Lucky Over 40 Ch. 02: His Lead

This is the second part of the story of two single 40somethings that met on-line and started an adventurous sexual relationship. It is mostly about exploring completely heterosexual kinks, and this part contains things like mild male dominance, mild exhibitionism, mild humiliation, 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 non-consensual sex, of any kind. If anything above bothers you, please don't be upset if you keep reading! (Please DO make use of the Tags for stories to see what you may like or not like.)

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All day my mind was filled with thoughts of Jill and with planning our date tonight. Yesterday was a fantastic sexual experience and the thought of it, and what might follow, had me distractingly horny all day. It had been our third date, when we had our first kiss, which was quickly followed by a wonderful time in bed together. Afterward, she had readily agreed with my suggestion that I could take the lead tonight and she do whatever I asked of her, although she would be able to decline anything she truly found objectionable.

I learned yesterday that she, like me, is very open to new things sexually, and is interested in doing some sexual exploration, of sorts, with me. I also found out that we each enjoy anal play, as both a receiver and a giver, but that she apparently had even less experience with it than I did. I wanted to pursue that tonight, and thought a trip to nearby 'adult store' to get a butt plug, or other anal toy, would be a fun little adventure for us to try together. I had a plan on how to carry this through and I thought she would find it erotic, novel, fun, and I hoped, not too uncomfortable, either emotionally or physically. I was also hoping that she would not refuse any of my requests tonight, but if she did, I thought we could work around it.

I went straight from work to Jill's house and when I arrived to pick her up she greeted me at the door in a cute floral dress that extended to about her mid-thigh. It did a nice job of accentuating her long, fit legs, slim waste, and moderate size, but very nicely shaped breasts, with some of her cleavage showing invitingly. Her shoulder length blond hair was in a ponytail. She greeted me with a big hug and a warm wet kiss. I eagerly returned the kiss and let my hands caress her shapely ass. After a full minute or more of tongue wrestling and groping each other, I stepped back and told her that she looked, felt and tasted great. She thanked me and said the feeling was very mutual. She complimented the look of my khakis and button down shirt. I asked her if she was ready to go out and she said she was. I told her that first there were a couple of adjustments to make and then we would go. "Take off your bra for me, please." She gave me a bit of a questioning look, and I said, "You agreed that I would lead tonight and you would do as I asked."

She rolled her eyes a little and nodded, turning around while slipping the straps of both her dress and bra off of her shoulders, exposing her sheer, lacy bra. She asked me to undo the bra clasp, which I did. She let it drop to the floor as I ran my hands around her sides to her front and fondled those pretty, perky breasts, while I kissed her shoulder and neck, and gazed at her lovely tits from behind. She moaned softly and tried to push her butt against my stiffening cock, but I turned her around, moving my mouth to her left breast and my hands down to fondle that cute ass again. After kissing and nibbling each of her erect nipples, I dropped down onto my knees, slid my hands up the backs of her thighs, under her skirt, and started to pull down her dainty panties. She said, "I thought we were about to leave for dinner, but you seem to be going somewhere else, not that I'm complaining."

"I said we had some adjustments to make first, and I'm just making one more change in your wardrobe." As I held her panties open at her feet I said, "Please step out of these." She complied and watched with a smile as I sat back on my heels, feeling her underwear and lifting them to my nose, saying, "Hmm, these are fairly wet and enticingly fragrant already."

"That's what your attention, as well as thinking about what will happen tonight, does to me. Are you complaining? Are you changing my wet undies? Did you bring a different matching set for me?"

"So many questions. No, I'm not complaining. I've been eagerly anticipating tonight for most of the day, and I glad you seem to have been, too. I'm also very pleased to see, and smell, that you appreciate my attention in that way. I like your wetness, its scent, and its taste! But, underwear interferes with the plans for this evening, so you won't be wearing any. As for leaving, we will in just a few moments, but as long as I am down here..." and I took hold of her ass, pulled her toward me, ducked my head under her dress and buried my face between her legs, licking at her wet lips while my hands grouped her ass.

