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  Even taking my time I was very close, pulsing, nipples throbbing, in all of three minutes. It was time.

  Not saying a word, and still wearing my stockings and heels, I rolled onto my knees astride Larry’s hips. I could feel his nice, average, cock at the spread lips of my pussy and I slide up and down his shaft, catching my clit on the roll of the condom. I had my hands on his chest. I was completely in charge.

  I reached back with one hand and angled his cock up into my very nearly gushing cunt. I pushed back until he was all the way in and then lifted myself to accommodate my own hand.

  “Put your hands under your bottom Larry and don’t you dare thrust unless I tell you too.” I said knowing the combination of his cock up my cunt and my own fingers on my hard little clit would push me over in just a few, slow, strokes. I pinched his right nipple between my long, blunt, artist’s nails and began to feel him grow absolutely hard. I loved that sensation. My tight little cunt completely engulfed him and, while I didn’t let him push, I could. In a moment or two I was at the edge and then, to my huge surprise, falling into the arms of a tremendous orgasm. I kept Larry still as I rode the waves and then, when I was completely done, I said, “Now, slowly, you may begin to push into me. I am going to pinch your nipples hard when I want you to come. Understand?”

  “Yes.” he gasped thrusting into me. Once the last waves of my orgasm are complete I quite like the sensation of being filled with a gentle, tame, cock. But not for too long, a minute or maybe three and then it is time. I pinched his nipples. Both nipples and was rewarded with his final orgasm. Underneath me. Where he belonged.

  Lovely.

  Larry left late. “I’ve extended checkout for you so enjoy the suite. I’ve ordered a suitcase for you as well and you can use my Uber account.” He gave me a fatherly peck on the cheek and as he did left a thick ivory envelope on the night table.

  I lay in that vast bed with the perfectly crisp, only slightly rumpled, sheets surrounding me and I wondered what the heck I was doing. But I knew. The question was would I do it again?

  I woke up, got packed and realized that my first adventure in the escorting trade had gone unbelievably well. Full on “Pretty Woman” which just does not happen. Except it did. Now, would it happen again? Just as I was wondering there was a knock on the door and a bellhop arrived with coffee, croissants, flowers and a note. “I am away for two weeks but will be calling on my return. Thank you, L.”

  So, sipping my coffee, I realized that I had two weeks and two thousand dollars and a suitcase full of gorgeous new clothes. Rent was paid. I didn’t have to see anyone else and Larry would be back. Which was all good, but a part of me wanted to see if I could escort and one date, no matter how perfect, is not quite it.

  I decided to get in touch with the other men on my short list. It turned out that each of the other men I had screened from that first escorting ad were all interested. Each was older and each was more than willing to play the escorting game my way.

  Larry had suggested that I concentrate on developing a very discerning clientele. Older, well off, a bit fatherly, interested in very safe encounters with a very low volume girl. “You’ll make more money and the risks are removed.”

  He was right. Instead of coming to escorting from a place where I was desperate for money – which I had been – I came to it as someone who was worth the price she asked her clients to pay. That simple reversal meant that all of a sudden I had the power in my escort dates.

  That power began with the fact I screened very hard. Not only did I have to be able to establish a potential client’s identity and contact information, I also decided that I wanted to spend a bit of time on the phone or over coffee before accepting a new client. Yes, this did slow things down at first. But it meant I never saw anyone I was even slightly uncomfortable with.

  My two hour minimum rule worked very well and so did my policy of not watching the clock at all. I went over time a few times but what is half an hour to ensure that a gentleman will be coming back again and again.

  I realized that if I wanted to have time to make art I needed to be very disciplined about my escorting. I set a basic target of three dates a week which provided me with all the money I needed. I soon learned that most of my clients preferred to see me mid-week. And I discovered that my clients, for one reason or another, liked to see me in one of four or five good hotels. Plus, and this was a bit of a surprise, I had as many mid to late afternoon dates as I did evening encounters. All of which was just fine with me.

  I have kept my advertising minimal. Once a month I place a small, discreet ad looking for “discerning gentlemen” and promising “an afternoon or evening of pleasure, laughter and conversation with a sophisticated, gamine, muse”. I have a small picture in black and white and my face remains in shadow. I don’t get quite the rush of business my first escort ad provoked but I usually find three or four gentlemen to add to my roster. Which is all I need really.

  I am into my third year escorting. The business is running itself and I am usually booked a couple of weeks in advance. I could see more clients but I think it would get pretty difficult to deliver a really quality service if I saw more than a few a week. I have raised my rates however. Not for my existing clients, just for new clients and that keeps my income very healthy.

  My way of escorting is not for everyone. I am lucky. I started very near the top. But I am also lucky because I escort to pay for my art and, because I can devote full time to my art, my work is getting better known and I am selling more.

