Chapter 2

“But you didn’t get to cum yet, did you, Darling?

“Don’t worry, I have an idea I think you might like. In fact, I think you’ll like it a lot.”

Lani kissed the tip of my nose, then with both her hands on my shoulders she slowly started to lift herself off me – and off my cock. And iIt might have been my imagination, but I think she had this look of... regret on her face...

One other thing I noticed that was kinda different – this time, since I didn’t cum in her (yet, I hoped!) she didn’t have to grab a bunch of Kleenex to catch stuff dripping from her pussy. But I was hoping that she was still pretty wet ... inside.

“C’mon, Lover.”

She took my hand and guided me up from the “amazing” chair and led me over to the bed, which was still kind of messed up from ... from what we did before lunch. She sat down on the bed, then stretched out, then still holding my hand she guided me onto the bed with her, my hard-on still leading the way.

“I know you haven’t cum yet, Sweetheart, but I have an idea of how we can fix that.” Then she smiled that “I know something you don’t know” smile. “In fact, I think you’re going to like my idea a lot.

“You remember that little thing I did this morning, when you were ready to cum but were too ... excited ... to let go? And remember that thing I did...?”

Yeah, I remembered – when she smeared the pats of butter on my bum – into my asshole – and worked them around ‘til I came. Yeah, I remembered. But why did she bring that up now?

“Yeah, you mean with the butter and stuff? Yeah, I remember. But...”

“Well, you know, Jason – you know how that butter ... how it felt when I spread it around – and in you, and how good it felt, and how it helped you relax...?” She turned all the way toward me and looked right in my eyes. “Well, sometimes something like that helps me to ... relax ... too.”

Was she telling me that she wanted me to smear butter on her and that it would help her... relax? Why would she need to “relax?” She couldn’t have been all tense down there like I’d been earlier, when I couldn’t cum?

“What we’re going to do, Jason ... I’m going to need a little ‘relaxing’ before we ... before both of us can really enjoy it.”

I still couldn’t figure out what the heck Gr ... Lani was getting at.

“I don’t understand – why do you need to relax? Aren’t you already ... relaxed? I mean, isn’t your...” and I kinda stumbled because I didn’t know how to say what I was thinking without sounding crude, “Isn’t your ... pussy ... already ... relaxed from ... from what we just did...?”

When I finished, Lani smiled, like she was amused at what I just said, but also because she understood why I was confused.

Still smiling, she said, “You know, Jason, there’s another place down there where a cock can fit very nicely?”

Ohhhh – did she mean...?

“You mean...?”

She smiled again.

“So ... do you think it’s time for you to get your fingers a little buttery...?”

She reached over to the bedside table and picked up a couple of the little butter packets she’d taken when we were coming back from lunch. She peeled off the tops and held them out to me.

I reached out to take them from her and then stopped for a second. But then I guess I knew I needed to cross that bridge. I put my first two fingers together and dug them into the first packet...

... and remembered something from this morning, something Lani said.

“This morning, when you were ... when you were using your finger to...,” and once again I wasn’t sure how to say it “politely,” “when you were rubbing the butter into...,” and stumbled again, “into my ... butt...,” there, I finally got it out, “when you were doing that you said something about my father...”

Lani smiled, but she didn’t say anything. She was going to wait and make me say it.

“You said something like how my father ‘isn’t the only man in the family who likes that’ – liked having butter rubbed up his ... butt.”

She still wasn’t going to say anything, like she was going to make me drag it out of her.

“And when I asked you said you’d explain later.” She just kept smiling, that “I know something you don’t know” smile of hers.

“Well...!”

She finally gave in.

“I guess you’ll find out anyway...”

Find out what?

“When Terri – your mom – decided that she was serious about your dad – he wasn’t your dad then, of course – they were still in college and they’d been dating for just a little while. Anyhow, when it was obvious that your mom and dad were getting serious, your Grandpa Bill – your mom’s father – and I had to make sure that if they got married, that your dad was ... that he was willing to be a part of our ... family relationships.