"Oh, that feels so good right now that it's making me a little weak in the knees. I don't want you to stop, but I need to sit down," and she turned slightly, taking a step back to sit in a large cushioned chair.

I followed her by turning a bit and leaning forward on my knees, with my head still beneath her dress, at her pussy. When she sat I took hold of her ankles, lifting her feet up and telling her to rest them on the edge of the chair cushion. Her legs were now up, with her knees bent, and I spread them apart more widely. As I licked at all of the wetness between her legs, She started to pull up her dress so she could see, as well as feel, what I was doing, but I pulled it back and told her "Pay no attention to the man behind the curtain. I'm just cleaning up all the deliciousness that has spilled down here. Mmm, I don't want it to go to waste." I was licking from her labia, between her thighs, then chasing the flow of wetness that had run down her perineum, into her ass crack and around her puckered anus. I lapped it all up, and then paid a bit more attention to that place I had plans for a little later. As I spread her ass cheeks and ran my tongue between them she whimpered and squirmed slightly. I teased her little brown rosebud and then started to push my tongue inside it. As I did, she began to audibly breathe heavier, panting, and pushing against my tongue to shove it in further.

"Ohhh, doing that is certainly going to make more for you to clean up," she moaned. "No one has ever licked me like that, not there. It seems so bad but it feels really good."

I leaned back a bit and said, "Mmm, I know it wouldn't seem like it should, but it tastes really good, too. Your arousal is so delicious. We'll get back to this later, I'm sure, so let me just have one more taste and give this a little kiss good bye, for now." As soon as I said that I ran my tongue up the length of her ass crack, pushing on her butt hole as I passed it. Once clear of that spot, I teased the hole gently with my thumb, as I slowly stopped spreading her ass apart. I continued to gently trace my tongue from her ass upwards up, pushing it between her moist lips until I reached her clit, which sucked into my mouth momentarily, and then gave it a little kiss. She moaned again and tried to clamp her legs together on my head, but I pulled away before she could trap me. I placed her feet back on the floor, stood, leaned in and kissed her, letting her taste herself on my lips. I then took her hands, pulled her up from the chair and said, "It's time to go now. Please grab a small towel to sit on in the car so you don't make a wet spot on that pretty dress."

"If I do, it's all your fault for causing the wetness, and for taking my panties, although they were probably too wet to protect my dress very well anyway. You really know how to give me an appetite, of sorts, and make my mouth water, among other places. I really didn't want you stop mopping up me up with your tongue."

During our short drive I asked her if she liked Japanese food, and she said she liked sushi rolls, but hadn't really had anything else. I told her that's fine, and let her know that there was a little errand for us to do before dinner. I also teased her some about being wet from anticipating the evening, but told her that I had a hard on for most of the day and my balls were becoming a bit tender from all the congestion that caused. She said she would love to help relieve that problem, and very gently caressed my crotch. I told her to pull up her skirt and let me see how the towel was holding up. As she did, she replied sarcastically, "I'm sure it is the towel you want to check out." Looking down, she continued, "Maybe not as wet as I was, but I'm still pretty damp."

I grinned back at her and said, "I think you should dip a finger or two in there to see just how damp it is, and you can give me another taste while you are at it."

"I'm thinking you just want to watch me finger myself, which I've never really done for anyone before, but since you're in charge..." She ran two fingers through her slit, then put them in my mouth to let me suck on them. "Ok, that felt good, and rubbing myself a little in front of you was kind-a hot, too. Do you need another appetizer before dinner?" She was rubbing herself again, perhaps almost unconsciously.

"I don't think I'll ever refuse a taste of your sexy nectar, but we are here now, so just give me a minute. You can rub around and get a nice serving ready for me while I park." I tried to watch her do what I suggested while I parked the car in a somewhat secluded part of the parking lot, near another building in the back. It was fun to see her sitting with her head back, eyes closed, knees wide open, and two fingers in her exposed snatch.

