Chapter 57

Once she was alone, Emma headed over to our apartment.

Jess opened the door and before Emma could greet her, Jess grabbed Emma’s arm and pulled her into the apartment.

“Tell me EVERYTHING!” Jess said excitedly. She led Emma over to the couch where they both sat down.

Emma was about to speak when she caught the sight of me on the floor. She blinked and was silent for a moment as she took in the scene.

I was on the floor on the other side of the room.

I was nude. That wasn’t the surprising part, of course. This time, however, I was on my back and hogtied, legs pulled up against my chest with my arms tied to them with rope. A rather large butt-plug was clearly visible sticking from my ass and a ball-gag completed the ensemble.

“Um, am I interrupting something?” Emma asked. Jess seemed legitimately confused before following her gaze to me on the floor.

“Huh? Oh! Nope, not at all. Today is our” - and by ‘our’ she meant ‘my’ - “anal training day. I’m gradually working Aaron up to accepting larger and larger plugs. He has to hold that plug for thirty minutes before we move on to a slightly wider one.”

“It looks like he doesn’t mind too much,” Emma commented, gesturing to my erection sticking up between my bound legs.

“No, but he’s not allowed to orgasm during this time. Sometimes the pressure on his prostate will cause him to ejaculate spontaneously, and he’s not punished for that, but he isn’t allowed to otherwise touch or play with himself during the training sessions,” Jess explained. She returned her gaze to Emma. “Now, tell me how things went!”

Emma stared at me for another few seconds before returning her attention to Jess. She gave jess a full play-by-play, leaving out no details.

“Jess, it was wonderful!” she finished. “I think that...” she said, trailing off.

“Yes? You think what?” Jess prompted.

“I think I might be falling in love with Brent,” Emma said quietly.

Jess paused a beat before responding. “Well, I’m very happy for you, but I feel obligated to say that your relationship is still in the very early stages. Don’t get too wrapped up in the lust and excitement and confuse it for more. But also don’t think I’m trying to rain on your parade at all!”

“No, I know you are right, and I’m going to be careful. It’s just that ... I’ve never felt this way about anyone before. It was INCREDIBLE. Not just the sex; it was good, of course, but you and Aaron have made me feel great as well. It was the intimacy, the closeness, that I’ve never had before,” Emma said.

Jess nodded knowingly. “I totally understand.”

“What ... what am I going to do about my panic attacks?” Emma asked fearfully.

“We’ll work on that. I will draw up a plan for your next sexual encounters. I’ll get it emailed over to you later today. I’m thinking-”

An old-fashioned wind-up alarm clock interrupted her as it rang on the end table. Jess turned around and silenced it. I groaned from behind the gag on the floor.

“Time for the next one,” Jess said to me as she stood up.

She knelt down behind me and took the butt-plug in her hand, grasping the base and slowly wiggling it back and forth until it popped free of my rectum. I grunted as my sphincter closed back up.

Jess placed it off to the side which allowed Emma to see its size for the first time.

“Holy shit, Jess! It’s huge!” she exclaimed. It wasn’t HUGE, but it was big. Bigger than the one Emma had seen used on me at Spooner’s, though not by much.

The next one that Jess was lubing up, however, WAS huge. And I already knew it. I groaned again.

“Hush, you,” Jess said as she stroked the silicone plug, working the lubricant all around it.

“Can I put it in him?” Emma asked. She left the couch and knelt next to Jess. The excitement in her voice was obvious. Jess’ answer, however, was surprising.