The Road From Sugarbaby To Escort

by Avery Day on May 6, 2013 · 18 comments

in Money, Prostitution

My SA profile

My SA profile

When you’re 23 and getting divorced after 5 years of staying home, the only logical thing to do is to look for a sugar daddy, no? It made perfect sense to me; I wasn’t interested in a serious relationship, but being taken out on nice dates and having help with the bills seemed like a win-win situation. I truly believed there were these handsome 30- and 40-something year old men who were just happily fluttering $100 bills in pretty girl’s faces; that they deemed it their responsibility to financially support young women.  My career in sex work started this naively.

Those illusions clashed with the reality of being a sugar baby as soon as I met “Jim,” who convinced me that he was a generous sponsor after a dinner at Beni Hana and an offer of a winter coat. I spent our dates high out of my mind, so my perception of things was undoubtedly flawed, and my memories of him confuse me to this day. But as I recall, we would go to his house where we had Thai delivered every time I came over. He was in such a rush to get upstairs that he would hurry me through dinner. His “son’s room” was like no child’s room I have ever seen – it looked to be straight out of a Pottery Barn catalogue with not one thing out of place. At the time, I didn’t think he really had a son, and looking back it makes me wonder what else he could have been lying about.

Each time we saw each other he gave me a couple hundred dollars, except for once. The last time we spent together, he slapped me across the face while we were in the middle of sex and began what he believed was dirty talk. “You like that, don’t you?  You like being my dirty little whore?” I was so shocked I didn’t respond at all, and when he dropped me off, he gave me $60 “for gas money this week.” Based on the agreement that he would give my girlfriend $40 each time for babysitting, this meant I ended up with $20 for being smacked around. I could discuss how much my sitter needed to be paid, but talking about my own compensation, for whatever reason, was too uncomfortable. For the first and last time, I had wrongly assumed that a man “just knew” what the magic number was.

“Samuel” picked me up in his 300Z and we went to Montana Grill where he spent the evening asking me “deep” questions, wanting to discuss in detail his exhaustively descriptive emails about books he’d read, articles he wanted me to read and share my opinion on, and lifelong dreams he wanted us to share in hopes of finding the all-elusive connection. His longing for an emotional connection was apparent. After that first dinner, he drove me back home and handed me $300, not asking for anything else from me. YES! I thought, this is more like it! When we got together again, he took me to his house in a suburb west of Denver. Turned out he lived with his parents, whom I was introduced to when I arrived. (It was the first of several times in my career I’d be introduced to parents.) I listened as he showed off all of his autographed porn star memorabilia. We spent some time in the bedroom before he took me back home, again giving me $300. Sam was looking for more of a girlfriend, and he wanted to have unprotected sex, which I was not comfortable with. Sam’s last relationship had been with an escort who eventually passed away from a drug addiction. He seemed deeply wounded, and was searching for an exact replacement.

Since it was evident it wasn’t going to work between Sam and I, he suggested that I try escorting. It was with him that I first encountered the notion of a “hobbyist,” and he told me he would be happy to write a review for me. It was with Sam that I realized not all sugar daddies are new, gullible, hesitant men who are reluctant to plunge into the escorting world; rather, they’re often hobbyists who are in search of less boundaries, cheaper “deals,” and more of a connection than is usually found at the standard hourly rate. We wished each other well, and a few months down the road when I decided to try actual escorting, he did write my first review.

But before I took that plunge outright, I branched out from specific sugar daddy sites to try my luck on Craigslist, coincidentally in the year the adult personal section was shut down. “Dave” —the first man I met from CL—was overly anxious and so we skipped the initial meet-and-greet dinner date that was standard protocol. I needed the cash, and less time spent bullshitting was fine by me. So he picked me up in his Jeep and took me downtown near the Capitol. He handed me the cash in an envelope and suggested I excuse myself to the bathroom to count it: all $350 was there.

