Escort Ch. 02: Talking to His Wife

Chapter 1 - Becoming an Escort

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I've always been a very sexual person and was fortunate to have been raised in an open and loving family environment which nurtured that side of me and allowed me to explore in a caring and secure environment. Once I had sex for the first time with my boyfriend at the age of fourteen, there was no stopping me and since then I have been with a number of men (and women) in a number of widely varying settings.

As a result I've grown accustomed to my daily (or more often) "fix" where my deepest and most innermost cravings can now be only satisfied through an orgasm - including the process in getting one. If I don't have a partner available (and often even when I do), masturbation is an alternative but no matter how hot it gets, doing yourself can never replace the real thing.

Going to college was a challenge for me in many of the same ways it is for most kids. In addition, more so than most kids my age I had the pressure of having to go without sex for extended periods of time. If it had not turned out that my first roomie was bi, I am not sure how I would have made it through my freshman year. Brenda was a lifesaver for me and she is still one of my closest friends. My sophomore year was quite a different story however. Although I was more mature in terms of leaving home and dealing with the college environment, my new roomie was just the opposite of Brenda when it come to her sexuality.

When I first saw Karen I thought maybe I would be lucky again. She was dressed in jeans and a halter that were at the bleeding edge of the school dress code and was an absolute fox. I quickly found out though that while she was a delicious tease and knew exactly what she had going for her, Karen was determined to be a virgin when she got married. Worse, at least for me, she defined virginity in a VERY broad manner. Karen believed that ANY form of sex was wrong before marriage - even masturbation and fondling!

Karen's views on clothing walked a fine line. Nudity was a total no-no but revealing shorts, miniskirts, halters, even a string bikini were OK. A few meager pieces of cloth were sufficient so long as they covered her pussy and nipples. I was shocked out first night when I went to go to bed and she was upset because I was nude. I didn't want to start off the year on the wrong foot with her so even though it had been nine years since I wore clothes to bed (other than when I was visiting someone) I spent my entire sophomore year sleeping in shorts and T-shirts.

I dealt with the situation for the first semester as best I could, mainly through a LOT of masturbating. After a holiday break at home, I returned to school "recharged" and then looked around my dorm room only to be struck me squarely between the eyes with the realization that another semester of secretive masturbation was facing me and my heart sank at the prospect. Now don't get me wrong - I LOVE to masturbate but girls like me needs more!

In desperation I found myself calling a few escort agencies in Columbus and selected the one that seemed the most professional and discriminating. I figured if they were that way when choosing their girls then hopefully they would be with the guys as well. The agency checked out potential clients to be sure they were not felons, wanted criminals or known sex offenders. Although the agency does not officially sell or promote sex, let's face - a guy doesn't pay $1,000 or more just for pleasant conversation.

I was warned that the men would assume that I was also available for additional "services" which were negotiated that evening between me and him. The agency's policy was that anything I arranged with him was entirely my business and responsibility. The guy paid the agency for the evening so I never had to deal with money which also provided protection against prostitution charges. It was up to me to establish what "tip" I got if I decided to go beyond the standard "date. The agency also provided transportation each way in the form of a taxi that picked me up at the school, dropped me off at the arranged location, and then was available to take me back no matter I called. I got a paycheck twice a month just like any other job, taxes deducted and all!

My first "job" was a bachelor party which turned out to be one of the most exciting events of my life to date. I can hardly express the thrill I got seeing ten guys lusting over me the way they did. It was a tremendous ego booster I can tell you that much for sure. I wound up doing more than just stripping - a LOT more.

When it came to the single escort duties I limited myself to married men over forty, preferable with a family and from out of state. My past experience with older guys was that they generally treated me better than the young ones. As for being married, I figured that would ensure they were discreet. I wanted them to be from out of state in hopes that would prevent them from trying to contact me afterwards. Finally, I also set a strict rule that only one date per guy - no repeats under any circumstances. I was doing this for fun and I wanted variety. Plus, I didn't want there to be even a remote chance that someone would think we would be forming any type of "relationship".

