Lucky Over 40 Ch. 12: Jill likes My Dream

"Um, Ok, it's in the cabinet behind the mirror." Jill washed her hands and retrieved the trimmer. She had done this for me (or to me) once before, but it was a while ago, and things had grown some. I never really did much "manscaping," but I understood that the shorter hair made all her wonderful oral attention nicer, for her at least. And, it was sexy to have her doing it for me. Maybe I should return the favor sometime, though she has a lot less to trim.

"Ok, stand in the shower and lift your arms so I can crop up there." 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 trimmer following.

"Not too short so it doesn't bug you. And we won't bother to give you a bikini line, since I don't want you strolling around in a speedo at the pool. You'd look really good, but that beautiful bulge isn't for the general public," she teased as she trimmed. "I like this hair, maybe 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 in? There isn't that much, but she appreciates having someone to commiserate with about the itch."

"That's fine. You know I love the look of your pretty pubes. It'll be a little more to love about you," I said, thinking about how appealing I find the soft golden curls around her pussy. I do love her bush, and when she's bent over with her legs parted--especially when she is aroused and it's damp--the sight of her pubic hair peaking between her legs is very alluring.

"Ok, all set in front, turn around and open up, Tiger." I did as requested, parting my legs for her. She pushed me to bend over and trimmed around my balls and perineum. The vibrations from the clipper sent tingles through my groin, and got my cock up again. "Now it's time to spread those cheeks, Babe." I pulled my ass open and she shaved in my crack and around my anus. Before she stood, she ran her fingers across my hole a couple times, followed by the tip of her tongue, slowly, but just once.

"Oh fuck, that's not fair," I said in response to her tease.

"Is that any way to thank me for grooming you so well?" she said, slapping my ass as I stood. "Ok, now it's time to get in the shower and clean up. And tell me about that dream, but no jerking off," she added as she playfully patted my erection when I turned to close the shower.

"Remember this was a dream, so some of it may not make sense, or may be unrealistic, or impossible. And it doesn't mean I really want to experience all this..."

Jill cut me off, "Or maybe it does. What would Dr. Freud think about it...? Anyway, get on with it. What was your wonderfully horny mind dreaming of?"

"Ok, but I don't really remember it all, so there are holes..."

"I bet there are! Lots of them," she giggled, "Sigmund and I wanna hear what happened with those holes."

"Yeah, whose wonderfully horny mind is at work now? So, Ok, I was with you, and JJ, and um, Deejay, and some other women, I don't really know who or how many. Maybe your sister, Barbara, was one, though I've never met her. It's kinda vague and dreams are weird... Um, so, I had this paper bag, like from the grocery store, over my head. And I was naked except for that and a skimpy thong like pouch thing. It was lighter than the one you got me, and it covered my semi-soft cock completely, but none of my butt. It's weird because the bag didn't let me see anything except straight down, but I was viewing everything from outside myself, like a movie. Dreams are odd, ya know?"

"Yeah, they are, but I'm starting to like this one. Get on with it."

"Ok, the women were all wearing dresses, or skirts, and sitting in nice chairs, or a couch, sipping drinks. I was standing and they had me turn around, bend over, sorta pose and stuff. They commented about my ass and what was in the pouch, and all that. Oh, and some had their phones out, taking pictures."

"Well, we do all think you have such a nice ass. And a very cute cock. Did we get to see it?"

"Uh, yeah. I stood right in front of the unknown woman, or women I guess, and they pulled the pouch out so they could peek in. Then one yanked it off and my partly stiff cock bumped her face when it popped free. She seemed to like that, and everyone else did, too."

"And did you like it? I bet you did. I might like to have your stiff cock slap my face sometime. You have such a nice cock, Tiger," she cooed while apparently staring at my growing erection though the shower glass. Recounting the dream, and hearing Jill's comments, was getting me aroused again.

"Um yeah, sure, I guess. I don't know for sure in the dream, but it's kinda exciting remembering it. Anyway, the others were telling her to rub her face against it, and kiss it, and lick it. She did, and I was really hard, and pretty big--bigger than real. It was a dream..."

"Um, hmm. I bet you got big and hard, real fast. I have to remember to try that sometime. Sounds like fun, and I bet you'd like it. A lot," she snickered.

Yeah, I bet I would with you doing it. Anyway, this unknown woman took hold of my cock and looked it over carefully, moving it all around, sort of inspecting it, or something. It was like she hadn't seen many.