He told me he’d created an “online story” about the two of us and was going to write our experience down like a journal entry. He also offered to be my manager and suggested that if I didn’t want to do official escorting regularly, I could just be a high-end courtesan and he could design a website for me. He reminded me of an overweight Gene Simmons, and he talked endlessly about his band and recreational drug use. He was the only 50-year-old I knew with a MySpace page. Dave whined half-heartedly that I insisted on a condom for everything, but didn’t resist.

Innocent me, in my first ever SA profile pic

Innocent me, in my first ever SA profile pic

It was a year later when I was working for an agency that a photographer made a comment about a particular hobbyist’s handle on a review board. I perked up remembering this was Dave’s email and MySpace page handle. His favorite pastime was apparently writing elaborate reviews of naïve girls just getting into the business, and what bareback services he was able to coax out of them before they “learned otherwise.”

When I first began dabbling in the sugar daddy world, I really had no intention of doing any consistent or long-term.  It was simply to bring in a little additional money when I needed it, and have a date with some rich guy who enjoyed arm candy. But then the child support payments dried up and my full-time job was only covering half of my monthly expenses. Being in a huge city essentially by myself with two young children, my options felt limited at the time. I was already meeting with strange men and accepting their money, so the step from the Craigslist personals section to the Backpage escort section was no large leap. After a particularly upsetting conversation with my ex-husband, I angrily posted my first ad on Backpage. I will never be dependent on someone else to support my children, I said to myself. And 5 years later, I still haven’t regretted that decision.

I met a few more men from these websites, but eventually abandoned the notion because I realized there was faster and better money to be made as a full-fledged escort. I enjoyed the business-like aspect of escorting much more than long drawn out emails and phone conversations. If a client was interested, they contacted me and we simply scheduled a time. The boundaries are so much more established, whereas being a sugar baby leaves so much gray area, at least in my eyes. My personality is very orderly and professional, and that clashes with trying to be the wide-eyed, affectionate baby doll sugar daddies seem to prefer.

My early days as an attempted sugar baby paved the way for me to escort and many of the things I learned — how to stay anonymous, sober, etc. — were as, if not more, important in the escort world. I also realized that by having a sugar daddy (or two,) most of my time was consumed with maintaining the illusion of an intimate connection with them, and my finances were, yet again, dependent on one person who could simply back out of the agreement at any point in time without warning or recourse. For my situation, and my personality, escorting made sense; I was able to remain in control of my own time and finances without the dread of a dysfunctional/delusional relationship distracting me.

While one might hope (or assume) that sugar daddies have far more discretionary income than the average escort client, it seems from my experiences to be the exact opposite. I’ve met both great and shitty men in both situations, and while my patience levels led me to focus on escorting exclusively; I also see the benefit of marketing to both pools. The unashamed ability to seamlessly push a relationship beyond the hourly commitment of escorting and into the SD/SB realm is an art, a skill that is developed over time, and it’s not for everyone. In the sugar daddy realm, I was never able to make it work in a way that was a profitable as I wanted.  However, over the few years that I have been escorting, I have developed several on-going relationships with regulars I met through that venue, and those developed into something more like the sugar roles than the traditional escort-client hourly agreement. The difference is that we still respect each other’s boundaries, personal lives, and occupations with no expectations of exclusivity. For me, that’s what has worked best.

{ 18 comments… read them below or add one }

Valerie Blair May 6, 2013 at 2:12 pm

Very well written, I also have a story to tell, and one day I hope I can share with the world. Way to go girl! Keep writing and achieving your dreams!

Xoxo, Valerie

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Ala May 9, 2013 at 1:13 am

This was great, and I agree with so much of it.

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M May 11, 2013 at 10:19 am

Great post! Someone once said “Those men who post on SA.com and other sugardaddy sites are simply men who failed escort screening”. The more time I spend in this business, the more I think that is true. There are men who completely lie about their income and employment in an effort to get women to have sex with them and there are men who are complete newbies and are terrified of getting an escort. I think those websites are an effective tool to find clients and some are receptive to screening. I have only met one man that was legitimately a sugar daddy who went above and beyond a pay for play type of situation. It’s unfortunate that many women flock to those sites thinking they’ll find some man to cater to their every whim, when in most cases men are trying to get the most out of a woman for the lowest cost.

