As we walked, I asked Willie who Charles was. He and Walter exchanged glances, and then Willie said, "Um, well, ah..." I'm staring at him, expecting to hear that Charles is Willie's real boyfriend, or something terrible, but Willie chuckles and mumbles, "He's a guy who has been in the same class as me since the fourth grade, including all through Prep school right up to the present."
I think I'm relieved, then Willie adds, "He's not an ex-boyfriend, but I had a juvenile crush on Charles, but I'd never managed to be included in his clique. The rumor is he's fucked a dozen boys at Prep, but I can't get him to fuck me. It's sort of a badge of honor to be one of the notches on Charles' belt, to use a gunfighter metaphor."
I mutter, "What, but you and I...." Willie says, "You and I are gold, Dylan. And, haha, I must be nuts introducing you to Charles because you'll fall for him instantly. I'm taking that chance, though, because you've helped me win a bet with him. We'll see. I've had a bet with Charles for three years about a boyfriend. I'll try collecting on it tonight. This might be so fucking cool, but I can't believe he came to a block party! He must be slumming it tonight."
Now I'm curious. This guy sounds like a rock star. We approached the DJ table, but nobody here was remotely rock-star material. That's good because I was not excited about this turn of events. Willie and I were having a good time together. I was nice to all his unusual friends, and now this shit with Willie being super interested in this Charles guy.
I had to hurry to keep pace with Willie, and then he squealed, "Oh my God, there he is!" I was looking for a super cute, hot guy but couldn't spot him. Willie runs up to this stocky kid about five foot eight inches tall and maybe a hundred seventy pounds. The guy was not cute, plus he had this superior expression that turned me off.
Willie gets right in front of him and jumps up and down like a six-year-old who needs to pee. The smug, stocky guy smirked and held out his arms, which apparently was the sign that it was okay for Willie to hug the guy while giggling excitedly, red in the face. I'm thinking: What the fuck? This is so unlike Willie! I mean, the guy isn't remotely cute. He's barely of average height and a bit heavy. Well, you know what?" He wasn't heavy so much as bulky, like a football player. His body is like Chubby's boss, Rickie. That's an unfortunate comparison, but accurate. There wasn't anything about Charles' appearance that impressed me.
He wasn't geeky-looking so much as he was bland. Willie has delicate facial features that all work well together. This guy's features weren't worth a second glance. He wore his very dark red hair in a Prep-school-longish, over-the-ears hairstyle, and he had this reddish complexion to go with the dark red hair, which clashed. There was no way his skin would tan, only sunburn. His blunt nose was peeling, and he had a low forehead. Well, okay, being fair, maybe a horny older woman would say Charles was handsome in some macho-looking way that I can't fathom. That's hard to believe, but I'm trying to be fair. He's not a gargoyle.
He was so not my type that it was amazing Willie could be in love with me and also have a crush on this totally opposite type of person simultaneously. Of course, Larry isn't a cutie either, and Willie thinks he's the greatest, so go figure. Charles tells Willie, "Don't make such a spectacle of yourself, William. God, you never change. I only sent Walter to find you because I need a ride home. My summer boyfriend, Nathan Rothmeiers, who you do not know, got sick eating some of the swill they served here, and he had to drive himself over to Mass General Hospital for possible food poisoning. How did I ever let him talk me into attending a 'block party?'"
When he said block party, he had such disdain in his voice as if he was so above a simple block party it's inconceivable he was here. I'm thinking, what a ginormous asshole! And why didn't he go to the hospital with his sick boyfriend? I didn't like Charles for several reasons, one of which is he seems to be the bully type of the big-man-on-campus variety. How a pompous asshole like him ever got to be the big man on campus, I can't imagine.
Charles hadn't paid the slightest attention to me, which I hope continues. He wasn't paying much attention to Willie either. Then, he looked right at him for the first time and did a phony theatrical double take while barking out a mean-spirited-sounding laugh, saying, "Does Larry know about that absurd haircut of yours, Worthington? Your ass will be an appropriate shade of red when he finds out."
