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19 Year Old Math Tutor Gets Surprised Ch. 02

By: willmasonwillmason



Jason was wearing those long nylon basketball shorts that came almost to his knees. The crotch was tented up, his cock straining to burst through the fabric. Jason sat back on the couch and turned up a cold beer, his legs spread wide. I couldn't take my eyes off that big bulge, despite trying to recover from not just the best blowjob of my life, but the best nut I had ever busted. Still taking deep breaths, I was nonetheless supremely relaxed. I reached over and caressed Jason's upper thigh, edging toward the edge of that bulge. Tentatively, I reached for his hardness and fondled his cock through the thin fabric. It was rock hard.

"Hey, dude," Jason said casually. "It's cool if you just chill. I didn't blow you expecting you to get me off. I love giving head."

"So how am I going to I know whether I like it or not, unless I try it out? You don't have any objection to being on the receiving end do you?"

Jason laughed and looked me in the eye, "Fuck, no. Just didn't want you to feel obligated. But if you're looking to try out something new, maybe I'll get a chance to tutor you for once."

I had enough of rubbing that big thing through cloth and started lowering Jason's shorts from the elastic top. Obligingly, he lifted his butt up off the couch and let me slide his shorts and boxers all the way to his feet. Jason kicked them off. I stared at the big boner, its perfect head topping a moderately thick shaft and its eye staring right at me. Jason was cut and there was a slightly darker ring where the foreskin had been removed just after birth. His balls hung loose. While he had a nice brown bush, it was obviously trimmed a bit at the top. His balls were smooth as a baby's butt. 

I reached in and cupped his balls with my left hand, gently massaging them like I did my own when I jacked off. My right hand grasped his shaft just below the head and I marveled at the feel of another guy's cock in my hand. It was silky smooth while hard as steel at the same time. I gently moved my hand up and down its length while continuing to play with his balls.

"Feels awesome, Jason. Just love on it like you like yours loved on ... oh yeah, like that...exactly like that."

With my gentle up and down stroking, a small clear drop of pre-cum started to emerge from the tip. On the next stroke upward, I squeezed gently under the head, making the drop bubble up. It was now or never and I got up the courage to lean down and lick the big clear drop off the tip of his impressive dick. It tasted slick and a bit salty, but surprisingly tasty. Emboldened, I took the head of his cock gently in my mouth and tasted its strange, spongy texture.

"Oh, yeah... nice, very nice," Jason murmured.

He leaned his head back and closed his eyes as I explored his cock inch by inch. I took another inch down, and then slurped back to the top, taking it all the way out of my mouth before gaining more confidence and plunging back down a little further than I had gone the last time. I kept this up, taking more and more until I had taken what must have been about 5 inches of it down, but hadn't reached the bottom yet. Trying to mimic what Jason had done to me, I figured he gave head like he liked to get it. Just couldn't get as much of his cock down as he could mine without hitting that gag reflex and having to back off. Every time I was at the top, I swirled my tongue around the swollen head, eliciting contented sighs from Jason that let me know I was pleasing him.

"That's really nice, man. Really nice. You're a fast learner. Just keep doing that ... oh, yeah, like that."

Jason was enjoying the head and I was focused on my work. After about 5 or 6 minutes of sucking, it dawned on me that I wasn't just pleasing him but was pleasing myself too. It felt good each time my mouth was filled with his big cock. I loved the texture, the taste, the occasional tangy hints of pre-cum that hit my tongue as I kept up the warm, wet, tongue-swirling in and out action. I found that I could get a little more, then a little more in my mouth until I at last felt his brown pubic hair brush against my nose, then my upper lip. At first, I had to suppress a gag and pulled his cock out quickly, but eventually I was able to bury his cock in my mouth and just hold it there. I felt Jason's head swell against the start of my throat.

"Wow, dude. That feels amazing. You better back off a sec. Let's hit the weed again. I want this to last a little longer."

I slowly took his cock out of my mouth and admired it. Glistening with my saliva and swollen with desire, it was -- I couldn't believe I was thinking this -- beautiful. I didn't want to stop. But Jason was leaning forward, fiddling with a lighter he had left on the table in front of the couch and then lighting his pipe. He took a big hit and offered it to me, but I waved him off. I knew what I wanted in my mouth, and it wasn't that cold glass pipe.

Jason popped another beer and handed it to me. I took a deep drink, and relaxed my jaw. After a few more sips, I figured Jason's urge to come had died down enough for me to put that big beautiful thing back in my mouth. I wanted it so bad my mouth watered. 

He was hard as steel, his cock pointing at the ceiling from his sitting position. Playfully grabbing his dick with one hand, I took another drink from my beer and decided to do a cheesy porn flick trick. Holding a little of the cold liquid in my mouth, I went back down on his dick and Jason opened his eyes wide. I kept going up and down, taking his dick from cool back to warm, then all the way to the balls. 

Jason took another swig off his beer and just closed his eyes in stoner ecstasy. This time, I added some hand action, gently jacking him while I sucked. Seeking a better angle, I moved over to the table and, sitting directly in front of him, engulfed his cock in my mouth. As I sucked, I was jacking him a little with my right hand, while my left alternated between his smooth balls and the taint just below them.

Again taking a cue from porn, I stared him in the eyes, my mouth filled to the max with his cock. Jason just grinned that big shit-eating grin.

I got a nice rhythm going, taking his cock all the way down, then working it with my hand as I eased my mouth off, then plunging down again and repeating the motions. When I felt myself gag a little, I moved my wet mouth and tongue down to those balls, working each one as Jason moaned while my right hand used my saliva to jerk his shaft in a wet, slick and sensuous jack-off motion. When I went back to work on his cock with my mouth, Jason would sigh with obvious pleasure and then gently move his hips to greet my movements. 

Sensing we were moving toward a conclusion, I sped up my sucking while slightly increasing my grip on his shaft in the seconds when it was momentarily out of my mouth, while massaging balls and taint in keeping with Jason's slow squirming. As I increased the pace, his hips rose and fell with my sucking motions. When I lingered near the head and paid special attention to the area just beneath the head on the underside, Jason let out a long "ooooooooohhhhhhh, fuuuuuuuckkkk, that's so gooood."

With my mouth full and my own dick starting to stir, I reached below the taint and edged toward Jason's ass. His squirming confirmed he liked that a lot too. I took a wet finger and ever so gently swirled it around the edges of his hole. Jason was almost thrusting into my mouth now and I kept plunging faster and faster, while working him with my left hand and massaging the opening to his ass with the other. 

"Oh fuck, oh fuck... I'm, I'm, I'm... not ... going ... to be able to ... stop. Oh fuuuuucckkkk..." He pumped my mouth with abandon. I welcomed it hungrily, knowing full well what was about to happen.

With a big thrust upward, Jason squinted his eyes and his engorged cock started to shoot. I felt the first spurt of his white hot cum hit the back of my mouth, like a surge. It felt strangely welcome, like mission accomplished. The second shot bigger than the first. I swallowed fast and kept milking him with my mouth. He shot again and again, his load filling me and fulfilling me all at once. I lessened my grip on his dick with my hand and just sucked, ever so gently as the spurts subsided. I savored the unusual flavor and made sure to clean every drop off his still huge but now slightly sagging dick. I licked him clean, then gently milked up the last drops from the base up to the top, sucking them out of him before finally taking the head out of my mouth and lightly kissing the head. 

Ever Mr. Cool, Jason just laid back, legs splayed and eyes closed in contented calm. His big dick flopped to one side, sitting wet and spent across his upper thigh. All I could think about was doing it again.

"That was fucking amazing, man. You don't need a tutor. But I might need to come back for another session soon."

I had six more weeks of summer in this town and I spent a lot more time with my math student-turned- object-of-desire. I was definitely on a voyage of discovery and was preparing for the next leg of life's adventure.

19 Year Old Math Tutor Gets Surprised Ch. 03



As the summer wore on, I came to understand that sucking a beautiful cock was a need for me, not merely a desire. I practiced on Jason's big tool, counting on his easy-going coaching and frequent expressions of delight to guide me to become a cocksucking pro. 

Sometimes, we talked all the way through a session, expressing every feeling and desire. I secretly taped a couple of these hot encounters. Many mornings, when I woke up with wood, I grabbed the lotion I kept by my alarm clock and jacked off with my eyes closed, listening to our suck sessions through headphones. 

Jason was completely comfortable and open about how much he loved sucking my dick, and about how he liked to get his sucked too. He was equally at ease, however, about not wanting to have any form of anal sex. Laughing, he told me he thought assholes were dirty and just not a turn-on, whether they were a guy's hairy butthole, or a smoking hot girl's pretty pick pucker. He just wasn't into them. As for his own ass, aside from a little stimulation around the outside edges, he wasn't interested in having anything – even a wet tongue – inside his. 

Fair enough; I was one lucky guy just to be Jason's suck buddy in the first place.

As August approached, my big move was only a few weeks away. Having gotten my degree early, I had decided over six months ago to transfer to a party school, take a few easy liberal arts classes and give up my studious ways. I had more than enough money in the bank from tutoring as well as my options trading success, a by-product of an obsessive semester I spent trying to figure out puts, calls, straddles and other strategies I heard about in a class on securities trading. I had the funds. I had the time. I was determined to live a little, to have some real fun. 

Fortunately, my suck buddy relationship with Jason had opened my eyes to exactly what I wanted to do first: to overdose on gorgeous college cock and see where that led. Given how I had binged on other things most of my life – though mostly of an academic nature -- only to be able to put things in perspective after satisfying myself, I figured my obsession with cocksucking just might be a phase. We'll see. There could be many more chapters after that in my quest for complete sexual self-awareness. On to Texas State University, the party school of all party schools!

