By Anna Pulley
By Erin Sherbert
By Chris Roberts
By Erin Sherbert
By Rachel Swan
By Joe Eskenazi
By Erin Sherbert
By Erin Sherbert
An attractive man makes his way across the wooden deck of the Castro's Patio Cafe, dodging waiters who are serving diet Cokes and Bloody Marys garnished with oversized celery stalks to a roomful of men. In the bright, airy dining area -- under the retractable sunroof, away from the Tiffany lamps, the hanging plants, and the speakers blasting Gloria Gaynor disco anthems -- the tall man, who has dark, wavy hair, is noticed.
"Now there's a good-looking Italian," says Patio brunch regular Bob Logg, catching a glimpse from a corner table. He puts down his fork to get a closer look, but quickly changes his mind. Despite a nice build and warm smile, some lingering laugh lines suggest the man has probably hit 30.
"Too old," Logg determines, going back to mopping up the egg yolks on his plate with a piece of toast.
It's a harsh assessment, considering that Logg is 70. But this septuagenarian likes his men young, and he can afford to be picky. A successful real estate speculator who calls himself a "rich, old queen," Logg is used to indulging his tastes. The double parlor in his million-dollar Victorian home is cluttered with 19th-century antiques and artwork. Chandeliers grace every room. Stained glass surrounds the shower. And young, beautiful men share his canopy bed. But like his Renaissance wall clocks and marble Roman garden statues, his men have a price.
Logg lavishes food, clothes, and other gifts on his current boyfriend -- a stunning, grandson-age 23-year-old. He also pays the young man's rent and college tuition bills. Since meeting Logg, the boyfriend doesn't have to work as a waiter anymore.
"The minute I saw him I almost dropped my teeth, he was so gorgeous," Logg says. "I knew I'd be putting him on the payroll."
But the arrangement is not just about paying for sex. Logg and his young boyfriend spend lots of time together outside the bedroom. They dine out, ride bikes in Golden Gate Park, and go for walks holding hands. They are lovers.
In this gay version of keeping a trophy wife, Logg is following a long tradition set by his wealthy straight counterparts, who divorce early and trade in often. Gender aside, the relationships still focus on the youth and status each lover has, but the other wants. They still deal with being seen and getting paid. The older gentlemen have something pretty to wear on their arms, and their young charges make easy livings.
For Logg, the May/December spectacle is no cause for embarrassment. Every Sunday, he takes his boyfriend to the Patio for brunch, where they -- both of them -- are on display. All the turned heads, long stares, and knowing winks are worth every penny.
"You think I eat in the Castro because of the food?" Logg says. "Having a trophy boy is like having a very elegant car. One reason you get one is to show the damn thing off."
There is always a line out the door during weekend brunch at the Patio. It is a popular place to be seen after a night of barhopping; the crowd is more interesting than the menu, and sex is in the air.
"There's a lot of prime beef around: muscle men, pretty boys, S/M guys in leather pants," says waiter Kevin Vu. "I get the impression I'm serving a lot of people who just met the night before. I look at them and feel they either want sex, just had sex, or want more sex."
Into that charged atmosphere, Logg and other sugar daddies bring their young boyfriends, so the elders can prove to the others they are still sexual competitors -- and winners. Vu says he can usually count a half-dozen tables with May/December couples when the restaurant is full, all quite obvious in their intentions to show off.
There are flashing glances of respect between the older men at the tables, checking out each other's newest buy. But not all the glances are favorable. Logg knows there are plenty of gay and straight people who don't approve of his relationship. He doesn't care what they think, dismissing the negative looks and hushed remarks as envy.
"All the queens, and even the straight women, drool over my boyfriend, and I know they're saying, 'What's that old fart doing with that gorgeous creature?' I know they just figure I have enough money to buy whatever I want," Logg says. "Well, I look back at them as if to say, 'Don't you wish you were fucking this?' "
If the Patio works well for the trophy-boy show, the pickup often happens across town in Pacific Heights at the Alta Plaza bar. There, the scene is as much about style as about sex.
"It's probably the most respectable and classiest gay bar in San Francisco, with-out the typical 800 coats of black paint," says bartender Scott Krumtum. "It's a place you'd have no problem taking your mother."
