The Jenna Arrangement Pt. 01

Author's note: I've gone back and edited this story to correct several punctuation, spelling, and grammar issues that have haunted me since I first published it.

ALL CHARACTERS ARE 18 YEARS OF AGE OR OLDER.

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I'm not rich, by any stretch, just a regular Working Joe like most guys. But I have needs, and I have fantasies...like most guys.

So occasionally I save up some cash, and find ways to make these fantasies happen.

At 53, I'm not deluded enough to think that much younger women would really be into me. When you hit a certain age, you become invisible to the younger generation, even though I was still in pretty good shape for my age.

I'd paid a few prostitutes here, a few massage parlors there, but found pretty quickly that paying for sex really didn't do all that much for me. I mean ok, yeah, I got off, and some of them were pretty fucking hot. But afterwards, there just wasn't much satisfaction.

I decided I wanted to try something different, and indulge two particular fantasies of mine: smelling a young woman's panties in front of her, and masturbating while she watched.

I suppose I could have gone the usual route and found a woman in the escort ads you can find online, but I was hoping to find someone more innocent, someone who wasn't an established sex worker, but maybe needed the money and would be willing to do something a little kinky for it.

I decided to place my own ad on some local college sites as well as a few of the other personal ads sites. I had to word it carefully, I didn't want it to be a solicitation for prostitution, but also wanted to make clear at least some of my intent.

My ad, after much editing and rewriting, read as follows:

"Older man seeking younger college girl to share an erotic fantasy with. No physical contact would be required on your part, nor any nudity. I am NOT looking for a prostitute. You would be compensated financially for your time of course. Willing to pay $200 cash for no longer than an hour's time. Willing to meet in public beforehand to discuss full details and make sure you are comfortable with the situation. I'll even buy lunch. Worst thing that can happen is you get a free meal and we go our separate ways if you decide my offer isn't for you. Contact me at the info listed below, we can discuss more details there as well."

I placed the ads, then waited.

A few days went by and nothing happened. Then I started getting responses. Most were exactly what I didn't want, "escorts" making all kinds of offers. I ignored them.

I'd all but given up when suddenly a response came in that caught my eye.

Her screen name read "Jenna62402," and the picture she used for her avatar looked promising. Young, red hair, short stylish cut that fell across her face beautifully, not quite shoulder length. Lovely green eyes, and a beautiful, very girl next door face. Not a supermodel, not exactly a Plain Jane either. Just a natural young, beautiful woman.

Her response read:

"Hi, I'm Jenna. I'm 19 and currently attending college, and could certainly use a few extra bucks. I can't believe I'm responding to this, so please don't make me regret it. I'm not a prostitute and certainly have no interest in becoming one. I'm not sure why I'm doing this. Like I said I could use the cash, and something about your ad piqued my interest. I'd at least be curious to hear what this 'erotic fantasy' involves."

I couldn't believe it. She seemed perfect. Almost too perfect. I was hoping I wasn't getting played, but it was the best response I'd gotten so far.

I took my time crafting my reply:

"HI Jenna, I'm Tom. Thank you for your response, I was beginning to think I'd never get one. I understand your reservations. I'm certainly nervous as well. So let me describe what I'm looking for."

I paused for a moment, debating. I decided to leave the panties aspect out of it for the time being, fearing that might frighten her off, having to offer up something so intimate to a stranger.

So I kept it to just the other fantasy:

"I have a fantasy of masturbating in front of a young woman in a casual setting. Let me stress, I would not require you to get naked, nor touch me in any way. I will not be touching you. I won't ask for anything such as dirty talk or whatever. You wouldn't have to do much at all actually. All I'd really want is for you to watch me as I do it. We could talk as you feel comfortable, nothing more.

"For the amount of cash I'm offering, I'd hope for it not to be a rushed experience. I'd like to relax, enjoy myself, take my time. But it would certainly take no longer than an hour, probably less depending.

"I'd be willing to meet face to face in a public place of your choosing so that we could both get to know each other a little better and ease any fears or concerns you might have. As my add said I'd at least buy you lunch if nothing else.

Hoping to hear back from you.

Tom

PS I'm attaching a picture of myself, fully clothed I assure you, just so you can see I'm a real person. "

I nervously hit send, then waited.

