19 Year Old Math Tutor Gets Surprised Ch. 05bywillmasonwillmason©
It had been a full week days since my late night encounter with the cocky but very hot high school senior, Sim. The emails and texts responding to my ad had stopped five days ago, as my post receded into the distant pages of craigslist history. So I was surprised to see a text from a local number that I didn't recognize. All it said was "U don't know me but call if you are avail."
Curious, I dialed the number from my apartment as soon as I got back from an errand. It was about 6 PM on a Saturday. A voice said, "Hello."
"Hi, this is Will. You texted me 20 minutes ago."
"Oh, hi. My name's Miles and my brother gave me your number. I think you know Sim?"
"Yes, sure do. Hi, Miles." I then recalled Sim saying he told everything to his brother.
"Well, this is kind of awkward, but I was wondering if you would be interested in you know, getting acquainted."
That was an interesting way to phrase it. Sim had obviously told his brother about me and had recommended that his brother call me if he was interested in some head. I wondered if the big brother was anything as gorgeous as the eighteen year old Sim. I quickly replied:
"Sure, Miles. I'm glad your brother passed along my number."
"Well, uhm, I know this is short notice and all, but would you like to come by for a beer now? I just picked up some cold ones."
"Sounds great, Miles. I can come by in about 30 minutes if that's cool."
"Yeah, sweet. I guess you know where I live, right?
"Sure do, pretty close to my place actually. See you in a few."
I took a quick shower and let my mind wander about what Miles might look like, picturing a slightly older Sim. Half an hour later, I walked up to the small apartment complex where I had been the weekend before and knocked on his door.
Miles welcomed me with a firm handshake and "good to meet you." As I walked in, another guy stood and shook my hand too, saying his name was JT. Miles hadn't mentioned a second dude. Miles handed me a cold Heineken and they invited me to follow them out by the pool that the small apartment complex was built around. Nobody else was out there. We settled around a table by the deep end. I felt better being outside, in public, until I could judge what these two guys were all about. Looking back on it, it was a smooth move by Miles to put me completely at ease in that way.
Miles was every bit as attractive as his younger brother, considerably taller and more mature looking. The family resemblance was strong, but this was a strapping young man, not a kid. Rather than the cherubic face of his sibling, Miles had a square jaw covered with a blond stubble. His body was long, lean and muscular, like a surfer's. As we talked, Miles's ease with conversation and his disarming manner contrasted sharply with the abrupt style of his younger brother.
JT was obviously of mixed racial heritage, but the exact components were hard to tell. He had a little African-American blood, but his features were more Caucasian. His skin a golden color that reminded me of cafait-au-lait. When JT smiled, I thought those white teeth wouldn't be out of place in a toothpaste commercial. He was athletic, attractive and exotic. I later learned his father was born in Curacao.
Miles and JT were lacrosse teammates and best friends. They were both 22 and on the five-year plan at TSU. JT was as easy-going and open as Miles. I liked the looks and easy-going attitude of both of them. It was a challenge, though, to think about how I could possibly handle two at once.
We chatted for about ten minutes, covering the standard ground about where we came from, how we got to TSU, etc. When JT went back inside to grab 3 more beers, Miles said he didn't mean to freak me out by having JT there, but that he was afraid of scaring me off if he mentioned it during our brief call.
"No problem, man. He's a chill guy and couldn't be nicer."
"So glad to hear that. I think I was afraid I'd chicken out if it was just us alone; I needed JT for backbone, you know what I mean?"
We both laughed and JT soon walked back up holding three new beers. I steered the conversation to the obvious reason we were all here:
"I appreciate you guys having me over for beers. Having met you, I definitely owe Sim for introducing me you. So how did you guys get interested?"
Miles spoke up: "My crazy fucking little brother. And not just his suggestion that I text you, but you see, he and his friend had this "arrangement" (Miles made quote signs with his fingers) last summer. At first, it shocked the hell out of me, but then he kept saying how great it was. It's been in the back of my mind ever since."
JT: "Yeah, Miles and I don't keep anything from each other, so Miles told me all about it, and I'd been thinking about it too the last few weeks."
Miles continued to tell the story: "Yeah, so my brother and his even crazier buddy, Tommy, caught this kid, well he was their age actually, staring at them in the showers at the community pool. It happened back in June. Tommy called him out, saying some shit to him like 'suck my dick, faggot.' But instead of running off, the kid actually tried to go for it!"