Live jazz music wafts up to a linen-napkin restaurant, situated on a landing that overlooks the bar. The decor is refined elegance: soft lighting, sleek interior design, and wood accents; the bar itself is made of fine cherry. It's a tie-and-sweater crowd, for sure. Lots of gay doctors and lawyers -- and the young men who like them. There's a running joke among the bartenders that sometimes, they should just call it Father/Son Night at the Alta Plaza.
The older men -- the "hunters," the bartenders call them -- gather at the third station of the bar, where it bends toward the door. The "point" offers the best view of the low balcony that runs in front of the bar, where a line of potential trophy boys are arrayed along a railing.
The hunters know a bar like the Alta Plaza is where they will have the best chance to bag a young boyfriend. It's their turf, and it's where they are comfortable. At a sex-driven dance club in SOMA, where everyone is good-looking and under 25, the elderly hunter is out of his element.
"If a 60-year-old went to the Badlands looking for a young stud, he'd just sit in the corner. It would be: 'Is he going to be a good lay? No.' " Krumtum says. "People could care less if he owned North America."
The sugar daddy knows the pretty boys hanging out at the Alta Plaza are at least available to date their elders. The boys are clean-cut and freshly scrubbed, dressed more casually than the hunter gentlemen -- who usually wear sport coats and slacks -- but preppier in style than others their age. Button-down polo shirts and chino pants are much in evidence.
"It's like they're ex-fraternity brothers who found out they were gay; it's not hustlerish or trailer-trash at all," Krumtum says. "And that's important. The gentleman needs someone he can be seen with ... can take to dinner and the ballet and show off. The kid has to have some sort of social grace; he can't be a blatant hustler."
The first move is reserved for the older man, who will send over a drink or walk up and introduce himself. The over-60 set still behaves with 1950s formality. The older men announce their names -- first and last -- and offer "pleased to meet you" handshakes. The etiquette is a little foreign to the just-21 newcomers, who often return these polite passes with tentative smiles, or a simple "Hi."
Small tables line the back wall; there, freshly paired couples can sit and talk over cocktails. A corporate VP who spent the day ruminating about derivatives and stock options now finds himself asking his young date trite questions such as, "So, what's your major?"
"Then the Jaguar or Mercedes he has parked outside gets mentioned -- usually within the first 10 minutes of the conversation," says Krumtum, who has overheard countless trophy pickups. "It's so funny, you have to laugh. They try so hard not to seem like pathetic, old men."
A Porsche Roadster drives slowly by the flagpole in front of the college, circling a young man wearing baggy jeans and a tight, white T-shirt over his sturdy build. Jay cannot react; he is trapped in conversation with one of his contemporaries from school. A student government officer, Jay hoped he could leave unnoticed today. But now his ride is here, and his schoolmate won't go away. Jay tries to ignore the Porsche, but it turns back a second time, and the driver starts to shoot impatient glances Jay's way. Then, the car stops and parks -- and Jay panics.
The 18-year-old freshman doesn't want anyone to know the 42-year-old man behind the wheel, who looks remarkably like Nick Nolte, is his boyfriend. So Jay tells his classmate that the man in the car is a co-worker of his mother's who has agreed to give him a ride home.
Trophy boys know that being adornment, or arm charms, is part of the payback for the gifts they receive from their older mates. But the public dating at fine restaurants and cocktail parties is all about running into the sugar daddy's friends, not the trophy boy's.
"My friends would flip if they found out I was dating someone over 24. They'd think I'm easy and have no taste," Jay says. "It's not a cool thing to them. It's really gross -- worse than dating a girl."
Away from their straight and gay friends, the trophy boys -- or twinks, as they like to call themselves -- share in a somewhat secret society. They network via the Internet and meet in person at father/son cocktail mixers. The "shindigs" or "social hours" are usually held the last Friday of the month, hosted by various sugar daddies in their Nob Hill homes. Twinks are encouraged to bring friends who are interested in being trophy boys, too. These social hours are subdued affairs, catering to the older men's tastes in classical music, cognac, and cigars.
"It's really posh; not like a raging party at all," Jay says. "I started eating liver pate on Melba toast since going to those things."
