess I’ll have to teach your body a lesson.”

At my words, Diana’s body flinched.

But the slight smile on her lips showed she was already looking forward to what was coming.

”D-Do it! No matter what, I won’t give in easily today.”

”Then I’ll start developing your little butthole, so relax.”

”Hng...?”

I lightly dabbed some aphrodisiac on a brush.

Then, I gently tickled around her pretty pink butthole with it.

”Ugh... Haa...! W-What are you doing?”

”I told you, I’m developing your butthole.”

”Eek! Haa! It’s ticklish. Is that what you call developing?”

”You have to approach it delicately at first.”

The anus is one of the most sensitive parts of the body.

Even men can feel a thrilling pleasure when it’s caressed.

’Most people don’t know since it’s rarely touched.’

When Medea caresses me, she sometimes brushes near my anus.

Even a slight graze feels quite intense.

Anyway, I kept tickling Diana’s cute little puckered butthole.

Her tight hole twitched repeatedly as the sensation started to build.

From her reactions, it seemed her anus was naturally quite sensitive.

”Ugh... Haa...! Uhhng!”

”What, already feeling good?”

”I don’t know... but something tingly keeps rising... Hng!”

”That’s proof you’re feeling it properly.”

Even an elf who’s lived for centuries likely never had her butthole touched.

Since it’s never felt pleasure before, it’s bound to be extra sensitive.

”Even so, you’re twitching more than I expected. Maybe you’re naturally talented for anal sex?”

”T-Talent, what...!”

”No, this definitely feels good.”

”Ahh... Stop... Stop tickling it like that... Hng!”

They say feisty women are weak in their anus.

Seeing Diana’s reactions, that seems somewhat true.

’Just brushing the entrance with a brush, and she’s already losing it.’

With continued stimulation, her anus couldn’t hold back and started pulsing.

The pink hole squirmed, overwhelmed by pleasure, looking quite cute.

”Come to think of it, you’ve never done anal before, have you?”

”Ugh! Haa... Obviously not.”

”Then I’ll be taking your anal virginity.”

”Anal virginity? You’re such a pervert... Uhhng♥”

For the final touch, I brushed from her butthole down to her perineum.

Her sensitive spots, hit by the brush, made her hips tremble with delight.

”Good. That should be loose enough.”

”...You’re not doing more?”

”Why? Want more?”

”Well... it was kind of nice, I guess.”

That last brush stroke must have felt really good.

Her hips twitched, as if hoping to feel that pleasure again.

”Service stops here. The real development starts now.”

I dripped aphrodisiac gel onto her pulsing anus.

Coating my fingers generously with the gel, I inserted them into her anus.

Sluuuuk

”Uhhttt?!”

My fingers went in easily without resistance.

The slippery gel made it impossible to stop, even if she reflexively tightened.

’The brushing already loosened her up.’

This was just about applying the aphrodisiac to her butthole.

I moved my fingers slowly, gently probing.

”Ah... Hng... Aah...!”

As my fingers moved in earnest, Diana let out moans.

Even if it wasn’t fully developed yet, it wasn’t without pleasure.

’She’s reacting this quickly even without full development.’

Either the refined aphrodisiac was highly effective, or Diana was just naturally gifted in her anus.

”Your hips are shaking a lot. Already feeling good?”

”Ahh...! I don’t know... It’s not intense, but this weird feeling keeps rising... Ugh!”

Even Diana, usually overflowing with lust, was practically a virgin when it came to her anus.

She was flustered by the unfamiliar pleasure.

Meanwhile, her anus was becoming more sensitive in real-time.

Not only was it getting used to the finger’s stimulation, but the aphrodisiac was spreading quickly.

’The walls there absorb drugs like this quite well.’

The anus is packed with nerves.

She didn’t feel it before due to unfamiliarity and shame.

But once she starts adapting, she can quickly gain pleasure.

”Good. Time for the next step.”

”Hoo! Hoo! Why are you doing so much...?”

”What’s wrong? You enjoyed it too. Isn’t this the kind of thing you like?”

”But the pleasure keeps teasing me without fully coming...”

Smirking, I pulled out a vibrating dildo.

It’s quite a bit smaller than my cock, not even half the size.

Probably about average size, right?

”W-What’s that? If you’re using something like that, just use your cock...”

”If I put my cock in your asshole now, it’d just hurt without much feeling.”

First, I need to develop this cocky elf’s butthole into a proper erogenous zone.

Fucking it comes after that.

”You’ve tried a vibrator before, right? This is that vibration in a dildo.”

Gulp.

Realizing what it’d feel like, Diana swallowed hard.

”If you have something like that, put it in my pussy instead.”

”Well, getting your little butthole used to stimulation is important. Let’s practice with this first.”

....

Karl: When I’m developing cute little butthole of Diana, how about you guys show some sincerity?

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