I think using getter/setter is simpler, but here's an example of what I did to make it work :
(It works fine for number and string, but not for date (error with @Temporal annotation)).
import com.cestpasdur.helpers.PredicateHelper;
import com.google.common.annotations.VisibleForTesting;
import com.google.common.base.Optional;
import org.apache.commons.lang.ObjectUtils;
import org.apache.commons.lang.StringUtils;
import org.hibernate.HibernateException;
import org.hibernate.usertype.UserType;
import org.joda.time.DateTime;
import java.io.Serializable;
import java.sql.*;
public class OptionUserType implements UserType {
@Override
public int[] sqlTypes() {
    return new int[]{
            Types.NULL
    };
}
@Override
public Class returnedClass() {
    return Optional.class;
}
@Override
public boolean equals(Object o, Object o2) throws HibernateException {
    return ObjectUtils.equals(o, o2);
}
@Override
public int hashCode(Object o) throws HibernateException {
    assert (o != null);
    return o.hashCode();
}
@Override
public Optional<? extends Object> nullSafeGet(ResultSet rs, String[] names, Object owner) throws HibernateException, SQLException {
    return Optional.fromNullable(rs.getObject(names[0]));
}
@VisibleForTesting
void handleDate(PreparedStatement st, Date value, int index) throws SQLException {
    st.setDate(index, value);
}
@VisibleForTesting
void handleNumber(PreparedStatement st, String stringValue, int index) throws SQLException {
    Double doubleValue = Double.valueOf(stringValue);
    st.setDouble(index, doubleValue);
}
@Override
public void nullSafeSet(PreparedStatement st, Object value, int index) throws SQLException {
    if (value != null) {
        if (value instanceof Optional) {
            Optional optionalValue = (Optional) value;
            if (optionalValue.isPresent()) {
                String stringValue = String.valueOf(optionalValue.get());
                if (StringUtils.isNotBlank(stringValue)) {
                    if (PredicateHelper.IS_DATE_PREDICATE.apply(stringValue)) {
                        handleDate(st, new Date(DateTime.parse(stringValue).getMillis()), index);
                    } else if (StringUtils.isNumeric(stringValue)) {
                        handleNumber(st, stringValue, index);
                    } else {
                        st.setString(index, optionalValue.get().toString());
                    }
                } else {
                    st.setString(index, null);
                }
            } else {
                System.out.println("else Some");
            }
        } else {
            //TODO replace with Preconditions guava
            throw new IllegalArgumentException(value + " is not implemented");
        }
    } else {
        st.setString(index, null);
    }
}
@Override
public Object deepCopy(Object o) throws HibernateException {
    return o;
}
@Override
public boolean isMutable() {
    return false;
}
@Override
public Serializable disassemble(Object o) throws HibernateException {
    return (Serializable) o;
}
@Override
public Object assemble(Serializable serializable, Object o) throws HibernateException {
    return serializable;
}
@Override
public Object replace(Object original, Object target, Object owner) throws HibernateException {
    return original;
}
}