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Introduction:

An unwelcome old flame gets taught a lesson
Believe it or no, the majority of this story is true.

Jobs for the Girls


Tuesday was an early start for me. I had to be in the office at 5am for an international conference call between a divorcing couple on different sides of the world. She was here, with her lawyer, but he was in Hong Kong, and I was carrying the bags and liaising with him across the world.

Never again. The early start made the wife and her lawyer ratty and it quickly broke down into a two-hour shouting match. After he got pissed and disconnected, and she stormed off waiting for the boutiques to open, I was left with her lawyer to clear up the mess and rack up some fees.

Having wasted a morning (except for the billable hours, of course), and frazzled from the early start, I was pretty much on edge. I took a walk to clear my head, but I was too riled to work. It was only 8.30, but I was pretty sure that I would be able to arrange a date for myself. I dialled a number and arranged something.

The place was only a five-minute walk from the office, but I hung around and ate breakfast. I had an appointment with Gemma, who was travelling in and starting early for my benefit – I assumed she live across town somewhere. I’d met her a year ago when she worked for a high quality incall agency, and gone with her when she decided to become self-employed. Unlike most girls working in town, she was English. I liked her a lot, and although she charged what she wanted, I liked to buy her presents as: in my mind she put a bit extra into things, and secondly I was a sap at heart. I stopped off at a designer-looking perfumery, and asked the assistant to wrap me up something expensive, I didn’t care what.

I pressed the intercom button for Gemma’s working flat, and she released the communal door remotely. The walk up the stairs of these places was one of the best things. Expectation if you knew the girl – anticipation if you didn’t. I reached the door to her place, and she opened it. Gemma was tall for an escort – very tall in fact – about 6’ in heels. She was wearing a very plain pencil skirt and a silk blouse, which looked good with her dark wavy hair. She smiled broadly and started acting. “I’m here for a job interview!” she said, I greeted her with a kiss and gave her the gift. She dropped the embryonic role-play for a second and thanked me. I also sorted out her fee – I didn’t like doing envelopes or anything, and she wasn’t proud.

I liked it when Gemma did this hopeful-job interview act as she was so bad at it. She clearly had never worked in an office, and unlike some girls didn’t do the whole glasses and stockings drama. She just acted like a dumb girl trying to land a job.

She pushed me back on her bed and unbuttoned her blouse to reveal her small but perfect tits clad in an quarter cup bra that allowed the nipples to peep over the rim. “I can’t type. I can’t use Excel. I’m terrible on the phone.” She turned around and dropping her skirt started on an a cappella lapdance.

“Um – why should I give you a job then, Gemma?” Still facing away from me, she gathered her hair up above her head with one hand, and removed her bra with the other.
“Because I’m so good at other things. Let me show you.”
Gemma was naked in front of me, but still facing away. She spread her legs wide and bent over so that she resembled a tripod. Because she was so tall, her beautiful pussy was right in my face. Her asshole stared up at me invitingly. I buried my face in her pussy lips, and licked them as she grunted and moaned from the floor. Letting me finish, she turned onto her knees between my legs, and undid my trousers. “Let me show you what I can do. She opened her bright red lips wide and took my whole length in her mouth right into the back of her throat. She proceeded to suck and lick my iron hard cock, and every third or fourth stroke would breathe and take a second to say something silly like “I need this job so much” or “Think of what we could do in meetings”.

Gemma used her expert tongue to flick the head of my cock and sucked it from the sides and top. I’d seen her several times, and she knew the routine I liked. She stopped for a second and produced a condom from her nightstand, which she rolled on to me with her mouth. A few more sucks to make sure I was still with her, and she stood up on the bed over me. From below, looking up at her endless legs and amazing pussy, she looked like some kind of titan hooker towering over me.

She squatted down on top and impaled herself on my dick. She writhed and bounced and pumped me before turning round into reverse cowgirl and repeating the process. I told her when I was getting close, and she climbed off, swung her long legs over and lay back. I re-entered her shaved hole in missionary position, and held her close. Her small natural tits rubbed against my chest as I fucked her hard. “Pull out, and rip that condom off!” She shouted. I felt myself ready to blow, and I did as she asked. I pulled out, straddled her chest and pulled the condom off. She grabbed my cock and jerked it a few times and sent a long stream of hot cum onto her breasts. With each extra stroke, she milked another spurt from me. Because they were quite small, they were almost completely covered, a siezable pool collecting between them. Gemma smiled and used one of her middle fingers to stir the puddle of cum. “Messy – but fun! So….do I get the job?” I just laughed.
“Sorry, babe – I gave up on the roleplaying about half an hour ago,” We had a chat and cleaned up. She gave me a massage for a while, and offered me another blowjob – but instead I settled for watching her finger fuck herself and then gave me an oily handjob at the end, with me cumming on her neck. We cleaned up again, I had a shower and took my time walking to the office.

*

I had just arrived and sat down when I noticed that Vivian, my PA had left a pile of printed emails on my desk along with a Post-it note that read “Remember – Tuesday 11am L. Gordon”.

I’d forgotten all about that situation.