I acted like I hadn't already heard about it and was amused at how the details had changed a little from Sim's telling of the story.
"So, Tommy started jacking with the kid, telling him to get in the car with them and all. Well, the kid did, and they went to Tommy's dad's place. Sim said they started doing tequila shots and one thing led to another, and this kid ended up sucking their dicks. After that, they'd just call him up and he'd come running every time. They were into treating him pretty rough from what Sim told me, but the kid liked it...It was too weird for me."
"Wow. Well, I'm not like that kid who was transformed from being a locker room peeping Tom into on-call cocksucker. But I do really get off on giving head to attractive straight dudes, as long as they treat me with the same respect they want themselves. Have you guys ever done anything like we're talking about?"
"No, never," said Miles. "I've usually had a girl, or two, I could always dial up for booty call... and what Sim and Tommy were doing this summer didn't turn my crank anyway. I wasn't into it being a dude and sure wasn't into the abusive talk and stuff."
JT leaned in and said in a soft voice, "Well, my buddy here is a bit more conservative than his brother, or me for that matter. I grew up in a different neighborhood than Miles did and while I have only been with women so far, I knew plenty of dudes who were always getting some head on the DL from a sissyboy... not that you're anything like that, dude. You're clearly no sissy."
"No offense taken," I was quick to say. "I don't see myself as a gay guy. I like girls too. I'm just going through a phase right now where I'm seeing where all my boundaries are about sex. So far, it's been real eye opening. You know when you study human sexuality, you learn these artificial labels society slaps on us, like "gay" or "straight," don't make a lot of sense. The Kinsey Report back 60 years ago or more wrote about a sexual preference scale and most of us being somewhere along the continuum, not 100% gay or 100% straight. I'm in the middle somewhere, exploring what both sexes have to offer."
Miles: "I've read about that too, and about how in some cultures the boundary lines aren't so black and white, just like they weren't in the time of the Roman Empire or ancient Greece either."
I responded, "I'm glad to meet some people who have read up on it and aren't hung up on labels. So, maybe we should go inside and continue the seminar, what do you say?"
We all got up and walked back into the apartment. Miles locked the door, then put on some music. He and I sat on the couch, with JT in a side chair to my right. JT pulled out a little water pipe and loaded a bowl. We started all getting high and drinking some more, then I followed up on my previous question.
" Miles, JT. So Sim's summer arrangement's what started you guys thinking. But I'm sure you have plenty of fine young ass in and out of your beds. What made you want to get head from a guy?"
Miles: "My fucking brother, dude. Once he finally woke up last Sunday afternoon and was able to communicate, he told a pretty amazing tale. He said he'd never gotten off like that in his life and I know he's had plenty of sex, starting the summer he turned 16. When I told JT here, he said we ought to check this shit out. So here we are"
JT: "Tell Will about your problem with your girl, dude; give him some perspective."
Miles looked at me, "My new girlfriend doesn't suck for shit; she can't get more than 3 inches in her mouth; she complains a lot; she is adamant about me never coming in her mouth..."
JT: "Yeah, these sorority girls can be like that...So, today we were drinking some beers after working out, and all Miles can do is bitch about his girl, so I finally said 'forget her and call that guy up now.' He knew who I was talking about. I egged him on till he finally texted you."
High and intoxicated by these model-quality 22 year old guys sitting right next to me, I looked directly at JT and said: "I'll do my best make sure you don't regret it."
With that, JT calmly stood up and turned toward where I was sitting on the couch, his crotch about even with my face and maybe eighteen inches away. I reached out with my right hand and ran my hand up his leg, inside his thigh and under his balls to his growing bulge. JT unbuckled his belt with a confident smile and popped the top button on his jeans. He had on those old school, button-fly Levi 501s. I used both hands to open them all at once.
JT was commando and his beautiful golden brown cock emerged in about a two-thirds hard state. Still seated, I leaned in and, without using my hands, turned my face sideways and picked up the head of his dick with my mouth. My face was slightly below his crotch as his cock wasn't fully standing up, yet. As I slowly engulfed 4 or 5 inches, Miles watched from the other side of me in fascination, one hand gently rubbing his dick through his athletic shorts.
