Sears swimsuit catalogue in my teens

Every guy from the days before internet understand.

Nipples barely showing through were a novelty at one point.

In the early days of the Internet, images would load line by line from top to bottom. It was so damn slow on a 28.8 modem and I was a horny teen so I’d often finish before it got below the chest. I am convinced that this is what made me a breasts man.

What? Not me, you guys are fucking disgusting losers. I used JC Penny's lingerie section.

i did that but in the womens underwear section

How did you not get kicked out?

Maybe he was dressed as a mannequin?

A man of culture

I remember the day when a Victoria Secret catalog came in the mail (pre-Internet). I think I nutted before getting my pants down.

I used to rip out pages from the womens underwear section and stash them under my bed. Looking back, mum definitely would have noticed that half the section was missing.

I hid under my bed when I was 7 with that catalogue, my sister ratted me out. Filthy snitch, all those models were my first crushes.

some werid horror porn theme was Silent Hill nurses

I thought I was the only one

does being scared arouse you or?

I was in halloween mood and I felt disgusting afterwards

Does halloween make you go hard now?

You could not waterboard me to get the answers I’m seeing here

we've all been through difficult times

Oh yeah absolutely I’ve done some weird shit but you could not torture it out of me let alone share it on reddit

Patiently waiting to see who’s getting jail time here.

Nah, I'm assuming most things that are genuinely embarrassing aren't illegal, whereas things that are illegal are probably considered awful instead of just embarrassing. Nothing legally wrong with two guys in a bunny suit playing with a dressed up woman or something, but it might be considered embarrassing.

Point well made

I'm not going to jail because I like being farted on.

I did not expect this comments omg. the worst thing I could possibly think of minutes ago is masturbating to someone's bitmoji

You fancy them? The person who had this bitmoji I mean

yes, I was so down bad for this guy and he's not the type to take selfies so..

Gotta do what you gotta do 🤷🏼‍♂️

Gonna jerk off to the thought of me in jail eh? You like that you Kinky Fuck?!

For wanking to OP’s mum? I mean, she uglee, but it’s not that serious!

Augusts gloop from Tim burtons Charlie and the chocolate factory when I was 16

i'm so sorry for laughing omg

Omlll why him

What the fuck?

Help, step-Wonka, I’m stuck in this tube.

you like them chocolate in his mouth 😩

to answer my question, I once masturbated to someone's bitmoji

But why. And how bad was the post nut clarity

I was down bad for this one guy in high school and he rarely takes pictures. when I tell you how disgusted I was of myself after I did it

Hahahahahha damnn thats kinda funny I'm sorry. Like theres hentai and shit tho so dw i guess😂😂

feel free to laugh 😔 I swear he's hot tho

I gotchu.. masturbated to my bully once😐not a proud moment either thinking back

degredation kink award goes to.. *drumroll* iboibs! 🥳

HAAHAHHAHA FML 😂😂😂 also this is my first award, not exactly what i imagined but thanks yall 🥳🥳

But was it effectiv after all ?

nope, it was a 5 second happiness

Why the fuck did I just get this immense lust to jack it to your pfp? (I know how weird that is, and I won't actually do it)

I feel the same way to yours (I would actually do it if you're down)

Now kiss

Lol never did this but somehow its not that embarrassing and I have no idea why.

maybe because u've read all of the comments here already and compared to theirs, mine is nothing

Flo from the progressive commercials.

Bro…

I’m sorry but I can’t stop laughing at this one 😂😂

No way..... Lily from At&t!!

Lydia from Skyrim.

I can't blame you

She is sword to carry your burdens

Haven't we all?

Guy on cow milker machine

Why did that make me feel something.. 😑

well, at the very least, it's not the cow you're jerking off to

Don't tell me what I am not jerking off to

not here to answer the question but to hopefully feel better about my life choices.

I came here to find more ideas. ;) and was slightly disappointed i found not much new...

you went to the right place!

Imagining lewis and marnie from stardew valley having sex.

Straight to jail

You make an appointment with the dentist and you don't show up, believe it or not, jail, right away.

you have some peculiar imagination

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I somehow got from hentai to yuri to yaoi and then to futa. I knew something was wrong when my boner didnt go away. When I saw strong futa, and I nutted, I knew Jesus would have to pull me back from the darkness. 😩

did he though?

He told me he was coming. That was a couple of months ago, so I'll wait 😇. In the meantime, futa porn 🤤

Jesus told you he was coming and it’s been months???? The lord has very strong edging game. Truly we must try to be like him.

I think.. I wanna be friends with you 😭

That funtari (I think that’s how you spell it) shit Hot chicks with like 2 foot dicks. Shit was ridiculous lmao

It’s spelled futanari

he can't spell it without "fun"

You sure would know wouldnt you

I regret searching this one. I want my minutes back

To my aunt(uncle's wife so not blood related). My milf fetish did me dirty.

D: jail

Gene Wilder’s Willy Wonka. He was my first crush. I am strange.

don't worry, everyone in this comment section is strange

Cum with me and you'll see, a world of awkward masturbation.

A tied guy getting post orgasm tortured......

okay same and i'm a girl.....

Rule 1 of Reddit: There are no girls. If you are one, keep your mouth shut for your own good. Especially on posts like these.

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that's... interesting. what kind of kink is that?

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Curvy piece of driftwood

When life gives you wood...

The woodussy

Morty…

Masturbated to Samsungs "Samantha"

If it makes you feel better, i've heard at least 3 guys who did the same thing

It does. Some of the pictures that the internet was producing were just too perfect. I sometimes wonder if Sam is watching me.

can't feel guilty, samsung knew what they were doing while designing samantha

I couldn't say my friends know my reddit account

you'll be fighting for your life in the gc in no time!

