Changing the Rules of the Happiness Game - Cover

Changing the Rules of the Happiness Game

Copyright© 2022 by NotReallyAshamed

Chapter 14

Romantic Sex Story: Chapter 14 - 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  

Dinner was nearly ready by the time I got back. I wanted, desperately, to sit next to Lily on the living room couch, to feel her next to me, calming me down, recentering me, but I told Mom that I felt gross after wearing the same clothes a second day in a row and that I was going to take a shower and change before dinner.

Standing under the hot water, which pounded my back much harder than the somewhat anemic flow in Timothy’s shower, I felt almost like I was outside myself, observing myself in the third person. He relaxes under the shower. He looks pretty good, tallish, blond hair, blond curly pubes. He is still aroused, his penis is standing straight up, reaching for his belly button. He is touching himself... I sighed, began to relieve myself, confused visions of Timothy and Lily swirling in my head. It couldn’t have taken longer than 30 seconds before I felt the familiar pressure building; I forced myself to concentrate on one image, of Lily letting her bathrobe fall open in front of me. I groaned quietly and spurted semen all over the shower wall, then diverted the shower spray to wash it off.

When I got out, I felt calmer, almost light-headed. I changed into a fresh pair of jeans and T-shirt and went to the dining room, where the table was already set for dinner. Lily was helping Mom carry the food in and I joined, bringing the big platter with the pork chops. “How was your sleepover?” Mom asked, in the kitchen. “Oh, we had fun. Played around with Timothy’s home computer, stuff like that,” I said, vaguely. Lily whispered to me as we walked into the dining room together: “I missed you!” I suddenly felt terrible. I forced myself to look in her eyes, praying that I wouldn’t start crying. “I missed you too, Lily.” She smiled, and as always when she did, I felt warmth suffusing me.

After dinner we sat for a long time on the living room couch, the lights dimmed, my arm around her shoulder. Mom and Dad apparently were giving us our privacy, or at least had something else to do; after a while, I took Lily’s hand and began to stroke it. We didn’t say much; we didn’t have to. I could feel all my anxiety subliming away, as I held my little sister’s small warmth next to me. She smelled nice, and I nuzzled her hair a little.

Finally she sighed, and whispered: “Touch me, Robbie!” I put my hand on her tummy, under her blouse, and stroked it in widening circles. The side of my hand was bumping up against the bottom of her bra. I cautiously put my fingers underneath and pulled the stretchy material away and up, freeing her small breasts. She looked up and I bent my head down to kiss her. As we played our tongues against each other, I cupped one breast, then the other, toyed with the stiff nipples, made circles around them with my fingers.

Lily put her hand on my crotch, but once again, as I had with Timothy, I gently moved it away. I was aroused, but didn’t really want the direct stimulation right now. For a moment she was at a loss, then began to stroke my shoulder and arm. It felt wonderful. I kept touching her breasts, keeping one ear out for footsteps. Mom and Dad had gone into their bedroom; I figured we’d have time to disengage if I heard them coming.

Lily had begun to clench her thighs rhythmically. I could sense the slight, musky odor rising from there, even through her jeans. After what seemed like an eternity - I was getting nervous that we were sure to be interrupted any minute now - her breathing got shallow and fast, and then she breathed in sharply and, trembling, had her orgasm. I held the kiss with her throughout, let up when, finally, she relaxed. “Oh, Robbie. That was nice.”

My heart was pounding. I’d missed her saying that, so much. I looked at her slightly disheveled form in the dim light. Even as tall as she had gotten recently, she seemed small, vulnerable, not so different from the little girl who had first crawled into my bed half a lifetime ago. I felt no sexual arousal now, just a desperate need just to hold her in my arms all night again, feel her body against mine, drift off to sleep entangled with her and wake up, renewed, the same way. And the knowledge that this was the one thing we could not do was agonizing.

I started to speak, realized I didn’t know what I was going to say, closed my mouth again. Gently I pulled her bra back down and removed my hand from under her blouse. “Lily,...” There was nothing, really, I could say. Finally, I just responded to what she had just said. “I’m glad.”

She rested against my chest and I sat there, arm around her shoulder, stroking her hair with my other hand. Presently, I realized she had fallen asleep. I was near drifting off myself, but eventually woke her up, whispered “Lily ... we should go to bed.” Sleepily, she got up, and we walked down the long, long hallway, to our separate rooms.

The next morning at breakfast I let my parents know I’d be staying over at Timothy’s again that night. They seemed to be very pleased at my newly active social life and repeated their earlier suggestion that I should ask him over myself at some point. Truth be told, I wasn’t thrilled at that idea. I couldn’t imagine my parents being able to engage in interesting conversation with Timothy around the dinner table the way his mother did with us. And, after staying over at his modest apartment, I was suddenly sensitive, in a way I’d never been before, of what he might think if he saw the rather grand building that we lived in.

I understood of course that we were reasonably well off, with Lily going to a private school and everything. I’d gone to a (different) private school myself for elementary school, and most of my friends, near as I could tell, came from even wealthier families, going on ski vacations every winter and to Europe in the summer; we’d never done that sort of thing. But the contrast between our doorman building, huge (by New York standards) apartment, and genteel neighborhood on the one hand, and Timothy’s Lower East Side, fifth-floor, converted-one-bedroom dilapidated walk-up on the other was uncomfortably in the forefront of my mind after successive nights at each.

I felt like I had entered a different world — not at all in a bad way! — when I’d visited them: a world in which the surroundings were rough, tight but cozy, the conversation was intimate and meaningful, and of course the cooking was fantastic. I wanted to experience more of that world, not to invite Timothy into my own, not very interesting world. Nevertheless, I promised my parents that I’d have Timothy over sooner or later, and, stuffing a change of clothes into my backpack, I happily escaped early enough to find him in the auditorium and hang out, covertly holding hands again, for a good half hour before class.

