Lucky Over 40 Ch. 09: Helping out


Author’s note: This is the ninth 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. You do not have to read previous parts to enjoy this, although some things would be better understood.

Please DO make use of story Tags to see what you may or may not like. If anything there bothers you, don’t be upset if you decide to keep reading.


I’ve been dating Jill for over a month, and we’ve been having sex for about three weeks and it has been incredible. I feel like the luckiest guy in the world to be with her. Her adult daughter, Becky, went away this past weekend and we had our first sleep over, spending the whole weekend together. Before that, Jill had “lent my services” to two friends to help them out with some sexual frustrations. We were supposed to meet one of them, Jill-2 I call her (because her name is also Jill), tonight at the adult sex toy store she owns, so that Jill can try “helping” Teddy, Jill-2’s 24 year old nephew. We are also meeting the other friend she lent me to, 25 year old Deejay, there as well. Jill and Jill-2 hope to set up these two young people to start dating.

Jill sent me a text this morning while I was at work asking if I could pick her up at her house around 4. I texted back that I thought I could, but would let her know if it turned out otherwise. I knew enough not to even bother asking why the time had been moved earlier.

Since there wasn’t much planned for me this evening — just Jill giving Teddy a blow job in the glory hole with me there to watch her — and the fact that it was a fairly busy Monday at work, I wasn’t as charged up and horny as I usually am before seeing Jill in the evening. Well, the nearly non-stop sex all weekend may also have had something to do with quenching my libido.

I was able to get off work early, but didn’t have time to go home first, so I arrived at Jill’s in chinos and a button-down dress shirt. She opened the door and told me I looked real nice. I said the same of her, complementing the top she had on as I stared her cleavage through the low cut front and at her erect nipples poking out.

I gave her a nice kiss and started to rub her ass, when she tried pulling back and I heard Becky call from inside, “It’s awfully quiet. Are you two sucking face out there? Well, don’t mind me.”

“Hi Becky,” I called out. “Just greeting your mom properly, like the gentleman I am, you know,” I teased back to her. I gave Jill’s breast a nice caress, followed by a gentle nipple pinch.

“Gentleman my ass,” Jill whispered to me, swatting my butt as I went by, and adding softly, “But you do have a cute ass.”

Becky had stepped into the foyer just in time to see and hear the last part. “Yup, he does. Do you like smacking him on it very often, mom?” she said with a big grin, and then a blush. “Sorry, I couldn’t resist. Oh, and I bet you couldn’t resist either!” she giggled.

I just stood there, somewhat embarrassed and a little confused. Becky was more like her mom than I thought, and was being much more open around me than she had been previously.

Jill blushed, and said “I talked to Becky last night, about us. Especially after my little investigator said she found her favorite pen, that she had misplaced, trapped between the cushions of the fold out couch in the den. She wondered how you could have slept on it without moving the cushions, since it’s too short for you without unfolding it. I said you didn’t and she promptly figured out where you did sleep. I wouldn’t lie to her.”

“Yeah,” I said, “I noticed yesterday that you were kinda skirting around the truth, without lying, when you implied I had slept in the den. Knowing that she IS a bright one, I wondered how long that would hold up, or if Becky would just give you a pass and let it go.”

“Oh, I rarely give passes,” Becky said. “Really, though, I’m glad you two are at that stage in your relationship. You’re grown adults and all that. I figure your sex drive is nothing like it was when you were my age, but you must still have some urges, so fine.” Jill and I looked at each other and tried not to laugh.

“I’d just rather not know when you’re doing it, or hear the details from mom later — well maybe just a few,” she said with big smirk. “But she sometimes shares too much about some things. It’s bad enough I have to see that cute ass around here, especially when I don’t have somebody’s to play with myself,” she said, somewhat wistfully.

“Speaking of sharing too much, young lady,” Jill half scolded.

“Well, thanks, Becky,” I said. “I’m flattered, sorta, but also so very surprised to hear that your mother might share too much. I’ll have to keep that in mind,” I said with a little glare to Jill, who just shrugged.

“Um, we need to get going, babe, I mean Rob,” Jill said, quickly trying to catch herself.

Becky chuckled and said, “Hey, I know how you two feel and all, so you can get lovey dovey, when I’m here, just keep it within reason and try pinbahis yeni giriş not to rub it in when I’m stuck without a boyfriend.”

“Sorry, Becky,” I said. “I wish I could help you with that.” Jill looked at me warily, perhaps wondering if I wanted to help Becky like Jill had me “helping” her friends. I looked back at her and just shook my head, “No.”

