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Assuming the Position: A Memoir of Hustling Hardcover August 24, 1999

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Although Assuming the Position is, as Rick Whitaker describes it, "a memoir of hustling," don't expect it to be particularly erotic. Whitaker thoroughly deglamorizes male prostitution, depicting it as banal and emotionally numbing rather than sexy or transgressive. Any potential arousal to be gleaned from his exploits is further dampened by the book's highly mannered tone and the rather ordinary quality of Whitaker's psychological "I was always pretending to be somebody's friend when I really only wanted his money," runs one such moment of self-reflection. "Of course this is just an extreme form of something we all do in order to get ahead, but such seeming friendliness is never good or heartfelt and it is always a cause, at least for me, of mental and emotional fatigue." Readers may also find themselves frustrated by the memoir's lack of narrative Whitaker did drugs and had sex with men for money for a while, then he stopped, then he wrote a book about how it made him feel. Unfortunately, being able to write grammatically correct sentences about his unusual experiences isn't enough to make Assuming the Position an interesting book. --Ron Hogan

Unknown Binding

First published January 1, 1999

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Rick Whitaker

10 books28 followers

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5 stars
13 (8%)
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40 (25%)
3 stars
74 (47%)
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22 (14%)
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Displaying 1 - 29 of 29 reviews
Profile Image for Richard Derus.
3,926 reviews2,246 followers
March 13, 2021
Real Rating: 3.75* of five

The Book Description: Rick Whitaker divulges the complex reasons that drove him to prostitution and reflects on the cost of a life of half-truths and emotional lies. With an unsentimental eye, Whitaker chronicles his descent and eventual resolution.

My Review: That's a pretty sparse description for a pretty intense book. It's a short thing, pared down to its essential points, and purged of prurient detail. (Darn it.)

Whitaker was the editorial assistant to publishing legend Gordon Lish. You know, Raymond Carver? Richard Ford? The one who edited, or quite possibly more than edited, their best stuff. He was, apparently, absorbing a lot from Lish (not a double entendre that I know of) because he wastes no words here describing his descent from broke publishing minion to crack-addled sex worker AND broke publishing minion.

It's amazingly easy to understand and sympathize with Whitaker. He's not some rotten-souled vile being who expresses himself by Doing Shocking Things. He's a guy who needs a center to his life, needs a sense of belonging and of mattering. I speak from experience here: If one needs those things, NEW YORK IS NOT THE PLACE TO LIVE. I watched it eat people alive, make others miserable, and all because the one thing those folks needed was the one thing the city does not reward.

Whitaker sold access to his body for drug money, for the momentary illusion of power, and for the sheer hell of it. He ended up not wanting what he found, and got out, and told his story so all the experience would not go to waste.

I like the book, where lots didn't much. I respect sex workers for the sheer magnitude of their performance capability. I admire their generosity of spirit (how many pretty people do you imagine subcontract their sex lives? Lots of old, lonely, ugly, fat folks do). I've had some very good friends (without benefits, thank you for asking) who did this demanding and difficult job. Whitaker's was a story I've heard with variations for years. It's not something I'd suggest one read for titillation, but any moralists who have accidentally stumbled into reading my reviews (you must feel so lost, poor lambs) should give it a whirl, as should those inclined to judge and find wanting all those billions and billions of people not precisely like themselves. (There is overlap in the categories, but they aren't all the same people.)

Empathy can be learned. Try this and see if you can't find some for a man searching for acceptance.
Profile Image for Sketchbook.
698 reviews260 followers
March 13, 2021
A best friend, CalTech grad (one of smartest peops
I've known), was "in the life" for 3 years while
writing op-eds on the polar ice melt for WSJ and DC
Post. Like the book's author, he needed admiration
and too much sex was never enough. Unlike the author,
he never touched drinks or drugs. This frank memoir
doesn't reveal anything you haven't imagined. There's
very little erotica.

But the skillful writing has an other worldly-dreamy
surreal quality -- albeit top-heavy on refs to Woolf,
Wilde, Whitman, Wittgenstein, Kierkegaard, Marvell.

