The Jenna Arrangement Pt. 06

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Tom receives a special, unexpected gift from Jenna.
3.7k words
4.74
18.7k
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Part 7 of the 29 part series

Updated 03/16/2024
Created 08/22/2021
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Djmac1031
Djmac1031
846 Followers

ALL CHARACTERS ARE 18 YEARS OF AGE OR OLDER.

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Three days had gone by since our little role-playing video chat, and although neither of us had the time since to do more than exchange a few texts and make plans for the weekend, my thoughts turned to that chat over and over again, especially at night, when I'd recreate her pics in my mind, (Snapchat had erased them all of course) and masturbate furiously to the memory of her voice calling me "daddy." It had turned me on much more than I thought it would.

Jenna had texted me the day before, asking if I was interested in going to a Movie On The Lake event happening on Saturday night. The idea was that you floated on a raft or tube on the water while watching the film projected on a large screen. They were showing Jaws, one of my all time favorites, and one Jenna remembered her father had liked, but she was always afraid to watch as a kid.

Jenna volunteered to pick up the tickets, but asked me if I could get something for us to use on the water.

I stopped at a local sporting goods store after work and had just scooped up two individual floatation tubes when I spotted a double seated one that looked interesting. It even had a little space in between to hold snacks or drinks, and I thought that could come in handy, since it was a BYOB event.

I debated for a few moments; would Jenna want to share the double seated tube with me, or, since we'd be in public, would she rather have her own individual tube?

I decided to buy all three; I could always return whichever one we didn't use. I also grabbed a small battery powered air pump to inflate them with.

The store also had swimsuits and after not remembering what shape my old suits were in, decided to buy a new one.

I was excited about the prospect of seeing Jenna again, but also a bit nervous. With the exception of our first meeting at the coffee shop, we'd never actually been out in public together, and I wasn't sure what the protocol would be. Was this a "date?" Just two friends hanging out? Would she know anyone there? Would she be embarrassed to be seen in public with a man old enough to be her father?

I took a deep breath and repeated the phrase that had become my mantra lately: "Don't overthink this." If Jenna was worried about any of that, she wouldn't have asked me to go, right?

By the time I got home it was late, and I didn't feel up to cooking. I knew Jenna was working at the diner this evening. She'd picked up a few extra shifts to make up for taking Saturday off.

I wondered if she'd mind if I came to the diner to eat. It would be nice to see her again, and I really did like the food there.

I decided to send her a text: "Would you mind if I came by the diner tonight to eat, or would that be weird for you?"

Several minutes went by before I got a reply. "No problem. Don't mind at all. Kinda slow tonight so service should be fast lol. Ask to be seated in my section, k?"

"Awesome. See you soon," I replied back, then went to freshen up and change clothes.

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The diner was indeed sparsely populated, and I found myself seated quickly in Jenna's section as I'd requested.

Jenna was soon at my table. "Hey there!" she said brightly. Then, more softly, "It's good to see you."

"Good to see you too, princess," I said, almost immediately regretting it. But Jenna just smiled, and I saw a hint of blush in her face.

"So, what can I get you? Prime rib again?" she asked, turning on her server charm.

"Nah, not sure what I want actually. What do you recommend?"

"They make a great lasagna here,"Jenna answered. "I take the leftovers home with me all the time. It's really good, always made fresh."

"Sounds perfect," I said.

"And to drink?" She asked.

I perused the menu for a moment. "Do they have anything good that doesn't have caffeine in it?"

"They have an herbal iced tea that's pretty good; no caffeine, not a lot of sugar."

"Not usually my cup of tea," I said, then groaned at my own pun. "But ok, I'll try it."

"Great. I'll put your order in and be back with your drink in a minute," said Jenna, spinning on her heels towards the counter.

As I watched her walk away, I admired her cute little outfit. Apparently the diner didn't have an official uniform, but Jenna and the two other female servers were all dressed similarly: a dark blue, long, flowing skirt and a white blouse. Stylish but comfortable looking.

Jenna brought me my drink, then went off to handle one of her other tables.

I tried not to stare at her too creepily as she worked, but I was enjoying watching her interact with other customers and her fellow servers as she bustled around, delivering some plates, clearing others.

