Lucky Over 40 Ch. 04: The Waitress

This is the fourth part of the story of two single 40somethings that met on-line and started an adventurous sexual relationship. The overall story is about exploring completely heterosexual kinks, and this part contains things like a 25ish female having sex with a 45ish male, mild female dominance, mild CFNM, face sitting, anal play, cum play -- including eating some of his own cum. Among other things, there is NONE of the following: pain, bondage, incest, underage sex, homosexuality, bisexuality, or nonconsensual sex, of any kind. 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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During our date Friday night, when Jill was the lead -- or in charge as she really seemed to consider it -- she had had recounted much of our kinkier moments, and exposed my naked erection, to our much younger dinner waitress. Jill not only exposed me to the girl, but when she said she desired some better, and more varied, sexual experience Jill offered to "loan" me to her for that purpose! The story of that date is in part 3 of this series. This is the story of how the "loan" to Deejay, our waitress, played out. (I'm including a few paragraphs from part 3 to tie it together and set the stage.)

Following our mutually satisfying orgasms, Jill and I cuddled in bed and discussed some of the evening's events and experiences. Well, mostly my experiences, and our thoughts about them. Of course, the topic of our waitress, my exposure to her, and especially the proffered "loan" to this perfect stranger featured in that conversation.

"Ok, I have a confession," Jill said, a little bashfully. "She isn't really a perfect stranger, not to me anyway. Deejay -- that's a nickname based on her initials -- is the daughter of a regular home care patient of mine. I've known her for several months, and we talk a lot while I care for her currently bedbound mother, as well as outside of her mother's earshot. We've had some frank discussions about her love life, and mine, and about sex, and her lack there of. I already knew she had disappointing boyfriends, and she knew I'd met this guy that rocked me sexually, and about a lot of our last date. I told her I'd be in charge at the next one and wanted to push your limits in a sexy way. She told me the restaurant she worked at had a secluded table with a bench seat that lovers liked, and suggested I could make use of it. I asked her to reserve it for us, to be sure to be our waitress, to follow my lead -- like you would be doing -- and not to be surprised at what transpired." It was all just sort of spilling out of her.

"She might've even been as pleasantly anxious about it all as you were," she continued. "But the last part, about loaning you to her -- and it IS just a loan, so we're clear on that -- wasn't really planned. The idea had crossed my mind when she was complaining to me, as she did tonight, about her unsatisfying, self-centered, vanilla boyfriends, but I didn't bring it up to her and I didn't plan to actually make the offer, until it seemed like a really good thing to do at the time. Are you mad at me? Do you want to back out?"

"I'm not mad," I gave her a kiss. "I don't really know what I am, other than maybe a little relieved that this wasn't quite the encounter with a stranger that I thought it was. Knowing that she knew at least some about our play time already, and that she was at least partially prepared for your antics, makes it less worrisome, I guess. I still have concerns with the ramifications of flashing a stranger, and in a public place. But actually, as I think about it, I guess I find it more erotic now, since it was essentially "safe" with her as a willing participant, yet a stranger to me. It's still kinda embarrassing, but, yeah, now I find it all more erotic than worrying. And, the loan portion is actually more appealing, too. If you really want to do that, and if she really wants the 'experience,' I think I'm up for it."

"Oh I know you'll be UP for it, babe," she said with a gentle squeeze of my cock and balls. And I really believe that Deejay is, too, or she wouldn't have given you her cell phone number. I recognized it since I've talked to her for work, and as friends. I think you should call it now. She's still working so you can just leave a voice message and give her your number and some info to finalize a time and place." Jill got up to find her purse with the number. I figured a voice mail might be more comfortable to start, for me at least, so I retrieved my cell phone and we sat together on my couch, both still naked, while I made the call.

Jill read me the numbers as I dialed. It rang and then a voice answered, just saying "Hello?" It wasn't voice mail, it was Deejay, in person! Oh shit!

I stammered, "Hi, um, it's Rob, Jill's friend from tonight, remember? I, um, thought you'd still be at work, but um, well, Jill wanted me to call now and leave you a message. I, um, didn't expect you to answer." (Yeah, I was real suave and smooth...)

