Lucky Over 40 Ch 01 Taking A Chance

I'm an over 40 single guy that got

really

lucky finding an over 40 widowed woman, who has a similar sexual appetite. This is the start of our sexual adventures, which are mostly about exploring some completely heterosexual kinks. This part is pretty tame, but contains things like oral sex, fingering, ass play, face sitting, and 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 decide to keep reading! (Please DO make use of the Tags for stories to see what you may like or not like.)

This is my first foray into story writing, or posting anything like this on-line. It is based on real events, but embellished somewhat, mostly by combining more than one episode. We've shared this tale with some close friends who like the story of how we "started," so we decided to try sharing it here to see what others think. It was intended to be erotic and so is heavy on the sex, but it also has a fair amount of "background" to set the stage for what may, hopefully, be some more tales of our ongoing adventure. Try to enjoy it for what it is, and not be too harsh in your judgement of my writing prowess, or lack thereof, in this first attempt. Specific, constructive criticism is always welcome.

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I was living in Florida when my girlfriend got a great new job and moved to California. I started trying to find some female companionship using on-line dating sites of various kinds. It was usually a pretty frustrating process, but I did get some occasional dates. I'm in my forties, over six feet tall and a little overweight, pushing 200. My hair was thinning so much that I decided it was time to try shaving what little was left on top and keep the sides cut very short, with my beard trimmed close as well. If rocking a bald look worked for guys like Bruce Willis, Jason Statham, and even Patrick Stewart, maybe it could work for me. Ok, I was nowhere near as good looking as any of them, but I am intelligent, well read, and have been told that I have a great sense of humor. But, I've never had a lot of luck with women and dating. Unfortunately tough, I have a raging libido. I've had my share of sexual partners, some more adventurous than others, and have been in some fairly long term relationships, but things just never worked out. Lately I'd gotten some "relief" with a few one-night stands thanks to some dating sites and from a couple "friends with benefits," but that's all pretty intermittent and not very reliable. I was not looking to get right back into another long term relationship, but I did want someone to spend more time with, to do various activities with, and to have more regular sex with, if that wasn't asking too much.

I saw the profile of a woman I'll call Jill on one of the dating sites, and I found her attractive in several ways, so I reached out. We started conversions on-line and by phone, and finally had a couple dates. She's my age, is pretty, slim, and has straight blond hair down to below her shoulders. She is as tall as I am, or nearly so, which had been a disadvantage for her, dating wise. She said it was an advantage playing basketball in college, but being taller than most guys she dated didn't work well, so she was looking forward to going out with a guy her height. We're both registered nurses, which gave us something else in common. Unlike me, she had been married, with a daughter in college. We went on a couple casual dates and neither of us made any moves so I didn't know where this would go. As I said, I'm not good at dating and really don't trust myself to read a woman's "signals" correctly. I don't have a lot of confidence with being forward, but I was trying to be more assertive and take more risks that way. On the afternoon of our third date, I guess maybe Jill decided she needed to stop waiting for me, and on our way out of a movie theater, after seeing some mundane film, she started to gently pat and rub my butt.

At first I was a bit shocked, since I wasn't used to that attention from a woman, but shock soon turned to arousal. I figured that this was probably a reliable sign and I should do something to help get things rolling in a physical direction. As we went out to the parking lot I rubbed my hand on her ass, which I had admired on previous occasions. She did not object to my caress, so I was encouraged. When we got to her car I led her to her door, spun her around gently, with one hand still cupping her ass, and I kissed her firmly. To my delight, yet not without some surprise, she didn't pull away, but put her arms around me. I kissed her more deeply and our tongues met while I started to caress her soft ass cheeks with both hands. I don't know where her hands were since all I was aware of was the sensuous kiss, the feel of her sexy ass, and her groin starting to push against my swelling cock. I didn't want to stop, but I didn't want to overdo it either, so I gently broke it off and walked to the other side of the car, trying to discreetly adjust my uncomfortably stiffening cock through my pants as I went. I silently settled into the passenger seat and tried to think what to say as she started to drive us back to her nearby house. Ever the sophisticated player (not!), I just said, "I hope you didn't mind my doing that, but it just seemed like the right thing to do at the time."

