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Women don’t really dress for men; we dress for other women. We choose “statement jewelry”, avoid over-matching and follow seasonal clothing rules, all for other women. A man doesn’t reject a woman for wearing white after Labor Day. It doesn’t even occur to him. But women, women will call the fashion police with their eyes. Those bitches.

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I met Pam at book club. She’s the girl next door, if the girl next door looks like Sheryl Crow and is effortlessly put together, humble and warm. Before the end of a night discussing Tina Fey’s Bossy Pants, she told us about a party she would be having called Estrogenfest. Women only. Hanging out. Mixing circles. She would ask all guests to wear comfy clothes, or what she called “birth control outfits”. An outfit you would wear at home, alone, maybe when you’re sick. The outfit that no man would be attracted to you in. There would be prizes.

I RSVPed yes immediately and actually had to choose between several outfits. I decided on light blue pajama pants covered in smiling yellow suns, white clouds and the word “sunshine” sprinkled all over. And for the top I wore a near-matching, hand-me-down, yellow cotton shirt with light blue three-quarter sleeves that had illustrations of famous dogs, Snoopy and Lassie on the chest.

I looked like a 9-year old ready for a slumber party. I put on yellow Snoopy socks to add to the “sunsemble”. The only thing missing from what felt like a memory of my youth was my braces and headgear.

My friend Jill offered to pick me up, which was ideal because then I could drink. But she asked me to wait for her at the Citibank parking lot across the street from my house because she was picking up Denise first and it was an easier route to Roscoe Village that way. My winter coat covered up Snoopy but the suns peeked out from under it. I walked across Ashland and waited with a large chocolate cake. I was in public. In these pants!

As I waited, a couple passed me. The man chuckled as he walked by, muttering, “Well those look comfortable”. Ugh. The bright yellow suns continued to smile. Stupid suns! Don’t you realize they’re laughing at YOU?

The cake just amplified the desperation of this outfit. When Jill pulled up with Denise, I was relieved. But as we were looking for parking near Pam’s, she backed up onto a one-way street, the wrong way. I let her know, in case she hadn’t noticed the sign. “Jill, I can’t die in these pants.”

We found a spot just half a block away. I would be safe inside soon. Or so I thought.

We walked through the living room of Pam’s appropriately-lovely single family home, toward the kitchen, the center of the chatter. It was a sea of black yoga pants. What’s going on here? I would sleep with any of those women! Those bitches. What about the embarrassment we’re supposed to feel TOGETHER. A guest walked past me, looked down and said, “Oh you’re definitely gonna win”.

We walked into the kitchen and I felt all the eyes on us. It was like a Halloween party, the kind where you’re the only one wearing a costume. We found Pam and she was overjoyed to see us, giving us the lowdown on who everyone was- coworkers, neighbors and women from another book club. Pam would later surprise everyone in a gorilla suit. PAM knows how to commit.

But right now, I felt so exposed. My worst was way worse than anyone else’s. Normally, I would have worn cute jeans and a sweater. A necklace thoughtfully purchased at an art fair. My hair tamed into a wave from its usual curly friz. But birth control was about friz. And no make up. I felt like a troll. Like the embodiment of PMS. I found comfort in a pan of cocktail weenies. I stood there, eating and contemplating the evening. Seeing my ruin from across the room, Jill and Denise rescued me from my hot dog binge and we went into the dining room to look at the jewelry that one of the women was selling as a side-show for the night.

“How much is this piece?” I asked looking at a silver chain with charms.
“Let me double check”, she said, picking up her price book. Then she looked down at my pants, “Oh! You’re so…frumpy!”

Was this a test? No one knew what to say to each other. I was hesitant to go up to some of the women and discuss their bad clothing choices because I wasn’t sure if they had deliberately made them. It would be like asking a woman about her pregnancy only to find out she’s not expecting. So I went back to the kitchen. And I ate more hot dogs.

This party had the best intention of breaking down walls giving us the ability to laugh at ourselves and each other. IF everyone played along. Which they didn’t. Those bitches. Some women were going out after, so OF COURSE THEY couldn’t wear something ugly. Our friend Sheri could have had this excuse- she had just come from work. But she stepped it up and brought something to change into. Something awful. A DARE shirt and striped pajama pants that only came down mid calf, exposing a layer of long underwear. She looked homeless. I immediately loved her even more.