"Oh sure, how could I forget," she said, with a little laugh. "You really SHOWED me a nice time," she continued, with a definite emphasis on showed. "I'm still at work, but since I'm on a break I could take the call. I didn't expect to hear from you so soon, but I'm glad I did, or I'd still be anxious, hoping you'd really call. I've been thinking about it ever since you guys left. So, what's up? It's still UP isn't it, or did Jill take care of that already?" She giggled a little.

She was obviously having some fun with me, but I thought there was also a bit of a tremble in her voice that made her sound somewhat nervous. I was certainly nervous, and replied, "Um, yeah, she did. She really did. She's right here, too." Jill was snuggling up to me, close enough to hear Deejay without being on speaker phone. She was caressing my chest with one hand while chuckling at Deejay's teasing, and my embarrassment. "Um, I'm, glad you liked what you, um, saw, with us, er, of me, and all." Jill patted my chest and told me to relax, that everybody enjoyed everything, even me, and that I should just be myself with Deejay. She began playing with my nipples, which was rather distracting, but probably a good thing, since a little distraction might help me relax more on the phone.

Deejay heard Jill, and said, "Yes, I really did enjoy it all, and though it's cute to hear you getting flustered with me, I'd really like you to be relaxed about this and just be yourself with me, too. Jill told me some stuff about you and I really liked it all. I'd like to learn more about the kinds of things you guys have done. Learn firsthand, that is, ya know? But I'm also kinda nervous about it, and I'm not thrilled with the idea of trying it with an old boyfriend or some other young guy, maybe that I don't know that well, and being worried he'll think I'm weird or something, ya know? But I think I wouldn't be worried about that with you, and Jill said you're really open to stuff, and really good in bed, or where ever you play around," she giggled some more.

She seemed to take a deep breath and continued, "So I'd really like it if you'd show me some stuff, Ok?" Then she got a little playful again, and added, "I mean do some stuff with me, you already SHOWED me some nice stuff earlier tonight, didn't ya."

They were both getting me to relax, and she really did seem to want to do this, and with me. Jill was encouraging it, too -- in fact, she really set it up -- so I felt more Ok with it in a few ways. As my mind whirled, thinking all about it, my cock was now stirring, from the thoughts of this arrangement, and probably from Jill's nipple teasing. "Yeah, um, I guess I did already show you something -- or Jill did," I responded. "And yeah, I can do that for you. Sure, I'm happy to help you any way I can."

"He's VERY happy to help you. ANY way he can," Jill chimed in loud enough to be sure she was heard on the phone. "You should see him rising to the occasion, if you follow me." She was embarrassing me again, and this time I enjoyed it, sort of. This was such a weird situation, but a very erotic one.

"Yeah, Jill, I got you," Deejay replied. "Seems like he's usually UP for anything, isn't he?" She giggled, and continued in a half whisper, "I like that about him, too. And I'm glad that he's getting UP for me. It's getting kinda WET around here, as I'm thinking about it." After a brief pause she spoke up again, "When can we try to do something to fix all this? I'm free Sunday afternoon and Monday evening if you can come over to my place. I'm covering at home with Mom then, in case she needs something, but we'd have plenty of privacy and she usually doesn't need much of anything. But I sure do, need something, I mean. So, when can you come help me?"

"I'm busy during both those time slots, so I won't be using him," Jill offered. "And I'll try not to wear him out before then."

"Gee, thanks," I said to Jill. "Either of those work for me, Deejay. Do you have a preference, and what was it you wanted the most help with? I was a little distracted earlier tonight when the two of you were chatting, until I heard myself being volunteered!" Jill tweaked my nipple again.

"Sunday would be great, I'd love to get started ASAP," Deejay replied. Her voice got quieter again, like she didn't want to be overheard, "and a little afternoon delight would be really nice, you know? That special massage is something I want to learn, and all the cum play sounded like a kinda kinky fun thing to try." Then she returned to a more normal volume, "I'm guessing that really anything you can do for me will be just fine. I am very interested in getting some work done on the BACK DOOR, and there might be something else that needs attention, too, or anything else you find to work on with me. Is that Ok? I'm not asking too much, am I?"

