Lucky Over 40 Ch. 12: Jill likes My Dream

Author's note: This is the (revised) twelfth part of the story of two single 40somethings who met on-line and eventually 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 some things might be better understood if you do.

Please check the story Tags to see what you may or may not like. If anything 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 while, and we've been having a lot sexy fun. I feel like the luckiest guy in the world to be with her. We have a pretty unusual relationship, especially the way Jill has occasionally "lent my services" to a couple friends in order to help them out with some sexual frustrations. Recently I realized that I've fallen in love with her, 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 kept me occupied a while afterwards. When I finally got home to my bed, I was asleep in about a minute. 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 you got 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 get in bed 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 texted last night has me looking forward to lavishing some attention on your beautiful 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 to visit recently. I'm afraid I'm kinda off limits right now," she said somewhat 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 women's non-verbal "signals" and such...

"No, that's not it. Boy, you really don't do well with women when we aren't perfectly 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 menopause, I'll be very happy to be done with all the cramps and stuff!"

"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 playing sports and 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 what 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, by all means, indulge yourself." I said, with a big smile. "Knowing you're enjoying what you're doing to me, gets me off better than just 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, it usually turns out to be a lot of fun," I chuckled. "Much 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.

"Oh, um, yeah, Ok," I muttered, still not fully awake and getting very distracted by her attention. "Mmm, that's good. Ok, I'll try to remember, if I can concentrate..."

"Well, if that's a problem, I'll just give you some relief and then the blood can move back up to your brain..." she laughed, touching my cock. "Oh I do like your penis, especially when it's so nice and hard. And its big, 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 teasing the opening.

"Oh yes, I like that," she said smiling at me as she stroked my raging hard-on. "I love running my tongue around this head and rim. It feels so velvety soft, and sensuous." She licked gently across my glans and all along its underside, tracing the rim.

"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."

Her tongue licked the underside of my shaft from bottom to top a few times, before she teased my frenulum and 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. There was a bunch 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 as if trying to pull all the built up cum out through a straw. Her saliva 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 felt like 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 fondle my ass. I really 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 my aching dick and back up once again. "And I like the perfect size of your big, hard cock." She enveloped it again, sucking hard for a few seconds. "Not too thick and not too long. It's such a pleasure to do this." Again, she sucked on my cock head and then slid me deep into her moist mouth for several seconds. "It fits my mouth, and my pussy, so very, very well." She stroked me with her hand and kissed the swollen purple head 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 each time, and she seemed to enjoy that so much she just kept doing it as she giggled.

"Oh, Princess..." I moaned, as she licked my dick. "No, she didn't... Oh fuck, you're making me nuts..." I tried to concentrate on what she had told me. "I didn't think she was serious about that. Does she really want to sell copies of my cock in her shop? That'd be weird, but flattering I guess. Oh Honey, I love what you're doing to me..."

Jill had been sucking and stroking me again, and she hummed "Uhmmm hmmm," in agreement with everything I was saying. The vibrations felt incredible, especially when my cock was deep in her mouth. When I moaned deeply, she hummed long and low, her lips gripping my shaft, and her tongue rubbing the underside. I moaned louder and caressed her hair.

Her fingers probed deeper into my ass crack. I bent my legs up and out to open myself to her and she hummed again. A finger pressed against my anus making me half whimper. She took her mouth off my cock, but continued stroking it, teasingly stating the obvious, "Oh, you like that." She wet a finger in her mouth, then pressed it into me, while licking the sensitive frenulum just below the head of my eager cock.

"Oh fuck, yeah!" I was fully awake now. "Oh, baby, you know I like it. If you keep doing all that it's definitely gonna make me cum." My penis 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 swishing all over it.

"FUCK, you're so good, Jill," I moaned loudly. I involuntarily pushed my cock up at her. I didn't need to be in deeper, I just wanted more of whatever she was doing to me. Her finger rubbed my prostate in unison with 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 reflexively, almost uncontrollably, from all she was doing to my penis and prostate.

Before long I called out that I was about to come. She hummed in response, 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 out of her mouth, 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, then wiped her cum covered lips across mine.

"Oh, fuck," I sighed in relief. "Yeah, my balls were getting pretty uncomfortable. I guess they were really full. Thanks, Princess! That was amazing, and just what I needed." I felt blissfully drained.

As I recovered, I said, "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 this 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 very much better.

"Please crawl in here to snuggle with me, will you?" She pulled off her top and bra. I started to get aroused again watching her beautiful breasts bobbing as she freed them and kicked off her shoes. Her nipples were fully erect and appeared to beg for attention. "Damn Jill, you are gorgeous!" She blushed a bit. I reached out and fondled one of her lovely breasts 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 marvelous mouth, Tiger, please?" she asked, holding her perfect tits for me.

"Oh Honey, 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, my tongue swirling 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 so firm and erect; so enticing. My tongue lavished it and I adored the feeling of her in my mouth. Judging from her sounds, so did Jill.

My teeth brushed against the nipple and she cried out in pleasure. "Oh Rob, bite it, gently, please. Yes, oh yeah..." I held the stiff nub in my teeth and tugged on it lightly. My fingers rolled and pinched the other one. I made love to her incredible breasts with my mouth for several minutes before she moaned, "Oh Honey, I'm gonna come. Oh fuck, it's gonna make me come."

I intensified my attention, and as my tongue teased over the tip of the nipple being pulled by my teeth, she shuddered and collapsed on top of me. I held her tightly, amazed at what had occurred. Giving a woman an orgasm just from nipple stimulation was a new experience for me. Well, I guess there was more to it than just that physical stimulation, and she may have been rubbing herself on my leg, too, but it was still pretty amazing to me.

After another minute or so, Jill got under the sheet with me, still wearing her scrub pants. 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 we snuggled and I held her close.

"I love you, too, Tiger." She said, softly. We kissed again, 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 so 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, even 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'm 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 you just had, then I really need to remember that 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 it 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. I bet she wanted to make good use of this beautiful dick. 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 `till she came on you face. I'm sure you did, though. Did she taste good? Hmm, did she?" Jill teased me and held my dick as it grew stiff in her hand. I'd been at least half hard since 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--does, and she says you'revery good at it. And at other things, too. Deejay really liked your tongue, too, and your other thing." She giggled, still toying with my erection. She was doing an excellent job of working me up again, whether she was trying to or not.

"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 the women she had arranged for me to have sex with, and who were also 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, then slapped my dick. "Get up and you can tell me while you shower. I'd offer to scrub your back, but your shower's really too small, so I'll just watch you rub yourself," she laughed.

We got up and headed to my bathroom, Jill leading me by my cock, as she likes to do. "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 squeezed my cock. It stiffened more in her hand, and she said, "I really like when it does that, too."

"Um, I'd love to let you, but it's hard to pee with a hard-on, and even harder to aim at the toilet."

"Hmm, Ok, we'll aim in the shower, then," she responded, turning me and patting my butt with her free hand. That got my dick to twitch again. I don't know why, but I love it when she fondles my ass.

She stood behind, reached around and held my cock. I closed my eyes and tried hard to relax. Eventually, the stream started and she watched around my shoulder. "Turn a little, please, so I can have a better view," she whispered in my ear, sexily. I put my arm around her neck.

This was about the third time she held me while I peed. I was enjoying it more than previously, maybe because it didn't seem as weird now. But it was arousing then, too; I love having her hand holding my cock. Plus, feeling her tits and hard nipples pressed against my back, and her other hand caressing my chest and nipple, was all very sexy. My dick got harder even while I was 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 her warmth 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 and I took a deep breath.