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MB May 16, 2013 at 1:26 am

Yepppp… My experience with sugar daddies has just about been the same. Nicely done.

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Coco May 17, 2013 at 6:00 pm

Had a very similar experience as you with SA, but in Europe where I believe there are slim pickings…

After feeling like an escort one to many times when that wasn’t the role I had chosen, I decided to go ahead and become one and take ownership of that. Otherwise, you’re left feeling jilted and used.

I really enjoyed your post!

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A.E. May 24, 2013 at 8:33 am

I made the same transition for the same reasons. Very well said 🙂

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Tiffani Jameson May 28, 2013 at 10:09 pm

This was awesome!
I have always said that SD’s drive women to escorting. SD’s that voice their opinion online talk about SB’s as if they’re just brainless, and don’t know that this is a P4P transaction.

I didn’t become a SB until I was over 30, and my guy just wants to be around good people, and I don’t play the old BBFS either. But when the opportunity presented itself when I was 20, my naivety wouldn’t allow me to accept the offers. I told the guy, “but you’re married!” LOL I often think about what would’ve happened had that meeting gone beyond dinner.

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Couture June 15, 2013 at 11:59 am

What an awesome story. It was so well written, too! Although my decision to start escorting was based on completely different circumstances, I still felt like you and I had a ton in common. The way we make life decisions or learn lessons seems similar, it was really interesting to see it from a different perspective.

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lagirl December 17, 2013 at 7:25 am

I agree. Sugardaddies or dating rich guys is too time consuming and you dont usually get compensated well, instead you get your time wasted and scammed. Escorting is like having your own biz and the better way to utilize your sexuality for money.

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Todd December 22, 2013 at 10:50 am

I enjoyed your story, but I’d like to relate the other side of this (the guy’s perspective).

I’m a hobbyist who decided to do the sugar daddy thing a few years ago. I hadn’t ever had any trouble with escort screening, but I wanted something that was a bit less businesslike. More than anything, the legal ramifications of using escorts bothered me. I didn’t want to end up as a mug shot on the evening news.

When I moved over to SA, I didn’t try to rip anyone off. I offered $200 to $300 per encounter, which is in line with higher end escort rates in my area.

I did have some good arrangements, a few of which lasted for 3 to 6 months. However, I eventually decided to go back to seeing escorts. Like you, I found that I was spending a *lot* of time emailing people on SA who didn’t have realistic expectations. And there was a *lot* of drama.

SA attracts a lot of very young women who believe that they are going to meet dashing 29-year-old millionaires on the site. The reality is that most of the real SDs are over 35–with 40- or 50-something being more typical. (I’m 45, BTW. I am no Brad Pitt; but I’m clean, reasonably good-looking, and height-weight proportionate).

A lot of the younger women on the site were looking for “a young, hot sugar daddy”. To me, this seems unrealistic. I asked a few of them: “If you just want to date young guys, why not just head to the campus bar or sign up for Zoosk? SA is a sugar daddy site.”

Then there were women who stated at the outset, “no sex”. I’m a gentleman, but I’m not interested in paying $200 to $300 to take a woman out to dinner. The idea of “arm candy” is mostly invented by women, I think. Few men really think that way. I never even bothered emailing most of these women.

Finally, there were a number of women between 28 and 40 who saw SA as a sort of high-end Match.com. Most of these women seemed to have decent incomes of their own, and they were looking to meet a doctor or attorney who would be “Mr. Right.”

There is nothing wrong with this desire, mind you; but that’s not the agenda of SA.

