When you bring up trying thigh riding to young Michael he was excited at the concept but not so sure when you get to trying it out.
And getting rather embarrassed that he's stripped down to only silk-like boxers (which you bought him special for more fun teasing sessions) and with you having taken your shirt off so he doesn't feel like the only one exposed really hasn't helped, because now he's flushed up to the neck, not sure if he's more uncomfortable from feeling perverted wanting to stare at your breasts or just how hard he already is.
You gently coax him to sit on your clothed thigh, jeans waiting to become his mess.
Tentatively he comes over to you, feeling more naked than ever under your lustful gaze as you pull him closer and help him to be correctly seated on you, grinning at his hardness pressed against your leg, he shakily inhales at the sensation.
"Don't worry baby boy." You murmur, carding your fingers through his hair while he gets more comfortable.
One hand resting on his lower back, fingers rubbing lightly above his waist band of his underwear making him shiver.
You lean up, lips brushing against his ear, hot breath making him harder by the second.
"Take all the time you need." He jolts feeling you nip his earlobe, already giving a quiet moan before he slowly starts moving, releasing breathy whimpers as the fabric of his boxers catch slightly on your jeans, your hands firmly grip his hips urging him to continue.
His blush goes all the way down to his chest, between voyeuristic-like embarrassment of being in such an open room and so turned on his skin feels like fire.
Compared to your cool hand going to the back of his neck, pushing his face into your neck as he moans, curling in against you, his grinding becomes uneven when your lips attach to his neck.
Michael turns the best he can to give you more access as you start sucking, biting him and marking him as your own,
He yelps as you bite again, pinching one of his nipples while he grinds faster, the other hand slipping down the back of his boxers to roughly grab his ass and groaning as you squeeze him
"Such a good boy for me" tears prick his eyes from stimulation and your praise. He moans again, this time louder as you grip his ass tighter, so close, his boxers soaked with precum as he desperately pushes against you again and again.
Whimpering so sweetly, "P-please"
You grin, nails coming to scrape his bare back causing him to arch against your touch, ragged breaths as you continue to mark his neck, already enjoying the color blooming on his normally pale skin.
"Come for me baby." He jolts, grinding against you one last time with a shaky moan, cum shooting into his boxers, he can feel it dripping a bigger mess against him as he rides his high, whimpering into your neck and arms wrapped around your back holding you against him.
Stuttering hips are dragging it out and pushing him further against you in his euphoria as he begins to soften.
His entire body is shaking as it ends, Michael slumps against you, out of breath and panting while you soothingly rub his bare back.
"Such a good boy"
You kiss his hair and carefully move so he falls onto the bed beside you, splayed out on the soft covers and chest heaving as you move to lay beside him, propping yourself up on one arm and wiping away the tears that escaped him.
Michael looks at you smiling, exhausted and glad he did good as you soothingly pet his hair, only moving just enough so he can snuggle against you to rest.