Shep

Shep was an interesting guy, and surprisingly set into motion quite quickly by Jake and Russ.

In retrospect, it was almost surprising how much of Shep’s personality revolved around being so well hung.  He was in decent shape, relatively attractive, but almost more than anything hung so well that that was what first came to mind when guys thought of him.

Openly, plenty of guys would make jokes about what a huge dick Shep had, to the point where it was easy for him to become shy and hesitant about just being out there, let alone naked, even though those same guys were quietly jealous of his being so well endowed, especially knowing they weren’t.

The effect on Shep was to make him more thoughtful somehow, as well as more respectful of differences, especially of the fairly broad array of cock sizes, especially the more time he spent working at the gym, coordinating various groups of guys working out.

So when he ran across Jake, who was almost as well hung, Russ, who either seemed not to care or to openly admire Jake, and Jeff, who all but worshipped Jake, Shep was at least intrigued.

And when he saw how they were so open about their sexual interests, it was almost like a new world opened to him, which he had quietly dreamed of every once in a while, but never really thought could actually happen, at least with him in it.

So even though they were a bit younger than him, Shep almost immediately embraced their friendship, and even more immediately embraced the opportunity to be who he had never really dreamed he might able to be, almost at one with Jake, almost immediately befriended by Russ, and even more quickly worshipped by Jeff, who had also struck Shep fairly quickly, mostly because of how happy he seemed to be evenly openly worshipping guys, and doing things Shep had never really thought anyone might openly do.

Unsurprisingly then, Shep was fairly restless that first night after Jake, Russ and even Travis (because he was the most popular of the three) had invited him to join their escapades with Jeff.  Of course Shep had often fantasized about sex, and was well aware privately of how huge his dick was, but this was a whole new opportunity, that more guys than he had imagined were more than happy to get involved in.

So that evening he had quietly met with Russ, and even shared these crazy nipple plugs with him, honestly wondering what Russ might actually do with them.  And the next morning he showed up a bit earlier than usual at the gym, mostly out of sheer curiosity.

But it quickly turned into way more than that as almost the first thing he ran into was Jeff actually sucking on Jake’s dick in the open, and even drinking his piss, with Russ almost proudly showing the whole thing off to Shep.  So for maybe the first time, Shep was looked at as a ringleader, with at least three, if not more, other guys happy to join in, whatever lead Shep might provide.

From there it wasn’t much of a stretch for Shep to escort them into the office, and even for Shep to end up fucking Jeff, right there in front of Jake and Russ, and even with the door ajar, as Shep tried to embrace the new opportunities as quickly as he could.

What he hadn’t really expected, however, was how much more involved Jake, Russ and Jeff seemed to be, let alone how comfortable Jeff was at being such a willing, and able, bottom, to say nothing of the ease with which Jeff took Shep’s entire dick, deep into what seemed like so much more experienced of a hole than Shep had imagined, even in some of his more wild fantasizings, as he quietly jerked off in his own bedroom.

But Shep had thought enough that he really was ready to run with things, so almost as soon as he unloaded in Jeff, and then let Jeff suck him clean (yet another surprise for Shep), Shep went out to start looking for volunteers for the plan he had concocted.

After overcoming his shock at how far various guys had gone with Jeff, even out on the field, Shep decided he would open a small gymnastics gym to a smaller group of guys, if they were interested, if nothing else just to see where things might lead.

Fortunately one of the first guys he saw was Travis, yet another curious one, since Travis outwardly seemed fairly popular, although Shep would learn Travis had plenty of quiet questions himself, which became one of those quick clues as to who might be more interested than Shep had imagined at getting involved with these other guys.

So far, Travis was clearly the last of the original group of four, but very happy as Shep reached out to him, and even more happy to be the first invitee to the gym, as well as to help Shep find others, as the two of them tried to figure out how big of a crowd would really make sense, at least at the outset.

Rodney was an easy first choice, both because, as Shep would learn, Travis had history with Rodney, and also because Rodney was yet another of those quiet well hung guys, who Shep could relate to all too easily.  So with Shep, Jake, Russ, and Travis, and of course Jeff, they were already up to 5, as Jake and Russ continued playing with Jeff in the office, and as Travis and Rodney now helped Shep shop around a bit more.