I picked up the phone handset to call Vivian, but she tapped on the open office door and stuck her head in. “Jerry – Ms. Gordon is waiting for you. I put her in the small conference room.”
“I totally forgot. Has she been here since 11?”
“Actually, no. She arrived at 11.30.”
“Oh, OK. Just bring her in here.”
I settled down, opened my briefcase and plugged in my phone when I heard Vivian lead in a second woman. In contrast to my professional and smartly suited PA, the second woman was slouched and pale with straggly, greasy, ash blonde hair. She wore battered skater shoes and a tired pair of sweat pants with the legs partially rolled up. For the first time in nearly two decades, I was face to face with Leanne Gordon.

*

Years ago, Leanne had been a smoking hot piece of teenaged ass. She was an active and excitable 17 year-old with a fantastic athletic body and a beautiful, almost elegant face. Unkempt blonde hair on a sporty 17 year-old is never a problem, and I have to tell you that I would have done anything for that girl. I was a year older, and we knew one another from a sports club in town that we had both been junior members of. I fantasized about her all the time, and eventually we became an item. I was completely inexperienced and never made any moves on her apart from some kissing. She fancied herself as being from the wrong side of the tracks as her mother was a single parent, but the truth was that she was from a pretty good home. Before University, I had a series of quite well paid jobs, and I treated her all the time, taking her places, going downtown to shows, movies, cool late night cafes – but Leanne never acknowledged me as a proper boyfriend, preferring to spend the rest of her time with a bunch of lowlife friends, scoring a couple of joints a week and listening to whatever was supposed to be the urban sound at the time. I bought her more and better presents, and took her to better places, and throughout my first year at University we carried on together – although I had been tempted by much better offers from other fresher girls, Leanne and I were “officially” together, but she still never offered anything more than a bit of companionship.

Finally, at the end of my first year, all the Law students were to get together for a formal dinner at the Hilton Metropole, courtesy of a the top three law firms in the city (always looking to catch the best students early on). Talking to my classmates, they spoke excitedly of hiring or cleaning their dinner jackets and ball gowns – and how proud and excited their dates were – most of the Law students would be spending the night at the Hotel – and amongst my friends, the talk was exclusively about how much pussy and head they’d be getting that night. I was still a virgin, and at the age of 19, my balls were ready to explode and kill me on a daily basis Situations didn’t get much better than this – a cool dinner, free bar, all expenses paid 5-star hotel room. I sent Leanne her invitation, and talked it through with her from a payphone in the student halls (these were the days before cellphones). She sounded enthusiastic, and said she’d meet me there on the day.

On the evening of the New Lawyers-to-Be Ball (as it was called), I took a cab to the Metropole with three of my friends, who all met up with their girls at the lobby. I knew a couple of them, and even though they were dizzy students by day, for this event they had turned on the charm and made themselves up as the sexiest young women possible in their flowing evening dresses, jewellery, heels and hosiery. Predictably, Leanne was late – but it wasn’t the lateness that had me reaching for the hard drinks.

The smell of expensive perfume made me feel light-headed as the other law students and their dates laughed and joked noisily in the lobby. Leanne was 20 minutes late now, which wasn’t unusual. I saw her marching purposefully through the revolving door, and for a split second I was pleased and relieved to see her, having gotten used to her familiar figure. Another half-second later, it hit me - Leanne was wearing a New York Yankees uniform shirt, and a pair of baggy Bermuda shorts. With her hair tied back in a rough pony tail, she looked a mess. I couldn’t say anything – I was literally lost for words. She bounded over to me and said “Hey, nice place. Wow – everyone’s dressed up. I thought about dressing up too, but – nah”

What could I do? The others started filing into the function rooms arm in arm. All I could do was take Leanne by the arm too and follow on. The embarrassment and humiliation was unbearable, but at least I was sitting with my friends who did their best not to laugh or mention my idiot date. Leanne was by no means a stupid girl. She knew what appropriate behaviour was – she simply didn’t give a shit about anyone except herself. As I sat there, burning with shame, I caught a glimpse of one of the girls in my class adjusting one of her stockings, and smoothing down her dress over a long shapely leg, finished off with a black stiletto. I looked back at Leanne, and I felt like throwing up. Suddenly, even the idea of losing my cherry and spending the night with her seemed very unappealing. As the evening wore on, I began to hate the girl next to me. She was only wearing a bra underneath her Yankees vest, and as she talked trash with someone next to her, whilst shovelling food into her mouth, she raised an arm to receive a bottle of wine. I instinctively looked down her sleeve, as you do in case you catch a sight of a girl’s breasts – and I saw that she hadn’t even bothered to shave under her arms – for several days. I felt sick to my stomach. I didn’t want to fuck her anymore; I didn’t even want to know her.

Hours later, although it felt like months, the party broke up. Tipsy couples made their way to the lifts holding one another, kissing and laughing. I decided to play it cool and see exactly what Leanne would do. She knew the invite was for the two of us to stay for the night. She knew I was looking forward to this after dating for nearly two years. I wanted to see what she would do now. For a moment, I wondered if fucking her would make up for all the humiliation. She answered that question for me.