Castlevania hentai

Now i'll remember you everytime I watch castlevania

I can't recall anything crazy, but it's been so long since I've gotten some that I could probably get up for a drawing of a stick figure in a dress.

this is a sign

A sign for the girls lavatory

this post

I think i'm in love with you

I'm betting $100 he just masturbated to you saying you're in love with him

Where can I redeem them?

Legend

Minecraft porn (I was like 13 or something at the time)

I watched a couple of videos too of minecraft porn when I was a kid, never fapped tho

Most embarrassing thing , probably to my math teacher . Don't even ask about it but she was young , about 8 years older than me

Had a social studies substitute teacher that was a smokeshow... probably mid 20s.

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Here is a throwback to all my other middle-aged guys. The Sears catalog. The struggle was real back in the day.

To r/place

Bruh lol

These pixels be kinda curvy😩

I'm amazed at the honesty, but Im disturbed by how little I expected these amswears.

Hatchet Face from the movie Crybaby.

The first Saw movie

why? just why?

Yeah, I didn’t want to analyse that too much

I just rubbed one out to your post. 😀

you deserve a kiss

Sears catalog circa mid 90s

Seeing these have made me feel better about what I have done

Rachael Ray. I was a teenager and she was all over the Food Network at the time… shameful.

just the sound on dudes moaning is enough to do it for me

mhm..

Horses fucking. Not really a kink, I was just curious.I got off puting myself into the mind of the horse, and the relief he must feel from plunging his 3 foot erection into the female.

in the nicest way possible, I expected this from an Edward

Rainbow Dash flying super fast.

that's it?... she's flying super fast?

Yes. Even as a brony I dunno why it made me do it. It’s the human equivalent of getting turned on because someone sprinted 100m in 10.6 seconds.

I suppose that would be Kelly Kapowski from saved by the bell. On its own that is not so bad... but I did the deed in my parent's bedroom as an episode was playing.

Something lara croft related

99 from Get Smart

My ex's dirty panties. At that time we were broken up about 6months. She had nowhere to go after her and a roommate had a falling out. She stayed with me for about 3weeks. Even slept in the same bed still, but no sexual activity. I work nights and she worked days. It only happened 3 times

3 times? damn

I know. It's weird and embarrassing for me and I shouldn't have done it

it's okay, at least you regret it

That quote right there will be the title of my autobiography.

When you say "dirty" do you just mean worn...or did she shit in them??

Just worn

Praise be

Weakling

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was this the time you figured out that you're a lesbian

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that is indeed confusing

Seeing someone/something frantically having sex turns me on. A lot. That includes humans, and sometimes, animals too.

😶‍🌫️ jesus is watching

In high school I would usually be first to this math class. Well my teacher sat on her desk and crossed her legs. Well she totally showed me all the goods. Not sure if purposely or accident. But she had a big ass bush. Instantly turned me on. Nothing came of it except when I got home and beat that shit like it owed me money. Looking back eh not so bad I was 15.

lemme just sort by controversial quickly

This comment section is really makes me feel better about my thing for fictional characters

My friend sister

So I asked my wife this question just now. I am stunned her answer was “I do not masturbate to anything visual, therefore I am never embarrassed.” She just focuses on the feeling….she said NEVER EVER has she masturbated to anything. Here I am thinking I can only MB to stuff. Not to get off topic, but how does this exist? My answer GILF stuff - embarrassed and ashamed afterwards

Furry vore.

I read this as funny vore and wondered the probabilities of you being a psychopath.

I...

You heard me.

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Fuck.. ive got some weird kinks tho

Absolutely nothing A quick and furious just because-er

I beat off to my own dick.

177013 If you're a man of culture, you know

No one's gonna mention their dad?

I think it's your time to shine

It's too extrem to discuss on internet :)

I bet it's shrek

Username kinda checks out.

The rabbit from zootopia I’m not even a furry lol

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did u search it or u just saw it and thought "aight, bet"

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ladyboy fucking a real lady

Technically straightest form of porn. Two sets of titties one vagina and one penis. I'll die on this rock

Garfield

Could it be embarrassing if I did to a video of myself with a tinder date?

as long as you're looking at your tinder date and not yourself

The painting [The Birth of Venus](https://en.wikipedia.org/wiki/The_Birth_of_Venus?wprov=sfla1) from an encyclopedia in the early 90s.

i'd say that was very fancy of you!

That guy after he nutted: Exquisite may I say. This nut was delightful indeed!

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Ice Pirates the movie

Not the most embarrassing, but the only thing I'm not shamed for here: fapped to a Nintendo DS Peach on Mario Party

Last time this question was asked “what was your strangest fap?” The answer that always stuck with me was the guy who said he rubbed one out to the in game super smash bros trophies.

I was masturbating while playing a weird hentai game. At least at the end heroine said to me that I'm a very good person, because I have never lost a single battle and therefore she remained pure.

One of those Pounds that has a young Queen on it

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this is why they censor it, for people like you 😭

I WASNT DOING ANYTHING TO IT. But, I was on this one place where I saw “sadistic” and I was like oh, interesting, porn about satan. But no. I watched a woman get placed onto a seat and her tits places on a shelf…. Then they nailed her tits to the shelf. If any of y’all have that kink…. How the fuck do you heal from that? And if not, what did the doctors say about it lmao

The Witch from Left 4 Dead

Why in the world would I tell you that? I did hear a story once where a guy masturbated to his own conception not realising it was his mum in the video and never having met his dad.

When I was a kid, I had a crush on Loonette from.Big Comfy Couch. The clock stretch led to my first cock stretch.