Lucky Over 40 Ch. 12: Jill likes My Dream – Erotic Couplings – Free Sex Story

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Author’s note: This is the twelfth part of the story of two single 40somethings who met on-line and started an adventurous sexual relationship. Overall, it’s about exploring various completely heterosexual kinks. You do not have to read previous parts of the series to enjoy this one, although somethings might be better understood if you do.

Please check the story Tags to see what you may or may not like. If anything there bothers you, it might be best if you move on to another story, otherwise, I hope you enjoy reading. If you like it, please add some stars at the end, and even a comment. Your feedback does help inspire me to continue writing.

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I’ve been dating Jill for a couple months, and we’ve been having a lot of great Sex for about half that time. I feel like the luckiest guy in the world to be with her. We have a pretty unusual relationship, especially since Jill has occasionally “lent my services” to a couple friends in order to help them out with some sexual frustrations. It’s become very apparent to me that I’ve fallen in Love with Jill, despite thinking I wanted to avoid another committed relationship right now.

I’d just finished a twelve hour Saturday night shift in the Emergency Department where I occasionally moonlight. I’m not used to working nights anymore, particularly for the long shift, so I was wiped when it was done, but something “came up” during work that also kept me occupied a while afterwards. When I finally got home to my bed, I was asleep in about a minute! But I guess the stress of the day, along with that little indecent, and its aftermath, was still working on my brain because I was having a really interesting dream when I was woken up by Jill, coming to check on me.

“Hey Tiger,” she said, softly, sitting down on the bed next to me. “Did you get some sleep? It’s been several hours since you’ve been home.”

“Yeah, Princess,” I said groggily. “I did, but I should get up so I don’t screw up my normal sleep schedule. Thanks for coming by. Are you still on call, or have another patient to see?”

“Nope, done for today! I’m all yours…or you’re all mine,” she said as she leaned down and kissed me, gently.

“Hmm, great! Why don’t you get undressed and join me here so we can make up for some lost time together this week. I just had a dream that got me kinda wound up — on top of everything that went on last night and this morning, all without any relief for me!”

“Oh, my poor, Tiger. Is Robbie Jr. starved for attention?” she teased me, as she reached under the sheet looking for my dick.

“He sure is, and that picture you sent me got me looking forward to lavishing some attention on your lovely breasts, not to mention your wonderful Pussy. Come on, get those clothes off and let me make Love to you, Princess.”

“Yeah, about that… I uh, had a friend come visit yesterday. I’m afraid I kinda off limits right now,” she said rather dejectedly.

“I don’t get it? You have company? Are you saying you can’t stay and have to get home to them?” I really wasn’t fully awake, but I’m also not used to female code-speak. I guess it went along with my inability to pick up on their “signals” and such…

“No. You really don’t do well with women when we aren’t very direct,” she chuckled. “My period started yesterday, well, Friday night really. As much as I’m not thrilled by all the symptoms that go along with the run up to menopause, I’ll be very happy to be done with this!”

“Oh! Sorry, no I’m not good at it. And we haven’t dealt with all that yet, for some reason. I’m sorry.”

“I’m sorry, too! Being premenopausal my cycle is off, but then again, it has been for much of my life anyway, especially when I was exercising a lot more. Well, exercising differently than the workouts I get with you…” she squeezed my erection, which she had been softly caressing. “I can still help this guy out. What would he like that doesn’t involve anything below my waist?” she purred.

“If you really want to, I’d be very happy with whatever attention you wanted to give him!”

“Yeah, I do. I always like giving your cute cock some attention. And you were so good with everything I threw at you last night in my texts, and then at Ruth’s this morning. What’ll it be, Tiger? Do you want me to suck him off, or stroke him off, or…?”

“Really, what pleases you will definitely please me. If there’s something you want to do, please, by all means, indulge yourself.” I said, with a big smile. “Really, knowing you’re enjoying what you’re doing to me, gets me off better than telling you what I want.”

“Ok, I get that. But I also like it when you tell me what to do. Like that special date we had a while back…”

“Hmm, that was fun. But I think you really enjoyed the next one, telling me what to do, much more!” I half joked. “You’re good at that. And generally, it’s really nice. Though sometimes it gets a little scary, but in a kinda fun way,” I chuckled. “Hmm, like the dream I was having just before you woke me.”

“Oh? You need to tell me about that. Maybe you should do that while I take care of this guy,” she said, kissing my erection.

