The Jenna Arrangement Pt 02

(Author's note: I'm going to apologize in advance. This chapter is going to take it's time getting to anything sexual. If you enjoyed the premise of part 1 and want to see how the relationship between our protagonists develop, you'll enjoy this. If you're just here to crank one out, you may wanna find another story. I won't be offended.

ALL CHARACTERS ARE AT LEAST 18 YEARS OF AGE OR OLDER)

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It had been over three months since my encounter with Jenna.

The day after our "arrangement" had concluded I sent her a simple note via the contact email we'd exchanged messages through before, thanking her for a wonderful time and hoping we could do it again soon. I got no response.

A few weeks later, I sent another, saying that I'd be interested in arranging another session, if she were still interested, and offered to pay the same rate as last time even though money was a bit tight just then. Still no reply.

A week later, I sent a third message. Still nothing.

I decided to let it go. Obviously she'd decided it was a one and done deal, a quick way to earn money to buy her needed books, nothing more.

I was feeling, well, several things. Horny, of course, but also strangely lonely, which was unusual for me. I found myself missing her company, which was ridiculous, seeing as the very short time we'd actually spent together was really just a business arrangement, nothing more.

The panties she'd given me to take home had long since dried out despite my efforts to preserve her scent by sealing them in a Ziplock bag. Still, I kept them, and often found myself still sniffing them during my solo sessions, although the scent was all but completely faded.

Time passed. I carried on in my same old dull routines. Get up, go to work, come home, dinner, work out every other night, masturbate almost every night, go to sleep. Rinse and repeat.

Weekends were just as boring. Sleep late, putter around my small apartment, run errands, maybe hit the pool at the gym, watch TV or go to a movie. Then suddenly it was Monday again.

I'd lost all of my friends in the divorce seven years ago. Well that's not exactly true. What I'd actually lost was all of my wife's friends; I found out the hard way that they'd only considered me a "friend" by proxy.

But that's all a long, sad and ultimately boring backstory you probably don't really give a shit about, do you?

So let's skip ahead a bit.

I came home from work late one Friday evening to find my refrigerator empty of all but some ancient condiment bottles. Not much in the cupboard, either.

I decided to take a drive to a little diner not too far away. I hadn't been there in quite some time, but I remembered they had a pretty decent prime rib.

The place was moderately busy when I came in, but the wait wasn't long, and I soon found myself in a booth.

I was mindlessly scrolling through my phone when I heard the waitress approach. "Good evening, sir, what can I..."

Her voice halted suddenly, and I heard the sound of what turned out to be her order pad hitting the floor, landing near my foot. I bent down, picked it up, sat back up to hand it to her, and froze.

It was Jenna! Her face was frozen like a deer in the headlights.

I was pretty shocked myself, of course. I recalled her mentioning a waitressing job, but not specifically where.

A thousand thoughts ran through my brain all at once as to how I should handle this. Ultimately I decided to simply play it straight.

"You dropped your pad, miss," I said casually, extending my hand out to give it to her.

Life suddenly returned to her face, and she eventually composed herself enough to respond, "Oh, oh, yes, of course, th-thank you sir."

"No problem," I replied, giving no hint of anything other than just being another customer.

"What...what can I get you to start?" She asked, finding her professionalism again, "Coffee? Soda?"

"Just water, thank you. And I'm ready to order now if that's OK. I already know what I want."

"Yes, of course sir, what would you like?" She asked in the friendly tone every server in America practices to hopefully increase their tips.

I had to bite back hard on replying, "Well a fresh pair of panties to start," and instead just ordered my prime rib, medium rare, with some mashed potatoes and spinach as my sides.

From there we went through the familiar routine. She brought my food, I ate, she'd occasionally stop back to refill my water and ask if I needed anything, then move on to the other tables.

Finally, I asked for the check, and she returned with it shortly. "Was everything OK, sir?" She asked, ever the professional waitress.

"Everything was wonderful, thank you Jenna." Yes, I used her name on purpose, just to see her reaction.

Her professional smile suddenly cracked with surprise, and then I saw...a REAL smile. The one I remembered from before, when we were involved in a very different kind of customer / server relationship.

