Warning: This fic contains heavy sexual content. If you are offended by such materials, do not read this.

XxStartxX

Astolfo thought that life was good. He was given one last mission by his Master. "To be among people". And he was more than fine with that. Astolfo was a man who craved adventure. He wanted to go everywhere, see everything, and do whatever the hell he wanted. He was a creature of brashness and impulsive action, and he knew it. But if there was another thing he loved, it was women. That made for the scene with the women on her back below him more believable.

It was a strange sight, for certain. Astolfo was not very tall, and his weight was considerably light as well. He dyed his hair pink and kept it in a long and thick braid. He tended to all his nails as well, and made sure his skin was as smooth as possible. All in all, when you couple these physical features with his choice of clothing (which usually included blouses, jackets stockings, and skirts), it was quite easy to mistake Astolfo for a female. And even stranger are the reasons behind his decision to appear that way.

Astolfo loved women. It was part of his legend, after all. He loved flirting with them, he loved pampering them, and he most definitely loved fucking them. He was as red-blooded a male you'd find anywhere, but when it came to love he couldn't care less the gender. That was something that just "happened" as far as Astolfo was concerned. Just look at him and Sieg. But still, despite finding women attractive and lavishing attention on them, he crossdresses so. And if you were to ask him "why", his answer would be this:

"Because it makes me look cute!"

Truly, that was the reason. He loved women so much that he despised the male form even upon himself. His vision of beauty was that of a female, so in his eyes, being beautiful involved emulating the fairer sex. He didn't want to be a girl by any means; his dick was his favorite part of his body. Astolfo just knew what he found attractive and aspired to be just that.

Of course, when disrobed, it became infinitely easier to discern his true gender. In life he was a Paladin, a warrior of valor. He fought for many people and engaged in many a battle. Despite how much he wanted to look "cute", there was a measure of physical fitness he could not avoid, granted it was very well contained. The muscles were tight, and were only readily noticeable upon close inspection, but the male definition was there. But that was not the biggest reason you'd be able to tell his true gender the minute his clothes come off. And that very reason was driving the voluptuous blonde women beneath Astolfo crazy.

"Ah... ah... mm~" The woman beneath Astolfo tried containing her voice, but Astolfo was too skilled.

The former Servant thrust deep, and knew just what spots to hit. Part of what made Astolfo so appealing in bed was his ability to read the tells of the women he lay with, and learn what turned them on. It took no more than five minutes into the act to find all the woman's good spots, and he wasted no time exploiting them. She was sensitive to being licked, and enjoyed her breasts being fondled. Astolfo grinned at the look on the woman's face. He saw the lust in her eyes and wanted to see more of it.

He pushed his body downwards, meeting his torso with hers. He dipped his head forward and sensually licked her neck, making sure to be as sultry as possible in his movements. While his right hand held firm on her hip to support his thrusts, his free found its way to her right breast. He squeezed and maneuvered the mounds of flesh with practiced ease, and periodically changed his grip to pinch her sensitive nipple. The woman began to thrash about her head, finding the pleasure unbearable. When Astolfo paused in his movements and began to grind his prick deep inside her, rotating his hips so he could scrape against her every wall... she lost it.

"Ah... ah... ah!"

Wrapping all her limbs around her lover, the woman tensed in orgasm. She shivered in pleasure as she rode out her climax. It was one of the best she'd ever had, and it came from this small, effeminate man above her. She had made a single mistake though. While cumming, her pussy and gripped Astolfo's cock like a vice, tensing and loosening with each contraction of her orgasm. Even for a man as practiced as the Rider of Black, the stimulation made him lose control.

Astolfo pulled out of the woman and rose on his knees. It allowed the woman to get a good look at him. He was completely naked, and his normally braided pink hair flowed loose behind him, reaching his mid-back. When her eyes traveled downwards though, she saw what really made him a man, leaving no mistakes.

Astolfo's cock was as formidable as his fighting prowess. It was thick and long, reaching almost ten inches. Angry veins adorned its length and bulged with each pulse of the monster. It bobbed up and down in accordance with Astolfo's heartbeat, and no woman could deny becoming captivated at the sight. Below the monstrous shaft was a proportionately impressive pair of testicles. A large sack that hung low, filled to the brim with churning seed that wanted nothing more than to flood the woman before him.

The woman's time to admire the paladin's endowment was short, and she was grasped by her hips and flipped onto her stomach. She felt her behind raised high, and almost immediately afterwards she was speared deep by Astolfo. If Astolfo had one fault as a lover, it was his tendency to get lost in the act. If a woman managed to hit his own buttons, he would sometimes lose control and become vigorous. The way the woman had tightened around him, caressing his length... it was enough to set him off.

He pierced her at an extremely fast pace, almost seeming frantic. Despite his speed, his thrusts lost no potency. He drew out at least seven inches with each thrust of his hips, causing long, pleasurable scrapes down the woman's flesh tunnel. The blonde woman had lost her ability to keep quiet. Where before she could stifle her vocalizations to that of sensual moans, Astolfo's newfound aggression made her lose all control. She moaned still, yes, but on some of the effeminate man's deeper thrusts caused her to yelp. His speed increased still more, and even as a Heroic Spirit Astolfo's breath became slightly hitched. His Endurance rank was pitiful anyways.

