Woulda Shoulda Coulda

Adventure #2: Steel-Gray Eyes

Part 2

© 2020 by Gamin Paramour


Welcome back to the second story in my series based on my own real experiences. This is Part 2. If you haven't read Part 1 yet I suggest you read it first.

Please note that this is mostly fiction, the fun that shoulda happened, and coulda happened if only...

For the record I do not advocate breaking the law. If we're sitting in jail the assholes win.

Need I remind you that Nifty is amazing? Please donate if you can.

I appreciate your feedback, so please email me and I will do my best to answer quickly.

Gamin Paramour, 2020


Part 2

Friday morning I awoke after eight to disappointing silence; no urgent knocking at my door, no sweet little sex buddy nude in my bed. I tried not to feel dispirited. What did I expect? That Terry would spend every waking moment pining for me? Oh, well, I thought, whatever will be will be.

Thank you, Doris Day.

I gave it until ten o'clock but it was still radio silence so I decided to try the pool. My heart rose when I saw the whole contingent already there, splashing and playing and shouting like the gleeful kids they were. Gary saw me first and ran across the pool deck to intercept me as I exited the changing room.

"Bill!" he cried, enfolding me in a dripping wet hug. I picked him up and carried him back to poolside, returning his grin.

"Hi, kids," I said to all as I surveyed the gaggle of young-uns.

Geri was wearing a remarkably sexy little swimsuit, still a one-piece like the other day but with a big cut-out in the front from below her navel to just under the bustline -- or what would have been the bustline if she had a bust. It was also deep cut in the back, showing everything from the nape of her neck to the dimple of her tailbone, exposed to view when her long hair was swept to one side. I decided that I'd better look away before someone noticed me ogling.

"Do I see some new faces today?" I asked.

Geri smiled up at me and indicated a smaller girl next to her, a very cute little blond in a royal blue bikini with a yellow floral print. She was maybe ten years old and didn't look a day over it. The girl wore a friendly smile which projected also from her pretty blue eyes.

"This is Hannah," Geri announced. "She's in Terry's class but she's my best friend."

"Hi," Hannah said in a very sweet, soft voice. I'm a lot more into boys than girls but I had to admit she looked mighty tasty.

"Geri says you're real fun in the pool," Hannah went on.

"Oh," I said. "My reputation precedes me. It's nice to meet you, Hannah, and I'll try to live up to expectations."

I could see that none of the kids knew what the hell I was talking about, so I resolved to pull back a little on the vocabulary.

"And who's this, then?" I asked, indicating the tallest kid I'd yet met, a black-haired boy a couple of inches taller than Casey but with a very young-looking face and body. He was cute, in his way, but didn't bowl me over.

"Miles," the boy said, and I noticed for the first time his emerald green eyes. OK, so that brought him a step closer to bowling me over. "I go to school with Terry and Casey."

Another ten-year-old I thought, though I might have guessed eleven given his height. "Nice to meet you too, Miles," I said as I sat on the edge of the pool and let myself easily into the water. With six of them I decided it wasn't safe to cannonball. That realization -- that I was drawing quite a crowd of juveniles -- was slightly alarming, and I decided I'd better keep things G-rated.

Terry immediately grabbed me and began to wrestle. Before I could react Casey was on me, then Geri. I focused on Geri, one hand on her trim bare tummy and the other in the small of her back as I picked her up and tossed her away, and she did in fact feel wonderful.

I growled, playfully getting into Hulk mode, and began flinging children this way and that, eliciting laughter and shrieks of joy. Both Hannah and Miles hung back at first, having met me all of one minute ago, but I didn't stand on ceremony and grabbed each of them in their turn. Quickly they became part of the mob, grabbing for me as eagerly as I grabbed for them. Other than some entirely accidental cheap feels I kept to my resolution and stayed out of the Stranger Danger zone.

Hannah was a super-soft little sweetie, and I got a small thrill for about three seconds when her bikini top rode up and revealed both tiny pink nipples. She was as flat as the jet-car track at Bonneville but her nips were cute and more or less erect.

Kinda-sorta.

Miles on the other hand had big brown nipples sharp as darts, the aureoles the size of nickles. I couldn't resist stealing a one-second feel, to which he did not react. The other highlight of wrestling with Miles was a quick cup of one slender butt cheek, which was surprisingly squishy for such a thin boy.

Casey was more aggressive in his wrestling than he had been in our previous outing. That day he had danced just out of reach most of the time, darting in to grab at me when he saw an opening. This time he kept himself close, allowing himself to be grabbed as often as he grabbed me, the contact seeming to be as much the goal as winning. I quickly dismissed that thought as wishful thinking.

I was a lot more certain of Terry's ulterior motives. More than once I felt small fingers between my legs, brushing and sometimes tweaking my dick. Our glorious morning in the sack instantly flooded my mind and my cock rose in seconds, Terry right in my face with a knowing smirk. I pushed his hand away but I couldn't help but smile at him and his eyes lit up in naughty glee.

Just then Geri launched a splash with the heel of her hand perfectly aimed at my face. I spun away and bumped into Hannah, who was also spinning away to avoid the splash. My stiff cock prodded solidly into her back and I was immediately mortified, pulling back as quickly as I could and looking to her for a reaction.

She turned back toward me with a look of shock and surprise on her pretty face, but not confusion. We made eye contact for a second and then she looked straight down at my crotch, completely understanding what it was that had just poked into her.

She turned away just as two pairs of small hands grabbed me from behind and I had to rejoin the battle or be dunked. I dispatched Terry and Miles in short order and turned to look for Hannah, fearful that she was off to tell her Mom about the bad man in the swimming pool, but instead I spotted her 15 feet away saying something to Geri. Geri looked uncomprehending and I read her lips saying, "What?" whereupon Hannah stood on tiptoe to reach Geri's ear and whispered something that made Geri shoot me a surprised, open-mouthed look.

