Jizz

Tron/Ghost in the Shell/Cortana inspired body drawing, [F]ulling a request idea ;) (a lot more inside)

gonewild

But Cortana is a hologram... (Halo)

DirtyGaming

A Cortana drawing I came across on twitter [NSFW]

gaming

Based on the trend, Cortana for Halo 5? (NSFW)

gaming, rule34

Halo 4: Cortana

rule34

My personal favorite Cortana pic

rule34

Fantastic Cortana Cosplay

gaming

Halo - Master Chief & Cortana.

rule34

Using Cortana's 3 holes

rule34

So that's what Cortana was doing when Chief was in a Cryonic Sleep

rule34

[Halo] Cortana

nsfwcosplay

My favorite Cortana Wallpaper

rule34

Anime Version Of Cortana [Halo]

rule34

I heard you liked Cortana

rule34

Cortana, you vixen.

ass

EDI & Cortana share two dildos

asseffect

[JigglyGirls] Halo - Cortana

rule34

Miranda Lawson and Cortana

rule34feet

Chief and Cortana [GIF]

rule34, rule34feet

My Cortana cosplay. I do it frequently at cons, maybe you'll see me! (The Chief is my ex, we built the armor prototype with pepakura.)

halo

Halo 4: Cortana's happy ending by Tarakanovich

rule34, WesternHentai, nerdyporn

"Hi Chief" by vempire (Cortana from Halo)

rule34

Cortana in missionary

HaloPorn, porntana

[SELF] Cortana cosplay @ Fan Expo Toronto

cosplay, arrow, gaming

Halo 4: Cortana's happy ending by Tarakanovich

WesternHentai

If she came like that, I'd upgrade to Windows 10 in no time! [Cortana] [Halo]

rule34, rubin34, HalloNSFW

Cortana NSFW.

pics

[NSFW] [NSFL] Cortana gets her holo-holes DESTROYED by the Chief (MUST SEE)

HaloCirclejerk

To check out the new voice commands I told Cortana to give me a blowjob. The Xbox Two is gonna' be wild.

xboxone

Cortana more realistic figure

fit2phat

Jannet Vinogradova as Cortana

gaming, halo

A.I. Cortana by KateStarling (female)

consentacles

Jannet Vinogradova as Cortana (Halo)

cosplaygirls

Camgirl Cortana Blue

JustOneBoob

Smol Cortana, Big Cocks (NeroXLIV)[Halo]

rule34, porntana, WesternHentai, HalloNSFW, Minigirls

Jenna, Cortana, Willow.

JennaJade, c0rtanablue, TrueFMK

Willow, Cortana, Jenna.

c0rtanablue, JennaJade

Thicc Cortana (Jinu) [Halo]

rule34, porntana, MOACdump, Jinu, HalloNSFW

Dominatrix Cortana (TheMaestroNoob) [Halo]

rule34, ThePlayfulSuccubus, porntana, HemdomBlog, CedehsHentai, MechanicalSluts, u_booberrysx, hentaifemdom, Hot34

WaifuBus - Cortana (Bokuman) [Halo]

MechanicalSluts, u_definitelynotaiko, WaifusOnCouch

Thicc & Curvy Cortana... (Ange1Witch) [Halo Series]

rule34, HalloNSFW

Master Chief relieves stress with Cortana before battle (B-Intend) [Halo]

rule34, AllHentai, MechanicalSluts, HalloNSFW

Cortana Fan art... Sexualised yes...sexy yes

mendrawingwomen

gay cock gay ruined cortana with their sjw agenda

HaloCirclejerk

[SciFi/TGTF/ASFR/Suiting] Hey, Cortana! by Kannel

Inanimate_TFs

Infinite possibilities - Cortana (Reiq) [Halo]

rule34, MonsterMen, HentaiBeast, porntana

Date night with Cortana (hotpinkevilbunny) [Halo]

rule34, Halo_NSFW, porntana

[ASFR] Cortana by AyyaSAP

Inanimate_TFs, rule34

Samus and Cortana Having Fun Before Bounty Hunting (dc139)

Metroid34

[F Human AI -> Rabbit Anthro, Post-TF, Cortana/Halo series] Bunny Cortana by Curse-M

transformation

Hypnotized Cortana (plsgts) [Halo]

HypnoHentai, rule34, porntana

Cortana (Halo)

Footjobhentai, rule34feet

Sex Drive Activated (Cortana / Halo) by Lordarkdeus - Accepting Requests

scifigirls, hentai, cyberporn

Cortana Blue

ibradome, needysluts, Slut, Slutsofonlyfans, ThePlUgGuY, LadyLebraa