I knew she'd spent all day in classes before coming here to work, but if she was tired, it didn't show. She was upbeat, perky and friendly to everyone she spoke with.

"Don't fall in love with her," I told myself, although it may have already been far too late for that advice.

Several more groups of people had come in since I'd been seated, but it wasn't a long wait for my food. "Here you go," Jenna said as she served me, "I know you'll love it." She leaned in a little, lowering her voice. "Sorry I can't socialize more, it got busy all of a sudden."

"No problem, kiddo, don't let me distract you," I said.

The lasagna was indeed superb; the herbal tea wasn't as bad as I expected either. In fact the more I sipped it, the more I liked it.

I ate my meal slowly, enjoying the hearty flavor of it. I looked around for Jenna but didn't see her anywhere. Perhaps she'd found a few minutes to rest, or was in the kitchen handling something. Eventually she reappeared, carrying some trays to a table.

I finished my food and was sipping the last of the surprisingly good tea when Jenna finally made her way back to my table. "Can I get you anything else? Dessert perhaps?"

"Nah, I'm stuffed. You were right, that lasagna was amazing. Tell the chef I said so."

Jenna laughed. "Told ya. Back in a few with your check." I tried not to stare at her ass too long as she left.

She returned a few minutes later, carrying the check and a small white paper bag.

"Your check, sir. And I bagged your dessert to take home," she said, casually putting the bag on the table.

I was confused. "But, I didn't order a..."

"I'm sure you'll enjoy it, sir. It's freshly made," Jenna said, cutting me off. "Although it's probably best you wait to open it til you get home, so it doesn't get...messy." With that, she dropped me a subtle wink, and was off.

I sat there with a confused grin on my face for a moment. Then I went off to pay my check, making sure I left Jenna a nice tip.

I turned to look for Jenna one last time before I walked out the door, but couldn't see her.

I had just gotten in my car when my phone buzzed; a text from Jenna: "Don't open it til you get home. Text me BEFORE you open it."

I may or may not have broken the speed limit on the drive back.

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I was already texting Jenna as I walked in my door: "I'm home."

While I waited for her reply, I kicked off my shoes and plopped on the couch, the little bag on my lap.

My phone buzzed. Jenna's text: "Did you open it yet?"

Me: "No. Waiting for permission."

Jenna: "Go for it. 😉"

I eagerly opened the bag, reached in, and pulled out a pair of soft, white cotton panties.

"Holy fuck," I said out loud.

I immediately brought them to my nose. They smelled of fresh sweat. She'd probably been wearing them her entire work shift if not all day. Turning them over I found the gusset; it was damp and discolored. Inhaling, I could smell the fresh, strong scent of pussy.

I fumbled for my phone.

Me: "Holy fuck, Jenna! Thank you!"

Jenna: "You like?"

Me: "Hell yes! They're amazing!"

Jenna: "You'll like this too..."

Moments after that text, a picture came through. Jenna from the waist down, blue skirt pulled up, the white panties clearly visible, snug up against her round, plump mound. I could see the shadow of her pubic hair through the fabric. A perfect cameltoe highlighted her slit, damp with arousal.

Before I could even reply to that, another picture came through. Jenna's thighs framed either side of the picture. Her panties were pulled down, stretched out between her knees. She must have taken it from a seated position, pointing the camera down. The gusset of the panties was clearly visible, with a wet, sticky spot right in the middle.

My cock was straining to get out of my jeans as I sniffed the panties again while looking at the pictures.

I started to type a reply when another text came through.

Jenna: "Wish I could chat more. Busy at work. Enjoy. Send me some pics, wanna see your reactions, can't check them at work though. TTYS OK? Have fun 😉 💋"

I typed back a quick "OK," then took another deep inhale of Jenna's powerfully fragrant feminine scent.

My addiction to the scent of pussy started from the first girl I'd ever fingered as a young man, and it had only grown over the many years. I hadn't had many girlfriends before I met the one who would become my wife, but I was always incredibly excited every time I was intimate enough with them to be able to smell their unique scent.

No two women smell exactly the same, although they all share the common pheromones that evolution had decided most attractive and alluring to the male of the species.

