Oh, by the way, my name is Dan, and I’m 37. Laura and I both grew up on Long Island, and after high school ended Laura met a guy and married him. Kevin was born the year Laura graduated from college, but tragically 1 year later, her husband died in a car wreck. Laura and Kevin came to live with me in Manhattan for a while, then they moved to a nice apartment in SoHo, back before it became so expensive. I ended up here in Chelsea, had a boyfriend for a few years, then broke up with him back in 2000. Since then, I’ve concentrated more on my career than chasing after guys, but I still get out once in a while.
Laura called me a couple of days ago, and told me that her father needed some help recovering from a broken hip. Her mom had died from cancer a few years back, and her father was all alone in the old farm house. She asked if I could look after Kevin for a few weeks during her sabbatical. It was summer, and although she had planned to bring Kevin along, the condition of her father made that nearly impossible. Of course, I agreed, since Kevin and I have always gotten along pretty well. He’s really a nice kid, and we even have some things in common. Last year, he confided in me that he too was gay, and asked for a bit of advice.
I wasn’t really surprised that Kevin was gay. Actually, it looked likely from a fairly early age, maybe 6 or 7. Now he’s 15, but he hardly looks more than 12. He’s short, with an unruly mop of blond hair, nicely sized lips and nose, and he always seems to have a smile. I’ve looked after him in the past, but never for such a long period of time.
Well, Laura came over that night with Kevin, and with a fairly large bag of his stuff. My apartment is a loft, so Kevin was going to have to sleep on the hide-a-bed, but he didn’t seem to mind much. Anyway, after a while, Laura left, and we got a chance to catch up on things. He told me about some of his past boyfriends, and some of the disappointment he’d experienced. Then he said something to me that I didn’t expect.
“You know, Dan, I want to try sex with an older guy. The guys my age just want to get off and go.”
I respond to him, saying “Umm…you know, you’re only 15. A lot of people would have a problem with that, and, besides, how can you be sure that the older guy isn’t just taking advantage of you?”
“Yeah, I know there’s a lot of freaks out there”, he replies, “but I’m not talking about finding some sugar daddy to take care of me-I’m just talking about looking for better sex than I’ve had so far. My mom seems to be ok with the idea, too. She said to me the other day ‘Honey, if you have sex with an older man, just be sure he isn’t taking advantage of your youth’. I mean, it’s not like I’m gonna hop in bed with the first guy that offers, either. I’ve turned down a lot of offers from guys on the street and online. Some of them offered me a lot of money, too.”
This last statement surprises me. “You’ve had guys offer you money for sex?”
“Oh, lots of times. One guy once offered me $1000! He wasn’t half bad looking, either, but I just didn’t trust him for some reason. I’m not into taking risks that big.”
“Damn, how’d you get so mature?” I ask. He just smiles and says “By taking good advice from people like you.”
He leans back on the couch, and continues. “Of course, I’ve done a few stupid things. Like James, my first boyfriend. I was 13, and he was 17. I was soooo in love with him. I let him fuck me, and he wasn’t gentle about it, either. I let him do it to me so many times, because I thought he loved me. Then he dumps me for another guy. I should’ve seen it coming, but I was stupid with love. Oh, well…..”
I ask him a bit more about his sex life, and he’s quite open about what his likes and dislikes are. He admits to being more of a bottom than a top, but he’s only been a top with one other boy, a friend named Jarred, who is 13. “You know, it was funny the first time Jarred and I got in bed together”, he says, “I thought that he just wanted to jerk off, but next thing I know, he’s got his butt up in the air, begging for me to fuck him. I did the best I could, but he wanted me to be more rough, and I just couldn’t do that. You know he wanted me to tie him up?” He hasn’t fucked anybody since then, but wonders if it would be more fulfilling with the right person.
We talk for a while longer, until I get tired and we both go off to bed. I show him how to open the bed, and he thanks me for being so hospitable. He gives me a nice, big hug, and a sloppy kiss on the cheek.
I wake up the next day, Saturday, and Kevin is already up. “Good Morning”, I say to him, on my way to the bathroom. I take care of my usual morning movements, then go turn on the shower, a nice double-sized unit I had installed back when I had a boyfriend here. I pop open the door to the bathroom half-way, to keep the steam from building up too much, and enter the shower.
