A few comments on the early part of the second loss:

is a strange tenuki, large but not vital. I would prefer to keep pressing in the upper left corner. Presumably W intends to repeat the pattern he played on the other side, crawling along the second line, which would be great for B. When you tenuki, W could cause trouble by pushing and cutting immediately. Fortunately he prefered to crawl, so you got a good result anyway. (Tesuji practice: if W pushes through and cuts after the B14-C13 exchange, how does B capture the cutting stone?)

is normal, but seems like the wrong direction here -- the left side is narrower and has less potential than the bottom side. How about a pincer instead?

has something of the same feel -- neither B nor W can make much territory here. Maybe invade the 3-3 point directly? Or invade/attack around J3? Or develop the top moyo with K16? You could even play N11 to mess with W

is a wasted move. What can W do here? If you are at all worried and want to play locally, pressing at C7 is a fine way to punish the last low W move.

is aji-keshi. After W connnects, you have gained nothing. Without this exchange, there is at least a remote possibility of a later invasion at R3 (perhaps after a P4-P3 exchange), and even a simple descent to S6 becomes larger. Better to just play Q9 for safety and center strength. Similarly,

would be better at Q9. The center is much more important than this tiny side territory. Besides, you really want to harass that W stone at O10
W is far behind at this point, so

is a good attempt to create complications and get back into the game. You treated this threat too lightly and got into trouble, perhaps lulled into a feeling of superiority by W previous play.

at S9 or

at S8 look like safe connections.
After getting cut off,

seems very risky. It is not too late to give up three stones on a small scale. Enlarging the group like this risks a big loss if they die, and W is pretty strong locally. But hey, its just a game, so go for it if you like. Through

you got a fine result. Now K9 and O11 are miai, so you are out of trouble and have a good center position.

is an endgame move, much too small now. (Tesuji practice: if W connects at D1, how do you make eyes in the corner, without risking ko?) K9 and O11 are incomparably larger.
After W passed with :w102: and you cut at P10 (which could perhaps more safely just block at O11), you should win any fight in this region. Maybe someone else will comment on the fighting.