Kendra was the name the escort service provided for her.  An extra level of anonymity given to their employees to make it difficult for clientele to stalk them.  She thought of herself as Kendra whenever she interacted with clientele.

February 14th, Valentine’s Day, was a normally busy day for a lot of escorts.  Lonely clientele trying to fill an empty spot in their lives by hiring a date for the loneliest day of the year.  Kendra preferred having that day off.  She’d arranged to have her birthday free for the past 15 years working at the agency.  This Valentine’s Day, Kendra received an email from the service making a date for August 1st.

Three days later the package arrived from the service with instructions.  Wrapped in the package was a garment box, received from the client with the request to wear the contents on the date with Jason.  Unusual to say the least; she’d heard of weirder requests from some of her co-workers, but Kendra recalled other occasions in which she’d received garments a client requested for the date.

Mostly the garments were slutty school uniform, or naughty nurse or maid.  The date was almost 6 months in the future.  Given her past experiences, she put the box away in her closet for later perusal.

***

ON JULY 15TH, A REMINDER popped up on Kendra’s calendar, two weeks in advance of her scheduled date with Jason.  The pop up reminded her of the box she’d set aside in February, still waiting in her closet, untouched, unopened, ignored for all these months.

Kendra opened her closet doors, much as she would any other time she prepared for a date with a client.  Though this time was somewhat different, not exactly preparation for a date given the two week lead time, but there was almost a sense of curiosity.  She wondered after putting it off for so long, what the client might be expecting of her.  The time was ripe for finding out whether the client’s perversion would provide a fresh surprise or end up being another in a long string of monotonous sameness.

If it were something new, the two week lead time would give her ample time to prepare for the upcoming date and if necessary research what kind of play the client might be expecting.

The nondescript garment box was anything but presumptuous.  Just a plain extra large white box with the front flap taped down with a label on top – Aug 1st.  Within, tissue paper covered whatever garment she was requested to wear.  An envelope lay atop the tissue paper, handwritten and addressed to Kendra.

The handwriting was how Kendra would expect a woman’s handwriting to appear, light, flowing, airy.  Kendra picked up the envelope, sure that the missive in the envelope would provide whatever context might explain the garment.  The envelope and stationery seemed expensive.  Kendra couldn’t imagine going to such lengths, but then again she couldn’t exactly imagine having an anniversary date.

Unfolding the note, Kendra found a photo of a young couple.  Setting the photo aside, she read inside.

Dear Kendra,

Every year, my husband and I have gone on an anniversary dinner date for nearly 25 years now.  I find myself ill this year and fear I will not be able to attend.  That is why I have asked your escort service to provide a dinner date for my husband Jason.  This is the same date that Jason and I have been on every anniversary.

I have provided the dress that I wear every year.  Please wear it so that he will think you are me in the lobby of the hotel where we always meet, Plaza Vista at 7 PM August 1st.  Reservations have been made and dinner is paid for.  Jason will know where to take you.  Shea’s is where we dine every year.  A band will be playing.  If Jason feels like dancing, please dance with him.  For after dinner, the Honeymoon Suite has been reserved at Plaza Vista in our names.  Please take him to bed there.  It has been so long since I have been able to attend to his physical needs.  Please do for him what I am no longer able to do.  Please be for him the woman I am no longer able to be.

Sylvia

It wasn’t uncommon for escorts to contract extra services with a client.  Ordinarily, the client would be a long standing customer, generous to a fault, and would naturally be somebody with whom the escort had some sort of affinity.  Kendra felt somewhat incredulous with respect to the request.

Reading the heart felt pleading of the note, Kendra discerned that she was to pretend to be the wife on the couple’s anniversary date.  She would have scoffed at the notion of a married woman asking an escort to take her place on an anniversary date, not to mention whatever might occur afterward in the confines of a Honeymoon Suite.  But there it was in a personally handwritten note.

Kendra experienced mixed emotions when thinking about this woman’s request.  She wondered if she would feel the same way if she had a husband; if she could no longer bring pleasure to her husband.  She had trouble putting herself in Sylvia’s place.  Maybe if she put on the dress, it would be easier to do so.

Looking at the photo, she could see that she resembled the younger Syvlia somewhat.  If she styled her hair more like in the photo, perhaps she could pull it off.  She’d definitely agree to wear a chosen garment, and also to attend a dinner and perhaps dancing afterward, but pretend to be his wife?  Well, she had pretended to be a niece once or twice.  Would a wife be so different?

She stared for long moments at the uncovered garment, tissue paper spread open.  The dress was definitely out of fashion, probably at least as old as the relationship alluded to in the accompanying letter, but that wasn’t what held her attention.