After everyone has been introduced, paired, or showed off, the party becomes more about the sugar daddies enjoying each other's company. The men take over the den; the bored twinks escape to the back porch, where they can be 19 again. Out there, it's cigarettes, beer, and lots of "girl talk." They gossip, swap war stories, and make fun of the men inside, joking about what it's like to have a boyfriend suffering from a midlife crisis or -- for big laughs -- impotence. They also brag about how well they're doing with the gifts.
"It's like a contest to see who lavishes their little stud puppy with more things," Jay says.
Beyond the social hours, Jay meets other twinks by administering a members-only Web community called California Naughty Boys, where young, gay men from the Bay Area post their photos and vital statistics for potential sugar daddies to peruse. The prettiest boys get the most responses, but beauty is in the eye of the sugar daddy. Although most of the older men are white, as are most twinks, sometimes a twink who is perceived as having an "exotic" look will beat out the competition. There is always a racial or ethnic niche that needs to be filled. Asian boys, for instance, have a strong sugar-daddy following. But Jay doesn't seem to mind -- or even be aware -- that his white boyfriends could be objectifying him based on how he looks.
"I'm usually the only dark guy at the parties, so for men who go for that, I'm in high demand," says Jay, an African-American, who sports a cool, hip-hop look that complements his nice build. Two looped earrings hang on each side of his boyish face and devilish grin.
Jay grew up in the Bay Area with his mom and older sister. His dad is not around. Jay doesn't know what he wants to do after college, but politics might be an option, if no grand juries ever find out about his life as a trophy boy. Nabbing a student council seat was easy for the college freshman, who is a smooth talker and wise for his age. As for why he entered the twink world, Jay has no explanation other than boredom.
"It's exciting doing something against society," he says. "It is forbidden, and that's what turns me on."
And being a trophy on display doesn't bother him either. "I know I'm being seen as a prize," he says. "But I like being the center of attention -- and I like the gifts."
Sugar daddy Logg says there is an understanding when older men parade young boyfriends around the Castro and at private parties. "It shouldn't bother the kid," he says. "Either he really wants to be there with you or, if he's just in it for the hustle, it's a great chance to advertise his wares and let people know he's peddling his ass to older men."
Jay has never put himself on the market at school. So the "mom's co-worker" excuse works -- this time. And soon, he's alone with his middle-aged boyfriend in a booth at a Mexican restaurant, sharing chicken nachos. There are kisses, too, but those come later, after "Nick Nolte" picks up the tab for lunch, and after a shopping spree that nets Jay a new jacket and ring.
Jay sings to his friend Harry, a fellow twink. They are hanging out on a Saturday afternoon, talking about boyfriends, as they get ready for a Halloween costume party. Jay is dressing as a cowboy: black leather chaps, a shiny red fringe shirt, and a silver sheriff's badge. Harry is painting his nails black so he can be a vampire.
Harry, a tall, French-Filipino mix with long, black hair that falls past his shoulders, knows why Jay is making that cash-register sound. Harry's 44-year-old boyfriend wants to buy the shy and soft-spoken 19-year-old a computer so they can e-mail erotic messages to one another. The boyfriend has also offered to pay for Harry's college tuition; if Harry still didn't live at home, rent would probably be provided, too. So far, though, Harry has refused any extravagant gifts.
"I'm afraid to take it. I don't want to owe him or be obligated to do anything I might not want to do," he says. "I should like a guy for his personality, not his checkbook. But everybody says I'm weird for saying that. Even my sister says take the computer, so she can use it."
Jay doesn't understand his friend's logic. Harry fits the twink mold: a young, good-looking guy who dates older men of means. But he's not working it.
"Why go out with an old man if you're not getting any gifts?" Jay asks. "You should milk him for all he's worth and then some."
"Well, some people are gold diggers," Harry tells Jay.
"Yeah, and some people are sluts who fuck for nothing," he snaps back.
And there's the difference: Harry actually likes older men. He finds their maturity appealing when compared to his unfocused, shallow, hormone-driven peers.
"I like the security of someone older. They've learned how to settle down and know how to treat someone right," Harry says. "They know a lot more and can show me something finer than sex."
