Jizz

The saddest picture I've ever seen (NSFW)

pics

The saddest picture you'll see today

pics

[Spoilers] The best (and saddest) written act of ME3

masseffect

One of the saddest moments in comic book history. [Major Spoilers]

comicbooks

So I've watched the first 114 episodes of Naruto in the last week, this was the saddest moment for me so far (please don't spoil anything for me :D)

Naruto

This is quite possibly the saddest animal I've ever seen.

pics

One of the saddest Moments in One Piece

OnePiece

The saddest death of Batman Death of the Family

batman

A mouse pad for the saddest and loneliest of souls [xpost /r/AmazonPrimeDeals]

nsfw_funny, pics, funny

[Spoilers] The Saddest Tears in the Game

Bioshock

[50/50] The best gif EVER! | The saddest gif ever [Possibly NSFL due to high sadness levels] ):

FiftyFifty

One of the saddest moments in video games for me (spoilers)

gaming

Re: Saddest moment in the entire Clone Wars series.

StarWars

Probably the saddest combination I've seen so far.

cardsagainsthumanity

One of the saddest & strongest pictures I've seen (nsfw)

pics

[Spoilers]Saddest scene of the season

thewalkingdead

The saddest face in My Little Pony

mylittlepony

Some of the saddest seconds from the last episode.

HarimeNui

[NSFW] The saddest moment from episode 24

KillLaKill

Turned into one of the saddest conversations I've ever had.

lolgrindr

On Draw Something I attempted to draw a lapdance. Now it looks like the saddest stripper.

nsfw

(F) Tonight I can write the saddest lines.

gonewild

Layman, how could you, you monster!? This is perhaps the saddest issue of Chew to date... (SPOILERS) (Chew #45)

comicbooks

[SPOILER] So many sad deaths in Injustice, but we've all ignored one of the saddest deaths, found at the very beginning.

DCcomics

[TW: sad lurkpot, body hair] in honor of saddest of svunts, recreate the classics.

fitnesscirclejerk

Possibly one of the saddest profiles I've ever seen. Just go eat something dude

lolgrindr

[Season 2][Spoilers] Saddest part of the finale

TrueDetective

[Rick and Morty Comic #4 SPOILERS] This issue has some of the saddest feels I've encountered in R&M

rickandmorty

Sharing because lonely orgasms are the saddest orgasms (PM me!)

ladybonersgw

[wife][daughter] The saddest part was that you came while you watched.

cuckoldcaptions

The saddest room in the game [minor spoiler]

fo4

Is this not the saddest image ever

survivor

One of the saddest endings to a comic I have ever read (Identity Crisis #7) [SPOILERS]

comicbooks

This has to be one of the images saddest I've seen of Epcot

WaltDisneyWorld

This will probably be the saddest guy when characters are re-rolled today

playrust

Top 10 Saddest Anime Deaths

FNaFShitposts

[Quest Spoilers] This was by far the saddest thing in Legion...

wow

Fulfilling another fan request. Close up of her asshole and pussy. The saddest part of my life is that she wont let me fuck that pretty little asshole of hers. And yes, thats my spit next to her holes... ;)

wifesharing, WouldYouFuckMyWife

One of the Saddest Characters in Gaming

gaming

Of all sad words of tongue or pen, the saddest are these: Zwiebelsaft was right again.

gaybroscirclejerk

[mom] The saddest part is that right after that awful exchange you jerked off several times in a row while re-reading it, and every time you think about it you have to jerk off again.

bangmybully, u_son1324mom

[Warning: Dying Fish] Quite possibly the saddest thing I've ever seen

Aquariums

Iris von Everec gives the saddest blowjob (bomyman) [witcher 3]

3DPorncraft

My kitten tiara broke yesterday and I'm the saddest ball of fluff ever!

adorableporn

Still probably the saddest picture ever.

worldpolitics

The saddest day of my life

UnfilteredCaptions, xxxcaptions

Kimmi was the saddest Character in Christory

ChrisChanSonichu