"No, dear, that's just fine," Jill cut in. "But that's probably too much for one afternoon. We don't want to rush it and ruin the experience by cramming in too much at once, figuratively and literally, you know."

"Especially if Jill wants more from me this weekend, too," I added. "But yes, we all want this to be a good experience for you, so too much at once won't work so well. We'll see how Sunday goes and take it from there. After what happened tonight I may be asking for trouble, but since this is about YOUR experience, I'll let you take the lead on Sunday. You decide what you want us, or me, to do."

"That sounds good, and very nice of you," she replied. "I haven't had that kind of experience before, not with this kinda activity. I really, really appreciate your help. I've needed something taken care of for a long time. I'm looking forward to Sunday. Is around noon Ok, with you?"

"Noon is fine," I said. "Jill can let me know how to get there. Do I need to bring condoms or anything?"

"Great! No protective equipment is needed. Jill knows that's all taken care of. Maybe you should bring some kind of lubricant for some of the work, though. I'm so excited to get this project underway, and I hope I can show my appreciation to you properly. I'll try my best. They need me back at work now so I gotta go. See you Sunday. Please don't be late! Bye, Rob." And she hung up.

"I really think she's excited about this, and I really liked how she was flirting with you, babe," Jill said as I put down the phone. "You're not an old man, and you're attractive -- maybe not a Hollywood hunk, but definitely attractive, in many ways," she said as she kissed me. "And you do have a nice looking dick, especially when it is hard, like it seems to be most of the time, at least when I see it anyway. I don't think she'd want to marry you, probably not even a dating relationship, but I can certainly understand why she'd want to hop in the sack with you or even go out with you a few times, especially after what she's heard -- and seen -- of you."

"This situation is all very strange to me, but it's good, I guess. As I've told you before, I haven't had much luck with dating -- until I met you! Not much luck with women in general, and especially not with knowing what they want. I've got very little confidence about it, unless someone really shows me they're interested in me."

"Babe, you really can be dense for someone who's so smart. She was telling you she's VERY interested through that whole call, and even some at dinner, too. Accept that this 25ish hot chick wants to jump your bones -- well, jump on your boner, really -- and she wants you to show her how to have some good kinky sex. Go with it!" Then she turned my attention back to her, well our, pleasure for the rest of the night.

On Saturday afternoon Jill and I went out together to a town fair nearby. Then we went for a walk in a park and ate some take out for dinner there. We held hands, did some light kissing and flirted a lot, but we were out in public the whole time so we didn't get really intimate. She patted my butt from time to time, and kept a hand in my back pocket quite a bit. She did cop a feel of my crotch a couple times, as did I of her various "naughty bits," but only when no one could see it. It was light and fun.

That evening we spent back at her house, where she's most comfortable, watching TV. We made out on the couch, with some moderate petting like two high school kids, and we cuddled until we fell asleep for a while. When we woke it was close to the time her daughter would be home so we fixed our clothes and I said good night. We didn't have sex or even an orgasm, which I think was a good thing since she pretty well drained me the night before, and she might have even been a little sore, too. Or, she might just have been holding me back for the next day, and her "loan" of me to Deejay.

Sunday rolled around and I started trying to think about what I would do with Deejay, which kept me horny most of the morning again. I headed up to her house, getting there about noon, as we arranged. I knocked on the door and she opened it pretty quickly, as if she'd been right there waiting. She was dressed in skimpy athletic shorts, and a tank top that did a nice job of highlighting her lovely firm, round tits, with their nipples clearly poking out front and center. Her dark wavy hair was pulled back and she was grinning, shyly, seeming a bit nervous.

"Hi, I was hoping you wouldn't be late. Jill told me she'd tell you to wear scrubs, to kinda blend in with the medical people that come by. You look really nice in them," she said, looking down. Was she just avoiding eye contact, or was she looking at the growing bulge in my crotch? "Come on in, and we'll go up to my room. Mom can't hear what's going on in that part of the house, but I have a baby monitor thing so I can hear her if she needs me." She turned and started up the stairs, my eyes glued on her very cute, round butt in those skimpy shorts. I thought I could just see a glimpse of her pussy; at least I was really trying to.

