Annie Rocks Trilogy

When deep in a hole, can Annie dig her way out?

This story is a standalone sequel to "Rock and a Hard Place." It isn't necessary for you to have read that story to understand (and hopefully enjoy) this one.

© SouthernCrossfire - 2025. All rights reserved.

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Early June 1968

"Hey, Annie," said Sal, my former boss, giving me a hug when I arrived at the bistro he'd named. "You're looking good but how are you holding up?"

I'd called him for help a few days earlier after he'd fired me from an excellent-paying job about two weeks before. The only job I'd found since was as a waitress at a diner making practically nothing, so I rolled my eyes at him. "I'd be looking a lot better and getting fewer worry lines on my face if I didn't have to worry so much about my financial situation," I groused at him.

"Honey, I think we're all dealing with that. Consider them beauty marks. They give a girl character."

"Says a man. Believe me, Sal, I've got enough damn characters in my life right now; I don't need them growing on my face."

He chuckled. "Well, it's against my better judgment, but maybe I can help."

"You found something for me?"

A headshake. "I may have a lead for you thatmaylead to something. Whether it's real, whether you really want it, or whether you'll be better off in the long run if you follow it, I can't say."

"What?" I demanded, my nerves on end. I really liked Sal, who'd been a great boss and much nicer to me than my own father had ever been, but his damn daddy-like concern (probably stemming from having two daughters in their late teens or early twenties) was starting to grow annoying considering he'd been responsible for me getting into the profession in the first place.

He leaned in and whispered, "I talked to one of our protective friends who spoke with one of his cohorts in another part of town. He said you're too hot to operate anywhere around here for a long while--"

I'd been a Ring Girl, also known as a working girl or just plain whore, at Krenlo's Gentlemen's Lounge, the front for a high-class brothel in Brooklyn, where Sal was the boss. A John who liked me too much had almost exposed the operation to the point that the guys on the take on the vice squad had trouble covering it up, forcing Sal to let me go.

"--but you should be okay well away from the locals and the local pressifyou keep your nose clean. He gave me this."

He took a paper from his pocket.

I reached for it but he shook his head. "The rules: you memorize the number and the reference name on this paper. Once you're done, I'm lighting the paper in this ash tray, so there won't be any proof as to where you got it and so no one else will have the info, but don't forget it since I won't have another copy, capeesh?"

"Yes."

"Two other things: when you call, use your first name only and do it from a phone booth well away from your apartment. It's doubtful, but you never know when someone might be listening in on a call."

"I'll do that and I'll be careful, Sal. And thanks so much for doing this for me. Do you think this might lead to a job?"

"Annie, I don't know what it means, who the number belongs to, or if it's even real, but the person you'll be calling supposedly does. Ihopethat it will lead to something for you, and I pray that you'll still want to thank me for doing it for you after you know how it pans out."

I placed my hand on his and gave it a squeeze. "I'm sure I will."

He patted my hand with his other one and then handed me the note. A few moments later, I handed it back and he lit it with his cigarette lighter, dropping it in the ashtray. "My wife's trying to get me to quit," he said, putting the lighter on the table and pulling a pack of cigs from his pocket.

I frowned at him and put my hand over his pack. From what I recalled, his wife had been trying to get him to quit smoking ever since I started at Krenlo's. "You really should. The surgeon general says it's bad for you."

He waved my hand away and popped the pack to pull out a cigarette. "Yeah, I think most people with a lick of common sense already knew that but we're too stubborn to do anything about it."

He looked at it and then pushed the protruding cigarette back into the pack, leading me to give him a smile. I doubted that he'd quit but I'd reinforced a thought that was already in his mind. Outside the diner just minutes later, I thanked him and gave him a hug only to be disappointed when I saw him lighting a cigarette as he walked away. Though I wanted to do it for his sake, I held my tongue on calling after him.

Like him with his cigarettes, I knew I should quit my profession. After all, prostitution, in whatever form, wasn't legal in NYC, and most of the cops wouldn't think twice about putting a girl in jail for it if they caught her. I knew that and that there was always a risk, just like the risk of cancer with Sal's smoking. We both knew the risks, but neither of us could bring ourselves to do the right thing. In my circumstance, the money was too good and I'd become too good at it to throw it all away.

