5 Times a Day

**Chapter 64**

I turned her around and guided her knees onto the seat of the chair so her legs hung off the front edge. Her hands gripped the top of the backrest hard for balance. The position forced her full, heavy ass out toward me in a perfect open presentation. There was no need to spread her cheeks; the tight pink ring of her asshole was already fully on display, still shiny and slightly swollen from my tongue.

I leaned in and started licking again.

The taste was still difficult to name, but it was rich and addictive. I dragged the flat of my tongue over the puckered entrance in slow, deliberate circles, then pressed the tip firmly against the center and pushed just enough to feel the muscle flutter and try to push me back out. I spent a long time there, coating her thoroughly, alternating between broad wet licks and focused pressure until the entire tight ring was slick and glistening with my spit.

She felt every stroke. Soft, controlled breaths left her, but almost no real moans at first. Unlike her pussy, the stimulation here did not translate into immediate sharp pleasure. Porn had lied about that part the same way it lied about nearly everything else.

Once she was wet enough, I brought one finger up and pressed the tip against the small opening. The resistance was immediate and strong. I pushed slowly, working the first knuckle inside with steady, patient pressure. The heat that closed around even that small intrusion was intense.

“Hmph…”

A short, uncomfortable whimper escaped her. Anal was always tricky. The area was dense with blood vessels, which meant the risk of tearing or bleeding was real if I rushed. Without numbing agents or heavy preparation, the only safe way was slow and careful. Mana had already shown me it could change the sensation for her. I decided to use it again.

I coated the finger already inside her with a thin, controlled layer of mana and pushed deeper, curling the pad against her inner walls and rubbing in short strokes.

“Aahhnn~~~”

The moan came instantly and seemed to surprise even her. She turned her head to look back at me, eyes wide and slightly glazed.

“What did… you… do…?”

“Just a little something,” I said, and began to move the finger more deliberately, rubbing the front wall of her passage while the mana sank into the sensitive tissue.

“Hhmmmnnn~~~”

The second moan was longer and completely unrestrained. The mana was doing its work. She could feel pleasure now, but it was different from anything her pussy gave her: deeper, stranger, more intense in a way that made her hips shift restlessly against my hand. After only a short time, she started pushing back, taking the full length of the finger on her own with small, needy rolls of her waist.

“Aahhhaaannnaa~~~!!!!”

The sound that left her was raw and open. She wanted more.

I coated my middle finger the same way and carefully worked it in beside the first. The stretch was significant. Her asshole clenched and released around both digits in tight, rhythmic pulses that felt almost alive: hot, soft, and powerfully restrictive at the same time. Every time the ring tightened, the pressure made my cock throb hard against my stomach. The inside of her was silky and burning hot, the walls fluttering and gripping in irregular waves. If it felt this good around my fingers, the real thing would be overwhelming.

That was also the problem. Mana heightened her pleasure and made the nerves numb, but it did not change her anatomy. My cock was far thicker than two fingers. Forcing it would risk real injury even with the extra sensation.

I opened the shop and searched quickly.

[Bleed removal]

[Type: Consumable]

[Effect: Makes a person not bleed, therefore preventing the loss of HP for ten minutes]

[Pain receptors are unaffected]

[Cost: 1000 coins]

It was the best option available on short notice. I bought it, summoned the thin paper into my free hand, and pressed it against the small of her back. The item sank into her skin with a brief flash only I could see. A dark mark appeared and immediately began to fade; the ten-minute timer had started.

I pulled both fingers free with a wet sound. Aunt Elise made a small sound of protest and started to turn.

“Why did you sto—”

The words died in her throat when she saw me stroking my cock and lining the thick, flushed head up against her still-open asshole. Pre-cum was already beading at the tip and dripping onto the tight pink ring.

“Tyler…” Her voice carried real hesitation now, almost fear. “Shouldn’t you lub-lubricate it a bit more?”

Seeing the actual size of what was about to push inside her had clearly sparked second thoughts. Fingers were one thing. The heavy, veined length of my cock was something else entirely.

“We can’t just stick to one thing,” I said quietly.

