Lucky Over 40 Ch. 07: Saturday

"I like a lot of things about your nice cock, have told you that?" she said fondling my member and waking it up some. "You don't tear me up or make my jaw ache from opening my mouth too much. You fit me very, very nicely." She gave me a big kiss, and a little squeeze to my dick.

"Anyway, as far as anal sex goes, I think you'd fit me better, and I know you'd get me much more ready for it, anal that is. The plugs showed me it would probably be fun. Oh, and if we put that new vibe in my pussy while you fucked my ass...maybe with yours stuffed in your cute butt at the same time. Oh yeah, that could be fun, Tiger!"

"You're a dirty girl," I said, kissing her. "A dirty, sexy, horny, smart, beautiful woman who makes my cock eager for her, and I love it!"

"Yeah, you say that to all the women you might get to fuck in the ass," she teased. "How many have you fucked someone in the ass, anyway, babe? Did they like it? Did you?"

"If you're really asking," I responded, "the short answers are: one, I don't really know and I don't remember. Yeah, It was several years ago and we were both fairly drunk. I only have a very vague recollection of it, but I'm 99% sure it happened and wasn't just a dream."

"Yeah, Ok, sorta sounds familiar," she said. "So, do you often have dreams like that? Have you had a sex dream about me, babe? When was the last time? When was the last time you had a wet dream? Have you had a wet dream about me?"

"Whoa there, hot stuff," I said, trying to stem the endless stream of questions. "I can't answer so many questions at once. Maybe you need to write them down and let me answer them like a blue book exam."

"Ok, professor, that's fair," she said acknowledging her excessive questioning. "It just turned out to be such an interesting topic that got me real curious so all these questions popped into my head. Maybe it's something we can explore more together, later."

"Yeah, I'd like to hear about your sex dreams, too, my curious little sex kitten," I said. "But I'd really like to get back to what else you think you want to explore together."

"I'd like to explore more of you, babe," she said, caressing my chest. "And have you explore me, too." I turned my head, and with a hand on her chin, pulled her mouth to mine, kissing her deeply. She sighed and I made a little sound of agreement. She put her head back on my shoulder, but in less than a minute she sat up and said, "We should watch some porn together, don't you think? I think I can cast it from my phone to the TV right here. I've never done it that way, just watched a little on my phone a few times. You do watch porn, too, right? What kind do you like?"

"Here you go again," I said with a laugh. "Let me catch up. Yeah, that sounds like a fun way to spend some time together nude. And yeah, I watch porn on my computer at home, I'm a guy, a horny guy, remember?"

"How can I forget? It's one of the many things I adore about you," she said, kissing me and rubbing a hand between my legs.

"Yeah, I'm sure it is," I said, giving her a little kiss and pussy rub in return. "I like various things, it depends on my mood. Mostly stuff with 'real' people, or 'real looking' people at least. Oversized and fake boobs, monster cocks, that kind of stuff doesn't really do it for me. To be honest, I guess I like it best when I can picture myself as the guy. And with this tall, mature, blonde, with long hair, lovely firm moderate sized breasts that match her slender frame, an unshaved pussy, and a GREAT ass. Yeah, that's my kinda porn babe."

"Hmm, I think I may have seen someone like that before," she said as she kissed me again. "You really know how to flatter a woman by telling her she's your dream porn star."

"Well, she's MY porn star, and she really is sexier than any in the videos you're likely to find on that site you're pulling up. The only problem is her taste in costars isn't very hot."

"Oh yes it IS," she retorted. "You're awfully hot to me. And Deejay thought so too, so she told me. And Jill at the store was into you."

"Jill-2, you mean. Yeah, that's a topic for discussion sometime," I said in a serious tone.

"Yeah, well," she said a little playfully. Then she deflected, "What do you mean 'Jill, too?"

"Oh, that's the name I have for her; she gave it to me. When she first told me her name, she said "I'm Jill, too,' as in also, but since she's the second Jill in my life right now, I think of it like Jill number two, sorta like the Dr. Seuss characters. Anyway, you set me up twice with her, didn't you?"

"Sort of," she said a little sheepishly. "She made a complimentary comment about you the first time we were in the store, and again when I was telling her you'd be in with Deejay to repeat our purchase. I said I wondered if you'd plug Deejay in the car, like with me, and she said she'd let you use a room. She joked that it was also a glory hole, and if she could get you to 'present' yourself to the room next door, she might like to give you a try -- because of my descriptions of how much I like your cock. She's never done it with a customer, but she's had lots of requests. You, mister, made her consider making an exception. Anyway, I thought it could be fun, for both of you, and so we made some plans with Deejay.

