Lucky Over 40 Ch. 06: The Weekend

This is the sixth part of the story of two single 40somethings that met on-line and started an adventurous sexual relationship. It's about exploring completely heterosexual kinks, and contains things like mild dominance by each partner, voyeurism, oral sex, anal play, spanking, 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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As I've said before, I really "got lucky," in a truly sexual sense, when I found Jill, and then discovered what a wild sexy babe she was. We both seemed perpetually horny and both had active sexual imaginations we liked to indulge, but never really had a good partner, until we found each other! If you've read the last couple parts of this storyline you know she had just "loaned" me to a 25ish year old friend of hers for the girl's sexual education, of sorts. It was great fun, and a real workout. But now I'm back to focusing on Jill again, and very happy about it.

When I got home Monday evening from Deejay's, I wanted to call Jill, but knowing she was busy I didn't want to leave a voice mail at home where her daughter could pick it up, nor did I want to ring her cell phone when she might be working. So, I sent her an email that was short and sweet, along the lines of "mission accomplished, loan fulfilled. I'm beat and going to bed, but wish you were here," etc. Then I ate the takeout I picked up on the way home, took a nice shower and headed to bed. If she called and woke me, that would be fine, even though I might be a little incoherent.

Tuesday was a regular workday and I was teaching a class in the evening. Jill was on-call the next evening, maybe two, so we likely wouldn't see each other until the weekend. Just as well since my dick probably needed the rest! Of course, I figured if I got thinking much about Jill, or the adventures of the past week, it would likely be trying to push its way out of my pants again anyway.

I got an email from Jill a little later in the day. She had already talked to Deejay and got the full scoop on both of our "study sessions," as she put it. She teased me about several things, including the escapade at the glory hole -- though she did not mention the part she played in setting it up. She also teased about spanking a new thing she thought sounded like something we should try together, adding a smiley face. She closed her note by saying her daughter might be going away to some concert over the weekend, and could be gone overnight, "hint, hint, hint..."

I emailed back and said the weekend sounded like a great idea. I also mentioned, teasingly, that maybe we needed to go back to the sex shop since I think maybe I owed Jill-2 something. And, I owed HER something as well, adding a link to an image from an erotic website showing a woman's bottom with her panties pulled down and a pair nice pink, freshly spanked ass cheeks. I wasn't sure how that would go over, but since she had written that maybe we should try spanking some time...

She replied to my email by writing only: "Really?!?! Hmmm," and a smiley. Since we both were busy we didn't have much contact again until Thursday, when Jill called my cellphone. She told me, excitedly, that her daughter would be leaving for the concert early Saturday morning, and not getting home until Sunday evening. She asked if I would like to spend the weekend at her place? I told her that sounded great. She asked if I'd go get dinner with her Friday evening and do some shopping for the weekend. She was thinking we should get some wine and pick out some things for snacking and for a nice meal to have at home. And, she didn't yet know what I liked for breakfast, but she was looking forward to having it with me, maybe in bed.

I told her that all sounded great, and I said quietly that my preferred breakfast might be her. She laughed, and teased back, then asked if I was at work. When I told her I was she started really teasing me, saying, "Well, I could certainly feed you a nice juicy pussy for your breakfast, while I find something tasty to suck on. I might want to have some fresh cream in my coffee, so fresh that I might milk it myself. I can't wait to see you; reach in your pants and feel you, pull you out and lick you all over. Are you getting hard for me? I'm so wet for you, Tiger, I think I need to put my hand in my panties and pretend they're your fingers. Tell me, are you hard, Tiger? Tell me, please."

"Yes, I am, very much so, and fortunately I'm at my desk right now. I'd love to respond to your proposal properly, in full, but I can't at the moment," I replied with some frustration in my voice.

"Oh, that's too bad, I'd love to hear you talk dirty to me. Since you're at your desk, you should pull out your beautiful hard cock and stroke it while thinking of me kneeling under there, between your legs, licking and sucking it. I'd love to do that if I were there. Mmmm."

"Wouldn't we both," I replied very truthfully. "I've got to work on a response to your proposal, and want to really concentrate on it. I'll be very happy to help you tomorrow, and to have you follow up on that idea. I really have to go now. Thanks for bringing all that to my attention."