While not always physically enamored of his middle-aged boyfriend, who has graying hair, Harry finds him romantic and intellectually attractive. And they do enjoy sex. "At first I thought, 'God, he's old,' " Harry says. "But I saw he is athletic and in really good shape. He's not too wrinkled or shriveled."
The situation has been less aesthetically pleasing for Jay. In two years, he has dated 12 men between the ages of 37 and 51. One, he figures, was OK-looking. He had all his hair, didn't smell bad, and wasn't tired or weak. A nice catch. But then there were the others, including a guy he privately nicknamed "Oompa-Loompa," after the squat characters in the movie Willy Wonka and the Chocolate Factory.
"I'd be lying if I said I was attracted to the older guys I met," he admits. "It's usually based on the gifts."
And getting the gifts with a minimum of sex. Jay tries to get by while putting out as little as possible, seeing how long he can string the sugar daddy along, keeping him content with hugs, kisses, and maybe a hand job. Sometimes, though, even a kiss can be hard to stomach. Last New Year's Eve, Jay was stuck next to his 51-year-old boyfriend when midnight hit.
"We had to kiss, and his tongue was so cold and slimy; it felt like a turtle. I wanted to puke," Jay recalls. "He was such an old man. To me, 51 was like, death."
Often, the older man -- either for kicks or because he is unable to perform himself -- prefers to ser-vice his young boyfriend without reciprocation. "I think they like our youthful bodies or the noises we make," says Harry.
For Jay, though, sex with a sugar daddy is not easy to enjoy, even when he doesn't have to touch back. "It's rare I'll let them give me blow jobs, because I have to meditate and work up my will just to get hard," he says.
Jay also refuses to go all the way. He'll move on to a new sugar daddy before anal sex becomes an issue; then he can start the tease-for-gifts cycle over again.
But there are times he's been caught: Sitting on the couch with the "Oompa-Loompa" boyfriend one night, Jay was modeling the new clothes and jewelry he was wearing. Oompa just quietly stared, shaking his head. A month earlier, Jay had politely asked for $400 so he could buy some clothes and take his friends out. Now he was freely asking for money all the time, almost demanding it.
"Hope you're happy with all your stuff," Oompa said with a hint of sarcasm.
"Yeah, thanks," Jay replied.
"Well, I'm a little disappointed," Oompa continued. "I'm not getting anything from you."
He was talking about sex, and Jay knew it was time to either put out or move on.
"He figured out I was with him only for the money; that I was a gold digger," Jay says. "Probably for a time I was. No, I always was. I can see no other reason for being with him."
While Jay holds out on sex with his older boyfriends, the raging hormones of this 18-year-old do not go unsatisfied. Jay quenches his sex drive by secretly sleeping with friends who are his own age and -- for a few hot moments -- can offer a gift better than money.
Logg says he has had no problem letting his young boyfriends have sex with younger guys -- as long as Logg is guaranteed a piece of the action. At 70, Logg boasts an active, Viagra-free sex life, and is not scared to tumble into bed with a man 50 years his junior. "I'd love to go like Rockefeller did, and die in the saddle," he says.
Logg won't tolerate a trophy boy who refuses sex. "I'm not going to have a line of boys out my front door waiting for a handout," he says. "I'd feel taken advantage of."
For Jay, though, getting a free ride is what being a trophy boy is all about. He admits initiating dates simply because there was something expensive he wanted that he didn't feel like buying.
"It's hard not to want to go for it, when there are men out there willing to pay," Jay says. "That's when the greed steps in."
Different as their approaches to gift-taking may be, neither Harry nor Jay will allow a sugar daddy to pay the rent. Their refusals to be kept relate to the power lines in trophy-boy relationships -- who has the upper hand. The trophy-boy game can be dangerous, and savvy ones like Jay know there are plenty of ways to get burned.
"These are experienced, older men who are not stupid," he says. "If you get into this thinking it's all fun and games, you can get tossed around. There are consequences."
Especially if the twink finds himself emotionally or financially dependent on the sugar daddy. The older men are often eager to provide for their trophy boys, doling out not just money, but advice and support, saying they like to take care of their boyfriends. Harry warns of hidden agendas.
"It's a nice gesture, but sometimes I wonder if it's not so much about being nice as it is controlling you," he says. "Their offers are tempting, but I keep myself in check. I'm too smart to get caught in a trap like that."
