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Cruel Developments Chapter Three
I had been edging Shane for about half an hour, when I finally got serious and let him cum. I counted six full jets of his cream pump into my mouth, then he just lay there trembling as his cock still oozed onto my tongue. I had already swallowed twice to get all his load inside me, then I slurped around the head and shaft to get any I had missed.
Shane threw his hand onto his forehead. "I think my head almost exploded that time. It was even better than the one by the river yesterday."
It was Monday after school, and we were in my room. Dad had gone out of town and wouldn't be back until Wednesday night, so Shane came home with me. When he had recovered some, he pulled me up beside him, then swooped down to swallow my dick. He was always good about returning the favor.
I had closed my eyes to enjoy his efforts, when he took my dick out of his mouth, I looked down in time to see him pull his middle finger from his lips. He moved my knee to the side and pushed his wet finger at my opening.
"Oh, Jesus!" I said as my pucker surrendered to his insistent finger. He slid it in about half way then moved it in and out a few times, before giving me the rest of it. I could feel him wiggling it around inside me, then he hit something that caused my balls to draw up and sent lightning to my head.
"Fuck!" I realized Shane had found my prostate, and he knew it too. He returned to sucking my dick as he rubbed my button.
I guess because I had edged him so long, he did all this at a snail's pace. Then he took his finger out and dribbled spit on two fingers, stretching my hole, he pushed them into me. His mouth went back to my dick as he began sliding his fingers in and out of me, making sure to hit my prostate on every thrust.
"Fuck! Shane, that feels so good!"
He stopped sucking long enough to say, "Think how good it would feel if it was my dick in there."
"Shut up and suck me. I'm about to cum!"
Shane increased his efforts on my cock and my button, and I exploded my load into his mouth. When I had stopped vibrating, he pulled his fingers out of me, then headed to the bathroom. I heard the water in the sink, then his stream of urine in the toilet.
"Same time tomorrow, Babe?" Shane asked as he dressed.
He was trying to find a pet name for me. He had already tried Darling' and Sweetheart'. Now it was `Babe'.
I nodded, and he bent down to kiss me. Then I heard him say "Good bye." to Grace, just before closing the front door. I still lay there recovering from an unbelievable orgasm brought on by Shane shoving two fingers in my ass. As my head cleared, I realized my ass felt empty and wanting. Did I want Shane to repeat the act? Definitely. Did I want something bigger up there? Hmmm.... The rest of the evening, I found myself thinking about my ass, that is how it felt to have something in there. I was even tempted to shove my own two fingers in. By tempted, I mean seriously considered.
When Shane called me that night he asked how I was feeling. "Fine," I replied simply.
"Just fine, that's it? I mean... is your butt hole sore or anything? Anything at all?"
"No, it doesn't hurt. You have my permission to do that again."
Tuesday, Shane came home with me again. We had a snack of brownies provided by Grace. Then up to my room where I swallowed Shane's load, and got two fingers up my ass in return. To be honest, I almost begged for it, then practically grabbed his hand, willing to shove the whole thing in me. How he managed to grin the entire time my dick was in his mouth is beyond me. And again he left me panting on the bed. My sphincter kept flexing, tightening and relaxing, probably looking like a fish mouth, trying to suck in its prey. But it went without, Shane had taken what it wanted with him.
I hadn't seen much of Robbie except at lunch.There was a new addition at their table. Since the game on Friday, Marshall had acquired a girlfriend. Of course she's the head cheerleader. By Wednesday, she was sitting on his lap, and other public displays of affection. Kinda made me want to puke. Marshall is hot, no doubt, athletic body and chiseled features. He had really nice green eyes too. But that tramp with the cantaloupe size tits obviously only wanted Marshall because he was the star quarterback, and it made great fodder for social media.
I didn't know for sure when Dad was coming home, so I told Shane he couldn't come over. He raised his two fingers, looked at them and said, "You hear that fellas? We're on our own tonight." He, and somehow his two fingers, looked sad.
As it turned out, Dad didn't get home until around ten thirty. He and I had a nice chat before I went to bed. I was only slightly disappointed because Shane could have come over after all. But I got permission for him to come after the game on Friday.
