Sort by
Relevancy

Most Relevant 'first-time bondage crossdressers' Porn Videos

Big Preview Date Added 2020-03-27

52Videos

90%
Play All Visit playlist

by: Joop52

First Time Virgin

90%
Big Preview Date Added 2021-02-28

27Videos

66%
Play All Visit playlist

by: ꭻσcк ᏼꮎꭲꭲꮎꮇ ɢᴜʏ

Curious First Time Bi Straight Bro Experience

66%
Big Preview Date Added 2023-05-18

137Videos

100%
Play All Visit playlist

by: itsmejc

FIRST TIME CASTING

100%
Big Preview Date Added 2023-06-04

7Videos

100%
Play All Visit playlist

by: xlfm888

Virgin first time

100%
Big Preview Date Added 2019-07-22

61Videos

100%
Play All Visit playlist

by: maninbigd

1st Time (Anal, BJ, HJ)

100%
Big Preview Date Added 2018-07-22

72Videos

92%
Play All Visit playlist

by: Dick Riding Power Bottom

Compilation & Poppers & PMV

92%
Big Preview Date Added 2018-09-11

35Videos

77%
Play All Visit playlist

by: PlaceboEffect666

ROUGH

77%
Big Preview Date Added 2019-03-17

131Videos

90%
Play All Visit playlist

by: Dick Riding Power Bottom

BIG Fat Dick Ass Fucking

90%
Big Preview Date Added 2019-03-17

58Videos

55%
Play All Visit playlist

by: Dick Riding Power Bottom

Long Gay PORNO

55%
Big Preview Date Added 2020-12-26

259Videos

80%
Play All Visit playlist

by: lust3r

mormon cleric

80%
Big Preview Date Added 2022-01-28

333Videos

100%
Play All Visit playlist

by: Kolela

moan

100%
Big Preview Date Added 2022-01-28

164Videos

100%
Play All Visit playlist

by: Kolela

forced

100%
Big Preview Date Added 2022-09-09

29Videos

100%
Play All Visit playlist

by: black rainbow_

abuse me daddy

100%
Big Preview Date Added 2023-05-25

22Videos

100%
Play All Visit playlist

by: Floydcharlesiiixvi

My personal

100%
Big Preview Date Added 2023-08-28

8Videos

100%
Play All Visit playlist

by: itsmejc

STR8BOYZ BJ

100%
Big Preview Date Added 2023-10-15

57Videos

100%
Play All Visit playlist

by: xtrajuice

seegasm

100%
Big Preview Date Added 2023-10-30

70Videos

100%
Play All Visit playlist

by: Kinkynld

Asian

100%
Big Preview Date Added 2021-11-28

40Videos

100%
Play All Visit playlist

by: dicktwink

best CH episodes

100%
Big Preview Date Added 2023-07-07

40Videos

100%
Play All Visit playlist

by: itsmejc

COMING-OF-AGE

100%
Big Preview Date Added 2023-07-10

12Videos

50%
Play All Visit playlist

by: Bondage42

07_2023

50%
Big Preview Date Added 2024-04-24

1Videos

50%
Play All Visit playlist

by: Bill Gate

Rhyehim shabazz

50%
Big Preview Date Added 2022-02-10

5Videos

50%
Play All Visit playlist

by: Bouchabeurs

3) First time - First ass penetration - Deflowering - Losen his virginity

50%
Big Preview Date Added 2023-04-20

165Videos

100%
Play All Visit playlist

by: CherryFlavouredStomachAche

first time/first dick

100%
Big Preview Date Added 2017-05-31

95Videos

88%
Play All Visit playlist

by: Davidmanor55

first time

88%
Big Preview Date Added 2017-07-19

1Videos

50%
Play All Visit playlist

by: Cam07

Amateur, webcam, homemade, New, First Time, Virgian

50%
Big Preview Date Added 2017-08-12

4Videos

80%
Play All Visit playlist

by: J T

First time

80%
Big Preview Date Added 2017-09-17

4Videos

0%
Play All Visit playlist

by: Boux601

first time

0%
Big Preview Date Added 2017-10-26

2Videos

75%
Play All Visit playlist

by: Mocha9x5

My First Time

75%
Big Preview Date Added 2017-10-29