Her room was bright and spacious, with a queen sized bed and a little sitting area, among other furnishings. She led me in and shut the door, then turned to me and said in a rush, "I don't know why I did that since there's no one else that can come in. Just nervous I guess. I've been thinking about this all morning, well ever since you called, really. I'm really excited about it, but, well, I'm pretty nervous, too."

I took her hands and said, "You know what, I'm pretty nervous, too. And, I've been thinking about it all morning, and longer than that, too. I've never done this sort of 'loan' or even 'sex ed' thing before, and Jill really arranged it all. But she did it for you, and today is all about you, and what you want to do, or learn, or whatever. I'm not really sure how to start, but how about if I give you a big hug?" I dropped her hands, opening my arms to her, and she came right in, putting her arms around me with her face against my chest. The top of her head come to just beneath my nose. Her hair smelled nice, her body felt soft and supple, and her hands felt great as they caressed my back.

My cock was stiffening and pushing against her belly. Deejay was very pleasantly curved, but not over weight. I slid my hands down from her back to her waist. I wanted to slide them down to grab that curvy ass, but I wasn't sure she was ready for that, even though we were there specifically to have sex. Finally I asked, "Are you Ok, with all this I mean? Do you want to sit and talk first, or something? Or we can just stay like this a little longer." I was clueless how to get started, and I really wanted her to be comfortable.

"Would you kiss me," she asked, and then turned her face up, looking me in the eyes, maybe for the first time. I bent down and gently kissed her sweet full lips, trying to take it slow. She however, quickly pushed in harder, opened her lips and pressed her tongue into my mouth. I responded without hesitation, and we were quickly devouring each other. Her hands ran down my back and grabbed my ass, pulling me into herself so that she must have felt my hard cock pushing back. I let my hand grope her ass, but before too much longer, she relaxed and pulled back slightly.

"Jill said you're a good kisser, and she's right. That was nice. And she was right about your ass, too," she said, blushing slightly. "She told me, like you just did, that this is all about me, and what I want, so I'm gonna try to let you know what I'd like today, but I'm not used to being able to do that, not during sex, and I'm still nervous -- but that kiss helped, I think." She paused a moment, took a deep breath, stepped back a bit and while looking towards my feet (or maybe my crotch), said, "I want you to take off those scrubs." Then took another step back and looked up at my face.

"Ok, that's a good start. I have a little experience stripping for a hot woman, so I can do that," I said, only half joking. I wasn't very nervous about stripping for her, except that Jill convinced me to wear something else, underneath. I pulled my scrub top off, and became a little self-conscious about my lack of anything resembling a "six pack." I slipped off my shoes as I untied the scrub bottoms, letting them drop and stepping out of them as gracefully as I could.

I was now standing there in just my socks and the red thong pouch thing she had previously seen me in, sort of. Like the last time, the whole head of my erect cock was poking out past the top of the pouch. I was, however, much less embarrassed than the last time, and actually a little eager to see if maybe she thought it was at all sexy. Her eyes opened wider, staring, and a big grin came across her face, so I think it was a winner. Whether she thought it looked sexy, cute, or comical, I couldn't tell, but she seemed pleased and that's what mattered.

She kept looking at my hard-on and moved toward me, reaching out to take hold of the sides of my waist band. She pulled it down to below my balls, as far as she could reach without bending over, but enough to have me fully exposed. "The other night was pretty dark, so this is a much better view. Jill told me I'd probably like it, and she was right about that too. I've seen my boyfriends before, of course, but not quite like this, not on my terms, and not in a relaxed way -- not that he's relaxed at all," she said, referring to my stiff cock. "He looks very eager. Is it really because of being here with me?"

"It sure is," I reassured her. "That, and what we were doing a couple minutes ago. And also about earlier when I was thinking about sex with this hot young woman I really don't know, yet. It's all a mixture of things, but it's because of you that I'm hard, that's for sure."

"You called me hot a couple'a times now. Do you really think so?" she asked.

"Yea, I do," I replied. "I've definitely got this hard-on because of you. What would you like to do about it, or with it, or have me do with you, or... Ok, I'm babbling. Do you want something now, or do you want me to take the next step?"