Escort Ch. 01: Dreams of His Daughter

Chapter 1 - Joining an Escort Agency

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Ever since I gave up my virginity almost six years ago I've had sex with a lot of guys in a wide range of situations. As varied as they may have seemed at first glance, until recently there was one thing that they all had in common. Either I knew who my partner were or at least someone I knew also knew who he was. In all that time I'd never gone out alone with some stranger just to have sex. When it comes right down to it, it wasn't so much that I didn't want to or was afraid of it, the opportunity just never came around.

Going to a strict religious school where any form of sexually-related conduct was forbidden had proven harder than I'd expected when I signed up. My freshman year turned out to be not so bad once I discovered that my roomie was bisexual. Unfortunately her parents decided to save some money so she was living at home our sophomore year leaving me with nice, but very virginal, new roomie.

Although there were some times during Thanksgiving and Christmas breaks when I was lucky enough to go home and enjoy myself, there were only a few other times that I was able to have sex with someone. Needless to say having been accustomed to having sex on an almost daily basis it was not easy for me to accept this sexless situation. When I was horny it didn't matter that I "knew what I was getting into." It's easy to think you can do something but sometimes putting it into practice can be a lot tougher.

In a recent diary entry about my first bachelor party I explained a lot more about all of this so I won't repeat everything here. Bottom line is I got to the point where I had to do something about the insatiable cravings growing within me or die of horniness. Well, maybe I wouldn't have physically died but it would've been a welcome respite!

What I DID do was to apply for a position at an escort agency and it wasn't long before I was the entertainment at my first bachelor party. I can't tell you how nervous I was before it started but it turned out to be an incredible experience! Having a room filled with horny men all staring at me with pure lust in their eyes and raging hard-ons was one of the most erotic things I've ever experienced!

Since I first noticed it happening as I was growing up, I've always loved it when I saw men looking at me like they want me, when they openly show signs that they desire my body and are willing to do just about anything just to see me naked let alone touch me - or do more. To have a whole roomful of them all at one time, and then to be fucked by each one in front of the others regardless of their age or marital status, was enough to make me cum over and over again.

After the complete success of that night, I was ready for more and tonight was going to be another first for me - being an escort for a total stranger.

One of the first things I learned was that there are some pretty strict rules if you're going to be in the escort business, at least if you're part of one of the legitimate agencies that's not serving as a front to a prostitution ring. First and foremost, such agencies do NOT sell or promote sex. They only arrange for a man to hire the services of a girl for a date - be it dinner, a movie, show, or business affair. Supposedly they check out the guys to be sure they're not felons or wanted by any police agencies or listed on any sex-offender lists. The main point again being that they are a legitimate service and not a pimping agency. If a guy just wants a hooker then he can cruise High Street in Columbus and take his chances.

Payment terms were something new for me as well. At my agency the client paid the agency directly for the evening so I never had to deal with cash or credit cards. This also had the added benefit of provided me with protection against prostitution charges as I wasn't handling money. I was paid by check twice a month just like any other job, paying taxes and all!

The agency also provided for my transportation each way in the form of a taxi that picked me up at school, dropped me off at the arranged location, and then was always available on a moment's notice to take me back whenever I called.

Of course, all that was said with a wink and a smile. During my indoctrination I was warned that most men would ask if I was available for additional "services". You can probably guess what such services consist of. The agency's official policy was that anything I arranged with a client AFTER the date was entirely my business AND my responsibility. It was up to me to establish what, if any, "tip" I wanted if I decided to go beyond the standard "date" rules.

Even though I knew this all up front, I still couldn't help but wonder just how it would all go in actual practice. One thing that made me feel better was that I was able to have a say regarding the guys I would meet. When I filled out my profile I limited myself from the start to only married men over forty, preferable with a family, and they had to be from out of state.

Yes, there was a method to my madness. Older guys had always treated me well. I figured married men would be more discreet and less likely to have STDs. As for being from out of state, I hoped that would keep them from any expectations that they might meet with me again afterwards.

