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, fiftth-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 — to 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.
We put some plates, silverware, and glasses out and presently Alice returned with a big white box in her hand. She looked over at us and said “Thanks, guys!” I replied, sincerely, “No, thank *you* Alice for getting the pizza!” She beamed and put the box in the middle of the table. “Folks, it’s scorching out there, and in here, and I just walked up four flights of stairs. Rob, would you mind terribly if I joined you guys in wearing a little less? I’m sure Timothy told you that we both usually strip down *en famille* when it’s this hot.” She looked a little anxious, which gave me a bit of a shock; she seemed like such an unflappable person in general. Trying to sound casual, I said “Sure, he did tell me and I don’t mind at all.” Alice looked relieved and ducked into the bedroom, then emerged wearing — well, I wasn’t an expert on women’s clothing, but basically it looked like a bikini except that it was clearly underwear, if that makes sense. When I think back on it now, I’m a little surprised that I wasn’t more… *interested* in looking at her. After all I hadn’t, at that point, had that many opportunities to see scantily-clad women (other than my sister, of course) up close. I think was I still basically putting her in the “friend’s mom” category, and as such not someone to look at in “that way.” And yet, objectively, she was quite attractive. She must have been in her 40s, somewhat younger than my parents – of course I already knew that she was worlds apart from my parents in terms of outlook and demeanor. I could sort of see Timothy in her face, but other than that there wasn’t a lot of physical resemblance; she was tall and fairly thin, with almost angular features and straight black hair, whereas Timothy was short, chubby, had curly hair (albeit as black as his mother’s), and his features were much softer. I vaguely mused on what his father might have looked like. We sat down, but before we could even open the pizza box Alice got up and walked past me to the kitchen. As she passed I noticed a few stray strands of pubic hair peeking out around her bikini underwear, and was unable to resist thinking briefly of what the underwear concealed; I was suddenly glad I was sitting down with my lower half concealed by the oilcloth hanging from the table. Alice came back with three small glasses and a bottle of red wine. “Rob, I don’t know if you drink,” she said. “Timothy sometimes has a little wine with dinner, you’re welcome to have some too.” I had literally never drunk anything alcoholic in my life – I knew my parents drank at parties and so on, and would sometimes have a cocktail in the evening, but I’d never known them to drink wine with dinner, much less offer me some. However, I certainly wasn’t going to admit that in front of Timothy and Alice, so, as I had with the eggplant-and-garlic pizza, I lied: “Oh, sure, I love wine.” Alice looked at me a bit quizzically, but poured me, then Timothy a half-glass each, then filled her own glass.
The eggplant-and-garlic pizza turned out to be the best pizza I had ever had in my life – so good, that I couldn’t imagine ever ordering pepperoni again. The eggplant was lightly breaded and fried and tasted rich, meaty, like nothing I’d ever had before, and the fresh garlic had me floating in air. I said as much and Timothy said, “See? I told you!” Alice laughed and said “Eggplant is just so versatile. I never make breaded cutlets like this myself, but I use it all the time – grilled, fried, ratatouille, baba ganoush, imam bayıldı, …” I suddenly remembered the dish she had made a couple of nights ago – it had cubes of something that I had just enjoyed and not questioned, but which I now realized must have been eggplant. “And the stew you made the other night, right?” She smiled widely. “Oh, the güveç? Yes, can’t make that without eggplant.” “That was delicious,” I said, and took a sip of wine. It was strong and slightly acidic, but not unpleasant. In fact it seemed like a perfect complement to the garlicky pizza, and I took another sip. I asked where this “gooey-vech” originated and Alice talked a little about Turkish cuisine. She said that she rarely ate meat these days and that it was surprising how satisfying a mostly-vegetarian diet could be; after three meals at her table I had to agree heartily. Soon the conversation shifted to travel and she told us a little about her travels on the “hippie trail” in the 60s; she’d fallen in love with Turkish and Persian food then. It sounded fascinating; she spoke frankly about drugs and free love and other topics that I’d never imagine I’d hear someone of my parents’ generation sharing with me. In the meantime I had polished off two slices and my half-glass of wine and without even thinking about it helped myself to more of each. My head was spinning a little. Timothy was talking about some novel he was in the process of reading that, near as I can tell, Alice had recommended or given to him. I’d never heard of the author, Tom Robbins, and resolved to ask him whether I could borrow it when he was done.
