I [20F at time of this story, F23 now] use to love sexting and playing with strangers online but I ended up stopping once I got a bf [22M]. Long story short, we ended up breaking up for a whole number of reasons but one of them being that I felt like we weren’t sexually compatible, I wanted to explore more and felt like a caged bird. The night we broke up we had tearful breakup sex and he left with his essentials and in a whir of emotion and loneliness I found myself back on the sites where I use to sext and play with strangers. Up until that night I had never met a stranger for fun before but my emotion took over, I made plans to meet with the first person [24M] I connected to in my city. We chatted about our kinks and he mentioned an interest in pegging and I already had a strap on from a previous relationship but had never pegged a man before (This next part of the story was extremely dangerous and I am thankful that nothing bad came of it, I have learned since then I swear!) I met this random stranger in his hotel room and I let him fuck my pussy raw hours after my ex boyfriend had fucked me for the last time… I felt so dirty, like I couldn’t go even a handful of hours without shoving a cock up my greedy cunt. After he fucked me raw I slipped on my strap and started fingering his asshole. He said he had never been pegged either and wanted to try it. I will always remember the sound of him groaning and squirming against me while I stretched him all the way out for the first time.