My pal got a security clearance and went into aerospace.
Now that's a Happy Ending.
Profile Image for Max Kelly.
208 reviews2 followers
October 10, 2023
Hardcover from a random small bookshop sale!

This book was a lot headier than I assumed and I really enjoyed it. I definitely went back and forth between chapters, though some were a lot more impactful and profound than I had anticipated.

I really appreciate Whittaker’s philosophical insights and humanistic approach to hustling, especially diving into some of his internal dissonance and making it accessible. I am really grateful that he shared this with us.
Profile Image for Dennis Holland.
286 reviews142 followers
March 12, 2022
I was unable to make a connection with this memoir of hustling. Just as if I were seeking a hustler IRL, I’m not sure who or what I wanted from the experience. But I know it wasn’t this or this guy. The account was, surprisingly, boring and left me feeling, appropriately enough, pretty empty.
Profile Image for Adam Dunn.
664 reviews21 followers
August 18, 2014
Ugh. Pretentious, short, filled with unnecessary quotes from long dead authors in the public domain.
The best line in the book I thought was went he went to a drug counsellor and said he was addicted to meth and doing it twice a day. The drug counsellor says So? Hows that working for you?
There's this moment when you realize your problems are not someone else's, that you can't blame your childhood on your current lifestyle forever, that no one cares or will care except yourself. And this is touched on for like 2 paragraphs, and then back to Nietzsche quotes, irrelevant notebook entries from years ago and lines that start with "Ludwig Wittgenstein wrote in the diary he kept during the First World War...".
Your eyes will be rolling as you read.
Profile Image for Richard Jespers.
Author 2 books21 followers
January 10, 2015
A memoir of hustler. Touching, plain speaking prose. Whitaker makes one thing very clear. Hustling is bad for the human spirit, yet he overcomes its addictions to survive (and flourish, I hope).
Profile Image for Stefan S.
139 reviews1 follower
November 20, 2021
Interesting book about a drug-addict and hustler. Rick's life was clearly on a self-destructive spiral, but it seemed like the author oscillated between pride and shame. The book was written shortly after the events so I'd he curious how the next 20 years developed and he had additional reflections after more time.

I found this book at a Detroit used book store for $8 and found it entertaining enough, but not sufficiently self-reflective.
Profile Image for Chris.
266 reviews24 followers
February 10, 2013
Most books about hustling involve the details about what the sex was like and what the guys were like who paid for it. You go in wanting to know more about the industry and leave with a view that something different happened for the author. Of course there is the other side to these kinds of books, the ones that get written are the ones who made it out, and the ones that don't get written are probably still doing it or they lost their lives to the drugs and sex of the culture it has.

Whitaker is someone that you can tell from the beginning has a great academic understanding of things, his ability to clearly convey a thought is shown by how he writes, what he thinks about, and the books he spends his time reading. No one with a solid education spends their time with things that holds them back, they look for things that will only further their understanding of things. Whitaker shows that, even when his life is spiraling out of control at times.

The story revolves around a young man who goes into hustling because of the need for money and in some small way, to find himself. For most of his life he grew up without a father, and so the need for a father figure was evident in the man he found the most pleasure in. He talks about all the relationships he has been in and what they mean to him but also how that affected him when he was hustling. There were times he hustled, in his mind, just to get back at a ex-lover.

The book takes a turn when he goes from hustling in the clubs as a free-agent to hustling for agencies. The world of escorts is one only for those who have it. In order to get picked to hustle, you have to have a look that clients want, otherwise you are wasting their time. Apparently he had a look, and a very young one at that. You will learn just what the escort service is like and how busy you can be but you also learn how it distorts the understanding of money. When you are making 150 to 300 an hour, it's difficult to justify going back to a job that pays you no where near those rates. Not only that but depending on the clients you only work with, you might walk away with 5 to 8 thousand easily just on a weekend trip somewhere with a client. The other issue to consider is all the drugs that are involved in this line of work. Many clients expect you to do it with them in order to have a good time. Those that see the clearer picture in this know that the drugs are used as a way to mask their behavior and to ignore any guilt they might feel from it at that moment.