1Videos

50%
Play All Visit playlist

by: mex

First time

50%
Big Preview Date Added 2017-11-23

2Videos

50%
Play All Visit playlist

by: joriskoe

First time geil

50%
Big Preview Date Added 2017-12-09

238Videos

60%
Play All Visit playlist

by: ChongBK

Asia -1 Gay Porn Collection

60%
Big Preview Date Added 2017-12-09

199Videos

40%
Play All Visit playlist

by: ChongBK

XGen -1 Porn Collection

40%
Big Preview Date Added 2017-12-21

291Videos

77%
Play All Visit playlist

by: ChongBK

FIRST TIME; Straight

77%
Big Preview Date Added 2017-12-26

4Videos

0%
Play All Visit playlist

by: ibethatfurrymotherfcukr

Str8, Bait, First Time & Pay

0%
Big Preview Date Added 2018-05-08

6Videos

50%
Play All Visit playlist

by: Dirk151196

Straight/First time

50%
Big Preview Date Added 2018-05-23

0Videos

50%
Play All Visit playlist

by: david199

https://www.boyfriendtv.com/videos/340526/straight--jocks--first-time/

50%
Big Preview Date Added 2018-05-23

1Videos

50%
Play All Visit playlist

by: david199

https://www.boyfriendtv.com/videos/359899/collins-first-time-with-a-dude/

50%
Big Preview Date Added 2018-06-01

1Videos

50%
Play All Visit playlist

by: david199

https://www.boyfriendtv.com/videos/339201/rockstar-first-time-ass/

50%
Big Preview Date Added 2018-06-09

290Videos

61%
Play All Visit playlist

by: Hung Nude Bouncer UK

a Birthday Party@home-GuestList MEN-ONLY&DressCode *BIRTHDAY*SUITS* {footwear only indoors}

61%
Big Preview Date Added 2018-07-04

166Videos

60%
Play All Visit playlist

by: Dick Riding Power Bottom

ALL GROUP sex

60%
Big Preview Date Added 2018-07-12

32Videos

0%
Play All Visit playlist

by: Hotintpa1

First time

0%
Big Preview Date Added 2018-07-25

75Videos

50%
Play All Visit playlist

by: Ardil37

First time

50%
Big Preview Date Added 2018-07-29

266Videos

77%
Play All Visit playlist

by: SC0TTY

TwinkS

77%
Big Preview Date Added 2018-08-19

16Videos

60%
Play All Visit playlist

by: VAguyATL

creampie

60%
Big Preview Date Added 2018-08-19

13Videos

75%
Play All Visit playlist

by: KCMBock13

Hot Huge Cock

75%
Big Preview Date Added 2018-08-19

3Videos

81%
Play All Visit playlist

by: KCMBock13

Hot Trainers

81%
Big Preview Date Added 2018-08-30

20Videos

50%
Play All Visit playlist

by: FlawlessMale

First Time™

50%
Big Preview Date Added 2018-09-06

82Videos

83%
Play All Visit playlist

by: zilking

Twink, Slut and Daddy

83%
Big Preview Date Added 2018-09-10

3Videos

100%
Play All Visit playlist

by: Bi-SexToy4you

First time gay & twinks sexuell experience

100%
Big Preview Date Added 2018-09-10

25Videos

100%
Play All Visit playlist

by: fayoric

seduced/experimenting/first-time

100%
Big Preview Date Added 2018-09-19

24Videos

88%
Play All Visit playlist

by: BallsDeep

22Esperm

88%
Big Preview Date Added 2018-10-22

88Videos

100%
Play All Visit playlist

by: jonnyd

First time /college

100%
Big Preview Date Added 2018-10-24

18Videos

50%
Play All Visit playlist

by: Jockwithcox

first time

50%
Big Preview Date Added 2018-10-26

237Videos

100%
Play All Visit playlist

by: Moe7991

First Time

100%
Big Preview Date Added 2018-11-23

7Videos

50%
Play All Visit playlist

by: Sergej

First Time

50%
Big Preview Date Added 2018-12-02

129Videos

50%
Play All Visit playlist

by: caucasiansos

First time

50%