Annie Rocks Trilogy

Falling into it is easy when they look so much alike, but getting out is another matter.

This story was written for the 2025 Pay to Play event. Many thanks to Lovecraft68 for sponsoring the event and for the invitation to participate.

© SouthernCrossfire - 2025. All rights reserved.

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The little fan rattled and seemed to be doing its best to blow cool air on us on a warm spring night in Iowa. It had probably been manufactured well before either of us was born so it wasn't working well, particularly not well enough for what we, both now in our mid-twenties, were doing.

Steve, his body well above me and supported on his hands and arms, continued to rail me as the sweat started glistening on him; it wasn't that hot outside, but he was getting a serious workout. A little drop ran as a rivulet down his temple and a real drop was starting to gather on the tip of his nose, pooling. He didn't seem to notice either, driving into me for all he was worth.

While gripping and bucking in time with him down below, I playfully wiped the drop before it fell, but he didn't notice that either, his total focus apparently on his cock slamming hard and fast into my depths, not even sensing when I clasped his arms and gave them a squeeze like my cooch was hugging his manhood. When he didn't acknowledge me the second time, I released my right hand and slid it down below where I hoped it would do more good.

At least for me.

Another drop started forming and this time I ignored it, much like I felt he was ignoring me-- well, most of me anyway. After things had started so well, I wondered how we'd reached this point where sex was so routine.

So boring.

My left hand fell away, too, as the newly formed drop fell, striking the flat between my tits, which were rocking frantically in time to his thrusts. I smiled at the image of the little splash it created, remembering the first time we'd tried to make love under the shower in the bathtub. The idiot plumber who'd installed the shower head however many decades earlier must have thought that people were 4-feet tall! Still, it was fun figuring things out back when we were so new as a couple and sex was still so exciting.

I'm going to need a shower after we're done here,I thought.

Steve's eyes were squeezed shut as he tried to reach that point of no return, where his balls would clench (or whatever the hell balls do) and explode with ropes of cum. He always loved that, though often not noticing that he'd finished without me.

Not noticing or not caring? I wasn't sure anymore, but I rubbed myself a little faster, hoping that wouldn't be the case this time.

My smile faded as I wondered if, inside his lids and his mind, he was imagining me or the busty red-headed waitress at the diner. While my tits weren't small, they didn't rival hers and he'd seemed to focus on them every time she came to our table to flirt with him during dinner. To make matters worse, Steve didn't seem interested in mine tonight as he fucked me, so I grabbed my left boob, stalling its motion at least somewhat since he wasn't going to.

Or maybe, instead of lack of interest, it was just the heat.

I hoped so.

Steve was a nice, good-looking guy, tall and lean, with short, dark hair and a handsome smile. His eyes, dark brown and probing, had captivated me when we first started dating; I thought we were in love so I was happy to scale back on my frustrating college career to focus on our relationship in hopes of us marrying and starting a family before too long.

That was over four years before and I now felt our lives were in a rut. While I still liked him a lot and hoped for more in the future, boredom had set in and the love we'd shared and the care he'd shown me in our early days had cooled. Even now, as he fucked me-- I don't think we'd really made love in well over a year-- I continued using my fingers on my clit in hopes of getting a release of my own in conjunction with him since I knew that he would be done as soon as he came.

Watching him, I saw his eyes were still clenched, screwed shut, so I followed suit, closing mine and letting my mind drift, trying to get my mind off his seeming indifference. It only took a moment before I settled on my favorite fantasy guy, which made me smile and try a little harder to please him and please Steve as a by-product.

Yet another drop of sweat fell, this one hitting me on my cheek, making me lose my image of Rock in the process. I opened my eyes once more, kneading my left tit and squeezing my nipple, trying anything to push that last little bit as I finally felt the special feeling building within me.

A moan escaped my lips, as much from my own efforts as his, as he slammed hard against me. My fingers flew as he pulled out, ripping the condom away to give himself a few quick wanks and send the cloudy stream flying. Something (me, my actions, the redhead, or whatever) must have done something for him because his first jet really flew, falling across my right tit, and the second--

I didn't care where the second or any subsequent ropes fell because I closed my eyes once more as that sweet release washed over me. My head-- no, my whole body-- seemed to float in the clouds and a smile crossed my face.

