Lucky Over 40 Ch. 09: Helping out

Jill was smiling broadly. Apparently I was blushing a bit, so both women started to laugh. "You can probably do more than just see him, if you like. The idea was that you two might wanna play a little while I have my first glory hole experience. If you want to, that is."

"Oh, like dinner and a show," Deejay said, laughing. "Sure, that works for me. But I'm a little jealous that you get to try the glory hole. It's sort of fantasy of mine. Do you think the dude on the other side might be up for a second round after you finish him off?"

"I think we may be able to work something out, sweetie," Jill replied, with a big wink, though I don't know which of us it was directed at.

"I wish I could figure a way to get that nice guy out front to come back here and let me give him a little 'customer service,'" Deejay said, somewhat wistfully. "Do you know him at all?"

"Um, I know he's Jill's nephew," my Jill replied, trying to act innocent. "He works here part-time, mostly maintaining the computers and electronic things. He's almost done with his degree work in IT. Jill says he's really nice. And he doesn't have a girlfriend," she added, sounding a little like the matchmaker she was really trying to be. "I've never talked to him, but Rob has."

Deejay looked at me, a little expectantly. "I haven't talked to him much," I said quickly. "Just about enough to know that he finds Jill-2 to be as much of a handful as I do. And for me to warn him to watch out for this Jill, as well. Beyond that, I can just confirm what Jill said. He does seem like a really nice kid, I mean, young man. And he seems very bright, too. Maybe a bit of a nerd, but nerds are nice. I'm a nerd, you know."

"Yeah, we know, and we love you anyway," Jill said, echoed by Deejay in similar words at the same time.

"Nerd or not, he's cute," Deejay went on. "Can you introduce me, maybe?"

"You seemed to be doing that yourself," I responded. "I saw you chatting with him up front earlier, or were you flirting?"

"Well, maybe...some," she replied, giggling.

"I think we can do something for you," Jill told her, with a big smile. Just about then we heard the door to the next room open and close, and we all fell silent.

Less than minute later one of the round holes on that wall opened and a thick, erect penis poked its way slowly through. Jill was staring at it wide eyed, as was Deejay, to a slightly lesser extent. Jill looked at me and I just raised my eyebrows and gestured as if to say "What are you waiting for?" She looked a little shell shocked and seemed unsure how to proceed. I gestured to her again, while sticking out my tongue, trying to look like I was licking something, but probably looking more like an idiot.

Jill knelt down by the cock and tentatively licked across the tip. The cock twitched and pulled back a moment, then slowly pushed farther into our room again. Jill took hold of it with one hand, licked the head more firmly and then took the full head into her mouth.

Deejay stood staring, her mouth agape. Even I was somewhat transfixed, wondering what both Jill and the young man on the other side of the wall were thinking. Did Teddy have any idea who it might be, what had Jill-2 told him to entice him into doing this, could he be wondering if it was Jill? Apparently this was not something he was accustomed to; in fact, it may well have been his first time participating in the glory hole experience.

Jill began sliding her mouth down the shaft and back to the head, several times. She was looking at me, her eyes wide and seemingly questioning. I went over to her and she took her mouth off the long, hard cock, slowly stroking it with her hand as she whispered to me. "I'm not sure what I should do. Just suck him, or something more?"

"Do what YOU want with him, don't worry about what he expects," I whispered back. "I'm, pretty damn sure he'll like whatever you do, and I don't think he really has a lot of expectations beyond getting off."

"Ok, I'll try that," she replied. "It's just not what I expected, I guess. Without the rest of a person attached, and all, I just don't know what I want. It's kinda weird." She started to suck the disembodied cock again, wrapping her lips around just the head for a while before sliding her mouth up and down the long, thick shaft several times again.

Deejay knelt down next to her, quietly making a suggestion of her own, "You could lick it a while. I'd love to lick that cock. It looks really hot. Do you like the feel of it in your mouth, Jill?"

After minute or so, Jill pulled her mouth off and gently stroked while whispering to Deejay, "I don't know. I'm just not into this as much as I thought I'd be. It's a nice penis, nothing wrong with it, particularly if you like big thick cocks, but... I don't know... Maybe I'm just too into my own stud." And she winked at me. "Would you like to take over, sweetie?" she asked Deejay.

