I Used to Work in Chicago Pt. 01

I met Sonia, a statuesque red head with a spectacular figure, through mutual friends while working in Chicago.

She was in her very early thirties, and an assertive, confident investment banker by profession. For those familiar with the industry she was probably four years out of business school, and had just made "Vice President" which is a sort of mid-level seniority. Not yet a "master of the universe", but steadily making her way up the greasy pole.

When we originally met I knew she had a serious boyfriend, and became engaged shortly afterwards so, although I found her very attractive, I didn't pay her much attention except in a polite, platonic, friendly way.

However one evening when we had just finished a night out with friends, and the others had dispersed, we were waiting on the sidewalk as I was chivalrously trying to get her a cab before heading home myself. We finally flagged one down and, as it pulled into the kerb, she suddenly pulled me towards her and kissed me on the mouth.

I was so surprised that I didn't know how to react. This may sound stupid, but I had her filed so firmly in the "long term boyfriend, therefore not available" category that it hadn't even occurred to me that she might find me attractive.

Although at the time I was single, I am generally a kind of a serial monogamist, so I genuinely find it difficult to understand why someone who is in a long term relationship (and I think she was actually engaged by this point) would suddenly lunge at one of her male friends. I am not judging, I simply don't think like that - probably just lack imagination!

After the kiss she stepped back, looked me straight in the eye, and said "that was nice."

Then, with a grin she jumped into the cab and, as it moved off, she stuck her head out of the window and shouted "call me" before disappearing into the night, leaving me staring dumbly after her.

I didn't have her number, so a few days later I had to get it, I hoped discreetly, from the mutual friend who had originally introduced us.

I was busy at work, and also a bit confused, so it wasn't until later the following week that I plucked up courage to call her at her office.

She answered professionally initially, and then, when she realised who was calling, she asked me to hold for a moment as she moved to somewhere more private, presumably an empty office.

"You took your time!" she teased. "Good to hear from you".

We chatted a bit and arranged to meet for a drink at the weekend. She didn't even mention her fiancé. I couldn't quite work out what her agenda was (and, yes, I do realise I am a bit slow!).

On Saturday she met me at my office around 6pm (I also worked in finance, so hours were pretty long and Saturday working was standard).

When she turned up at the reception of my office building I was slightly less unclear as to her agenda. She was wearing a tight black leather skirt, white t-shirt/body and a black leather jacket. Her long red hair was loose and flowing down her back.

She looked fantastic, and very classy - re-reading my description of her outfit I realise it could sound as if it was a bit tacky, but quite the opposite, the outfit was understated, sophisticated, and very sexy. Not an easy thing to pull off, but she had nailed it.

It was clear that others thought so too, as a couple of my colleagues who were also in the lobby gave me a knowing, raised eyebrow, look. However, I take more convincing and still wasn't 100% sure whether I was on a "date" or not.

I greeted her with a friendly double kiss "you look amazing - what's the occasion!?"

" We'll have to see won't we!!" she replied with a cheeky smile.

We went off to a bar to have some martinis - in my opinion America's crowning cultural achievement (although I realise this may be a controversial opinion, and I am prepared to hear opposing arguments in favour of the Peanut M&M).

We started into the martinis and after the third Sonia reminded me of Dorothy Parker's famous aphorism about four martinis...

"So who is the host I replied?" finally getting the message loud and clear.

"Well, if we go back to your place, you will be!" she responded looking me directly in the eye.

That was sufficiently unambiguous even for me "I think we should go" I said smiling, but also nervous. Heart beating fast, butterflies in my stomach "One more for the road?"

"Well that would make four..." she replied pointedly.

" Quite!" I responded.

The drinks came and we snuggled up together in our booth. Her hip pressed against mine, her hand straying to my arm, my leg as she emphasised various points she was making.

We left the bar and started to walk back to my apartment, which wasn't far away. She walked close and her hip bumped repeatedly against mine. She slipped her arm around my waist and pulled in close. I put my arm over her shoulders and did the same. With the hand that was not around my waist she reached up and took the hand that was around her shoulder, and gently but firmly pulled it down so it was resting on her right breast. As I think I have mentioned, she had a spectacular figure - I was to find out later she was a 34E - and I took the weight of her breast in my hand, massaging it gently. She nestled in closer and said "hmm, that's nice".