All the couples were parading into the lobby and turning toward the lifts or bar. Leanne headed out the other direction – toward the exits. She turned back to me and scratched her ass. “Well, that was a cool evening, Jerry. Thanks a lot for inviting me along as your date. Glad I could oblige, what are girlfriends for? I’d love to stay over, but y’know my friend Stacey? Well she’s kind of got a situation going with her sister and her sister’s boyfriend, it kind of came up last night. She said she might be home tonight, so I said I’d go home too and wait in case she calls, and I might go round…anyway – thanks again.” Leanne leaned over and gave me a kiss on the lips, before bouncing off out the exit. That was the last time I ever wanted to see her.

I waited for the other couples to disappear and quietly made my way up and sat on the bed in the hotel room. A bottle of champagne had been delivered and was sitting in an ice bucket next to the nightstand. I sat very still for maybe ten minutes just thinking, not even believing what had just happened. The girl I’d spent two years chasing after had just treated me like dogshit in front of all my friends – simply because she genuinely didn’t give a crap about me. I heard the muffled sound of a champagne cork popping from the room next door, and sat there for the longest time. After a while, I had to turn the TV on to drown out the sound of other law students fucking one another’s eyes out. The night I had waited for, the girl I had chased after, everything put in place for me, and I was sitting alone in a hotel room with a melting ice bucket, watching a nature programme about leopards. I resolved never to speak to her or see her ever again.

*

“Leanne,” I said to the wretched figure in front of me. “Long time, no see.” I stood and pulled up a chair in front of my desk, “Please, have a seat,” I pulled my chair around the desk so that I’d be sitting directly in front of her – she wasn’t a client or a colleague, after all. “I heard you made an appointment, and you wanted to see me – after all this time – I mean, what can I do for you?”
“Jerry, man it’s good to see you – I saw your name in the paper, that you were a partner in this firm, so I thought I’d come and see you – catch up , y’know?” She launched into a long monologue about her life, without actually saying anything at all. “Yeah, yeah, I’ve been busy, real busy. Been doing so much stuff y’know?” After a few minutes, I realised she was just talking bullshit. I gathered from her clothes and appearance that life hadn’t really been a bed of roses for her. I looked at my watch, it was nearly noon, and for a moment I wanted to slap her on the back and take her down to the bistro on the ground floor, have some lunch and just catch up….but then I remembered the last time we had sat together, and I dismissed the thought. I let her talk for ten minutes as I just looked at her. She still had the same beautiful features under all that messy, greasy hair, and she looked in good shape, although I suspected it was probably from continually running away from the landlord or ex-boyfriends that kept her like that.

She stopped talking, I didn’t speak at all. I just let the silence take over the room. The pause was really uncomfortable. Leanne spoke again. “Ok Jerry. Look, I’ve fucked up. I’ve fucked my life up. I’ve got nothing, no job, no friends, no money, no home. I haven’t even got a fucking phone. I’m living on my mother’s couch again. I just spent years with my old friends, and some of them went to jail, one OD’d, the rest are just fucking around doing nothing. I got in trouble with some loans, and had to pay out everything I owned, I got not job anymore – I got fired from every job I had. I mean it, I got nothing left. I wanted to kill myself, but then I saw your picture in the paper, I read about how well you’ve done. I read that some of the most junior lawyers in your firm earn over a hundred an hour.” She paused. I wondered if she was going to talk about us. “And I thought, if they can do it – so can I. You’re the only person left in the world that I can turn to.

“Everyone else hates me, I owe them money, or I pissed them off somehow. I always thought we were good together, though. I need a favour, Jerry. Can you take me on in your firm? Not as a lawyer, obviously – but anything. I want to work my way up, and earn a hundred an hour.

“I can’t do anything. I fucked up working at the clothing stores, I fucked up working at the supermarket, I even fucked up at McDonalds. I need someone I know, someone smart and caring to help me.” She paused again. “Please, Jerry.”

No mention of us. No mention of the last time we were together, no apology. Just all about her, and what she needs. We sat in silence for a few minutes as I thought. “Alright Leanne,” I said, “because of old times, I’ll help you out. I’ll give you a two-week internship, like we give the students in the summer. I’ll put you with one of the associates, and you can help them out as a junior clerk or junior paralegal would. I’ll give you the chance to learn how people earn a hundred an hour. At the end of the internship, even if you do well, I don’t think it would be a good idea for you to work at this firm, but it would be a step in the right direction, you’d have some experience, and my name and this firm’s name on a good reference goes a long way in town.” She looked up and I could see the joy and expectation in her eyes, “And in return – you just shut up and do as you’re told. No messing about, no more fuck-ups. Smarten yourself up a bit – you know how, and be on time. You can make this work, Leanne. Is that ok?” She jumped up out of her seat and half danced, half bounced on the spot for a second or two.
“Yes! I knew you’d come through for me, Jerry! I knew my luck would change, thanks- I’ll make something of myself – you’ll see. One hundred an hour, baby!”