Oh, Christ, I thought. I just started an amazing relationship with an eager preteen boy and it was already ruined. I would have to keep away from any and all kids for the foreseeable future, at least until I could move away and try again elsewhere. Having just begun my apartment lease that would mean a whole year of cowering in fear with the Sword of Damn-I-Fucked-Up hanging over my head.

Then Geri's shocked expression morphed into a cheeky grin.

Surprised to say the least, I returned a tentative smile. Geri and Hannah shared a glance and then both of them beamed big smiles my way.

I was still pondering exactly what the hell had just happened when I was blindsided by all four of the boys and found myself unceremoniously under water. I struggled to regain my feet, clutching at the amorphous blur of hands and legs of my young attackers.

I felt a small hand firmly grip my burgeoning cock and I reached up between the closest pair of legs, finding the small stiffness I expected. We fondled each other until my breath ran out and I had to stop pretending to be overcome and stood up just as the owner of the little stiffy in my hand pulled away.

I came up with a smile and wiped the water from my eyes, only to find that Terry was clear on the other side of the pool! The boy with whom I'd actually shared a feel-up had to be either Casey or Miles, who stood smiling together a few feet away.

I didn't have a clue which!

Now it was my turn to shoot a shocked, open-mouthed look. I scanned their eyes but I couldn't read anything but amused delight. They were in chest-deep water so I couldn't check their swimsuits for bulges, either. I was thrilled and confused but also frightened. What I just did is illegal as hell, so it's pretty important who knows it.

I heard Geri's voice right behind me, "Let's rest a minute, you guys."

Hannah and the boys mumbled assent and we all drifted into the shallow water to loll against the side, as was becoming the norm. I tried to evaluate the six little faces for any telling sign but everybody seemed fine.

Gary took his now-accustomed place on my left knee and Casey pressed against my left side, but instead of Terry on my right Geri made a point of sidling in and cozying up. Her bare leg came over and touched mine -- accidentally I think -- and her soft smoothness was delicious. She had my cautious interest, cute and sexy in her revealing swimsuit. It could only have been better if she was hiding a nice little dick and balls underneath it.

Geri looked around, making sure no adults were in earshot. Fortunately the only grownups at the pool this time on a weekday morning were the young mothers watching their toddlers splash around the separate kiddie pool about 20 feet away. Geri and I locked eyes and exchanged a lot of information in a silent five seconds.

"I know about boners," she whispered, smiling coyly. "I have two brothers!"

Hannah leaned in close and added, "And I have a boy cousin who likes to show it to me." After a pause she added, "Actually he shows it to everybody."

I stifled my immediate impulse to ask if the cousin lives nearby. Even these youngsters would realize it meant I was hot to see the kid's cock.

Geri gave me a very friendly smile and said, "Don't worry, we won't tell. It's just something that happens with boys."

I looked around the group and saw six friendly smiles, but also noticed a slight reddening of Casey's cheeks. I glanced at his crotch hoping to confirm an erection but I couldn't tell.

There was no doubt I would try to take things further with whichever boy had traded gropes with me -- assuming he wanted to -- but I fervently hoped it would be Casey. I had nearly talked myself into broaching some sort of naughty subject just to see each kid's reaction when a grown female voice came from outside the fence.

"Casey!" it said. "Please come here. I need to talk to you."

"OK, Mom," Casey said and disengaged from my side. He climbed out of the pool and trotted over to her, along the way grabbing his towel from a chair and wrapping it around his waist. It was all the confirmation I needed that the kid had a hard-on.

They spoke through the fence for a minute or so, too softly for me to hear. She was an attractive woman in her mid-30s I would guess, probably really hot a few years ago. Her long blond hair was in a pony-tail held by one of those elastic scrunchy things, hot pink. Her manner seemed affectionate toward Casey, at least from this distance, and at one point she put her fingers through the bars and Casey reached over to touch them. I was pleased that he had at least one parent who seemed to like him.

Then Casey's Mom turned and looked directly at me and asked Casey a question. Casey gestured in our direction and answered, then nodded his head and trotted back over to me.

"My Mom wants to say hi," he said. "Do you mind coming over to the fence?"

I forced a stone face while inside my head the alarm bells were deafening. I pasted on a smile and hoisted myself out of the pool, following Casey's example and grabbing my towel to cover myself -- though at this point there was nothing to hide.

Funny how unexpectedly encountering The Mom instantly deflates even the stiffest stiffy.

She was smiling as the boy and I approached. "Hi," she said when we were a few feet away. "I'm Brandi, Casey's Mom. You must be the famous Bill."

I smiled self-effacingly, or at least that's what I was going for. "I don't know about famous," I said, "but I am Bill. Nice to meet you, Brandi."

"Casey thinks you're really something," she said. "Last night it was all Bill-this and Bill-that."

"Aw, Mom!" Casey complained. "It wasn't that bad."

Brandi smiled and said, "I didn't say it was bad. I talked to Mary Foy this morning and the three of hers can't stop talking about you either. Especially Terry."

I think I blushed a little, knowing exactly why Terry was so enamored. "They're all terrific kids," I said. "I'm new around here and they couldn't have been nicer or more welcoming." Then smiling directly into Brandi's blue eyes I added, "And I see where they get it, from terrific parents."

Boy, if I shoveled it on any deeper I'd need hip boots.

"I want to thank you, too," she said, eating up my copious fertilizer. "I took a personal day today, but I'm usually at work and I worry when the kids are at the pool all day with no lifeguard, or any adults at all half the time. You have no obligation of course, but when you're here I can rest a little easier knowing there's a responsible adult just in case something happens."

I usually feel weird about statements like that, given that what I really want to be responsible for is her son's orgasm. I deflected with a joke.

"Don't worry," I said. "Back at my old apartment not a single one of those drownings was ever pinned on me."

Brandi gave a short laugh, which actually snorted out through her nose just like Casey the other day. She didn't make any more sound but she grinned at me.