The day after I got to San Marcos, Texas, I put my plan into action. I definitely wasn't interested in the gay scene. Being honest with myself, I only liked straight guys who had sex with girls. I knew from my experiences with Jason that at least some of them would also like a no-strings, sweet blowjob from a non-threatening guy who really knew what he was doing. 

With no way to tell which of the great looking guys on this campus might fall into that category (and which ones might deck me if they knew what I was thinking), I decided to take out an ad on Craigslist. A lot of horny guys looked at Craigslist late at night, usually just for kicks. So I placed this ad in Casual Encounters, under "Women seek Men" as that's where the straight guys were likely to be:

New transfer to TSU. I'm a guy posting here because I'm str8 and I only like other str8 guys. I just turned 20, am good looking and an athlete. 6'2 and 177. Blond hair with a nice face and body. I like chicks, but occasionally get off sucking a hot guy too. Total safety, complete discretion. Amazing head and nobody will know but you and me. Late night and horned up? Text me at *** 51 ***2, four eleven, then 9 twenty-seven zero. Why not? (Be fit and around my age only please.)

I took a nice torso-only shot, shirtless of course, with my new iPhone and hit "Post" just after midnight. I followed the instructions to make sure my ad appeared. I opened my special Yahoo email that I had set up just for this craigslist experiment and waited to see if I got emails or texts. A half hour later, my ad appeared. Not much happened until after 1 am when I got a few "what's up?" emails and a request for a face pic.

I was a bit disappointed when at 2:30 am, none of the email inquiries had worked out. I went down a few rabbit trails but nobody was even close to what I was looking for. There were definitely some weirdoes out there... then just when I was about to turn my laptop off and crash, a tone let me know I had a new text message.

"Saw your CL ad. Straight guy here. Never done this before just checking it out." 

I texted him back:

Thxs for reply. My name is Will. What can I tell you?

Jeff here. You for real? 20? Really clean?

Yes, ad was 100% honest. Tell me about you

Cool. I'm 19, 6 ft and 155. Not ugly. 

Where are you?

Englebrook Apts across from stadium

Close by. I have a garage apt a 3 minute walk away. Come have a beer?

Wait, dude. Nervous here. Face pic?

I sent him a great shot of me with a big grin on my face. Jason had taken it two weeks ago with my phone when I told him about my plan to find some guys almost as hot as he was when I got to San Marcos. Ever the good-natured friend, Jason took several pics of my in various states of dress and undress. I thought this was a good one to assure Jeff that yes, I was just 20 and that I was attractive.

Nice. You weren't lying. I'm just nervous and wonder what the catch is.

No catch. I just moved here and was horny. I didn't know anybody, so I tried an ad. My first ad ever

OK cool. Here's me

The photo he sent was G rated but he was a great looking guy, tall enough, trim waist, built like he worked out a few times a week but not a gym god. What really caught my attention was his smile and piercing green eyes. I needed to see this guy naked and the sooner the better. My mouth was watering at the idea of seeing what was in his shorts, of giving him toe-curling head.

You look awesome, dude. Come have a cold beer and if you aren't comfortable with anything more than that, I'll make sure it's not awkward.

I gave Jeff my address and he asked if we could talk on the phone first. Sure, I said and the phone rang within seconds. Jeff and I chatted for at least five minutes as I tried to make him comfortable that I was real, not some weirdo and not a serial killer. Jeff had been out to the local pub, the Triple Crown, had a few pitchers with his buddies and was now home alone. He needed to take his dog out, and I figured that it would make him more comfortable to just walk over here with his pup.

"Bring him, " I offered. "I love dogs and have been missing my old lab lately. He'd love the river."

"OK. I guess I'll go for it... See you in 4 or 5 minutes. I'll just knock on your door."

Jeff was here in no time and his mixed breed pup couldn't have been friendlier. The dog instantly picked up on my being a dog lover and wouldn't leave me alone. What a great ice breaker. I handed Jeff a beer and was careful not to get too up close and personal at first. We chatted about TSU and my transfer in. I omitted the fact I already had an engineering degree from Rice, letting him think I had been building my GPA at a Houston community college so I could "get into" TSU. 

Jeff played club soccer, not on the university team, and he had a girlfriend who popped in about every other weekend. When she wasn't around, he had hooked up with a few girls, but he didn't want any entanglements that would rock the boat with his girlfriend. He had a close call a few weeks ago when his girl was in town and they ran into a hook-up from last spring who had been doing too many shots to keep her cool. The hook-up got a little too friendly and Jeff had to talk his way out of a jam, claiming the drunk girl was just someone he had only seen out at bars and parties. 

Jeff pulled out a perfectly rolled joint and asked if I smoked. I produced a big BBQ grill lighter and we shared the joint out on my porch, along with a second cold beer. We sat on the bench my landlord had provided, on a nice little balcony where we enjoyed the night air. Jeff relaxed considerably when the weed started to work its magic.

"Man, I can't believe I'm here – and why I'm here. I really have never done anything with a guy before."

"That's cool; until three months ago, I hadn't either." 

"Really? So what happened? How'd you get into guys?"

I told him an abridged story of my tutoring a friend from one of my classes in math – changing some details to fit easier junior college courses, but keeping all the exciting good parts about how Jason had brought over some beers to celebrate a great exam grade, then casually asked me if I wanted a BJ. Jeff was as amazed at Jason's cool as I had been back in early June when it happened. He wanted me to tell him how it went down, in detail, and I did my best to relate how it unfolded, step by delicious step. 

Jeff and I were both wearing shorts, mine long gym shorts and him preppy-looking khakis. Jeff's pants were starting to tent up in front as I described the amazing blowjob Jason had given me as my introduction to sex with another guy. Then I told him about how I decided on the spot to return the favor, leading me to where we were right now – with me posting an ad saying I wanted to suck str8 college cock, and Jeff texting me his tentative interest.

Jeff's hard-on was straining to get free and I said:

"Looks like my initiation story got your dick's undivided attention."

Blushing, but making no move to cover up, Jeff adjusted his bulging crotch and with his hand still on his dick, said:

"So are we gonna do this?"

That was all I needed. The balcony was dark and it was after 3 am. There was nobody around and no one could see us up on this bench. So I moved over next to Jeff and gently massaged his bulge, feeling for where his cock was and trying to give his balls a little rub through the thick khaki fabric. Jeff sat back and closed his eyes, my signal to free the serpent in his shorts. 

I tugged at the tight zipper and then unbuttoned the top of his shorts. Jeff's flat washboard stomach was a total turn-on and I ran my left hand up under his shirt, feeling his hard body. With the button undone and the zipper down, it was easy to free the straining cock from those shorts. It popped up, hard as steel and perfectly shaped. I lightly stroked it up and down, letting Jeff feel how gentle I would be. He moved his hips ever so slightly, clearly loving the attention. 

Just as Jeff opened his eyes to watch what I was doing, I leaned down and slowly but steadily engulfed his entire cock in my mouth, all the way to the base. He watched in obvious bliss as I slowly worked my way back up his shaft and swirled my tongue under the ample head of his rock-hard cock. Then I slowly plunged down to the base, repeating the action again and again. 

"Oh, fuck. Awesome dude... no chick has ever taken it down to the balls like that before."

I didn't respond, other than to continue my wet warm envelopment of this wonderful piece of teen cock. Unlike Jason's dick, the only other one I had ever sucked, Jeff's didn't immediately start leaking pre-cum, but it tasted fantastic nonetheless. My own dick was so hard it almost hurt, and I reached down to free it down the leg of my shorts. Jeff saw it and was staring at my dick, then his cock disappearing into my mouth. He exhaled and relaxed.

I just kept sucking Jeff's big hard cock, making sure it was wet and well-loved by my mouth and my swirling, licking tongue. Jeff gave me approving sighs and soft moans, his eyes rolling back in his head when I moved down to his balls, working them thoroughly with my mouth and tongue, then languidly taking his whole length back in my mouth. 

After maybe fifteen minutes of giving Jeff the best head I could out on this bench, I suggested we move back inside my garage apartment where there was a big couch. Stoned and blissed out from the head, Jeff slowly got up and walked the four steps to my door, his 7 inch cock pointing straight ahead like a perfectly level diving board. He stumbled over to the couch, telling his pup to "stay" under the table where he had been napping. I quickly grabbed 2 new beers out of the fridge, handed one to Jeff and settled in on the floor between his legs, grasping his big pole with both hands. 

"I'm glad you took the leap and came over," I said, staring into those green eyes. "This big pole is sure fun to suck on."

"Well, as you can tell, I'm not exactly hating it, man."

I went back to work, if anything with even more vigor and determination now that we were behind closed doors. I slurped a bit louder and soon started to taste the familiar, but so far absent, taste of pre-cum flowing from the tip of that beautiful tool.

"Ummm. Pre-cum. I like that," I said.

"I've never been a big pre-cummer and a lot of times when I jack off, none even comes out."

"Well it's flowing now. Very nice," I managed to say between deep sucks.

"What does it taste like?"

I liked where this conversation was going. When I placed the ad, I figured I'd get to suck some cock, if I was lucky. I thought finding someone who wanted to blow me too would be a lot harder, especially with my ad asking for str8 guys who wanted late night head. But asking me what it tasted like was very promising indeed – an indication Jeff was thinking about having a dick in his mouth too. I decided to drive him a little crazier before seeing how serious he was. 

So I just said, " slick, a little sweet, a little salty, and very nice," savoring the taste at the tip of his raging hard cock.