"Jesus, Annie, with that smile, that must have been as good for you as it was for me," he said, falling onto the bed beside me as he finally reached up to touch me. He squeezed my tit, gently, and then kissed my arm and shoulder, wiping a strand of my brown hair out of the way, smiling at me.

Maybe he'd been thinking of me the whole time.

Maybe he still cared?

I rolled over, reaching up to caress his face and kiss him, my cum-covered breast dragging lightly through the sweat on his chest.

Yes, I'm definitely going to need a shower after this.

Maybe he didn't notice, but his hand slipped across my belly and swiped through his spunk, smearing it all around before kissing me again, kissing my nipple, and falling back on the bed beside me.

"Let's get married, babe."

I looked over at him, already feeling gross in my sweat and his sprayed spunk all over my tit and belly. He wasn't even looking at me as he said it, staring up at the ceiling instead.

"Steve, is that a proposal?"

"Yeah, babe. Let's get fucking married."

He was probably lucky my glare didn't kill him. "Are youfuckingserious?" I asked, mimicking his reply but he didn't even notice.

Neither my inflection nor the glare.

"Yeah, we'll go to Des Moines, get married at the courthouse, and rent a room so we can fuck and eat room service all weekend. It'll be so cool!"

I'd dreamed of how he'd propose in our early days. I'd still wondered as reality slowly set in and the dream became somewhat faded. However, I'd never imagined this scenario.

And now I knew why.

And going to Des Moines to do it? We went to Des Moines fairly often-- after all, it was less than an hour away-- so it wasn't like going to Chicago or New York or... anywhere the least bit romantic.

"Steve, the only thing that would becoolright now is a cold shower and clean sheets," I quipped as I climbed out of bed, showing him my backside as I headed for the bathroom.

He always said I had a very sexy ass so I thought I might get one of his silly little wolf whistles or some other Steve-like sound of appreciation, but there was only silence so I looked back to see disappointment in his eyes. Whether it was my lack of enthusiasm for his "proposal" or the disappointment of not getting to fuck and eat room service in Boring-town all weekend, I wasn't sure but I didn't like to see him like that. I turned back toward him and got a real smile when he saw me full frontal. I reached out to take his hand but he climbed out of bed to stand in front of me.

"You don't want to get married?" he asked, sounding surprised.

I took both of his hands and gave them a little squeeze. "Steve, seriously, we haven't discussed this recently, so I think we should think about this some more and, you know, really talk about it?"

I left off the "and make the proposal a bit more romantic" part but I was sure thinking it.

We talked, a lot more than I expected, and fucked some more over the next few days, but much of our talk seemed to be at cross-purposes and our sex, while somewhat better, wasn't enough to save us, even with Steve having picked up a new box fan. I had a lot to consider before I finally went with my first impression, declining his offer, and, with some regret, ending our relationship.

We were both a little sad about that last part, but neither of us wasthatsad or even that surprised. I moved out the next day and, within a few days while staying with a girlfriend, I'd developed a new plan.

*****

I never intended to do it, but like many young women who arrive in the Big Apple to find their place in life, what they find isn't what they'd expected.

Coming from a mid-sized town in Iowa by way of Ames, I knew New York was big but I didn't have a clue about how big. I also knew that it was different, with lots of new opportunities for the girl who'd been raised by strait-laced, Bible-thumping parents with serious attitudes. Even years going to college part-time in Ames and several years beyond working various dead-end jobs while struggling to find long-term work didn't prepare me for what I was to find.

With the introduction of the birth control pill a few years earlier and the arrival of The Beatles the year before, I arrived at a time when controversy was running rampant on the United States becoming increasingly involved in Vietnam and on the perceived materialism that some claimed was overrunning the country. It wasn't uncommon to see small groups of young adults, often brightly clad, "protesting" with the aid of Mary Jane or even stronger narcotics followed by a time of "free outward expression and togetherness."