Finally, I also set a strict rule that only one date per guy - no repeats. Unlike most of the whores I met at the training class who were plainly in it for the money, I was doing this for fun and so I wanted variety over quantity. Plus, I didn't want there to be any chance that someone would think we were starting to form any type of "relationship".

Chapter 2 - Getting Ready

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The agency must have had a lot of guys applying because despite my tight restrictions it wasn't long before I was getting numerous e-mails from the agency regarding potential clients. One guy caught my eye right away. He looked pretty handsome and had written a clever and entertaining introduction. He was from Chicago but what caught my eye was that he'd always been married to the same woman and even had two daughters, the oldest who was my age. He seemed to be the right one to start with so I replied to the e-mail and soon received a confirmation for the upcoming Friday.

For the rest of the week all I could think about was my upcoming "date". I had been on blind dates before and I knew most guys expected to have sex so that wasn't the issue. The difference here was that nobody had ever paid me to go on a date with them which put everything in a while new light. On a blind date, if I didn't like the guy I didn't even have to leave my house with him. In this case I was being paid to at least have dinner with the guy, no matter who he turned out to be.

I had never been this nervous before a date before! The night before I could barely sleep wondering what else he would want to do beside just have dinner. At the same time I was getting hornier each day wondering the same thing. The fact that I had no idea what he might want to do with me was exciting. Would he want just a hand job in the restaurant? A blowjob in the car? Would he take me to his hotel room? Would he want it rough or gentle? What if he was into something kinky? The possibilities were endless and I masturbated several times a day thinking of a different scenario each time.

Friday classes for me were over by noon this semester making it easy for me to get ready in plenty of time. The biggest decision was the same I faced before any date - what to wear. I toyed with the idea of going for the traditional schoolgirl look but decided on something with more sophistication. In the back of my closet was a nice slit black dress I'd bought for a dance once with my cousin which showed off my figure nicely without being TOO slutty. Although it caught a few close looks from the chaperones but they let me get back. It would be perfect!

Looking through my lingerie, I selected a sexy black thong that rode high on my hips such that when I crossed my legs and let the slit in the dress do its thing you might be tempted to wonder if I was wearing anything under it. A strapless Wonder Bra provided a bit of enhancement to my less than optimal cleavage. Finally, a pair of stiletto high heels with thin straps finished it off which also helped to firm up and show off my legs to their best advantage.

I spent the afternoon trying to add some body to my hair which, as usual, valiantly resisted all attempts at putting any body into it. This time I finally won the battle although I still envied those girls with the naturally bouncy full hair! I knew if things got a bit exciting tonight that it would go flat again but by then I figured he wouldn't be looking at my hair anymore, if he ever did in the first place. It wouldn't be the first date where I came home wondering if the guy even knew what color my hair was!

I've never been big on makeup except during a terrible bout with acne when I was fifteen that fortunately lasted only for a few months. Looking in my mirror I saw a "girl next door" face and wondered whether he wanted that or someone more sophisticated. I compromised with a bit of foundation, some eyeliner and lipstick. Nothing too bright or wild but enough to add some color.

Finally the package was all together. I had my hair in place, makeup ready, and dressed to kill. Now all I had to do was wait for the taxi.

While I was waiting my roomie was back from dinner. Karen looked at me and I could imagine the line of questions she wanted to ask me. I wasn't dressed like a slut but at the same time, it certainly wasn't an outfit I'd ever think about wearing to chapel. In the end she just smiled sweetly and asked, "Ummmmm, got a date?"

It was all I could do to keep from laughing out loud. Actually, this was one time I could tell her the truth about my plans for the evening. Well, at least it would be true so far as what I told her.

"Yeah, going out for dinner tonight in Columbus," I answered coyly.

"Must be somewhere fancy. Anyplace I know?" she asked.

"Someplace downtown, can't remember the name," I replied, which was technically the truth once again. You can't remember something you never knew in the first place.

