Confessions of a Boob Fluffer

I’m a sucker for bad drag. I don’t know why or what it is about bad drag but, damn, I love it. Good drag is nice (there’s that polite Midwest word for things we just don’t get) but since I long ago moved away from the Midwest (and moved back again) my appreciation for bad drag has blossomed. Movies are filled with wonderfully bad drag like Cillian Murphy in Breakfast on Pluto (so adorable!), Ed Wood (Johnny Depp in luscious sweater girl drag), Gael Garcia Bernal in Bad Education (so cute!) and When Night Falls (Johnny Depp (again!) fabulous as Bon Bon!) but not: Martin Lawrence in Big Momma (just plain bad), Dustin Hoffman in Tootsie (too frumpy) and Jack Lemmon in Some Like It Hot (Marilyn, hot, Jack, not). So when a guy comes into the store and wants some help dressing in drag I leap at the opportunity. That’s when Dean entered my life.

Dean was a student at the university and a photographer. We initially met when I hired him to photograph a fundraising calendar for the local rape crisis center. He came by the store with his portfolio hoping that I would hire him. He’d been highly recommended by friends. He was (still is) a talented photographer and I hired him immediately to shoot the calendar photos. While I was thrilled to find a photographer, I think he was thrilled to find lingerie. He wandered the store touching everything and asking lots of questions. When he left he had a glazed look about him from an overload of frilly girlie things.

A week or so later Dean visited the store to shop for his girlfriend. He wasn’t sure what he wanted to buy her so I gave him the grand tour again. I showed him everything from teddies, body stockings and chemises to g-strings, garter belts and bustiers. I even showed him some thongs for him in case he was interested. I asked lots of questions so I could help him find just the right piece of lingerie for his girlfriend. He finally settled on a white stretch lace garter belt with matching panties and white lace top fishnet stockings. As a little bonus I gift wrapped it so he could surprise her.

About a month later the store was busy selling pushup bra pads, opera length gloves and feather boas for the huge drag ball coming up that weekend. It was a nice little bump in weekday business in addition to our usual Sunday drag queen business. Everyone was busy with preparations for the big event. It was one of the best parties in town all year and every one dressed in some variation of drag, even the straight guys.

Denise and I were busy planning our own outfits for the party. We visited thrift stores and vintage shops trying on tons of old fifties date dresses. After mountains of tulle, yards of ruffles and enough sequins and bruised velvet flowers to make any crafty grandma swoon, we settled on vintage men’s tuxes. After some minor alterations by our handy seamstress friend Susie, our tuxes were ready. Since the unspoken theme was “anything over the top” we knew our tuxes would be too plain. After much discussion, over cocktails of course, we decided on a sort of reverse drag queen. We would wear little red dominatrix bob style wigs borrowed from the store mannequins and lots of drag queen style makeup. Since we wanted to “pass” as guys (in drag makeup) we were going to wrap our boobs in ace bandages, wear men’s shoes and white gloves to hide our smaller-than-a-man’s hands. The only thing missing was a prominent adams apple.

We were so excited about our unique look for the ball. But we kept it a secret from our friends whom we hoped wouldn’t recognize us, at least not right away. As the day of the drag ball grew closer some of our male friends came to us for help with their own outfits.

Curtis was one of those friends. He was over six feet tall, thin, with da Vinci’s Vitruvian Man tattooed on his back. He wanted us to help him dress in drag because he “wanted to get in touch with his feminine side”. Curtis was a talented artist whom we thought was already “in touch with his feminine side”. After asking him a few gazillion questions, we took him to a vintage store to shop for a dress.

Finding a dress to fit a tall skinny guy wasn’t easy. That he thought he had some say in what he wore complicated things. For some inexplicable reason, he wanted a strapless dress. After much trial and error, he insisted on trying on a strapless acid green tulle confection that couldn’t have looked good on the original wearer let alone a potential 6’ 3” drag queen.

I looked at him hard and said “what do you think you are going to hold up that dress with? You have NO BOOBS! And you have some chest hair, there” (I yanked it) “that has to go if you plan to look good let alone pass as a woman which is the whole point of dressing in drag”.