"Oh! Well, yeah, if you're sure," she replied softly, with only a hint of reservation. "If you want to finish him off, let me know, otherwise I'll be happy to do it." Jill nodded and moved back, letting go of the dick as Deejay moved in and took hold. She stroked it a couple times while she looked at it admiringly, then gave it a few slow, wet licks along the full length, finishing the last by running her tongue all around the large, somewhat pointy head.

Jill moved back over to me and said, "Well, maybe that's one more off my bucket list. It just wasn't what I expected it to be. I really, really like sucking you off, but something just wasn't doing it for me here."

"Really? You sure you didn't just say that to give Deejay a chance with Teddy?" I whispered in her ear as she hugged me. I kissed her temple and held her tightly, saying, "You're a good friend, and a very good lover. I know you have no trouble pleasing a nice cock, so I think this is just part of your plan."

"No, really, babe," she said. "I had wanted to give her a turn with him, maybe even finishing him off, but I really just wasn't into it like I thought I'd be. I don't know why exactly. I guess it's a combination of things. Bottom line, I'd really just rather suck your cock, anytime, anywhere, but maybe not through a hole in a wall."

Jill opened my pants again and said, "In fact, I think I wanna suck you off right now, how about that. Can I suck your cute cock right here, while we watch her sucking him? Hmm?" Before I could answer, she had pulled me over with my back to the wall near Deejay and dropped to her knees in front of me. She looked up at my face and as soon as I smiled at her she eagerly licked my cock from bottom to top.

Jill began doing to my cock what Deejay was doing to Teddy's, but without a wall in between us. Before long Jill's hands were also playing with my balls and my ass, and Deejay was watching her. She slid her mouth off Teddy and said to Jill, "Yeah I'm missing that part, too."

Deejay slid open a small door, about eight or so inches square, near the hole where Teddy's cock was. She put one hand into the opening while she gently pushed Teddy's cock back through the wall. I guess he got the idea because she was soon pulling her hand back through the door, holding onto the long, thick cock. Now a tight set of balls were also visible, and her other hand began to fondle them while her mouth enveloped the cock head.

Deejay began to giggle as she lustily kissed, licked, fondled and sucked on Teddy's rigid cock. The hand on his balls soon pushed farther between his legs and, I assumed, started playing with his ass. The cock and balls pushed farther into our room through the little door. Jill was watching all this as she licked and kissed my dick, fondling my ass and balls, and making soft vocal sounds of enjoyment.

After another minute or so of this toying and teasing, Deejay began to vigorously suck on Teddy, sliding her mouth in and out along most of the length of his shaft, leaving it glistening with her saliva. One hand cupped and caressed his balls and one was still apparently playing with his backside through the little door. She was sucking hard, making wet noises and moaning softly. Deep, quite moans could be heard coming from the other room. Jill began to suck harder on me as well, and a finger wiggled into my asshole, teasing me more.

A couple minutes later Teddy was moaning and groaning louder, then we heard him say, "Oh, mam, I'm gonna come. Watch out, I'm gonna come mam."

Deejay moaned back, loudly, "Umm, hmm, yeahhh," around his cock as her mouth kept moving along its shaft. Very shortly thereafter, her eyes opened wide as the cock twitched and Teddy groaned. She closed her lips tightly around just the head and hummed, "MMMmmm." Teddy groaned deeper.

After several seconds the twitching lessened and Deejay relaxed her lips. Some cum dribbled down her chin and she caught it in her hand. She slid her lips off his cock, licked the head once and then licked the cum from her hand. She pulled her other hand back in and wiped her mouth with it. When the cock retired through the door she gave the head big kiss. After it disappeared, she put her face to the opening and looking in said, "Thanks, big boy" before closing the door.

Deejay turned, put her back against the wall and slid down to sit on the floor, with her eyes closed and a satisfied smile on her face. Jill had stopped sucking me and was absent mindedly stroking my dick as her young friend finished. She let go of me and went to Deejay.

"Looks like you enjoyed that, sweetie," Jill said to her. "Did you get a good look at him through the little window thing?"

"Yup, and nope," Deejay replied, dreamily. She opened her eyes and continued, sounding more alert, "It was great, but all I saw were his jeans as he was putting away that really nice cock. Thanks for letting me take over. It was...wonderful," she sighed, closing her eyes again. Jill was smiling at her.

