I had a straight coworker once who was like a disgruntled, pessimistic type. Cute, but always going on about his lack of girlfriend/sex life. He knew that I was gay, and used to ask my advice for hitting on women, or he'd run pickup lines by me. It was all very strange, as if he was looking for my approval somehow. One night, out of the clear blue sky he sent me a text. We had exchanged numbers but rarely text each other. His text asked, "Can I show you something?" I sent back of course, thinking it would be...God knows what. He was certainly cute, but odd. What I got was a series of FIVE dick pics. One was flaccid, one was semi erect, and the last three were fully erect, from different angles. I sent him, "Wow, that's not what I was expecting." He proceeded to ask if I thought he had a good size and an attractive dick. Also he trimmed his pubic hair for the first time and wanted me to tell him if he did a good job. I answered all the questions, and I thought that was that.
About 2 hours passed and he sent me, "Sheesh you're not even gonna send me one?" I asked him if he wanted me to, and he said he just thought I would. I didn't immediately and he sent, "Well?" I told him to hold on, and in the interim he said, "It's not like I can't look at one." So I sent him a series of erect cock shots. He sent back "Nice" and proceeded to get into a brief conversation with me about being uncut.
That was on the weekend, and on Monday at work he brought it up again. He asked me 20 questions about being uncut and was so persistent about it all day that he eventually just had me show it to him in person in the employee bathroom. I got hard, and he showed me his but didn't get hard. A little plumped though.
The weird part of it all comes next. A week or so later, we got sent to a different city to help open up a new store. We shared a hotel room and on the first night, I took a shower before bed. I came out of the bathroom in my briefs, but took those off as I sat down, in order to sleep naked. He started pitching a fit that I would sleep naked with him in the room. Not even the same bed, there were two of course. We were there a week and I never once saw him shirtless even, or in his underwear, nothing. He changed in the bathroom exclusively. I just kept sleeping naked. LOL It was just such an odd 180 from "Show me your hard cock" to "Why are you in your underwear?"