Greg was my first escort. He had looked handsome in his profile picture and had written a clever and entertaining introduction. He was from Chicago but what caught my eye was that he had always been married to the same woman. After days of anticipation we met and it turned out to be a fun and sexual evening. It turned out that he had a daughter my age and a hidden desire to have sex with her. Morally he could never do that in real life so I became his "daughter" for the evening. It was the first time I had played out someone's fantasy in such an intense and erotic fashion which is probably why I reached orgasm several times during the course of the evening. The success of that night was enough to convince me to continue on with my escort career.

Chapter 2 - Getting Ready for My Second Client

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So anyway, given all this I was once again in a taxi, heading to the east side and a rendezvous with my next client. According to his profile, John was 45 and had been married to his wife for ten years yet he had four children, three by previous marriages (it didn't say just how just how many marriages!) and a fifteen year-old boy with his current wife. Doing the math with this guy was next to impossible! I figured they must have had a child out of wedlock or maybe even while he was married to someone else.

Any way you looked at it, he wasn't the poster child for marital stability, that was for sure! What drew me to him and agree to meet was the profile introduction that he had written. As you might guess, I like a guy who is literate and can express himself. I also have a low tolerance for men who beat around the bush (no pun intended) and can't (or won't) express their true feelings. Well, Mike's profile description was certainly not vague. I copied it here to help out all the guys who want to know what I look for in a guy!

"Hello!

My name is John and I'm a 45 year-old father of four currently living in the St. Louis suburbs. At 6 feet and 220 pounds I may not be as I was when in my college prime but I still wear a 36 inch belt with the original holes. All the curly hair I was born with is still hanging in there and I was blessed by my parents with their Irish heritage and looks. I'm a professional with a PhD in political science so I would like to think that I am not totally stupid although some of my past wives might have a different opinion.

Speaking of past marriages, three of my children are from them and as wonderful as they are it is a relief for them to all be out of school and out on their own. My fourth was a product of my union with Dana, my lovely wife of ten years and counting. He's fifteen now and quite the lady's man - a chip off the old block if you don't mind me saying that. What I mean is the old man knows how to treat a woman and can't get enough of them as you may have guessed from the lasting power of my earlier marriages. Dana should know me better than to expect me to be a faithful husband disdaining all others. After all, she was one of my "other women" which including bearing my son during my previous marriage. I guess she must be either totally in love with me or just naive because she truly believes I am so infatuated with her that I stopped my womanizing when we got married. Thankfully she still doesn't know I did her sister during our wedding reception (and not for the first OR last time)! Bless her heart, I love her dearly and hope to spend the rest of my life with her but hey, some things are just in the genes.

So why would any sane woman want to spend an evening with someone like me? Quite simply, you know exactly what you're getting - no games or pretenses. I can promise an evening you won't soon forget, no matter what your background or experience. I travel extensively around the world and when my evenings are free I enjoy spending them with women of all shapes, sizes and cultures so don't worry that you may not be my "type". I grew up in a generation that taught men to respect all woman and to be a gentleman meaning I will always show consideration for you. As for being a gentleman, well let's just say I promise to behave myself in public. Do you really want me to otherwise?

So let's hit the town and see what happens. Nothing premeditated; dinner at a comedy club? A rousing round of competitive miniature gold? An intense evening of political debate over a remarkable Chablis? Hey, I'm game for most anything so see you soon!"

Quite the profile isn't it? Well, there are a lot of folks on some of the adult websites I've looked at could take some lessons. Once I read this in the profile my agency sent me I was instantly hooked - he sounded like just the type of guy I signed up for in the first place. Face it, I wasn't looking for a boyfriend or a lover. All I wanted was to have some fun and get laid and John sounded like just the ticket.