He gave me an exasperated look and said “I’m not shaving my chest and I’m not trying to pass. I just thought I would wear a dress and some makeup, maybe a little lingerie underneath. You know, “get in touch with my feminine side”. I thought you would understand”.

I gave him the squinty eye and said “In case you haven’t noticed, I am female there fore already “in touch with my feminine side” and have never felt the urge to “get in touch with my masculine side” so there is no possible way I could understand what it is you are talking about, you asshole, and if you want to wear that 50’s frou-frou nightmare of a prom dress with your chest hair hanging out that’s fine with me even though you would look so much better in one of these groovy 60’s mini sheath dresses, so, let’s just get that Baby Jane nightmare of a dress and go”. I came up for air, grabbed the putrid green dress and went off to find the cashier.

We went back to Scarlett’s with the tacky 50’s prom dress in tow. For some strange reason, oh yeah, duh, he wanted to “get in touch with his feminine side”, Curtis wanted to wear a corset underneath with stockings. It was hard for me to not laugh when he said this. Corsets are made for curves and Curtis’s body was the antithesis of that. But professionalism, for once, took over.

“Yeah, sure, we can get you in a corset”. I turned my back, rolled my eyes at Denise and snickered a bit at the thought of getting him in a corset.

Thankfully, she jumped in. “Curtis, come on over here and let’s look at what’s available. Now, this would be a good choice for you as it has small cups and you have nothing to put in them” she said after quickly perusing the corsets.

“Yeah, but I want something in red. Maybe in lace” he answered.

“Well, you’re not going to get one to fit you” she answered firmly. “It’s this black lace one or nothing. Here let’s get you in a fitting room and see if this works” she said as she dragged Curtis into a fitting room with the black lace corset. “Let me know when you need some help”.

She came out of the fitting room with a big grin on her face. “This should be interesting”.

After a few minutes of letting Curtis struggle with the corset himself, Denise went to check on him. “How are you doing in there?” she asked.

“I think I need some help. How the hell do you put this on?” he asked.

“I’m coming in” she said parting the curtains.

“Quit fidgeting” I heard come from the fitting room. “I’ll hook up the back if you just stand still”.

After a few minutes, Denise asked me to bring her several sets of pushup pads. “Big ones, little ones, I need them all”.

I handed her the pads through the curtain and waited. After a few minutes, she said “Well I think this is as good as it gets. Come have a look” she said to me.

I caught a glimpse of Curtis wearing the black lace corset, the cups stuffed with pads giving him the disconcerting illusion of mini boobs with hair sprouting from them. “That’s a good look with those boxers” I said leaving the fitting room so I could laugh in private.

Denise yelled out to me “bring me the prom dress from hell”.

I handed her the ugly prom dress through the curtain and waited to see the results.

After a few minutes she came out and said “go in and you tell me what you think”. I darted through the doorway and parted the curtains not sure what to expect. There stood Curtis in his baby puke green prom dress with little fake fiberfill boobs filling out the front and a big full tulle skirt hiding his lack of hips. All he needed was a wrist corsage.

“You look so beautiful. Will you be my date?” I asked. “I’ll expect you to put out at the end of the night.”

“Fuck off, I still need some stockings”. He said, ever the gentleman.

“I’m not sure we have any that look good with boxer shorts” I said.

“I’m not wearing the boxer shorts with this. I’m wearing these” he said holding up a pair of black lace bikini panties.

“Uh, okayyyyyy” I said. “The only ones we have in talls are seamed, but the fishnets might stretch enough”.

“Oh yeah, I want fishnets” he answered.

“I don’t think fishnets would be the best choice for this dress (like there was a best choice to go with slime green). I would go with the seamed”.

“I don’t want any runs in my stocking and there is no way I can put on stockings without getting runs” he answered a tad too prissily. “Give me the fishnets”.

“Ok, I think we can work with the fishnets. We have some beige colored ones that could work with this dress. You try, you buy though” I said tossing him the package.

“Yeah, sure, add them to my bill.” I left the fitting room.

“He’s all yours again” I said to Denise “you can do his stockings”. It was getting too hard for me to keep a straight face while helping him.

