“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.
“Ryan,” I said. “One more thing.”
“What’s that?” he replied. He didn’t look up because he was so intent on getting the condom on right.
“When you are close, pull out of her, take the condom off, and cum all over her ass. OK?”
“Sure. Sure.” I don’t think he cared. He was about to fuck a beautiful woman in a park on a warm spring day. He was in no mood to quibble with the details.
A long moment later, his cock was sheathed and ready to go, and he plunged into her without further delay. Lisa’s body rocked forward, toward me, and her mouth opened, and I pushed my cockhead into the opening, between her lips. But Lisa had other ideas. She took a tight grip on my shaft and pulled her mouth off me and stuck her tongue out and swirled it over my swollen pink tip. While one cock filled her backside, she was going to take her time with the one in front of her.
Ryan may have begun timidly, but now he fucked Lisa with gusto, rocking her body with enough force that it was difficult for her to hold my cock against her tongue. But she seemed determined not to take it all in too fast. She licked the shaft, up and down, and kissed and caressed the bulbous head with her tongue and lips. Lisa already had revealed that she liked giving oral sex on her site, and her pleasure with my member was obvious.
At last, she encircled the head in her mouth and took it in. I didn’t have a monster cock, but it was big enough, and it was impressive how skillfully Lisa took the whole thing into her mouth, stretching her lips and cheeks. She gagged slightly but kept at it.
“Lisa, look at me, darling,” I said.
Lisa looked up at me with wide adoring, lusty eyes. I recorded her with my phone. I knew her subscribers would love seeing videos of her blowing my cock from the man’s point of view. The woman wasn’t a pro, but she knew how to perform. I looked up at the other camera, on its tripod, recording the scene from another angle: Lisa from the side, being spit-roasted for the first time, in a public place no less. She would look brazen, lewd, even slutty, and her subscribers would love every frame and moment of seeing her that way. I loved it. I think Lisa loved it. And I could tell Ryan loved it.
He groaned.
“Remember what I said,” I called to him.
“I’m going to come soon,” he said.
“Excellent,” I said.
“Mmmmph,” Lisa said. She continued looking up, into the camera, while her lips aggressively slurped my cock.
In only minutes, I couldn’t take it anymore. I was close.
“I’m going to pull out, Lisa. Open your mouth and stick out your tongue.”
Lisa did so, and not a moment too soon, because my dam burst, and a spray of cum erupted from my cock head onto Lisa’s stretched-out tongue, and on her lips and cheeks, too. It was a thick, creamy mess, and I captured every ounce and inch of it on camera. Lisa held her tongue open, and a thick dollop of cream pooled and glistened on it.
She withdrew her tongue and gulped my cum down her throat. I could hear it. Her subscribers would hear it, too.
I wanted the camera to linger on her face, but I didn’t have much time, because Ryan said he was about to come too, and I had to get footage of that.