"Interesting," was all Jeff said. 

I definitely liked that reaction and went back to work on getting Jeff off. My jaws were starting to get a bit tired and I started using more hand action on any part of Jeff's cock that wasn't being covered by my mouth, while working his ample but not huge balls with the free hand. 

"Tell me what you like, Jeff. What feels good; what should I do more?"

"It's all soooo good man, I swear. I've never had head like this and I couldn't begin to tell you how to improve on it. Can you improve on perfection?"

I just kept working that cock, loving every mouth-stuffing moment. Then I said, 

"Well, if there's something you want to tell me or want, let it fly man."

As I worked and worked, Jeff seemed to react when my right hand helped my mouth work that cock and my left squeezed and massaged his balls with a degree of firmness that I might have found verging on the uncomfortable myself. What the hell; he liked it and I wanted to get him off. I worked on his balls like he obviously wanted.

"Oh yeah... oh yeah.. like that .... Ummmh. Yeah work those balls, work 'em."

I not only didn't mind his getting verbal, but responded to it with a little more pressure on his balls. I was also making clear I was obeying his commands.

"Oh yeah, harder, harder... oh fuck that feels good... suck that cock too. Yeah, suck that cock."

I worked harder and squeezed more, prompting Jeff to finally start really talking:

"Suck that cock, suck it...oh yeah, grab those balls, squeeze that big load out of me. You want it in your mouth don't you? You want it? Yeah you do... Oh fuck...

I was furiously sucking his cock and massaging and squeezing his balls as he commanded me.

"Suck it, oh fuuuccckkk, yeah. Suck it yeah, you're going to get it, you're going to get that load, suck my cock, suck my cock, OOOOHHH SHIT here it comes, here it comes ...:" then just heavy, heavy breaths.

Jeff's hips were thrusting up and I met every thrust, his cock almost gagging me but I wanted his cum as bad as he wanted to shoot it and I never let up. With a few more mighty thrusts and commands that I "suck that big cock," Jeff put his hands on either side if my head and started to blow his load. 

His orgasm was so intense that his legs were shaking as he emptied his balls into my hungry mouth. Jeff's breathing was loud, heavy and a bit irregular as his cock dribbled out the last of his creamy, but by no means massive, load. It tasted very good and I savored the taste I had been missing since the last time I sucked off Jason a couple of weeks back. I gently licked him clean, getting every drop before slowly withdrawing his wet cock from my finally satisfied mouth. 

"Holy shit, dude, I have never, never, ever come like that before. That was amazing."

"It was every bit as much fun for me, man, very intense and a huge turn-on when you finally got comfortable enough to start telling me what to do. I liked the dirty talk. The other guy I sucked never did that."

"So you really were telling the truth? You only sucked one other guy's cock?" Wow, I guess you really are safe, clean I mean... Shit, you know, I was worried about letting some guy suck my dick... And I'm glad my 'suck my cock' talk wasn't taken as abusive or an insult."

"I loved it because it was real, unlike some of that fake shit you hear girls, and guys, say in pornos. And yes, I'm as clean as I hope you are."

"Completely clean, man. Never had sex of any kind with a guy before and have only been with my girlfriend since a couple of close calls made me lay off the local hook ups a few weeks back."

"Well," Jeff said, now completely with his guard down, "Let's get one more beer and talk about this some more."

We popped two more and hit the joint again. I put some music on and sat back down next to Jeff, my cock still hard down my left leg of my shorts. 

Jeff continued: "I'm having trouble believing I'm saying this, but here goes. I'm clean; you're clean; it's not like this is unsafe or anything.... And I love what just happened and, well, I was wondering if I'd like to try it out. You know, try your side of the fun myself."

"I'd be happy to serve as guinea pig, but there's no way I could last as long as you did... do you always take that long to bust?"

"Hell no, man. I jacked off less than an hour before I texted you. I read your ad and was so horny, debating with myself as to whether to go ahead with answering your ad. I thought jerking off would kill the desire, but it didn't work. Just the opposite. My girlfriend and I always fuck at least twice at night before we go to sleep, then sometimes we do it again in the middle of the night. Then always again in the morning, I guess because we only get together on weekends, a couple of times a month at most. So one nut just made my hornier... and here I am."

"Well that explains the hard labor you put me through. But it was definitely worth it. Now what can I tell you about sucking cock?"

"A lot, I guess. I had never really thought about it until I saw how much you were enjoying it. It occurred to me that I'm an open minded guy and maybe I'd want to at least see what it felt like."

Jeff and I had a lot to talk about. I also had a big hard-on in my pants and Jeff was staring at it now. 

(To be continued)



19 Year Old Math Tutor Gets Surprised Ch. 04



Jeff didn't take too much time in deciding he wanted to see what it felt like to suck a dick, specifically mine. I walked over to him, standing directly in front of where he was sitting, my bulging crotch at eye level. 

Jeff nervously pulled down my gym shorts and boxers. My rock-hard 7 inch cut cock sprang up and now was pointing right at him. Jeff tentatively took it in his hand, staring at it intensely and feeling it all over. Jeff had clearly never before handled a dick other than his own. Slowly, he started to jack it up and down. With his free hand, he reached for my balls and gently felt them too. Still looking right at my cock, Jeff was psyching himself up for taking the plunge.

Like a kid on the high dive who is scared to jump, but determined not to climb back down the ladder in shame, he suddenly moved his head forward and took my dick into his mouth, going about half-way down its shaft in one gulp. Then he started the old in-and-out sucking, sometimes looking up at my face as if looking for approval. Jeff was an eager student. Once he got over the shock that he, a straight dude who had been banging girls since tenth grade, was actually sucking a cock, he started doing a pretty good job.



I coached him and taught him how to suck. I gently urged him to use his tongue to make me feel like he would want to feel, if the roles were reversed -- as they were just a few moments ago. He really got into learning some skills, slurping under the head where I was most sensitive and asking me over and over "like that?" Seeing his big green eyes looking up at me with my dick in his mouth was such a huge turn on.



I was so horned up from my work-out on his big dick that I was ready to blow my own load pretty fast. Showing Jeff how to use his hands to take me over the top, I concentrated on getting off and getting this kid out the door. Jeff wasn't ready to taste cum yet, so when I warned him, he pulled off my cock and pointed it away from his mouth. Jeff looked fascinated as he watched me shoot several times. I blasted a pretty nice load, relieved at last. My cum covered his hand and it felt really good when Jeff used it to keep milking my cock with his hand, watching with wonder as the last drops oozed out the tip. Not bad, but this guy would need some work if he was going to be a regular suck bud.  

Jeff left my apartment just before 4 am, promising to get back in touch after he had time to process all that had gone down in the last hour. I was pretty tired, but was also excited that my craigslist ad had worked so well. I decided to check my email and text messages one last time before crashing.



And there it was: a text from a guy that somehow I couldn't resist answering. It was from only 15 minutes before, and it read:

If you're serious, text me back. Younger than u. Super horned up now.



I sent back a quick text: "serious, but only if you are legal age."

The response came in seconds: "turned 18 last month; high school senior"

Intrigued, I sent another: "home with parents?"

"No. School not started yet. Staying with brother at TSU. He's sleeping at his girlfriend's apt"

I texted him back, suggesting we talk on the phone. He called my number as soon as my text got there. His name was Sim and he didn't want to use last names. He was a high school lacrosse player, not much of a student, and he liked girls, he wanted to make sure I knew. He also liked to come visit his brother any chance he had, to party with some guys he knew from home who had graduated from his high school last year. He had a rush of blunt questions about me: was I a "full-on gay dude," did I have AIDS, what kind of risks was he taking if he let me suck his dick. I calmly reassured him it was safe and that I was just a normal guy who liked to suck on occasion. 

Sim: "I mean, this is some fucked up shit that I'm even talking to you, you know what I mean?"

"Yeah, I felt the same way posting that ad," I responded, patiently reassuring this kid.

Sim sounded more jittery than drunk, but he was definitely interested in getting a blowjob. I explained that I was always a straight guy before about three months ago and still liked girls, but had just expanded my horizons a little. Sim didn't sound very smart, but had more of the dumb jock profile. Yet, despite the blunt questions, he didn't seem like an asshole either. I had to admit to myself that I would have had the same thoughts if I had answered some random craigslist ad before I had even gone off to college. 

Intrigued by the fact he was still in high school and just how very different he was from the other two more thoughtful guys I had been with, I figured this might be an interesting new adventure. I tried to convince him to come over, mentioning I lived by myself and had a few cold beers left. 

Sim: "I can't drive, dude. Too fucked up."

"Well, OK. Where are you?"

Sim: "My brother's apartment, on West Woods Street. "

He was practically next door. Now it was my turn to quiz him a bit. I asked who was there, if the brother might come home and some questions about what Sim looked like. Sim wanted me to come now before he decided this was "too fucked p." It was a 2 or 3 minute walk, across the street and down a couple of blocks. Everything else checked out, so I figured "why the hell not?"

I walked over and knocked quietly on Sim's brother's door. He just cracked the door open, looking me up and down with the chain still on the door. When he saw what I looked like, he went ahead and let me in. Rather than shake hands or otherwise introduce himself, the kid just turned his back and walked inside with a mumbled "What's up?"

I followed him in and marveled at what I saw: This kid was beautiful. Blond curly hair and a young, innocent face that looked like he hadn't even been shaving that long. The word "cherubic" from something I had to read in English class long ago came to mind. Below that man-child face, his body was lean and muscular, the product of running up and down the lacrosse fields and probably lifting some weights too. I immediately thought about the porno sites that advertised "barely legal" and smiled to myself. I was about to stuff some barely legal teen cock in my mouth. 

