Chapter 1

Authors Note: This was a P A T R E O N supported story I wrote over the summer. If you want to support me (and get early access to some of my stories) you can find a link here: https://www.deviantart.com/polarisdreamer/journal/ I-made-a-**-918180558
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First Year of Law School

Looking back, my first year of law school was everything I had hoped it would be. In many ways it was like senior year of college part two, only with a lot more work sprinkled throughout and, consequently, slightly less fun. Like college, I got good grades, made some friends and dated a few beautiful ladies. Actually, ‘dated’ is probably not the right term. I’ve got this thing about making commitments, I’ve really never had a steady girlfriend.

This year a number of ladies expressed an interest in dating me exclusively, but I just didn’t want to limit my options. However, there were two girls that I really liked: Beth and Jillian. They were smart. They were sexy. And they were roommates. This is the rather complicated story of my relationships with Jillian and Beth…

I had my eye on Jillian since the first week of Law School. I first saw her in passing during orientation and I met her in the library about a week later. I remember pulling my head out of a book I was studying, and all of a sudden being drawn to her gorgeous figure approaching me.

Her beautiful long blonde hair covered most of her face, but I knew I'd see it soon enough. My eyes drifted lower and paused at her ample breasts, her blouse was strategically unbuttoned revealing just a taste of cleavage. I continued scanning downward and appreciated the way her trim waist and luscious hips hugged her high-waisted skirt. The young lady had clearly mastered the fine art of making conservative attire rather provocative. Without a doubt she maintained a perfect hourglass figure but looked a little thin for my tastes.

She put her books on the table and sat down to join me, coyly asking, “Is this seat taken?”

She didn’t actually wait for me to answer before she rested her pert behind next to me. I didn’t voice one word of protest. I thought she had the most beautiful green eyes. Whether we were talking or flirting after that, we enjoyed each other’s company. Jillian was 5’8 and looked to weigh an athletic 135lbs. She explained she’d ran cross-country in college and judging from her fit features, especially her legs, I wasn’t inclined to doubt her.

Jillian was ambitious, sharp with her questions, and clearly loved intellectually sparing in a competitive way. She was a natural lawyer. She certainly seemed focused on achieving anything she put her mind to, and that night her mind was clearly set on hooking up with me.

Enter Jillian’s roommate, Beth. I’d met Jillian’s lovely friend in passing nearly a dozen times the first month of law school. At the time I was fooling around with Jillian on the regular, but never really got the chance to hang out with Beth alone and get to know her. However, as my fling with Jillian evolved into more of a ‘friends with benefits’ situation, thanks to the rigors of the semester taking over her schedule, I saw an opportunity.

Unlike Jillian, Beth and I were taking many of the same classes, studying in the same library and eating at the same times in the cafeteria. It was only natural that we slowly gravitated toward one another. I remember making my first move like it was yesterday. After a morning class we shared I noticed her sitting alone in the cafeteria. She was wearing a sleeveless white blouse, the same one she’d had on in class, but she’d since untucked the garment from her formfitting black dress pants.

“Hey Beth, mind if I join you?” I’d said, noticing Jillian’s roommate had grabbed two donuts for breakfast rather than something more nutritious.

Smiling nervously, Beth appeared tongue-tied, motioning for me to sit down instead of saying anything at first. Beth was a pretty bottom-heavy young woman with large breasts, a sweet personality and long wavy red hair. At 5’4 and a curvy 140lbs, she really filled out her pair of dress pants. Her hips were certainly wider than Jillian’s, and her thighs appeared thick but firm. I would only later discover this attribute was a remnant of her days playing soccer in college.

After that day, the more I got to know her, the more she began to open up to me. I came to realize from our time together that she was a sweet, sensitive, and passionate young woman who seemed out of place in the cut-throat world of law school. Built a bit thicker than Jillian, Beth’s body was more in line with my typical tastes, but still not thick enough to be perfect.

As I was growing closer to Beth, Jillian and I were still seeing each other now and again. After all, earth-shattering sex was a fantastic way to cope with the stress of law school, but as Jillian obsessed over her class rank and made less time for me, the time we did spent together tended to be shorter and more physical in nature than the time I was spending with Beth. Beth was well aware of my connection to her equally stunning roommate, so it took a few weeks before she began to warm up to me and lower her defenses.

The first time we hooked up was in the aftermath of a party after midterms. We were both **, Jillian was a no show since she had an exam the next day, and Beth finally confessed she liked me far more than a friend should. Reminding her that my relationship with Jillian wasn’t exclusive, Beth planted her first tentative kiss upon me.

The sex we had that that night was notably less aerobic than when I was with Jillian, I couldn’t help comparing, but strangely I found it more intimate and emotional. Whereas Jillian enjoyed taking charge during sex, often opting to ride me like she was at the Kentucky derby, Beth was far more submissive and enjoyed being told what to do. When I bent her over doggie style, with a perfect view of her shapely butt, we were both in heaven.