"Then things jumped around, or I've forgotten stuff, but the next thing I remember is that I was standing there jerking off while they watched and cheered me on. And then you were standing behind me, stroking my cock and telling the mystery girl how to do it. I said something and you covered my mouth with your free hand, telling me not to speak unless told to. Well, JJ really liked that, and so did Ruth--oh, I guess Ruth was there, too. Oh, the paper bag was gone! Weird... Anyway, you kept stroking me from behind while others came over and played with my balls, rubbed my ass, or even licked my cock head. Some took pictures.

"Oh, this sounds like a lot of fun. That paper bag thing was odd, but kinda interesting. Like some X-rated Gong Show guy; the 'Unknown Stripper,' or something... So where did that idea come from?"

"Um, I don't know. Well, Ok, I guess I've seen some CFNM pics or videos with guys wearing only bags over their heads while girls jerk them off. So maybe..."

"Hmm, do you like CFNM videos? Is that a turn on for you, Tiger?"

"Umm... Well, Ok, yeah, sorta, I guess...as a fantasy thing. I don't want to really do this..."

"Ok, just wondering," she had that tone that told me there was more going on in her mind than a passing curiosity. There was more going on in my mind, too, but I didn't want to tell her that the idea of being watched, even objectified, and played with by a bunch of women did have a sort of allure for some reason. I'm not into humiliation, and this was almost the opposite, since they liked what they saw, and felt, and they made that known. I was pondering this when Jill asked, "What else did we do with you?"

"Uh, it's hard to remember what happened when, or in what order, or anything. I remember little pieces. The stranger, or strangers were sitting and you stood me in front of them so they could each fondle, or lick my dick. Someone said that made my cock jump. Others encouraged her to suck it, but she balked. So Ruth, I think...well someone, jumped up and showed her how to suck hard on my cock head, and then on the whole thing.

"Um, I remember I was just standing there, holding my hands behind my head, while everyone took turns sucking me for a little bit. Someone, maybe JJ, started playing with a plug that was in my ass while others sucked and groped me. I don't know when the plug got put in," I said, musingly, trying to make sense of it. Jill laughed at me. Through the shower glass, it looked like she was holding her breast and may have had her other hand in her pants.

"Then I remember being on all fours with someone using some kind of T shaped black toy in my ass while others took turns jerking me off. I was eating out someone who was sitting on the couch as the others stroked me and massaged my prostate with the toy."

"Oh that's good," Jill enthused. "You really were horny weren't you? I like this dream. Did you like it? I'm sure you did. I can see how hard you're getting, even through that steamy glass. I'd like to be stroking that gorgeous thing while you keep telling more about this dream. Finish up and get out here and maybe I will. You wouldn't mind, would you?"

"Mmm, no, I like it when you stroke me," I replied with a big grin she probably couldn't see. What I could see was that she had pulled her scrub pants down and had a hand between her legs, with the other on her breast. "You don't usually jerk me off. Have you ever really given me a hand job?"

"Hmm, no, I don't think so, but it'd be fun," she answered, smiling. "Sometime I wanna do it like in your dream, with you on all fours, and a toy in that sexy ass; rubbing your cock and your prostate `till you give me lots of your creamy cum. Did you blow a big load in the dream, Tiger?"

"No, I don't think so, not before I woke up. I don't recall much more except that the other women had me eat them, too, while I was on my hands and knees, still getting played with. But, yes, I liked it in the dream I guess...and I guess I do thinking about it now, too." It did seem pretty fucking hot, even if maybe I didn't really want to admit it, at least not right now.

"Oh, yeah, I remember that at some point I was on my back with one woman riding my cock and another riding my mouth, both wearing dresses that were draped over me so I couldn't see their bodies. Oh, and I vaguely recall something about JJ and her ex, I think. She said she wanted all of them to use him, too, and I saw some other guy was getting pegged. He was protesting about it, sort of.... That part's all really fuzzy. I'm trying to picture it again...

"I really can't recall this well, but he was bound and getting pegged hard...with someone's crotch pushed in his face. He didn't seem too happy, but he was also moaning a lot, like it felt good. The girls all really liked seeing it. Anyway, I woke up around then, so I think that's about it." I opened the shower and reached for a towel as Jill pulled her hand out of her undies.

"Sure you don't need some help with that," I grinned at her, before drying my face with the towel.