"OK, Tiger. Don't jerk off too much before I see you. Save all your nice cum until you see me," she teased back. "I'm really looking forward to seeing ALL of you after work on Friday. Bye, babe."

There was more teasing via email. Also some links to very suggestive -- and a couple explicit -- pics, sent both ways, via text. That way we could open them on our cell phones, even at work, and she didn't need to use the "household" computer that her daughter, Becky, might also use.

Finally Friday arrived. After work I went home for a quick shower and changed into shorts and a polo shirt, then I was soon knocking on the door to her house. Jill answered and welcomed me in.

I was thrilled to see her again, and my cock immediately surged at the sight of her smile, bright blue eyes, and long blond hair pulled pack. She was wearing a simple pink top that showed a bit of cleavage and accented the shape of those perky, firm round breasts, just over a handful in size, which I so adored. I could swear I saw the nipples hardening and poking out as soon as we locked eyes on each other. She also had on a cute short skirt that showed off her long slender legs.

I wanted to jump her right there as I walked in, but she put a hand on my chest, kissed me on the cheek and nodded toward the kitchen area. Becky was doing something there in the kitchen and called out "Hi Rob!" as I came in. I went over and chatted with her briefly about her weekend plans and she said, "I told mom that you two really ought to spend the weekend having some fun together, since I'll be away."

I smiled and said to Jill, with a wink, "Yeah, maybe we should. I'm free this whole weekend and I'd enjoy spending more time with you, if that's Ok."

"Oh I bet it will be," Becky responded, before Jill could. "Ya know, she hasn't dated anyone else since she started seeing you, and she told me you guys had some really fun dates, but she doesn't tell me much about where you go. I like to see her getting out and having fun, and I don't want to cramp her style, which I think maybe I've been doing just by being around. So, now you two have the house to yourselves for a while, and I'll call before I get home on Sunday, Ok? Oh, and I'm actually spending tonight at a friend's, so we can get going earlier tomorrow morning. So, I hope you brought your jammies," she said to me with a big wink.

"Becky!" Jill exclaimed with a little scold in her voice. But then she said to me, "I think you have Becky's seal of approval to date me, Rob! Becks, I appreciate your encouragement, but Rob knows I'm not sure about any big relationship right now, and he isn't ready for that right now either."

"Hey, there's a pullout bed in the den for company, and I'm not telling you to get married, just spend some more time together and have some fun doing whatever old folks like you do. I like Rob, mom; much better than the few other guys you had some dates with. Some of them seemed creepy. Ya know, though, I think maybe you guys should think about going away for a weekend together sometime."

"Are you trying to get me out of the house so you can have a weekend party, Becks?" Jill asked.

"Damn, ya caught me!" she threw back. "No, you haven't had a weekend away with friends in a long time. I think it would be good for you. And, somehow, I trust Rob not to take advantage of you at all. Anyway, I gotta finish packing so you do what you need to do and if I don't see you until Sunday, have fun!" She winked at me again as she headed to her room in the other end of the house.

When we heard the door to her room close Jill said, "Wow, that was unexpected. I wonder what she's thinking. Or what she's up to!"

"If she's like her mother, I'm not going there," I said, half joking. "Do you think she was giving us permission to fool around? Or that she already thinks we are? Are you Ok about either of those possibilities?"

"I don't know, and I don't know," Jill said, a little contemplatively. "Could be either, could be both, and if so, I guess maybe it could be a good thing. I'm trying to come to terms with her being 22, which is about how old I was when she was conceived. But I was married then -- not that we weren't 'active' prior to that. I'm almost certain she's been sexually active, but I made sure she's on the pill -- better safe than sorry -- and I trust her to be careful of STDs and such since she's very health conscious. I just don't think I want to KNOW that she's currently sleeping with someone, and especially not here when I'm around. The same way I'm not ready to fool around with you here when she's in the house, or have her come home and find us at it. I guess I need to have a discussion with her about all of it; to let her know it's Ok if she is fooling around -- not like a slut mind you -- and to let her know that we might be, or are," she grinned.

