Katrina Thompson, Trouble Ch. 01

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Might her liabilities exceed her fetching assets?
6k words
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Part 1 of the 2 part series

Updated 06/07/2023
Created 10/31/2015
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Part One of a two act story.

They had said that Trina Thompson was high-maintenance. Of course they were right, James and Nigel and Stash, and if anybody should have known it was them, and I ought to have heeded their advice. But I couldn't help myself.

I was in the grip of very great lust, not for the first time in my life, and I had reckoned that my keen and innate talents were sufficient to overcome whatever obstacles were in the way. Boy, was I in for a surprise.

"She is one predatory bitch," said Stash, perched on the armrest of our beat-up couch, his eyebrows furrowed, as he popped the top of his fourth Pabst of the night.

"But look at her," I insisted. "She's got a chest to fucking die for. And the way she flaunts it, waves it around, wears those tight tops? She's asking for it man, I tell you."

"Yep, asking all right," said Stash, between droughts. "And you are gonna pay for it. And pay for it, and pay for it until you wished you'd never set your miserable fucking eyes on her."

"But that's the trouble. I have set eyes on her. Those mighty tits. That Kardashian ass she wiggles around. Those big full lips on her mouth that deserve to be running up and down my cock." I gyrated my pelvis enough that Nigel laughed.

"That large-lipped luscious cunt those big broad hips just have to be holding, that will suck up my sperm up like a 100 watt Wet/Dry Vac."

Stash, whose ironic nickname referred to the sparseness of his determined but pathetic mustache, laughed hard, spilling some beer on our well-worn student-housing carpet.

"You know, of course, that she's plowed her way through just about the whole offensive line of the football team? Probably most of the linebackers too. Half of Delta Smegma."

James chuckled at this little joke of ours. Of course this referred to Delta Sigma Phi. All the cocks in our little foursome were circumcised, we couldn't help poking fun at the "sword in the scabbard" lot who tended, for reasons unclear, to dominate the ranks of that fraternity. Don't ask how we possessed this bit of intelligence.

"You don't believe us, go talk to one of them." James leered at me. "Don't do it, Chris, you will be one sorry hombre."

"She's eaten up and spit out better men than you, Chris," said Nigel.

I bridled at this. "You don't think my cock is up for a challenge?" I asked, eyes flashing. "I did Alisa Churchill four times one night last October, then filled her mouth good once more the next morning."

(This assertion was not strictly accurate, but was within our group's standard deviation of boasts, plus or minus one, except that we always rounded up. Still a higher truth-value than our beer consumption calculations, however.)

"Not concerned about your cock, Chris. Well, maybe a little. It is the peripherals that are gonna fucking kill you."

We argued back and forth a bit, but it didn't do any good. I was smitten. I wanted my prick doing all sorts of lovely things to this buxom big strumpet, my penis lodged in various places of her anatomy, having her sexual energy winding up my clock, coaxing me into catatonic states of climax. I wanted to be intimate and playing with every square inch of her body.

The guys listened and just shook their heads.

Stash sighed. "You go ahead man, go ahead. Don't let us stop you. But don't come back whining later, either."

Of course I had met Trina before, you could hardly miss her on campus, she occupied a lot of airspace, but that Monday morning before class I had run into her in line at the Starbucks just opposite the main entrance to the university. We traded chat for a few minutes at one of the unoccupied tables over our cups before we rushed off in our separate directions.

She is one big girl, taller than me when she has heels on, but round, broad, hefty. Her jeans were tight, her meaty thighs straining the fabric. A jaunty red beret topped her wild unruly dark hair, a leather jacket kept the early March cold of Boston at bay.

The only, albeit minor, aspects of her appearance (besides the fact that she wasn't supermodel thin, which didn't bother me in the slightest) that kept her from a five-star rating involved, unfortunately, her face.

Not that it was unpleasant - I liked her flashing brown eyes and beckoning smile, her hair and overall features. But she had one of those short pointed chins that doesn't really stick out much and mostly just retreated into her thick, fleshy throat. She also possessed a sharp, prominent nose. Together they gave her a vaguely porcine appearance. Nonetheless, she would rank at the top in looks for any girl I had ever dated, and she turned heads wherever she went.