  Larry did indeed return and after our next encounter proposed an arrangement which we have to this day: he sees me twice a month at my normal rates but with a bit of shopping thrown in and no clock at all. I swear we keep my personal shopper, Amy, in designer clothes just on her commissions. Larry is wonderful and so generous. He likes to tease me about being his mistress but, as he has never proposed an allowance, I tease him right back about not being able to make a commitment. (I let him have my backdoor three times a year…It is not that I don’t like anal, I don’t really but Larry is very average; it is that a girl needs a treat to give a man who gives her so much. I pretend to be reluctant but very submissive and Larry loves it. You want to keep a man like Larry interested.)

  My own plan is to keep escorting for at least the next two or three years. For me the whole transformation from starving artist to courtesan in the space of an hour is amazing. Being “Jane” takes me entirely away from art for a few hours which I think is actually good for my work. Plus, because “Jane” has a fair bit of cash from escorting I don’t get into the whole self-pity thing which I don’t think is good for artists. The cash plus “Jane’s” persona gives me a lot of self-confidence.

  It funny how often I see Jane’s clients at my gallery openings and group shows. Once I have known a client for a while I will tell him my art name – which is also not my real name – and it is pleasing to see the little red dots land on my work. My clients are becoming my patrons which is very close to perfect.

  Annie | Tonya | Kelly

  Back to School – College Escorting 101

  As summer winds down the great migration of college students all over North America is beginning. Bags are packed, computer stowed and, yikes, tuition fees paid. And in cities and towns all across America little ads begin to appear.

  “College girl seeking company.” “A GFA with a college girl next door”; yes, many of the girls advertising have not been within a thousand yards of a campus in years. However, more than a few girls work as escorts to put themselves through college or just to have a bit of spending money.

  Whether it is retail escorting, being kept as a mistress or occasionally going on a “paying date” college girls know that there is a real market for their companionship. How they approach this market while keeping up with their course work is an interesting balancing act. I spoke to three girls in three very different situations.

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  Annie is a twenty five year ol
d graduate student at a university on the Eastern seaboard. “I’m a little older than the typical college girl escort. I love university and I love doing advanced work in history. I suppose, eventually, I’ll get a “real job” but right now I like going to my seminars and writing my papers. What I didn’t like when I was an undergraduate was constantly being broke.

  As an undergraduate the escorting thing was not really an option because I was in a really small college town a long way from the anonymity of the city. But I certainly looked at the possibility. So, when I was accepted into the graduate program I am in I very deliberately tested the escorting waters in the city the university was in.

  Even before I moved to the city I was researching – PhD candidates are very good at researching – the business in that city. Based on my research I spotted what I thought would be a comfortable, up market, niche. The city is a fairly serious financial center and there are a lot of men travelling into town.

  I was very deliberate. I wanted a certain sort of client. Older, well off, very safe. I read a lot about the business. Everything from advertising to protecting myself legally to how various girls organized their business. I didn’t need to make a fortune escorting. Just enough to cover a nice apartment and have a few treats. I had a fellowship which covered my tuition so it was just my living expenses I was worried about.

  I wanted to keep my privacy. I had a nice apartment but in a small building and even a few different men arriving would have been suspicious. Obviously I didn’t want my fellow grad students or profs figuring out that I was escorting. Easy enough. I bought a dedicated smart phone which was switched off during the time I was on campus. I could check texts, emails and messages discretely but I usually did not return the calls until I had lunch, off campus, and again on my way home. Of course, one of the pleasures of graduate student life is that I only had classes two days a week. For extra privacy, I never went directly from campus to a date so my peers never saw my escort look.

  I paid attention to that “look”. I wanted to have a polished, professional style even though I was planning on advertising as a student. Because I knew the gentlemen I was targeting would be older professionals and there was no way I could see them in the grad student uniform of jeans and a top or even a peasant dress. Again, I did my research and with a little money I had saved found a couple of smart pencil skirts and professional grade white cotton shirts. A couple of jackets and I looked like the sort of up and coming girl who drops off papers to business executives at odd hours of the evening. Now, underneath, and in my very demure advertising pictures, I was all about white, semi-sheer, lacy bras and pretty stockings: but on the outside I was all business. I had professional pictures done on a “Time for Prints”, in this case a CD, basis. Sexy, but a very long way from slutty. And my face never showed. Neither did anything more provocative that the outline of a nipple.

  I wanted to see businessmen from out of town in good hotels. So that is exactly what I advertised for. “Attractive, intelligent, graduate student seeking evening conversations with discrete, older businessmen. Executive hotels only. Expensive but worth every penny. I never watch the clock. Dinner? Of course. Email preferred.” I put that ad up on a couple of the more exclusive escort advertising sites. And then I waited.

  I didn’t have to wait long.

  At my rates I needed two dates a week to do well, three to have plenty of treats. The day I put my ad up I had six emails, three realistic and booked two dates. The next day I had nine, five realistic and booked three more dates.

  I was not the least bit nervous about my first “escort” date. I treated it like any other date. I met my client for a drink in the lobby of his hotel and, when we hit it off – which we did as he was a rather nice, if slightly balding, guy – we went up to his room. I always carry what is known as a lawyer’s bag on my dates. It is a really big leather brief case, about three times as thick as a regular brief case. In it I have everything from sexier heels to condoms to candles to unscented shower gel. A couple of toys, a riding crop and a little Bluetooth speaker for my smartphone. It is a great prop. What escort is going to carry that around? Well I do. And it serves me well.