Willie acted contrite, lying that Larry knew about it. He'd told him right after he had it cut, and he, Willie, knew what his punishment would be, but he had to do the haircut as a favor for his boyfriend. And with that inaccurate background information, Willie said, "Come over here, Dylan." Hesitating a second or two, I took three steps to stand beside him, and he said, "Charles, I'd like to introduce my boyfriend, Dylan Newman. Dylan, this is THE MAN at Prep school, 'the' Charles Neil."
Throw up!
But I knew Willie expected this of me, so I held my hand and said, "It's a pleasure to make your acquaintance, Charles." He rolled his eyes and blew some air out between his lips as if saying, Can I believe this shit? After a quick glance at Willie, he mutters, "Yeah, what's up, Newman?" and barely touches my hand for a weak, soft handshake. It was almost the same greeting I received from that snooty Prep School kid Willie was with at the movies two months ago. The Prep School lads don't take to commoners like myself very well.
Willie babbled on, "Isn't he cool, Dylan? Charles and I go way back, but I never expected he'd be at a block party." Then, looking at Charles, who was going through his pockets with a disturbed expression, Willie says, "Well, Charles, does Dylan qualify?" Charles says, "That idiot Nathan took the cigarettes with him! Who has a cigarette?" Willie's like, "Dylan, give Charles one of ours, please."
I held out the pack, and Charles said, "Anyone have non-filters? These pussy smokes are worthless." He swiveled his head around, but the guys had drifted away like I wished I could do. What a bore Charles is. With no other option, Charles grabbed my Marlboro Light pack from my hand, took a few out, put some in his shirt pocket, and broke the filter off one to smoke now. He handed my depleted pack back, saying, "Lighter!" When I held out my Bic lighter, Willie grabbed it from me and lit Charles' cigarette. Throw up again!
Charles says, "Let's get going, William; I've had all of this block party I need for the rest of my life." Those two started heading away from the party, with Willie saying, "I had to park my car way over on Elm; the parking situation in Cambridge sucks." Charles grumpily replied, "Among other things." Then he muttered, "That's quite an impressive hickey you got on your boy's neck, though. Looks like something Carl would do and Larry would approve."
I'm walking behind them on the sidewalk, but I can hear Willie say, "Yes, well, I don't know about Carl, but Larry's been mentoring me through each step of my relationship with Dylan. I've made some missteps, and Larry thinks I'm spoiling Dylan. I am, too, but I love him." Charles says, "Please stop; I'll heave up whatever I ate back there. No more romance stories about your girlie boyfriend. You are such a loser, Will." Willie says, "I know, I know; I'll never learn. But, ah, do you remember what you said last year at Spring break?"
Charles didn't really seem all that interested in what he'd said at Spring break. He flicked his cigarette butt high in the air, broke off the filter of another, and put the new cigarette in his mouth. In an uninterested manner, he mumbled, "Spring break? No, how the fuck am I supposed to remember what I said at Spring break? Get me a light, and where the fuck is your car?."
Willie reached around to me and said, "Your lighter, Dylan." I grimaced in disapproval but handed him the lighter. Willie lit Charles' cigarette, saying, "The car's parked on the next block. Ah, Charles, last Spring break at Snyth's party, you said you'd never fuck me one on one, but if I got a hot enough boyfriend, you'd consider a three-way. Remember?" At that comment, Charles did that dismissive bark of a laugh again and said, "Yeah... and?" Willie whines, "Well, I've got my boyfriend, and we're all here, and you know how much I've always wanted to do buddy-sex with you. Right?"
Willie tried to keep it light and humorous as he groveled and begged simultaneously. "Come on, Charles, we can stop at my house on the way to yours." Charles blows a lot of smoke out and says, "You are quite the pain in the ass, but I do remember saying something like that. However, I said a hot boyfriend, not some cute girly boy, and, by the way, have you got him in those frilly panties you're always talking about? I'd want to check that out for laughs."
Willie mutters, "No, not yet, but I'll put a pair on him tonight if you'll stop at my place and play gay for a while. You did promise, Charles." He goes, "Yeah, I guess, but for only forty-five minutes tops. I'm horny anyway, what with Nathan throwing his guts up tonight and, therefore, being unavailable. I was going to do that boy a new asshole tonight."
