Adorable hottie241396 over a year ago How deep do I have to go to actually finger myself n break my hymen so tht my first time will b less painful Loading... Guest over a year ago If you're looking to do that, finger urslef with something big so it breaks! Reply Loading... Adorable hottie241396 over a year ago I kno a dildo would wrk but. N how deep would I have to go to break my hymen Reply Loading...