Midway Mindset

Lessons Learned – It's Never Too Late to Take Flight

As a woman of uncertain means, I’ve ventured into new experiences using discounts from sites like Living Social and Groupon. The list of sources I like massages from is a short one – my boyfriend (still waiting), my daughter, and the chair at the nail salon. Though I have had a few massages from strangers, they tended to leave me feeling a bit less touched by an angel and a bit more ‘where have your hands been and what are you thinking of?’

Coupon in hand, I went to see “Chester” at his studio. It was an older building and all but one of the doors into the building was chained shut and the windows were barred. His actual office was neat and clean but smelled vaguely of Vaseline and fear. I knew where the fear was coming from and I had a bad feeling about the Vaseline. Chester greeted me wearing orange scrubs and a smile. He was a kind but squirrely little man with a lisp, tattoos and a Mohawk. I peaked outside for the prison work truck he might have rolled off of. I tried to wipe the concern from my mind just as I hoped he had thoroughly wiped the massage table. I quickly filled out an intake sheet and took the time to text a friend reminding her I had no identifiable tattoos and where to start looking for my hands and feet come nightfall.

Chester told me to undress to my comfort level. My capris and tank were already beyond my comfort level, but the massage was paid for and I wasn’t going to have some guy rubbing me through my clothes like a 14-year old boy at a freshman mixer. I disrobed, all except for my underwear, wishing I’d given better thought to what my bottom layer was. Red lace indicated I was trying too hard and I certainly didn’t want to give Chester the wrong impression. I looked at the table, wondering what to do now. He had told me to lie ‘face down.’ Easy enough – but surely I’m supposed to be covered up. Where’s the blanket? I saw a tiny square of cloth lying beside the massage table and figured this must be for me. But, what do I cover? My underwear already covered my ass, so I lay down and threw the small band of terrycloth over my back like a tiny cape. I was Super Girl and I was going to get a Super Massage. Chester knocked and walked in. Then, Chester hit the brakes and walked out.

“You’re supposed to be UNDER the sheets. And the hand towels is mine.”


I got situated correctly (rookie mistake) and Chester got started. He kept telling me to relax. Highly improbable given I was practically naked, getting a discount rubdown from someone I wasn’t even convinced even had a key to the building. Chester tried to make small talk and I noticed that, in addition to his lisp, he added an “s” to almost everything. And apparently now was the ‘getting to know you’ part of the massage.

“I likes your feets!” he said, as he rubbed my arches.

Umm…they get me where I need to go, Chester …

“Is that a band-aids?”

Why yes, Chester. Very good. It IS a band-aid.

“Do most womens shaves their own legs?” he asked.

Umm…that would be yes. I’m not sure who Chester thought was out shaving women’s legs door to door for extra cash. Perhaps he was looking for a career alternative if the massage thing didn’t work out?

Next, as he was working on my lower back he growled, “Does you likes this, Precious?”

Umm….excuse me, Chester? (Oh…my…gosh…I think he just called me Precious!)

He repeated himself with emphasis. “DOES you LIKES this PRECIOUS?”

My heart began to race, my pits were getting sweaty and I was wondering how far down St. Mary’s Street I could get in nothing but a hand towel and a thong. It was time for action.

Chester…I think it’s best if you don’t call me precious. My name is Katie.

To which he replied, “I didn’t calls you Precious. I asked “Does you likes this PRESSURES?”

Awkward. Oh, God. Oh, God. Oh, God. So, so awkward.

Yes, Chester. The PRESSURES is fine, thank you for asking.

Halfway through, Chester asked me to turn over, and lay on my back. I began to wonder exactly what parts on my front he was going to attempt to rub. He stood at the bottom of the massage table and began, with both hands, to make his way up my legs, the sides of my stomach and up my arms, to my neck. Now Chester is a short guy, and I was wondering how standing at the bottom of the table he was capable of reaching all of the ways up to my face. I decided to take a quick peek. Chester’s face was about an inch away from mine, tongue hanging to the side as he made the long stretch on tippy toes. Our eyes met.

Chesters and I screamed.

Chester said, “It’s better if you keeps your eyes closed.” I tended to agree.

I took a deep breath and decided I was going to focus on enjoying myself, and not get caught up into who was rubbing me down for half price and why. Once I stopped worrying about Chester, I realized he was actually very good at what he did and I was finally able to enjoy myself.

I’d like to say I became one of Chester’s regulars. Though we’d been through a lot together, sometimes there’s no going back. That night, as I gave him a glowing online review, I realized that I let apprehension and appearances get in the way of a really good massage.

I opened my eyes to Chester and tracked him down on Facebook (cyber-stalk is such a dirty word.) I was able to discern that he was a single dad. I saw Chester grilling burgers with friends and Chester dressed up for Halloween. And then, there were photographs of Chester graduating from massage therapy school with his mom standing proudly beside him. Chester was beaming, not at all self-conscious about his missing teeth. Chester was a dad, a friend, and a son. He was merely trying to make it in this world and take care of the ones he loves – just like most of us.

We all cross paths with Chesters in the course of our days. They’re getting started, they’re just learning their jobs, they might be a little unpolished, maybe even a little strange. But, once I opened my eyes to Chester and really saw him, all of the weirdness went away. He became very real to me and the odd became endearing. I said a little prayer and wished Chester the best. And that felt better than any high-priced massage ever could.

13 thoughts on “Tales of a Massage Virgin

  1. evansithink says:

    Great story. Very visual.

    Liked by 1 person

    1. Thank you! That means a lot coming from you.


  2. Tammy says:

    I’m dying….. 1. Because my dad’s name is Chester and 2. Because you wore a red thong for a massage !

    Liked by 1 person

    1. I forgot your dad’s name was Chester. Hopefully, he appreciates the story 🙂 And learned a lot about massage attire since this happened!


  3. pawluv says:

    Hysterical! Love your writing style.


    1. Thank you for the support!


  4. dereklc says:

    Good story! My first massage was from an Amazon of a nordic lady named Olga… it was a 90 minute Christmas gift and I enjoyed it thoroughly…


    1. I wish I’d had that option! Thanks for reading!


  5. peggy taylor says:

    this is wonderful, Katie. and so funny. Thanks for giving the Chesters of the world their own special recognition. That is so necessary but rarely happens. You are a special kind of person. Love.


    1. Heck, Peggy – I’m a Chester most days! Thank you for your kind words and support. It is extremely appreciated in this new endeavor!


  6. Gary Lewis says:

    Katie, you have a Ceilia Rivenbark, Erma Bombeck quality to your writing. Great story! Keep up the good work!


    1. Those are high compliments! Thank you so much. Not everything I write is as funny, but I try to find the humor in everything. Thanks for reading!


    2. Two of my idols! That’s a high compliment. Thank you.


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