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.