In The Sandman, Loki after having his neck broken and his eyes eaten by the Corinthian tries to goad Thor into killing him by revealing that he had seduced Thor's wife Sif. He goes into rather lurid detail too.
Endgame by Tara O'Shea, the first-known Galaxy Rangers fanfic on the web, used this.
Gender-reversed a couple of times in The Shadow Chronicles, first with a spider demon taunting Akane about what she'd done to Ranma and later with a succubus taunting Sailor Moon about what she'd done to Tuxedo Mask.
Used symbolically in Cori Falls's fic "The Power That's Inside", where the leader of the Scyther swarm taunts Meowth with how he destroyed Jessie's hair to goad him into losing his focus during their fight.
Rosario Vampire: Brightest Darkness Act II uses this spectacularly. Miyabi rapes Mizore, and when Tsukune and the others find out, he taunts Dark, Mizore's new boyfriend, by remarking, "If it makes you any feel better, she wasn't that good. She didn't even scream for me." He gets his just desserts soon after.
In The Devil's Advocate: "Well, on a scale of 1 to 10 — 10 being the most depraved act of sexual theatre known to man, 1 being your average Friday night run-through at the Lomaxes' household—I'd say, not to be immodest, Mary Ann and I got it on at about...SEVEN!"
In The Film of the Book of The Crow, Tin-Tin taunts Eric Draven, whose girlfriend was raped by him and his friends. He comes to regret these words.
In Gladiator, Commodus tells Maximus that his wife "moaned like a whore" while Commodus's men raped her. Since Maximus had already spent nearly the entire movie in an Unstoppable Rage, ramping it up from there over a few last minute insults would have just been unnecessary. Doesn't mean Maximus didn't kill him when he got the chance, though.
Highlander - Centuries after the Kurgan rapes Macleod's wife, the Kurgan taunts Macleod that this is the reason his wife never told him about it.
Kickboxer does this trope slightly less subtle. "Good fuck." This is in reference to Kurt Sloane's girlfriend Mylee, whom Tong Po had beaten and raped a few days before the big fight.
In Rob Roy Archibald Cunningham rapes Robert Roy MacGregor's wife, who avoids telling her husband for fear that he will do something reckless to avenge her honor. Rob does eventually find out, and when he's captured by Cunningham they have the following conversation:
Robert Roy McGregor: You're a thief, a murderer and a violator of women. Archibald Cunningham: Aah... I had hoped you'd come to me long since on that score. Robert Roy McGregor: If I had known earlier you would have been dead sooner. Archibald Cunningham: I will tell you something, to take with you. Your wife was far sweeter forced than many are willing. And truth put to it, I think not all of her objected...
A number of bad guys in the James Bond film series have used this.
Downplayed in Goldeneye. Alec Trevelyan doesn't actually rape the damsel in distress (as far as we see) but does force a kiss on her and then gloat to Bond:
Trevelyan: Lovely girl. Tastes like strawberries. Bond: I wouldn't know. Trevelyan:I would.
In Licence to Kill, Dario and his men taunt Felix Leiter with news of their murder of his new wife, among other things telling him, "We gave her a nice honeymoon," implying that they raped her before killing her. Then they feed Felix to a shark.
In The World Is Not Enough, as Bond prepares to execute the villain Renard, the latter quickly picks up on Bond's feelings for Elektra and taunts him thus:
Renard: "She's beautiful, isn't she? You should have had her before, when she was innocent. How does it feel to know I broke her in for you?"
In Wild Things, teacher Sam Lombardo is accused of rape by a female student and another girl. They both claim that after the deed he told them "no little bitch could ever make me cum". Subverted later on when it turns out that Sam and the two girls were running a scam together.
In the finale of Kiss The Girls, Casanova taunts Alex Cross how he molested his kidnapped niece for ten days purely to press his Relative Button. However, Cross maintains his calculating demeanor long enough to defuse the Taking You with Me situation.
In The Jester by James Patterson, one of the antagonists pulls this on the hero, whose wife was kidnapped while he was participating in the crusades.
In the Outlander series, evil Depraved Bisexual Captain John Randall loves doing this to Jamie. He tries to make Jamie think that he raped his sister, as well as his wife. Despite the fact that it was later revealed that, in both cases, he was incapable of getting himself sufficiently hard to do that. Why would he do that? Because he's in love with Jamie, and in his messed up mind, he loves seeing Jamie hate him.
In Roald Dahl's short story The Great Switcheroo the protagonist Vic entices his friend into a mutual Bed Trick so they can sleep with each other's wives. They go to great lengths to make sure the wives don't find out, wearing each other's cologne, discussing their bedtime routine, technique and so on. Vic is dismissive of his friend's technique, but is crushed the next morning when his wife tells him that she had never really enjoyed sex until last night.
Euron: She came to me wet and willing. It seems Victarion is big everywhere but where it matters.
A minor villain in The Destroyer believes that it is not only a man's right, but in fact his duty and obligation to have sex with women whenever he can, regardless of what they feel about it. He even boasts that he's "shown a few lesbians what they're missing out on." Needless to say, no one feels any sympathy for him when he gets his at the hands of Remo and Chiun.
