SHEMALE • SECRETARY 259 videos

Popular Latest Top rated

23:21 92%

Brandy Scott - Secretary Fuck

13 years ago

AShemaleTube

blonde, vintage, secretary, shemale
25:21 92%

Asian secretary ladyboy is doing a great job

5 years ago

xHamster

teen (18+), asian, teen anal (18+), 18, secretary, domination
41:49 91%

Yasmin Lee In Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

2 years ago

ShemaleZ

asian, BDSM, big cock, secretary, cum in mouth, domination, boss
34:19 90%

Crossdresser japanese secretary fucking intensely

2 years ago

XXXDan

amateur, couple, japanese, lingerie, crossdresser, secretary, hardcore
27:50 90%

Lady-man hammered By Boss And Secretary

6 years ago

ShemaleZ

secretary, boss, shemale
18:06 90%

Ebony secretary must learn how to serve a big dick of her futanari MILF boss

3 years ago

AnySex

MILF, secretary, futanari, boss, ebony, black
28:19 89%

Jane Marie - Fabulous Sex Scene Shemale Big Tits Best Ever Seen

3 years ago

TXXX

stockings, big ass, big tits, secretary, shemale, ass
34:28 89%

Blonde Dicke Titten Sekretarin Shemale Anal Und Sperma Abgespritzt 35 Min

3 years ago

ShemaleZ

anal, fetish, MILF, big tits, 18, sperm, secretary
25:28 89%

Blonde big ass shemale get anal fuck

3 years ago

xHamster

german, latina, blonde, secretary
24:29 88%

Shemale Secretary Bia Bastos in Hot Fucking Dick Flapping Action

4 years ago

TrannyOne

nipples, glasses, secretary, shemale
16:49 88%

Your Secretary

1 year ago

AShemaleTube

mature, redhead, crossdresser, masturbation, secretary, cum in mouth
30:04 88%

Sexy boss fucks with secretary

14 years ago

AShemaleTube

secretary, boss
34:58 88%

Blonde big tits secretary shemale anal and cumshot

3 years ago

xHamster

anal, teen anal (18+), big tits, secretary, bareback
23:35 85%

Horny Ebony Milf Gets Fucked By Her Big Titted Big Cock Trans Boss In The Office, Swallows All Her Cum - Carla Morelli And Lizzy Laynes

1 year ago

BeMyHole

handjob, ebony, shemale, POV, chubby, MILF, big tits
22:34 85%

The secretary, the tranny and I

5 years ago

xHamster

italian, secretary, shemale fucks guy
28:15 85%

Bbusty Milf Alura Joins Her Hubby In Fucking His Ts Secretary With Alura Jenson And Shiri Trap

1 year ago

ShemaleZ

secretary, shemale, stockings, threesome, blonde
43:56 85%

Secretary gets her pussy plowed by her hung tranny boss

9 years ago

TrannyOne

secretary, boss, MILF
56:22 83%

Grazyeli Silva - Slutty Secretary Tranny Fucked By 2 C

2 years ago

Upornia

shemale, threesome, stockings, fetish, secretary
15:10 83%

Cliff Jensen And Brittney Kade - Sexy Secretary Gets Free-use Fucked At The Office For Bosss Birthday

1 year ago

ShemaleZ

secretary, shemale, POV, big tits, office
34:33 83%

Shemale boss and female secretary have some amazing sex together

6 years ago

TrannyOne

secretary, boss
34:15 83%

Crossdresser japanese secretary fucking intensely.

7 years ago

xHamster

teen (18+), teen anal (18+), japanese, crossdresser, secretary, shemale fucks guy
36:59 82%

Gorgeous TS secretary fucks his bosss ass nice and hard

4 years ago

TrannyOne

secretary, anal
16:42 82%

Guy fucks secretary tgirl

14 years ago

AShemaleTube

secretary, stockings
16:13 81%

Little angel uses vibrator

7 years ago

ShemaleZ

POV, couple, MILF, fisting, BBW, BDSM, masturbation
16:47 81%

Sissy secretary gets fucked in toilets by the Boss

7 years ago

ShemaleZ

toilet, secretary, sissy, boss
23:26 80%

Lizzy Laynez And Carla Morelli In Horny Ebony Milf Gets Fucked By Her Big Titted Big Cock Trans Boss In The Office, Swallows All Her Cum Lizzy Laynes 24 Min