When the car came to a stop she opened her eyes, slipped her fingers out and quickly leaned towards me as she put them in my mouth again. I sucked her fingers and she stroked my tongue lightly with them. She looked around and asked why I parked there, and not in front of the restaurant. Then she asked if we still had an errand to do before dinner. I said we did, and got out of the car. She pulled down her skirt some and opened her door as I extended my hand to help her out of the car. I led her toward the building in the back, with my hand on her ass, and told her we were going to do that errand right now. She looked up and saw the sign for a store with a name hyping "intimate apparel," and then looked back at me with raised eyebrows, saying "I've never been in here. Planning to get me some new undies to replace the ones you removed earlier?"

"No. I believe they have other things here that might be more interesting. I want you to help me pick out a little something for you, well, for us. Though it may turn out to be something you'll end up wearing, in a manner of speaking." Her eyes showed additional puzzlement, and some amusement.

As we entered it appeared that the store was empty of people, except for the 30 something woman behind the counter who gave us a welcoming smile and told us to just let her know if we needed any help. I thanked her and said we certainly would. As we went deeper inside, Jill started to head towards the clothing area, but I steered her off in a different direction, saying, "Yesterday we both seemed to enjoy playing around the backdoor, so to speak, so I thought we should try looking for something that might help us explore that some more."

"Oh you did? Well, I guess maybe we do think alike. Exploring that kind of thing some more had crossed my mind earlier today, too. Then your attention before we left my house tonight made me sure I wanted to. But, did you think I don't have any sex toys of my own at home?"

"Well, I might have had a little hope that you have some, but I assumed that none of them would be anal toys since you said you didn't really have any experience with that kind of play before yesterday. Let's browse around and see what might be of interest. I'm figuring on something at a beginner's level, at this point anyway. And we don't have to get anything at all if nothing has any appeal to you."

"I'm certainly up for browsing around, and I'm very interested in seeing what might appeal to us both. I'm really curious to get to know more about the things you'll find alluring in here. Did you already have anything in mind?"

"Ok, I admit that I had thoughts of us trying a butt plug, or something along that line. I think this little thing would be cute on, or in, you, especially when you bend over for me," I said, pointing out a silver teardrop shaped plug with a jeweled end that was down at the lower part of the display rack. "Get that for me, will you, I want to get a better look."

She looked over her shoulder at me, glanced around the room to see if anyone else was there, and then bent over at the waist, pulling her dress up as she did, so that I had a nice view of her beautiful ass. "I know what you really wanted to get a better look at, but I'm curious about this kind-a toy, too, so I'll play along."

"Well, you wanted to know what I found alluring here, and this is the most alluring thing in the store to me, right now," I said as I rubbed her ass, and slid a finger down to her pussy lips, feeling her wetness again.

She stood quickly, pulling down her dress, turned and said, "No trying out the merchandise in the store. You break it you buy it. And all such slogans that I can apply to say don't do that where someone might see it! And, don't get me started dripping again!" Then she smiled, handed me the box, along with a little kiss, and lightly squeezed my crotch.

"Hey, no trying out the merchandise, or something like that," I teased her, with a grin. "You're the one who lifted you skirt, though. How was I supposed to resist that?" I glanced at the box she gave me, then pointed to some rubber plugs with tee shaped handles, "Or, we could go with something more plain, like these. We could try a single style, or an assortment. What do you about them?"

"I think that little silver jeweled thing would look cute in YOUR butt, especially when you bend over for ME. I hadn't really thought much about this sort of thing before, but after yesterday, I think some kind of plug thingy might be fun to try, on, both of us. I could go for the metal one with bling, but I wonder if a rubber one would just be more comfortable."

"That's a fair point. I have no experience with these. I wanted to do some research today, but really couldn't at work. Maybe we should ask the nice lady up front."

"Ok, I'll do that, girl to girl," and off she went with a couple sample items. I kept looking around the same section trying to find something that seemed right for our needs at this point. There were so many items, but most were just a minor variation of a few designs or products. Aside from the major function and design style, the big choices seemed to be size and material. Comfort and practicality were certainly important factors to consider. Simple stimulation was the main idea right now, so I wasn't considering vibration and such, but the idea of a remote control was certainly something to keep in mind for the future.