"You're not a cop or anything are you? Sim asked

"No, I'm a student here at TSU and I'm less than two years older than you."

"Good," was all he said.

Sim walked over to a glass top coffee table and picked up a little plastic bag. Now I knew why he was still up at 4 in the morning and why sounded more jittery than drunk; he had been doing coke. He cut up a small mound of white powder into two short lines with a razor blade and offered me one.

"No, you go for it and I'll just take a beer," I said, helping myself to a green bottle of Heineken from the fridge.

Sim did a short line of powdered courage, then sat down on the couch. Fortified by the blow, he got right to the point:

"Well, you're here to suck my cock, right?" 

"Sure, that's the deal. Where do you want to do it, here or in the bedroom?"

Sim: "Uh, here's cool," as he sat down on the couch past the glass top table.

Now I was the one who wasted no time. I sat right next to him, fondling his cock through the loose fitting sweatpants he was wearing. Sim pulled his shirt off over his head and said:

"Let's go, dude."

His body was Abercrombie & Fitch model perfect, with broad shoulders and a hairless well-defined chest, flat stomach and just a faint blond happy trail below his outie navel. I pulled down the front of his sweats and he lifted his ass up to let me slide them down to his knees. His semi-hard cock and balls sat below a patch of soft curly blond pubes. I gently cupped his balls with my left hand and leaned down to pick up the head of his cock with my mouth, taking care to slowly swirl my tongue around the head of his cock, getting it nice and wet before I took it deeper into my mouth. 

Sim wasn't the least bit shy. He kicked off his sweatpants and put one hand on my head, not roughly, but with the clear signal to take him deeper. 

Sim: "Oh, yeah dude, suck that cock... suck it nice and slow..."

I did exactly that, only better than he had ever imagined, judging from his vocal reactions. 

"Shit, that's good head. That's fucking amazing head. Suck it, Oh yeah; holy fuck that's good."

I went to work on Sim's nice now-fully erect and jutting cock, occasionally taking it all the way out of my mouth and licking one ball, then the other, then gently taking each of them in my mouth before returning to his cock. Sim let me know how I was doing with an almost uninterrupted stream of low-budget-porn-film dialogue. To say he loved it would be an understatement.

I got the sense Sim had had his cock sucked before, by a guy. The way he was acting and talking to me was not how a high school guy, even an arrogant jock stud, would treat a girl. But it was new and surprisingly exciting. I had been reading about "sub" guys and while that wasn't my deal, it was fun to play around with being told what to do and treated like a cocksucking slut. It was all part of the adventure.

Sim was definitely into being "serviced," as the Craigslist ads sometimes say. I was there to suck his cock. He was in charge and he told me how he wanted it. My job was to get him off. He never touched me except to direct my head. I was amused and turned on at the same time. Definitely a new experience.

"Balls," he mumbled gutturally, and I dutifully went down to loll those lovely orbs around in my mouth, all while using my accumulated saliva to slowly but steadily keep jerking him toward busting that nut. His balls were covered in this faint blond peach fuzz that I found to be a real turn-on too. I loved this cocky kid's body, every inch of it. 

"Good. Good... Uhmmm, OK, now suck my dick again. Yeah, that's right. Take it down to the balls. Oh fuck, yeah, swallow that cock, oh fuck..."

Sim's cock looked like it was about 6, or 6 and a half, inches long and a little thicker than my own. It fit perfectly in my mouth. The length was just right for taking all the way down to his balls in a single stroke without any hint of a gag. I took him deep over and over. He kept letting me know how much he liked it. Along with the words of encouragement came a lot of insistent orders. 

"Look up at me." Sim quietly commanded and I obligingly starred him in the eyes, maintaining steady eye contact as I took him down to the base and back six or seven times. He was getting off on the power trip. I just kept sucking that lovely tool.

"Oh yeah... oh yeah, fuck, fuuuckk, uhhhhhhh...." Sim was getting close, breathing really heavily and thrusting his hips to meet every suck.

With no warning, Sim's eyes squinted shut and thrust his cock deeper in my mouth than he had before. A torrent of cum shot out of his cock and deep into my mouth, most of the first volley going straight down my throat. Sim let out a loud and completely unselfconscious "AHHHHhhhhh...yessss...fuuuccckkk." His second shot, larger and stronger, surged out of his cock and sprayed my mouth with a large amount landing on my tongue. I gulped and swallowed for all I was worth, letting him keep shooting into my hungry mouth. His cum tasted the best of the three guys I had swallowed and I eagerly drank it down. As his pulsations subsided, I lapped it up, gently sucking the head of his dick and milking it with my hand to get every drop. Sim loudly moaned his approval.

When I finally removed his cock from my mouth, Sim was panting like a dog that had run and run. He was looking at me with wide eyes and what could only be described as a look of wonder. Finally after a long couple of minutes, he spoke:

"Damn dude, I never got sucked off like that. And I know I never came like that before. That was fucking intense. We gotta fucking do that again." 

That's an 18 year old for you; ready to go again as soon as he regains his breath. His dick was pointing straight up at the ceiling, all wet and red, still as hard as it was when he unloaded in my mouth. I needed to rest a minute, even though the whole blowjob hadn't taken more than 8 or 10 minutes. 

Now I had some questions for the young stud who had definitely used my mouth like he had done this before.

"I had fun too, man, but I get the feeling that's not your first time with a dude sucking you off."

Sim: "Yeah, so how'd you know?"

"Just a hunch. You know what you like and you aren't afraid to say it. I like that. Guys understand what each other want and need, in ways that chicks just can't ever understand."

"Yeah, earlier this summer, my best friend and I kind of stumbled into this situation with a kid who goes to another high school. He was hanging around the city pool changing rooms and we caught him staring at guys getting naked, so we called him out. And he ended up sucking our dicks all summer."

Yeah? How'd that go down?" This was really interesting.

"My buddy Tommy and I had seen him hanging around the pool, but I never thought much about it. Then one day in June, we were the only ones in the changing room after swimming to cool off after our summer jobs mowing yards. This city pool is so fucking chlorinated that it kills your eyes. We were showering, trying to get the chlorine out. That's when this kid came in the changing room, which isn't all that big, and just hung around. He was obviously watching us shower, while acting like he wasn't really looking. Tommy's one of these guys who will say just about anything, to anybody, you know? And so Tommy laughs and yells over to the guy 'Hey, dude, you like staring at our cocks so much, come over here and soap mine up for me."

"So what happened? Did the kid run off?"

Sim: "No, soon as he yelled at him, Tommy came out of the shower, walking fast, all soapy and buck naked, of course. He cornered the guy before he could get away. I couldn't believe what Tommy was doing, but he said:

'OK faggot, go ahead. Touch it. You know you want to.'" 

"Jeez, that must have been uncomfortable, for the peeping Tom at least."

Sim: "Yeah he was freaked. Tommy's a beast, about twice this kid's size. I thought Tommy was just fucking around. But then the faggot actually did it; he reached out and grabbed Tommy's cock, right there in the locker room."

"Whoa! I hope your friend didn't hit him."



Sim: "No, Tommy just jerked the fag's hand off his dick, saying to the kid 'If you want more of that, meet us outside in 5 minutes. Now get outta here.' 

Sim continued: "And that's how we got our own personal cocksucker. I couldn't believe Tommy was planning to take it that far, but I went along to see. The kid was waiting outside the fence around the pool, kind of cowering. But he sure was there like Tommy told him to be. So, we took him back to Tommy's dad's house; his parents are divorced. And after we all had some drinks, Tommy made him – or let him -- suck his cock. 

"Wow, just like that? You'd never had a guy do anythng before?"

"Fuck no. I started getting laid when I was 16 and never did anything homo, ever. But Tommy was leading the charge and I figured I'd see how crazy things got. We did about 4 or 5 tequila shots and then Tommy just took down his shorts and shoved his cock in this faggot's mouth. The kid fucking loved it and starred slurping and sucking for all he was worth. It surprised the hell out of me, but my dick started to chub up and then Tommy said, 'Hey, faggot, you're ignoring my buddy here.'"

"So you let him suck you?" I wanted to hear more.

"Yeah, why the fuck not at that point. I knew Tommy was no queer -- and that blowjob he was getting looked damn good... so when the kid reached for my dick, I let him fish it out and start sucking it too."

"Freak you out?" I asked

"Nah, I was plenty buzzed by then and I wanted to get off. He blew me twice and Tommy three times before we drove him back and dropped him off where he left his bike."

"Sounds like you found a good arrangement. So you did this all summer?

Sim: "Yeah, it was a sweet deal. The rest of the summer, anytime we couldn't get any pussy, we'd get drunk and just text this guy. He'd be over in a matter of minutes to suck our cocks. It's like he was addicted or something. "

"I imagine he was. Sounds like it worked out well for him too."

Sim: "You're the only person who knows about it except me and Tommy, and well, I told my brother because I tell him everything ... I guess it doesn't matter telling you. Hey, speaking of cocksucking, can you blow me again before you go? This coke is making me super horny."

Sim was too cocky for his own good, but looking into that young "barely legal" face, how could I say no? 



[In the next chapter, a number I don't recognize texts me out of the blue...]



19 Year Old Math Tutor Gets Surprised Ch. 05



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.

Miles continued, 

"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. 




19 Year Old Math Tutor Gets Surprised Ch. 05



JT then gently pushed me by the chest, back on the couch. He calmly leaned in and scooped up some jizz that had landed on my chest, using it to lube my already dripping cock.

