I'm Lew Carver. I'm a Private Detective, recently retired from the Chicago Police Department, and recently divorced. My former wife got just about half of everything I had before the divorce, and now she gets half of my retirement pay. That's not enough for me to live on - at least not how I want to live, so I've started my own business as a security consultant and a private investigator. My apartment is directly above my office, so I don't have any distance to get to work.
It's been slow getting my business off the ground, but I've had a couple of interesting cases that have paid off OK. One was watching a client's younger wife to see if she was cheating on him while he was traveling. It turned out that she was, and in the investigation, I was able to get a few photos through her boyfriend's bedroom window. It was one afternoon, and with the bright sunlight illuminating the bedroom perfectly, I caught her completely naked and riding the cock of her country club tennis teacher boyfriend. The photos turned out well, and I admit that when I gave the prints to her soon to be ex-husband, I kept several extra copies for my own evening pleasure.
Now don't get me wrong - I have an active sex life with a couple of ladies that I know, but some evenings I'm home alone, and I get horny, and have to take things into my own hands, so to speak. The photos of that trophy wife riding the other guy's cock with her back arched, and her firm breasts pointed forward work nicely for me as a masturbation aid.
Today, it's a long Thursday summer afternoon. I'm in a bit of a lull at work, in between jobs, so I'm sitting at my desk looking into the front window of the Lakeside Insurance office across the street from me. That window is full height, going from just above the floor level up to the ceiling.
The insurance agent's office assistant is Sheryl. Sheryl is single, but a couple of times I've watched a guy drop her off at work. A few times we've been in the same diner for lunch, and we've sat at the same table and chatted. She's friendly and a bit flirty, but I haven't been able to get her to agree to go for dinner and drinks with me after work. Sheryl is about five and a half feet tall, has medium length natural red hair and big blue eyes. She has nice C-cup breasts and shapely legs. But her best feature is her ass. I'd have to say Sheryl has about the most perfect ass that I've ever seen. She frequently wears tight, short dresses that really show off the shape of her derriere. I get really horny in the mornings watching her walk down the sidewalk from the bus stop at the corner into her office, her lovely ass slightly swaying from side to side.
So anyway, I'm sitting here at my desk looking at Sheryl and fantasizing about her. Today must be a casual day over there, because she's wearing a really tight pair of blue jeans. From my view here, they almost look painted on. Those jeans really define the shape of that stunning butt of hers. Sheryl looks across into my office, sees me looking at her, smiles and waves at me. I smile and wave back. Then, she walks over to a file cabinet and bends over at the waist to open the bottom drawer. I know that she knows that I'm watching her, and she presents me with an incredible view of her ass. Maybe it's my imagination, but I swear that she wiggles it back and forth a couple of times. But instead of staying bent over at her waist, she squats down, with her knees bent. Her ass is now the shape of an upside-down heart with her jeans riding up tight into her butt crack, just perfect. My cock is getting harder, and I start rubbing it through my pants, sitting there behind my desk, imagining what I could do with her. Now she stands back up, after finding whatever file she was looking for. Flashing me another quick smile, she walks into her boss's office.
I keep watching and thinking about her ass. But she doesn't come back out of her boss's office, so I give up, grab my hat, and head to Chuck's Bar, a couple of streets over, where I've had a bit of success hooking up with a couple of women after work. Chuck's place is just the right kind of quiet, fairly dark place that's good for talking with others. It has a faint, but not annoying smell of beer and cigarettes. And it's in my neighborhood and is one of my favorite hangouts when I'm looking for company.
But today doesn't look it's going to be successful for me -- there are only a couple of tables with guys sitting at them, so I go up to the bar, park my butt on a stool, and get Chuck to bring me a Guinness beer. Chuck and I chat for a while, then he moves off to check on a couple of other customers, leaving me alone there on the bar stool.
There's a big mirror behind the bar, and from where I'm sitting, I can see the front door reflected in it. A motion at the door catches my eye, and in walks a gorgeous, tall blonde honey. She's taller than Sheryl, like almost six feet tall, and possibly even better looking. She has everything stacked perfectly in all the right places - tits, waist and ass. She has big breasts - at least D cups. Probably implants, but I'm not fussy. She's wearing a low-cut tight dress that buttons up the front and shows a lot of cleavage. Her skirt ends about mid-thigh, and it really shows off her trim waist and slender hips. Her legs are long and smooth and shapely, with well-defined calves and firm thighs. She looks to be in her early to mid-thirties. I like what I'm seeing.