When Jill returned she echoed these basic points and brought up a couple other things as well. We settled on a "beginner's set" of 3 silver aluminum plugs with jeweled ends, in small, medium and large. And of course, plenty of lube. I paid the girl up front and she winked at Jill, saying, "Let me know how it goes."

Jill smiled, winked back, and just nodded in reply. I raised my eyebrows at the two of them, and said to Jill, "That was awfully chummy. Anything I should know about?"

"Nope, just girl talk. But I, or we, may have to come back here and browse around some more. Are we going to dinner now?"

"Very soon, one more thing to do first," and I walked us to the car, opening the back door of my SUV and directing her to get in. "We need to get you dressed first," I said as I opened the box of plugs and retrieved the small one. I reached into the center storage area of the car and got some alcohol hand sanitizer and began clearing the plug as I told her to kneel on the seat, facing backwards, and to lift up her dress. She gave me one of those looks again, but did as she was told.

I sat there a minute, openly admiring the view, as I finished cleaning the new toy and placing it, along with the tube of lube, on the seat next to me. Then I caressed her ass cheeks and spread them apart, commenting on how nice she looked, and smelled, with her pussy getting wetter by the minute. She wiggled her ass at me and sort of giggled. I moved my thumbs into her crack and toward her hole, rubbing softly around it. She cooed. I continued rubbing as I leaned in and kissed her ass cheeks, kissed her pussy near her crack, then licked up to her anus, and teased around it, with my tongue. While still holding her cheeks apart, I slid my thumbs down to down to her pussy lips and teased them as well.

She was now moaning, pushing her ass into my face and spreading her legs a little farther apart. I licked harder right on her butt hole, and soon I started to push my tongue into it. Her sweet juices were almost dripping from her pussy, and I moved one hand so that I could slide two fingers into her hot sex. She squirmed a bit while moaning louder while pushing back on my face and fingers. I shoved my tongue into her harder and rubbed on her g-spot with my fingers. Her hands went to her ass, pulling it open, while she groaned and ground herself against me. I moved my tongue in and out of her while continuing to caress the sweet spot inside her vagina, until she came, with a great shudder, and slumped forward against the seat back, away from my face. I slid my fingers out of her and put them to her lips for her to suck, then picked up the plug and lube from the seat with my other hand, and I licked at her hole a little more.

Putting a generous bit of lube on the plug, I smeared it around with a finger, then put that finger to her ass, rubbing around and inside her opening. Jill pushed back against my finger and said, "Umm, yeah, let's do it." And I put the plug against her open pucker. With gentle pressure and a little twisting back and forth, the plug began to slip in. She moaned and pushed back, pulling her ass cheeks apart with her hands. I told her how really sexy she looked and sounded, encouraging her to take the plug into her hot ass. Soon she pushed back a bit more and it slipped all the way in.

"Good girl, babe, that really does look hot," I told her. "Now let's go to dinner."

"Are you going to take it back out first?"

"No, that would spoil it. I want you to wear it through dinner. I'll take it out back at your house, after I come in your pussy. Are you Ok with that?"

"Well, I think I can deal with that, considering the reward," she said. How quick can we finish dinner?"

"Are you in that much of a hurry to get the plug out of your ass? Don't you like the feeling?"

"Oh, I do like it, although I'm a kind-a nervous about wearing it in public. What I'm really looking forward to is your dick in me. I'd like to suck you off right here if you let me. Or I can keep kneeling on this seat while you can slide your hot cock into me from behind. That would be really nice."

"I love the way you think," I told her, "but we need to get some dinner, and then we can go home where we'll be much more comfortable sucking and fucking."

"Then let's get going, you're wasting time," and she was out the door.

We went in the restaurant and I said, "Why don't we sit at the bar and have a drink first."

"Really? There are so many reasons I want to get home as soon as we can," and sighed, "but it is your night to be in charge. And you should know that I WILL remember all this when it is my turn to lead you around by your," stopping mid-sentence, then continued, "Hmm, what a fun thought I just had," but she didn't say more.