“You see, your Grandpa Bill was itching to get into your mom from the time her tits started showing, and by the time she was 14 we decided she was ready...”

We decided??

“Anyway, when it looked like they were serious we made it clear...” Again, we? “We made it clear that if she was going to have a fiance’ he was going to have to be someone who would be able accept the ... accept her relations with her dad. In fact, we talked it over and decided that anyone she married was going to have to be willing to participate in all our family activities. Terri and her father were going to continue enjoying each other, and any guy that Terri settled on had better be ready to show her mom some love, too – literally. When we made this clear to Terri she said, simply, ‘Don’t worry, Mom – I don’t think that’ll be a problem with Jeff.’

“Turns out, it was as easy as pie. Your dad came home with Terri for spring break and we were all out by the pool and your Grandpa Bill started things off by asking your mom to do him a favor and spread some sunscreen on him, and your mom got up and went over to the lounge where her dad was and kneeled over him and started spreading the Hawaiian Tropic on his back and then moved down and started doing his legs and thighs.

“Then Bill said, ‘Mind doin’ my front, too, Baby?’ and rolled over on his back. Bill usually had a nice package in front, and it got even nicer when your mom started working on his thighs. I’d been talking with Jeff, and when Bill turned over I made a point of looking over to where your mom was applying the sunscreen to your grandpa’s legs, very thoroughly. And I made sure your dad noticed, too.

“So I said to your dad, ‘That looks like a good idea, Jeff. Would you mind putting some lotion on me?” and I knew that there was no way he was going to refuse. For one thing, it would have been ‘ungentlemanly’ for him to refuse, seeing that his girlfriend was oiling up her dad real good and that her dad was obviously enjoying it real good.

“The other thing was, I knew from things your mom had told me that your dad thought I was ‘a hot piece of ass’ so I didn’t even consider the possibility that he’d pass up the chance to run his slippery hands over his girlfriend’s ‘hot piece of ass’ mother.

“Your mom tossed him the bottle of sunscreen and he got on the lounge where I was laying. I turned on my stomach for him to start, but after a minute or two I asked him to undo my bikini top so I wouldn’t have tan lines. Ten seconds later I rolled over onto my back, and then there was no way he could miss the invitation to rub his creamy hands all over his girlfriend’s mom’s naked tits.

“So like you’d guess, we – the four of us – spent all of that spring break fucking and sucking and anything else we could think of...”

But then she added something that really knocked me for a loop.

“That’s when your mom discovered that she liked having two men at the same time.”

She paused her story and looked up at me and touched her buttered finger to the tip of my nose.

“And that’s how I know your father likes having his asshole lubed with butter.

“And speaking of butter...” She looked toward my hand.

I’d completely forgotten that I had a blob of butter on my fingers. I also realized I had no idea what to do with it.

Lani saw my problem and smiled. She rolled over, then crouched down on the bed with her front pressed against the bed sheet and her cute little butt sticking up in the air, and there was no mistaking what I was supposed to do. I got up on my knees beside her and started to move my right hand – the one with the fingers with the butter – toward that cute upraised ass...

And I stopped. It was like I was chickening out. It was obvious what I was supposed to do, but in my head I’m saying, “You’re going to put butter on your grandmother’s asshole!” And I thought, “Yeah, I know that she did the same thing to me this morning, and yeah, it felt good and I liked it – really liked it! And yeah, I know that she wants me to do it – practically told me to do it! But still,...”

“It’s not polite to keep a lady waiting, Jason.” Then she added, “Especially one that’s naked and wiggling her ass at you.”

As I was learning, Lani always said just the right thing, just the right way. I stuck my buttered fingers out toward her little pink-brown pucker and touched ... there, and I waited to see if she reacted. She didn’t do anything, so I pressed one finger into her ... there.

“Mmmm, that’s nice, Jason. Now move it around a little – massage me, like I did you.”

I guessed that meant it was good so I pressed a little more, and when I did my finger was so slick with the butter that it slid into her all the way to the first knuckle...

