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.
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….
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I can certainly try, Bobby. Let’s focus on those fantasies you’ve been having. No doubt that even as you think of bottoming, it makes you a bit hard, doesn’t it, jock? 
Very good. Allow yourself to start with that. Allow yourself to get so nice and hard as you begin to submit deeper to My voice, just like you’ll find it’s so easy for you to begin submitting sexually. And as you begin to feel that pleasure, you can begin to strip down. First down to those briefs, feeling just how hard the idea of bottoming makes you. And when you are ready, you can strip down to your socks, stripping away all remaining inhibitions and all resistance as you do.
As the two came over for more programming, I emphasized that lust more and more – but I also positioned Judd in such a way that he would feel safe. Safe in his bro’s arms, as Cedrick held him tight during their make out session. Soon the boys were relaxing naked in a deep trance.