Summer of Sydney

"How about at the same time?"

"Get naked and I'll strip for you. That should be enough to get you hard, shouldn't it?"

I was out of my clothes faster than I've ever been in my life. I was acutely aware of my cock, soft but chubby, bobbing faintly and drooping towards the floor. I felt pretty self-conscious about it.

Sydney stripped, but it wasn't a strip tease. First, she shimmied out of her shorts and boxers, then she shucked her tank top. She wore a lightly padded nude bra. Her torso was long and her belly was soft.

With a deft move, she reached behind her back with both hands, popped the hooks loose, and slipped the bra off. Her breasts were two nice little handfuls, with pale, puffy areolas. They hung slightly heavy.

They fascinated me. As many times as we'd fucked, I'd never seen them before. As Sydney predicted, her close presence, fully nude for the first time, was more than enough. My cock stuck straight out.

She was looking down at it under heavy eyelids. Her expression was hard to read.

Softly, she said, "I'd like to touch it."

"Please."

Instead of clasping it in her hand, she reached under and clutched my sweating balls, sort of tilting the heavy part of my cock upwards with her wrist. Her fingertips dug gently into the back of my scrotum.

She murmured, "You're in my world now. I get to do what I want, to you or anyone else. You need to be okay with that."

I nodded. Then, realizing she was still looking at my cock, I mumbled an affirmative. Whatever she wanted was fine with me. She could have asked me to rob a bank and I probably would have. God, I wanted her.

Her free hand went to the back of my head. I prepared myself for a breathtaking, tongue-sucking, spit-soaked Sydney kiss. Instead, she turned my head to the side, put her lips on my ear, and whispered.

"Put your hands behind your back. Clasp them together. Don't let go unless I tell you."

I complied. How could I refuse? My balls were in her grip.

Her hand came around from the back of my head, fingertips trailing across my sweaty, unwashed face. She squeezed my cheeks, distorting my lips. She whispered again, still in my ear, her breath warming me.

"You want this pussy?"

I nodded.

"Say it."

"I want this pussy."

I could feel her other hand stroking me now. Not jerking me off. Just letting me know she was there.

She said, "You're gonna get this pussy..."

She still had my face pointed sideways. I couldn't really look at her. A moment passed when neither of us talked. Then I felt her tongue touch my neck and slide slowly, wetly up the side of my face.

Then she said, "But only if you're a good boy."

X.

I could feel her spit cooling on the side of my face, a strange mix of sensations that wasn't exactly comfortable. But it made me hyperconscious of her closeness, little puffs of breath on my skin.

"Mm," she said, smacking her tongue. "You taste like shit."

I giggled. She laughed.

"Let's get you cleaned up," she said.

I thought for a moment that she wanted to shower together. I almost warned her that my shower was a narrow stall, probably not big enough for both of us. Especially long, tall, broad Sydney.

Instead, she gripped my cheeks again, licked the side of my face, licked again, and kept going until my whole face felt cold from her drying spittle from the base of my neck up to the top of my forehead.

Then she turned my face to look at her, fixing my gaze with hers, not letting me look away. Her eyes were intense, like sunlight passing through a glass of cold coffee. The eye contact of predator and prey.

She said, "If anything's too much, you say 'red light.' Anything else and we keep going. Understood?"

"Yes."

"Some of the stuff we're going to do might be outside of your comfort zone. Do you trust me?"

"Yes."

"Sit down on the edge of the bed. Don't let go of your hands."

I did so. She knelt on the bed next to me, towering over me, her lovely tits just inches from the side of my face.

"You like them?" she said.

I nodded. "I like them very much."

"You want to suck on them?"

"Yes."

I put my lips on the one nearest to me, the left one, and started out by kissing and sucking gently at the tip of the nipple. She squealed a little, then told me not to tickle her. So I sucked harder.

This, she apparently liked. In fact, I'd say she liked it very much. She breathed and gasped and shivered as much as she'd done that first night I'd eaten her pussy. She periodically made me switch sides.

Soon, both of her nipples were rock hard, distended, slightly bruise-colored. I ended up staying on the left one. She gripped my head, mashed my face into her chest. I couldn't breathe. But still I sucked.

She grunted and gasped, and I realized she was having an orgasm, and it was all I could do to keep up this rough, sloppy suction, my sore tongue flicking her inside my mouth, until she pulled away from me.

