My Wild New Year's Anal Disaster

So I posted about going home for Thanksgiving and hooking up with my friend’s ex-husband because I knew he had a huge dick and wanted to try it.

I flew home again yesterday for family time and New Years, but mostly to see him again. We’ve been messaging a lot. I was also talking with my friend so it was like the dual POV romance novels I read where both sides have their perspective, except I was the slutty antagonist, lol. No HEA or HFN here 😅

We talked about what we wanted to do and arranged everything. He came to my hotel room last night. He asked if I was ready. I hadn’t eaten that day and had already used an enema. I masturbated anally with a dildo to somewhat practice and I was nervous but at least confident about hygiene.

We ate some gummies and then got naked and I kept my heels on like he asked. Still amazed how his dick went from normal to huge while I sucked it, like a crazy magic trick.

Lube and condoms ready but at the last moment he tried to pressure me to not use the condom but I made it clear that no rubber meant no anal since I expected to have PIV sex with him. He grumbled and it reminded me of why I don’t like him as a person.

I lay over the edge of the bed with my feet on the ground so he could stand behind me. His size and my nervousness made it frustrating to get it in and he was getting irritated, slapping my ass and telling me, Fucking relax! in a laughing way but also not so nice. It got to the point that I snapped back, I’m fucking trying!

When he finally pushed in it was pure agony. I felt like I was tearing in half. He started pounding away and it was like I was taking the most massive shit over and over again. I was gritting my teeth and sobbing, rubbing my clit while he fucked my ass. He was loving it and I kept waiting for it to stop hurting but it just was too much.

I think maybe he fucked me for a few minutes but it felt like an eternity. And then he got so turned on that I was “squirting”, but I wasn’t squirting I was just dribbling pee because he was fucking my ass so hard with that huge dick.

That was when I tapped out and told him to stop. He pulled out and while I’m panting and sobbing and still dribbling pee down my leg, he makes a joke about how gaped my asshole is, which utterly infuriates me.

I stormed off to the bathroom to pee and clean up. When I came back, he was just lying on the bed watching porn on his phone and jerking off and smirking at me. At this point I’m kind of hating him which makes the sex wild and angry.

I rode him like before, my ass sore as hell but still climaxing so hard on that cock of his. He just lay there smirking and pinching my nipples and slapping my tits the way I love and the more I hate that bastard, the more I cum. Of course, he teases me about the faces and sounds I make when I orgasm.

I’m a quivering mess when he rolls me over and fucks me in his favorite position, prone bone while pushing my face into the mattress and pulling my hair. He knows how rough to be with me, just going over the edge enough to make me lose control.

When he finally cums, he pulls out and finishes on my back and neck and deliberately into my hair, just to piss me off more.

We showered together in the fancy shower and then relaxed by the balcony. I’m starving so we eat and talk and he does his usual political garbage and talks shit about his ex-wife. He’s teasing me and bragging how I came home just to fuck him again, which makes me mad though it is true. Again, I recall why I do not like this man at all.

He finally says he has to go. We both know we won’t see each other again. He takes off my clothes and tells me to put the heels on again and suck his dick. I do but he can’t get hard. He tries to kiss me goodbye but I don’t like him that way, in fact he’s an insufferable jerk no matter how good he fucks. Crazy good sex, but happy to close the door on him.

So that was last night, my 2025 ending with a bang. Sorry if some of the details were gross. Hope you all have a Happy New Year!