@Lalanichols,
He sounds like a fantastic guy, and you are one billionaire girl, making love nearly every day!!! I'm soooo jealous.
If this were me, I wouldn't have a problem if - you tell you feel insecure and he quells your insecurities by showing you all these messages - both ways. If he starts being coy or demanding privacy then I'd be more insecure. If he hasn't got a problem with that then you haven't got a problem! The secret is communication, openness and really caring for each other.
With regards to the weight, if you felt even more gorgeous and sexy that would go a long way to alleviating some of your self esteem which is probably at the root of this issue.
Good luck girl x