"I'm...I'm glad to hear that. Have a great evening, sir. Come see us again soon, ok?" She said, managing to put her waitress persona back on.

"I'm sure I will," I replied, and she simply turned and walked away.

I grinned to myself, shaking my head. "Small world," I thought, then shrugged. "I'll leave her a nice tip."

As I picked up the check to go pay, I noticed something odd, and turning it over, saw a post-it note stuck to the back. There was a message hand written on it.

"I get off at 10pm. Call me! PLEASE! - J" Below was a phone number.

I damn near dropped the thing. Instead, I pocketed the note and made my way up to the cashier.

I took one last look on my way out the door. Jenna was busy with other customers, but I thought I saw her glance my way. I gave a quick nod towards her, confirmed that she saw it, then simply left.

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A light drizzle had begun as I got into my car, and by the end of my short drive home it had become a steady rain.

I still had about two hours to wait until Jenna's shift ended, and I spent most of that time deep in thought.

She'd recognized me right away, that much I knew. What I wasn't sure of is whether I'd played it so cool she thought I didn't recognize her until I actually said her name. Didn't matter, I suppose, given the note she left me.

She wanted to talk. Why? Why had she ignored my emails all this time, only to give me her phone number at a chance meeting?

I honestly couldn't decide if I was angry or thrilled about this situation.

Time ticked by slowly. I decided to clean myself up a bit; shave, take a shower, fresh deodorant, clean clothes. I don't know why I put in all this effort, it was only gonna be a damn phone call.

And yet I was prepping like a high school boy getting ready for a date.

"Just killing time," I thought to myself.

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It was 10:05pm. Her number was dialed into my phone, but my thumb refused to hit Send.

I was sweating nervously. So much for that shower. Whatever.

Finally I found my guts and made the call.

She answered on the second ring. "Tom?" Her voice was quivering, but unmistakable. "I was...afraid you decided not to call."

"Sorry, lost track of time," I lied. Then I cut right to it. "I tried to email you several times. You never responded. What happened?" I found there was no anger in my voice, just hurt confusion.

"Look, it's...complicated," she said, then before I could respond, suddenly switched gears. "I hate to ask you this, and you have every right to say no, but could you...could you come give me a ride home? I usually walk, but it's several blocks away and it's pouring rain. "

She must have mistaken my shocked silence for anger, because she continued quickly, "Look, nevermind, forget I asked, I'll be fi..."

"Jenna," I broke in, finally finding my voice, "It's fine. I'll be right there. I'm only five minutes away."

The relief in her voice was palpable. "Really? Oh, thank you, so much."

"No problem, see you shortly," I replied coolly, and hung up.

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It took longer than I expected to get back to the diner. The rain seemed to be getting worse by the minute. High winds were now whipping through the trees, threatening the powerlines, and several streets were flooded.

I pulled up near the entrance to see Jenna standing inside the foyer, looking out. I called her cell as I parked. "I'm here," I said when she answered. "I can see you by the door. Stay there, I'm bringing you an umbrella. "

I scrambled out the door, grabbing the umbrella and the cheap plastic raincoat I kept in the glove box for emergencies.

The umbrella turned out to be totally fucking useless. A strong gust of wind utterly destroyed the thing as soon as I opened it, and between that and the heavy rain, I was soaked head to toe by the time I reached the diner door.

Jenna stood there, staring at me with a mix of sympathy and amusement.

Our eyes met. Any anger or resentment I might have had in me towards her washed away with the rain still dripping down my face.

I simply smiled at her, held up the tattered remains of the umbrella, and shrugged.

She burst into laughter, as did I. The tension had broken.

"Oh my god, I am SO sorry, I didn't expect you to do that," she was apologizing between giggles.

"That's what I get for trying to be chivalrous," I joked, grinning.

"My hero," she fake swooned. Then, despite my nearly drowned state, she swooped in and gave me a hug.

She came away from the hug with some wet splotches across the front of her waitress uniform. She noticed it, and grinning an embarrassed grin, sheepishly folded her arms across her chest.

I decided not to comment on it, instead simply saying, "Look, my car's still running outside, do you wanna make a dash for it or try and wait it out? I brought you this." I held up what turned out to be a rather pathetically cheap rain poncho.

