Early 2000's Chatroulette

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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NudeBaG
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Early 2000's Chatroulette

Post by NudeBaG »

Posted in General Discussion as well, but thought it could go here too, as I really DO want to know

PLEASE tell me if anyone had similar experiences.

Hey I personally haven’t posted in a while, but I know my partner has been writing.
I’ve had a bug up my butt for a while about this.
Been reminiscing and remembering a lot from my early teen years and the pre-hyper restricted internet.
I remember Friday nights with my best friend in the early 2000’s.
After school, I would go over to her place for sleepovers.
These events take place between the ages of 12 and 17.
It all started with yahoo checkers (lame, I know lol).
But remember, this was before online gaming on consoles was big.
We would mostly just chat with randos.
After 4-5 ‘normal’ and polite conversations that got boring, we would finally come across a guy that was just ‘looking to chat’.
After ALWAYS lying about the whole ASL thing, (we were always 18, F, Florida)
The guys would ALWAYS start asking for pics.
We never sent any, and the guys would always send a nude that was OBVIOUSLY not really them.
Like, most were too dumb to even crop out the borders signifying which porn site they took a screenshot of.
And the guys in the pics were obviously WAY older than the 15-18 year old guys we were chatting up.
But, whatever.
We weren’t showing anything, and we weren’t exactly ‘mad’ about seeing so many dicks, but they were always staged ‘professional’ pictures.

Let’s fast forward a year into our online activities.
My friends and I are probably 13-15 now.
Random Video Webcam Chat sites were huge, AND FREE.
Think Omegle and Chatroulette in their prime.
It was Friday night.
Sleepover time.
4 of us teenage girls at home alone in our pj’s.
All of us are still virgins, and our body’s are changing.
I know that at that age, I personally was probably the horniest I’ve ever been.
Now, I mentioned that the accounts we’d used in yahoo checkers were previously sent random porn pics, so, it isn’t like we are unfamiliar with what a cock and balls looked like.
All of us had seen plenty at this point.
But they were always gigantic ‘porn star’ cocks.
Not that I didn’t enjoy looking at them, but it wasn’t the same as seeing ‘a real boy in person’.
Anyway,
It’s Friday, parents are out, just us girls and one of my friends’ new computer WITH a built in webcam.
“Have you guys ever been on Chatroulette?” She asked.
After explaining what it was and that she had just tried it for the first time a couple nights ago and had already seen “SO MANY COCKS!” we all readily agreed to check it out.
We follow her to the computer room.
She sits down with the 3 of us huddled around behind her.
All of us are in our cute teenager PJ’s, btw.
She types in a website and ‘poof!’
There we are huddled and framed in one of 2 screens.
She hovered the cursor over the ‘spin’ icon and clicked.
It didn’t take take long before we had seen several completely naked guys, dicks in all shapes and sizes and even a few cumshots!
Hours went by.
It was ALL entertaining, but only ‘hot’ a few times.
Funny most of the time, with a few gross out moments.

I can go into more detail if requested,
But I was wondering if anyone else had any experiences with these kind of sites when they were in their prime.
Thesyguy
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Re: Early 2000's Chatroulette

Post by Thesyguy »

I remember Chatroulette back in the day, but to me it’s more just NM stuff; the guys seemed so proud and excited about their dick pics. I really only find ENM interesting, especially when situations go completely wrong and/or unintentional circumstances happen; and then people are left humiliated. 👩🏻👩🏻👩🏻☺️👩🏻👩🏻👩🏻

I was such a perv in that era, I liked those GirlsGoneWild videos back then, but now I feel creepy for watching them 🫣
Themarble
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Re: Early 2000's Chatroulette

Post by Themarble »

When I was around 14-15, me and a group of my friends all used a laptop at a house party to go on omeagle. At first we only saw people to talk to and spent time talking to them. One of the girls my friend really liked but after a bit of going between people, the dicks started to come out. Quite literally. Once it passed a certain time at night it was just constant dicks, people asking for dick ratings. We of course skipped or were skipped before we could skip. These guys were clearly interested in flashing for girls, but we found it hilarious.

Eventually we saw a girl around our age who flashed use a breast and the thing she was wearing. That was truly a night lol.
NudeBaG
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Re: Early 2000's Chatroulette

Post by NudeBaG »

Like I said, I might go into more detail, but at that time for my friends and I, we were ALL boy crazy and curious.
We all had different reactions over that period of time.
TONS of fun and exciting memories.
Oh jeez, it’s taking me back.
I think a few of my friends became addicted for a while.
Especially those of us that were more modest or shy.
It wasn’t like being in the same room as the guy, but still getting to see all the fun bits lol!
Jeez!
I was such a horney little shit😅
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Re: Early 2000's Chatroulette

Post by Themarble »

I would love to hear some more. What is the most memorable occurance? Like what time seeing a boy/dick on there is so vivid in your mind?
Thesyguy
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Re: Early 2000's Chatroulette

Post by Thesyguy »

Yes, I also need to ask about gym class. Back then I remember if the girls didn’t sit carefully I would look up their shorts so I could see what colour their underwear was.☺️ Are the girls actively peeking also? Because I remember this guy once wasn’t sitting properly in gym and he was wearing shorts and boxers and I inadvertently looked in his direction and I saw his dong. 🫤 (I was a prude and always sat carefully however)🧎🏻‍♂️
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