"God," she gasped, sitting on the bed, her big shoulders slumped, chest heaving, nipples shining with copious saliva.

I was shocked and amazed. I hadn't realized this was the kind of thing that could make someone come.

"That was so hot," I said, the admiration in my voice genuine.

She suddenly focused on me.

"I didn't tell you to talk," she said.

She said it sweetly, but there was steel in it. I decided in that moment it would be best to keep any further comments to myself.

She pushed me down onto my back. I tried to keep my hands where they were, but it was awkward. She told me to stop, that I looked ridiculous, so I released my hands and let them splay out to my sides.

She swung one of those big, powerful legs over me, facing away from me. Her generous ass was in my face, hairy pussy and anus shamelessly on display. I didn't know what to expect. Reverse cowgirl? 69?

Then she put the sole of her bare foot on my face. Slowly, but firmly, it pushed, until I was looking away to the side, helpless to move my head. Not that I resisted, but she could have overpowered me if I had.

Her foot was smaller than I would have thought. I don't know why I thought she'd have big feet. I'd never really looked. The scent wasn't bad--dirt and work sweat, faintly--but it was directly in my nose.

"Knees up," she said.

I did as I was told.

"Higher," she said. "Lift your feet off the bed. Pretend you're trying to balance a glass of water on your ass."

I was puzzled, but, again, I did as I was told.

I felt her clutching my balls again, her fingertips squeezing into the back of them, lifting them. Her palm was warm. I heard Sydney's unladylike snort. Then I felt a wet trickle down my balls and asshole.

My heart pounded in my chest. Whatever this was...

Red light.

Red light.

Red light.

I couldn't bring myself to say it.

I was terrified that I was about to get fisted or something. What I felt was the gentle pressing of a single fingertip against my anus. Just pressure at first, then swirling, pushing around the outside.

My initial response was shock, as if it had happened by mistake, as if we should both be embarrassed that I even had an asshole, let alone that someone might be so unfortunate as to see it or touch it.

Then her other hand gripped my cock, and I felt her mouth on the end of it, my first time in Sydney's mouth, lots of tongue, lots of spit, lots of suction, especially on the end of it. No fuss, no theatrics.

The anal massage component of it was weird, not at all pleasant at first. But the more she did it, it felt less shocking, more naughty. This wasn't supposed to happen. It was starting to feel interesting.

She took a brief respite from my cock to spit on me again, re-lubricating me. Then she put me in her mouth again. Her fingers doubled their efforts, thoroughly kneading my damp anus and taint.

It felt so good. Her foot in my face, her fingertips threatening me at the doorstep of my body's most private place, and her direct, no-nonsense blowjob, no doubt honed on dozens of men, if not hundreds.

Then I felt that familiar feeling, deep inside, hot, insistent, and I panicked.

"Oh fuck," I slurred against her foot, "I'm gonna come."

She lifted her head. "Good. I give you permission."

Then she went right back to what she had been doing. If I could ascribe emotions and intentions to a blowjob, it was as if she knew I was trying to hold out for her pussy, and she was mocking my efforts.

Finally, I couldn't stop it anymore, or maybe I just stopped caring enough to try. With orgasms, there probably isn't a difference. I let myself unload. She took it all into her wonderfully hot, wet mouth.

Only once I had thoroughly emptied myself, when my output dribbled its last onto her plush tongue, she released my softening cock and my warmed, tenderized anus, took her foot away, and swung off of me.

My brain buzzed, my body hummed, my limbs were loose and heavy, lying there limp upon my bed. Then her face was close to mine, and she laid her body on mine, between my legs, like a man would lie on a woman.

She lowered her head and kissed me, passionately, invasively. She passed something into my mouth, a gooey melange of spit and cum. She told me to swallow, and I did. I felt it slithering into my stomach.

My eyes slowly came into focus. She looked at me, not quite with passion in her eyes. It was more like fascination. For the first time, she seemed eager, like I was more than just a cock of convenience.

I think she'd found a new toy.

XI.

Moments or minutes passed; I couldn't tell. When I could form the words, I apologized. She looked down at me quizzically from where she sat next to me on the bed.

I said, "I really wanted this to end with sex."

She said, "Okay, first off, what do you call what just happened? Second of all, we have all night. Do you really think this is over?"

