Lucky Over 40 Ch. 03: Her Lead

Finally, I warned her that I was about to come. She hummed "Mmm," and took me deeper in her mouth, letting go with her hand, but still caressing my prostate with her finger, until I exploded in climax, lifting my pelvis involuntarily and pushing my cock into her mouth. She grunted slightly, in surprise, and some of the load leaked out of her mouth, running down my shaft. I had another spasm, shooting another load into her mouth, and we both moaned. More cum leaked down my cock. She slid her mouth off my cock and moved a bit, but her finger stayed in my ass, still rubbing, but much more gently, and I shot again, onto my belly. Her other hand went behind my head and lifted it slightly as she brought her lips to mine for a kiss. As our lips touched, and parted, cum ran into my mouth, followed by her tongue.

As we kissed, I squirted another shot of semen, onto my belly, then drippled some more until she slipped her finger out of me and just rubbed along my ass crack tenderly. My cock twitched as cum stopped flowing, and it began to shrink faster than I think it ever had before in Jill's presence. She broke our kiss and asked, "Did you like THAT, babe? Did you like coming in my mouth so hard? Just so you know, I normally don't care if you warn me before you come, but this time I'm glad you did! It was such a big load, I couldn't keep it all in, and it felt weirdly hot leaking out of my mouth. It was even hotter letting it run into your mouth when I kissed you." She looked down at the cum I had spilled on myself, dipping her fingers in it.

"You KNOW I liked that, lover. It was pretty amazing. I've had some big orgasms, but I don't think I ever came for that long. For a first time prostate masseuse you did a fantastic job, even if I have nothing to compare to." As I fished speaking she put her cum covered fingers in my mouth and moved her body so she could lick the cum from my belly.

As she moved back up, cuddling next to me and wiping her fingers across my lips, she said, "You taste good, don't you? Maybe the pineapple juice is working." Then she kissed me again, with her cum covered lips. She settled her head back down by mine, both of us enjoying the post orgasm feeling of deep relaxation, even though hers was several minutes ago.

She returned to her previous conversation, both of us less distracted now, "I liked giving you that special massage. You're really my first ass play partner. You're my first dominance play partner, in either role, and believe it or not, you're really my first partner for exploring the wider world of sex beyond sucking then fucking then done."

"You're very attractive and very sexy so, yeah, I find that kinda surprising," I replied. "But you married young and haven't been single a long time. So, even though you've been using the dating sites, maybe I shouldn't be surprised. Anyway, I can say the same of you for most of those firsts. I'm glad you were, and look forward to more firsts for us. Tonight you gave me my first experience with being an exhibitionist, reluctantly I might add, and it wasn't really the kind of first I hope to have more of."

"You seemed to be enjoying it more after a while. I think you liked that sweet young thing flirting with you, and her staring at your cock. Maybe I should've gotten her to do more than just stare," she teased, at least I hope she was teasing.

"I'm glad you didn't," I said in earnest. "It was bad enough having you tell a stranger about our sexual activity, and right in front of me, but then being exposed to her! Ok, though, I'll admit her positive reactions to it all were kinda erotic for me, and maybe a bit flattering, too. Yeah, I was starting to enjoy it by the end -- not that I wanted it to go any farther -- BUT, then you offered me to her, a perfect stranger, as a sort of living sex toy!"

"Ok, I have a confession," she 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 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 out of her mother's earshot. We've had some frank discussions about her love life, and mine, and sex, and the 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 all just sort of spilled 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, just 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 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 about 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 was still concerned with the ramification 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, but still a stranger to me. It's still kinda embarrassing, but, yeah, now I find it all more erotic. 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." She 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. (You can read how that call went in part 4 of this series!)

After a somewhat awkward call that turned out to be live, rather than the voice mail I expected, I said to Jill, "This situation is all very odd to me, but good, I guess. As I've told you before, I haven't had good luck with dating -- until I met you! -- or 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 bone, really -- and she wants you to show her how to have some good kinky sex. Go with it!" And she squeezed my cock again, which was now pretty hard from her toying with it for several minutes. "Now, speaking of some good kinky sex, MY night isn't over yet, and I've more for you to do with me, or to me, so get with it!"

She quickly got up and made sure the drapes were fully closed across the window behind the couch, then stood on the couch and put her pussy in my face. "Show me again that you know how to eat me until I come, babe. I wanna be sure you can do it for Deejay, too, since her boyfriends haven't been very good at it. Yeah, that's it, kiss me there. Ooo, yes, your tongue feels good." She had hold of my head and was moving it around as she also moved herself.

"Yeah, you're good at this. Yeah, push that tongue in. Now, play with my ass, too, oh yeah. She'll like it if you do that for her, babe. Oh, suck my clit, YES. Oh, yes, yes, push those fingers in my pussy and rub my g-spot! Oh yes, keep wiggling that finger in my naughty butt. Suck me! Suck it, I'm gonna come. Yes, YES, don't stop, don't stop any of it! Oh, oh, oohhh, yes, YESSS, uuuggggghhHHH," she stiffened up as she groaned, and held my head tightly. She pulled my face almost off her pussy, then all the way off, then she sank down in my lap, and I let my fingers slide out of her holes. We sat there with my arms around her while she wrapped her arms around my neck and shoulders. "Oh, that was good," she said, leaning back after a while. "That's another new position you taught me."

"That I taught YOU? You're the one who climbed up on top of me and shoved my face into your gorgeous crotch, or the other way around" I said, incredulously, but with a big smile. "I'm not complaining, though! It was good. And your wet pussy against my cock right now is good too, but it could be better..."

"Oh yeah? What, do you want me to sit on your dick? Right now, right here? I could do that," she teased. "But I think we'll have more fun back in bed," and she got up, pulled me up by my stiff dick, and lead me back to bed. She climbed on top and fucked me -- yes that's right, she was definitely in charge and was definitely fucking me, using my cock in her, but I'm not complaining one bit -- and we did several other things she directed. I'm not sure I really got to initiate much of anything, that night. I did clean her up, or out, after our last copulation, but she initiated that, too, by climbing up my body and placing her cream pie cunt in my face. Once again, I didn't mind. I didn't mind any of it, even though during dinner I was, at various times, pretty embarrassed, uncomfortable, or at least very self-conscious. But at the time I was also quite aroused, and now, knowing what I didn't know then, I find it was all really erotic. I think she accomplished her goal, maybe both our goals, I guess, for this female led date.

Do I want to be shown off in public again or have my sex life discussed with others I don't know, especially in a public setting, probably not, but that night was a turn on and thinking back on it can still turn me on. Do I want Jill to take the lead again? Sure, although I know that to her it's more than that, she really takes charge, that's how she is. She's not a BSDM Mistress type, (not now, anyway, maybe she could be) but she certainly can get Dominant with a capital D, when given the chance. I don't want to be just her sub, either, but it can be fun to do as she "commands" and to release all control to her, now and then. I like to see where her imagination takes us, and she seems to like it when I do that with her. It's hard to have two drivers in the same car, at the same time, and it can be like that with sex sometimes, too. You may, or may not, need to know the destination each other has in mind, but the ride can be very enjoyable when you leave the driving to someone else.

Check out part 4 to see what happened with Deejay.