“We were just about to shoot the next video. Lisa, turn over and get on all fours.”
“I’ve . . . never seen anything like this,” Ryan murmured, still bug-eyed. Lisa looked at me with a curious expression on her face.
“What’s next?” she said with a smile.
“You’ll see.”
Lisa complied, turning over and getting on her hands and knees, ass pointed straight at Ryan. I loved that ass. So, apparently, did Ryan, because he stared rapturously at Lisa’s exposed anus and vulva, only a few feet from him.
“This is amazing,” he repeated. “She’s gorgeous.”
“She is, isn’t she? She has a great body, and she likes to show it off.”
“Now you’re speaking for me?” Lisa asked, laughing.
“Of course, I am! I know you so well by now.”
I turned to our visitor, who was still frozen in place behind Lisa, staring at her upturned ass.
“Ryan,” I said, “can you help me do something? I have a task for you while I am recording this.”
“Uh, I guess,” he said not turning away from Lisa.
I pulled something out of the tote bag and offered it to him. It was a big stainless steel butt plug with a purple jewel cap.
“I want you to put this inside her while I film. OK?”
“Really?”
“Really.”
He took it from me.
“It looks awfully big,” he said. “Are you sure that’s going to fit?”
“I am certain, although it will be snug, for sure. You ready, Lisa?”
“As ready as I’ll ever be,” she said. “It’s all kind of relative at this point.”
“You’re going to need this,” I said to Ryan, holding up a squeeze bottle of lube. “Squeeze it into the crack right above the hole, and then use the tip to work it in.”
He looked skeptical. From his expression, I wondered if he had ever pushed a butt plug into a woman’s anus before. It WAS a big plug, and Lisa was a petite woman. But I knew she liked plugs, had a collection of them at home, and used them often in her online postings.
Ryan did as I instructed, holding the tube bottle over Lisa’s ass and squeezing until a thin, clear, gloopy stream spilled straight into the crack of her ass, right on target, and begin trickling toward her asshole. It was mesmerizing to watch, and I recorded every second of it. Lisa’s subscribers would be very happy, and I imagined how many cocks would be stroked watching Lisa like this. Many, I reckoned.
Ryan placed the steel tip of the plug right on top of Lisa’s asshole, and he pushed. It didn’t go anywhere. He dipped It into the lube puddle and then tried again. The tight ring of Lisa’s ass gave way a tiny bit, but not much.
“I don’t think it’s going to fit,” Ryan said.
“It will,” I said. “Just keep trying. You can do it. Lisa can do it, too. Right, Lisa?”
“I’m good!” she said.
Ryan kept trying, twisting and turning the butt plug as he pushed, until, at least, it began to worm its way in. The ring of Lisa’s anus expanded and stretched tantalizingly over the smooth steel. Ryan pushed more.
Lisa moaned.
“You OK, Lisa?” I asked
“Don’t stop!” she cried.
A pleasant breeze stirred the leaves of the tree and unseen birds chirped nearby, as the steel plug kept working its way into Lisa’s tight, reluctant hole.
Finally, the skin of her anus stretched over the plug at its widest, and with one more effort from Ryan, the plug plopped swiftly into Lisa. Ryan tapped the purple cap with his finger. It was all the way in.
I was getting some great video.
“That just looks so incredible,” Ryan said.
“Doesn’t her pussy look great from this angle, too?”
The inner lips of Lisa’s pussy were delicate and pink and peeled back just enough to permit a view inside her. A hint of her clitoris peeked out from under its fleshy hood.
“It’s hot,” Ryan said. He breathed heavily. I knew what he wanted.
“You can touch her if you want,” I said. “But you need this first.”
I drew a squirt bottle of hand sanitizer out of the bag.
“Are you sure?” Ryan asked.
“I’m sure.”
He held out his hands, and I squirted the sanitizer into his palms. He worked the liquid thoroughly into his skin, never taking his eyes off Lisa’s pussy.
Ryan paused, as though not knowing what to do next.
“Go ahead,” I said.
Gingerly, almost timidly, Ryan reached a long index finger toward Lisa. He touched one lip first and ran a finger down its length.
Lisa’s body noticeably shivered.
“Doing OK, Lisa?” I asked.
“Yes, it just tickled. It feels good.”
“You like having a strange man’s fingers on your pussy, don’t you?”
“I love it,” she said. I believed her.
Gradually, Ryan grew bolder. He used his fingers to open her.
“You can put your finger inside if you want to,” I said.
“Oh my God,” Ryan said.
He stuck his index finger into her depths, finding the channel of her pussy, and pushing in until it disappeared. He rotated it.
“It feels good, doesn’t it? Lisa’s pussy?”
“It feels fantastic.”
“See how many fingers you can put inside her,” I said.
I had seen Lisa put her own fingers in her pussy and in her ass on camera, but Ryan’s fingers were much thicker. I had no idea how many he could fit.
He pushed two inside, and the camera captured the way his digits stretched her pussy wider. What a sight. Then he added a third, and that was an even bigger stretch. He began to rock all three of his fingers in unison in and out of her, rotating all three of them together. Lisa moaned and even squealed.
It was hot to watch. I didn’t bother telling Ryan that he was dipping his fingers into my cum every time he pushed them deeply into Lisa’s pussy.
I noticed Ryan was grabbing and kneading his crotch while he finger-fucked Lisa.
“So hot,” he murmured. “I want that so badly.”
“You want to fuck her? You want to feel your cock inside her?”
“God yes,” he replied.
“Just a sec,” I said.
I moved to Lisa’s front and looked her in the eyes.
“What do you want, darling? Do you want him to fuck you? It’s up to you.”
She said nothing for a few moments, just looked at me. I could tell the feeling of Ryan’s fingers in her was so intense that it made responding difficult. If I could have captured the look on her face at that moment in a bottle, I would have. There was every kind of expression in that face: hesitancy, uncertainty, maybe a bit of fear, but also the yearning of a wild, restless spirit, wanton and brazen, a keen, burning desire to go someplace she’d never been.
“Do you want him to fuck you, Lisa?” I repeated.
She nodded, barely, and softly, almost imperceptibly, with her eyes fixed on mine, she said, “Yes.”
I looked away from Lisa to Ryan, who was waiting, poised.
“Fuck her,” I said. “But you have to use a condom. It’s in the bag.” I inclined my chin toward it.
Ryan pulled his fingers, now soaked with Lisa’s wetness, out of her, and he scrambled to fish the condom packet out of the bag. His hands fumbled for it, and I thought, when he finally pulled it out, that he was going to drop it into the dirt because his hands were shaking so hard. But he managed to hold on to it. He unzipped his pants and removed a penis that was longer and thicker than I would have expected. And it was hard, already. He tore the package off and began to wrap the latex over his cock.
While Ryan prepared his cock, I unzipped my pants and removed mine, now hard, and pointed straight at Lisa’s face, inches away.