For about 3 years I dated a guy named Zach. He was 3 years younger than me (26 at the time, when I was 29) and he had a short, twinky body with a very cute face. We had a good relationship and it ended on pretty good terms. We were in a closed relationship, but secretly I thought the idea of him getting topped by other guys was really hot (I used to jerk off thinking about it), but I never told him.
We stayed in touch over the next year or two, until one day he told me he was in a new relationship with a guy named Milton, and that he was finally trying being in an open relationship. I was really happy for him but didn't ask too many questions. I did have a look on his social media and saw a few photos of them (Milton was a bit bigger built than Zach, but still lean and shorter than me), but didn't think much more of it as our relationship was quite long ago.
A few months after that (a few weeks ago), I was chatting with a guy online that I hit it off with. He was quite handsome and said he was a vers top. I prefer to top, and he wanted to trying bottoming more so seemed like it could work. We had some hot chats, and turned out we were both into anon role play. We'd shared some photos of each other, but not enough that a blindfold wouldn't be hot. We discussed how I'd leave a key out for him, and he'd let himself into my apartment before I got home from work, and wait for me on his knees, nude, and blindfolded. I'd come home, feed him my cock, and then wait in the other room until he left. We didn't make any solid plans, but both jerked off to this idea.
One night I finished work at about 10pm and was super horny. I logged on when I got in my car and he messaged me right away, straight up suggesting we should hook up that night. I was pretty tired but was starting to get a little turned on after he sent me a cute ass pic. I started playing with myself a bit in the car and quickly got quite horny. He was begging me to send him photos of my dick, so I told him to send another cute picture of himself and I'd think about it (I'm a bit of a tease). So he sent me a picture of himself... with another guy. My ex-boyfriend, Zach. A shiver went up my spine. I asked his name and he said Milton, and told me that was his boyfriend in the photo. My whole body shook, my cock getting even hard at the prospect of hooking up with my ex's current boyfriend. I was starting to leak in my shorts and quickly messaged him back with a photo of my cock. It's about 8.5" and has a good girth. He asked me how big it was, so I told him. He said he'd never taken a cock that big personally, but his boyfriend's ex apparently had a similar size and it was the biggest cock he'd (Zach) had ever taken. Milton said he was a bit jealous... but mostly about the fact that Zach had got to experience a bigger cock than him! Knowing that I was still the biggest cock Zach had ever taken made me even harder and more determined to hookup with Milton.