Lucky Over 40 Ch. 08: Weekend Ends

"Well, the glory hole situation, or setting, or whatever, intrigues me. I thought about doing you in there, but I know who you are and I'd just picture you in my head. Even if I went in not knowing who's cock it would be, I'd know yours if it came through. I'd know your cock if I were blindfolded."

"That's something we haven't tried," I interrupted. "Blindfolds could be fun. Sensory deprivation, I mean. Heightening all the other sensory inputs..."

"Yeah, I like that idea, too," she said, "but let's put a pin in that for now as well. Shit, it's usually me that gets us off track. Don't start taking my quirks, Ok?

"So, anyway," she went on. "Teddy is a safe guy to try it with. And even if I do know it's his dick coming through the wall, I haven't even talked to him at all yet, so it isn't like I know HIM. I can barely even picture his face. I just know who he is.

"But Jill said he's really lonely," she went on. "He can't seem to get a date `cause girls just think he's a geek or something, but he's really sweet, she says. He's very giving and all. So that's when I thought about Deejay. She needs someone like that and maybe he'd really like someone like her, but they're probably too shy to find each other.

"As for me doing him in the glory hole, well, I thought he'd enjoy it. And, well, I want to try that kind of situation, and this'll be safe. And I can practice my blow job technique before trying it on you," she said with a smirk and a wink.

"Oh, and you can be there and watch. You won't be able to see him, I mean, not much of him anyway. I'd like it if you were there, unless you really don't want to be," she said sort of pleading.

I chuckled at her, "You're a hoot sometimes, Jill. So, you ARE 'doing a friend a favor,' in a way. Doing Jill a favor, and doing her nephew, who you don't really know, a favor. AND getting yourself off at the same time. And rationalizing it by thinking that you 'need practice' for my sake. Yeah, Ok. Well I'm all for you getting extracurricular practice to make your pretty spectacular blow jobs even better. Sure, I get that," I teased her.

"As for me being there, well, maybe. I mean, If I can do you doggie style while you suck him, or if I can do Jill-2, or get sucked off by her while watching you, then maybe I'd be interested in being there," I said as a bigger tease.

I think it took her a little bit to catch on that I wasn't serious. Then she said, "Well, yeah, that could all be fun, but distracting for me. I mean you fucking or getting head from some hot chick while I'm trying to suck off some other cock, well, how could I concentrate?" she replied. I think she was teasing back, but...

"Nah, I could deal with it if that's what you really want," she continued. "Seriously, if you don't want to be there, fine. If one of them wants to be, then that could be cool. Jill may, or may not, want to get a look at her nephew's dick, even sort of 'detached' from the rest of him, so that could factor in, and I don't know who'd be watching the store.

"Anyway, I called Deejay this morning and she might be able to meet us there. We're all working out the time. Tomorrow evening is what we're shooting for. Ok? Again, if that is bad for you, it's Ok. If Deejay or Jill can't help you while I'm helping Teddy, could you still come and watch? Maybe just jack off -- no, don't do that, I'd really want to watch that, without any other distraction."

"Yeah," I said chuckling again, and shaking my head slightly at her comment about wanting to watch me masturbate. "I can be there for you. You're getting me to push my boundaries again, but that's good, maybe."

I almost said I'd be there for her because I love her, but I caught myself. I really felt that, but I wasn't ready to say it. Was it real, of just my libido? Was I ready to "commit" myself, in a way, by saying that?

"Great!" she said, and pulled me over for a little kiss. "Jill's checking with Teddy, to be sure he's 'up' for it," she giggled, slightly. It seemed she was turned on by this latest scheme.

"The other thing we talked about, that I need to run by you," she continued, "is about pegging. I liked those videos, and I got the idea that it's something you might be interested in, too. Am I right?"

"Um, yeah," I replied, a little thrown by the sudden shift on topic, and where she might be going with it.

"Good," she went on. "Well I told all that to Jill and it turns out it's an interest of hers, too. She tried it once with someone, but it didn't go too well, I'm not sure why or how. She brought it up to her last partner -- the one she just threw out -- and he got on about it being too gay or some such shit. Personally, she and I think that a real man, one who cares about his partner, and about having good sex with her, should be able to let her fuck him like he fucks her, at least once."

