The first time I [F] had something in my ass was on Omegle

I was 19 at the time that this happened and had just purchased my first dildo.

When I got back to my dorm room after classes were over, I entered to see my roommate wasn’t there so I decided take a shower then hop on Omegle. I hadn’t been on the website since I was in high school, but I had fond memories of it and was horny so why not. The first person I was connected with came within seconds of me taking my shirt off after I had been teasing him for a while. I was disappointed I didn’t get to show off my freshly shaved pussy but so turned on by the cum and wanted more. The next guy and I were able to have some more fun. I started off by just smiling and rubbing my hard nipples through my shirt. Then I whipped out my new dildo and spent some time slowly kissing it, drooling on it, and licking it up occasionally. When I saw his dick jump I swallowed it whole and showed off my bulging throat. He came a huge load instantly. I still hadn’t cum myself so I decided to stay on.

I spent the next 30 or so minutes making multiple men cum. Then I came across a guy (around 30 years old) in VR glasses and that’s when things got interesting. I teased him and stripped like with all the others, showing off my huge tits and tight pussy. Apparently he wasn’t satisfied by that and asked me to flip over so he could see my asshole up close too. I spread my cheeks and backed up a little closer to my camera. “That’s nice baby now put a finger in” he said starting to stroke a little faster. I hadn’t tried anal play before so I was a little hesitant. “Be a good girl for daddy”. I made a big show of sucking my finger to lube it up then turned back around and gingerly inserted it up my unsurprisingly tight virgin asshole. I gasped at the sensation but got so turned on I stuck another in and started fucking myself without being asked.

As I was about to reach climax he told me to stop and so obediently I did. “You know what would make daddy really happy…” he asked “if you put that dildo in your ass”. I wanted to say no way since it was my first time doing anal play, but I knew deep down it was what I was craving I was just too shy to admit it. “How about I put in just the tip” I said. I spit on the head of the dildo and added some lube around my asshole just for good measure. I took a deep breath and pressed the dildo against my ass until I felt it slip in. It wasn’t painful like I thought it would be so I went a little deeper. Eventually something came over me and I started fucking myself with the dildo. Hard. It started to slide in and out with ease so I went a little faster taking it to the base and then all the way out again quickly until I came so hard I couldn’t move.

I lay there face down ass up both holes twitching to the camera. When I turned around I saw the VR guy had skipped me and I was on full display for another man. That’s when I heard keys jangling outside my door. I thought it was my roommate so I hastily closed up shop and pretended to be asleep. It turned out to be the girl next door but I was exhausted from cumming so I just took a nap anyways.

Source: reddit.com/r/gonewildstories/comments/ld77n6/the_first_time_i_f_had_something_in_my_ass_was_on