Life of Paul Ch. 05: Jamie

All characters appearing or mentioned in this story are 18 years old or older. This story is a work of fiction and any reference or description to actual persons is unintentionally.

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April 2019

Her screams finally subsiding from her first orgasm, I pulled my length out of her as torturously as I had entered her. Just before the head come completely out, I thrust back in with all the force I had left. I'd already cum once this evening but a second was very close now.

I sped up my pace, slamming into this ass with as much need as I'd ever had. Her breath was caught in her throat as I continued my assault on her sex, her creamy folds tightening around my cock once again.

I knew I could make her cum again, so to play into her desires I slowed my pace slightly and reach to the ass on my right. She was still wet and ready from the fucking I'd had given her first. Without warning I plunged by two middle finger deep into her pussy. I knew well where her g-spot was so I stimulated it with intensity, getting her close in very short order.

Once close I withdrew my hand, still fucking the ass that liked to be kept waiting, and concentrated on my office sluts clitoris. Rapid circles and pressure elicited throaty moans from her and in a minute or so she came with a higher pitched "Ohhhhhhh". This made the ass I was fucking very envious.

To be kind though, after I made my office slut cum on my fingers and quickened my pace once again and didn't relent until I was ready to cum. I grabbed her waist hard and pounded into her until I blasted everything I had left into her silken sex. I came in a half dozen glorious blasts and felt, rather weakly, another orgasm from her as I withdrew my length from her.

I was totally spent but happy I was able to service all of these beautiful asses. As the festivities were now finished, I thought of nothing but a shower and sleep. However all four of the owners of these asses had other ideas.

They approached me, hands stroking my cock back to life slowly, a mouth or two on my neck to encourage it faster. I was whispered suggestions on what to do next and all of them sounded terrific. Those same hands now led me cock first up the stairs to my large steam shower.

A shower, definitely yes, but sleep; not likely.

#

May 2018

Tolstoy said 'The two most powerful warriors are patience and time'. What he didn't say was that those warriors often worked together and, more often than not, against you.

Before I knew what the fuck was happening, my 20 year high school reunion was upon me. The scary people heading the reunion committee tracked nearly all 500 of our graduating class members from 1998. And while I didn't hide who I am or where I was on social media, I went to great lengths to protect my personal phone number that only four people on the planet had. Since I was one of those people, and the other three were sitting with me watching a rom-com, I instantly knew who it was.

Ugh. No I don't remember you. Yes, I was aware it was coming up. No, I don't want to donate to the fund for decoration. Yes reconnecting is fun. Yes... No...I don't know... oh FUCK, fine. I'll be there, just email me the invoice. I hung up.

Seriously, the CIA interrogators could learn a lot from high school reunion committees.

"So," Amber said, amused, "Rancho Vally's 20th? Are you gonna go?"

"Are you," I shot back.

"Oh hell no," Amber said. "I hated almost everyone there and the ones I don't hate are either dead or here."

I tried not to wish I was a part of the former list of people she liked, but that didn't help that I was wrangled into going to a reunion. Shit. I really didn't want to talk to those people. Still, it would be neat to see how all the guys from the skater/surfer group turned out. Torn, I contemplated backing out until Tanya spoke up.

"Well," Tanya said, "if Amber doesn't want to go then I will. I'd love to see where you guys grew up." She was always up for an adventure of discovery. "Jess, what do you say?"

Jessica shook her head. "Nnoooooooope. I'm staying here with Amber. Reunions are pissing contests for guys, and even worse for women, and I don't care for that sort of shit. Besides, I already know Amber and Paul have the best 'where are they now' story, so why even bother going." She smiled in my direction. "And if no one believes you Paul, just show them the pics from our trip last month. They'll probably retroactively make you prom king for the awesomeness factor alone."

I smiled at the thought of those pics and that trip. The four of us in Germany's more colorful establishments, a couple of bottles of cherry brandy and damn few clothes.

That would certainly one up anyone else's tales by far.

I mulled it over for a bit longer. "Fuck it," I said. "Fine. I'll go. Tanya," I turned to her, batting my eyes sweetly, "would you be my date to my reunion? It would be fun to show you my hometown, and, as a side bonus, you would make spectacular arm candy to make me look super awesome."

