Henry probably first started suffering from periodic bouts of impotency during his marriage to Anne Boleyn.  Of course such things were always the womans fault then and not the sort of thing readily admitted to.  It's interesting to see that Henry didn't have too many mistresses as he got older probably for the very reason you mention Hannah.  He always preferred to marry them anyway! 

A great book on this subject is, The Mistresses of Henry VIII, by Kelly Hart.  She writes of all the mistresses and the wives.  In her chronology she states;

 “1537: Queen Jane died giving birth to the future Edward VI.  There were no further rumors of Henry having extramarital affairs, except those which led to marriage.  He was 46.”

“1538: Henry began looking for a fourth wife.  Mary Skipworth and Mary Shelton (not Madge) were considered to be contenders, as well as several princesses.”

“1540: Henry married Anne of Cleves, but was unwilling to consumate the union.  After six months, the marriage was annulled and he wed Anne's teenage maid of honor, Catherine Howard.”  Personally I think he was impotent during this period.

“1542: Catherine Howard was executed for adultery.  Henry was rumored to be considering Elizabeth Brooke or Anne Bassett as her replacement.”

Others mentioned after he married Katheryn Parr were Katherine Wiloughby, Brandon's second wife; and later there was a  failed attempt by the Howard's to make another one of their own a mistress.  This was lady Mary Howard.  Those involved in this little scheme were sentenced to be executed.

Katherine Wiloughby was married to Charles Brandon, the Duke of Suffolk.  Charles was Henry's best friend.  Charles married Katherine shortly after Henry's sister, and Charles' first wife Mary, died. Charles died in 1544 (dont quote me on that date.  It was around then)  Katherine was Catherine Parr's best friend.  When Catherine Parr died after giving birth to Thomas Seymour's child, Katherine Wiloughby took the baby into her home.  The baby was a girl named Mary.  She was a young child when she died.

I never heard the story about the girl and her Father. 

I agree, Bella44: Katherine Wiloughby is very interesting. I’ll admit, though, that I have a bit of sown-in prejudice for her because I love Mary Tudor aka Katherine’s husband Charles Brandon’s first wife.

Seems that Charles Brandon was just as busy as Henry was when it came to women!!

Here's what I think:  I think by they time Henry and Anne Boleyn got together, Henry was a diabetic because of his ballooning waistline (he was certainly not the spring chicken that The Tudors would have us all believe).  This would explain the impotency and the trouble with his leg.  I can't claim this theory as my own:  I'm pretty sure I read it somewhere, but it certainly makes sense.

Henry certainly had a delicate ego, but I also think that one of the reasons why he insisted on marrying woman after woman was because he was, for the most part, in the midst of a mid-life crisis.  He was getting older and simply couldn't let go of the virulent, active King he had been when he was married to KoA (and I think that KoA's aging was one of his many, many reasons for wanting to divorce her–she reminded him that he, too, was getting older).  All that to point out, that, because of his mid-life crisis, he was probably going around still sleeping with women in the court.  Maybe not at many as, say, the French king, but I think he needed to stroke his ego and that was one way of doing it.

As for keeping his impotency quiet…if you were in his court and you saw how ruthless he was becoming, would you say anything about his ability to perform (or lack thereof)?  Not I.  I would keep my mouth shut if just to keep my head.  I think his impotency was probably well-known in court, but it was not frequently spoken of.  Think about it:  Anne and George we know spoke about it.  And if we can clearly see that Anne of Cleves was attractive, then Henry's “refusal” to consummate the marriage would probably have risen some eyebrows.  For all of Henry's blustering that it was Anne's fault, I'm willing to bet that there were many shared, knowing looks about court.  If Henry was suffering from bouts of impotency with AB, then I'm also willing to bet that part of the reason it took JS so long to fall pregnant was also due in part to impotency.  Just because they were sleeping together doesn't mean they were “sleeping” together.  

And there was very nearly another one, Elizabeth Grey. On Charles Brandon's page in The Peerage, it rather bluntly describes the situation thusly:

On 3 Dec. [1512], he received a grant of the wardship of Elizabeth, daughter and sole heiress of John Grey, viscount Lisle, of which he very soon took advantage in a rather questionable way, by making a contract of marriage with her; and next year, on 15 May, he was created Viscount Lisle, with succession to the heirs male of himself and Elizabeth Grey, viscountess Lisle, his wife, as she is called in the patent. But in point of fact she was not his wife, for when she came of age she refused to marry him, and the patent was cancelled.

Elizabeth Grey died in 1516, unmarried and childless. Wow!

http://www.thepeerage.com/e413.htm

Henry strikes me as a bit of an anomaly amongst kings of that period. Besides Elizabeth Blount, Mary Boleyn and a few short lived flings he never really had what one would consider to be a 'mistress', at least not in the sense that other kings at the time did. That is not to say that he did not have one-night stands, or (as I mentioned before) other short lived flings. Compare him to someone like Francis and Henry seems positively chaste!

He tried to make Anne his official mistress, only to be sharply rebuked and after that he never really seemed to try and take up an official mistress again, instead preferring to marry the objects of his affection (ie Jane Seymour and Katherine Howard). I would agree that this probably has something to do with the onset of old age an impotence, or maybe Henry was just a romantic at heart?

I know this post is suppose to discuss Henry's mistresses, but this questions connects. In anyone's readings about Henry's illegitimate children come across the name Thomas Stucley.

I am currently reading The Pirate Queen: Queen Elizabeth I, Her Pirate Adventurers, and The Dawn of Empire by Susan Ronald. She mentiones Thomas Stucley, a known pirate who was charged with piracy in 1558. There was a rumor that he was Henry VIII 'base-born son,” however the author does not elaborate any futher.

Sharon said:

In the book, The Other Tudors, Henry VIII's Mistresses and Bastards, Phillipa Jones names one of the women who was a mistress, Jane Pollard.  Henry and Jane supposedly had a son by the name of Thomas Stukeley.  Spelled many different ways: Stucley,Stukely Stukeley to name a few.  He was quite the adventurer. He died at the battle of Alacer Quibar when a cannonball cut off his legs.  1578.

Thanks, Sharon. I think this is the same guy. I don't have Philippa Jones's book, and I could not find any information about Thomas in my other Tudor books.

How interesting!! I've never heard of Stucley before…fascinating…