In The Wheel of Time, Eamon Valda tries to provoke Galad by gloating about how he raped Galad's stepmother.
Valda: She was the best ride I ever had, and I hope to ride her again someday.
Subverted in PLAGUE, book 4 of the GONE series; Drake Merwin does gloat about raping Brianna to her lesbian best friend Dekka Talent (who's in love with her), but it's a lie, and he never did rape her, only said so to upset Dekka.
Drake: I broke her legs so she couldn't run. She was screaming, but I think she liked it.
Occurs in the memoir Lucky by Alice Sebold, author of The Lovely Bones. The man who raped and beat her was not found until the next year after they happened to run into each other and he taunted her ("I know you from somewhere"). She called the police and he was eventually convicted, though at first she had trouble identifying him in a lineup (he apparently brought a friend who looked like him to confuse her.)
Live Action TV
An episode of Brimstone did this. The hero had to send his wife's rapist back to Hell.
This is also the main reason Zeke was in Hell in the first place. He tracked down his wife's rapist. The guy bragged about it. Zeke opened fire.
Done in an episode of Cold Case, when a father tracked down and confronted the pedophile who had abducted his son, and again, when the younger brother of a rape victim confronted the rapist.
Also with Serial Killer George Marks. Although he didn't rape any of his victims, he seems particularly smug about putting the fear of that possibility into them, especially the 14-year-old girl who had escaped an Attempted Rape sometime prior. He sleazily implies that the girl went from being terrified that she would be raped—he forced her to strip to her underwear—to practically offering herself to him in the futile hopes that this would make him reconsider killing her:
"You have no idea of the things a woman will beg you to do, if you'll just let her live."
In the Criminal Minds episode "Paradise," the Un Sub asks one of his victims if she's ever wondered what it's like to be with a real man right before he rapes her in front of her unconscious husband. Then he taunts them both about the husband's "weakness" for being unable to protect the wife.
On Heroes, Sylar possesses Matt Parkman's body and sleeps with his wife. He later brags that she enjoyed Sylar's version more than she ever enjoyed Matt's.
Invoked a couple of times on Robin Hood between Guy, Marian and Robin. Guy never actually does manage to deflower Marian; but after their coercive engagement Guy tells Robin: "I'll laugh every time I..." (interrupted by Robin's punch) and then later says: "I'll think of you when I take her to the marriage bed."
In Game of Thrones, Brienne and Jaime come across the bodies of three women who were strung up by Stark bannermen for sleeping with Lannisters. When their killers arrive suddenly, one taunts Brienne by saying "Two died quick. One died slow." This, predictably, mashes Brienne's Berserk Button, and she gives the man a Meaningful Echo of that line while driving a sword into his genitals.
On Law & Order (and the Law & Order: UK episode based on it), as the detectives listen (watch) the recording of Olivet's (Alesha's) rape, they hear the assailant taunting her throughout, telling that she ''begged for it", calling her "bitch" and "slut" before finally finishing with "didn't that feel good?", all over her repeated pleas for him to stop.
A female villain/female hero/male victim variant occurs in the Agents of S.H.I.E.L.D. episode "Yes Men". The villain Lorelei boasts to Agent Mei about using her Mind Control powers to rape Mei's lover Agent Ward. Lorelei also taunts Lady Sif about having used Mind Control to rape Sif's Love Interest.
''Highlander had an episode involving two Immortals, Jacob and Irena Galati. Irena was raped by a man, but because she and Jacob are gypsies, the townspeople don't do anything about it. As they and Duncan try to walk away with some dignity, the rapist and his friends taunt them. When the rapist says he should be paid a stud fee for his actions, Jacob loses it and goes after him.
In the elf campaign of Heroes of Might and Magic IV, the hero's rival steals his bride and uses sorcery to get her to be his willing wife, in every way. When confronted, he gloats that he will always be her first. Luckily, the hero uses a magical mirror to reverse the spell, although she still remembers all that's happened.
A rather unique (but no less depressing) example occurs in A Dance with Rogues. The protagonist is a female, and it is her who ends up being a victim of rape; immediately afterwards, the rapist laughs at her pain and callously taunts her. Later, this man (who she is forced to work with as an ally) makes constant jabs at her, spreading nasty lies and making snide comments all over the place in regards to what he did to her. If he falls in love with her, he stops this behavior, treats her much better, and is genuinely remorseful for what he did. Doesn't make up for it, but it's the thought that counts.
In GTA San Andreas Freddie make such taunts toward OJ Loc, his hormer "punk" before being killed by CJ.
In Family Guy, when Stewie is trying to get rid of Brian's replacement, New Brian, he tells him that nobody in the family likes him. New Brian retorts that Stewie's teddy bear Rupert seemed to like him while he was humping him last night, as "he just lay there and took it." Stewie remains calm and silent for a moment, then the scene cuts to him dragging a blood-stained trash bag out to the curb.