Two days went by, and I figured this was just never gonna happen. Then, finally, a notification came in. A reply from Jenna!

"I'm sorry for the delay in replying. I'd be lying if I said I wasn't still nervous about this, but something has come up and I really could use the cash, so I'm at least willing to meet with you. I know it's last second, but could we meet tomorrow, around 4pm? I'll include the address of a little coffee shop that's near my campus.

Jenna.

PS thanks for including the pic and for it not being a nude lol. I'm attaching another pic of me, just my face, sorry, but so you know I'm real too."

The picture she attached was different from the one she used as her avatar, just a selfie really, but she certainly looked like the same girl, and just as cute.

I replied back immediately:

"Tomorrow would be perfect actually. I very much look forward to meeting you. Attaching another pic of my face so you'll be able to recognize me.

See you soon,

Tom."

I actually had to hastily snap a few selfies then sort through them. I picked the one I thought was the least terrible and attached it.

I lay awake that night, my mind racing. Would she even show up? Would she decide, after our time together, to opt out, take her free meal and run?

If she agreed to it, when could we make it happen? Tomorrow night? Another day?

I pulled up her last message on my phone and enlarged her picture.

It was just her face, not much hint of her body at all, but she looked like the type that was pretty petite. Her eyes were bright green. She looked happy enough in it with a pleasant smile, and I could even make out some very faint freckles on her cheeks and nose. Perfectly adorable, I thought.

I debated on masturbating. I hadn't jerked off in a few days; now I was wondering if I should wait til our meeting and see what happened, or ease some pressure now.

I decided to wait. If things went the way I'd hoped, it would only make that eventual release even sweeter.

The next day finally came. I had to work that morning but my job is pretty flexible, and I managed to knock off early.

Went home, showered and groomed...just in case.

I arrived at the coffee shop about 10 minutes early. I sat in the parking lot for a few minutes, trying to calm my nerves. Taking a few deep breaths, I headed inside.

It was a small shop, not too crowded. I looked around for Jenna. Not seeing her, I found a booth and sat facing the door so I could spot her if she showed up.

To her credit, she arrived right on time.

I recognized her as soon as she walked in the door, and my face lit up with joy; she was absolutely perfect.

As I'd guessed, she was very petite. Her short red hair flowed loose and casual, with a few random stands across her freckled face.

This was my first actual look at her body, and I wasn't disappointed.

A green tank top displayed her small but firm breasts nicely. I couldn't be sure if she was wearing a bra or not.

A short (but not too short) denim skirt framed her surprisingly curvy hips for such a tiny frame. Her pale, shapely legs seemed bare, no stockings.

All in all, it was an outfit that gave me hope. While certainly nothing that could be considered slutty or super revealing, it said she wasn't embarrassed about highlighting her physical attributes for me either.

She stood frozen in the door a moment, her eyes wide and nervous.

I stood, waved, and called her name.

"Jenna? Hi. Over here." I smiled my warmest smile.

She looked at me, her face blank for a moment. I thought she might actually turn and run, but then she smiled back and came over.

"Tom? Hi. Nice to meet you. Been waiting long?" She asked.

I stood to greet her. "Not at all," I replied, "just a few minutes really."

An awkward pause followed in which I wasn't sure if I should offer my hand. I decided against it since I'd promised no touching.

"So," I started, trying to break the ice, "I at least promised you some food. What would you like? Anything you want."

They didn't have servers, so we went to the counter to order. Jenna ordered a salad and an iced coffee. I ordered a regular coffee and, since I wasn't all that hungry, a nice chocolate chip muffin that looked appetizing.

We sat back at our booth, and between bites and sips we exchanged stories.

She was in her freshman year at college. She'd gotten a scholarship, but still had to pay for many expenses like her books, personal items etc. Her mother helped when she could, (her father had sadly passed when she was young) and she also worked part time as a waitress, but money was always a struggle.

"I have a class coming up in a few weeks I need some new books for, and that's kinda what pushed me to answer your ad," she explained between bites.

"Well maybe this can certainly become mutually beneficial for both of us then," I said, sipping my coffee.

She looked up from her bowl, for the first time really looking at me.

"So I have to ask," she said, swallowing her last mouthful, "You look like a pretty normal guy. You single? Married? What?"