And it was like a jolt of electricity went straight from my finger to my brain. I can’t explain it, but maybe it was all the things together – seeing Lani’s hot, sexy body, and the feel of the silky insides of her asshole squeezing my greasy finger, and knowing that I was going to be using my fingers, working them around inside her ... there. And also, that the feeling around my finger was like the feeling my cock was going to feel when I put it inside her ... there – when I fuck Lani in the ass!

A slight wiggle and Lani reminded me that I was supposed to be getting her ready for ... for that. I thought of pushing my one finger in deeper but then remembered that I was supposed to be massaging her anus and getting it all relaxed and ready for ... bigger things.

I worked my finger around, pressing against the sides of her asshole while I was moving them in and out a little. Lani must’ve liked that, ‘cause her ass kinda swayed with the massage I was giving her.

“I think I’m ready for that next finger, Jason.”

I took the other buttered-up finger and put it up against the first one and used the two of them together to massage the puckered hole and all around it. And it surprised me when I realized that Lani’s asshole was getting looser. In fact, it was almost like it was getting larger.

“Now inside, Jason.”

I kept my two fingers together and kind of... wormed ... them into Lani’s asshole, and that’s when she really started moving her ass around, almost like she was trying to screw herself on my fingers – like she was fucking my fingers with her ass!

By now I was pretty sure I was doing it right and wasn’t making a fool of myself and that Lani seemed to be liking her “relaxing massage” – a lot! I closed my eyes and concentrated on moving my slippery fingers around inside Lani, and thinking what I was doing – picturing my fingers moving around there, touching the insides of her asshole – and feeling Lani’s ass moving with my fingers, like I said, like she was fucking my fingers with her ass – I almost got lost in the whole thing...

“Jason? Jason, honey – I think it’s time...”

Time for ... oh, yeah, we were planning on doing more than this. Though I gotta admit, relaxing – okay – finger-fucking – Lani’s ass mighta been the sexiest thing we’ve done this whole crazy day.

But then I realized – we – she – had never actually said what it was we were going to do. But sticking her butt up in the air and having me smear butter on it and work my fingers around in her asshole so it’ll get “relaxed” – there had to be only one reason for all of that: Lani and I were going to do anal sex.

I was going to fuck “my Lani” in the ass.

But I didn’t have a clue as to how to do it. Sure, I seen porn where they did anal, but it was usually hard to see what was happening very good. The ones I had seen, though, the woman was usually on her hands and knees, or sometimes she was crouched down like Lani was now, and the guy was on his knees behind her. But Lani had other ideas.

She reached back and pushed my hand gently, letting me know that now it was time for me to take my fingers – with most of the butter gone now – out of her ass. Once my fingers were all the way out she paused for a minute, like she was trying to get used to my fingers being gone and her rectum being empty now. Then she got off her knees and laid on her back, and then she held her hands out to me and pulled me down in between her legs.

“I know, Jason – most of that porn you watch, when people have anal sex the woman is on her hands and knees and the man fucks her asshole from behind.” How could she know that? “But there’s another way, a way I think you’ll like even more.”

There’s another way?

She reached over to the bedside table for a plastic bottle with some purple writing on it and squeezed some of the clear stuff that was in the bottle onto her fingers. Then she told me to “lift up a bit” and she grabbed my cock and started spreading the clear stuff – it was like some kind of gel – all around it.

“For what we were going to do, all that butter you so lovingly applied inside me isn’t going to be enough ... at least for the first time.”

So when my cock was slick enough she pulled her legs back and this caused her asshole to “tilt” so she’s not laying on it and it’s more aimed upwards toward me. Then she took my cock by the tip and put it right up against her asshole and slid it around a bit so it’s perfectly lined up with the center and then said, “Now, Jason, press against me ‘til you feel me start to open.”

I wasn’t sure what she was getting at but I did what she said and pressed my cock against her. And I felt it – I felt her ass open – just like she said! With all that lube and all the butter that I rubbed around inside her and all the loosening I’d done, and with the little bit of the gel she smeared on me at the last minute, just that little press and she opened up for me and the head of my cock slipped completely inside her ass!