"Yo, Miles, our boy here just earned a big nut, if not two, so help me out here." JT slowly and sensuously jerked my cock up and down.

Miles, his chest still heaving from his orgasm, tentatively leaned in, joining JT in working my cock and balls. He stared at my dick and followed JT's lead on pleasing me.

"So how you like it, fast or slow?" JT asked.

"Just like you're doing, then I'll tell you when to speed up." 

I was so excited from sucking those amazing cocks and having them erupt in my mouth that I knew I wouldn't last long. As Miles got the hang of jacking me off and JT kneaded my balls like a pro, I told them to slowly speed up -- and that in a minute they'd have to watch out where they were pointing that thing. They laughed and seemed to really get into my handjob. 

It was just too hot having those two gorgeous, naked jocks jacking me off. I told them to be careful or they'd get it in the eye. I was moaning a bit and soon told them "three seconds." JT pointed my cock straight up just as my first volley shot out. It felt so good to shoot that load. JT used the first blasts of cum as lube to keep jacking me through a long and mind blowing orgasm. I shot five or six times then continued to leak a little more as the guys slowed down but their hands kept moving up and down my dripping dick.

JT's and Miles's hands were covered with my jizz, but they didn't act grossed out at all. They just kept slowly jacking me, wanting me to feel good too. Finally, I said "that's enough" and we collapsed backwards and all laughed. Miles grabbed his boxers off the floor and he and JT used them to clean off their hands. Then we just sat there and talked about how hot it all was. 

Miles said "that was a first," explaining that he'd never touched a dick other than his own before, but then he quickly turned to saying how amazing the blowjob was. 

"Sim was so fucking right. That head was a mind bender, completely beyond anything I even knew was possible."

JT was resting contentedly with his eyes closed and Miles continued:

"I realized when I was watching you go down on JT, before you even started on me, that I had never had my dick sucked right before. Those sorority girls who think they know how to suck cock need some tutoring... And then, I never came like that before either... it was just fucking amazing." 

JT was silent but had a supremely satisfied smile on his face. I knew it wouldn't be the last time I saw that smile or tasted his big cock. 

Before I could finish my next beer, Miles was already talking about doing it again...



19 Year Old Math Tutor Gets Surprised Ch. 06



Being the self-analytical type, I decided to stop and take stock of where my sexual exploration had led me. A single Craigslist post had led to four great adventures in just over a week, the best being the cocky high school senior, Sim, who had roughly told me to suck his cock, then his much more considerate older brother, Miles and his delicious mixed-race jock buddy, JT. Unable to decide what had turned me on more, I was pondering what was next on my menu of adventures.

I decided to try a little experiment: to not have sex with anybody and not even jack off for a few days, then use my fantasies and desires to help guide me toward my next adventure. I kept busy with school and errands all the way till the weekend, ignoring even the most insistent morning wood. I was disciplined in keeping my hands off my dick except to take a leak or scratch an itch. 

By the weekend, I was so horned up I didn't think I could stand it any longer. Walking by San Marcos City Park, where shirtless frat boys were showing off their fine bodies throwing the football, I decided it was time to put my little experiment in action. 

To clear my mind of too many mutli-tracks on my internal dialogue, I smoked just a little of some really nice weed and cracked a cold beer. Then, opening my laptop, I selected three different porn sites. I took off my clothes and switched back and forth between them, watching the scenes and seeing what turned me on the most. It was not unlike using a Ouija board to see where it led me, except my hand was on my cock instead of a Ouija planchette.

I picked a video of a supposedly straight frat boy getting serviced by his friend on JustUsBoys.com as my proxy for a one-on-one meeting with another gorgeous, hard-bodied frat boy. I slowly but lightly stroked as I watched the boy on his knees slurping and sucking the big cock in front of him. It was hot and after a while, the boys switched. In this video, they were more or less equals, each working to get the other off.

I picked a slightly raunchier skeezy.com video for my two-on-one fantasy, closely paralleling the scene with Miles and JT, even to the point of the two suckees playing with the sucker's dick, but only with their hands, while he switch sucked the two lucky recipients. 

Finally, I put on an Xtube video of a small group of college jocks watching some kind of game on TV when a good looking but slightly less masculine pizza delivery guy came in with a couple of pizzas. After a crude joke about "I've got a tip for him" and some laughter, the pizza boy stops at the door before leaving and stammers that it was his last delivery and, then even more nervously, if they were serious, he was um, interested.

"Hey, looks like we got a cocksucker for the night," one buzzed but beautiful college guy says to the room. Immediately, he grabs the pizza boy's arm and pulls him toward him. Pizza boy drops to his knees and quickly unzips, then starts eagerly servicing, the guy on the couch, while the other frat jocks start to undress. There was no reciprocation going to happen here, but a clear role delineation that seemed to suit everyone just fine.

All the actors (or amateurs, if you believed the hype) on all the videos were hot and the same age range as what was available to me here at Texas State. I switched between them and tried to decide which scene was the bigger turn on. 

After about 8 or 10 minutes of watching and stroking, it was no contest; I found myself about to shoot a load all over my stomach as I watched the scene with the cock-hungry pizza boy as the four beer-guzzling jocks took turns stuffing their cocks in his mouth. They were treating him just a little rough in a good natured way. 

Just to be sure, I looked one more time at the other two also quite hot scenes, but returned to the pizza boy scene, blowing my four day load just as two of the guys blasted ropes of cum on his face and in his hungry mouth.

After I recovered a bit, I devised my plan. I rejected posting the fantasy on craigslist and having to go through the process of fielding calls and texts before I found – maybe – the right scene. Instead, I decided to text JT and see if he was interested in lining up a little party. I had been thinking a lot about JT's big, hard coffee-colored cock... 

It was still broad daylight when I found JT's number and carefully composed my text:

"JT, it's Will. When you get a sec, call me. Got an idea of a little scene I'd like to set up, if you're game."

An hour or so later, the reply came back: "Yo Will. Just got in from running and saw your text. Give me 10 min to shower and I'll call."

The ten minutes ticked by like slow torture as I imagined the soapy water running down JT's hard body and streaming off his fine, thick dick. Finally the phone rang.

"Willie, what you got in mind, bro?"

"I'll just spit it out, man: I've been fantasizing about getting a small group of guys together, you know three or so, all friendly stuff and no abuse, but with me as the entertainment so to speak."

JT: "Whoa, like, um, sure. That would be hot... I can think of a couple of buds who'd be into that, or fools if they weren't, right? ... Like tonight?"

Me: "No time like the present, but whenever you could get it together, JT. I'll get a case of beers and I have some pretty good smoke here if you want to come to my place."

JT: "Lemme see what I can do. Hang close by and I'll call back in an hour or less."

I hurried to the nearby grocery and loaded up on some beer, just getting back when JT called.

"OK, got your party ready, say 8 o'clock?"

Wow, I thought, this was really going to happen.

"Um, sure. 8 it is." I gave JT directions and quickly got off the phone without asking who or how many. 

I found some bad ass straight porn as I figured that was what the guys would like and put the beers in an Igloo cooler by the couch. I arranged chairs so everybody could face the TV and I could face them, then waited for my latest adventure to unfold. I sat out on the porch and sipped a couple more beers, trying to get loosened up for the first awkward minute or two, before things started to get hot.

About 8:15, I saw JT and three athletic looking buddies round the corner and head to my driveway, laughing and shoving each other along. JT bounded up the stairs and his friends followed. Holy shit. Four of them. But all four were hotter than any of the porn actors I had drooled over earlier. They were in fact gorgeous. My mouth started to water. 

JT, to my surprise, was the only non-white guy. His friends were Cody, a lax teammate his age from outside of Houston, and two younger guys, Tad and Jason, who seemed a little buzzed already. The younger guys were freshmen and were part of the crowd Sim hung out with when he visited his brother. They were perfect hard-bodied specimens. Both had dark hair and nice faces. Jason sported a little stubble while Tad was clean shaven. 

Cody, a well-muscled dude with closely cropped dirty blond hair, knew exactly what was up. It appeared he and JT had brought the younger guys along with just a vague promise of a good time if they kept their minds open. JT introduced the guys, then said we should definitely try out that weed I had mentioned.

We smoked out and drank beers for about 15 minutes, just casually shooting the shit. Then JT grabbed my TV remote and started looking around. He soon found the straight porno all cued up on my blu-ray. JT hit "play" and said "Hey look at Will's jack-off material, guys!"

Through the haze of pot smoke, the guys hooted and commented on the action, then JT said he could sure use some sloppy wet head right about now. Cody was stroking himself through his jeans and talking loud about that sword-swallowing young hottie on the video and what he could do with her. 

Jason and Tad looked stoned and a bit drunk, just staring at the porn with big bulges in their shorts. 

"Yo, Will," JT said, "get over here and show my teammates why you invited us over today." With that, JT confidently unzipped his jeans and pulled out his big, beautifully colored rod.

Mesmerized, I moved over in front of JT, who was sitting on the couch next to Cody. I quickly engulfed that big cock in my mouth, coming up for air and plunging back down to almost the base. With my right hand, I reached over to massage Cody's crotch. JT groaned with approval as I inhaled his dick. Cody quickly pulled his shorts down to his knees, giving me full access to his nice cut 7 inch cock and big furry balls.

Tad and Jason just stared at us, their eyes as big as saucers. Soon both were silently rubbing their dicks through their shorts as they watched me suck and slurp on JT's huge hard-on. I slowly jacked Cody's big white tool to the same rhythm. I guess they weren't going to leave. That's good, I thought. Very good. 