"OK, I get it," she said to Casey. "The man's a riot. Just don't make too much of a pest of yourself, OK? Grownups have a lot more to do than entertain a bunch of kids."

"I won't be a pest," Casey said.

"Perish the thought," I said, smiling into his luscious gray eyes. They came alive and he gave with the megawatts.

I basked in it.

"OK, then," Brandi said just a bit uneasily, and I worried that maybe she had picked up a vibe from my moment of eye-flirting with Casey. "I guess I'll leave you to it," she said, and turning to Casey, "Remember you're having lunch at Terry's house today, and then you can play with them the rest of the afternoon until I get home from my errands around five. Don't be late because Tony is coming for dinner."

"I remember, Mom," Casey said with a hint of resignation. I remembered Geri saying that Casey was often ditched by his Mom so she could go out with her boyfriend, who I presumed was Tony.

It had to be hard to be totally abandoned by one parent and then all but abandoned by the other one too. My heart went out to the boy, but I saw a tinge of regret in Brandi's eyes too. She probably knew it didn't go down well with Casey but she was trying to make things better in the long term, by finding a solid relationship and making a stable home for her son. And if Tony was not a good enough guy then that could be chalked up to kissing a lot of frogs while searching for a prince.

I've often been called a sap for assuming the best motives in people, some of whom don't deserve such charity. For all I knew Brandi might have been a common slut who palmed her kid off on anybody who'd take him so he's not in her way of a good time and a good buzz. In fairness I had seen no evidence of that so I decided to go with my charitable first assessment until such time as Brandi proved it wrong.

Back in the pool the naughty vibe had completely dissipated and the kids were playing and splashing innocently. It was just as well since the Friday afternoon young-adult crowd was starting to show up, the unmarried 20-something guys and girls who knocked off work early on a Friday and used the pool as a place to see and be seen and hopefully hook up.

A singles bar with chlorine.

It wasn't my scene at all so I played with the kids until they started leaving for home. They all bid me a smiling see-ya-later but they didn't seem too broken up about it. I don't know what the hell I expected, but I couldn't help feeling disappointed.

A rainy cold front came through on Saturday so there was no chance of casually running into the kids outdoors. I made myself a half-assed casserole of Kraft mac and cheese and a can of tuna -- a half-asserole if you will -- and ate it in front of the TV, all the while hoping for that firm knock on the door from my little buddy Terry.

It never came.

I spent virtually the entire wet weekend working on my book, but my mind wasn't really on it and I wasn't entirely happy with anything I'd written. It was my first attempt at long-form fiction and I was pretty much flailing with structure and especially theme. Character and dialog, sure, but that's not nearly enough. I threw away my outline and started over.

When it was still fucking raining on Monday and I hadn't seen any of the kids I was convinced that I had been merely a passing fancy for them. I was good for a laugh for a couple of days but now they'd moved on.

I smoked several bowls of nice Colombian and jerked off twice, once to the memory of Terry in my bed and once to a fantasy of passionate lovemaking with Casey right there at poolside, while Geri and Hanna 69'd on the adjacent chaise lounge. I shot even more the second time than the first, which made my melancholy even worse by confirming just how much of a thing I had for Casey. When the fantasy of one boy beats the reality of another it tells you something.

Tuesday dawned with sunny skies and somewhat renewed hope for some kid contact, though I really had no particular reason for optimism other than a good night's sleep. Still no knock at my door so I ventured out at ten to try the pool.

When I got there the place appeared deserted and my heart dropped until I noticed a towel and a small t-shirt draped over one of the chairs. I still didn't see anyone and I thought maybe some kid had left that stuff here overnight, but then I heard a tiny splash and a small, sun-bleached head broke the surface of the water in the deep end. I hurried closer and, sure enough, it was Casey all by himself.

My heart pumped with blood and another organ threatened to do so as well. As I approached the pool the boy saw me and grinned broadly, switching on those steel-gray searchlights.

"Hi, Casey," I said. "I haven't seen you in days."

"It rained all weekend and Mom wouldn't let me go anyplace but Terry's," he said, holding onto the pool gutter just in front of me while I peeled off my t-shirt and toed off my flip-flops. "And then yesterday she made me go to Jasmine's house. It's kind of a day-care, and it's really no fun because most of the kids are like three years old. I have to help Jasmine take care of them so Mom doesn't have to pay for me to be there."

"Don't you usually stay with the Rhyming Kids?" I asked, and Casey looked at me quizzically. "Geri, Terry and Gary?" I prompted.

"Hey!" he exclaimed. "They do rhyme!"

I gave him an incredulous look. "Seriously? This is really the first time you noticed that their names all rhyme?"

He gave me a cheeky smile. "Nah, I'm just messin' with you," he said. "How could you miss that everybody's name rhymes? Even their parents."

"Whew!" I said. "That's a relief. I was starting to think you were a little light on brain cells, like maybe the reason you never wear shoes is because you don't know how to tie 'em."

Casey tried to project indignation at this teasing but his smiling eyes were dancing the Quick-step.

"Let's see you come over here and say that!" he challenged in a playful tone.

"OK," I said, stepping off the pool deck right next to him and splashing him right in the pretty face.

He wiped his eyes and turned back to me with a grin. "I'll get you for that," he said mock-threateningly and made a lunge for me. I caught him by both arms and pulled him into a restraining hold that was actually a barely-disguised cuddle.

"Looks like I've got you instead, tough guy," I said with a grin, and he pretended to struggle but didn't really try to get away. I pulled him along into the deeper water until he couldn't touch bottom and he wrapped his legs around me for support.

My cock was hard as iron.

Surely he must have felt it, crushed up against his thigh as it was, but he didn't acknowledge it. He made no attempt to dislodge it either, and so I pressed even more firmly against his softness and enjoyed the sensation.

