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We were curious about the backstage antics at Brooklyn’s annual small-penis pageant, and so we turned to two-time contestant Rip van Dinkle (above, at the 2015 contest) for some answers to our questions – and we had quite a few of them. Who, for example, is allowed in the contestants’ dressing room? Do participants suffer from pre-pageant jitters, or from the sudden realization that one’s penis will soon be on display for hundreds of boisterous women? Does Rip have bedroom fantasies about the women who saw (and judged) him in his birthday suit?
Grouchy Editor – Tell us about the scene in your dressing area before the pageants. Are women allowed in there?
Rip Van Dinkle – Oh, man, aside from the contestants, it’s all women backstage. Some of them are supposed to be there, like the pageant organizers and media people who are there for interviews. But there are some people who just wander in, with no real reason for being there except, I suppose, to ogle us. But there were also a few naked women backstage. In the first pageant, “Cherry Pitz” [Editor’s note: burlesque queen Cyndi Freeman] was in the show, and she stripped down to a black thong – and nothing up top – right in front of me. I believe she was 49 at the time, and married, and looking hot. There was also a female musician parading around topless during the pageant this year.
GE – Tell us about the media. It reminds us of female reporters in the men’s locker room at professional sporting events, which was quite controversial.
RVD – They say you have to be brassy to be a good reporter, and that was certainly true of the ballsy bunch I saw in the dressing area. A reporter from Gawker [Editor’s note: Victor Jeffreys II], one of the few male reporters, drew me aside to ask questions. At some point, I glanced down and saw that he was holding his cell-phone camera in front of my groin; he’d been taking close-up pictures during the interview. That kind of pissed me off, but he certainly got what he wanted. I checked out his story in Gawker and there were all these shots of my junk in huge close-up, including shots he took later when the judges were measuring our cocks on stage.
Gawker published these intimate pictures of Rip submitting to penis-measurements by judges Cyndi Freeman, left, and Aimee Arciuolo, center. At right, one of Jeffreys’ surreptitious crotch shots.
A female photographer at the first pageant spotted me sitting alone, drinking a Coke, and asked if she could take pictures. I said sure and brushed my hair a bit, but that was unnecessary because she wasn’t interested in my hair. She just kind of leaned over and stuck her camera between my thighs and began taking pictures. I should mention that I wasn’t completely naked; I was wearing one of those tuxedo thongs. But she and the Gawker guy were there to get pictures of our genitals and by God that’s what they got.
GE – You mentioned the foreign press …
RVD – Oh yes. There was this gorgeous reporter from Brazil, Anna something [Editor’s note: Anna Gabriela Ribeiro], and she came up to ask me questions. One thing almost every interviewer asks me is, “How small is your penis?” She didn’t ask me that, which I thought was kind of odd until I realized what I was wearing. We didn’t have mirrors to look at ourselves backstage, and this was our first costume, which I thought covered us up. I was wrong. It was black underwear but with a see-thru patch right over the genitals, so this girl had a clear view of my twig and berries, dangling just inches below her notepad. She would have no trouble describing my shortcomings for her readers. It might also have explained the smile on her face while she was interviewing me. She also took pictures during the show. Several of them popped up on Spanish-language Web sites.
Ribeiro and her view while interviewing Rip
GE – OK, enough about journalists. Who else was in the dressing room?
RVD – At both pageants, Aimee Arciuolo was there helping us adjust our costumes. She was the creator of the pageant and had a hand in designing the costumes. She wanted us as exposed as possible, and told me before the first pageant that our underwear would be as transparent as plastic wrap. For the 2015 pageant, Bobbie Chaset pretty much took over managing duties, so she was always around. Legally, we weren’t supposed to get completely naked during the show, but I discussed flashing the audience with Bobbie beforehand and she encouraged me to do it. So I did.
GE – Anyone else backstage?
RVD – There were the “penis kittens,” of course. They had various duties, but mostly they just had to look cute. Some of them, I think, used Super Soakers to wet our crotches before the penis measuring.
“Penis Kittens” from left to right: Racheal, Audrey, Amanda
GE – We should come clean here. We really aren’t interested in hearing any more about your experiences at the pageant. What we really wanted to do was find an excuse to run pictures of some of the good-looking women associated with the contest. We wanted to turn the tables on some of the females who ogled you guys. We’d love your comments on these pictures.
RVD – Excellent. Let’s do it.
GE – We’d also like you to give us a favorite sex fantasy about each of them.
RVD – That sounds sexist. Count me in.
“Rip van Dinkle flew in from Minnesota to shake his shrimpy spigot before 100 onlookers.” – Erin Calabrese and Kate Briquelet, New York Post
The Leering Ladies
Pageant creator/manager/judge Aimee Arciuolo
RVD – Aimee has a great rack and nice legs. I guess she could relate to us guys in the pageant since she’s a bit of an exhibitionist, herself. Until I saw these pictures, I had no idea she let her tits hang out in public. Great-looking tits, blue or any other color.
Aimee told Gothamist that she and her friends discussed ways to make us get erections during the pageant, I suppose so they could measure us limp-dicked and also with boners. Aimee really wanted to give the females in the bar a good show. She was upset that a city ordinance wouldn’t let us show cock, so she and her mother designed “penis tuxedoes” so that our balls hung out for all to see.
But I was game for anything at the pageant. If Aimee had said to me, “Rip, there are women with cameras out there who want their money’s worth. Will you ejaculate on stage so they can get souvenir pictures?” I would have said to her, “Yes, ma’am. If that’s what you want, no problem.” Humiliating, I suppose, but I’m sure she would have loved that.