"Divorced," I replied. "Several years ago. Been single ever since."

"So no girlfriends? No one you could...you know, enjoy this...fantasy...with?"

"I've had a few girlfriends here and there, nothing really long term. They just..." I hesitated, then decided there was no reason not to be honest. "I don't think I'm very good at relationships. I'm a nice person, don't get me wrong. Never abusive or cruel to anyone, even my ex wife. But I can be selfish and a bit of a loner, and I think sometimes women want more from me than I'm capable of giving."

She considered that thoughtfully for a few moments. Okay, I guess I get you. Not really my business anyway I suppose. Just wondering what led up to this particular...thing. I mean couldn't you just hire a hooker or go to a strip club or something?"

"Oh I have," I answered frankly. "I just tend to find those types of encounters...unfulfilling."

"I see," She said simply.

Jenna had another sip of her iced coffee, then spoke again.

"Ok so I'm just gonna be blunt," she began. "This is, without a doubt, the weirdest fucking thing I've ever even considered doing. And I won't lie and say I'm not still afraid. But you seem nice, normal. And I can really use the cash."

"No touching, right?" she asked.

"Absolutely not," I replied.

"You're not gonna suddenly ask me to strip, or jerk you off or blow you or something?" she questioned.

"No, nothing like that at all. Only one naked is me. Only one touching me is me. I won't lay a finger on you I promise."

She looked like she had another question. "Go on, say what's on your mind," I prompted her.

She hesitated for a moment. "I know you said $200, cash, for no longer than an hour. But I need $300 for my books. I can't do it for less than that."

She paused there, probably expecting me to object or get angry.

Instead, I saw an opportunity.

"Well that's quite a bit of money honestly. I'm not rich. This is a special treat for myself to check a little fantasy off the bucket list. Nothing more. But I suppose perhaps we could negotiate something else..."

"I'm not getting naked, no," she broke in. "Sorry. That's a deal breaker. Can't do it."

"I wasn't going to ask that," I replied calmly, trying to keep her relaxed. Don't blow this now, I thought.

I continued, "How would you feel about giving me the panties you're wearing while I...did my thing? NOT get naked, you could remove them in private. Keep the rest of your clothes on around me the entire time. That's all."

"My panties?" She asked, surprised. "What would you do with my..." She stopped herself, then laughed, "Yeah ok, silly question I guess. I get the idea. Let me think about this for a minute. Um, can I get another iced coffee?"

"Absolutely," I said. I went to the counter to order it, leaving her alone to process everything.

When I came back with her drink a few minutes later, she seemed more calm and relaxed, even smiled and thanked me as I handed her the drink.

"Ok so I've thought it over and...ok, I can't believe I'm saying this but...you have a deal." Suddenly Jenna put out her hand. She wanted to shake on it!

I laughed and shook her soft, tiny hand. "Deal. You have no idea how happy this makes me."

She laughed as well. "I'm sure I'll get an idea," she said with a wink.

Damn she was cute. And if she's warming up to the idea, even better!

"Oh I'm sure," I chuckled. "So, next question: when do we do this? And where?"

"Today. Right now in fact," she replied. "My dorm is just a few blocks from here. We can walk there. My roommates will be gone til late. No one I know should see you with me."

She paused, then continued, "IF someone I know sees us, you're my uncle, dropping by to, well, visit and lend me some money. Only a partial lie I guess."

"Good thinking," I said. "Last thing I wanna do is cause you any embarrassment."

"Oh I'm sure I'll be embarrassed at some point...later," she said smiling, "but I'm still new here and don't know that many people really. I'm sure it will be fine. Oh, just a few last things..." Jenna hesitated.

"Go for it," I encouraged her.

"I'm going to have my cell phone handy, with 911 on speed dial. At any point you attempt to...break our deal, try and touch me, try to hurt me, I'll call the cops and report an attempted rape. I also carry pepper spray..." she pulled it out of her purse to show me, "...this will also be handy. And I'm not afraid to use it."

"Fair enough," I said calmly, "but I assure you you'll need neither. You're smart to be cautious, though. I'd expect nothing less."

"Then let's do this before I lose my nerve," she giggled, and with no further discussion, we headed for the exit.