Paul was another sure bet.  Another fairly quiet guy, well hung, and smarter than guys gave him credit for being.  Even if Shep didn’t know that Paul and Jeff already had a fairly long history already, as Shep would learn fairly quickly. So now with 6, Shep was already wondering out loud just how big a group they should start with.

But at this point, Travis knew he had to invite his neighbor Don, and then they decided to go a bit out on a limb, as they focused more and more on the better hung quiet ones, settling in for Darrell, who also happened to be a neighbor to Jeff, and Barker.  Almost universally, all of these guys were not part of any big crowd, and usually hung back while others seemed to take the lead.  What no one had focused much on, it seemed, was just exactly what these guys’ sexuality was. 

Shep smiled.  9 was a pretty big crowd, at least to start.  And having never supervised a crowd like this, Shep was interested in watching things develop, as he headed back to the office to calm Jake and Russ down, and to let them know what was in the works.

Planned sessions were broken down to just an hour, so Shep’s expectations were modest as they all headed off to the gym, while the rest of the regulars headed outside, even if there seemed to be plenty of chatter about the new group, even more so as most guys knew the majority of them weren’t really either necessarily the best athletes or the most popular.

So when they got to the gym, Shep welcomed them, as he pulled Jeff close to him, then lifted up his shirt and clearly felt his tits as he thanked everyone for being part of this experiment, and invited them to be as free and open as they cared to be, even going so far as to let them know Jeff was as happy to see them all as Shep was, and noting that Jake and Russ were at least partially involved in setting the whole thing up, as Shep’s hand went down the back of Jeff’s gym shorts, pushing them down as his fingers clearly entered Jeff’s hole, as Travis came closer.

From there things just kind of naturally, even if sometimes a bit awkwardly, took off, with Shep more or less supervising, assisted in part by Jake and Russ, all three of whom had already shot that morning (Jake even more so, even though only he and Jeff knew about the night they had spent together).

Travis had missed out on the evening’s (and morning’s) activities, so he was the first to get more intimate, followed fairly soon by his buddy Don, who he actually helped get comfortable with using Jeff in front of the others.  Travis was actually also the first to kiss Jeff in the open, even as others watched, signaling even more clearly that guys should feel as free and open as they cared to feel.

It was only an hour, and everyone had things they still needed to get to, apparently other than Jake and Russ, who were still curious about whether Shep had anything more in mind than just this one event, so it was a bit of a challenge just to make sure everyone who wanted to got to shoot at least one load.

Shep himself actually proved to be a kinder than expected trainer, which was often not the case in the more typical setting the guys were used to, as he showed special care to both Darrell and Barker, who he suspected weren’t as familiar with all that was going on as others, even if they were both curious and increasingly interested, even as Shep made sure Jeff sucked them off, and Darrell even succeeded in dropping a load in Jeff’s hungry hole.

Over time it would become apparent that all the others had already been with Jeff at least once, and Jeff was a better than anticipated group bottom.  And although Shep was clearly the ringleader here, it became more and more interesting to see the various relationships that were emerging, both in terms of who hoped to be an even more real ringleader, and in terms of what relationships had already forged and were developing even further

So the guys had their fun, and gradually headed off to shower and move on, with Jake especially curious, it seemed, to see how this might personally affect him moving forward.  Shep even ended by thanking the guys, hoping they had had a good time, and letting them know they were more than welcome to continue developing things however they saw fit.

All in all, as Jake tried to evaluate things with Shep, Jake learned that Shep was very happy to have given some shy guys a chance to be more out there, even though no one really talked about how gay anything was. 

“Who knows, some of these guys may just be opening up, or just getting off.  Honestly, I’m just hoping they all had a good time.”

Even Jeff chimed in.  “Thanks Shep.  That may have been the most interesting group I’ve ever been involved with, so far.”

Shep missed nothing:  “Glad you put that emphasis on so far.  I’m surprised how much I love watching guys have sex with guys, and be more open with their sexuality.  This last hour may have been the best hour of my life.  So far.”