  Ninety percent of my dates are very “meat and potatoes” sex. I tease a little and then get down to sucking my client’s cock. Big, small, in between, men just love a girl who will, without asking, go down on them. Sometimes, if the guy seems nice, I will suck his cock without a condom. But, when I feel him getting ready to come, I always slide away. Who wants to swallow? (I will, but it is a very expensive extra.) But what I am usually doing is getting that cock ready for a condom and for my pussy.

  I always make sure to lubricate before a date so when he’s ready, I’m ready. I am delighted to have a guy cum a couple of times during a date. With Viagra most of my dates are up at least twice and three or four times is not out of the question. But, past two, I insist on having my pussy licked. For a while. I never have a cock anywhere near my pussy without a condom. No regrets I say.

  From that date forward I have been booked two or three evenings a week. As I say in my ad, I don’t watch the clock but on average, from drinks to taxi home is about two and a half hours. Dinner adds, at most an hour unless I am having a great time in which case, who cares.

  On average I am making a little over $5000 a month. For a very part time commitment with no serious expenses I am pretty happy with that. I bank two thousand and keep the rest in cash for treats and fun. Almost all my dates are from Monday to Thursday. My clients like to fly out on Friday.

  I’ve been doing this for two years and have a set of a dozen or so regulars who I see every month or, maybe, six weeks. Of course I prefer my regulars. Less hassle, no screening, usually a good dinner. My biggest problem is too many great meals. I have to make sure I work out on about a one to one ratio.

  I don’t think escorting is for every girl. You have to be a little detached and really understand it’s a business. I see really young girls, 18 or 19, advertising and I am not sure they are ready. But, their choice. I’ve made mine and I’m happy with it.

  Down the road? Well I have three years to finish my thesis. Then we’ll see. It is easy to escort when you are a student, not so easy if you have a real job. But I can’t see giving up my regulars. They are a really nice bunch of men.

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  Tonya, twenty, vivacious on Skype and very, very blonde, has an entirely different story. She is at a Mid-Western school in a fairly big city.

  I was in my second year as an undergraduate and I was just loving my courses and my profs. I like living on my own though. I lived in a dorm in first year and it was awful. I guess I am really private and I really, really like to study. The dorm was too loud, too much of a party. So I got a cute little apartment off campus with a room mate. Which worked great until my room mate decided to have a serious melt down and move out nine days before rent was due. I have a really nice landlord and I figured I’d tell him what the problem was and ask for an extension on the rent until I found a new room mate. He had another suggestion. Well, the rent was $500 and I have to admit I sort of like the idea of getting half off for a few consenting adult activities on the quiet a couple of times a month. So, I said yes.

  I have to say he was a great way of getting into the business. Gentle, clean and not very demanding. In fact I would say he sort of lulled me into the whole thing. And once I had given my first “professional” blow job, the rest was pretty easy. My landlord is not the old fat smelly guy, he’s the ambitious, young, no time for a girlfriend guy.

  The nice thing about my apartment is that it is very private. It is above a garage in a busy downtown neighbourhood. Lots of trees out back and a very simple layout: just a little kitchen, a nice big bathroom and a bedroom and living room all in one room divided by two of those Ikea cube shelving units. My door is up a flight of stairs and just off an alley one house in. I thought that it would be pretty easy to see clients without anyone really knowing what I was doing and I was righ
t.

  I needed a bit of money every month. My parents were financing my tuition and giving me a bit of extra money but it was really tight, even with half my rent being paid by my landlord. With the internet this was really easy. I put up an ad once in a while, had about a hundred calls every time. I like the soccer dads. You know, the guys in the mini-vans with a couple of kid seats in the back. They are really safe, really grateful and some of them are kinda hot.

  My ads are really basic. “College student available for GFE. Blonde, 34 D, love my work!” I am actually a C cup but I have never yet had a guy check. I don’t see many guys. I could, I guess, but I am really religious about screening. I want nice, clean, dads who have way more to lose than I do. And there they are parked at the end of my little alley.

  I have to admit I really like dates around 7 in the evening. I’ll do one at 7, one at 8:30. No rush and I can go and hang with my girlfriends by 10 and they all think I’m a study bunny.

  The sex? Blow jobs. I’d say 60% or more of the guys I see come five minutes into a blow job. It’s what they want. I am good at blow jobs. I can deep throat anything up to about eight inches which they love. But the secret is that a blow job is just a wet hand job with kisses. You swallow the sword a couple of time but mainly you are just jerking them off. They have to wear a condom so, no mess. My rates without a condom are double. So I suck cock most of the time and, once in a while, a guy will want to bang me which is fine but a bit boring. I mean I am there for them so I don’t get off very often.

  A few guys will want to go down on me which, honestly, I wish they wouldn’t. It is sort of like kissing. I’ll kiss a date but I won’t like it. I like the soccer dads who just want a bit of unfamiliar flesh, a girl who wants to blow them. Totally worth it.