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The walk to her dorm was short and quiet. It was a beautiful, warm evening, with a nice breeze that I enjoyed watching blow Jenna's lovely red hair around her face.

I tried not to stare too much at her body just yet, but did finally get a good look at her cute firm little ass swaying beneath her skirt. I couldn't help but wonder what kind of panties lay beneath.

Were they fresh? Or had she been wearing them all day? Was any of this, of what was about to happen, even slightly arousing for her? Would they be wet when she took them off to let me smell them? There was no guarantee of anything I suppose. It's not like I made any kind of deal that said she had to cum in the panties first. I'd take what I got I suppose, and hope for the best.

We arrived at her dorm without incident, and as she unlocked the door, she told me, "Wait here. Back in a few minutes. "

With that she closed the door, and I heard the latch turn.

I stood there waiting nervously, hoping no one would come by. And hoping yet again that she hadn't changed her mind.

The door opened again and Jenna ushered me inside, quickly closing it behind her.

"Sorry," she said. "Just making sure no one was home. And I...well, I had to pee. Too much iced coffee." She gave a nervous laugh.

And you didn't want me inside your apartment while you did that, I thought. Smart girl. I couldn't fault her for being cautious.

I looked around the place. It was larger than I expected. The door opened into what was their common area living room, with a couch and a few cushioned chairs. A large wide-screen TV sat on it's stand in the center.

Beyond that was a small kitchen area, and a hallway that went off to the right that I assumed led to the bedrooms.

"I live with three other roommates," Jenna said. "There's four bedrooms and the bathroom down that hall. It's not as crowded as you'd think, we're hardly ever all here at the same time."

"Do you mind if I use the restroom myself?" I asked, wanting to fully empty my bladder before we got started.

"Oh! Of course, sorry. End of the hall, you can't miss it," she said.

I took care of business quickly, not wanting her to think anything suspicious, and washed my hands well. I noticed a laundry basket in the corner, and it was tempting. But I didn't want to ruin my deal with Jenna by doing something stupid and invasive. I finished up and came back to the living room.

Jenna was seated on a chair closest to the door, and on the little end table beside it sat her cellphone and pepper spray.

Smart girl, I thought again. Sit close to the exit. Just in case.

"So," she said, her voice trying not to shake, "how do we start this?"

"Well first, your payment," I said, pulling the cash from my wallet. "I want to give this to you right up front so you're not worried about getting stiffed afterwards. Put it somewhere safe," I instructed.

She hesitated for only a moment, then took the money. "Thank you," she said, then put it in the drawer of the end table.

That showed a little trust, I thought. Trust I wouldn't try to steal it back after.

"Now I suppose in the interests of being tidy, you might want to find a towel you don't mind getting messy to put down on the couch, oh and also some tissues perhaps?"

Her eyes questioned, then quickly understood. "Of course," she said, and headed off to the bathroom. She took the pepper spray with her. Smart girl.

She came back quickly with a towel and the tissues, handed them to me, then sat back down in her chair by the table.

She put the pepper spray by the phone, and as I spread the towel out on the couch across from her I noticed her checking the drawer to see if the cash was still there. I admired her for that.

She looked at me again, wide eyed. I saw nervousness and caution, but no fear. Good.

I checked the time on my phone. "Okay, let me explain how this will go from here. It's just past 5pm now. I promise you I'll be out your door by no later than 6, probably earlier."

"I'm going to undress completely; I prefer being completely nude while pleasuring myself. As I explained before, I don't need you to do anything. You can simply sit and watch, quiet as a mouse if you want. That being said, I'd hope you'd be comfortable enough to talk with me during, even ask questions if you want. You don't have to talk dirty, but I wouldn't object if you did. I may want to talk a little dirty, but if I make you uncomfortable, tell me. I just want you to be comfortable. And maybe once this gets started you'll find it enjoyable on some level, if not actually arousing. I understand most women don't generally get turned on watching a man masturbating, or at least not a stranger. But I'd hope..." Here I paused, then continued, "I'd hope by the end you'd have at least found it interesting, and not some regrettable experience. "

She smiled and looked at me calmly. "Yeah no promises there I suppose, but I'm not feeling as nervous as I was earlier. I am...curious...as to how I'll react to this," she laughed. "So, um, do you want the panties now, or...?"