tagErotic CouplingsAnna's Dilemma

Anna's Dilemma


Just a short disclaimer: This is fiction. I'm not Anna, and will ignore feedback from those who think so.

Other feedback and comments is of course always appreciated. Love to all and enjoy the read. –Lin

It was morning. I could tell by the fact that I was about to wake up, like so many times before. Before I even knew who or where I was, I knew that it was morning. That was, and still is, the greatest blessing of my life. To be able to wake up, in my own pace, without the hammering siren of an alarm clock calling me to yet another nine-to-five torture day.

The rest, the money, the comfort, the clothes and the ease of day-to-day worries, was just icing on the cake. I would never have to worry about paying the bills. In fact, I would never even see the bills. All that was taken care of.

Slowly, my mind floated up to the surface of consciousness, a shimmering dot of sunlight in the darkness of dreams. As one by one my senses returned, I began to come to grips with the world around me, and what my senses told caused the gears in my head to start rolling. There was something not quite right here.

Maybe not wrong, but certainly out of the ordinary.

The smell was different. This was not the stale air of a closed bedroom and warm eiderdow sheets. This was not the light smell of my skin and my soap. No, this was the smell of sweat, musky cologne and the meaty, sweet tell-tale odours of a night before that must have been nothing short of amazing. Now, you might think that the thought of that would give me that ever so familiar, warm feeling that waking up after such a night can give.

Now it was just annoying, because as hard as I tried, I could not even recall the smallest detail about the day before. Nothing, my memory was blank.

The taste in my mouth told me the same thing. It seemed like I had been a good bad girl last night. The odd thought about whether soaking in THAT a whole night might be bad for the teeth or not passed drearily through my mind. But no pointer, no flashes, no recollection at all.

I could hear the sound of a serene sleeping breathing next to my left ear, and my bed was heaving underneath me in rhythm with the breaths, pressing against my chest.

Wait. That was no mattress. That was skin. Warm, sweaty, sticky, bare skin against mine. As I came to my senses, I could feel that naked body underneath me. I was lying right on top of someone. A man, a man with a strong, muscular chest where I rested my head, just underneath his neck and chin. My hand on the front of his shoulder, my legs straddling his right thigh. An arm was wrapped around me on one side, probably to prevent me from sliding off him, and it’s hand was resting firmly on my ass. A finger had even snuck in between my buttocks.

Where the hell was I? Who the hell was this man? Finally, I reached the surface of awareness, shook off the last traces of sleep, and opened my eyes. Ok, the surroundings were familiar. I was at home, in my own bed, but not alone. I lifted my head to look down at the face of the man underneath me.

I knew him. His name was Daniel. I knew him so well, much better than he knew me. And then, I suddenly remembered. Yesterday came rushing back...


He had been there for over a year. That kind, handsome, cheerful man. Always smiling, always helpful, polite, respectful. He lived two doors down, in an expensive apartment just like mine. We had shared the quietness in the elevator, we had shared short moments of idle chit-chat while waiting for cabs in the lobby, we had shared cabs sometimes, short walks in the corridors. A smile, a greeting, a comment on the weather, a brief discussion about whatever was on the news. Short moments in each others' homes, as we also shared books, occasional CDs and DVD movies. He had a lot of books.

The almost daily routine of polite greetings soon turned into mutual jestful, friendly flirting and five minutes of yapping about new books or movies. The encounters with Daniel became more and more important for me. It was a patch of normality in my extraordinary life, a break from the crazy roller-coaster that was my work. In my business, the mundane and the everyday becomes a cherished hobby.

In time, we got to share more than just books. He shared his musings on everything under the sun, I shared my laughter at his easygoing way of approaching even the most serious matters. He shared stories about his family, I listened and relished, but didn't open up about mine. How could I, when I had none? He told me at length about his work, chief developer and co-owner of a successful software development company. A position which immediately made me label him a geek. All in good fun of course. He was my geek, I was his bookworm. He told me on a regular basis about meetings and characters he met at the office. I kept my mouth shut about my days. I mean, come on. How could I ever tell him? Fortunately, he took the hint of my reluctance to share, and asked no prying questions. Always careful, always respectful.

But still, how he must have wondered.

