One sided! She deserves a good fucking.. Let her have some big loads.. she will love having your sperm leaking out of her pussy throughout the day..
my first non virgin pussy was a 33 year old waitress when I was 17. she wasn't fat but she was thick. I wasn't fully grown as I was about 7'' in length and close to 5'' girth (grew since then) and she was really tight our first time going in but man she drenched my cock and she most times had me pull out and cum in her ass. the tightest pussy (non virgin) I ever had was this 5'8'' 120 lb (at most) fit as fuck ginger. the loosest was this barely 5' and probably 90 lb cute Korean girl. I also had a really loose girl in college probably 5'10'' and 300 lbs but had another girl who was similar in size and she was so tight I had to use a lot of lube just to get in. basically I have had had it both ways.
Some bigger women it's just impossible I'm a little above average size and this one bigger lady I couldn't keep it in save my life she is fun to play with anyways