Flashback Friday: Getting Comfortable With It

First Friday of the Month usually features a flashback to a previous story, sometimes with improvements added. Original Here.

Coach loved pairing up the jocks, and he especially loved seeing when his eye for chemistry was confirmed with explosive passion. Yet, that didn’t always mean all pairings were then ready to go without any further work from Coach. Many needed help finding their natural positions, especially when many had come from a culture of toxic masculinity where bottoming was seen as a “girly” thing to do.

Although Coach often promoted proper masculinity for his jocks, he also wanted his jocks to realize that bedroom roles had nothing to do with it. When one of his new star recruits showed hesitation to do more than receive a blow job, Coach set out to make him completely comfortable with bottoming.

As the teammates that had already bonded played on the bed, Coach went to work with his suggestions. Soon the jocks had stripped away their inhibitions along with their clothing, and a dildo was brought out to help break in the reluctant jock as his new boyfriend Terry assisted.

That’s right …. in this relaxed state it becomes so easy for you to allow that dildo to just slide in. And as Terry begins to slide it back and forth for you, every thrust inside of you helps you become more comfortable with the idea of being fucked. Because if a dildo can feel this good, you know that Terry’s cock will feel one hundred times better. And so it won’t matter if you’ve only ever fucked girls in the past. Your ass is now primed to be fucked and you’ll find that you always prefer to bottom from now on….

And so the training continued, the jock relaxing to Coach’s voice as Terry slowly and methodically opened up his hole. The more he relaxed for Coach, the deeper Terry managed to slide it in. And the deeper he went and that it went, the more pleasure he felt. Any pleasures he had felt before as the fucker could not compare to the pleasure now being programmed into him as the jock that would love to always be sexually submissive for his boyfriend, his Coach, and the team. Finally, it was time. Terry laid back as his boyfriend carefully sat on his dick, sliding it in just like that dildo – and realizing that this felt even better. Terry would end up fucking him from multiple positions, each position getting the jock more and more comfortable with his new favorite role.