That seemed to satisfy her and she went about to her business. Karen was a virgin through and through. The girl didn't even masturbate! Even so, she was great looking and knew it. She might not have sex but she knew how to tease and flirt with the best of them. She went out on a lot of dates and wasn't afraid to dress to the hilt. I always felt sorry for the guys though. Seeing her in some of her wilder outfits they must have thought they'd hit the jackpot. I could've told them not to get their hopes up. Karen was totally brainwashed in that she had to save herself for marriage and no guy had a chance of breaking through that barrier!

It was a few minutes before eight so I went out to the lobby and saw that a taxi was just pulling up. I figured it must be mine so I went out and sure enough it was. The driver already had instructions on where to take me so I just got in and rode quietly for the next hour or so, getting more nervous and more horny with each passing minute.

Chapter 3 - Dinner

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The taxi pulled up to the curb of a fancy Italian restaurant in the Arena district of Columbus. I quickly got out and went inside where I gave the hostess my name. Amazingly she seemed to know who I was and immediately directed me to a table where a man was already sitting.

Seeing me coming the guy rose to his feet and smiled at me. My heart beat rose a few notches as I looked him over quickly. He was dressed in an expensive suit with an off-white shirt and brilliant blue tie. Although I knew from his profile that he was forty four, he still had a full head of hair which was graying at the temples but that only lent an air of sophistication. He looked to be about six feet tall and obviously worked out from the trim build and just the way he carried himself. He was handsome in a classic manner, standard white protestant male. Clean shaven, he had a pleasant smile without showing too much teeth. He tried to act nonchalant but I saw his eyes giving me the once over quickly.

So far, so good! As I approached he extended his hand and gently shook my hand. Nothing too firm as if I was a business pal but perfect for a lady to hold.

"Good evening... Kelly I presume?" he said, "I'm Greg. It's a pleasure to finally meet you."

I smiled sweetly as he helped me off with my coat. The hostess took it and left, but not before I saw her smile a bit and shake her head just enough to signal that she knew what was going on. Oh well, I didn't know her anyway so who cares? Greg pulled out my chair for me to sit in. Wow, I actually felt like a schoolgirl on a first date, not really sure what to say. Greg seemed to sense my awkwardness and he carried most of the conversation at the start. After some small talk about the weather and school, he reached across and put his hand on mine.

"Just to put your mind at ease, Kelly" he said, "I'm happily married and I even have a daughter your age. Actually I just became a grandpa last month when my older son and his wife had a little girl. I've never dated anyone like this before so trust me, I'm more nervous than you are!"

The part about his son hadn't been in the profile which raised a small alarm within me. What else had he left out? Still, I laughed a little at that and immediately blushed as it made me sound like a teenager giggling at some boyfriend's remarks. Greg smiled and held my hand.

"You really are cute you know. Do you mind if I ask if you do this sort of thing a lot?"

Suddenly I felt so young for some reason. He was so much older and mature than me that is was almost intimidating. Sure I'd been with older men before on dates before, including my father, but Greg was like right out of a Victorian romance novel! I shook my head and although I meant to speak, my reply came out more as a hoarse whisper.

"No, I've actually never done anything this before."

That seemed to break the ice. I think we were both relieved to find that we each were "virgins" at this game so it wasn't like we felt we needed to measure up to a past history of liaisons. From there we talked about ourselves and our families. I was surprised at how much Greg shared about his wife and kids. He obviously loved them very much and adored his daughters. He even showed me a picture of them from his wallet!

Greg then asked me why I was doing this tonight and I tried to explain to him my need for something new and different while at school. Much to my chagrin, he chuckled at that although he explained it was because he thought that I'd certainly gone overboard in my quest!

When I asked him the same question he got quiet for a moment and I wondered if I'd broken some code of conduct for escorts such as, "Never ask the client why he is doing this."

Greg looked me straight in the eye and said, "To be perfectly honest, I turned forty four last month and I started to think about the fact that I'm not getting any younger. I see my kids growing up and now my oldest daughters isn't even a teenager anymore. I remember what it was like to be with a young women, to feel the excitement of the chase, the thrill of the unknown and I want to feel that again in me. My wife Claire is wonderful and has always been a great partner, friend and lover. I'd never want to hurt her in any way but the thrill is gone and I need to feel that again, if only for one last time before it's too late. Sorry... I hope this doesn't make me sound like some kind of a jerk to you."