Cody looked over at JT for approval and when JT winked, Cody grinned. Cody took my face in his hands, gently but firmly guiding me off JT's cock and over to his straining boner. Having warmed up on JT's big tool, I took Cody down to the balls on my first plunge, eliciting a "holy shit!" out of Cody. I started giving Cody my best sloppy wet head. 

"You weren't lying, JT, this is some crazy good head."

Cody was soon moaning and starting to leak some sweet, salty pre-cum as I slurped up and down his dick. I loved the feel of it in my mouth and increased my pace until JT guided me back to his delicious dick. I urged them to scoot a little closer together on my couch and started to switch suck these two studs. I gave them four to six sucks each, while using my hands to keep them ready for the next assault of my watering mouth.

Tad said "what the fuck" and unleashed his long hard dick from his shorts. He started stroking it to the rhythm of my sucking, his eyes glued to whichever dick I was sucking at the moment. Jason was watching too, rubbing his cock through his jeans, but hadn't pulled it out yet. I wondered what it looked like.

Cody looked over at the freshmen and said to me,

"Yo, cocksucker, how about taking care of our boys here before they feel left out of the fun?"

I winced, but at the same time felt a rush of excitement at being called "cocksucker." I swiftly moved over in front of Jason and helped him out of his pants while I gently gripped and jacked Tad's long cut cock. As soon as Jason's huge tool was free, I dived down on Tad while stroking Jason's thick meat. Jason's dick was an uncut beauty, almost twice as thick as Tad's but not nearly as long. I wondered about how I would stuff something that wide in my mouth.

I worked up the courage to try and, holding it before me, said to it and the room "That's the fattest cock I've ever seen," then proceeded to stuff it in my mouth. Jason moaned in ecstasy. I came up for air, then slurped wetly under the big head as he wriggled in pleasure. What an awesome cock!

JT and Cody gathered around, sitting on the table in front of Jason and Tad, allowing me to switch suck the freshmen while I jacked Cody and JT with my hands. Everyone was moaning and saying shit like "Oh yeah, suck that fat cock, suck it all, take it!"

I did as I was told as Cody called the plays, while Tad and Jason steadily fed their big cocks into my mouth. I obediently moved back and forth between all four boys, making sure nobody was neglected for too long and making sure everyone got a turn being sucked every minute or two. 

I was deliriously driven to suck and suck and suck. I had so much cock in my mouth, in my hands, all around me -- and I loved every inch of it. At one point, Cody stood up and fucked my face, ramming his dick in and out while I tried to keep pace. All I could say was "uhmmm, uhmmm, uhmmm," with pure lust and total submission.

JT then moved me off the table and laid me down on my back on the couch, with my head on the arm rest. He then stood, positioning himself above me so I could suck him upside down. JT was in standing position, with me leaning my head back to get the right angle for his cock to enter my throat. He started out slow, then picked it up until he was slow-motion face-fucking me with about half to two-thirds of his impressive length. As his balls covered my eyes, his cock slowly went in and out of my mouth, I choked some. But I loved it so much I suppressed the gag reflex as best I could.

JT gave me maybe a half inch at a time, helping me get it deeper and deeper without gagging. As I relaxed my throat, he coaxed me, saying "yeah, that's it; take that cock nice and easy down that throat." I slowly got the hang of it. Soon, JT had his entire length buried in my throat. 

JT gently massaged my exposed throat as he impaled me, showing the other guys how my throat expanded around his dick.

"Shit, look, you can see it! See how far my cock is down his throat." 

It was an amazing turn on to be the object of this talk, to be talked about like I was just a cocksucker there to service them. My own needs, my own comfort, even whether I could breathe or not was not even on their radar. I was here to serve.

As my throat got stretched, I grasped for two more cocks and jacked them off the best I could, trying to make sure everyone was being taken care of while my mouth got fucked. The fourth guy fetched new beers for everyone but me, then he took his place getting jacked off while he watched me get fed a huge cock.

One by one, each guy took turns throat fucking me, until Jason tried to get his massively thick beast down my gullet. Fortunately, he was at least a couple of inches shorter than the other guys. I did my best to take that monster too, but gagged a lot. With my mouth and throat stuffed so full of cock I could hardly think, I heard a chorus of things like "Yeah, take that cock, swallow it. Suck it, yeah like that. Just like that."

I loved the role of cocksucker, servicing these wonderful cocks. My own cock felt like it was going to explode, even though nobody had so much as touched it through my shorts, which were still very much on. 

After everyone had a turn getting deep throated with me lying on my back, they boys pulled me up and turned me back around. They sat me on the table in front of them and let the show go on. After about 10 minutes back in that position, I could tell Tad was getting close. When it was his turn, he thrust wildly, then suddenly pulled out of my mouth and pushed my hand away when I tried to jack him as the next cock in line replaced his in my mouth.

"Somebody better feed me a load," I managed to say between slurps and plunges on Jason's thick monster. My jaws were sore and it was time to bring this to a close. I wanted to feel all four of their beautiful cocks shoot in my mouth.

"Who's close?" JT asked. "Number one rule of the party: you gotta shoot it where we can all see it, like in a porn flick!"

Jason was moaning under my wet assault on his tool when Tad spoke up:

"I'm about to blow, big time. Where you want it, dude?"

Before I could answer, Cody answered for me:

"Shoot it all over his face, Tad-man, and watch that hungry cocksucker go for it." 

Then looking at me, Cody said "You know you want that cum, don't you cocksucker?"

My mouth was full, so all I could say was "Uh Huh," as in an emphatic yes.

With that, Jason pulled out of my mouth and started jacking off close to my face. I pulled Tad's long hard cock back in for some final encouragement. I wanted his cum so bad. I wanted everybody's cum. And I wanted it now.

Tad was pumping my face and moaning like a mad man, his cock pistoning in and out while I tried to keep up. I was holding his balls, slowly massaging them, urging him to shoot. After 30 seconds or so of his thrusting, I felt his balls pull up close to his body as he got ready to unload.

"Oh fuck. Oh Fuck. I'm cumming, I'm cumming, I'm ..."

Just then I felt the first spurt hit the back of my mouth. Yum. Tad quickly pulled out, so the second and much bigger shot surged out of the tip of his engorged cock and landed all over my face. To whoops and cheers, Tad kept shooting that big tool, aiming at my open mouth and eager tongue while he kept milking it from the middle of his long shaft. 

When Tad's spurts started to slow, I took his cock back in my messy mouth, all the way, making Tad's eyes roll back in his head as he continued to drain his balls into my mouth. He thrust his hips against my mouth with his dick all the way in, then just held it there. I sucked him gently till there was no more cum to drink and he collapsed back into the couch with quiet comments about how fucking amazing that nut was.

Jason's huge piece quickly replaced Tad's cock in my mouth as I swallowed the last delicious drops of Tad's juices. I wondered if it turned him on to know his cock was thrusting into some of Tad's hot jizz. It sure turned me on. I knew I would savor this moment many times again in the days to come. 

"Yeah, Jason, feed him that monster dick. Stuff him. Shoot a big load this cocksucker won't soon forget. Feed him that load." 

Cody was once again calling the plays and Jason was in bliss as he worked toward that big nut.

I wanted this one bad and stretched my mouth to give that big cock the best sucking it had ever had. Jason was grunting and moaning that he was about to blow, when without further warning he flooded my mouth with his sweet load. Like Tad, he tried to pull out, but was a little late. I had to swallow two volleys fast. Still, he painted my face with three or four more spurts and rubbed his cock all over my mouth and lips as he dribbled out more of his sweet juices. I wished it had been filmed as it was a hot, hot scene. The other guys definitely approved of how Jason gave them a show. 

I licked off what I could off my lips then Cody instructed Jason to feed me that cum with his fingers. Jason took his index finger and scooped up what I couldn't reach off my chin and under an eye, then offered his gooey finger to my mouth. I eagerly sucked the warm nectar off his finger as the guys looked on approvingly. 

Nobody had looked at the porno in at least 45 minutes.

Then after all the cum had been fed to me off Jason's finger, I pulled his fat cock back into my mouth to clean it, licking the cum off the sides then the drops that oozed out of the tip when I squeezed it from the base up. I had never tongued an uncut cock before and delighted in swirling my tongue around and under the foreskin, looking for any drops I missed.

"Damn," was all Jason said. "Damn."

The whole time Tad and Jason had been feeding me their ample loads, Cody and JT had been slowly stroking their cocks, mesmerized by watching the young guys fill my mouth and shoot their jizz on my face.

"Let's give him a double treat, JT," Cody said, moving in and jacking furiously toward my face. JT moved in too and they both jacked off, just inches from my mouth. I sucked each of them in again, but they wanted to time this for a show. The boys took complete control of when I could suck and when I was to just watch and wait for those loads. I played with their balls and did as I was told while the older guys talked dirty about how much I wanted it, how much I needed it. 

"You want it boy? Tell us if you need it."

"Yes, I live for your cum," I said, saying whatever worked for their fantasy – and mine.

As the trash talk continued, JT said he was getting real close and that seemed to spur Cody on.

Cody: "Open wide, suck-boy. A big reward is coming your way. And you're gonna drink it all." 

I opened and the big milk chocolate colored cock belonging to JT started to erupt all over my mouth. JT's second bigger shot of creamy white cum landed on my tongue, taking Cody over the ledge. 

Cody yelled "Oh fuck yeah!" as his huge white hard-on spurted its first juices on my lips. He shot his thick white load on my lips and in my open mouth. Their aim was almost perfect and their jizz mixed together in my mouth. 




