Money Sex Page 5

  Because I knew I would be seeing my time share mistress clients more regularly than ordinary escorting clients, I really got to know them. Eventually I had four which was pretty much as many as I could service. All in, that was about twenty encounters a month so there was not that much time left for regular escort dates. But, as any clever mistress will tell you, it pays to be looking for the next patron so I kept my stress management ads running.

  I did, however, raise my rates. A lot. What I had not realized about San Francisco was just how much money these guys had. There was a reason why there are a lot of $10,000 a month apartments on San Francisco Craigslist: these guys can afford it.

  I realized that one of the main ways of choosing an escort if you are really well off is to assume that, like fast cars and great red wine, price is a pretty good indicator of quality. These were not guys who read hobbyist reviews. Quite the opposite, it was a feature that I had no reviews. In fact, it was a feature that I presented myself in my ads, on my website and in conversation as barely an escort at all.

  The greatest luxury of all turned out not to be the fluffy towels or the honed oral technique; it was the illusion that a really pretty, elegant girl wanted to spend time with an otherwise harassed, stressed and wildly busy guy. Whether it was a straight escorting date or a time share arrangement, I tried to keep the whole money end of things very much in the background. Of course I like my envelope but I try to leave my clients with the impression that I enjoy my time with them regardless of the money.

  That impression is, in fact, true. Unlike my escorting in Portland, in San Francisco I created a business which was very exclusive. The men I see, especially the men I see on the time share basis, are actually men I would probably date. No, it is not the Pretty Woman scenario with the billionaire white knight on a charger, just nice guys who, realistically, don’t have the time for a real relationship. For them, while I am an escort, I am also that great girl who does not need any maintenance at all.

  The real luxury for these guys is having a break from making decisions and inventing the future. Most of my clients are a little older than I am but I have two who are younger. What they value is being able to sit for a little while, sip some wine, have a few nibbles and know that if they turn their phone off – which I insist on – the outside world is on hold. Of course they enjoy the consenting adult activities but the reality is they enjoy the break even more.

  Trish

  Mile High Escort

  We were looking through some escort ads the other day and were struck by a pretty girl in Denver Colorado whose picture seemed to jump off the page. It was not that she was particularly striking to look at, there were more beautiful girls on the page, but her face has a certain welcome which is very hard to miss.

  The copy to the ad was equally inviting in a fresh, sunny, very gentle way.

  “I love what I do. I take wonderful care of myself and I would love to take care of you. No hurry, gentle with a deliciously wicked streak. Let’s chat.”

  So we did. By Skype. “Trish” turned out to be twenty seven and just as bubbly as her ad had made her sound.

  “I really do love what I do. I have a nice clientele, about three quarters regulars. I don’t run my ad all the time. I will put it up when I have a few blank days the next week. They always fill up.” said Trish pushing her honey blonde hair off her face.

  “I like men. I always have but, to tell the truth, when I first got into the business I did it all wrong. First off, I got into the business because I was desperate for money. Which is not a good place to start. Second I wasn’t in Denver, I was in LA. LA is a very tough town to escort in much less start escorting in. Super competitive with all those wannabe movie stars and those porn star girls who escort on the side. So you have to use an agency which is a whole other mess. I was with three and two of them didn’t pay me what they owed me as soon as they found out I was leaving.

  Working with an agency is not at all for me. I needed the work so I did it but I hated all the politics. The bookers knew who the good dates were and they gave them to their friends. I got either random guys the agency had barely checked or known goofs. Not dangerous but not a heck of a lot of fun either. Plus, the one agency which I stuck with was crazy about time. They would “fine” you if you went ten minutes overtime. It was awful. But setting up as an independent in LA is crazy expensive because if you do in calls you have to have a nice place which is money. If you do outcalls you either have to have a car or you take a cab which takes forever and is crazy expensive and then, when you leave, you have to find another cab and that can take hours. At the end of six months I was a wreck and I was still pretty desperate for money.

  I guess I had a bit of a breakdown. And I got careless. I was OK but I got one of those dates which just creep you out. It wasn’t what the guy wanted to do, that was pretty ordinary, it was just how much he wanted to verbally abuse me while he was doing it. Just nasty, creepy stuff. I got out in one piece and I didn’t get out of bed or answer my phone for three days. And I forgot I had an afternoon date with one of the few regulars that I had managed to sneak past the agency and he knocked on my door and I was a total, kinda smelly, mess.

  What a nice man. He took one look at me and said, “OK, off you go to the shower, don’t bother with makeup, put your hair in a bun and I’m taking you to lunch.” Saved my f’ing life. No, really. I didn’t know him that well but it turned out he was an executive recruiter. “I see this all the time. You hit a wall.” he said in a nice restaurant which was half empty at three. We talked for a couple of hours and I felt a little better. I figured the least I could do was invite him back to my place and do my best.

  “Not a chance.” he said, “You are taking a few days off escorting in LA. Call your agency. I’d suggest you simply quit but up to you.” I quit. At least they didn’t owe me any money they could stiff me for. While I was calling he was on his phone.