And it was warm and soft, like warm, moist velvet holding me all around the head of my cock, and I knew that this was a feeling I’d never forget.

She smiled, a wonderful smile that told me, “That’s it, Jason, you’re doing it, and soon we’re both going to be feeling the most wonderful feelings...”

And that’s when I realized the other thing about doing anal sex this way – that Lani and I could look at each other and see each other’s faces and how we were liking what we’re doing. And just when I was thinking that, Lani pulled me down to her and kissed me, this real tender kiss.

“Now, Jason – make your lover happy.”

And with her telling me that, I knew what to do. I needed to press my cock the rest of the way into her, steady and smooth, so I didn’t hurt Lani, and also so I’d have time to enjoy the feeling of my cock sliding into that warm, slick, tight channel.

I pushed steadily, and it was the most amazing feeling. Not like when I was sliding my cock into her cunt – although that felt amazing too. Now her ass grasped my whole cock, the same way all at once, and it was still that warm velvet feeling but now it wasn’t just the head of my cock – it was the whole length.

But what really hit me was the heat. Inside her asshole it was so warm, it was almost like it was hot. I never even thought about that, but now ... now it was like my cock was being gripped by this almost-hot velvet glove, and it was like that for the whole length. My whole cock was being bathed in this hot velvety grip...

And Lani knew it.

She smiled. “Is it like what you thought, Jason? Does it feel like you thought it would in your dirty little fantasies?”

No ... it felt a hundred – a thousand times better!

“Because it feels wonderful to me, Jason. Having your cock inside me ... there ... feels even better than I imagined it would all those nights.”

And that blew my mind, too – the idea that Lani – my ”Gram” – had been fantasizing how it would feel to her, having my cock filling up her ass.

And hearing her say it!

And without her having to tell me, I started moving ... sliding ... my cock in and out of that hot velvet tunnel. And once I got into a little rhythm, Lani started moving with me so it was like she was fucking me back.

And the way we were, with me on top and us facing each other, I could look at down at her and see how she’d turned her face sideways and closed her eyes and was biting her lip...

And then she opened her eyes and looked up at me and she smiled this kind of “nasty” smile. She grabbed my head and pulled me down to her and kissed me. But then she bit my bottom lip, not real hard, but hard enough that it still hurt, and then she stopped and looked at me, into my eyes, and pulled my face down again and started licking me, around my mouth, then smearing her lips and mouth against mine, and something told me that she wanted me to do that back to her, so I licked her lips, too, and her chin, and then I rubbed my mouth around on hers and it was like we were fucking each other with our tongues and our mouths.

“Oh, Jason, baby – you’re fucking my ass so good. Do you like it, Jason – do you like how my ass feels around your cock? Because my ass loves how your cock feels inside it.”

Before I’d just been sliding my cock inside her and she’d been sliding herself to match me. But after she said that I started making longer strokes so that I was feeling more and more of her asshole on every stroke. And I realized that now, with the longer moves I was making in and out, that I – that my cock – could feel her ... feel Lani’s asshole better ... more. So I kept up with the longer in-and-out strokes but I slowed down, and doing it that way it felt like I could feel every millimeter of her hot velvet ass sliding along the skin of my cock.

So now I know – this is what anal sex is about – this is why anal sex is supposed to be so great and why people, especially guys, are so hot to get it, to get into a girl’s ass. And that I’m actually doing it – anal sex – that my cock is buried all the way up my cute, petite, sexy grandmother’s ass – and that she’s liking it!

And then I got this other thought: This feeling, of Lani’s hot rectum sliding against my cock skin while I slide in and out of her asshole – will I ever be able to get it enough? Or will I be I hooked, maybe for my whole life?

“Ohhh – like that, Jason, just like that.”

So I guess she likes it, me doing it this way. But then,

“Like that – deeper, Jason – deeper – that’s it – all the way in...”

My cock was already all the way inside her but when she said that I pushed even harder. Lani groaned when I did that and put her arms around me and pulled me closer to her, and she threw her legs over my thighs and squeezed so she was holding me right where I was, pressed as deep into her asshole as I could get.