“Well, if you can send a nice young sexy medic or flight nurse my way… Males only, please.” Becky kidded, as Jill dragged me out the door. At least I think she was kidding, but it wasn’t a bad idea. I know a lot of nice, eligible young men at the ambulance and medical helicopter service where I’m the Operations Manager.

As we drove over to the sex store, I reassured Jill that Becky was off limits for me and that I was 99% sure she was kidding. “But on the other hand, it seems apparent that she is her mother’s daughter, so…” That comment earned me a smack on the arm from Jill, but she smiled when she did it.

I told Jill that I missed her in bed last night and it was a little hard getting to sleep alone, but that I had a sexy dream about her. She, of course, wanted all the details, which I just couldn’t remember, as much as I wished I could.

“Yeah, I usually can’t remember my dreams either,” she said. “Even when they’re about you. And I had some trouble being in my bed without you, too. I hadn’t changed the sheets and it smelled like you. It was very nice, but made me miss you more.”

Then she bit her lip, looked away and added, “I even ducked down under the sheets to smell the remnants of our lovemaking on them. It was kinda sexy, babe,” she said looking back at me with a shy grin.

“Oh, yeah?” I said, thinking it was kinda sexy. “Could you smell ‘us’ at all?” I asked.

“Yup,” she said with a smile, “And we smell almost as good as we taste, Tiger.”

We both laughed and I squeezed her hand in mine.

“Hey,” she said, changing the subject. “My sister, Barbara, who works for the Mouse, I mean Disney, remember? Well, she says she wants to give us some sort of special comped park tickets for the weekend after next. And some paper fast passes, too, that get us right onto rides without a big line.

“Wow, that’s really nice of her,” I said.

“It’s got to do with some event going on at the current Epcot Festival, I think,” Jill explained. “We’re getting the VIP package they give to people like travel agents, journalists, bloggers, and such. A couple people had to cancel and she’s giving us their stuff. But that’s part of why she really wants Becky to come; to write an article or something. Becky’s happy to, but she’s disappointed that she doesn’t have a boyfriend to bring with her. Of course, that could change in a week, knowing her.

“Yeah, if she’s like her mom,” I said. “She’s certainly very pretty, just like her mom!”

Jill ignored me and went on, “Anyway, Barbara, says she’s really happy that I ‘found’ someone and said she’s really looking forward to meeting you then. Oh, and the hotel’s comped, too. But she won’t say where. Either they haven’t nailed it down or she has some surprise, I guess. I hope it isn’t one of the motel like ‘value’ places. I’m betting it’s likely to be someplace moderate though, but we’ll see. We can check in anytime on Friday after one. So, is that weekend Ok, and could you get off early on Friday, or maybe the whole day?”

“Uh, sure, I don’t think I have anything going on then.” I replied. I didn’t have a problem with the idea, and a weekend away at “fantasy land” with Jill sounded great. Meeting the family was another step I wasn’t sure I was all that ready to take, but then again, maybe I was, with her. “I have to check my little black book, though,” I teased.

“Oh you do? Have to check all the other dates you already have lined up, huh?” she teased back. “Well, I’ll just have to ask one of my other hunks, then. Hey babe, we don’t have to if you don’t really want to. Just a thought, and her normal park ticket comps aren’t time sensitive. Though she might be, sensitive I mean, maybe. Or, we don’t have to go at all if you aren’t into the Disney thing.” She seemed disappointed, which I didn’t want to do to her. I wasn’t really against it, just nervous for some reason.

“Princess, my beautiful Princess, I’m interested. I’m just processing it, that’s all,” I tried to reassure her. “Ok, let me be fully honest. I’ve told you I’m nervous because things are moving faster than maybe I’m ready for, or thought I was ready for. Meeting family sort of, I don’t know, makes that more intense. I like Disney, I do, but probably not as much as you do. But, um, I’d go almost anywhere with you — or maybe anywhere. So, yeah, I can deal with the arrangements from your very generous sister, and I’ll go, happily. I just need to be sure I can get off. Get TIME off, I mean.”

“Babe, I get all that. Actually, when Barbara said she wanted to meet you my stomach twitched a little, but maybe in a good way. She’s Ok, and I think — no, I know — she’ll really like you and be happy for me. And pinbahis giriş hey, we’ll have fun! Oh, and I’ll be sure you get off, and I’m NOT talking time off…”

She went on, “I know a great kinda romantic resort, without many kids, especially this time of year, where I can book us if we don’t like what she has in store. We’ll eat and drink our way around Epcot and have some fun on rides all day, then make love like crazy in our hotel room at night, until the neighbors complain.” She was grinning and happy and that made me happy with her.