We were at the car, and, as an afterthought, Charles nodded back at me and asked Willie, "Did you cover all this with her yet?" Willie turns around and tells me, "We're going to stop off at my house, and the three of us will play around a little. Some gay fun." I said nothing as usual; I just shook my head. Nope.
Charles sees that and, laughing out loud, says, "Who's under whose thumb, William? God, you are the biggest loser I know of. If we hadn't gone to elementary school together, at Prep, I'd be taking your lunch money and locking you in a locker like I did with that Dwight kid last year. Remember him?"
Willie wasn't listening to Charles, though. He'd grabbed my arm and dragged me away from the car a few steps. He has a strong grip when he's pissed off. Charles watched us, mockingly laughing as he got in the shotgun seat of the car. With a bright red face, Willie said, "C'mon, Dylan. Help me out. This is a bucket list thing. I want to check it off. Please., Dylan."
"I don't like him at all." Willie asaks, "You do recall your promise to do something big for me to make up for you backing out on the Maine trip." I say, "I didn't back out. I was disinvited to the Maine trip." Willie says, "That's because you wouldn't agree to do the swapping part. You promised to do something important to me."
This was the second time tonight he'd gotten really wicked pissed off at me. We got over the first silly fight, and then we were having such a nice night, and now this. I said, "I don't like him, Willie, and he doesn't like me, and I don't want to do anything with him."
Willie looked up in the air with an impatient expression, which I had recognized from about ten times I'd seen it. He raised his eyebrows, waiting, staring at me; then, "Your promised, please." I said, "Okay, Willie. You're distorting what I promised, but we love each other, so I'll do it for you." He said, "Thank you."
Hw was still angry with me for embarrassing him in front of Charles, but he nodded and looked at Charles, who was yucking it up at us inferior beings, Willie and me. Charles muttered, "Yeah, well, like I said, I'm horny tonight, so it's your lucky day." Getting in the car, Charles says, Worthington, did I ever tell you about the three-way with Larry, big Bill Wright, and me at the ski lodge last Winter break? Jesus, we were all smashed...."
I can't think of anyone I've ever met who I disliked as much as I delight Charles, so I didn't listen to his bullshit story. I was squeezed in the back of what, basically, is a two-seater sports car with this tiny backseat and zero legroom. Plus, Charles had his seat back as far as it would go. He's only five-eight at the tallest and doesn't need the seat pushed all the way back! The fucker!
I noticed Willie pulling his seat up so I'd have a little space to stuff my legs behind the driver's seat. Willie hates driving close to the steering wheel, so it was considerate of him. I'm into a serious pout and didn't say anything the entire ride. As we were driving up Willie's long driveway, I was conflicted between telling those two I'd rather walk home from here than have a three-way with that asshole Charles or close my eyes and get through it. After all, I rationalized to myself that I'd had a three-way with Larry and Carl that turned out to be pretty hot, and then the four-way with Larry, Carl, Willie, and me, which was really hot, too.
Earlier, Willie had said "safe sex," so that meant condoms, and I don't want to walk home, so I guess I'll make the best of it. Getting out of the car on Willie's side, he pulled me over and hugged me. Oh, God, I love being hugged by him. His eyes shining in the light from the spotlights blaring down at us from over the garages, he said, "I'm sorry about this, and I swear I'll make it up to you; just please go along with Charles tonight. It means a lot to me."
I snuggled against him, murmuring, "I'll do it for you, Willie. I love you." He whispered, "Just one time I'd like to get Charles to do something I want; one time in my life. That's all." Walking around the car to where we're standing, Charles mutters, "No whispering, girls, don't worry, there's enough man in me for both of you with plenty left over. Forty-five minutes, William, that's it!"
We went in the side door and were almost to Willie's room when the housekeeper asked Willie if he'd be needing anything. It was a little after seven o'clock, and Willie asked, "Do you need anything, Charles?" He mumbles, "Well, yeah, a big bottle of something cold, like Gatorade." Willie looks at me and softly asks, "Can I get you anything, Dylan?" I shake my head. The housekeeper gets a quart of red Gatorade for Charles. She says she'll be in her apartment, and the three of us go up the big staircase, down the hall, and into Willie's bedroom.
