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

Lily's Anal Initiation by Harry Ch. 02

... 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 ...