All characters appearing or mentioned in this story are 18 years old or older. This story is a work of fiction and any reference or description to actual persons is unintentional.
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If you are enjoying these stories, leave a comment about what you liked or didn't, or things you want to ready more of. I'll take advice into consideration when I'm working out the next parts of the LoP stories.
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December 1999
"Almost there," I told Maryanne as I slowly made my move. "Just relax."
"It's feels so god damn big; how did it ever fit in there," she said, agitated more than a little.
"Just a little more," I said, trying to be as gentle as possible.
"Just do it," she demanded. "Make it quick and I'll deal with the pain later."
"Alright," I said, taking a breath myself.
"Ow, FUCK," she yelped at the sensation.
In one swift motion, I'd quickly pulled on the tightly held tweezers, moving out and away from her eye. The culprit, a feather from my down pillows, came away cleanly and intact.
"Oh my fucking god," Maryanne yelled in relief. "You have got to get some new pillows."
She rubbed her eye roughly, trying to get the gunk out and feeling back into her blue-grey orb.
We'd been having sex and, at her insistence, giving anal another try. She had been practicing with a dildo at home, and things were going well; she was in doggy position, I had inserted about a third of my generous length into her tight, lubed up ass. Her head was buried in a pillow so her cries were muffled but audible, and I had just started to get a rhythm going when she screamed in sudden pain and jumped off of me. Which resulted in her screaming again, but in a different kind of pain.
After ten minutes though, the crisis was over. She could see clearly, no pain was present, and she was still wanting to continue our session.
"OK," she said, settling back into missionary position, pulling her knees back towards her shoulders to allow me to enter. "Until you get new pillows, you're just going to have to face me when you fuck my ass."
With Maryanne in this particular position, waiting with her legs spread open, her pussy and ass just mine for the taking, I couldn't help but appreciate such an exquisite beauty such as she presented.
"Well," I said, settling between her spread open legs. I gave my cock a stroke and played the head along her ass, pleased to see that the lube was still wet. "It will be nice to see your face when I push in, that's for sure."
I started to apply pressure to her hole, working the head of my cock into her ass gently. It popped in and we both had a moment our breath caught in our throats.
"Oh, damn," she said, looking down at the action. "It looks impossible to fit in there. But its so hot to think how good it'll feel when you work it in all the way."
She looked back at me with a mixture of pleasure and anxiety. "How does it look?"
"Fucking spectacular," I said as I pushed in further.
"Ohhhhhhhhh," she called out, squeezing her eyes shut as I impaled her deeper. Maryann started rubbing her pussy with one hand, putting pressure on her clit with her palm and working her fingers around her entrance. Her other hand had a light-pink nipple of her C-cup breasts in an absolute death grip. The nipple in question was turning purple as she pinched it. Even with this assault, her nipples were, for lack of a better word, perfect. Shape, color, size, placement, they were wonderful to look at and even better to lick and nibble on.
I withdrew and pushed in again, going even deeper. Her ass was incredibly tight and difficult to push into. We'd only done anal very rarely, but Maryanne was determined to take it all today. She said she'd been working with a dildo in the shower, trying to train herself to take something as large as my cock. She'd made progress, but that still didn't make it easy for her as I pumped my long, thick cock into her ass.
Her eyes were squeezed shut and her mouth was in an O shape. I was going slowly but that didn't mean she liked it.
"How're you holding up?" I asked.
Her eyes fluttered open and she smiled up at me.
"I'm going to cum so god damn hard I might explode," she said breathily, her pussy-rubbing hand moving even faster.
"Push that bus-sized meat into me all the way. I want to take it all."
I withdrew most of the way. I reached over and applied a large dab of lube at the point of our joining. I worked it in a little to make it as easy going as possible for her. She nodded her ascent and I pushed slowly into her. I didn't stop until I had bottomed out inside her gloriously tight and hot ass.
"Oh fuck me," I said as I thrust into her, "that is phenomenal". I let her get use to the size for a few moments, but I could see that she was building up to a pretty solid orgasm. Her eyes were still on me, but her mouth was back into the O shape, breathing quickly.
She nodded again and I began pumping into her ass at a slow pace. Her hand was still moving quickly over her pussy, her other hand switching to the other nipple to squeeze.
"Faster," she said in a near whisper. I increased the pace, which increased the sensation. As I watched her masturbate while I fucked her ass, the sight of it all got my orgasm built up faster than I expected.
"Holy shit, I'm going to cum soon," I said after only a couple minutes. I started pumping into her faster, but still trying not to hurt her.
"Do it," she commanded through gritted teeth. She stopped her rubbing and used her fingers to spread open her flushed, beautiful pink pussy.
"Fire off in my ass. But pull out and spray me. I want to masturbate with your cum."
"Oh, shit, you are so fucking hot," I said as I started to slam into her with lust and need. I had only gotten a dozen or so more strokes in before I felt the dam break.