Jim stood there as Ruby and Jackie both crawled over to him from the couch. They took their time, and when they reached him they started to crawl up him, running their hands all over him, with the occasional stroke of his dick or fondling of his balls for fun. When they both got to full height, which was about shoulder height on Jim, they each grabbed a hand and led him over to the couch. He didn't know what they had planned just yet, but he hoped it wasn't anything too outrageous. They were Liz's friends after all, so anything was possible.
Once they got him to the couch, they pushed him into a seated position, and that's when he saw Jackie grab the purple strap-on that Liz had used on her earlier. He immediately puckered up a little, afraid of what they might be thinking of doing to him, when Ruby got his attention by taking most of his shaft into her mouth.
He wasn't as sensitive as he would've been after cumming, so it didn't set him off right away, for which he was thankful. As he enjoyed the gentle blowjob she was giving him, he turned his attention back to Jackie, who was finishing up adjusting. He saw that the harness actually had a small dildo on the inside, allowing the wearer to also enjoy the fun of bumping uglies. As she finished up, he became aware that Ruby had stopped sucking on him and was now sliding a cock ring and condom onto his junk.
As she finished unrolling the condom, Jackie started to lube up the purple dildo she was now sporting, and Jim puckered a bit more. Ruby pulled him down a little, scooting him closer to the edge of the couch, and then climbed on top of him. As she lined up his tip with her pussy, Jackie came up behind her and started to caress Ruby's ass before sliding a thumb up her ass. She gave a light moan and then pushed herself down slowly onto Jim.
On top of the condom, Jim was also feeling pretty spent, so he didn't feel it as strongly as he had the first few times. Despite that though, the cock ring kept him standing tall as Ruby got her first taste of Jim inside her. She was almost all the way down when Jackie pulled out her thumb and proceeded to slide her purple toy right up Ruby's rear end.
This was a new sensation for Jim as he felt the dildo through Ruby's vaginal wall rubbing against him, but apparently it was just what Ruby liked. She gripped Jim's shoulders hard, her mouth open but no sound coming out. She then let out a low moan as she buried her head in the nape of his neck, and Jim was now fully hard and ready to rock.
"So big boy, whaddya say we show Miss Ruby here the wonders of double penetration?" Jackie mused as Ruby convulsed lightly on Jim's chest.
Jim looked down at Ruby, who looked up at him with pleasure still written across her face, and he smiled. He gave her ass a smack, which elicited a yelp of excitement from Ruby, and then grabbed her ass firmly and started to grind her. Jackie smiled back at him, took hold of her hips, and then started to slowly fuck Ruby in the ass.
It was a feeling unlike anything Jim had experienced yet. Once they got a rhythm going, Ruby was nothing more than a moaning mess lost in pleasure. She had leaned back to an upright riding position, which gave Jim room to fondle her breasts as she started to grind on him on her own. It wasn't very long before Ruby finally hit the point of no return and came hard.