1 year ago

ShemaleZ

ebony, POV, big ass, interracial, MILF, office, swallow
21:00 80%

Secret sheboy Secretary Opens pleasant butt For Boss

8 years ago

ShemaleZ

secretary, boss, shemale
30:48 80%

TS Eating The Secretary

8 years ago

ShemaleZ

secretary
35:34 80%

Bearded dude gets spit roasted by delicious busty tranny secretaries

8 years ago

TrannyOne

threesome, secretary
41:59 80%

Secretarys Dommination

6 years ago

ShemaleZ

BDSM, secretary
30:16 80%

TS Eating The Secretary

6 years ago

ShemaleZ

shemale, secretary
15:13 80%

Secretary gets her pussy plowed by her sexy tranny boss

9 years ago

TrannyOne

secretary, boss
23:22 80%

Young assistant interviews new secretary in shemale video

9 years ago

TrannyOne

audition, secretary
15:51 79%

The Secretary and The Boss

4 years ago

TrannyOne

secretary, small tits, boss, shemale
26:16 79%

Old boss with her tranny secretary

7 years ago

ShemaleZ

mature, creampie, fetish, outdoor, lingerie, ladyboy, uniform
21:36 79%

Nasty lad in a whorey Skirt gets a Double Facial

1 year ago

ShemaleMovie

tattoo, facial, upskirt, secretary, cum in mouth, domination, skirt
15:01 78%

Trans secretary urprincesspea caught jerking off

2 years ago

AShemaleTube

homemade, stockings, caught, jerking, masturbation, secretary, sissy
34:41 77%

Girl/girl Enjoy in Underwear

6 years ago

TrannyGem

pantyhose, stockings, strapon, lesbian, office, shemale and girl, strip
39:55 75%

Horny boss gets his old fat ass banged hard by the horny TS secretary

4 years ago

TrannyOne

fat, office, secretary, boss
28:50 75%

Lewd Secretaries gang Up On Their penis Manager

5 years ago

TrannyGem

office, gangbang, secretary, cum in mouth, domination, penis, webcam
34:46 75%

Foxy Angel - Secretary

4 years ago

TrannyOne

heels, secretary
1:02:12 75%

Chinese secretary 4

6 years ago

TXXX

BDSM, chinese, secretary, asian
50:37 71%

Horny Mature Secretary Turns Her Boss Into A Submissive Bitch

5 years ago

BeMyHole

mature anal, office, secretary, boss, shemale fucks guy
16:19 71%

Hot teen fucked by black monster cock

7 years ago

ShemaleZ

cute, black, creampie, POV, couple, interracial, asian
57:51 71%

The transsexual secretary starring pasha ( 1981 uncommon flick )

5 years ago

ShemaleTaxi

vintage, secretary
2:12:07 70%

Sissy Slut Secretary

6 years ago

ShemaleZ

secretary, slut, sissy, shemale
41:03 70%

Shemale Lesbian

7 years ago

ShemaleZ

lesbian, secretary
26:29 70%

Transvestite Secretary (uk 1992) Part 2 End

4 years ago

Upornia

vintage, secretary, amateur
39:05 70%

Jane Marie Is A Ladyboy That Wants To Plow A Secretary

5 years ago

ShemaleZ

tattoo, ass licking, secretary
27:29 70%

Heels, stockings and Heavenly crevice

1 year ago

ShemaleMovie

pantyhose, lingerie, crossdresser, office, heels, secretary
16:36 67%

Aphrodite Adams - Ts Trans Secretary Drilled Raw On The Table

3 years ago

TXXX

big cock, secretary, stepmom, amateur, big tits
2:12:38 67%

Sissy Slut Secretary

4 years ago

TrannyOne

office, secretary, slut, sissy
15:39 67%

TRANSFIXED - Sexy Secretary Brittney Kade Gets FREE-USE Fucked At The Office For Boss's Birthday

1 year ago

xHamster

blowjob, office, big cock, secretary, bareback, boss
23:53 67%

Horny tranny secretary Kelly Klaymour strokes till cumming in streams

8 years ago

TrannyOne

secretary
28:06 67%

Caged Sissy Secretary Rides Thick Anal Dildo

1 year ago

$$ FapHouse

sissy, secretary, dildo
15:08 67%

Ebony model fucks in hot tub

7 years ago

ShemaleZ

ebony, creampie, POV, couple, fetish, asian, fisting
20:20 67%

Fatman and Secretary

6 years ago

ShemaleZ

redhead, secretary
55:23 65%

Hot skinny trans secretary gets stuffed and filled with cum by big cocks

11 months ago

XXXVogue

stockings, blowjob, group, vintage, secretary, cum in mouth, skinny
26:42 64%

Young Boss Tests His Mature Secretary's Cunt For Strength!

