Speaking of women of size and anal sex, the first time I had anal sex was with a woman of size, and it was fucking phenomenal. I dramatized it for the novella “Four Days”, which is in Butt Stuff, and if you like what you read here, you might seriously consider picking up the book.
Maggie’s ass, the biggest ass I’d ever spanked, was bright red already from my hand by the time I took out the bath brush. It was wood, long-handled, with a round head; I’d found it at Wal-Mart when I first went shopping for supplies for my dorm. I didn’t give her a chance to protest; I just started smacking her ass with it. She moaned and clutched the bedspread and threw her head back and forth, but she didn’t use her safeword. She took it without protest, the bath brush cracking and smacking and thwacking her cheeks, making them bounce and shift and jiggle as they turned a deep, hot crimson, round bruises forming in several places.
“Now!” she screamed. “Now now now!”
I knew what she wanted; we’d already discussed it. I tossed the bath brush aside and grabbed the little tube of Astroglide off the nightstand. I slathered some on my cock, and as Maggie spread herself open, I dripped it between her cheeks.
Neither my ex-girlfriend nor Anna had let me try this, and I really wanted to know what it was like. Maggie was probably my best chance, and I wasn’t going to blow it. I don’t know if she played with herself before I got there, but my cock isn’t tiny — it’s not huge, but it’s not small either — and it wasn’t difficult at all to push my way into her ass.
Once the head was in, Maggie shoved her ass back and, in an instant, that tight ring of muscle was grabbing the hilt of my cock. Her insides were hot, but her ass was on fire where it pressed against me. I grabbed her cheeks hard and she moaned; the heat of the spanking seemed almost to burn my palms. “Fuck me,” she groaned. “Fuck me, please, fuck me!”
I shifted my hips, pulling almost all the way out, and then thrust hard into her ass.
Maggie let out a sob halfway between pain and pleasure as her ass tightened and she came.
She came from me fucking her ass.
It was, perhaps, the hottest thing I’d ever experienced.
And it drove me right over the edge. I fucked Maggie’s ass then, as hard and deep as I would have if we were doing it the usual way. She was howling out orgasm after orgasm, squeezing so hard that my cock almost hurt, but I wasn’t going to stop for anything.
Except for my own orgasm, that is; I felt it first in my eyes, which started watering. The tingling spread down my spine, through my backside, and when I came it was like nothing I’d ever felt. Maggie came one last time, so hard that I swear she was going to pull my cock off my body and keep it for herself.
No wonder I became so anally-focused after Maggie; with a first assfuck like that, how could I not?