French, 18th century, After the Antique, Bust of Antinous, white marble (est. £100,000- 150,000) #SothebysErotic as a god.
This rare and superbly carved marble bust depicts Antinous, the male lover of the Roman Emperor Hadrian, who has been celebrated throughout history for his good looks, and has subsequently become a symbol of same sex love. It combines the allure of the biographical portrait with an idealised classical representation of male beauty. In Rome, there was no clear distinction between heterosexual and homosexual love, and the relationship between Antinous and Hadrian – between a younger and an older man – would not have been unusual in Roman society. Antinous was in Hadrian’s retinue by A.D. 130, but their story took a tragic turn when Antinous mysteriously drowned in the Nile at the tender age of 19, plunging the Emperor into prolonged mourning for his favourite. The effect of Antinous’ death on Hadrian was profound – he established a city in Egypt, Antinoopolis, in the Grecian youth’s honour, and even encouraged his veneration Richard Avedon, Nastassja Kinski and the Serpent, Los Angeles, California, 1981, oversized silver print (est. £50,000-70,000) Exuding a timeless eroticism, this iconic image was taken during a two hour shoot when Kinski was at the height of her career and Avedon was already a world renowned fashion photographer.

Intertwined with a boa constrictor, grappling with temptation, seduction and power, Kinski is clearly referencing deeply rooted concepts in classical art and mythology, most notoriously the story of Adam and Eve and the serpent that tricked Eve to take an apple from the Tree of Knowledge. Commissioned for Vogue, the only fashion emblem present is the Patricia von Musulin bracelet which the editor of Vogue at the time noted she regretted including within the photograph.

Tracey Emin, How I Think I Feel, acrylic on canvas, 2007 (est. £50,000-70,000)
Powerfully intimate and revealing, How I Think I Feel was one of a small selection of canvases chosen to represent Great Britain at the 52nd Venice Biennale in 2007. Not only a striking and sensuous image, it is also a deeply personal and moving insight into Emin’s own psyche. The artist brilliantly employs her draughtsmanship to great effect; urgent brushstrokes delineate a female body to create an image which turns viewer into voyeur. Playboy Entertainment for Men Issue #1, [December 1953] (est. £3,000-5,000)

The most iconic and recognisable first issue of any magazine ever, the inaugural issue of Playboy was published by Hugh Hefner in December 1953. The first issue is not dated, as Hefner was unsure there would be second. 50,000 copies immediately sold (for the price of 50¢ each) and Playboy was born. Attributed to Sir Peter Lely and Studio, Portrait of Elizabeth Trentham, Viscountess Cullen, as Venus, oil on canvas (est. £80,000-120,000) This alluringly provocative painting is exceptionally rare in British art of the 17th century – possibly the only fully nude portrait of a noblewoman painted in England in that century. Though its existence has been known, it is only sparsely documented in the literature and is not thought to have been seen in public since its original creation. Neither simply an allegorical representation of Venus nor an anonymous nude, the picture astonishes for the fact that it is a portrait. ‘The beautiful Lady Cullen’, Elizabeth Trentham, Viscountess Cullen (1640-1713) was Lady of the Bedchamber to Queen Catherine and a celebrated Restoration Court beauty of equivocal reputation – notorious for her physical charm, her extravagance and her immorality. The Restoration Court of King Charles II, and his brother the Duke of York (later James II), was notoriously licentious, though even by the standards of Restoration England, the painting is exceptional in its overt eroticism. Yves Klein, Venus Bleue (S41), blue pigment and synthetic resin on plaster, conceived in 1962 and executed posthumously in 1982 (est. £50,000-70,000) ‘Blue...is beyond dimensions, whereas the other colours are not’ Known for his audacious experiments and provocative techniques, Yves Klein produced a series of beautifully poetic and intense works in his trademark ultramarine pigment, International Klein Blue.

Frederic, Lord Leighton, The Sluggard, bronze (est. £18,000-25,000)

The Sluggard is one of the iconic masterpieces of 19th-century British sculpture, its languid pose capturing the essence of male beauty and the masculine ideal. The subject was inspired when Leighton’s muscular male model, Giuseppe Valone, began slowly stretching after a long sitting. He rapidly captured the pose in clay, which he exhibited at the Royal Academy in 1886. Originally titled ‘Athlete awakening from sleeping’, The Sluggard was conceived as the pendant to the artist’s earlier masterpiece, ‘An Athlete struggling with a Python’, exhibited at the RA in 1877.