Loki and strange punishments...

Loki discussing rescuing Lorelei and Sigurd.   Because, yes, he is an expert at escaping crazy / strange punishments. 

  Strange punishments (including self-made ones) Loki has suffered in Marvel canon:

  Note: Some of these the punishment was repeated in other Marvel incarnations and multiple sources are listed for those particular instances.  

  1.  Loki's mouth being sewn shut. (Trials of Loki / Norse mythology.) 2.  Being chained under a snake dripping venom into his eyes. (Trials of Loki / Norse mythology). 3.  Being chained under a snake dripping venom over his face (slightly different). (Avengers: Earth's Mightiest heroes animated series / Norse Mythology). 4.  Being manacled to Sigyn (His wife). (Classic comics). 5.  Being turned into a tree until someone weeps for him. (Mythology / classic) 6.  Being banished to Hel. (Hulk vs. Thor / Hulk and the Agents of SMASH)  7.  Being banished to the Greek underworld. (Classic comics) 8.  Being banished to the isle of silence (nothing can speak there) (Avengers: Earth's mightiest Heroes and classic comics). 9.  Temporarily being manacled and muzzled to prevent the use of his powers. (Marvel cinematic universe). 10.  Life sentence in the dungeon. (Marvel cinematic universe) 11.  Being left in another dimension. (Avengers Assemble and Ultimate Spider-Man animated series. 12. Ten thousand years in the Asgard prison / Dungeon (Hulk and the agents of S.M.A.S.H) 13.  Twenty thousand years in the Asgard prison / Dungeon (Hulk and the agents of S.M.A.S.H. 14.   Death by Zombies (Marvel Zombies Destroy!) 15.   Death by void explosion (Siege) 16.   Beaten with Thor's hammer. (Thor & Loki: Blood brothers). 17.  Essence being trapping in a Magpie (Journey into Mystery). 18.  Being resurrected as a twelve-year-old Boy with no memories of his past yet being held accountable for it. (Thor / Journey into Mystery / Young Avengers). 19.   Haunted by the ghost of his innocent incarnation once he regains all of his past life's memories. 20.   An indefinite Sentence in The Raft (or on a freakin' pog) (Avenges: Disc Wars anime). 21.   Held indefinitely by SHIELD on a helicarrier. (Avengers movie / Marvel 001 point 1 2014, Loki Agent of Asgard issue 1). 22.  Held in an elaborate restraint chair. (Marvel Now 001 Point 1 2014). 23.  Held in wrist and ankle restraints bolted to a cell wall (Loki Agent of Asgard Issue 1). 24.   Held in a cell with no door in the bowels of Asgardia's dungeons. (Loki Agent of Asgard 5). (Note this is in regard to potential Future Loki AKA King Loki). 25.  Being turned into a baby via magical norn stone.  (Ultimate Spider-Man: Itsy Bitsy Spider-Man). 26.  Being beaten up by Hulk.   (Hulk vs. Thor / Avengers (Marvel cinematic universe), Loki Agent of Asgard issue 1 / Ultimate Spider-Man: Web Warrior's Avenging Spider-Man Part 2.)     27.  Being made unable to lie (Loki Agent of Asgard issue 9). 28.  Being sealed in a box outside of time (Loki Agent of Asgard issue 6). 29.  Actually feeling guilt and remorse. (Thor / Journey into mystery / Young Avengers / Loki Agent of Asgard / Marvel Heroes)

30.  Being forced to help save the world. (Siege and Marvel Heroes).

31.  His children being slain. (Mythology).

32.  Having to give birth to a horse.  (Mythology / classic comics / subtlety referenced in the Thor movie.)

33.  Being "Trapped" inside Sif's body.  (Marvel comics).

34.  Being beaten up by Thor. (Lots of sources...)

35.  Having to deal with Deadpool... (multiple comics and Marvel Heroes.)