No, Kendra’s sight was riveted to the fan of 100 dollar bills partially spread across the bodice of the linen dress beneath, an amount that was beyond her fevered dreams.  If it was as much as it appeared to be, it would more than cover any extra services.

Kendra closed the box lid, unable to believe what had been within.  She imagined that whatever it was that she’d seen would disappear while she held the lid closed under the palms of her hands.  It must be some mistake she thought.  It was beyond normal that anybody would provide such a bounteous tip for an escort of her scant reputation, or so it seemed to her.  And yet, there it was when she lifted the lid once more.

Okay Kendra thought, maybe for this much money, she could.  Besides, Kendra couldn’t quite bring herself to return the package to the client.  It would be just one night or one assignation, however long that may be.  Besides, the wife, Sylvia seemed so sincere.

***

WEARING THE DRESS SENT by Sylvia had Kendra feeling almost retro.  It fit well enough, but in the back of her mind, it was a married woman’s dress that Kendra was wearing to go on a date with that same married woman’s husband.

Kendra thought everybody would know that the Pastel Lavender Linen dress with the sweetheart neckline cutout and the empire waistline belonged to somebody other than the person wearing it.  She thought her cocoa colored coif would be too dark.  It was much darker than the customer’s photo indicated.  She had a bit more cleavage as well.

In the Plaza Vista bar, Kendra ordered a Chocolatini, but immediately changed her mind and decided on a vodka martini with a lemon twist to calm her nerves.  Spilling a chocolate cocktail on a customer’s linen dress would be the pinnacle of faux pas.

Carrying her drink back toward the lobby, Kendra thought a man resembling Jason from the picture walked through.  He headed to the hotel desk, though, so maybe that wasn’t him.  She went to a high table with a view to the entry.  The dress skirt was a bit longer than she usually wore, but it folded nicely against her legs as she sat, facing the lobby doors.

Kendra waited and watched and listened to the hustle and bustle of the hotel lobby; and began to relax a little bit, for which she was grateful.

“I recognize that dress,” said a man’s voice beside her, “I wondered why Sylvia told me to look for her here.  She put you up to this, didn’t she?”

Kendra turned her head to catch a glimpse of the speaker.  It was the same man she’d seen earlier.  He was older than in the photo, streaks of gray in his hair, 10 pounds heavier.  But it was unmistakable now that she had a better view that he was the same man.  Not for the first time, Kendra was curious about how much the husband knew with regard to the date this evening.  His question seemed to confirm that he wasn’t expecting her.

“Jason?” to which he nodded in the affirmative.  “Yes, my name is Kendra.  Sylvia wanted me to help you remember her since she couldn’t be here.  Your anniversary date, right?”

Once again, Jason nodded.  “I don’t remember you Kendra.  Are you a friend of hers?”

Kendra decided honesty was the better choice here, “No, Sylvia wanted to be here tonight actually, but she sent me in her stead.  She arranged this several months ago.  Are you disappointed?”

“No.  I don’t think I’d say disappointed Kendra.  Surprised.  You do kind of remind me of Sylvia faintly, wearing her dress.”

“I understand this is the dress she wears to all your anniversary dinners?  It’s what she told me.”

“It is...” and a pained expression washed his features, “or rather, it was.  She’s unfortunately in no shape to wear it now.  I can hope, but it doesn’t look likely that she’ll wear it any more.”

The silence hung between them for a few moments and seemed as if it would keep stretching out unless one of them broke the ice.

“Sylvia went to a bit of effort to make sure you had an enjoyable anniversary Jason, she said that dinner reservations were made and that you knew where to take me.  And perhaps you should call me Sylvia instead, I think that’s what she wanted.”

Kendra watched him a few moments while he pulled himself together.  With a final visible shudder he appeared to join the present.  “Quite right.  Do you want to finish your drink?”

Kendra looked at the martini and back at Jason, “No, I’m fine.”

Jason held his hand out to Kendra, offering to help her rise.  It was such an unusual gesture, and it kind of enamored her to him.  “Let’s take a cab Kendra... Sylvia.  You look so elegant, I can’t picture you riding in my old beater.”

“Your wife never rode with you?”

Jason chuckled, “She did, but she always changed into that dress before we went to the restaurant.  And... we took a cab.  Have you been to Shea’s before?”

“Let’s pretend that I have, okay?  Keep to the spirit of the occasion.  What do you say?”

“Well, I hope you aren’t allergic to shellfish then, because she always ordered the scallops.”

“Sylvia didn’t mention that.  It’s okay, I’m not allergic.  Are they good?”