She slapped by arm but smiled. "Don't be an asshole. Yes, I'll go. But you're buying me a new dress. Something with slink."

Tanya in a slinky dress? Maybe this won't be so bad after all.

"If we're gonna go and do this, we're going to at least have fun. How about a road trip? We'll stop a few places along the way, take a couple days to drive down. You know, enjoy the trip." I let the implication hang in the air.

Tanya smile slyly at that. "Now you're talkin'. This is gonna be the best reunion ever!"

#

August 2018

I really thought I would never see this place again. Not because it held any bad memories or because it had some weird vibe. Simply because I had outgrown it. It was a town that had less than 100,000 people when I left, which contributed to the huge student body of Rancho Valley High School. Now it was a city with nearly twice the population and had four high schools. It's footprint easily tripled taking up space in what use to be scrub land and desert. The vineyards, which it was famous for all over the country, also gained land beyond their old borders.

Despite the changes, it was weirdly nice to be back. My parents had long moved away and I had no family close by, so Tanya and I stayed at the nicest hotel in town, located on the Indian reservation, which was actually pretty nice. I booked us a room in their high roller suite even though I had no intention of doing any gambling. They were not overjoyed at this, but since I was paying for a room they

generally gave away, they looked past that.

The whole trip down was fun for Tanya and I. We stopped in San Francisco for a day and two nights and saw the sights and, at Tanyas insistence, shopped the shops. She picked up an awesome dress for the reunion as well as some other things for herself, as well as some things for Jessica and Amber. One of those things she modeled for me that evening, and I must say it was worth every penny.

After checking in and unpacking, I showed her the town.

It was really just like any other suburb you can think of. It had buildings that didn't go above four stories, apartments as far as the eye can see, an 'old town' section, a street that the kids cruised down, and of course the make out spot in the surrounding hills, which Tanya also found very enjoyable to visit.

The reunion was that evening so we retired to the hotel to change. I saw Tanya's dress on the rack and in the bag, but seeing her in it made me all kinds of glad that I bought it.

Sexy was a word for it. Seductive was better. But provocative would be my favorite adjective to use.

The dress was a gold patterned knee length number with the right shoulder purposely sewn down so it looked like it was falling off. The V down the chest was deep and showed ample side boob (or inner boob I guess), and the slit up the front of the left leg went well past her hip and above her belly button level. It was high enough to show that she wasn't wearing any panties and exposed a generous portion of hip and her entire left, perfectly smooth, chocolate thigh.

Black strappy heels finished the ensemble and her hair, normally a wild and free afro, was tied back in a tight bun.

My jaw was on the floor as she turned a full circle, letting me see the full view. If she stood still it could be considered a sensual outfit, but when she moved the top of the thigh slit shifted slightly away from her body, but never exposing her crotch. It was one of the sexiest things imaginable, and worth every penny of the outrageous price I paid the boutique.

"I take it," she mused, "that this meets with your approval? You mentioned being arm candy for you, so I wanted to make sure that everyone knew just how lucky you are." She turned around again and struck a pose, extending her left thigh out so it was in full view.

"You look amazing," I said, clearing my throat in an effort to breath normally. Even after all this time, she was a vision to behold.

She moved to check herself out in the multiple mirrors in the bedroom. "You know," she started, "I like the dress, but not sure it's practical for my plans."

Huh? What plans?

"May I inquire as to your possibly dastardly plans?"

"Well," she started, walking back to me she lifted the slit of her dress to reveal her freshly wax vulva, "I don't know if this lifts high enough for someone to say, smash their face into my pussy should the need arise."

Her smooth, hot sex was right in front of my face now, just begging to be touched, and licked, and possibly more. But not wanting to give totally in, I tried to sound cool.

"I can see the potential issue there. Here," I said, sliding off the bed onto my knees. I lifted her left leg over my right shoulder, "In this position, one could very easily reach you pussy with hands and/or mouth."

She stared down at me, smiling. "Shall I demonstrate?" I said, and dove into pussy with my tongue before she had a chance to respond. Her excited inhale was exciting for me to hear.