I accepted the appointment and the agency hooked us up through their brand new e-mail system which maintained both of our privacies. We exchanged a couple of messages and he offered to take me out to a GameWorks club in a fancy mall on the east side of Columbus. I checked it out on the Internet and found it to be advertised as "the ultimate destination for a total entertainment experience where guests can eat, drink, party and play." I had never even heard of it let alone been there but when I mentioned it to some of my friends they all said it was a great place so I accepted and we were set.

Riding in the back seat of the cab, I pulled out a mirror from my purse and gave myself a once-over. I was dressed totally different from my first escorting job. Instead of a killer evening dress and an all-afternoon fight trying to make my hair do SOMETHING, I was wearing a pair of tight jeans and a peasant girl style sleeveless halter top. The jeans were a size (or two) too small making them a challenge to get on but by sucking in my stomach and clenching my butt I was able to finally zip them up and button them. It was worth the effort when I saw how they form-fitted my ass as if they had been painted on. Well, no panties with these babies on, that was for sure! Hopefully I wouldn't have to use the little girls room too often either.

I didn't want to wear anything that had to be tucked in plus the halter showed off my flat stomach which I starved myself to keep so why not let people see it! I had chosen what was normally the unthinkable and wore a strapless bra under my halter. With the peasant-style halter the way it was it didn't matter if I wore one in terms of showing off since I could have leaned completely across a table and not showed anything. Instead I was thinking of what might happen later and hoped that the bra would make the act of undressing a bit more sensual and erotic. Bras may be a pain in the ass (at least for those of us who don't need them to keep our boobs off our laps) but they are always a sure-fire way to turn on guys! This one was not exactly from Victoria Secret but rather straight of the JC Penny winter catalog juniors section. Again, I was thinking ahead and hoping it would give me more of that "little girl" appeal to this older man.

To finish things off I wore a pair of white sneakers with white anklets. I decided to go sans jewelry, not even a watch. Instead of spending hours trying to put some life in my useless hair, I just pulled it back into a pony tail and let it go at that. Minimal makeup - just enough blush to give some color to my cheeks, a bit of shadow to deepen my eyes, and some light lipstick to make my lips look moist. I pulled my trusty old bottle of Charlie from my purse and freshened myself up just as we pulled into the parking garage.

The taxi stopped at the entrance inside the garage and I signed the slip for the driver. He gave me his card and said to call him when I was done and let him know where I was. I smiled a bit at that, obviously he knew this was not to be my final destination tonight! This must have been a pretty good gig for him. Since the agency didn't know when I would be finished, he was on call the entire night so I wouldn't have to wait for someone to be located to pick me up just in case I needed to leave quickly. Hey, the agency was paying for it!

I entered the mall, went up the steps and walked past a comedy club - a pace I would love to go sometime if I could, and saw the GameWorks on the other side of the hallway. I had a red ribbon tied to my purse as we had arranged so when I approached the entrance a gentleman stepped forward and greeted me.

Chapter 3 - Playing Games With Mike

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"Hi!! You must be Kelly. Wow! You look even better in person than you do on your profile. I'm John, your date for the evening."

Well, that was a pleasant if not overwhelming introduction. He took my hand and shook it warmly, looking me in the eye and smiling. The one thing I noticed most was he did NOT do. Most guys never get to my eyes; they start at my legs, move up to my waist and then work their way to my boobs and either stop there or go back down again. John actually looked at ME, as if he was truly interested in Kelly and not just her body. Hmmmmmm, this was interesting and I felt a bit unnerved actually.

To be honest, over the years I have learned to deal with the stares and ogling eyes and actually have grown to appreciate them as a testimony to my sexuality. In that moment I realized that I actually EXPECTED to be objectified and so when this stranger didn't follow the routine I was thrown off balance for a second. Usually at this point all I had to do was wiggle my hips a bit or let my boobs bounce and I knew he was hooked. Mike was going to be interesting, that much I could tell already.

We chatted for a brief moment about the usual stuff - my trip down, the weather and how we were both doing (both doing well of course). Then Mike lead me to the entrance where he had already purchased passes for the evening. He helped fasten mine around my wrist and just that easy we were in.

