Dylan and Friends

Willie is waiting At the bus stop for Dylan after Dylan's sweaty Tuesday work day. The drive to Willie's house and get hotter sand sweatier playing B-ball, then fucking in the hammock. Willie is sorry for his attitude their last date and admits Dylan's been right all along, so...

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  • 17 Min Read

Getting off the bus, I expected to see Willie as he said he'd pick me up here, and there he is across the street sitting in his convertible with the top down, smoking a cigarette.  Oh, shit! He picked up the smoking habit from me. My bad!

This is the first time I've seen him smoking without me smoking with him. What a cool-looking guy he is. He casually blew smoke rings into the humid, late afternoon air. I'd seen him do that before and wondered how he'd learn to do it. Willie didn't see me, so I watched him put the cigarette in the corner of his mouth, squinting his eye above the cigarette, and then he mussed his hair in the rearview mirror. Willie's hair was unruly now that the silly flattops had grown out.

He looked cute; his youthful appearance was fun to look at, and I had half a stiffy in my pants, knowing he was my boyfriend.  I'd bet anything that most gay teen boys would love to have Willie as their boyfriend. Too bad, guys, he's mine.  Pulling a Marlboro Light from my pack, I shouted at him, "Hey, stuck-up, got a light?" His head snapped around, always ready for a fight, but instead, his face lit up when he saw it was me!  It's so nice to see how happy someone is to see you.

I strolled to his car, trying to be as cool as he is, and leaned on the passenger side door to quietly say, "You're the hottest looking boy sitting in a convertible with a grown-out flattop, smoking a cigarette that I've seen today."  Willie grinned, leaned right over to grab the front of my T-shirt, and pulled me down to kiss me on the lips. People walking and driving by meant nothing to him. He held the kiss for maybe five seconds, with a lot of saliva and tongue.  My boner was a little over six inches of hard flesh and blood by now.  

Taking a deep breath, I said, "Love you," he muttered, "I know you do. C'mom, get in the car, I love you too."  Almost in a trance, I got in and, flicking his cigarette butt over my head into the street; Willie did a wheelie away from the curb. God, he's fun to be with. We looked at each other, grinning and smirking as we drove along, and I could tell he was as happy to see me as I was to see him.  I feel so comfortable with Willie now; I'm totally relaxed around him, knowing everything's been taken care of. We occasionally have disagreements and bumps in the road, but most of my time with Willie is awesome.  I was a bit dirty and sweaty after working all day, but that didn't worry me because Willie would have anticipated I'd be like this, and he'd already have figured out what to do about it, too.

We drove directly to his house and wandered, holding hands, down the brick path to the tennis and basketball courts near the pool.  This was new, the hand-holding. Usually, he has his arm around my waist. In a long-winded manner, he told me that he was sorry about how he acted on our last date.  He described how it was so obvious to him now that I was the one he cared about.  Not Charles, Larry, or anyone from that entire Prep school gay crowd. They acted like such big deals mentoring him at prep school, but they were mostly interested in impressing themselves and each other, not Willie.  He was like their abused mascot.  

He said, "They treat me like shit, Dylan. I didn't have fun with them like I do with you.  Sure, Larry and Carl fuck me fine, it feels great, but I liked the couple of times you fucked me much better.  And I like fucking you even better than you fucking me. You're the one I want to be with, and I don't want to go to Maine. I'll go this last time, though, because I said I would, and they've made plans and all that, but this is definitely the last time. And I'm going with a different attitude.  They won't like it one bit, but tough shit, I'm a new person thanks to you".

Everything Willie said was positive from my perspective. I loved hearing it; I have finally won the day, getting Willie to change his mind about Larry's dominant sex-partner philosophy. Before today I thought I was losing out to that dumb-ass dominant philosophy and I was giving in on some things, but only because it's harmless. I am okay with doing little silly things for Willie as long as the big things get tossed out via our compromise. The biggest one to get tossed was that mind-numbing concept of training me to be submissive ... plueeeeze!

Anyway, he finally says, "Enough of me talking about me, Dylan. How about if you talk about me for a while!"  Then he laughed at his self-deprecating joke, pulling me against him. We hugged and did a quick kiss before Willie asked, "Are you mad at me, Dylan?  You know, because of our last date..." I said, "I was a little bit angry, but like always, you won me over in the end.  Being your boyfriend means a lot to me.  I love it..." He blinked his eyes and bit his bottom lip, then mumbled, "Thanks Dylan; you too."

We were at the swimming pool area, next to the basketball half-court. Willie, acting upbeat, said, "Let's shoot some hoops."  I was up for that, and as we walked onto the basketball court, I thought about Willie's reaction to my comment that being his boyfriend was important to me. It reminded me that Willie can be very emotional.  Little displays of affection from me can often get him choked up. I sometimes forget that he has spent his whole life kind of alone and on his own.  No brothers or sisters, only casual grandparents' interaction, and no parental guidance at all. Since the first grade, he's been in boarding schools, and when on vacations from school, his globe-trotting parents are rarely at home. Willie's major influence comes from the gay students at Prep school, and he's had bad luck with that, too.