After that, I called HR and had her assigned a phone and an ID card. I called Andy Tang, the most patient and mild-mannered associate we had and explained to him that he was getting a new intern. Andy accepted this without question. “Listen, Andy –me and this girl go way back. Girl. She’s a 36 year old woman. Sorry, just do what we do, and catch up with me in a week, ok?” Andy nodded. I called Information Services and had them issue her a laptop. I hung up, but then called them back. I wanted them to put on a keystroke recorder on the laptop, and some other tracking software that we normally only used for countering industrial espionage, or other security situations.

The first week passed, and I saw Leanne once or twice wandering around the office in an ill-fitting skirt and shirt. When she saw me, she’d smile and give me a big thumbs up, or an “OK” gesture with her thumb and forefinger. I laughed. At the end of the week, I wasn’t laughing anymore.

Andy Tang, and one of the geeks from IS sat infront of me in the small conference room. The techie set up a laptop and a few gadgets. Andy had a single sheet of paper. “So guys, tell me about Ms.Gordon after her first week. Andy?” Andy was polite and concise. He was never one to bad mouth anyone. I was surprised he ever became a lawyer.
“Ms. Gordon has been on time two days out of five, her lateness have been due to a variety of domestic situations mostly to do with friends or pets. She does not seem good at using public transport, either. On the work front, she does not seem to be able to apply herself well to the tasks at hand. Filing and retrieving casefiles have been a problem, as has typing. Summarising information and word processing has not been particularly fruitful.”
“Is she good at anything?” There was a pause.
“In a word –no.”
“Ok, thank you, Andy. Josh – what has she been doing?” The techie spoke, not once looking up from his screen.
“Mostly surfing the net, mostly music and nightclub sites but more than anything she’s been using MSN and facebook. Over 18 hours this week.”
“Fuck me,” I said “she’s only contracted to work 40. Let me see her Facebook page.” The techie tapped a few keys then turned the laptop toward me. “Thanks guys, I’ll see you later.” They both left.

I stared at Leanne’s homepage. It was just as I would have imagined it in my worst nightmare. She had listed her occupation as “Qualified Lawyer”, and under hobbies had written “Earning a hundred an hour, baby!” I scanned though most of her recent posts, between her and what looked like a small sample of her 2389 loser friends. It mostly revolved around what a great job she had scored for herself now, and how she was a real success story. She mentioned on several occasions how she had done it all by herself, and taken herself from the brink of homelessness and suicide to being (apparently) a real self-made go-getter. All of a sudden all the anger and hatred from years ago came flooding back into me. I picked up the netbook and snapped it in half at the hinge, and tossed the separate parts in the bin.

I felt like kicking the chairs across the room, but stopped myself. I was a partner in this firm – so they were partly my chairs – why should I wreck them? I looked at what had been partly my netbook, and felt a mixture of regret and rage. I took a few minutes staring out the window to calm myself down. When I had control of myself, I picked up the telephone, and dialled Andy Tang. “Andy, you haven’t got Ms. Gordon anymore. Tell her that she’s changing departments and that at 9am sharp on Monday morning, she reports directly to me in my office.” It was time to put Leanne where she belonged.

*

Leanne showed up at my office at 9.36am. I closed the door and yelled at her until 9.42am. She then begged me not to fire her until 9.47am, and told me about her sad life until 9.55am. I yelled at her some more until 10.02am. Finally, I stopped yelling. “Leanne, let’s be honest. You’re a fuck-up. You always were. All you’ve done since you got here is take the piss out of me. You can’t type a summary, but you can type for 15 hours on facebook. You just don’t have it, I can’t keep you here doing this.”
“Jerry! No! Please – you said – you promised me that you’d teach me how to be a lawyer and how to earn a hundred an hour…”
“Leanne, shut the fuck up about hourly rates. You just don’t have it. You are essentially unemployable. The only reason you’re here now is because when we were kids, I loved you. I wanted to be with you, I wanted to sleep with you. That didn’t work out. I thought for old time’s sake, I’d try and help you out. But you’re not a kid anymore, Leanne. If a dumb 19 year-old hottie comes in here and fucks up, it’s cute. When a 36-year-old woman does it, it’s a Greek fucking tragedy.” There was silence for the longest time. It felt like an hour, but in reality, I think it was about 20 seconds.
“Jerry….” Leanne stopped. She walked to my side and slowly took her jacket off. She waited to see my reaction. I did nothing but look at the floor. Leanne kicked her shoes off. I stared at them. They were tatty and scuffed. Her tights had holes in the toes and were obviously too big for her as the heel reinforcement rode up by her Achilles tendon. I felt sick just like the time I saw her unshaven armpits. I sat down in my chair. “I know what we can do, Jerry,” Leanne breathed. She stood upright and clumsily peeled her tights off, unzipped her skirt and unbuttoned her blouse, dropping them to the floor.