Logg, who has played sugar daddy to four young men, concedes there is more to his attraction to young men than nubile bodies. He prefers that his trophy boys not have good jobs or drive nice cars. And they must have needs that go beyond gifts and spending cash.
"I want them to be dependent on me. I want to take care of them. I like to be in control," Logg says, arguing that many young men -- who come from split families and want father figures -- are searching for what he offers. "Maybe they'd like a little discipline. They'll get it -- and a lot of affection, too."
Jay says the control sugar daddies exert is most evident at the social hours when the twinks are gathered together, unwittingly mirroring their boyfriends' mannerisms, speech, and thought processes. The twinks joke about it, exchanging "you're acting just like your father" teases. But Jay says there is nothing humorous about losing one's own identity.
"Your sugar daddy's characteristics will rub off on you if you're not careful," he says. "Unless you are resistant, they will mold you into what they want. If you're a weak kid and not strong-willed, it's real easy to fall down."
The power dynamics of May/December gay relationships are grounded in one inescapable fact: Trophy boys grow up. They know they won't always be 19, and they know sugar daddies won't give a guy -- no matter how good-looking -- a second glance if he's over 25.
While 25 may still seem like a ripe age for a straight trophy wife, society's obsession with age and beauty is intensified in the gay world. From fighting negative feminine stereotypes to buying the argument that being gay is only about sex, there are any number of explanations for what drives some gay men to become gym fanatics and believe that youth and good looks are their only assets.
"We'd like to think it's forever, but there is an age limit. We can be replaced," Jay says. "As soon as you turn 21, you're pushing it. You are used, expired, and old. You're not fresh meat anymore, and you're about to lose it all: upper hand, the gifts, everything."
But twinks are hardly powerless. In addition to withholding sex and refusing to be completely kept, twinks can assert themselves in a relationship by altering how they behave in public. Jay says he lets his sugar daddies know he has no qualms about being "disobedient" or rude in front of their friends. The fear of embarrassment can go a long way in negotiating the sexual balance of power in a sugar daddy-twink relationship. From simple mouthing off to a full-blown temper tantrum, the twink can quickly torpedo his sugar daddy's image.
"If the old guy's friends know he's bought some punk kid, he will be looked at as a sucker," Jay says.
More times than not, it's the trophy boy who becomes the sucker. Used up and thrown out in their mid-20s, many of them never learn how to survive financially -- or emotionally -- on their own. Bartender Krumtum sees it all too often with each successive batch of trophy boys to come through the door of the Alta Plaza. Krumtum will watch one get picked up for a couple of years. But before long, the same kid ends up sitting at the bar alone, passed up for the newer models. He's hoping for another run, but is too old.
"Those are the stupid ones," Jay says. "They make it their life without thinking of the consequences."
Jay doesn't apologize for being a trophy boy. Given the chance, he'll defend his propensities, or at least point out that the same process unfolds in the straight world all the time: Consider Donald Trump or Anna Nicole Smith. Jay realizes straight society views its trophy relationships with raised eyebrows and that gays find it unacceptable in their community, too. What upsets him most, however, is the double standard: The gay version is somehow deemed more sordid.
Jay notices how people in straight restaurants react when they see him with an older man.
"They give us looks of disgust, as if by seeing us, they can say gay people are even dirtier than they already thought we were," Jay says. "Yeah, they called Anna Nicole Smith a tramp, but they didn't hate her. But if you reversed it, and she was Leonardo DiCaprio, they'd say, 'Look at that deviant of society; that gold-digging fag.' "
Child molestation, however, is one deviance -- gay or straight -- that is hard to defend. Jay went out with his first boyfriend, a 40-year-old man, when he was 16. He dated a dozen middle-aged men when he was between the ages of 16 and 18. Some of the twinks attending social hours in sugar-daddy homes are still in high school. While sexual contact between the men and teen-age boys might be considered illegal, Jay doesn't see it that way.