In other words, people bitched without offering any real solutions, they smoked pot or took drugs to relax and forget the problems they were bitching about, and then they had sex while they felt good.

While I wasn't one to worry about religion like my parents and while I enjoyed sex as much as the next girl, I wasn't one to forget the need to pay the rent and to put food on the table and clothes on my back. Therefore, while I envied parts of what the so-called "hippie" movement was doing, I didn't join them. Instead, I found a job in a factory and I worked.

In fact, I worked hard, quickly moving up from an entry-level seamstress to a Level One, and, in less than a year, I was promoted to Level One-A to oversee the work of the other five girls in my section. While I didn't do quality control, it meant that my machine faced theirs and I was responsible for making sure they were sewing and not slacking. For that, I got an extra eight cents an hour, bringing my total pay to $2.12 per hour, well above the $1.25 I'd be able to make back home, assuming that I could find the good, long-term job that had eluded me for so long.

Feeling pretty good about my situation despite the higher cost of living in New York, I occasionally went out with some of the girls and it wasn't long before I had a date. With brown eyes and hair to match topping an at least fairly pretty face and what Steve had claimed was a killer body, more dates with more guys followed. Most of the time, such dates ended at the door to my apartment (which I shared with three other girls), but I eventually met Bobby, a nice, funny guy, who rocked my world when I took a chance and invited him inside for "a drink."

Bobby stayed until late the next afternoon, taunting and tempting me with his talents, opening me up to new pleasures and teaching me new skills I'd never dreamed were possible.

Or at least which Steve had never dreamed were possible.

Unfortunately, I never saw Bobby again after that but I silently thanked him over time as I used what he'd taught me to great effect. As a result, I felt that I was probably as comfortable with my body as those bra-less, stringy-haired hippie girls were with theirs, and I got to be very choosy with my very rare lovers rather than accepting, as they did, from within their limited, drugged-out packs.

I smiled as I thought about that. Maybe I was too hard on the hippies, but my life was good as it was.

*****

In the late summer of 1966, I'd been at the factory for almost fourteen months when the first sign of trouble came. While our output was good, sales had reportedly declined-- our immediate supervisor blamed "the damn hippies" for not buying new business clothing among other things-- so plant management mandated a 10-percent across-the-board pay cut for everyone in our non-union shop. They claimed that the "everyone" included the owner and shop managers, but we had our doubts about all of it.

After all, how often would a person who became a hippie buy a dress shirt or a business suit? Most hippies were younger and had probably never worked for any significant length of time in a business environment so I suspected we hadn't lost that many sales as a result of their transformation. And what was the chance that our company's owner, a perceived tightass who'd fought unionization for years, would share the pain with us?

There were protests outside the plant the next morning that would have taught the anti-war protesters of the time a thing or two, so management delayed our opening by several hours as they brought in some muscle to control access to the facility and gain control over our picket line. As we stood outside with our hand-made signs, the plant manager told us to return to work at once and said, in no uncertain terms, that any further protests would result in suspension or outright termination.

We were a production staff made up primarily of females in a city where finding good jobs for women was a lot more difficult than I'd expected. We didn't like any of it but most of us couldn't afford the risk so we lowered our signs and our heads and trudged back inside, feeling the crushing weight of defeat on our shoulders.

A proud few held firmly to their principles though, holding up their signs and yelling for us to come back.

"Don't give up, ladies!"

"Fight the management!"

"We can beat them and get a good wage!"

My heart was torn as I listened to them, their shouted arguments making me feel guilty that my financial situation was forcing me to give up. For the first time in ages, I said a silent prayer for all of us as I entered the building and punched in on the clock.

Like so many others, that prayer went unanswered. The few who remained outside, refusing to end their strike, were terminated immediately and were not even allowed back in the building, but things didn't get better for the rest of us either. In addition to the pay cut that had been announced the previous day, our abbreviated strike and the opening delay cut our hours and our daily production, and, in turn, we didn't get our little incentive bonus for the day or the week, causing our complaints, though mostly silent, to continue.