That all came to an end that one afternoon, when I heard that familiar tappeti-tap-tap knock on my door. I went to open it, and as expected, Daniel stood outside. I wondered what he might want. Maybe something fun had happened at work that he wanted to share? Maybe he had found that book we were both looking for?

"Hey, geekboy!" I said and gave him a friendly hug. "What's up?"

"Oh, not much, Anna. Say, are you big on musicals?"

"Musicals? I don't know, I think people bursting out into song just looks so silly in a movie. Not since Mary Poppins, if you ask me."

"Oh, I don't talk about the movie kind, but the real thing, on stage. That's a whole different thing. See, the reason I'm asking is that I've got two tickets to a new show tonight. I don't know quite what it is, but It's supposed to be really good. But my date decided to stand me up and spend the evening doing adult things with her ex instead. So, I'm all alone, with first class seats, and no date. Wanna be my replacement for the night?"

That's when my brain shut down and caution flew out the window.

"Wow, can I come!?"

"You know, I just asked. Duh."

"Smartass. Of course I wanna go! When is it?"

"At eight. We'd better take a cab at seven to get there safe on time. Unless, Are you hungry?"


"Then just put something nice on, and I'll meet you in the lobby in ten minutes."

"Make that twenty." I said. "I'm a girl, you know."

"You are!?" he said with feigned chock.

"Very funny. Twenty minutes. Now scram, so I can take a shower."

"Need any help?"

"Haha. Go away, you naughty boy."

"Yes ma'am. See you then!"

We had dinner at a small Lebanese restaurant nearby, with excellent food and a good selection of wine. Most of all, it was quiet, good service, and not as snobby a clientele as in the uptown joints. We enjoyed our meals and went on with the same old yap and banter that we always did, about movies, books, now also musicals, and almost anything under the sun. Then we hailed a cab and aimed for Broadway.

I don't remember anything about the musical, except that it was the rocky kind and that the music was a bit loud. I wasn't paying attention like Daniel was, I was too caught up in the moment. This was the first time in years that I had gone out and done something like this - in private. Being myself, relaxed, with a good friend. So I just sat there and enjoyed being on a regular date. Yes, this was a date, I realised. A date with a good, nice, normal man. When did that happened last? Had I ever had that before?

After the show, the night was far from over. We rushed to the nearest bar, and ordered in silly drinks with umbrellas. We drank, we talked, we drank some more, we laughed, giggled, danced, laughed some more, drank some more, threw peanuts at eachother, threw peanuts at other guests, were told to stop that, bought drinks to all that we had thrown nuts at, and danced danced danced until our feet hurt.

Finally we found ourselves cooling off in a cabride home, and then, in the elevator up to our floor, I turned to look at him. Drunk from alcohol, summer heat, and a boldness that came leaping on me from nowhere, my dam finally burst. I wanted him so bad, I needed him to be all mine, wanted to give him the real me, share all my secrets with him. But I couldn't I just couldn't tell him, I was so afraid of what he might say, or think.

So, that night, I gave in to the easy route, and gave him what I right then thought I safely could. My body.

I was too far gone to think it over, too washed over with wine, desire and infatuation to remember that there was a tomorrow, that I would have to wake up. That was for later, now there was only him.

There, in the elevator, his top buttons open, his hair in an irresistible mess, his arm around my waist, hand on the summer sweaty skin of my bare midriffs, me leaned against him, I passed the point of no return. I faced him, grabbed him by the head and placed my lips on his in a feverish, intense kiss.

After a few seconds of stunned surprise, Daniel managed to get a grip on himself and pry me away.

"Woah! What are you doing?" he asked.

"Shut up." I murmured, and launched another attack at his mouth.

He didn't resist this time. Instead, he put both his arms around me and pulled me closer. My body pressed up against his, his hands on my back, our lips parted, seeking out eachother. When he sucked my tongue into his mouth, the world around me melted away, blurred and all that mattered was his hands on me, his torso against my breasts, and his lips on mine. The elevator reached our floor, opened and closed the door, and started down again, we didn't notice.

Five minutes of occupying the elevator later we staggered, much to the relief of the other hotel guests, out of the elevator, lips still locked, hands all over each other, and across the corridor, straight into my apartment.

