Anna's Dilemma

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Linbido
Linbido
7 Followers

"Call it what you will." I told him. "I guess I go by the names Elite Courtesan or International Escort if you were to ask my agency, but we all know those are just silly labels. I'm a prostitute, and I'm not above admitting it. In fact, I wouldn't have it any other way. Whatever you do, don't think I don't have options. I could wait tables, I could go back to the Uni and get a degree, and I intend to one day. But for now I choose this. So don't make the mistake to pity me. This may sound weird, because not many do, but I actually like my job. I love sex, but it has never been very sacred to me, if you know what I mean. I gladly fuck a nice man who respects me, and all my clients are very nice to me. Now I make more money than I thought I'd ever make in my whole life, doing something that I'd do for free anyway. I might be the only one in the world, but yes, I'm a happy whore. Well, there you have it. That's me. So what do you say?"

"Wow." Daniel said. "That was...different. I thought you were damn good..."

"I am good, that's what I'm paid for."

"...and so modest too..." he said with a little smile. "Anyway, I never would had gotten the idea that you might be a, well, pro." he said, and fell silent for a few seconds.

Then suddenly, a tentative question. "Do I...owe you something?"

Shit. I knew it. I knew he wouldn't get it. For some reason that stung, it really bit me. I felt a lump in my throat that I couldn't really explain. I'd known he might misunderstand. But it still hurt.

"I can't believe you said that." I whispered in a small voice.

"Sorry, I'm sorry. I...I didn't mean to...I don't know what I mean. I don't know how to react, I don't know what to expect. You surprised me."

"You're my friend. You have been my friend for so long. I'd never fuck you for money. That is work, you're not work. And we didn't just have sex last night, you know that. We made love. That's different. Besides, I'd never let a customer into my home. Never."

"Hey, chill it. I'm sorry, I apologise. Ok?"

We sat there in awkward silence for a minute. I had no idea what else to say. The cat was out of the bag now. It was up to Daniel to continue this. When he did, it was in a quiet voice, carefully choosing his words.

"When I first saw you, the same day that you moved in, I fell for you. The way you walked, the way you carried a suitcase, your voice, your beauty. I didn't dare to walk up then and say hello. You looked too good to handle, if you know what I mean. This year has been torture. Wonderful, exquisite torture. You are so perfect. Outgoing, funny, smart, sexy, beautiful. You've been my one and only fantasy, from day one. So close, but such an impossible dream. I never dared to try and make it more. You'd surely laugh me off, maybe even close the door to friendship, since you are way out of my league."

"Out of YOUR league?" I interrupted. "You need to take a look in the mirror."

He laughed a soft laugh.

"Thank you...I guess. Anyway, now you know me. I'm crazy about you, and that is not going to change. If you do what you do, and you feel good about it, I'm not going to be the one who judge you. Everyone is free to do whatever they want to, and I have no moral zealot standpoint about that. I was actually about to call a girl like you. I browsed the net for escorts, and found a site with a young lady who actually reminded me of you. Your height, your hair, your skin. I couldn't see if she had your face, it was blurred. I figured that if I had her over, and closed my eyes, maybe I could pretend that she was Anna, beautiful Anna down the hall. My bookworm... That's when I finally gathered the strength to ask you out instead. I figured that if I was rejected, I'd toss the tickets and have this Sheri as my backup plan. Pathetic, I know, but I was so nervous."

Now it was my turn to laugh.

"Sheri? Not Sheri Wallace?!"

"That's the one. Why? Do you know her? Oh, please don't tell her, I'm embarrassed enough already."

"You silly, wonderful thing!" I said. "I am Sheri Wallace, my agency made that website. Those blurred pictures was of me!"

He just stared, his jaw dropped. "Wh...wha...you?! You're name is Sheri?"

"No, I'm still Anna. Do you really think that I would put my real name on a website where I promoted my ass for rent? There are too many psychos and fanatic moralists out there for that."

"Then..."

