I’ve been sharing a lot of firsts recently (losing my virginity, first time fucking a girl), so I decided to share the story of how my ex-boyfriend took my anal virginity. He eventually took me from an anal virgin to an anal-loving slut, though, not right away. Honestly, it took about a year of hard work and dedication from both of us… We broke up about 6 months ago, and I actually still haven’t let anyone else fuck my ass yet, so he’s the only one who ever has. I’m Sophie and use reddit to share stories of my past and present sexual adventures. I’m writing this one at 5:30 in a coffee shop/wine bar near my office after work still in my little black office dress, which feels pretty naughty. Hoping that no one sitting behind me has good enough eyesight to see my computer screen.

 I’m sure there will be a few stories about my ex, Ben, so I think that warrants a little bit of background. When we first met, I was actually dating someone else and so was he (oops). It was a steamy, long distance workplace affair at a previous job of mine. We worked for the same company but lived in different cities. He was handsome, much more senior, and quite a bit higher-paid then me. Before we actually started dating he’d fly me out to hotels in various cities to fuck. Eventually, we both ended our other relationships, I moved to his city and moved in with him. As you might imagine, our relationship was kind of destined to crash and burn. But while we dated, we did have a lot of really hot sex, and we’d often have threesomes with other girls. Hence, the reason you’ll be seeing some future stories about our relationships.

But, back to the story at hand. During the pandemic, we weren’t traveling and we were both stuck at home bored out of our minds. So the two of us started sexting aggressively during this time. Turning him on and making him cum drove me crazy, and the thought of him getting off to a video or photo I sent him makes me instantly wet. I loved getting pictures of his perfect cock, and videos of him making a mess with his cum. As we chatted endlessly about things we’ve done in the past, and our sexual likes and dislikes, things got increasingly kinky. I told him that even though I had tried before with a couple of partners, I’ve never been able to successfully have anal sex without it hurting too much,  but I knew that the thought turned him on. In an attempt to make him a video that I knew would drive him crazy - I once made him a video of me putting a butt plug in and getting off with it in. He liked it even more than I expected which made me very happy and turned on. Not long after that, he told me that he really wanted to cum in my ass the next time that he saw me.

The thought of him using me like that and being the first person to ever cum in my ass definitely turned me on, even though the thought of anal didn’t really turn me on very much at all. I told him that even though it had not worked in the past, I’d be willing to try again with him. I thought that maybe if I was turned on enough it might be a bit less painful. This all seemed a bit hypothetical because I didn’t really have any idea when we’d actually be seeing each other next, if we even would at all.

However eventually, the pandemic started to ease up, and it seemed like our schedules would align nicely, and we decided to meet for four days in a hotel in Vegas. Both making up excuses about a fire-drill work trip to our SOs. By this time, we had a laundry list of things we wanted to do and him cumming in my ass was definitely on that list. However, we spent the weekend building up to it… The first night we just our typical dirty, passionate sex. The second to last night we were there, he started playing with my ass, and experimented with using a few fingers. The third night, we fucked while I had a butt plug that I had bought specifically for this occasion. 

Then, our final night there he asked if I was finally ready to try. I was quite nervous but really wanted to do it for him and show him what a good girl I can be. I flipped over, he got the lube, and very very slowly started to try and push himself inside. However, it caused a searing pain as soon as he tried, and I tensed up. He was telling me to relax and going as slow as he could, but it just hurt so bad and each time I reacted by just trying to move away from him and tensing up. After a few minutes, he gave up and said I’d have to be more relaxed for it to work. I got super sad because I felt like a disappointment, and like we had talked about it so much only for me to him let him down. He assured me this wasn’t the case and we left go out to a fancy dinner.