Actually, it endeared me to him somewhat. After all the guys I'd met and chatted with that complained about their wives and wanted to cheat on them, Greg was a bit different. I also knew what he wanted for the evening and that I was the perfect girl for him.

The thing is, what he SAID that he wanted and what I knew that he did, even if just subconsciously, may not necessarily be the same. The secret was in the way he described his family and his love for them. I knew that he was feeling a bit guilty about his wife and that he loved his older daughter Mandy. I had a feeling that there was something about Mandy that I could exploit to make this a memorable evening for both of us and still let him go home to Claire with a faithful heart, if not a faithful cock.

Greg ordered dinner for both of us and I was thankful when he asked for something rather light. First, I wasn't very hungry with my stomach in knots all night and next, although I loved Italian food, it's a pain to eat without making a mess. He started to order wine but then remembered my age and smiled to himself as he put aside the wine list. I just drank some ice water with lemon although for a second I was afraid he might order me a glass of milk!

We somehow made it through dinner and I had a small lemon sorbet for desert. So far we'd kept the discussion away from anything other than ourselves and dinner so I had no idea what his plans were for the rest of the evening. So far he'd not made any move on me other than to hold my hand across the table! Sooner or later we would have to address the elephant in the room and as inexperienced as I was, I didn't know if it was up to me or him to break the ice.

In the end I figured I was obligated for dinner and nothing more so it was up to him of wanted anything else. After he paid the check - cash I noticed, I started to feel nervous again as I waited for him to say something. It wasn't long before he did...

"Kelly, you've been an absolute dream to be with tonight," he started out. "I just want you to know that dinner has been everything I could have hoped for and if you feel you should go home now I would completely understand."

I was a bit touched at his sincerity. I'd hoped for a pleasant evening of course but deep down I had this fear that it would end up being dinner with some ugly lecherous guy trying to grope me from the minute I sat down and then expecting me to fuck him all night. If it wasn't for the fact that I knew he was paying for me to be there, I could have been at a pleasant dinner with a new boyfriend given the way things had gone so far. To be honest, I WANTED to be with him. If anything, taking money from him would ruin the atmosphere that had been created, cheapen it in a way I didn't want to happen.

"Oh no Greg," I answered, "I have no desire to go home yet. This has been a wonderful evening and I appreciate everything so far. I'm not ready for it to end quite yet - if that's what you want I mean."

Well, if he couldn't pick up on that hint then he would have to be a lot less perceptive than I thought! Greg didn't fail me though. He stood up and took my hand, helping me to my feet. He smiled and softly said to me, "Then if it's OK with you Kelly I would love you to join me in a more... intimate setting shall we say."

I reached up and kissed him on the cheek, settling back on my heels with a shy grin on my face. For goodness sake here I was a slut being paid to go out with this guy yet somehow I was feeling more like a princess on a date! He called for my coat and we left for the parking lot where he had a nice rental car to take us to his hotel. On the trip back we just talked about the city. Neither of us was really familiar with Columbus so it was like a tourist ride for both of us.

Once again I was surprised in that Greg was a total gentleman, never once trying anything so far as touching me or feeling me. Even on regular dates it wasn't unusual for me to give head once we got in his car and here I was being paid and yet not doing anything!

Chapter 4 - The Hotel

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Upon our arrival at the hotel, Greg dropped the car off with the valet and we entered through the main lobby. No sneaking in the back door or otherwise trying to hide; instead Greg offered me his arm and we entered like two lovers returning from an evening out on the town. Even so, I imagine we got more than a couple of looks given the age difference between us. The guys most likely were wishing they were Greg while the women probably considered me as slut - or worse and Greg as some dirty old man! No matter, we got into the elevator and went to his floor and then to the room without hardly a word between us.