"Wow," I said with true astonishment. "I figured you were behind it, but wasn't sure, until now. So it was your story telling that made her consider it. But what about yesterday, and my 'returning the favor,' that was you again, wasn't it?"

"Hey, you made the suggestion, I just passed it along. She does like you, and she told me she was really horny since she had to throw out her cheating scum bag boyfriend months ago. She really won't do anything with the customers, for many reasons. But she considers me more of a friend, and you too, by extension. So, when I told her what you said, she asked me if it was really an offer, and if I minded. I told it was all good, and you know the rest."

"I really didn't expect you'd tell her, but I should have known better," I said. "I'm glad you were there, so it didn't go farther. How did you feel watching me eat her?"

"You know, I got me hot as hell. My pussy was dripping and I really wanted to rub myself, but I guess I wasn't comfortable enough. I was kinda like a deer in headlights watching you, and her reaction to you was, like, wow! It was like watching 3D porn or something, and with my very favorite porn star!" she said as she kissed me. "I think I would've liked to see you doing Deejay, or her doing you, or both! You didn't film it, did you, babe?"

"NO, we didn't film it! Unless she has some hidden camera," I joked. At least I hope it was just a joke.

"Too bad. Maybe next time," she said with her sly grin that didn't always indicate she was just kidding. "Ok, I got the porn site up on the TV now, and have it set for 'Amateur' videos. Do you want a sub category, or just browse this big list?"

"Um, either way I guess. I don't know what category to head to. I haven't watched porn with someone else. I don't know your preferences, either, so I'm fine if you pick something."

"Ok, babe," she said, more readily than I expected. "Here's one with a compilation of handjobs by amateur women. Oh, that's a nice start, jerking him off from behind, at the bathroom sink. Hmm, I need to try that, don't I, babe?" She gently rubbed her hand on my stiffening cock as I indicated that it was just fine with me.

"Oh, now we're in the car together," she teased in my ear while watching a woman stroke her passenger's big cock while she was apparently driving along. "Yeah, that's fun, but you may make a big mess on your clothes, since I can't lean over to catch it in my mouth," she giggled she was stroking me in time with the image on the screen. Between that, the video, and her sexy banter, I was getting very excited.

"This one has her playing with his ass, too. I do like to see you when I rub your prostate; it turns me on to see you so turned on. We may need to reenact this one right now." She paused the video, told me to get in position like the guy on the TV. As I did, she ran to the bedroom, coming back with a bottle of lube and an exam glove. I was up on my hands and knees and she said, "Mmm, you look good babe. It makes me wet to see your swollen cock hanging like that."

She sat behind me, leaned in and kissed me on the ass, then licked the length of my open butt crack before zeroing in on my hole and tonguing it. Her hand fondled my balls, then took hold of my eager cock, stroking it gently a few times before letting go to put the glove on one hand, then some lube on her finger and my ass. She started the video again and began to stroke me slowly as her slippery, gloved finger entered my waiting asshole.

"Oh yeah, kitten, that's really good," I told her. "And it's hot watching it at the same time." She kept working me until the scene changed to a clothed girl sitting next to a naked guy on a couch, jerking him off, and licking his cock occasionally. She stopped fingering me, but didn't pull out. She continued to gently stroke.

"I wanna do that, too, but I'm not making you move," she said. We'll put a pin in that and come back to it, babe." I just moaned in agreement.

The next scene was another prostate job, with the guy on his back. "Ooo, I like it, we'll do that now, Ok?" She asked, I told her that's fine and she pulled her finger out so I could reposition myself. I was soon lying on my back, holding my legs up by my chest and spread wide. She sat between them, turned on the video again, then slid her magic finger back in me and started stroking my cock.

The video had no dialog here, but she was adding her own, asking, "Do you like this, babe? Your cock tells me you do. Your prostate is nice and full. I don't want to milk it though; you need more juice for later. I want you to give me lots of cum all day today. Am I a cum slut? I only want YOUR cum. And I'm going to share it with you. I'm going to suck your cum from you, like she's doing, but then I'm going to kiss you, babe. Do you like that idea? I like doing this; stroking your beautiful cock, and wiggling my finger deep inside you. Rubbing your p-spot, to make you cum, like you do to me. You like to make me cum, too, don't you, babe?" She went on like that and it was erotic as hell to me.

