Welcome back to the second story in my series based on my own real experiences. This is Part 3. If you haven't read the earlier parts I suggest you read them 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
After showering off the evidence of sex Terry and I headed to the pool, where his siblings and the usual gang of other kids were already playing. Casey gave me a bit of a look when he saw us arrive together, but when I shot him a smile he returned it eagerly.
"Where were you guys?" he asked me quietly the first chance he had away from the others. He didn't look mad as far as I could tell. I wanted to be honest with Casey sometime soon, but he wasn't ready yet and in any event I wasn't going to start that conversation out here in public.
"Terry came by a little while ago to see if I was coming to the pool," I said, "so we just came over together."
He gave me that slightly weird look again. "Geri said Terry left home like, two hours ago."
"I couldn't tell you when he left home," I said innocently. "He hung around at my place for a bit while I took a shower."
Casey thought for a second. "Why take a shower if you're coming to the pool?"
Uh-oh. Didn't think that one through. I thought I might have to tell him part of the truth and risk a) scaring him off, or b) making him jealous. I was struggling with how much to tell him when a workable line of bullshit suddenly came to me.
"I spilled Coke all down my front," I said. "It was getting really sticky..." I leaned in close and whispered in his ear, "...on my dick and balls."
Casey's mouth came open in a shocked explosion of laughter.
"Quiet!" I admonished. "That's just for you to know, not the whole world."
Casey stifled his laughter but his bright gray eyes shone with merriment.
"And don't talk to Terry about it, either," I said. "I already swore him to secrecy."
"OK," Casey said, and it occurred to me that it might have cemented our relationship even more, that I trusted him with something I found embarrassing. I guess it might have actually meant something if it hadn't been a lie.
Pool play ensued in the usual way, as lovely for me as always. In one particularly intense scrum with smooth preteen limbs tangled like last year's Christmas tree lights, one of the boys was on my back with his arms around my neck and his body crushed against me. I felt the distinct prod of a stiff dick, a feeling I'd know anywhere. I pressed back against it and felt the unidentified boy push more firmly against me.
I know what you're thinking, that this must have been Terry being predictably cheeky, or Casey finally taking the chance to accelerate things, but it wasn't. I suddenly noticed that the steely hard boycock that pushed against my back was considerably larger than any I had yet encountered. In fact, it was really big for a boy that age, and when I craned around to get a look at him I found myself eye to emerald-green eye with Miles.
He humped it against me a few more times then disengaged, swimming away on his back and grinning at me. His bulge broke the surface and I'll tell you, it was impressive. Had that been the one I had groped the other day I would certainly have noticed its size, so the kid I groped must have been Casey.
Good news on both counts, of course. It confirmed that Casey gets boners for me, and that yet a third boy was interested in naughty fun and games.
There were thunderstorms Friday morning and the pool was closed. Terry came to my apartment but Casey was with him and, though I was confident that Casey would come around if Terry and I started something, Terry clearly didn't want to risk it.
It's scary with your best friend. If he freaks out you'll lose him.
Saturday 7pm came and I knocked on Brandi's door, freshly showered, dressed nicely but casually, and carrying a small strawberry cream cheesecake from a local bakery. I had considered bringing wine but didn't want to undermine her image of me as a big, innocent kid. It had the bonus, too, of being something Casey could enjoy with us.
A smiling Brandi opened the door with effusive greetings. The moment he could elbow past her Casey wrapped his arms around my waist and laid his face flat against my stomach. I mussed his hair and said an affectionate "Hi, kiddo," as Brandi ushered me inside.
In the living room was a smallish, dark-haired and goateed man not quite 40, fairly attractive and in good physical shape. He was swallowing a healthy slug of Budweiser as he sprawled on the couch watching a baseball game on TV. He held up a finger in the "just one minute" gesture while he watched a routine fly ball be inevitably caught.
That play wasn't exactly a nail-biter, but I allowed that some fans are truly fanatical so I waited patiently.
He turned to me but didn't get up. "You're Bill, huh?" he said.
"Yes," I said, stepping forward to offer a handshake. "You must be Tony." He didn't move, so I took one more step forward and shook his hand where he sat. He wasn't being precisely rude, but he sure wasn't rolling out the red carpet either.
Tony watched a routine grounder end the inning. "I ought to be pissed at you, dude," he said, in a tone of voice that was apparently intended to sound joking. "You took the kid to that movie and now it's E.T. every five seconds."