Standing there on the sidewalk as Sal disappeared into the crowd down the street, I wrote down what I'd memorized. When I passed by a phone booth a few minutes later, I glanced around. Seeing no police and no one I knew, I stepped inside, deposited my dime, and called.

*****

The word on the paper kept the woman on the other end of the line from hanging up on me. When I gave my first name, there was a pause for a moment before she replied with an address and a time."Be there, dressed for going on a date,"she said before ending the connection.

The address was in Manhattan, where I wasn't known. It was in an apartment building, so when I knocked on the door to the specified unit, a woman's voice came from the other side, "Who is it?"

"My name's Annie," I said in reply, leaning in and trying to keep my voice down. A series of locks and chains sounded a moment later and the door opened to reveal a well-dressed woman in her mid-to-late 40s.

I extended my hand and repeated, "Hi, my name's Annie."

She took my hand and shook it, but only replied, "Come in, Annie. Hang your jacket there and have a seat on the couch. Can I get you anything to drink?"

She joined me a few moments later, setting the drinks on the table and letting me take a sip before saying, "Annie, I'd like to look at you. Please stand up and step right over there. Turn. Slowly."

It was mid-June and warm outside so I'd worn a little black dress, black heels, and a set of pearls that I'd been given under a light summer jacket in an attempt to be a little less conspicuous. The hem on bottom of the dress was a bit short, highlighting my legs, and the bodice with spaghetti shoulder straps showing my girls to good effect.

"Good," she commented, though it didn't really sound like a compliment. "One more turn, please-- stop."

Over the few minutes, I felt sort of like a rotisserie chicken in the front window of a butcher shop, starting and stopping, lifting my arms, holding them out, putting them down, and so forth as she commanded. I was starting to worry that I might start perspiring like being under the heat lamps in that window.

"Very good," she concluded. "Now, strip."

I looked at her questioningly. Wearing a tailored, lavender dress with a broad white collar coming to sharp points, she looked very nice, her trim waist circled with a white belt accenting her hourglass shape. She had ample, well-formed breasts and a Goldilocks ass-- not too big and not too small-- that many men would drool over. I suspected that her blonde hair was a dye job, but it was very well done, if so, and it did a nice job highlighting her pretty face and dark eyes. In short, she looked like a total package.

And she looked dressed.

"Excuse me?"

"You're entertaining a man, a date if you will, that you wish to please. You wish to excite him in preparation to have sex with him. Show me how you'd strip for him."

Considering the job I was seeking, I figured my potential employer would want to look me over, but I hadn't figured on her look-see going that far, making me get naked, so I hesitated, not sure of myself.

Her right eyebrow seemed to go up a bit, revealing her growing impatience.

"Ah, yes, ma'am," I replied, starting to sway as I did. There was no music, so I counted beats in my head, trying to go at a steady pace, turning, swaying, waving my hem, weaving my hips. After establishing a pattern for a few counts, it was easy to continue without them.

She leaned back on the couch, her right leg crossing her knee, as she watched. I wasn't sure if she was transfixed or if she was grading me, so I continued, looking into her eyes as if she was the man I was supposed to be enticing to fuck me. Her eyes were locked on me, sometimes on my body, and sometimes my eyes, but she didn't smile, making me wonder if what I was doing wasn't enough.

I tried harder as a result, giving a smile of my own as my hands moved up to my tits, caressing them, pushing them up and in at times, dropping a strap at others, working the black cloth down a little, teasing the eventual result. As I turned away from her, looking back over my shoulder as my friend Connie had once taught me, I pulled the cups down, exposing my nipples for a moment but only from the side, giving her a glimpse of my sideboob, before my turn hid me from her direct view.

As I swayed with my back to her, I saw her smile, but then realized her eyes were focused a bit to the side--

A fucking mirror!

She was watching me in it, but it was too late, so I let her get another glimpse, but not too much, of the side as I turned back toward her. If she wanted to see my girls, she would, but she'd get the whole show first. I cupped them and pushed up, making them practically pop the tops of the cups of the dress, and I smiled, giving a little wink when I saw more than a little interest.

Indeed, the woman's face had gone from being composed, reserved even, to interested, maybe even eager for what was to come. Her breathing seemed fast and shallow, and she bit her lower lip, almost chewing it as she uncrossed and recrossed her legs the other way. If she'd been a guy, I would have expected him to be adjusting a tenting problem, so I wondered....