Thursday morning was interesting. As I entered the kitchen, Grace was loading the dishwasher and Dad was drinking coffee with his paper as usual. Grace said a quick "Morning Clay," over her shoulder as she scurried from the room.
"Morning Dad," I said as I grabbed a pop tart and a cup of coffee. When I sat down, Dad slid a folded paper towel toward me. When I just looked at him blankly he reached over and unfolded it. There lay the condom that Shane had tried on during the weekend.
"Grace found this in your waste basket. Care to explain?"
"It's not what you think, Dad. Notice there is nothing in it. Shane just tried it on."
Using his index finger and thumb, Dad picked it up by the tip. About seven inches of stretched out condom hung from his fingers, but not truly indicative of his size. "This fit him?" he asked, unbelievingly.
"Well, he didn't roll it all the way down to the base, but yeah."
His eyebrows went up, he smiled a little and nodded. He didn't ask what my friend was doing with an erection, in my room, with me present, so I added, "We shower after gym every day and have changed clothes together. I've seen him naked numerous times." Of course that didn't explain the erection part, but he seemed to accept it.
I learned two things from this encounter. One, we have to be more careful with leftover evidence. And two, Grace is a snitch.
We won the game on Friday, and Shane came home with me. It was a great weekend. Swimming, XBox, Dad grilled again. And by Sunday afternoon, I had graduated to three fingers.
I could barely open my eyes as I watched Shane return from the bathroom, his big cock swayed with each step. He climbed back into the bed and snuggled up behind me. "I know what you're doing. Training my butt. Getting it ready to take your big cock," I accused.
Shane raised up on his elbow and acted shocked and insulted. "What? I would never do anything as sneaky as that!" Then he gave an impish smile, "Is it working?"
"Probably, since I keep letting you shove your fingers up my ass."
He leaned down and kissed my neck. I felt his cock start to get hard against my butt crack. "Not today, Lover!" I said as I rolled out of bed.
I decided to tease him a bit and roamed around the room pretending to do stuff, but really just displaying my body to him. When I looked at him, he was stroking his hard cock. He stopped when he saw me watching and just waved it back and forth at me. He stroked some more, then waved some more, repaying my tease.
It worked. I sat on the bed and grabbed his cock. He put his arms under his head and let me play. After stroking it for a few minutes I said, "I can't believe you want to destroy my tiny butt with this big thing."
"Oh, believe it. I do, I definitely do!"
I played with his balls for a minute. I love his balls. Then I started jerking him in earnest. It took a while, and my arm was getting tired, but he finally said, "I'm gonna cum!"
I bent over and took the fat knob of his cock into my mouth to receive his offering. When he was drained, he reached for my dick to return the favor. "No, it's getting late and I have homework to finish. Do you want my dad to drive you home?"
"That would be great. After that hand job, I don't think I can walk that far," he laughed.
After Shane left, I lay there contemplating my life, specifically more recent events in my life. I had been just your regular kid, just bopping through life without a care. Then came that day, waking up in the hospital and my world had turned upside down. Then I met Shane. Before him, I had only suspected that I might be gay. I knew I liked boys, but wasn't sure to what extent.
Now I was having regular sex with a boy. I thought about him constantly. I liked the feel of his cock in my mouth, it felt natural somehow. I liked holding his cock, examining every facet of it. From the fat knob with its single eye, down the shaft with its spider web of veins, right down to his delectable nutsack. God! How I loved slathering my tongue on that wrinkled bag of goodies.
My birthday is coming up next weekend, I will be fourteen, and already I can see myself spending the rest of my life with Shane. I even love the crooked little smirk he has when he thinks he's getting away with something. Maybe first love is always like this for everyone.
Dad worked at home a lot, and sometimes at his office. His schedule was never the same, so I didn't know when he'd be home or at the office. He usually told me if he was going to be late getting home so I wouldn't worry about him. If he didn't say anything, most likely he was working at home that day.
Dad asked me what I wanted to do for my birthday a month earlier, I said "Nothing." I was still depressed about the accident, and school hadn't started, so I hadn't met Shane.
"Dad, I've changed my mind," I told him Monday morning. "I want to invite some friends from school to dinner and a movie. Oh! And you too of course. Then a sleepover after."
"How many friends?"
"Just three."
"Your birthday is Saturday. Is that when you want to do this?"