Quickly the wrestling pretense slipped away and we simply held each other, smiling eye to eye. I was quickly becoming enamored of this boy and fancied some of the same vibes were coming back my way. In any event he allowed me to tow him around the pool, cuddling and talking softly.

"So how come you have to go be a slave boy at Jasmine's instead of staying with Terry's family?"

"Mom doesn't like to impose on them every single day," he said. "Mrs. Foy says she doesn't mind, but it makes Mom feel bad."

"I can understand that," I said, and we fell silent again, just cruising around the cool water.

When it occurred to me that the pool was clearly visible from several nearby balconies I decided that 15 minutes of openly cuddling a 10-year-old boy was tempting fate, and so I reluctantly moved us back to shallow water and set him on his feet. He seemed as disappointed as I was.

"So where are Terry and the kids?" I asked to break the slightly awkward silence.

"I don't know," Casey said. "I was supposed to spend all day with them, but when I got there this morning nobody was home."

I thought about the implications. "They were supposed to take care of you today while your Mom's at work?"

"Yeah," he said. "That's what Mom said when she left, but they weren't home so I just came to the pool."

"Let's get out and dry in the sun for a few minutes, then we'll go over there and see if they're back."

After confirming that the Foy apartment was dark and quiet we ambled back along the sidewalk, Casey looking adorable in his Calvin & Hobbes t-shirt and bare feet. I don't know what the boy had against shoes but I found it cute and endearing that he was always barefoot.

"I'm getting hungry," he said.

"Oh, crap," I exclaimed softly. "They were supposed to feed you lunch, weren't they?"

"Yeah," he said.

"You're big enough to make your own lunch though, right?" I asked. "You must have peanut butter or something at home.

"I can't go home," he said. "I didn't take my key 'cause I figured I wouldn't need it."

"I'd give you lunch," I said. "but I don't have shit to eat at my house."

"That's OK," Casey said. "I wouldn't want to eat shit anyway."

I stopped in my tracks and regarded him with respect. That was a great joke for a ten-year-old, and really quick, too. He returned my grin and his gray eyes sparkled.

"Do you like McDonald's?" I asked, amused when, as expected, his whole face lit up.

"I love McDonald's!" he gushed, but then his face dropped again. "I don't have any money, though."

"No, dummy," I said, teasing. "It's my treat."

"Really? That would be awesome!"

"But we should call your Mom first, so she knows where you are and who you're with," I said. "Do you know her number at work?"

"No," he said. "It's on the refrigerator at home, but I don't have my key."

"Well, do you know where she works?"

"Yeah. She's the receptionist at a place called Kennedy Electric."

"OK, cool," I said. "If she's the receptionist she'll be the one who answers the phone. Come on."

I let us into to my apartment and looked the place up in the phone book. No Internet in those days, just big heavy paper phone directories. I dialed the number and handed him the phone.

"Mom?" he began. "It's Casey."

I was pretty sure she didn't need him to identify himself by name, probably getting relatively few calls from young boys calling her Mom.

"No, nothing's wrong," Casey said. "Only the Foys weren't home when I got there. I think they went somewhere, and now I'm locked out of our house because I don't have my key. No, you don't have to come home. I'm with Bill. He invited me to McDonald's for lunch. Can I go? Yeah he's right here. Hold on."

I took the phone and put on a bright voice. "Hi, Brandi."

"I'm so sorry you got caught in the middle of this," she said. "Mary told me she was taking the kids to see their grandmother but I thought it was only tomorrow. Apparently it's both days."

"No harm done," I said. "I found him at the pool and he's fine, just a little hungry now."

"Thanks so much for taking him to McDonald's," she said. "I'll pay you back when I see you."

"Oh, don't worry about it," I said. "It's my treat, and then he can spend the afternoon with me and he'll see you after work."

"Are you sure you don't mind?" she asked sincerely. "I hate to impose."

"Nonsense," I said. "These things happen. Honestly, I'm happy to help."

"Thank you very much," she said. "But promise you'll let me know if he misbehaves."

I was really hoping for a certain kind of misbehaving, but I didn't say so.

"I'm sure he'll be fine," I said. "Here, I'll put him back on." I handed the phone over to Casey.

"Yes, Mom," he said in that deferential, you've-got-Mom-where-you-want-her-so-don't-screw-it-up-now tone of voice. "I will. Yes, I promise I'll be good, don't worry. I like Bill. I wouldn't be bad for him. OK. Yeah. I love you too Mom. Bye!"

We couldn't eat inside McDonald's because Casey was barefoot. No shirt, no shoes, no service.

No shit.

We went through the drive-up and he ordered a McNugget Happy Meal, and laughed out loud when I called it a Crappy Meal. Easy joke, but it sure lit up those steel-gray eyes. I'd do damn near anything to make those eyes light up. As a bonus he gave me a truly affectionate look and once again I basked in Casey's warmth.

While Terry was a sweet boy and one of the best bed-buddies I'd ever had, and with even better adventures promised for "next time," I was starting to fall hard for Casey, more than any boy since The Love of my Life, whose beautiful little heart I had broken several years earlier.

The Regret of my Life.

Someday I'll tell that story but I can't handle it right now. Let's just say it taught me a valuable lesson about not overthinking the whole inter-generational thing. The boys don't see it as defining the entire rest of their lives and their men shouldn't either.

We took the food back to the complex and ate at a picnic table near the pool. Just before we finished Miles arrived with a very cute younger boy with light brown hair and friendly brown eyes. The smaller kid was identified as Justin, Miles' just-turned-nine-year-old cousin who was visiting for the day. He was a bright and happy boy and when Casey offered that we would join them shortly for swimming I eagerly seconded the motion.

The afternoon went pleasantly and innocently. There were quite a number of young mothers on hand and in any case I didn't want to be too aggressive with Justin around, so I kept it PG. He was a real cutie and didn't mind being cuddled, though he was no innocent little child. He was sharp as a cactus needle and got every reference by me and the older kids, and even made a few sly comments himself. I thoroughly enjoyed both Justin's company and his sleek little body but never ventured into call-the-police territory.

