Leslie and I had a good working relationship. I respected her and she respected me. She was twice my age, but we treated each other as equals. This is probably why she seemed so upset when I gave her my notice, but also why we were able to remain in touch after I quit to go back to school.
I'd worked at the framing shop Leslie owned and ran with her husband. He took care of the store downtown and she took care of the workshop in the west end. Whenever they were in the same together they fought and apparently he basically lived in the basement at home. I started working there when I was 21 so I guess she would have been around 46. Thinking back twenty-five years later, I guess she looked a bit older than her age. She had partied a lot in the 70s and 80s and still smoked and drank regularly, but she knew how to carry herself, and how to flirt.
She was petite, maybe 5'5", with a bit of a tummy and a small chest. She wore black jeans that really sculpted her hips and butt. Her black hair was thick and curly and her skin was a dark olive complexion. She went to a tanning salon in the winter, but I don't think she overdid it.
At a picture framing shop there's a lot of bending over and reaching and I learned when to look for the best view. She might have caught me peeking now and then but she never said anything. I never saw much anyway. Maybe the waist of her panties poking up over her jeans or the edge of her bra as she reached to grab a pencil, nothing too exciting, but enough to keep my fantasies about her going.
Over the years we developed a good rapport and I began to sense a real affection towards me. Her daughter was entering into those horrible teenage years and Leslie told me she was waiting for her to be old enough before she would divorce her dad. I'm not sure that was the best course of action, but the fact she confided this in me made me feel like we had a connection.
I was her best worker by a long shot and our conversations sometimes seemed to keep her sane after a big stupid fight with her husband. On my last day she gave me a hug and a kiss on the cheek and said good luck. She held my shoulders and looked up into my eyes. I thought she was going to cry. She was fifty years old and I was 25 but I really felt like there was something more than a boss/employee relationship there.
I'd dropped out of college when I was 19 and took some time to find myself or whatever. When I went back, I actually felt ready to learn and had an amazing first year. I met a lot of new friends, got along great with my professors and my grades were better than anything I'd seen in high school. But, as the summer came around I was having a lot of trouble finding a job related to my field of study, so I called Leslie to see if she needed help at the shop. She was overjoyed. They'd actually just had someone quit to go backpacking and were about to post an ad.
That weekend I showed up for work and she gave me such a warm hug. When she finally stepped back and looked at me, I swear there was something else in her eyes. There was something in my eyes too, she looked hot. She was wearing strappy short heels, showing off a fresh pedicure, white capri pants, a white button-up shirt, unbuttoned to about halfway down with a white tank top under it. She had a chunky necklace with matching earrings and bracelet. I drank in the view and after a moment she walked me through some of the work in progress she needed me to finish off.
The day went great, from my perspective anyway. There was a lot of backlog to get through and not very many customers. We chatted about the past year and I heard all about the various little dramas with her daughter and husband and the staff person they hired to replace me. Around three o'clock she took a call from her daughter in the back office and I could hear Leslie lecturing her about courtesy and letting her know when things came up further in advance. I got the whole story after she hung up. Leslie had been planning to take Ally to the opera that night, but meanwhile her husband had bought her tickets to see a concert at the arena. Obviously, the teenager much preferred to go to the concert with her friends, so that left Leslie with an extra ticket to the opera. Of course, she asked me if I wanted to come.
She picked me up in her little green sports car and drove through the city like she was delivering a donor organ. I would have taken the subway and met her there, but she insisted on picking me up.. She wore a leather skirt and jacket and preferred to drive barefoot. Every time she put in the clutch and shifted gears her skirt rose up a little bit more.
The opera was amazing, but it was difficult to keep my mind off my boss in the seat next to me. Every time she leaned over to whisper a comment to me she placed her hand on my thigh, and I felt like her lips were closer to my ear than they really needed to be. I started to fantasize about where that evening might go, and tried to think of a reason to invite her into my apartment, but my apartment was a dump in a basement accessed through an alleyway. I was resigned to the fact I would probably be taking care of myself that night and did my best to remember every detail of how she looked for later.