He wasn't thinking thoughts like that, though, he was dribbling and shooting the basketball.  He's quite graceful on the basketball court, a pretty good ball handler and a very good shooter.  That's not surprising considering his talents as a tennis player, he has excellent eye/hand coordination, and he's a good dancer, too. He plays basketball with a grin on his face, always looking at me.  

We played two games of HORSE, and then Willie said, "Let's get naked, Dylan.  No one comes down here."  As I dropped my shorts and pulled my T-shirt over my head, I expected we'd be going in for a swim, but when we were both naked, Willie took my hand and led me to the same hammock; we had so much sexy fun in on our second date, or was it our third?  After the basketball games, we were both sweaty, not just me.  

Our bodies slipped against one another as Willie pulled me into him. We hugged and kissed, leaning back against the hammock. Willie's kisses are so sexy, and as we were rubbing our noses together, our tongues were out, smearing saliva on each other; my cock got so hard it felt stretched. I reached down and stroked it as Willie, catching his breath, mumbled, "Hop up on the hammock with me, Dylan," and as we awkwardly mounted the swaying hammock, Willie's long boner bounced against my belly and poked me in my side. I did a large inhale, thinking that his seven-plus inches of hard cock would soon be way up inside me.  My body shuddered with anticipation as Willie positioned me on my back with my legs spread.

He murmured, "Perfect," and got between my legs on his knees, breathing in spurts.  He grunted, "I love doing this more than anything in the world. Keep your legs spread, try to get your pussy up a little more for me."  I pulled my legs back with a hand behind each thigh, the result was my ass pulling up off the bed of the hammock, and Willie muttered, "Oh yeah... that's good." He leaned forward and drooled a long string of clear bubbly saliva right on my asshole, hunched forward a little on his knees, lined up his boner with my hole, and humped his hard dick inside me, moaning, "Ooooooh... that feels good."

I scrunched up my face, absorbing the pain of that precum-for-lube entrance. He murmured, "Sorry," and inched forward, pushing his boner in all the way, and then stayed like that, biting his lower lip with his eyes closed, murmuring,  "Mmm," and slowly, opening his eyes, he grinned at me, and did a dozen four-inch quick thrusts that had me imitating Willie by biting my lip and moaning, "Ooooooh, yeah, just. like that,"  breathing quick short breaths as he lengthened his thrusts, and sweating like mad, he fucked me steadily until I squealed, "I'm cuming! Ahhhh, ohhh," and cum shot up on my belly as I closed my sphincter ring and Willie unloaded his gooey sperm into my bowels, some running down both buttocks, drooling out around his cock.

He said nothing, his face very red, as he grunted with each shot of cum.  My hole was slippery with it, and then he fell forward and we wrapped our arms around each other's sweaty bodies.  The side of his face slid on the side of my face as our sweat combined, warm and slippery.  From Willie's initial penetration to my climax was less than three minutes.  

Getting comfortable, Willie and I squirmed around gently in each other's arms as the hammock swayed easily under our weight. It was such a great feeling having his cock inside me. Snuggling into Willie's embrace, it occurred to me how sorry I was for boys who can't appreciate the depth of sexual feelings being fucked well by another boy can generate inside you.  It can't be described adequately, but getting fucked is surely my greatest sexual pleasure, and it's hard to imagine anything feeling better than the way Willie fucks me.

The few times I've been the one to do the fucking, I think, "Wow! This is the greatest, but that feeling only holds up until the next time a guy fucks me, and I learn all over again that that's the most intense sexual pleasure for me.  My entire body tingles with my climax, my toes and fingers curl up tightly, and I shudder all over. Well, as I said, I can't articulate how wonderful it feels.  I start looking forward to the next time as soon as it's over.

Hugging Willie's slim, sweaty body and feeling him kiss and lick the side of my face, I can't get enough of him, and when he begins making out with me, I feel his cock hardening and swelling inside my ass, my own cock follows his example, and I grow another boner, too. Willie fucks me so slowly and lusciously the second time around I almost get hypnotized by the rhythm of it, the sensuous feeling inside my ass and the urgency of Willie's sexual needs, and the need he has to hear me tell him how good it feels. For us two now, it's almost like a dance. "Oh my God, this feels so good, Dylan. Nothing feels as good as my cock inside your body. Mmmm, ahhh."  