After a few minutes, Denise came out of the fitting room and said “he wants you to see how he looks”. She covered her mouth with her hand hiding a huge smile.

I entered the fitting room to see Curtis wearing his mucus green prom dress with the beige fishnets and no shoes, “We need to find you some high heels” I said.

“I thing I’m just going to wear my Doc Martins” he answered.

“Well, that really won’t go with this dress (like anything would go with that dress). But it would be hard to find you shoes to fit on such short notice” I said glancing at his large fishnet covered feet.

“I don’t think I could walk in heels if I did find some”.

“Doc Martin’s it is” I said leaving the fitting room “Oh, do you need some help getting out of that?”

“Uh, yeah”

“All yours, Denise” I said to her. She went back to the fitting room to help him get out of his (hideous) dress and (lovely, though weird on him) corset.

A few minutes later they came to the register. “How about some gloves to wear with your dress? Not that we have anything to match that particular shade of fungus green. Maybe some condoms in case you get lucky?”

It was his turn to roll his eyes. “I’m going to need help getting dressed” he said. “And I want someone to do my makeup. And I need a wig” he said glancing around at our mannequins. “That blond wig looks good” he said pointing to a mannequin in the window wearing a huge curly blond wig.

“Yeah, sure, I’ll pull it off the mannequin the day of the drag ball” I said. “Why don’t you swing by the house in the afternoon and we can help you get dressed and fix your makeup”.

“It’s a date!” he said leaving the store with his purchases.

“Hey! Don’t forget your boobs” I yelled after him tossing him the bag with all the bra pads in it.

As the week progressed, several of our guy friends came by looking for help with their outfits for the drag ball. Fortunately, they were not looking for the amount of help that Curtis needed. Mostly they wanted ideas for dresses and where to buy them. A few asked if we could help them with their makeup. Before long we had four guys lined up to have their faces painted in varying amounts of drag queen style makeup.

The day of the ball, Dean came by the store looking for some help. He was very vague about what kind of help he needed. After evading most of our questions we agreed that he could come by our house to help him get dressed. Oh, and could he come by at a time when no one else would be there? And could he borrow a wig? A blond wig? (what was it about the blond wigs?)

The day of the ball we closed the store a little early so we could get home to help our guy friends get dressed and made up. A steady stream of guys came by our house including a few friends of friends who needed last minute help. After helping Curtis with his black lace corset, fake boobies, fishnet stockings and pond scum green dress, we shellacked his face in a thick layer of drag queen style makeup. No amount of makeup was going to minimize his prominent adams apple or cover his chest hair which sprouted out of the top of his mildew green dress. I gave his fake boobs a squeeze.

“I feel violated” he said.

“Get used ot it” I said. “I’m sure I’m the first of a long line of boob squeezers you will meet tonight”.

Shortly after Curtis left, Dean showed up carrying a bag with his outfit. He seemed much more nervous than our previous “clients” so I offered him a drink to loosen him up. After he inhaled his drink he pulled a nurses uniform out of the bag along with the same white stretch lace garter belt, matching bikini panty’s and lace top fishnet stockings I sold him for his girlfriend.

“Wow, this stuff looks familiar” I said holding up the garter belt, bikinis and stockings.

“Uh, yeah, I bought it for my girlfriend but she didn’t like it so I thought I would wear it tonight with this nurses dress. I also bought a bra to go with it but not from your store. Sorry” he said holding up one of those serious looking, all business, full coverage, industrial strength bras.

“That’s ok” I said. “It’s getting late so let’s get you dressed”.

Denise and I helped him put on the bra stuffing it with the white tube socks he brought with him. We excused our selves to the kitchen to fortify ourselves with another drink while he put on the white satin and lace bikini panty’s. When we returned he had them on and it was readily apparent that they were not providing sufficient coverage. Of course, it was the first thing we checked upon returning with our drinks. I winked at Denise and we each took a sip of our cocktails, smiling behind our glasses. Meanwhile Dean had the garter belt on and was attempting to put on the fishnet stockings. I had to admit he was doing an admirable job of it. We helped him clip the stockings in place even though he looked like he knew what he was doing.

