“You’re gonna need a bigger condom”

“You’re too big, so I don’t think that the condom will fit.” Sandy informed Jeremy, doing her best to sound dispassionate.

“Oh.” Jeremy didn’t really know what to say in response to that revelation.

“It sure feels big.” Courtney observed as she softly moved the palm of her hand over his cockhead, making Jeremy clench his buttocks together while letting out a short, baritone moan.

Letting go off Jeremy’s cock, Courtney giggled at his reaction to her touching it.

“Let me try it on.” Jeremy volunteered.

“I’m not sure that that’s such a good idea.” Sandy protested.

“You’re not using anything, are you?” Jeremy asked Courtney, adding a rather weak “Pills or something?” to which Courtney responded by shaking her head and biting her lip.

“Right, hand it over.” Jeremy ordered Sandy, who handed the condom and lube to Courtney.

“If you’re going to try it, you’d better be properly lubed up first.” Sandy informed the two teens.

Her hands shaking a little, Courtney struggled to undo the cap of the tube of lube, and then squirted a healthy portion of it onto her left palm.

“Are you ready?” She asked Jeremy, who nodded his head.

Jeremy sighed as Courtney put her hand against the root of his cock, the lube feeling cool against the surface of his member.

Gulping a little as she looked down at Jeremy’s dick, Courtney began rubbing the lube all over it with a gentle touch, still feeling a little awkward about how much she enjoyed having her hand wrapped around its considerable girth.

Unsurprisingly, Jeremy was thoroughly enjoying what Courtney was doing as she took her sweet time in administering the lube onto his cock, gently running her hand all over it again and again until all of it was glistening and the lube covered every bit of it.

“No Courtney, you don’t have to…” Sandy protested as Courtney squirted out a little more of the lube into her hands and set to work on Jeremy’s balls, but the older woman shut herself up as she realized that Courtney probably knew that anyway.

Jeremy laid on his back, incapable of doing anything more productive than groaning over and over again as Courtney lovingly fondled his balls, subjecting the two heavy orbs to her sweet touch as she meticulously spread the lube all over them until they were as glossy as his cock.

“Alright Courtney, now you’ll take a firm hold of Jeremy’s cock,” Sandy had to stop and wait for Jeremy to let out a guttural noise in response to Courtney grabbing his hard dick once again, “and then roll the condom onto it.”

Courtney followed Sandy’s instructions, and at first it felt pretty good to Jeremy. But soon things began to fill way too tight as the condom was clamped against his member, fitting it all too tightly in a way that was quickly becoming very uncomfortable.

“Ah!” The football star protested, “Get it off me!”

Immediately concerned by Jeremy’s holler, Courtney began to pull the condom back upwards again until her puppy-love’s member was freed from its grip.

“Are you alright?” Courtney asked as she got down next to Jeremy and wrapped one arm across his broad chest, her voice filled with concern.

“Yeah,” Jeremy’s voice was pretty thin as he responded to her question, though he could smile a few seconds later as he added “You’re the smart one, remember?”

“Poor baby,” Courtney kissed Jeremy on the cheek and caressed his stomach. As if to signal that he was alright, Jeremy grabbed Courtney’s hand and moved it down to his cock.

“I was afraid of this,” Sandy said, then making her own interpretation of the famous quote from Jaws by declaring “You’re gonna need a bigger condom.”

“Or we could try without.” Courtney suggested to Jeremy, “You could pull out when you’re about to cum and…”

Courtney bit her lip as she abruptly halted herself from saying anything more. She wasn’t entirely sure if it was alright for her to find the idea of Jeremy shooting his cum all over her tits and stomach so exciting.