I’d been standing under the water for about a minute when I hear Kevin in the bathroom. “How’s the water?”, he asks. “Oh, it’s fine and warm”, I say, just as the door opens. Kevin enters, naked, of course, and joins me under the second nozzle. I hadn’t seen him unclothed in at least 3 years, and was a bit surprised at just how well he had matured. Although his face was that of a 12 year-old, his body was fairly buff, especially the legs and thighs, but his penis was something altogether unexpected. He had a large, uncut, man-sized dick and balls-probably would be 8 inches erect, and fairly big around too. I might add that it isn’t what you’d call a “grower”, either. A nice patch of blond pubic hair topped it.
“My lord, I didn’t know you’d grown so much, Kev”, I blurt out. He smiles, then says softly, “Yeah, but not in the places I wanted to grow. I’d be fine with a dick half this size if I could be 6” taller”. He plays a bit with it, holding it in his hand, pulling the foreskin back a bit, then continues “..but….every guy who sees it likes it, so it isn’t so bad, I guess.”
Kevin looks up at me, sizing up my chest and my rapidly inflating penis. “Man, you’re still hot”, he says. I notice that his penis is likewise becoming erect. I feel a little uncomfortable, so I say “You know, maybe this isn’t such a good idea, being together like this. I mean, what would people think?”
“I don’t care a fuck what people would think. Besides, we’ve showered together before, and naked, too.” Yes, it’s true-I showered with him once, down at the Y, when he was about 9, so I say to him “Yeah, but you were just a little kid back then”
He smiles again. “You don’t think I was checking you out, even then? I used to fantasize about you, you know. In fact, the first real orgasm I had, I was jerking off thinking about you, remembering the way you held me back on that day in September, 2 years ago.”
I remember that day well-his mom worked in the Trade Center complex and should’ve been on the 95th floor of the north tower that morning. Luckily, she was late getting in and was actually just at the elevator transfer when the plane hit. Kevin was just going to school when he saw the plane. He tried to call his mom on his phone, but couldn’t get through to her. He was near my apartment, and he came to me for comfort and support. It was probably the longest 4 hours of either of our lives that day. I held him in my arms while he cried like a baby.
I put my arms on his narrow shoulders. “ I never knew you felt that way about me”, I say. He puts his right hand on my chest, then runs his fingers down my abdomen, the says “Well, it’s true. I do.”
He wraps his fingers around my hard penis, then he looks up at me. “Dan, don’t worry. I’m not going to tell anybody about anything we do here. I know that you could get in trouble, and I wouldn’t ever, ever do something like that to you. You can trust me, and I know that I can trust you.” He bends down a bit, then wraps his lips around my dick.
“Umm…Kev…why don’t we take this out to the bed, where we can do this properly, OK?” He looks up at me, with my penis fully inside his mouth, then pulls back. “OK, sure”, he responds, turning the shower off.
We dry each other off, and in a minute we're both on my bed. I lay down and place him on top of me, straddling me, with his penis on top of mine. I hold them both in my hand, his penis now completely unsheathed and red. “Kevin, your penis is bigger than mine, and you're only 15. I wonder how big it will end up being?” I slide him forward a bit, so that I can take his big, uncut dick in my mouth.
Kevin enjoys my attention to his big penis quite a bit. I play a bit with his soft foreskin first, pulling it forward, and slipping my tongue between it and his glans, then running it all the way around. Then, I slip it inside my mouth, and use my tongue on the underside of his big fat pole. He starts to slide it in and out a bit, so I grasp his muscular buttcheeks, one in each hand. He gets a nice, slow speed going, like a guy who knows how to enjoy sex. He gently runs his fingers through my hair, and occasionally makes a moan of pleasure.
After several minutes-quite a feat for a boy of 15, I might add, he whispers “I’m gonna come soon. I don’t know it you want it in or out.” I respond by taking his dick even farther down my throat than before. “OK, get ready-I’m holding as hard as I can”. He gives a few more thrusts, then starts moaning. “Uuuh…ooo….AAAAAH!” he exclaims, and he shoots his semen deep into my throat. I keep swallowing, as jet after jet of his spunk squirts out. I swear that he keeps pumping for 15 or 20 seconds! In all my years, I’ve never experienced an orgasm as forceful as the one Kevin has. I wrap my arms around Kev’s nice, muscular buttocks as he finally stops ejaculating. I continue swallowing, in order to get it all down my throat.
