Top 10

Top 50+: Accidental Teen & MILF Upskirt Pussy Pics, GIFs (2022)

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#1. Brazzers
#2. RealityKings
#3. Chaturbate

When hottest pornstars no longer do it for you and when top porn sites feel like an afterthought, we go for “accidental” nudity. Yeah, it’s all fake, but who cares. When it comes to cock hardness levels, it can pop from 1 to 11 if you know how to party. Of course, I do mean nudity with clothes on! Sorry, the same applies to the pussy wetness levels if you are a female.

Your imagination is the best tool to get you horny, and is there anything much better than upskirt pictures? Well, maybe accidental upskirt GIFs if you prefer moving imagery. For your pleasure, I have a collection of nothing but extremely sexy upskirt pussy pics! From teens, MILFs, amateurs, cheerleaders, and everyone in-between. So, shall we proceed?

Fuck Doll MILF

I’ll fuck this MILF cunt with or without a condom; she looks more than casual fun. The goddess of male cum must have created her from the desires of all men. There’s hardly a better container for your dick. My mind is running out of excuses not to jerk off right now, even if we’ve just started.

Every way you look is perfect, from breasts to pussy to lips. Even hair strands aren’t thin or ruined. Nails do look beautiful too.

Her Dress is Slippery

I’m sure she was wearing no panties by accident! Also, the whole upskirt slip results from her dress’ material. Imagine this happening when you’ve asked your hot sister’s friend to clean up the desk. Well, I would cum on the same desk just for her to clean it up again. This time with her mouth.

Car Washing with Short Skirt

This was done by Hustler or some other popular magazine, and not your random amateurs from Snapchat or Facebook. The following picture is slightly enhanced, and I mean hand-picked. Other women did not wear panties of skin color.

That’s too bad, though, as dark brown is the only acceptable color for upskirt porn addicts.

Climbing the Stairs

Recently, my female friend was asked not to climb stairs because of this very reason. She is not a pornstar or anything and does wear panties. However, which one would you prefer? An intentional nude or something that just happened?

Whatever your answer is, don’t sweat it! We have so many more upskirt pics that you will find at least a few to jerk off to.

Stewardess Upskirt

Another teen that needs more attention and at least a few miles of dicks. She could be from Sweden or Norway, judging by her face. A pale-skin natural blond with a fabulous butt crack and a blue flight attendant uniform.

Now that’s one hardcore slut, which could do wonders in the cockpit. Get it? Because men were the only ones that had the privilege to fly a plane. That was a stupid time.

Cheerleader Practice

A short upskirt with as much pussy as your eyes can perceive. That’s one of the trickiest angles that reveal everything and nothing simultaneously. This horny cheerleader knows how to take a selfie and could cause a lot of damage to men around her.

What kind of damage? Have you heard about the term titled “blue balls”? That’s the worst pain a guy can feel in the groin area.

A Bottom Pussy and Upskirt Shot

My ex would constantly tease me with pics like this one. The only difference is that her face would be visible as well. I am sure it was an intentional shot and not done by a creep that follows women around.

On the other hand, what kind of person does not wear panties? It could be a hot summer day, but you have an extremely short skirt and no panties. That’s just asking for trouble.

Public Upskirt without Panties

Either these new phones can take pictures of DSLR quality, or this is a scripted picture. My dick is reaching the level of numbness at this point, where it’s so sore that I can’t feel it anything. Every pussy is a good-looking one, but this one takes if not the cake, then at least a cookie.

She’s wearing a light summer dress, has shaved her private parts, and has that crazy bitch look in her eyes. And you know what they about crazy women. These are the best girls to bang.

Upskirt Photo in Church

In the old, wooden church, where no one is watching but God, we have a dirty teen and her short dress. It’s too short to cover anything! Imagine old grandma’s reactions when one enters the holy place wearing nothing but this outfit.

Yes, it’s trashy and hot, and we demand more of the same, but with other people in photos.

Grocery Store Show

Inappropriate and admirable, that’s my take on this photo. She has planned it all, but my goodness… I don’t even care about cute-ass pornstars at this point; this is the one. A sane person would not be shocked to learn that she does porn.

How can one have a butt so round? My dick feels like the groceries in the background, ready to pop. My mouth is also ready for some of her apple jacks.

Teen Outfit Fantasies

She could be a cheerleader, a football player, or a tennis player. It does not matter in the end, as I have already stroked my cock twice. Whatever the case, we all know this teen is good with balls. She took a picture in the comfort of her own home while smiling just for you.