I picked up the nurses dress to help him put it on. This was no typical nurses uniform, this was a naughty nurse uniform. It fit Dean snugly with a low cut bodice and a very short hemline showing off the stockings and garters but fortunately, not showing off the miniscule bikini panty’s. At least not until he bent over to put on his naughty nurse white high heels. Where did he find heels in his size, I wondered? Apparently Dean was a resourceful fellow. And a bit of an enigma. Together Denise and I applied his makeup and slipped a long straight blond wig on his head.

“You’re all set there Nurse Betty” I said. “We need to get ready ourselves so we’ll see you there”.

Dean left and Denise and I hurriedly put on our men’s tuxes, red dominatrix wigs and helped each other apply drag queen style makeup. Realizing we’d forgotten to tape our boobs down with ace bandages we undressed, taped, then redressed in our tuxes. The ace bandages were important as we were trying to pass as guys. Makeup applied and wigs on we left for the ball. I’d even found a top hat and a cane to add to the overall effect.

We got to the ball and made our way to the bar. A friend of ours was bartending and I turned to Denise and said “Don’t say one word to anybody. Don’t even smile. We don’t want any one to recognize us just yet”. I nodded to our bartender friend and pointed to the beer that someone was drinking and then pointed to the two of us so he would bring us two beers. The noise around the bar was almost deafening so I guess he didn’t think it was unusual that we didn’t speak. I was thrilled that we hadn’t been outted yet.

Drinks in hand, we slowly walked around checking out all the fun costumes. I was flattered when a few of the drag queens pinched us on the ass. A secret thrill passed through me. we were passing as guys in drag! A few stopped to try and engage us in conversation but we just smiled, waved and moved on.

Not only was the place filled with great drag but there were loads of cute straight guys in very bad drag too. So Denise and I started pinching their asses as they walked by. When they turned around giving us that homophobic glare thinking we were gay men pinching their ass, we would just smile and wave. It wasn’t until some guy threatened to kick my ass that we stopped pinching them. It was definitely time to move on and find our friends.

Spotting the table where our friends were gathered, we moved over to stand near them. We had to turn our heads and giggle when our friend Rob commented that he couldn’t believe we weren’t there yet and the drag show was about to start. Oh, and did I mention that Rob looked fabulous in his long gown, tiara and well-groomed goatee?

We eavesdropped a little more on them when we heard Rob’s partner, Bill say to him “Hey who are those two cute queens in the tuxes? Do you think I should try to pick them up to party with us later?”

Knowing Bill was always bringing home some cute playmate for Rob and him to “party with”, Denise and I busted out laughing. All of our friends heard and turned to stare at us. The jig was up. Our friends went crazy about our costumes and I told Bill that as long as I got to wear the strap-on, I would go home with them.

The drag ball was a blast and we loved all the costumes. Even our friend Curtis was having a good time and, despite the fact that he was straight, had collected several phone numbers from drag queens. All part of his campaign to “get in touch with his feminine side”. We even saw Naughty Nurse Dean who looked like he was having a good time using a stethoscope on anyone who would let him.

A few days later Dean came into the store to return the wig he had borrowed. He thanked us for all our help and said he too had a great time. Oh and could he buy a black lace garter belt, bikini panty’s and black fishnet stockings like the set in white he already owned. I didn’t ask any questions and found him just what he needed. He left the store smiling, bag of lingerie in hand. I didn’t know if he gave it to his girlfriend or what he did with the lingerie he bought that day.

I saw Dean a few times after that when he photographed the images for the fund raising calendar I had originally hired him to do. We didn’t talk much and he was very professional to work with. The photos were outstanding. A few years later I was living in New York and saw an announcement in the Village Voice for a photography show for a guy with, coincidentally, Deans name. Could it be the same person, I thought? Of course, I had to go.

I waited until a few days after the opening so I could slip in surreptitiously. There on the walls were huge images of Dean alternately wearing the white or black garter belt, bikini panty’s and matching fishnet stockings. I guess that answered what he did with the lingerie he bought from my store. Oh, and the images? Spectacular!