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i was in pain, but it was really pleasurable

i was in pain, but it was really pleasurable

Braces are painful but worth it.

Braces are painful but worth it.

She was in Pain from my Huge Cock, but my Stepsister will never Give up Sex.

She was in Pain from my Huge Cock, but my Stepsister will never Give up Sex.

Me and my new GIANT dong. It hurt to get it in but well worth the pain.

Me and my new GIANT dong. It hurt to get it in but well worth the pain.

The noise at the end... not sure if that’s pain or pleasure but either way I’m having fun 😜😋❤️💋

The noise at the end... not sure if that’s pain or pleasure but either way I’m

She had just returned from school and we were learning to deal with pain from vaginismus. We kept things slow, but god it was fun...

She had just returned from school and we were learning to deal with pain from vaginismus.

gonna wear these all day. way more painful than i thought but i deserve it

gonna wear these all day. way more painful than i thought but i deserve it

My boobs are resting, but I'm in pain

My boobs are resting, but I'm in pain

my back pain doesn’t love my heavy, big, perky tits but I hope you’ll love them ;) [OC]

my back pain doesn’t love my heavy, big, perky tits but I hope you’ll love them

Love anal, but I’m painfully tight. Tips welcome?

Love anal, but I’m painfully tight. Tips welcome?

It wasn't without pain and effort but she was determined to take him all the way in her ass! You should be proud of your slut aswell!

It wasn't without pain and effort but she was determined to take him all the way

it's weird and painful, but there are definitely orgasmic contractions! [:03 & :40] (has audio)

it's weird and painful, but there are definitely orgasmic contractions! [:03 &

No disrespect doggy style community but seeing your lady faces of pleasure and pain is next level

No disrespect doggy style community but seeing your lady faces of pleasure and pain

This is what vaginismus looks like. It took two years of patience and pain to get this far, but Diana is incredible and keeps working through it. (If anybody knows an appropriate sub for this, feel free to X-post)

This is what vaginismus looks like. It took two years of patience and pain to get

Jamie's asshole gets broken in early in her career, looks like a painful process but she gave it all she had ???❤

Jamie's asshole gets broken in early in her career, looks like a painful process

Not exactly painal but does feature some pain. Want to help?

Not exactly painal but does feature some pain. Want to help?

She can’t help but enjoy your pain

She can’t help but enjoy your pain

I want to remake this clip but what can I do to make in more painful? Ideas?

I want to remake this clip but what can I do to make in more painful? Ideas?

She is impaling herself on my big cock, but no pain no gain! OC

She is impaling herself on my big cock, but no pain no gain! OC

Innocent Lady had Pain in her A$$ & Went to Hospital but H0rny Doctor had some other Plans for her Full 13Min+ F©king Video!! Don't Miss Link in Comments

Innocent Lady had Pain in her A$$ & Went to Hospital but H0rny Doctor had

The pain is temporary but reward will last forever

The pain is temporary but reward will last forever

He Thinks His Blue Balls are Going to PoP in Ball Crusher! But I know They Can Take More Pain for Mistress Loow. 😈

He Thinks His Blue Balls are Going to PoP in Ball Crusher! But I know They Can Take

He was so long I was worried it would be painful from behind. As soon as I realised it was nothing but pure pleasure feeling him so deep, I just submit 😈

He was so long I was worried it would be painful from behind. As soon as I realised

A little pain always makes me giggle. New to sub but love it so far. [36F]

A little pain always makes me giggle. New to sub but love it so far. [36F]

My dominant wife make my anal training a little painful but fast progression 🥹

My dominant wife make my anal training a little painful but fast progression 🥹

It's finally the weekend. This week was a pain up the arse - but hey-ho 🤷

It's finally the weekend. This week was a pain up the arse - but hey-ho 🤷

And my adult braces are back. Super painful, but nothing I can’t handle. Elastics in 4 weeks! ☺️

And my adult braces are back. Super painful, but nothing I can’t handle. Elastics

this was so painful, but I loved it

this was so painful, but I loved it

Owww little painful, but I really like it. Wanna help ?[F]

Owww little painful, but I really like it. Wanna help ?[F]

Sweetie agreed to double anal, but it turns out to be more than she could actual handle as she taps out due to the pain and ends the scene early 🔥🔥🔥

Sweetie agreed to double anal, but it turns out to be more than she could actual

suffering today but maybe my pain can be your pleasure 😈[f]

suffering today but maybe my pain can be your pleasure 😈[f]

try to go no hands, but it's so painful

try to go no hands, but it's so painful

These will make you pain in pants but if you asked nicely 🙂

These will make you pain in pants but if you asked nicely 🙂

My Son is such a pain...but I love him anyway

My Son is such a pain...but I love him anyway

This girl made me the hardest I'd ever been. I know it was a little painful for her but it felt so good! I need another petite girl!