Several seconds later Deejay went on, "I really enjoyed that. And knowing that you had sort of 'cleared' whoever it was before hand, since you have the same concerns I do about strange dicks in here, made me really comfortable with it. Do you have any idea who it might have been? Should I just ask the other Jill? Somehow I thought he was maybe kinda young, like around my age, maybe."

"Well, is there anyone one you'd like it to be?" Jill asked.

Deejay gave her a puzzled look and said, "What does that mean? I wish it had been that cute guy at the front desk, but it can't be since he's working. Right? But, to be honest, I was sorta picturing him while I was working that dick. It made it hotter."

Jill smiled broadly and said, "I guess I didn't say earlier, but the guy out front is named Teddy. I can see how picturing a guy you think is hot could make a difference. Somehow I didn't think of that, or really, I was too busy thinking about my hot guy instead. Anyway, I think you got your wish."

"What?" Deejay said, very puzzled now. "Wadda you mean you think I got my wish? What wish?"

"Jill, that's Jill two, by the way," my Jill said, "had set it up so I would blow Teddy in here." Deejay's eyes went wide and her mouth fell open. "He's very lonely, and apparently pretty horny, and I needed a 'strange' but 'safe' cock. Since I've never even said 'Hi' to Teddy, he's basically a stranger." Jill chuckled and continued, "But it was all stranger than I thought it would be."

"You're shitting me," Deejay said in amazement. "Was that REALLY the cute guy from out front? Does he know it was me? Well, you and me? Oh man! I don't know what to say." She seemed happy and confused, and maybe embarrassed, all at the same time.

I smiled at them both as I tucked my unsatisfied but now semi-erect cock back in my pants, saying, "I'll head out front so you two can have some time for girl-talk." I was chuckling as I closed the door behind me and walked down the hall. I soon saw Jill-2 coming toward me.

"How'd it go?" she said. "Did everyone in your room have a good time? I'm pretty sure Teddy did. He was almost floating when he came back behind the counter, but didn't say anything. I tried to ask him but he just blushed and went into the back room with a big smile on his face."

"Jill should fill you in on the details," I said, "but yeah, I think a good time was had. She let Deejay take over pretty quickly, and then went to work on me. She never did quite finish though. The others were too good a show. Deejay now knows it was Teddy, and apparently is very pleased about that fact."

"Well, that's good news," she responded. "I'm sorry about you, but I bet we can make it up to you in the second part of the night." I looked at her a bit confused and she went on, "did you forget that the three of us are going to have a pegging session tonight?"

"Oh, ugh, yeah," I said, it having actually slipped my mind. "Looking forward to it."

"That's good. So am I, stud," she said. "Do you wanna go out and have a little chat with Teddy and I'll check in on the girls. See you out front in a bit. Oh and there's another employee out there now, taking over so I can go home. Just tell Barry I sent you back to see Teddy."

"Um Ok, not sure what to chat about." I said. Then catching on I added, "Oh, yeah, Ok, guess I'm just not as good at this matchmaking thing as you girls are."

I went out front and saw a big burly guy behind the counter, wearing a leather vest with a gay pride patch on it. 'Why not, all shapes and sizes, right?' I thought to myself as I said, "Hi, Barry, right? Jill sent me back to see Teddy. Ok if I just go in back?"

"Yeah, sure pal. You're one a Jill's friends, right?" he responded.

"Yup, I'm Rob," I said, extending my hand as I went behind the counter. "Been working here long? I haven't seen you before, not that I'm here a lot anyway."

"Oh, a moth or so, maybe more now." He said, shaking my hand with a grip much looser than I expected from a guy his size. "I'm just part-time. Thought it would be interesting, and it has been. Teddy, you got a visitor," he called in back as he opened the door for me.

"Hi Teddy," I said going in the door. "Remember me, I'm Rob, a friend of your Aunt."

"Oh yeah, sure," he said. "Nice to see you again. Um, your with my Aunt's other friend, right? Jill, I think her name is too. Were you guys back in the video rooms earlier?" he asked with a little bit of embarrassment.

"Yeah, we were, which is kinda why I'm here," I said with a little embarrassed myself. "Hmm, this is kind of awkward I think. My Jill and your aunt sort of arranged for Jill to give you a little, well, what they refer to as 'help' I guess." Teddy shifted uncomfortably in his chair. "It's Ok, I know, and I was there with her. Yeah, this is all very weird. But don't be embarrassed. Did you enjoy it?"

"Um, yeah, sure, who wouldn't," he said, still apparently unsure about this conversation.