“Um, yeah, Ok,” I muttered, still half awake. “Mmm, that’s good. I’ll try to remember, if I can concentrate…”

“Well, maybe I’ll just give you some relief and then you can get the blood moved up to your brain…” she laughed, touching my cock. “Oh I do like your penis, especially when it’s so nice and hard. And this beautiful head, so round and firm, with a well-defined ridge that feels so good inside me. Mmm.” She wrapped her lips around my engorged glans. Her tongue danced all over it, and explored every bit, running around the lower edge several times before finishing by teasing the opening.

“Oh yes, I like that,” she said smiling at me. “I Love running my tongue around this head and rim. It feels so soft, and sensuous.” She ran her tongue across my glans and all along its underside, tracing the edge.

“Ahh,” I sighed, “I Love that, too. You feel so good…”

“I’m so glad you like it,” she smiled up at me with her tongue peeking between her lips.

“I do, honey, I do. That felt — oh, and feels — wonderful.”

She licked the underside of my shaft from bottom to top a few times, before tickling by the little V at the base of my cock head with the tip of her tongue.

“Mmm. You taste wonderful, especially your sweet precum leaking out. I think there was some dried all around this head. You must have been leaking quite a bit last night,” she giggled. “Let me see if I can get some more out of you. You’ve been drinking your pineapple juice, right?” she laughed a bit before taking me fully into her warm, wet, wonderful mouth.

She sucked on me like on a straw, as if trying to pull all the built up cum right out of my swollen balls. Her mouth bathed my cock. She started to bob her head up and down along my shaft; whenever she got to the top, her talented tongue teased and swirled all around and under the head.

“Um, yeah, oh, fuck you are good at that,” I sighed dreamily. “Oh yeah. I don’t want to try thinking about anything else right now. I really Love what you’re doing. I really Love you, Princess. How did I ever get so lucky.” I was in heaven, or very, very close to it.

Her hand began stroking my shaft, following her mouth, and her other hand caressed my balls. After a bit, that other hand slid between my legs to my Ass cheeks. I enjoyed that attention. After a few minutes she popped her mouth off my cock and smiled at me again, still gently stroking me.

“Mmm, I like doing that. You feel so good in my mouth.” She slid her mouth down me once again. “And I like the perfect size of your big, hard cock. Not too thick and not too long. It’s such a pleasure to do this.” She enveloped it again, sucking hard for a few seconds. “And it fits my Pussy so very, very well.” She stroked me again.

“Oh yeah, did JJ tell you she got the kit she needs to make a mold of this cute cock? This … beautiful… gorgeous … perfect … penis.” She punctuated each word with a wet kiss and little lick on a different part of my throbbing dick. It twitched with each kiss, and she seemed to enjoy that so much she just kept kissing.

“Oh, Honey,” I moaned. “No, she didn’t,” I tried to concentrate on what she had told me. “I didn’t think she was serious about that… Oh fuck, you’re good. Does she really want to sell copies of my cock in her shop? That’d be weird, but flattering I guess. Oh baby, I Love what you’re doing to me…”

Jill was sucking and stroking me again, and she hummed in agreement with everything I was saying. The vibrations felt incredible, especially when my cock was deep in her mouth.

Her hand moved into my Ass crack. I bent my legs up and out to open myself up to her more. A finger pressed against my asshole and I moaned. She took her mouth off my cock, but continued stroking it as she teasingly stated the obvious, “Oh, you like that.” She wet her finger in her mouth, then pressed it into me, while licking the sensitive frenulum just below the head of my cock.

“Oh fuck, yeah!” I was now fully awake. “Oh, baby, you know I like it. If you keep doing all that I’m gonna cum pretty damn soon.” My cock was throbbing and I was about to beg when she pushed her finger deeper into my Ass and wiggled it inside me. It felt incredible and I groaned with pleasure. She took my swollen glans back in her mouth and sucked hard, her tongue teasing all over and around it.

FUCK, you’re so good, Jill,” I moaned loudly. I involuntarily pushed my cock up at her mouth. I didn’t need to be in deeper, just wanted more of whatever she was doing to me. Her finger rubbed my prostate in time with her stroking my shaft. All the while she continued to suck and lick my cock head, noisily and sloppily, her saliva running down my cock as her hand jerked me off.

I was squirming and moaning and, before long, telling her I was gonna come. She hummed back at me, and that added stimulation was all it took to finish me off. I exploded, almost literally, into her mouth. So much cum was built up from several days without her, without jerking off, but with quite a bit of sexual stimulation in the past twelve hours. I’m sure she wasn’t ready for what I gave her. Her head jerked, she coughed once and cum leaked down my cock and onto my balls.

