The latest email discovered in Bashar al-Assad's email account could throw up awkward questions for Syria's president from his British-born wife Asma.
Clad in skimpy white lingerie, the unnamed woman looks over her shoulder at the camera lens, her clothes discarded on the floor around her.
The photograph, discovered among thousands of emails from the personal accounts of the Syrian president and his wife, was sent to Mr Assad on December 11 last year by a woman who is not his wife.
The email contains no words and the identity of the woman is not known.
On the day Mr Assad received the photograph, his troops opened fire on a number of funeral processions in Syria, killing at least 12 people.
Mr Assad's personal account contains dozens of emails from a Yahoo account where the sender offers advice and passes on messages from people outside Syria. While the emails deal largely with affairs of state they have a relaxed and often joking tone.
Members of the Syrian opposition believe the woman may also have a second email address under a false name which she used to send Mr Assad more intimate messages. This account appears to have been set up on December 1 last year and as an apparent test an email was sent to Mr Assad's address saying simply "hi". Around 18 minutes later he replied "Hi and a half".
Over several weeks, the exchange becomes more flirtatious as they swapped romantic music by the popular Lebanese singer Fairuz and at one point he appears to send her a gift certificate.
On January 17, Mr Assad received an email from the second account with a single Arabic character meaning "I love you" and on January 25 another email contains only an x, the popular sign for a kiss.
While there is no direct evidence of a sexual relationship, the revelation could prove damaging for Mr Assad, who has sought to present a united front with his British-born wife, Asma al-Assad.
There is evidence the Assads began to cling closer as the fighting grew fiercer in Syria. On December 28, she wrote to him: "If we are strong together, we will overcome this together … I love you." He replied: "I'm not worry about this, and I have no doubt."
The Daily Telegraph tried to contact Mr Assad's correspondent using the email addresses found in Mr Assad's in-box but received no reply.