“Oh, shit, Jason, your cock’s so deep in me, I’m so full of you I don’t think I ever want to let it go. Will you do that, Jason? Will you always fill up my empty asshole with your beautiful hard cock? Will you do that for me, Baby? Will you, Jason?”

When she said that I kinda got lost in my head. My cock was inside Lani’s hot ass, as far in as I – and she – could possibly get, and I got lost in feeling how my cock was being squeezed tight by that hot velvet flesh, and I think I didn’t ever want to have to leave that place but I knew that sometime I would have to.

And then there were Lani’s words: “Will you always fill up my empty asshole with your beautiful hard cock? Will you do that for me, Baby? Will you, Jason?”

And I thought maybe she’s just saying that now ‘cause she’s so turned on, or maybe to excite me.

Or, maybe, she meant it – meant that I could “fill up her empty asshole” anytime I want to, as often I want...

Then I felt her arms loosen a little and she slid her legs down and off my thighs so I thought that meant I should start moving again, stroking in and out of her ass again. And it felt... amazing!

Too amazing, because in spite of my fantasy of never wanting to leave this place, Lani’s ass, my cock was starting to make those pulsing feelings they do when I’m almost ready to cum. I think Lani could feel them too ‘cause she said, “Wait a minute, Jason,” and worked her hand down between us and pressed it against my chest, not to push me away but more like to guide me back and off her a bit. So I lifted back just a little and she slid her hand farther down, and I couldn’t see but I could feel her hands working on her pussy and her clit, and that was the signal that I could cum whenever I wanted to.

“Now, Jason, let that beautiful hard cock of yours come in my ass – come in your Lani’s ass.”

And as soon as she said that my cock took over and I felt myself just let go of everything I’d been building up since this morning and since Lani screwed herself on me on the desk chair but didn’t let me cum. And I never thought I’d say this, but now I’m glad she didn’t. She didn’t let me cum all that time so that I’d have all that built up pressure, and all that built-up cum, to put in her ass – to “come in my Lani’s ass.”

And then my head got lost again, thinking about what I was doing – I was cumming in my Gram’s ass! And all I could think of was how dirty this is – squirting an enormous load of my cum deep in my cute, petite, sexy, hot grandmother-Lani’s little ass.

And in the middle of my cum I felt Lani’s hand grabbing at her pussy faster and harder, and then she arched her whole body up against mine and she went stiff, and then she made this sound, “Oooohhh... ,” except it was more like a howl, like a sound an animal would make, and she grabbed my back and dug her fingernails into my back and shoulders. And it hurt. But the weird thing was, it made me feel like I was cumming even harder. And I was sure that she knew it would. God! All the stuff I’m learning from her about sex that I never would have thought.

So my cock finishes pulsing into her and I let my body sag onto her and she lets up with her fingernails in my back and now that I’m laying down on her she sinks her teeth into my shoulder, but not real hard this time, but enough that I can feel it. And like with her nails, her teeth in my shoulder turn me on and I can feel my cock get a little thicker, even though there’s no way I can do anything more with it.

So we’re laying there like that, with me resting on her and her arms around me, and I can feel her lower her legs down to the bed and we’re slowly catching our breaths, and Lani takes one hand and starts stroking my hair and she says,

“Oh, Jason, Sweetheart, you fucked my ass sooo good. You made your Lani cum so hard – maybe one of the hardest cums I ever had in my life. Did you know that, Jason, Sweetheart – did you know how good you made your Lani cum?”

And I felt about ten feet tall and like a million bucks and all that. Me, a high-school virgin, making a mature woman – a mature, sexy woman – cum – maybe the best cum in her life!

But by now my ten-foot million-dollar cock is shrinking real fast inside her warm and very wet asshole, and I stay in as long as I can but finally I’m too small and she’s so wet that I finally slip out.

And Lani makes this adorable little “Ohhh...” sound like she’s disappointed, but then she smiles at me and kisses me on the lips and gives me a nudge in a way that let’s me know that I should roll off her.

