bakerstreet | Asks from the heart

K. Come here.

[She pulled a couple pillows over to the middle of the bed, gesturing for him to lay on them with his hips propped up.]

So, do you just want me to do oral, or would you be okay with one of those finger vibe things?

Uh...

[He's gonna think on that as he sits on the bed, not quite laying over the pillows just yet. Just kind of- taking it all in.]

Maybe- we can try both? It won't be too intense? Or- that would probably a good thing. Intense. That's how it's supposed to feel?

Well, it's probably going to be intense for you because you haven't experienced any of it before. So I'll do oral for a bit, then when you're nice and worked up, we'll try a vibrator. On low. One of those finger pad ones. Then we'll see how you like that. If not, I can go back to just oral. But you are definitely going to come from just ass play, James. I plan on showing you what a prostate orgasm is.

[ He laughs softly- it's nerves- but he nods. ]

Okay.

And- you're sure you're okay with this?

James.

[She moved over to where he was, cupping his cheek and lowering her head to give him a kiss.]

I suggested it because I'm okay with it. I'm a little sad that I know things about the male body that you don't and you're the one with it. The fact you haven't even played around with your perineum while jerking off? I want you to find all the parts of your body that make you feel good, and then I want you to be okay with enjoying it. It's okay to like things. And you enjoying yourself, sexually, is hot as fuck to me.

[He looks at her, giving her a small nod.]

Thanks, Jess. I'm really glad you find it hot as fuck too. I'm excited. Nervous but excited.

I get to be your first for some things. And hopefully your only. That's... I like that. A lot.

[She smoothed her hands over his back, then gave his ass a slap.]

Now get comfy. And be vocal, okay? If you don't like something, tell me. If you're not sure or need a break, it's okay to say so. Or if you want me to keep doing something, say that too.

First and only. I like that a lot too.

[His smile grows wider and he leans in to kiss her once again, before he moves to lay on the pillows now.]

Okay- sounds good.

[She waits until he gets comfortable, then moves over to pet her hands over him. Down through his hair, along his back, down over his ass and legs. Touching him, just to touch him and because she wanted to. She moved to get between his legs, sliding his knees apart to help him prop up the way she wanted him to be as she leaned in and pressed a kiss to one ass cheek.]

I really do love your ass.

[ It's easier for him to relax once again, with her massage still sunken into his skin. He spreads his legs a little at her prompting, resting his head on his arms. On his face, there's a smile. ]

Pretty sure that's the first thing you mentioned to me when we started talking. Glad to hear it still rings true.

It's a nice ass. It's plushy. Biteable. Squishy, and yet still firm.

[She let her hands play with his butt, squishing it and patting it, but she was working towards letting her hands move closer to where his crack was. Down near the base, closer to his taint.]

Squishy yet still firm- thank goodness.

[He likes it when she plays with his ass. Likes how much she likes it. Likes where her hand is traveling too, so he lets out a soft, pleasurable sound.]

Oh, all of you is firm. Especially in all my favorite places.

[She knelt down and got comfortable, seeing where his cock hung down and pressed against the pillows, his balls resting over that, then the patch of skin that was taut and pale up until she saw his asshole. She leaned in and blew gently, tongue touching at the taint, then working up to kiss just over his hole.]

[He tenses up at first, just from the feel of her blowing out against his hole, then feeling her lips there.]

Tickles.

[He murmurs, but tries to relax again, despite his subconscious urge to pull away. He doesn't really want to pull away, though. He's happy where he is.]

[She uses the flat of her tongue, dragging it over the entirety of his hole, then moves her hand in to press her thumb against that flat bit of skin, gently moving it around as she pressed her mouth in against him more. She'd get him worked up from the outside first before she started playing with entering him a bit.]

[ He sucks in a slow breath at the feel of her tongue along his hole. Maybe it really is insane that he's never felt this before, but he doesn't think he would've ever let anyone but Jess do it anyway.

He's tense here and there, but always relaxes until he finally lets out a soft moan. ]

Jesus... feels good.

[She'll stay with that for a little while, alternating between tonguing his taint and massaging it, then up to tease his ass. She can see his cock, so she knows he's still turned on, and she waits until he's made a few more of those needy pleasure sounds before she starts to let her tongue work to press into him.]

[ Oh, he's real turned on. It's a whole new sensation, but he's loving it so far. When her tongue presses in he gasps, fingers curling in the sheets a little. ]

Oh, wow.

[She hums against him, hoping the vibration feels as good there for him as she knows it does other places. Then she starts to work in earnest with her tongue, pressing it into him, sucking at him, working him open with just her mouth- but all while keeping her hands and body free from touching his dick at all.]

Ah.... fuck, Jess.

[He groans when she presses into him more, and his body clenches in a different kind of way, nothing tense about it. He can't believe he's never felt this before. It's got his squirming a little.]

That's good... fuck, it's good.

[She drew back, blowing on him a bit just for that added temperature play, then kissed the swell of his ass.]

You want more? Because this is where I'd start using a finger, if you're okay with that.

Yeah... yeah, I'm okay with that.

[He says it a little breathless, but not as hesitant as he was earlier.]

[She moved to bring a bottle of lube over, along with the finger vibe. It wasn't quite time for either yet, but she wanted to make sure she didn't have to search around for it when she needed it.

She sucked at her finger, then licked at his ass again while she pressed one digit slowly against him. Just in a little, just enough for him to get used to while she licked around and back down to his taint again.]

[ He can hear her sucking on her finger, and really that alone sends a tingle through him. He bites his lip, waiting in anticipation as her tongue drags back along his hole, leaving him aching for more.

He gets it a moment later when her finger presses in, feeling a lot more solid than her tongue did. She really is so good at getting him to feel all these sensations at once. ]

Oh... fuck. That feels weird. But not- bad. Just weird.

[She told him to talk so he's talking.]

Weird is okay. We can work with weird. Just let me know if it gets to bad. We're going to do this slowly. A little bit at a time.

[She licked at that spot again, then up to work her mouth around the muscle that had her finger inside it. A little wiggle, but only to get him adjusted to the idea of something in there that moved. She was barely up to the first knuckle.]

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