I was moaning and groaning in pleasure, often answering her questions with only grunts of agreement. It felt so good I might have agreed to almost anything. When she started to ask me if I was ready to come, would I come for her, did I want her to make me come? I answered, "Yes, baby, make me come, make me come for you, I want to come for you baby." I babbled, and moaned, and almost begged.

She pushed harder on my prostate, stroked me, and took the head of my cock in her mouth, sucking on it and working her tongue all around, until she pushed me over the edge. "I'm gonna come. Here I come. I'm coming, baby, ugh, ahg, Ah, AAHHhhh." I filled her mouth with my cream and she gave a long and apparently very satisfied hum.

She slipped her finger out of my ass and stood, moving up by my head. The video was still playing in the background as she kissed me with her mouth full of cum. When she was done, she said, "Oh that was good babe. I liked that a lot. And you did too, didn't you?" She sat back down, placing my head in her lap. "Hmm, what shall we watch now..."

"How about something where I get to make you cum, and cum hard?" I suggested.

"Oh, that would be nice. Any preference, babe?"

"It's for your pleasure, so I'll throw it back to you, but pussy eating and face sitting, might be good options. A compilation of female orgasms ought to have some good scenes to try, or just watch," I offered.

"Ok, let me browse a bit. Oh, what's that one? Pegging? That's anal with a strap-on, isn't it? Hmm, it looks hot to me, even if it isn't centered on her pleasure. Maybe I'll try sitting on your lovely mouth while watching this collection of pegging scenes. That should get me off pretty quick. Can I sit on your face, babe?" she teased.

I slid down the couch a bit and she straddled my head, planting her very wet pussy on my mouth. It was hard to see the TV, but I was more interested in the beautiful bush in my face. Soon I heard the typical crappy music of a porn film, with a little moaning in the background, but mostly Jill's commentary as she moved around getting my tongue where she wanted it at that moment.

"Yeah, lick me there, oh good. This looks like fun, babe, would you like me to fuck you like this? Plunging that dildo in and out of your ass? I'd think that could be fun... Oh, right there, push that tongue in my ass. Yeah, just like I'd pound your tight ass... Oh, yeah, this is gonna get me off!"

Suddenly she stopped moving and said, "Hey, does that girl look like Deejay? She looks good with that strap on, doesn't she?" I tried to turn my head to see better, and Jill moved a bit so I could. "See? You didn't do this with her, did you? Yet?" she teased -- at least I think it was a tease.... She moved her pussy back over my mouth but at an angle so I had a little better view of the video.

"Would you like it if Deejay fucked your ass, babe? How about Jill, I mean, um, Jill-2? Should she peg you? Oh, yeah, lick me like that," she said when I distracted her. "I bet she's experienced at it, huh, don'cha think? Ooo, I'd like to fuck you and stroke your cock, like that girl's doing to him. And then watch you come. I wanna watch you cum for MEEeee. Oh yeah, suck my clitty, babe."

As she ground her pussy into my mouth I managed to slide two fingers into her cunt and found her g-spot. She moaned loudly, not even talking any more. I figured maybe it was time to see if I could finish her off, so with my other hand I fingered her asshole.

"Oh yes! Suck me and finger me in both those holes, babe. Push them in me. Oh suck my clit and... OH your tongue, is...going...to...maaake meeee...CUMMMM." She clenched everything up, her hands were gripping my hips as she leaned forward, with her snatch tight against my mouth, my fingers gripped by her pussy and ass. Then she started to shake and quiver, finally rubbing herself against my face and exhaling heavily.

"Wow, that was good. Damn, Tiger, you give me the best orgasms," she said as she slumped forward, laying on me, hugging my legs with her chin nestled in just below my balls.

"I'm glad you find me pleasing, sweetheart," I said with a little tease. "Think you'll keep me around a while, then?"

"Yes, I think so," she said and she hugged my legs a little tighter, snuggled her cheek on my thigh, and wiggled her ass just below my chin. Then she got up, turned around, and lay back down with me on the couch, cuddling. "Yeah, you're definitely worth keeping around," she said as she kissed me.

We lay there a while, ignoring the end of the video. Before long, we both fell asleep, nude on the couch, wrapped in each other's arms. Something woke us a while later and Jill said, "I'm getting sorta hungry, how about you? Maybe we could have some cheese and crackers and some wine, or something."

