Lily's Anal Initiation by Harry Ch. 02 - Sex Stories

Lily's Anal Initiation by Harry Ch. 02

"Go for it, Harry my dear, keep going like that, I love what you're doing to me with your tongue," I told him.

Encouraged by my words, Harry now presses his mouth entirely against my anus. His lips, wide open, also work to massage the entire area of my opening. After a few minutes, he lifts his head to admire the result. This gentle massage has completely relaxed me. My anal opening is now completely relaxed, and the skin all around is perfectly dilated. I'm sure that now I am ready to receive, without any pain, any male organ, no matter how large! And I have never felt better than today.

"Lily darling, please don't move... Stay in this position... I'll be right back," he said, rushing to a chest of drawers. He quickly returns holding an object I have never seen before. He places it on the bed, right in front of my eyes, and goes to get a bottle of massage oil from the nightstand drawer that I sometimes use to massage my legs. The object in question is made of transparent glass, in the shape of a large elongated egg, with one end pointed and the other narrowed into a neck that ends in a large pink pearl cut into a shape resembling a large diamond."

''Lily, my dear, I'm going to insert this plug into your anus, it will keep it perfectly open and dilated... don't be afraid... I won't hurt you, my dear, I'll put plenty of oil on it," he tells me.

Seeing the size of this object, I admit I'm a bit scared of what he's going to do to me, but I also know that if Harry ...

... does this to me, it's solely for my well-being and to introduce me to new pleasures.

"Arch your back well, my dear Lily, just like earlier, and push your hips up... the oil is a bit cold, but it will do you a lot of good," he tells me.

He opens the bottle and lets a long stream of oil flow onto my widely open anal opening. I shudder at the contact of the cold liquid overflowing quickly from my anus onto my vulva, then running down my stomach. He also generously applies oil to the plug, and after making sure with his fingers that my anus is perfectly lubricated, he points the tip of the cold object at my opening, watching for my reactions, ready to stop if I show any resistance. I tremble a bit at the cold touch of the plug but I don't pull away, because deep down, I am so eager to experience this new pleasure.

"Put it in me, my dear Harry... go ahead... put it deep in my ass please... I want it so much!" I say, moaning.

And, acting on my words, I make it clear by firmly grasping my buttocks with my hands and pushing them towards the delightful object, to spread them further apart. Encouraged by my gesture, he gently pushes the pointed end against my anus, still watching my reactions. Thanks to the oil, I feel the edges of my opening easily parting under the pressure to grip it firmly. Seeing that I don't resist and that my anus seems to welcome this exquisite pleasure object, he presses it further until reaching the widest part. There, he stops pushing it and does ...