Beth later confessed to me that she had a thing for smart, funny, and athletic men such as myself. At that time, I was a lean 160lbs on my 5’11 frame with defined musculature all over my upper body. My muscles weren’t huge, but Beth clearly couldn’t get enough of them.

Over the next few weeks, we continued enjoying each others company and she seemed to accept my many rationalizations for why I wasn’t ready to dump Jillian and date exclusively. I made it clear that even though I was taking a break of sorts from the beautiful blonde the door between Jillian and I was always open.

Making my new ‘friends with benefits’ situation more complicated was the fact that my roommate Brian also took an interest in Beth shortly after I started seeing her. At 6’2 and 230lbs, Brian was hardly in as good of shape as me. It wasn’t all that surprising to me that Beth routinely dismissed his advances in a polite way.

Over winter break, things between Beth and I went on hold as we each spent time apart with our respective families. I lived in town, but Beth’s family resided all the way in New Jersey. Facing the prospect of being alone for nearly six weeks, I hit it off with a local fitness instructor and enjoyed some harmless fun during my downtime. Early second semester, I’d put things with my fitness fling behind me and was quick to rekindle my relationship with Beth. However, after a party one night Jillian and I rekindled things as well.

Beth had been out of commission with a bit of a cold. I remember vividly seeing Jillian approach me across the dancefloor, her beautiful long blonde hair pulled back into a tight ponytail. Her glowing green eyes fixated on me. My eyes drifted down from her intent stare to appreciate her ample breasts, before continuing down to her… her softened midsection?

Where once a thin and trim tummy existed, in its place now was a perfectly round little gut clearly straining every strand of the button-down long-sleeve crop top trying to contain it. Her newfound belly even bulged slightly over the waistband of her tight jeans. Her stomach was exposed. So entranced and excited was I by this unexpected development, that I didn’t realizes my eyes had lingered too long.

Her gorgeous green eyes noticed me staring at her puffy midriff, and she began to blush. She apologized to me, saying that she needed to invest in some bigger clothes, while I observed the strained button on her tight jeans with a certain sense of delight.

Playing it cool I sought to alleviate her budding insecurities, “Why? Tight clothes look sexy on you.”

“You think so? They’re a little uncomfortable, I wouldn’t mind some help taking them off.” Jillian seductively winked grabbing my hand and leading me away from the party to a secluded bench outside of my apartment where we quietly began to explore each other’s bodies.

I could feel that Jillian was no longer as firm as she’d once been, law school was clearly taking a toll on her figure. When she wasn’t coping with the stress of it all by having sex with me, I guess she was turning to comfort food. Instead of a lean 135lbs, she was more like a slightly out of shape 145lbs. Although still thin, she was now a little softer around the middle. Since there was no way I’d be able to make it up the stairs to my apartment without exploding, I led Jillian to the soft grass behind the bushes of my apartment complex’s backyard.

After Jillian and I hooked up again, it was a little awkward between Beth and Jillian. Since they were good friends and I had already stated that I wasn’t going to exclusively date anyone this year, we decided to address the awkwardness and make a deal with each other. Since we were law students, we decided to form a written agreement. They decided that it was alright to fool around with me as much as they each wanted, as long as I didn’t date anyone exclusively.

In the weeks after the arrangement was struck, the deal seemed to work out for all of us. The girls no longer felt like they were betraying or competing with each other every time they hooked up with me and I gained two reliable sexual outlets for both pleasure and stress relief as we all dug in for our rapidly approaching second semester midterms.

However, it soon became clear to me that Beth wasn’t nearly as excited about our arrangement as myself or Jillian. She revealed to me, she only went along with it, in hopes that I would eventually make an exclusive commitment to her sometime next year. Being a more sensitive person, I realized Beth required more emotional investment and aftercare than just cuddles after sex, so I made it a point to spend more time with her in the mornings after sex by making her breakfast in bed from then on out.

Beth had an appetite, and it was always a treat to watch her pig out, whether it was in the cafeteria, theater, a restaurant or in the bedroom. The beautiful red head really could pack away a lot of food, a talent she attributed to her days spent gorging herself with carbs after soccer practices in college.

As the semester wrapped up, I was delighted to discover one night that it wasn’t just Jillian putting on a few extra pounds. All the food she’d eaten over the course of the semester had taken a bit of a toll on Beth’s figure too. Seven pounds to be exact. At 147lbs the extra padding had found its way to Beth’s hips, thighs, rear and tummy. It wasn’t much, but I was all for it. I prayed that over summer break, both of my muses softening figures would continue to expand.