I flicked my tongue quickly over her as I kneaded her ass from between her legs, switching between flicking and lapping circles around her clip. My fingers finding her warm folds and playing with her wetness before slipping my thumb into her pussy. She moaned deeply as I inserted, and deeper still when I applied pressure to her clit.

Standing sex in any form is sometimes difficult. More so given the usually vast differences in height, flexibility, and other factors. However in this position, with her left braced on the bed and her hand gripping my head, I was able to lick Tanya's clit effectively with my tongue while playing with her entrance with my thumb. After a few minutes of this the effect was what I had hoped to for.

"Yes, shit, that feels awesome, fuck, just like that," she panted, gently bucking her hips to my mouth. "Holy crap that's gonna make me cum. Keep fucking me with your thumb, deeper, deeper, thats it. Fuck fuck FUUUUUUCCCCKKK" she moaned loudly. I felt her pussy convulse around my thumb, but I held the pressure through her orgasm. When she finished I withdrew and she put her leg back down, sitting down heavily on the bed and laying back.

"God damn, Paul, that was awesome," she said. She spotted the large bulge in my pants and turned over towards me. Her hand touched the bulge my long, thick cock was making, and it responded to her touch with enthusiasm.

"My, my, what have we here," she quipped. She stroked the front of my pants a bit, quickly moving towards the buckle. A few deft movements and my erection popped out. She stroked the shaft and stared planting small kisses around the base, moving up the shaft and finally rolling her tongue around the head, licking at the pre cum that had formed.

She tongued the head and then slowly, carefully, started taking me into her mouth. Her lips were stretched over my girth but she was still going down. She stopped about half way and started bobbing up and down, stroking the shaft in time with her head movements.

Her tight, wet mouth did a quick job of getting me ready to cum. I usually last a lot longer, but it seems she had a mission to get me off as quickly as possible. Her quick but steady speed and the wetness her mouth was giving were enough to do the job well.

"Im gonna cum soon," I told her.

She raised her head from the blowjob. "Good. Cum in my mouth, I don't want to get anything on my dress or hair." She resumed her blowjob at the same pace. After another minute of her awesome oral assault, I felt the first spurts of cum explode into her waiting mouth. She stopped the head bobbing but continue to jack me off, stroking out every bit of cum she could.

When I was spent, she made a show of opening her mouth, showing off the lake of cum I shot, and swallowed it with a loud gulp. "That was fun, but we really should get ready," she said, and hopped off the bed.

After a blowjob like that, I highly doubted the rest of the evening was going to be much fun.

I should have learned by now not to doubt such things.

#

The gym, where I spent very little time except in phys. ed. class, was just as cavernous as I remember. Its max capacity in my time was 3 thousand, but they seemed to expand it so it could easily hold twice that number; two full size basketball courts end to end were marked out on the floor.

You'd think the least they could do was rent a carpet or something to make it less gym-like. Oh well. The gym looked suitably festive with the banners for the various '98 sports teams achievements, academic teams accomplishments, and even all the old clubs banners hanging around the perimeter. A stage at the far end was setup with a DJ playing all the hits of the mid-late 90's to complete this trip down memory lane.

Honestly, it was weird more than anything, but it was also great to see some old friends. A lot of talk happened between us; about where we were now, what we were doing, who we married (or didn't), and how I landed as fine a babe as Tanya. It was not uncommon for me to be considered un-cool, cause you know, high school. So the fact that Tanya was with me made many a former nay-sayer speechless.

"Met her in a parking lot," I told them. Which, technically, was true. They didn't need to know the rest.

After quite a while of this I retired to the table we were assigned, Tanya having two empty wine glasses in front of her already.

"Drinking till' I'm pretty," I asked as I sat down next to her. "No," she replied, "but this wine is amazing."

I looked at the bottles. It was grown just down the road. There were perks of living right next to wine country. I snagged a glass as well.

"Hey Paul," a feminine voice called from behind me. I turned to see and was gobbsmacked at who I saw.

Jamie.

Of all the women I knew from high school, Jamie was always funny, good people to hang out with, and cute in her tomboy-ish ways and dress. After Amber brought me into the wide world of women, I always suspected that Jamie was something special. She never was obvious or flirty, but she had a quiet humor and near constant smirk.