"Oh, sure," I interrupted, a bit sarcastically. "Is that supposed to help me make up I mind?"

"Shit, no, that's not what I meant," she quickly replied, stopping in her tracks and holding my hand tightly. "I mean, well, I mean what I said, but it wasn't aimed at you or trying to get you to do something you don't want to. Like I said before, I already thought you were interested in getting pegged, and I know you care about me, and about great sex. Shit, I guess that could have sounded manipulative, but it wasn't. Really!"

"Yeah, I know that," I said. "Or at least I trust that to be true. But it did sort of come across like a ploy, or something." I started walking with her again, still holding hands. "He sounds like a really jerk. Jill's ex, I mean. You know."

"Yup, and we don't know the half of it," she said. "Or I don't, you know even less. It's a long story, but the last straw was finding him cheating on her. And he was doing it with some customers, plural apparently. She didn't mind him screwing someone else so much, but he was hiding it from her. And using her store like his personal hook-up service, or something.

"Remember that Jill does NOT do customers," she suddenly shifted her tone slightly, and stopped walking again. "You're something else. Well, yeah, you really are 'something else' in several ways," she smirked and gave me a peck on the lips. "But that's not what I meant. She first sucked you off because we were friends, and I vouched for you. And now you're friends, too, I think. You know all that, right?"

"Well, yeah," I replied with a little reservation. "I mean, I don't know her really at all, despite sort of knowing her in the biblical sense. I wouldn't mind knowing her better, and more about her. There seems to be quite a bit more than meets the eye with her, not that what meets the eye isn't very nice," I said with a big smirk.

Jill squeezed my hand and jerked my arm, saying, "Yeah, I bet you feel that way about her bod. She is kinda hot, in several ways. If I was to ever try something with a woman -- IF mind you -- I could see doing it with her. But that's really not something I'm considering right now."

"Damn, THAT I might like to watch," I said as a tease, but I was half serious. Even though girl-on-girl was not something I was really interested in, those two together could be pretty hot.

"Well, I'll keep that in mind," she retorted. "Jill is interesting. You know, she was in a Master's program in Pysch, working to be a sex therapist. She took a part-time job at the store to both help financially and get some related experience for her degree. She's really very bright, intellectually."

"Yeah, I picked up on that," I said. "But I had no idea she might have had a Master's, and was a sex therapist -- Ok, that part does make a lot of sense."

"Well, she didn't complete the degree, because of what happened," she went on. "The owner of the store really liked her, I mean as an employee and person. There was nothing going on between them, sexually, you know? Well, he had no family any more, and he sort of treated her like a daughter. Long story, but to cut to the chase, her got pneumonia and died. Before he passed, he told her he was leaving all he had to her, to do with as she saw fit. The store, the house she lives in now, a nice nest egg, everything.

"She was floored, to say the least," Jill continued. "She though the store might help with her career as a sex therapist and wanted to keep it going. But it's been a struggle to find good help and such. It required so much time and attention that she had to drop out of school a year or so ago. Teddy is a big help, but he should be moving on to his own career soon, now that his IT degree is almost complete."

"Wow, that's quite a story," I said, truly surprised. "I hope she can go back and finish that degree, if that's what she really wants. The store might be an asset in that line of work. Hell, she could make one of the video rooms into a therapy office -- with a glory hole! That would be, well, unique, I think. But there might be some issue with professional ethics," I said with a laugh.

"Um, yeah, NO!" was Jill's reply. "Anyway, where the hell were we? Oh yeah, pegging. Would you like to get pegged or not, babe?"

"Yeah, I'd like to try that with you, I think." I was a little hesitant. "Honestly, I like our ass play, a lot, especially the prostate stimulation. The idea of it is pretty hot to me, but there is something that makes me a little skittish. I'm not sure why. Maybe the full submission, or heavy femdom overtones -- although a little bit of femdom has appeal. I just don't want a femdom lifestyle or for that to be a major thing with us.

"On the other hand," I went on, "I guess it can be more consensual, no that's the wrong word. Um, cooperative? More like just regular sex, but with roles sort of reversed. If it's with the right person I guess. I'm talking about pegging there, right, not femdom being that way." I was starting to get kind of flustered for some reason.