Pour yourself a cold drink, take your pants off and let her slowly sit down on you. As you gulp the glass, the fragrance of warm pussy fills your nostrils.

No Panties and No Shame

Here’s a divine pussy. An even better-looking pet in the shot and one kinky female. Now I know that many people go for a walk, especially in parks, to take photos like this one.

The only bad part is those red heels; they do not match anything unless you have Hulk eyes. We could teach her fashion as I pound her. My love for petite women is at its peak, and this one is perfect.

A Secret Upskirt Pussy Shot

So, your girlfriend wants to have fun, and you both are out of ideas. Here’s one! Why not take a decent-length dress, remove panties, and take a few photos? I cannot even imagine my reaction if an upskirt slip like this appeared in real life.

Like, if you have accidentally fallen or dropped your phone. You lift your head only to see the best view ever.

Exposed Skirt Slip

Fucking epic, ridiculous, and all kinds of mind-blowing. I am confident that this was not intentional. Either she forgot to wear the panties or did not care about showing her pussy at all. What kind of conference was this and how do I enter? Was this about uniforms? Maybe some nonsense talk about the fear of public speaking?

One simply does not give a damn if you have a hot diva like this one exposing her vagina.

Girls Changing

If you are one of those guys who does not care about shipping with their girl, think about it again. You can have so much fun, given the opportunity. This couple is beyond sane. There’s one thing to wear no panties, but another is to have your nipples poking in public.

Not only that, but she gets “hard” by the sheer thought of public upskirt shots. Look at how happy this amateur is. I am honored to be viewing this one.

Hot Nurse with Her Upskirt Reveal

I pray that future patients do not have any heart issues or high blood pressure issues. A weak heart can’t take upskirt pictures like this one. She has no panties and is ready for some hardcore party.

Slightly chubby? Maybe. Nonetheless, don’t you lie to me. There is no straight person in this universe that did not just get horny. In case you aren’t as lucky, check with your local doctor. Maybe this experience will repeat itself.

Picking the Flowers

One of the more innocent teen pussy upskirt pics, and people around her would not even suspect a thing. You have a petite amateur posing for the camera and that’s it. Now they can’t see the sheer joy that her bottom is.

That’s how women should take selfies anyway, or photos in general. At least if they want to have more likes than their best friend.

Exposing Herself

Not so much of an upskirt teen pic, as more of a teaser. A dry pussy is better than no pussy, of course. Yet, assuming she was taking this one with her boyfriend, at least spit on her or something. At least you get a nice view of a fresh, 18-year-old teen pussy. All legal and open for business.

An Upside-Down Teen Pussy

Watch out, everyone; we have an art student here, but for the better. Some women just can’t be ordinary and take regular nude pics. No, they will instead go for something much wilder; in this case, it’s the inverse upskirt shot.

You have one happy babe and many men watching her.

An Upskirt Ass Photo

It does not look like this horny bitch has any panties whatsoever, but what we do know. We are here just for the ride. So take your hand off your pussy or dick for a moment and study this picture. It’s a given that people who took these pictures got to fuck them all in the end.

Now that’s one fact you can’t argue with.

Froget the See Through Panties

It’s always awesome to see the pussy slips due to the magical panties, but even better are photos like these. Still, I’m so grateful for all the cheap Chinese underwear and other outfits. One would not have this low density if it were an expensive brand.

Upskirt Sideways

Are we looking at the food commercial, or it’s one of the most photogenetic pussies? Being careful not to reveal the butthole, a teen college student remains one of the greatest mysteries. Is there more? Will we ever get the answer? What’s behind the skirt?

Maybe it’s a horny MILF amateur… So many questions!

Teen Upskirt Pic with Panties

Here is one fat pussy, and I mean the overall meatiness of her shower curtains, not an overall build. A bit disappointed by the sheer number of pimples, to be honest with you. On the other hand, maybe she is going through the phase of hormone imbalance.

You can see her panties and a nice blue dress to match the pink.

Kinky GILF Skirt

Contributing to the cum waste, a wet GILF joins our party as we hold our pesky sausages in our hands. How can a granny be so sexy anyway? I can assure you that the people in a circle of friends don’t even suspect a thing. Most perceive older adults as boring.

Pussy Tattoos and Short Skirt

Okay, this must be Japanese. Who else would tattoo tentacles and other nonsense if it wasn’t for crazy Asian girlfriends? I’d say this is on par with some of the best pornstars with tattoos. Equally as bizarre as our top 10 GIF picks there.

