It was a new era at Chaldea.
 Astolfo, once a constant party member… wasn’t getting picked anymore. Oh, sure he might ride along for the bond points, but he wasn’t fighting.
 “Leave it up to us!”
 The frontline servants would save the day and Astolfo would sit there, looking pretty. In fact, that’s what Gudako seemed to want.
 “Don’t worry, Astolfo. We’ve got this. Just look cute and come along with us.”
 Astolfo sighed and came along. He was never getting used at this rate. Eldritch horrors, demon pillars, third rate gods, he watched them all get handled with ease.
 One day, Gudako entered his room with some clothing in a hanger bag.
 Astolfo perked up. He liked new clothes a lot.
 “Do you have a sexy new outfit for me, master?”
 Gudako nodded. “That’s right, Astolfo!” She unveiled from the bag- a vertical sweater in pink and some jeans?
 Astolfo protested. This couldn’t be right.
 “How am I going to look sexy in mom jeans?” He asked.
 Gudako also placed a pair of knee high leather boots on the bed, with blocky heels.
 “Astolfo… I have a mommy kink.” Gudako said matter-of-factly.
 Astolfo titled his head. “Eh? So… Raikou, Arturia, Boudicca, Scathach… these women weren’t available?”
 Gudako shook her head.
 “Honestly… I thought it would be kinky and fun if you did it. And I trust you. I mean, you took my virginity and all.”
 Astolfo said “Oh yeah… aha…” knowing full well he certainly did.
 “Just… put it on for me. Please?”
 Astolfo looked into those puppy dog eyes.
 “Alright, fine.”
 Astolfo disrobed right there, which is what Gudako wanted. He slipped on the jeans… they did feel comfortable, he had to give them that. He slid the sweater on… it was soft!
 “Vlad knit that for you. He was happy to do so.”
 Astolfo beamed at the thought of one of his Servant friends doing this for him.
 Finally, he put on the big boots… They made him at least 3 inches taller and feel really sexy.
 “Ok, this part I can understand, your boot kink is off the charts. But what about the rest?”
 Astolfo had barely finished his thought when he saw Gudako had raised her arm towards him, with one of the command seals glowing.
 “By the power of my command seal, become my mommy, Astolfo!”
 The seal disappeared from Gudako’s hand. Astolfo gasped. Even his dense brain knew what would likely be happening next.
 He felt a twinge in his chest, and suddenly noticed the sweater started to push out a little bit from where it originally sat. He looked down the neck hole to see…
 “Titties! Milkers!” He said, having very mixed feelings about the whole thing.
 While he was examining his new breasts, he felt his jeans get tighter around the hips. Sure enough, his thighs were growing rather thunderous.
 “Master, why are you doing this to me?”
 Gudako looked at him indifferently. “To test my abilities.”
 Astolfo squeaked.
 “And, also because I find this fun. You’ve always been my favorite Astolfo, so welcome to my family.”
 Astolfo then felt something… opening… in his crotch. Still in his usual manner, he thrust his hand down into his swelling jeans.
 “I HAVE A PUSSY?”
 Gudako nodded. “I think the command spell was pretty clear.”
 Astolfo felt faint. He felt… different.
 “That’s crazy, even for me!!! That’s just weird, it’s… it’s…!”
 Then, a smile came across his face.
 “It’s just wonderful, dearie!” He said with a musical lilt in his voice. He clasped his hands together beside his face and smiled as he closed his eyes for emphasis. His mom transformation was complete.
 His breasts had finished growing. He hadn’t beat Raikou, but anyone short of Jeanne Alter would be jealous. They filled out his sweater quite nicely!
 “Speaking of those new… assets, here, have one of these.” Gudako handed Astolfo a new, plush bra.
 Astolfo raised a hand to his face and gasped. “Oh my goodness! This is lovely… now, turn around, momma has to put this on…”
 Gudako did actually turn around, but playfully looked back at Astolfo. He didn’t seem to mind much. He was just happy to be supported! He clasped his own breasts and felt glad. He then slipped his vertical sweater back on.