Most of my past lovers, including my now ex-wife, indulged my obsession with an amused indifference. They were happy to let me sniff their panties as part of our foreplay, even happier to allow me to spend great lengths of time going down on them, savoring their taste and scent as my tongue brought them to orgasm over and over again before finally fucking them.

But very few actually offered their panties to me voluntarily. Only one early girlfriend had left her panties on my pillow once as a surprise birthday gift.

After my divorce, indulging in my worn panties fetish was relegated exclusively to purchasing them online. Although, as with paying for a prostitute, I found this overall less satisfying. No matter how beautiful the woman I'd purchased them from was or how wonderful her scent, it still felt impersonal.

Panties always smelled better, were more arousing, when they were from someone I knew personally. But since I didn't date often anymore, and I certainly wasn't some creep who would go through female friends laundry baskets, (ok, full disclosure, I'd done that kind of thing in my younger years, then I learned about consent and respect for privacy) getting my hands on a fresh pair of worn, smelly panties was very rare.

The first pair I'd purchased from Jenna as part of our initial "arrangement" had been incredible. Warm, sweaty from a full days wear, and damp with her arousal at watching me strip and masturbate to her.

I'd cherished those panties for weeks after, despite the eventual fading of scent.

These, though, were even more special. Jenna had offered them to me freely, unexpectedly, and of course without the incentive of money.

Again they smelled of young fresh female sweat from at least several hours worth of wear, and of course they also smelled strongly of aroused vagina.

But unlike last time, I was almost positive Jenna hadn't simply gotten aroused in this pair, but had fully masturbated and had an orgasm while wearing them. How she found the time at work, I had no idea.

I examined them closer, resisting the urge to bury my nose in them.

They weren't what I'd call "sexy" panties, the kind women wear specifically to look good. These were a practical pair of everyday, plain white panties, designed more for comfort than appearance. Not that it mattered to me, of course. Jenna didn't know I was coming by the diner before she'd dressed. She hadn't planned on giving them to me hours earlier. It was just...spontaneous.

Examining the gusset closer, there was a thick dollop of white cream, still fresh and glistening. She'd cum hard in them. I knew I had to taste her.

I lapped at her cream gently, not wanting to gobble it all up in one lick. I flicked at it softly, collecting a small drop of it on my tongue and savoring her taste.

It was heavenly. I rolled her cum around on my tongue and up against the roof of my mouth. It was thick and smooth in texture, and tasted tangy, almost citrusy, but also a hint of sweetness. My blood was on fire in my veins, most especially in my engorged cock.

I stood up and stripped off my clothes quickly, and almost sat back down again when I finally remembered I'd want some lube.

I took the panties and my phone with me to my bedroom, pulled my lube out of the dresser, and relaxed on my bed.

I sniffed Jenna's fragrance yet again, and was about to take another taste when I remembered I was supposed to send her some pictures.

I felt a little awkward about it at first, especially since she wasn't really available to actually chat at the moment. But she had asked, so I figured I'd try to make it interesting.

I held the panties to my nose with one hand, my phone off to the side with the other. I had to use the timer, and it took me several tries before I got one that captured the moment just right.

I tried another one, this time with my tongue extended, tasting another drop of her gooey cum. Again this took several tries.

I sorted through them, sent the two I felt best, and deleted the rest.

I had an idea for one more picture I wanted to send. I put a pillow by the edge of my bed and laid Jenna's panties out over them, spread out flat with the crotch facing forward. Placing my fully erect cock over them, I positioned it so it was laying directly over the crotch, where her pussy would be if she was wearing them. I took the picture and sent it with a message: "wishing you were here."

Satisfied for the moment with taking pictures, I settled in on my bed. I opened the pictures Jenna had sent me on my phone and lay it next to me within easy view.

I squirted out some lube carefully, not wanting to get too messy, held the panties in my left, lube free hand, and began slowly stroking with my right.

I alternated between inhaling Jenna's scent and tasting her flavor, each sending thrills of pleasure through my body as I slowly masturbated. My eyes constantly gazed at her pictures, especially the one with her skirt pulled up, showing the panties on her body.

I used my fingers to enlarge that picture, zooming in on her panty covered pussy until it filled the screen. I could see the outline of every curve and fold under the thin white fabric of the panties I was now again holding to my nose, as I imagined breathing in her scent while they were still on her.

