Summer of Sydney

Ah. The real owner.

"I guess I'm not sure what I'm looking for," I admitted.

"Well," she said, "I don't think you can tell people what they're looking for. At least, I can't. 20 years of hosting these things, I'm still not any better at understanding what people really need."

I laughed. "It sounds like you've had this conversation before."

She smiled. "There's always one--some confused boy, all alone after the group he was playing with falls apart. I don't do the play rooms, so I'm usually the person they find when they come downstairs."

"So what do you do?"

"Play," she said, fixing me with a coolly interested gaze. "Just because I don't do the festivities doesn't mean I don't want to go to bed with someone."

Then she added, "That is, if you feel like it."

XV.

She led me inside. Instead of taking me upstairs, she led me through a side door of the rec room that had been closed. The den we walked through was pretty normal compared to the rooms I'd already seen.

Watching her walk ahead of me was fascinating to me. All rolls, wide hips, dimpled ass, swaying back and forth with every step. I had no idea where we were going, no sense of geography. All I saw was her.

We ended up in a bedroom, not like the staged rooms where play happened, but an ordinary bedroom where someone lived. There was a bed, again ordinary, and she lied on her back in the middle of it.

I climbed on, and I was on top of her, and we kissed, and she clutched my buttocks, and my hardening cock pushed into her big, soft thigh. Her body was wonderful to touch, so round and fleshy and warm.

I sucked one of her big, hard nipples, her areola so wide and flat, covering so much of her huge heavy tit. Then she moved my head with her hands, and I sucked the other, until both shined with my spit.

She breathed heavily, enjoying the spectacle if nothing else. I had never pictured myself with a woman like her, but I could have felt her up forever. She was delectable to me, an abundant, luxurious treat.

She produced a condom. I unwrapped it and rolled it on as quickly as I could. I fell into her buttery depths. I felt small, vaguely pathetic, humping between her large legs, but her body felt incredible.

I hadn't come yet, hadn't fully slaked myself on this mystery woman. Nevertheless, I slowed from fatigue, and she suggested that we change up. By her request, we sat crosslegged across from each other.

She asked me, "When was the last time you said no to something in bed?"

I didn't say anything for a minute, like I was thinking hard about it. But I knew instantly what it was.

"Someone offered to eat my ass while I jerked off," I finally said.

"And you told them no?"

"I told them no."

"Had you ever had your ass eaten?"

"No."

"Are you curious about it?"

No. Red light. Abort.

The truth slipped out in a voiceless hiss.

"Yes. Very curious."

"Have you ever eaten someone else's ass?"

"No."

"Would you?"

I thought about it for a second.

"I don't think so," I admitted.

She gazed into me. Her expression was flat, clinical, but her eyes caught the light in a way that made her seem amused.

"Let me ask you this," she said. "If I told you I wanted you to eat my ass right now, that it's how I want to get off tonight, would you?"

"Yes," I said, this time not hesitating.

She smiled. "That's what I thought."

She went into a drawer in the side table and found what I now knew to be a dental dam.

"Now's your chance to change your mind. No big deal. We finish what we're doing here, and, at the end of the night, we both go to bed happy."

Unbidden, I heard my mouth telling her the truth.

She went into a drawer in the side table and found what I now knew to be a dental dam. She found an item in her drawer and plugged it in--a magic wand, renowned for its many appearances in my porn consumption.

She also produced a condom, which puzzled me, until she unrolled it on the toy.

I thought she would lie on her back with her knees up and tilt her hips. Instead, she prostrated herself, facing away from me, her ass in front of me, her anus just a little visible between her asscheeks.

"Put the dam on me," she said, her voice partially muffled by the mattress.

I picked it up from the bed, opened it, applied it, with the slow, deliberate motions of hypnosis. I spread apart her soft, heavy cheeks with my thumbs and laid the dam over her asshole with my fingertips.

"You're doing good, sweety," she said.

I leaned in, put my tongue on it, was gratified to find that it wasn't nearly as weird as I thought it would be. I tasted latex, smelled mostly pool water. I licked more aggressively, feeling the ridges.

There was a murmur welling up from her. I thought she might be giving me directions, a la Sydney, something I was not opposed to given that I had my tongue between her asscheeks with no idea what to do with it.

A sleepy sounding "mmm, keep doing that" was all I got.

Emboldened, I pushed the tip of my tongue right into the tightly clenched pucker. She was more relaxed than I'd thought, or maybe she was relaxing it on purpose, because I felt her loosen, just a little.

I wriggled the tip of my tongue, just a few millimeters of it, inside the opening of her anus through the thin latex of the dental dam. I heard a click and the whirr of the vibrator bringing itself to life.

It was a strange sensation that I felt through my tongue, my chin, my hands on her bountiful flesh. The vibrator was powerful. If I could feel it through her body, it must have been making jelly of her pussy.

She was making noises in the back of her throat, little halting grunts, that occasionally emerged as more instructions.

"Don't stop."

"Mm, that's good."

"Lick my ass... lick my fucking ass..."

Then she howled, filling the small room with the sound, almost certainly alerting everyone else in the house that an orgasm was being had. She did not pull away, but bucked and rubbed against my mouth.

She switched the vibrator off, let it roll away from her hand on top of the covers, and collapsed, the dam still clinging partially to one of her prodigious asscheeks. The air was heavy with chlorine and sex.

It was a surprise and a relief. I didn't feel like I'd done a particularly good job. But the beautiful naked woman sprawled on her belly in front of me made me feel like someone who would try anything.