I coated my cock in mana the same way I had coated my fingers, feeling the energy sink into the skin and make every nerve more sensitive. Then I took a mana potion from the shop to keep my reserves stable. Once everything was ready, I settled the swollen head firmly against the tight entrance and pushed with slow, steady, unrelenting pressure.

The ring resisted for a long moment, the muscle trying to stay closed. Then, gradually, it began to give way. The head slipped inside with a thick, stretching pop of sensation.

“Ungh!”

The grunt was short and strained. A heartbeat later, mana took full effect, and her body reacted hard.

“Aaaannnhhh~~~~~~~!!!”

Her back arched sharply, and a full-body tremor ran through her as the thick head stretched her open. The heat and pressure around me were immediate and extreme. Her asshole clamped down like a living fist, hotter and tighter than anything I had ever felt in my life. The silky inner walls fluttered and squeezed in panicked, pleasurable waves, trying to adjust to the sudden invasion. The sensation was so intense that my vision narrowed and the urge to cum hit me like a physical blow to the gut.

The system, almost mercifully, flashed an item.

[Hold back]

[Type: Consumable]

[Effect: The person the item has been used on cannot ejaculate]

[The sensation from ejaculation would remain]

[Duration: 5 minutes]

[Cost: 200 coins]

I bought and activated it in less than a second. The climax was locked away, but the full feeling of being right on the edge remained, turning every pulse and flutter of her body around the head of my cock into pure, sustained, torturous pleasure. My thighs shook. Sweat broke out across my back.

“Haa… haa…”

I breathed through it in short, controlled gasps while Aunt Elise moaned beneath me, head lowered, the sounds soft and continuous and rising.

“Hng~~~ oh~ ooohhh~~~ ahhnn~~”

I forced myself to keep control and began to push deeper. Inch by careful inch, the tight passage swallowed more of me. The pressure never eased; it only grew denser and hotter the farther I went. Her inner walls dragged along every vein and ridge of my cock in a silky, burning grip that felt like it was trying to milk me even though I could not cum. The stretch of her asshole around my shaft was visible every time I glanced down: the pink ring forced wide, shiny with spit and her own juices, clinging tightly to the thick girth forcing its way inside.

Aunt Elise suddenly gasped, the sound sharp and shocked and almost disbelieving.

“OH, MY GOOD LORD!!!”

She was not a religious woman. Hearing those words tear out of her mouth was all the encouragement I needed. I kept pressing forward, feeling every ridge and flutter of her inner walls drag along my shaft in tight, wet friction. Halfway in, her body began to convulse in deep, rhythmic waves. Her head stayed down at first, but the way her pussy clenched and released in time with the spasms of her asshole told me exactly what was happening.

She was cumming hard.

Clear fluid sprayed from her pussy in strong, uncontrolled pulses, soaking my feet, the chair, and the floor. At the same time, a second, warmer stream joined it. She was squirting and pissing together, the mixed scent rising between us in a thick, filthy, intoxicating wave that only made my cock throb harder inside the crushing heat of her ass. The knowledge that I was buried in her most private hole while she lost control of both her bladder and her orgasm sent a dark, possessive heat straight through me.

I did not stop.

I pushed through the last of the resistance in one continuous, relentless motion. Her voice climbed into a long, broken, almost desperate scream.

“OH MY FUCKKKKK~~~~~~~~~!!!!!”

Her head snapped back, face flushed deep red, expression locked somewhere between overload and pure raw sensation. The muscles in her neck stood out. The spray from her pussy intensified into a hard, continuous jet that kept pulsing with every inch I forced inside her. The sight of her completely losing control, the impossible tightness strangling my cock, and the wet, filthy sounds of her body finally broke the last of my restraint.

“Gah—!”

One deep, animal thrust buried me to the hilt. My hips pressed flush against the soft, full, jiggling cheeks of her ass. Every single inch of my cock was locked inside the hottest, tightest, most overwhelming heat I had ever felt. Her asshole fluttered and spasmed around the base in rapid, helpless pulses, trying to adjust to being completely filled.

“AAAAHHHH~~~~~~!!!!”

Her cry filled the bedroom as her body clamped down around me in another violent, full-body orgasm, and I stayed buried to the root, fully inside my aunt’s ass for the first time, feeling every tremor and every wet, filthy pulse of her release while the denied climax burned like fire at the base of my own cock.