She stops a few paces inside the door, and I see that she's on her phone. She's angry - actually very pissed off about something - I can see that in her eyes and in the expression on her face. She and the person on the other end are having an argument, but she's not speaking loud enough for me to hear what she's saying. I'm looking at her attractive body there in the mirror, and I read her lips as she says, "Well, fuck you, too!" She ends the call, stands there for a few seconds tapping her foot on the floor, then she looks around and walks over to the bar. She sits on the bar stool that's two away from me, and waves Chuck over.
I'm still looking at her in the mirror, and I see that she's calming down a bit. She orders a single malt Scotch, neat, with a water back. Wow, this babe has class, I'm thinking. And she reminds me a bit of Sheryl, somehow.
I turn to her and say, "Well, it appears that didn't end well." She turns her head my direction and just glares at me. I'm prepared for her to tell me to fuck off like she did the person on the phone, but then she relaxes a bit and smiles a little.
"Yeah, it's a guy I've been dating for a while. He just broke up with me on the phone. The ass hole...." She has a throaty, sexy voice that piques my interest.
"Well, just relax and enjoy your drink. If he doesn't get back with you, it's his loss." I reply. She smiles back at me again, and I can see that her anger is dissipating.
"I'm sorry, just because I'm royally pissed off at him, I shouldn't take out my anger on you. Let's start over. My name is Diane." She moves over onto the bar stool that's next to me, extends her hand with long, slender fingers and well-manicured red nails and shakes my hand. Her hand is nice and smooth and warm, and she holds onto mine for a few seconds longer than I would have expected.
Not wanting to miss my chance here, I introduce myself and tell her that I'm a private detective, just starting out in my own business. "Well, Lew Carver. So, you're a private dick, huh?" She smiles and winks at me as she's saying that. It's looking like things might be going my way this evening after all, but I'm not going to push too hard just yet.
So, we're just chatting about all sorts of meaningless stuff for a few minutes, staying away from anything to do with her argument with her now ex-boyfriend. The more I look at her, the more I like what I'm seeing. She has nice brown eyes, and full, kind of pouty, lips. What I like to call DSL - 'Dick Sucking Lips'. And yes, I'm thinking about her lips sucking my dick.
Diane's sitting there with her legs crossed, showing a nice amount of thigh, with her skirt ending just below the point where her thighs turn into her ass. And her ass, from this side view, is looking good. It's really kind of small, and looks very firm, like she could crack a walnut between her ass cheeks. I like it!
So, we keep talking for a while and I ask if she wants another Scotch. "Yeah," she replies. "But only if you'll have one with me, and I'm buying this round." She smiles again at me, and runs her tongue slowly over those full, red lips of hers. Yes, the evening is looking better! We continue chatting and each have a couple more drinks.
"Say, Diane. I've never seen you in here before. What brings you to Chuck's place?" I ask.
She tells me that her cousin works in an insurance agency a couple of blocks away, and she was supposed to meet her for drinks here in Chuck's. But her cousin ended up having to stay late at work, so Diane called her boyfriend to see if he'd meet her here. And that's when her boyfriend informed her that he didn't want to continue their relationship.
"By any chance, is your cousin named Sheryl?" I asked. "Does she work at Lakeside Insurance?"
Diane is kind of looking at me in a surprised way. "What the hell! Are you spying on me, you son of a bitch? Did someone hire you to check me out?"
I'm sensing that my chances with Diane are fading away, unless I can convince her that I'm not the dirty private detective that she thinks I am. "No, no, no. No one has hired me to watch you, and today is the first that I've heard your name. It's purely a coincidence. Sheryl and I work across the street from each other, and we've been to lunch a couple of times. That's all. I've even asked her out on a date, but she hasn't said yes yet." I'm explaining this to her, and I can sense that she's calming down again.
By now, I'm beginning to feel a little lightheaded from all the booze on my empty stomach. I need something to eat. So, I suggest, "Hey, let's walk down to this little Italian restaurant a couple of streets over, and have some dinner. I'll buy."
