Stretched and Sore: An Anal Adventure

My boyfriend and I (both 27) were getting tired for the night around midnight, so we decided to go to bed. He usually takes longer to get ready, so I was already lying down when he finally came in. He got completely naked and told me to take off my pants, who am I to argue with sexy fun time? I was lying there in just an oversized T-shirt.

He laid face down between my legs, wrapped his hands around my thighs, spread them open, and went to town on me.

He started by licking my clit, and holy cow does he know how to eat. He went at my pussy like it was the last thing in the world to drink, licking and sucking until my back arched off the bed and I was in heaven. He’s a big guy, so he has a big, wet, sloppy tongue that does wonders.

Next thing I knew, he laid his head on my thigh and used his left hand to start fingering me. Just one finger was enough. He loves to build me up before letting me finish, and that’s exactly what he did. He curled his finger inside me and hit my spot just right, moving in and out and making me wetter by the second.

I get self-conscious about taking too long to orgasm, and I know that having my ass played with is an instant trigger for me. I asked him if he’d finger my ass too. He never goes there unless I ask, just to make sure he doesn’t hurt me.

He shoved one finger in my ass and one in my pussy while still giving my clit soft licks. I could feel my orgasm building, but I couldn’t get enough of feeling him inside me. I asked if he’d fuck my ass, and he said yes.

Just knowing I’d be stretched out made me so wet — he’s quite girthy. He got up, put a cock ring on (holy moly, that thing makes him even thicker and last longer), and it REALLY stretches me out.

I got on all fours at the edge of the bed, ready to give him my tight ass. He slipped a condom on and tried to ease the head in slowly, but it was too tight and kept pushing him out. That’s not usually a problem, but the cock ring added more girth than I was used to. I asked him to use lube because there was no way I was going to sleep without being fucked in the ass.

He finally got the head in, dripped lube on my ass, then grabbed my cheeks and spread them to work it in.

Oh. My. Fucking. God.

It hurt so bad (he was so big) but I wasn’t giving up. I started playing with my pussy, getting my fingers wet, and making circles around my clit while he slowly worked his full length inside me. As soon as he was all the way in, he pushed me down into the bed and damn near climbed on top of me.

He started thrusting hard and fast, and my orgasm built up almost instantly. I swear I lasted maybe a minute before I couldn’t hold it anymore. We finished at the same time. Him inside my ass, me with my hand between my legs.

When he pulled out, I was a little sore. Afterward, when I went to clean up with a wipe, I noticed some blood. He said, “I think I ripped your ass a little, babe.”

He most certainly did.

I’m writing this the day after, and there’s still a little bleeding. I’d totally go through it again, though. I can’t help myself — I love feeling filled by him in any hole.