Charles chugs a third of the Gatorade bottle, then mutters, "Everything off, girls, and I want both of you in panties... chop chop!" As I get undressed, Willie's going through his bureau drawers. He mutters, "Here they are," and holds up three pairs of ladies' underpants, frilly, silky, with little bows around the leg openings. Charles pulled his shirt over his head and dropped his baggy shorts. He was wearing a jockey underwear. He stepped out of them and fondled his cock and balls.
I was naked, staring at Charle's fat cock. It was the length of my dick, which is a little under six inches, but Charles' cock was almost twice as big around, twice as fat with a bulging dark red head. He sees me staring and mutters, "You want to suck it, don't you?" I looked up, "Huh, wha...?" He gave me a look like he just stepped in dog shit and said, "Get your panties on, and you can suck it while I do your girlfriend."
Willie tossed me a pink panty with little white and pink bows. As I pulled them on, he burst out laughing, quickly saying, "Sorry, Dylan, I'm not laughing at you. This panty thing gets me laughing." He stepped into a pair of white silk panties with baby blue bows as decoration. They were too small for Willie, his long cock and his scrotum full of nuts straining the material outward. I had to laugh at Willie's big package, which challenged the integrity of the silk material, plus the goofy look on his face.
It's stupid, but we both laughed. Charles was laughing a little, too, and for once, it sounded like he thought something was funny rather than just laughing from scorn as he did earlier. As ludicrous as they looked on us, the silky material felt good. Willie and I grabbed our crotches and pranced around, with Charles laughing harder now. He had half a boner, too, which he was playing with. The thought that Willie and I had too much vodka at the block party flashed through my mind. I was grateful for it, actually.
Charles pointed at me, saying, "You, suck my cock," and then, pointing at Willie, "Worthington, you get a condom and pull your panties down to your knees." I tried not to like this, but I liked sucking cock, and Charles had a big cock. I wish it were on someone else, but this cock was a fun blowjob challenge. I'm on my knees in front of him, looking up for instructions. Charles said, "Go ahead, lick it." Gently picking it up in my fingers, I licked the head of his cock, and he said, "Take it all in your mouth, kid. I want lots of tongue action."
Nodding, I sucked and lapped it, and incredibly it got wider, fatter. It was a mouthful, for sure. After two minutes, I had spit running down my chin, and his cock was as hard as a baseball bat. He cupped the back of my head, humped the head into my throat, and pulled forward on my head, getting the fat head into my throat two or three inches. I became as docile as a kitten for him, totally dominated without even thinking the word.
He fucked my throat for thirty seconds, tears streaming down my cheeks. Panicking was the worst possible thing I could do, so I concentrated on being submissive. He overwhelmed me in ten seconds, and I wasn't remotely prepared for that. He pulled his cock out of my throat, then completely out of my mouth, and said, "Get behind me and get your tongue up my asshole. I'll fuck your girlfriend first and then you." I didn't give a second's worth of thought to not doing what he said. I scrambled around behind him and spread his fatty buttocks, and licked up his ass crack and over his anus. He was clean, but even if he weren't, he'd put me in a submissive trance, and I would have tried pleasing my dominant top anyway.
Willie mumbled, "You got me a little nervous now that it's finally my turn, Charles. That's a big one you've got there." Charles said, "Jesus, Worthington, you're finally getting what you've been begging me for all these years, and you whine about it. Jeez, what a cunt! Roll that condom on me and turn around."
I don't like Willie being talked to like that, so the submissive trance that felt so calming dissipates, and now I don't like Charles again, the pig. I stop rimming and spit in disgust. I heard Willie say, "OW! Go slow, Charles, please; it hurts." Charles says, "Oh, for Christ's sake, will you be quiet!" Willie screamed out a little as Charles did a big hump forward and then another one. I sat back on my ankles, waiting for him to notice I'm not rimming his ass. All I could think about was how this could be a sexy experience if it, for example, was Carl instead of Charles. As it is, this is the least sexy sex I've ever had.
Willie never sounded like he was experiencing anything but pain. His groaning and complaining got weaker and weaker the longer Charles fucked him, but it never turned into those pleasure sounds Willie and I are used to. After five minutes, Charles starts smacking Willie's ass. From the grunts and more frantic humping, I guessed Charles was close to climax, and with two last violent humps into Willie, Charles goes, "Agggg, ah... oh fuck!!" and stops thrusting.
