First Anal
“M-Master, what are you saying?! A-anal sex?! Th-that place isn’t meant for… Hyaah?! S-stop!!!”
Hearing my choice of anal exploration, Selena cried out in panic even as I eased a finger a little way into her anus and spoke.
“It’s fine. People use this place for that too. I’ve seen plenty of it.”
Two fingers, even. Hell, three. Well—I hadn’t seen it in person, exactly.
I said it while recalling the videos I sometimes—really, only very occasionally—looked up to soothe myself. Selena shook her head hard and shouted back.
“Wh-whatever Master saw was all fiction! Hiiik?! There—!!! It’s just some pervert’s fantasy! S-so—! Get your hand out of that dirty place?!”
No, it was real… Still, does this world only have erotic novels for adult material? Video might be hard, but what about comics or something?
I argued silently against Selena’s insistence that I must have only read dirty stories—she still refused to believe I’d reincarnated into another world—and while I briefly pondered this world’s adult entertainment, I pushed the last remaining joint of my finger into her anus.
The entrance itself was painfully tight, but inside it was… slick somehow… A cock is several times thicker than a finger, so the squeeze should feel even better, right? I’d heard the peristalsis that tries to push a cock back out feels insanely good. To feel that, though, I’d have to loosen her anus first.
“It’s not fantasy. Some people do it here before the pussy, you know? There are even people who put a whole fist in. I’ve never tried it myself, but supposedly when something that fills the rectum all the way is pulled out, the pleasure feels like your soul is being sucked out.”
I spoke while resolving to develop her properly—if only to make up for the relative emptiness of the rectum compared to the overwhelming grip of the anus itself. Selena’s body jerked and she cried out.
“Hiiik?! S-stop with the ridiculous lies and p-pull it out, Masteeer!!! Hnngh!!! D-don’t press!!!”
I lightly pressed against her rectal wall as she begged, dismissing everything I’d heard as lies, then rotated the finger buried in her anus in various directions while I spoke.
“Uh-uh. Doubting your Master’s words? Looks like you need a punishment.”
The word “punishment” made Selena flustered; she shook her head frantically.
“N-no! I’m not doubting Master’s words or anything?! Th-that…! F-fine! I get it! I believe you! Hyaah! I believe everything, so please! Please just let me wash! I-I’ll accept everything after I wash, so pleaseee!!!”
I had been preparing to add a second finger into the narrow gap that formed each time the first one moved among her folds. Hearing her near-screaming plea, I thought, Well, no need to force it.
It looked clean enough anyway. No smell, nothing stuck to it.
Still, granting her request and securing free access to her anus afterward would be better for the long run than pushing through now. I pulled my finger free from the tight grip of her anus.
Ohhh.
I watched in admiration as her anus clung stickily to the withdrawing finger, stretching long before snapping back into shape the instant it lost the tip. Meanwhile Selena hurriedly straightened her waist and bolted for the river.
She returned with infinitely slower steps than the ones that had carried her away, then looked at my cock—standing so hard it seemed ready to pierce the sky—and spoke.
“W-wow. Y-your cock looks like it’s suffering so much. M-Master, wouldn’t it be better to make your cock feel good first? Right? L-like every morning, with my mouth and my chest? O-or… m-my pussy… with my pussy?”
Even though she had promised to accept everything, residual resistance to offering her anus still remained. Selena let out awkward little gasps and deliberately used lewd words, trying hard to redirect my attention elsewhere.
But my head was already full of the “anal free-pass” I intended to use, already overflowing with anticipation of expanding her anus as soon as possible so we could have anal sex. Her efforts weren’t nearly enough to turn me aside.
“That can wait. The night’s long. It’s not even past midnight yet, is it? Come on. Brace yourself over there like before.”
At my order Selena made a tearful face and pleaded.
“M-Master. I-I said I’d accept everything, but… p-please… e-even two fingers barely fit. I-if Master’s c-cock goes in, I’ll really… Ngh? P-please…”
Of course I had no intention of putting my cock in on the very first day of development… well, a tiny part of me had, but I knew it was realistically impossible. I guided Selena’s hands toward the tree and spoke.
“Don’t worry. I know it’ll take a long time of expansion before you can take my cock. Today I’m only using fingers.”
