Creative Outlet – a blog full of stories and personal musings


Dear Diary – Chapter 30

Dear diary,

I.. hm.. well, I left you off at me prostituting myself to a reasonably powerful woman and I enjoyed it. I still enjoy it, I am still doing it and I don't have any interest in stopping. I feel satisfied, sexually - but I am missing a connection emotionally. Not that I ever expected that she could fulfill such a role, but I do miss the tenderness I received from Malene back "in the days".

The "adventures" with her, .. Sheila, as we are to call her, have been pretty adventurous, to say the last. Let me explain just how an average week works out:

Monday to Friday I go to school, but Monday, Wednesday and Friday she tells me to come over immediately after. That is, to her office. During the 1-3 hours I'm there, she's locked the door, we're playing and generally walking around naked - it is essentially an office of lust at this point. Sometimes she has to answer the phone or do something urgently and I am encouraged to continue our "session", or if it drags out, either act as a secretary (she gave me a brief introduction to it, just so I can pass off as it if it came to that) or do homework. The latter 2 becomes increasingly hard, mainly because my mindset is instantly turned into sex freak as soon as I arrive and she loves it. I am all out dominating, which makes for interesting phone conversation (granted, this is only when she gives me the get go to "interrupt"). A lot of toys get used every time and I've even had to replace several, as they just wore down - which is insane, I've never thought that could happen.

But, a few weeks ago, she suddenly had to go out of town for a lot of meetings over the weekend. She asked me to come with as a secretary, with a wink on her face and a smirk, but I wasn't sure if I could spend an entire weekend with someone I barely know (except I know her body almost perfectly - what felt good and what didn't, which I suppose is my job now). I tried to shrug it off with excuses that she would be in meetings all the time and that I wouldn't have anything to do but somehow got me convinced by using the words "Come on, it'll be fun.".. yeah, fun it was.

I had packed my bags, given a convenient lie to Malene, who I barely saw anyway and went with her. The car ride there, in her pretty BMW, was pretty much silent. We've never had the chance to small talk, other than dirty talk or to discuss the arrangement of our "deal". During this ride, I immediately regretted going and knew that this would be the most awkward weekend in my life. I blamed myself, mostly, being terrible at small talk - but someone I knew so intimately and yet rarely knew is a very .. special social encounter. I had little interest in her work, though I admired her since she is essentially the wheel that keeps the business turning, she is pretty, can stand on her own damn legs and has an amazing body for her age (late 30s).

As we rolled up to our destination, I realized I hadn't really asked the important question: Where. That where turned out to be the most prestigious, luxury hotel in the entire country. Oh yeah, I forgot to mention she had given me several business suits, much like hers, to wear at such occasions - but I could not feel more out of place anywhere than right there, as we stood in the reception, checking in. I held my bags, while trying to look as small as possible, as fat business men looked at me in my tight skirt as she checked in. A loud ding pulled me back to the real world as a man asked to take my bags. Reluctantly, I gave them over, thinking they were my last defense in a society run by the richest and horniest of them all. In the elevator, the deafening silence made me make up my mind and come clean about this to her, I know she is reasonable so I figured she'd be able to see it from my point of view. But, as we entered the hotel room, I was hit in the face with just what kind of luxury money can buy.

Thinking back, I probably decided to "abuse" this opportunity, but all I merely did was do what Sheila wanted me to do; enjoy myself as well as take care of her. I got paid a lot of money for this weekend as well as felt luxury close to my body. I do not come from poor qualms, but having a Jacuzzi, sauna, huge shower, huge TV with what-have-you extras, huge bed, huge room, the best kind of food a phone call away and the best view I have ever seen is .. relatively memorable, to say the least. I barely moved outside of the room.

Sheila had to go to a meeting as she arrived, to introduce herself and make sure everyone is here she said, and asked me to go with her. I wasn't sure - I was still extremely shy and didn't really know the agenda that usually happens at such meetings, but she took my hand, gave me a tender, lustful kiss and I followed blindly. The meeting was with some of the guys I saw down in the reception. Sheila and I were the only females there and I immediately felt that everyone was looking at both me and her. I was later told that there isn't much of a professional routine during the introduction meeting, so she usually got a glimpse of just how male dominated and perverted the big suits are, which made her quite happy that she finally had somehow to get these frustrations out with me being there. She also indulged that several of them had tried to get her drunk and sleep with them and had generally received the idea that most of them think that a woman should be in the kitchen or on their dicks.

All of them were from very very big companies and the meeting was apparently about a new law that would change a few things for them. The proper meeting itself would start Saturday morning, which meant Sheila and I had the rest of the day off. This being Friday evening.

Ah hell, might as well explain everything that happened this weekend, if just to relive the memories.

After getting "acquainted" with the room and all it's locations for .. fun and having studied the content of one of my bags, Sheila told me that we needed to loosen up. I agreed and said that I have felt that I don't really know you well enough to small talk or just generally chat. She nodded and agreed and said she also saw me as a friend as well as .. well, what I am. A prostitute, a lover for money. Her lover, though. I was, however, glad to hear that and smiled. I felt the same to her, which isn't hard when you spend 3 days a week with her, especially in the way we spend time together.