"No, not today, thanks," she said a little shyly. "That's a great story, Tiger. JJ would probably like that last part. I wish you had more. Maybe you could make up some more for me...or maybe I will," she added with a faraway look, until I started drying my butt and my back. That made my semi-erect dick bounce around, and it made Jill smile.

"Ooo, you look so nice like that." I dried my balls and got even stiffer. "The girls would like this show."

"I wanna play with that nice hard cock and jerk you off. Or should I watch you jerk off for me? Would you do that? Can I watch you stroke that lovely cock?" I began rub my dick with the towel, not really thinking about it, as I stepped out of the shower. "Oh yeah, that looks nice. Yes, I like seeing that." She began playing with my balls. "Umm, but it makes me wanna take over and do it myself." She took hold of my cock from the side and gently pumped. Soon her other hand was fiddling with my ass again.

"Do you like this, Tiger?" she purred, staring intently at my erection. "I like stroking this beautiful cock. It's so big and hard and hot. I wish I could put it in my pussy, but we'll both have to wait until next weekend. Then you can bend me over and slide it deep into my warm, wet, pussy. Oh it'll feel soooo good, Tiger. I love your cock." She went on and on, making me think about being inside her, fucking her from behind, knowing it was working on me, and I bet it was on her, too.

Her hand was gripping me just tight enough as it slid up and down my shaft. When she got down to my base her thumb would rub over my frenulum, the sensitive strip on the underside, just below the head. Fuck, she was good at this. Where did she learn it?

A finger pressed against my wet anus and I pushed back onto it, squatting a bit. "You want this in there? Ok, Tiger. Let me find that magic spot for you." She grinned broadly as her finger sought my prostate, and I moaned. "It feels good, doesn't it? Remember the Feeldoe? You liked getting pegged, as it rubbed your p-spot. Mmm, and I liked you putting this lovely cock in my ass, too. Sliding in and out...it feels so good...

Between what her hands and her sex talk were doing to me, and that dream still in my mind, it wasn't very long before I felt an orgasm building. "Ummm, I'm gonna come for you real soon, Honey..."

Suddenly she let go of my cock me and slid her finger out of me. FUCK, I was almost there. I looked at her with wide eyes and almost yelled, "What the hell, Jill?"

"Oh Tiger, I'm sorry. I just got so hot thinking about you fucking my ass and thought you should do that now. Would you? Would you like to put your beautiful cock in my bottom and fuck me? Please Tiger?"

She looked at me with her beautiful eyes begging me to butt fuck her. How could I refuse her? "You know I'll do almost anything for you, Princess," I replied, with only a hint of sarcasm. She immediately stepped past me, grabbed my cock again and pulled me to the bedroom at a brisk pace.

When she got to the bed she pulled down her panties and stepped out of them as she reached in the bedside table. She handed me a condom, saying "Put this on so we don't have so much to clean up later." As I did, she pulled out something else out and said "Oh, this will be fun, too. Bend over and open your nice ass for me, Tiger." She showed me the bullet vibe as put some lube on it.

"Whose ass is getting fucked?" I asked her.

"Mine, but you can have some butt fun, too. Your prostate will thank me later..." she said as she fingered my ass and then slid the vibe in me. Once it was in place she knelt on the bed and wiggled her gorgeous ass at me. "Come on stud, fill me up. I need that big, beautiful cock."

I bent down behind her, kissed her lovely ass checks, then spread them apart to lick up the length of her butt crack, and back, finally teasing her anus with my tongue. "Oh damn, that feels good. I do love your tongue, but I want that cock. Please, Babe, lube me up and slide it in me."

"Your wish is my command, Princess," I said as I put some lube on two of my fingers. I rubbed it onto, and then into her puckered hole as she moaned and pushed back against my fingers, coaxing them inside her ass. She wiggled her bottom and moaned, while her hand went to her crotch and rubbed. "I'm so fucking hot! Please Tiger, I want your cock in me." With that, she turned on the vibe in my ass and a tingle went through my groin.

I stood behind her and rubbed my cock head against her, mixing my pre-cum with the lube on her backdoor. She moaned loudly and pushed back against it. Before I even had a chance to try to penetrate her, the head was already halfway in. "Yeah!" she exclaimed, pushing back again until my head popped fully inside her. "Oh fuck, that feels good! Put some more lube on and pump me full of your cock, Babe." I did just that, and soon had half my dick inside her. She moaned, and fiddled with the vibe remote, causing it to alternate buzzing and thumping inside me.