Astolfo was enjoying himself immensely. It had been a long while since he'd torn apart a pussy so good. He had a goofy grin on his face, showing just how far into his primal lusts he'd fallen. A particularly hard thrust sent the woman into orgasm again, and he winced under the pressure. He grit his teeth and moaned at the feeling of her velvety walls pulsating around his huge member. This woman was top notch in Astolfo's eyes, one of the best he'd ever had. The woman's second orgasm proved to only hasten the former Servant's desire for climax. Adding more strength behind his thrusts, he began to grunt in pleasure as he hit her deeper than ever, bashing at the door to her womb.

When the head of Astolfo's massive cock began to collide with her cervix, the woman lost all control of her lower body and went completely slack. But even as she fell forward to lay flat on her stomach, the young man mounted upon her showed no sign of slowing down. He simply fucked her flat, the frequency of his grunts increasing. His grip on her buttocks was tighter than ever, almost painfully so. It was obvious to the woman that the man was lost in his lusts. Astolfo managed to continue that blinding pace for almost fifteen minutes. The woman below him was still happily moaning and screaming, already having been brought to orgasm two more times. Eventually, Astolfo managed to pierce her cervix. With the head of his member directly in her womb, he found no reason to delay any longer.

Astolfo's cock visibly swelled, and the woman it was inside could definitely feel it stretch her even further than before. His egg-sized testicles ascended from their spot on the bed, preparing to inseminate the woman before him. With a gasp from Astolfo, the first shot of his load began its trip to her womb. Somebody watching where Astolfo and the woman were joined would have seen the testicles pulse, before a bulge traveled from the base of the cock and into her vagina, visibly stretching her entrance even more as the seed passed through.

After what seemed like forever, yet was no more than a second, a pure white stream of thick, white semen entered the woman's womb at high pressure. It was a ridiculous volume as well, the entire shot managing to actually begin to fill her womb. The pink-haired warrior was far from done though, as his balls continued to pulse, sending more and more of his thick cum to be deposited in her sacred room. Astolfo's body was completely rigid, all his muscles coiled tight in rapture. His head was titled upwards, and drool escaped from his slightly opened mouth. He gasped with each contraction of his orgasm, focusing on nothing but completely filling the woman beneath him.

The woman herself couldn't believe he was still cumming. While she had climaxed at the same time as him, hers had already subsided. Astolfo, on the other hand, was still happily pumping her full with his thick baby batter. She even began to feel pressure in her stomach as her womb actually SWELLED to contain his copious amounts of seed. She began to feel herself getting tired. The rapture from her orgasm had subsided, but for some reason she felt a certain degree of vitality leave her. She drifted off into a deep sleep before the dick inside her had even stopped spewing its load. All things came to an end though, and eventually Astolfo stopped pumping the woman beneath him full of cum. He collapsed forward onto her back, panting from what might have been one of the most extreme orgasms since he'd been summoned as a Servant.

He was almost unable to remember to drain her prana when he climaxed. It was his way of staying rooted in the living world despite being a construct of prana. Sieg passively provided him prana from his resting place, but it wasn't enough for Astolfo entirely. He would use his A+ in Luck to successfully flirt with women, and use the sex as a one-sided tantric ritual of sorts. It left the women exhausted, but he would always play it off as fucking them so hard they passed out. The amount he took never hurt them, and he got to keep on living.

Once Astolfo's breathing had evened out, he slowly extracted his limp self from the tunnel he'd been buried in for the past thirty minutes. Like the plug to a dam, the minute his cock (still considerably large despite having gone flaccid) slipped out of the woman with an audible "plop", a thick river of his cum poured out of her in a steady stream, eventually subsiding but leaving a sizable puddle in its wake on the sheets.

Astolfo scratched his head when he realized he might have gone a little overboard. It wasn't often he had such a great time with a random civilian woman, but somehow he'd managed to hit the jackpot. If he didn't love traveling so much, he'd debate staying around to fuck her some more. With a grunt of exertion, Astolfo pulled himself off the bed and stool up tall. He stretched out his arms, and it became ever-the-more obvious that he looked nothing like the sexual deviant he was. The innocent look on his girlish face had returned, and his pink hair and lithe form stood out still. A slightly small-statured man with a bubbly personality and girlish looks had just fucked a random woman he'd seduced into a veritable coma of orgasms and violent twitches.

Astolfo grabbed his clothes, which also did nothing to support his status as a male, and began getting dressed. He hadn't sweat so much during sex in a while, but he knew that if he entered his astral state the fluids would remove themselves. As he left the hotel room, he looked back at the sleeping form of the woman, still covered in sweat and cum. He'd never even bothered to learn her name, but it was usually like that.

Giving the desk attendant some money to contribute to the bill for the room when the woman woke up, Astolfo waltzed his way outside. The city of Prague was gorgeous, and the women equally so. He'd definitely have to come back here when he was in the area again. Calling upon his Hippogriff, Astolfo jumped into the air and ascended to the skies upon his mount.

He'd felt like visiting England. He hadn't been there since he was alive, so why not?

XxEndxX

This is my very first experience writing smut, but I am an extremely avid reader of it. I started reading "Fate/Apocrypha", and Astolfo's character design hit all my dark and sexy preferences. I couldn't find a single thing online that took advantage of his character being with a girl, and went ahead and did it myself. I hope you enjoyed, and don't expect me to keep on writing smut like this. I'm not certain if it's something I really want to do. Rider of Black showing his womanizing ways to an extreme degree in bed was just something I felt I needed to write.

Xeno out.