"I didn't mind your kiss at all, it was really nice, and so was your attention to my butt. I like your butt, too, by the way," she said with a big smile. Then she looked at me and said, "Oh, or do you mean did I mind you touching yourself before you got in the car? I assumed you needed to adjust something I felt pressing against me during our kiss. My late-husband did that kind of move, so I recognized it. Really, it's nice to know I had that sort of effect, and I find it sort of sexy, so I don't mind that either."

"Um, you weren't supposed to see that maneuver, but I guess it's obvious that I really enjoyed the first part, too. I hope we can do more of that." Then I continued kind of nervously, "I've just got to say that honestly, I'm terrible at dating, and so don't have a lot of confidence with it. Frankly, I have no idea how to read a woman's signals, so you have to be kind of obvious with me. I assumed your hand on my butt was an overt gesture, and since that kind of touch tends to turn me on, I decided to take a chance. I'm glad it didn't seem to be a mistake."

"No, it wasn't a mistake, and your hands on my butt and your very nice kiss, not to mention what was pushing into me through your pants, were a turn on for me as well. I'd been hoping you would kiss me for a while, but didn't want to initiate it myself. I found it hard to resist giving your cute butt a little pat, though, and now I'm really glad I did."

"I'm really glad too! Oh, and I really like your ass, too. And your kiss," I replied, awkwardly, but gaining some confidence. "We haven't really talked about this sort of thing much, and I'm still a little shy about it, but let me try to be open and honest. You know my last long term relationship recently ended and that I'm still unsure about starting a new long tem thing, but I do want -- and need --romantic companionship. I've told you already that the last relationship wasn't very physical, not nearly enough for me anyway, but at the risk of being too honest, I need to let you know that I definitely don't want to be in another relationship like that right now. Our kiss, and the caressing, reminded me how very much I miss that sort of thing, and other things. It's been way too long."

"Well, that's good to hear, because the feel of your hands, lips, tongue, and um, you know, got me warmed right up," she said with perhaps some slight embarrassment. "When you just said that you hope we can do more of it, I wanted to blurt out 'yes please, and soon! It's been too long for me, too.'"

Without really thinking about it, I instinctively reached across and put my hand on her upper leg, on top of her jeans with my fingers lightly touching her inner thigh. "That's great news. You taste and feel so good, and I'll confess that you have me pretty horny right now."

"I like the sound of that, and sure I like your touch. Confession is good for you, so let me say that I'd like to taste and feel a lot more of you right now, too. Your hand is getting me hotter and it seems like this bulge in your pants wants to escape," she said as she gently laid a hand on my crotch. "My daughter should be at work for the next few hours, so we can do something about it at my place."

"That sounds really good to me. I'm glad to hear we both seem to have a similar desire, and I'm even happier that we have some private time to indulge it. And, yes, I'm pretty uncomfortably constrained."

As I was saying that, she pulled into her driveway and shut off the car. She quickly undid her seatbelt and leaned over to lick my lips once as she squeezed my cock through my jeans. Just a quickly, she got out of the car and headed to her front door. I followed as fast as I could, impeded by my erection that was painfully askew, trapped inside my pants. I caught up to her as she opened the door and I squeezed her ass firmly as she stepped inside. Once inside, she shoved me against the wall as she closed the door, and kissed me hard, with her mouth open and her tongue pushing deep into mine. She pushed her pelvis straight into me and I groaned, as my cock was still trying to extend itself upright. She smiled and said, "Let's head to my bedroom and let you out of those pants," as she grabbed me by the belt and pulled me to the bedroom.

Once we got inside, she turned and kissed me again, more gently, but just as passionately, while she worked at unbuckling my belt and opening my pants. I slid my hands up her sides then started to unbutton the top of her blouse, working my way down. My hands brushed against her shapely, medium sized breasts, then reached in to gently cup them. "They aren't very big I'm afraid," she said, "but they really like your touch."

"I've never been overly enamored with big breasts," I replied. "I like nice round, proportionally sized ones that are soft but firm, exactly like these; with responsive nipples that get enticingly erect and are sensitive to my attention, just like these seem to be." She pushed down my pants and pulled at my briefs. As she did so, I said, "I'm not very large either, just about average I'd say."