"Screw it, we're both wet now, let's just go for it," she grinned. She slipped on the cheap poncho, which barely covered her shoulders, and we made a mad dash for the car.

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The ride to her place was slow and tedious. The rain made visibility a nightmare, and the winds kept trying to blow us off the street.

The only thing the poncho had saved Jenna from getting wet was her hair. The rest of her was as soaked as I was. I had the heat up on full blast, trying to dry us out and still our chattering teeth.

"Hurricane, ya think?" Jenna managed through her shivers.

"I dunno," I replied shakily. "Maybe we all just really pissed God off again. I thought I saw an Ark float by on my way to the diner."

She bellowed a laugh despite the tense situation. The rest of the ride was quiet as I concentrated on trying to just stay on the road.

We finally pulled into the parking lot near her dorm / apartment. It was approximately twenty yards from the lot to her front door, and the rain hadn't let up one drop. We both sat there, looking out the windows, then at each other.

"We can wait here for it to slow down if you want," I said to her.

"I just wanna g-g-go in and dry off," she said, still shaking despite my apparently insufficient car heater.

"Ok well I guess this is where we say goodbye then," I said cautiously.

"No!" she blurted. "I...I mean, can you...come in with me, you can at least dry off a bit and wait this storm out. I'd hate to think of you getting in an accident on the way home, especially since it's my fault you're out in this," she said, sounding concerned.

"Are...are you sure? What about your roommates?" I asked.

"Two of them went home for the summer early, the other is staying the night at her boyfriends," Amy said, shrugging. "It'll be fine. Please, come in. I don't want you driving in this and," she paused, "and I really did want to talk to you."

"Ok," I shrugged back, "you talked me into it. Race ya?" I said with a wink.

She grinned a sly grin, then chirped, "Winner gets the first hot shower!" Before I could respond, her door was already open and she was sprinting for the house.

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I'd almost caught up to her despite her head start, until I slipped in the mud and fell flat on my ass.

She'd made the front door by then and was keying it when she must have heard my surprised yelp and subsequent splat. Quickly, she rushed back over to me.

"Are you ok???" she shouted above the rain, reaching down to help me up and immediately slipping to fall right next to me.

Now I was up and trying to help her regain her feet. We were both caked in mud and rain, and laughing hysterically.

We finally made it to the front door, and Jenna had a moment of panic when she couldn't find her keys. I went back and retrieved them from where she'd fallen. After a moment's struggle with the lock, we finally made it inside.

We both just stood there, gasping for breath and already leaving a large puddle on the welcome mat.

"Jesus," Jenna muttered, catching her breath.

"I think he took the night off," I sniped, causing another fit of giggles from her. I realized how much I enjoyed making her laugh.

There was an awkward pause once she stopped laughing, and we simply looked at each other.

Even currently doing her best imitation of a drowned rat, (but then again so was I) she still looked simply adorable. I couldn't help but notice how her drenched clothes were clinging to her curves, compromising her modesty. I quickly averted my eyes, not wanting to make her suddenly uncomfortable.

"So, um..." Jenna started, "I really, like REALLY need to get out of these filthy clothes, but I can't run through the place like this. Can you...could you...you know, turn around?"

I got her drift and respectfully turned away, facing the door.

"No peeking, promise?" Her voice came nervously from behind me.

"I promise," I said solemnly. I did a quick criss-cross over my heart and again heard her giggle.

Over the sounds of her struggling to remove her wet clothes, she grunted, "Once I get this stuff...off...I'll make a beeline to the bathroom. Then I'll...come back out and...bring...you a towel, and you can...undress here while I...take a quick shower," she finished, breathing with relief as she'd, I'd assumed, finally removed the last of her wet clothing.

"No peeking! I'll be right back!" I could already hear her voice retreating away and the sounds of her bare feet running across the floor. Moments later I heard the bathroom door close.

I figured it was safe to turn around now, and looking down, I saw her wet clothing piled on the floor, including her bra and panties. I had to smile, imagining her running bare assed naked through her living room.

I stood there, shivering and hugging myself trying to warm up, when Jenna suddenly reappeared from the hallway.

She was wearing only a large, fluffy white towel, and carrying another one.