Willie had been jerking himself off but never actually climaxed by the time Charles pulled out. There were smears of pink coloring on the condom. Apparently, he'd broken some blood vessels up Willie's ass. Willie's face was pale as he walked into the bathroom, saying, "I've got to take a shit." Charles was breathing noisily as he turned to me, and putting an arm around my shoulders, he leaned on me for thirty seconds, then laughed and said, "Christ, I should have fucked him years ago. What a tight pussy! Jeez, great cum shot. Almost blew my condom off, ha ha."
In mid-sentence, he seemed to realize he was commiserating with a nobody. He made a face like, oh, it's you. Then snarled, " "Get this condom off me, kid". I pulled it off; it had a big load of cum, leading the way when I tossed it in the trashcan. I couldn't flush it because Willie was on the toilet, and I wasn't going to hold it until he got off.
Still naked, Charles grabbed the Gatorade for a big gulp and then fumbled the last of my Marlboro Lights out of the pocket of his shirt, which was lying on the chair. He looked around, and I knew what he needed, but I waited for him to ask. He looked at me, pointed at the cigarette in his mouth, and muttered, "Duh, I need a light, Darren?" I took my time getting my lighter out of my shorts and said nothing. Charles grabbed the lighter, lit his cigarette, smoked the Marlboro with the filter intact this time, and drank his Gatorade.
We waited for Willie without talking. I can outlast almost anybody with the silent treatment. I can remain perfectly still and let the silence build until the silence is screaming in the other person's head. It didn't bother Charles, though. Willie finally came out of the bathroom with his girlie panties pulled up. He was holding his ass with both hands, saying, "I needed to put a tampon up there, Charles, it was bleeding." Charles goes, "You've got your period, that's all," and then did that mean sounding forced laugh again.
Willie came over and put an arm around my neck, looking for sympathy, so I hugged him and kissed his cheek; then he kissed my lips, and Charles said, "You girls, hold off on that shit until I'm out of here or I'll vomit this Gatorade all over your nice silk sheets there on your bed, Worthington." Willie ignored that and said, "Let's have a cigarette, Dylan." We shared one like Chubby, and I do it. Charles mumbles, "Your boyfriend was giving me the creeps, Will; he's like a zombie or something."
Willie snapped, "He is not!" Charles says, "Oh, fuck this. What a lost night! I'm going to kick Nathan's ass for leaving me at that fucking block party. I didn't want to go to in the first place." Willie looked at me as if he was sorry about Charles. He said, "Your friend git sick, Charles. You should have gone to the hospital with him."
Charles glared at Willie, then said, "The day I need your advice, I'll know it's time to jump off the Prudential building. As I said, I'll fuck your boyfriend's pussy, so he'll at least know what a real fuck feels like. I'll get him squealing like a little girl, but unfortunately, your skinny little dick, Worthington, might not do it for him anymore afterward". Then, once more, a forced laugh before adding, "We're done tonight after that. Got it?"
Willie said, "You don't need to do this, Dylan." I murmured, "I don't want to, Willie." He turns to Charles, "Nah, I don't want you to fuck him, Charles. This whole thing was another one of my bad ideas." Charles is indignant, "What the fuck? It was your fucking idea, not mine. It's his loss; let's get out of here. Christ!"
We quickly pulled on our shorts and shirt, and, in silence, Willie drove Charles home. His parents' house was only three miles from Willie's. When Charles got out of the car, he said, "I didn't care for your attitude at your house, Worthington, so don't come sucking around me at Prep. You're a loser, and I don't hang with losers!" Willie said nothing, and neither did I. Charles left the car door wide open. I climbed into the front passenger seat and closed the door. Willie looked at me with a grin, patted my thigh, and said, "Sorry, I wish I could blame it all on the vodka, but I'll take the blame for this disaster. The idea about the three-way with that arrogant bastard really sucked. What'd I ever see in him all these years? I'll make it up to you, Dylan. I promise!"