After a while Timothy got up, wrapped the remaining half of the pizza in tinfoil and put it in the fridge, and I washed the plates and silverware. Alice divided the remainder of the wine among our glasses — “oh well, might as well make merry while we may,” she said, cryptically — and we retired to the sitting area, Timothy and me on the couch and Alice on the ratty-looking loveseat opposite. I sat there, lightheaded, now gazing quite openly at Alice. She really was attractive, I thought – sitting, legs crossed, on the loveseat, with just a hint of pubic hair visible around heir panties, and the nipples of her small, slightly saggy breasts visible unapologetically through the fabric of her bra. I could feel myself getting hard again, but in my somewhat dazed state I didn’t worry about it too much, opting just to sit in such a way that — I thought — it wouldn’t be too obvious. For his part, Timothy was inching closer and closer to me on the couch, periodically interjecting wry, funny, and frankly wise comments as Alice continued to hold forth about the glories of the free love days. I had the heady sense that I had been given the unique privilege of admission to an intimate *pas de deux*; Alice was both a fascinating storyteller and a great conversationalist, making me feel that even what little I had to say (my head was really spinning now) was worthy of deep consideration, and Timothy was the perfect foil to her seriousness; his commentary kept cracking both of us up. I’m sure Alice realized I was drunk, but she didn’t make any comments about it, and I felt filled with warmth and a deep kind of ease with the universe that I hadn’t felt for a long time. Nevertheless, I froze when Timothy finally made contact. His bare arm touched mine and he leaned his head against my shoulder. I desperately pretended I didn’t notice, searched Alice’s face for signs she disapproved, but she didn’t bat an eyelash. I could tell that Timothy wanted me to put my arm around him but I just couldn’t bring myself to make such an overt move. I actually felt quite full of affection for him at that moment — for making me and Alice laugh, for being his usual cute self, for initiating me after such a short time into this lovely intimacy — but I still imagined that Alice, for all her talk of free love, would not be OK with my cuddling her son right in front of her. After a short while Timothy pulled back a little — I didn’t dare look at his face — and the conversation continued to swirl about for at least an hour more, until Alice yawned and said, “guys, I’m going to hit the sack. Rob, do you need anything? Toothbrush, towel, whatever?” I said I still had the toothbrush from the other night but would appreciate a towel. She stood up, found one in the hall closet, and tossed it to me. Timothy walked over to her and she embraced him in a big, tight hug. In my wine-emboldened state I went over and, when they finally disengaged, said, trying to sound jokey, “me next!” Alice didn’t hesitate but gathered me up into her arms, pulling me close. She was roughly my height and I was acutely conscious of her breasts pressed against my chest, her hands on my butt, and the slight fragrance of her perspiration. The hug felt wonderful, not “motherly” at all, and seemed to last an eternity; I put all my mental effort into not getting an erection.
Finally, she let go, and said lightly, almost — it seemed to me — a little wistfully, “Good night, kids. Try not to have too much fun.” She went into her room, leaving me pondering what she could have meant by that. Timothy and I took turns brushing our teeth, then retired to his tiny room and closed the door. He wasted no time pulling down his underwear and I saw, unsurprised, that he was erect, his small penis springing to life as he straightened up. I was hard myself — I was unsure of exactly what mix of events had aroused me, but it didn’t really matter; I wanted Timothy’s body, now. When I took off my briefs, I could see that Timothy was staring unabashedly at my erection. “God, Rob,” he murmured. “You are so beautiful.” Jokingly, I struck a glamour pose, but Timothy, for once, looked completely serious. “Come over, you,” I said, and he did. I took him into my embrace, pressing my penis against his soft belly. He moaned softly. I could hear Alice finishing her evening ablutions in the bathroom, then closing her bedroom door, and reminded myself that we would need to keep it down. Alice’s bedroom was adjacent and I had no idea whether sound could make it through the walls; in our apartment the interior walls were thick and solid but I had a sneaking suspicion that this place might have cheaper construction. I motioned to Timothy and we sat down together on the bed. He looked up at me and I mentally shrugged, leaned over and began to kiss him. I could still taste the minty toothpaste in his mouth. As our tongues played he reached for my erection and I let him encircle it and begin to stroke. I put my hand down and he obligingly spread his legs a bit to give me access. I toyed with him, now stroking, now caressing, now just barely touching, and felt him shake as the conflicting sensations collided. Then all of a sudden I heard it, incredibly faintly, almost drowned out by Timothy’s breathing, but unmistakeable nonetheless: the sound of throaty moans from the other side of the wall. I