She'd managed to get her wet red hair in some semblance of order, but it was still streaked with mud. Whatever makeup she'd had on at the diner was utterly washed away from the rain. But her freckled face was radiant, despite the flecks of mud that still caked it here and there.

I felt another shiver run through me, but this time not from the cold.

If she noticed my stare, she didn't say anything. Instead she just handed me the towel and said, "Here, undress and use this to cover up. I'm going to shower, then you can hop in after me, ok?"

"Sounds like a plan," I sputtered, my hair still dripping water down my face.

I started to undress as she turned back towards the hallway. I was down to my underwear when I heard her voice call out from behind me, "I'll be as quick as I can, I promise. Oh, and I turned the heat up a bit to help keep you warm."

I turned and saw her standing by the hall entrance, watching me with a wry grin.

"I thought we agreed, no peeking," I said in mock annoyance.

Her grin widened. "Hey, you agreed to that, not me. Besides, it's nothing I haven't seen before, right?" With that she dropped a wink and disappeared down the hall before I removed my boxers.

I did my best to dry myself, then covered my nudity, wrapping the oversized towel around my waist.

I was still too damp and dirty to actually sit on any furniture, so I stood there, alone, still shivering, and bored. I'd left my phone in the car, which was probably smart in retrospect considering my wet muddy fall, but I didn't even have that to occupy me as I waited, shifting my feet and trying NOT to think of Jenna naked in the shower that I could hear running faintly from down the hall.

At least I was feeling the place start to warm up from the heater, and my shivering finally subsided.

After what felt like eternity but was probably only about ten minutes, I heard the shower stop. Five more minutes passed, then the door opened, and Jenna called out, "Sorry, I know I took forever. I saved you some hot water, I promise. I'm going to duck in my bedroom, when you hear that door close you can head into the bathroom. I laid out everything you'll need." Seconds later I heard her bedroom door close, and I carefully made my way to the bathroom.

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I stepped out from my considerably shorter shower, wrapped in a fresh towel, to find Jenna throwing our filthy clothes in the small washer / dryer combo occupying a utility closer next to the bathroom.

She was wearing a long, maroon bathrobe. Her hair looked freshly blow dried, her lightly freckled face now fully clean and still bare of any makeup.

"Gonna have to wash these," she smiled apologetically, "I'll see what I can find for you to wear in the meantime."

"As long as it's nothing too lacy," I deadpanned, causing her smile to widen. Her green eyes were filled with mirth, and I caught my gaze lingering a bit too long before I broke eye contact to continue down the hall. I found the couch and plopped down on it, exhausted.

Jenna joined me a few moments later, carrying what I at first thought was a blanket. Then I realized it was one of those Snuggie things you'd see advertised on TV. It was bright pink.

"Sorry," she said, not looking the least bit sorry, "I don't have anything that would possibly fit you, but you can use this to cover up and keep warm if you want."

"I'm actually warm enough now, thank you, but I'll use it to cover myself if that makes you more comfortable," I offered.

"Well, actually, I kinda need that towel, I wanna wash it with the rest of the stuff," she said, a slight flush now showing on her face.

I stood up, managed to put on the ridiculous pink Snuggie, then slipped the towel off from under it and handed it to her. She blushed harder, then went to throw it in the machine.

I sat back down and wrestled with the Snuggie, adjusting it around me to make sure I was properly covered.

Jenna came back into the room as I was finishing, and burst into a fresh fit of laughter.

"Sorry, I really am," she said between giggles, "I wish I had something better for you, but..."

I grinned sheepishly, and shrugged. "Hey I've been in far more ridiculous scenarios I suppose," I said with a wink.

She blushed again, but winked back, and my heart skipped a beat at how adorable she was.

Jenna took the same chair she'd sat in last time I was there, under much stranger circumstances I suppose, and breathed a sigh of relief to finally be off her feet.

We sat in silence for a few minutes, just taking a moment to chill from all the recent craziness.

Jenna finally broke the silence. "So I guess we need to talk."

"Jenna, look," I said calmly, "you don't have to explain yourself to me. We had a deal, the deal was done, and you decided that was enough. I get it. I just wish you'd at least have responded to my messages to tell me, ya know?"