In one way, I was so jaded, so bored out of my skull with this. But in another way, it was so good, so real, so incredibly long ago. Long ago? No, forever. I was a virgin, my deflowering incredible. I was a virgin, taken a thousand times before, with fingers, tongues and cocks in every hole, fucked senseless, pumped full of white hot cum.

And still, I was a virgin. Because I had never been made love to.

Clothes were pulled, buttons popped loose, my blouse accidentally torn, as we stripped ourselves and eachother in an almost panicked whirlwind of pent up desire. When I was down to my panties and a bra with one strap already down, I finally managed to snap out of the frenzy and staggered back. Breathless, pulses racing, mouths open, we stared at eachother.

"What are we doing?" Daniel panted. "It's the wine, the drinks. This is... This is crazy."

"Is it?" I breathed bach.

"Yeah, I mean... Isn't it?"

Yes it was. Crazy as hell. More crazy than he could ever guess. But the words just came out of my mouth by themselves.

"I'm not that drunk. I'm perfectly clear. No, this is not crazy, this is wonderful. I want you. I want you so much, Daniel. Don't tell me you're not attracted to me."

"Oh, god yes, I am. But it will change things. You and me won't be the same anymore. We haven't crossed that line, yet. We can still back out, and you can still be the girl next door. My bookworm. What if we break that?"

"I don't give a shit! I can't stand this! I want you. I want you inside of me. I need you to fuck me all night long, or I'll go insane! Please!"

In two steps he stepped up to me, took a firm grip at the laced front edge of my bra and just ripped it off my body. It all went so fast that I didn't even feel any strain at the straps or on my back, just a faint sting across my back, like from a torn band-aid. It wasn't until after a few seconds that I realised that my chest was bare and that the torn piece of lace and strings that Daniel tossed aside was what I'd just been wearing. Then he promptly picked me up, like I weighed nothing at all, and carried me into the bedroom.

"Don't do anything, let me." was all he said, as he gently laid me down in the middle of the bed.

It was happening. I felt like in a dream, the edges were blurry, I felt so warm, so oblivious of anything outside of our two bodies, so safe, so completely taken care of. Daniel leaned over me, kissed me softly on the lips, and placed kiss after kiss after kiss down my body, spending some extra time to suck on my nipples, lick my belly button and blow some warm air on my crotch. Then he sat on his knees, and started pulling my panties down. I lifted my hips to allow them to slip off my ass, then raised my legs as he freed me from them entirely. He then held them up and looked at them with a smile. He held the panties under my nose, and the scent of my own sex filled my lungs.

"Feel that?" he murmured. "Feel how wet you are? When did you get this wet?"

"In the elevator." I breathed.

He held up the panties to his own face and took a deep breath. "That smells so good. It must taste even better..."

He threw away the panties and positioned himself between my legs. I instinctively spread them as wide as I could. Slowly, ever so slowly, I felt his tongue come in contact with my pussy lips, parting them, and slide deeper in. A rush of pleasure washed over me, and I moaned in delight, as he just kept sinking deeper and deeper inside. Then his hands were there. fingers tracing the slit, lubricating in my juices, before sliding up to my clit. When Daniel's fingers reached it and started moving in small circles over the sensitive knob, I totally lost it. I just arched my head back, and gave myself to his skilful caress and tougning. Another lubricated finger had been placed on my anus, rubbing gently, but not penetrating.

"Push... push it in..." I panted.

"My finger? Do you want my finger in your ass?"

"Mmmm, yes! Please..."

He pushed, and the finger slipped in first one knuckle and then the second. I love a finger up from behind, and Daniel seemed like he knew what to do with it too. He began to wriggle it around slowly, and pushed it in and out in a slow, fucking motion, in rhythm with the movement of his tongue. I had his fingers on my clit and in my ass, his tongue fucking my cunt and my own hands pulling and pinching my nipples. I could feel my orgasm coming like the train, and when it hit me, it felt like being hit by a train. My mind exploded, my body tensed up, and I let out a loud, long moan. Before my orgasm had fully subsided, Daniel had sat up, taken his hands and mouth off me and climbed up to position his cock at my pussy hole.