“Uuuh…”
Hearing a consolation that wasn’t really a consolation, Selena let out a little sob and obediently braced against the tree, pushing her hips back.
When I lifted the hem of her robe, her still-damp anus came into view.
She’d said two barely fit, so today I’d stick to two… Wait? I only put one in earlier.
Chewing over the tearful words Selena had spoken, I brought my finger toward her anus, then realized the oddity and tilted my head.
“I only put one finger in earlier. What do you mean two barely fit? Don’t tell me you usually masturbate anally…? And you said you hated it just to hide that…?”
At my suspicious tone, Selena—who had been trembling as she waited for the finger’s invasion—shook her head hard and answered.
“N-no! Absolutely not, Master! I-I’ve never even masturbated, let alone a-anal masturbation?! I-I’ve never done anything like that, never even heard of it!”
Hmm… She’s so desperate it only makes her more suspicious.
Sensing my doubt, Selena hurriedly added,
“I-it was just… after washing… I wondered if I could really take Master’s big c-cock, so I t-tried putting them in for just a second… R-really, just for a moment I put two in! I’m not some pervert who does anal masturbation!”
Uh… is she calling me a pervert for wanting to use her anus, just in a roundabout way? If so, I might have no choice but to turn her into a pervert who masturbates anally every day.
I briefly considered ordering Selena to finger her own anus daily, but decided the evidence was still insufficient and put it off for later.
“Don’t worry about whether it’s possible. I’ll take full responsibility and develop you until you can swallow my cock naturally.”
Relieved to have escaped the suspicion of being a woman who enjoyed anal masturbation, Selena carefully made one last resistance.
“D-do we really have to…? Th-there’s a place that can take it right away without any e-expansion…”
I lightly ignored Selena’s resistance and brought the stiffly extended index finger of my right hand toward the anus that was twitching in fear.
“Hnn!”
Feeling the foreign object dig into her tightly gathered folds, Selena reflexively clenched her anus and let out a moan.
Ohh.
Still feeling that overwhelming squeeze, I pushed my finger in joint by joint, then slowly moved the finger buried inside her anus.
“Hnn?! Mmph!”
Every time my fairly long finger overcame the grip of her anus and moved, lewd little moans spilled from Selena’s mouth.
They weren’t moans of pleasure so much as startled sounds at the sensation of movement inside her anus and intestines. Listening to them while playing with my finger, I brought the index finger of my left hand to the small gap created by the movement of my right.
Feeling the new finger touch her sensitive folds, Selena let out a sharp cry.
“Hiiik?!”
The new index finger slowly dug into the anus of the startled, moaning Selena.
“Haaah…”
With the added finger the squeeze of her anus grew even tighter, and Selena’s body convulsed in fine tremors as she let out pitiful moans.
Looking down at her gently rippling hips, I finished pushing the left index finger all the way in, then crossed the two touching fingers and moved them to stimulate her anus.
“Haahk! Hnnngh! M-Master! J-just a little… Mmph!? Haaa…”
I enjoyed the panting that spilled from Selena every time my fingers moved freely in every direction, stimulating her anus for a long while.
When the grip that had felt ready to snap my fingers off seemed a little looser than at the start, I put strength into both fingers and gently spread her anus open.
As the fingers that had been pressed back-to-back parted a little, night wind slipped into the small hole of unknowable depth and brushed along her rectal wall. Selena convulsed violently all over and cried out.
“Haahk?! M-Masteeer?! W-wind?!”
The moment I created a hole just large enough for one finger, the anus I had thought was slightly loosened contracted far more powerfully than at the beginning, trying to close the sudden opening.
I endured the crushing force on my fingers as long as I could before the hard-won hole closed again. Unlike games where you could just ram away without caring about the character’s reactions and the anus would expand in proportion to the number of times, I realized that developing a real anus was harder than expected.
Would tools make it easier? I wonder if this world even has anal toys like the sticks or beads I used in games…
Hoping this world had something that could help with the anal development that had hit a snag, I opened and closed her anus a few more times.
“Hnn! Haaah!!! M-Masteeer! I-it’s weird! Th-the wind again!”
Until I could feel that Selena’s anus—trembling every time night wind brushed past her rectum whenever a hole was made—had loosened, ever so slightly, compared to the beginning.
…It had loosened, right?