The Company Retreat - Sex Stories

The Company Retreat

... mind?"

She pulled back up onto all fours and reached back, pulling one of her large ass cheeks apart. "How about you slide that snake into my asshole?" The adrenaline in me surged again. I was a big lover of anal but hadn't had the chance to partake once Kate and I had gotten together yeas ago.

I probably looked a little eager because as I got into position behind her, she let go of her ass and pressed her hand against my hip. "Go slow. This is my first time taking it in the butt." Surprised, I replied, "Seriously? Your invitation sounded like this is something you had experience with."

Her expression became a bit bashful as she held her hand against my hip to make her point. "I mean, I've had dildos up there. I loved that feeling so I've wanted to try the real thing." She paused before continuing, "But you are way thicker than any dildo I own, so... Take. It. Slow."

I nodded and said, "Don't worry, I've got you." Annie let her hand drop from my hip and got back onto all fours. "I don't have any lube here so we'll have to use what we've got," she said.

Looking down at her exposed asshole which was drenched from her squirting earlier, I said, "I don't think that's going to be a problem."

I settled back behind her and thrust my cock back into her dripping pussy, making her jump. "Hey! You're in the wrong hole!" I laughed and smacked her ass replying, "Relax, I'm making do with what we've got."

Pulling back out, I laid my cock between her large ass cheeks, ...

... the tip resting just outside of her asshole. Gripping her ass from both sides, I spread her to expose her sphincter more clearly. "Here we go," I said, pressing the tip against her ass.

"Mmmm," she hummed, "feeling that pressure."

I leaned more forward, gently putting a little more force against the resistance. I could feel her sphincter instinctively clenching and releasing against the tip. "Relax a bit," I said quietly. She took a deep breath and I felt her hole relax considerably, allowing the head of my cock to slip in.

"Ohhhh..." she said with a low moan. "Wait... just wait a second." I nodded silently, my body frozen in position as I felt the ring of muscles squeezing around my cock head, trying to push me back out. As the clenching subsided, I leaned forward again, the widest part of my cock pushing past the barrier.

"Fuuuuuuuuuck..." Annie hissed, "You might be too big... you're stretching my little hole apart..." I reached down below my cock and slid my hand through her wet slit. Rubbing her fresh juices around my cock, the new slickness combined with my renewed pressure suddenly made my cock slide all the way into her asshole. I found myself with my hips resting on her huge ass as she collapsed to the bed.

"FUCK! You asshole, I said go slow! You're all the way in!" She was trying to sound angry but it came across more as a combination of pain and laughing. I chuckled lowly in her ear and stayed where I was, revelling in the sensation of feeling the hot ...