Lucky Over 40 Ch. 08: Weekend Ends

I quickly went back to work kissing, licking and tongue fucking her twitching anus. As I pushed my mouth against her ass, my nose was pushed into her pussy. She smelled wonderful. I wanted to eat it again so badly. As I've said before, I'm not attracted to hairless pussies, but this bare cunny was really turning me on right now.

I kissed and sucked on her bung hole, and rammed my tongue in it. I made my tongue as stiff as possible and extended it as far as I could, then fucked her ass with it by moving my whole head forward and back. Each time I broke all contact with her hole and then filled it again as much as I could, over and over. Her feet were now on my back. She was squirming and moaning and I swear I could see pussy juice running down from her cunt, she was so wet.

After a minute or so of that I just pushed my tongue in as far as I could and shook my head fast against her ass. Then I licked her anus several times, licked up her crack, and entered her pussy again with my tongue. My mouth covered her lips and I sucked at her wetness. She was starting to go wild and took hold of my head, pulling me into her. I shook my head again as my tongue thrashed in her snatch. Fuck, she tasted good.

After a while she pulled me up to her clit. Through her moans she said, "Suck it stud. Suck my clit. Make me cum again." It was then I realized she had probably had a couple little orgasms, most likely when she was squirming hard or pushed in tight against me and barley moving. I confess, sometimes I was paying more attention to what I was enjoying than to what she was doing, but I was realizing that her reactions were part of why I was enjoying this so much.

I began to suck her clit in earnest, while running my tongue over and around it. Every time I licked hard across it she would spasm and moan louder. I maneuvered two fingers of one hand into her cunt and felt for that special place on the anterior wall that should be her g-spot, slowly rubbing it as I licked around her clit. When I licked across it, I pushed on her g-spot.

She apparently came twice as I licked her clit while rubbing her magic spot. She arched her back and pushed into my face, gripping my head and groaning, FUUUUuuck!" The second time she pushed my head away and held it with her hands spread across my cheeks. I saw a small amount of fluid shoot out of her pussy before it hit my chin and mouth. Shit, did she just squirt?

"Oh fuck, that was a good one," Jill-2 said with a sigh. "Oh, did I cum on you? Sometimes I squirt a little, when it's a really good orgasm. Those two were good. You hit all the right places at once, well, almost. Wish you had something in my ass at the same time. Hey, let me get that."

She pulled my face to hers, licking my chin, then planting her lips on mine. She gave me a big open mouthed kiss, with her tongue thrusting in and wrestling with mine. When she broke, she licked my chin again, and said "Mmm, taste good don't I? Pineapple juice," she teased.

She fell back on the bed and said, "I haven't cum like that in a while. Jill was right, you ARE good at that, stud."

"Yes, he is," my Jill chimed in. "You guys even made me cum just watching." She was sort of flopped in the chair, but holding her phone.

"Just watching, huh?" Jill-2 said. "I saw you with your hand in your shorts, and I know you have that vibe in. I also saw you with that phone. I couldn't concentrate enough to see what you were doing, but I bet you had a good wank, and that you took some pictures of us."

"Well, a video," Jill said, blushing a bit. "You guys were so fucking hot. It's just for us though, I won't send it to anyone else. Promise. Really!"

"Maybe I'll watch it later," Jill-2 said. "Right now I'm watching that cock. That nice hard, swollen cock, and thinking it needs something. Why don't you stroke it for us again, stud?"

Both Jills were looking at me, expectantly. "Really? What do you want me to do, jerk off? Now, in front of you?"

"Yes," both Jills said, together. Following it up by each confirming, at the same time, that they wanted to watch me masturbate and even see me come.

"Yeah?" I said, a little surprised, but also quite horny and with my cock aching for some relief. "Well, if you want to watch, I'll try to give a decent show with this little dick." And I started to stroke.

"Oh, it's not little, stud," Jill-2 said. "I bet it's the same size as some of the anatomically correct dildos at the store. How big are you, Rob?" I just made a quizzical face and shrugged my shoulders indicating I don't know, as I kept jerking my cock. "Never measured it? Really? Oh, we need to do that," she replied.

She ran out and came back with a wooden ruler. Removing my hand and taking hold of my cock herself, she said "I don't think you're quite as hard as you were a few minutes ago. Probably stage fright," she giggled.

Jill-2 placed the ruler along the top of my erection and reported, "Even so, I see you're a more than six and a quarter inches right now. Moving the ruler around she added, "And about an inch and a half across your shaft. This pretty head, with its well defined rim, the corona, is more than one and three quarters across."

