Lucky Over 40 – Chap 09: Helping out by Reek57

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.”

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