RedCherry

[4] The Final Dare

Added 2025-02-04 00:00:04 +0000 UTC

Ashley, with reddened lips and a flustered expression, sits in the back seat. Jake, still aroused, looks at him with a smirk.

*Ashley:* (complaining) Jake, my lips hurt... I can’t do this anymore...

*Jake:* (smirking) Alright, you can take a break. But I’ve got another idea.

*Ashley:* (warily) What is it?

*Jake:* (calmly) I want to put it in your ass.

*Ashley:* (shocked) What? No, Jake, that’s too much...

*Jake:* (persuasively) We can stop if you ask me to. I promise.

Ashley, his heart racing, looks at Jake. He hesitates but finally nods.

*Ashley:* (whispering) Okay... but only if I can ask you to stop...

*Jake:* (pleased) Of course.

Jake helps Ashley lie on his back, lifts his legs, and begins to slowly insert his thick cock. Ashley moans from the pain and unexpected pleasure.

*Ashley:* (moaning) Oh, Jake... this feels so weird...

*Jake:* (gently) Relax, Ashley. You’re doing great.

Jake starts moving, changing positions, sometimes sitting Ashley on top of him, other times pressing him against the seat. Ashley gasps and moans, his body gradually adjusting to the new sensations.

*Ashley:* (crying out) Jake, I can’t... it’s too much...

*Jake:* (breathlessly) You can, Ashley. You’re doing so well...

As they approach the climax, Jake, his face tense, says:

*Jake:* (moaning) I’m about to cum...

*Ashley:* (panicking) No, Jake, not inside...

But Jake, ignoring his plea, keeps thrusting until he reaches his climax. Ashley tries to push him away, but Jake holds him firmly.

*Jake:* (quietly) Wait a minute... let it fill you completely...

Ashley, from these words, also reaches his orgasm, his body trembling with pleasure. Jake, satisfied, releases him.

*Jake:* (smiling) So, how was it?

*Ashley:* (flustered) I... I don’t know... it was... incredible...

Jake, looking at him, offers one final dare.

*Jake:* (playfully) Now go take a walk around the city like this.

*Ashley:* (shocked) What? No, I can’t...

*Jake:* (persuasively) You’re still riding the high, Ashley. You can handle it.

Ashley, under the influence of his emotions, agrees. He steps out of the car, still in the dress and stockings, and walks down the street, feeling a mix of shame and excitement.