Many a truth is told in jest, and in 30 seconds with this guy I knew that he considered Casey to be an imposition that he barely tolerated, and had utter disdain for any adult male who bothered with the silliness of children. In his mind he was a man and I might as well be a girl.
"I'm glad he had such a good time," I said, smiling sweetly. Tony didn't smile back.
"Bill brought a cheesecake for dessert," Brandi said brightly from behind me.
"Oh, yeah?" Tony said. "Did you bake it yourself?"
His eyes twinkled at his own joke and I forced a chuckle while imagining my fist driving his teeth down his throat. I didn't need this prick to approve of me spending time with Casey, as I was sure Brandi would be the one to make that decision, but it wouldn't help things to have him actively undermine me.
"Nope, just picked it up from this little bakery I know," I said, pretending I didn't catch his dig. I nodded toward the TV. "Are we still up five to four?" I asked. "That's the last I heard on the radio."
He perked up a little. Apparently liking baseball is at least a step in the manly direction. "Ramirez led off the 6th with a homer," he said. "It's six to four in the middle of the seventh."
"Nice," I said with a smile. "If we hang on we should move into second place in the division."
"Yeah," he said, warming to the discussion if not to me. "Pittsburgh lost this afternoon, so we'll at least tie for second no matter what."
"Cool," I said, making eye contact. "With the top of the pitching rotation coming up we ought to take the San Diego series."
"Yeah, man," he said, gaining enthusiasm. "Salazar is career twelve and two against the Padres. He mows 'em down!"
"Dinner, boys," Brandi called from the kitchen, and I was glad of the timing because I was almost out of baseball talk.
The truth was I followed baseball casually at best and had no idea of the standings or the pitching rotation or any of that. Oh, I knew the game itself, having played like a fiend as a kid, but I could never get very worked up over which team of millionaires beat which other team of millionaires. I had listened to the game while I was getting ready and memorized some of the shit the announcers said, figuring it might come in handy.
We small-talked over a lovely dinner of chicken and dumplings made in a crock pot, Tony shushing us every few minutes when it sounded like something was happening in the game. I was my usual droll self, getting several laughs from Brandi and Casey and even a few from Tony. I still felt his disdain, albeit tempered by baseball.
I noticed that Casey was unusually quiet and I tried to engage him several times, but he would shoot a look at Tony and then mumble a short reply that invited no follow-up. He was clearly intimidated by the guy, which made me hate him even more.
As Brandi and Casey cleared the dinner dishes and she prepared to serve dessert and coffee -- terrific cook and hostess, by the way, that Brandi -- Tony looked me in the eye and said, "So, Bill...you and the kid get along pretty well, huh?"
My deflector shields went up: Yellow Alert.
"Yeah, sure," I said casually. "He's a nice boy."
"He sure likes you," Tony said. "Wants to spend all his time with you, it seems like."
That sounded suspiciously like a compliment, and I wondered where it was going.
"So you like to spend time with him too, huh?" Tony said, more of a statement than a question.
Brandi came in from the kitchen with a coffee pot and three cups on a tray. "Tony," she admonished gently, and I sensed that she was soft-pedaling so as not to set him off. "We said we weren't going to bring that up until after dinner."
The man's jaw set and Brandi's eyes registered wariness. "It is after dinner," he said, and Brandi immediately backed off.
"I'll get the cheesecake," she said, scurrying back into the kitchen as Casey came in with dessert plates and forks.
"I hear you're taking some time off... don't have a job these days," he said, focusing intently on my eyes.
I looked him in the eye right back.
"You hear right," I said, deciding not to mention that I was working on a novel. It would be another chink in my masculinity for this lout.
"And you don't have a girlfriend or anything," he said, "takin' up your free time." He said it in a tone that made clear it didn't surprise him at all.
"No," I said flatly. "I just moved here, and I haven't met anyone yet."
"Right," he said just a tiny bit sarcastically, and I couldn't tell if he was calling me queer or just too much of a wimp to attract women.
Now, despite being what I call an asymmetrically pansexual boylover -- that is, someone who enjoys sex with all ages and genders, but with a very strong preference for boys -- I present absolutely straight and masculine to the world. I'm a big guy with a broad chest and pretty good musculature, and in fact most gay guys I meet are surprised when they find out.
They get over their shock about the time their cockhead enters my throat.
I decided Tony was merely calling me a wimp, which in the circumstances was oddly a relief. I effected a non-confrontational tone.
"What are you getting at, Tony?" I asked as Brandi brought in the cake.