We walked like this the few minutes back to my building, and went up in the elevator to my 10th floor apartment.

We entered my apartment, which she knew, having been there a number of times previously with groups of people, but this was the first time she had been there alone with me.

Suddenly there was a slight awkwardness as to what to do next. For once I was smart enough to take the initiative and slipped my arms around her waist under the leather jacket and pulled her in to me for a kiss. I felt her magnificent breasts squash into my chest as I leant down to meet her offered lips.

She was tall, probably 5'9" or so, and in her "fuck me" heels she must have been nudging six feet. Still a few inches shorter than I, but the height differential worked pretty well.

As we kissed, our tongues entwined, exploring each others' mouths, and I took my left hand from her waist and put it behind her neck to pull her into me harder. Her groin rubbed against mine and she moaned gently as she relaxed into the embrace and also felt my cock hardening into her crotch.

I slipped off her leather jacket and threw it onto a nearby chair. I then unzipped her leather skirt and let it fall to the floor. Now I could see that the t-shirt was indeed a "body", cut very high around the legs and hips and with a thong back, completely exposing her magnificent arse.

I continued to undress her, enjoying the dynamic of my remaining fully clothed while she was, increasingly, naked. I kissed down the side of her neck onto her shoulders and then down to the tops of her breasts. As I kissed further down to the fabric of the body I slipped it off her shoulders and pulled the top down to her waist, exposing her breasts that were supported by a lacy silk bra.

She moaned as I kissed down her breasts and then I reached behind her to unfasten the bra. I slipped it off her shoulders to reveal the full magnificence of her breasts. The light freckling on her shoulders ended at the top of her breasts which were perfectly milky white. They hung firm but pendulous. Erect nipples pointing out 45 degrees each side. I kissed further down to take a nipple in my mouth.

Suddenly I noticed a tension in her. She was no longer relaxed and pulled her arms together almost as if she was trying to hide her breasts. She was looking down and to one side, not wanting to meet my eyes. I realised she was actually embarrassed by her exposed body.

It was unbelievable to me that anyone with such a magnificent body should feel embarrassed by it, but I also realised that a lot of people have quite unwarranted hang-ups about their physical self, and she was clearly no exception.

"Do you know how beautiful you are?" I whispered. " You have an unbelievable body".

I kissed her breasts again and then sank to my knees in front of her, kissing my way down her belly. I continued to pull the "body" down over her hips and then down to her thighs, exposing her pussy, nestling inside a neatly trimmed red bush. I kissed her there, inhaling the musky odour of her arousal. I grasped her arse cheeks in each hand and drew her crotch into my face. I pulled the body down her thighs and let it fall to her feet so she could step out of it.

She was now completely naked and I was still fully clothed.

I knelt back on my heels to look up at her, admiring her naked form.

Her red hair falling over her now naked shoulders; pale skin with light freckles. Large, creamy white breasts jutting proud, shapely arse, delicate spare tyre roll of fat around her belly, shapely but powerful thighs and long legs.

By day she might be an assertive and high powered investment banker but here, now, naked with me, she was simply a spectacular body, built for sex.

I looked up at her admiringly and said "I can't believe you are here with me in my apartment, naked"

She laughed in a slightly bashful manner "I can hardly believe it myself. For someone as slow on the uptake as you it takes real work!"

"Sorry!" I laughed.

The ice was broken and she seemed more relaxed.

"You are so fucking gorgeous!!" I said, shaking my head slowly. "It just didn't occur to me."

I pulled her groin into my face again, and kissed her pussy. Then I continued my journey downwards, down one leg, kissing her inner thigh, to her calves and feet, kissing her toes. I then went up the other leg in the same manner, until I reached her pussy again.

This time I gently opened her up with my thumbs, pulling her lips apart to allow me access to the moist interior. I licked her tentatively. Savouring the wonderful flavour. I circled her a few times, teasing her clitoris, eliciting little gasps from her. I then slipped my hand between her legs and teased her arsehole as I licked, which caused a sharp intake of breath and an involuntary clenching of her buttocks.

"I looked up and said, grinning, did you like that?"