If you plan on reading this know that you will be in for a ride that times you through the ups and downs of life as a hustler, and if you are reading this because you want to get into the business; my advice is, don't read it and go back to school and earn a living the honest way. Yes it's hard to actually do it but your conscience will thank you for it in the end. Like I said before, the only reason this book was made was because he made it out, for all the rest, those books will never reach your hands.
Profile Image for cam.
51 reviews13 followers
July 21, 2022
This memoir was thrilling to read. Whitaker sustains a deep capacity for verbal self-awareness, interrogating his actions as if he were an unrelated onlooker. He describes the feelings that result from addiction—thrill, disgust, power, and shame—with such clarity it felt like I relapsed with him, again and again. Such a refreshing and honest read about how one hides from himself: about distraction, ignoring one’s own needs until he becomes a shell of a person, and of trying to remember how to return to the body.

As a reader, I craved a deeper understanding into why and how Whitaker used sex, drugs, and prostitution as a method of distraction. Perhaps the author himself did too, which is why he included the chapters about his childhood, instability, and fatherlessness. While some reviews accuse Whitaker of “blaming” his childhood for his choices, I think he was more trying to make connections, to interrogate the past’s influence on the present. Though, as with the other reviewers, I agree that he misses the mark—the association feels vague and underdeveloped, as if the reader should simply accept the logic that his addiction is purely a direct result of his shared anecdotes. An analysis of desirability, power, and masculinity, I believe, was the missing puzzle piece to making this memoir more compelling and robust, one that would satiate both the reader and author more completely. After all, Whitaker has no problem attracting men and money through his traditionally masculine features, yet makes no connection between his ability to sustain his addiction and his desirability. Also, you would think someone that reads so much Freud would have more to say about his dreams featuring his father’s penis.

Ultimately, I recommend this memoir, especially to people who feel they have a complicated relationship with sex. If you have ever leveraged your body—be it for validation, money, Uber rides, free dinners or drinks—or relied on sex for self-worth, this memoir will help verbalize that experience.
Profile Image for Broodingferret.
343 reviews11 followers
May 13, 2011
A memoir of life as a New York gay prostitute, Assuming the Position appears to have been written primarily as a step in the healing process of the author. Whitaker does a good job of conveying both the frenetic desperation of drug addiction and the emotional detachment that many prostitutes have to adopt in order to go through the motions of their trade. He doesn't delve too far into the sordid details of most his encounters, and when he does it's only to help drive home the damaging nature of the transactions, though the damage is as often self-induced as otherwise. While by no means endorsing the hustler lifestyle, Whitaker does make it clear that the experiences and traumas of the book are his, and that prostitution is not as damaging to everyone who engages in it as it was to him. Though he does fall a little too fully into the "I'm this way because of my upbringing and society" mindset for my tastes, his acknowledgement of at least some responsibility kept the book from being a complete exercise in self-pity. Certainly worth a read for anyone interested in seeing the emotional toll that such a lifestyle can take on a person.
Profile Image for Love.
198 reviews20 followers
May 30, 2011
So I loved the thought of reading this because Of CHICKEN..which if you have not read it yet was very good. I like to read about the male side of the prostitution. I am afraid to report that I did not like this book as much. Rick came across as trying to act smarter than he actually is. I hated that he felt the need to quote so many authors, and to talk about classical music. The entire book I was thinking is he just putting this in here to seem smarter than he is?? This might not be the case but this is the way I took it. I wanted more stories of his John's & his drug addiction. Or his childhood for that matter. I also found it disturbing that he dreamt of having sexual relatrions with his father. "Enjoying His Cock"???? WTH. Who even thinks that let alone writes about it right? SICK!! I also found it way to short. 179 pages was enough for a book I disliked though. I gave this 3 stars because I do feel he must have suffered something in his past to think and act the way he says he did. Maybe he was molested by dear old dad and this is why he dreamt about sex with him. I do feel this book kind of wasted my time :(
Profile Image for Caty.
Author 1 book70 followers
December 10, 2008
A nuanced + literary but totally apolitical memoir of hustling--he confuses his hustling w/his drug use, since they were sort of concurrent + is WAY too into amateur psychoanalysis for my tastes--still, an interesting read, though he is a slightly self-hating sex worker.
Why can't people ever say "sex work is wrong for ME" rather than "[insert generalization about hustling]" ?
Profile Image for Jeremy.
8 reviews2 followers
July 6, 2010
This is my favorite book of all time! I like to read it over and over!
1,335 reviews88 followers
May 31, 2022
How this book got published I'll never know. It's incredibly dull, repetitive, unorganized, and pointless. Also extremely short at 180 little quarter-pages with lots of space, meaning if you put it on a full piece of paper it would total less than 25 two-sided. Namely, it's a long magazine article or college term paper, but that would be giving it too much credit.