The first thing that struck me was the noise! The place was playing loud music and there were games of all types making random sounds while flashing colored lights. Although it was only 8:00, the place was already packed and I noticed most of the crowd was on the younger side making Mike one of the older-looking men there. I didn't mind, he was even more handsome than his profile picture and the self-depreciating comment in his profile about his weight didn't do him justice. He was in better shape than half the young guys and looked much more self-assured and mature. I felt comfortable by his side and felt sort of proud actually to be seen as his date.

For the next hour we moved through the place trying out the various games. It was wild and the simulation games proved to be my favorites. I loved the racecar races and we competed against each other over and over. He was the perfect date in that while I beat him every time, I was never sure if he let me or not. As we worked our way around he would first hold me by the waist or put his arm around my shoulder. I noticed though that it didn't take long for his hands to begin to wander and soon instead of resting on my hips I felt one holding my ass. When I didn't resist it emboldened him to start squeezing it. I looked up at him and smiled sweetly.

"Hmmmmmm, so you like my ass Mike?" I said in a teasing voice.

"You know damn well I do you little tease," he replied with a chuckle. "In fact, I think you know EXACTLY what you've been doing every step of the way so far tonight."

I gave him an innocent pout saying, "Now what do you mean by that Mike?"

Mike reached down lower, cupped my ass cheek in his hand, and lifted me up to the point where he was actually bringing me up onto my toes.

"Now won't get me wrong but I didn't fall off the turnip truck yesterday and you're not the first escort I've been with. I have to say though that you've got the 'naive school girl' routine down to an art form and I love it." He paused and looked deep into my eyes. His grip on my ass loosened and his tone softened. "I AM curious about one thing about you though. When do I get to see the real Kelly?"

I kept looking at him with the same innocent look and he slapped my butt as he said in a more forceful voice, "I know you understood me. You intrigue me and trust me, that hasn't happened for me with anyone for a long time. I want the REAL Kelly. What is it you want? I mean really want and no more games, OK?"

I had no clue what to say. For a moment I thought I might cry. I knew what I wanted but how could I tell him? I was the escort and he was the client. Why couldn't he just play along and fuck me? If I wanted a date there were a lot of guys who would take me out at school and I frequently went out with a number of friends. Only problem was the damn Lifestyle Guidelines at school that expressly forbade sex. People who have never attended a school like mine have no idea the pressure that is applied to follow these rules and the result was while I had a good time, I never got to even so much as give a blowjob. There was only one reason I was here tonight and it wasn't the money. I just wanted sex - was that too much to ask?

Mike brushed the back of his fingers against my cheek. "Now now, don't get all emotional on me. Let's be honest, we're not here tonight to play video games. I think you want exactly what I do so why don't we leave and go do it?"

Thank goodness, enough of the charade and down to business. As he said this his hand was working my ass again, squeezing it and lifting up on it. I glanced around to see if anyone was seeing what he was doing to me but so far he had me positioned in a corner such that his groping hand was hidden from view.

Actually I liked what he was doing - no, I should say that I loved it. My entire ass has always been a major erotic zone for me and I love it when anyone plays with it, even myself. His hand was big enough to cup my entire butt cheek in it and his grip on me felt fantastic! Despite what he had said, it was time to get back into the game so I reached down do his crotch and pressed my palm against him and was pleased to feel the hardness behind his pants. I flashed a foxy smile...

"Well Mike," I answered by in the sexiest voice I had in my arsenal, "it sounds like you know what you want so why not just do it - or should I say, do me?"

Mike laughed and started to lead me out. "That's my girl," he chuckled, "Damn, I can't believe we wasted away an entire hour here!"

Mike led me by the ass to the parking garage, never taking his hand off me the entire way despite the looks of more than a few people in the crowd. He opened the door of a large white SUV that he had rented judging by the sticker with the bar code in the back window. Only thing was, he didn't open the door to the passenger side but rather the one to the back seat! I gave him with a questioning look and he just smiled saying, "I'm in no hurry to get to the hotel, are you?"