“You got me, Princess. I haven’t been there in a while, and don’t know the place like you do, but how could I not enjoy being at the ‘happiest place on earth’ with my own Disney Princess. I’ll be the luckiest guy on earth, I’m sure. Really, this is sounding good.” It really was. What reluctance, or nervousness, or whatever I felt was fading. A weekend escape in a fantasy world with my fantasy-come-true lover should be fantastic.

We got to Jill-2’s store and went in hand in hand. She was wandering around out front and greeted us warmly, with a hug and kiss on the cheek for Jill and a kiss on the lips for me, which was a surprise. A male customer was just coming out of the back where the video viewing rooms are and said “Hey doll, how do I get some of that sugar? I come in here all the time and you don’t treat me that way.”

Jill didn’t even turn around to look at him, but fired off, “That’s `cause you’re a customer, Cal. And yeah, you do COME in here all the time, but you don’t always clean up after yourself, either. These two are friends, and they get special treatment if they stop by to visit.” He grumbled a bit and wandered out the door, none of us paying any attention to what he was muttering.

“Hey Teddy, mind the counter Ok,” Jill-2 called out as she took us back into the “toy” section. “I got a couple things to run by you before you go take care of your business in the back, and we take care of ours later, you know.” I didn’t understand the last part, but being the Jills, I let it slide.

We went back to the section with dildos, dongs and strap-ons. There was a pretty extensive variety considering they all have pretty much the same rather limited function. Some of them were huge and I couldn’t imagine actually using them vaginally, let alone anally. Some other things must have been beginner or training devices since they were pretty small and or slender.

“Ok, we’re really just interested in pegging right now,” Jill-2 said, “so I’ll point out a couple things and then there’s one I want to show you. For true pegging, most of the time you’ll need a harness, and almost any dildo with a base can be used with one, as long as it fits.”

“Fits the harness or the recipient?” I asked, half joking.

“I was referring to the harness, stud,” Jill-2 said, and then continued with a smile, “The recipient is far more adjustable. You’d be amazed what will fit.”

“Yeah, I know,” I said, shaking my head slightly. “I worked in the Emergency Department long enough to see, or hear about, some amazing things…”

“Yeah, I bet. Anyway, you can use a double ended dong, like these, without a harness,” she said indicating some about 16 inches long, or more, that looked like two cocks connected base to base and pointing in opposite directions. “You just put each end wherever you want it, one in yourself and the other end in you, too, or in a friend,” she chuckled. “They’re fun, but in a different way than typical pegging.”

“Then there are double ended dongs that do use a harness, where a shorter end goes in the wearer and the main dildo is for the recipient.” We looked a few styles of those. Jill was, of course, more interested than I was in the smaller end. I was just concerned with the enormity of some of the working ends, so to speak, and hoping they weren’t thinking of trying to impale me with one.

Jill-2 moved us along to the more “standard” dildos. “The typical dildo strap-on has to use a harness of some kind and the base of the dildo or the harness might rub against your clit, if it lines up right. They’re the least reliable at giving physical stimulation to the wearer. Of course there are different styles of dildos, too. From anatomically correct to plain peg like things. Some have bent or bulbous ends for better internal stimulation.”

They took a little time to inspect some of these. The anatomically correct ones gave me mixed feelings. Some certainly did look erotic to me, but I don’t like the idea of an actual cock in my ass, so the thought of Jill using a toy on me that even looked that real gave me pause.

“Harnesses can also vary in style and form, as you can see,” Jill-2 went on, moving down the display area. “Typically, they have a few straps to go around your waist and legs, or thorough your crotch, and a ring of some kind in front to slip the dildo through. Some, however, use a peg or other attachment, but you need a matching phallus. There are also ones that are like a pair of panties with a place for the dildo to be inserted pinbahis güvenilirmi or attached. As you can see, they can have a very simple look or be elaborate; sexy or kinda butch, I guess you could say. It depends if you’re into simple pegging, femdom, or whatever.”

I was happy to see that Jill seemed more interested in the sexy type of things than the dungeon mistress look. But she did linger over one with the image of a definite dominatrix on the package as she glanced back at me with her sly smile. I hoped it was a tease, but then again, it might be interesting.