On the way out of the theatre Leslie couldn't stop talking about the production and the performances. She compared it to other operas she had seen and asked me if I was familiar with them. I wasn't and she acted like I'd never heard of the Beatles.
"Oh, you have to hear Der Rosenkavalier!" she said, with a reasonable German accent. I said I'd check it out and she wanted to know about my stereo. I had a discman and a pair of earbuds, which apparently was not good enough. About halfway to my place I realized she wasn't heading to my place, she was taking me home.
"Uh, shouldn't we turn up that way?" I asked as we passed my street.
"No, you need to hear Tosca on a proper hi-fi sound system." she said.
"Okay." I said, "I don't have any other plans."
As we pulled into her driveway I noticed a For Sale sign in the year. That was news to me, but I didn't mention it. I guess they felt like Ally was old enough for her parents to split up.
She led me inside and the house looked pristine. I'd been over for a BBQ before and it had never looked like this. We left our shoes by the front door and Leslie led me into the kitchen, padding barefoot on the tiled floor. Without asking she pulled two martini glasses from the cupboard and began to make us some drinks.
"So," I ventured, "the house is for sale?"
"Oh, yes! Didn't I tell you?" she said. "I bought a condo last year and it's almost done so Ron and I are finally moving on."
"That's great, good for you!"
Leslie handed me the martini and we clinked glasses. It was stronger than I expected it to be, but pretty tasty.
"The condo is going to be gorgeous. Floor to ceiling windows, south facing, towards the lake, twenty storeys up. Finally! A place of my own!"
"Did you do all this staging yourself?" I asked.
"Oh god no, the agent did this." she said, "isn't it wild? This house has never looked this good. She made us take out all kinds of furniture that didn't suit this style, but..."
She picked up her glass and started walking towards her bedroom.
"I told them they had to leave the stereo." she said, "Come on, you have to hear Tosca on this system."
I followed behind as her bare feet made smick-smack sounds on the tiles and her hips swayed from side to side. Her bedroom was immaculate. The king sized bed was made, the carpet looked freshly vacuumed and every surface was perfectly dust free. The stereo was set up on a cabinet with hundreds of CDs and two big speakers on either side. She put down her drink and tossed her leather jacket onto the bed, then knelt down in front of me to look through her collection for the Der Rosenkavalier CDs.
I sipped my drink and stood awkwardly to the side. There was nowhere to sit, except for the bed. From where I was standing I could see down her half-open blouse and tank top. I might have been staring, because I didn't catch anything she said about the recording she was about to play for me.
She put the first CD into the player and hit play. The overture began and she stood to turn up the volume, then moved past me to close the door. She looked at me like, "Isn't this incredible?", then turned the volume up some more.
I sipped more of my martini. She sat down on the end of the bed and let the sound wash over her. It was almost uncomfortably loud, and I stood to the side unsure of what to do, or how long this would go on for.
"Come." she commanded, and patted the bed next to her. "You need to be centred to get the stereo mix".
I finished my martini and put the glass on a coaster next to the stereo. I took a seat a few inches away from Leslie and she smiled.
"Listen to that!" She said, arms outstretched.
"It's amazing," I said. She had a really great sound system. The bass rumbled in your chest and even though it was loud, there was no tinniness or uncomfortable resonance.
Leslie leaned back on the bed, propped up on her elbows.
"Have you met any nice girls at school?" She asked.
I turned to answer her. Her pose was so inviting, but I still wasn't sure what this was.
"Uh, there are a few I guess," I said. "But my class is mostly 18 year olds. They seem so young."
"Young can be good," she said, smiling. "I was going out with a 28 year old when I was 16. But I guess it was the '70s. We met at a concert. He had weed and I wanted weed."
She laughed and stood in front of me to get her glass and drink the last of her martini. She put the empty glass back on the cabinet and without turning around she backed up to sit down on the bed again. I guess I could have warned her, but instead I just let her sit down half on my lap. The moment she realized she was on me she placed her hand down to steady herself and it landed between my thighs. She lost her balance and leaned into me, knocking us both onto our backs.
"You okay there, Leslie?" I asked.
