My [F] first time anal [consent][painful]

It was a Greek guy I had met online. We texted a lot and talked about each others sexual experiences and turn ons. We meet a few times and the sex with him was absolutely awesome.

Some day I told him that I always found the idea of anal very interesting (since I had read a very hot NSFW comic when I was 15), but never tried before. All the guys I’ve been with before told me they would never do it as they thought it was disgusting.
But that guy was totally up for introducing me into anal! I was so excited to try it out.
So he suggested I should buy some butt plugs, and he also sent me some “first time anal” porn videos, and they turned me on A LOT.

The next days I began playing with my asshole when I masturbated.
Oh damn, what did it hurt when I started shoving my dildo inside, so I went to buy some lube (I’ve never needed lube before, as my pussy is always wet – but for anal I noticed that need to be lubed up properly).
As he told me that it would be best for me if I would start wearing butt plugs to “destress” my asshole, I also bought some in various sizes and started wearing one throughout the day. In the beginning it was a very small one for only some minutes, going up to wearing a very large one for an hour or two.

When we finally met for “popping my anal cherry” a few weeks later I was sooo excited to finally feel a cock up my ass, and he was to (of course).
He never had fucked an anal virgin before, and knowing he’d be the first in my ass made him oh so horny.
I already had the big plug in my ass which made me dripping wet even hours before we met.

First thing he did after kissing hello: he lifted my skirt and reached down to check if I wore a plug. Feeling him pushing it deeper made me even more horny.

I dropped to my knees and looked up to him. I wanted to suck his cock so badly, I LOVE giving blowjobs and he had such a nice big cock! I knew he couldn’t resist me kneeling there, so he got his cock out and I slurped and licked and deepthroated it like it was my last meal on earth. I was just so incredibly horny…

After a few minutes he lifted me up and pushed me into his bed. He smiled when he saw the bottom of the but plug covering my asshole. He shoved two fingers inside my dripping wet pussy, and told me how hot it is feeling the huge plug in my ass. That I’m such a good girl needing her ass fucked. That I’m such a good whore wearing a plug as big as this in my tight virgin ass.
He got me hornier with each second and I begged him to fuck my ass. He laughed and told me, that I have to wait as my pussy was so wet he can’t resist. He rammed his hard cock in my pussy and fucked me rough and hard until I came three times. And yes, he left the plug up my ass, it felt so intense…

Then he got some lube, removed the plug – and slowly began shoving his cock in my ass.

Although I had that plug inside before, and although I had practiced with dildos, it did HURT so MUCH!

He smiled when he saw my eyes watering, and slowly, but steadily kept pushing himself deeper. I whimpered and tears began rolling down my cheeks, begging him to go slowly or to maybe even stop, but he didn’t. When he was balls deep he paused for some seconds until the pain decreased a bit.
He fucked my ass very very slowly for some minutes until I was relaxed and was fine with that new feeling.
I felt better then. His cock in my ass felt good, but not as good as I thought it would. I was a bit disappointed. It was a strange feeling and it still hurt.

I guess he noticed because a devilish smile appeared on his face. He pulled out of my ass, turned me over and began fucking me from behind – he loved my big round ass and I always love being pounded doggy style.

What I didn’t knew: in this position he could get even deeper in my ass, and he pushed me down with his total weight.
He rammed his cock inside my asshole and started pounding me very roughly.
It hurt so much, and I cried and screamed like crazy. But after a minute of my ass getting fucked relentlessly it began feeling incredibly good and I just LOVED it!
My screams turned into moans, I begged him to never stop fucking my ass.
I came like a dozen times just from getting fucked anal.

When I left him a few hours later I was a complete mess. My asshole sore, cum dripping out of pussy and ass, my throat sore from all that screaming and throat fucking – and a big smile on my face.

And since then I really REALLY like anal.

Source: reddit.com/r/eroticliterature/comments/eqxqks/my_f_first_time_anal_consentpainful