Some women just ignored the birth control theme and wore cute dresses or jeans. One woman in particular was actually wearing a cute dress over jeans. Jill and Denise were having a deep conversation about being short and busty and how that can make shopping a challenge. Dress over jeans lady came over to commiserate. Tall and tipsy, she begged for our sympathy, “What about skinny girl problems?”

Skinny girl problems? Are those like rich people problems, except that you don’t have to worry about tax shelters? The three of us have no idea what skinny problems are. We couldn’t even acknowledge this woman after her inquiry. And then she proceeded to pose with us in every photo we tried to take.

Sheri and I collected our well-earned prizes. I went home and my boyfriend begged to come over and see my look. I thought about changing but that would defeat the purpose. Upon seeing me, he picked me up and hugged me and said, “You look so cute! What are you talking about with this whole birth control thing?” I was grateful that indeed I was not a troll. Or PMS. I was brave enough to wear my freak flag.

Finally, the suns on my pants weren’t the only ones smiling.

Weeks later, we had dinner and drinks with Pam. She told us that our skinny dress over jeans pal had a little issue after the party. On the way to her next destination, she threw up in her cab and was kicked out.

I guess THAT’S a skinny girl problem.

1988. Chicago. Seventh grade. Braces. Headgear at night. My musical epiphanies were Richard Marx and the Bangles. The only things that mattered to me were keeping up my grades, playing softball and practicing my Torah portions for my Bat Mitzvah.

Richard Marx photographed in 1987.  © Bernhard Kuhmstedt / Retna Ltd.

This year, we got a new math teacher. His name was Mr. Black. He was pretty dreamy for a math teacher- dark hair, blue eyes and dimples on top of an athletic physique. 26 years old, an ex-marine full of great comebacks to our failed math attempts like, “close doesn’t count except in horseshoes and hand grenades”. We never had a teacher like Mr. Black before. All our other teachers were older and unrelatable and their teaching methods were slow death by repetition and boredom. Mr. Black was anything but.

He had an edge and a point of view on the seemingly smallest details in math. For instance, he forbade us from using the word “and” when discussing numbers. 100 and 1 was now 101. Dots were now points.  He made us speak about math like smart people. He treated us like adults.

He also teased us- not so much to give us a complex. After all, my class- my whole grade was just 13 girls. It was a small private school and somehow all the boys decided to leave after 5th grade. He teased one girl about the height of her bangs calling her “ski slope”.  I was actually envious- my bangs wouldn’t do that flippy thing that was in style.  What I did do was wear a lot of make-up. Which is odd because I don’t actually wear make up now. He called me “Maybelline”.

We wondered about him and his private life. We took note of the car he drove and the clothes he wore. He was the mysterious stranger that came to town. And I think it’s safe to say that we all had a bit of a crush on Mr. Black, even though no one would admit it.

One of my older sisters was in her third year at Depaul. I visited her at her dorm in Lincoln Park. I was excited to one day live in a dorm just like her and have all my friends down the hall. It was pretty crazy that the dorm was girls and boys on the same floor. This was all before things like the Real World was on tv so the concept of opposite sexes living together was very new to me.

Upon meeting her friends, I immediately developed a crush on a boy named Andy. This wasn’t the first time- I frequently fell in love with my older sister’s friends and dates. These were the only boys I knew. I wondered if maybe she would date Andy. She should. I would have. Or at least called him my boyfriend and talked on the phone, which is what I thought dating was.

But my Depaul sister wasn’t dating anyone. Until she met some guy at a Depaul Blue Demons basketball game. She told me about him and how crazy it was that they met. He was a Depaul alum. And they got on the topic of where he lived…Lakeview. And what he did for a living…teaching. His name was Ben. Ben Black.

My sister started dating my math teacher.

I wasn’t sure what I thought of it. It seemed like it could have perks- I would be an insider on the life and times of Mr. Black. I could go into the teacher’s lounge and not get in trouble. Maybe I could have bragging rights.

But that’s not what happened. When news got out, I was ridiculed. Students from my grade. Students from other grades. Then teachers. Everything from teasing me that I would now get better grades to raunchy comments about my sister, comments I barely understood. I could only tell from the tone that these remarks were mean spirited. I was surrounded by bullies. School used to be a place where I was my best. Now it was my biggest challenge.

How do you fight back? How do you take on your peers? Or authority figures? There’s no HR in middle school. All bets were off.

My greatest accomplishment was making the cheerleading squad. I had practiced everyday- cart wheels, round offs, every cheer I knew. And splits, even though I could only do them leaning to one side or by propping myself up on both hands. But even this became heartbreak when rumors started. As the head basketball coach, Mr. Black was one of the cheerleading judges. And everyone said I only made the cut because the voting was skewed. They assumed I couldn’t have made it on my own.