He smiled. "Me and my girlfriend," he said with slightly insulting emphasis, "have a chance to get away next week to my buddy's cabin up in Wisconsin. Brandi's got some personal days coming at work, right, baby?"
"I have to use vacation days, but yeah," she said, slicing the cheesecake.
I could hardly believe where it seemed this was going.
Tony said, "So we were hoping you could maybe take care of the kid while we're gone."
My heart leaped in joy, but I managed not to show it. Casey on the other hand threw his hands up and whooped, "All right!" Megawatts beamed my direction.
"I'd want to pay you, of course," Brandi interjected quickly, but shrunk back when Tony gave her a venomous look.
"Now honey," he said, the emphasis this time slightly threatening. "Let's not insult our new friend."
I realized two things in that instant: a) Tony's actual preference would be to jettison Casey from his life forever, and b) he and Brandi would never last. Sooner or later she would choose her son over him and he'd call her a bitch and move on to less-encumbered pussy. I felt sorry for Brandi, but for the moment it was working in my favor.
"That's this coming week?" I asked, pretending to mull it over. "Yeah, I think I can swing that for a couple of nights."
"Three nights," Tony said. "If you could take him Monday so we can get on the road right after work, then Tuesday and Wednesday, it would be great. We'll be home sometime Thursday afternoon. You don't have anything important to do those days, right?"
I put on an entirely fake smile. "You've got me all figured out, don't you Tony?"
He and I both forced laughter, but neither of us bought the phony bonhomie. He thought I had acquiesced because I was too wimpy to challenge his will, while of course I was actually playing his arrogance and stupidity to get three whole nights alone with Casey. That should be time enough for him to loosen up and go for what he secretly desires. My heart was doing handsprings.
After dessert Brandi provided me with health insurance information and a note authorizing me to make medical decisions for Casey (which in retrospect I'm sure wasn't legal.) When the evening wrapped up I had goodbye hugs for Casey and Brandi and an insincere nod for Tony. As I walked back to my place I whistled a little tune and grinned at how things had worked out.
Sunday morning the now-commonplace knock came at my door around a quarter to eight. I checked the peep hole and saw two little heads, but both with dark hair. I was sure the brown hair was Terry's and deduced that the black hair belonged to Miles.
"Hi, fellas," I said brightly as I opened the door, feeling pretty sure this was going to be a very fun morning.
"Hi, Bill!" Terry chirped with his usual enthusiasm, and as usual walked right in like he owned the place. "I brought Miles today."
"I see that," I said with a sly smile as I closed and locked the door. "You boys have been busy, haven't you?" Miles only grinned but Terry laughed out loud.
"Yeah! Miles and me fooled around at his house yesterday. His Mom went shopping and left us alone, and Miles came right out and asked me if I like to do sex stuff. I said, Boy do I!"
Miles turned his green eyes to me a bit shyly. "I saw you guys feel each other's dicks in the pool, so I figured you liked it."
"Boy, do I!" I said, and they both laughed. "So that's why all of a sudden you rubbed your boner against me," I said. "That was one way to let me know!"
Terry grabbed my hand and started pulling me toward the bedroom. "Let's don't just talk about it," he said. "Let's do it!"
The instant we got there Terry stripped in approximately three-point-eight seconds. He jumped onto the bed and grinned at us in puppy-dog eagerness. Miles pulled off his t-shirt but stopped there, looking expectantly at me. I figured he wanted a show, so with smiling eye contact I slowly slipped down my sole garment, my ubiquitous sleep shorts.
Miles watched intently and his smile widened when he saw my straining hard-on. "You weren't kidding, Terry," he said in appreciation. "He does have a big thick one!"
"Miles has a big one, too!" Terry piped in.
"I know," I said. "I made its acquaintance in the pool." If the boys didn't know the precise definition of the word acquaintance they got the general meaning.
"I guess it's pretty big," Miles said, "because guys keep saying so."
That sounded encouraging, that lots of guys have seen and commented on his dick.
"Well let's have a look," I said gently, not sure why this aggressive boy seemed to need coaxing.
"Will you pull 'em down for me?" he asked. "I like that."
Terry piped, "I did it yesterday!"
I gave him a knowing look. "I'll bet you did lots of things yesterday," and both boys laughed.
I slipped to my knees in front of Miles and sat on my heels. (I could still do that when I was 27.) I smiled up at him and he smiled down. I took hold of the legs of his very baggy shorts, effective for disguising even a boner his size, and began to pull. The shorts slipped easily over his slim hips and fell right to the floor, exposing a pair of white briefs that did nothing whatsoever to disguise anything.