She was half on top of me, which made it awkward for her to try to sit up. Each time she tried, her backside ground into my crotch before she lost her balance and fell back again. She laughed and apologized, but really seemed to struggle. After the third attempt she decided to roll away from me and ended up on her hands and knees on the bed, facing me as I lied back. I could see right down her shirt to her small, tanned breasts. I think she caught me looking, but I don't think she minded because the next thing she did was lean forward and kiss me on the lips.
It was kind of just a peck, and she withdrew a little right after to see my reaction I guess. I wasn't sure what to do, but she didn't give me much time to think about it. She kissed me again, but longer this time and our lips parted and her tongue found its way into my mouth and I kissed her back.
I reached up with my left hand as we kissed and cupped her breast over her clothing. She responded by reaching under my shirt and running her hands through my chest hair. Her kissing became more intense. She sucked on my lip and thirstily drove her tongue into my mouth. I felt her nipple and moved my thumb over it drawing moans of pleasure from her throat. Soon, she was shifting her position and she moved her leg over my hips. She hiked her leather skirt up and straddled me, never breaking contact with my mouth.
She seemed to weigh hardly anything, but she began to grind on me as we kissed. Finally, she placed her hands on my chest and held herself up to look at me.
"How old are you again?" she asked.
"Twenty-five" I answered.
"Oh yeah" she said, half remembering, and half revelling in the salaciousness of it.
She sat back onto my couch and began to undo the buttons of her top. With her skirt hiked up I could see the lacey white panties she was wearing and the bulge in my pants pressing against her. She tossed her blouse to the side and pulled her tank top up and over her head. The white lace bra matched her panties and seemed exceptionally white against her tanned skin.
She reached behind her and unhooked her bra, letting it fall off her body, revealing a small pair of perfectly tanned, fifty-year old breasts. I instinctively reached up to cup them and squeezed until her nipples were between my thumbs and forefingers. She against my crotch and leaned forward to kiss me again. My hands moved down her body to her backside and I held her ass cheeks as she devoured my tongue. Then, I found the zipper on the side of her skirt and pulled it down, but it stopped halfway.
"It only goes so far." she said and began to shimmy off of me to stand on the floor.
I looked her up and down and shook my head in appreciation.
"You're so fucking hot Leslie" I said.
She waved away the complement but smiled and did a little turn, revealing that her lacey white panties were a thong. I sat up on the edge of the bed and she stepped forward to stand between my knees. I placed my hands on her hips and began to kiss her chest and suck on her nipple. She ran her fingers through my hair and moaned. My hands moved back and I caressed her ass cheeks. My tongue ran circles around her nipple and then I closed my teeth on it, gently, just enough to tug on her breast. She responded with a moan that rivaled the opera blasting from the speakers behind her.
I brought my hands back up to her waist and pulled her panties down, letting them drop to the floor. I continued to suck on her nipple as I stroked up the inside of her thigh until I reached her soft, wet pussy. She exhaled and held my head to her breast more tightly as my fingers slid back and forth along her slit. My cock was straining against my pants, but I was enjoying the effect I was having on her. I inserted my middle finger and began stroking it in and out of her, sliding over her clit and dipping back in.
I started to work her g-spot, and could feel that she might be close to an orgasm, but that's when she stopped me, saying "not yet, not yet".
I looked up at her and smiled, "I wanna make you cum, Leslie"
"Oh you will," she said, "but I want something from you first."
She pulled my shirt over my head and tossed it again, then ran her hands over my shoulders and biceps as she got onto her knees between my legs. She unfastened my belt and the button of my pants before unzipping the fly.
"Let's see what you've been hiding from me all these years," she said with a naughty smirk.
She hooked her fingers into the waist of my pants and my boxers and pulled them down at the same time. My hard, thick cock stood straight up from my crotch, just inches from my boss' lips. A gleam of precum shone on the tip.
"Oh," she moaned appreciatively as she wrapped her petite hand around my cock. "Oh, Michael."
She slowly stroked her hand up and down my seven inches, then milked a drop of precum out as she pointed it towards her mouth. She licked her lips, then leaned forward to lick the drop from my cock. Watching my boss do this was almost enough for me to lose my load at that moment, but I, but I looked over her head and took some deep breaths to control myself.