Sadly, this is her only photo. I’d love to see her front.

Let’s Just Fuck

Forget the panties and forget taking things slowly. Instead, pull your cock and smash that pussy until she collapses from exhaustion.

Cheap, semi-transparent dress, and a dark room. What could go wrong here? That’s the famous quote from Jeremy Clarkson.

An Afternoon Pray

These accidental upskirt pics always get me, and I mean the setting. That’s the same view you would see if some college babe were in this position. Just a regular-length skirt and tiny panties that give you a decent view.

Not sure about you, but that’s how I like my upskirt pictures without full nudity.

College Upskirt Pussy

A random slut crashed in your bed after a hardcore drinking session, and this is the view. More like a gift from God. Now, do you risk of fucking everything up by trying to kiss her, or simply take what the universe gives?

Give it a sniff, take a few pics, and jerk off to this memory for the rest of the decade.

Accidental Upskirt Pussy Slip

Of course, there are no accidents. You invite your good friend for a night out and randomly take pictures as you both talk… The night approaches, you do a few more shots and leave with blue balls, just like every other night. On the other hand, she complains about her current boyfriend you envy so much.

Well, the moment she asks you to send her pics from the night, you start sweating. That’s after you realize that it’s more than just random pictures! It was an accidental pussy reveal and your best work.

Like What You See?

There’s not much happening here, other than a random teen and her lifted upskirt. Wait, that was the whole point of this post! Shove your fingers down the cock hole and pleasure yourself as you stare at yet another kinky slut.

Dress Up, Panties Down

See that asshole? It’s as reliable as a new Toyota, and man, can it take miles. You can tell that this girl loves anal, because of the multiple rings visible on her asshole. That’s a compliment, at least from my point of view.

Regular sex is as boring as random YouTube videos, just don’t do it for many of us. At least we have an 18+ teen in this top 50 that is open to something dirty.

Sexy Shopping

Yes, please reach that thing at the very bottom… What a fucking epic MILF and a hot one too. Short white dress with yellow stripes, a leather jacket, and a face worth millions.

When I’m done with her, she would beg for those “wipe me” napkins on the top floor. So don’t even mind the trashy heels.

Windy Day

I’d like to think about the scenario in which someone took this picture. She was the one to lift her dress, but what was the discussion? Can you please snap a picture as I pretend it was a windy day?

Other than that, you have another 18-year-old and her sexual fantasies.

Wet Spots

This teen upskirt pic takes some time to figure out, but I’m sure you can figure it out. That is one of the cleanest, best-looking pussies out of a bunch. Also, with a perfect tiny hole that will eat your cock alive. What puzzles me are those wet spots at the very top of a photo.

Did she just piss in bed or something?

Horny MILF and Her Upskirt

Oh yes, this happened by accident, just like every other photo. I bet some of you are pissed for the watermark placement, but that’s just the way it is, bro. This is one sexy mature woman, with a bush and money in the bank.

That’s the impression I get from her expensive make-up.

Slut Carnival

Gather around for the carnival of sluts or some sort of art project. I’ve shown this one to my ex and she was confused for a moment on what the fuck this was.

Well, it’s just a backseat of a budget bike and I bet this slut would love a hard ride.

Short Skirt and No Panties

It’s spring in the hair (unless you are from Australia), and women drop their warm clothes for something lighter. It’s the season of new profile pictures, skin exposure, and erotic shots like this one.

She does need some tanning lotion or a spray to go from 6 to 10; we have the whole summer in front of us.

Tits, Ass and Abs

I swear this dress has been making rounds out there. This isn’t the first slut to have an identical skirt. Is this the official cheerleader outfit or something? If only the golden letters were not covered with her hair. Does it say “Harvard”? Can anyone of the more intelligent people figure this one out for us?

Reaching for Something

Men do check everyone’s ass, especially in a position like this. You know, when a female bends over or tries to reach something far away. Thankfully, this photo is much better with her short dress and panties that give you nothing else to see.

That’s what makes me excited!

It’s Windy Out There

Isn’t this the wildest fantasy of many men? An attractive or semi-attractive female is doing her thing when a gush of strong wind approaches. But, of course, she has no panties and boom, the shocking reveal of her pussy!

Upskirt with Panties

Is this hotter than most upskirt pussy pics where women have no panties? That’s the case, at least for me. You have the see-through violet panties that reveal some interesting details about her pussy.

First, you can see the big lip, and then there appear to be tiny hair bits? It looks like she did not shave all her places and did want to trick the camera.

