Superheroes have been involved with many women many of whom have also been villains. Here is a list of Marvel superheroes who have been involved with super villains:
Emma Frost and Cyclops
Though Cyclops and Jean Grey had their ups and downs, the couple was the best that the X-Men franchise had to offer. Jean had been putting off Wolvie because she loved Scott Summers, but then Jean dies in the dark Phoenix saga at the hands of Wolverine. This shocked the fans but had a little impact as after Jean’s death, Emma Frost and Scott come into a legitimate relationship.
Hulk and Umar
Yeah, He has banged the sister of Dormammu. Though he was not so much in his senses or didn’t even dominate. It was Umar who was doing it all, she wanted to do it “with the strongest one” The two banged so hard that they even bent reality. Hulk-Smash.
Black Cat and Wolverine
Felicia Hardy is quite a famous character in the Marvel universe, she’s more famous as her alter ego though. The Black Cat is known to be a constant flirtatious girl for Spidey comics, but that is nothing compared to what she has with Wolverine. The two have a pretty adrenaline rushing relationship with more flirting kissing and slashing that one can imagine.
Emma Frost and Iron Man
Yep, the diamond girl strikes again. Frost is known to be a real big bad deal when it comes to having flings with superheroes, the villain from the Hellfire Club, who also has had some crazy shit with Cyclops went down and dirty with Tony Stark as well. The two did some sort of ‘friends with benefits’ kinda stuff in Civil War.
Wolverine and Mystique
She loves him, she hates him. He loves her, he hates her. This dude has quite a complex relationship. From being eternal enemies as one id in the Brotherhood of mutants while other an X-Men, these two have traded blows a whole number of times. But also have slipped into bed equal if not more number of times.
She Hulk and Juggernaut
Well, Juggernaut truly is unstoppable, and so is She, the second strongest that there is. The two could be seen making out after Juggernaut gets to shield and she is his lawyer and is impressed by him, invites him into her bed.
Black Cat and Spider-Man
There was a time when Spider-Man and Black Cat aka Felecia, who was also Peter Parker’s classmate were involved in an intimate relationship. Though confusing, this relationship was an ecstatic one, both fighting off criminals and high on adrenaline kissing each other. Where Peter was fighting off criminals like the Kingpin and Doc. Ock, she could be seen working alongside them, though both could be seen fighting criminals alongside and she trying to unleash Spidey’s wild side but after finding out that Spidey is actually Peter, she loses interest in him, leaving him emotionally broken.