I gave Miles a show, slowly taking in JT's delicious cock inch by inch, then withdrawing almost all before taking in more each time. JT was soon hard as steel. JT was softly saying things like "Oh yeah, that's real nice, real nice, man."
About the time I got all of JT's golden rod in my mouth, I reached over with my left hand and started playing with Miles's dick through the nylon fabric of his shorts. Miles, who hadn't taken his eyes off of JT's cock going in and out of my mouth, was rock hard before I ever touched him. I tugged at his elastic waistband and Miles obligingly slipped out of his shorts and boxers all in one swoosh. His impressive cut cock sprang straight up from a patch of blond hair that looked just like his kid brother's.
Miles was in a kind of stunned silence, watching intently as I swallowed JT's big pole then pulled my head off momentarily and worked the head with my lips and tongue before plunging back down. I felt the dampness of a trickle of pre-cum as I slowly jacked Miles's hard cock up and down in the same rhythm as I was sucking his buddy's pole. I kept this up for at least three or four minutes, varying speed and technique. JT continuously praised my work.
Miles finally found his voice: "That looks so fucking good, JT. You're not gonna keep it all for yourself are you?"
"This is hands-down the best head I can remember, dude and yes, I am going to keep it all to myself," JT laughed and then we all laughed, causing me to pause a second.
"Sorry, Miles, I like this one," I joked and plunged down to JT's balls, causing JT to emit a "Ho-oh-ly Shit!"
I did like JT's big cock, which must have been about eight inches long and plenty thick without being too big to properly suck. I of course wanted to taste Miles too and see what it was like to suck two cocks at basically the same time. Miles had a beautiful hard-on, almost as big as JT's and not quite as thick. Both cocks were cut and I loved the mushroom heads on each. Resting my jaw a minute, I held one in each hand, admiring the golden loveliness that rose from JT's dark trimmed bush and the big white stalk rising out of Miles's blond patch.
Miles had bigger balls with the same blond peach fuzz that drove me crazy on his little brother, while JT had shaved his coffee-colored balls smooth. I wanted it all in my hungry mouth.
"Miles," I nodded at him. "Why don't you move over onto this coffee table. It looks plenty sturdy. And JT, you sit beside him and give me access to this feast all at once."
They eagerly moved in place in front of me, sitting close beside each other on the low table, their big hard poles both pointing at me. My mouth watered for more. Miles and JT then took off their Tshirts and were finally totally naked. Their bodies were hard and beautiful. Miles had a golden tan above and below the lines of his shorts, but naked, the contrast between their skin was striking. I drank in the comparison between JT's golden brown thighs and ass and the perfect white skin Miles revealed when his shorts came off.
Still teasing Miles, I leaned in and engulfed JT's cock again in one big plunge.
"Oh, fuck, that's good," JT moaned and I increased my pace, going faster and faster while jacking Miles's straining cock is rhythm. Suddenly, I pulled off JT's dick and asked Miles if he thought he could stand a little attention.
"If you don't start soon, I'm gonna make JT suck it," Miles smiled and JT joined him in a good natured laugh.
These guys were so comfortable with each other, even sitting naked with their thighs touching and their hard cocks out, getting worked on just inches apart. I suspected they had done a lot hooking up with girls together. I'd have to find out, after I had some more fun.
Miles was so ready to get his cock sucked that he was trembling a little. I lowered my mouth slowly to his cock and licked it from base to tip, then slowly tongued his big beautiful balls, getting them wet and glowing. I traced my tongue up from his balls, all the way up the underside of his cock, then slowly took his head in my mouth at last, working the head and wetly nibbling the underside with my lips and tongue. Miles threw his head back in ecstasy and inhaled deeply. His dick seemed to grow another half inch in my mouth as I took him down to his balls.
"Oh shit, that's better than it even looked ... Oh fuck that's so good. That's sooo fucking nice."
As I slowly took Miles all the way in and then plunged up and down on his cock, I looked up at JT who smiled at me approvingly and winked. I kept up my assault on Miles's dick while giving JT as good a handjob as I could. JT watched Miles's blowjob just like Miles had done when I was sucking JT. After about 5 minutes of steady sucking, Miles warned me to slow down and I immediately plunged back down on JT's cock.
