Lucky Over 40 Ch. 08: Weekend Ends

I repeated the same routine once more, and then the next time I pulled out a bit and then put on more lube before pushing in. It went deeper on the way in that time; the inch I had pulled out, plus maybe two more. One more time deep push and I was in all the way, my balls touching her pussy. She must have felt it because she reached between her legs and caressed my scrotum.

"Oh babe, you're in. You're all the way in me. You feel so big, like you've filled me up. Oh yeah."

She started to move forward and back, sliding me in an out. At first I tried to follow her and then began to move opposite, so I would pull out farther and go back in a little faster. It felt great, but as we got into it we didn't coordinate well and I came all the way out.

"Oh!" she yelped. I quickly grabbed my cock and pushed on her anus. It slipped right back in like it belonged there -- like her hand does on my ass. "Uhmm, that's better," she sighed. "Oh yeah, this is good. You feel so good in there. Not the same as in my pussy. Not better, not worse, just different, and good. Fuck me, Tiger. Fuck my ass. You be in charge so you don't come out again."

I told her she felt really great, tighter than her pussy, but not as wet and slippery, and not as, I don't know, welcoming, maybe. Yeah, different, but really good. I picked up speed and depth in my thrusting. I dribbled on a little more lube at one point, remembering that Jill-2 said you can't really have too much.

Jill moved one hand off the bed, between her legs. She was rubbing her pussy, or her clit, I assumed. I reached up and took a breast in each hand. I kissed her back, squeezed her tits and then started rolling the nipples between my fingers. Oh I do love her breasts. They fill my hands, or my mouth, so nicely.

"Mmm, yes, pinch them, Tiger. Pull my nipples -- not too hard, but be a little rough," she encouraged me. "Oh, fuck my hot ass. Push your big cock in my horny ass, Tiger. Oh, yeah, play with my titties and fuck my ass. Oh shit, yes. Oh, fuck, your making me... Oh, ummm. Yesss."

She seemed to be coming, or was very close. The squishy sound of my lubed up dick moving in and out of her, the intermittent slap of my thighs on hers, my balls hitting her pussy -- and knowing it was her wet pussy -- her moans and dirty talk, plus the tight feel of her rectum holding onto my cock, all had me approaching climax, too.

I picked up the pace, grunting some and telling her how much I liked her tight ass. Her dirty, tight ass. Her tasty tight ass that I love to eat, or finger, or stuff things in, like my hard cock. I told her I was going to cum in her ass, deep in her tight ass. I said I loved her tight ass, and I loved her.

Shit, I thought to myself, I said it!

Then I heard her say, "I love you in my ass, Tiger, and I love you too. I'm gonna cum. Ohh, unnngghhh, caaahhh. Come. With. Meeeeee. Tigerrrrr. OOoohhhhhhh."

Shit, we had both said it. Oh Shit, I thought, where's this going? Going too fast! Then suddenly I realized, I'm coming, oh shit!

"Fuuuckkkk," I grunted. Uuuuuggghhhhh. Uunnngggghhhhh. Yeahhhhh," I let out as exhalation.

Jill slumped forward and I followed on top of her. I rolled us on our sides with me spooning her, my dick still in her ass.

After we both regained ourselves, she said, "Oh that was good. Whew. And you feel good still in me, but I think he's shrinking some. Oh, yeah, I can feel him getting smaller," she giggled.

I pulled out and rolled onto my back next to her. She moved over and snuggled on my chest, her arm across me and mine around her. We lay like that a few minutes before we heard her phone go off again. I sat up to find it, and handed it to her.

"It's from Becky," she said. "It says 'Two minute warning,' that's all," and she laughed. She suddenly stopped laughing and said, "Shit, two minutes to get cleaned up, dressed and be sure the house doesn't look like we've been fucking all weekend, even though we have!"

She started laughing again, kissed me hard, but quickly, and hopped out of bed to get things in order. I followed right behind her.

We darted around, checking that all looked in good order still naked, then ran out to the patio and put on our clothes. We heard a car door slam outside just as we were about done dressing. I looked up at Jill and saw she had buttoned her blouse askew, each button off by one hole. I pointed to it, my eyes wide, and she quickly started fixing herself, getting the last one done just as the front door opened.

