I didn’t get the whole backstory. He found me on Tumblr and started a conversation that centered around his wife. His request was we meet, and I fuck her ass. This was going to be a simple one-off; there would be no oral, no pussy, just anal. He had gleaned from my posts that this was something I might be good at. He was correct in his assumption. But honestly, I wasn’t surprised by this dynamic. He intimated she was an anal virgin, and he wanted her first experience to be unforgettable from a size standpoint. Normally, I prefer a lot of foreplay to get her ready for this sort of penetration, particularly because I am very well-endowed.
We met in the lounge. She was gorgeous and quiet; he was cordial but a bit aloof.
We had one drink when he said, “Shall we?”
She dropped her gaze and nodded submissively. I arose from my seat and the three of us went to the elevator. As the elevator rose (it was one of those glass ones) he pulled her close, kissed her, and began to whisper in her ear. As he did, he lifted her skirt showing me and anyone watching the elevator her ass. She turned bright red as the doors opened. We arrived at their room, and she led the way in.
He sat in one of the chairs in the anteroom. He motioned to her to remove her clothes but leave her lingerie on. He commanded her to turn to give me a full look. Then he bade her bend over and show me her tiny asshole. She complied and I must admit her tiny rosebud was gorgeous. It was small and freshly waxed. It was difficult to imagine how my large cock was going to fit inside. My cock hardened at the thought of penetrating her resisting sphincter. My mouth began to water when I imagined her protestations and lamentations as she lost her anal virginity.
“Tell him. Tell him what you want him to do. Be a good girl and tell him,” he commanded.
Barely audibly, she whispered, “Fuck my ass.”
“Say it louder and ask nicely, baby girl,” he commanded.
“Please fuck my ass.” She said it much louder this time.
He looked at me and nodded and I disrobed completely, my large heavy cock hardening. As she watched, her eyes widened, She looked at him, fearful yet just a bit sultry, and whispered, “I can’t. You know I’ve never. Please I won’t. he’s too much.”
Since I am nine inches in length and about six and a half inches around, I wasn’t surprised by her comment. Just the head of my cock is going to stretch her tiny butthole by a magnitude of three.
“Tell him everything, now,” he said forcefully.
She turned and faced me; her eyes were on my rock-hard cock and she subtly licked her lips. She said clearly, “I want you to fuck my ass. I want you to fuck it until you cum and fill me with your thick cum. I need you to fuck my ass, please.”
With that, she turned around and placed her head in his lap, pulling her thong down so that all I could see was her pretty little asshole. If this was a different encounter, I would spend the next ten minutes working up to a two-finger penetration before I would even bring my cock to bear. He nodded to me, and I grabbed the lube I had hidden in my hand. I poured a copious amount into my hand and coated my cock thoroughly. I placed the head of my cock on her little rosebud and began to push, gently but insistently.
I could feel her tense up trying to prevent the intrusion. I eased off a bit and went again. This took two or three minutes before her muscles began to release allowing just the thick head of my cock in. I watched her tiny orifice battle my insistent pressure. As I pulled back out, I reapplied the lube and pressed again. This time I got about two inches inside her anus and stopped, allowing her to breathe and get used to the penetration. As I felt her relax, I slid myself in just a bit more and stopped. I continued in this way for about ten minutes until my entire shaft was inside. When I stopped this time, her breathing began quickening. Her anal passage began to quiver around my thick member. It was involuntary as was the moan that followed.
He pulled her hair back and whispered, “He’s all in now. You have a big cock in your ass, like I promised. How do you like it? You’re such a beautiful slut with a cock in your ass. I hope you are ready.”
She whimpered, “Oh god. I’m so full. I can’t. Please, Daddy, don’t make me. I promise I’ll be a good girl.” He looked at me as I slid the full length of my cock out leaving the head just inside her tight passage. He nodded at me. I added more lube and began to slide in and out of her ass. She started to move her ass and fuck me back making little mewing sounds as her pleasure began to build. I continued to draw the full length of my cock out and driving it back in. I wasn’t going hard and fast, but I was insistent in my ministrations.
“Oh, fuck that feels good. It’s really good. I’m going to cum. Oh god. Can I cum, please, oh please Daddy let your little slut cum. Let me cum with this big dick in my ass, please, please, please.” She was whimpering.
He said, “Not yet baby girl. Soon.” He looked at me and nodded again and mouthed “Do her harder.” I grabbed her hips and began to pound her pretty little butt. She began to howl with pleasure as I pummeled her ass. Listening to her howl, my cock was steel hard as I kept my ejaculation under control. Her legs began to shake as she fought the waves of pleasure overtaking her. I wasn’t going to let up. This is what they both wanted from me, and I was going to deliver the hardest, deepest most ass-ravaging fucking I could.
“Can’t cum, can’t cum, can’t cum,” she repeated over and over.
Finally, he pulled her chin up and commanded, “Cum. Now.”
Her ass clenched down on my cock as her pussy squirted her juices down her legs and pooled on the floor. Her legs were shaking uncontrollably, her ass was moving up and down and her orgasm took over her body.
He looked at me and said, “Fill her up, fill the slut’s ass with cum.”
With those words, I began to fuck her with wild abandon now. Lifting her and plowing her previously tight passage, my rock-hard cock attacked her ass. Her tiny hole was gaping open and clenching my cock in a desperate attempt to slow my assault. Her asshole was wide open now and ready for what was to come. Like a man possessed I could feel my balls swelling as my cum began to rise from the depths. In a few short moments, I was on the cusp of letting go. I roared my orgasm deep into her bowels, filling her with my cum. It felt like I left buckets of cum in her cute ass.
As I pulled out and she slumped to the floor, her head still in his lap, she said,” Thank you, Daddy. Thank you.”
I dressed quietly and left them to their reverie.