  “So, here is what we are going to do.” he said and I nodded. “We’re going to Denver. LA is a terrible place to escort and you are showing all the signs. Time for some Rocky Mountain air.”

  I grew up in the Valley. I’d never been out of LA and the whole thing seemed like a dream. I wasn’t arguing. “Anything at your apartment you can’t live without? Cat? Goldfish?” There was nothing. Not one damned thing. After six months of escorting I had a second hand couch and a bed which was way too hard.

  “OK then” he said, “I’ve cleared my schedule. Time for a road trip. We can swing by your apartment for you to pick up a few things and then mine and then we are off.”

  I have to admit I really didn’t care where I was going. Or what I was going to do when I got there. Somehow David, that was his name, seemed to have everything figured out. “We’ll take Highway 15. We’ll stay overnight in Barstow which is not a huge drive and then see how far we get tomorrow. If you decide you don’t want to go to Denver we can turn around in Barstow and be back in LA by lunch.”

  Which is what we did. Drove out of LA and through the Valley. We didn’t talk much on the way to Barstow. I just sat in the passenger seat and thought about what the hell I was going to do in Denver. Before I figured that out Dan was pulling into a motel in Barstow. We dropped our bags and headed out to an Italian Restaurant.

  “So,” said David when our meals had arrived and we had a bit of privacy, “Do you like being an escort?”

  It was a question I really had not considered. I escorted because I needed money and this seemed like the best, and maybe only way to get it. “Not really.” I said. “Well, actually, I like the actual escorting part of it. I like meeting new guys and I enjoy being able to give them a lot of really intense pleasure. It’s all the rest that I don’t like.”

  David was, and is, a really good listener. He knows how to get people to talk about themselves. Maybe because of being an executive recruiter. By the time we’d finished dinner he knew more about what I hated about escorting and what I liked about it than I did. As he paid
our bill he said, “There is a lot here to think about. We can talk about it in the morning whether we are driving back to LA or on to Denver. I want to think a bit about what sort of game plan is going to make sense for you going forward.” He said things like “going forward” and “game plan”. That was his world.

  It was funny. When we got back to our hotel room he was very shy when I suggested a few consenting adult activities. I finally had to put my foot down. “You are working really hard and spending a lot of money to give me a new direction. I am a professional and I want to make sure you are well taken care of.” There are very few men, no matter how nice, who turn down that sort of offer from a girl kneeling in front of them in nothing but her bra and panties unzipping his pants. I sucked his cock, no condom, until he came in my mouth and I swallowed every drop of his cum. All the while looking right up at him like the desperate, dirty, little slut I was sure he thought I was. He went to sleep with a smile on his face.

  The next morning, after I attended to the morning wood David, like most men wakes up with, he said to me. “OK, Denver or back to LA?”

  “Denver.” I said without a second’s hesitation.

  “Escorting?”

  “I think so. I mean I could get a straight job but doing what and for how long?” I said. The fact is that I had very little training and had spent most of high school perfecting my outfits. I never really learned how to work.

  “OK.” said David. “We’re off. We’ll get breakfast down the road. I’d like to get some miles covered if that’s ok with you. We can pick up coffee on the way out of town.”

  There is a lot less traffic in the early morning on Highway 15 between Barstow and Las Vegas. We sipped out coffee and drove through the high desert. Fortunately it was late Fall so it was not super hot. David liked to talk and I was all ears because he was talking about what actually made a successful person.

  “It does not matter what you are doing. You can be working in a Wal-Mart or running a big company or escorting. It is what you bring to the job. Honestly, it really is all about attitude.”

  It is only two and a half hours from Barstow to Las Vegas and we postponed breakfast until we could hit an amazing “Best Breakfast in Vegas” restaurant. It’s funny, I grew up all of five hours from Vegas and had never been there. David had been there dozens of times and he grew up in Kansas. About 2000 calories later we were back on the road. But not the direct route to Denver.

  “I’ve always wanted to see the Grand Canyon. We’re not in any hurry, at least I’m not. Let’s go.” So we did. We drove all the way down to the North Rim and it was amazing. Then we took our time driving quiet two lane highways which stretched across miles of high plains and through these amazing National Forests. Places I had never even knew existed. A lot of the roads we took would have been snowed in during the winter which was not far off.

  We stayed overnight in Moab. By now David and I were really comfortable with each other. We could play a little and I am afraid we shocked the nice ladies at a cute little consignment store where David wanted to buy me a few clothes. David is certainly a gentleman but, well, I did mention I loved the consenting adult end of escorting and part of that is teasing. He was well and truly teased.

  The secret to a great tease is, believe it or not, a full slip. And in the Moab consignment store they had one, beautiful, black satin slip with a zip on the side. I wore that and nothing else to try on my outfits and, to David’s delight, my nipples kept slipping out and once in a while my cute little bum would peek out when I was pulling a dress over my head. Too bad they didn’t have any stockings.

  Over dinner David talked about setting up a really excellent escorting business in Denver.