"Big dicks aren't all they are imagined to be either," she replied. "And this one looks like plenty of fun to me. I can't wait to see how it tastes." She slid down to her knees, moving my clothes all the way down to my ankles, and licked the length of the underside of my rigid cock. She planted a soft, wet kiss on the purple head, covering it with her lips and swirling her tongue around it while sighing, "mmmm," as if in satisfaction. I uttered a similar soft sigh and watched her take my shaft into her mouth.

I wanted to kiss her, caress and fondle her, suck her nipples, and definitely eat her out. I was crazy to get my mouth and hands on her, but I couldn't reach any of that, and her mouth felt too good on my cock to interrupt her. Still, I didn't want to come, not yet. I wanted to do much more to heighten and extend both our pleasure. I didn't want to grab her head and face fuck her either. I never liked the idea of forcing my cock down a woman's throat, but if she wants to take me that deep on her own, I won't object at all. Jill was not trying to deep throat me, she was still concentration mostly on my cock head with her lips and especially her tongue. After just a minute or two (I actually have no idea how much time, my mind was racing too much, it could have been 5 or ten), she slipped her mouth off me, saying, "You do taste good, and I'll probably want a lot more of that before too long. But right now we need to get you all the way out of these clothes."

"I was thinking the same about you; that I need to see if those breasts and nipples are as succulent as I think. Then I need to kiss you again, on all your lips. I'm anxious to see if you're as wet as I'm hard."

"Oh, I think I am, and I'd love to let you get a taste of anything your mouth desires. Your pre-cum was delightful by the way, and has me looking forward to the real thing."

I pulled her to her feet and kissed her deeply. My hands fumbled to get her blouse off, and slid down her bra straps, as she pulled at my polo shirt, tugging it over my head. When we had to break the kiss, I slid off my shoes and bent over to remove my socks, pants and briefs. She undid her bra and I saw it drop to the floor and her shoes kicked away. As I stood, I marveled at the firm roundness of her breasts, with erect nipples sticking out and pointing slightly upwards. She undid her pants, dropped and stepped out of them, then started to push down her. She turned as she let them fall, exposing her luscious ass to me when she started to bend over. Then I saw the soft, light brown, wisps of hair between her legs as she lifted a leg to remove the panties. My mouth watered. She turned back around, fully naked, and shyly said, "I don't shave much. I hope you don't mind."

"No, not at all, it's beautiful!" I replied eagerly. "I much prefer the sight of a fully mature woman to a totally bare pussy like a little girl. A well-trimmed bush is a delight see, and keeps me from getting too much hair in my teeth"

"I'm glad you like it, and understand your preference," she said. "As for hair in the teeth, and related issues, I may want to give you a little trim, if you let me. That isn't too kinky for you, is it?"

"As long as you don't want to shave me bare," I replied. "I think it might be fun to have you tidy up down there, as you see fit. I don't really consider that kinky, but I have to confess that I can get a bit kinky."

"Oh, really, I want to learn more about that!" She said with a big grin. "Right now, c'mere so our lips and hands can explore. I want to tongue wrestle some more, and feel that nice ass without the jeans in the way."

"Mmm, I like the way you think." We kissed deeply and sensuously, while her hands squeezed my ass and pulled my cheeks apart. My hands slid up her back, and around to cup her breasts. My thumbs stroked across her firm nipples. I caught them between my thumbs and forefingers, rolling, rubbing, gently pinching and gently pulling them. She moaned softly into my mouth and her fingers started teasing along my butt crack.

I broke our kiss after a while and worked my lips down her neck, kissing, nibbling and teasing with my tongue. Jill leaned back a bit, making some space that let me move my mouth to her beast. I opened wide and took in as much as I could, swirling my tongue around her areola and across the nipple. A minute or so later, I did the same to other. She hummed contentedly and took advantage of the space between us to move one hand to my crotch, sliding her open pam down the length of my shaft to my balls and between my legs as I parted them slightly. She gently gasped my round, tight sack and then took hold of my cock, all the while her other hand was teasing in between my ass cheeks. I had turned my body slightly to open the space between us a little more, and moved one hand to her pussy, slowly moving through her bush and down to her moist lips, parting them, I ran one, and then two fingers up and down between them, teasing her opening and just brushing her clit. My other hand was fondling the breast that my mouth wasn't devouring.

