Changing the Rules of the Happiness Game - Cover

Changing the Rules of the Happiness Game

Copyright© 2022 by NotReallyAshamed

Chapter 20

Romantic Sex Story: Chapter 20 - 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  

Timothy and I had a nice time in the Village. We went to Tower Records, and for the first time I ventured upstairs to the balcony where they had folk music, looking for records of the kind of music we had been singing the night before. Timothy didn’t know the names of most of the songs, or who had sung them, but he thought that the first song we’d sung, the one about “finding a better place,” was by a group called Pentangle, and I found a few albums by them in the P section. I didn’t know whether any of them had the song I’d liked — there were no lyrics on the album cover and no song whose title sounded particularly like it was about finding a better place — but I bought three of the most likely-looking ones anyway.

After the record store, we just walked around the crowded streets for a while. I could tell that Timothy was hoping I’d take his hand again, but, as much as I was enjoying hanging out with him, the sense of acute affection I’d felt for him the night before had faded, and I felt weird thinking about being too demonstrative with him in public even if we had done so before. It wasn’t at all implausible that we might run into someone we knew and, though I suspected all our friends already had figured out that something was going was on between us, I didn’t really relish removing all doubt.

I felt guilty. Timothy obviously had deeper feelings for me that I didn’t fully reciprocate, even as I continued to be physically involved with him. I didn’t want to stop seeing him, especially as that would certainly mean no longer being able to see Alice either. Every minute I spent over there, I felt that I was expanding my horizons, learning about aspects of life that I’d never dreamed about in my sheltered, uptown existence.

But at the same time, I wished that Timothy weren’t so... serious about me. I didn’t know how to stay close to them without continuing to let him — and Alice — believe that we were a “couple.” All I knew was that, as affectionate as I felt towards Timothy, and as much as I was turned on by the fact that he was obviously infatuated with me, I couldn’t truly think of him — or any male — as a romantic partner.

And that led me to the inexorable conclusion that I was abusing our friendship, allowing him to believe that I felt the way he did, just so that — so that what, actually? So that I could get my rocks off? I didn’t need that, I reminded myself. Lily and I were lovers now. No, I had to admit to myself that it was really much more about how much I enjoyed spending time in this odd, intimate little family that was so different from anything I’d ever known. I didn’t want to give that up, and it felt like letting Timothy believe that I felt the same way about him as he did about me was a prerequisite. But I didn’t feel good about it.

We ate an indifferent lunch on Bleecker Street, then simply wandered around for a few hours. When the afternoon heat began to tire us, we got Italian ices; then Timothy suggested we go back to his apartment: “at least we can get out of our sweaty clothes.” When we got there, Alice was out. Timothy suggested that we shower together. I of course wasn’t under any illusions about what he wanted, but I was starting to feel a little horny myself and I agreed.

We stripped in his bedroom, then went to the bathroom and started the water. As always, I liked looking at him naked. He was just kind of soft and cute and his chubbiness, his immature genitals and mostly hairless body gave him a kind of androgynous look. We got into the shower and paid lip service to actually washing, then got down to what we were really there for.

After we had touched each other for a while and were both fully erect, Timothy asked me shyly if I wanted to try taking him from behind. I rubbed myself against his butt crack for a while, but when he clarified that he wanted me to try actually penetrating him, I didn’t really feel ready for that; I wasn’t even sure it would be physically possible. When I’d had my finger in him the night before, there simply didn’t seem to be enough room to accommodate my penis, which, relative to his at least, was pretty thick.

I didn’t turn him down outright, but instead took the soap and played around with washing his butt, then tried putting a finger in again. His reaction was gratifying; he moaned and tried to push himself back onto my finger. I had an idea; pushing the shower curtain out a little, I sat on the side of the tub. That positioned me to take his penis into my mouth. The clean, slightly soapy taste and smell felt strange; last time I had tasted him he had been sweaty and musky. I pushed my finger in and out of his anus as I sucked and tongued him. Quite soon he began to groan loudly and then, climaxing, spilled a surprising amount of semen into my mouth. The last time I’d sucked him there had been hardly any; this time I nearly choked as I tried to swallow it. At the moment of his orgasm, Timothy’s knees almost buckled out from under him; I had to hold him hard around his waist to steady him.

After he had calmed down, I let him go. Remaining on the side of the tub, I motioned to him sit down on my lap and planted his ample buttocks around my erection. I closed my eyes and, putting my arms around his hips and my hand on his chubby belly, I rocked him back and forth, my shaft sliding between his wet cheeks until I felt myself getting close; then, I raised one hand to his breasts and, imagining Lily, fondled them.

When I finally came, spraying his backside, it was with a sense of mild shame. I felt conflicted; the orgasm had satisfied me physically but left me a bit empty. I missed Lily. As we washed ourselves off, I tried to reassure myself that I would see her tomorrow, and that perhaps Timothy would, after this “afternoon delight,” be OK with just sleeping tonight. My feeling of shame, however, did not dissipate after we had dried ourselves and walked out of the bathroom, without even towels around our waists, only to find Alice — fully dressed — already home and indeed standing in the hallway near her bedroom door, only a few steps from the bathroom.