Jason cocked an eyebrow.  Kendra closed her eyes and gave herself a mental kick in the pants.  “Sorry, of course.  Why else would Sylvia order them every year?  Okay, I’m a little bit slow, but I think I’m catching up.  Let’s go get me some scallops.”

Jason led Kendra out of the entryway, and hailed a cab.  While they waited for a cab to stop, Kendra suggested, “If there’s something I can do to make your experience more pleasurable, please let me know Jason.”

“Sure.  I will... um, Sylvia.  It’s funny, the very first time we went to Shea’s we couldn’t afford much,” Jason reminisced, “We shared a surf and turf.  Sylvia took the scallops and I took the steak.  After that, she tried the Scallops and Linguine in a Cream Sherry sauce, and ordered it every time since.”

The cab ride wasn’t very long, eight or nine minutes at most, spent in silence.  Jason didn’t seem interested in making small talk, so Kendra didn’t push, rather just spent the time in comfortable companionship trying to think of light conversation she could make without dwelling on a sore point, like Sylvia’s absence.

When the cab stopped, Jason exited first and again offered his hand to assist Kendra’s exit.  It was impressive, at least for the fact that this was her first customer who was charming without seeming to want to have his way with her in bed.

“I’m sorry Kendra, I’m being a bit of an ass, talking about Sylvia all this time.  You should order what you would prefer for dinner.  You don’t need to be her, or even pretend.  I imagine you’ve got better things to do than entertain me on my anniversary.”

“I’m certain this is what Sylvia wanted, and there’s nowhere else I’d rather be anyway Jason.”  Kendra followed Jason to the restaurant doors which he opened for her.  “Sylvia also mentioned that dinner is paid for.  I assume that means she ordered the usual.  I’m fine with the scallops, but thank you.”

“Sounds like Sylvia.  She probably ordered the Rosé for us as well.  It’s a bit dry for my taste, but it was the restaurant’s recommendation for pairing with our first surf and turf dinner.”

Through the doors, Jason approached the maître d’ and said, “Reservation for Bowman.”

After glancing at the reservation list, the man replied, “Ah yes, Jason and Sylvia.  Happy 25th anniversary, Maxine will see you to your table.”

Jason glanced in Kendra’s direction as if he expected she would have some reaction to the staff thinking she was Sylvia.  For her part, Kendra wasn’t upset that they did.  Many times her client would introduced her as somebody closely related to themselves.  In her business, it was to be expected. 

What was unusual was that Jason seemed apologetic for it, though not vocally.  He nodded at the maître d’ and reached out to take her arm as if she were his Sylvia.  It was almost endearing and Kendra hadn’t mentioned she was in the escort business earlier.  That made it seem just about like a real date.

A woman looking almost as magisterial as the maître d’ stepped forward and smiled at Jason and Kendra.  As she led them away she informed them, “When the manager heard it was your 25th, she set aside a private table for you two instead of your usual.  We at Shea’s hope it is an enjoyable evening.”

As they walked arm in arm following Maxine, Kendra began wondering if she was missing such interactions in her life.  She’d never had somebody take her on as elaborate a date as this.  Had she been at this too long and become too jaded?  Was it time to get out of the escort business?

Maxine stopped at a curtained opening and drew it open from one side, motioning Jason and Kendra within.  The private dining area was furnished with one round table and two chairs and a serving table.  Jason pulled back one of the chairs for Kendra making sure she was seated before he himself sat.  There was a low bouquet and one candle holder as well as the two dinner settings.  Maxine lit the candles when they were settled.  Then the sommelier opened the wine bottle, and poured a glass for each of them.

Kendra took up her wineglass and raised it, “To 25 years!” as a server set a basket of steaming soft bread sticks on the table and departed through the now closed curtain.

Jason raised his when they were alone again and added, “Technically we didn’t actually get married until our 5th anniversary, but yes, this is the 25th.  Our family calls it our 20th this year.  Even so, I still kind of think we were married for the first 5.  We attended different colleges, but spent every possible waking moment together.  Heh, except when we were asleep in each other’s arms.”

“I’ll bet there’s quite a story how you two met.”

He huffed slightly, “Not really much of a story actually.  The both of us returned books to the library the first day we met.  Mine was overdue and she paid the fine,” Jason paused a moment looking a little misty eyed before continuing, “I wanted to pay her back right away, and insisted she follow me home so that I could do so immediately.  I didn’t want to be beholden to her, but it didn’t matter.  I was anyway, from that moment forward.”

“How so?”

“She was caught in a torrential downpour less than a block away walking back home.  Sylvia returned to our front door soaked to the bone.  And she was shivering so much she couldn’t talk without her teeth chattering.  After that I looked for any way I could to make it up to her for being so bone-headed.”

