Search results - First Sissy

Total found: 300 videos (page 2)

my first becoming a sissy bitch video featuring me, Mark Moran0:47
2 years ago xHamster

My first becoming a sissy bitch video featuring me, Mark Moran

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Sequel to Pegging of Sissy Slut for the First Time30:11
2 years ago xHamster

Sequel to Pegging of Sissy Slut for the First Time

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Hot 18 year old young man tries his best friend's cock for the first time when there is no one in his house5:12
2 years ago xHamster

Hot 18 year old young man tries his best friend's cock for the first time when there is no one in his house

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A young gay is training for the first sex with a trans, wants to put it in doggy style and start with the ass1:13
2 years ago xHamster

A young gay is training for the first sex with a trans, wants to put it in doggy style and start with the ass

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First anal fun with little dildo on exercise bike 12x2,5cm. Tiny dildo in big bubblebutt.24:44
2 years ago xHamster

First anal fun with little dildo on exercise bike 12x2,5cm. Tiny dildo in big bubblebutt.

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JOI GAY- CUM FIRST TIME ANAL (in spanish dirty)6:16
2 years ago xHamster

JOI GAY- CUM FIRST TIME ANAL (in spanish dirty)

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Happy new year first sexy video for this year my new tiger dress was very sexy and seductive that make you horny enjoy2:09
2 years ago xHamster

Happy new year first sexy video for this year my new tiger dress was very sexy and seductive that make you horny enjoy

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2 years ago xHamster

First time curious young sissy crossdressing in wifes lingerie and playing with her toys

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First Time in Heels, Nylon and having Fun with a Toy2:31
2 years ago xHamster

First Time in Heels, Nylon and having Fun with a Toy

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My first straw of the year I dress as a FemBoy to enjoy better.2:43
2 years ago xHamster

My first straw of the year I dress as a FemBoy to enjoy better.

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2 years ago xHamster

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2 years ago xHamster

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2 years ago xHamster

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2 years ago Gay Ck

First-Timer turkish transgender princess pop-shot

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2 years ago xHamster

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2 years ago xHamster

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2 years ago xHamster

Riding 14 inch for first time

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2 years ago xHamster

Cock locked in chastity for the first night ever

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Superstar first masturbation video #110:25
2 years ago xHamster

Superstar first masturbation video #11

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My first masturbation video #110:26
2 years ago xHamster

My first masturbation video #11

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My first video here, just casually stroking my dick... #110:28
2 years ago xHamster

My first video here, just casually stroking my dick... #11

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my first time cumming on a heel.3:13
2 years ago xHamster

My first time cumming on a heel.

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2 years ago xHamster

Indian Virgin boy's First hard sex

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First time in high heels0:32
2 years ago xHamster

First time in high heels

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2 years ago xHamster

Quick Test when I first got New machine

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Blonde Twink try his first Video session7:27
2 years ago xHamster

Blonde Twink try his first Video session

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2 years ago xHamster

Straight Boys First time Crossdressing

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2 years ago xHamster

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My first video for Daddy1:04
2 years ago xHamster

My first video for Daddy

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2 years ago xHamster

Straight boy uses toy for the first time

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2 years ago xHamster

My first solo dildo fuck

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2 years ago xHamster

First time cumming in my inverted chastity device 5 inch urethral catheter tube

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2 years ago xHamster

First time fisted

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2 years ago FapHouse

My first solo for you

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2 years ago FapHouse

First time using a fuck machine

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2 years ago FapHouse

First-step shown myself

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2 years ago FapHouse

First meal of the day

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2 years ago FapHouse

First to last

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3 years ago FapHouse

My first vid ever filmed in heels! Stockings, heels, pose play and cum!

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Hot sissy crossdresser femboy Sweet Lollipop pissing in a drinking glass to taste it for the first time ever.9:16
3 years ago FapHouse

Hot sissy crossdresser femboy Sweet Lollipop pissing in a drinking glass to taste it for the first time ever.

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3 years ago FapHouse

First time anal

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Unboxed and Inside Me - First time with Big Daddy (L) - 13 inch dildo from Hankey's Toys25:32
2 years ago xHamster

Unboxed and Inside Me - First time with Big Daddy (L) - 13 inch dildo from Hankey's Toys

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Heterosexual Twunk First-Ever Time Ass-Fuck (JIZZ FLOW)9:19
2 years ago Gay Ck

Heterosexual Twunk First-Ever Time Ass-Fuck (JIZZ FLOW)

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Pink Glass dildo part 2. If you liked the first one watch this one as I fuck myself again for you all to see.2:29
2 years ago xHamster

Pink Glass dildo part 2. If you liked the first one watch this one as I fuck myself again for you all to see.

