All of this takes place online, so this isn’t your usual story but still an interesting experience. I don’t know much about the other participants in this story so let your imagination fill in the gaps.
Being a bit bored in the evening, I headed over to Omegle just to pass the time. As opposed to heading over to the cam / video section and seeing old men wanking, I headed over to the chat-only option. After entering a couple keywords so we had a topic to talk about when we matched, I started spinning the wheel. Still about 90% of dudes but that’s only expected I guess.
Never really had any interesting experiences before and wasn’t having much luck tonight either, so was about to close down and head to bed when all of a sudden this happened. The below is full transcript, edited slightly to make it easier to read but no changes to the story nor dramatized.
**You’re now chatting with a random stranger.**
**You both like free use.**
You: hey
Stranger: hi
You: how are you
You: m29 here
Stranger: i’m good
Stranger: f20
You: oh really, are you rreeeaall?
You: so many bots here have to ask hah
Stranger: yes, I’m real :)
You: hah cool
You: so you’re into free use?
Stranger: yeah ;)
You: as a fantasy or as something you’re actively doing with your bf?
Stranger: we’ve done it a few times
You: a few times? how does that work? it’s not something you turn on / off is it?
Stranger: It’s a little bit of planning, which isn’t so fun, but like, ‘hey, want to put it on the table for this weekend?’ and then we know what to expect
You: put it on the table
You: quite literally hehe
You: what brings you to omegle and this topic then?
Stranger: just wanted to fantasize about it and work off some horny energy?
*At this moment, I was like, shit, this is happening. I’m on omegle and finally talking to a horny girl but not having any clue how to proceed from here. A somewhat awkward conversation followed.*
You: nice, if you’re horny then you need to take care of yourself
You: I recently made a list with loads of fantasies that I have, one of them being going away on holiday / road trip and being free use during that time
You: just adds an extra element to it, rather than just doing it at home. Could have different plays in different places during the holiday
Stranger: totally. i’d love to have, like toys, with it too. wearing a plug or viberator to play with and tease
You: ah yes, a remote controlled bullet
You: or vibrating panties
You: Need to scout out a few cities near mountains where they have a gondola ride going up
You: need to be quick, but could be fun to go down while going up 😏
Stranger: sometimes it’s more fun to know you only have a little time, that you might not finish, but you’re going to use each other anyway
You: exactly
You: Tell me about the times you did free use, what was the most unexpected moment? Or was it just straight fucking the whole time until you’re sore?
Stranger: My favorites are when I’m writing on my computer, and he’ll just put me onto my stomach and my knees and start by eating me out and then fucking me, usually slow, like we have all the time in the world.
You: hm that’s hot, would you wear different clothes during a weekend like that? easy access is helpful I imagine?
Stranger: usually loose clothes, we both like sweatpants, even if it’s not as easy as skirt, because of, like, putting them back up and going back to normal things
You: ask me a question or tell me something
You: seems like I’m asking all the questions here haha
*I wasn’t sure how to progress anymore and the conversation seemed to die out a little bit. Lucky this helped!*
Stranger: Do you prefer rough when you do free use? Or more of a build up?
You: Hmmm I think free use and how you’re being used should be a surprise every time
You: so a bit of a mix I guess, sometimes straight in there and hard fucking, while other times first rubbing a little bit over any clothes before going further and slowly building up
Stranger: the surprise is kind of a good part, i agree. Like, first, just that it’s starting and then how you’re being used
You: yeah exactly
You: how is that horny mood of you going? why don’t you ask your bf to come over and eat you out?
You: while we chat hehe
*Pushing my luck here I guess, but whatever, what’s the worst that can happen that she disconnects like so many before? Who cares. I was quite surprised with the response however.*
Stranger: that’s a good idea…
Stranger: would definitely work me up more, but in a better way, if that makes sense
You: let me know what he says after you ask him
Stranger: sure, one sec
**silence**
Stranger: mmm, he said yes
You: just yes hah
You: i guess he’s expecting something in return later though
Stranger: he said he wouldn’t make me cum, so it’s going to be slow but extensive
You: that’s kinda mean no?
You: so how’s your setup, you’re on the couch with your phone? in front of the computer at a desk?
Stranger: on my laptop, going to set up lying with a pillow under my chest and he’ll pull me up onto my knees
You: I see, you can’t see him then, don’t you prefer the other way around with you on your back so you can see him eating you out?
You: have you got any toys he uses on you?
Stranger: hmm, it’d be too easy to grab onto his hair that way
Stranger: some, though I think we forget about them when we do free use
You: I see
You: how’s it going over there? is he getting in there yet?
You: or still warming up slowly?
Stranger: he’s warming up, just little kitten licks everywhere while he holds me open
*Shit, this guy was taking his sweet time, still warming up, this was a good 5 minutes after he got involved – she was a very slow typer, her mind and possibly hand must have been somewhat otherwise occupied. Not sure what else to say at this point, ask her to have a look at my list of fantasies.*
You: have a look at this list I compiled : https://www.reddit.com/r/SexFantasies/comments/r8awwu/65_year_of_fun_my_sex_goals/
You: anything that interests you in this list?