My heart leapt into my throat and my cheeks burned hotly. It was bad enough that she saw us leaving the bathroom together but — I wasn’t clear on when she had got back — surely she might have heard Timothy moaning, or even my own vocalizations? There could be no mystery about what we had been doing in there.

But Alice simply smiled and greeted us. As we stood there, awkwardly, she asked how our day had gone, then announced brightly: “Hey, you guys, why don’t we just go nudist tonight, shall we? Like in the old days.” I didn’t know what old days she was referring to. “I’m going to take a shower,” she continued, “then we’ll see about getting pizza.”

We retreated to Timothy’s room. He made no move to get dressed, even pull on underwear, and I asked him if his mother had been serious about “going nudist.” “Yeah,” he sighed. “We always used to go naked when I was younger. Even sometimes nowadays she likes to. I think Mom was part of a nudist colony or something once.” He didn’t seem super-enthusiastic about it, but he also didn’t pull on underwear, so I didn’t either.

I was a bit irritated, though. After the embarrassment of being caught leaving the shower together I had rather the urge to hide. It didn’t help that Alice had acted utterly nonchalant about it. I almost had the absurd feeling that she was forcing us to go naked as a kind of punishment, although that was obviously nonsense: Timothy had just made it clear that it had been a habit by them long before I had come around. Still, it bothered me a little that I didn’t feel comfortable going against the tide and even just putting on briefs. I wasn’t going to do it if Timothy didn’t, obviously, but I would have preferred if Alice had just suggested our usual lounging-around-the-house attire.

Sure enough, Alice emerged from the bathroom stark naked and stayed that way. Timothy and I walked out — just a tiny bit reluctantly, it seemed to me — and we sat for a while on the sofa, Alice as usual on the loveseat opposite. I thought it a bit odd that Alice didn’t mind all of us sitting there without even a towel between us and the furniture, but I figured we were all freshly showered and in the end our butts weren’t going to make the somewhat ratty upholstery any worse than it already was.

We talked. She was in fine form, and the conversation veered from politics to the environment to protestors to punks to drugs to music and so forth; I was getting caught up in the fun of discussing and debating with her and Timothy and my discomfiture at the (almost) enforced nudism was starting to fade. It was easy to forget that you weren’t wearing clothes when we were all focusing on each other’s thoughts, not our bodies.

At some point Alice went to the kitchen phone and ordered a large eggplant and garlic pizza. I was figuring that she’d have to get dressed to go get it, and thought about perhaps volunteering myself and then just not getting undressed again when I came back, but Alice surprised me by asking if the place delivered. Apparently they did, and she gave them the address. “Hey, Friday and Saturday night they have free delivery,” she beamed, when she returned, with an open bottle of red wine and three glasses in her hands. She poured for each of us.

I was starting to feel confident about this new drinking habit, after successfully fending off a hangover the night before, and I accepted the wine gratefully. We sipped and talked, and I started to feel, on the whole, much better. The better part of an hour later, the pizza arrived. Alice went and grabbed a bathrobe to answer the door, then shed it again as soon as she had paid and closed the door.

It was still relatively early, not even 7 yet, but we ate hungrily, putting the pizza on paper plates the delivery guy had brought, drinking more wine to go along with it. Eventually we ran out of wine — Alice and I were doing most of the drinking, I realized; Timothy had had only two glasses if I had kept track right — and she brought out another bottle.

I had an uneasy feeling that I shouldn’t drink any more, but I felt so good at that moment that I accepted another glass. When the daylight started to subside in the apartment, Alice lit candles again, then pulled out her guitar. This was the moment I’d eagerly awaited, and I lost myself in the singing for the next hour or two, my head swimming with the wine.

I was already getting a bit sleepy when Alice put down the guitar and went into her bedroom. She brought a few items out that I didn’t recognize, a small, thin green packet and a decorated hexagonal box. Timothy said, “Mom...” in a cautious voice. “Timothy doesn’t partake,” Alice explained. “But it’s nice sometimes, in good company. Do you mind?”

I didn’t know at first what she was talking about, but figured it out when she opened the box, took out some material, put it on a paper from the green packet and began to roll. She lit the joint in the flame of the candle and breathed the smoke in, holding it for a while before exhaling. “Want a toke, Rob?”

I had, of course, never smoked pot, and in fact thought of it as a seriously delinquent practice. I knew of course that some of my classmates partook, and hanging out in Washington Square one occasionally saw even relatively normal-looking NYU students getting stoned in broad daylight. That didn’t mean I’d ever intended to try the stuff. But the wine had lowered my inhibitions, I was feeling pretty good, and I was curious. I accepted the joint, took a deep puff, tried to hold it in as Alice had and immediately broke out in a coughing fit.

Alice giggled, took the joint back, and handed me my wineglass. When I’d recovered sufficiently to drink, I took a sip, then asked her for water. She stood up — I remember staring quite openly at her naked body and thinking how beautiful it was in the candlelight — and fetched a pitcher with ice water and more glasses. I took a long draught of the cooling water and when the ache in my throat began to subside, indicated that I was ready to try again. Timothy didn’t say anything. Alice passed me the joint and again I inhaled, trying to be a little more careful. This time at least I didn’t cough, although I wasn’t able to hold the smoke for very long.

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