The first time I ended up swallowing another man’s cum was during a threesome. By this I mean that in the past I had “tasted” another man’s sperm experimentally. I had never kept sucking until the guy had finished cumming in my mouth and then swallowed his load, and my gag reflex did not kick in. It was not being able to keep from gagging not the taste that bothered me and kept me from enjoying it. As I mentioned I was in a threesome with the wife and another man. I was in a 69 with her while the other guy fucked her from behind. He eventually came and as he slowed his pace, and while I continued to lick her clit he backed away. As he did pull out, a huge glob of his cum landed in my mouth. At first, I did not know what to do, it was hot and sweet and after just pausing for a second, I swallowed it and much to my surprise did not gag.
However, I think if I was answering what I think the question is in the strictest sense, then the first time was at a glory hole. I have shared the glory hole story in another thread so I won’t repeat it here. The short version is I worked this guys cock over at a glory hole and after a few minutes he told how good it felt which only made me more in to it. As he was about to cum, he said, “I’m getting ready to blow” and the next thing I knew I could feel his cum landing on my tongue in spurts that matched his grunts and he was telling me how wonderful it felt. I continued to suck until I was sure he had finished cumming and I had gotten his entire load and then I swallowed all of his cum. As he calmed down he told me that I was really good and that it felt great. This was the first time I truly gave a man a blowjob to completion without pulling him out of my mouth and jerking him off. It was exciting to feel a man’s cock pulse as he cums and a huge turn on to hear him tell me he is about to cum moaning and groaning as he orgasms. At first, I was unsure of what my reaction would be, so I kept sucking while he came and focused on him while swallowing his cum. Initially, I did think I might gag as had happened on past attempts, but I resisted the urge and finished him off. It also didn’t hurt that I had had quite a few drinks that night…lol.