Lucky Over 40 Ch. 02: His Lead

We went to the bar and she sat on a stool, while I watched with anticipation to see how she reacted to the plug she had almost forgotten was in her ass. She sat, jumped back up a bit, and then settled down again more gingerly, looking at me and saying "Oh! You were counting on that, weren't you? I'll remember all this, mister!" And she wiggled her butt a bit on the stool, smiling as she did.

We had a drink and watched the staff making sushi orders, then moved to a booth, sitting beside each other. Being anxious to get back to her house, we just ordered a couple sushi rolls to share. I reached down and slid my hand up her thigh until I was playing with her pussy. She reached over and tried to unzip my pants, but I interrupted her. I told her she needed to slide her skirt up again so she wouldn't get it wet and, after a little hesitation, she complied. As she lifted her ass to do so, I reached under her and gently pushed on the end of the plug in her ass. She gave a soft moan, with her head tipped back, then pulled my hand out, and sat back down. The food came, we ate, paid, and headed back to the car, without wasting any time.

I opened the car door for her, and told her to reach in and fix the towel on the seat. She bent over without thinking and I lifted her skirt as she did so. She quickly started to stand back up, but I put a hand on her back to let her know to stay put, and slid my other hand between her legs, along her warm, moist pussy lips, across her taint and wiggled the little gem in her ass. I walked over to my side of the car and when I got in she said "Would you do me a favor and drive over to the adult store a minute. I need to go in quick to do something." I did, without asking anything, and she hurried inside, as carefully as she could with a plug in her ass, coming back out after just a couple minutes. She settled into the seat, carefully, putting the towel under her bottom, and just said, "Girl talk."

While driving home I told her she needed to lift her skirt again. She did, and asked me if she could take out my cock. I told her that would be fine, if she was careful not to interfere with my driving, or making a mess. She reached over and gently rubbed my crotch, unzipped my pants, undid my belt and then my pants button. Reaching in, she slid her hand over my briefs, and said, "Oh, something has been leaking. How did that happen? Let me see if I can find out where that came from," and she reached inside, taking my hard, aching cock in her hand and rubbing her thumb across the end of my swollen head. "Um, I think I found it," she continued, "I'd love to lap it all up for you, but don't think I should do that while we're driving. Maybe I can just wipe it up and lick it off my thumb," and she started to do exactly that. She continued rubbing and stroking my hard on for the next few minutes until we pulled into her driveway. Then she quickly sat back in her seat, opened her door, and said, "Time to go inside. Last one there licks the other `till they come." She had turned the tables on me, knowing full well I could never get my pants fixed quickly enough to beat her to the house, but somehow, I didn't really mind. And it was fun to see her start to run, suddenly remember the plug in her butt, and then press one hand on her ass as she ran.

When I did get inside, she was already in the bedroom, calling for me to hurry up. She was out of her dress and on the bed, up on her hands and knees with her ass facing to the door, swaying it back and forth. I was just holding my pants closed, and dropped them when I saw her. Kicking off my shoes, and stepping out of my pants, while unbuttoning my shirt enough to pull it off over my head, I just about dove at her, burring my face in her from behind. "That jewelry really does look so good on you, but I can't wait to eat that delicious pussy right now," and I took hold of her legs, flipping her over onto her back. I spread her legs, climbed between them so they draped over my shoulders, and tried to devour her hot sex with my open mouth, lapping at her wetness with my tongue while making animalistic noises.

She grabbed my head, pulled it into herself, and growled, "Yes, eat me, eat me and make me come, then give me that cock." I did my very best to follow her instructions, not caring anymore who was supposed to be leading who tonight. I wanted her to come, I wanted to sink my cock into her, and my balls wanted to release what they had been accumulating all day as I thought about this night. With my mouth and fingers I soon made her quiver and quake with a satisfying orgasm. I always love to see that!

She pulled my sodden face from between her legs and up to her mouth, kissing me deeply and humming, "Mmm. That felt so good, and I do taste good, too. Now I need you to put your very own plug in my hot cunt and fuck me." She pulled my cock toward her crotch and I plunged right into her warm wetness. "Oh, I need you right there. I don't really like the word I just used, but I am so horny right now that cunt just seems to be right one," she said, emphasizing 'cunt' like a grunt.

"Dirty words have their time and place, and right now your hot, horny mouth, to say nothing of your hot, wet cunt, have me fully wound up," I replied, while pumping my cock deeply in and almost all the way back out, as slowly as I could, using as much self-control as I could muster. I kissed her deeply again and tried to distract myself from the urge to just pound into her until I finally got to let go of all the cum building in my balls. This felt too good to be over that soon. Then I noticed that her pussy felt different, something was rubbing on my dick in a way I was not familiar with, but was very, very nice. "That cute little butt plug in your amazing ass is rubbing against my cock. It's really different, in a very good way."