I hadn't even noticed when he took off his pants. Now his hard naked cock slid in without any resistance, it filled me up, he stayed still for a few seconds and I could feel every detail of it inside of me. I looked up to find him looking straight into my eyes, and from that moment, I could look nowhere else. I was hypnotised. Trapped. When his cock began pumping in and out of me, the gaze remained still, steady, intense like nothing else. While Daniel's cock was fucking my cunt, his eyes were making love to my soul. When he finally came, erupted and unloaded his seed inside of me, he closed his eyes and arched his body, then sunk down on me, emptying the last drops in my womb with a series of short, fast thrust.

For the second time in only a matter of minutes, I also came again, clung to Daniel's upper body, bit down on his shoulder, and grunted in pace with the thrusts. We rolled over to the side, and his cock slipped out of me, as his eyes found mine again.

"Happy?" he said with a smile. I just grinned and kissed him on the nose.

"Hey, that wasn't 'all night'." I teased him.

"Take it easy, bookworm. I'm a guy, you know how we work. I need some time to, you know, reboot."

I laughed.

"Reboot?! You geek! Well I need some rest too." I said and rolled over to the other side. "Let me know when you're up for some dessert."

Sexual tension out of the way, my saner side returned with faint objections. This was the man that I had sworn I'd never let that close. The man that unknowingly was the centrepiece in my daily routine, but that I thought I needed out there, distant, polite, normal. Well, fuck that. There was no way to go back now. And I was too spent to be pondering tomorrow. Then Daniel turned around, kissed the back of my neck, slipped a hand around my waist, and pulled me close. For a while, spooned and feeling so comfortable and safe, I allowed myself to drift off to sleep.

After only a few minutes I woke again, feeling that familiar tingling between the legs. Daniel had not fallen asleep, but was absently stroking my hair with one hand and the skin on my tummy with the other. I sat up, looked down at him and smiled.

"Ready for more?" I said.

"I thought you'd never ask."

We kissed, we licked, we caressed, we fucked, we sucked, we came, we groaned, we screamed... How many different ways? How many times that night? I can't remember. But from the way I woke up this morning, I'd say that the last time was with me on top. I like that. That's where I'm at my best. It's always appreciated.


That was yesterday, and now I had woken up, it was morning, and the magic of the night was wearing off. Left was the mess, the situation that I had put myself in, my situation, and my strange, strange life. A life that I now had to drag Daniel into. Poor Daniel, he didn't deserve that. He deserved a simple, good, romantic relationship with a nice, normal girl. And I'm not that. Not at all. Sure, I can act nice. But normal? That's a joke.

So now I was sitting there, at the edge of my bed, now knowing what to do. This was such a weird situation, I could had read a million Cosmopolitans through my teens, and watched Oprah for fiftytwelve seasons before anyone addressed anything even remotely close to my situation.

"Hey, lover." his voice called. He had woken up.

I didn't reply, but before I could stop myself, I had let out a troubled sigh.

"Huh? Are you ok?" came the voice from behind my back. I turned around to face him. It was time for the truth.

"Look..." I started, but interrupted myself, still struggling for words. "Shit! I knew this was going to happen, sooner or later. Damn it!"

"What's the matter?" he asked.

"I really like you."

There. I blurted it out. So what the hell, I might just as well wing it from there, and see where it got me, I thought. "I might even...I might even be in love with you."

First he didn't say anything. Then; "Wow. I'm glad to hear that, because I really don't want this morning to be the end of us."

I sighed. "And that's what makes this so damn hard. But I can't lie to you. If you want to keep seeing me, you'll have to know the real me."

"The real you. And who might that be?"

"Just shut up, and promise that you let me finish."

"Sure. I promise."

I told him everything. Everything that I thought I could never tell anyone outside of my business. I told him what, where and how I made the money to rent this great apartment, and what I did when I was away for those nights and weekends all the time.

I told him all about how I was the welcoming arms for the rich and mighty. How I was the ultimate discrete 'adventure' for many public persons in this big city. How I was the travel companion and no-commitments all-night sex-partner in upscale hotel rooms all over the world, the instructor of advanced intercourse for the young, rich and restless family-money brats, the dominating aggressive slut for a few regular business execs and the obedient fuck-toy for yet a handful more. All that I was, and all that I told him about, every sordid detail, every role I'd play for the right price.

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byLinbido© 9 comments/ 22893 views/ 2 favorites

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