  “Here’s the thing. What you told me you hated about escorting in LA was all about bad planning and not really thinking about what you like doing. You like the actual escorting. Seeing men, being paid for your time and your talent. There are lots of men in Denver but to really make a go of it you need to have a sustainable plan for not just your escorting business but the rest of your time.”

  “In LA, between dates, you sat in front of a TV or a computer screen. You were waiting for the phone to ring because that’s what you thought escorts did. And, I suspect, that is in fact what most escorts do; but they don’t have to. You told me that most of your appointments were in the late afternoon or evening. So, in Denver, why not simply say that you only book appointments from four o’clock to ten o’clock. That gives you your days to yourself.

  Escorting will give you the income to do other things.”

  “Like what?” I asked.

  “If I were you I would look for two things: first a part time job and second something to study which will give you a credential you can use to get a better job. It seems to me that “just escorting” does not suit you at all. You need much more going on. Do more.”

  We finished dinner and went back to our hotel. I tried on a few of the things David had bought and, as you might guess, that teased him all over again and we had a delicious round of consenting adult activities.

  He was up early and on his laptop. “We have to get going. I’ve found you two furnished apartments to look at.”

  “But I have no money. Like $50.00.”

  “Yes, but I certainly didn’t expect you to go on this road trip for free. You’ll be fine.”

  And I was. It was funny to watch the landlords take one look at David’s watch – which really was a gold Rolex – and his car which was German and very sleek and quickly conclude that he was renting the apartment for his mistress or girlfriend. I guess I looked a bit like a mistress because David had bought me a really pretty Ralph Lauren dress which was very body conscious. Very. And it didn’t hurt that he paid the security deposit and first month’s rent on a Platinum American Express card. He used the same card to get me a smart phone and a cute little laptop computer.

  We had great fun shooting pictures of me using the phone camera. David was a bit of a computer whiz and in an hour he had a gorgeous website put together on my laptop which he showed me how to update. When it came to putting up prices David asked me what I wanted to charge. Of course I didn’t know. He put in an hourly rate which seemed crazy high. “You can always go down.” he said. “But the sorts of clients you want are not going to blink at a little less than they are paying their lawyers. Escorts are way more fun than lawyers.”

  We drove around Denver a bit. I could really feel the altitude. It is not called the mile high city for nothing. David stayed the night and, in the morning went out on his own for an hour. When he came back he had an envelope. In the envelope was $1000 and four prepaid Visa cards.

  “Well, time to be headed back to LA. This will get you started. I’ll be flying via Denver pretty regularly so, if you need anything…” he kissed me on my cheek and hopped in his car.

  The next day my ad went live. Pretty much the ad you saw. With a main picture David had taken of me standing looking over the Grand Canyon. Nothing terrifically sexy and probably the very opposite of what most people would think an escort would look like.

  I have to admit I was a bit nervous. Would anyone call? But, I had my rent paid and some, well to me, quite a lot, of money. More importantly, I had just seen some of the most beautiful places in the US. Because David liked photographing me, I’d stripped naked and briefly, very briefly jumped into a crystal clear pool fed by a mountain stream with the Rockies as my backdrop – and yes it was very, very cold. I had a new world and a new life and I was not going to screw it up.

  One of the things David had said was that I should take my time and be really, really picky. Which was amazing because I really had never thought of escorting that way. I’d thought that a girl would make the most money if she took every date. That’s what the agency told me. But David pointed out that without the agency and with my new prices I would make lots of money with five or six dates a week. “Why work hard when you can work smart? The guys I recruit can work very hard if they hav
e to, but they rarely have to because they are thinking all the time.”

  I took a little time to figure out which were the better hotels in Denver and I had a nice time checking each of them out. My thinking was that I would prefer to start with outcalls – until I found the best location for an incall – and if I was going to do outcalls I only wanted clients staying in really good hotels. David had insisted I buy a couple of really conservative pieces in the consignment store. “But I look like a frump.” He just laughed.

  I realized he was right when, dressed in the frumpiest, least “escort” looking outfit I had I had an early drink in one of the hotels. I think there may have been a couple of working girls at the bar but I took a book and sat at a slightly secluded corner table. It didn’t take long for a rather chubby 50 something guy to offer to buy me a drink and two hours later my cash reserve was replenished.

  All the while my phone was clicking discreetly with emails and texts from would be gentlemen callers. It had a clever notification light system I eventually learned how to use.

  I was in business. I was escorting a completely different way. When David flew into Denver three weeks later we went for dinner. “Mountain air agrees with you.” he said.

  He was right. Somehow moving to Denver changed how I looked, how I felt, how I did my escorting business. I even had a part time job. Nothing fancy. I was working retail at a cute little consignment store in a nice older part of Denver.

  That was nearly five years ago, forever in escort time. But I don’t live in escort time, I have my life and a part, a small part, of it is escorting.

  Sybil

  Lesbian Experience

  In the gay male world escorts and paid for encounters are simply part of the scene. It is not a particularly big deal and a surprising number of gay men have, at one time or another, been escorts.