"Well, Shane will probably be here Friday night, but I'll invite the others for Saturday. Maybe start early, go swimming then the movie. Instead of dinner, you could do hotdogs on the grill for lunch. Just a suggestion."
"Are you going to the football game on Friday?"
"Yeah. It's in Middleton. Shane's mom already said she'd take us and bring us back here. She's even staying to watch the game."
"Sounds good. I'll just plan to work that day."
Dad didn't go to the office Monday, but Tuesday and Wednesday he did. So Monday, I didn't have Shane with me when I came home. The next two days I did. Grace had made a strawberry cake, two slices disappeared quickly. Then straight to my room. Five minutes after we put our forks down, I had three fingers in my ass. I was humping my dick up at Shane's mouth, then shoving my ass down on his hand.
By now, Shane was an expert on how to get me off sexually. He'd had plenty of practice. I had asked him before how he knew so much without any experience. "Research. You can find out anything on the net if you're determined and know where to look," he replied. If what he did to me was any example, then I had to believe it was true.
As my post orgasmic dick withered in his mouth, Shane removed his fingers from my stretched rectum. He jumped up and went to the bathroom, where I heard water running in the sink. He came back, his mighty cock looking like a large metronome needle swinging back and forth as he walked, and jumped into bed behind me.
He threw his arm around my chest and drew me closer to him.. I felt his large cock along the top of my butt crack and lower back. I pressed back at him, letting his cock nestle into my cleft. He started moving it back and forth, humping my entire nether region. There was plenty of lube leftover from his fingering me to allow sliding smoothly. I relaxed and let him enjoy himself. I could feel his cock head pass over my hole, and it sent shivers through me. He would pause with it knocking at my door, then slide up to my back.
I wanted it, and he knew I wanted it. He was just waiting for permission to impale me. I almost wish he'd just do it, just take what he obviously wanted. I was also grateful he didn't. It would bruise our relationship, and he knew that as well.
Shane continued to hump me, after a few minutes he said, "This feels so good." He kissed and nuzzled my neck. "Like how it was meant to be. Us together like this."
I had thought he was saying it felt good physically. But he was talking about emotional feelings. I had to agree, to both actually.
After a few more minutes, Shane grabbed his cock, pointed it down, and jerked himself to a finish, shooting his load on my balls and thighs. But I know where he wished it had gone.
We cuddled for a while, then he dressed and left. I lay there thinking about how far we've come in just a couple of weeks. Each step we took was at his guidance, and I was happily following along.
Wednesday was almost a repeat of Tuesday, except instead of laying on our sides while he humped me, I was in the submissive position on my stomach with Shane on my back and between my legs. I couldn't have been more vulnerable, he could have easily taken me. His cock slid along my crevice, occasionally pausing at my entrance. He'd rub it teasingly over my hole as if to say "I know you want this, but you can't have it." before continuing on its journey to my lack. And for his finale, he placed his cock against my hole as he shot his load. I felt it wanting to get into me, and oozing down onto my balls. With the lube, and the cock slime, he could have impaled me, but still he resisted.
Friday's game was another close one, but we won with a last minute field goal. When Shane's mom dropped us off, Dad was waiting up for us. Shane excitedly told him about the game, and Dad seemed to enjoy the camaraderie Shane shared with him. Like he might with a son in law?
When we finally got to my room I was about ready to chew nails. I hadn't gotten off since Wednesday and my ass was hungry for some fingerwork. I grabbed Shane and kissed him as I reached for his belt buckle.
"Wait, I've got something for you," he said as he stopped me from raping him. "Actually several things," he corrected and reached for his backpack.
He pulled out a long thin box. "I know you don't want to be out, so I can't get you an engagement ring or anything. But I want to sorta lay claim to you, even if we're the only ones who know it. Happy birthday."
Inside the box was a half inch wide gold link bracelet. I chuckled as he fastened it to my wrist. "Lay claim? What am I, homestead property? Are you going to plant a flag on me?"
"Shut up, you know what I mean." Then he kissed me to seal the deal. He reached for his backpack again. "Um... I also got something that would make things... uh... less messy."
This box contained an enema bulb. "That's pretty presumptuous. I haven't decided to go that far yet."
"NO... It's just so I won't have to jump and run to wash my hands after we..."
