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50 Shades Of May: 15 Times Aunt May Got Lucky

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50 Shades Of May: 15 Times Aunt May Got Lucky

During his time as the regular writer on Amazing Spider-Man, first with Steve Ditko and then with John Romita, Stan Lee adhered to a number of “go to” ideas. One of them was Peter Parker thinking about giving up being Spider-Man, which was used at least five times before Lee’s first run ended with Amazing Spider-Man #100. Another very common plot point was that Peter Parker would have to find a way to save his beloved Aunt May, who raised him with her husband, Ben Parker, after Peter’s parents were killed when he was very young.

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Following Ben’s tragic death (which inspired Peter to become a superhero), May’s health deteriorated and Peter was constantly faced with instances where the only way to save her life was to get Mystery Serum X. As the years went by, May was allowed to slowly get a life of her own and became more than just a burden on poor Peter. She has had a number of boyfriends since, including three engagements and one marriage! Just so we’re all clear, we’re counting Trouble for this list, even though it has since been deemed non-canonical.


The miniseries Trouble was part of a bold initiative by Marvel to try to do romance comic books again. They wanted to support the line by putting some of their top creators on the concept. However, the first one, Trouble, by star creators Mark Millar and Terry and Rachel Dodson was a flop, leading Marvel to abandon the initiative and also determine that Trouble was not part of Marvel continuity.

Originally, it told the story of four young people, including young May Reilly, going to work at a resort (think Dirty Dancing) and falling in love. May gets pregnant and decides to go off on her own. She is picked up by a sketchy guy in a trailer and she ends up living with him for a few months. He is abusive and May eventually gets out of there with the help of her old friend, Mary.


As mentioned before, Trouble was an attempt by Marvel to do a popular romance comic book, a genre that they hadn’t had success with in 40 years at the time. Mark Millar, though, wanted to give it a modern twist, which of course meant that it was going to have lots and lots of sex in the story.

May and her best friend Mary are headed to work on a resort for the summer and meet fellow workers, brothers Ben and Richard. When the two pairs meet up, May and Ben get paired up and they are soon back at her quarters, but Ben doesn’t have a condom. In a stunning bit, May lets him know that she has protection and that, “Face it tiger — you just hit the jackpot.” It is hard to un-see Aunt May like that.


In a classic two-part story by Mark Waid and Marcos Martin, Spider-Man has to save the passengers of a subway car after the Shocker tried to kill them because the car was made up of members of the jury for a mob boss. Spider-Man was able to get them back to safety. During the whole time, he was especially friendly with one older man who handled himself calmly the whole time. Spider-Man then learned that this man was J. Jonah Jameson Sr., father of the Daily Bugle’s owner of the same name!

Betty Brant then introduced Jay Jameson to Aunt May and they hit it off. Peter Parker learned just how well they hit it off when he stopped by Aunt May’s house to change his clothes and accidentally walked in on May and Jay having sex! Quite a way to make a first impression!


For a while there, the popular magazine about comic books, Wizard, would occasionally work with DC and Marvel to create original comic book stories that would be included in bagged issues of Wizard. Most of them were #1/2 issues, but some of them were #0s, like Deadpool #0 (by Joe Kelly, Yancey Labat and Sean Parsons), where Deadpool ends up fighting against the geneticist, Arnim Zola.

Zola has created “bio husks,” short-lived clones of dead villains and heroes who worked for Zola. Deadpool killed off these clones and came across two clones Zola had made of Ben and May (who was believed to be dead at the time). Deadpool “killed” them, as well. Zola only managed to escape once he hooked Deadpool up with some Gwen Stacy clones!


During Trouble, May begins to carry on an affair with Richard, the boyfriend of her best friend, Mary, thereby cheating on her own boyfriend, Ben, who happened to be Richard’s brother. Ben knew Richard was cheating on Mary and Mary knew that May was cheating on Ben, but they didn’t know that Richard and Mary were cheating with each other!

This was made painfully obvious when Ben actually walked in on Richard and May having sex. Despite it being his own girlfriend, Ben was so distraught at walking in on his brother that he quickly looked away. And since he saw Mary coming, he intentionally came up with an excuse to let Richard and the mystery girl escape from the room, not knowing he was helping his own girlfriend cheat on him!


A lot of the main plot of Trouble revolves around, believe it or not, a fortune teller. Mary and May had visited a fortune teller and the psychic had laid out two very dramatic pronouncements. The first was that Mary would be a mother before she was 20 and that May would never be called “mom” by anyone. It was her fear over that prediction that led Mary to decide not to have sex with Richard.

Meanwhile, May and Ben were having sex constantly all over the resort, and it all served to drive Richard crazy when he was spending all of his time with the chaste Mary. The predictions turned out to be true, by the way, when May got pregnant but Mary agreed to raise the child as if it were her own. So yes, for a time Peter Parker was going to be revealed as Aunt May’s biological son.


After years of being a solo hero, Spider-Man’s life changed dramatically when he became a member of the newly reformed Avengers. Around the same time, Aunt May’s home was destroyed by a supervillain. Tony Stark invited Peter, Mary Jane and May to move into Avengers Tower if they wanted a safe place to live. This was during a point in time when May knew Peter’s secret identity — she later lost that information, along with everyone else in the world.

While there, May had an almost instant spark with the Avengers’ trusty butler, Edwin Jarvis. They began to date. When Peter found out that they were doing more than just “spending time with each other,” he had a bad reaction to the thought of the two of them hooking up with each other.


