Lucky Over 40 Ch 05 Deejay Pt 02

This is the fifth part of the story of two single 40somethings that met on-line and started an adventurous sexual relationship. It is about exploring completely heterosexual kinks, and contains things like a 45ish male being "loaned" to 25ish female to have sex, mild female dominance, mild CFNM, anal play, ass licking, butt plugs, play at a glory hole, prostate massage, cum play -- including tasting some of his own cum. If anything above bothers you, don't be upset if you decide to keep reading. (Please DO make use of story Tags to see what you may like, or not.)

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I certainly "got lucky" when I found Jill, especially when I found out what a strong sex drive she has. I thought I was probably an over sexed guy, but she may actually surpass me, and she is just as kinky. She even arranged for me to be "loaned out" to her young friend, Deejay, who had a deep need to experience better sex than the selfish "suck and fuck and done" that her prior boyfriends had with her. This entry is the conclusion of that time with Deejay. (You can read the start in part 4 of this series.)

Yesterday afternoon I had a wonderful time with Deejay, showing her new experiences, and maybe getting some of my own. After our 69 session, we had fallen asleep snuggling with each other, until the baby monitor sounded when Deejay's bed ridden mom called for her help with something. We decided to call it a day at that point. She threw on some clothes and hurried down to her mom, and I dressed and headed home, promising to call her later. She still had unfinished items on her "list" and was anxious to get it all wrapped up tomorrow evening since we were both free and Jill wasn't "going to be using me," as she put it.

When I got home, there was an email from Jill waiting on my computer, asking (telling?) me to give her a call when I got home, to let her know how it went. I called right away, and told her that I thought it went really well, but I didn't feel right telling her a bunch of details about Deejay without her knowledge. She'd have to get them from Deejay, since they talked pretty intimately anyway, or else she needed to have Deejay tell me it was Ok. I did let her know that we were both pretty nervous at first, but after a nice kiss we both loosened up, and after I ate her out, there was basically no more nervousness.

I also told her what items we checked off Deejay's "list," and that we were going to check some more off tomorrow evening. We'd start it off with a stop at the adult store to get her a plug, and then go from there. Yes, I agreed, it sounded familiar, but no, it isn't my routine with all my second sexual dates. It just went so well with Jill, and it's the kind of thing Deejay wanted, so I thought it was worth repeating. And, since Jill had shared so much about our sex life with Deejay, it wasn't really just my idea. I think she really knew all that, and was just yanking my chain, sort of like she yanks my cock.

We chatted some more, about things like how her day was, and then about what she thought I should do with Deejay tomorrow. After all that, she told me she couldn't wait to get her hands, and mouth, on me again, and vice-versa. She said she wanted to see if I picked up anything new over these two days, and so on. She had me hard in no time, as is so easy for her to do. But I was beat, and I still had to make arrangements for tomorrow, so we wrapped up the call. Even though a little phone sex would have been nice, she understood and said I'd just have to make it up to her later. I promised her that I would be very happy to do so.

Next, I called Deejay and we agreed I should come over right after I was done at work tomorrow. She arranged for someone to cover taking care of her mom for a little longer so we had some time to run our "errand." I told her I was going to try to get out of work early since I was supposed to put in some extra time one day later this week. I expected I could be at her place by 3. "I hope you won't be late," she said, sweetly, "but I won't be as anxious as I was today since I'm not really nervous about any of this anymore. I'm just eager to get to the stuff on the rest of my list. I'm really glad we're doing this right away! I'm looking forward to seeing you -- ALL of you -- then!"

She was sweet, and attractive, and hot in bed, but she was 20 years younger and I had absolutely no thoughts of a romantic relationship with her. Friends-with-benefits might be an option though... But I tried to push even that thought from my mind.

I had no problem leaving work early and got to her place just before 3. She met me at the door, wearing a button down shirt and short plaid skirt that was perfect for today, even though I hadn't told her what to wear. Had Jill, I wondered...

"Hi Teacher, I'm ready for our next lesson, or session, or...," she said with a big smile and a flirt in her behavior that even I recognized. "We ought to get going right away, or else I'd invite you in for 'something,' but there'll be time for lots of that later when we get back and the person watching over mom right now can go home."