Yes, those of us who were still employed gritted our teeth and continued working, showing up on time and meeting our quotas, but there was some very quiet talk about the possibility of another vote on unionization in the days that followed. I questioned the wisdom of that, wondering if times were already so tough that union demands might actually make them worse since we didn't have much leverage.

As I expected, my already-tight budget became even tighter when my paycheck came the following week and I found myself between the proverbial rock and a hard place. Knowing it would get even worse over time, I picked up a newspaper and started looking for a new job.

I had the classified section spread out all over my bed on Saturday afternoon with lots of entries X-ed out and a paper filled with all of two possibilities when Kimberly, one of my apartment-mates, stuck her head in my room.

"Annie! What'cha doing?"

I sighed. Kimberly was my best friend in NYC, but she'd been out late, had made some noise to wake me up when she came home around 3 a.m., and now she was interrupting my train of thought. "Hi, Kimberly. I'm looking for new job opportunities. Close the door on your way out, okay?"

Kimberly didn't take the hint, moving in to sit down on the corner of my bed instead. "What's wrong, Annie? Are you short on the rent money?" Unlike her usual bubbly attitude, she seemed genuinely concerned, possibly on realizing that without my contribution to the rent, it might put her and our other roommates on the hook for more since I was on a sublease and their former roommate hadn't been heard from since I moved in.

"No," I said, sighing again. "Not now. I have some money in savings for the rent, but that won't last long so things are going to be tight for a while until I can find a new job. Or at least a part-time job."

"Pfffh! Annie, I gotcha, babe!" she replied, waving my trouble off like it was nothing. "Listen, I've been working part-time at the lounge-- Krenlo's, two blocks down and around the corner-- for a few weeks now. Let me introduce you to Sal, the manager. He might be able to set you up with Friday and Saturday night shifts-- you know, part-time, like me-- so you can keep your day job but earn more per hour with tips than you'd make at the plant. Wanna try?"

With past experience as a waitress back in Iowa and few options on my paper (and none that looked that good), I gave one final sigh, this one long and deep. "Yeah, thanks, sweetie. I guess."

And that very night, Sal hired me and I started working two nights per week at Krenlo's lounge.

*****

The place was a so-called "gentlemen's club," with topless girls with great tits, nice butts, and sexy legs dancing on the stage under flashing, flickering lights and the girls with prettier faces and skimpy outfits that suggested more serving drinks among the patrons.

He looked at my face for a moment and then his eyes wandered up and down my body.

"I won't dance," I said, fearing that was what he would offer.

"No, problem. I usually keep pretty girls with good personalities and at least half a brain closest to the customers where they can see them and the girls can get the orders right," Sal whispered to me. Looking serious, he listed four drinks and an appetizer and told me to repeat it back to him.

I did and he nodded. "See? Customers watch the girls on the stage and think they look better than they actually do from a distance, while you pretty serving-girls get their drinks right. Customers tend to drink more and tip better in response. Hey! It's a win-win that way."

It sounded like he'd meant it as a compliment so I smiled.

"You see, Annie? You're beautiful when you smile."

Since I was only there on Fridays and Saturdays, the busiest nights by far, from 6 to closing, I learned faces of staff members and some regulars but I didn't get to know anyone very well and really didn't pay much attention to the club's operation beyond the bar and the tables. I did my job and thought happy thoughts to make smiling easier.

More smiles generally meant more tips and more tips meant more smiles, so as Kimberly had claimed, I got paid more with tips considered than at the plant. As soon as I got off at 2 a.m. on Sunday, I went home to get some rest so I could work at the plant again on Monday. It was tiring and my already limited dating life sucked even worse than before, but, on the good side, my financial troubles seemed to be a thing of the past.

And that thought brought the biggest smile of all.

Kimberly went full-time at the lounge a few weeks later. "You ought to try it," she said. "I'm making a lot more than I did as a receptionist, and I may even get promoted soon, if all goes well."