Kevin strokes the back of my head, then he starts to pull out. I unwrap my arms, and allow him to flop down on the bed. I come over to him, and straddle his body with my legs. “Oh, Dan, that was just awesome! I’ve had anybody give me a blowjob like that before! And I don’t think I’ve ever squirted out so much cum, either. Thank you soooo much.” I bend over and kiss those nice, full lips of his. “Man, you are good, kid”, I tell him, continuing “I can’t believe you lasted so long.”
“Yeah, I wanted to make it last, and so did you. I can only imagine what it would be like to have you fuck me. I’d really like to try that, you know. I’ve had much bigger dicks up my ass before, so you don’t have to worry about hurting me.” Kevin brings his knees up to his chest, exposing his pink hole. “You want to?”, he asks, smiling.
I reach over to the night stand, and pull out a condom. I put it on my dick, then lube it up good with KY before laying down next to Kevin. “Here, try it this way”, I say to him, holding my rigid penis straight upright, ”this way you can control just how fast you want it.” Kevin straddles my chest again with this knees, then lowers his butt downward, until his hole is resting on the tip of my well-lubed penis. I ask “Are you sure you are ready?” Kevin looks right at. “Yes. I’m sure. I’ve been waiting for this moment for years. I want to feel you inside me. Let’s do it.”
He presses downward, and my penis slides easily inside his warm ass. He keeps lowering himself steadily until I’m completely inside him and his balls are resting on my abdomen. He stops for a minute and his erection starts to return. “Oh, man, that feels good”, he whispers as he slowly starts to slide up and down on my rigid pole. He works my dick with his sphincter, squeezing it as he slides upward, then relaxing it as he lowers himself downward. He’s obviously quite experienced at this.
By now, his penis is hard once again, his semi-uncovered glans pointing straight at me. I reach over and gently slide his soft foreskin back, then forward, holding it together with my thumb and forefinger, covering his head. “You really like my foreskin, huh?”, he asks with a smile. I slide it back again, then say “Yeah, it’s nice, really soft and sexy. Foreskins are a real turn-on for me. I guess it’s because they used to be so rare. Still, you have a beautiful penis, Kev.”
I continue sliding his soft, supple skin back and forth as he slowly rides my dick up and down. After a minute or s, I feel his sphincter tighten just as he moans a low “oooh”, and he comes again, onto my stomach with 3 short squirts. “Wow, even after that last orgasm, you can still come?” I ask him. He giggles, then replies “Yeah, I guess I’m just a horny teenager, aren’t I?” He starts to tighten his sphincter more than before, increasing my pleasure, and bringing me closer to orgasm. He lengthens his stroke a bit, and in a few seconds I’m ready to burst. I put my hands on his thighs, pressing him downward so that I can push my penis as far into him as possible. He squeezes me hard as I erupt volley after volley inside him.
“Wow, Dan, that was fantastic! You really know how to make a guy happy, don’t you”, he says, as he squeezes the last drops of cum out of his penis. “I experience really does make a difference.” He slowly raises himself upward, letting my latex enshrouded dick slide out of his hole. I grab a towel as he stands up. “Guess we need to clean up again, huh?”, I say to him as I wipe his ropy semen off my stomach. “Maybe later, I’ll let you return the favor, if you’d like”. Kevin grins, and says “Yeah, I’d really like that. Hey-race you to the shower!” He takes off running toward the bathroom, with me in hot pursuit. We both run into the shower, turn on the water, and enjoy the next few moments exploring every bit of each other’s bodies.
After lunch, Kevin asks me what I usually do about that time of day. “Well”, I tell him, “unless I have something planned, I usually go for a haircut, then go down to the gym.” Kevin’s face lights up. “Hey, could we go together? I run, you know, and if there’s a track, it’d be good for me to practice. I need a haircut, too.” “Sure, Kev, you can run while I use the weights, then we can both go for a swim afterwards.” “Cool”, he says.
Our first stop was my barber, Maurice. He’s an old queen, brobably in his late 50’s, and a damn good barber. We enter, and Maurice greets us. “Well, Daniel”, he says, lisping, “who is the young man that’s with you today?” I introduce Kevin to him, and let him have the seat first. “Well, young man, what would you like me to do with your hair, then?”, Maurice asks him, running his hair through Kev’s thick blong mop. “Well, sir, I’d like my hair to be shorter. I’m tired of looking like a kid, the way my mom cuts my hair. I’d like something that will make me look more mature, and will get the guys to look at me.” Maurice looks at Kevin, then replies “My, how young and proud you are! I remember a time when a lad your age wouldn’t dare be as open as you are. You can’t imagine how lucky you are to be gay these days. OK, young man, I’ll make you look more mature, but those rosy cheeks of yours will still keep you looking young!”