I laid next to her, and she rolled onto her side, and we made out a while, our hands trailing listlessly over each other's naked bodies, my hard cock against her soft thigh. It was charmingly old-fashioned.

She didn't say anything. She just eventually gave me a look that said, "Ready?"

XVI.

I assumed the position, on my knees with my ass in the air and my face buried in my arms. I heard the sound of her opening a new dam, shortly followed by the feeling of her fingers on my anus through the latex.

Her fingertips glided over my asscheeks, making me shiver. Her nails were quite short. I barely felt them. Then I felt her thumbs spreading me wide open, an illicit, invasive sensation that made me even harder.

Then the tropical sensation of her open mouth and the broadness of her tongue covering me from my asshole damn near to the backs of my balls, not doing anything, not agitating me, but holding there, wet and warm.

She pulled away. Wetness trickled past the border of the dam onto the back of my balls. I was hyperconscious of her presence, of her breath, so close. The only other person who ever saw me like this was Sydney.

I could feel her licking me, the tip of her tongue making tight little circles around me, prodding me, pushing into me, leaving trails of spittle that cooled quickly just on the other side of the dental dam.

It was baffling at first. It wasn't doing anything for me in the sense of getting me closer to orgasm. But it was a strange, powerful sensation. My head felt fuzzy and far away. Everything felt charged.

She ordered me to squeeze down as hard as I could, and I did. Then she told me to count to three and relax myself, and I did. I felt myself open up to her, right as she pushed in with the tip of her tongue.

God, it was weird. She couldn't have been that far in--just a little bit inside, as I had been. It was like being penetrated by a soft, wet, impossibly warm finger, so alien. I felt incredibly vulnerable.

Unbidden, my hand found its way to my cock. I was conscious, for the first time in a long time, of how hot and rock hard it felt in my grip. I was jerking off. The condom made squishy, plasticky noises.

What this woman was doing to my asshole made my pleasure uncanny. Everything felt... enhanced. I regretted turning down Sydney's offer. I regretted every chance I ever had to try something I didn't know.

The woman ate my ass, and I jerked off, feeling so strange, coming so close so many times, only to back off at the last second. She must have sensed it. I felt her release me. I suddenly felt cold and wet.

"Lie on your back," she said. "Knees up."

I obeyed.

She lifted my balls and reapplied the dam. It was stranger yet, being able to watch her. Then she picked up the magic wand and handed it to me. I gave her a look that must have seemed pathetically clueless.

"Put it on your cock," she said. "Use it."

Again, I was baffled, but again, I obeyed.

It took a moment, shifting through settings and running from the head of my dick to the base of my balls and back again. But, sure enough, I found a spot that felt positively lovely, just underneath my glans.

She licked and suckled my ass, and the vibrator sent waves of sensation through my cock, until I had to switch it off, so powerful was the sensation. But she kept going, licking and poking and sucking.

I crossed the rubicon, wracked with an orgasm that started squarely around her tongue in my asshole, then spread throughout my body, through my balls, my cock, up to the tips of my ears and back again.

I gasped and grunted and, ultimately, howled. I was helpless to control the feeling, this strange sensation that also felt old and familiar. My ass clenched frantically during my copious ejaculation.

I laid there sweating, my cock drooping, the overfilled reservoir tip of the condom resting somewhere near my navel. Somewhere in the great distance, I heard her dispose of the dam and the condom from the toy.

Once my mind started coming back together, I saw her moving around the room, gathering towels. She had a cap over her hair. She showed me to her private bathroom and invited me to take a shower with her.

I disposed of the condom in the trash can next to the toilet while she stepped inside the large stall, all clear glass. She started the water and it fogged up quickly. I followed her in and closed the door.

We didn't have sex, didn't even do anything particularly scandalous. She seemed to enjoy touching another person's body for its own sake, helping me wash myself, paying special attention to certain places.

For my part, it was paradise, having free license to touch this woman, to feel her through a film of slippery soap. She refused to let me be shy about her, making me lift her rolls, slip in between her folds.

I was deeply ashamed to think that if I'd seen her on the street, I wouldn't have noticed her, wouldn't have evaluated her as a potential partner. Too old, too fat. But her body was so pleasurable to touch.

And she'd given me what might have been the best orgasm I'd ever had. I felt it in my gut, my penis, my asshole, still thrumming. I imagined I might be able to feel it forever. A memory lingering in my body.

After the shower, she put on a comfy-looking terrycloth robe, then took me around the house, helping me find my clothes. Still no Sydney in sight. I was promised that she would be given a safe ride home.

I got dressed. Before I left, I sat a while with the woman. She'd gone back to her lounger, back to her book. We didn't chat. I stared at the pool, through its untroubled surface. Clear all the way to the bottom.

EPILOGUE

On the last day, Sydney left without much fanfare. Some got hugs. I got a wave. I guess we had to maintain appearances. At any rate, the rest of us still had half a day of work ahead of us, and so we worked.

For the first time in weeks, the air outside was cool, threatening rain. The shop wasn't sweltering like usual. The mood was amiable; it almost felt like we were just hanging out as friends, like a vacation.

After the end, one by one, everyone either moved away or took on responsibilities that ensured they wouldn't be back next year, including me. None of us ever met again. Times changed. They had to.

Everywhere I end up, I find new people and try new things. I owe this outlook to the friends I made over the course of one very singular summer. Perhaps I owe it to the summer itself. The summer of Sydney.

~THE END~