You: or anything that you’ve done before?
Stranger: let me see
Stranger: definitely done secret head/fingering, both kinds of the threesomes. I’d love to try the sex with a tail buttplug and he says he’d try edging me
You: well from the sounds of it he wants to edge you right now, or is he just going to be a lazy pussy licker and not going to get anywhere near?
Stranger: going slow like he’s doing gets me really wet, but not anywhere near cumming
You: sounds like he just wants to get you incredibly horny so you will do anything for him hehe
You: will you?
Stranger: definitely ;)
You: you shouldn’t give in so easily
You: need to make him work for it a bit right
Stranger: I really like him fucking me though
You: I think he should make you cum first this time
You: and then you can cum again when he’s fucking you
Stranger: he says maybe you can pick how he fucks me
*I mean I was kind of already planning this, but this was promising.*
Stranger: fuck, he’s licking deeper too
You: sounds like it’s getting steamy in there
You: tell me about the time you gave secret head, if you still can concentrate
Stranger: okay
Stranger: we were early to a party, just a few other people there. I said I would suck his cock and he could pick wherever he wanted us to do it. Of course, he chose the corner, which was at least a little dark
Stranger: we could hear our friends in the kitchen, and I took as much of him as possible right away and he grabbed my hair to keep me going fast
You: must have been quick blowjob? hope he came hard inside your mouth
Stranger: I wasn’t ready and some spilled out down my chin
You: hope nobody saw it and you cleaned it up
You: is he still licking you right now?
Stranger: he’s got his fucking tongue inside me, moaning and making it hard to type
You: you’re getting closer?
Stranger: I’m trying to ride his face, but he won’t let me
You: is he eating you from below?
You: or is he just behind you?
Stranger: from behind
You: tell him to get below you and then you can slowly adjust yourself so you’re sitting on him
Stranger: mmm, yeah. that’s really good, he’s a little deeper too
You: just let him do his thing for a bit and then in a minute or so you can start taking control and riding him
You: and don’t stop until you cum, just tell him you’re close if he wants you to stop
You: do you think you can do that? or is he going to throw you off and start fucking you
Stranger: yeah, yeah, I can do it.
Stranger: he’s going to spank me as I ride him, i bet
You: go make yourself cum and come back here to let me know how it went
Stranger: ookay
**silence* Every time when there was a long silence in the chat I thought I had lost her and they went off to fuck. Maybe 2-3 minutes later she came back, and let’s say, she was quite happy.*
Stranger: oh fuck that was really good
You: are you ready to be fucked now or do you need a break?
Stranger: yes, please, ready to be fucked
You: is he hard?
Stranger: definitely ;)
You: get him to stand next to you at the laptop, and stroke him a little bit while I explain
You: we wouldn’t want to lose momentum
Stranger: okay
You: bob him up and down a few times, but not too much just to build anticipation
Stranger: nice and slow
You: go down as far as possible and just stay there for 2-3 seconds before coming back up
*At this point I was pretty tired, considering that I was about to log off and go to bed when this chat started, now about 40 minutes later. So I prepared a grand finale and last push and let’s see what happens.*
You: now I want you to choose between doggy or missionary, don’t do it yet but tell me which one you prefer
Stranger: doggy
You: ok, in a moment get into position so he can enter you, while he enters you I want him to film how he slides in that wet pussy of yours that just orgasmed. No need to make a full sex tape out of it, just sliding in and a few thrusts 15-30 seconds
You: after that go wild, fuck like rabbits
You: once you’re done, maybe you’d like to send me a private message (reddit) with the video – if you dare?
Stranger: if it’s any good, maybe
You: Oh it will be good
You: any questions? Do you need any further instructions?
Stranger: no, no, just tell us when
You: enjoy, I look forward to your message later 😉
Stranger: thank you ;) ;)
*I stayed on the chat, while I was taking care of some personal things, just in case they wanted to chat after. God knows how long they were going to be though. Some time later, maybe 5-10 minutes*
Stranger: mmm, you still there?
You: sure am
Stranger: kinda fucked out right now
You: where did he cum
Stranger: inside me ;)
You: Do you want to taste it?
Stranger: yeah…i do
You: grab his hand and take one of his fingers in your mouth to make it wet
You: then just take his hand and force that finger inside your pussy
You: then rather than sticking it inside your mouth again, slowly lick up all the juices from his finger with your tongue
Stranger: treat his finger like his cock, licking and licking
You: Exactly
You: how’s your horniness now? Satisfied?
Stranger: fuck yes
You: well this was fun
You: bit more so for you guys than it was for me
You: but still fun!
Stranger: so much fun, and very unexpected
You: hah, same for me
You: this isn’t really what I had in mind when coming to omegle
You: not sure what I had in mind, just wanted to pass time
You: hows the video looking? or did you 2 chicken out of that one?
Stranger: ha, me too
*There was a long silence, I didn’t want too be too pushy about the video, and maybe she wanted to say something else. But then it happened.*
**Stranger has disconnected.**
Whether there’s a video, or no video, we might never know.
Source: reddit.com/r/gonewildstories/comments/rc3g5y/i_m_gave_a_girl_f20_instructions_on_how_to_get