I looked at her slit, clearly defined in the picture, then at the panties in my hand. These had been right up against her pussy, had touched it as I had never done, had soaked up her juices as they dripped from her aroused vagina.

I inhaled yet again, shuddering in pleasure. I was taking my time stroking myself, imagining my face buried between her legs, feeling the heat of her hot young pussy under the thin material, feeling her juices soaking through them onto my tongue, hearing her moans and squeals as I pleased her.

I licked the panties again, imagining tasting her cream directly from the source.

I stared at the curve of her mound, the shadow of her bush in the picture. I looked inside her panties at the fabric that would have been directly against her pubic mound and to my delight found two short, fine red hairs. I picked them up carefully and rolled them between my fingers, feeling their soft texture. I thrilled at the touch. Although they were just hairs, they were from Jenna's most intimate parts, and I was finally touching her there, if only indirectly.

I tucked the hairs inside the little pocket-like piece of fabric in the gusset, then ran my fingers along it, feeling Jenna's sticky juices, knowing I was touching something that had come directly from her sweet young pussy.

I stroked faster despite myself, my cock swelling as I imagined touching, not her panties, but the warm, soft, sensitive flesh they concealed beneath them. I'd still never seen her pussy, just the hint of it in pictures, but I could imagine it quite clearly; soft, delicate pink labia, swollen clitoral hood, crowned by a fine patch of wispy red pubes springing from her rounded prominence of pubic mound.

My cock strained for release, and I could deny it no longer. I licked the fabric one last time, scooping up her remaining cream with my tongue, then buried my nose in them. I wanted her taste in my mouth and her scent in my nose as I came.

My cock exploded as images of Jenna, skirt hiked up and masturbating over her panties in the bathroom stall of the diner raced through my mind. I could see her eyes close and her teeth clench as she tried to stifle her squeals. Saw her creamy drippings filling her panties as my own cum splattered across my chest and stomach.

I thought about Jenna, bustling around the diner, serving customers completely unaware that their lovely young server was pantiless under her skirt.

I continued to inhale her scent as my orgasm slowly subsided.

Finally sated, I carefully picked up my phone, trying not to get it messy, and took one last picture of my cum covered cock, still mostly erect and glistening with lube and spunk. I sent it to Jenna along with a text: "Look what you do to me. Thank you for this special treat, you're amazing."

I reluctantly got up to go clean myself, then found a little baggie for the panties. I opened my dresser to put them with the original pair Jenna had given me, then wound up taking that pair out. It had been awhile since I'd looked at them, and the scent had faded long ago, but I still cherished them. They were a symbol of this strange journey that had begun months ago with an ad I'd placed to satisfy a kinky fantasy, a journey that had taken several unexpected turns since then and had led to this moment of adding a second pair of panties to what I'd hoped would be a growing collection.

I had no idea where this journey was headed next, only that I was really looking forward to the weekend.

I looked at the clock; it was just after 9pm. I knew Jenna wouldn't get done work until 10. Wanting to see her again, I sent another text: "Let me know if you want a ride home from work."

I found something brainless to watch on TV, my mind too occupied with other thoughts to truly focus on it.

10 o'clock rolled around. Then 10:15. Then 10:30.

I received a text from Jenna at 10:45. "Sorry, it was a nice night, needed the walk home to clear my head. Just got out of the shower, settling in for bed. Glad you enjoyed my present. ❤ your pics. I'm exhausted but gonna enjoy them for a bit 😉 😉 then get some 😴 TTYS. 💋 "

I smiled to myself, and replied back. "No problem. Get some rest. Don't stay up too late. 😉 Sweet dreams."

I waited a few minutes to see if she would reply, and when she didn't, decided to go to bed myself.

But sleep wouldn't come. I lay there in the dark, thinking about Jenna now in her bed, possibly, as she'd hinted, masturbating at this very moment to the pictures I'd sent her. I grabbed my phone and opened her pictures again. It suddenly hit me that she'd sent them via regular text instead of Snapchat, so I could keep them and look at them whenever I wanted. They didn't show her face of course, but still, it showed her trust in me was growing.

Something else was growing too. With a sigh, I retrieved her fresh panties from my dresser.

It only took a few sniffs before I was fully hard again.

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Djmac1031
Djmac1031
846 Followers
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