 “Thank you dearie. This helps me an awful lot!”
 Astolfo went to give his daughter (?) a hug. Gudako loved being embraced by that soft new body with large breasts.
 “Looking good, “mom”.” Gudako smiled as she buried herself in Astolfo’s new chest.
 “Thank you honey. You’re too nice to your old mom.” He rubbed her head and smiled.
 Gudako’s hand started to infiltrate Astolfo’s shirt. It started around his hips and slowly slid up his sweater to the puppies that lie within.
 “What are you doing, darling?” He said, as clueless as ever. He’d gotten bustier but not smarter.
 Gudako’a face surfaced from within Astolfo’s tits with a snarl like a hungry shark.
 “I’m getting my hands on these new MOMMY MILKERS!”
 Gudako’s hand squeezed on those fat tits and loved every second of it. Astolfo squeaked as he realized what was happening.
 “Oh my goodness! What are you doing, frightening your poor mom like that?” He panted as Gudako fondled his breasts.
 “That command spell worked really well… you really are playing the mom part well.” Gudako said, mostly to herself.
 “Once your mother, always your mother. I think I might need to discipline you!” Astolfo retorted.
 But he reacted too late- Gudako lifted his sweater over his udders and pulled down part of his new bra- and she started to suck on his new, big nipple.
 “Oooh, ooh!” Astolfo exclaimed as he felt this new sensation. This was something totally different… his nipples were sensitive before he grew female breasts and now he felt like he was going to double over.
 He composed himself enough to place his hand on Gudako’s head… and he rubbed her, gently.
 “That’s alright, dear. Drink what you want. Momma is just not used to her new body yet. I want you to feel good like I do.” Astolfo smiled warmly and motherly. His child could do no wrong and was cute to boot.
 As Gudako sucked, she had one of her hands wander down below. She felt a large bulge in Astolfo’s new jeans- even though Astolfo grew a pussy, he hadn’t left behind his massive meat.
 She started to rub it beneath the denim and felt as it steadily grew larger. She was really liking this. Astolfo was the perfect Servant- no, the perfect mother!
 “Mmm… aah! Nnnoooo… it’s too much to suck your mother’s breasts and rub her cock!” Astolfo cried in protest.
 “On the contrary, I think it’s just enough!” Gudako said as she came up for air. She blew gently on the exposed nipple which made Astolfo shudder.
 She swiftly undid the buttons on Astolfo’s jeans. She saw that cock flop out of the denim, aching to be free.
 “I think I want some milk from that too…” Gudako said lustily.
 Gudako got on her knees and had to stretch up a bit thanks to Astolfo’s new high boots, but she swallowed his cock down to the base. He put his hand in her hair and guided her. Gudako was totally blissful.
 “Puah! I think it’s time for something new…” she said, and then Astolfo lead her to the bed. He pushed her playfully and then got on top of her. Astolfo’s cock lay dangerously close to Gudako’s pussy. He smiled.
 “I told you that I was going to have to discipline my child. I’m still your mother.” He smiled with his eyes closed. Gudako sweated.
 His dick started to make headway… and then Gudako pulled a reversal.
 Gudako in an instant had flipped them around, with Astolfo’s breasts bouncing as he was now the one lying on his back, cock flopping and slit soaking.
 “Uwahh!” He exclaimed. It’s the same thing he would’ve said had he not been transformed.
 “I’m going to give you the mating press, mommy. I’ve been having fun and I am NOT going into time out.” Gudako quickly slid her dick into Astolfo’s Fertile Crescent.
 “Oooh… oooh! How dare you… do this to your own mother! You’re so naughty!” Astolfo cried out, as the pounding began. Gudako went from 0-100, it felt like.
 Gudako was panting, almost slobbering at this divine pussy.