We went on like this for a while, with me switch sucking them and the guys exchanging superlatives in describing how I was doing. It was a surprising turn on for me when JT and Miles would talk to each other about my sucking; I liked hearing them describe what I was doing, how it felt and how much they were loving it. I also liked them talking as if I wasn't there. It turned me on to be a cocksucker for these two fine looking dudes. My own cock was as hard as the ones I was worshipping with my mouth and tongue.
Miles: "Fuck, JT. Just to think I would have missed out on this if you hadn't made me text this guy."
JT: "Maybe you won't be such a pussy next time you need some head, bud. A man's gotta ask for what he needs."
Miles: "Well I won't be so shy next time -- and I think Will here likes what we brought him to play with, right Will?"
All I could do was nod yes with my mouth stuffed full of cock. I loved sucking their cocks and couldn't get enough. Miles was getting closer and so I worked harder on JT's meat, wanting them to explode all at once. After close to a half hour of hard work, Miles announced he wasn't going to last much more, even with the way I was taking it easier on him.
JT: "So, Will, how do you want this to go down? We are LOVING this and the last thing my buddy and I want to do is run you off. So what do you want to do when we start blowing our loads?
I pulled JT's big wet cock out of my mouth and looked up at both of them:
"I want you to both come in my mouth."
I returned to sucking JT's cock and let the words sink in. Out of the corner of my eye, I saw the guys exchange raised eyebrow looks. I switched over to give Miles a little oral attention and added:
"It would be hot if you got off together, but however it works out, I'll love it. I'm close to busting a nut myself, getting off sucking your big cocks."
JT: "Fuck, man, get out of those clothes. With all the work you're doing, you deserve a big nut too."
I said I didn't want to freak them out and they both laughed at me like I was crazy. Miles pointed out he and JT here were sitting side by side with the biggest boners of their lives, watching each other get sucked by a dude.
"Why in the world would we mind you getting naked at this point, dude? Now that would be the kind of weird selfish shit my brother would do, but not us, right JT."
JT simply said: "Off with the clothes, Will."
I wasted no time, my hard cock joining theirs in the fresh air. I then went back to work on first JT and then Miles, working them back to the edge. When I had a free hand, I would jack myself in unison with sucking one and jerking another of their cocks.
I was surprised but very pleased when JT reached over and took over for me, grabbing my dick while I was working on Miles's pole. Miles's eyes grew wide for a second, watching JT's brown hand slowly jerking my big white cock up and down in rhythm to Miles's blowjob. I was even more surprised when I switched to sucking JT again, and Miles reached over to start playing with my cock, then fondle my balls. "Mmmmmm" was all I could manage with my mouth so full.
"Yeah, you're gonna get me there if you keep that up," JT announced, spurring me to increase the pace a little. "Oh fuck yeah, close baby, getting me close... oh yeah..."
Meanwhile, Miles was moaning he was going to blow soon too and I quickly switched to suck him down to the balls a couple of time, then back to JT. I could feel JT's orgasm rising and saw his balls tighten. From the furious jacking Miles was now almost unconsciously giving my cock, I knew Miles was close too. Both were breathing heavily and moving their hips in faint imitation of fucking.
"I want it," I managed to get out between sucking both those big cocks in and out. That sent Miles over the top and he gently guided my head off of JT's cock and to his dick just before the first spurt of jizz erupted. Miles thrust his hips up once and yelled out "Oh fuuuuuuccckkkk..." as his big cock unloaded four or five times on my tongue and in my mouth. I swallowed what I could then opened again, gently milking the cum out of Miles, opening my mouth between gulps so JT could see it shoot. JT jacked his cock with his eyes locked on Miles's cock still spurting in my mouth.
JT then moved in and aimed at my open mouth, saying in low growl that he was coming too. His first blast joined Miles's cum on my tongue. Both cocks were at my lips and I took down JT's delicious load, milking his delicious dick the same way I had milked Miles's. Then with the willing cooperation of Miles and JT, I took both cockheads in my mouth at the same time, licking them both together while they both continued to leak out the last of drops of jizz. Miles was shaking with pleasure. JT pulled out of my mouth and proudly leaned back, watching his cock stick straight out, pointing at my cum covered lips. I licked both dicks clean, then squeezed one last drop out of the cock of the still shuddering Miles, licking it off the glistening tip.