She swallowed and nodded quickly. Not trusting her voice, to speak. Or not being ready to admit, out loud, what she really felt.

"Hmm. Interesting".

I left her pussy and kissed and licked my way up her body, over her belly, up between her breasts and then onto each of them, licking and sucking on each nipple in turn. I then went up her neck to her beautiful face and kissed her full on the mouth. Forcing her to taste her own pussy on my lips and tongue.

As I did this I put one hand firmly on each of her arse cheeks and grasped them firmly, pulling her naked body towards me, squashing her breasts into my chest.

We were standing in front of a full length mirror, which gave me a fantastic view of her naked body from the rear.

I span her around so that she was looking at herself full length, naked, in the mirror, with me standing behind her.

She tried to look away and down so she wouldn't see herself in the reflection. I held her head so she had to face forward. I saw her looking reluctantly at the image before her.

I kissed the top of her head " You look absolutely ravishing".

I cupped her breasts in my hands and feeling their weight, started massaging them gently. After a bit she moved her hands to mine and stopped me doing the massage. I wasn't quite sure what she meant by this but then she took my fingers in each hand and placed them on her extended nipples. She closed my fingers tightly over each nipple and squeezed in a way that must have been painful. Then she looked at me in the eye, via the mirror and said "Squeeze. Hurt my nipples."

"What? I responded, confused.

"I want you to hurt my breasts. Squeeze the nipples. Crush them. Hurt me. I like to be hurt. It turns me on. Makes me wet." she twisted her head to look up at me directly rather than via the reflection in the mirror "Am I a terrible pervert?" she asked, with an embarrassed smile.

I took her face by the chin and pulled her into me for a deep kiss "I don't think you're a pervert."

With that I grasped a nipple with the fingers of each hand and squeezed slowly but firmly, with ever increasing pressure. She moaned gently and then I started to twist her nipples. Hard. She cried out and gasped again. I lifted her breasts by the nipples, allowing them to take the whole of their substantial weight. I dug my nails into her flesh and twisted again.

Then I released her breasts and gently manoeuvred her forward, towards the mirror. I pushed her up against it, forcing her breasts against the cold glass. She gasped at the shock of the cold on this most intimate and sensitive area.

I reached between her legs and found her pussy from behind. I slipped one, two then three fingers into her slick interior and started to finger-fuck her pussy as I pressed her breasts against the cold glass.

I kissed my way down her back to her arse. I planted kisses all over her beautiful buttocks, gradually moving towards the crack between them. I pulled her cheeks apart kissing deeper and deeper into the crack. Smelling the musky, sweaty aromas that inevitably result when a woman spends an evening wearing a tight leather skirt, and gradually getting more and more aroused.

My tongue eventually found her anus, and circled it gently before probing inside the sphincter. The sweat-musk smell was overlain by a slightly acrid note of shit and I probed deeper, pulling her cheeks as wide as I could to allow me to force my tongue deeper and deeper into her fragrant arse. She was gasping and moaning, initially making ineffectual protestations, before writhing her hips, and thrusting back at my tongue as she surrendered to this intrusion.

I am not by any means a coprophilic, but that note of shit in the mix of scents and flavours added a real sense of depravity to the act, which I found highly erotic.

I see anilingus as having the potential to be both a dominant or a submissive act. Here it was dominant as I was "forcing" it on here. I was opening her up in the most intimate way possible. I wasn't giving her a choice, but rather, bit by bit imposing myself on her, allowing her to protest, but also allowing time for her token protestations to morph into acceptance, and desire. Obviously it is a fine line to judge when protestation is real or "token" - and we hadn't, at that stage, done anything so formal as agree "safe words", so that is why it was important to go slowly and see how things developed.

Conversely if, as I certainly hoped to do, I was later to "force" her to lick my arse, and she acquiesced, that would clearly be a submissive act, and I was certainly getting the sense that under her confident investment banker facade, there was a submissive masochist lurking not far from the surface.

But I digress...

As I continued to tongue her arsehole I kept my three fingers in her pussy, now sopping wet and I pistoned back and forth, almost fisting her as she became more and more aroused.

I then had an idea. The interior walls of the warehose style apartment were exposed brick, and the mirror was bolted direct to the wall, so the mirror was surrounded by brick.

