Popular history is so well versed in the six wives of Henry VIII that they require little introduction. From the colourful bodice-ripper series The Tudors (2007–10) to the flickering candlelight of Wolf Hall (2015), we are reminded of the old mantra we learned at school: divorced, beheaded, died, divorced, beheaded, survived.


We might also be forgiven for thinking that the king was so busy keeping up with the women to whom he was legally united that he had little time for any others. However, Henry, with his “angelic” face, athletic build and red-gold hair, had an eye for the ladies, and in his early years, particularly, few were able to resist him.

Paradoxically, we can learn most about Henry’s mistresses through his wives. Anne Boleyn’s refusal to sleep with the king in the late 1520s was all the more successful because until this point he was accustomed to other women saying yes. Two of them in particular are known to us: Elizabeth Blount and Anne’s own sister, Mary, who were Henry’s lovers in the late 1510s and early 1520s after he started to question his marriage to Catherine of Aragon.

Bessie Blount

Elizabeth, or ‘Bessie’, is the first woman who is known, with any certainty, to have been Henry’s mistress. She was born at Kinlet in Shropshire in around 1500, making her just a teenager at the time she arrived at Henry’s court. Her family home fell under the jurisdiction of Catherine of Aragon’s first husband, Arthur, so it is not impossible that the young Catherine saw Bessie as a baby during her residence at Ludlow Castle in 1501–02. In fact, it is quite likely that Bessie’s parents capitalised on this early connection to place their daughter in the queen’s household.

Two court dances suggest the duration of Bessie’s tenure. Bessie is recorded as being one of eight in a masque performed to celebrate new year 1515, partnered by Henry himself. Then, in October 1518 she was paired with courtier Francis Bryan during a masque performed at Durham House in London. It was around this time that she fell pregnant with Henry’s son.

The pregnant Bessie disappeared from court, taken in secret by Henry’s leading minister, Thomas Wolsey, into the safety of the Essex countryside. There, at the Augustinian priory of St Laurence at Blackmore, also known as ‘Jericho’, Bessie gave birth to Henry Fitzroy, the king’s only acknowledged illegitimate child.

Henry stayed at two of his nearby properties that summer, Havering-atte-Bowe (aka Havering-atte-Bower) in August and Beaulieu in September, which would have allowed him to visit his newborn son, had he been minded to do so. What Catherine thought of the arrangement, or whether she was then aware of the situation, is not recorded. Wolsey stood in as godfather and the boy would later be given such significant titles as the Duke of Somerset and Richmond.

A marriage was arranged for Bessie to Gilbert Tailboys in 1522 (although some sources suggest 1519) and she retired from court for a time, bearing at least two more children (some sources suggest three while others say four) in the early 1520s. The uncertainty of the children’s birth dates has led to speculation that they were fathered by Henry, although by this time we know he had moved on to Mary Boleyn. Bessie remarried in the 1530s following Tailboys’ death and lived long enough to predecease Henry Fitzroy (who died in 1536), serving briefly as a lady-in-waiting to Anne of Cleves shortly before her own death in around 1540.

Mary Boleyn

Another masque marks the entry of the Boleyn sisters to the Tudor scene. In March 1522, Mary took the part of Kindness and Anne that of Perseverance in the Chateau Vert pageant at York Place. Henry was among the eight men led by the figure of ‘Ardent Desire’ to lay siege to the castle to rescue the women.

Anne had recently returned from the French court, which Mary had left several years before – rumours still persisted that Mary had been intimate with Francis I. In February 1520 Henry had attended Mary’s wedding to his gentleman of the privy chamber, William Carey, or at least sent a gift in addition to his offering of 8s 6d. The exact moment Mary became Henry’s mistress is unclear, but it is interesting that her marriage coincided with substantial gifts from Henry to her father and husband.

Much of Mary’s personality and education eludes us, as do the details and duration of her affair with Henry. Both she and Anne were already known to Henry as the daughters of Sir Thomas Boleyn who, along with Wolsey, had masterminded the magnificent Anglo-French meeting at the Field of Cloth of Gold. Yet it was Mary who caught Henry’s eye first and her two children, Catherine and Henry, born in 1524 and 1526 respectively, have sometimes been attributed to the king. As Mary was married, though, the children were legally considered to be those of her husband, who always treated them as such.

By the time of Henry Carey’s birth, though, the king’s attention had wandered to the enchanting, dark-eyed Anne Boleyn. We only know about his prior relationship with Mary because he required a dispensation to marry her sister, and had to admit to the affair. When questioned about his relations with the Boleyn girls and their mother, Henry replied, tellingly, “never with the mother”.

After Carey’s death from the sweating sickness, Mary remarried for love, returning briefly to court during her sister’s reign and admitting her secret. Mary was banished for her indiscretion and lived out her days in the Essex countryside.

Henry’s relations with Bessie and Mary are known to us almost by accident. If Henry Fitzroy had not lived, or had Henry not been forced to declare his past relationship with Mary, he might today be lauded by historians for his faithfulness to Catherine of Aragon.

These accidental survivals raise the question of what other secrets have remained concealed in Henry’s private life. Glimmers of possible affairs can be read into his associations with other women at his court. In 1534, during the king’s marriage to Anne Boleyn, the imperial ambassador Eustace Chapuys wrote that Henry had “renewed and increased the love which he formerly bore to another very handsome young lady of his court” and that Anne attempted to “dismiss the damsel from her service”.