I moved forward, toward her, around the coffee table, getting close and leaning in, giving her a view of my cleavage before dancing back when she reached out before she realized what she was doing. The offending hand jerked back when she realized she'd almost violated the cardinal rule of strip-tease-- "Look, don't touch"-- but I grinned, shimmying back in for another view before moving back and starting my hem upward toward the finale.

Side to side moved the bottom of my dress, creeping upward a little at a time, dropping a bit at times, before moving up even more. She could see the tops of my nylons, the hooks of the garter belt, and her focus was now down there, watching my thighs, trying to glimpse my panties. I exercised a lot to stay in shape, and she seemed to be appreciating it.

The woman grinned as the hem continued up, dancing, teasing, my black lace panties and part of the garter belt now visible. The front and center gusset were solid silk, with the lace on the sides and rear, so I turned, slowly, giving her a good look at the lace in the back, along with my rounded assets.

I turned toward her and she practically gasped, the bottom of the dress now high enough to expose my belly.

"Now," she breathed, but I shook my head. She was no longer in charge; she made me do this so she'd see it through to the end. I continued on, moving the hem upward, showing more of my torso, past my waist and bellybutton, gathering a bit of the material in my hands as I did, moving closer and closer to my girls.

Then it was there, the skirt and more fully gathered in my hands, pushing up, exposing the white skin of my tits above my almost-full summer tan. Knowing that lots of guys love suntan lines, I'd spent about an hour a day since being fired sunning on the roof of the apartment building and now this lady would be the first to see the result.

And she seemed to be liking it, with her right hand slipping down, pushing the bottom of her dress between her legs. She was so absorbed in watching, I wasn't sure she realized she was doing it.

The gathered-up dress shifted back and forth, up and down just a bit, exposing the bottom of each of my boobs before taking it back. I moved in close again, the gather rising, the woman leaning in, me dancing out, and then--

The point of no return was reached and my tits slipped free, dropping to give a bounce as I ripped the dress off over my head and tossed it onto the recliner to the side.

The woman was grinning, her hands clapped together, the tips of her fingers covering part of her mouth, whether in abject excitement or prayerful thanksgiving, I couldn't be sure.

"It's easier when there's music," I said.

"That was... quite good," she breathed. "Quite... lovely. Now, turn."

I was just wearing my panties, nylons and garter belt, and my 3-inch heels, but I turned, standing tall, erect, my tits jutted out proudly as I did a slow 360.

"Very nice," she whispered. "Now, take off the rest."

"Ahem, I'm not a--"

"I didn't say you were. I said to take off the rest of your things. You see, I run an escort service and I like to know my girls. If a client says that he's unhappy with my service because the girl he was with had, say, three nipples, you can be damn sure that I already know whether it's true or not, and if it's true, I know where the extra one is. Now, take off your fucking panties and the rest."

There was no striptease for this, just unhooking the belt and two thumbs hooking the panties and my nylons, taking it all down at once before I stood up to face her, pushing my heels off with a toe, one at a time.

She was staring at my muff. "You've trimmed it for your bathing suit to sun, I see, but it needs to be smaller. And shorter. My clients tend to be very... visual... and they like to see and enjoy the merchandise."

She walked around me, staring at me, before reaching out to cup my tits. "Good, they're real. You may not believe it but I had a prospective employee come through a year or so ago who'd had a set of those new implant things stuck in her boobs. It made her look nice but felt funny as hell and I didn't hire her."

"Wow." I'd heard rumors that some women had begun to get such implants, but I couldn't imagine anyone actually doing it and hadn't a clue what to say.

"Now, squat down, holding the edge of the coffee table. Let me see you ride like a cowgirl."

I looked at her and couldn't believe she had a damn stopwatch in her hand. "Ride!" she demanded.

Using a hip swivel rather than an up-and-down motion, I pretended to ride like she instructed. She smiled when she saw it and gave me a nod. I have no idea how long I went, but my legs were aching when she finally said "Stop!" and clicked on the stop button.

"Very good. Now, sit on the couch."

I did, glad to be seated after that workout.

"Spread your legs wide," she said as she moved in front of me and dropped to her knees.