I got a little concerned, but she began to laugh as she continued trying to take it all and swallow it. The laughing made her leak more, but she just sucked and licked it up, giggling. “Wow, Tiger, if I had any idea how much you’d stored up I would’ve jerked you off just to watch the geyser! I couldn’t even save any in my mouth to share with you,” she laughed, wiping her lips.

“Oh, fuck,” I sighed in relief. “Yeah, my balls were getting a little uncomfortable. I guess they were pretty full. Thanks, Princess! That was amazing, and just what I needed.”

As I caught my breath I continued, “I hope you enjoyed that some, too, Princess. It was a great climax. I’m so glad I saved it all for you!” I chuckled, but really meant it. Coming with Jill was so much better than it would have been with Ruth. I mean, a good Orgasm is always great, but it was so much more, I don’t know, satisfying, being with my lover. With my Love. Yup, I’m in Love with Jill, and that makes Sex with her so much better.

“Come on and crawl in here to snuggle with me, will you?” She pulled off her top and her bra. I started to get aroused again watching her beautiful breasts bobbing as she freed them, and then kicked off her shoes. Her nipples were fully erect and seemed to beg for attention. “Damn baby, you are gorgeous!” She blushed a bit. I reached out to fondle one and she moaned softly.

“They’re really sensitive right now, and you got me pretty Hot with that wonderful cock of yours, being so hard and full of cum for me. Will you give these some attention with your lovely mouth, Tiger, please?” she asked, holding her perfect tits.

“Oh baby, I’d Love to do that!” She crawled above me and lowered her breast to my eager mouth. My hands cupped them as I took one of her stiff nipples between my lips and suckled it. My tongue swirled around it. Jill moaned and caressed my head. I kissed my way across her chest to the other breast until that nipple was in my mouth. It felt amazing, so firm and erect. My tongue lavished it and I adored the feeling of her in my mouth. From her sounds, so did Jill.

My teeth brushed against the nipple and she cried out, not in pain, but pleasure. “Oh Rob, bite it, gently, please. Yes, oh yeah…” I held the stiff nub in my teeth and tugged on it gently. My fingers rolled and pinched the other one. “Oh Babe, I’m gonna come. Oh fuck, it’s gonna make me come.” As my tongue teased over the tip of the nipple being pulled by my teeth, she shuddered and collapsed on top of me. I help her tightly, amazed at what had occurred. It was a new experience for me, giving a woman an Orgasm just from nipple stimulation.

After another minute or so, Jill got under the sheet with me, her light scrub pants still on. She cuddled up next to me as we hugged and kissed each other. Damn, I Love this woman.

“I Love you, Princess,” I said, kissing her head as I held her close.

“I Love you, too, Tiger.” She said, softly. We kissed deeply, tenderly, lazily. It was wonderful.

We laid there a while, wrapped in each other’s arms. I started to fall back to sleep, but she caught me and said, “Ok, time to get you up so your body clock doesn’t get all screwed up.”

“Yeah, you’re right, but this is really nice, and comfortable. I miss lying in bed with you, and waking up with you. It’s only been a week, but it seems like much, much longer.”

“I’ve missed it, too. Maybe we can spend tonight together. Since I’m out of bounds for your attention right now, or some of me is anyway, you could probably come stay at my place with Becky home. But we also have all next weekend together, at Disney, Tiger. We’ll have a great time, I know it, even if we can’t spend the whole time in bed, or even naked,” she said with a laugh. I’m sure we both started thinking about the weekend we spent together at her place, and more than a day with no clothes on…

“We’ll see about tonight. I pretty sure we can’t go the whole night without fooling around in some manner, and Becky probably knows that, too. Anyway, I’m looking forward to next weekend, too. But I’ve got lots to do this week so I can take Friday off. And that means a good night’s sleep tonight.”

“Ok. Well, if a few days of no Sex — unless you’ve got something on the side I don’t know about, or been jerking off, without me… You know I wanna watch you do that. Um, where was I, oh yeah, if a few days off lets you build up a load like that, I really need to remember about it and find a good way to make use of it.” She had that sly, almost devious, smile of hers. I know it means something is up that could be trouble, but usually turns out to be fun in the end.

