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Chapter 16 by jk89 jk89

Which hole do you pick?

Her ass, of course!

"Oh Carolyn, I can tell already you won't be "just another cougar pussy", but if you're offering me anal sex, I definitely won't say no."

"I had a feeling you'd say that." she says laughing and making her way to her night stand to retrieve a bottle of lube. She pours a liberal amount on her hand before massaging it onto your shaft, making sure every inch is covered, then bends forward in front of you, working an oiled digit into her brown, puckered hole. Moving to her bed, she lies on her side then directs you behind her. "Have you fucked a lot of girls in the ass before David?"

"I don't know that I'd say a lot, but some." you tell her slipping in behind her and moving your cock towards her ass.

"Good. As much fun as it would be to say I popped your anal cherry, I think I'd rather have someone that knows what they're doing." Lifting her right leg in the air to spread herself apart for you, she looks over her shoulder to give one more instruction before letting you slide yourself in her. "Just start slow for me. Let me get used to it and then you can fuck me as hard as you want."

You line up your cock with her tight sphincter and nudge forward, feeling the oiled head slip inside. Her muscled walls reflexively tighten at the intrusion, clamping down on you. As she begins to relax, you're able to slowly inch more of your length inside her.

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"Oh yeah, there you go." she says, wiggling her ass against you and moving a hand between her legs. "Oh, that's perfect. Just a little more."

With your next nudge, you manage to slide the rest of your cock inside her, then hold yourself there, letting her accommodate to your girth. Once you feel her muscled walls loosen their grip around you, you're able to start working your length in and out of her. After having been in two, shall we say more experienced, cougar pussies earlier today, the change in pressure around your cock is immediately noticable. "Holy shit you're tight!" you tell her, picking up your pace.

Through her grunts and groans, she manages to respond to you. "Fuck! That's because I don't think I've ever had anyone this big in my ass before! You're going to stretch me out and ruin me for everyone else!"

Her tight, oiled sheath squeezes every inch of you as you pump in and out. Whenever you've had anal before, it had never been as good as you had imagined it would be, with the girl always tensing up and making you take it so slow that it was hardly worth it. Carolyn is different, though. Obviously experienced in getting fucked up her back door, she's letting you set the pace and appears to be loving every second.

"Oh fuck!.. Yes!.. Yes!" she screams out. "Fuck my ass, baby!"

Seeing how into this she is, you decide to try something you've never been able to do yourself, only having seen it done in porn before. You grab hold under her left leg and roll her on top of you so that she's now riding you, and begin hammering in and out of her bung hole. Carolyn goes right along with it, pulling her feet underneath her and leaning back onto her hands. You move a free hand around her and begin diddling her clit while she groans through clenched teeth.

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It doesn't take long for Carolyn to decide to contribute to your efforts and begins bouncing up and down on your cock to thrust you further inside her ass. "Oh fuck! Yes! Yes! Fuck that ass you big stud! FUCK IT!!

You can't believe how hard this anal whore is letting you fuck her and the tight fit of her asshole plus the rapid pace the two of you have set, has your balls quickly tightening and your cum boiling to the surface. Despite already cumming two times this morning, you can feel your third round is not far behind. As your release gets closer you start thinking about where you want to cum. You're sure she'll let you cum wherever you want, you just have to figure out where.

Where do you decide?

More fun
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