Then he quietly said, "On your stomach now, Dylan, and get your pussy up." I did that, and he slid his cock back up my ass, asking, "How's that feel?" I'm in ecstasy, murmuring, "Oh, god, yes, right there, Willie,  faster. Ohhh, yeah, Willie, oh, Willie!" It was a methodical fucking that lasted maybe ten minutes, and when I had my second climax, it felt so fantastic I almost screamed. It was only a spurt or two of cum, but it felt like a geyser of cum.  Willie continued fucking me for a few more minutes before he climaxed inside me for his second blast of the evening. His climax felt as if it were more than a spurt, and then he tied me up tightly in his arms and legs, his cock still inside me, and he gave me a hickey on the front side of my neck.

He sucked on my neck and licked the spot so long it went past the burning, itchy stage all the way to the numb stage.  At one point, he whispered in my ear, "You're so perfect tonight, Dylan.  It's exactly like I knew you'd be."  Well, after he said that, I wasn't about to complain about how long it took him to give me that big hickey, but it sure was a beauty. I felt it with my fingertip.

Willie pulled his softened cock out of me, saying, "That's a good hickey right there, baby. Not too many guys could do a better one, but you're worth it. Then, "Oooh, my dick is so sore."  I mumbled, "So is my asshole."

No one was home, so we stayed naked, and with each step we took toward his house, I felt Willie's cum drooling from my ass and slowly running down the inside of my thighs.  I loved that it was his cum. We talked about us and how we were made for one another. I can't remember Willie being this relaxed and easy-going. When we met at Carl's party, Willie was sweet and shy. Then, later, in Sea Isle City, he was beginning to get aggressively dominant, following his idiot mentor's instructions. Now he's reverting back to the original Willie. The one I first knew, who I believe to be the real Willie.  

Whatever. Right now, I'm enjoying this version of Willie. Sure, he still likes acting a little dominant in deciding when we have sex and in what form it takes, and he calls me baby or sweetheart, and he still calls my ass a pussy, but none of those things bother me anymore, and in fact, I kind of like it when he does those things.  I've come to like them because it's all part of Willie's unique personality, not an important part at all, just a few little harmless quirks of his. And maybe it's weird, but I enjoy being in the Willie role when Robby and I are doing stuff together. With Robby, I'm the boss as much as Willie's the boss between us.  

Inside the house, we got cold drinks, which we took outside so we could smoke while we drank them.  Willie says, "I hate that you got me hooked on cigarettes, even though it looks cool smoking." I pretended to be shocked, "I got you hooked on something? Surely you jest! I do what you say." Willie laughed, "How can you say that with a straight face? You run the show, Dylan." I mutter, "Ha! That's a good one!"

A little later, we took a long shower together.  I love Willie shampooing my hair and scrubbing my body with a rough washcloth, lots of soapy lather drooling down all over my body.  Then I returned the favor, and it gave me a boner. Willie whispered in my ear, "You love all kinds of sexy activities, don't you?" I nod, and he strokes my boner, murmuring, "Turn around." As soon as I turn, the head of his cock is at my asshole thar hadn't closed up all the way yet. He's pushing firmly, and it slides in a few inches. Gasping at the pain, I go up on my toes.

He grunted, "I can only do a little Dylan; my cock is too tender to really fuck you hard."  With that, he did a pretty good impression of fucking me hard. The hurt faded quickly, though, and it felt even hotter than normal because it was unexpected. Plus, we'd never done it in the shower, and that's especially surprising considering how many showers we take together.  He got going pretty well, and I started pushing back with my ass trying to get his cock further up my rectum. That's how good it started feeling, sore ass or not.

I was blowing saliva sprays into the cascading shower water at how good each deep thrust of Willie's long cock felt.  Sore cock or not, we both got caught up in the fuck, and he had me bent over after a while, me grabbing onto the shower door handle as Willie fucked me in a frenzy.  He was groaning out as if in pain with each penetration, but he wouldn't or couldn't stop.  I think I finally sprayed some drops of cum, at least it felt like I did, into the shower spray.  Felt fantastic! The third fuck tonight, and it was still feeling way good.  

I know Willie shot some cum up my ass because it came back out a few minutes later. He pulled out, half laughing and half moaning in pain, "Holy shit, Dylan.  We need chaperones or something; I can't control myself around you."  He was hurting but loving it too, "Ow, ow, ow," as water sprayed on the sore-looking, red head of his cock; it looked just like Dodger's cock that time in the half bath when Robby had called me to look at it. For some reason, Robby and Dodger thought I might have some remedy for a tender dick head.  My advice to the lad was simple. I told him to stop playing with it, but I wasn't inclined to tell Willie that.

We finished our shower after that and lay together on his bed naked, drying off. Willie had his arm under my neck, holding me against him as he talked more about how he now saw the guys at Prep school differently than before this summer with me.  He asked me very seriously, "Do you love me, Dylan?  You're not just saying you do to make me feel good, are you?"  