Late in the afternoon Miles' mother and another woman greatly resembling her -- a sister it turned out -- came to the pool and rousted their boys to come get dressed for dinner. All but one of the young mothers had gone by then and the remaining one was severely busy with twin toddlers, so I risked getting touchy with Casey again. He beamed in response.

"Did you have fun with Justin?" he asked after a few minutes in my embrace, and I searched his eyes for signs of jealousy.

It was inconclusive.

"I guess," I said. "He seems like a nice boy."

"So you like him, then?"

"Yeah, sure," I said, then added, "But I like you more."

The eyes switched on. "Really?"

There was no one in earshot so I leaned in close and said, "I like you more than any other boy."

I'm ashamed to admit I've said such things to boys just because it was what they wanted to hear -- and perhaps would get me somewhere -- but in this case it was true.

Casey's eyes were never brighter. His arms had been around my neck as I towed him around the pool and he pulled himself tighter to me.

"I like you better than anybody, too," he whispered into my ear, then lay his beautiful wet head against my shoulder.

I glanced around and nobody seemed to be watching, so I took my chance. I kissed him quickly on the neck and hugged him tightly.

Casey sighed and I felt his whole body relax in my arms. I knew the boy was needy, especially for adult male affection given the unmitigated shit-show of his father, but I could also tell that I wasn't just any port in his emotional storm. We genuinely clicked, a real mutual attraction becoming obvious.

My heart was glad, and I suddenly realized it wasn't all about my dick with this one. Maybe it was the luxury of already having Terry for that need, but right then I knew that I would be happy to have Casey in my life even if I never had him in my bed. It was his little heart and mind that I wanted. Not that I would refuse if he offered his body, but suddenly I didn't need it.

After a while Casey nudged himself away from me. "It's after five," he said, which I verified on the big clock over the door. "My Mom is probably home from work." I could see that he was reluctant to leave me, but he knew he had to.

"It's OK," I said, smiling my broadest. "I had a great day, Casey."

"Me too," he said. "I love hanging out with you."

"Me too, kid," I said.

I walked Casey home just to get a few more minutes with him. I told you I had it bad.

Brandi opened the door with a huge smile. "Hi, Baby," she said, enfolding Casey in her arms. She didn't try to pick him up, but then she was kind of a little thing and probably couldn't. She kissed him on the head and said to me, "Thank you again, Bill. You were a life saver today."

"Oh yeah?" I said with a straight face. "What flavor?"

Brandi looked at me in confusion, then the light bulb went on over her head. "I don't know," she laughed. "Wintergreen, maybe?" Casey got the joke then too, and we all laughed together.

"See, Mom?" he said. "I told you he was funny."

"Yes you did, honey," she said. "About a hundred times."

"Corny is more like it," I said as the laughter trailed off.

Brandi looked like she was about to say something but changed her mind.

"What?" I asked with a smile.

"No, I shouldn't," she said. "You've already done so much."

"Nonsense," I said. "It's my pleasure to help."

"No," she said again. "I'll find someone else. I don't really know her but maybe Miles' Mom can take him tomorrow."

I made sincere eye contact with her. "I thought you had tomorrow covered."

Brandi looked at the floor, embarrassed. "Tony was supposed to come watch him," she said. "My boyfriend. But he called and said he couldn't do it because he's going to the race track instead." Brandi looked at the floor again. "Last minute invitation, I guess."

I glanced down at Casey and he was grinning.

"Not to worry," I said. "I'd be happy to have Casey again. In fact, I've been wanting to see that new Spielberg movie everybody's talking about, the one with the kids on the flying bicycles. Going to the movies alone is slightly pathetic, so it'd actually be doing me a favor to have Casey along. If he'd like to go, of course."

"Would I!" he gushed. "Please, Mom! Please let me go! I'm the only kid around here who hasn't seen it yet!"

Brandi looked relieved. "If you're sure you don't mind," she said. Reaching for her purse she added, "Only this time it's my turn to treat. And I'll pay for your lunch. I insist."

She fished out a $20 bill, which would way more than cover it in 1982, even with lunch and popcorn. I didn't argue, just thanked her.

I watched Brandi carefully as Casey threw his arms around my waist and gave a heartfelt goodbye, and an eager "See you in the morning!" Her eyes remained happy, which was a great sign.

The knock came at my door at five minutes before 8am, a grinning Casey arriving barefoot in his usual swimsuit and t-shirt, but carrying a backpack with a change of clothes and a pair of sneakers for the trip to the movies. My fevered brain immediately envisioned watching him change clothes, even though I knew he'd probably do so in the bathroom.

The morning was again about pool play, which thanks to the lack of fellow swimmers mostly consisted of cuddling and canoodling in the water. I not only didn't conceal my erection, I made a point of pressing it against him looking for some sort of reaction. Still he ignored it until I was forced to conclude that Casey enjoyed my intimacies and wanted them to continue, but was pointedly leaving himself an escape route if things went badly.

Plausible deniability the politicians call it. Eventually I would confront the situation but not right then, not at the pool.

We went back to my apartment for lunch. I had gone to the store the previous evening and spent some of Brandi's twenty, stocking up on kid-friendly staples: peanut butter, tuna fish, mac and cheese in a box and so forth.

"Let's take a quick shower to get the chlorine off," I said. "Then we'll dress for the movies, have lunch and head out."

"OK," he replied happily.

"I only have one bathroom," I said, ushering him to it, disappointed when he grabbed up his backpack on the way. "There's soap and shampoo on the shelf in the shower and I'll put out a clean towel for you."

"Thanks," Casey said with a shy smile, then simply stood looking at me. Five seconds passed.

"OK," I said in small embarrassment. "I'll get that towel and leave you to it, then."

I kept the smile on my face while my mind said shit shit shit, he won't strip in front of me. I had no choice but to take the hint though, so I stepped out to the hallway linen closet and got him a towel. He closed himself in and a few seconds later I heard the shower come on.

