The Company Retreat

"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 walls of her ass all around my cock, her O ring clenching tightly around the root of my cock.

"Goddamn, you feel enormous, my butt feels so full," she whispered. As her complaints subsided, I slowly pulled my cock out of her until only the head stayed inside of her. She whimpered quietly in anticipation, waiting for the reentry. I didn't disappoint, thrusting forward with more force.

Annie gasped as I bottomed out in her hole again. "Ooooohhhhh," she keened. I paused again while fully inside of her but this time she bucked her hips against me. "No more training wheels, I want you to plunder my asshole. I want you to buttfuck me as hard as you can until you fill me full of cum," she insisted.

Needing no further encouragement, I started fucking her ass with much more vigor. With every thrust, I could hear Annie grunting louder and louder, matching the force that I was using to plow her ass.

Between thrusts, she raised her hips off the mattress and I felt her hand brush against my thighs as she slipped a couple of fingers into her cunt. Soon her hand was moving quickly as she fingered herself at a much faster pace than I could keep up with.

That didn't mean I didn't try though. I was soon fucking her ass violently, every thrust forcing air from her lungs as she nearly screamed. "Fuck, goddamn, fuck. You're tearing me apart. Fuuuuuuu.." her voice went silent as her body froze beneath my pounding. This was followed by a long, low, guttural groan as I felt my inner thighs get soaked, her orgasm spraying everywhere across the bed under and behind us.

That warm feeling against my legs and hearing her come pushed me past the point of no return. With a final slam into her abused anus, my cock erupted, painting the inside of her ass with layer after layer of cum.

I collapsed on top of her, the both of us gasping desperately from the exertion. As her breath started slowing, she turned her head so she was facing me as best as she could. "How are you still hard in my ass?" she asked incredulously. Before I could answer, she rolled to her side and I rolled with her. "Get your cock out of my butt, fuck! I can't take any more of that right now."

I laughed and tilted my hips so that my cock pulled out of her sphincter with a small popping sound. She whimpered a little but it sounded more out of regret that I was no longer inside of her than of pain. I laid on my back, still breathing pretty hard as she sat up.

"Jesus, you filled by butt up with cum. I don't know if anymore could fit up there." She turned and crawled away from me me. My eyes followed her and I could see some of my cum starting to drip out of her gaping asshole.

She reached for a glass of water on her nightstand. After drinking deeply, she wiped her mouth and set the glass back down. Turning back to me and said, "Finally you start to get a little soft." I looked down at my cock and it had indeed softened slightly but was still looking quite large.

With a gleam in her eye, she crawled back across the bed toward me, her eyes directly on my cock. She grabbed it by the base and started to lower her face to it.

"Whoa, whoa!" I exclaimed. "Are you sure you want to do that?"

She looked at me innocently and shrugged, replying, "Either it tastes like my juices which I love or it tastes like shit which I'm sure I won't. No reason not to find out!"

I shook my head and watched as her face got closer to my cock. She sniffed at it a bit and then touched it with the tip of her tongue. Without further comment, she made the head of my dick disappear between her lips. "Mmm hmm!" she hummed around my cock, pleased with her decision.

I was quickly hard once again and she took advantage. She rapidly bounced her head up and down, cleaning my cock of the taste of her juices, my cum and, presumably, her ass. Her fingers played around my balls and then slid further down, dancing around my asshole. The feeling was fantastic.

Without warning, she sat up, my dick falling out of her mouth. "Come on, off the bed," she said mysteriously. Not one to argue, I scooted across the bed and stood in front of her. She turned me back to face the bed so that she was behind me. She took hold of my cock and started stroking me while she kissed my back. I felt her kiss lower and lower, kneeling down behind me. She shoved her face between my ass cheeks and once again began lapping at my sphincter, stroking my cock at the same time. I bent over at the waist, resting my weight on my elbows on the mattress as I experienced this amazing feeling.

Despite just having come like crazy, this started blowing my mind and the sensations were overwhelming. Annie let go of my cock and repositioned herself so that she could grab it from between my legs. She kept stroking me as she started fucking my asshole with her tongue.

"Damn, that's going to make me come again, all over your sheets," I gasped.

"Mmm mm," I heard her hum into my ass as she shook her head. Leaning back slightly she laughed, "We can't have all of that tasty cum go to waste!" With some maneuvering, she pulled my cock backwards between my legs so that it was pointing back at her. I thought it was going to be uncomfortable but she found a good angle as my cock was once again engulfed in her mouth.

Her lips formed a tight ring around my shaft as she moved her head quickly up and down my cock. She pushed it deeper until it hit the back of her throat. She gagged once more but when she pressed it again, suddenly the barrier opened up and my cock slid down her throat with ease.

Annie made a squeal of pride and delight around my cock as she started fucking me with her throat. Looking down between my legs, I could only see her chin as it thrust forward and back but I saw her reach to her pussy with her free hand, getting her fingers soaked. She reached back up and slid a finger into my ass up to the second knuckle.

That did it. With a yell, I came like I had never come before. She slammed her face into my crotch, holding my dick as deep into her throat as possible. My entire body jerked with every spasm of my cock. I could feel my asshole clenching her finger like a vice in time with the ropes of cum I was shooting directly into her stomach.

As I kept coming, Annie gripped my cock and slid it from her throat, out of her mouth and pointed it at her face. I kept firing shot after shot, quickly glazing her face until she was wearing a mask of cum.

Finally, my orgasm subsided and I collapsed to my knees. She released my cock and slipped her finger out of my ass. "My god," I panted.

She stood up and looked at herself in a nearby mirror. "I don't know where you keep all of that cum," she said with a laugh, watching my jizz starting to drip from her chin onto her tits. "I had to stop swallowing because I wasn't sure I could take anymore." She admired her reflection. "This is new for me, I like this," she said cheerfully, her eyes peering through pools of cum on her face.

After a few moments I stood up and she tossed me my clothes. "It's four in the morning," she said. "I thought this was going to be a quick 15 minutes and a good night's sleep. Not some crazy marathon fuck session where half my bed is soaking wet, my asshole is stretched out of shape and my face is dripping with cum."

I laughed and replied, "This has definitely been an unexpected, unparalleled night."

"It has indeed," she replied. "But you need to get out of here, because I need sleep before my first meeting tomorrow and if you stick around, I'm going to ride your face all night."

I grinned and got dressed quickly. I noted that she still hadn't cleaned her face of my cum. Catching my glance, she said, "I might keep it there for a bit, I want to save this memory because it's fucking hot. I'm going to jerk off to you for at least the next six weeks."

There was no way to top that so I made my exit and walked back to my hotel. I've never seen Annie since but wow, what a night. I wonder what next year's company retreat will bring?