couldn’t believe Timothy didn’t hear it, but if he did, he paid it no mind. As I thought about the implication, my penis became almost unbearably hard; Timothy stroked it with all his might, and I finally began to give way to all the pent-up arousal of the evening. As I felt the pressure build, I concentrated on pumping Timothy’s small penis with the same intensity he was devoting to mine, and when finally he broke the kiss and stammered “I’m… I’mm…” I let go and spurted an enormous quantity of semen with what seemed to me like unprecedented force, It landed on Timothy’s chest and face and hair and almost simultaneously, he came too, wetting my fist and my thighs and belly and his own, and then he collapsed, putting his head in my lap, his face against my softening penis. In a daze, I just sat there, listening to Timothy’s heavy breathing and the muffled moans from the other side of the wall. After a while I whispered, “hey.” Timothy said, wistfully, “It’s so beautiful, Rob.” For a moment I didn’t know what he meant, then he continued, “I wish I were as big as you.” I whispered, “hey, man, I really like you the way you are.” He smiled wanly, sat up. I finally couldn’t stand it anymore, gestured at the wall “Is that…?” “Yeah, sometimes she does that.” He looked embarrassed, didn’t say anymore. I made light of it: “hey, don’t we all?” We pulled the light sheet over ourselves, and lay silently, face to face, lightly embracing, for a while. After a few minutes the moans turned into gasps and then stopped, followed by a loud sigh. I raised my eyebrow and Timothy, still looking in my face, suppressed a giggle. It was so cute that I couldn’t resist kissing his forehead and again I was rewarded with a big smile. He got up to turn out the light, and we fell into an easy sleep.
The next morning I felt like crap warmed over: my head ached, my throat was dry. I had the presence of mind to recognize it as my first hangover and as I thought back to how I’d behaved the night before, staring at Alice, asking for a hug, I felt ashamed to boot. I was in no condition to cuddle with Timothy as we had the other morning, and moreover when I looked over at the clock it was surprisingly late, almost 6:30. I lay staring miserably at the ceiling for a few minutes, hoping Timothy would wake up, I finally got up, grabbed the towel Alice had given me, pulled on the previous day’s underwear and walked out into the hallway, gently closing the door, and into the bathroom. I closed the door – there was no lock – started the shower and washed the grime off. Even though it was still hot in the apartment, the hot water felt good, and I decided to wash my hair. Suddenly the door opened. Initially I thought it must be Timothy but I was shocked to see, through the transparent curtains, that it was Alice who’d walked in — and even more shocked to see that she was stark naked. Alice looked straight at me but seemed entirely unperturbed. “Oh, hi Rob. Sorry, I assumed it was Timothy in there.” I wondered – was she in the habit of just walking in, naked, on Timothy when he was in the shower? But she didn’t back out or apologize further, but simply walked over to the toilet and sat down with a sigh. I simply could not believe what was happening. The shower curtain was not designed well and didn’t reach all the way around the tub — fortunately the relatively anemic spray didn’t reach out the end. With only the sink between the tub and the toilet, I could see Alice’s face and breasts, and was uncomfortably conscious of the fact that she could surely see me as well, at least out of the corner of her eye; she was facing forward. I tried not to look. I closed my eyes and rinsed my hair; when I opened them again, I saw that Alice had turned towards the tub and was staring straight at me. She saw me notice and, to her credit, looked embarrassed. “Sorry, Rob. Didn’t mean to embarrass you. We’re family now, right?” It seemed like an odd thing to say. Family — and I was thinking of course of my parents; Lily was something else entirely — were the last people I’d expect to be seeing me naked in the shower. I tried to maintain my aplomb and muttered, “Sure.” Alice got up off the toilet, wiped her front, threw the tissue in and flushed. I yelped in spite of myself as the water suddenly ran hot and Alice apologized: “Oh geez, Rob, I’m sorry. I always forget, Timothy gets so pissed at me.” I said, “It’s OK, I was done anyway,” and turned off the water. I don’t know what prompted me; perhaps it was just wanting to match her nonchalance, but I pulled aside the shower curtain and clambered out, dripping. Alice stepped over, picked up my towel and, without even asking, began to dry me. She rubbed my hair vigorously with the towel, spinning me around so I was facing the door, then dried my back, then finally gently took my shoulder, turned me back around, and began to towel my chest. I was looking straight at her nakedness, and she of course was looking at me, and I think it was only the hangover and perhaps the sheer unexpectedness of the situation that saved me from embarrassing myself with an erection right then and there. Finally, she said lightly, “you’re good to go! Go wake Timothy up, you guys are going to be late.” Numbly, I put the towel in the laundry bin and walked back to Timothy’s room, forgetting my underwear on the bathroom floor.