19 Year Old Math Tutor Gets Surprised Ch. 06



They came and came, coaxing me all along with their porno track talk. I heard Tad murmur, "That's so fucking hot" just as I started slurping up the cum off these last two cocks to shoot. 

Jason and Tad had leaned up from the couch to watch the finale and they stared in amazement. Both the younger guys unconsciously started to slowly jack their spent cocks as they watched JT's and Cody's big hard cocks get lovingly cleaned by my hungry tongue and mouth. 

I squeezed up the last almost clear droplets off JT's slowly deflating cock and licked them off. He shuddered and smiled. I then did the same to an appreciative Cody, who found a little of his – or somebody's -- jizz on my cheek next to my left ear and fed it to me with his fingers. 

"Ummm. So fucking good," I softly thanked him.

I was spent like I had never been spent before. When I made it to the shower a minute after they staggered out, I soaped up and jacked off in a matter of seconds, releasing my pent up load. I was gently fingering my ass as I shot, giving me thoughts about what I would do next.



19 Year Old Math Tutor Gets Surprised Ch. 07



After the night with JT and his teammates, I woke up early with a sore jaw and more than my usual morning wood. I must have dreamed about sucking their cocks all night; my need to get off again could not have been more urgent. I decided to watch some porn and was increasingly drawn to blowjob scenes that led to anal action. I had been playing with my ass while jerking off for a few days, but up until this point had not seen myself in the "bottom" role. 

Just a few months ago, I was a "straight" guy who got a surprise blowjob from a fellow student I had been tutoring. Now I was a full-on cocksucker for a group of lacrosse players, albeit one who still liked to look at the sexy girls walking by in their ass-hugging little shorts. I hadn't gotten laid in months, but I definitely liked to get my dick sucked. I decided I was becoming a sexual omnivore – one who had the best of both worlds.

Some of the porn studio anal videos were a turn-off, but the pleasure on the faces of some of the amateur guys as they got fucked -- and the loads of very real cum they shot while getting plowed --intrigued me. Using some lube and a thin white candle, I did some careful probing of my ass. While I got some interesting feelings, I don't think I hit my prostrate. With a candle up my ass and my cock in my well-lubed hand, I decided to see what it felt like to have a cock up there. After shooting all over my chest and stomach, I showered and biked over to the local grocery store.

I went first to the produce section and selected a couple of cucumbers. I settled on one looked like the right size to start training myself, then a slightly thicker cucumber, then one that looked about the size of a normal white boy cock. I also bought a four pack of Fleets enemas, using the self-checkout aisle to avoid embarrassment at my rather obvious purchases. 

After a couple of days of experimenting with lots of lube and stretching my ass to the point that I thought I could take a normal sized cock, I decided it was time to find a candidate to deflower me. I considered my options among the guys I had blown: Miles had the perfect tool, not too long or too fat, but I was very skeptical as to whether he'd be up for it. He was legitimately straight and I only ended up swallowing his beautiful cock because his little brother, Sim, egged him on to call me. 

I was pretty certain JT would be happy to plow me, but I wanted start with a smaller cock, not his thick café-au-lait monster. Cody's cock was also just about the right size, but he was so damn aggressive, calling me "cocksucker" when he had just met me, that I feared he wouldn't take it slow enough. This was supposed to be fun for me too, not an exercise in pain. 

Later that night, after a few beers and some more experimentation with the larger of the two cuckes, I couldn't get my mind off of Miles, his perfect cock, his muscled flat stomach and his cute blond stubble. Of all the guys I had sucked, he had treated me with the most kindness. I recalled he had mentioned reading about the fluidity of sexual preference in other cultures, like in classical Greece and ancient Rome. So maybe he was more open-minded than his straight gay demeanor would at first suggest. Besides, I hadn't seen him in a while.

Around 9 PM, a few more beers later, I decided to reach out with a short text. Miles responded almost as soon as I sent it:

"Just heading out for a party. What's up?"

"Chilling at home, finishing a project. Stop by later?" I wanted to be quick and to the point. 

"Sure, I mean, if I don't get lucky that is. I ditched the girlfriend a week back and have been on the hunt."

"Cool. I won't expect a text, but feel free if it doesn't work out. Will be up late, trying to turn a B paper into an A." 

I hoped the hook was set. If Miles gets laid tonight, more power to him. He needed to ditch that worthless sorority girl who hated giving head. But if he ended up coming home alone and horny, my invitation would be in the back of his mind. The certainty that he can at least get a blowjob tonight, no matter what, may even make him more selective in who he targets at the party. I intended to be ready, in case the evening's developments brought the young blond jock to my door about 2 or 3 am.

About midnight, I decided to trim up, shave my ass and clean out. I kept my pubic hair trimmed, but had never shaved my balls or ass before. In a steamy shower, with ample amounts of moisturizing shaving gel and a hand-held mirror, I shaved my nuts as smooth as a baby's behind, then sat on the floor of the shower for the awkward job of removing hair from my crack. When the job was done (nick-free, happily), I was amazed at how everything felt. It was highly erotic. By 1:30 or so, I was fully prepared for whatever might happen.

The waiting was torture. By about 2:30, I figured Miles had found some hot young girl and was happily pounding her pussy. I was sound asleep when I felt my phone buzz next to me in my bed. 

"Am I too late? Got teased bad. On way home." Miles was doing some reaching out himself!

"No, not too late. Come on by."

I heard him bound up the stairs about 10 minutes later and then knock lightly on the door. I was in my boxers and didn't bother to throw on my jeans before I answered the door.

"Hey, Miles," I greeted him with a handshake and a big smile. Miles surprised me by pulling the handshake into a quick hug. He then plopped down on the couch, kicking off his tennis shoes. He looked a little disheveled and was breathing kind of hard.

"Dude," he exhaled, " I thought I was about to fuck the hottest little piece of ass and I was soooo close." 

Looking at his eyes as I brought him a cold brew, Miles looked like his pupils were dilated. He didn't seem drunk, but he was definitely on something. I would have been surprised if he had done blow because he had been so critical of his little brother for it.

As we sat on my sofa, Miles gave a stream-of-consciousness report on his evening. The party had been at a senior's house off campus, a guy who had played lacrosse until he blew an ACL last year. It was not the usual crowd Miles hung out with, but there were some hot girls there he had never met, so he hung around. The party wasn't very big and he soon learned that everyone was on some kind of hallucinogen, mostly acid, which was definitely not Miles's thing. But before he decided to take off, he met this girl named Renee. She was, as he blurted out, a little hippy chick, cute face, dark hair, a body like a gymnast and a tiny tattoo on one ankle. 

"Dude, things were going so right. Within an hour of meeting her, I swear it wasn't even 11 o'clock, we were sitting outside in the back yard and she had her tongue in my mouth."

Miles went on to breathlessly describe how they made out and talked, then she pulled out this little bag of "molly," that "wasn't blow and you didn't snort it" He reported that she stuck her little finger in the bag and licked it off, then stuck it back in the bag and right in Miles's mouth. He sucked it while staring into her eyes, then they started making out again. He ended up back at her place by 12:30 and spent the next two hours trying to fuck her.

"Dude, her body was perfect, just fucking perfect. It was no problem to get her completely naked. We wallowed around in her bed and it was so fucking hot. I ate her shaved little pussy and she was soooo wet. She was so into it and I got her off big time, but, dude, she wouldn't touch my junk! I took off my jeans but she just avoided my dick, even when it was poking her all over as we rolled around."

"Sounds frustrating," I added sympathetically.

"It sucked! At one point I gently asked her what was up, you know, that I wanted to please her more completely, and then everything sorta changed. She said she didn't give head to guys she just met and didn't fuck unless she was in a relationship. Like she didn't realize she had just had a wild orgasm while I ate her pussy?! I mean what the fuck, you know?"

Miles then described how he kept trying a little longer, but that it was wasted effort. Renee kept doing molly and said she wanted to over to a girlfriend's apartment. This was after 2 and Miles wasn't invited, so he reluctantly got dressed and walked outside to clear his head. He looked down at his phone to check texts and remembered my offer, so here he was.

At that point, I walked into my bedroom and told Miles to come in so I could take care of his frustrations. I didn't want to just blow him on the couch, so I made up something about having a good porno cued up in my room. Miles followed me in, shucking his clothes as he approached my bed. With only the light from the front room as light, I took my boxers off too and got down between his legs as soon as he laid down on my bed. It was the first time I had ever been naked when I blew a guy. 

Miles's cock was only a little chubbed up when he hit the bed. I easily took it all the way in my mouth on first suck, eliciting a low moan of pleasure from its owner. As I worked him up to full mast, Miles put his hands on my shoulders and started slowly rubbing and massaging them in a sensuous way. He had never gotten reciprocal with me at all in the past. He had been polite and always friendly, but never showed me anything like affection before. Now he was rubbing, massaging and kneading me without any inhibition at all as I worked on his wonderful cock. Interesting. 

The molly, basically a powder form of ecstasy, had made Miles very touchy-feely. His hands were massaging me more like a lover, quite the opposite of the "take it, cocksucker" treatment I had gotten when sucking off JT, Cody and the two freshman guys. Miles wriggled his ass around and met some of my sucking moves with gentle thrusts, rubbing the head of his beautiful tool against the insides of my cheeks or the back of my mouth. He watched and smiled euphorically as my cheeks bulged out with the outline of his cock and our eyes met as he and I met in the most sensual, slow face fucking exercise I had ever experienced. I was incredibly turned on.

Miles's hands occasionally reached down my back below the shoulders, massaging me with full warm palms. At times, he would raise his head and shoulders up to watch me sucking his big cock, his face contorting in horny pleasure. We both kept the pace slow and sensuous, enjoying a long slow sucking session with no urgency to finish. 