It occurred to me that every sexual encounter I'd ever had, I had come and that had been the end of it. Whether at my behest or the behest of whatever sweet young thing had deigned to open her legs for me.

She added, "Unless you have somewhere to be in the morning."

"No," I said, nearly interrupting her.

"Just don't expect me to suck you off again. Cum only tastes good on the first round."

Duly noted.

"Don't expect me to eat your ass, either," she said. "That's one thing I'm not interested in doing to someone who hasn't taken a shower."

"It's okay," I said. "I'm good."

"You don't want your ass eaten?"

I hauled myself up onto my elbows, my stomach muscles shaking a little. It felt weird to talk with her with my head so far back.

"I'm just not into it," I said.

"You don't like having your ass eaten?"

"I've never had my ass eaten."

"Then how do you know you don't like it?"

"I just don't want it."

"That's too bad," she said.

Then she pushed my chest, and I was on my back again. She got on all fours, her tits dangling over my chest, her face close to mine.

"I could really go for a nice, clean, yummy asshole right now," she cooed, her breath in my nose. "If only I could find a nice man who wanted my tongue in his ass, maybe while jerking himself off."

I knew I was getting the hard sell. But I was still pretty sure I wasn't buying.

"You meet a lot of guys who like butt stuff?" I said.

"I turn them into guys who like butt stuff," she whispered, low and breathy. "Find me a man who's not into it and I'll lick his asshole until he comes all over his own chest. He'll remember me forever."

An image popped into my head, of Sydney eating the ass of some random guy, an amalgam of men compiled together from who knows where in my memory. I was surprised to find myself getting turned on by it.

"What else do you do with this guy?" I asked.

"First, I stroke his asshole, and I suck his dick, and I keep stroking his asshole and sucking his dick until, finally, he busts in my mouth. I rub his sweet little pucker until he's all emptied out."

Mm. This was getting me there. My cock was already rising up, a little semi-arc pointing out of my lap. Sydney and her phantom man, doing the filthiest things while I watched from the perch of my imagination.

"Then," she said, in her lowest whisper, our mouths nearly touching, "he tells me he's not into butt stuff."

Okay. I guess I had that coming.

"Just give me some time," I said. "Maybe we can try it later."

She sighed and got up, sitting crosslegged next to me.

"I don't know if there's going to be a next time for us," she said, rueful.

Fuck. She was right. There was, what, a week and some change before the last day of work? We only had a few shifts together, and it wasn't like she was going to shack up with me every night until then.

Unless...

"Stay with me," I blurted out. "Just until you have to leave."

She smiled. "You're not the only person I have to see before I go."

Oh. Right. This was Sydney, who surely had an anus in every port.

She said, "Oh, it's not all bad. We have tonight, right? And you're a cute enough guy. Some day, when you come to your senses, there'll be a whole line of people ready and waiting to eat your butt."

"I'm not like you."

"You want sex, right? You meet someone you're attracted to, you immediately wonder what it would be like to fuck them, right? That's everyone. Well, not everyone, but it's more people than you'd think."

"I guess I just don't know what to do to make it happen."

She imitated my voice. "'Hi, you're cute. Wanna have a drink later? If not, that's totally fine.'"

I laughed. "I mean, I have no idea how to get from that to... you know."

"Butt stuff?"

"Sure, let's go with that."

She did my voice again. "'Well, it appears we're in one of our houses. I don't know about you, but I'd like to have sex now. By the way, I'd be open to some butt stuff, if you're into it. If not, no biggie.'"

"Has anyone seriously ever tried that with you?"

"You did."

"What?"

"The night we chatted by the van. I told you about my ex-boyfriend. About Eliza and her boyfriend. And--"

"Yeah, I remember than night."

"You asked if you could kiss me."

"That's a little different than asking a total stranger to lick my asshole."

Sydney laid down and stretched out next to me. She didn't reach for me, nor I for her, but our arms and legs were touching.

She spoke as if to the ceiling.

"Once you stop farting around and just ask for something you want, what's stopping you from asking for everything you want? Even if it's something outlandish, the worst that can happen is that they say no."

"But who besides me has ever done that?"

"Eliza did. You know that."

"But she didn't just say, 'Sydney, my boyfriend wants to fuck two chicks at the same time. You interested?'"