Leanne stood in front of me one hand on a hip. I looked quizzically at her grey and faded knickers – she must have taken a miscue and pulled them down to her ankles. I looked at them. They were crinkled and stained in the gusset, and probably the same pair she wore to the New Lawyers Ball, 18 years ago. She had a large natural growth of pubic hair and scratched it unconsciously as she proceeded to remove her unmatching but equally faded bra. I gave myself the facepalm and swiveled around in my chair so that I was facing away from her. Again, she misread this and came up behind me, placing her hands on my shoulders. I spun around again to face her. As always, she had a fine body – but the entire package repulsed me. I lifted up my feet and braced them against my desk – and shoved away hard so that my chair wheeled backward six or seven feet. I jumped out of my chair.
“OH MY FUCKING CHRIST, LEANNE!” I didn’t care who heard me, “THIS IS THE FUCKING LIMIT! WILL YOU JUST LOOK AT YOURSELF!??” I picked up an umbrella from a stand next to my shelf of statutes. I pointed at her with the umbrella “Just look at yourself – you’re a fucking mess. You think I want this? Now?” She looked down at herself, but didn’t seem to understand the point I was making. “Leanne, there are secretaries and interns at this firm that are hotter than the sun, and dress a million dollars too. Not 100 yards from this office there are hookers that are so awesome that any man would crawl through a barrel of broken glass just to stick peanuts in their shits. And you come to me – a filthy, spaced-out skank, and try to offer me…this? You’re insane. You’re not trying to score a few Es or a quarter ounce of weed by giving one of your lowlife friends a blowjob in a dirty bedsit somewhere. You’re trying to play in the big leagues here.” I opened my desk and pulled out a large legal envelope and creased it open. I used the tip of the umbrella to pick up Leanne’s soiled pants and flicked them into the envelope. “Now that we understand one another, and I know exactly where you’re coming from – it’s time to really start your work here.” I opened my wallet and counted out some money. Then I stopped and counted some more. “Here’s five hundred – no seven hundred,” Get out of here, and get some proper clothes. Get a decent haircut, some proper make-up and get your fucking pussy waxed. Get some perfume that cost more that 2.99 and doesn’t come out of an aerosol can. And for the love of god, get your underarms shaved.” One of our associates, Maxine, had worked for a women’s glossy magazine before becoming a lawyer – she was still particularly good at making people over – although we normally used her talents to make skanky witnesses look angelic, or rich asshole plaintiffs look poor and honest. I called Maxine and asked her to come up as soon as she could. I turned back to Leanne “Go with this lady and get sorted out. Take the whole day, and be back here tomorrow at 8am sharp – not a second over, or you may as well not turn up at all – no excuses.” Then I added, “And don’t even think about hanging around with any of your retard friends until this is all over.” I used the umbrella to flick Leanne’s clothes up into her arms, and I threw the envelope at her. “Maxine will be here in about two minutes. Better get those clothes back on.” I sat down and didn’t look up until she had gone.

*

I sent an email to the office manager to make sure Leanne was in at 8am, then have her sit in the conference room until 10am, at which point she was to send her across the street to the St. Martins Apartments. The firm had a fairly smart serviced apartment on retainer across the road, it was intended for visiting witnesses or experts or even for partners working very late that couldn’t get home for one reason or another. There were strict instructions that the Apartment was not to be used as a love nest. This didn’t apply – this was all business.

Having left instructions that I was off-site all day, I sat in the apartment since getting into town first thing. I liked the apartment – it was spotlessly clean and furnished beautifully with the latest modern stuff. Through the glass doors of the balcony, I often looked at the city and down onto the people going about their business below.

I heard a tapping on the door. It could only be Leanne, but I checked through the viewer first before letting her in. I shut and locked the door behind her and gestured her into the lounge –although I didn’t offer her a seat. I sat down on the couch, and looked her over. I was actually quite impressed by the improvement on the previous day’s debacle, although I tried my best not to show it. She’d had at least 3 or 4 inches of her hair taken off in a fashionable mid-length style and although still the dirty blonde colour, it did frame her face nicely. It wasn’t tied up, and she still didn’t look like a professional businesswoman, but it was a huge leap. She was wearing a black suit that actually fit today, heels, and presumably the correct size nylons. Under her jacket she wore an open necked royal blue blouse – which was unusual, but didn’t look bad. I had smelled her as she walked past – and she smelled a bit more expensive than before.
Best of all, her she was doing her face justice. She looked like she’d had it overhauled at a salon, and had made an effort with some make-up. “Much better,” I said, and she smiled by opening her bottom lip widely, “that wasn’t too hard, was it?”
“No, but I-” I cut her off with a raised finger.
“Sh. What did I say about shutting up, yesterday?” She sealed her lips and turned her eyes to look out the window whilst keeping her head still. “Right, after yesterday – maybe we can start over,” I held out a straight arm, gesturing her to sit down on the couch opposite mine. There was normally a coffee table in between, but I had moved it well out of the way earlier. She sat down, knees together and leaning forward with her hands clasped in front of her as though she had come here to sell me life insurance.