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First time with the fuck machine5:45
2 years ago xHamster

First time with the fuck machine

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2 years ago xHamster

Fem Chubs First Dildo experience

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2 years ago Gay Ck

Jizzing two Times from Sissy Hump Girl for the First-Ever time

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Crazy Hoe Likes Boink His Bootie * FIRST-TIMER ASSFUCKING ONANISM FUCK STICKS9:20
2 years ago Gay Ck

Crazy Hoe Likes Boink His Bootie * FIRST-TIMER ASSFUCKING ONANISM FUCK STICKS

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2 years ago xHamster

New dildo, first time in virgin ass.. it's fucking big

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2 years ago xHamster

First outdoors jerk

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2 years ago xHamster

Giving my brand new dildo it's first good ride with this perfect chub ass and tight horny hole

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SometimesNiki first try toy missionary11:36
2 years ago xHamster

SometimesNiki first try toy missionary

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2 years ago xHamster

Lola CD showing off her body the first time

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2 years ago xHamster

First Time Self Fisting!

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1 year ago xHamster

Asian gay boy puts a huge dildo inside his tight ass for the first time

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1 year ago xHamster

Sissys first orgasm in chastity

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Joslynn DeCheeks Gets Analyzed By The Fucking Machine For First Time!3:26
1 year ago xHamster

Joslynn DeCheeks Gets Analyzed By The Fucking Machine For First Time!

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1 year ago xHamster

Efreakme riding the very first dildo he started with and got me hooked

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1 year ago xHamster

My first toys

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For the first time I took my girlfriend to the woods and fucked2:52
1 year ago xHamster

For the first time I took my girlfriend to the woods and fucked

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For the first time I took my girlfriend to the woods and fucked5:16
1 year ago xHamster

For the first time I took my girlfriend to the woods and fucked

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My first handsfree Orgasm1:30
1 year ago xHamster

My first handsfree Orgasm

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Dr. Prof. Wolf Part 2 - My first visit at the Sissy-Doctor with examination1:00:39
1 year ago xHamster

Dr. Prof. Wolf Part 2 - My first visit at the Sissy-Doctor with examination

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Dr. Prof. Wolf Part 1 - My first visit at the Sissy-Doctor with examination47:17
1 year ago xHamster

Dr. Prof. Wolf Part 1 - My first visit at the Sissy-Doctor with examination

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Sissy Beginner - First video7:20
1 year ago xHamster

Sissy Beginner - First video

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1 year ago xHamster

My stepbrother Young Beautiful Big Ass First Time I Touch and Seduced him in midnight

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1 year ago xHamster

Rofiqul fuking Hindi doy the first time

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1 year ago xHamster

Straight scandinavian boy moans from anal training + first bbc dildo

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1 year ago xHamster

The first video

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1 year ago xHamster

First Time Suck Stepbrother big cock and cum inside mouth

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1 year ago xHamster

That first drip of precum

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1 year ago xHamster

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1 year ago xHamster

First time fully dressed

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1 year ago xHamster

Unrealme17 femboy tried fuck machine for the first time

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1 year ago xHamster

Finally! My first Sissygasm!

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1 year ago xHamster

New Fuck Buddy First Time Making a Sex Video 3

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At first, I scream so hard from a big dick in my ass and from a strong buzz! A powerful orgy of student guys11:56
1 year ago xHamster

At first, I scream so hard from a big dick in my ass and from a strong buzz! A powerful orgy of student guys

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1 year ago xHamster

Getngetout88 playing with his first love, a BBC dildo

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1 year ago xHamster

Interracial First

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1 year ago xHamster

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1 year ago xHamster

First Time Playing with a Glassdildo

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1 year ago xHamster

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1 year ago Gay Ck

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1 year ago xHamster

To prepare myself for fisting for the first time I break my ass with two bottles of two different sizes. Ass stretching training

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1 year ago xHamster

My First BBC Anal Toy

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1 year ago xHamster

First Stretching 2024 Warmup with some midsize dildos

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

Codis First Time Cumming on Cam.

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1 year ago xHamster

Sissy trying anal for the first time

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

My First Girlie Panties Play Complete HD Version

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

Goth bitch Natalie backs up on dildo for first video

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1 year ago xHamster

First time hold my stepbrother big monster cock in hand

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1 year ago xHamster

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1 year ago xHamster

Gaping Right After the First Fuck

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

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1 year ago xHamster

First Attempt

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11 months ago xHamster

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11 months ago xHamster

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11 months ago xHamster

Straight Skinny boy takes big one first attempt

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Part 3 of a live stream, Sean More camming online. Double Penetration, from the same session & getting DP for the first time!13:20
10 months ago xHamster

Part 3 of a live stream, Sean More camming online. Double Penetration, from the same session & getting DP for the first time!

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10 months ago xHamster

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10 months ago xHamster

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10 months ago xHamster

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10 months ago xHamster

Femboy tries Fuck Machine for the first time - Crossdresser gets his big ass fucked

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10 months ago xHamster

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