I wanted so badly to pop my head in "to make sure he's OK," but really of course to get a look at his delectable goodies. I didn't, though. I honestly did respect every boy's right to choose if and when to take things further, even while rebuking myself for once again being too nice a guy, passing up a great opportunity with a beautiful boy who almost certainly wanted things to happen but just couldn't be the one to initiate it. He only needed me to give a nudge, but I didn't.

In 10 minutes he emerged dressed in a fetching, tight-fitting outfit consisting of a powder blue t-shirt and dark blue cargo shorts, still barefoot and carrying a pair of formerly white sneakers. The powder blue magnificently complemented his steel-gray eyes, which projected his signature megawatts when he saw my enraptured reaction. His sun-bleached hair was wild and I made him go back and comb it, watching him in the mirror and falling ever harder for him. When he turned and presented himself for inspection I couldn't help but gush.

"Damn, Casey!" I said. "You look fantastic! What a beautiful boy you are!"

My language was far too romantic but it didn't seem to upset him. In fact he beamed at me with those lovely twin lighthouses and blushed coquettishly, like a teenage girl proud of her pretty prom dress.

This kid was killing me with contradicting signs.

I regained my composure. "OK, then," I said. "You figure out what you want for lunch and I'll grab my shower."

I very deliberately took no clothes with me into the bathroom, leaving the door wide open as I stripped off my swim trunks.

"Gets too steamy with the door closed," I said over my shoulder as I turned on the shower, keeping my back to him but knowing that he could see my semi-stiff cock in the mirror. I didn't look back but I knew full well he was watching.

When I finished showering and threw open the curtain Casey wasn't nearby. He was sitting on the far end of the living room sofa -- the only seat where he could see in through the bathroom door. I made no effort to hide myself as he watched me dry off, apply deodorant and comb my hair, though he tried to be circumspect about it.

In a moment I stepped naked into my bedroom, calling out, "So what did you decide for lunch?" As expected he came to the bedroom door to answer.

"I was thinking tuna fish, if that's OK," he said as I put on underwear with my back to him. When I turned around my boxer-briefs were bulging like I was smuggling an eggplant through Customs, and his mouth fell open.

"Fine," I said. "I like minced onion in mine but we can skip that if you don't like it."

"Huh?" Casey asked, having heard not a word, his eyes still fixed on my bulge.

"Onion," I repeated with a playful smile, "in the tuna fish." Then, "What's the matter? Haven't you ever seen a guy with a boner before?"

"Um, yeah," he stammered. "Only kids, though."

"Same thing, only bigger," I said. "It's just something that happens. Perfectly natural. You're a guy, you must get 'em too."

"Um, sometimes," he stammered again, looking away in embarrassment. I tried to see if now might be one of those times but I couldn't tell in the cargo shorts.

Casey turned away abruptly. "Let's eat," he said. "I'm hungry."

After our tuna repast, which for the record contained a little bit of minced onion, we went to the movies. It was great fun watching Casey watch the movie as he reacted emotionally to all the different beats Spielberg so masterfully hit. The boy was excited, scared, sad and happy in all the right places, but there was one moment I'll cherish forever.

Elliott was placed into quarantine with the apparently dead E.T. (Henry Thomas cute as hell, I might add, in his clinging thermal underwear bottoms and no shirt.) I glanced over at Casey and saw his lower lip tremble, and then a single tear appeared in one eye and trickled down his lovely face.

If I wasn't a goner before that I certainly was after. To this day it is the single most endearing image of a boy in my long, long memory.

All the way home and right up until I returned him to his mother Casey jabbered about the movie. We relived virtually every scene, each time beginning with the boy's enthusiastic, "Remember when...?" followed by the likes of "...E.T. was hiding in the closet with the stuffed animals?" or "... E.T. drank beer and Elliott got drunk too?" I noted that he didn't reminisce about the sad scenes.

"What did you think," I interjected at one point, "about the fact that Elliott's Dad didn't live with them?"

"Dads go away sometimes," Casey said with little to no emotion. "It isn't Elliott's fault. Just sometimes Moms and Dads can't be with each other anymore."

This was obviously his mother talking, and it brought the mood down quickly. I wished I hadn't mentioned it.

Casey made a point of smiling up at me. "Don't worry, though," he said. "Elliott can be happy with just a Mom, especially if he finds somebody nice to have fun with."

I knew full well that he was referring to me, and not in the sexual sense of having fun, but I pushed on to get another piece of information.

"Do you have fun with Tony?" I asked.

Casey made a face. "No," he said. "I don't think he likes me, and I sure don't like him! I was really happy that I got to be with you today instead of him."

It was my turn to switch on the eyeball-megawatts.

"Me too, kid," I said affectionately. "I wish I could spend every day with you."

Casey beamed, and somewhere in the back of my mind the L-word peeked around a corner.

Back at their apartment Casey launched right into a recap of the movie for his Mom, starting at the top. I was glad he was so enthusiastic and that I was able to give him such a fun day, but Jesus, enough with E.T. already!

"OK, kid," I said, "I'd better get going. Maybe I'll see you tomorrow at the pool."

Casey stopped his prattling cold and ran into my arms. It just seemed right to lift him up, and he gripped me around the waist with his legs and around the neck with his arms. He hugged me tightly and thanked me over and over for "the best day ever!" I caught Brandi's eye and she was looking on 100% approvingly.

It was 1982 and people did not yet automatically question the motives of every unmarried man who likes kids, plus I think it helped that I was eight or ten years younger than Brandi and she could think of me as just a big kid myself. In any event she saw "free babysitter that Casey loves to be with" and not "filthy perv who wants to debauch my son."

It worked for me.

"Listen," Brandi said. "I'd really like to thank you for being so good to Casey. Why don't you join us for dinner Saturday night? Tony will be here and we can all get to know one another better."