4 years ago

xHamster

beauty, russian, fisting, old and young (18+), food, secretary, boss
57:08 64%

Horny Latina Secretaries Enslave And Dominate Their Boss

4 years ago

TrannyOne

BDSM, latina, secretary, domination, boss
50:05 63%

Hot Latina Secretaries Abuse And Dominate Their Boss

4 years ago

TrannyOne

shemale, secretary, boss, threesome
26:29 62%

Riley Storm Assistant Pummel

5 years ago

TrannyGem

creampie, anal, office, old and young (18+), secretary, boss, shemale
21:56 61%

Blonde tranny secretary is asked to fuck her bosss tight ass nice and hard

4 years ago

TrannyOne

office, secretary, tight
16:02 60%

Boss makes trans secretary Anna Rose kneel down for a mouthful

1 year ago

XXXVogue

secretary, amateur, homemade, POV, boss
55:30 60%

Transvestite Secretary

7 years ago

ShemaleZ

secretary, crossdresser
30:24 60%

Zucchini and carrot in the mature pussy of a MILF secretary.

5 years ago

xHamster

russian, MILF, fisting, glasses, insertion, close up, secretary
17:06 60%

Cutie assistant public remote manage

5 years ago

TrannyGem

public, secretary, vibrator, chastity, crossdresser
57:21 59%

Horny latina secretaries enslave and dominate their boss

4 years ago

AShemaleTube

mature, fetish, uniform, group, secretary, domination, boss
29:51 57%

30 mins no break fellate spitroast contest!

9 months ago

TrannyGem

double anal, contest, gangbang, deepthroat, heels, secretary, slut
15:51 57%

Cute TS Secretary with Her Boss

10 years ago

TXXX

cute, creampie, secretary, small tits, boss
43:19 57%

Stunning assistant try on haul in the chief office

3 years ago

ShemaleTaxi

feet, office, heels, secretary, taxi, crossdresser
26:04 57%

Secretary by Elliotyip male x futa

5 months ago

TXXX

mature, secretary, cartoon, futanari
28:50 57%

Sexy horny secretaries make their boss service their dicks and eat cum

4 years ago

TrannyOne

secretary, boss
49:49 57%

Horny latina secretary seduces and dominates her weenie boss

4 years ago

TrannyOne

secretary, boss, office, seduced
42:51 55%

Horny latina secretary gives it to her boss good and hard

5 years ago

AShemaleTube

mature, homemade, secretary, domination, webcam, boss
27:16 53%

Young Boss exposes his older secretary to a lustful slut!

4 years ago

TrannyOne

mature, secretary, slut, boss, shemale
19:13 53%

Jeanne Pink Transformation Into A Sexy Secretary No Secrets

2 years ago

IcePorn

big tits, secretary, solo
22:55 50%

Sissy Secretary in horny after work activities

3 years ago

xHamster

stockings, masturbation, secretary, nylon, sissy, chastity
42:38 48%

Horny Latina Secretary Gives It To Her Boss Good And Hard

5 years ago

BeMyHole

pantyhose, mature anal, office, secretary, webcam, boss, shemale fucks guy
22:07 43%

Secretary Blow

2 years ago

XXXDan

vintage, secretary
26:37 40%

The Secretarys Dirty Report, Dildo, Orgasm, Pissing

4 months ago

$$ FapHouse

pissing, pantyhose, anal, polish, orgasm, dildo, cumshot
37:14 38%

Latina Secretary And The Boss Have A Naughty Fling

4 years ago

HClips

mature, amateur, latina, secretary, webcam, boss
22:49 33%

Sissy Secretary In Horny After Work Activities

3 years ago

ShemaleZ

stockings, secretary, webcam, sissy
17:03 25%

AB0381 Beauty secretary public remote control

5 years ago

xHamster

public, outdoor, secretary, stockings
25:08 20%

Sissy Assistant crud abjected After Work

5 years ago

TrannyGem

office, prostitute, secretary, slut, sissy
15:17 20%

Hot secretary with gigantic donk wants promotion, boss

7 months ago

IcePorn

shemale, bareback, ladyboy, boss, secretary
24:45 20%

Sasha Foxxx predominates the entire Office

1 year ago

ShemaleMovie

feet, footjob, BDSM, office, secretary, domination, sensual
50:37 13%

Horny secretary has her way with the boss

4 years ago

TrannyOne

office, secretary, boss
24:45

Sensual-domination, jasmine-wolff, foot-job

4 days ago

XXXVogue

feet, footjob, shemale, domination, BDSM, sensual
24:05

Ts-ejaculation, curvy-body, mexico

2 weeks ago

XXXVogue

ebony, black, shemale, POV, chubby, orgasm, office
15:10

Sexy Secretary Brittney Kade Gets FREE-USE Fucked At The Office For Bosss Birthday