Jill squeezed, tugged and stroked my cock. She moaned softly, spreading her legs a bit to allow me better access to her inner lips. I dipped a finger, then two, inside her slick opening and she gave a slight growl, squeezed my cock head, teased my anus, and thrust her tongue in my mouth. I gently bit her nipple, rubbed her g-spot, and felt her shudder as a small orgasm shook her. She said, "I want you now, in my mouth or in my pussy. I want you to come for me."

"What would you prefer?" I asked her. She pushed me back on the bed, licking up along my cock, taking me quickly in her mouth, sliding her lips up and down my shaft a few times, and then she climbed over me until she could slide me in her dripping pussy. I moaned loudly and grabbed both her tits as she started to ride me. Before long I rolled her over on her back and pulled her legs up with her knees toward her chest, plunging into her as deeply as I could, but gently and sensuously, telling her how incredible she felt.

Her hands were on my chest teasing my nipples, something I had never experienced before. I reached down and rubbed her clit with my thumb and picked up my pace as I started to feel my orgasm building. Jill moaned and started to come, her vagina pulsing around my cock and before long I was shooting my load inside her as I kissed her deeply again.

We cuddled and kissed until my cock shrank and slipped out of her, spilling my semen down toward her ass. She said she should get a towel, but, not wanting her to go, another thought occurred to me. I slid myself down, lifted her legs, and began to lick, cleaning the cum from her butt up to her pussy. I continued moving up to tease her still swollen clit with my mouth. I licked back down to her slit, pushing my tongue as far in her as I could, eating our mixed juices as she squirmed with pleasure.

"No one has ever eaten me after sex. That's so hot," She gushed. "I guess you

are

pretty kinky, and I love it." I moved my mouth up to her clit again, and started to suck. She moaned and said, "You're gonna make me come again," as she grabbed my head and held me there until her third orgasm subsided and she pushed my mouth off her. I moved up to kiss her and she pushed her tongue deep I my mouth, swirling it around. Then, with our lips still touching, she whispered, "Mmm, we taste good together."

"Yes, we do, but I'm looking forward to getting a good long taste of just your arousal, without my contribution," I told her. "I bet it's delicious."

By this time, my cock was growing again, and she could feel it pressing against her. She rolled me onto my back and said, "And I want to get a good taste of just your special sauce, right from the source. I bet you still have some in there for me. I need to give you another orgasm to start to even the score, so lie back and let me have some fun."

She proceeded to kiss, lick, fondle and tease everywhere between my legs until I was fully erect and nearly ready to give her what she wanted. Her mouth was sliding up and down almost the full length of my cock while she sucked and rubbed her tongue along it. Her hands were caressing and exploring my ass again, and soon a finger was rubbing around my hole. I was trying to move my hips to increase the pleasure from her mouth, and also to coax her finger into my ass.

My hands were roaming all around, without thought, caressing the sides of her breasts, her back, and around her ass. She moved her hips around and lifted them until her pussy became available to my mouth and I tried to eat her, while my fingers started to explore her ass crack and rosebud. She took her mouth off my cock and swatted at me with her free hand, saying, "No, it's too distracting. You're my plaything right now, just enjoy it and admire the view." And I did enjoy the view between her legs, and the scent of her musk as she worked on driving me to come in her mouth.

Her finger worked its way inside me, wiggling and probing, but not very deeply. Her mouth was bobbing, slurping, licking, and sucking. It was a feeling I can barely describe, except to say that I couldn't wait to come, yet I didn't want it to stop, either. And then I suddenly gave her a quick warning, tightened up, and started to ejaculate into her warm, wet mouth. I moaned, "Ohhhh," and she hummed, "Mmmm" with a little self-satisfied chuckle thrown in, never taking her mouth off me. We were both happily satisfied.