Chapter 60

“Mistress Emma, Brent Sir,” Jess said, ignoring my frustrated groans, “May I suggest you have a seat at the table before the food grows cold?”

Up to that point, neither Emma nor Brent had noticed the card table we had set up in the second half of the living room. Other, more interesting, sights had occupied their attention.

Jess and I both pulled out chairs for our guests; I for Emma, Jess for Brent. On the table, we had set up a steak dinner with salad and baked potato.

Jess opened a bottle of wine on the table (screw top, not exactly the finest of vintages, but our guests weren’t really there for the beverage selection) and poured glasses for both.

Jess and I both stood at attention with our hands behind our backs while Emma and Brent began eating.

“Jess, this steak is delicious!” Emma said, momentarily forgetting the ‘slave’ bit. Brent readily agreed.

“Yes, delicious! You guys did a great job with this meal,” Brent said. He turned to face Jess and saw that thanks to her position where she stood near him, Jess’ bald pussy was only a foot away from his eyes. He quickly turned his gaze back to the food.

“Thank you, sir, Mistress,” Jess said to each of them. She turned to Emma.

“Mistress Emma, perhaps you’d like some entertainment during dinner?” Jess suggested.

“Huh? Uh, maybe some music?” Emma said uncertainly. Jess smile faded just a bit.

“Absolutely. Slave Aaron, can you turn on the radio?” Jess said to me. I went and did so, putting on the local light rock station. Something by Bryan Adams started softly in the background.

“Mistress, I was actually thinking more along the lines of Slave Aaron and me providing entertainment for you two,” Jess said. Emma looked at her blankly, still not getting it. Brent was ignoring the exchange. Struggling to control a sigh, Jess grabbed my dick and cleared her throat.

“Oh! Entertainment! Right! Ummm...” Emma faltered after that. Jess touched my dick again, then put a hand on her ass. Emma’s eyes widened; she glanced over at Brent who was trying hard to focus on his steak. Looking back to Jess, she shook her head rapidly “NO!”

Jess’ eyes narrowed and she mouthed the word “YES.” Despite not saying a word aloud, Emma knew the tone that would have been conveyed. Her shoulders slumped a bit in resignation.

“Yes, sl-slave. Um...” She couldn’t bring herself to say it. Jess’ eyes darted to Brent who still wasn’t looking at us. Back to Emma, she mouthed “come on!”

“Why don’t, don’t, you guys have se-sex for us,” she finished.

“Of course, Mistress. And where, specifically, should Slave Aaron, put this?” Jess asked pointedly, holding my erection up.

Emma cringed; Jess was rubbing her ass cheek with the hand not holding my cock. She wasn’t pulling any punches tonight.

“In ... in your butt,” she said softly, but not softly enough that it didn’t catch Brent’s attention. His head shot up and looked first at Emma, then the two of us. His eyes went to my member which Jess was still holding.

“As you wish, Mistress,” Jess said with a huge grin. “Mistress, is it ok if Slave Aaron applies lube to my asshole before he fucks it, or do you wish him to fuck it dry?”

Jess really hoped Emma didn’t choose the latter. She didn’t particularly care for anal sex as it was and the thought of dry anal sex REALLY didn’t appeal to her, but she loved saying it out loud. As hoped for, she saw Brent adjusting the uncomfortable looking bulge in his pants again.

Emma seemed to consider for a longer period than Jess would have liked. I could see her tense just a little while waiting for the answer.

“Um, Slave Aaron can apply lube to you,” she said finally. I saw Jess let her breath out that she had been holding.

“Slave Aaron, would you please get the lubricant from the other room?” she said. This whole exchange was as casual as discussing the weather; except instead of the weather, it was anal sex. Anal sex while eating dinner. Well, while two other people were eating dinner. Jess and I had eaten earlier. She told me I’d need the energy.

I departed to retrieve the lube. Jess stood with her hands behind her back, waiting for further instructions. “Anything that you would like me to do while I wait, Mistress?”

Emma thought fast. “Slave Jess ... um, while we wait, please t-touch yourself,” she said. Jess was glad that she was growing bolder.

“Yes, Mistress,” she said. Her hands came around to her front. She pushed the middle finger of her right hand into her slit. The digit was thrust in-between the folds a couple of times before she pulled it back out. Brent was watching her intently and Jess held eye contact with him as she put the finger into her mouth. She sucked on it like a lollipop before returning it to her pussy.

She bit her lower lip seductively as she rubbed the digit against her clit. She used her other hand to tug at one of the nipple clamps, causing the nipple to pull taut while she diddled herself.

As I returned with the lube, I saw the Brent and Emma had both ceased eating as they watched my wife masturbate in front of them.

“Ok, Mistress Emma, Slave Aaron has returned. May he now lube this slave’s ass?” Jess asked.

“Yes. He can,” Emma said. She punctuated it with an authoritative nod.

Jess dropped down on all fours. She made sure her ass was pointed towards Brent so he would have the best seat in the house for the show. She pushed her face down onto the carpet so that she could reach behind her and pull her ass cheeks apart for me.

I stood there holding the bottle, stupidly staring at Jess’ ass along with our two guests. Jess cleared her throat very loudly.

“Oh! Sorry!” I said as I dropped down to my knees between her legs. I flipped the lid of the bottle open and squirted a stream directly on Jess’ rosebud. The trickle ran down her ass towards the floor but I reached in and caught it with my index finger.

Out of the corner of my eye, I could tell Emma and Brent were watching intently; not that I blamed them, I would have been too.

I pushed my greasy finger against Jess’ back door. The tip of my digit penetrated her sphincter and I rotated it to work the lube in. With a few short pushes, my finger plunged all the way into her hole and I fingered her for a few seconds before pulling out.

“Don’t be stingy with the lube, Slave Aaron,” Jess said over her shoulder. I squirted a second round of lube onto her and fingered her again until I was confident that her tunnel was as slick as it was going to get. For good measure, though, I squirted some onto my hard member also and worked it around the shaft.

I positioned my cock head at Jess’ hole.

“Ask permission!” she hissed quietly to me.

“Oh, uh, Slave Jess, can I enter?” I said. Jess sighed in disgust.

“Slave Aaron,” she said, her tone one of exasperation. “It is not my place to give you permission to the ass belonging to Mistress Emma. Perhaps you should get her permission?”

Whoops. Duh.

“Oh, right. Mistress Emma, may I now, um, fuck Slave Jess’ ass? Please?” I wasn’t sure if I should say please, but figured it couldn’t hurt.

Emma opened her mouth to answer, but then seemed to think of something and closed it. She turned to Brent.

“I’m not sure. What do you think, Brent?” she asked casually.

“Huh?” Brent was stunned by everything he was watching and had no brain cells left to process Emma’s question.

“Jess’ asshole. Should Aaron be allowed to fuck it?” Emma asked. She enjoyed someone else being uncomfortable rather than her.