"Yeah, I think I know what you're saying," she said, squeezing my hand and pulling into my side closer as we continued walking. "I think that too. Ok, maybe there is a little bit of femdom with the pegging thing, like wanting to be in control and wanting to fuck you from behind, that plays into it for me. But you let me fuck you when I get on top, or you have, anyway. I like that, and I think you do, too. I'm in control then, but there's no dominance-submission thing going on."

"Yeah, except for that night when you were 'in charge,'" I replied, with a smile. "And that was fun, too."

"Yeah, it was," she said with a smile. "Would you wanna get pegged by Jill-2?"

I thought for a moment, and said, "Yeah, I think that would be Ok. Maybe better than Ok, knowing what I do now. She is fun. I assume you'd really want to watch, too."

"Yeah, I would, but I don't have to," she replied. It was a little surprising to me, but not fully out of character, either.

"I did tell her I'd ask you about a 'loan' to her," she said a little sheepishly. Then she added with more intensity, sort of trying to plead with me again, "She's really kinda lonely since she had to dump the cheating bastard. I think that she may be even lonelier because she felt so betrayed, even used. And she was! And, well, she's pretty fucking horny, too. Like she said, working in the sex shop makes it tough. Not just `cause of all the stuff. She sees lots of couples coming in, looking to enhance their sex lives, and she doesn't have any, and what she had turned out to be shitty."

"So I'd be helping out a friend, right?" I said with more than a hint of sarcasm, but quite a bit of truth as well.

"Yeah, exactly," she said with a laugh. "You're catching on to this! You'd be helping someone in need. And not like you wouldn't get rewarded for it, you know what I mean?" she laughed. "No, really, she needs a good fuck and I think you'd find her to be a good fuck."

"Um, didn't I just give her a good fuck, or some good orgasms, at least?" I asked.

"Um, well, yeah, but it was just some oral sex and not what she's really wants or needs right now. I mean a night, or day, of full on passionate screwing. Maybe like our first time, but without the same personal attraction, ya know?"

"I think I know what you mean. But do you think I can keep her from falling for me, though? Like you did, remember? I can't just turn this irritable sex appeal off, you know," I said, trying to keep a straight face.

"Um, yeah, right," she said. "She's gonna like you, if she doesn't already. And I KNOW she likes your cock. She wasn't messing with you when she was complimenting it this morning. And I feel the same way. Such a nice cock," she said as she turned and cupped the front of my shorts, feeling my soft, but now stiffening cock.

"Don't get me started, not here," I said, still wary of doing too much in public. Even though we had not seen anyone on our walk so far, there was another car in the lot, and we didn't know who else might have arrived behind us, or who could be there without a car, on a bike, or whatever.

"Come on, big guy," she teased as she tuned to me full on, her hand still cupping me. "Kiss me, Tiger," she whispered, pressing her lips to mine and pushing her tongue into my mouth. We kissed passionately, each with a hand that quickly found the other's butt, and her other hand rubbing my growing erection.

Suddenly, we heard laughter. We broke the kiss, pulled our hands off each other and looked about, seeing a younger couple with a dog come around a curve in the trail. We began to laugh, held hands, and walked toward them, saying "Hi." They returned the greeting and moved past like they knew nothing. I was glad Jill hadn't pulled out my cock, or done more, a few moments ago. I was also glad she didn't decide to tell them what they might have missed seeing, as seemed to be her style lately.

After walking and chatting a little more I said, "I really need to pee, we ought to get back. I've been ignoring it for a while, but it's getting harder."

"Oh, you're getting harder now?" Jill giggled. "Why don't you just step off the trail and pee, babe? Guys can do that much easier than we gals, can." I declined, thinking about the couple that nearly snuck up on us. I just walked faster.

Around the next curve Jill said, "Hey, there's a big Lancewood bush, babe. Let's go behind there and you can have a pee." It did look like good cover, and I really wanted to go, so I stepped off the trail. Jill followed, which seemed a little weird, but it was Jill.

She stood behind me as I turned my back to her, opened my shorts, and got my dick out. I was just about to pee when her hands came around my waist, one pulling away the hand I was holding myself with and the other taking my dick at the same time. "Here, let me help with that," she cooed in my ear. "You know I wanted to do this. Don't know why, maybe just jealous that you can pee this way. Aiming it anywhere you like. Come, on, let it go," she giggled.