I pointed both my index fingers at her knees and drew my fingers apart in one motion, indicating to her to open her knees. She did so about 8 inches before being restricted by her skirt. I kept my fingers moving to emphasise that she shouldn’t stop, and she obliged by hiking her skirt right up to her waist. Her long legs were punctuated mid-thigh by the thick banded tops of her nylons. “You went for the hold-ups,” I commented. “just remember that if you wear stockings instead, that your knickers go on after – so you can get them off without taking anything else off.” With her hands on her knees, and her legs wide apart, I focused on where they met. I nodded approval for a plain but small black thong that she wore. “Shirt.” I said simply. Leanne obliged again, unbuttoning it from the top to reveal a new black bra holding her breasts in. I gestured for her to stand up, which she did. “Skirt.” It fell to the floor a couple of seconds later.

Leanne stood in front of me in her lingerie – fully 5’8” in her heels. I couldn’t deny it – she looked hot, and although older, she appeared more or less as I had hoped she would have all those years ago. I gestured her to sit back down. “Now, first job of the day is to start getting yourself all hot and wet. Fingers only, but take your time – no rush.” She paused a second, before opening her legs wide and leaning back. She placed her left hand at the top of the triangle of her thong, and used the fingers to slowly stroke herself in an upward motion. Then with the middle finger of her right hand she rubbed and stroked vertically along the length of her slit, wobbling her finger a little at the top when she reached her clitoris. She did this for about a minute as I watched, then with one hand pulled the fabric aside to reveal a well shaven and smooth pink pussy. I presumed she had never had the cash to have surgery, but even so she had neat and short outer lips. As she continued stroking herself, she gradually used the other hand to separate those lips to reveal a slightly darker inside, glistening with fluid. The only sound I could hear was her breathing, and the soft squelch of her fingers working herself. She had closed her eyes, and now started pushing a pair of fingers inside herself rhythmically. As she pulled them out, they too glistened with her juices. I let her do this for a while before I stood and walked to her.

She opened her eyes and looked up at me. I motioned for her to stand and turn around – she did. Facing away from me, I moved her to the side of the couch and holding one of her hands in mine, bent her over, bracing herself against the top of the seat. I placed her other hand – the one that she had been fingering herself with – inside her mouth. Again, she closed her eyes, tossed her head back and tasted herself. I rubbed myself up and down against her firm ass, before standing back a pace and undressing completely. I was rock hard with 20 odd years of making up to do. Standing directly behind her again, I unclasped her bra, and let it fall forward on her arms, allowing her tits to fall out. Then with one action, I grabbed the back join of her thong with one hand, and one side with the other – and snapped it off as hard as I could. The flimsy material gave way easily, and after ripping her underwear off, I placed one hand around front of her, cupping her pussy and grabbing a soft round breast with the other. There was already pre-cum dripping off the head of my penis. I bent my knees and entered her pussy from behind. It was so wet and smooth that I ploughed straight in all the way. She made a sharp intake of breath as my first stroke pushed deep inside her, but she didn’t complain or resist. Still holding her by the pubis and one breast, I fucked her from behind as hard as I could. With every stroke, I tried to force out all the anger and frustration that I had left behind years ago. I was trying to take out revenge for all the humiliation on her soaking wet cunt. Looking down at her, with her well-groomed blonde hair and still wearing her hold-ups and heels, she looked no different from one of the 500-dollar hookers that haunted the rooms around here – but she felt different. This was my skanky ex-girlfriend whom I had transformed into an illusion of respectability and whose pussy I was now pounding with everything I had to exorcise the ghosts of years gone by.

As I thrust harder and harder, she began to moan and pant. “This is it, Leanne,” I whispered in her ear as I reamed her wet hole. “wouldn’t it have been simpler to have just given it up back then?” She didn’t reply. I could feel my balls tightening and the sensation in the head of my cock building. I slowed my strokes, but tried to deepen them even further, trying to force my dick all the way into her guts. Two strokes later, I shouted out as I shot a load of cum deep inside her. Leanne cried out as cum filed her and coated the inside of her vagina. I pulled out after the first spurt, and made sure the second and third ejaculations covered her pussy lips. I then pulled back, and let the last few ripples squirt onto her ass. I rubbed the head of my cock on her thigh, and smoothed the cum on her ass all down her legs to the top of her nylons. I reached round and scooped up a couple of fingerfuls of my semen that was dripping from her pussy and carefully wiped it on each of her nipples. To her credit, she had stayed there and taken it and not moved. I spun her around on the spot and pushed her gently backward over the arm of the couch so that she fell back onto it. Lying there with her Roman goddess face and clad in the black nylons, she could have been a model from an Annie Liebowitz coffee table book – except for the mess of sperm leaking from her wrecked pussy, and the two smears of spunk on each of her tits. “Now stay there and don’t move at all.”

I got up and fixed myself a drink, offering her a glass of water – which she accepted. I sat down and looked at Leanne who was absent-mindedly stroking her dripping cunt. After a few minutes, she opened her mouth as though she would speak, but caught herself and didn’t. I drank a bit more, and then asked her if she fucked a lot – she replied that she didn’t, unless she really wanted something. In her degenerate circles, she had acquired a reputation for being more trouble than she was worth, and there were a lot of younger and easier skanks around.

