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?