Becky called out, "I'm home!" and we walked in off the patio as nonchalantly as we could manage. Jill gave her a big hug, after which Becky stepped back and looked at Jill with her head slightly cocked. She said, "What's up? Or, what have you been up to? Come on, mom, fess up."

"What?" Jill replied, her eyes wider than usual. I was afraid she was about to panic at Becky's apparent knowledge that all was not as we wanted it to appear.

"Did you have a good weekend? Did you have a sleep over? Did you behave yourselves? I hope not," Becky said with a tease in her voice.

Oh, great, I thought to myself, she had just been messing with her mom a moment a go. Wonder where she gets that from...?

Jill seemed to breathe a sigh of relief and said, "Yes, we had a very nice, but pretty active, weekend. Rob did stay over. We have a pretty nice guestroom in the den, you know. And he was a perfect gentleman. He even gave me a nice massage out on the patio a little while ago."

A nice guestroom in the den, I thought, we didn't even set foot in there all weekend, did we? A perfect gentleman? Well, I guess you could say that, I thought. Gentlemen still have sex. But do they pee on their lady? Or eat her ass, or her friend's ass? And if she knew what that massage turned into...

"Oh, a gentleman was he?" Becky said. "And a massage huh? What kind of massage was that? Good thing the patio is so private, huh?" the she began to giggle.

Shit! I thought. Can she read minds like Jill? Then when she giggled I figured she was still just messing with her mom, and maybe me, too.

"Well, I'm glad you had fun and had the extra time together. I had a good time at the concert, and hanging out at a beach with my friends, and stuff. Would have been nice if I had a boyfriend for the weekend, too, though. But I may not have been so well behaved," she said with a grin. "Although I would have loved a massage from him. Do you take new customers, Rob?" She added as she headed to her room with her bags.

Jill looked at me wide eyed and we both started to laugh, but very quietly. "Need to have that talk with her about 'Us' pretty quick I guess," she said.

Becky came back in, and opened the fridge. "Ooo, some wine. Mind if I have a glass?"

"No, you're certainly old enough," Jill said. "I'll join you. How about you, Rob?"

"I'll have a small one, then I should head home I think. We'll need to open another bottle, so I'll take care of it," I offered.

We all chatted while sharing the wine. It was nice and relaxed, and not something we'd done yet with Becky. She mentioned again how much she was glad I was part of Jill's life, and was very complimentary about me. I asked her how she could feel that way about me, since she hadn't known me very well.

"Hey, I did my research. I'm a journalism major, and hope to specialize in investigative journalism. I also try to look out for my mom. For one thing, I've talked to some kids at school who took classes with you, or knew some who did. And I even know someone who worked with you, or for you maybe, as a helicopter nurse."

"Flight nurse," I interjected. "Really?"

"Yeah, that's it, but he's a paramedic I guess. You're the flight nurse, or manager now, aren't you." she corrected herself. "Anyway, everyone said you were great, and really liked you. I only saw one negative 'review,' on someone's social media. But she was critical of a lot of her professors, since they apparently don't give her the grades she deserves or the extra time she needs for her assignments, especially after a holiday weekend when they should know she's been busy with parties. Reading her stuff I bet she did get the grades she deserved, if not ones that were higher than they should have been," she laughed. "But anyway, you're pretty great as far as I can tell. Definitely above average."

"Definitely above average, indeed," Jill added. "Who else said that recently about you. Or about one of your attributes?"

"Hmm, what's that?" Becky asked.

"Nothing," I responded, quickly. "Your mom is just having a little joke with me. She and one of her friends, well OUR friend... Anyway, they were teasing me this morning. About a little personal stuff."

"Not little, remember?" Jill teased again. "And yes, OUR friend. Sorry, Becks, I couldn't resist teasing him, but it was nothing you really need to hear about. We were just having some fun when he was helping her out with something at her house." She winked at me, out of Becky's sight.

After a little more banter, I gathered my things and headed home. That night I had a little trouble sleeping, missing Jill beside me, or on top of me, or... I got to thinking that the last time I was in that bed it was fooling round with her, that morning. Eventually, I did fall asleep, and had a sex dream for the first time in I don't know how long. It was about Jill, of course...

See part 9 to see where things go next.