Miles' bulge was even more impressive than I had realized from my brief glimpse in the pool. The thick protuberance came almost up to the waistband of his undies and tented out an inch or more.
I was reminded of my first encounter with a boy older than my usual range of attraction, an eager 14-year-old named Aaron, who was so excited to get his first-ever blow job that he could hold out only about 15 seconds before shooting a fierce teenage blast down my throat. Not to worry though, because he then stayed steely hard for the next half hour while I sucked and slurped and plunged up and down until I earned another big load straight from his spigot. I thoroughly enjoyed that boy despite his overabundance of birthdays.
Normally if I'm going to have someone beyond puberty I go for a teen who is actually legal, at least 18. Why risk prison for someone too old to really do it for me? With Aaron it just sort of happened and I was glad it did, but the point of mentioning Aaron at all is that Miles looked to be nearly that size at only ten years old. I began to fear that I would skin down those briefs and find a thick black bush of pubic hair.
The boy gods were kind, and when I skinned them down I found a long and thick, yet completely bald, five-inch cock. He was beautiful from this glorious angle, looking up his tall, slim body with that big meaty thing jutting up in supreme stiffness. His hairless balls remained 10-year-old sized, hanging loose but small as marbles. I drank in his musk, as earthy and enticing an aroma as I'd ever encountered. I still preferred smaller cocks to bigger ones, but there was no doubt I wanted Miles in my mouth right that second.
I guess he recognized the look on my face because his emerald eyes sparkled as he backed up to the bed and sat on the edge, opening his slim, smooth legs. "Come on," he said. "I like to start this way."
I knee-walked closer until I was right in position, staring down the barrel of his formidable weapon. It was cut, as was everyone in America in those days, but neatly so, and its slightly elongated deep pink head seemed to tremble atop his steeply angled shaft. Like the rest of him the cock was darkish-white, not quite olive, with not even a shadow of a blue vein to mar its perfection. It slowly rose and fell with his breathing, and I licked my lips as I bent to my task.
"Ahhh," the boy sighed as I engulfed the first third of his length. "Mmmm, feels nice."
Terry's round face was suddenly there. "Bill sucks good," he said, and I swirled my tongue around Miles' cockhead in demonstration.
"I can tell," he said, then humping up to me slightly, "Take it all, man. Suck it deep for a minute, and then come back and do the head."
The kid knew what he wanted, and I aimed to please. I slid all the way down the thick shaft, the tip very nearly entering my throat, and sucked firmly. Miles moaned softly and took my head in both of his hands. He held me to him for many seconds before coaxing me to slide back up, where I passionately slurped and nibbled his glans.
"Oh, man!" he cried. "Suck, Bill! Go back down!"
This boy obviously had plenty of experience, and I was pleased that he seemed to place me in his upper echelon of cocksuckers. I resolved to give him my absolute best, which of course I always did for every boy.
After several mutually thrilling minutes Miles lay back on the bed and said, "Come give me some, Terry," whereupon my eager little bed buddy climbed astride Miles' narrow chest and fed his stony cocklet between his friend's waiting lips.
I watched in fascination as Terry's soft round ass clenched with every thrust and Miles made ravenous, gluttonous sounds as the boy fucked his face. I altered my rhythm to match Terry's and Miles moaned even more passionately.
Miles and I sucked and sucked and Terry and I pumped and pumped for a long time. I felt Miles' slim thighs tense and relax and a few seconds later it happened again, this time along with his gut, again and again until I was sure he was about to cum. I wouldn't have been surprised to taste a trickle of fluid, but when his eruption came -- strong and long and pulsing that thick boy-cock like a high-pressure hose -- there was no payload at all. It seemed his tiny hairless nuts were not yet open for business.
He barely slackened after his climax and I gently nursed on him as Terry pumped away into his mouth. I very much admired how Miles let his friend finish, showing a lovely generosity. Terry's ass clenched hard and held that way for several seconds as he grunted his dry little-boy cum into Miles' mouth.
"Wow!" Terry exclaimed as he rolled off of Miles' face onto the bed beside him. "That was so cool!" He quickly slipped down a little and placed a deep, wet kiss onto his sexy friend. I was happy to watch them eagerly tongue-wrestle.
I climbed onto the bed with them and said dryly, "Pass the lips, please. I'm starving!"
Boy giggles burst into each other's mouths, and then they laughed at that, too. I gathered a boy to each side and kissed each in turn, finding Terry his passionate self and Miles an enthusiastic second. I bounced back and forth between them like a shuttlecock until I felt a hand on my cock.