We ended up in the hotel's bar downstairs, downing everything the bar had while she was telling stories about the other guys she were meeting her. While I usually don't like backtalk, it was nice to hear them being knocked down a notch, so they don't seem so intimidating to me. We got very drunk very fast. Suddenly she wanted to try out some fun publicly, so we were suddenly kissing madly at one of the hotel's toilets. Thankfully, no one were there, since she was extremely loud for maybe there was just a big echo inside that huge toilet.

At around 3 in the morning, we decided to call it quits, so we slurried our way to an elevator, where we, as intoxicated as we were, kissed passionately. Suddenly, however, I noticed out of the corner of my eyes about 6 of the suits with a big grin on their face, looking at us. They were drunk, most of them, but as Sheila noticed them, she merely winked and smiled at them and kissed me again, fondling my breast. They were visibly affected by this but luckily, our elevator arrived and we hurried in before they could enter. She continued feeling me up, taking the initiative, which she rarely does except if I command it, in the elevator and eventually I found myself in the bed, exhausted, drunk, dizzy yet smiling with Sheila snoring next to me.

Next day, she had a hangover. I was more lucky. But, she then remembered what happened and started to become unlike something I have ever seen in her before; she became uncertain and almost panicked. The woman who is so constantly in control was struck by uncertainty about how her "unprofessional actions" could change her career in the meeting. I hoped she was just speaking out loud because I had absolutely no idea how to help her out in this. I hugged her, however, and gave her a reassuring kiss, like a girlfriend would, rather than a lover. She cooled down a bit, kissed me back and went to the meeting after a quickie in the shower.

Thankfully, according to her, the meeting went professionally. No one questioned her power, but she could feel that everybody there knew her .. tendencies. The uncertainty this gave made her feel powerless and she wasn't sure if it'd stay with them or move around and eventually come back to her own company.

But, here is the amazing thing about Sheila. She only thinks about it a few times before knowing she can't do anything right now. She doesn't break down due to uncertainty, but rather keeps on going until she is forced to stop. I admire that. Oh, I admire that. I wish I could be like that but this just shows how she became so successful and I am fairly certain it took a lot of sacrifice to arrive where she is at. Essentially, this was once I realized that I was very fascinated, even cared for this woman. She was the direct opposite of Malene, didn't need help to stand up, took what she wanted and pushed herself to reach her goals. I didn't need to support her, but granted, we didn't have the emotional connection - this is purely me whoring myself out to her. And getting paid for it. I started to feel bad about getting paid for something I'd do if she asked, at this point. I enjoyed it just as much as she did, I didn't see it as a job and she is my only client.

Saturday went with sex. A lot of sex. Everywhere. Again. It was relaxing and fun. She told me to dominate her completely so she didn't have to think about anything else than please her "mistress", as she called me in those situations. Roomservice was ordered and we ate it while sitting in the jacuzzi, watching TV. It was intense, amazing. I wanted to tell her about my predicaments, but I didn't want to stop this "dream", I was having. This was even better than the best sexual dream I've had. We went at it until we fell asleep in each others arms.

We had to be out reasonably early the next day, so there wasn't a lot of anything, except cleaning my "baggage" and packing. Sheila was mostly quiet, but pinched me every now and then for fun with a wink and a smile. I told myself that I would tell her when we were in the car. And I did. On the way back, I breathed in and told her everything I have been thinking about; regarding her paying me for something I'd do free, telling her that if she needed any sort of emotional help, I'd be there and just .. I dunno. I couldn't stop talking and eventually she pulled over and stopped the car and said: "Look, you're not exactly 18, are you?" I didn't know what to respond to this, other than blush and feel like the most guilty person in the world. She, thankfully, continued "I know that, you're doing school work not exactly at an 18 plus level. But," I had to look away at this point, because I could feel on her that she was emotional - not the calculated genius on two long, pretty legs she usually is. This weekend tore a lot on her and here I am, blabbering teenage shit at her - when I could have just had a regular conversation about this "job". "I think I need to pay you, to cover up my guilt about sleeping with someone who isn't over 18. I know it's not illegal here, but there is a reason I wanted it as distant as possible." She sighed. "But I've taken a liking to you." I looked back at her. She had tears in her eyes. I only muttered "likewise". She sniffled up, took a deep breath and then said in her professional, calculated voice: "I will stop paying you out of my personal pocket, but still keep you on the company's, if that is alright - you'll be paid overtime for accompanying me here, of course. I will keep inviting you to the office when I am able, but other than that, I think you are very welcome in my home." She ended with my name, said very softly. It made my heart beat faster. I think this is the start of our relationship. I nodded.

As I said, this had been a few weeks ago. In this time, quite a few things have been happening. The kiss she shared with me did hit her, as one of the guys attending the meeting contacted her about him "keeping quiet". Sheila, however, have been able to get dirt on all of the ones who saw us, and told him this. She told me later, in confidence, that the dirt on that guy was after a "business" trip to Thailand, he'd been seen with a less than legal prostitute. I still visit her at the office, mainly sex, though the days have been more irregular, since she is the one calling me when she have some time available. This weekend, she asked me if I wanted to get a tour of her house. I happily accepted.

Till next time, dear diary.

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