I thought about it briefly and said, "Yes, I really do love you, Willie.  Well, let me be totally honest and say that I love you to the extent I know about love." He grinned and pulled my head over to kiss my forehead, mumbling, "You say something great and then qualify it, so it isn't as great, but I think I know what you're saying. We're two young gay kids; what do we know about anything, right?  But, as far as we know, we love each other, right?"

Grinning, I nod, "Exactly!"  He talked for another half hour; Willie likes to talk, and I like listening, so we are a good couple. Everything he talked about had to do with comparing what he used to think about a young gay relationship and our relationship. He said many things that assured me that Larry and the Prep school boys had lost their number one disciple. We'd bungled around a lot with our relationship this summer, but somehow it seems to be working out how I hoped it would.  Of course, the better my relationship with Willie is, the harder my dilemma becomes because of how I feel about Robby Dickers.

Getting dressed in the expensive-looking clothes Willie put out for me. He's looking at my work sneakers lying on the floor, muttering, "Those grass-stained Nikes won't look too good with what you've got on, so here, put these on," and he flipped me a pair of his Birkenstock Taupe Suede sandals that I'd seen him wear a few times on our dates.  Sweet!  I said, "Okay, but I'm only borrowing these sandals."

Shrugging, Willie got dressed in almost identical clothes. We're twins! For dinner, Willie took me, of all places, to Ken's Steak House. We both had prime ribs of beef, mashed potatoes, and the house salad, which was the same dinner Chubby and I had months ago. The big difference between Chubby's and my time here was that Willie didn't attempt to order beers, so we were saved from experiencing that embarrassment. Again, the dinner was excellent, and for dessert, I ordered coffee and white cake with white icing, which was the same thing Chub and I had.  

Knowing I wouldn't see Willie until a week or two from tomorrow was disappointing. Still, I can't go to Maine even if I was invited. I work, which these guys don't need to do 'cause they're from rich families. Plus, the memory of Larry and Charles was disturbing and reinforced why I'm glad I'm not going to Maine. Carl fucks great, but I have two boyfriends now, so...

This entire date tonight had been fun, but I was surprised that we held hands at the table while waiting for dessert. I'd unconsciously taken hold of his hand when he'd help it out to me as we talked excitedly about our date in Sea Isle City during my Wildwood vacation. My face got bright red when the waitress plopped our dessert down on the table and said, "Here you go, sweeties." Then grinned, asking,  "Which one of you is the girl, and which is the boy?"  I tried to pull my hand away, but Willie anticipated that and held it tightly, saying, "That was insulting and no way to talk to customers, even if we were teenagers."

She muttered, "Whatever you say, teenager," and arrogantly walks off with her fat ass swaying from side to side.  She couldn't care less that Willie had called her out.  Her obnoxious behavior took the fun out of dessert. Willie saw me struggling to swallow a forkful of cake and said, "Let's get out of here."  He left money on the check, and we left.  Willie stopped at the reception desk and complained that our waitress had been rude and homophobic while serving us. He'd be complaining about it in writing to appropriate advocate groups.  The lady at the desk frowned and looked around as she tried to follow what this kid, who appeared to be about fifteen, was talking about... and where his parents were.  She looked back to where Willie and I had come from, but no adults were following.

Outside I burst out with a relieved laugh, and Willie was chuckling, too, saying, "That cunt!  What can we do, though?"  We got really going with that theme for a while; Willie said, "I hope that cunt enjoys the three-cent tip I left." and we worked that to death, too. A little later, Willie pulled into the same DQ that Chubby and I went to the night we ate at Ken's.  That night with Chubby, I found myself in a fistfight with the tall dude who insulted me, so I looked suspiciously at the few tall kids I could see this evening; he wasn't one of them. There were the same milling groups of teens here this Friday night in August as there were the night Chubby and I were here in June.

I stayed in the car, and Willie got us cones that we ate as he drove the short distance to my condo. He didn't ask or hesitate tonight but instead just parked at the curb and kissed me like a lover's kiss, long and deep.  Holding my head between both his hands, he got a little emotional, telling me again how I'd changed his life and how much he loved me. Then another long kiss, with the convertible top down.

Those things don't bother Willie; he doesn't think of them because he's been 'out' as gay in every respect since age twelve.  Me, I'm in the fucking closet, and we're right in front of my house at twelve o'clock at night with street lights seemingly acting like high-powered spotlights.  Nonetheless, I didn't pull away; it felt so good to be loved like this.  When I'm with Willie, I don't care who knows I'm gay. Well, I mean, except for that waitress at Ken's, Chubby, the moms, and my neighbors on either side of our condo, plus anyone driving by that I go to high school with; and, who else?

I thought those thoughts while lying in bed. I was also wondering if it would be honorable to tell Willie about Robby and Robby about Willie, or if that would be stupid, making both guys feel bad, or what should I do?

To be continued...

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