Letting go of my cock she told me to keep jerking and stated, "All that makes you above the average big boy. Certainly not little. You aren't a cunt stuffer, but it's more than enough to feel damn good, and just about perfect to fill an ass without tearing it apart."

I was stroking my dick again, and both my eyes and tempo picked up after her last comment. I think she noticed. "Do you like ass fucking? Is Jill's ass a good fuck, stud?" she asked.

"We haven't done that yet," my girlfriend said before I could open my mouth. "I did once with my late husband, and Rob did once with someone, but that's it, and it wasn't all that great for either of us. But I wanna try it with him, I think. I'm nervous. He isn't huge, but he is still kinda big, especially that wonderful pinkish purplish head. Oh fuck it looks so good while you're doing that."

"The head is pretty pliable, and his shaft is the same width as the medium butt plug in that set I sold you. He'll fit great," Jill-2 said to my Jill. Looking back at me she remarked, lustfully, "Oh yes, he does look great pumping his cock like that." She flopped down on the bed with her eyes fixed on my dick.

Suddenly, I felt a sort of tingle inside my ass, then a pulsing, and I realized my Jill had turned on my bullet vibe. I wiggled my pelvis and clenched my ass cheeks involuntarily in response.

"Oh yeah, that's a nice little dance, babe," my Jill giggled. "You like that little toy deep in your ass. You'd like to fuck my ass, wouldn't you? Would you like me to fuck your ass? I'm fucking it with this vibe right now." She fiddled with the ring remote and the pulsing intensified, mixed with buzzing vibrations. "Stroke your beautiful cock for us while I fuck you tight ass, Tiger. We want to see you shoot your cum."

"Oh yes, we want to see that, stud," Jill-2 said, lying prone with her head at the edge of the bed. "Shoot it over here, right on my face. Now's your chance to squirt on my face like I squirted on yours. Oh yeah, beat that meat faster. Oh you like this, don't you? You two are fucking hot!"

"We like this, Tiger," my Jill interjected. "You're so sexy stroking yourself and looking like you're getting ready to come. You want to come on her face, don't you? Shoot your spunk on her for us." She changed the vibe to just a strong, pounding pulse and all the stimulation, including their encouragement, and the thought of Jill-2 wanting me to cum on her, had me set to climax.

"Yeeess," I exhaled like a grunt. "I'm gonna come. Cum on you," I grunted as I felt my load about to fire. I stepped in closer to Jill-2's face and pointed my cock down at her, only a couple inches away. "AAAaaahhhhhh," I groaned as I started to shoot a string of cum that hit her chin and neck.

"Oh fuck! Look at that!" my Jill exclaimed.

Jill-2 opened her mouth and lowered her head a bit to catch the next shot, but I had also raised my cock slightly, so it hit her nose. She quickly closed her eyes just before more cum splashed across them. I pushed my pelvis forward so my cock was less than an inch from her mouth and one more shot went right in. I knew that was all I had, since my Jill had taken so much from me in the last 36 hours or so.

Jill-2 pulled herself forward and took my cock head in her mouth, sucking to get all there was. Then she got up on her knees, put a hand on the back of my neck and pulled my face to hers, kissing me. She pushed some cum into my mouth, along with her tongue.

"Holy fuck, that was hot to see! You need to clean your jizz off her face for her, babe," my Jill offered.

I broke the kiss and took her cute nose into my mouth, licking the cum off it.

"Oh, shit, that tickles," Jill-2 giggled, pulling her face back and pushing her hands against my chest. She wiped her face with one hand, licked it once, and then wiped it on her breast. "Fuck, that was fun. I don't know how many times I came today, but there were definitely a couple really, really good ones in there. You're a lucky lady, Jill."

"I sure am," she answered. He's my Tiger and I love him, and his love making."

Shit, I thought, did she just say she loves me? Just a figure of speech, I'm sure. I almost said that a couple times yesterday and today, but I caught myself. Are we really falling in love? Could she be? Am I? Am I ready for that.... So much was going through my mind, when Jill-2 brought me out of it.

Toying with my soft, but decidedly still chubby cock Jill-2 said, "I think Robbie Jr. here might want some rest for a while. He may be kinda worn out, from all the attention between the two of us."