It wasn't easy to get started with someone else, much less this really hot MILF holding my cock. But I had to go so bad that after a few seconds I got used to her holding me and I was peeing full force. She seemed to be enjoying herself, and my dick was starting to enjoy her touch enough that it was swelling up. She seemed to like that, too.

When my stream finally slowed to a trickle, she asked, "What now, do I shake it?"

"Not yet, just hold on," I said, squeezing my pelvic muscles to push out the last few spurts of urine. Those muscles also tend to squeeze my butt cheeks, which Jill was pressed against.

"Ummm, I like that little caress you just gave me, babe," she teased.

"Yeah, right. Ok, you can give me a little shake now, not that it usually matters, but I figure you'll enjoy doing it," I teased back at her.

She did shake my dick a few times, then quickly stepped around, bent down in front of me without letting go, and took my semi flaccid dick fully in her mouth. "Mmmm," she hummed as she sucked and bathed it with her tongue, making it grow.

I sighed softly, "Uhhhhhhhhh," as my cock stiffened in her mouth. She began to bob her head along it as it hardened, until it was fully erect. Man, it felt good.

When I was completely hard and fully extended she slid her mouth off and said as she stood, "Ok, that had a little salty urine taste, but I really, really like feeling you get hard in my mouth. It's so hot, in several ways. Should I suck you off until you come, babe?" She fondled my balls and kissed me, gently.

"Damn, honey, I like that, too," I said with a sigh. "You are really good at getting me up. But, I think I'll pass on the full treatment right now, for a few reasons."

"Ok, I'm not offended," she said with a smile and a light kiss, while giving my cock a pat. "Like Jill said earlier, we probably did drain you with all our activity this morning, and all day yesterday, and..." She stopped and chuckled, then continued, "After that load you lost in your shorts I'm surprised you had anything for later anyway."

"Yeah, me too," I chuckled, as I tucked my dick away and closed my shorts. "But if you think that little accident made you miss out on getting another mouthful, just remember who caused it."

"Sorry about that, again," she said as we went back to the trail. "But, you know, I want to use that vibe in your cute ass to try it again sometime, but not when you have any clothes on. No, this time I want to see you blow a huge load without anything else touching your cock or you. Oh I wish I could have seen it explode like that. Then I could finish you off with my mouth, and maybe find a nice way to clean up all the cum. Or watch you do it, or.... Shit, I'm getting wet thinking about it."

"I bet you are," I teased, as I slid my hand up a leg of her shorts from behind and felt the dampness between her legs.

"Fuck!" she said as she jumped a bit at my unexpected groping. Then she settled and rubbed herself on my hand, saying, "Hhmm, that's nice. But what if someone comes up behind us and sees what you're doing to me back there?" she said feigning innocence as she teased me.

She stopped walking, turned into me, opening her legs, and said, "So how wet am I, Tiger?" as she kissed me deeply. I continued to finger her pussy, as we kissed, then moved my hand to play with her asshole. She squirmed, but before I could push inside her we both heard noises down the trail, and turned to look. I pulled my hand back just as we saw another couple come into view. "Ok," she said, "we can continue this someplace more private."

It was a short walk back to the car. When we got there, I went to open her door for her, but before I could she pulled me to her, grabbed my ass, and kissed me passionately. My hands held her shapely ass and we kissed for a full minute or more. When we stopped, she said, "Doing that next to the car always reminds me of the first time you kissed me. And, what followed," she added with a big smile."

On the drive back to Jill's house we talked about several things, but both steered around the subject of our growing feelings for each other or what kind of a future we may have together. We were both just too nervous to think that this might really turn into something, and more scared, that we might really want it to, only to have it fall apart.

At one point, her phone buzzed with a text. "Oh, Deejay says she can meet us at 5 tomorrow evening. I think that should work fine. Don't you?" I agreed. "Great, I'll tell her that I'll text Jill to be sure it works on her end, then let her know." By the time she was done with her electronic conversations we were back at her place. Everything was set, as far as I could tell.

We went in and Jill said, "Hey, it's about lunch time and I could use a snack. How about some more of that wine and cheese and stuff from yesterday?" I thought that sounded fine. I poured the wine and then stood behind her kissing her neck and fondling her tits over her shirt while she put some plates together, giggling and then moaning softly.