That afternoon we went straight over to his apartment and trudged up the four flights of stairs, panting a little in the summer heat. Alice wasn’t home from work yet, and Timothy let us in with his key. The apartment was hot and stuffy and I suggested Timothy turn on the AC. He looked at me blankly. “Air conditioning,” I said, then felt stupid - looking over at the half-open window I could see no sign of any AC unit. Timothy said “Oh. We don’t have that.”

Embarrassed, I stammered quickly: “It’s OK.” Timothy looked like he was suffering even more than I in the heat; he was visibly sweating. Hesitantly, he said: “Actually, when it’s this hot ... we, um ... we usually just hang out in our underwear.” I started to laugh, then abruptly shut up when I realized he wasn’t joking. “Huh? What if your mom comes back?”

Timothy turned a little pink, and mumbled “Sorry, I didn’t mean...” I must have looked confused, because he continued: “ ... no, I mean, she does too. I mean, she wouldn’t mind, she usually wears underwear around the house herself. I mean, obviously not when there are visitors...” He stopped, looked miserable. I was momentarily dumbfounded, and he hurriedly said: “I mean, sorry, never mind, I didn’t mean to suggest...”

I was in parts bemused and intrigued by Timothy’s suggestion. I found it hard to accept that Alice wouldn’t be shocked if she came back to find us in our underwear, and couldn’t understand how he would think that was OK. I could just imagine my parents’ discomfiture if I wore only underwear around them! (True, we had air conditioning, so why would I?) At the same time, I was, even after such a short time, so enamored with this odd, intimate little family that I couldn’t deny I was somewhat excited by the idea that Alice wouldn’t mind if I stripped down, would apparently do so herself. I just had trouble believing it was true.

Finally, I said to Timothy, who was looking like he wished he’d never brought up the subject: “Seriously, man? If we stripped to our underwear your mom wouldn’t be shocked?” “No,” he replied, earnestly. “Really. We usually do. It was hot last night, too, Mom got undressed as soon as she got home. She probably would’ve the night before, too, but...” I understood; she didn’t want to shock the “visitor.” “And, so, you think she wouldn’t be upset if I did too?” “Nah, she’ll just be happy she didn’t have to stay dressed all evening in this heat.” “Well,...” I said, hesitantly. “If you’re sure...”

Timothy looked relieved, nodded, and began to take off his jeans. I followed suit, neatly folding my clothes and leaving them on a nearby chair in case Timothy was wrong and I needed to get dressed quick. We sat at his home computer in just our tighty-whities, playing an adventure game. Timothy looked a lot more comfortable than he had before, and I had to admit that it was a nice feeling to wear the bare minimum on a hot summer evening.

My heart still leapt into my throat, however, when I heard the key in the lock. I was sure that I was about to have some explaining to do, but Alice simply looked over, said “Hey, guys! Have a good day?” and, without waiting for an answer, disappeared into her bedroom. A few minutes later, she came out. I was disappointed to see that she wasn’t wearing underwear; she’d changed out of her work clothes into shorts and a T-shirt.

She came over to the computer desk, and I felt bashfully compelled to justify my state of undress. Lamely, I said, “Sorry, Mrs ... Alice. Timothy said, you know, because it was so hot, we could...” Alice smiled warmly. “Oh, that’s perfectly fine, Rob! We’re really informal here. I don’t see how anyone could stand to stay in hot clothes in this weather!” Nevertheless, I still felt keenly embarrassed to be almost nude in front of her. My friend’s mom, for God’s sake. And I noticed she hadn’t stripped down. She was probably just being polite - or had Timothy been lying to me? I felt a flush spreading to my cheeks and looked at him, but he seemed unperturbed.

Alice spoke again: “Guys, it is waaaay too hot to cook tonight. Would you both mind if I just went out and got, I don’t know, pizza or something?” Timothy looked absurdly excited. “Mom, that’d be awesome!” “Does that work for you too, Rob?” “Sure, M ... Alice. I love pizza.” Alice smiled and said “We don’t do this very often, but like I said — too hot to hoot tonight.” Hoot? I thought. “Eggplant OK with you?”

I’d never had eggplant pizza and it honestly didn’t sound very appetizing; pepperoni was more my speed, but of course I wasn’t going to say that. I said, “that sounds great.” Timothy said, “you’ll like it, man, I promise.” “Oh, I love eggplant,” I lied. “I’ll get garlic, too,” said Alice, “unless you prefer it without? Eggplant and garlic, Timothy’s favorite.” I looked over at him in surprise; the few times we’d gotten pizza for lunch — there was a pretty good place near school — so far as I remembered, he’d ordered pepperoni as well. But he looked genuinely excited about the prospect of eggplant-and-garlic pizza, so I said, “Awesome!”

Alice called the order in, and busied herself with something in the kitchen area as Timothy and I continued playing the adventure game. About half an hour later, Alice said she was going out to get the pizza. As she left, I suddenly realized I should have asked her if I could help, or — jeez — shouldn’t I be offering to pay for part of it? All of it? I realized how awkward that might come out, and didn’t know what to do.

Finally I said to Timothy, “Maybe we should set the table?” Timothy looked a bit surprised, as if it hadn’t occurred to him, but agreed. We stood up, and with a bit of a shock I noticed a small tent in his underwear. Was he sitting there erect the whole time?

Playing a dungeons-and-dragons type adventure game, I hadn’t really been thinking about anything sexual. Now I was suddenly getting worried that I’d pop a boner in front of Alice or something. But it was too late to get dressed again; I’d just have to do my best not to get hard, or failing that, keep that area hidden.

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