"What do you have planned for that, Miles?" I asked, and he grinned mischievously.
"Terry says you put it up him," the boy said, sounding shy again. I don't know why he sometimes slipped into that voice, but it was actually very endearing, and maybe that was the point.
"Do you want that too?" I asked.
"No!" he laughed quickly. "I'm too scared to let a grownup do it, but maybe someday, I guess."
"It feels awesome!" Terry encouraged. "I was scared too at first, but I did it."
"No, Terry," I said gently, "don't talk him into it. With me, nobody ever has to do anything they don't want to do."
"Then what do you want to do, Miles?" Terry asked.
"I want to see Bill put it in you," he said. "I've only seen boys do it to each other."
"OK!" Terry agreed instantly. "I love to get fucked!"
"I know," Miles said with a lascivious chuckle.
I caught Miles' eye. "You did him yesterday, didn't you?"
Miles eyes lit up. "Yeah," he said excitedly. "I never fucked a boy who liked it as much as him. It made it super fun for me!"
"Have you fucked a lot of boys?" I asked. The image of this big-dicked kid slamming into Terry's welcoming hole had my cock pounding harder than I ever remembered.
"Not that many," Miles demurred. "Maybe like eight... Oh and two girls."
"Whoa!" Terry exclaimed. "You've fucked girls?"
"Yeah," Miles said, a tinge of disappointment in his voice. "I like boys better, I think. Boys have dicks to suck and balls to play with, and when we get done we just go back outside and play. Girls want you to be their boyfriend and carry their books home from school and stuff." After a pause he said, "And besides, the back hole is way tighter than the front hole."
I laughed out loud, and the boys joined in.
"So who were the girls?" Terry asked wickedly.
Miles looked at him, aghast. "I can't tell you that," he insisted. "Would you like it if I told people that I fucked you?"
Terry's excitement instantly crashed. "No, I guess not," he said. "But can you at least tell me if it's somebody I know?"
"Nope," Miles said flatly. "I promised."
"Leave it alone, Terry," I said, then to Miles, "I'm really proud of you for keeping your word."
Miles beamed, then eagerly changed the subject. "So are you gonna fuck him now?"
"Yeah!" Terry cried, his excitement turned back up to 11. "I'll get the K-Y!" He scooted to the side of the bed where he could reach into the nightstand, retrieving the tube of joy goo. "Did you ever use this stuff before?" Terry asked, handing Miles the tube. "It's super slippery."
Terry examined the label. "No," he said. "I usually use Vaseline like yesterday, except one kid likes baby oil. I think that's too runny, though. One time I got home and found, like, shiny spots in my underpants."
"Did your Mom see it?" Terry asked in a mildly horrified voice.
"No," Miles said. "I hid them until she was washing underwear, then I snuck them into the washer when she wasn't looking."
"That was smart," I said. "Don't worry, K-Y washes off pretty well. We'll make sure you get home nice and clean."
"OK, then," Terry said with a grin, presenting his round backside. "Get me ready!"
"You've got the lube, Miles," I said. "Why don't you do the honors?"
"Lick me first, Miles," Terry begged. "Nice and deep like yesterday."
Holy Christ, I thought as Miles eagerly parted Terry's buns and introduced Mr. Tongue to Mr. Butthole. These kids do it all!
"Oh, yeah!" Terry sighed as Miles' lingually teased his tender entryway. I had to squeeze myself as I watched Miles get deeper and deeper into his little friend. I was already leaking pre-cum.
"Grease him up, Miles," I said, and recognized the hunger in my own voice. The slim 10-year-old squeezed a glob of lube onto his index finger and began to swirl the fingertip around Terry's open pink anus.
"Hey!" Miles exclaimed happily. "This stuff is great!"
"Come on, Miles," Terry said softly. "Stick your finger in."
Miles adroitly inserted his greasy finger and worked it around inside, then got more lube and inserted two fingers. After about a minute he slipped his fingers out and turned to me.
"You now," he said, and squeezing the tube again filled his palm with gel. He deftly coated my cock from root to tip and while this was fun in its own right Miles was taking his time, and I needed to forge ahead.
"Let's do it a different way this time," I said to Terry. "Turn on your side, and I'll be on my side behind you." Terry looked a bit confused but he complied. "This is called spooning," I said, scooting closer. "It's a very comfortable position and Miles will be able to see everything."