She yelled inside that she was going, then literally ran out to my car and hopped in. When I got in I saw she had her skirt hiked up and her knees parted, showing that she wasn't wearing any panties -- it was already obvious she wasn't wearing a bra. "This is the proper dress for the drive, right?" she said with a sly smile. "I'm wet already, just thinking about our next lesson."

"Yes, that's just fine, my hot, sexy student," I replied as we started down the driveway. "I would have loved a taste of you before we left, but you're right, there's more time for that later. Before I leave the driveway and get on the road, though, maybe I could get a nibble of the luscious melons in your blouse." She agreed that would be nice, and opened her shirt to expose her firm, round breasts.

I leaned over as she leaned toward me, holding my head and guiding my mouth to her tit. I opened wide and took all I could, fondling the other with my hand. My fingers and tongue soon went to the already firm nipple of their respective breast and teased it, making her moan with pleasure. "Yes, those are very succulent, and I'll want more of them later, but let's be on our way now."

The drive was about 15 minutes. I teased her pussy some with my fingers, until traffic picked up. When I had to stop, I sucked on my fingers and told her she was very, very tasty. She played with herself some, both above and below, and teased me verbally as we continued driving. Occasionally she reached over and rubbed my crotch, making comments about confinement and wishing I could come out to play, etc. I had to readjust myself a couple times, to her delight.

She was a very good tease, and I was somewhat relieved when we arrived at our destination. I parked, and immediately leaned over to her, rubbing her snatch with my whole hand and tweaking a nipple with the other, then told her, "Time to cover yourself up, for now. Let's go shopping, sweetie."

As we went on into the store, Deejay took my hand and squeezed it, while gazing all around with some obvious fascination. The place seemed to be as devoid of customers as last time, but it was a weekday afternoon. The same, nice looking, 30something girl was behind the counter. "Nice to see you again. If you have any questions, just tell your cute new friend to come see me," she said, with a friendly, but knowing sort of smile. I paused and Deejay let go of my hand, going ahead to look around.

I opened my mouth to try to explain to the girl that it wasn't what it probably looked like, but before I could say anything she said, "It's Ok, Jill told me you two would be in, and what was going on. You know where those toys are, and she can come see me if she needs anything at all. Be sure to point out the stuff on the bottom of the rack again," she said with a grin. I was puzzled, but she continued, in a more hushed voice, "I had a nice view on the store camera the last time," nodding at a set of monitors that were behind the counter. "I liked it, looked like Jill liked it, and so will she, I bet," she said with a wink.

I was probably blushing some, but I thought, "Well, that's one 'secret' I can't blame Jill for revealing." I just smiled back at her and said, "Thanks, I'll be sure do that," trying not to show my embarrassment, "I appreciate all your help." I walked back into the area where the various sex "toys" and such are located, finding Deejay looking at the vibrators. "Come on, my little hottie, the things we need today are right over here," I told her.

She came along saying, "They've got some really interesting things here. I've only got a Magic Wand massager for sore muscles. But I also use it sometimes when I need a little 'special' relief, if you know what I mean. I may wanna come back here and look around a lot more. Maybe I can get Jill to come with me."

"I'm sure she would be happy to," I said truthfully, but a little sarcastically. "Here are the plugs, and related items. Although there's lots of things in the store that you -- or we -- could have fun with, Butt Plugs were what you had on your list, I think. There are plenty of them here. If you want to revise your list, we can change our plans for tonight, but we don't have much time to shop around before you need to get back, so what would you like to look at?"

"I think what I'd like to look at is one of these things in your cute ass," she said with a giggle. "Yeah, let's stay with the plugs. I don't wanna spend a lot of time, because I wanna get back and try them right away," she said eagerly and with a sexy smile. "So is there anything you'd recommend?"

"I don't have a lot of personal experience with these either, but why don't you bend over and get that box way down there, please. It looks interesting," I said taking a clue from the girl's comment earlier.

"Oh, you want me to BEND OVER and get that one down there, do you?" She said, in an odd way. Jill had told her, I guessed. "Sure, I can do that, just be sure no one sees when my skirt comes up and flashes my ass. That's what you're really interested in looking at, right?" She bent over, tossing her skirt up on her back as she did. She wiggled her ass at me and said, "Can you tell if I'm wet yet? You should check baby." I glanced around, saw the security camera and gave it a little wave, then reached out and lightly rubbed Deejay's inviting pussy. I thought I heard someone in the distance say, "Atta boy," but it may have been my imagination.

