Stripping for strangers on Omegle for the first time 20[F]

As I mentioned in previous post, I’ve been very sexually repressed my entire life and have struggled with showing people my body (even in basic ways like with semi tight jeans). And in person, no one has ever seen me naked. I decided to make a slut bucket list to slowly embrace my sluthood and do more and more slutty things.

One of these things was stripping for strangers on omegle, inspired by a challenge suggestion on r/stupidslutsclub.

I went onto omegle at night, when everyone else at home was asleep. I felt nervous and uncertain, and I really really wanted to strip. But because of my nerves I decided I’d be happy if I could even just grope my tits over my clothes for today. That was my goal for that night.

I’ve gone on omegle in the past and I have been annoyed with the constant flailing dicks. Even when I went on it this particular night with the intention of putting on a show, the dicks annoyed me. This night I felt nervous and so the obvious horny men felt like far too much to jump into straight away. So I skipped past all of the dicks.

I ended up on a man’s chest and decided to talk to him. We spoke for a good 15mins, mainly about the weather. He pretty much immediately hinted at why he was there. He told me thats he’s topless because of it being so hot, then asked me if I’m hot too. I didn’t take the bait (yes, I know I should have, but I was very nervous and defaulted to pretending to be oblivious). After a while he asked me what I’m doing on here so late and I decided to just outright say:

‘Honestly I’m here because I want to strip and play with myself in front of strangers’

He was pretty shocked and excited over that. ?

I did then elaborate and explain that I’ve never done it before and that I am very nervous, so that probably won’t happen. But it’s what I want.

He was super gentle and understanding. He asked if I’m comfortable and told me to not be scared but that he’s going to stand up. So, he did, and put his hands in his pockets and started moving them around.

I got confused and asked him what’s in his pockets, to which he showed me there’s nothing. And so I was very confused as he continued moving his hands in his pocket till I realised and asked ‘Oh! are you touching yourself?’, and he explained that he is…yes I can be a bit oblivious at times.

He asked me if I’d like to see his bulge grow, and I enthusiastically said yes, so he told me it’s my turn to take my top off now. I was wearing a blue cotton dress with black pants underneath. I reached down, hesitating a few times before I moved to slowly take it off. I was wearing a pink lace bra underneath.

He complimented me a lot which made me feel quite happy. I loved the attention and positive words. He then said it’s his turn, so he started obviously rubbing his bulge over his shorts.

He then told me to drop a bra strap. It sounds so ridiculous, but I started heavy breathing pretty extremely loudly at this point. Almost hyperventilating. I hadn’t expected myself to get anywhere near nude with someone I’d just met but it was approaching and feeling more possible. And I felt so lusty and I wanted to so bad. I dropped a bra strap. He then told me it’s his turn and he touched himself over his shorts, and then told me to drop the other bra strap. So, I did. My bra was precariously perched on top of my boobs. My boobs are medium-ish, size 34C/D.

He said he really likes backs, and wanted to see my back. So I held onto my bra, then stood up and turned around to show him my back which he complimented. I didn’t know that’s a thing but I’m glad he liked my back! He then asked me to unhook my bra and let it fall. I unhooked it and let it fall to my hand, where it just dangled in my hand as I froze there. He told me to drop it, so I did, and I then grabbed my boobs and covered my nipples to turn around. As I turned around I was laughing loudly at the absurdity of me choosing to cover myself when I was heading towards being entirely naked. He was relentlessly accepting and comforting and told me to make a handbra and sit down again.

I just loudly giggled for a while. I was finding it so fun. I’m pretty silly and laugh easily when excited, or nervous, or enjoying myself, and I was all of the above. I found it so funny that here I am, entirely topless, hiding my nipples from this guy who is probably going to see them in probably just 2 minutes anyways. It felt futile but I still felt shy and like I wanted to conserve some modesty for the time being. And the slow reveal felt so arousing. I was buzzing with so much excited arousal.

He then removed his underpants and let his dick spring out. He started rubbing himself as I sat there with my hands covering myself. He told me to rub my boobs, so I did, and I got pretty carried away moaning loudly and squeezing myself, keeping my nipples still covered. I worried I might wake someone up but I was just touching with wreckless abandon. He said, ‘Show me now’, to which I continued rubbing my boobs but moved my hands to the side, pushing my boobs forward so he could see my nipples. It felt easy to do that, I was so in the zone, so aroused, so desperate to show more. He said ‘Mmm brown nipples’. That made me very very happy. I didn’t realise that being complimented on my body could excite me so much.