So now she’s laying next to me and were both pretty wet and – I hate to say it – slimy from ... from what we been doing, and both of us really oughta take a shower...

But it’s so nice laying here next to her after what we just did, and neither one of us makes a move to get out of where we are now.

Parents and “experts” are always talking about how sex and “sexual feelings” can be “confusing” for young people. Well, I’m confused.

I’m laying here in this king-sized hotel bed after a day of having amazing sex with Lani. Except that Lani is also my grandmother and has been for all my life, and I’m feeling something I think might be falling in love with her.

Sure, you’re supposed to love your grandmother, but you not supposed to be IN LOVE with your grandmother! You know that’s weird, right? But what else is weird? She’s the kind of woman I’d want for a girlfriend – if and when I ever get a girlfriend. She’s cute, and she has this sexy little body, and she really likes sex – and she’s really good at it! But she’s also kind, and she’s really thoughtful and considerate about my inexperience and about teaching me how to be good at sex. And she loves me – and not just as a grandson. I think she’s feeling some kind of love for me as a guy – as a man. If she was 35 years younger she’s exactly the kind of girl that I want to be my girlfriend.

So yeah, I’m kinda confused.

So we’re laying there and I’ve just about managed to stop thinking about these things and finally doze off when Lani says,

“This is nice, Jason, lying here like this, with your arms around me.”

Awww, fuuckkk...

“Jason? Jason?? Are you awake? Jason, sweetheart, are you awake??”

My brain started to return to the present but I musta really been out ‘cause it took me four or five seconds before I could come out of what might’ve been the most wonderful nap of my life, and Lani’s saying, “Jason? Jason, are you hungry? Because I’m really hungry –I don’t think my stomach’s ever felt so empty.”

When she said that part, about feeling so empty, of course I wanted to think that maybe the reason she was feeling so empty was because she didn’t have my cock inside of her somewhere. But before I could keep congratulating myself on what a stud and a woman-pleaser I am she says, “But we need to shower – both of us – before we can go anywhere.”

So she grabs my hand and takes us into the bathroom and slides back the shower curtain and gets the water started. Then, like it’s almost without thinking, she sits down on the toilet and starts peeing. I guess I musta looked shocked – I was! – when she looks up at me with a look of complete ... understanding ... and says, “Jace, after what we’ve just done and what we’ve been doing all day I don’t think this is too ... personal – do you?”

And no, I guess when you put it that way – “in the present context,” as they’d say in my poli. sci. book – that it’s not that far out.

Lani got off the toilet, flushed, and said “Next?” and I realized that I really did have to go, so I stepped over, only to realize that I was still so turned on from our fucking – and from having an audience – that it took me about ten seconds to relax enough to actually do anything.

But finally I finished peeing and then realized that Lani was still there and that she was still watching me and she had this little smirk on her face. But then she pulled the shower curtain aside and said “Shall we?” and stepped in and held her hand out for me to join her.

Except in our bathroom the shower wasn’t part of a bathtub. Instead it was a shower stall that you walk into (I think maybe it was because they gave us the last room available and it happened to be a handicapped-accessible room) and it had several railings all around inside it to hold onto. So I stepped into the shower stall and Lani had already loaded up her hands with the bath-and-shower gel from the dispenser on the wall and started spreading it around my chest.

And it felt so good, and not just the shower gel – it was the whole thing – the gel, the warm water and the steam, and Lani’s small, soft hands touching me. She went up from my chest and used her fingertips to spread the gel real gently around my face. I instinctively closed my eyes so she could wash my whole face, and with my eyes closed like that I could focus on her gentle fingers touching my forehead and my cheeks and my chin. And the way her fingers were touching me, the word that came to my mind was “lovingly.”

She told me to turn around and then did the same things with my neck and my shoulders and back, and then down to my feet and working up my legs, with her hands around my lower legs and then all around my thighs, and then she finally moved up to my butt. And she spent lots of time there, and it wasn’t just washing – she worked her fingers around, at first just stroking my skin, but then working my butt, even digging her fingers into the muscles. And I was surprised how strong Gram’s fingers are.