Her eyes had showed interest while we talked at Starbucks, it was not my imagination. While I cannot claim, at that stage, that we "flirted," there was definitely something going on.

We had traded phone numbers and I texted her later that day, seeing if I could buy her lunch Wednesday. She responded sooner than I might have thought, a big Yes. Hot damn.

We had a good time that Wednesday at Rudi's, a sandwich place just off-campus, and my notion of some chemistry between us accumulated further evidence. She wore a blouse unbuttoned down a daring distance, and she made sure I got a good look at her cleavage when she leaned forward to talk with me over her pastrami-on-rye, those creamy big breasts of hers squeezed together into a lovely valley.

No doubt there was possibility here. She had a saucy smile and her eyes took in my shoulders, carefully cultivated flat stomach, and what I considered to be an acceptably handsome face. She absolutely oozed interest. I asked her out Friday night, to a restaurant usually beyond my means, hoping for good things. She said yes. Later that evening, back at our flat, my excitement in telling my suite-mates this piece of news had resulted in them voicing their dismal opinions on the whole matter.

I had planned to get us to the restaurant via the Redline "T" on Friday but she insisted on driving. A car, eh? This was apparently not your usual poverty-stricken undergraduate. Yes, she was a senior, and me only a sophomore, and the way she dressed did not suggest food vouchers were part of her life, but I still was completely blown away when she showed up at the curb in front of my flat in a screaming red Porsche.

Her smile - was it triumphant? taunting? - said it all. She was in charge - the BWOC, I then christened her in my head - the Big Wench On Campus. I hopped in the passenger seat, in a couple months she would likely have had the top down and her long dark hair flying in the breeze, but not yet, not now in early March.

She drove fast, confidently, and I admit I envied her ride, wondered what it would be like on a nice winding mountain road, what kind of drift I could get out of the car with the stability control disabled. I watched her hand on the gearshift while we drove, imagining those adroit fingers with the black fingernail polish running up and down my penis. I licked my lips.

It was a good dinner, although I confess to some panic at the prices on the menu. She laughed at my jokes, we each found out a bit more about each other. She was an only child, of an Anglo lawyer father and an Italian-American teacher mom, from mid-state.

It didn't appear that money had been much of an issue growing up. She was studying economics, no clear career plans yet. Her eyes flashed at times while we talked, an erotic challenge sent straight my way.

When it was dessert time I sidled over next to her in her booth and found a way to spoon-feed her bits of the luscious creme brulee we were sharing. Watching her tongue take in the creamy dollops I piloted to her mouth was intoxicating.

I had developed erotic plans for that tongue, that mouth with the soft big lips. She noticed my gaze and accurately read my mind, which I suppose was not all that difficult.

"You aiming to get into my shorts by any chance?" she asked, her face had a wry, amused smile.

"I think you would enjoy that as much as I would," I replied, a bit unaccustomed to this sort of directness but not afraid to send the ball straight back over the net. I tried to maintain a confident tone, and I certainly did not lack conviction.

"Couple things you'll have to do before that will happen," she said, folding her hands in front of her, taking me a bit by surprise.

"Although I am not necessarily adverse," she added, noting my somewhat unsettleed expression.

"You'll need a clean health report. The campus clinic can do this and have results within four or five days." Her brown eyes pierced me, unblinking.

This meant that tonight was perhaps not going to be an option. I flinched.

"Ah, but I have protection," I countered. "With me. No need." I patted my pant's back pocket.

She wrinkled up her face. "I hate condoms. And doesn't matter anyway, you will have to prove you are clear before anything happens." She stared at me evenly. "Pregnancy's not an issue but the other stuff is."

I should have gotten some idea then how this all was going to play out, all the different angles that would be worked, how I would get maneuvered around, but I was dumb stupid with desire.

And sure, I went in my head, if she wants to fuck bareback, making sure we were safe, there was nothing wrong with that. She hadn't said "no" - in fact she seemed to think a little sex with me was a fine idea. I could not refuse.

"Okay," I said with a confident smile. "You're on."

It turned out she was away for the rest of that weekend anyway, so my chances for some immediate excitement were not as great as I might have hoped, but we made a date for the next Friday. I sported an uncomfortable erection all week long just thinking about her, especially after I got the printed proof of my clean sexual condition on Thursday.