I started to ask her about how she had felt about me back in the day. She replied that she hadn’t really given it a lot of thought. She sounded sincere. I asked her if she had any intention of fucking me that night at the Hilton. She thought about it, then replied not really – there just seemed to be so much more important stuff to do at the time – like hanging with her other friends. I started to feel the blood rushing to my head, and a surge in my heart. My cock was growing hard again as my anger with her seemed to act as a natural Viagra. Within another minute, I was so hard that I thought my dick was going to burst open. It felt like a slab of stone attached to my groin. “Well, Leanne,” I said, “let’s catch up a bit more. Get on your knees.”

Kneeling down in front of me, Leanne opened her mouth and accepted the tip of my penis. I pushed firmly into her mouth, and hit the back of the roof. She seemed pretty good at this, and quickly started salivating all over my cock as much as she could before holding the base in one hand and starting out on a competent blowjob. She stroked with her hand as I thrust occasionally and she combined with strong sucking and whirling her tongue around the head. The sensation was incredible and I soon lost myself in the moment. I had only cum twenty minutes or so earlier, but this was bringing me off again. I stopped and pulled out of her mouth. “Just lick up and down the shaft for a minute, Leanne. I want to ask you – would you have done this for me when we were dating?”
“I don’t think so,”
“Well, I guess it’s ‘Yay me’, then.” And I thrust back into her mouth. To ease things, she had been drooling and spitting a lot, but now I held her head and really skull fucked her for maybe two dozen strokes. I had my eyes closed with ecstasy, but I looked down at her for a second. To my surprise, she was looking up at me. I noticed her mascara running and blowjob tears welling in the corners of her eyes. This sent me over the edge, and with another thrust, I pulled out and shot a powerful wad of cum onto her lips, and then sprayed the rest over her face and chin. When I had stopped, I used the head of my cock to smear it over her mouth and cheeks. Leanne didn’t protest, and even held it as I did so.

I looked at the clock on the wall. It read 11.58am. “Hmm,” I said “working lunch? What do you fancy?” Leanne didn’t seem surprised by this, and piped up a bit.
“How about steak sandwich? Can you get that sent up?” We both laughed a bit,
“Sure. I’ll make a call.”

Half an hour later, we both sat naked at the dining table eating baguettes and drinking fruit juice. I hadn’t let her clean herself up, although I had had a shower. The cum on her face had mostly dried to a beautiful glaze, and the mixture of pre-cum and saliva that had drooled out of her mouth had run in long streaks down her neck and breasts, making long lines down her pale skin. She was leaking like anything from her pussy still, and she shifted uncomfortably on the dining chair. She ate quite carefully, using only her fingertips, and as she licked her lips, I imagined even more sperm being swallowed down into her belly, or coating the inside of her mouth. We shared a chocolate mousse for dessert and bizarrely she took the plates and cutlery to the sink for washing, “It’s ok – there’s a machine,” I called out, “get back over here.”

Leanne lay down on the carpet this time, and I lay on top of her. I was hard again (as I had been through lunch) and with the mess her pussy was in, I slid inside like a spoon going into jelly. I massaged her tits from the top, and had her gently stroke my asshole with one of her fingers. It was fun but messy and there was no friction at all inside her – so I moved up to tit-fuck her. She pressed them together and looked down almost cross-eyed as the head flicked out from between her globes. I sat up on her and fucked her breasts over and over, as I stuck three fingers of one hand into her. At last, I sprayed a fairly small load over her neck and tits. As I stood, I looked down at her. “Pearl necklace – just about the only thing I didn’t buy you. Funnily enough, although I used to think about you every day – I don’t think I ever imagined cumming on your tits. I was only young, though.”

I stretched. “Ok, I’ve got work to do.” I put on a bathrobe and set up my laptop at the dining table.
“What shall I do?” Leanne asked.
“Are you cold?” She shook her head – it was very comfortably warm in the apartment.
“In that case, you just lie there on that couch, covered in sperm. Think things over. Watch TV if you want, but not too loud. It’s only 1.45pm, so you’ve got three hours of being a cum bucket still to go. I don’t think I’ll fuck you again today.”

Leanne nodded as if it were the most natural thing in the world and made herself comfortable on the couch as I got down to work. Later, she did switch on the TV. I looked over at her every so often, she was watching Friends or some other shit and laughing quietly at the antics on the show, but all the time with three big loads of cum inside her pussy and mouth, and glazing more or less her entire body.

At 4pm, I snapped my laptop shut. “That’s it for me,” I declared. “I’m off home. No such luck for the juniors, though. You have another hour of lying there covered in my cum. You can finish at 5pm. Same time, same place tomorrow. Make sure you’ve got clean everything – buy new clothes if you have to. Good work today, though. You’re really making progress.” I dressed, and waved to her before I left. I was sure that she would stay until five.

On Wednesday, Leanne showed up at the apartment well dressed again. Same suit, but a cream blouse this time, and seamed hold-ups. She’d also had her hair styled in the morning. We started with a long sloppy blowjob, before giving her another big facial. After that I fucked her doggy style and came inside her. We had lunch naked again – pasta this time and afterwards I wasn’t intending to do her again, but I thought what the hell, and got her to give me a well lubricated handjob and I came over her hair. Again, she spent most of the day watching TV on the couch with sperm drooling out of her pussy as it set hard in her hair as well.