"Hey, it's not my fault. You're the one who shoved your fingers up my ass."
"Well, it's just that I want..."
"Shut up and give it to me." I took the box and headed to the bathroom. I read and followed the directions. It was kinda gross, but I do like his fingers up there, so it's worth doing it. When I finished, I hid the bulb in an overnight case in the back of my closet. Hopefully Grace won't find it there. I had told Shane about the condom conversation. He thought it hysterical imagining my dad holding a condom that had been on his cock. I didn't laugh.
Shane had me laying on my stomach again with him sitting Indian style beside me, as he worked two fingers into me. In short order, he added a third, all the while I lay face down, panting and moaning, as he fingered me to oblivion. In five minutes, without my dick being touched, I was laying in a puddle of cum. And Shane was quite proud of himself, grinning like Alice's Cheshire cat.
"I take it you enjoyed that," Shane smirked.
I smacked him on his shoulder. "It's not like you're the first to ever make someone cum, you smug bastard." Then I kissed him. "But that was fabulous."
"Yes, and notice how clean my fingers are." That earned him another slap on the shoulder. But then I rewarded him by sucking his cock.
Robbie and Marshall showed up around ten on Saturday morning. Fortunately we were already awake (and had traded bj's). They were wearing their swimsuits under their clothes, but followed Shane and I to my room to change. We all took off our clothes at the same time, but they didn't need to put on suits. Shane and I did, removing our underwear and slipping into shorts style suits. Marshall's speedo didn't escape my attention. What he was packing appeared to be even bigger than Shane's. Did he just take a second look at my butt? Naaa.
Robbie noticed the bracelet right away. "Is that new?"
"Yeah, It was a birthday gift." I replied without elaborating.
"Your Dad must really love you," Marshall concluded.
"Yes, he does," I answered, still being vague. Shane and I exchanged a grin.
Dad did a great job on the grill, putting out mouth watering burgers and dogs. Grace made potato salad and mac & cheese. Not to mention a wonderful chocolate cake. I did notice Dad gave several curious looks at the bracelet, but didn't say anything.
After swimming, eating, and swimming some more, we went back to my room to get ready for a 6 o'clock movie.
"Damn, Clay,those burgers were great. Beat the hell out of M'cD's and Wendy's," Marshall said just as he pulled down his speedo. I don't know if he was trying to draw my attention to watching him wiggle out of that wet, tight suit, but that is what happened.His large cock and pendulous balls hypnotized me. I was still watching as he dried his legs and crotch. Shane finally brought me out of my fog by clearing his throat loudly. When I turned toward him, he narrowed his brows and gave me a stern look.
The movie was just OK. If you ask me, Hollywood hasn't been the same since Covid. But that's just my opinion, the guys seemed to enjoy it.
Robbie had given me the latest G.T.A. game for my birthday, so we played that for a couple of hours.
Then Robbie and Marshall threw their sleeping bags on the floor and stripped to their underwear. Shane and I stripped too, and Robbie watched Shane crawl into my bed. When he would spend the night, he always slept on the floor in a sleeping bag, he never shared my bed. I turned out the lights and settled in beside Shane, facing him. His hand went straight to my dick, and mine to his, and we fell asleep like that.
I was the first to awake, and tiptoed around my two friends on the floor to the bathroom. When I returned, Marshall was standing with his arms above his head, stretching out the sleepiness. His big hard cock was stretching out his boxer briefs. Damn! What a sight! Pointing to his hip bone, through the material, I could just make out the shape of his piss slit indented in the fat head. I had been too preoccupied to notice that Robbie was also awake. His eyes followed my line of vision, then back to me. He grinned as he sat up on his sleeping bag. Shane rolled out of bed and sleepily followed his erection to the bathroom. Robbie didn't miss that either.
Marshall followed Shane, and I heard him say "Move over, Dude." Then he said "Nice one."
Shane replied, "Your's is too." A minute of silence was followed by the sound of two streams of urine hitting the water.
Robbie put on his jeans and waited for the other two to return. I guess he didn't want to embarrass himself next to the two hung studs.
I watched Shane and Marshal pull jeans up over their impressive bulges. "I'm flattered, but are you going to get dressed, or are you staying like that all day?" Marshall asked dodding toward my crotch.
My erection had subsided with my pissing, but with all the eye candy, it had returned with a vengeance.