“What I really wanted to show you is the type referred to as a strapless strap-on,” Jill-2 said, rolling her eyes. “Yeah, a stupid sounding name, but I can’t really think of a better description. I guess maybe that’s why the person who is supposed to have invented the prototype called it something else: the Feeldoe. Like dildo, but it’s supposed to let the wearer feel a lot more, so, feel doe, I guess that’s where the name came from.

“Anyway, they’re so popular the maker often sells out. Of course, like any popular item, there are several imitators. I don’t carry any yet, but we’re going to try the original out tonight, and you’ll get a good look in person,” Jill-2 said with a smile.

“Um, what?” I asked. “You guys have something planned?”

“Yeah, I thought I told you,” Jill said. “Didn’t I? The plan is to try pegging. Over at Jill’s house, Jill-2’s house I mean. After my rendezvous with Teddy in the Glory Hole, that is.”

“I’m guessing I’m the Peggee,” I said. “I’m not sure I knew about that scheduled activity. I remember you two asking me if I’d like to try it, but…”

They both spoke at the same time, saying, essentially, “Yes, you are, and I thought you’d like the idea.”

“Yeah, um, I’m Ok with it. I just would’ve liked to know. To kinda get my head wrapped around what my butt’s gonna be wrapped around, I guess.” I didn’t say it, but the idea was getting me aroused. Jill’s playing with my prostate over the weekend got me more interested in this kind of thing, and if we were doing it as a threesome, well… Hmm…

“I knew you would be, Tiger,” Jill said as she kissed me on the cheek.

“So, are you ready to ‘meet’ Teddy?” Jill-2 asked my Jill with a grin. “I’ve talked to him and convinced him it would be ‘helping out a friend’ of mine, but didn’t tell him who. I think he’s looking forward to it, but he’s kinda shy and doesn’t let on. I honestly don’t know if he’s done this before or not, in a glory hole, I mean. I’m pretty sure he’s gotten sucked off, he’s not a virgin.”

“Yeah, I’m ready,” Jill said. “And I’m definitely looking forward to trying it, even though I’m a little nervous. You still Ok with being in there for me, babe?”

“Yup, I’ll be with you,” I said. “I’m not sure how much I want to see you sucking another dick, but at least I won’t see the whole guy. Now that I think about it, I don’t know if that’s more weird or less…”

“You two go get settled down there and I’ll send him along in a few minutes,” Jill-2 said.

As we headed back to the video viewing rooms and glory holes, we noticed that Deejay had arrived and was chatting to Teddy at the front counter. “Hmm, that’s interesting,” Jill said, “I didn’t know she knew Teddy. Maybe they didn’t need our help after all.”

“Maybe you underestimated them.” I said. “If they do have something starting, or already going, I hope she doesn’t mind you horning in and sucking him off. Even if it is ‘anonymously,’ sort of”

“I think I can check on that before we start, and if she does, I can alter my plans for tonight. I may just have to settle for my favorite cock instead,” she said with a smile and a pat on my ass as we stepped into our familiar room, number 3.

Jill followed me in and shut the door, then wrapped both her arms around me from behind, caressing my chest and kissing the back of my neck. Her hands slid down my front until they were caressing my semi hard dick through my pants. “Mmm, I haven’t gotten to greet this guy yet today, and I’ve missed him,” she purred in my ear as she unzipped my fly.

I turned around in her arms, then slipped my hands into the back of her shorts, fondling her ass, and said, “The feeling is mutual,” before kissing her. As our tongues found each other she undid my belt, while my fingers felt the moisture gathering between her legs. Just as her hand moved into my pants and found my erect member, there were a couple raps on the door and it opened. Deejay was here.

“Oops, sorry to interrupt,” she giggled. “Glad you weren’t fully engaged, yet. Maybe you should have locked the door,” she added as she did just that.

“Nah,” Jill replied, “then we would’ve had to stop to let you in.” She pulled her hands from my pants and I removed mine from hers as she went to give Deejay a hug. “Hi sweetie, glad you could make it.”

“I’m glad you invited me,” Deejay replied. “I haven’t seen this guy in a while,” she said turning to me and moving closer. As I opened my arms to hug her she reached into my open pants and pulled the waistband of my briefs out to get a look at my obvious erection. “Or this guy either. Mmm, both good looking as ever.” She let go of my underwear, patted my cock through the cloth and leaned up to give me a little kiss on the mouth.

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