Timothy was already awake and I whispered to him, “hey, listen, your mom…” He looked at me curiously. “She, she came in when I was taking a shower.” I didn’t mention the rest of it. He looked puzzled. “Yeah?” I said, “Isn’t that a bit…” He shrugged. “Did she flush the toilet while you were in there? I hate when she does that, she always forgets that it makes the water get hot.” I laughed. “Yeah, that’s what happened.” “Well… sorry if you got burned.” “No, no, I just wasn’t expecting her to come in, you know…” I realized he didn’t really understand what I was getting at. I elaborated: “I mean, my parents would never come into the bathroom when I was, when we were..” As I said it I realized how dumb I was being; we had three bathrooms in our apartment. Timothy said, “oh, yeah, well, Mom never really asks; we go in all the time when the other one is in there. She probably just forgot you’re not me.” I laughed. He got up and said, “speaking of showers, I’d better take one.” I could hear that Alice was in the shower herself and wondered whether he was going to barge in on her, but he hung around for a few seconds until Alice called, “Timothy, I’m almost done.” He walked out, stark naked, and headed straight for the bathroom. As I got dressed I could hear him and Alice talking in the bathroom and surmised that he was using the toilet while she was finishing her shower. I pulled on my fresh underwear, jeans and T-shirt and walked out into the hall. I noted without much surprise that the door was open; Alice was just stepping out of the tub and Timothy was stepping in. I shrugged, went and sat at the kitchen table. Presently Alice emerged, a towel around her head but otherwise naked. She looked fresh and clean. She came over to the table, leaned over, and whispered, “Rob, I realize I probably embarrassed you in there before, and I’m sorry. Timothy and I don’t really worry that much about privacy; it’s hard in a small apartment like this. One bathroom, and we both have to get ready in the morning. He and I have lived, just the two of us, for so long that I tend to forget that some of our ways might be a little off-putting to anyone else. And we all got so comfortable last night, I almost forgot that you’re not part of the family.” There was that word again, “family.” “Will you forgive me?” she continued. I suddenly realized that I desperately *wanted* to be “part of the family,” if it meant being as comfortable with each other as Alice was with Timothy and vice-versa, if it meant being comfortable in our underwear, talking together until late at night, drinking wine and eating wonderful food, getting big hugs, not worrying about seeing each other nude. I tried to formulate a reply so as not to ruin everything. It came out sounding surprisingly coherent; I barely recognized myself saying it. “It’s all right, Alice. I’m not embarrassed. I think it’s great that you and Timothy are so comfortable with each other, and I like feeling that comfortable with you both, too. I was a bit surprised this morning but it’s perfectly OK.” Alice looked relieved, straightened up, and grinned. It suddenly clicked that she was still an attractive, naked woman standing right in front of me. I could see the water beaded up on her thick mat of pubic hair; I didn’t quite dare to look up. Past her I could see Timothy walking out of the bathroom, still naked, towards his room. Alice turned around and walked towards her bedroom; heart pounding, I watched her butt shake as she went.
Breakfast was quick and plain, just toast and butter and a delicious red spread that Alice called *ajvar*. She apologized that she had to get to work early that morning. I told her the ajvar was great, as usual, and she said, mischievously, “yet another way to sneak that eggplant into you, my dear Rob!” Timothy giggled. (I’m aware that would be a *double entendre* among the younger set today, but I want to emphasize that neither Alice, nor I, nor Timothy, nor so far as I know anyone else was thinking of eggplants that way back then.) After breakfast we all left the apartment at the same time. Alice headed downtown, giving us each a hug on the sidewalk before she went; Timothy and I started towards school. Halfway there, I realized to my chagrin that I’d left my underwear on the bathroom floor. I mentioned it to Timothy and he promised he’d retrieve it when he got back. “Or maybe you could just come over again?” It was tempting, and part of just wanted to say “what the hell” and commit myself to going, but I also felt I needed time to think about everything that happened. I didn’t want to be a bother to Alice, either. I told Timothy we could perhaps get together over the weekend, even do something in the city, and that seemed to satisfy him. We arrived at school just in time for first period.
Source: reddit.com/r/sexystories/comments/oy9a9t/changing_the_rules_of_the_happiness_game_part_5