We were in front of my condo before nine o'clock. My Mom wouldn't be home until around one in the morning, and when Willie said he was coming in, I said, "Cool." It felt good in the condo, with the air conditioner maintaining seventy-two degrees, and it was the first real peace and quiet we had experienced all day. My arms went around Willie's neck, and his arms held me tightly around the waist, our mouths together, and we made out like lovers do, savoring the kisses, doing everything slowly, gently, lovingly.
I soon felt Willie's boner bumping against mine and then wetness at the head of my cock. I thought about pulling away, but before I could, Willie slid his lips off mine and snickered. "Dylan, I almost blew a load in my pants and remembered we're still wearing girlie underpants." I'd forgotten, but now I thought how nice my junk felt in silky underwear. We chuckled and had a few more kisses, and then Willie wanted something to drink, so we each had a Coke out on the front steps, smoking a cigarette. Willie told me he'd almost bought a pack of Marlboro in a convenience store the other day. "See, you got me hooked on this nasty habit, Dylan. You got me hooked on you too, baby." We kissed on my front steps, smoke drifting out of our mouths as we did it. I'm going to be outed by somebody someday soon if I keep this up, but Willie arouses me, and I can't resist him.
Inside, Willie, in a mischievous mood, says, "Do you want to play a computer game?" I shake my head and hug his neck, murmuring, "I'd like you to fuck my boy pussy for me" Willie goes, "You're so perfect! What did I ever see in that arrogant asshole, Charles?" He gave me a sweet, loving kiss that made me feel dizzy. Willie, the romantic. Something so nice. He whispered, "Your bedroom again?" I took his hand and led him to my bedroom, where we did it earlier tonight.
Smiling at one another, we removed our clothes, including our girlie, frilly, silk undies. Our boners bounced in front of us as we moved. Willie was doing his usual quick breathing as he got behind me and grabbed two fistfuls of my buttocks, maybe a little bit too roughly, saying, "Bend over and lean on your little bed there." His wet cock head was immediately at my hole. I said, "Use some lube, Willie". He didn't have any, and he didn't like Vaseline, but I said, "Please," and he said, "Sure."
Using tissues to keep it off my hands, I spread Vaseline on my anus and the head of his seven-plus-inch boner. I leaned over on the mattress, and Willie gripped my hips and went right up against my asshole with the slippery head of his boner. I pushed my ass back at his boner, and he took in a big breath and then humped hard, his boner going up inside me four inches. Vaseline is messy but very slippery, too. Willie moaned, "Ohhhh," and I tried not to scream in pain. It didn't take long before the hurt turned into the most fabulous feeling I've ever felt. Willie pushed in his full seven-plus inches and did a fast, full fucking of my ass with me, uttering, "AH!" with every full penetration. We both wanted to get off badly, and I floated with the stars as Willie fucked me.
I can't tell you how wonderful it felt. Willie was rough, but gentle, too. I know that sounds crazy, but I felt his love from beginning to end, which wasn't very long. Too quickly, I had a fantastic climax blowing cum all over my sheets. My heart pounded as I gasped a deep inhale, and my whole body shuddered with pleasure. He'd never had an orgasm during that geek, Charles, fucking him, but thirty seconds after I blasted off, Willie shot a lot of his creamy teen cum up my ass.
He dragged me up on the bed, and we did that tight hug and some kissing. He eventually had me in such a tight ball of arms, legs, dicks, and bodies I didn't know my dick from his. He got his boner up inside me a little later and did a slow fuck on me that had us both moaning in pleasure. The second climax was only a wet spray, but it felt good. Willie giggled about the panties some more and then told me how much he loved me, going on for fifteen straight minutes talking in a whispery voice that had me totally mesmerized. I could hardly move a limb the entire time.
We were sweaty and sticky with cum, so a little later, we took another quick shower together, crammed into my small shower. We made plans for our Tuesday date. I also tried to talk him out of going to Maine later in the week, and he said, "You've got me reconsidering everything, Dylan, but who'll be my roommate if Larry throws me out?"
It was like we didn't want to part, but Willie finally left, and I got ready for bed. After I had finished in the bathroom, I lay in bed, thinking, how can I love both Willie and Robby and then have a special love for Chubby that's even stronger than my other loves?
To be continued.....