This girl made me the hardest I'd ever been. I know it was a little painful for her

I can barely wrap my fingers around his cock and I had to tap out the first time he tried sliding it in my ass, but this slut don't give up. Pro tip: talk about how fucking good it feels & the sensation transitions from intense pain to intense pleasure.

I can barely wrap my fingers around his cock and I had to tap out the first time

This is painful to watch I thought it was a one time thing but my bully’s fucking mom again. And why is she letting him film her ffs

This is painful to watch I thought it was a one time thing but my bully’s fucking

I love getting punched in the face and chest.❤️ It was so painful, but it felt so good.🙈🙈

I love getting punched in the face and chest.❤️ It was so painful, but it felt

[💜OF] i used to feel pain but now i just feel pleasure!

[💜OF] i used to feel pain but now i just feel pleasure!

I know it's painful, but I deserve this reward, Mom!

I know it's painful, but I deserve this reward, Mom!

[Reddit] Are you serious right now...?? You're still have these painful boners?? I thought we were just going for a walk in the park! Okay..fine..pull it out. But this will be the last time...okay??

[Reddit] Are you serious right now...?? You're still have these painful boners??

She’s a great ballbuster when she has you in pain but still leaking 🍆 💦

She’s a great ballbuster when she has you in pain but still leaking 🍆 💦

She likes it, but it's a bit of a pain in the ass...

She likes it, but it's a bit of a pain in the ass...

This beta is craving for humiliation. My friends have given him a lot of pain on WhatsApp but that's not enough for him. So here I'm serving you some fresh meat. Enjoy and have a good laugh

This beta is craving for humiliation. My friends have given him a lot of pain on

Still reeling from the pain of waxing...But worth it! ❤️

Still reeling from the pain of waxing...But worth it! ❤️

This was painful, but love my bruises... 🙈

This was painful, but love my bruises... 🙈

There is a thin line between Pain and pleasure, i got my ass destroyed but got my o’s too

There is a thin line between Pain and pleasure, i got my ass destroyed but got my

i’m such a pain slut i can’t help but smile and moan after each slap 🥰

i’m such a pain slut i can’t help but smile and moan after each slap 🥰

#Edging 😈 You know how eager the slave is! 😋 But I grabbed his head and pulled his mouth on my dick!🥵 He loves to suck! He loves my sperm. Combining his favorite activity with pain...that's real transformation.😏 #CBT

#Edging 😈 You know how eager the slave is! 😋 But I grabbed his head and pulled

I was torn from pain, but remained silent

I was torn from pain, but remained silent

Tittie drops just feel so good, ya know?? 😌It kinda hurts but the pain just makes it more pleasurable, like getting spanked 🤤🫠❤️‍🔥

Tittie drops just feel so good, ya know?? 😌It kinda hurts but the pain just makes

A busty British domme pegging you with a cock this big will be a painful but pleasing experience like no other, will you bend over?

A busty British domme pegging you with a cock this big will be a painful but pleasing

James Bond - Casino Royale! But my version is much more painful!

James Bond - Casino Royale! But my version is much more painful!

[HardX] "Can You Just Slap My Fucking Face?" April Olsen Shows She's Not Just a Double Anal Slut, But a Pain Slut as Well

[HardX] "Can You Just Slap My Fucking Face?" April Olsen Shows She's Not

Sorry I'm a little late to locktober but finally painfully locked and pinched my pathetic clit into chastity

Sorry I'm a little late to locktober but finally painfully locked and pinched my

Thinking about bleaching my tight hole, but i'm scared of the pain

Thinking about bleaching my tight hole, but i'm scared of the pain

I think this was made by [chumaki23], but Twitter's a pain in the ass

I think this was made by [chumaki23], but Twitter's a pain in the ass

Hitting the clitoris with a dildo hurts, but it's a pleasurable pain.

Hitting the clitoris with a dildo hurts, but it's a pleasurable pain.

I think I'm a little weird but even though it sometimes causes a little pain I want to do it harder and harder.... 😍

I think I'm a little weird but even though it sometimes causes a little pain I want

This is one of the most wonderful feelings on earth.... although sometimes it can be a bit painful but it is worth it 😏

This is one of the most wonderful feelings on earth.... although sometimes it can

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