"Oh I bet he'll be awake again before too long," my Jill said. "He's pretty amazing that way. But let's take that thing outta his butt so he CAN get some rest. I know I'm ready to get mine out." She grabbed a tissue, pushed on my shoulder so I bent over, then tugged on the plastic cord, pulling the vibe from my ass.

"Thanks," I said. "And thanks for the kind words. And the all wonderful attention you've shown that little guy, both of you."

"I'm telling you, he isn't that little," Jill-2 said. "Don't downplay your gorgeous cock." Turning to Jill she said, "Hey you got a few more minutes?" Jill nodded. "Let him, or them, get some rest and come talk with me while I take a quick shower and get dressed. You can wash both those vibes in the sink, unless you decide to leave yours in," she teased.

Jill-2 gathered some clothes and they went off to the bathroom together. I stretched out on the bed and quickly fell asleep.

Sometime later I started to wake with my Jill's mouth on my flaccid dick. It inflated pretty rapidly as she sucked and twirled her tongue around it. By the time I was coherent, she pulled her mouth off my nearly fully erect cock with a popping sound. "Oh, that WAS nice," she exclaimed. "I like feeling you grow in my mouth. I've wanted to see what that was like for quite a while, and I'll be looking for more opportunities in the future. It's not often I get to see him when he isn't already hard, or almost there."

Tossing me my shorts and shirt she said, "Come on, babe," Jill needs to get going and we should find something to do today."

"Hey, are you gonna leave him like that, all nice and hard but abandoned?" Jill-2 asked. "If you don't want to finish what you started, then I do. I can be a few minutes late opening up the store, I'm the owner," she said with a smile. My Jill nodded her head and gestured for Jill-2 to go ahead.

I wasn't really paying attention to them, and was pulling my shirt over my head when I felt someone take hold of my dick. I heard Jill-2 saying, "Come over here, Rob," as she pulled me next to the bed while she sat on the edge of it. My cock got harder, reacting to her stroking it with one hand and my balls with her other.

"Isn't it a nice cock?" my Jill was saying. "I told you it was. I love the look of it, and the feel; so soft but firm, and warm. It's so nicely shaped and that head is so very handsome, whether it's hard or soft. Look at that opening, showing how eager he is for attention, probably getting ready to leak cum. I love to see it do that that, or shoot cum. Or take a pee, for that matter," she giggled. I was a flattered buy all this attention, but a little embarrassed as well.

"Yes it is," Jill 2 said. "I wasn't kidding when I said it looks a lot like some of the dildos in my store. Maybe I should make a mold of it and start to market my own line? I like this nice tight ball sack, too," she said fondling my scrotum.

"That feels great, but be careful, they're pretty sensitive," I said. "Really, I usually can't even deal with them being sucked on. But they like licking and gentle stroking. Oh, and I like that, too, oh yeah," I added as she slowly licked across my balls and up the underside of my shaft to the head. The tip of her tongue teased my frenulum, just under the ridge. She was smiling and watching my face, which made it even hotter.

"Mmm, I like this head, too," Jill-2 said licking it. "It's got a great shape and such a well-defined ridge," she added, rubbing her finger on it, and then running the tip of her tongue around it several times, while moaning appreciatively.

"And yes, such a nice slit, gapping open when the head is so swollen like this," she said, flicking the tip of her tongue across it. "Mmm, it's leaking some tasty stuff right now." Then she took my cock in her mouth and swirled her tongue all around the head.

"Fuck, that's good," I said, putting my hands on my hips as I arched my back and closed my eyes. She was sucking the head, hard, and her tongue never stopped moving in an unpredictable manner. One hand held the base of my cock and the other was gently caressing my balls.

She popped her mouth off me while still applying suction and looked up at me with her dark, brown eyes. Her long black hair was half covering her face and tickling my dick. I reached down with both hands, sweeping her hair behind her ears, but most of it fell forward again. I gathered it together and gently held it behind her with one hand. She looked me in the eyes and slid her mouth halfway down my shaft and back to the tip, kissing it once, then slid her lips back down the shaft. Fuck, she was good, and she looked so hot doing it.

I noticed my Jill was watching, fascinated, with one hand in her shorts massaging her pussy again. She saw me look at her and said, "She looks like she really enjoys it. I wish I could do you that well."

"You do, lover, just differently," I told her.

Taking her mouth off me and licking up my shaft once, Jill-2 said, "Oh I do like it," and she licked my shaft and head. "I like this cock," she licked it, ending with a kiss on the tip. "You should be proud of it," she gave its head a wet kiss and a big quick lick.

