Top 50+: “Accidental” Teen Upskirt Pussy Pics & MILF Upskirt GIFs (2019)

Hottest upskirt pussy pictures and sexiest accidental panty reveals.

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Top 50:
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#1. Brazzers
#2. RealityKings
#3. True Amateurs

When hottest pornstars no longer do it for you and when top porn sites feel like an afterthought, we go for accidental nudity. When it comes to cock hardness levels, it can pow from 10 to 11, if you know how to party. Of course, I do mean nudity with clothes on! Sorry, same applies for 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.

55Truth or Dare

Imagine yourself playing truth or dare with one of the hottest MILFs in your work. You ask her a question about her sexual experience and she instead goes for a dare.

Now, the sane person would simply tell her to shout something stupid, but a horny dick will command otherwise. Show your upskirt is what we would say.

54Her Dress is Slippery

I’m sure she was wearing no panties by accident! Also, the whole upskirt slip is the result of her dress’ material. You’ve just asked your hot sister’s friend to clean-up the desk and this happened. Well, I personally would cum on the very same desk, just for her to clean it all up again. This time with her mouth.

53Car Washing with Short Skirt

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

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

52Climbing the Stairs

Recently, my female friend was asked not to climb stairs, because of this very reason. Obviously, she is not a pornstar or anything, and does wear panties. However, which one would you prefer? An obviously 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 few to jerk off to.

51Stewardess Upskirt

Another teen that needs more attention and at least few miles of dicks. She could be from Sweden or Norway, at least 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 a privilege to fly a plane. That was a stupid time.

50Cheerleader Practice

An upskirt short with as much pussy as your eyes can perceive. That’s one of the trickiest angles that reveals everything and nothing at the same time. 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 kind of pain a guy can feel in the groin area.

49A 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. This I am sure 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.

48Public Upskirt without Panties

Either these new phones can take pictures of DSLR quality, or this is a scripted shot. My dick is reaching the level of numbness at this point, where it’s so sore that I can’t feel it no more. 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.

47Upskirt Photo in Church

In the old, wooden church, where no-one is watching but the God, we have a dirty teen and her short dress. It’s too short to cover anything! Imagine old grandmas’ 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.

46Grocery Store Show

Inappropriate and admirable, that’s my take on this photo. She obviously has planned it all, but my goodness… I don’t even care about cute ass pornstars at this point, this is the one. 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.

45Teen 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 is, we all know that this teen is good with balls. Taking a picture at the comfort of her own home and 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 drink and the fragrance of warm pussy fills your nostrils.

44No Panties and No Shame

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

The only bad part is those green heels. It does not match with anything, unless she has Hulk eyes. She could learn some fashion rules as I pound her. My love for petite women is at the peak, and this one is perfect.

43A Secret Upskirt Pussy Shot

So, your girlfriend wants to have some fun and you both are out of ideas. Here’s one! Why not take a decent length dress, remove panties and just take 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.

42Exposed Skirt Slip

Fucking epic, ridiculous and all kinds of mind-blowing. I am certain 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 non-sense 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.

41Girls Changing

If you are one of those guys that 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 then another is to have your nipples showing 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.

40Hot Nurse with Her Upskirt Reveal

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

Slightly chubby? Maybe. Nonetheless, don’t you fucking 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 in reality.

39Picking 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 what they can’t see is 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.

38Exposing 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.

37An 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 and in this case, it’s the inverse upskirt shot.

One happy slut and many men watching her, also happy.

36An 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. Take your hand off your pussy or dick for a moment and study this one, or any other pic. 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.

35See Through Panties

You can almost see her pussy lips on this one, all thanks to the magical panties. I’m so grateful for all the cheap Chinese underwear and other outfits. One would not have this kind of low density if it was an expensive brand.

34Upskirt Sideways

One of those too good to be real pussy shots, but I will accept it. Just a random amateur, MILF or a teen college student, lying on her side.

This could be a perfect ad for one of those plastic vaginas. It’s just there, bro. Come and stick your dick in.

33Teen Upskirt Pic with Panties

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

Anyway, you can see her panties and a nice blue dress to match the pink.

32Kinky GILF Skirt

Okay, who makes these short skirts anyway? No-one wears them in public or I live in the wrong neighborhood. Is this just for sex games and other adult games? Whatever the case is, this GILF managed to snap a one stunning photo.

31Pussy Tattoos and Short Skirt

Okay, this must be Japanese. Who else would tattoo tentacles and other non-sense if it wasn’t for crazy Asian girlfriends? I’d say this is on pair 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.

30Let’s Just Fuck

Forget the panties and forget taking things slowly. Pull your cock and smash her until she collapses from the exhaustion.

Cheap, semi-transparent dress and a dark room. What could possibly go wrong here?

29An Afternoon Pray

These accidental upskirt pics always get me, and I do mean the setting. That’s the exact view you would see if some teen would be 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.

28College 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 few pics and jerk off to this memory for the rest of decade.

27Accidental Upskirt Pussy Slip

You invite your good friend for a night out, and you just randomly take pictures as you both talk… The night approaches, you do few more shots and leave with blue balls, just like every other night. She in the other hand complains about her current boyfriend that 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.

26Like What You See?

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.

25Dress Up, Panties Down

See that asshole? It’s as reliable as a new Toyota, and boy 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 a boring as random YouTube videos, just doesn’t do it for many of us. At least there is a girl in this top 50 that is open for something dirty.

24Sexy Shopping

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

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

23Windy Day

I’d like to think about the scenario in which this picture was taken. Obviously, she was the one to lift her dress, but what was the discussion? Oh, 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.

22Wet 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?

21Horny 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. Anyway, 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.

20Slut 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.

19Short 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 spray to go from 6 to 10, but we have the whole summer in front of us.

18Tits, Ass and Abs

I swear this outfit has been making rounds out there. This isn’t the first slut to have 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?

17Reaching for Something

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

That’s what makes me excited!

16It’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. Of course, she has no panties and behold, the shocking reveal of her pussy!

15Upskirt with Panties

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

First, you can see her right lip and then there appears to be hair bits? Looks like she did not shave all her places and did want to trick the camera.

14Mirror Upskirt

Ask men to design buildings without any 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 worse. What if it was a fat female convention?

13MILF Pussy Reveal in Public

College teens are not the only ones who are crazy in public. Here’s one trashy, attractive and definitely naked MILF, casually sitting in the chair. However, it does not take a rocket-scientist 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 few more years and improve the looks.

12Lifting Her Skirt

Having personally collected close to 50 of these, I can now safely say that in the end, men just want to fuck. 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 afterwards, marry her.

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

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

11Just a Spin

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

10Upskirt Masturbation

Another heavy hitter, and this is straight form 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.

9Kitchen 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 pair with most homemade videos. She does not act too obvious, but we get it… It’s staged.

8Dirty Shoppers

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

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

7An Obvious Upskirt Attempt

Well, this one is just that, a lonely girl and her long dress. Not liking her pussy look, but it’s better than fucking your own hand. At least her sense of fashion is admirable. Bright clothes, great colors and the rest is okay too.

That will do pig, that will do.

6Date without Panties

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

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

5Playing 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.

4Bending Over in College

You are stuck in the dorms and your boyfriend is now coming as it’s snowing 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.

3Free 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 be sure that you want are making a correct decision. No cumming inside allowed, you’ve been warned.

2Teen Upskirt

Another of the kitchen 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 clearly a woman of dreams.

1Dirty 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 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?

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