"Yeah, that sounds good. I need to stretch some anyway," I replied. "I'll, open the wine." I poured two glasses as she prepared a couple plates of cheese, fruit and crackers.

We returned to the couch and decided we had enough porn, for now anyway. We chatted as we snacked, still fully nude. It was different, but fun, and we talked about that.

Jill wondered if we should go to one of the nude beaches in Florida, sometime. She'd never tried it, but thought about it a couple times. I told her I'd be too concerned about getting aroused, especially with her around, and then having to try to hide my hard-on -- a problem she didn't have to worry about having.

She said she understood, but added, "I'd love to see you strolling the beach with your beautiful cock sticking out. I love to see it sway and bob when you move around. Oh, look, it's growing now, hearing me talk about it," she teased, and gently fondled me, making it grow even more. I tweaked her nipple in return, making it get hard, and told her if that happened on a nude beach she could always say she was just cold. She leaned in and kissed me. We snuggled as we sipped our wine.

My cock continued to grow and she played with it, teasing me physically and verbally. Pretty soon she had me sitting between her legs, with my back against her chest, as she gave me a full-on hand job.

"I've wanted to do this for a while, but never really had the chance," she whispered in my ear. "There's something about really jerking you off that seems so erotic. And, I'm gonna to get to watch you come for me. I don't usually get to see you come. In fact, I don't think I've actually seen you shoot your load, just felt it, and tasted it, or watched you as it filled your shorts," she laughed, then got sheepish remembering that accident was her fault.

She continued to stroke me, her other hand playing with my nipples or my balls, while she whispered in my ear, and nibbled on it. Her breasts rubbed against my back and I could feel her erect nubs brushing my skin. Eventually the pre-cum was flowing and she was getting me close.

She took her wine glass and drained it, then sexily whispered, "Oh, it's empty. You'll fill it for me, with white, right babe? I'm going to have you cum in this glass for me. All your pretty cum from your lovely cock shooting into this glass. You're going to come for me soon, aren't you? I want to see you come for me. I want to feel your cock pulse in my hand as you spill all that delicious semen in my glass like you do in my pretty, warm, wet, pussy. You want to do that for me, don't you, babe?"

"Yes, I do, and I will, very soon," I said as I tried to turn my head to kiss her, but she wouldn't let me. Instead, she teased me with her tongue touching my lips, then my ear, and my neck as she stared at my cock that was getting ready to unload. "You tease," I said.

That got her to tighten her grip and stroke me harder. I moaned and told her I was about to come for her. She held her wine glass by my cock, and pulled my cock down as she stroked so its tip was just inside the rim. She began to giggle, then stopped as I tensed up and began to shoot my jizz into the glass. She was leaning over my shoulder as much as she could, eyes wide open in apparent wonderment. I gripped her thighs and moaned as the cum flowed for her. When it finished, she wiped the end of my dick against the rim of the glass, gathering the last drops, then kissed my cheek before lifting the glass to examine the contents.

"Mmm, doesn't that look good, babe. There's not a lot here, but your been a busy boy in the past 24 hours, so your tank must be pretty low," she said before putting the glass to her mouth and drinking the contents like a shot. "Mmm, yup, I like your cum, babe." And she moved around me to kiss me on the mouth, deeply and sensuously. Then we cuddled together on the couch, once more.

We decided we should watch a movie, a normal movie, nothing more than R rated. As we were trying to think what we could watch I noticed some DVDs on a shelf near the TV. I got up to look at them and commented that a bunch looked like they were from Becky's much younger days. Jill said, "No, they're really all mine, maybe some that are sort of ours," meaning Becky's and hers.

"Really, all these Disney Princess films, like 'Cinderella' and 'Beauty and the Beast'?" I asked. "I think that last one could be our story."

"Nah, you don't have anywhere near enough hair, babe," she said with a big grin.

Then she looked a little serious and said, "I have a confession to make. I'm a Disney Princess. Well was going to be, sort of. Back in my college years I worked as a seasonal cast member at Disney World. My sister worked there -- she still does, actually -- and she got me an audition. I wanted to be a Princess, but it turns out they have height restrictions, and I'm too tall for any of the female characters. I could be a 'furry' though, that's one of the animals that wears a big fake head, like Mickey or Donald. I found out then that anyone who's going to be a face character -- that's one who doesn't wear a fake head -- has to start out as a furry anyway. Well, even those options were few for me, due to being a tall woman. Long story short, I was what they refer to as 'Tigger's fiend' for a while and even 'Goofy's friend' sometimes."