"Oh... Sorry, I was just..."
"No worries, I only wish Cheryl looked at it that way." Cheryl is the melon titted girlfriend's name.
Did his response imply he knew about my lust for boys? I hoped not.
After a breakfast of Eggo waffles and a bunch of playful banter, the guys all left.
Shane's birthday was coming up on Thursday. I thought it would be nice to give him a bracelet just like the one he gave me. So on Monday after school, I rode my bike to the store whose name was on the box mine came in. Even from the outside, the store looked pretty posh. I walked in and was immediately approached by a sales clerk.
"A friend bought this bracelet here, and I was wondering if you had another like it?"
"Yes, I remember this. A nice young man bought it. I think we have another one. Ah yes right over here," he said, leading me to a glass case.
I was happy they had one, until I looked at the price tag. "You're kidding me right? Are you sure it's exactly the same?"
"Positive. Like I said, I sold that one. They're eighteen karat gold. Designed by a well known artist and goldsmith in Texas."
Jesus! I couldn't believe Shane spent that much on me. I checked to see if they had a smaller silver bracelet, but even that was out of my price range. I don't think there was anything in that store I could afford.
I peddled over to the nearest chain jewelry store at the mall, and found a silver bracelet I could afford. Well actually, I could afford the other store really. I have some money saved, and I received some from my mother's insurance. But I didn't want to spend that much on a gift for a boy, even though I thought I was in love with him.
Dad worked at home most of the week, but was going out of town again on Friday. Not to return until Tuesday. So I didn't have a chance to give Shane his gift until after the game on Friday. His mom picked us up after the game, which was another close one, we barely squeaked a win at 14 to 13. I was a little surprised when I hadn't been invited to a birthday party at his house that weekend. I wasn't invited because there wasn't one. That seemed strange to me, and as I thought about it, Shane had never invited me to his house at all.
His mom dropped us at my house as usual. We had a quick snack, then headed to my room. We had the house to ourselves, so we could have done it on the kitchen floor, which would have suited Shane fine. He was anxious to get to it. I fought off his attempts at grabbing my dick and told him to wait till we got in bed.
In my room, I presented him with his gift. "I didn't expect you to get me anything," he said as he unwrapped it. When he saw it, I thought he was going to cry. "It's beautiful." I snapped it to his wrist, and he pulled me close for a passionate kiss.
Fifteen seconds later we were naked on the bed, wrapped in each other's arms. When he reached for my butt, I stopped him so I could go get cleaned out. When I returned he already had lube on his fingers and quickly inserted two, then three.
When he started to blow me, I stopped him again. "It's your birthday, you should go first," I said and turned onto my stomach.
Shane quickly mounted my back and laid his cock along my butt crack. He was kissing my neck and slowly sliding through my crevice. "Put it in," I whispered breathlessly.
He froze. I could feel his eyes on me as he said, "Are you sure?"
"Well, if you don't want to..."" I replied and made a motion as if I were going to roll over.
"No, no. I do, I do!"
Shane raised up off my body for a moment, then I felt his cock rubbing against my pucker. I felt pressure and my hole was resisting. But not for long. Suddenly his fat knob popped inside. I'd just had three fingers in there, and had several times in the past few weeks, but his cock must be fatter because it hurt pretty bad. I grunted in pain, and Shane froze again.
"Are you okay, Baby?"
"Yeah," I groaned. "Just give me a minute."
Shane leaned down and kissed my neck while I adjusted to being gored by his big cock.
Once I gave him permission to proceed, Shane began working his cock deeper into my bowels. Each additional inch elicited a moan from me. It took a while, but eventually I felt his pelvis pressed tightly to my butt cheeks.
I think my dick had receded into my abdomen, but as he started the age old motion, it started to respond. Shane lay down fully onto my back and slid his hand under me onto my dick. He pulled almost completely out of me, then slowly pushed all the way in. The sensation caused my dick to expand even more. By his third long slow stroke, I was as hard as I'd ever been.
He began thrusting faster, taking about half length strokes. "You're starting to like it," he said, giving my dick a squeeze.
"Yes. You smug bastard. I like it, so fuck me."
