Shep

Darrell

Shep’s take on things was rather different than most would have expected from what seemed to be a first venture into more open expressions of sexuality.

More than noticing the more popular guys showing off their being slightly well-hung, Shep quickly took an interest in those even better hung, who seemed to be as quiet and unassuming as he had always been.  Sure, he had had plenty of moments when others wanted to have a closer look at him, but that had almost seemed to increase his being almost backward socially.

So seeing Jake and Russ be so open with him was somehow a welcome change from what he had become accustomed to, and it seemed to take surprisingly little effort on Shep’s part for others younger than him to quickly fall into line, as it were, only behind Jake and Russ, even though it didn’t really seem like either of them were out there very much at all.

That somehow got Shep to focus even more on Darrell and Barker, each of whom seemed even more shy than most, despite them both being hung considerably more than average, both of them being in pretty impressive shape, and both of them being more handsome than not.  So could it really be that there were that many shy guys out there, or was it that the better hung ones actually tended to be more shy than average?

In any event, Shep found himself relating to them very easily, perhaps even more than with Jake and Russ, as Shep began to focus on what he might do to give these guys more confidence, at least when this select group got together, even if it was mostly to use Jeff.  Whether Shep was starting down a path of getting more and more guys to at least try out being gay would be something Shep decided he would leave to the future.

As luck would have it, Darrell and Jeff actually lived right next to each other, so it wasn’t all that difficult for Shep to get Darrell and Jeff talking together, at least a bit, once they had finished their workout fuck sessions.  Even better, Darrell proved to be even more cool than either Jeff or Shep had anticipated, and even more flattered than most at the new attention he was receiving.

Darrell had never really had much of a girlfriend.  No one seemed to know why either.  He was well built, fairly hairless, other than a bit under his arms and a bit above his dick.  And his cut dick was actually quite attractive, considerably thicker than most, and probably an inch or two longer, with balls to match.

Getting Darrell to join in with the gang that fucked Jeff was easier than Shep had expected, despite Darrell’s seeming to have not had much experience, maybe with sex at all.  So it also wasn’t all that hard for Shep to invite Jeff and Darrell to meet with him together, just the three of them.  Shep was still trying to figure out whether he was really enjoying watching all these guys use Jeff, or whether he really was going down a path of helping shy hung men work on being gay, as much as Shep possibly could.

The first time Shep just invited Darrell and Jeff to hang back, much as Jake and Russ had done at the very beginning.  But Shep had the advantage of access to the office, where he could give Darrell some private lessons on how to enjoy himself even more, as the group continued to develop, and even as Shep began working on putting an older crowd together as well, unsurprisingly built on these quiet, almost shy, hung guys.

Shep was as kind as one could imagine to Darrell, and Darrell was quickly flattered at the attention he had seldom, if ever, been given prior to that.  And Jeff had easily fallen into his role of being the group’s bottom, quickly becoming even more curious than Shep at what Shep was setting out to do.

That first time was a surprise to all, since Darrell had already shot with the crowd, so when Shep told Darrell to relax, and just watch, as Shep instructed Jeff to pull down Darrell’s shorts and jock, Jeff was fully expecting a soft spent cock, not an already throbbing, precumming, hard one.

Shep smiled.  Jeff was impressed:  “Wow, man.  You’re even bigger now than you were with the gang.”

Darrell was almost embarrassed, and turned a bit red.

“Don’t be ashamed at all, man.  Your cock is gorgeous.”

Of course Shep was watching over:  “Enough flattery, bitch.  You know where it belongs.”

Jeff smiled as he softly took Darrell’s throbbing knob into his mouth, with Darrell leaking more and more precum the more Jeff licked it.

“Take control man.  You know he wants you to.  That cock looks amazing.”

And that was all it took from Shep for Darrell to start shooting, almost looking for Shep’s approval as he did, almost half a dozen thick white shots of cum, as Shep rubbed Darrell’s back, and made sure all of Darrell’s cum went straight into Jeff’s willing throat.  “Take your time to totally unload, man.  That may well be the most impressive cumshot we’ve seen all morning.  Fuck.  You may even get me hard again, man.”

Shep even reached out and kissed Darrell’s cheek as Darrell continued to drain his still hard cock into Jeff’s mouth, as Darrell turned red yet again.  “Fuck man.  Keep it hard.  I’d love to help you fuck him as well.”

That got one more shot out of Darrell, who now smiled at Shep.  “Wow.  That was even nicer than with the group, man.  Thank you.”  As Shep reached down to help drain the last of that load out of Darrell’s cock:  “Let’s go for it, man.  You know Jeff would love to have you quietly fuck him again.”  Even as Shep grabbed his own crotch, with his own cock clearly growing hard again.  “This is more fun than I expected, to be honest.  You’re one hot man.”

Darrell was still a bit shy:  “Really?”

“Fuck man.  This may be the hottest sex I’ve seen.  Let’s strip him and get that cock back in that cummy hole.”

And with that Darrell actually helped Shep strip Jeff down and bend him over, as Shep actually held Darrell’s cock as it went back in Jeff’s hole, still leaking cum from the earlier bang.

“Talk to me, man.  How is it, for real?”

“Fuck, man.  I wasn’t really thinking about anything than just trying to fit in with the crowd before, but this is pretty damned amazing.”

Shep smiled again:  “Damn.  I should have been doing this a long time ago already.  Fuck it slowly, man.  Enjoy it.  With him living right next to you, we should make sure this happens at least once a day.  Now drive all the way in and listen to that cunt beg for your seed.”

Both Shep and Darrell paid close attention as Darrell’s thick cock went all the way in, then came all the way out, of Jeff’s already swollen hole.  “Sounds pretty fucking hot, no?”

Darrell smiled.  “This is actually pretty amazing, man.  Thank you.”

Shep smiled, and leaned in to kiss Darrell a second time, with Darrell even turning his mouth to meet Shep’s lips, even as Shep started pulling his own now hardened cock out.  “Mind if we take turns a bit?”

“Wow.  Your cock is amazing, man.”

Darrell was so sincerely impressed, even Shep blushed a bit.

“I really had no idea this would be so fun, Darrell.”  Even as Darrell pulled out of Jeff’s hole, as Darrell even asked Shep if he might help Shep the way Shep had helped him.

And Darrell even chanced a kiss on Shep’s cheek, as Shep’s huge cock slid in.

“Feed it to him, Darrell.  We can take turns there too.”

Jeff, meanwhile, was in heaven.  This whole thing was so much sexier than the bigger group had been...