Losing my anal virginity post breakup [FM]

*Skip to the ———- for the sex* (kinda long)

I[F27] had broken up with R[M30] a few weeks ago after the last several months of the relationship had felt like constant fighting due to personal battles. Despite his low sex drive, the sex had always been great and was still getting better by the time things had ended. We’d recently started getting into ass play but had never made it all the way. It was beginning to frustrate me a bit to get so close then just not.

Fast forward to last night. I texted R, asking if he’d like to get coffee. He hadn’t been handling the breakup well, and we’d barely been speaking since, but I wanted to make sure he was okay. Shockingly, he agreed. R was tense and on guard, as expected. Despite saying nothing’s changed and he’s not doing well, he was looking better. As I was driving him home, I turned the conversation to how I didn’t understand why he didn’t just fuck my ass, when I’d made it clear I wanted to try. There had been so many occasions where I’d come over with lube and it was just never used. He didn’t really have a reason and there were no implications from the conversation. I figured that was that, as he’d already said sex had been on his mind even less than before.

As I pulled into the driveway, R asked if I’d like to come in to see the pets I’ve missed. I said no, as I wasn’t getting the feeling he wanted to be around me, and I didn’t want to complicate things. But he insisted that he wanted me to come in and that it wouldn’t take too long. My eyes lit up as it dawned on me what R was wanting- this was the last thing I expected.

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I followed him inside and to the bedroom. We wordlessly get into bed and started kissing. Soft slow kisses building as our hands grabbed all over eachother and he slapped my ass. I had been dizzyingly horny for most of the last couple weeks. So much so that, with plenty of lube, I had even succefully fucked myself in the ass with a sizeable dildo. We quickly stripped down and R went right to my nipples, licking and sucking them gently as I felt myself getting wet. He positioned himself at the entrance into my pussy, and had no problem sliding all the way in. We gasped at the feeling after so long, having been nearly a month. R began fucking me slow and deep. Punctuated by passionate kisses on the lips and neck. I knew I’d end up with hickies but didn’t care. I traced his lips with my thumb and felt my pussy get even wetter when he took it in his mouth, looking me in the eyes while buried inside me. Soon he picked up his pace while putting a hand around my throat. I couldn’t help but smile and tell him to tell me how much he missed my pussy. Truthfully, I’d been thinking about his cock too, and I let it be known. When I asked if he wanted to switch positions, he said no, that he liked kissing me.

When R leaned back, I asked to suck it. Being short on time, I didnt waste any of it on easing into things as he kneeled by my face, swallowing his entire cock in one go. I moved up and down, gagging slightly when I reached the base, and swirling my tongue around the tip when I reached it, knowing that drives him crazt. I spread my legs, moaning into his cock as he rubbed my clit and fingered my dripping pussy with one hand, grabbing my hair with the other. It wasn’t long till it was my turn. R laid down in front of me, and ran his tongue along the length of my pussy, making me gasp loudly. He worked it expertly around my clit, licking and sucking, getting me wetter and wetter. Soon he was back to fucking me. I loved watching his cock sliding in and out of my pussy but I wanted to get fucked from behind before he came.

I turned around and got on all fours. R grabbed my ass with both hands as he pulled me onto him, bouncing me on his cock. I told him to finger my ass as he fucked me, and felt that intense feeling of something moving in and out of both holes. It wasnt long before I felt him pull out and position himself at my asshole. I know I’d brought up the topic earlier but I wasn’t expecting any of this tonight. We didn’t even have any lube, and I didn’t know how prepared my body was. Despite my concerns I was determined to give it my best try- I’d been practing for this moment on my own after all. My breathing quickened and the pressure and pain of R slowly stretching out my tight asshole. I gasped loudly as I felt the pop of his head pushing all the way through. Much of the pain subsided until he bottomed out. He slowly guided me into laying flat on my stomach as I got accustomed to the feeling of a cock deep in my ass, checking in to see if I was okay. R slid his hands up to interlace his fingers in mine. I gripped them tightly, assuring him I was okay, and that I wanted him to tell me how it felt. He continued thrusting slowly, still holding my hand, whispering in my ear how tight and hot it felt. I couldn’t believe I’d actually done it. The pain of R being balls deep in my essentially virgin asshole was almost too overwhelming, but I was determined. He worked his way up to  fucking me at a steady pace as the pain disappeared and my body began to relax. All I could think about was my ass being filled with cum. This position is his kryptonite and it wasn’t long after saying what I was thinking that R finished, pumping into me what I could tell was a huge load. He stayed inside me for a moment as we relished the accomplished, before pulling out to lay beside me.

Source: reddit.com/r/gonewildstories/comments/l421j2/losing_my_anal_virginity_post_breakup_fm