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 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 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 could have gone the usual route I supposed and found a woman in the escort adds 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 add on some local college sites as well as a few of the other personal adds 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 add, after much editing and rewriting, it 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 hours 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 adds, 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 like a real person. 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 add 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 certainly am 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 was figuring this was just never gonna happen. Then all of a sudden, 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 terrified 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 pic 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 to help you be able to recognize me.
See you soon.
Tom”
I actually had to hastily snap a few selfies then sort though them. I picked the one I thought 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 a few minutes, trying not to sweat or be nervous. I calmed myself down, and went in.
It was a small shop, not too crowded. I looked around for Jenna. I didn’t see her, so I found a booth and sat facing the door so I could spot her if she arrived.
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 petite, and short. 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 petite frame. Her pale thin legs seemed bare, no stockings.
All in all an outfit that gave me hope. It said she wasn’t embarrassed about highlighting her physical attributes for me, but certainly nothing that could be considered slutty or super revealing.
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 finally meet you. Been waiting long?” She said.
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 and 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, just 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 add” 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 at me 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’s 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, then replied “ok 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.
We finished our food in silence. Then she 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, so I said “go on, say what’s on your mind.”
She hesitated, then said “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…”
She broke in “I’m not getting naked, no. Sorry. That’s a deal breaker. Can’t do it.”
“I wasn’t going to ask that” I continued calmly, trying to keep her relaxed. Don’t blow this now, I thought. Then 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, and 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 coffee.
“Ok so I’ve thought it over and…ok, I can’t believe I’m saying this but…you have a deal.” And suddenly she put out her hand. She wanted to shake on it!
I laughed, smiled, 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, and winked.
Damn she was cute. And if she’s warming 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 room is just a few blocks from here. We can walk there. My roommates will be gone til late I happen to know. No one I know should see you with me.” She paused, then went on. “IF someone I know sees us, you’re my uncle, dropping by to, well, visit and lend me some money” and again she laughed. “Only a partial lie.”
“Good thinking, ” I said. “Last thing I wanna do is cause you any embarrassment.”
“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.” She blurted.
“Go for it” I said.
“I’m going to have my cellphone handy with 911 on speed dial. At any point you attempt to…break our deal, try and touch me, try to hurt me, and I’m calling the cops and reporting an attempted rape. I also carry pepper spray,” and 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. “I assure you you’ll need neither. But you’re smart to be cautious, I’d expect nothing less.”
“Then let’s do this before I lose my nerve” she giggled, and with no further talk, we headed for the exit.
————————————————-
The walk to her dorm room was short and quiet. It was a warm evening but 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, and could not help but imagine 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. ”
And with that she closed the door and I heard the lock latch.
I stood waiting nervously, hoping no one would come by. And hoping yet again she hadn’t changed her mind.
Then the door opened again and Jenna ushered me inside, quickly closing the door behind her.
“Sorry,” she said. “Just making sure no one was home. And I…well, I had to pee. Too much iced coffee ” she laughed nervously.
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, and a large wide-screen TV 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.” She finished.
“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.
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 I noticed. 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 check 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 in her eyes, but no fear. Good.
I checked the time on my phone quickly, then said “ok 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 disrobe 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, looked at me calmly and replied “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…?” She questioned.
I thought for a moment, then answered. “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 simply, and started to undress.
I struggled to keep my face calm but inside I was a storm of emotions. Excited, nervous, scared even. I was about to get completely naked in front of a beautiful young 19 year old college girl who I’d only just met. And 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 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 quiet the whole time. Hopefully.
“Really?” I laughed. “Well I suppose I can’t blame them. You truly are beautiful.” I said.
She blushed, then said “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 tingly touches with my fingertips. I also 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 asked suddenly “So what, no lube?”
Lube! I’d totally forgotten! Dammit, how could I forget the damn lube???
I cursed myself, but said calmly ” guess I didn’t think about that ” and laughed.
“Hold on a sec” she said, and stood up, headed towards the bedroom hallway.
She 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.”
Then she did something that 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 I almost forgot to say stop as the slippery lube oozed down my shaft, making my cock slippery and slick.
“Ok, stop” I finally stammered, then “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, because she said “trying to get your money’s worth, eh?”
I laughed. “Yeah I’m a thrifty consumer.”
“Well you also paid for something else, I think it’s about time you got it.” She said. And with that she suddenly 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 again, 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; 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 young vagina, mere seconds ago.
She’d already sat back down when my eyes finally found her again, and I looked at her, questioning with my eyes.
“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.” As she finished, she 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 kinds of 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 casually open. 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 again.
Then 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 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…34B. I know, they’re small, but…”
“They’re perfect ” I said as she paused. “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.
Her, her gaze alternating between my crotch and my face buried in her panties.
She finally broke the silence again. “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 30 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 20” I laughed.
“Oh come on, you don’t give yourself enough credit. You’re a good looking guy. Great hair, not balding, no gray. 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? 6 and a half? 7 inches?”
“Just under 7” I answered. This was great. This 19 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” she stopped herself again, like she was getting embarrassed talking about 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 ” and winked at her playfully.
She smiled again, and then replied “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, and I quickly continued “off your panties! I want to taste your panties I meant.”
“Ah, ok,” she relaxed and laughed. “Go for it.”
My tongue darted out and I tasted the sweet nectar of her essence that had leaked out onto the soft cotton gusset, and my senses went into overload.
This is what heaven tastes like I thought, and took another lick.
Again she must have read my face because she said “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 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, but then got silent as she realized I was getting close.
I looked over at her one more time.
Her green eyes sparkling, her lips pursed in anticipation.
Our eyes locked. Her lips smiled. “Go for it. Cum for me” she said.
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. My eyes opened 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 ” I finished simply.
“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. ”
Once again 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 as 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 ” I said.
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, and there was an awkward silence.
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, ” she replied. ” 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, paused. 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 feel 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, she suddenly cried “Oh wait! Don’t forget!” And ran back to the living room. She 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?” She said and smiled.
“Really? Thank you, Jenna. I’ll certainly…treasure these.” I smiled slyly.
“I’m sure you will. Get your money’s worth” she cracked back with a wink.
“Til next time then” I said and blew her a kiss as she closed the door.
It was 5:59pm.