One of the hottest things I've done.
First off, I'm gay. Known it for awhile, out for a year.
Secondly, he's straight. Let's call him Trevor.
Trevor and I have known each other for about a year. We both work at this breakfast diner during the summer. He started last year, I the year before. For the first summer, we barely talked because he was 'in training'. I also kinda found him very shy, which I do find very hot. However, I didn't want to creep him out.
By the way, I'm tall (six foot one), blonde, and blue eyed. He is shorter (five foot eight). Also blonde and blue eyed. He's cute but not hot. And me, not really hot to be honest, but cute enough to get guys.
Anyhow, well this summer I was scheduled to work with him almost everyday so we eventually bonded over our busboying and cashiering. He really began to open up and we talked on the job. Outside of work, nothing. But I started to find myself crushing the straight guy (you know you've done it too...) and so I initiated the first move and got his number.
I texted him later that night (like last week), and we talked like usual, pretty much just chitchat. Then out of nowhere, he made a sexual reference to jacking off and I took the bait and we then talked for hours about how we do it, where, when, to what, etc.
We kept this up for a week, talking every night about whatever came to the conversation (but it was always about sex of some sort).
Last night the conversation started out normal. He told me he was horny all day at the diner and how he had a boner the whole day (I was off). I asked if he had taken care of it. He said 'No, not yet. I was hoping for some inspiration.' I asked what he meant. And he replied that he wanted a picture. Here my mind starts turning about how I'm gonna deal with this. but he responds 'a picture of you'. And I pretended to play dumb, saying he would need to send me one first.
Lo and behold! He sent one within five seconds. I quickly tore down my pants and took a pic and sent it to him. We sent pics back and forth until we shot our loads.
He was off today, but tomorrow we are working together and I hope to take it further.
Leave comments if you want the updates.