Casey's grip tightened around my neck at the mention of Tony's name, but he kept quiet.

"Why not?" I replied. "I'd love to."

Of course I wouldn't really love to, Tony sounding to me like a world-class asshole, but I guessed I could put up with some macho bonehead for one evening if it got me more solidly into Brandi's trust. Arrangements were made for 7pm on Saturday, and with cheerful goodbyes from both mother and son I took off.

At ten minutes to eight Thursday morning the expected knock came on my door. I threw it open with the words, "Good morning, Casey!" ready on my lips, but I had to stop short when a grinning Terry pushed right inside.

"Hi, Bill!" he called cheerily. "Did you miss me? I sure missed you. It's been almost a whole week!" As my mouth hung open in surprise Terry closed the door and threw the deadbolt. "Kiss me!" he demanded with a naughty smile. "Hurry up!"

There's nothing like a randy 10-year-old to get you past a moment of shock and into the mood. I lifted him into my arms and our mouths met with the same passion as our previous encounter. Terry's tongue pushed into my mouth and suddenly we were soul kissing like mad.

After a solid, fierce minute we broke apart and he held my gaze with all his intensity. "Take me to the bedroom!" he urged huskily. "I need it real bad!"

Twenty seconds later we were naked in my bed, him on his back and me slurping his bone-hard little thing between my lips. It seemed even smaller than last time somehow, but it was firm and hot and thrummed with life as he undulated his hips up to my face.

I caught my rhythm in seconds and I began working him the way I knew he liked. I plunged all the way down and pulled back slowly, sucking and slurping and tonguing the blunt little head and nibbling the glans and going back to deep plunges, starting all over again until I felt his thighs and belly tense and release five or six major times. Finally he buried it deep in my mouth, crushing my head tightly to him as his tiny bald nuts struggled in vain to shoot me a load.

"Whew!" he exhaled as he collapsed to the mattress. "Man I needed that! I haven't even had a chance to play with it since the last time I saw you."

"Poor baby," I said, climbing up to nuzzle his neck and peck tiny kisses all over his face.

"I know, right?" he said with a grin. And then in a low, conspiratorial hush, "You know what I want to do today, doncha?"

"Are you sure you're ready for that?" I asked. "You know you don't have to if you're not ready. In fact you never have to."

"I know," he said, "but I really want to. I've been thinking about it for days! I think if we go real slow and use lots of grease it'll be OK."

"I don't want to hurt you, Terry."

"You won't," he said. "I promise I'll stop you if it hurts too much."

"OK," I said. "Just tell me what you want."

"Let's suck each other at the same time, then you can lick out my butthole for a long time and get it really wide open."

Terry spun around and we slipped into 69 position on our sides. My mind went briefly to wondering if Casey's knock would come at the door sometime in the middle of this, but then soft 10-year-old lips closed around my cockhead and all other thoughts went bye-bye.

His skinny, less-than-three-incher was raging hard again, and I had to scrunch myself into a pretzel to accommodate our height difference, but again I eagerly took it into my mouth. I knew I could never get enough of any hairless cock that was attached to a tender young boy. Zaftig little Terry was not my physical ideal, but I adored boys in all shapes, sizes and colors. I'd sucked skinny kids and fat kids, Black kids, Latin kids and Asian kids, the very young and the slightly-too-old.

They were all my favorites.

After a while I moved from his bony little cock to his small, tight nutsack. It tasted so sweet and the little pills felt so right rolling around on my tongue that I wished for a second that we could finish just like this, and I could lick and lave and suck these little rocks until I fired my thick, gooey wads into the talented little mouth that pulled at me so eagerly. But then I thought of Terry's tiny pink asshole, gaping open and practically crying out for my thick meat. I imagined my turgid length disappearing millimeter by millimeter into the depths of his loving little body, and how much he really and truly wanted it, and I knew that was how it was destined to be.

I scooted forward a bit and left his saliva-coated nuts for the dusky crevice that guarded his most intimate entry. With both hands I pulled his soft round buns apart and licked into his hole.

"Mmmmm!" he moaned around my cock, renewing his sucking to an even more intense level. My cum wasn't rising yet, but it wouldn't take too long if he kept that up.

The tip of my tongue flicked across his tender anal ring and Terry moaned even louder. I pushed it through the ring and I felt him willing himself relaxed, opening himself for the intruder. I stiffened my tongue and probed even harder, pushing in a half inch or so. Terry's high-pitched moan came louder yet and his sucking intensity vaulted again.

"Careful, baby," I warned. "Don't make me shoot."

I felt him temper his ministrations on my steaming hot dick and my urgency retreated. On and on our mutual oral pleasure went until I knew he was fully pliant and ready.

"Do you want to try now, sweetheart?" I asked, and the boy immediately pulled off of my cock and spun around to face me.

"Do you have the K-Y?" he asked breathlessly.

"Right here," I said, grabbing from the nightstand drawer the brand-new tube I had purchased the day after our first encounter.

"Gimee!" he ordered, practically ripping it out of my hand. "Lay on your back."

He was not-so-large but fully in charge, so I let him lead. He spun off the cap and squirted a copious amount of the goo into his hand, then began smearing it liberally onto my upward-jutting cock. It felt great in its own right as he carefully coated every inch in a thick layer, topping it off with a sizable glob right on the tip. With a grin Terry climbed astride me, face to face, with one knee on the bed and the other lifted high as he worked another generous squeeze of jelly into his own hole.

Unmindful of the excess K-Y that streaked my chest and side as he steadied himself with his hands, the boy carefully positioned himself just above my pulsing organ. He settled a fraction at a time until my blunt dick-tip touched its target, zeroing in until it was precisely aligned with his tiny pucker. With a devilish smile he began to lower himself onto me.

I registered the fiery heat of his glorious inner channel, but only on the very tip of my cock. It was barely nosed into him, already stretching him wider than he'd been with my finger. A glance downward confirmed that his own little cock was still jutting up stiffly, and I searched his face for discomfort but saw only the bright eyes of mischief.