He then asked me to do the entire unbuttoning, unzipping, and turning around to take my pants off. Between each of the steps he’d tell me to sit and watch him touch himself. I didn’t feel so nervous about taking my pants off, I was so horny and was feeling pretty obsessive at getting more naked at that point. So, I did this pretty easily. I had white lace panties on, and when I turned around, he commented on how we had matching underpants.

He said ‘touch her’. That’s so vague! So I asked ‘her? who’s her? Do you mean my belly?’ and I started rubbing my belly. And then smacking it and pretending to play a beat on it whilst giggling and bouncing up and down. He actually liked that! And said ‘that’s so hot, do it again’. That surprised me, but I did it again.

He was then more specific and said ‘rub yourself over your panties’, so I rubbed my upper thighs where my underwear was. I wanted to be a tease but only three seconds later I started rubbing over where my cunt is. And my panties were so damp! The entire build up to this point was amazing.

I can’t exactly remember the succession of the next few things that happened or what led to them or how. I was feeling horny and lustful and not thinking clearly, so it’s a bit fuzzy. I felt like I was on autopilot and just following his dirty suggestions and didn’t say anything in response to him. Also I had stayed up far too late for this (it was 3am…) so that doesn’t help either. I mostly just remember feeling overwhelming arousal and breathing really heavily and trying to make sure I’m not moaning too loudly to wake others.

He kept touching himself and instructing me to do more and more. I ended up taking my underwear off, and he ordered me to spread my legs and rub above my clit. He told me to rub slower but firmer, which was so sexy, being instructed to that extent and being made to hold back. And then he counted down and told me to stop. That frustrated me in a good way. He then told me to spread my legs more, and then spread my pussy lips, and repeat the same thing. I rubbed my pussy lips and showed him my wet finger under the flash of my phone.

He then asked if I’m comfortable, it made me really happy how he asked this repeatedly throughout. And he told me to lean against the wall and put my legs up on either side of the webcam, to display my pussy. OH MY GOD, was that so arousing. To show him a close up of myself. To present my holes to an absolute stranger who hasn’t even seen my face. And whose face I hadn’t seen. It was amazing. I felt so much exhilaration.

And then

And then his webcam fell.

I saw his face flash on screen and I looked away, knowing that he wouldn’t want me to see. His screen went black and he used the text function to tell me that he ‘nearly got busted’. He couldn’t get his webcam to work. He said we’d disconnect and try to find another again, and I was worried as I thought this wouldn’t work, but we tried it.

I put my cotton dress on to cover most of myself as I went through various people trying to find him, and at some point I stood up and felt a bit of wetness dripping down my leg that clung to the inside of my dress. I was worried im dirtying my dress but I tried to ignore it, and ignore my burning desire to touch to just click through people to find him. I THINK I actually pressed disconnect on him when I saw him again! But I’m not sure. I then kept clicking reconnect for the next 35 + mins (yes this is an absurdly long time but damn it I was desperate).

It didn’t work! :( I never found him again.

It was extremely late at this point but I was extremely horny and desperate. So I decided I’d try find another good person. Someone had their face out, so I decided to talk to him. We spoke for 10mins, and I felt too nervous to instigate and I worried that I might offend him or get rejected if I asked. So I didn’t ask him. He disconnected (or maybe one of our wifis were acting up) when there was a lull in conversation. I was sad, he was attractive, but oh well.

I decided I’d just go orgasm with my vibrator and go to sleep instead. It was 4am by now, and I had work the next day. I orgasmed to the thoughts of the first guy I stripped for.

I feel so horny and sensitive having written this, weirdly my body is almost tingly and my head feels sensitive to the touch of my headphones. Even now I keep obsessing over how I showed him my boobs and put my legs up and showed him my pussy and it is making me so excited.

I’m so excited to go on omegle again.

Source: reddit.com/r/gonewildstories/comments/l9dqxc/stripping_for_strangers_on_omegle_for_the_first