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A Sittingbourne school has issued a warning to parents after two female pupils were approached by a suspicious man.
Teachers at The Westlands urged pupils to stop using a shortcut to get to school after the two separate incidents.
They also warned of the dangers of youngsters befriending people they do not know on social networking sites - after recent cases of children making friends with strangers online who have then gone on to ask for inappropriate pictures or to arrange meetings.
In a letter to parents, the school asked parents to talk to children about keeping safe when walking around the town after two female pupils were approached by a man while on their own.
The first happened in an alleyway behind Gadby Road on Friday, February 14 at 3.40pm.
The other was in the Woolett Road area at 8.15am last Tuesday. Both incidents have been reported to Kent police.
Assistant head teacher Maureen Fazakerley, who is in charge of safeguarding, said in the letter: "We would advise that pupils either stop using this short cut or at least walk with someone else rather than on their own.
"The school runs a regular programme of E Safety but despite our best efforts, pupils still take chances particularly when meeting people or sending pictures.
"We have had recent issues whereby via the social media, pupils have made friends with strangers who have gone on to ask for inappropriate pictures or to arrange meetings..." - assistant head teacher Maureen Fazakerley
"Please monitor your child's access to social media either by mobile phone, laptop, iPad, gaming box or any other device you know they have access to. Pupils make friends with people they have never met in person, but think because it is on line, that they are safe.
"We have had recent issues whereby via the social media, pupils have made friends with strangers who have gone on to ask for inappropriate pictures or to arrange meetings.
"These strangers are very convincing and teenagers are not always fully appreciative of the dangers.
"Pictures once sent cannot be removed and the person receiving them can do what they like with them. Teenagers are also susceptible to sending pictures, sometimes inappropriate, to each other.
"Please remind your son/daughter to not send inappropriate pictures either to friends or strangers. Remind them that once sent or posted, it remains out there forever. Pupils who pass on inappropriate images of other pupils are breaking the law."
Head of school Simon Cox said: "When incidents occur which threaten childrens' safety out in the community we often feel obliged to inform and educate parents about safeguarding issues. Hence the letter."