The Jenna Arrangement Pt. 01

I thought about it for a moment. "I'd like you to keep them on for now, if you don't mind. I'll ask for them...shortly."

She nodded and sat back, her eyes glancing over at her phone and pepper spray, then back to me.

"Then let's begin, " I said, and started to undress.

I struggled to keep my face calm, but inside I was a storm of emotions. Excited, nervous, even scared. I was about to get completely naked in front of a beautiful young 19 year old college girl who I'd only just met. What's more, I was going to masturbate in front of her. She was going to see my hard cock as I stroked it and pleasured myself, while smelling her panties.

Every nerve of my body felt electric.

To her credit, Jenna was already earning her pay. Her eyes stayed with me as I undressed; shoes and socks, shirt, then my jeans.

Standing now before her in simply my black boxer briefs, her eyes met mine, then scanned my body.

"You're in good shape for your age," she commented casually.

"Thanks," I said, "I work out a bit. Not a gym rat, but enough to keep the weight down," I laughed. She smiled back.

I had a brief moment of fear that my penis was gonna fail me because of my nerves, but glancing down I saw the bulge that showed off my package pretty well. Not fully erect yet, no, but a good start.

Jenna's eyes followed mine; she'd noticed my bulge too.

"You ok so far?" I asked.

"Yes," she said simply.

And with that, I slid down my boxers, removed them, and stood facing her, now fully nude.

I looked at her and watched for her reactions. Her face flushed, but she didn't appear scared or freaked out.

I was afraid she might avoid looking, but her eyes went right to my dick, which was, thankfully, starting to fill up completely.

Within moments, it went from plump semi to full raging erection.

I was still looking at her when her eyes met mine again. She smiled, a good sign.

"That's...impressive," she said after a few moments. "I've seen a few dicks before of course, but they were always already hard by the time I saw them. Never saw one actually grow before," she volunteered.

I was glad she was talking. It meant she felt comfortable and wasn't going to sit there quietly the whole time. Hopefully.

"Really?" I laughed. "Well I suppose I can't blame them. You're very beautiful."

Jenna blushed. "Thank you. I guess I'm glad I...you know, do it for you." She smiled again.

"Oh you do," I said, smiling. "Very much so."

With that, I sat down on the towel covered chair, and began to touch myself.

I started slowly, my right hand simply holding and applying gentle pressure to my shaft. I used the fingers of my left hand to gently tickle my balls. I wanted to take my time with this, enjoy every sensation, knowing this sexy, adorable young woman was seeing everything.

I kept my gaze on her as I teased myself. She was really starting to relax more, leaning forward a bit as if trying to get a better view, her eyes a mix of curiosity and...excitement? Or was that my imagination? Doesn't matter I suppose.

"So..." She started, paused, then continued, "so you're tickling your balls? I thought guys liked them more, you know...squeezed?"

She's asking questions! This was better than I'd hoped.

"Every guy is different I suppose. Some like a rougher touch there. I prefer a lighter, gentler play." I continued to demonstrate to her just how I liked my balls gently caressed, light, feathery touches with my fingertips. I started to slowly stroke my cock, which was so erect the veins were bulging. I hoped she could see them.

I was stroking slowly, teasing, really getting into it, when she suddenly asked, "So what, no lube?"

Lube! I'd totally forgotten! Dammit, how could I forget the damn lube???

I cursed myself, but replied calmly, "I guess I didn't think about that," and laughed.

"Hold on a sec," she said, and stood up, headed towards the bedroom hallway.

Jenna was back in moments with a tube of lube. "Yeah it's mine," she volunteered with an embarrassed giggle, "but you're welcome to some."

What Jenna did next shocked me. She popped the top off, held the tube right above the tip of my cock, and started to squeeze. "Say when," she said.

I was so surprised that I almost forgot to say stop as the lube oozed down my shaft, making my cock slippery and slick.

"Ok, stop," I finally stammered, "thank you."

She placed the tube of lube on the arm of the couch beside me. "In case you need more," she shrugged, as she sat back down in her chair. Her eyes once again focused on my cock as I worked the lube into it with my hand.

I quietly stroked myself for several minutes, really getting into exactly what was happening right now, this fantasy come true. I felt myself coming close to spurting, so I slowed down, almost stopped, and just breathed for a moment.

She must have understood. "Trying to get your money's worth, eh?"

I laughed. "Yeah, I'm a thrifty consumer."

"Well, you also paid for something else; I guess it's about time you got it." And with that, she quickly stood up and walked around behind her chair.

Her eyes met mine as her hands went to her skirt. I couldn't see anything, but I knew what she was doing as she reached under, bent down low, then straightened back up again.

She came up holding the most beautiful pink panties I'd ever seen.

She walked over to me, her face fully flushed now, but smiling as she held them out for me.

I took them in my left hand, the hand not covered with lube. My eyes were wide, my body humming with what felt like electricity.

"Thank you," I managed to stammer. "Jenna, these are...wow, these are perfect. Exactly what I'd hoped for."

They were hipster style panties; soft, cotton, pink except for the little white lace frill along the top.