The author thinks he's quite a writer (he's not) who has unique experiences (he doesn't) and knows how to find the meaning in prostituting himself to other men (nope). He breaks up with a hustling boyfriend and to get back at him Whitaker goes into selling himself to other guys, mostly through an agency. The problem is that he only sticks with it a little over a year and beds around 100 guys. That's nothing--based on what he wrote I have lots more experience and interesting bedroom stories than he has.

Add to that the non-stop drug usage, claiming that it helps him stay hard, going to bed at 5 a.m. and sleeping the day away. Then he wonders why he doesn't get work or has no money in the bank. He also blames the drugs for his failure to recall more than a dozen of his hookups. The guy is dumb (he graduated from college with a degree in philosophy!), impractical, uncaring when it comes to other humans, and totally selfish. A real jerk and who wants to read a book about a jerk who thinks he's hot stuff? I guess he was smart enough to find a publisher to print this, but maybe he just slept with the right guy.

There aren't enough specifics about his sex work. He manages to skip over some of the most interesting things in his past, including his mother's six husbands, the saunas he sat in with naked dads with kids, and the author's many dreams about sex with his father. The author alludes to the possibility that his dad sexually abused him when drunk but it's nothing beyond a hint, yet you have to wonder why he keeps dreaming about servicing his father's hard manhood.

Worst is that he blames his clients for his bad choices and unhappiness when the evidence is right there that, after as a boy seeing his mother have sex with dozens of strangers, he came by his profession naturally following in his mom's footsteps. He, like all men, make their own choices as adults and can't shift responsibility to their pasts or the ones they later claim are abused their bodies.

Skip this. Other than showing readers the typical warped thinking of a selfish gay man this book has nothing going for it.
Profile Image for Alex Anderson.
356 reviews4 followers
December 4, 2021
Read this over the course of 3 hours after it was given to me by a friend (who also just stumbled upon it). Very short and straightforward account of the author’s time as a prostitute and drug addict. It seems he wrote it almost immediately after deciding to stop hustling (as he puts it), since there seems to be little introspection. From my perspective, and I think anyone else who reads it, it seems like he had a traumatic and tumultuous upbringing and was looking for love and excitement in all the wrong places. He didn’t seem to connect those dots though, which I wonder if more time and therapy would change his feelings. I personally was shocked at how ubiquitous escort services were - this was in the 90’s, so I wonder how that’s changed with the rise of social media and online dating apps. Ultimately didn’t take much away from this since it felt more like a therapeutic journal versus a story an audience could connect to. I hope the author has since found inner peace!
Profile Image for Brian Kovesci.
895 reviews15 followers
February 26, 2022
A peek into this man's life as a hustler in late 90's NYC.