I lifted Terry's top leg to expose his full boyness: asshole, perineum, balls and stiff, stiff little cock. Instinctively Terry grabbed himself behind his knee and held his leg aloft. I scooted up a bit more and aimed my red throbbing member at his glistening little hole, pausing a moment just touching his scorching flesh.
"Do it, Bill," Terry breathed. "Put it in me!"
I pressed forward and the little sphincter yielded easily, accepting me like the Statue of Liberty with the huddled masses.
Not lately, but I digress.
"Ohhhh!" Terry moaned in delight. "Oh yeah! Give me that big thing!"
"Holy crap!" Miles exclaimed. "Terry! Doesn't it hurt?"
"No, man!" the boy groaned. "It feels fantastic! It fills me right up, and it's touching that place inside that feels so, so good!"
"That little bump thing?" Miles asked, but Terry's wide open mouth was no longer available for conversation, making no sound as my big invader drove slowly deeper.
"It's his prostate," I grunted, somehow able to deliver an anatomy lecture at a time like this. "It's the most sensitive spot there is."
"I'll say!" Terry squealed as my cock settled into his deepest nook. "Oh, man, I think you get even deeper this way than when I'm on top! Why didn't we do this before?"
I didn't answer, being fairly preoccupied at the moment. I slid about halfway back, then slowly pushed in once more, eliciting moans from the boy that you would have thought was agony if you couldn't see the ecstasy on his face. I began fucking him in half-strokes, slowly and deliberately, registering the increased pleasure in his body every time my cock traced over his magic button.
"Oh, fuck me!" he moaned, and I'd never heard a boy sound more earnest.
"Wow!" Miles exclaimed. "I can't believe that big thing fits in there!"
"Come on, man," Terry urged. "Fuck me faster!"
I picked up the pace, pretty soon driving full strokes home about one per second. I glanced over and Miles was masturbating his big meat at the same pace, which gave me an idea.
I began to slow down, still going full depth but bringing myself to a complete halt inside the boy.
"Why did you stop?" Terry whined. "I was starting to get there!"
"Wanna get in on the action, Miles?" I asked, and a huge grin replaced his confused expression.
"What should I do?" he asked eagerly.
"Grease up your dick," I said, "and get behind me just like I'm behind Terry."
Miles instantly realized what I had in mind. "Oh, boy!" he exclaimed as he fumbled with the K-Y. "You'll be the monkey in the middle!"
"Put a glob in my hole," I said, "then scoot right in and do your thing!"
I felt his slight presence behind, which suddenly felt a lot more substantial when Miles' oversize prick started prodding me. I felt him align himself with my channel, impressed by how such a young boy knew just the right angle of approach. Miles' small, soft hands gripped me by one hip bone and the opposite shoulder, and with this leverage he began to push himself into me.
I exhaled deeply and opened myself, drawing him inside. Until then I had only bottomed for grown men with their grown cocks, and while I usually enjoyed it and sometimes adored it, there was always significant initial pain. Miles, though, was exactly the right size; not too big and not too small. I felt that intensely stiff thing slide almost effortlessly through my anal ring and I welcomed his delicious warmth. In one steady push he entered me, and soon I felt his cockhead brush my waiting prostate. The shudder of excitement that coursed through me was electric.
"I'm in!" Miles said in triumph, and drew back to give me a few slow thrusts, experimenting to see how far back he could pull without popping out. It wasn't the amazing fullness of being with a man, but it was without doubt the nicest and most comfortable fuck of my life.
"OK Miles," I said, "push in deep and stop. I'm going to take over, and both you guys just hold still, all right?"
When Miles was in place I gripped Terry's hip and drove into him, which served as a backstroke for Miles. Terry grunted appreciatively as I bottomed inside of him and Miles sucked in his breath. Then I reversed, slowly pulling back from Terry and impaling myself again on Miles.
"Oh, wow!" Miles cried. "It's like your butt is swallowing me!"
I increased my speed, thrusting hard into the silky-soft boycunt in front and slamming back onto the rock-solid boycock behind. Terry grabbed his little dick and began stroking it as well, and both boys moaned and grunted in rhythm with my pounding. Soon the double-time slap of skin-on-skin-on-skin grew louder and syncopated our erotic rhapsody. With heaving breath I drove my hips, forward and back, forward and back, my own moans coming louder as my excitement grew.
"I'm getting close!" Terry cried, throwing his head back in ecstasy. "Fuck me, man! Fuck me!"
I bore down, not sure where my concentration should be, the magnificently tight orifice that pulled at my cock or the sweet hardness that firmly stimulated my prostate. I felt my seed rising.
"Miles!" I cried too loudly, "can you get there?"