Better, they were WARM. Fresh off her young, 19 year old body.

These had literally just been covering her cute round ass, and pressed up against her teen vagina, mere seconds ago.

She'd already sat back down when my eyes finally found her again, and I looked at her, questioningly.

"Go ahead," she said, "you paid for them."

I turned them over in my hand to find the gusset, the soft little cotton patch that had been directly touching her pussy just moments ago. They looked...damp! Oh my God they were WET!

"I've been wearing them all day," she said, noticing my reaction. "It's been warm today so they're probably a bit...sweaty. But you'll probably like that, right?"

"Also," she continued before I could reply, "they might have that other scent you're looking for. I suppose this excited me more than I thought." Jenna looked a little embarrassed, like she'd said more than she meant to.

I decided to say nothing, then just held them to my nose, and breathed her in.

So many scents hit me at once I almost reeled. A soft hint of fruit; maybe perfume, maybe bath soap. The distinct, salty scent of sweat. Not pungent like the body order of someone unwashed and filthy, but the clean fresh scent of a perspiring young female.

But the strongest scent was of course the unmistakable musk of her vagina.

It was incredible. Sweet, yet tangy. Floral yet earthy. The absolute incredible combination of scents that can come from nowhere else but the vagina of a sexually aroused woman.

I wanted to cum and pass out at the same time. The pleasure was simply too much.

My face must have looked strange to her. Suddenly she flushed again and began to stammer, like she was embarrassed. "Sorry, I hope they don't smell nasty, maybe I should have put on a clean pair earlier, but I wasn't expecting..."

I cut her off, gently. "Jenna, these smell amazing. Heavenly. It's the most beautiful scent I've ever smelled." I said with no lie.

She relaxed at that, then grinned sheepishly. "Oh. Ok, well then...good. Sorry, I panicked there. I've heard guys make jokes about how pussy smells, and I worried..."

Again I stopped her. "Don't pay attention to those idiots. Most men find the scent of a woman's pussy highly arousing. It's very natural, very normal. Highly erotic. Especially for me. The ones who make jokes are immature assholes."

I smiled at her, then took another deep breath of her panties.

It was an incredible feeling. To be smelling this young woman's most intimate scent, right in front of her. Looking in her eyes while I smelled her panties with one hand, masturbated with the other.

Her eyes went back to my cock as I returned my attention to it.

She was sitting more relaxed now, her legs open casually.Not open enough to see up her skirt, but certainly giving me a hint. She saw where my eyes were focused.

"You ok?" I asked. "Don't mind me...looking at you?"

"I'm fine," she said, smiling. "Get your money's worth I guess," she joked.

She crossed her legs in a way that caused her skirt to ride up just a little. Again, I couldn't see anything truly revealing, but certainly had a nice look at her upper thigh and where it would curve back around to her ass.

She caught my eye again, and winked.

She was having fun. Enjoying herself. Maybe not sexually aroused, or not entirely, but certainly relaxed, having some fun with it, and comfortable enough to even be teasing me. It was as much as I could possibly hope for.

My eyes went from her legs to her breasts. I remember wondering earlier if she was wearing a bra. Now, I was pretty sure she wasn't. I could clearly see the outlines of her perky nipples protruding through her tank top. And maybe it was my imagination, but I could swear it was showing a little more cleavage than at the coffee shop.

"Can I ask, what size are your breasts?" I ventured cautiously.

"Oh, um...34A. I know, they're small, but..."

"They're perfect," I said. "Don't apologize. They suit your frame wonderfully. "

She smiled, said nothing more.

We sat silent again for a few more minutes. Me, jerking my straining erection, testing the limits of my endurance while continuing to smell her divine panties, my eyes drinking in looking at her young nubile teenage body.

Jenna, her gaze alternating between my crotch and my face, buried in her panties.

She broke the silence. "So by the way you're looking at me...you find me attractive I take it? Sexy?" Her voice was questioning, unsure.

"You're incredibly beautiful and sexy, Jenna. I can't take my eyes off you. If I were thirty years younger and...well, not in THIS situation, I'd be tempted to ask you out on a proper date."

"Tempted?" she questioned.

"Well I assume you have a boyfriend or something already and...ah hell, who am I kidding? You're out of my league even when I was twenty," I laughed.

"Oh come on, you don't give yourself enough credit. You're a good looking guy. Great hair, not balding, no gray. Although gray can be hot on some guys. Good body for a middle aged dude. Certainly not like all the overweight dads I see dropping off their kids here. I bet 30 years ago you were pretty damn good looking."

"I was a tall skinny geek," I replied, "but thank you, Jenna."

"Plus you've got a great dick," she spat suddenly, then bit her lip like she didn't mean to say it.

I laughed. "You really think so? You can be honest. I won't try to push any boundaries of our agreement, I promise. But you can tell me what you honestly think."

She smiled, relaxed. "Yeah ok. No really, it's a nice dick. Big, but not TOO big. I'd guess, what? Six and a half? Seven inches?"

"Just under seven," I answered. This was great. This nineteen year old was talking about my dick as I was jerking it.