"That's all probably tough to grapple with, and I don't envy you. I'm here to help if you need me, but I honestly don't know what I can do. I've never been a parent...that I know of," I said with a big smirk.

She smacked my butt and laughed some, saying, "Yeah, guys can make `em and leave, but women can't just walk away after the fun part's over." She sighed some, then said, "Well since I may have her permission to fool around, let's not waste any time. Let's get ready to go shopping."

She suddenly stepped into the kitchen, where I could see her, but she was out of sight if Becky came out of her room. She turned away from me and bent over, flipping up her skirt to show me her gorgeous naked ass, no panties to block the view, and the jeweled end of a plug peeking out between her cheeks. She looked at me through her legs and said, "I'm ready, but you're not. Into the bedroom quick, big boy." She ran past me to her bedroom, sort of giggling, and I walked in behind her.

Once inside, she locked the door and said quietly, "Ok quick now mister, drop those shorts, bend over by the bed, and spread `em." She opened a bedside drawer, pulling out a plug, an exam glove, and some lube. Watching me intently as I followed her directions, she put on the glove and applied lube to the plug and her gloved fingers, while quietly saying "Open those legs a little more, and stick out that butt. Yes, I do like that view. Hmm, such a nice package, even from the back. Use your hands to spread those cheeks for me. Yeah, that's it. Here we go, just relax and enjoy, big fella."

A slippery finger slid into my ass, moving in and out and all around. It was then joined by another finger, entering more slowly, but soon moving around to further stretch my receptive hole. She withdrew her fingers and I felt the plug start to push against my dark place, while the gloved hand with slippery fingers started to play with my growing crock. She whispered words of encouragement in my ear as the plug twisted and turned, pushing into my ass until it suddenly popped into place.

"That's much better big boy," she said patting my ass, squeezing my cock and kissing the side of my face, all that the same time. "Get your shorts on and let's get going. Oh, I see they've got a built in lining so you don't need any undies, that's convenient!" As I pulled up my shorts she asked, still in a hushed voice, "How's it feel, Tiger? I'm wearing the medium one this time, even though Deejay told me it fits you fine. I gave you the small one again because I didn't want to try jumping up to the big one when we're in a rush."

"It feels, fine, but maybe not as good as your fingers just did, and your hand on my cock," I replied, quietly. My cock wasn't sure if it wanted to keep growing or just relax again. "I'm really sorry we didn't have time for more, but you did say you didn't want to fool around with Becky in the house. This wasn't fooling around I guess," I said teasingly. "Anyway, since you got us dressed in matching attire, I'm guessing you have something else in store."

"Ok, maybe this was pushing it a little with her still home, but that's why I locked the door, and made it quick. I didn't want to do it out in the car, like some people," she said wryly. "but I really wanted to slip that in your cute tushy so you'd be in a good mindset as we run some errands and stuff." She walked out of the bedroom, saw that Becky was apparently still in her room -- hopefully none the wiser -- then beckoned me to come on out.

We went right out to her car and Jill drove us to the big wine and liquor store and then a grocery store for our weekend necessities, as she put it. It was fun to shop with her in public while knowing she had no underwear on, nor did I really, and that we both had plugs in our asses. Every now and then she would pat my ass, sometimes right on the plug, intentionally I'm sure.

We'd frequently make silly suggestive remarks, like her talking about my meat in the deli department, and giggling as she commented while examining cucumbers and other produce. I said evocative things about her luscious melons, and the hard buds that were obviously poking out against her blouse. At one point she started to bend over and looked like she was about to flash her ass to me, but some older guy came into the aisle and she quickly turned back toward me, blushing. It was all very silly and even rather juvenile, yet very arousing in the long run.

When we got to the car and had put everything inside, she took me in her arms and kissed me, hard and passionately. I pushed her back against the car, with my hands holding her ass. After we got in, she remarked that it was almost like our first kiss, in the cinema parking lot, but that she was even wetter now, and didn't have any panties on to catch it. As she started to drive I slid my hand between her legs and confirmed that she was nice and moist, sliding a finger in her as she gasped. After I removed it, I sucked on the finger, slowly and suggestively. She asked if that's how I wanted her to suck my cock later. We were both definitely horny.