"I'm close!" he replied, barely able to speak. "Oh, shit I'm close!"
"Here I go!" Terry cried as his sweet young ass clenched my cock with all its strength and a pulsing orgasm flooded him. I had maybe five seconds so I drove deeply five more times and crushed myself there just as my essence jetted into his steaming, squeezing depths. Miles reacted to the end of my thrusting and jabbed himself into me three times more and suddenly we were all moaning and clenching and pulsing and cumming.
It was astounding, the one and only time in my life that I've had three such intense, overwhelming sensations at once: Terry's incredibly tight asshole clenching my cock like a vise, my own cock pulsing and straining over and over deep inside him long after my full load was spent, and Miles' baby monster of a dick spasming dryly inside me. We clutched together and shook and quaked for many seconds until all of our energy was gone and we lay unmoving save for our breathless gasps, still joined together and loath to separate.
Miles softened before I did, and the boy fell away from me onto his back. "Oh my God," he breathed softly. "Oh my God."
I was still 90 percent erect but I eased back from Terry's sweet bottom, carefully slipping out and watching my abundant semen drool from his gaping red rectum. I carefully rolled onto my back as well, nestling next to the gasping Miles and pulling Terry to me for a kiss. He returned it with a loving look in his brown eyes, but he was far too wiped out to display his usual enthusiasm. I turned my head the other way and kissed Miles, who merely allowed it at first but then initiated another that was much more passionate. He smiled a weary but happy smile.
"God I love sex!" Terry announced, and we all laughed through our ragged breathing.
There were showers and another hour of tender kissing and oral, and I taught the boys how to pleasure my sharp and sensitive nipples with fingers and mouths, but there were no more orgasms for any of us. Terry had fun learning to deep-throat Miles and promised that someday soon he would do the same for me. Miles gave me an enthusiastic blow job but wouldn't take much more than the head, despite admonitions from Terry that he could do more if he only tried.
It was great as far as I was concerned.
Finally we finished with Terry and me rimming Miles for more than 20 minutes straight, trading off every time our tongues got tired. I was fascinated by the marked difference between slim Miles' butt and pudgy Terry's, unable to decide which I preferred. Terry had that beautiful soft roundness compared to Miles' relatively bony, narrow posterior, but then I could open Miles' tender cleft much wider and really get my tongue into his delicious, tight anus. I was glad I didn't have to choose.
Miles loved every second and insisted that he would have cum for sure if he hadn't already had two orgasms in two hours.
I could relate.
Believe it or not Terry, Miles and I were burned out on sex after our acrobatic morning so the afternoon's pool play transpired with nary a fondle. To my disappointment Casey wasn't there, and Geri said that because he wouldn't see his Mom for three days she made him spend Sunday with her. I hoped for Casey's sake that Tony wasn't along, though it seemed unlikely the asshole would subject himself to Mother and Child Day.
Monday morning the knock came at twenty to eight. It kept getting earlier.
It was Casey, carrying the same backpack he had brought the day we went to the movies, plus a small suitcase. Evidently my stewardship of the boy had already begun, which actually suited me fine.
He was wearing a sky blue Izod-style pullover shirt and navy dress shorts, although barefoot as usual. Like the more casual outfit he wore to the movies the colors perfectly brought out his magnificent gray eyes. That Brandi sure knew how to dress him.
"No swimsuit?" I asked, following our happy greetings and a hug.
He made a face. "My Mom wanted to be sure I had a nice outfit in case we go out for dinner or something," he said. "She made me try this on so she could see if everything fit right and went together and stuff, and by that time she was late for work so I didn't have time to change back. My swimsuit is in my backpack."
"We won't go to the pool for another hour at least," I said, "but maybe you should go ahead and change now, so you don't get your good clothes dirty."
"Good idea," he said, then with a cheeky smile, "I wouldn't want to do anything really stupid like spill Coke all over my dick and balls."
"Why I oughta..." I said, curling up my fist in his direction but grinning as he heartily laughed.
We shared a truly meaningful eye-lock and inside my head I heard the word "love" loud and clear. It's not like I didn't see it coming for a mile, but I didn't expect to find myself so solidly on the hook. For the second time in my life I was fully, romantically in love with a preteen boy.
Self-consciously I looked away, saying, "OK, so why don't you get changed?" I handed him the small backpack and gestured toward the back hallway that led to the bathroom and bedroom. To my surprise Casey didn't move from where he stood.
"You need to put your suit on too, right?" he asked shyly.