I experimented with using my hands on his body as well, leaving his cock and ballsac to roam his flat stomach, chest and pecs. Miles seemed to like the attention as I lingered over his nipples as well. My mouth never left his cock, his balls and the tender underside below his scrotum. Miles writhed in ecstasy, pun intended. This went on for an hour or more, with Miles's dick hard as steel the whole time, but with no sign he was building to an orgasm. 

After using as many variations as I could imagine, I moved around to get another angle on sucking his pole, not quite a 69 position but one that gave me a different approach – and gave Miles's hands better access to more of me that my head and shoulders. Without hesitation, Miles started running his hands all the way down my back and to my firm ass. I had always been told I had a cute butt by the girls. Miles wasted no time massaging my checks and grabbing full handfuls when the sucking brought him to a particular point of pleasure. His eyes were half closed in a dreamy state as I devoured his now leaking tool and he kneaded my ass with his dominant left hand, his right hand rubbing my shoulders and occasionally my face and ears as I sucked and sucked and sucked.

After what seemed like an eternity, but a blissful one on my end, Miles gently held my face and spoke.

"Hey Dude, that feels so fucking good, but I'm worried about you. That molly I ate is making it hard for me to bust. I'm afraid you'll get so tired of sucking my dick you'll never want to do it again."

We both laughed and I assured him I would never get tired of his big beautiful cock. We talked a little about ecstasy and how it was making him feel and he really opened up, telling me how warm my skin felt and how he was enjoying not only my sucking but all the body contact we were having. I told him I was loving it too, all of it. All the time we talked, Miles kept touching and caressing me. 

"Don't get me wrong, dude, I'm not looking to kiss you or anything, but the feelings of our hands on each other is really intense, you know."

"I'm not interested in kissing guys either, Miles, so no worries, but I can't see any harm in doing anything that feels good as long as we both think it's fun."

With that, Miles pulled me toward him and hugged me, bro style, like he would a relative he hadn't seen I a while. But it was a warm hug and we just held it there. When we broke the hug, Miles kept talking:

"OK man, I am worried about you working so damn hard to get me off and me not being able to bust. I mean you're making me feel so good, but I started wondering if I needed to get you off too or something."

"Miles, I love how honest we're being with each other and it's great that you are thinking about me too. You're an awesome guy and I hope we'll stay friends with benefits for a long, long time. But the last thing I would want is for you to do something out of a sense of obligation. I love to get my dick sucked, but it's better when the person doing it is really into it. "

"That makes sense, and I don't really want to suck cock, but that doesn't make me feel any better about feeling selfish here."

I decided there would never be a better time to ask for what I wanted.

"Miles, let's look to see if there's a win-win situation here that we're overlooking."

"Yeah, cool, like what are you thinking?" All the while, Miles was still massaging my shoulders, obviously enjoying the warmth of flash against flesh. My cock was harder than ever, rubbing against my sheets while Miles massaged me and talked.

"Promise you won't be freaked out if I ask you something." 

Miles treated that as ridiculous: "Dude, we're here, naked in your bed, you've been sucking my dick. I've been rubbing all over you and enjoying the hell out of it, so why would I be freaked out at anything? Say it, man." 

"OK, here goes: You know I've been exploring my sexuality and trying out things, and I've decided I may be right about in the center of the scale – you know, like enjoying being with girls and with guys. But it's a big mystery to me about these gay dudes who like to get fucked and say it's the most intense orgasm they ever had, so I've been thinking I needed to at least try getting fucked. There, I said it."

"Whoa, man, I never thought about putting it in your ass, but I guess, guess (he stuttered a little) ... I mean an ass is an ass, right? I mean if nobody will ever know, I guess I'd be willing to try it. I'm not going to bust a nut just getting head tonight anyway."

Damn. This was really going to happen. I went back down on Miles's dick and made sure he was as rock hard as ever. He was in a state of pure bliss when I pulled out my Astroglide lube and a condom. 

Miles started exploring my ass, slipping his finger closer and closer to my hole then lightly flicking his fingers over the opening. He slowly inserted a finger, then tried his thumb. As Miles played with my ass, I opened a condom and stretched it onto his hard on, then used a generous amount of lube and jacked him up and down with it. 

I figured he'd rather look at my smooth shaved ass than a cock and balls, so I rolled over into the doggy position and told him to go really slow at first. I was facing the mirror on the dresser opposite my bed, the perfect way to see Miles approach me from behind with that big tool standing almost straight up. Miles got up on his knees and slowly rubbed the head of his cock against my hole. I pushed back gently, letting him know I was ready for him to try to penetrate me. 

Miles took his dick in his left hand, while resting his right one on my right ass cheek. He squeezed and caressed my ass as he slowly guided his rid into my canal. I relaxed as much as I could. I grimaced at the initial pain, glad I had worked out with the cucumber that most closely approximated his thickness. 

The head popped in and Miles just held it there, asking me if I was OK. I said it hurt a little, but I was ready for him to push in more, and he slowly forced another inch up my rear. I kept saying "keep going" until he passed the inner ring and slowly buried his entire bone up my ass. I felt his balls hit just above mine and knew he was in to the hilt. The pain had melted into a strange but wonderful fullness. I soon started to sense more pleasure than pain. Miles just held still, his cock buried all the way in.

"OK, man, start fucking me real slow and let's see how it feels for both of us."

"It feels unbelievably tight to me, and really, really good," Miles was starting to fuck in and out, slowly and deliberately at first, then with more and more of his cock coming out and ramming back in until he was stroking me with the entire length.

"Still OK, dude?"

"Not just OK but soooo fucking good. Please keep going. Pick up the pace and fuck me like you like it. Go for it!"

With that Miles started fucking me harder, varying the pace some and staring down at his cock disappearing in and out of my hole. He grabbed both my hips and really started working me, rearranging the nerve endings inside my virgin ass, hitting places I didn't know existed and had never found with my candle and cucumber. I watched him in the mirror. The lust on his face made me wish I had a way to film this and play it over and over when alone. 

We got into this wonderful fucking rhythm. Miles started sweating, drops from his forehead falling on my lower back and ass. I was in heaven and it was very obvious that Miles was too. 

To say he fucked and fucked and fucked me would be such an understatement that I won't even try to estimate the number of long delicious strokes or even the minutes we stayed in the doggy position. Miles was working now, working for that nut he hadn't been able to get, working to pound my ass like I never imagined, fucking with a passion and a purpose that nobody in a porn flick can imitate with all those people and cameras around.

"I want to turn you over and fuck you face to face," he said, heaving his chest and not slowing down his pounding of my ass.

Not saying a word, I started to pull away to get on my back, when Miles grabbed me and helped flip me over, his cock withdrawing for just a second while he lined it up at my hole once again. As turned on as I was, my dick was only half hard; all my pleasure was centered in my ass and the revelation of how incredibly good it felt to be fucked and fucked well. I rolled my legs up high, giving Miles maximum access to my ass. He pounded it like a pro as we both watched his huge pole go in and out of me. 

"You're so fucking smooth, dude... " Miles whispered as he rammed that cock into me again and again, hitting new places that made me feel like I was about to explode. 

"Oh fuck, man, I'm going to get off getting fucked. Fuck me harder, give it to me... "

My cock had swelled back into a hard on as I watched Miles's chest heave above me. I was mesmerized by his cock pounding in and out. The visuals were amazing and I was getting to the point where I knew I was about to explode. I reached down and started jacking my cock a little, grinding into Miles when he pounded in and out, pressing what must be my prostate. The feeling was unlike anything I had even imagined or felt before. Miles, sweating profusely, red in the face, just kept fucking and fucking, staring at his dick as it pistoned in and out of me.

We were building to a mutual climax as Miles's grunts and thrusts told me his explosion was near. I started moaning almost involuntarily as waves of pleasure swept over me and consumed me. 




19 Year Old Math Tutor Gets Surprised Ch. 07



"I'm coming, oh fuck, I'm coming...." 

I was practically yelling as Miles intensified his ramming with a look of almost demonic determination on his face. As my cock started to erupt in what would be the biggest orgasm of my young life, Miles's eyes grew wide as he watched me spurt. Seeing my hot white jizz literally get fucked out of me sent him over the edge. As he pumped his load into me, his eyes almost went back into his head. Suddenly, I needed to taste that cumload and I yelled at him to pull out and shoot the rest of it in my mouth.

Miles pulled his erupting dick out, ripped off that condom and met my mouth halfway as I dived for the spurting prize. I got there in time and was rewarded with several more volleys of cum. The feeling of my wet willing mouth after all that time sheathed in a Trojan gave Miles new sensations too and prolonged his long delayed orgasm even more. I sucked like a mad man as Miles writhed on his back saying how incredible that felt.

When his cock stopped spewing jizz and I had swallowed everything that he didn't shoot into the condom, we rolled back on our backs, side by side, and just lay there with our chests still heaving. There was no post-orgasm guilt this time. Miles made no move to get up. Instead, we both started laughing, our arms across each other, our hands grasping each other in gentle caresses.

"That... was... fucking ... a - maaa - zing!" Those were Miles's first words.

"Me too buddy. Me too. I'm not ready to try to do it justice with words yet."

After just lying there and touching a few minutes, I got a warm hand towel, cleaned the splattered cum off my chest and where some had landed on Miles's stomach. He just laughed like a kid giggling over how much fun he was having. I got us two ice cold water bottles, remembering the need to hydrate and thinking about the workout we had both had. Miles didn't leave that night, but fell asleep in my bed with a hand on my shoulder.