She had said 8:30, Friday evening, at her place. I contemplated bringing flowers or something and decided that was absurdly over the top, but I did take more care in showering and dressing than usual and stuck my toothbrush and a change of clothes in my backpack.

She lived in a suite with two other girls. She had said each of them had their own room, this intelligence had been imparted with a knowing glint in her eye. We wouldn't have to do the college roommate-in-the-way dance thing. Hot damn.

Her place was near campus, the second-floor flat of an old Victorian, a little rough around the edges but way nicer than any of my friends would have been able to afford. She greeted me with a short kiss and twinkling eyes at the street-level entrance.

She was dressed exceedingly causally. She had on a pair of those loose pants that were in style, with soft, patterned fabric, almost like pajama bottoms. Her bulging rump looked luscious as I followed her up the narrow wooden stairs, her ass crack clearly defined as she went, the soft fabric clinging to her cheeks.

Once inside I noted the short top that barely hung down over her balcony tits, you could just glimpse her navel from time to time in her soft belly as she walked about. Her boobs jiggled around enchantingly inside. Her hair was back in a ponytail. Just a little eye-shadow, but vibrant red lipstick.

The place itself was comfortable enough, high narrow windows with a view out to the street and the winter bare-leafed trees, dark wood wainscoting. It was handsomely appointed by student standards. Trina led me to their large living room, with a couch, a big TV and some furniture.

I was surprised at the presence of other folks, although I knew she had roommates. Another guy was sitting at a table, it looked like he had been opposite Trina's vacated spot, but maybe he was one of the other girls' boyfriends. I heard female voices in another room.

"This is Jared," she said, and the guy stood up and shook my hand. Tall preppy-looking white guy, confident face, polo shirt and khakis. He looked studious, practical, straight-laced. He eyed me keenly, almost uncomfortably.

"Engineering?" I ventured.

"Good guess," he smiled reluctantly. "You're right. Mechanical. And you?"

"Psychology," I replied.

We stood awkwardly for a moment.

"Your clinic report?" Trina finally asked, holding out a hand. It felt a little funny, but I took it out and passed it over to her, then noticed an identical form on the table next to Trina's spot. The name "Jared Williams" was on it.

I looked closely at her. What was up?

She laughed at my expression.

"Asta? Roberta?" she called into the next room. "Would you all come in here when you get a chance?"

My mouth must have been open, but Trina went on as if nothing was amiss. "Get you a beer?" she asked. I nodded and she fetched me a Heineken, more upscale than usual for me.

Asta and Roberta came in and we were introduced. I had seen Asta on campus, but Roberta was new to me. Asta looked Nordic, tall and almost too slender, with an angular face and thin narrow lips. Roberta was blonde and tightly built, like she rowed on crew.

I was getting increasingly confused, this was not the scene I was expecting.

"So, thanks for coming," Trina addressed Jared and me.

Jared and I exchanged a look. He appeared as undone as I was.

"It seems each of you has a notion of some intimacy with me, correct?" Trina looked closely at each of us.

How else was I going to respond?

"Absolutely," I said with conviction.

"Wouldn't be here otherwise," Jared said but shifted tentatively on his feet.

"Excellent!" Trina beamed. "So here is the deal, let me explain." The other two girls exchanged a smirk.

"I have always liked contests," Trina began. "Game shows on TV, feats of skill, singing, dancing, fitness, speed, contests of all sorts. When I was thirteen I loved watching re-runs of the Dating Game, all that kind of kitschy stuff. Tonight will be 'Friday Night at Trina's'!"

Jared and I eyed each other. What were we supposed to do, jump up and down and scream "hurray"? Would we be stuck answering trivia questions all night?

"Tonight's winner gets to have me," she said, "although not tonight, for reasons which soon will become clear. I will be your grand prize and I guarantee the winner will not regret it."

It turned out this last statement would not prove reliable.

"So here's the deal, boys. Thanks for your clean bills of health," she pointed at the clinic forms. "I like the looks of both of you. I like sex even more." She ran her tongue along her upper lip.

"You've cleared the first hurdle, proven yourselves clean. Now I want to get some measure of your, ah, stamina." She finished with a wave of a hand.

"I take sex seriously and expect that you do too. We'll find out just how good you guys are, how well your pleasure equipment is constructed, and it will be great amusement all around."