It wasn’t just bad at school. At home, at family gatherings, I didn’t know how to address my math teacher. Everyone called him Ben, his secret identity. Ben was his Clark Kent. So I just called him “Black”. It would be better this way- so that I wouldn’t slip and call him Ben at school. And it was as informal as I could get with the man who was ruining my 7th grade life.

One weekend I stayed at my sister’s dorm. She was particularly sad. She and Ben had broken up. I could hardly contain my excitement. But quickly realized it was not welcome and disguised my smile as concern. I think he wanted more of a commitment than she could give. She was after all only 20. I was sad for her but secretly grateful not to have any other single good looking teachers.

My sister ended up finding love just fine on her own, love that was way out of the universe of my life. As for Black, he started dating the science teacher- a scandal that wiped my sister and me right off the map.

Pink bagI make sure my coworkers aren’t anywhere near my office and I type “sex toy party” into a search. I find an 800 number for a place called Fantasy World in Lexington, Kentucky.

“Thank you for callin Fantasy Whiirld. How ken we heehlp yew?

“Uh. Hi. I’m in Chicago and I’m planning a fundraiser for a breast cancer walk. I’m trying to do a party where some of the sales can go to charity. Do you have someone who could do that?”

“Well, our closest representative’s in Indiana. You know, yew could become a sales representative and do the party on yer own.

“… How would I do THAT?”

“We seand you out a kit, you tayke the orders and we send yew the products to distribute. The commission starts at 50 percent”.

“Does the kit cost something?”

“We have a bunch of different packages. Fer yew, I’d suggest our mid-raynge kit. It’s $119, includes shippin and you typically make the muhney back in yer first party”.

“Let me think about it and call you back.”

I hang up the phone and wilt on my desk. It wasn’t supposed to go this way. I didn’t mind when one of my older wiser girlfriends suggested having a sex toy themed fundraiser. But I wasn’t supposed to be the one selling them.

I’m 26 years old. I’m uncomfortable with the idea of sex toys, and really with sex in general. Growing up, my mom completely skipped the birds and bees talk opting for a don’t ask, don’t tell policy. The only time sex came up was when my parents debated which movies I was allowed to watch. “No, not that one, it has s-e-x”, as if I couldn’t spell at 13.

But I’m desperate to raise money. I call Fantasy World and I order the mid-range kit.

The following week, I get a call from my building’s management company. “We have a large box for you in the office. We’re open til 6.”

I hurry home, worried that my delivery has an obvious label or worse, a hole.

When I get there, I find the box is big but under the radar. I scoot it down the hall and up the stairs to my apartment. I jam an exacto blade into the tape to slide the box open. The first thing I see is flesh colored. I try to pull it out but it just keeps on going. Two feet of rubber. With a penis on each end? What is this for? I dig further and find multiple bottles of lube. Various sizes of flexible penises in an array of colors. Some even have faces in their mold, making the tip look like a head with a bob haircut. I find vibrating metal bullets. Vibrating rings. A vibrating lipstick. And a vibrating duck.

I have never held a sex toy before, let alone owned a collection, one that is now the centerpiece of my 300 sq foot studio. This is all too much. I am reduced to tears.

After rummaging through this box, the contents won’t fit back in. And I need them to disappear. I start clearing out kitchen cabinets to fit a credit card machine, chocolate body paint, an army of dildos, a masturbation sleeve and a leather flogger.

I call my friend Heather who is 32, so she knows everything. I ask her for help planning this party and she offers up her home, her creativity and a great recipe for quiche. I invite all the women I know. It’s for a good cause so most RSVP yes. And the ones who can’t make it, just send a check. It’s already working!

The day of the party I pack up my collection and bring it to Heather’s apartment. She puts batteries in a large purple penis and hands it to me. I twist the dial to “on” and the vibration is so startling, I drop it on the floor.

By noon, our lady friends start showing up. They look around and ask me questions I can’t answer. My customers know far more than I do but graciously buy a few items and thank me for having them.

I raise half the money I need in sales and donations. I’m ecstatic. But I can’t stop here. I schedule more at home parties, planning to learn as I go.

At my next party, a woman inquires about some sort of deep throat cream. I check my bags. Green apple lube. Chinese shrink cream. Chocolate after sex mints. No deep throat cream.