What I was looking for was a fit, clean, attractive 21 to 35 year old woman who would occasionally get together for adult fun for $200 to $300 each time. I did find a few of these, but–like you, Avery, I found that I was spending an excessive amount of time on situations that went nowhere, in which my expectations were totally different from the other party’s.

There were also women who were open to sex, but only if you committed to paying a $2,000 ~ $5,000 monthly “allowance” at the outset. No thanks.

I’m now back to seeing escorts. But now I’m spending more time researching each one on the various review sites. I’m also seeing only 2 to 3 escorts on an ongoing basis, so I don’t have to worry about the legal issues as much, and there is more familiarity. (Like you said, it is more like an SD/SB relationship with realistic expectations on both sides)

I think the real takeaway from all this is that we need to change the laws. In my view, SA, when used for actual arrangements, is basically a way to work around the prostitution laws (because it’s “dating”). We need to change the laws to make the adult world better for men as well as women.

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Hanna January 4, 2014 at 12:14 pm

So…basically you ARE looking for an escort, but you simply don’t want to call her an escort… Riiiiiiiiiight. #smh

If you would offer me 300$ per meet and would only want to fuck me and nothing else, then I’d consider that an insult, and most SBs I know would agree with me. It is common practise to pay a monthly allowance to SBs and to support them financially, it excited a wealthy man to spoil a girl and to get her time and attention in return. Sex is almost always optional in these relationships, not what we SBs get paid for predominantly. You, a gentleman? Don’t make me laugh!

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Todd January 10, 2014 at 5:32 pm

Hanna, you might actually read the above article before giving your opinions (which are mostly based on wishful thinking, I suspect). Avery Day is basically saying what I’m saying, albeit from the female perspective.

People don’t just hand other people significant amounts of money for nothing. The real world doesn’t work that way. No man is going to “pay a monthly allowance” and “support someone financially” in a situation where “sex is optional”.

Yes, some SB/SD relationships do develop into longtime, ongoing arrangements. However, there are very few men out there who are going to commit to “supporting” anyone from the get-go.

Most arrangements start out on a per-meeting basis. In my area (the Midwest), there are plenty of women on the arrangement sites who will agree to $200 to $300 per meeting (with intimacy included).

There are, however, (as I detailed above) many ladies who enter the site with unrealistic expectations. They inevitably end up dropping off after a few weeks.

But don’t take my word for it. Read the above article.

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Deloi May 22, 2014 at 10:46 pm

I stumble across this blog, and found this interesting. I find SA interesting, yet weird. This type of arrangement is interesting and could work, but I find the women on the site to be, well; Delusional. As you noted:

SA attracts a lot of very young women who believe that they are going to meet dashing 29-year-old millionaires on the site. The reality is that most of the real SDs are over 35–with 40- or 50-something being more typical. (I’m 45, BTW. I am no Brad Pitt; but I’m clean, reasonably good-looking, and height-weight proportionate).

A lot of the younger women on the site were looking for “a young, hot sugar daddy”. To me, this seems unrealistic. I asked a few of them: “If you just want to date young guys, why not just head to the campus bar or sign up for Zoosk? SA is a sugar daddy site.”

Then there were women who stated at the outset, “no sex”. I’m a gentleman, but I’m not interested in paying $200 to $300 to take a woman out to dinner. The idea of “arm candy” is mostly invented by women, I think. Few men really think that way. I never even bothered emailing most of these women.

Finally, there were a number of women between 28 and 40 who saw SA as a sort of high-end Match.com. Most of these women seemed to have decent incomes of their own, and they were looking to meet a doctor or attorney who would be “Mr. Right.”

There is nothing wrong with this desire, mind you; but that’s not the agenda of SA.