"The plug is feeling pretty good from my side right now, too. I'm really glad we tried it." And she squealed a bit as she said the last part. "I'm right on the edge of another orgasm. Oh, oh fuck, yeah, YEAH!" Her vagina squeezed me and I let loose inside her, moaning loudly with satisfaction. "Oh babe, did you like that? I wanted you to come in me, and it kicked me over the edge," she panted while shuddering a bit. When she relaxed some, she continued, "Now it's my turn to clean you up, and taste your juice."

She kissed me again, then rolled me off her and climbed over me, taking my nearly spent penis in her mouth, with her pussy and ass near my head. I kissed her inner thighs and licked up toward her pussy, while my finger probed her labia and teased her clit, making her squirm some. My cum was starting to leak out of her and I licked at the trail running down her leg, which made her squirm more, but she stopped me, turning her head and saying, "This is your night in charge and I have clean up duty right now." She threw her leg over me and laid on top of my body, saying, "I really appreciate what you're doing, but it's distracting me from pleasing you right now," and returned to sucking our cum off my cock.

I told her, "Well then, if you're going to concentrate on me, I want you to really show me how much you like my cock, but not just by sucking on it." I'd never really received "cock worship" but was curious to see if she could, or would, show me what it was like. "Do you follow me? Can you do that?"

"Oh yes, I can do that! It's such a nice cock," she kissed the head, "and a tasty cock," then she licked up the now stiff shaft. "I think it looks very nice," she fondled it, moving it all around as if inspecting it, "I much prefer a circumcised penis," and she put a big wet slobbery kiss on its swelling head, "especially to suck on," and she did, but only briefly. "I also think it's just the right size for me," she stroked it, "not too big to choke me," she deep throated me up and down a couple times, teasing with her tongue as she did, "or bang my cervix, or stretch me too much," she stroked it again, all wet with her saliva, "but big enough to hit all the right places," she kissed it, "in the right ways," and she kissed it wetly it all over. "Yes, I really like this cock," and she continued to kiss, lick, stroke and intermittently suck on me, while making sloppy, sexy noises, and continuing her bits of commentary. It was a new experience and a real turn on for me. Besides the flattering I find that sound adds to sex, whether words, dirty or not, vocalizations, or just the physical sounds, especially the wet ones. A loud slap can also be arousing..."

I told her, as I caressed her ass, that she could start sucking me off when she was ready to do that. After a little while, I began to play with the end of the plug, eventually starting to slowly pull on it. She began to hum and moan around my cock, which was now fully in her mouth. She spread her legs a little further and wiggled her ass in a way that worked the plug around her ass more, while I was still gently tugging on it. She fingered her pussy some, and then put that finger to my ass, covered with her wetness. She teased and pushed, and then slid it inside me. She pushed it in and out, like she was fucking me, and it brushed against my prostate just enough for me to feel it. Her finger started to wiggle and squirm, and before long, so did I. She kept making noises around my cock; moans, hums, and wet sloppy sounds as he moved her head up and down. It was all very hot, and it was all building to a climax, literally.

When I finally came in her mouth I pulled harder on plug in her ass and as the widest part popped past her sphincter, she grunted and collapsed on my chest. I rubbed her back and she let my softening dick slip from her mouth. "Mmm, that was good," she said as she turned herself around on top of me. She kissed me again, letting me taste some of the cream she just sucked out of me, as we embraced.

We lay cuddling together for a few minutes, as she gently caressed my chest, before she said, "I wasn't really sure about all this when the night started. I guess I didn't know what I expected on a date where I was supposed to just follow your commands all night, but it sounded interesting. What you'd planned was a real surprise. I wasn't all that into the butt plug idea at first, but the girl at the store helped convince me. Then, when you actually wanted to put it in me, and in the back of car, I got a little scared again, but you got me really worked up. Wearing it the rest of the night was stimulating and kind-a scary at the same time. From the drive home to now, it just kept getting hotter. I'm looking forward to doing more "exploring" with you. But next time, it's my turn to be in charge and I won't forget how much you pushed my buttons tonight, buddy." She kissed me again and took hold of my cock, which was growing hard once more.

"I hope the buttons I pushed were good ones. They certainly seem to be ones that turned you on, instead of off -- just like you're pushing my On button now. I know that I probably took you out of your comfort zone sometimes, and I meant to do that, a little at least. Was being in new territory arousing?"