Referred to as the ‘imperial lady’, the identity of this woman cannot be verified, but her presence seems to have put a strain upon Henry’s marriage, occasioning harsh words between husband and wife. ‘Imperial’ may not have referred to the woman’s origins but instead highlighted her sympathies to the cause of Rome and Henry’s rejected daughter, Mary.

Also from this era date the rumours of Henry’s involvement with Anne Boleyn’s cousin, Margaret (or ‘Madge’) Shelton, who may be the same person as a Mary Shelton, who until recently was assumed to be Anne’s sister. Chapuys’ letters from February 1535 make reference to a Mistress Shelton, and any affair she had with Henry would date to that year. Early in 1536 Madge was engaged to the ill-fated Henry Norris, who lost his head along with Anne Boleyn that May. Mistress Shelton was suggested as a potential wife for the widowed king two years later, but she married another man in 1546 and lived well into the reign of Elizabeth I.

Other women

Most of the other reputed mistresses who may have shared Henry’s bed date from the earlier part of his reign. During Catherine of Aragon’s first pregnancy, in 1509, Henry was embroiled with Anne Hastings, sister of the Duke of Buckingham and a newly married member of Catherine’s household. Henry’s close friend William Compton appears to have acted as a go-between, although Anne later went on to have an affair with Compton himself. Henry sent her away from court in retaliation.

There was also a ‘Madame the Bastard’ who kept Henry dancing into the small hours of the morning in 1513 at the court of Margaret of Savoy, and Étiennette de la Baume, whose plaintive letter to Henry asking for assistance reminded him of the promise he had made her when leaving France that year, and that he had called her his ‘page’.

There was the mysterious Jane Popincourt, who was refused entry to France by Louis XII, with the comment that she should be burned, plus a host of other ladies who received gifts from Henry at some point, or danced with him in a masque. Their connections with Henry are only fleeting and suggested, yet they might hint at secrets that the king had hidden more successfully than those of Bessie and Mary.

Given Henry’s desire for an heir, it is unsurprising that various stories survive that connect him with illegitimate paternity. The timing of these is interesting, with three in particular dating from the period when the king was wooing Anne Boleyn and, apparently, refraining from sex. If Henry did not sleep with Anne until 1532, Tudor medicine would have advised him not to remain completely celibate, as this would have been thought to imperil his health. Accordingly, Henry may have sought solace elsewhere.

Mary Berkeley had been married in 1526 to her uncle’s ward, Thomas Perrot, settling in Pembrokeshire. Perrot had been knighted by Henry that year and was a great hunter; it is thought that Mary was part of Catherine’s household, placing the pair at court during these years. Mary’s eldest son, John, was born in November 1528 and reputedly bore a great resemblance to the king. As a young man John was in the king’s favour – Henry once intervened to prevent him from being punished after he was drawn into a brawl. Later involved with piracy, debt, deception and scandal, John’s reputed parentage may have been a convenient way to escape retribution.

In the same way, another man claimed to be Henry’s son, with perhaps the same intentions. Thomas Stukeley was employed as a standard bearer in 1547, placing him in his late teens. The son of Jane Pollard, who was married in around 1520 to Sir Hugh Stukeley, Thomas is thought to have been conceived when Henry stayed at their Devon home of Affeton Castle. Thomas was something of a romantic figure, and poems and plays written about him after his death (for example, George Peele’s 1590s work The Battle of Alcazar) served to inflame such rumours.

Finally, the child arguably most likely to be related to Henry is an Ethelreda, or Audrey, Malte. If Henry had sought sexual satisfaction from someone other than Anne Boleyn, he is more likely to have turned to a woman of the lower classes, who were considered to be more ‘earthy’ and would not complicate lines of dynastic inheritance. Audrey’s mother was a Joan or Joanna Dingley, employed as a royal laundress, and the girl was raised by one of the cutters in the king’s wardrobe [who cut clothing patterns out of cloth]. John Malte “and Awdrye his base daughter” received a grant of £1,312 from the king while he lay on his deathbed, a huge sum for mere servants. Nothing more is known of Joanna or her daughter.

What this exploration of Henry’s love life makes tantalisingly clear is the fragile nature of the surviving sources. Henry’s desire for secrecy, and his ability to achieve it, are coupled with the problematic nature of rumour and second-hand accounts that date from this period. It may be that Chapuys exaggerated, or that Perrot made false claims; perhaps, in the case of Jane Popincourt, Louis XII was mistaken; or Anne Hastings’ sister was being over-protective.

What we know for certain is that our scant knowledge of Henry’s affairs with Bessie and Mary reached us accidentally and indirectly. Far from being a prude, Henry was a very private man and took measures to cover his tracks. When it comes to the question of who shared the king’s bed, it is likely that we will never know the full truth.

Amy Licence is a journalist and historian and the author of books including In Bed With the Tudors (Amberley Publishing, 2012), The Six Wives and Many Mistresses of Henry VIII, (Amberley Publishing, 2014) and Elizabeth of York: The Forgotten Tudor Queen (Amberley Publishing, 2013). You can follow Amy on Twitter @PrufrocksPeach or visit her website amylicence.weebly.com


This article was first published by History Extra in February 2016.