As noted before, Richard was being driven up the wall in Trouble with the idea of Mary not wanting to have sex while he saw his brother and his girlfriend, May, constantly hooking up. There was also that basic brotherly jealousy at play when Richard began to desire May. For her part, May found herself attracted to Richard’s “bad boy” charms (which were much different from Ben’s steadfast nature).

Being from a poor part of the city, May was constantly picked on at the resort by the rich snobs who attended the resort with their families. One of them gave May a particularly hard time and she was so pissed that she ran into a room. Richard followed and the two ended up having sex….the first of 47 times they would hook up over that summer!


During the “Superior Spider-Man” storyline that began in Amazing Spider-Man #698, Doctor Octopus managed to successfully swap minds with Peter Parker before Octopus’ body finally died. So Octopus was now in control of Spider-Man’s body, but due to the memories of Spider-Man’s strong sense of responsibility, he decides to still be a superhero, just a superior one to the original Spider-Man!

Before “dying” in Octopus’ body, Peter has access to Doctor Octopus’ memories, as well, but that turns out to be a bad thing when he learns what happened just before she almost married Doctor Octopus. To explain, May was Octopus’ housekeeper, and while working in that role, he learned that she had inherited some rare real estate, so he married her to gain access to the land. In any event, Aunt May had sex with Otto before their ceremony, and Peter had to experience it through Octopus’ memories!


During the late 1990s, Marvel and DC would often come up with ideas for gimmick numbering. For instance, after Zero Hour in 1994, every DC Comics title had a #0 issue. At the end of the decade, during DC One Million, every DC Comics title had a #1,000,000 issue, as well. Marvel’s counter to this was 1997’s “Flashback Month,” where every comic book was number #-1 and was set before the events of that comic’s first issue.

So the four Spider-Man titles all had to tell stories about Peter Parker when he was kid. In Spectacular Spider-Man #-1 (by J.M. DeMatteis, Luke Ross and Dan Green), Peter runs into Flash Thompson for the first time during a forced “go play outside for an hour” time. While Peter is away, Ben and May make sure to play, too.


In Amazing Spider-Man #597, during the “American Son” storyline that saw Norman Osborn (then in charge of S.H.I.E.L.D. following his heroics during Secret Invasion, which he promptly re-named H.A.M.M.E.R.) meet Spider-Man for the first time since Peter Parker’s secret identity was wiped from the memories of everyone in the world, May is planning her wedding to J. Jonah Jameson Sr.

However, what she and Jay do not know is that they are being stalked by drones sent by Doctor Octopus, May’s former fiancee, who was nearing the end of his life at the time and was none too pleased about his former fiancee marrying someone else! However, when their power cut out, it was the perfect time for Jameson to convince May to have the old people equivalent of a “quickie.”


In the early days of Marvel (back when it was still called Timely), the publisher put out a number of comic books in the style of Archie Comics: teen humor sort of titles. Stan Lee began working with an artist named Dan DeCarlo who would soon become the most popular teen humor comic book artist of all time. DeCarlo was eventually wooed over to Archie Comics, where he was so popular that they literally changed their style of art so that all of their artists would draw like DeCarlo.

They worked well enough together that the two men also tried to do a comic strip about a friendly mailman named Willie Lumpkin. It didn’t succeed, but when Stan Lee launched the Marvel Age of Comics, he didn’t forget Willie! He had him become the Fantastic Four’s mailman. Years later, after the death of her fiancee, Aunt May and Willie began dating.


While it is hard to picture her as a gangster’s moll, for a while there, that seemed like it might be the path that May Reilly was headed in her life. In Spectacular Spider-Man Annual #4 (by Bill Mantlo, Kerry Gammill and Sal Buscema), May began to receive letters from an old boyfriend. As it turned out, the old boyfriend was a gangster who had just been released from prison!

We see flashbacks to young May being wooed by young Johnny Jerome, who showers her with pricey gifts (that she makes a point to not accept). Meanwhile, steadfast Ben Parker keeps telling her that he’s up to no good. Since the story was set during Prohibition, it might be a stretch to say that May actually slept with the guy, but Boardwalk Empire certainly showed us that there was still a lot of loving going on in the Roaring 20s.


Up until recently, the most notable of May’s boyfriends after the death of Ben Parker was clearly Nathan Lubensky. May first met Nathan when they were both living in a nursing home. However, May then decided to convert her Forest Hills home into a boarding house. She invited Nathan to move into the house with her.

Nathan had a lot of problems, as he was a grumpy guy (he routinely would complain about how flaky May’s nephew, Peter, was) and he was also addicted to gambling. Tragically, he later developed a heart condition and died of a heart attack in a confrontation with the Vulture. May and Nathan were engaged when he died. It’s debatable if Nathan and May were able to get intimate, but since they were together for 10 years, we think it is pretty safe to say that they slept with each other.


Web of Spider-Man #3 (by J.M. DeMatteis and Val Semeiks) showed the honeymoon of May and Jay Jameson. The story opens with the maids at their hotel complaining about a pair of newlyweds who just would refuse to leave their room and let the maids come in to clean everything. While complaining, a naked Jay Jameson came to the door to apologize!

We learned that Jay and May had spent plenty of time breaking in their new room, but eventually they spent the rest of their honeymoon traveling around the world (which was a first for May, who rarely had ever left New York before this time). Tragically, Jay would later come down with an illness and pass away, making May a widow twice-over.

Who was your favorite Aunt May love interest (outside of Uncle Ben)? Let us know in the comments section!

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