I felt the head of my cock become engulfed by the warm wetness of Leslie's mouth and her tongue began flicking the underside of the head.
"Holy shit" I breathed.
She opened her mouth and let her saliva trail down my shaft to be picked up by her hand. She slid her fist up and down my shaft as she sucked on the head of my cock and moaned with pleasure. Her brow furrowed every time she coaxed a drop of pre-cum onto her tongue. It was incredible, but I would not last if she kept this up and I wanted to be inside her.
"Okay," I said. "Get up?"
She stopped sucking and looked at me, but kept her hand on my swollen cock.
"Get up, and turn around," I suggested.
She released her grip and stood up, then turned around facing the stereo system. I stood behind her, my cock standing out like the plank of a pirate ship.
I placed my hands on her hips, then a hand on her back to have her bend towards the cabinet. There she stood in exactly the position I would watch her in at work. Legs, shoulder-width apart, slightly bent forward, her hips shifting from side to side.
I reached between her legs and slid my fingers into her pussy. She moaned and I stepped forward, positioning my cock at her hole. She reached back and guided me in. I entered just a little at a time. She felt tight, but ready. Before long I was deep inside her, grinding into her and holding onto her hips like she belonged to me. I slid my cock out and back in again as the opera singers bellowed and the orchestra swelled. We got into a good rhythm and it felt amazing to be inside my boss like this. And then the music stopped. The room was quiet except for our panting and the sound of my cock sliding in and out of Leslie's wet pussy.
But there was something else. On the other side of the door we could hear cupboard doors opening and closing. A girl's voice and the deep rumble of her father making a comment. I stopped in mid thrust. Ally and Ron were home from the concert. There was a third voice, Ally's friend.
"Oh shit." said Leslie, more annoyed than worried. She hit eject on the CD player and got the second CD of the opera from the case, all while I was still inside her. She hit play and the music swelled to fill the room once again.
"They know not to bother me if the music is on" She said and wiggled her backside against me. "C'mon, don't stop".
I had started to go soft from the distraction, so I made shallow thrusts until I began to grow again. Soon enough I was harder than before and taking long, deep thrusts. I looked down and watched her pussy lips grip my shaft as I withdrew. She felt incredible. I reached in front of her and began squeezing her breasts and pulling her nipples. She responded by pushing back into my cock so I fucked her hard and deeper. I slammed into her from behind, the slap of our flesh drowned out by the music.
I grabbed her hips and held her tight as I fucked her until she was having trouble keeping her balance. I penetrated deep inside her then straightened her into a standing position so I could hold onto her with one arm across her chest. My other hand went between her legs and I spread her pussy juice over her clit as I ground my cock against her g-spot.
Leslie began to gasp in short, sharp breaths and I could feel she was close. I continued to circle her clit with my fingers and increased the intensity of my thrusts until her orgasm finally washed over her. Her legs went weak, but I held her in place and continued to fucked her. She held onto me as another orgasm crashed through her body.
"Oh yes" I whispered into her ear and I kept going.
The music thundered around us and Leslie cried out as her pussy gushed through my fingers and sprayed onto the cabinet in front of us.
"Holy shit" I said.
Leslie's legs shuddered and her pussy clamped onto me. She pulled my hand away from her sensitive nub and I withdrew my cock, sending another shudder through her entire body. She steadied herself against the cabinet and looked at me. I was drenched with sweat. My cock stuck out and pointed at her.
"You can really go, can't you?" she asked.
She looked at the fluid on the cabinet, the CD cases and the carpet and shrugged. She turned to me and placed her hand against my chest, pushing me gently backwards onto the bed. I sat, my balls hanging off the edge, my cock pointed at the ceiling. Leslie got on her knees and took my cock in her hand.
"We're going to have to take care of this now," she said.
She opened her mouth and licked my shaft from the base to the tip, savouring the taste of her own pussy on me. She fondled my balls and tickled just under them as she sucked on the head of my cock. Her tongue stroked up and down the underside and swirled around the head. She then pointed my cock forwards and slowly slid it into her mouth and to the back of her throat. She couldn't take all of it, but she tried.