 “You must have new skills, Astolfo. I swear you have Golden Rule (Body) now. I’m thinking…. It’s EX!” She bounced up and down, relishing the soft body of the boy who was now more fem than boy.
 “You’re speaking to your mother so sweetly, yet…. Hah… pounding her so harshly!!” Astolfo was struggling to speak. The dick was making his already addled mind go crazy.
 Gudako slid the sweater off of Astolfo’s head, with him raising his arms to ease the transition. She instantly started sucking away on one of his breasts and kept thrusting.
 “Darling, I don’t think you’ll be able to pull o…oooout!” Astolfo cried.
 “I…. don’t…want… to!” Gudako panted.
 Astolfo’s legs, now acting on instinct, wrapped around Gudako’s torso as she pumped into him. Gudako felt those sexy boots on her back and got even hornier, if that was possible.
 Gudako surged inside of Astolfo’s new pussy, flooding it with cum. She was panting, and eventually stopped thrusting but remained very tightly wrapped around Astolfo. Astolfo, for his part, was patting Gudako’s head and still had her in a boot lock.
 Eventually, he let her go and Gudako watched as her semen spilled forth like water from a sieve. She licked at a bit of it and was surprised at the taste. Post-nut clarity was settling in.
 “Well… that was certainly a new experience for your mother.” Astolfo sighed, still lying back, facing the ceiling. His legs were shaking on the bed as cum flowed forth from between his legs.
 “Hey, look at this.” Gudako said. Astolfo lifted his head wearily.
 There was a splattering all on Gudako’s mystic code. Astolfo’s cock hadn’t been able to contain itself either. He laughed, and Gudako slurped the semen off of his dick.
 “Ahh… I’m going to just lie with you, mommy. If that’s ok.”
 Gudako lay down beside Astolfo and hugged him from the side. Astolfo did the same and was petting her head again.
 “My baby…” He said. He vaguely remembered being just a male Servant, but this was all he knew now. Mother to one of the greatest Masters who had ever lived.
 He also felt inside of him- maybe it was due to some extra sensory Servant ability, but Gudako had knocked him up- as if no one knew from the splooge shower that was his cunt right now. He was definitely pregnant, and was going to start growing larger soon… but he looked forward to it, greeting each new challenge with a smile.
 Just like he always did.
 ——
 “Bye mom!” Gudako leaned up to kiss Astolfo goodbye.
 “Goodbye, dear. Food will be waiting when you come back from your singularity.” He smiled and rubbed his belly unconsciously. He was doing that a lot these days. His belly had swollen with their child. His brain didn’t see any reason why that was weird, a mother would do anything for their child… even get impregnated. To Astolfo’s mind, it made sense.
 Astolfo hadn’t taken the sweater, jeans or boots off since that day. His other outfits seemed passé and no longer interested him. Gudako swore she would get him some new clothes soon. Vlad was working as hard as he could and soon called on Ms. Crane’s assistance, who was delighted to see Astolfo glowing and pregnant. She had rubbed his belly so much… The other servants seemed to ignore it. Astolfo stayed largely in his room- in their room- since he was now out of action for the foreseeable future.
 “Oh, and, Astolfo?” Gudako called from the door.
 Astolfo looked up from the lovely meal he was preparing with a smile.
 “When we get back… you’re going to try on that outfit I stole from Raikou’s room.” Gudako smiled sinisterly.
 Astolfo started to get wet between his legs. Of course he knew which one- one of the copies of the bodysuit that Raikou wore each day. Astolfo thought it was so sexy and Raikou had been easy to fool. Gudako snuck inside when she was out and pilfered the sexy suit. Now that Astolfo and Raikou had similar figures, it would fit him so tightly…
 “Y-yes dear. I can’t wait. I’ve been thinking about it for a long time.” Astolfo shakily admitted.
 Gudako went to close the door- “Love you, mom.”
 Astolfo smiled sweetly. “Love you too, dearie.”