I stood up, keeping my fingers in her pussy and guided her off the mirror and instead pressed her firmly against the wall and rubbed her breasts to and fro against the rough brickwork.

She moaned in alarm as she felt her nipples abrading against the bricks. I held her head in my hand to protect her beautiful face from the rough surface, but pushed hard to press her breasts and belly against the harsh wall, all the time continuing to hand-fuck her roughly from behind.

It must have been incredibly uncomfortable. Not to say painful, to have her nipples abraded like this, but she was moaning and crying in apparent ecstacy.

I then gave her arse an exploratory slap with my hand to judge her reaction. It wasn't hard, but firm enough to show intent, and she moaned gratifyingly at the impact. I then gave her a couple more slaps and she moaned again.

"Do you like being spanked?"

"Yes" she whispered, into the wall. I grasped her by the chin and turned her head to look at me. "Do you want me to spank you harder? Punish you properly like a naughty girl?" She nodded and whispered again "yes".

" I can't hear you"

"Yes please" she said more loudly. "Spank me - hard. Please"

I responded with a couple of much firmer spanks, which, in in addition to causing her to gasp with pain from the impact, also had the effect of forcing her breasts up against the wall, rubbing them more painfully against the brickwork.

I spanked harder and harder, and whispered in her ear "You are a very, very bad girl. Standing here naked, letting a strange man lick your arse and finger your cunt".

"Are you a dirty slut who needs to be punished?"

"Yes, yes, I am. I am a filthy little slut who deserves to be punished".

I grasped her by the wrists, pulling her hands behind her back, and forced her to hold my erect cock. Then I rubbed it along her crack from her pussy to her anus. As it rested against her anal hole she tensed "No!"

"Don't worry I am not going to put it in there. At least not today. And not without a condom. But I am going to put it in here - moving the end of my cock to test against her pussy - if you have brought some condoms"

She said nothing "Did you bring condoms? I think you planned to get fucked tonight, so I think you probably brought some with you. Did you?"

"Yes"

"Where are they"

"In my jacket pocket."

"Go and get one"

I released her and she turned around, displaying her scratched and abraded breasts. She walked across to where her jacket lay on the chair, bent down, displaying her magnificent, and now slightly pink, arse and reached into the jacket pocket. She returned with a condom in its foil packet.

I, of course, had condoms in the apartment, but the erotic power play of making her confess to also having brought some was too good an opportunity to miss.

"Are you a little slut who goes out with packets of condoms all the time in the hope of getting fucked by strange men".

She said nothing.

"Are you?" I asked, louder. "And by the way, I whole heartedly approve of that strategy!"

"Yes, I guess I am" and she laughed shyly, releasing the tension.

With that she knelt down in front of me, naked and opened the foil wrapper. She took out the condom and, at my instruction, rolled it onto and down my erect cock, which, as I remained fully clothed, stuck out of the fly of my trousers. I was still enjoying the power dynamic of remaining fully clothed while she was naked.

Once sheathed in latex she took my cock in her hands and stroked it appreciatively, before taking it into her mouth to give it a suck.

Then I took her by the hands and pulled her to her feet. I pulled her towards me, with my hard cock sandwiched between us and then grasped her arse and picked her up. She instinctively wrapped her legs around my waist and with one arm around my neck, used her other hand to feed my cock into her welcoming vagina. She was tight, but very wet, and my cock forced its way through the initial resistance before sliding smoothly home. With my cock securely inside her she put the other hand round my neck and pulled herself in tight.

She wasn't a lightweight and she seemed to revel in being picked up and fucked. I turned and banged her hard up against the wall. This time tormenting her back and arse cheeks against the brickwork.

I fucked her brutally and she screamed and moaned, digging her nails into my back. Even through my shirt I wondered whether she had drawn blood.

She found my mouth and we kissed deeply and passionately as we held each other tight.

We continued to fuck, roughly and then gently. I would pull my cock all the way out, and then thrust it brutally all the way back in. A couple of times I teased her anus again with the head if my cock, nuzzling at her sphincter. Each time I noted the tension this produced in her, and concluded that she genuinely wasn't ready for this intrusion today.