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 not attempt anything more. My anal opening is now at its maximum dilation and I don't think I can take it any more.

"My dear, don't be afraid, I will push it in a bit more and you will now tighten your buttocks with all your strength to close your opening... the plug will then enter on its own all the way into your anus... don't be afraid, my dear, and trust me... thanks to the oil I applied, you won't feel any pain, you'll see," he reassures me.

I am a bit scared at the thought of doing what he asks me, but still confident, I start tightening my buttocks with all my strength, but my opening is so dilated by the size of the plug that I can't manage to close it. And to reassure me further, Harry leans over me to kiss my left buttock while caressing the lower part of my back with his other hand.

"I'll help you a bit, my dear... try again to tighten your buttocks while I push it... there you go... you see, it's starting to go in... you're doing very well, my dear, it's as if you've been doing this all your life," he tells me, seeing the efforts I'm making to close my anus.

Feeling ashamed and confused by what he just said, I hide my face in the sheets and start doing what he asks of me. And then, as Harry pushes it with his hand... suddenly, overcome by my efforts and his patience with me, the plug quickly penetrates all the way into my anus, while my opening closes tightly around its narrow neck. The large pink heart-shaped bead, whose role I quickly understand, presses against my opening, preventing the plug from entering fully into my rectum. As Harry promised me, I feel no pain, on the contrary, I feel well-filled and happy to experience such a thing for the first time in my life.

"Well done my dear, I'm proud of you... you learn quickly... you will keep this plug until I remove it... it will keep your anus well dilated and prepare you for the penetration of my penis," he said, lightly pulling on the pink bead to ensure it hasn't moved and is securely in place. Harry has finally revealed to me the purpose and role of these pleasure objects, and deep down I feel very lucky to know him. The idea of keeping this delightful object in my anus fills me with joy and happiness, but I am also very eager to be penetrated by his penis and finally experience the sensation of having my rectum filled by a male organ. However, I also believe that Harry, with all his experience and knowledge, must know the exact moment when I will be ready to receive his penis. Therefore, I decide to trust him and be patient.

"Lily darling, lie down on your back now... I will taste your other charms... you have many other treasures I would like to discover," he said as if he had guessed my thoughts.

Impatient, I willingly obey Harry and lie back on my back, while he rises from the floor to position himself above me, kneeling between my legs. He lowers his head towards me, nuzzling into my neck. There, he starts kissing me gently behind my ears, whispering kind words. I tilt my neck towards his lips and place my hands on his back to pull him closer to me.

Her ample chest presses against mine as he continues to kiss me on the neck. After a while, his mouth leaves my neck and moves towards my mouth, his lips crushing mine in a passionate kiss. He uses his lips to make me open mine, and his tongue meets mine. We spend a long time kissing and playing with our respective tongues, mixing our saliva. My desire for Harry is now so strong that my legs rise in the air to wrap around his back and shoulders. I try to bring his belly closer to mine, seeking a more precise contact, the touch of his penis that sometimes brushes against my vulva, but he resists me.

-"Be patient, my darling... spread your thighs wide... lift your legs towards your neck and let me take over," he says.

to be continued