When I was 18, I worked a summer job as a lifeguard before going to college. This supervisor ("Jen" for the sake of the story) was pretty good looking, decently fit, in her late 20s, great ass, so naturally I was into her. This was the second summer I had worked as a lifeguard with her, the previous summer we were absolutely not on flirting terms lol but we could get into small talk every now and then on my down times.

Anyways, about a month or so into the summer, it gets hot, like stupid hot, about 100+ degrees (way hotter than we were used to in our neck of the woods). We worked in an outdoor pool/water park aquatic center, so every couple hours we would clear the pool and us lifeguards would be able to get cooled off for like 10 minutes. Naturally, because I'm quite large, my swim trunks cling to my dick and show off a very noticeable print whenever I leave the pool. Normally I'm pretty good about shuffling things around as I'm getting out so its not as noticeable, but for whatever reason I didn't one time. As the guards ran up to Jen to get our stuff to get ready to go back to work, I see her eyes dart down to my bulge and she lets out an audible "woah". Someone asks her what's up and she said never mind, but I knew what she saw, and she knew that I knew.

Fast forward to the next day, and before our shift starts Jen pulls me aside for an "impromptu CPR review". I'm about to start performing on the dummy we have, when Jen starts talking pretty awkwardly. (Paraphrasing) "So... did you like... bring your phone in the pool during your cooling off period yesterday or something?" "Uhh, no?" "Oh... soooo what was that... thing... that I saw in your shorts?" (I turned pretty red lol) "Uh well that was my... private parts." "Oh... really... does it always... stand out like that?" "Yeah, pretty much." "Okay..."

I resume my CPR review and perform on the dummy for a few minutes, and she's about ready to let me go until... "Wait, Camctrail... would you maybe want to, like... visit my apartment or something? I have movies... games... other things. Is that okay?" "Uh, yeah sure. Tomorrow night maybe, since tomorrow's Friday?" "Okay... yeah that's good." "Cool. Thank you Jen."

Friday night comes, and no later than 30 minutes into my stay there we were already feeling each other up. She saw my cock for the first time and said "Jesus Christ it's bigger than i thought", and we went to town on each other for a couple hours. Safe to say that we had graduated from just occasional small talk from now on.