Deejay giggled, then stood up straight and turned to me, saying "You're a dirty not-so-old man, aren't you?" and she gave me little kiss on the lips. "So, is this the set you guys got? Jill thinks it's pretty good. It should do just fine, but I kinda like this version with the little heart on the end instead of the round gem. And that one with a little tail looks cute. I have to go get some advice. Be right back," she said with a big smile and a wink, then almost skipped off to the girls at the font counter. I occupied myself looking at the ones she mentioned, and some of the ones I saw earlier, with remote controlled vibrators in them.

Deejay was back before very long and said, "Yup, it's hearts for me, their more romantic," she said as she snuggled up to me, teasingly. I gave her a little kiss and told her I enjoyed her flirting since it showed she wasn't real nervous again. We put the other items back, picked up some lube and headed up front.

As I was paying the girl at the counter said, "You gonna wear that home? If so I've got a more comfortable place for you to get it in place than the back of your car."

"Jill!" I thought, but accidently said out loud.

"Yes?" the girl at the counter responded. I looked at her with a puzzled expression and she replied "I'm Jill, did you want to tell me something?" She had a really big and knowing smile on her face, then laughed and said, "Yeah, my name's Jill, too. That's one of the reasons your Jill and I hit it off. She told me today that you two would be coming in.

"Seriously, if you want to have some playtime in one of the video rooms, the store is really quiet right now, being a Monday afternoon. I'll just let you have the room free of charge, unless you want to watch a flick while you're in there. Room 3 would be my choice."

"Well, Jill, it's nice to meet you, sort of. Sort of meet you, that is. It's definitely nice. You know what I mean," I stammered, and I wasn't even nervous. "Thanks for the offer. Let me talk to my hot friend here and we may very well take you up on it."

"Jill said you were a real smooth operator," she chuckled at me. "She also said you have other very endearing qualities. Anyway, you really should make use of that room to try it on to see if it fits. But sorry, no returns if it doesn't," she added with a wink.

Deejay chimed right in, "Yeah, we'll take you up on that. It's too light out this time of day for me to want to do it in the parking lot. We might take a little while though," she giggled.

"That's fine, take your time," Jill-2 encouraged. "Like I said, it's quite on a day like this. Don't worry, no cameras in there, so have fun! Oh, and if you want to make use of an adjoining room, and the little 'connecting doors,' to warm up, or finish up, be my guest. Just clean up after yourselves, Ok." She winked at us, or at me, or at Deejay, I wasn't sure who, but I had a feeling there had been some "girl talk" earlier. Before I knew it, Deejay was gone, headed into the video area and the rooms in the back.

Room 3 was a middle room, apparently bigger than most of the others. Inside it had two chairs, a vinyl cushioned bench like in a booth at a restaurant, as well as the expected coin or token operated video player in the wall, a bunch of graffiti on other walls, standard bathroom fixtures, and some round covers on the side walls near some rectangular doors about 8 inches square. "Oh, it's also a Glory Hole," I said, and Deejay asked what that was, so I told her, briefly. She said she understood it all now, which was a little puzzling to me.

While I cleaned the smallest plug of the set at the sink, I told her she should kneel up on the bench, backwards, and lift her skirt up. She said I might as well wash all three plugs while I doing the one, just in case she wanted to try a different size. I thought that was silly, but I did it anyway, and set them each back in the plastic tray that was in the box. I put the plugs, and the lube, together on a chair nearby. Deejay got up on the bench seat and looked at me over her shoulder while she waggled her bare ass in front of me. Her pussy lips glistened and her scent was in the air. My mouth was already watering when she said, "Ok stud, get over here and warm me up with your tongue." Who was I to argue with that request, or was it an invitation, or a command? Who cares! I didn't waste any time getting on my knees and putting my mouth to work.