I know he had a huge grin on his face as he really got into it. He varied the pace and stroke length, finding what worked best for both of us. He kissed my neck and fondled my dick the whole time. I rewarded him with moans and gasps of pleasure.
"Should I pull out to cum?" he asked after a few minutes.
Neither of us had given Dad's gift condoms a thought before we started. Since we were both virgins, and I can't get pregnant, I replied, "Don't you dare!" rather threateningly.
Shane's strokes became very forceful. Long and hard as if he was trying to fuck me into the matress. He kept this up for a couple of minutes, then growled in my ear "Do you like my cock in you?"
"Yes," I grunted as he slammed me hard.
"Tell me," he whispered.
"Oh God, Shane. I love your cock! It feels so good inside me!"
He slammed into me twice more and I felt his cock throb as he filled me with his cum.
Shane lay on my back, slowly pumping his still firm cock in me. "God, your ass is amazing!"
"Like you've had so much to compare it to," I moaned in reply. Still basking in his efforts.
"Yeah, there goes that pesky virginity," he chuckled. "But still, your ass is amazing."
His cock softened only slightly before becoming rigid again. "I knew it would feel like this with you," he whispered into my ear.
I wiggled my ass against his groin. "Are you going to talk all night, or are you going to fuck me again?"
That started round two. The one that made his head swell even bigger because he made me cum. I think I shall never hear the end of that bit of bragging rights.
About an hour after round two, I was fast asleep spooned in front of him with his arm around me, when he started round three by shoving his cock up my ass again. Round four came about 6 A.M. round five after breakfast at eleven. Round six was in the pool. Seven started during a boring movie. For eight, he bent me over the dining room table while I still held a hot dog in my hand. That was just Saturday. By the time he left on Sunday, I had fifteen loads of his cum in me. I was bloated and my ass was raw, but we both had huge smiles on our faces.
"Best birthday ever!" he declared as I closed the door behind him.
I got a text from him an hour later. "Mom just asked me why I can't stop smiling. I'm dying to tell her."
"I'm sure that would go over well. `Well Mom, I spent the whole weekend fucking Clay senseless.' Don't you dare say anything to her!
"I made you cum eleven of those times, I deserve to brag a little."
"If you say anything, that will be the last time you make me cum," I threatened.
He came home with me after school Monday. We both came twice while he fucked me doggie style. Dad came home Tuesday, so Shane and I didn't get together. That's okay, my ass could use the rest! Dad worked at home the rest of the week, and I didn't want to get caught in an afternoon romp
We lost Friday's game by a slim margin, but that didn't dampen our enthusiasm. We were suffering from withdrawals, and hardly made it to my room before his cock was up my ass. I'm glad I had thought ahead, and cleaned before going to the game.
We did it three times Friday night. And after making sure Dad was in his room, we managed three more on Saturday night.
Monday, my world fell apart again. I was in my room texting with Shane. He hadn't been in school that day, so I was telling him about how Melon Tits wasn't at lunch. Marshall was bemoaning the fact that she was embarrassed because we lost the game. She wouldn't even return his calls, much less give him his usual hand job for winning.
We were laughing our asses off when Dad yelled for me from the living room. I told Shane I'd get back to him later, and went to see what Dad wanted.
When I walked in, I noticed the tv was on, but the feed was paused with just the news anchorman's picture, obviously caught mid sentence.
"I think you need to see this," my dad said, and pressed a button on the remote.
"... in the pretrial hearing. Michael Donahue is the son of the former District Judge, Shane Donahue. The Donahues are reportedly the third wealthiest family in the state. Michael Donahue is charged with two counts of vehicular homicide."
My mouth dropped open as the scene changed to outside the courthouse. Reporters were firing questions at a group of people as they tried to make their way down the steps. Cops were holding back the crowd as three men pushed through, Behind the three men was another man. Behind him was Shane and his mother.
I was paralyzed. "No! This can't be!"
Dad put his arms around me. "I'm sorry, Son."
I collapsed against his chest, sobbing. It was half an hour before I could drag myself to my room. Just as I was about to throw myself onto my bed, I saw my phone lying there.
My next text to Shane read, "YOU FUCKING ASSHOLE!!! NEVER SPEAK TO ME AGAIN. I HOPE YOU DIE A SLOW AND PAINFUL DEATH!!!"
Final Chaptercoming soon
© Cutter09
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