I got this because Chip designed the cover. And because queer sex working.
Profile Image for Sebastian.
47 reviews1 follower
February 3, 2024
I already tend to enjoy memoirs but I especially loved this particular flavor of introspection. a short but really valuable read imo
Profile Image for Jerome Baladad.
Author 1 book25 followers
January 21, 2011
This book maybe found interesting by those who are curious about what goes on in the daily lives of hustlers. Or this can be a handy reference guide for those who are pondering on getting into the hustling business, given challenges of looking for jobs, even part-time jobs in today's economic environment. It is not in any way encouraging others to get into the trade, given its inherent difficulties (found in most businesses) plus the attitude of most people in society who may not know any better about hustlers except from those movies or TV shows they've seen. The author, who himself went into the hustling business, was candid in describing his experiences - nothing prevents the reader from imagining how things go about during these commercial transactions. The author may have looked like any of those goodlooking fellows you've met on the subway. It is to his credit that he decided to find meaning and substance from what he went through while engaged in the hustling business.

The book is not graphic at all in describing what maybe considered 'sexual' but enough can be read to get a poignant feel of the business. It's surprising to read about someone who has been into the trade and at the same time able to write very well about his hustling experiences. The book's not at all dramatic by design - it's actually an honest cautionary tale. It's about those who have chosen the path to make a business out of their physical assets that are deemed marketable by those whose ideas of youth and beauty are defined by what's generally shown in regular media outlets.
Profile Image for Tiffany Gallant.
Author 2 books8 followers
February 13, 2017
I read half of this book and was so disgusted I threw it away. I have been reading memoirs of prostitution and human trafficking to get ideas for my own memoir. I always come across books written from the female perspective but this is the first one I ever found from the male's perspective. I did not like it at all and found it to be too graphic. I think the writer lacks boundaries and was writing for shock value. I think this book could have been better written if it were written to help discourage hustling. The writer obviously had a painful childhood, and I believe that helped his addiction and promiscuity. There were certain details in the book that were unnecessary and a bit horrifying.
Profile Image for Allan.
1 review
January 24, 2010
Definitely an interesting read. Some may complain that it's not political or analytical of the industry as a whole; but it's a -memoir-, so that's definitely not the point. Whitaker takes the reader on a somewhat detached journey through his experience in the world of hustling, and gives an excellent personal account of his insights during and after his stint. If you take the book at face value, as the story of a male prostitute and the effects of the work on his life, you'll enjoy it. If you expect some deep analysis of the life of a hustler, go read an academic text. He presents us something simple: his story and his thoughts, without bogging us down in tedious explanations of every little detail, and it's definitely an extremely enjoyable (and quick) read.
Profile Image for Tory.
316 reviews
October 16, 2007
I didn't think that I was a big fan of memoirs, but I might like them. A little. Or at least I'm starting to.

I thought that this book would be a lot more sordid and dark, being the tale of a New York hustler and all... but it wasn't. I think because it was written in a rather detatched manor. Feelings, addiction, the Johns, were told about rather than too deeply discussed.

It was... just a story I guess. Everyone has one, just every one's doesn't include prostitution.
Profile Image for Kelly.
Author 26 books691 followers
January 18, 2012
I wanted my first read for the year to be nonfiction (for no clear reason), and this popped up in BN.com while I was looking for something else, so I ordered a copy.

It was frank and interesting, but it didn't leave me with any profound sense of having learned much about the author, so I'm kind of torn on whether I liked the book or not.
Profile Image for Sarah.
1,227 reviews31 followers
March 30, 2013
This was a look at a world I know nothing about and will never experience, the life of a gay prostitute. It is a fascinating glimpse at a life out of control. I did find part of it a bit tedious with the constant mention of different boyfriends- and the author's pondering on his life was a little hard to follow at times.
Profile Image for Ruddy.
34 reviews3 followers
July 31, 2007
Interesting memoir of a gay prostitute in NYC. Hes very sincere and graphic. The book is real and a very short read.
Profile Image for Jenny.
2,013 reviews52 followers
September 14, 2008
Quick read. Not quite what I imagined a gay prostitute would have to say but it was still interesting and there were many eloquent sentences and thoughts that I felt compelled to share.
Profile Image for Darrell.
186 reviews8 followers
December 24, 2008
an Anglo hustler turned novelist recounts his days on the job - interesting stuff
sort of has a Denis Cooper/Bret Easton Ellis vibe to it
Displaying 1 - 29 of 29 reviews

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