Summer Break

Staying at my apartment over the summer, only without Brian to keep me company, I didn’t follow the normal employment path most law students take. I hadn’t applied for any legal internships or paid clerking positions. Instead for employment I turned to a local water park called Wild Water World. Jillian had called me crazy when I’d first shared my plans with her and eagerly bragged about the competitive internship with her father’s law office that she had lined up. When I told Beth, she was more surprised than anything else, and shared she was less than enthusiastic about the plans she’d made to intern at a modest county courthouse back home. However, after a little bit of processing, Beth also questioned my logic.

My logic, as I explained it, was this: Law school was taxing on the mind and body, so I wanted to avoid burnout at all costs. I’d worked at Wild Water World every single summer away from college and had a wonderful time. The park was staffed largely by fit and attractive college-aged young adults, most were in fact college students.

What was better than hanging out with good looking girls in bikini’s all day? Hanging out with them at night, that’s what. Aside from that notable perk, the job didn’t pay well, but the water park did provide a 50% employee discount on food, plus rides would be free for employees to enjoy when they weren’t clocked in.

Working at the water park also gave me more time to spend with my younger brother Paul, who’d recently graduated high school and was poised to enter college in the fall. Paul was a shy sensitive guy, but a good, reliable brother. However, I couldn’t help but notice he didn’t have much luck with the ladies his senior year. He was 19 years of age, but never had a high school girlfriend. I’d always hoped growing up that some of my ‘mojo’ would rub off on him. I was constantly on the lookout for any opportunity for him to get some action. But for most of our adult lives, I was unsuccessful.

At 5’10 and around 190lbs he wasn’t a bad looking guy; he was just a little overweight and inexperienced around women. Two problems that I hoped to help him solve this summer working together at the water park as his personal trainer and wingman. After all he was about to enter college, he deserved to get some female attention.

Perhaps because of the honest admission I’d made about the motivations behind my strange choice in summer work, or because of the prospect of me meeting and dating other women, shortly after I’d told her about it, Beth spontaneously decided to remain in town over the summer and join me at the water park. Immediately my imagination got the best of me. Wild Water World had the longest enclosed waterslide in the world, ‘The Tunnel’, nearly half a mile long. The best part was that two people could ride the slide together, as long as their combined weight did not exceed 350lbs.

The idea of being in a hot, dark, wet environment for over three minutes with Beth laying on top of me sounded too good to be true. However, once Jillian caught wind of Beth’s plan to join me, she quickly backed out of her internship plans and hopped on board the water park train.

I was ecstatic, Beth was less enthusiastic.

Having two gorgeous law school hotties at my fingertips over the summer was a huge privilege, but also a problem. As rewarding it might be in the short term, juggling two women was never easy. As a partial solution, I decided I wanted to share my law school ladies with my inexperienced younger brother, if they were up for it of course.

My brother was the first person I needed to get on board, so after heading home across town, we talked. When I told him my plan for the summer, particularly regarding ‘The Tunnel’ and the fact that if he played ball, there would occasionally be two hot law school ladies in bathing suits lying on top of him, he was in. With that settled, I wasted no time in introducing him to my two lovers and seeing what they thought of my proposal.

For Jillian and Beth, they were open to the idea, but they had some concerns. Each thought my brother was cute and didn’t mind the idea of educating him on the art of making out before he shipped off to college but each of them made it clear that they wanted to share time with me as equally as possible. So, after some negotiation, we drafted a new contract for the water park and signed it.

1) We each commit to spending at least four days or evenings at the waterpark together and working the same shifts (as best we could manage). [Group’s idea]
2) While off duty at the waterpark our primary ride will be ‘The Tunnel.’ [My idea, which everyone liked]
3) We will alternate partners for ‘The Tunnel,’ opposite gender only, at every possible opportunity (Unless Jillian or Beth ever wanted to go down together). [The group thought of this idea, but that last addendum was all me. Call it wishful thinking]
4) There will be no exclusive dating of anyone signing the contract while we are working at the waterpark. [My idea, but everyone seemed to agree with this one]

Unknown to Paul… Beth, Jillian and I formed another secret fifth rule regulating ‘sleepovers.’ We decided that whom I spend any given night with during the work week would be determined by whomever road ‘the tunnel’ the most with me on any given day. [Thus, Jillian and Beth had a strong sexual incentive to ride ‘the tunnel’ as much as possible]

Overall, it seemed to be an agreement that everyone could live with. Paul liked that he was guaranteed to go down the slide with one of the girls every time, assuming that their combined weight remained under 350 pounds. The girls liked that they would be alternating turns with me, there was no exclusive dating, and that they could be rewarded for their participation by earning ‘sleepovers’ with me. I liked that I would be able to fool around with two exceedingly attractive aspiring young lawyers all summer long.