Terry reveled in this, the most forbidden of all acts between a man and a boy, maybe precisely because it was forbidden. It seemed to me to be the ultimate bold and cheeky move for a boy with a rebellious mind, but who was fundamentally good in his heart. I would never believe that Terry could actually hurt anyone, but I sure believed he liked the hell out of defying what the world expected of him and going his own way, doing things that felt great but would make society -- and especially his parents -- have heart failure.

As long as it was secret, of course.

His face tightened in resolve as he pushed himself downward. I felt him slip a half-inch and his mouth opened wide at the pain. I gave him a concerned look but he forced a ragged smile, uttering huskily, "It's OK. I'm OK."

He kept himself there for ten seconds, his anal ring stretched drum-tight around my cockhead just above its widest point, seemingly stuck. I was sorely disappointed when I saw that his boner had retreated, the first time I'd ever seen him limp and incredibly tiny. Terry gulped a big breath and his face tightened again in determination, and then he willed himself further open while forcing himself down and the rest of my cockhead popped into his vise-grip rectum.

"Oh-ohh-ohhh-ohhhh!" he cried, the moan modulated into four distinct syllables but with a tinge of pleasure mixed in with the pain. I grabbed his buns and held his weight up with my hands as his body vibrated and his belly clenched.

"Oh my God!" Terry exclaimed softly. "It's so big! Oh, man!"

"Do you want to stop?" I asked in deep concern. I couldn't tell if it was killing him or thrilling him.

"No!" he cried instantly. "It's OK," he insisted. "It's really big but it's OK. Just give me a minute."

It was almost the full predicted minute that I held his weight above me while I felt him rhythmically tighten and relax his butthole, willing it to open. Soon I realized that it was starting to work as the intense grip he had on my cock began to infinitesimally loosen.

"OK," he breathed. "Let me down some more."

I carefully let him resume control and he slid down a solid two inches before stalling again. He had about half my cock at that point and he grinned at me in triumph.

"It's working!" he cried. "I knew I could take it!"

Terry lifted himself slightly and settled down again, another two inches of my shaft plowing into his deep, searing recesses. It was amazingly hot and tight, gripping me on all sides and thumping with our combined heartbeats. He pulled up one last time and let himself settle until his soft, smooth ass cheeks touched my thighs.

"It's all the way in, isn't it Bill?" he implored, needing to hear me say it.

I smiled into his radiantly happy face. "Yes, baby," I said lovingly. "You have all of me now. Are you sure you're OK?"

"Yeah!" he said happily. "It feels amazing! I love having it up me!" He sat impaled for maybe fifteen seconds, and I was thrilled to see his dick inflate again to damn near full erection.

Then he began to move. It started as just a wiggle, then grew into a rock, and finally into a grind. He threw his head back in ecstasy and moaned in pure pleasure.

"It feels so good!" Terry moaned. "I feel all the way full!"

I held him by the hips and rocked along with him. It was pretty goddamn amazing for me, too.

"OK," he said after a while. "I'm gonna lean back now, but don't let me lean back too far. Hold me around my middle and I'll tell you when I get to just the right place."

I didn't know what he was doing but I figured it must be something he had learned with Brian. I put my hands behind his lower back and counterbalanced his backward leaning. I could feel the angle changing inside him as the top surface of my cock made firmer contact with the upper wall of his rectum. I felt a small, firm protuberance and I knew it was his prostate.

"Right there!" he cried. "Hold me just like that and fuck me! Fuck me hard!"

I grunted like a bull as my lust rose in an instant and took complete, animal control of my being. I was in full-on deep fucking mode in the blink of an eye, and I began to thrust upward into his hot, tight little asshole like the world depended on it. In two seconds I was pounding hard and fast into him, my cock tickling his love button and our greasy skin slapping wetly together in double time. He was grinding fiercely down onto me as well, and we fucked and fucked until the sweat was running off of both of us. My eyes were fixed on his little face and I saw nothing but the delight of a boy getting exactly what he'd dreamed of.

"Oh, Bill, I'm almost there!" Terry cried. "Cum in me! Shoot it inside me!"

My own orgasm loomed and I strove for it. Terry's ass clenched strongly around my shaft and I pounded even harder to push through this new resistance. I felt the rhythmic pulses that said he was cumming and his mouth opened in a silent scream. I slammed deeply into him for fifteen more seconds and finally rushed over the edge, my hot jets of cum spurting over and over inside him. He fell forward onto my chest and our heavy breath mingled as we both began a long, slow drift back down from the stratosphere.

I held Terry tightly, still impaled to the hilt. My vision was fogged, little bursts of light twinkling randomly in the darkness like flash bulbs at an arena rock show. My cock remained stiff for a surprisingly long time and he made no effort to relinquish it. Little aftershocks shook him and made him squeeze me, which didn't help me deflate. Finally my dick partially retreated and I had enough control to kiss his forehead and ease him off of me to the side.

It felt weird to no longer be inside him.

As our breath returned Terry snuggled up into the crook of my arm, his head on my shoulder, smiling happily. It was great to see, and I kissed him sweetly.

"Are you OK?" I asked.

"Yeah," he replied. "I think my butt's gonna be sore for a few days, but it was totally worth it. I'm so glad we did it!"

I hugged him closer. "Me too," I said. "You know, I've only done that with one other boy, and it was great, but you were amazing!"

Terry swelled with pride. He laid his head on my chest. "I love making you feel good."

I think we fell asleep for a while, as the next thing I remember is rousing him off of my chest and taking him into the bathroom.


Thanks for reading Part 2 of Woulda Shoulda Coulda #2: Steel-Gray Eyes. I hope you enjoyed it. Part 3 is coming soon to Nifty's Adult-Youth category. Of course you can also check my story archive here on my Prolific Authors page.


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