"That's a good size. Big enough to be filling. Not big enough to hurt. And the curve is nice too. Not too curvy or bent. Just enough to hit the...the right spots." Jenna stopped herself again, like she was getting embarrassed talking like this.

I didn't want to push her too hard, so I just said, "Well thanks for the feedback, I'm glad it meets your approval." I winked at her playfully.

She smiled again. "Yeah, it does. Maybe another place, another time, I mean... I wouldn't date you now, of course. It would never work. But I hope when I'm your age I'd have a guy that's in your kinda shape and still has the ability to use what he's got."

We both fell quite again, and I focused my attention back to masturbating.

I'd already been edging for quite some time, and had used the opportunity of our conversations to relax and let things ease up a bit. But I could only hold things off for so long I suppose.

Suddenly I realized I hadn't done something yet.

"Jenna?" I asked. "I hope you don't mind, but...I really want to taste your pussy."

Her eyes went wide, shocked. I quickly continued, "Off your panties! I want to taste your panties, I mean."

"Ah, ok," she relaxed and laughed,"go for it."

My tongue darted out and I tasted the sweet flavor of her essence that had leaked out onto the soft cotton gusset. My senses went into overload.

This is what heaven tastes like I thought, as I took another lick.

Jenna must have read my face. "That good, huh?"

"Oh Jenna you have no idea, it's..." I was speechless now, absorbed in her scents and tastes, my penis raging, begging to be allowed to finally explode.

Wanting both hands free, I managed to slip her panties over my head so that the still warm, wet crotch was directly over my nose, then focused on teasing my balls while my other hand worked more steadily up and down my throbbing shaft.

I heard Jenna giggle. She must have found me a pretty funny sight with her panties over my face. Then she fell silent as she realized I was getting close.

I looked over at her one more time.

Her green eyes were sparkling, her lips pursed in anticipation.

Our eyes locked. Jenna smiled. "Go for it. Cum for me."

And that was all it took.

The first blast of cum launched from the tip of my cock in a long, thick stream, landing with a wet plop on my chest and stomach. Wave after wave of pleasure shot through my entire body as my back arched in the chair and my cock blasted spurt after spurt of hot cum.

I think my orgasm lasted at least a full minute, maybe longer. Time was a blur by then.

Finally I came back down to earth. My body relaxed. I opened my eyes to see Jenna still sitting there, smiling a huge grin. When she saw my eyes open, she laughed and applauded.

"Wow. That looked like a really good one! Was it as good as you'd hoped?" she asked.

I still felt tongue tied. Finally I managed, "That was far better than I'd ever dared hope or imagine. It was...amazing."

"Well I'm glad you got your money's worth," she laughed.

I started cleaning up with the tissues, feeling a little self conscious all of a sudden, when she said, "Hang on, let me get you something better. "

She went down the hallway towards the bathroom, and returned a few moments later with a warm washcloth.

"Don't worry, it's mine, I don't mind. I'll wash it later," she said simply. I accepted it gratefully.

As I started to get dressed, I stole a glance at the clock. "5:45 pm. I'm right on time, as promised."

This is where it gets awkward I suppose, I told myself. The part where we both feel self conscious about what just happened. Hopefully she doesn't feel too weird, I thought.

I finished dressing, tied my shoes, then stood up. We were facing each other. Our eyes met. Her face was stoic, unreadable.

Suddenly, we both laughed, breaking the awkward tension.

"Thank you, Jenna. That was truly wonderful. You were exactly what I'd hoped for, and this experience was exactly what I wanted. No, scratch that. It was better than I'd ever could have expected. So thank you."

"You're welcome," said Jenna, "and thank you for being a perfect gentleman, for not trying to push the boundaries of our agreement. I appreciate that, and, well, I appreciate the money. It really will come in handy."

"A mutually beneficial arrangement then," I said, and again we laughed.

"And now as a man of my word, I must be going. I promised to be out your door by 6pm."

She walked me to the door. Then, to my surprise, gave me a hug.

I returned the hug, keeping it platonic, not trying to touch her intimately. But I couldn't help but notice her pert little breasts against my chest. Nor could I not think about her naked under her skirt as I looked down at her ass.

As she pulled away, she gave me a light peck on the cheek.

"Maybe...if you want, you know...maybe...we could do it again sometime?" she stammered nervously.

"Jenna, look, I'm not rich, but yeah, maybe..."

She quickly replied, "Oh I know, it's expensive. Perhaps next time we can, you know...negotiate. "

She really wants a next time, I thought. Fascinating.

"Well, I have your contact email. I can reach out to you again soon I suppose, if you're interested," I ventured.

"That'd be gr...fine. That'd be fine," she said.

As I headed out the door, Jenna cried suddenly, "Oh wait! Don't forget!" She ran back to the living room, scooped up the panties I'd left on the couch and handed them to me.

"Keep them. I mean, you did pay for them, right?" Jenna blushed and smiled.

"Really? Thank you, Jenna. I'll certainly...treasure these." I grinned slyly.

"I'm sure you will. Get your money's worth," she cracked back with a wink.

"Til next time then," I said, blowing her a kiss as she closed the door.

It was 5:59pm.

To be continued...