My imagination was only just beginning to get some traction and I hoped I was wrong.

Trina looked at her watch. "Quarter to nine it is. Whoever can come the most in the next two hours will be King of Friday night, Trina's new Best Friend. The Big Date will officially begin tomorrow for the lucky boy, enough time for rest and recovery and some first-class fun."

I never considered it a good sign when someone referred to themselves in the third-person.

Jared and I looked at each other, bewildered.

"You want us to jerk off in front of you?" asked Jared, taking a stab at the nature of our "contest."

"Seriously? And the guy who creams the most times is the winner?" His face grimaced in disbelief.

"No, no, no," Trina shook her head energetically, her pony tail went back and forth.

"That's too easy and isn't necessarily indicative of how your penis will respond when someone else is stimulating it. I imagine you both know your own cocks extremely well, how to prolong your pleasure, how to come a lot and so on. I am well acquainted with the sex behaviors of adolescent males and cannot imagine either of you guys is any different. Tonight has to be handled under a more controlled environment."

"Each of you will take a seat in one of those chairs," she pointed to two reclining type seats in opposing corners of the living room. I noted that each had been covered with a clean sheet. My stomach did a bit of a somersault as things became clearer.

"My esteemed apartment-mates will take turns coaxing your excitement forth, and the guy who comes the most times in two hours, that's a reasonable amount of time for a good love session, he's The Man." She clapped her hands together like a ten year old girl at the circus.

My inner wise-guy couldn't resist. "Aren't you going to measure semen volume too? That ought to count for something." Trina shot me a look that was both intrigued and dismissive.

"I care more about how many times a guy can get it up for me than the amount of sperm he squirts, to tell you the truth." She looked defiant.

"Gentlemen, take your places!" She waved her arms with a flourish, her tits swaying enchantingly. She sounded like a boxing referee.

Jared and I looked at each other. I shrugged and we each went to a chair. We were about to sit down when Trina told us to disrobe, completely.

This was totally odd, and of course Jared and I each stole surreptitious looks at each other while taking our clothes off, knowing that the girls were checking us out too. He had a nice body, I grant you, flat stomach, healthy looking shoulders, but I was more nervous than I wanted to let on.

My penis is very small usually, until excitement hits it. Jared's prick looked a lot longer, it was uncut, which always makes a cock look bigger. It hung and waved nicely, but it is always so difficult to tell, maybe I would be bigger than him when we were both erect. In any event, there was nothing to do about it, and we sat back, buck naked in front of these three girls. Luckily the heat was cranked up in the room or we would have been uncomfortably cool on the fresh cotton sheets.

Asta came to my side, Roberta to Jared's. I noted with some alarm that each of them had a length of rope in their hands.

"Put your arms behind you," commanded Trina.

"Huh? What the fuck is this, Trina?" I shot back. "What's the deal with trying to tie us up?" I was really pissed-off now.

"Hey relax, you big stud." Her eyes flashed.

"There is no harm involved. We're not gonna hurt you. Anytime you want to leave, you say the word, we'll let you free. But that means a forfeit." Her eyes drifted to Jared meaningfully. "It turns out that it is just better all around if your hands are restrained behind you and you aren't tempted, at all, to 'help out' while your mighty member is being stroked by the girls."

In a flash and with a sinking feeling I realized that this was not the first time this little "contest" had been held here. I knew from earlier discussion that Trina's name was the primary on the lease, was this one way her suite-mates repaid some of their rent obligations? Or was this just a game they all enjoyed? I swallowed hard.

Trina stood hands on hips, glaring at me, waiting for a comeback. God, her chest looked nice.

I cussed under my breath but put my hands behind me. Asta secured each wrist, looping the rope around the chair, not all that tightly, but enough so that I would neither be able to get off the chair without being untied, nor touch any part of my body with my hands.

So in a couple minutes Jared and I were secured, and a pair of hands began to work over each of our cocks. Asta was soft, slow, but given the situation it really didn't take long before I was hard. Jared took a little longer under Roberta's fingers, and I was relieved that fully erect we both looked to be about the same size. His cockhead had poked free from his foreskin, it looked smooth, red, arrow-shaped.

Trina had a gleam in her eyes. She went to a desk in the corner, opened a drawer and came back with a leather-covered notebook and a cloth tape measure.

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