I agree with this. Women seem to not understand the pool of very wealthy (and by this, I mean guys who have true net worth of at least $10 million and up) men is very slim. And while wealth is getting younger thanks to tech, the youthful wealth of Mark Zuckerbergs are a very rare breed. I notice women have ridiculous demands and standards on here…ladies, being pretty is not an exclusive trait. You’re not in the driver’s seat in this world. And once you hit 30, your “Value” starts to drop when your in a open and competitive platform like SA. You want $10,000+/month allowance? Really? Just because you think you’re pretty? Honey, look around, you’re surrounded by equal age and younger women who are just as interesting-if not more-as you. I hate to equate this to economics, but the demand is WAY higher than the value of the supply in this market.

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JuliaDevine November 19, 2015 at 10:49 am

I mainly agree with what your saying. The part that isnt mentioned is where these delusions come from. Just watch a Dr Phil episode, or some Sugar Daddy special on NBC. The media has glamorized the Sugar World by making the 2% rare cases of lucrative wealth, stand out as the stereotype. Basically there is this super wealthy older gentleman dishing out cars and condos to pretty college gals. And although it definitely exists and I have been in one of those 2% relationships more than once, it is not the majority.

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JuliaDevine November 19, 2015 at 10:41 am

Hey Todd

Thanks so much for your insight. That is the one thing us girls overlook, is the other sides perspective. I learned the hard way in the Sugar world, and I ended up deciding that escorting is a better flow from week to week. The girls that usually accept 200 per meet. Are very naive, very in need of money and also dont realize that a mere hour as an escort would get them 200 bucks. I remember the days when someone would pay me 350 and I’d literally sit with them for half the day. Now I know that they were ex hobbyist looking for a beautiful, educated lady unfamiliar with the other side of the tracks for a cheaper price. I wish it hadnt taken so many years to figure out, but at least now I use SA for what it really is designed for. The older, very wealthy SD. I will do per date situations, but not for a dime less than 1000 per meet. And even if I spend a few hours, I still calculate it as an escort in my head and make sure I am never going below 250 per hour.

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DrDr July 29, 2014 at 1:09 am

I concur with both Todd and Deloi’s assessment.

Myself, I started with massages, then escorts, then SA/Sugardaddy.com. SA yielded the highest quality of person, IMHO. Just as Todd stated, there were many women who had their own net worth, and were seeking alternative relationships. Either outside their own dead marriage, relationship or what I call ‘Alpha Woman’- Women who had very high net worths, but clearly a darker side/approach to dating; whom also sought out similar “Alpha Males”.

Men who use SA, generally fail at escorting is probably among the dumbest idea I’ve ever heard. It’s actually the complete opposite. Myself and 3 of my closest friends who have high annual incomes, would be described as ‘Playboys’. We work hard, and play, harder. No pun intended.

Sure arm candy is nice, but nicer when when her 19-25 y/o ass is naked walking around the pool.

We pay for what we want, when we want, and the convenience. Sure, there have been a few girls where real friendships were born; the reality is that I’d say there’s guilt on both sides in the naive department.

Bluntness, honesty and straight forwardness is the key to success with these relationships.

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gothceltgirl April 30, 2016 at 4:21 am

What an insightful blog. I was actually considering this, since I’ve been having so many difficulties lately, long story. Not looking for too much, not going to be unrealistic in my demands or expectations. Maybe a few encounters from a few different SDs per week so that I’d have a nice amount. But I’ve always preferred escorting TBH. It’s so much more straightforward. I never really liked the idea of all of the pretense. I’d wondered if there was this unwritten expectation as the blog writer mentioned of being a pretend girlfriend. I’d need low pressure & a fee per encounter. I’d need something basic, but low-pressure. Maybe if I went middle of the road. Not too many demands from me & maybe a once a week sort of thing… I suppose. Plus I may be able to finally get some reviews so that I’ll be more established and can get professional photos for my site. I’m trying to find out all I can before I take the plunge though. -LeilaGreene

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gothceltgirl April 30, 2016 at 4:29 am

Oh & Avery, I too am baffled by these guys that want to get it on with you w/o any condom. What is wrong with them? It’s like “We just met!”. No way. I’d have to be with a real boyfriend a while before that’d happen.

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