Changing the Rules of the Happiness Game
Copyright© 2022 by NotReallyAshamed
Chapter 22
Romantic Sex Story: Chapter 22 - What's the secret to happiness? Rob thinks he's found it when his sister snuggles up to him, but as time passes the rules of the game keep changing out from under him. And his relationship with his best friend and his friend's mother is confusing, to say the least.
Caution: This Romantic Sex Story contains strong sexual content, including Mult Teenagers Consensual Romantic Gay BiSexual Heterosexual Fiction Incest Brother Sister Masturbation Oral Sex Petting Small Breasts
That weekend I made good on my resolution, staying at home and knocking off two papers, English and government, and convincing myself that I was in good shape for the math exam, traditionally my weakest subject. Lily sat quietly with on my bed much of the weekend, providing moral support and encouragement, and occasionally going out to bring me snacks and water.
She also read my papers — I expected find them boring or incomprehensible, but she surprised me with a few cogent comments. As quiet and unassuming as she usually presented herself, it was easy to forget that she was an unusually intelligent person; probably smarter than I had been at that age. She wasn’t the sort to tie herself into knots analyzing things, but her instincts were reliable and the ease with which she understood the gist of my high school senior course-level papers belied her age.
On Monday morning, as we took the elevator down together, she wished me good luck on the test then surprised me with a deep kiss, letting go just before the doors opened into the lobby. I felt a little ashamed that I hadn’t asked her much about what she was facing at school; surely at the very least end-of-term tests? Her summer break, I thought, would begin around the same time as mine.
The math test turned out to be a breeze. I’d never exactly been great shakes at math, but pre-calc as they called it basically seemed to be a rehash of stuff I’d already picked up in algebra, geometry, and other earlier classes. And our teacher was pretty good. Or maybe I was just getting better at math. I figured I was probably going to get at least a 90 in the class, maybe even better, and I was in a very good mood when I met Timothy and the guys for lunch.
It didn’t hurt that I had two term papers in my backpack ready to turn in early, if I wanted to, though I had been thinking about taking Timothy up on his offer to go over and retype them into his home computer, since they weren’t actually due until the next week. He had a so-called “word-processing” program that apparently would let me generate a perfect copy with no errors, and while he didn’t have a printer, one his friends, David did and had offered to print all of our papers out. hey’d been doing this since freshman year and I’d seen Timothy’s papers and been impressed; they looked professional.
Timothy brought the offer up at lunch and I agreed — I’d go over there on Friday and we could type the papers, hang out, and generally have ourselves another fun weekend. I was a bit apprehensive about seeing Alice again, but I figured I’d politely decline any wine and grass and hopefully nothing too bizarre would happen. As for getting physical with Timothy, as he evidently was expecting — well, I’d deal with that when the time came.
My mood only got better that evening, when Lily confided in me that her period had arrived - in fact a bit earlier than she’d expected. I hadn’t realized how my anxiety about her getting pregnant had been hanging around in the back of my mind, adding to my general feeling of stress. The good news buoyed my spirits, indeed made me feel almost giddy, to the extent that Dad even commented at dinner that I seemed to be unusually happy and asked, only half-jokingly, whether I’d met a girl at school.
I winked surreptitiously at Lily and, following her lead, mumbled something about having a crush on someone named “Alice” (I regretted the choice of name as I said it). If I thought that would get him off my back, I was greatly disappointed; he pressed for details, as Lily tried desperately to keep from cracking up, and I did my best to invent a generic-seeming not-really-girlfriend based on a girl in our friend group (who in fact I had had a bit of a crush on at one point — it seemed an eternity ago, though).
That night Lily came at midnight, not naked this time but wearing panties with a pad, as she did during that time of month. The sight of her topless, with her tummy protruding just a tiny bit over the white cotton of her panties reminded me of the days before we’d started sleeping fully nude every night and I was instantly erect.
She was eager as ever to make love, but I wasn’t quite sure how that would work — wasn’t she bleeding down there? I was unclear on the anatomical details. In the end we found a good solution; Lily clambered on top of me, took me between her thighs and rubbed herself back and forth against my hardness, clenching her thighs rhythmically. When I could tell from her breathing that she was getting close, I put my hand down the back of her panties and toyed with her anus, something I knew from experience excited her immensely. She slipped smoothly into an orgasm and then rested on top of me.
When she rolled off and saw that I was still hard, she asked shyly if she could taste it. I remembered the intense pleasure she — and I — had experienced when I had licked her down there the previous week; but I also, without knowing exactly why, didn’t feel totally comfortable with the prospect of her reciprocating.
Part of it might have been that I worried she would find the smell or taste off-putting, or that I wasn’t sure how she’d react if I ejaculated in her mouth or on her face. Or perhaps I just didn’t want to let go of her? Gazing into her eyes made me happy. So I guided her hand down and her fingers encircled my shaft, and, just as she had so many times before, she gently pulled back and forth until I moaned a warning and then glazed her tummy with hot semen. “That was so nice, Robby,” she said, quietly.
On Wednesday night, our parents dropped a small bombshell. They had been invited by friends of theirs (I didn’t recognize the name) to a weekend getaway in the Berkshires. There was some outdoor concert opening that weekend and their friends had two extra tickets; it was apparently a fairly big deal. They were planning to leave Friday afternoon, before we got back from school, and wouldn’t be back until Sunday evening. We were, they felt, old enough to stay by ourselves for a few days — after all they had frequently left us alone when they went for an evening — but they wanted me to promise that I’d be in charge and not leave Lily by herself.
I was of course thrilled at this development, though I anticipated some awkwardness with Timothy since I’d promised him I’d be spending the weekend with him, hanging out and entering our term papers into his computer. What I wasn’t expecting was the deeply hurt expression with which he greeted the news when I told him the next day at lunch, even though I framed it as having to take care of my little sister and explained that I had no choice in the matter (which of course was true, even if taking care of Lily was literally the thing I most wanted to do in the world). He acted chilly towards me for the rest of the hour and said he was too busy studying to hang out that afternoon.
I didn’t want to hurt Timothy, of course, but I thought it was unreasonable of him to be getting that upset — things come up! In any case, my overall elation with how things were shaping up and the general end-of-term excitement conspired to prevent me from worrying too much about it. I would be spending a whole weekend alone with Lily! We could spend two whole nights in each other’s arms without worrying about being caught. We could take baths together again. We could have dinner together and pretend to be a couple — hell, we could even go out for dinner and pretend to be a couple! Lil’ll enjoy that, I thought.