You can clip the image context to the path of an image
// Start the image context
UIGraphicsBeginImageContextWithOptions(pinImage.size, NO, 0.0);
UIImage *resultImage = nil;
// Get the graphics context
CGContextRef context = UIGraphicsGetCurrentContext();
// Draw the first image
[pinImage drawInRect:CGRectMake(0, 0, pinImage.size.width, pinImage.size.height)];
// Get the frame of the second image
CGRect rect = CGRectMake(20.0, 10.0, user.size.width/2, user.size.height/2)
// Add the path of an ellipse to the context
// If the rect is a square the shape will be a circle
CGContextAddEllipseInRect(context, rect);
// Clip the context to that path
CGContextClip(context);
// Do the second image which will be clipped to that circle
[user drawInRect:rect];
// Get the result
UIImage *resultImage = UIGraphicsGetImageFromCurrentImageContext();
// End the image context
UIGraphicsEndImageContext();