"It fits so well in my mouth, without tiring my jaw out." She took me in her mouth and sucked as she slid down to the hand holding me at the base, then right back up and off with a pop. "I really like how that ridge feels." She sucked on just the head, with her lips gripping me under the corona and moaning, "mmm."

"I'm jealous that you get this all you want, Jill." She sucked hard on the head again; washing it with her tongue. After several seconds she began to vigorously suck up and down my shaft, very wet and noisily.

"Oh, fuck," I sighed, holding her hair and watching her bob up and down on me. The sight and sound, to say nothing of the incredible feel of her wet sucking and tongue lashing, had me almost ready to cum. Then the hand on my balls slid back and wiggled a finger into my asshole. It squirmed around in my rectum as she blew me.

"Oh fuck, I'm gonna cum, Jill," I moaned. "Ohhhhh, uuuurrrrrgghh."

"Tiger is purring for you, or maybe roaring quietly," my Jill giggled. "This is so hot! I love sucking that cock, but I really like seeing you do it, Jilly. I didn't think watching you do this could be almost as much fun as doing it myself. Almost..." It looked like she was rubbing her clit, pretty hard. Suddenly she sat on the chair, her legs trembling.

As I came, Jill-2 took her hand off the base of my cock and slid her mouth down until she had it all in, with her nose in my trimmed pubic hair. She held me like that, her tongue pressing against the underside of my cock, as it twitched in her mouth. When I went still and relaxed, she slowly slid her mouth back, her lips continuing to grip me, and applying a little suction. Her finger came out of my ass gently and she held me by my butt cheeks.

She paused with just my cock head still in her mouth, running her tongue around it and sucking more, taking the last of what cum I had left. She slid her lips off my cock, ending with a gentle press of them to the very tip in a tender, lingering kiss.

As I let go of her hair, she pulled herself up off her knees, gripping my hips. She palmed my cock with one hand, her finger tips on my scrotum, and kissed me gently, opening her mouth to share a little taste of cum on her tongue.

"I think we really did drain you today, stud. You, and this guy," she said rubbing my softening dick, "ought to be satisfied for a while, I think. Thanks for all the treats you gave me today."

"Any time," I replied, sincerely. "I might as well say that, since Jill will anyway!" I teased them both as I pulled on my shorts and shoes. "But really, it was my pleasure to give you pleasure, and to get pleasured by you. Ok, that sounded a little lame but you know what I mean."

They both laughed, and Jill-2 said, "Yeah, I do. Same for me, stud. I've gotta run, but Jill will fill you in on some things we talked about. I'm hoping we can work out some stuff. Maybe I'll see you both tomorrow." I raised my eyebrows quizzically and looked from one Jill to the other.

My Jill said, "Hey, I didn't volunteer you for anything. Not really, not yet," she snickered. "I'll tell you about it in a bit. See ya, Jill, and thanks for the great show!"

"Hey, now I can say, 'any time!' And I mean that," she said with a grin, as we got in our cars.

"So, we got your stuff, and got both you and Jill off, now what should we do today? I was thinking maybe we could go for a walk. How about that nature trail place, we went there on one of our first dates. I'll tell you all about what Jill told me, and some thoughts I had." As I was telling her that sounded like a good idea, her phone rang.

"Hi Sis!" she said. "Hey, that's great, thanks. Yeah, we'd love to see you there. Lunch or something would be great. I don't know, but she probably would, if she's free. I don't think she has a boyfriend, but she might. That would be great, too. Yeah, I don't know. I was thinking Port Orleans, but I need to check with Rob, and look at some other things. Yeah, he's right next to me, he's driving us to a park for a nice walk. Yeah, well, he had a big workout this morning, so a relaxing walk will be nice." She winked at me. "Yeah. Ok, I'll be in touch and we'll work out all the details. This will be fun. Thanks again! Bye."

"Hey, babe, you got all that, right?" she asked me, sarcastically. "My sister would like to give us passes to Disney for the weekend after next, if that timing works. She wants to meet us for lunch or something. She hopes Becky might come, and she can bring a "friend" if she'd like. And, she'll use some of her perks to help us get a nice room someplace. It's somewhat short notice, but there's one of the Epcot festivals going on and she can arrange a lot of this because of that somehow. How's that sound to you?"

"Sounds good," I said, "I don't think I have anything on that weekend, except fooling around with you. I don't know if we could do any of that there, but I'll survive," I teased.