I'm not sure if this is actually a cuckolding story, but someone in another sub told me it was, so here it goes:
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This weekend I drove my husband Gary an hour and a half to another city to help him explore his sexuality.
This has been building for a while. We're swingers (and also do other CNM) so he's touched men plenty of times in the context of group sex, but then about two months ago during a gangbang we threw for my birthday he got fucked in the ass by another man for the first time and liked it, which made him want to try having sex with a man more intentionally.
We live in the middle of nowhere and it wouldn't really be safe to be out locally, so he downloaded grindr and set his location to a larger city, and not the one closest to us. He got a ton of matches. Apparently there's a lot of interest in a short chubby 40 something in the gay community. He picked out an absolutely ripped guy in his 30s who was almost a foot taller than him.
Gary was nervous about having his first real gay sex, so he asked his grindr date if it was okay if I was there helping. Ethan was cool with it, said he hadn't been in a room with a naked woman in a long time and he thought that a threesome would be cool as long as he wasn't expected to touch me, which he wasn't.
We went to Ethan's apartment, he offered us drinks, and generally gave off a safe, confident vibe. Before we finished our first drink he kissed Gary and led us to the bedroom.
At first I just watched them and touched myself. Gary reached out a few times to hold my hand, pet my thigh or tits, but soon I couldn't help myself. I put my tits in Gary's mouth while Ethan was going down on him. I spanked him and stroked his dick while he was going down on Ethan. When Ethan started getting Gary's ass ready with lube and his fingers I put my pussy in front of Gary's mouth so he could lick me, and then held his head in my lap while Ethan entered him with his cock.
After that I stepped back again and let him enjoy his time. I've never heard my husband make those kinds of noises, not even when I've pegged him. I could see him leaking precum all over the towels that Ethan put down while his ass got plowed and he begged for more. I couldn't stop masturbating but also couldn't take my eyes off of him.
Gary came from anal, which I've never gotten him to do with my strap on, so I guess he likes the real thing better. I'm not hurt, though. I'm proud of him. Ethan was the right amount of strong and kind. He said afterwards that the whole thing was surreal for him, since he's actually just gay and not interested in women, but also he said that having me there made it hotter. He said that he fucks too many married men who don't tell their wives and that this was refreshingly wholesome for him.
We will definitely be doing this again.