I licked at her wonderfully wet pussy, but this was not the best position to access it properly. On the other hand, that wasn't really why we were there, so I dragged my tongue up higher. Spreading her ass apart with my hands, I plunged into her darker hole. She giggled and squirmed and said, "Yeah stud, that's it, lick me good, right there. Oh yeah, right THERE. Get that tongue in me, and put some fingers in my cunt, it needs something in there." I did all that she asked, and also had an idea of my own. I blindly reached over with my free hand and picked up the medium plug, holding it in my hand to warm the aluminum body. After finger fucking her a while, still licking her asshole, I moved my wet fingers from her pussy to her ass, pushing with one slowly, in place of my tongue. As I did that, I began to push the plug into her hot, wet cunt. She oo'ed and ah'ed as I played with both her holes.

I had to hold onto the plug tightly because the end "cap" would not prevent it from getting lost in her snatch like it would keep it from disappearing in her ass. Before very long I took it out and put some lube on two of the fingers that had been teasing with her ass. I rubbed lube all around her hole, inside and out, then slid one finger right in, twisting it around, and then pushed in the other beside it. I hadn't had two fingers in her ass yet, and doubted she ever did, but she was into it. She pushed against my hand to get them in deeper and moved her ass around. Her moaning began to get louder. "Is that it, is it in? Did you plug me?" she asked.

"No not yet sweetie," I replied. "Just two fingers, but you took them well and I'm going to get the plug lubed up now." I slide my fingers out of her and she sighed like she'd lost something. I put a good amount of lube on the smallest plug and brought it to her ass. She was trying to watch, and trying to keep her ass still, sort of. She was pretty worked up. "Ok, time to plug my hottie's hot ass." (Yeah, I'm smooth...) I pushed it against her hole and she immediately pushed back into it, making some really great vocal noises. "If you bear down a little, like you're going to poop, it can help, even though something is going in," I told her. I twisted to and fro as I pushed in slowly, deeper and deeper, and then, pop, it was there. I patted her ass and said, "There, all in. What do you think?"

"Well, it started great, then hurt for a bit, and just as I was thinking I should stop you, it went in, which felt weird and good at the same time. Weirdly good, I guess," she mused. "It feels kinda odd, in a good way, but I don't really notice it too much."

"Ok, so far so good. Just sit back and relax," I told her, waiting to see how that went.

She turned and sat on the bench, immediately jumping up a bit and saying, "Oh, fuck. Oh, now I feel it there." She squirmed around a bit, smiling, and then settled down. "Yeah, that's interesting! I think I like it, yeah.

After less than minute she said, "Hey, tell me again, whose night is this? Mine? For me to do what I want with you, for my education and all, right?" I nodded and agreed, wondering what she was up to. "Good, now drop those pants, it's your turn to kneel up on this bench, longwise, so I can bend you down more if I need to." I looked at her and she looked back, cocking her head and pointing to the bench.

I pulled down my pants and briefs, and knelt on all fours along the length of the padded bench seat. She stood smiling nearby, where I could see her. She started to rub my ass, then in my ass crack, and down to my balls, sayin "Nice, very nice, you look good like this."

She went to the end of the bench and started to pull my ass open with her hands, and then I felt her tongue on me, and on my hole, teasing around it, licking on it, pushing against it, and making sexy vocal noises that really sounded hot to me. As she pushed her face in, one hand had moved between my legs to play with my balls and my stiff cock. Then she moved it to reach around my leg and stroke my cock from under my belly while still licking my ass. It all felt great!

Her other hand had found the lube, and she pulled her face away, quickly appling lube to my anus, saying, "Was that good stud, did you like my tongue in your ass. I thought it was hot, especially when I felt your pulsing dick in my hand." Slipping a finger in my ass, she continued, "How's this feel? Good?" Her finger moved all around inside me; in, out, twisting, wiggling, rubbing, as she kept talking to me. I moaned to her that is was good. She let go of my dick and applied some more lube, then pushed in a second finger.

Her other hand returned to teasing my cock, occasionally stroking, but not jerking me off. After a bit of this, she let her fingers come all the out of me, and lubed up the medium plug, which had recently been in her snatch. She said, "Jill told me she thought you probably didn't even need the small one the first time, so I could use the medium if I wanted to plug you. I thought that was a great idea, and since we have the whole set all ready, why not do it right now. We'll both have one in, and I think that's sexy."