We got back from the Vegas steakhouse feeling quite drunk and started hooking up in the bathroom. We were literally on the bathroom floor when he said “you should let me try to fuck your ass again.” I got scared and tense again, but I really wanted to try again – I wanted him to take my anal virginity so bad. I didn’t say anything but just nodded my head yes. After using some lube, he started to try again. It hurt just as bad, but I remembered him telling me to relax earlier so I tried as hard as I could to just lie still and let him enter. It felt like forever before he told me that he was fully in my ass, and he slowly began to thrust. It hurt badly and I felt paralyzed on the floor, yet somehow accomplished. After what felt like forever to me, but apparently was only a minute or two, I started begging him to cum because I didn’t know how much more I could take. He started going much harder and told me he was about to cum. I felt a wave a relief wash over me despite the still searing pain, knowing it was almost over, and then he filled up my ass with cum for the first time ever - as I anticipated I thought that was super hot, and it turned me on later to think about. I told him after that I wasn’t sure if I’d ever try to have anal again. 

But, flash forward about a month, and I was planning to go visit him, and I had already told him I wanted to let him fuck my ass again and had been teasing him with videos and pictures with my new pretty butt plug – that I bought just for him. I was nervous knowing that it would hurt, but it gets me so turned on thinking about how much he likes using my little asshole to make himself cum, even as I struggle and writhe on the floor. I put in my buttplug as a surprise for him, so when he ordered me to go put it in, I smiled and told him it was already in. He pulled me onto the floor, and I gave him a blowjob on my knees while he could see my buttplug in his bedroom mirror. I was already enjoying feeling like his good little slut. I love the nervous anticipation of knowing that he can do whatever he wants with me and that I can’t stop him once we start. He turned me around and started fucking me on all fours while my buttplug was in until I came hard on the floor. I knew what was coming next… I was about to let him fuck my ass for the second time…

He pulled my buttplug out, started to slowly try and push himself inside, I felt the same sharp pain that I do each time, but this time I was a little more confident that I could take it. That didn’t stop me from subconsciously trying to wiggle away though. He went slow at first, continually re-adjusting my body and holding me still in the best position for him. He pulled my face back towards him to makeout with him while his cock was pushed as far into my ass as he could go. He was fucking me on the floor, and I kept searching for something to grab on to with hands because of the pain. It wasn’t long before I was entirely overwhelmed again, and just started begging him to cum so it could be over. At one point he slipped out of me, and I yelped out a bit in dismay because him going inside of me is the most painful part. I would never want to ask him to stop before he cums inside of me because I love hearing how good cumming in my ass feels for him. But it backfired, because once I started begging him to cum, he grabbed onto my sides, and started fucking my ass much harder than he had the first time. I didn’t know if I could take it and I felt like I was on the verge of tears. I just told myself it would be over soon as I kept writhing and whimpering. Finally, with a few hard thrusts, I felt his cock start to pulse and I felt the two or three warm streams of cum filling me up, as I basically collapsed into a heap on the floor. As I laid there, he called me his good little anal slut and all I could do was nod in agreement while I hid my face, feeling very used… 

Eventually, he helped pick me up and cuddled with me and made out with me on the bed, and soon he was starting to finger me and tell me what a good girl I was for letting him use my ass and telling me how wet I was. Then he pushed his cock inside of me, filling me up, which felt incredible as it always does… He started choking me and fucking me incredibly hard. I loved the feeling of belonging completely to him, letting him fuck me in whatever hole he liked, and being told what a good girl I was. In that moment I felt both protected and used at the same as he was on top of me, enveloping my body, fucking me increasingly hard. I was so incredibly wet, and soon I felt an orgasm building. I just wrapped my body as tightly around him as I possibly could, and started to cum, and before long, he started to cum inside of me too. I fucking loved the feeling of him filling me up with cum just a few minutes after he came inside of my ass. After he pulled out of me, I wiggled in between his legs and started to clean off his cock, tasting us both mixed together, enjoying the feeling of being in his lap. After this second time, I basically knew that whenever I saw him, I would let him use my ass without any control over how rough he is, or what position he wants to have me in. I loved the feeling of being a good little slut for him way too much…. 

Hope you enjoyed my story. Check out my page for more stories and let me know what I should share next :)