"I guess you're right about that," I affirmed. "Did you know who would be in the other room when you went down there?"

"I knew it was one of my Aunt's friends. Her female friends, I mean," he added quickly. "Aunt Jill didn't tell me much, but I sorta thought it might be your girl when I saw you guys here. I guess I sorta hoped it would be. She's pretty hot. And not just her looks, you know. Something about her, I don't know."

"Yeah, I know what you mean," I said. "Well, that's all good. And Jill did start you off, but she didn't finish you. You might say it was a team effort."

"What?" he questioned. "Um, well, I did notice a change. She was good, but kinda, um, hesitant maybe. But then she suddenly seemed to get much more, um, intense, I guess. I just thought she was getting into it more. Now that I think about it, I guess there were other differences that I sorta noticed, but didn't think too much about at the time. I was kinda preoccupied, I guess, `cause it was, well, it was really good."

"So, any thoughts on who the mystery woman was that was so good?" I asked him.

He sat a moment, staring off, then said, still looking off elsewhere, "Um, no I guess not. Unless...could it be that cute girl?" He looked at me now, saying "I was talking to this cute girl, about my age, a little while before I went down there. And I think she walked into the video area too, now that I think about it. She was nice, but probably outa my league."

"Oh, maybe not," I said, trying to be encouraging.

"Yeah, right, not her. Wouldn't be her. Can you tell me who it was?" he asked.

"You misunderstand," I tried to explain. "The cute girl is called Deejay, and she's a friend of ours, too. Yes, it was her, and she thinks you're pretty cute yourself. Man, I feel like I'm in high school playing go between to tell you that girl you like likes you, too. Can't say I ever did that then, but well, I guess I'm doing it now. Anyway, what do you think about that."

"Um, I don't know what to think," he said, seeming a bit bewildered. "I never did that in high school either. Never really had much contact with girls then. Never went to dances. Only had one real date, and that didn't go real great. And no one ever told me that some girl liked me. Shit, she doesn't even know me."

"Well, barely," I said. "She talked to you a bit and she's attracted to you, and apparently, you are to her, without even knowing her either, so..."

"Um, yeah, I am. What did you say her name was, Dee something?"

"Deejay. It's a nickname from her initials. She's really sweet, a little shy, but she can also be a real flirt when she warms up to you. And she's quite smart, just like you seem to be. Honestly, Jill wanted to set you two up, but it seems she didn't need to."

By this point I heard the girls' voices approaching. "I believe they're on their way back. Get on out there and see if you can chat with her again. You don't need to let on you know it was her in there. She might know it was you, but she may be too shy to let you know that -- or not. You never know with these women. Anyway, go ask her out or something. Get her phone number at least." I left the room before he could say anything else. As I left I thought to myself, 'Listen to me, of all people, giving dating advice!'

Teddy appeared behind the counter and looked at Deejay, who looked at him, and they both turned away, briefly at least. Then the Jills motioned for me to follow them and we stepped away. As we wandered off I heard Deejay say "Thanks again. You've been really nice, and all." I thought I heard him say something about him needing to thank her, but I wasn't sure.

Jill-2 said "Let me get my stuff and we can head to my place. If you get there first, the side door is open so head on in. There's white wine in the fridge and some red on the counter if you want any. I'm looking forward to a nice big glass of red. Oh, and we need some dinner. Shit, I didn't think that none of us have eaten yet."

"We'll pick up something on the way. Pizza OK?" I offered.

"Yeah, that's fine. Thanks! Oh, no anchovies and we probably want to skip the garlic" Jill-2 said, with a laugh. "See you there."

As soon as we got in my car I handed Jill my phone, with the number for a pizza place near my apartment already cued up. She placed an order and we picked it up on the way, since it was on the way to Jill-2's place. As we walked into her house and put the food in the kitchen, Jill-2 came in wearing that sexy, short, oriental type robe she had on last time we were there.

We all sat down with some wine and dined on a tasty, but tame, mushroom pizza. We talked about Teddy and Deejay seeming to work out well so far, and wondered how their first date would go -- assuming this wasn't really a date. Would Teddy return the "favor" that Deejay had just bestowed up him? Would Deejay suck him off again? Would they just jump into bed and screw? Or would they both play shy and just have a "normal" date ending with a chaste good night kiss or maybe an old fashioned make out session? The girls were better at imagining the various scenarios. I just hoped he got her number.