"Yes, it was, tonight was anyway," she replied while aimlessly caressing my cock and balls. "Now I have to figure out what I want to do to give you the same kind of experience, being uncomfortable in a really arousing way. I think this is going to be fun, and stimulating, and hope it turns out as good as tonight has --for me at least, since it's going to be MY night, you know."

"If it ends up with both of us getting each other off I think it'll be great. We really seem to have similar tastes and thought processes, but can still surprise each other. I'm sure you know that the brain is really the biggest sex organ, and when it's used right as part of the play, there's a lot more fun. I'm confident you'll come up with something that will be pleasing, for both of us."

"Yeah, I don't think my Ex ever liked to use his brain near as much as he liked to use his dick. That may explain a lot," she said with a little remorse in her voice. Anyway, l like I said, next time it'll be MY night, so I'm more concerned with you pleasing me than with getting us both off, but you'll probably have a good time, too," she said very teasingly as she gently squeezed my 'package.'

"You may be taking this idea of being the 'lead' a little too far -- or maybe you're just trying to play with my brain and push my comfort zone already -- but it is about exploring so I'm kind of anxious, in more ways than one, to see where you go with this. And pleasing you by giving you orgasms is always a good time for me, so far anyway." After a pause I asked her "So, when will we have this next date?"

"Most week nights seem to be out for one of us or the other, so I hope you can wait until Friday -- I hope I can! But my daughter may be home, so how about I get you at your place?"

"That's fine, and I think maybe I can wait until Friday, but if it may not be easy. Anticipating tonight had me hard most of the day. But, speaking of your daughter, do we need to start putting clothes back on?"

"Yes, we probably should, just to be safe. I think I may need to encourage her to take a weekend away with friends pretty soon."

"Hmm, or maybe we could take a weekend away someplace," I replied as I got up to gather my clothes. "We'll have to look into that sometime. But right now, I'm just looking forward to Friday."

"I think I could arrange to take a weekend away with you. If my daughter went away, maybe we could just spend a whole weekend right here in my big bed," she said, kissing me playfully. "I'm really looking forward to Friday, too, but we won't be spending the whole night in bed, I have some other thoughts."

"I hope they're nicely naughty thoughts. If the anticipation is anything like what I had today, or I even just get thinking about it too much during the next several days, I may have to take things into my own hand, if you get my drift. I'll try to behave, though," I said teasingly, as I put on my briefs.

"You better behave, mister. I don't think you'll be fooling around with anyone else, but I don't want you jerking off all week, either. Save that cum for me," she said as she gave my 'package' a gentle squeeze through my briefs. I gave her a questioning kind of look, "Ok, at least save the last few days for me!" And she patted my crotch. "Oh, and there's something else I've been reading about, that I'm not going to explain now, you can google it. I know you like eating fresh pineapple, what do think about pineapple juice?" I indicated it was fine, though a bit sweet to me. "Good, I'd like you to pick some up on your way home and drink at least a glass a day, two would be better. Will you do that for me, for us, babe?

"Sure, I'll pick some up and do my best to have a glass or two daily," I agreed. "For how long? Is this supposed to make me big and strong, or is it good for my heart, or for my libido, as if I need to be any hornier with you around. Or maybe it's good for my endurance, `cause of lots of fructose."

"Now who has a lot of questions? Just drink it every day, and if it becomes an issue at some point, let me know. I told you I'm not going to explain it now, just google it if you need to know what it's for. I did say it's supposed be good for us both, though. That is, your drinking it should be good for both of us. It may turn out not to be, but let's "explore" it, Ok?" She kissed me again, gently, but deeply.

As I headed to the door she gave my ass a big tweak, making me jump a bit. "Just remember that your ass, and everything else in that area below your belt, is mine right now. I intend to make good use of them on Friday, so don't be abusing them in anyway before then," she said with a big smile. "And don't forget that pineapple juice!"

I did like her playfulness, and her interest in my ass, etc., but there was a hint, or more possessiveness in her comment that gave me a little concern, as was much of what she said on the latter part of the evening. She wasn't going to turn out to be a crazy lady who would tie me up in the basement and make me her sex slave, would she? If he did, would that be terrible? Well, yeah, it would, in the long run, and I'm not that into BDSM anyway. Oh, could that be part of her plan for Friday? If so, am I ready for that, and if I object will she actually listen? I had told her my boundaries, how much would she try to push them? I really liked the time we had so far, and thought things could continue well. I wasn't 'smitten' with her, not yet, but I was very happy to be dating her and not looking for anyone else on-line, or anywhere else, right now. But, at the same time, I really was wondering what she already had in mind, and what had I gotten myself into. Little did I know what was in store on Friday.

Stay tuned for that story.