"At 16, you're not oblivious to what's happening. The twinks all want it," he says, emphasizing that he attended the parties, flirted, and dated on his own accord. "It's not like the men are roaming the park saying, 'Touch my penis, little boy.' "
Logg, whose youngest trophy boy was 19, says the sugar daddies who dabble in the high school set are asking for trouble. "I do find the older I get, the younger I like them -- but not 16; that's too young," Logg says. "It's probably illegal. But I wouldn't want them regardless. I like fully developed men, not boys."
aving sent his young boyfriend home -- they spent the day gardening together -- Logg sits in his back parlor, surrounded by a gaudy mix of European art, furniture, and red shag carpet. The "Italian madness" decor, as Logg calls it, reminds him of the decorator -- his partner of 34 years, who died in 1992 at the age of 62.
It wasn't until a few years after Albert died, after the depression and the spontaneous outbursts of tears subsided, that Logg thought of dating again. But it wouldn't be the same as when he met and fell in love with Albert, when both were in their 20s. Logg was now a senior citizen, and nothing made him realize his years more than heading back into the singles scene. His friends tried to introduce him to other gentlemen his age, but there were no sparks.
"They were nice guys, but they were old men," Logg says. "I said, 'No thanks, forget it.' I'm not going to bed with some old man."
Going out was worse. Logg's friends preferred the Twin Peaks bar, a Castro institution that is now dubbed the "crystal coffin." A giant, picture window wraps around the front of the bar; patrons look out at markedly younger passers-by on the street.
"It's a bunch of old farts sitting in the window who can't do anything but talk about their ailments, pop pills, and eat bananas," Logg says. "It pulls you down."
Wanting to reclaim his youth and able to spend plenty of money trying, Logg entered the world of trophy boys. He didn't want to rattle around in his big house alone and become an old maid. His friends thought he was crazy.
"They said the kids would either kill me in bed or rip me off," Logg says. "But I've been pretty lucky. I've never really had anyone put the hustle on me. I know a lot of them are out there just for the money, but none of my boys have asked, 'How much are you going to pay me?'
"Which is nice."
Of course, when his trophy boys are attentive, Logg is generous. He has no family to share his wealth and, at his age, feels it's just going to waste sitting in the bank. He figures he might as well find something worthwhile -- and fun -- to spend it on.
"If you got the money, and it makes the kids happy, and they're pleasing you, why not?" Logg reasons. "I like to see a kid in a nice jacket, and if I feel they are deserving, I'll pay their rent and help them through school, too. Being with me sure beats having to work at Taco Bell for $4 an hour."
Logg's 23-year-old boyfriend declined to be interviewed. Logg says he is shy and leery of the shame others might project on him for being kept. At the same time, Logg contends the young man is not embarrassed by a relationship with a 70-year-old.
"I feel the affection from him, and that he really wants to be with me," Logg says. "We'll be walking alone in a straight neighborhood, and he'll still want to put his arm around me. It must be a Beauty and the Beast thing."
Actually, with his piercing blue eyes and full head of strawberry blond hair, Logg does not look, or act, anything like his age. He is passionate about yoga and can do seven-minute handstands. He wears tennis shoes and power walks with quick strides. His conversation is animated, propelled by bursts of energy.
Logg says his boyfriend enjoys hearing about his life's adventures and experiences, and has even asked to record them. It's enough to make Logg believe there is something more meaningful about the relationship than sex for him and money for the kid.
"There's been a void since Albert died, and now I have someone to care for," Logg says. "And you'd be surprised how many young kids are attracted to older men, whether they have money or not, simply because they want a father figure. They feel they can benefit from what we've been through."
There is, indeed, a generational cycle affecting trophy boys and their sugar daddies.
Almost 50 years ago, when Logg was in his 20s, an older man took an interest in him. The well-established San Francisco lawyer, then 60 years old, was closeted, but still wined and dined his young protege, giving him gifts and teaching him about sex. Logg was impressed by the man's knowledge and travels, and found his stories about business and insider politics fascinating.
"I just want my boys to experience what I had," Logg says. "And while they can't give back now, maybe they'll take a hint at what I'm trying to accomplish."
Jay, the trophy boy, knows exactly what Logg means.
"They lavish you with gifts and mold you until you reach a certain age, and then they let you out in the world," Jay says, matter-of-factly. But hearing this quick synopsis from his own lips makes him pause. He begins to reflect on what he's just said, almost with apprehension.
"Someday," he says finally, a hint of disconcerted wonder in his voice, "you become what they are.