“And?”

“I found out where she lived when my Mum drove her home.  I went there every day for two weeks to ask her how I could make up for what I’d done, and every time, she’d tell me that she would think about it and I should come back tomorrow.”

“Wow.  Sylvia sounds like a bit of a tease.”

“That’s not all, I was about to give up, I was just almost ready to quit, and then she said, ‘Give me a kiss, and come back tomorrow.’ until I eventually forgot to ask what to do to make up and just gave her a kiss.  After a month, she asked me why I hadn’t asked her out on a date yet.”

Kendra laughed, “That’s cute!  I’m guessing you didn’t need to be asked twice.”

He got quiet when a server entered to bring in an appetizer, so she didn’t press further, glad to wait until they would be alone again.  The bread sticks were no longer steaming.  The appetizer was breaded zucchini sticks with a ranch dip.  It made Kendra’s mouth water, so she speared one and pulled it onto her plate adding a spoonful of ranch dip.  She worried that a gurgling stomach would interrupt the conversation and sliced a bite from the steaming zucchini.

Jason followed her cue, and helped himself to a couple of spears of the appetizer, though he wasn’t in a hurry to eat.  He also pulled a bread stick from the basket.

Alone again, Jason asked, “So how did you know my wife?”

“Casually, mostly through my employer, but that’s nowhere near as interesting as your story,” Kendra said attempting to steer the conversation away from her being an escort his wife hired for the date, “Tell me about your first date.”

“She made me work for it actually.  Sylvia made me guess what she considered an acceptable first date.  It took me a couple of days to work out that she wanted me to take her roller skating.  I’d never roller skated before, but I think she could have been a pro if she wanted to.  I was so sore after falling down so many times I just about had second thoughts.  But I was hooked on her kisses, the way her lips would stretch into a grin while we kissed.  It was maddening and intoxicating at the same time.”

“Yeah.  I think it would be wouldn’t it?  I’ve never had a kiss like that.  Just hearing you talk about it I kind of wish I could be kissed like that.”

“I can’t kiss like that, not like she could.  Sometimes I just wanted to kiss the smirk off her face,” he giggled, “Never managed to though.  Sylvia was always in control of the kissing.”  Jason choked up then, “Lately, she’s been in too much pain to kiss like that.”

“Change of subject then.”

Jason nodded his head, acknowledging Kendra’s suggestion.  While it took a couple of minutes for Jason as he collected himself a server came through the curtain to deliver the main course of the meal.  The two of them, Jason and Kendra, were silent while the server was present.  They hadn’t eaten much while they were talking.  The server asked if they were finished with the bread sticks and appetizer.  Jason indicated they were not, though the practical side of Kendra thought the food would be wasted, she also figured it would detract from the spirit of the occasion to mention it.

After the server departed, Jason asked, “What about you Kendra, do you roller skate?”

“Nope.  Never.  Not even ice skating.  I’d much rather hike.  I’ve been on the 5 mile trail at the Botanical Gardens quite a few times, and attempted the Appalachian Trail once without much success, but I spend most of my time walking a treadmill.  Did you and Sylvia ever go hiking?”

Jason assumed the look of a person remembering the past with fondness.  Kendra wondered if she’d said something wrong, whether what she had asked triggered a memory that was somehow painful, the last thing she wanted to do.  She asked, “What?  Did I say something wrong?”

Jason came back to the present, “No,” but didn’t elaborate, and took a breath.  “Did you know that the Botanical Society would often hold dinners for the Friends of the Society?  Sylvia and I were lifetime donors, and always on the list.  Many times, we would attend the sunset dinners there and stroll through the gardens in the evening.  Not a bad memory at all... one I’d forgotten about since...”

Kendra waited to see if he would add anything.  On the one hand, she was under the impression that Sylvia wanted Jason to remember all the good times they’d experience.  But on the other, Sylvia had also hired her to what, help her say good-bye?  Sylvia had asked her to be a woman, a sexual woman to her husband.  And the weight of it all pressed down on her shoulders.  She closed her eyes and fought back the urge to become emotionally involved.

She wanted to stay professional, to just be what her client needed her to be, but with Jason and Sylvia, it was proving harder than normal to keep her distance.  And if this tug-of-war between being a good listener and fending off Jason’s queries about how she knew his wife, and trying to steer him back toward remembering Sylvia were any indication... it was beginning to seem like this was going to end up being a total foul up.

Jason cleared his throat, “Oops sorry, where were we?”

“Um... I think I need to use the powder room,” she said.

“Oh.