I felt her head move. I turned my head. She was looking at me. There was an impatience in her eyes, probably born of how difficult and morose I was being. She got this way when she said important things.

"Here's what Eliza said, verbatim. 'I wouldn't say this if I didn't trust you, but I have this fantasy about having sex with a woman while my boyfriend watches.' Then she told me, 'I'd like it to be you.'"

"That's all it took?"

"Well, there was planning involved. Negotiating. But as far as the initial approach goes, yeah, that's all it took."

"There was nothing weird about being asked by a coworker if you'd like to have lesbian sex with her in front of her boyfriend?"

"I don't think it was weird. I was flattered."

"Did he really just watch? Isn't that kind of..."

"Creepy?"

"Yeah."

"If you've never had sex in front of someone, I guess it can be hard to imagine. But there's something really exciting about being watched. Feeling their eyes on you, knowing you're a living fantasy for them."

"I thought you said it was a threesome."

"It was. He joined in and they both lavished me with attention, which was really nice. But even if all I'd done was get her off in front of her boyfriend, that's still a threesome. Voyeurism is a sexual act."

I was going to protest once more that a threesome was utterly out of reach for me, that such an idea might as well be science fiction. But I realized I had nothing more to say. She'd demolished my argument.

Now that all my sexual frustration was revealed to be a product of timidity and my own lack of imagination, I had to address my other problem, which was that Sydney's story had gotten me very horny.

I guess it must have gotten her going, too. She rolled over to face me, her tits pressing against my arm. Sydney's kiss wasn't aggressive as usual, but still sloppy in that way that she seemed to enjoy.

We ended up having a pretty mundane fuck, with her sitting upright astride my hips, her legs and belly flexing and her ass brushing my thighs as she humped to and fro aboard my hard, slightly sore cock.

Sydney got herself off early, then laid upon me and let me hold her soft, substantial body while I fucked her from underneath. My orgasm was nice, but the second round ejaculation was understandably weak.

She laid upon me a while. My cock did not release itself until it was soft enough to slip out of her on its own. I grew to love her warmth, her sweat, the weight of her. I tried fiercely to commit it to memory.

She climbed off and headed for the bathroom. I heard her pissing, then the start of the shower. After she was done, I took my turn. When I came back to bed, she was naked, half under the covers, sound asleep.

XII.

By the time I woke up in the morning, Sydney had left. I had work that day, but she didn't. She and I were scheduled together again a week later. We had our usual humid nighttime fuck in the parking lot.

The next shift I had with her, it was much the same, but it wasn't like it had been.

Sure, she still had me upright against the side of the van, and she was fucking me standing up, my cock perfectly angled between her long legs. But there was a touch of melancholy to it, a wistful finality.

It was the last time.

Her next shift would be the half-shift on the last day of work. She would wave to us all, we would wave back, we would wish her safe travels, she would be out the door, and she would be gone forever.

Oh, that wasn't the end of the story. The real end of the story came just a few nights after she stayed with me--before we went back to the usual routine of hot, humid, grimy, tired, upright parking lot fucks.

The morning I woke up to find her already gone, I found a paper invitation to a special kind of party. Written on it in her writing, she said she'd originally planned to go with her now ex-boyfriend.

"You're on deck," her note said. Dot-dot-dot, "if you want."

The evening soon arrived. The only information I had was the details on the invitation, plus where and when to pick her up. I put on a nice shirt and black jeans. I had no idea what people wore to these things.

When I picked Sydney up, she was wearing a black sports bra and matching booty shorts that rode high enough to show that she had shaved her pubic hair. Needless to say, she looked incredible.

(Having said that, when I saw her from behind, I briefly worried that she was showing an arrestable amount of skin.)

If she had thoughts about my outfit, she kept them to herself. She kissed me when she got into the car. Nothing too scandalous. Her presence in the seat next to me filled my head with unclean thoughts.

It was already after dark when we got there. The house was huge. As the invitation had instructed, we went through the side gate into a sprawling back yard walled off on all sides by a tall privacy fence.

The first person to greet us was a fat middle-aged woman who was reclined on a float in the middle of a glowing swimming pool. She smiled a radiant smile and waved to us in welcome when she saw us.

Other than a swim cap decorated with pink flowers, the woman was completely naked. A sheen of sweat and pool water gleamed on her tits, belly, and thighs, sparkling in her dark puff of pubic hair.