She wasn't wearing her smirk now, but a friendly and wide smile. Her dark brown hair was in a messy up-style affair, and her round face, high, freckle covered cheeks and vibrant hazel eyes were exactly as I remembered. She was a head shorter than me, petite but curvier than I recall, although that was probably due to me never having seen her in a dress before now. Her dress was delightfully unexpected from what I remember her favoring back in the day.

A deep blue, the dress was short, tight, and had a bandage look that is popular it seems. A significant portion of the middle, mostly the cleavage area, was a diaphanous polka dot material in a deep v shape, with side panels going from her arm pit to the top of her hip in the same material, showing off no small amount of side boob and hip.

What also shocked me pleasantly was how large her breasts were. At least a full DD, they stood high and proud on her frame, creating a deep valley in the front and an awesome side view as well.

We're this a normal high school function she'd be escorted out for such a dress. But then again so would half the women here. Showing off at reunions was to be expected and something I was wholly grateful for.

My expression was probably obvious, cause Jamie stood there amused. "I guess this is a bit different look than you remember seeing me in, huh?"

"Wow," I said as I stood and gave her a hug, "you look amazing, but I always thought you were lovely."

She smiled, "Yea, but with a 3XL to large sweater that went over everything." She sat down at the chair next to mine.

"Ahem," I heard from my opposite side. Tanya was smirking as she sipper her wine. Doh!

"Ah, sorry, Jamie, this is Tanya, Tanya, this is Jamie, my friend through photography, science, cooking, and drafting classes."

"I was just playing with Paul," said Tanya, smiling. She shook hands with Jamie. "That dress would make any man stumble. You look great."

"Thanks, yours too," Jamie said, blushing slightly and absently smoothing her dress. "I never wear things like this so I thought it'd be fun."

We chatted for a half hour or so, reminiscing about classes and teachers, laughing at how some folks turned out and remembering absent friends. Jamie seemed happy to speak of the old days, but also sounded to have a lot of sadness, like she missed something small but significant. I tried to place it but was distracted when Jamie mentioned the beach parties we use to have. I mentioned to Tanya that we should hit the beach before we leave, not for the least reason but to see her in a bikini.

"Oh," Jamie said "Speaking of which...a bunch of the group were meeting up to go night surfing. Not sure if you knew or not."

"Really!?" I was stoked to go night surfing, mostly cause I hadn't been in years. But I didn't want to leave Jamie alone, and I really, really wanted to talk to her more; especially while she was wearing that dress. Thankfully, one of my better demons was there for me.

"Go ahead and surfer boy out," Tanya said. "I'll keep Jamie company." Jamie seemed pleased at this idea.

"Awesome! And I know just where to start. Rolled tacos!"

"Awwww," I whined, "you're hitting up Albertos without me? Traitor!"

I saw a hint of that playful smirk again. "You surf, you lose. But don't worry, they're open 24 hours, we can get some later." That sounded promising indeed.

I rose and told Tanya I'd see her back at the hotel. She pulled me into a quick kiss, whispering in my ear. "Take your time, have fun, but don't hurry back. Jamie seems to need someone to talk to and I want to help her."

I nodded understanding to Tanya, pecked her cheek and went off to my friends, already gathering for our departure to the beach.

#

It was late when I got back to our suite. At least 3am. We surfed and talked and ate tacos around a beach fire. It was as if we'd never been apart. But thats the good

thing about good friends; you pick up right where you left off.

I entered the suite to find an empty room service cart with a couple bottles of wine, and an extra suitcase I didn't recognize. For a moment I thought I was in the wrong suite until Tanya emerged from the bedroom. She was slipping on a robe but not before I saw that was naked. It, as always, left me stunned until she covered up with the robe.

She sat down on the sofa and poured the last little bit of wine into a glass. Without preamble Tanya announced "Your friend is in trouble."

I sat down next to her. Tanya continued. "Jamie got out of a shit relationship a few days ago. That asshole basically said she was worthless, told her to go to this reunion and that he'd be gone with she got back."

She downed her wine in one go. There wasn't a lot in there but the effect was dramatic.