"Yes, this could had gotten really weird." I smiled and put my arms around him. "I'm glad you didn't call. I had a wonderful time yesterday. If you had called, I don't know... Who knows how I'd had reacted?"

I snuggled up against his chest. He stoke my hair, and we shared that silent moment.

"So..." I finally said. I had to get this last thing out of the way. "Are you ok with me...getting in bed with all those other men? I mean, could we be together, in the middle of that?"

"I never said I was ok with it." he replied. "I guess I'll have to figure that one out as we go along. I guess you don't want to quit, do you?"

"No, I really like it. You'll have to know that from the start. Even if I quit the job, I think that I'd want to keep the sex thing a bit...liberal. That's me, take it or leave it. Just promise me that we'll at least be friends."

"Absolutely. But if we're together, could I really share the graces like that? Maybe I'm the jealous kind? I don't know...yet."

"Jealous?" I said with a giggle, and cupped his balls with one hand, as I pushed him onto his back with the other. "Why would you be jealous? What we have won't be just about sex, you know that. I'll give you all that they get, and more, for free."

"Woah!" he gasped when I wrapped my hand around his hardening cock. "When you put it that way...it doesn't...oh...sound so...bad...jesus! What do you do with those hands?!"

"I told you I'm good." I chided him. I kneeled by the the bed, my head hovering just above his glistering cockhead. I gave it a light, almost friendly kiss on the tip, and licked off a drop of pre-cum.

"Want to know what a thousand dollar blowjob is all about?"

"Sounds...nice." he crooned, completely under the spell of my slowly pumping hand.

I lowered my mouth onto his now rock hard cock, eased the head in between my lips and sucked lightly on it. Daniel groaned, and placed a hand on the back of my head. I promptly removed it. His cock was my violin, and I knew how to play it without his help. I had done it so many times before, brought many men so close to the edge that I could feel their balls twitch in anticipation, then backed off, ignored their pleas, only to bring them close, so close, again and again. The taste of cock didn't really do anything for me, but the worship, the pleas and the men at my complete mercy was such a turn-on. Finally, after about thirty minutes of pleasureable torture, when the climax was closing in again, I didn't back off. Instead, I pushed myself as far down Daniel's cock as I possibly could, ignored all gagging impulses, and sucked with my throat, my mouth, the length of my tongue, until I felt the spasms in Daniel's body, heard his loud grunts, and felt his juices shoot straight deep down into my throat. I held my breath, and let his climax end completely before letting him slide out of my mouth. I slowly licked the cum-soaked cock clean, while Daniel was trying to catch his breath.

"Did you like it?" I asked him.

"Like?! That was the most...intense...thing...ever!"

"Boy, you're in for a surprise then. We have at least a hundred more things on our to-do list. But first, it's your turn."

I had no appointments scheduled for the whole weekend, so this lovely man was not going to leave my bed. I'd make sure he didn't.

Linbido
Linbido
7 Followers
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9 Comments
LouXIVLouXIVover 18 years ago
His eyes were making love to my soul....

Great story - wonderful surprising transition from virgin to prostitute. Have you read "Eleven Minutes" yet? Ciao, LouXIV

AnonymousAnonymousover 18 years ago
Good writing-good details and very good story line

A very good written story and loved the story line. I guess it proves that even "whores' are human beings with human, womanly feelings. I hope you'll write more about these characters.

Thanks Joe

AnonymousAnonymousabout 20 years ago
The foreward

is off putting, I don't think I've read story on Lit that had one like that. but I still enjoyed the story :)

ffreakffreakabout 20 years ago
Good writing

Loved it. Your character tells a wonderful remembrance and then brings us to the present, even the author talking to us in the front fits neatly into the story.

Hope you do more stories.

damppantiesdamppantiesabout 20 years ago
Loved it

The writing style is great. Casual and unpretentious. I really enjoyed reading it and there were regular gem moments in the story at intervals which made me smile again and again so that I was anticipating the next one. I wasn't disappointed. Thanks for writing this one and don't make us wait too much for the next. :)

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