Maurice does a nice job with Kevin’s hair-not cutting it too short, but making it look good on his roundish face. Still, he did look a bit young for his age, but at least he looked more presentable. I take the seat next, and Maurice gives me my usual weekly trim, then we leave for the gym.
We get down to the gym, and Kevin puts on his workout clothes. His tank top is tight, really showing off his form well, and his shorts are…..well, short. They show off just about as much of his legs as is possible, which is probably what he had planned. I’m sure he’s trying to look as provocative as possible, but I’m also sure he can take care of himself. “Umm, Kev…..just don’t lead any of the guys here on too far, ok?” I tell him. “Don’t worry, Dan, I won’t.” We go upstairs, and Kevin goes over to the elevated track. I get a chance to see him each time he completes a lap while I’m working out in the weight training area.
After he’d done several laps, I notice that he’s pacing with an older guy, maybe about 35 or so. They are both keeping up a fairly good pace, both looking like they were natural-born runners, and they seem to be having a conversation as they run. Kev occasionally smiles as they continue. After about 30 minutes, I’m done with my workout, so I go over to the track to wait for Kevin. After they pass me once, the next lap they both slow down and leave the track. “Thanks for the workout, kid”, the older guy says as he leaves, heading for the weight training area. Kevin smiles at the man, And says “Thanks, Sam”, then he looks me. “Hey, I guess I’m just popular”, he says, panting. His body is glistening with sweat, but he still seems to have a lot of energy left. “OK, where’s the pool?”, he asks.
We go back to the locker room and change into our swimwear. I have a pair of trunks, but Kevin wears a speedo. Figures. Anyway, we go to the pool and find it fairly quiet, with only a few guys swimming laps over on the half of the pool set aside for that. I decide to do a few laps while Kevin checks out the whirlpool.
After doing 20 laps, I head over to the whirlpool to join Kevin. He’s in the bubbling water, talking with a gangly-looking boy with reddish hair. The boy looks to be about Kevin’s age, and I can see he’s a bit uncomfortable about me joining them. After a minute, the red-haired boy gets up, and says “Well, catch ya later” to Kevin. As he walks away, I can see that Kevin is watching his thin, almost bony body as he walks away. The boy is wearing a fairly voluminous pair of boardshorts, which only makes him look skinnier.
“Well, what do you think, Kev? Gay or straight?” I ask him. Kevin sighs, “Gay, but too shy. He’s cute, but he wouldn’t open up. Oh, well…”. Kevin turns to me and asks “Are you gonna use the steam room next?” “Sure”, I tell him, adding “I’m sure you’ll like it, if you can stand the heat.” Kevin smiles and leans back, putting his arms up on the edge of the whirlpool. “I love heat. Don’t worry about me, I can handle it”.
We head back into the locker room, first to the showers. In no time at all, Kevin peels his speedo off, once again letting his dick hang free and visible. We rinse off, then head to the sauna. I hang my suit and towel on the rail, and Kevin does likewise. Just as I’m about to enter, Kevin says “I’ll be there in just a second. I want to weigh myself first, OK?” “Sure”, I say, and Kevin walks over toward where the scale is, completely uncovered. I notice that Sam is weighing himself at that moment. Instead of watching, I let him head over alone.
Kevin walks up toward Sam, who is standing naked on the scale. “Hey, Sam-how’s it going?”, he asks, after looking at Sam’s muscular buttocks. “Oh, pretty good, Kid”, he replies, “just about got all those pounds off that I was trying to.” Sam turns, and looks at Kevin’s nude body. “Ahem….looks like you don’t need to watch your weight yet” Sam says, trying unsuccessfully to not look at Kevin’s large penis.
Kevin smiles, then says to Sam, “No, but I’d really like to add some muscle. My thighs and my butt are the only part of me that doesn’t need work, it seems. Dan, my mom’s friend that you saw me with earlier, thinks that I’m getting too worried. He says that muscles will come with age, so not to worry”.
Sam looks unabashedly at Kevin’s body. “Well, kid, you don’t have much to worry about. Your abs look good, and you already have a bit of a chest, too. Just work on a few weight exercises, and you’ll be fine.”