“Time off to refill helps, but I think what really charged me up was your picture on my cell phone, and then…”

“And then fooling around with Ruth, huh?” she interrupted. “Did she try jerking you off, or blowing you? She wanted to. She wanted to fuck you, I bet. And you would’ve liked it, wouldn’t you? How long have you wanted a piece of her? You haven’t told me if you liked eating her `til she came on you face. I’m sure you did, though. Did she taste good? Hmm, did she?” Jill was teasing me now, and holding my dick as it grew more in her hand. I’ve been at least half hard since I was sucking her luscious tits.

“Not nearly as good as you do, Princess.” I said, truthfully, though Ruth did taste pretty damn fine.

“Oh, good answer,” she said as she stroked my cock a bit and leaned in to kiss me. “I Love it when you make me come with your mouth. You’re really very good at it. I don’t have many guys to compare it to, but Jill, um JJ — got to remember to call her JJ — says you’re very good at that. And at other things, too. Deejay really liked your tongue as well, and your “other thing.” She giggled, still toying with my erection. Was she trying to work me up, again?

“Yeah, well, thanks for the affirmation. But I really do prefer you,” I said as I rolled toward her and kissed her deeply. It was weird having her talk about these women that she had arranged for me to have Sex with, and who were all part of that bizarre but very erotic dream I was having. My mind wandered back to it and I was a little spacy when Jill looked at me after our kiss.

“Hey, Tiger? Where’d you go? Not falling asleep again? Are you day dreaming? Oh, you were gonna tell me about your sexy dream before I made you lose your train of thought, somehow…” she giggled, and squeezed my cock. “Get up and you can tell me while you Shower. I’d offer to scrub your back, but your Shower is really too small for two to be comfortable in, so I’ll just watch.”

We got up and headed to my bathroom. “I got to pee first,” I said.

“You know I like to help with that, can I, please?” she asked, stepping towards me with a little kiss as she took hold of my cock again. She giggled as she watched it swell more in her hand, saying “I really like when it does that, too.”

“Um, I’d Love to, but it’s hard to pee with a stiffy, and even harder to aim at the toilet.”

“Hmm, Ok, well, let’s aim in the Shower, then,” she responded, turning me and patting my butt with her Free hand. That got my dick to twitch. I don’t know why, but I Love it when she fondles my Ass. She reached around me and gently held my cock as I closed my eyes and tried to relax. The stream started and she watched around my shoulder. “Lift this arm up, please, so I can have a better view,” she giggled. I put my arm around her.

This was probably the third time she had held me while I peed. I was enjoying it, more than previously, although it was arousing then, too. It didn’t seem as weird now, and of course, I loved having my cock in her hand. Plus, feeling her tits and hard nipples pressed against my back, and her other hand caressing my chest and nipple, was all definitely sexy. I got fairly hard while I was still peeing.

“You seem to like my help, Tiger,” she purred in my ear, then licked it. My stream was a trickle now, and my cock was pretty hard so it ran down my shaft. As the flow stopped completely she whispered in my ear, “Thank you, babe. I liked that.” She kissed my cheek and stepped back, patting my Ass again as she let go of me. I instantly missed the warmth of her pressed against my back, but loved that hand on my bottom.

“Ok, get in there and clean up, Babe. No, wait! Hey, where’s your beard trimmer? This is a good time to let me give you a little trim to tidy things up, down here,” she said as she ran her fingers through my pubes, down across my balls, and between my legs. My cock twitched again. Fuck, I Love her touch.

“Um, Ok, it’s in the cabinet.” She retrieved it and I stood in the Shower. She had done this once before, but it was a while ago, and things had grown some. I never really did much trimming in that area, but I understood that the shorter hair made all her wonderful oral attention nicer, for her at least. And, it was sorta sexy to have her doing this for me. I think I really should return the favor sometime.

“Ok, first lift your arms and let me trim up there, before we spend time at the pool next weekend.” She quickly trimmed my armpits, something I rarely think to do. As she knelt down in front of me, she rubbed her hand across my moderately hairy chest, saying, “We’ll leave all this lovely fur just as it is, Tiger. Down here can use a little attention, though.” Her hand ran across my pubes, the cordless trimmer following.

“Not too short so it doesn’t bug you. And we don’t need to give you a bikini line, since I don’t want you strolling around in a speedo at the pool. It’s a really nice look on you, but that beautiful bulge isn’t for the general public,” she teased as she trimmed. “I like this hair, just like you enjoy seeing mine. Oh, did I tell you that since JJ is letting hers grow back, I’m supporting her by letting more of mine grow back? There isn’t that much, but she appreciates having someone to commiserate with about the itch.”

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