"Oh fuck, don't change that setting. It feels great pounding my prostate."

"Good, now pound me with that pecker." I pulled back and slid in again, deeper. Out a little and back in more, until I was touching her ass with my pelvis. "Oh yes, that's it! Now do me, Tiger. Fuck me!" We quickly had a rhythm going, both moving together to slide my cock in and out of her tight bum. The rubber dulled the sensation on my cock some, but the vibe more than made up for that loss of stimulation.

She rubbed her pussy and I leaned forward to caress her swaying breasts. We were both moaning each time I plunged into her, again and again. Our bodies slapped against each other: smack, smack, smack!

"Oh this is what I need! You feel so good inside me. Pull on my nipples. Oh yeah, like that!"

After a few minutes of ass pumping, prostate pounding, pussy rubbing, nipple tweaking, and a lot of loud moaning, she said, "Oh fuck, Tiger, I'm so close..."

"Me, too, Honey. I hope I don't come too soon for you," I said almost breathlessly. I was trying to hold back, but it was very, very hard. Damn it felt so good. "Unngg, can't hold... Coming..." My hands gripped her breasts, squeezing her nipples between my fingers as I pushed hard into her. I pulled back a bit and exploded as I pushed in again as far as I could while my cock twitched inside her.

"Fuck...me tooooo....," she cried, as she trembled, pushing back onto me and squeezing my cock with her ass.

We held still, pressed against each other, as her tremors subsided and my cock relaxed. I loosened my grip on her breasts, cradling them gently, while I kissed her shoulder blade. Jill stretched her head back and rubbed it against mine, as the hand at her crotch slid down and caressed my balls. Then she found the vibe leash and tugged, so it popped out of my ass.

"Oh, wow! I didn't know anal sex could be that good! Ok, that could get me to look forward to having my period. Maybe." She laughed and I just shook my head.

"It was definitely the best ass fucking I've ever done. And I'll be happy to do it again whenever you want, but I 'm really looking forward to enjoying your pussy as soon as I can," I said as I slowly slid out of her and flopped on the bed, pulling her next to me.

"So am I, Tiger, so am I," she replied as I hugged her. And we kissed; deeply, tenderly, lovingly.

"Oh that was nice, but my pussy wants much more! My brain and all still say no, not now. Oh, I don't know... Just kiss me Tiger, please."

"That's totally your call, sweetheart, but know that I'm Ok with it if you want some pussy play," I told her, before kissing her deeply. Our tongues danced and I hugged her close.

Eventually she broke the kiss, saying, "It's tempting, but I'm just not comfortable with vaginal sex during this time. Maybe sometime we'll try, but only if you're really, really sure. My late husband really, really wasn't. I don't know, maybe that's part of my problem..." She went quiet and I didn't push her. I had former girlfriends who were very uncomfortable with it, so though it truly didn't bug me, I let it drop.

After a bit, Jill shook her head as if to clear it and said, "We need to get up and get dressed `cause I really need some food!" She got out of the bed, and gave me a playful swat on the ass when I rolled over.

I got dressed and Jill decided to wear one of my button-down shirts, not bothering with her bra or all the buttons, and leaving it untucked from her scrub pants so it just covered her cute butt. Damn, she looked sexy like that.

We headed out to have a quick late lunch at a little place not far away. Being after 2 by now, we had no trouble finding a quiet back table where we could relax and talk. After we ordered, Jill said she had some news, and I told her I had some thoughts I wanted to run by her, too.

Jill started by telling me she had her last visiting nurse session with Deejay's mom this week. She's no longer bed bound. Though not fully back to normal, she can function without needing someone there all the time, so Deejay's thinking about going back to finish college locally, as a day student.

"Hey, that's great. Do you know what she's studying?"

"Journalism I think, or some writing major I'm pretty sure; it's been a while since I talked to her about that specifically. She and Teddy had a wonderful date last week. They had intercourse yet, but she's sucked him off again, and he's returned the favor. She said he did a very good job, though not as good as you!" She smiled at me and squeezed my hand across the table. "But she thinks he could get there with some coaching. Anyway, she's really looking forward to sleeping with him...but not sleeping." She laughed. "Oh, they had another date last night, so maybe she did! I haven't talked to her yet..."