"Ah, ma'am, I said I'm not a lesbian," I repeated, not liking where this appeared to be headed.

"I'm not asking you to be," she said. "However, like what I said earlier, some of our clients like to go down on women or have them go down on them. I won't ask you to return the favor to prove your prowess since you claim not to be a lesbian, but I'm going to see your response or I'll get Claude, my guest in the bedroom, to come out and do it for you. Personally, I'd rather keep him to myself."

I wasn't sure if she was telling the truth or spinning a yarn, but I didn't want to take a chance, so I leaned back and closed my eyes before spreading my legs to imagine Rock Hudson, the famous movie star and my absolute dream date, doing me.

And do me she did! While I'd been nervous, she obviously knew what she was doing eating pussy and it was only toward the big finale, as my little moans became more intense, that I opened my eyes to watch her, fully clothed, pleasuring me.

"Oh God!" I called as a major orgasm swept through me.

I felt like collapsing when I felt her shift. A moment later, she plopped down on the couch next to me, leaning into me and kissing the outside of my shoulder before shifting back to give me a little space.

"Definitely shouldn't have any legitimate complaints in that department either," she giggled. "Unless you'd consider changing your mind, I'm guessing Lesbians everywhere are the losers that you don't, ahem, switch hit." She draped her hand over my arm and I patted her.

"I'm sorry," I said. "I've never had feelings that way and--"

"Stop! No. It's not your fault, it's just the way you're built. Don't worry about it. But if you ever change your mind, I hope you'd consider me for your first time. I've always gone both ways."

"Thanks," I said, sitting there stark naked on the couch, wondering if I'd ruined the leather.

"Tell me, how good are you with blow jobs?"

"Really good, I've been told, but I suspect we're going to have a problem if you want me to prove that one to you."

She laughed. "No, that's actually why I had Claude here, but I'm convinced you have what it takes so we can dispense with him. Unless you just want to suck him off, I mean."

"Unless he's paying, no thanks."

"Good answer," she replied with a chuckle. "I'm Maureen, by the way. You can put your clothes on, if you'd like, and I have some paperwork for you to fill out."

Over the next hour or so, she asked a lot of questions and I answered most of them. I refused to tell her where I'd worked, of course, but she was convinced about my background and that I wasn't a police plant trying to infiltrate her operation to bust her.

"I run an escort and dating service," she told me. "My girls go to dinner or other events with customers for a fixed fee. I keep the bulk of that fee and pay you minimum wage on an hourly basis for going on the date, and you get to enjoy a good dinner or whatever just like on a regular date. However, rather than you arranging them like regular dates, these dates are arranged by me and are matched based on the caller's responses and your profile."

"What do you mean, my profile? That I like teddy bears and cute bunnies, and dream about Rock Hudson?"

She laughed. "No, this one." She held out one of the papers I'd filled out a few minutes early, telling what I was willing to do and what I wasn't.

"Now, that's where you get a chance to make your money, big money, if you do it right. If you and your date get along well and he wants to, say, invite you up to his room for a nightcap, then you can negotiate whatever additional fee might be appropriate based on whatever he wants. I won't know anything about that and you won't tell me."

She stopped and looked at one of the papers I'd completed. "For example, let's say he calls to arrange the date and specifically says he wants anal sex or bondage, then you wouldn't be matched since those are 'no goes' for you. However, if he wants, let's see, assorted sex, blowjobs, performing cunnilingus, mild spanking, et cetera, or just to keep it open like a lot of guys, you'd be a potential match, and might be chosen if you generally match his preferred appearance and physical types. If you're chosen and go on the date, you'd have to do the final negotiations about what's on the table and what's off limits. You'd also have to negotiate the price for your service."

"Do a lot of guys want, ahem, kinky stuff?"

"Depends on what you call kinky." She chuckled at my expression when she said that, but continued, "Seriously, some do, but you'd be surprised at the percentage who want a nice roll in the sack with a svelte, beautiful girl who really puts out and puts their plump little wife and mother of five or six five munchkins back home to shame. Yes, quite a large percentage are married, but that's not something I ask. What I do ask is for their BankAmericard, MasterCharge, or American Express number, and I make sure it's good before I finalize the date arrangements with you. They pay you cash for any 'add-ons' that you've negotiated after dinner. The amount paid is up to the two of you."