Jizz

Furified Cortana [F]

yiff

Ever made a girl a promise you knew you couldn't keep? For everyone who misses Cortana, even a little

gaming

Daaaaamnn Cortana

halo

Halo 4's Cortana

doppelbangher

Based on the trend, this is Cortana for Halo 5 (NSFW) [FIXED]

gaming

Sexy Cortana

HaloPorn

A Slightly More Risqué Cortana (Cosplay)

halo

A Picture of Cortana From Halo that I made in Illustrator (Possibly NSFW)

gaming

Feelin some Cortana

gonewild, gonewildcolor

For all the Cortana Lovers

halo

Halo 4's Cortana (mildly nsfw) [1361x845]

GamerPorn

Anyone want to try and draw me as Cortana?

drawme

Exhibitionist Cortana in the woods of requiem in front of soldiers

hentai

Badass Cortana cosplay/bodypaint (Kinda NSFW)

gaming

Pick a Cortana

NSFWscifi

How 'Chief deals with life without Cortana.

rule34

Unfinished Cortana Art

rule34

Testing out Cortana on wp8.1 when this happened

nsfw

In honor of the Master Chief Collection, I drew Cortana.

rule34

[NSFW] No Cortana, that is not what I meant.

pics, funny

I told Cortana to "remind me to make my ID Card"...

windowsphone

Master Chief fucks Cortana - by Ozzy

porntana

Adding to the list of odd things Cortana's been doing lately

crowdgroped

Why is Cortana returning results with 'Nigger' in them when I search the word 'Monkey'?

windowsphone

I think Cortana misinterpreted my search. [NSFW]?

windowsphone

Hey Cortana!

funny

So I asked Cortana about Master Chief, I wasn't expecting THIS. NSFW spoilers

gaming, halo

I asked cortana if she thought I was pretty. Not disappointed :3

pcmasterrace

Said to Cortana: "P---, Sh--, Fu--." She gave me this.

funny

[NSFW] Cortana has seen some things from me

windowsphone

Halo 4 - Cortana’s happy ending

Tarakanovich

Liara and Ashley with Cortana

asseffect

[Halo 5 Spoilers!] The Evolution of Cortana

gaming

[Halo] Meg Turney as Cortana (found)

cosplay_nsfwshoops

Master Chief cumming on Cortana's ass - by noname55

porntana

The lovely Ms. Cortana and her giant penis

CortanaBlue

Jannet Vinogradova as Cortana (Halo)

gaming, halo, NSFW_Faves

Kinzie and Cortana(sleepy-dino)

SaintsRowPorn, WesternHentai, HalloNSFW

Evolution of Cortana's posterior

gaming

Rampant Cortana

spnati

Geez Cortana, I'm not that much of a deviant

assholedesign

F25 Add me for free nudes & sexting Snapchat: cortana.blue93

snapchatgw

NSFW Cortana Fanart, ink and colored pencil

NSFWart, hentai, rule34

Laika aka Cortanas underboob

underboob, TheUnderboob

Halo Cortana i did (@HentaiFungus on Twitter)

nsfw

Halo - Cortana x Flood Carrier

NSFWart, rule34

[ASFR] Cortana by Didi-Esmeralda

Inanimate_TFs

Headless Cortana 1

NaturalBodyMagic

Headless Cortana 2

NaturalBodyMagic