"Eventually, yeah," I said.
"We could both change now," he said tentatively. "Then we'd be ready."
"I guess we could," I said. "Whatever. Anyway the bathroom is free right now."
Casey nervously licked his lips and avoided eye contact as he said, "I could just, you know, change in the bedroom with you."
I stood staring, my heartbeat loud in my ears. Was this really what it seemed? Did he see this sleepover as a golden opportunity the way I did? Casey looked more anxious the more I hesitated. He opened his mouth to say something, which I was sure would be some form of backtracking.
"Sure!" I said quickly, to head it off. "That's a good idea."
Casey closed his mouth and smiled shyly, his gray eyes locked on mine, seeking assurance. I smiled and gestured toward the hallway again, following him into the bedroom.
He dropped his backpack onto the bed and rummaged inside, pulling out a tiny blue swimsuit with a white diagonal accent stripe on one leg. I had never seen this suit before and registered immediately that, while not quite a Speedo, it was much briefer than the trunks he usually wore.
"I got my Mom to buy me this yesterday," Casey said. "She thought it'd be uncomfortable, but I like it."
"I think it'll look fantastic on you," I said, hoping it didn't come out sounding pervy because I meant it in all sincerity.
Casey watched as I pulled a clean swimsuit out of a dresser drawer. With our suits in our hands we faced each other like Old West gunfighters, waiting for the other to make the first move. I decided to break the standoff.
I smiled and lowered my sleep shorts, standing fully and openly nude before him. Casey's gray eyes fixed on my cock, which somehow remained flaccid despite my intense excitement. I think I was still so shocked by this unexpected turn of events that my libido hadn't yet caught up. Maybe it was good, because as a grower, not a show‑er, it must have been less intimidating for him. I let him look me over for half a minute before making a "go ahead" gesture.
He took the hint and gave a shy smile as he peeled off his shirt and folded it neatly on the bed, then shimmied down his shorts without unzipping. He folded them as well and then stood facing me in his tiny white briefs, which seemed to me to be tented a bit. I didn't have to speculate for long.
Casey shucked them down and stood to face me, beautifully, gloriously naked. His narrow hip bones framed his utterly hairless pubic area in a pronounced V, and seemed to point like an arrow to his diamond-hard three-inch boycock. I sucked in my breath as I drank in the sight, which made him smile shyly.
"What's the matter?" he asked. "Haven't you ever seen a guy with a boner before?"
Before I could get out a reply a knock came at the front door and we both jerked our heads toward the sound. When I looked back Casey was already stepping into the little blue swimsuit and hurriedly pulling it up. As I watched with my mouth open he brushed past me, muttering, "I have to go to the bathroom," and in another two seconds the door closed behind him with a thunk.
Shit! I thought. What terrible timing!
"Coming," I called, hurrying into my suit and striding for the door. I knew perfectly well who it was but I couldn't blame him because he couldn't possibly know what he had interrupted. I checked the peep hole and it was indeed Terry, by himself. I opened the door with my finger already at my lips.
"Shhhh!" I hushed, and he looked up at me, confused. "Come in," I whispered, "but don't say anything sexy. Casey is in the bathroom." He looked disappointed, but silently came inside.
"Maybe Casey would wanna..." Terry began, but abruptly shut up when the bathroom door burst open and Casey emerged in only the tight little blue swimsuit -- notably with zero evidence of erection.
Casey stared at Terry in annoyance. "What are you doing here?"
"I was, um..." Terry hesitated, but then with suddenly bright eyes finished, "...looking for you," he said. "You usually come over to my house when your Mom goes to work."
"I brought my stuff over 'cause I'm staying with Bill for a few days," Casey said. "Remember?"
"Sure," Terry said, "but I thought that wasn't till tonight."
"What was I supposed to do with my suitcase?" Casey challenged. "Bring it to the pool?"
I had never seen Casey speak so sharply to his best friend, or to anyone else for that matter. Maybe he was as frustrated at being interrupted as I was.
"Speaking of which," I said, preempting any heated words that might follow, "it's a little early but if we go now we can probably have the pool to ourselves."
"Yeah, OK," Terry said with a deferential smile, placating Casey.
"I'll get my shirt and towel," Casey said and went into the bedroom.
Terry gestured for me to lean down to him and whispered in my ear, "Too bad for you. I was gonna give you a good long blow job!"
And thus I was doubly disappointed.
Thanks for reading Part 3 of Woulda Shoulda Coulda #2: Steel-Gray Eyes. I hope you enjoyed it. Part 4 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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