Kevin looks at Sam’s naked body, then says “You know, I wish I had muscles like you. You really have a good body.” Sam looks at Kevin for a few seconds. “Um, Kevin, isn’t it…..umm…are you “hitting” on me?” Kevin smirks a little, and says “well, …yeah, I guess I am. I think you’re hot. I…I know I’m kinda young, but I am experienced. I’m not a virgin, and I’m usually more discreet than this.”
Sam looks a bit dumbstruck, but he manages to respond-“well, you certainly are forthright. You’re kinda hot and cute at the same time, you know? And you’ve got one hell of big package there, too.” Kevin smiles, a bit embarrassed, then says “you know, I’ve seen you around the neighborhood before-down at the coffee shop. Will you be there tomorrow, like, maybe around 2? I’d like to talk a bit more with you? It might be easier without my mom’s friend being around.”
“Umm…yeah, ….sure” Sam says, “I could see you tomorrow at 2,”
“Thanks”, Kevin says, “I’ll be looking forward to it”, then he turns around
and walks over to the steam room.
Kevin enters the steamroom, then comes and sits next to me. We’re the only people in there, so we can talk freely. “So, Kevin, how’s your weight?’, I ask him. “Oh, it’s fine. I’m still 122 lbs, but I really want to add some muscle. I talked a bit with Sam over there about some exercises I could do.” Kevin smiles at me, then continues, “besides, I just had to check him out. Man, he’s hot! And, no, he didn’t try to “hit” on me, even though I was standing naked right in front of him, so don’t worry.”
“Well, Kevin, I’m really not that worried. I know you have an eye for older guys. Just remember to be careful and be discreet. Even if you don’t intend to, you could still get a guy into trouble”. Kevin turns to me, then says “Yeah, I know. I guess standing naked in public in front of him was a bit much, but, hey, at least I know he’s a decent guy now, since he didn’t try to take advantage of me. I really like him actually.”
Right about then, the tall red-headed kid enters the steamroom, alone, still wearing the boardshorts. “Hey, Colin, nice to see you again”, Kev says to him Colin sits down on a seat near the door, and Kevin gets up and joins him. There is just enough distance between them and myself that I can’t hear their conversation, but I do notice that Kevin makes Colin laugh lightly about something. Kevin turns toward Colin, and puts one foot up on the seat, certainly giving Colin a better view of his large penis.
After a few minutes of talking, Kevin gets up and turns on the shower in the corner, setting it on cool. “If you take a cool shower, you can keep from overheating”, I hear him say, as he stands under the stream of water. Colin gets up, looks at Kevin’s naked body, then he unties his waistband and drops his shorts on the floor. Colin’s penis is long and thin, circumcised, and not entirely flaccid, either. In fact, I notice that Kevin’s penis is showing signs of enlargement, so I try looking away, to give them a bit of privacy.
After a minute or so, I look back at the 2 naked boys under the stream, both now obviously aroused (Colin more so than Kevin), holding each other’s hands. “I like you”, I hear Colin say to Kevin. “I like you too”, Kevin says to Colin. They turn off the water and sit down together, facing each other. I notice that Colin extends his hand toward Kevin’s penis, obviously feeling it, probably playing with Kevin’s foreskin. I can clearly see Kevin reach forward and caress Colin’s testicles. After a minute, Kevin stops, stands up, and walks over towards me, his semi-erect penis swaying side to side with each step.
“Umm..Dan….uh…me and Colin are gonna go out for a few minutes-OK?” “Sure Kev”, I say, whispering “you can use the stall in the corner-just don’t make too much noise”. “Sure, Dan, thanks”. Kevin walks back over to Colin, he stands up, grabbing his shorts, and they walk out of the steam room together.
I’m changing into my street clothes a few minutes later when a freshly showered Kevin and Colin come over to the locker. It turns out that Colin’s locker is right behind mine. “You both look happy”, I say to the 2 naked teens. Colin makes a shy smile, and says quietly “Yeah, I guess we are”. Kevin smiles. “So am I, Colin.” He puts his arm around Colin’s bony body, and kisses him on the lips. “For a guy who’s never done anything, you were great, Colin. You really were.” Colin gets an erection almost intantly.
“Ummm…boys…maybe you should make a date to see each other sometime, somewhere a bit more…..private?” I say to them. Kevin breaks off his kiss, and replies “Yeah, maybe we should. I’ll give you my cell number, and we’ll make some time to meet later, OK?” Colin mumbles “Yeah, I’d really like to. I like you a lot” He gives Kev a peck on the cheek.