After a few minutes.
"Sweetie, looks like the waiting time is over. Let's get to the real business here", says Lily. Harry agrees with her. The anticipation of what's about to happen fills with excitement and arousal.
"Now, get down on your knees and bend over while lifting your ass", Lilith tells him. After he bends over, she spreads his butt cheeks and plays with them for a bit.
Seeing that dildo has stretched his ass to its size. She slowly pulls it out, and when it's almost completely outside. She smirks as she gets an idea, which she implements by shoving the dildo back inside in a single stroke. This sudden intrusion causes him to moan loudly.
"Ahhhh...."
She repeats this motion again and again for a few minutes, causing him to moan repeatedly.
"Ahhhh....ahhh...ahhhh...ahhhh"
"Ahhh... Mom, push....ahhh... it harder"
"And...ahhhh ....faster...ahhh....en deeper"
"Ahhhh....I am going....ahhh...to cummm!...ahhh"
Hearing that, Lily stopped moving the dildo any further and removed it completely.
Feeling her sudden actions, Harry turns his head around and asks, "Mom, why did you stop? I was about to cum."
"Don't worry, I have something planned for you. Now, stay as you are and let me do the rest." Saying that, Lilith takes out a bead-type anal buttplug with 10 beads. The girth of the smallest bead is 2 inches, while the largest is 4 inches.
She then inserts the beads one by one, slowly. The first bead goes in easily, but as the size increases, it becomes harder, and the last bead took a significant effort. Once all the beads are placed inside, the only thing visible is the strap and ring connected to the beads.
While Harry stays in doggy-style position and Lily leans on his back from behind, pressing her boobs on his back and starts stroking his dick with one hand. She slowly starts increasing her speed. She uses her other hand to spank his ass roughly, leaving behind deep-red handprints.
Each time she spanks him, his insides clench around the buttplug tightly. He moans on top of his lungs as her spanks cause him to feel both pain and immense pleasure.
She continues to stroke him and spank him every few seconds for some time. His cock starts twitching as he feels his orgasm build up. She felt it too, so she quickened her pace. Just as he was feeling, he was about to cum, she stopped stroking him. Just as he was about to wonder why she stopped, she grabbed the ring of the buttplug and used all her strength to instantly pull out the buttplug from inside him in a single motion.
This action causes him to experience an overwhelming amount of pleasure at once, which makes him have a massive orgasm, causes his eyes to roll back and makes him scream so loudly that anyone in the mansion could have heard it.
"Aahhhhh!" After finishing his biggest orgasm in his life, he collapses on the bed unconscious as his mind is unable to handle such mind-numbing pleasure.
"How was that surprise attack?" Lily asks him, but seeing that he didn't respond to her, she looks down to see his face, only to find him unconscious.
'Looks like I overdid it, and that last scream was really loud. Good thing I set up a silencing ward before starting', Lily thought as lays down and placed Harry on top of her with his head resting on top of her breasts and her cock between his thighs.
She then creases his buttcheeks softly and plays with them. After 30 minutes, he wakes up slowly. As he lifts his face, he sees her face. So, he leans forward and kisses her. At first, it was a small kiss, but slowly they got more passionate until they were French kissing each other passionately for 10 minutes straight.
"That was amazing," Harry said as he got up and places her cock on her stomach and sat on top of her cock. Her cock gets sandwiched between his asscheeks, and then he moves his hips back and forth. Her dick gets massaged by his buttcheeks, causing her to moan softly.
"Ummhhh..... Thanks, Sweetie", Lily moaned lightly and said, "Sorry that I went overboard by being so rough there.
Harry replies, "Although you were rough, I liked it, so it's ok. Especially when you spanked my ass. I really loved it even though it was painful too. I might have developed a slight fetish for getting spanked, so next time, don't do it so roughly."
"Oh my! I didn't expect you to develop such a fetish so young. You are such a naughty boy, Harry. Let's stop her for now, we can continue the rest next week. So, let me put this buttplug in your ass and then we can go to sleep." Lily said that as she flipped him over and inserted a buttplug.
1 year & 3 months later~~~
{12, December, 1994}
Time passed quickly, in the blink of an eye, more than a year had passed since we started training, and Harry's birthday was over a bit more than four months ago. His progress over the year was good, and now he can take a 14-inch cock without any discomfort. Today was the last day of his training, so he was excited about it.
"Well, Sweetie, you completed my training last week. So, I planned something special for today. You can think of it as a graduation gift." Lily said that as she takes out a buttplug with an oval-shaped base with a crystal embedded on it.
"What's that for mom?" Harry asks, confused.
"Sweetie, you are going to wear this every day from now on, even when you are at Hogwarts. The only time you take it off is when you are going to use the restroom or have anal sex." Lily said that as she pushed the buttplug inside.
"But, Mom, what if other guys see it when I am in Hogwarts?" Harry asks her, concerned.
Lily then replies, "Don't worry, it is enchanted so that only a futanari can see it. So, no one will notice it even if they stare at it. Now, enough talk, go to sleep."
Then, they both slept with Lily spooning him, while placing her cock between his thighs.