1 year ago

BeMyHole

blowjob, office, secretary, reality, domination, boss
19:33

Iranian shemale has sex with an Egyptian woman, hot sex

2 years ago

xHamster

femdom, bisexual, maid, upskirt, secretary, cum in mouth
17:53

Horny secretary Sucked off Company chief to Promote Herself

1 month ago

ShemaleTaxi

thai, big ass, brazil, asian, japanese, BBW, ladyboy
17:51

Naughty Secretary Sucked off Company Boss to Promote Herself

11 months ago

$$ FapHouse

big ass, brazil, BBW, tattoo, latina, 18, secretary
2:01:12

Dass-658 Arrogant Shemale Secretary Gets Flowers By Her Boss And Gives Him Anal Entertainment Renka Yuzuki

1 year ago

ShemaleZ

asian, japanese, shemale, stockings, secretary
22:43

Brandy Scott - Secretary Fuck

6 years ago

TXXX

stockings, lingerie, blonde, secretary
15:32

TGIRLS XXX - Compilation Updates 31st Mar to 4th Apr 2

2 months ago

XoZilla

secretary, beauty, shemale, solo, masturbation, compilation
35:08

Towheaded dicke titten Sekretärin tranny ass-fuck und sperma abgespritzt

1 year ago

ShemaleMovie

german, sperm, ass, secretary, cum in mouth, cum in ass
30:44

Sissy secretary lunchtime fucking by boss

6 years ago

ShemaleZ

secretary, sissy, boss
22:18

His secretary is a secret transsexual

12 years ago

AShemaleTube

interracial, secretary
24:29

Hawt Ladyboy Secretary Bia Very Precious Fuck

12 years ago

TXXX

ladyboy, secretary
37:08

Trans Secretary Andreza Gets Fucked In The Ass And Cummed On Glasses - Andreza Fernandes

1 year ago

ShemaleZ

brazil, big tits, tattoo, glasses, ass, secretary, cum in ass
15:49

Transex secretary giving Her chief

1 year ago

ShemaleTaxi

cumshot, shemale fucks guy, brazil, secretary
47:07

Horny trans secretaries gang up on their weenie boss

4 years ago

TrannyOne

office, secretary, boss
24:05

Black-and-white, big-natural-tits, ts-ejaculation

1 month ago

XXXVogue

office, shemale, ebony, orgasm, black, handjob
48:42

C4 Film (april 20, 2025) the boss Is a slut on a flick Conference with Her Banker.

1 year ago

ShemaleMovie

handjob, french, train, lingerie, BDSM, crossdresser, prostitute
28:27

Brooke smashes Assistant receives Her enchanting rump porked

6 years ago

TrannyGem

office, secretary, cute
16:07

Shemale Secretaries

1 week ago

$$ FapHouse

masturbation, shemale
36:41

Individual Secretary Gets Up Close And Private - Jade Venus

4 months ago

KeekAss

blonde, close up, secretary
54:00

Secretary Cumshow

8 months ago

$$ FapHouse

masturbation, creampie, mature anal, secretary
32:00

Dressing a Secretary to Put on the Sidewalk

9 months ago

$$ FapHouse

mature, shemale, amateur, secretary, bondage
15:01

MESMERIZED - COUGAR Magician Penny Barber & Secretary Zariah Aura Argue During Experience, HAVE STIFF FUCKY-FUCKY

1 year ago

TrannyGem

squirt, MILF, orgasm, dogging, shemale and girl, riding, cougar
40:52

Asian amateur ladyboy secretary getting fucked by her bosses

5 years ago

xHamster

teen (18+), teen anal (18+), ladyboy, secretary, boss, homemade
23:59

Lovely tranny Secretary Bia Very lusty plow

7 years ago

ShemaleZ

secretary
35:00

Blonde big titties assistant transgender princess anal and cumshot

2 months ago

ShemaleMovie

teen (18+), german, anal, big ass, teen anal (18+), facial, swallow
16:21

A day at the office

1 year ago

XXXDan

secretary, mature, office, crossdresser
24:55

The Secretary Gets Her Mouth Filled with Sperm. Big in Deep Throat and Fisting in the Final. Vanessabitchx

9 months ago

$$ FapHouse

french, fisting, bondage, sperm, deepthroat, secretary, cum in mouth
1:14:03

SexyGirlStephanieJames - sissy secretary fellating man meat is necessary

9 months ago

ShemaleTaxi

fat, chubby, BBW, dildo, ass, secretary, toys
15:01

This married chief enjoys to eat cock and asshole of his secretary before fuck her

11 months ago

ShemaleMovie

anal, stockings, blowjob, shemale, secretary
17:08

AB0381 Beauty secretary public remote control

1 year ago

JizzBunker

chinese, beauty, big ass, secretary, public

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