Mirror Upskirt

Ask men to design buildings without repercussions, and mirror floors will be on their to-do list. She could be a pornstar, but who cares. Just enjoy the view. I’d love to have more of these mirror pussy photos, it’s like 3D porn but better.

On the other hand, when I think about mirror floors, things could turn for the worse. What if it was a fat female convention?

MILF Pussy Reveal in Public

College teens are not the only ones who are crazy in public. Here’s one trashy, attractive, and naked MILF, casually sitting in the chair. However, it does not take a rocket science degree to figure out what is happening here.

As for her age, I’ll give her 35. Although with evening make-up you could shave a few more years and improve the looks.

Lifting Her Skirt

Having personally collected close to 50 of these, I can safely say that men just want to fuck in the end. It does not matter how good or mediocre your girl is; you will fuck her. However, the afterthought is where true love can appear. If you still want to be with her afterward, marry her.

The same goes for all these teen upskirt pictures. You might want to fuck all these amateurs, but once your balls are empty, it’s “meh” and nothing else.

Now, let’s switch the top 10 upskirt porn GIFs!

Just a Spin

As we switch to upskirt GIFs, I’d like to show you one of the best teases. She knows that video quality sucks, and she plays with that. Spinning fast enough not to show her underwear or pussy! Just not too slow so you can’t figure out the rest.

Upskirt Masturbation

Another heavy hitter and this one is straight from porn. I’m sure you are aware of the tens of amateur porn sites that we have with more of this.

If not, consider yourself educated. You now know how women behave during their orgasms. Also, what is the upskirt view like?

Kitchen Games

Horny MILF with her white underwear and round ass. The most gorgeous women can sometimes be found in the place they hate. Her acting is on par with most homemade videos. She does not act too obvious, but we get it.

Dirty Shoppers

This must be a shopping mall of dreams, where you have horny shoppers like these. Although judging from the outfits it sells, could it be the used clothes store?

Hopefully, there are cameras so geeky virgins can jerk off to acts of these people.

An Obvious Upskirt Attempt

Well, this one is just that, a lonely teen college student and her long dress. I like the pussy look; much better than fucking your hand. Also, her sense of fashion is admirable. Bright clothes, great colors and the rest is okay too.

Whatever you do, don’t say that will do, pig, that will do to your girlfriend.

Date without Panties

Hey, this is what you don’t get to see after one of your dates ends. Ultimately, she is left with a lonely pussy and full stomach. But, at least you got to pay her bills, which is more than other neckbeards will ever do.

Who would love to see how the rest of this scenario goes? Hopefully, there are at least two dildos and ten horny men.

Playing Outside

Just a random Snapchat to her boyfriend or the rest of us. It’s sunny outside so why not tan that pussy a bit? Lifting her long dress and posting for the camera.

Just one of many teens trying to show their pussy for a piece of attention. That’s fine! More power to her and other bitches.

Bending Over After College

You are stuck in the dorms or car and your boyfriend is now coming as it’s sunny outside. What else can you do to have some fun? Drop the underwear and party hard!

That’s one exotic pussy upskirt GIF, slightly browner than the rest. As she bends over, I’d like to bend my dick inside her asshole.

Free Pussy Trial

Well, we have already seen so many of the upskirt pics, so… Why not go for something straight out of the porn or sex cam shows?

Would you like to test this one out? You know, just to ensure you are making a correct decision. No cumming inside allowed! You’ve been warned.

Teen Upskirt

Another of the public GIFs and this one drives me wild. Man, if someone were to pay me a penny for every fap session I had during the compilation of this post… I’d have two cents, which is not a bad start.

Anyway, whoever did this video, marry this teen as she is a woman of dreams.

Dirty Climbing

You demanded hot underwear GIFs, and I am certain this post has delivered on the promise. To end it all, here is the boss of all upskirt videos. For more porn like this, be sure to visit our top amateur porn sites list.

It’s just a teen with a short skirt, nothing wrong with that. Well, maybe she accidentally forgot her underwear at home. What happens inside those pipes is no one’s business. Now, would you like to clean her pipes?

Sam Kingwin

Sam has been working in the adult business since 1997, starting from the bottom of the barrel as the director's assistant, thinking of transitioning to male performer only to resume behind the scenes work, which was the most rewarding creativity wise. As of the 2010s, Sam has been covering top pornstars and best porn sites. Everything I ever say is either a fiction or a joke. Anyway, sharing is caring and there is nothing like helping guys discover hidden talents or porn networks that deserve their attention.