On Thursday, Leanne wore proper stockings with a suspender belt. She seemed to be a quick learner when she applied herself, and didn’t forget to put her thong on over the straps. I had decided to fuck her ass that day. She said she’d only done it once before, so I wasn’t rough. I used plenty of a “realistic” lube that I had, and fucked her for a good twenty minutes before releasing a load inside her guts. I wanted to make sure that all her holes were dripping, so after a shower, I pussy fucked her and had a blowjob after lunch and she swallowed. I left early that day, so she had three hours to herself in the apartment with spunk in every one of her orifices. “Last day tomorrow,” I said “So we’re finished in the apartment. Meet back in my office at 9am. Look your best, and see if you can wear something a bit different underneath. See ya.”

Friday morning, Leanne was on time again. She had made the extra effort and had gotten hold of a black corset somewhere. I never bothered to ask if she’d waxed or shaved her pussy – but it was still perfectly smooth. The corset only covered her midriff, and her tits spilled out over the top as I stroked her vaginal lips from my seated position. “Nice long blowjob to start with – then I’ll cum inside you – then we’ll finish with something special.” Leanne was in the zone by now, and complied happily. She licked and sucked my cock hard, before bobbing up and down on it at the same time as stroking the shaft with her hands. I let her do this for ten minutes, but I could feel myself nearing an orgasm. I picked her up and she straddled me on the chair face to face. We fucked like that for a bit longer, before I shot my load inside her soaking pussy.

“Well done, Leanne. You’re almost done. I’ve been keeping something for you.” I went to a cupboard and produced a bottle of champagne. “What do you think?” I asked her. She read the label.
“Lanson NV 1992 – is that good? It looks old,”
“It is old. I’ve had it since I was in University. Never opened it when I should have.”
“Ok, so what then?”
“I thought you’d do a bit of a dance then fuck yourself with the bottle. Take off the foil and the wire, of course. And make sure you’re well lubed. We don’t want that bad boy shooting the cork up inside you.”
“I think there’s more than enough cum in there to make it a smooth ride,” Leanne replied with a hint of fun in her voice. She took the bottle from me and removed the top wrapper and wire cork cage. Out of concern, I handed her the lube, and she worked it over the top of the bottle as though she were giving a handjob. She then leaned back on my desk and slowly inserted the bottle into her dripping vagina. She worked it back and forward, the dark green of the bottle disappearing in and out of her fleshy hole. She grunted and squealed as it flashed in and out, a combination of her juices and my semen running down the sides and collecting on her hands. She slowed, then sped up, before cumming violently with one foot planted on the desk, the other on the floor. She stopped, but her pussy muscles contacted around the dark neck of the bottle. She withdrew it, and a sticky thread of goo followed the cork from her hole. I could only nod in approval.
“You’re a good sport. Well done.” I took the bottle from her, licked the cork, then popped it. I fetched two glasses from the same cupboard, and poured a tall one for each of us. We talked and laughed like the old friends we should have been, and shared a second glass each. The Lanson wasn’t the most expensive champagne, and being NV it would only have tasted very middle range anyway – but to me it was like drinking from the pussy lips of Aphrodite. It wasn’t clear and clean – small threads of cum, lubricant and pussy juice had contaminated what had been poured into the glasses, but it was the most delicious drink I’d ever had.
I’d received that bottle on my lowest day ever, having been meant to share it with the same woman. Now I was finally opening it, having got everything I ever wanted from her. Not being a big drinker, maybe it affected me too quickly, but I looked straight into Leanne’s face. I noticed the freckles for the first time since that evening in the Hilton Metropole. “Leanne,” I said finally, “You’ll never make a lawyer. But I’ve kept my promise. You’re ready to be a hooker now, just take it easy, make sure you look the part and treat your clients like you’ve treated me this last week and they’ll pay you and happily come back. I’ve asked the manager of the St. Martins Apartments to start you off with a few contacts if you need them. Just don’t sell yourself short, stay safe and don’t go back to what you were.
“I promised you I’d show you how to earn a hundred an hour – but I actually think you could go for two hundred.” I stopped and looked into her eyes. I couldn’t tell if she was surprised or shocked that she had gone from aspiring lawyer to cum-filled whore in four days – or if she had expected this outcome.
“Do you still hate me, Jerry?” she asked simply.
“No, Leanne. All my hate for you sprayed onto your face and into your pussy and dripped out onto that couch, I don’t hate you any more.” Then I added, “But I don’t think we were ever very good together, so best we leave it at that.”

I didn’t see her again after that day, but I hear she’s doing well for herself now.
3 comments

anonymous readerReport

2013-07-30 11:14:56
Fantastic story with a great plot!

anonymous readerReport

2012-01-07 05:08:52
This piece was a lifejacket that saved me from dowrning.

anonymous readerReport

2010-09-01 17:40:07
Please write more - you're wonderful!

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