The next day I call Fantasy World. It’s not the first time I have called them for sex ed. They are my dirty hotline, always ready with an answer, even though they never say the word penis. Never. In Kentucky, it’s a pecker.

“Thank you for callin’ Fantasy Whiirld. How ken we heehlp yew?

“Hi. I had a party and someone asked for a certain kind of cream. For deep throating? I think it’s to numb your…”

“Oh sure. We don’t have something with that nayme but we have anaLISE and that would work grayt.”

“Oh. Ok. AnaLISE.”

“You should have it in your kiit”

I search through boxes. Nothing.

I call back. “I’m supposed to have a cream called AnaLISE and I don’t think I have it”.

“It’s a little whaht tube in a red box.”

I dig through the packages and find the red box. I feel stupid and embarrassed all over again.

It’s not Analise. It’s Anal Ease. I don’t understand sex or English.

“That stuff is grayt. It’s even good fer burns. We tayke off the laybel and we keeeap it around the house.

“So, is this something people can put down their throat?

“Sure. Anything you can use back there, is sayfe enough to put in yer mouth.”

Experiment 1: Anal Ease

I’m excited to email my customer and let her know I found a numbing cream but first, I need to verify that it works. I squeeze a dollop of it on my finger and place it on the back of my tongue. I swallow it, spreading it around the back of my throat. And I wait. In less than a minute, I try to swallow and I can’t. I can’t feel my throat. I can’t breathe. My heart is racing. I run around in circles, gasping. Trying to swallow.

After a few uncomfortable minutes like this, my throat comes back to life. I survived! It works! I did it! So I decide to do more product research.

Experiment 2: Anal beads

I don’t understand the concept. I mean, I get it. But it seems like a lot of trouble. Putting beads up your ass and pulling them out in some specific way, all while during some sex act. I didn’t have a sex act to try this during or at least one that I wanted to bring jewelry to. So I would need to go it alone. Anal Ease or the natural route? I mean, what’s more wet than water? I take them into the shower and slowly coax them up there. The beads are hard rubber, graduated from pea size to super ball. I only get up to 3 out of 10, which I think it technically failing.

I decide I’m done with this activity and I tug on the beads. Oh my god. What if they’re stuck? I don’t have a plan. Do I need a plan? I let go of them for a moment. They just hang there. I wag them like a tail. I DON’T understand anal beads. For my review, I say, it’s like pooping backwards. And taking them out, is like righting the wrong. It’s a relief. I can now recommend choosing the sturdy easy-to-clean rubber set over the cheap plastic ones on a string.

After a few parties and side orders, I end up with more than enough money for the breast cancer walk but have come to like this side business and I still have extra inventory. Unfortunately, my friends are now fully stocked and I need to find new customers. But where?

I work across from Whole Foods where it’s easy to spend $20 on lunch alone. Rich people must shop there. I decide to put up a sign about sex toy parties on the big community board and wait for rich people to call to schedule parties. But you know who else shops at Whole Foods? Couples. Looking for a third.

I take down my sign.

One day, on a walk, I stumble onto a local sex toy store I have never seen before called Honeysuckle. I meet Steve who owns the store with his wife Leann. He tells me, “We’re going to start doing events soon. You should come!”

Without missing a beat, I tell him, “I do events!” And just like that, a new partnership is born.

Leann and Steve are laid back hippies. They have two sons. They joke that in the same way religious families have kids who grow up to be hell raisers, their two sons will most likely grow up to be priests. They give real advice, like that anal ease is not recommended because you should never try to numb your body’s pain or discomfort. And they use the word penis.

After going through their “sex educator training”, they start sending me out to night club events, store promotions and bachelorette parties.

My favorite sales are always to first time buyers. I tell them, “You might not want to jump right into the rabbit. How about this vibrating bullet? Or better yet, buy them both because they’re like a flat and a heel- totally different but essential. You’ll love them. You might give up dating.”

Women don’t just ask me about products. They have questions about sex and even about their bodies. I can’t offer science-based answers but I can listen without judgment and I find that THIS is the most important thing.

After three years and a Saturday night where I have to lug my rolling bag up four flights of stairs to a bachelorette party, I decide my time is worth more than the supplemental income and novelty of the business.

Sometimes I think about selling again. I got really good at it. I can say cock ring without even lowering my voice. But I don’t really need it anymore- I’ve already walked away with an unexpected confidence in something that used to terrify me.

And now I welcome and seek out new challenges. Because I know all I need to succeed, is the right lube.