Chapter 47

Emma shrugged. “Sure, what did you have in mind?”

Jess didn’t answer, but left the room, heading towards our bedroom. She returned a minute later holding a strap-on which dangled from her hand by the harness.

“My husband isn’t going to fuck you tonight, but how would you like to fuck him?” Jess asked. Emma’s eyes went wide.

“I, uh, don’t...” she said. Jess clapped Emma on the shoulder and waved the dildo in my face.

“Come on, live a little. He loves it. I’m sure he’ll get a kick out of you doing it, too,” Jess said. Emma just stared without answering.

“Aaron, strip!” Jess barked. She pointed the dildo at me threateningly. I immediately began to undress even though Emma hadn’t actually agreed yet. I was sure that thing would wind up in me regardless of her decision.

Jess turned back to Emma. “Have you ever pegged a guy? What am I saying, of course you haven’t. But you’ve played with my husband’s ass enough to get the general idea, I’m sure. Let’s get you stripped too, missy. Aaron, hold this,” she said, handing me the dildo.

Jess began pulling Emma’s t-shirt up above her stomach while I stood there, dumbly holding the toy that would soon be rammed into me.

Emma made no effort to stop Jess as Jess undressed her. Tossing Emma’s t-shirt to the side, Jess quickly moved to strip off Emma’s bra.

“Why do I have to be naked to, uh, peg him?” Emma inquired. She didn’t seem to mind being undressed, she merely sounded curious.

“You don’t. It’ll just be more fun this way,” Jess said as she unbuttoned Emma’s pants.

A minute later and Emma was as naked as I was. Jess put her hands on her hips and nodded approvingly at the two of us. She then retreated back to the bedroom.

“Can I see that?” Emma asked, gesturing to the strap-on. I shrugged and handed it to her.

She turned it around in her hand and squeezed it, seeing how firm it was.

“Huh. Surprisingly life-like, ‘cept for the temperature,” she remarked.

“Uh, sometimes Jess will heat them up in warm water for more authenticity,” I responded. Jess ended the discussion when she returned with the bottle of lube.

Flipping the cap open, she handed the bottle to Emma.

“Lube it good,” she instructed. Emma squirted a stream of clear liquid onto the rubber phallus and I watched it trickle down one side before she wrapped her hand around it. She stroked up and down, like she had when she masturbated me, and I saw the toy gleam in the light as she coated it thoroughly.

“Do we lock him or up something?” Emma asked Jess, pointing at me with the dildo.

Jess put a finger to her chin while she eyed me and considered.

“No, I don’t think so,” Jess said after reflection. “He is just going to get down on all fours and keep himself there. Ironically, it is more humiliating for him to willingly submit to being pegged. If he’s restrained, he can pretend that he doesn’t really like it and is being forced against his will. When you make him present himself to be fucked in the ass, he has to acknowledge that he enjoys it,” Jess explained.

“Isn’t that right, Aaron?” Jess asked me.

“Yes, Ma’am,” I said quietly.

“Go get the ottoman to bend over and present yourself to Emma while I prep her,” she instructed.

I went and retrieved the soft, plush ottoman from in front of the couch while Jess secured the strap-on harness around Emma’s back. As I positioned the ottoman, I glanced at Emma and saw the dildo sticking obscenely from her waistline, her bald pussy completely exposed below it.

I got down on my knees and faced the ottoman. I leaned over it, my stomach pressing against the top and my ass pointing backward.

“K, Emma, kneel behind Aaron,” Jess instructed. I heard rustling behind me and felt the dildo bounce against an ass cheek as she did so.

“Aaron, please spread your cheeks for Emma.”

I sighed as I reached behind me and pulled my cheeks apart.

“I heard that sigh, Aaron.” - Oh boy - “Please ask Emma to fuck your ass.”

I almost sighed again, but caught myself in time. “Miss Emma, would you fuck my ass?”

Emma started to answer but Jess cut her off. I felt a sharp sting as a hand struck my left ass cheek.

“Really, Aaron? We don’t even say ‘Please’ anymore? Hmmm?” Jess said accusingly.

There was a pause while I built up my courage.

“Miss Emma, please fuck my ass,” I said. There was no response from behind me.

“Emma, I don’t think he really wants you to. Tease his asshole with the dildo to get him going,” Jess instructed.

“How do I do that?” Emma asked.

“Brush the head against his rosebud. Press lightly against it. Push just enough for him to feel it. And want it.”

A moment later, Emma did exactly as she was told. I felt the firm rubber press against my sphincter, bounce against it a few times, then stop by penetrating me ever so slightly.

“Now, Aaron, ask AGAIN,” Jess said, her tone firm.

“Please, Miss Emma, please fuck my ass. Fuck it hard. Fuck it hard with your dildo,” I said. I probably went a bit overboard, but didn’t want to have to ask again. I glanced over my shoulder to see if it was acceptable and was relieved to see Jess smiling at me, her arms crossed over her chest.

“Very good! K, Em, back away for a moment so I can get Aaron’s hole lubed up.”

The tip of the dildo left my butt and I heard the click of the cap to the lube from behind me. A second after that, the familiar cold stream of liquid hit my ass and trickled down to my ball-sack.

I felt Jess’ finger press against my rosebud and push some of the cool liquid into me. More pressure and her finger pushed all the way in until her knuckles bottomed out on my ass cheeks.