The erotic banter continued as she drove. I soon noticed she was headed toward the sex shop rather than home, and said so. She said, "You're very observant. We have one more errand to do, well, maybe a couple, but only one more stop."

When we arrived, she parked the car and got out quickly. She made fun of me for not getting out very fast because of my bent erection trapped in my shorts. She giggled when I got out and adjusted myself. I untucked my shirt trying to cover the bulge in front.

"I like seeing you do that," she said with a smile. "I mean fixing your hard dick, because I get you excited. I'd be happy to help if you'd like," she teased, taking my hand as we walked into the shop.

It was no surprise to see Jill-2 there behind the counter. "Two of my favorite customers," she said with a big mile. "How ya doin' Jill? And you Rob? Little Robbie looks like a growing boy, too, I see," she teased.

"I'm doin' real good Jill," my Jill answered, cheerily.

"Hi, Jill. I'm doing good, too," I said less cheerfully. Then I asked, somewhat concerned, "Does it really show that much?"

"Nah," she said, smiling. "I'm messing with ya. Knowing you, and who you're with, I just figured you'd be fairly hard right now. Hey, you didn't thank me for the extra service I gave you last time you were here. You know that was not at all standard practice right? Just helping out a friend, so to speak. I hear you might think you should return the favor, is that right?" She was teasing me, I assumed, I hoped, sort of.

"Well, ah, I might've told my Jill here something like that, sort of, in confidence," I said with a playful glare at "my" Jill. "It was really nice and all, really, but I didn't know you were helping me out," I said a little nervously. Then I thought I ought to play it back at them both. "However, I'm always ready to help, or to repay a favor to a friend, so sure, whatever I can do to help you, just let me know." I thought I was calling her, or their, bluff.

The Jills looked at each other, then smiled, and Jill-2 turned back to me, "Absolutely, I can surely use your help with something that I haven't had any help with in too long. Come right along and let me show you what you can do for me, if you're still willin' to help." Was she giving me an out, or calling MY bluff, or was there really some issue at the store that needed attention? I was puzzled, but I wasn't going to back out, and if it was what I thought, well she was attractive, although not exactly my type. And she had gotten me off once. So far. And they both seemed down with it. So...

"No, sure, whadda you need? I'm always ready to help out a lady." I said as casually as I could.

"I'm sure you are, cutie. Step into video room 3, in the back, you remember it, right?" she said.

"Do you need me to watch the counter?" my Jill asked.

"Nope. Teddy's working right here in the back and he can come out to stand by for a few minutes," Jill-2 said, and stepped into a room behind the counter for a few seconds. She came out and walked toward the back of the video section, where she'd been directing me. "Come on Jill, if you wanna watch, or whatever." As we all walked back to room 3, she continued, "Teddy's my nephew. He takes care of the store computers and CCTV and all that tech stuff here. He's finishing a degree in Computers and IT. He's really bright and a great kid, but the girls all seem to think he's just a nerd. Ok, step inside and we'll get to work."

We went into the largest of the "private video" rooms, where I'd been recently with Deejay. It has a padded bench seat, like from a restaurant, and couple chairs. As I found out last time, the room also served as a glory-hole with openings to its two adjoining rooms. I assumed the other few video rooms all did as well.

"So, Rob, last time I serviced your need and I'd appreciate your helping me with mine. Jill here says you're really good at oral. It's been a long time since my lover left -- well, since I threw his sorry ass out -- and I'd really like to feel someone get me off. You won't mind if Jill wants to watch, will you? You two can have the room to do what you need after I get mine. Ok? Oh, and as I've already told Jill, I got tested after I threw that cheating asshole out of my life, and haven't been with anyone since -- hence my need for some help. You ready to do that for me, cutie?"

Even though I had some idea that this kind of thing might be what was in store, I was still surprised it was really happening. I looked at my Jill, who had taken a seat on one of the chairs, backwards, with her chin resting on her crossed arms on top of the seat back, facing us. She was just watching, and smiling, silent for a change.