“If Aimee had said to me, ‘Rip, there are women with cameras out there who want their money’s worth. Will you ejaculate on stage so they can get souvenir pictures?’ I would have said to her, ‘Yes, ma’am.’”
Rip: “For a woman who claims to favor small dicks, Aimee looks pretty pleased to see Flo Rida’s big pecker.”
RVD – These screen caps and the video below are from the first pageant. A guy calling himself Flo Rida broke the rules and flashed his dick. I’m pretty sure this kind of rule-breaking pleased Aimee, even though she acts shocked in these pictures.
Rip’s Sex Fantasy: She’s kind of a show-off, so I’d love to do her doggie-style on stage. At a biker bar. Hey – remember, this is the girl who put me through the indignity of measuring my penis on stage in front of a bar full of women. With cameras.
In the video above, Cyndi (big wig) and Aimee measure little manhoods on stage. Rip is the contestant in the middle.
Bartender/manager Bobbie Chaset
Rip is interviewed by Rolling Stone while Bobbie Chaset, right, looks on
RVD – These pictures surprise me. They must be some years old. I thought Bobbie was too reserved to dress in such a sexy costume and in such “fuck me” poses. Also, are those panties see-thru? Looks to me like some pussy hair poking through, but that could be my wishful thinking.
Rip’s Sex Fantasy: Those pictures remind me of bondage. It would be fun to tie her up, put a gag in her mouth, and do her on stage. At a biker bar.
Journalist Anna Gabriela Ribeiro
RVD – After she interviewed me, she took a bunch of pictures during the contest. They were published on South American Web sites, but I noticed my crotch was “black barred” in them.
Rip’s Sex Fantasy: Probably we’d do a scene for a Brazilian porno flick. Does Brazil have porno flicks?
“Penis Kittens” Amanda Hollenbeck, Audrey Selles-Czuk, Racheal Selles-Czuk
Left to right: Racheal Selles-Czuk, Amanda Hollenbeck, Audrey Selles-Czuk
RVD – Honestly, I’m not sure what they did. I believe they were supposed to hose our crotches with Super Soakers, but it was too chaotic to notice who was squirting what. Cute girls, though. Look at Amanda – doesn’t she look like some glamorous 1940s film star?
Rip’s Sex Fantasy: Racheal and Audrey are sisters, so of course we’d have a threesome. Amanda has kind of that classic, movie-star look, so I’d do her classic missionary-style. At a biker bar.
Burlesque queen Cyndi Freeman
RVD – Looks pretty good for 50, doesn’t she? I guess she has a very understanding husband, since she spends so much time parading around half-naked in front of other men. She struck me as one horny lady. During the second pageant, which I did not attend, she basically dry humped a contestant who, from the look of the pictures, was wearing only a shirt – no underwear. In other words, Cyndi in her thong grinding pussy against his genitals. [Editor’s note: See GIF at bottom] She also seems to enjoy eyeballing Flo Rida’s big prick in the pictures [above and below]. And she was one of the judges who measured my manhood on stage.
Rip’s Sex Fantasy: I think she’s kinky, so I’d have her down on her knees, giving me head while her husband watches. By the way, Cyndi once did a soft-core TV show for Showtime. It has Cyndi tits, Cyndi ass, Cyndi getting fucked by a sleazy dude – check it out.
Gawker reporter Victor Jeffreys II
RVD – Annoying dude, but he was there for dick pics and he got them – especially mine. [Editor’s note: That’s Jeffreys below the yellow arrow in the picture, watching Dinkle get measured.]
Rip’s Sex Fantasy: Go fuck yourself. Although there is a scene in Deliverance that comes to mind.
Left to right, judges Natalie Shure, Krystyna Hutchinson
RVD – The brunette, Krystyna Hutchinson, was super hot. The one in the glasses looks hot in her picture, but what you can’t tell from it is that she is a very big girl. Big everywhere. Not my cup of tea.
Rip’s Sex Fantasy: Krystyna, anal sex. Natalie, boob sex.
The 2015 judges were unimpressed by Rip’s puny pecker, pictured above. After finishing in second place at the 2013 pageant, Rip and his (normally) 1.75-inch penis experienced shrinkage, demoted to fourth place by Shure and Hutchinson.
Gothamist photographer Melanie Rieders
Rieders enjoys hanging with big dicks (far right) as well as wee ones
RVD – This girl Melanie probably captured the most explicit shot of my wiener (below). I was surprised to see it posted on Gothamist, which is a fairly mainstream Web site, because her photo doesn’t leave anything to the imagination. From the stage, I didn’t notice her, but she must have been in the front row and prepared for my flash, because I didn’t have my bathrobe open for more than a few seconds.
Photo by Melanie Rieders
Rieders in the crowd, moments after capturing a shot of Rip’s dick
Rip’s Sex Fantasy: I looked her up on the Web and discovered a bikini shot of her (below). My God, does she have a humpable, pumpable little ass, or what? I’m thinking I’d do her doggie-style, right there on that raft. Guys like me aren’t built for big-bottomed girls, because we have to make it past all that butt cheek, but Melanie’s perky bubble butt? I’m thinking I could squeeze into that.
Cyndi Freeman, aka Cherry Pitz, dry humps a bare-bottomed contestant
To read more about Rip’s adventures at the Smallest Penis in Brooklyn pageant, click here or here.
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