Author's note: This is the second in a series of (generally) shorter stories about the couple in the
Lucky Over 40
series, and their friends. They have a rather adventurous sexual relationship, and are very much in love. Overall, these tales are about them exploring various sexual kinks. You do not have to read any of that series to enjoy this, although some things might be better understood if you do.
Please check the story Tags to see what you may or may not like.
There is also reluctance, some cock worship, a prostate massage, and a cum kiss. If anything bothers you, it might be best to try another story, otherwise, I hope you enjoy reading this one. If you like it, please add some stars, and even a comment at the end. Your feedback does help inspire me to continue writing.
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Jill and I have been having a lot of fun sexually "exploring," by trying different things. It all started about a month after we began dating, and took off like a rocket from there. I feel like the luckiest guy in the world to be with her. We also have a pretty unusual relationship in that Jill occasionally "lends my services" to friends, like JJ, in order to ease their sexual frustrations. JJ has become a good friend to us both ever since we met her, when I took Jill to JJ's Adult Toy Store on a special kind of date. We call her JJ because her name is also Jill, and though that's part of why the girls bonded, it also got confusing, especially in certain situations.
On the drive to JJ's store I told Jill some of what happened earlier this week. "So, I sent Ron to JJ's store to look for bachelor party stuff while they were on standby with the Ambulance the other day. He was working with Donna, who thought it was pretty fun. She did some browsing of her own while JJ showed Ron around and suggested some stuff. But they got an Ambulance call and had to run before buying anything -- apparently Donna had already made some purchases, though. They stopped back a few hours later and found JJ had picked out a bunch of things for Ron so he just bought the lot; putting it on my tab!" Jill laughed at that part.
"Yeah, I'll get some of it back when others chip in, maybe. Either way, it's worth it to me. I asked him if she was helpful and he said 'very much.' I told him Jill's really nice, and he agreed. I said she's really attractive, too, and he called her 'hot.'"
"I bet he did, `cause she is! She gets
you
going," Jill added, grinning.
I laughed, "Yeah, well bottom line is, I convinced him to ask her out on a date -- after I checked to see if JJ'd be interested, of course. I called her just to say 'Did my guy come over, and did you help him out?' kind of thing. She said something like 'I'm always happy to help a man in uniform, especially a hunky one.' And yup, she's interested."
"Yeah, I know all about her side of it. We talked already."
"I should have known. They were supposed to have a date last night, you know about that I assume."
"Of course, she told me this morning. They had a nice casual time, but really hit it off. She gave him a goodnight kiss, and wanted to jump his bones, but decided it would be better to hold off and go for the long game instead of a one night stand. She's supposed to see him again soon."
"Yeah, she sure is. Ron's looking forward to another date, too. I think I did Ok, so far..."
"Yeah, good for you!" she said, squeezing my hand. "What about your little gloryhole escapade, with a blowjob for the guy getting married..."
"Less," I sort of interrupted.
"Yeah, him, getting one last anonymous blowjob...from Ruth, right? And Ron getting one from JJ, but not knowing it's her. Still planning on trying that?"
"We sure are. JJ's gonna see him -- or a part of him -- tonight, in just a little while. And we're gonna help, sort of. That's why we're headed there now."
"What, really? Does JJ know? I think she would've told me..."
"Yeah, she knows. Look, I've played along with your plans several times, and now I need you to play along with mine tonight. Will you do that? For this to work right I need your full cooperation, Ok?"
"Um, yeah, Rob, sure," she said, a bit confused, or maybe concerned, or both.
"Hey, you trust me right?"
"Of course."
"Good. Just follow my lead and do what I need you to at the store, like I do for you on your adventures. Then this'll all work out, just like yours do, Ok?"
"Yeah, Ok," she smiled at me and squeezed my hand again. "I'm not sure what's really going on, or what we're supposed to do, but I trust you and I'll do what you need, for JJ."
"Great. If you play along like I tell you to, I think you'll really enjoy it."
"Ok, Tiger, whatever you say."
When we got to the store JJ saw us as soon as we walked in, waving for us to follow her down the hallway to the video rooms with the gloryholes. "They may be here any minute and I wanna be sure they don't see any of us." She ushered us into the larger room, number 3, and closed the door behind us.
JJ gave us each a hug and kiss, then said to me, "Thanks for doing your little set-up thing the other day. We had fun last night, and I hope we both do today, too, even if he doesn't know it's us, I mean me. This is a little weird, maybe, but hopefully he won't think it was too weird when he finds out later. Shit, suddenly I'm nervous."
"If you do a good job, I'm sure he'll be very happy. I told him you have a pretty strict rule about not
doing
customers, so..."
"Um, sorta strict, considering technically you're a customer, and so is he."
"The point is he shouldn't suspect it's you until you tell him, if and when you want to. Anyway, are you ready to meet
little
Ron..."
"Cute. Yeah, I'm ready. But he may not be all that little -- just like
little
Robbie," she laughed.
"Hey what about Less? Where's Ruth, or whoever is taking care of him? Are they using another room? And why do we need to be here?" Jill was full of more questions than usual.
"Relax, it's under control. I know you like watching, and you'll like this. Just do what I say, remember?"
JJ winked at me, then turned to Jill, "I dunno what all he has up his sleeve, but just do what he says, don't ask so many questions, and don't mess this up for me, please?"
"Yeah, Ok," Jill replied, still sounding unsure.
Just then we heard someone enter the room next-door, followed by the one on the other side. "Alright ladies, places, it's almost show time," I said quietly. "Jill,
you're
going to do Less while JJ sucks Ron. You've told JJ you still want to try the gloryhole."
"
What
?" she said, looking shocked.
"You also said you'd like to get spit-roasted sometime, so if you do a good job on him, I'm gonna fuck you from behind while you finish him off. So drop your shorts and kneel down over there, right now!"
"Um, I'm not sure about this... But I'll try it... for JJ," she giggled, taking off her shorts and undies. "Wait, how do we know who's who?"
"Deejay's out front and directed them back here, with Ron in number 2 and your guy in 4. She's supposed to tell them to use the little doors instead of the round holes, so we get better access."
Just as she said that, one door in the wall opened and a stiff cock emerged near Jill's face. Soon after, the same thing happened on the other wall.
The girls knelt down and started to stroke the cocks, when the door to our room suddenly opened, startling us all. Deejay stepped in, saying "Hi!" a bit too loudly, then whispered "I had to come down to check. Ooo, I see, you've got a nice grip on Ron, and Less is in good hands with Jill," she tittered.
With that confirmation, JJ kissed the purple head in front of her, gave it a long lick, then wrapped her lips around it. Jill watched her a moment, looked back at the thick cock she was holding, let out a deep breath, and did the same.
"So who's minding the store?" I asked Deejay.
"Oh, Teddy is. He knew how interested I was and
finally
told me I could go down and check it out. Or whatever..."
"Whatever?" I asked.
"Well, he knows Jill, um... sorta got stage fright when she tried this on him, and wondered if it might happen again. He thought I should be a good friend and back her up. Just in case, you know?"
"That was
his
idea?"