Amanda Discovers Her New Side Ch. 01

And I obeyed. I skipped all the teasing this time and I dove right in. I got as far down as I did last time, about an inch past his head. To myself, I made a goal to see how much of his dick I could possibly fit in my mouth, so each time I went down, I would try to fit just a tiny bit more in my mouth. As I slowly tried to fit more and more of his massive cock in me, I also stroked the base of it with one hand.

While doing this, I thought of the last time I gave a blowjob. All of the other times it was a lot easier to fit in my mouth. Not only was Jack's dick long, it was also really thick. I didn't think I'd ever fit the whole thing in me. It was so thick that I don't think it was possible for my mouth to open any wider to accommodate more! And that's when I remembered I didn't even give Alex head yet! This was wrong on a lot of levels, and the guilt hit me pretty hard. When I saw Alex again I would have to make it all up to him.

But I was absolutely loving this. I was on my knees pleasuring this guy who I had only met just recently. He was so ripped, his muscles showed everywhere and I loved his hard body. He was kind of an asshole but it didn't matter at this point. All that mattered was finishing off Jack and getting to see him cum.

My lips were now about a third of the way down his cock. I knew I could fit more, but I wanted to take my time, at least a little. Jack was definitely enjoying it, I looked up at him occasionally to see him watching me; he still had his hand on my head and fingers through my hair, gently guiding me. I slid my other hand into my panties again. My pussy was soaked in my own wetness, even more so than before. Once again I involuntarily moaned out loud, my mouth vibrating on his dick.

"Shit, girl," Jack said, as he thrust his hips against my face a few times, "keep that up." I could tell he wasn't too close to cumming, but he was definitely getting there. And that's when I decided the gloves were coming off and it was time to go all in.

Just for a moment I stopped sucking him and brought my other hand back up. I noticed it was wet from my cunt and did something I never had before, at least with someone else watching me; I put those fingers in my mouth and licked them dry (mostly), keeping eye contact with Jack the whole time. I wasn't sure why I had the urge to do something like that, but it felt great in the moment.

Upon seeing this, Jack moaned again. "I bet you can't wait to cum all over me," I said through a smile, still stroking the base of his cock. And then I spit right on the head of his throbbing shaft. My hand stroked the full length of his cock now, getting it completely lubed up. My other hand joined it after I made a few full strokes.

"Your cock is so big, I can't wait to taste your cum." I really felt like such a slut now. Jack's little slut, here to please him and make him feel good. He pushed gently on my head again, urging me forward to accept his dick into my mouth. I went down, this time easier since his cock was absolutely soaked. I used one hand to play with his balls again and the other I gripped his thigh with.

I wanted to see exactly how much I could handle before I had to stop. My lips slid down his shaft, almost hitting halfway and stopped for a couple of seconds. I moved my head a little and could feel his tip poking around in my throat. I licked the underside of his shaft with my tongue. After a few seconds, it was uncomfortable so I went back up.

But my lips never left his thick cock. I went back down for more, pausing again as far as I could go down and using my tongue to please him more. I did that, again and again, until I fit half of his massive dick in my mouth. Jack was really enjoying this, his hand never left the back of my head, always guiding me up and down his hard dick. I was pleased with being able to fit all that in my mouth, but I made a mental note that I'd want to fit even more next time (which hopefully there wasn't a "next time!").

I brought my hands back up to his cock now. I decided it was time to finish him off. My hands joined my mouth in pleasuring Jack, placed one after the other so that they made up for what my mouth couldn't reach. This made it so that every time I went down, one of my hands easily reached the bottom. My hands and mouth were covered in my own spit, some of it was actually Jack's precum, but I didn't care at this point. In fact it made me feel sexier and even more like a slut.

Up and down I went on his cock, working as hard as I could. I heard Jack start to grunt and moan louder, unable to contain his lust. I increased my pace just a little bit more, confident in the fact that he was ready to cum.

"Oh fuck baby, I'm gonna cum," he said. I went up and down a few more times, then I went as far down as I could and tried to fit as much of his dick in my mouth as I did before. I got about halfway again, still stroking him with one hand. I lightly grabbed ahold of his balls with my other hand when I felt him finally blow his load into my mouth.

He shot one burst into my mouth, it tasted salty and felt gooey but I loved it, I savored it. Another jet went into my mouth, but this time it was too much for me not to gag so I went up for air. Feeling like a complete slut at this point, I still needed to finish the job. I kept stroking him with one hand, pointing him directly at my wide open mouth, tongue sticking out. It seemed to come out in pearly white ropes, the first one hitting me all over my cheek, the second one on my tongue and chin, the next one on my other cheek.

For the first time in my life, my face was completely covered in somebody's cum. I had never let anyone do this to me before. I felt like such a slut. It was like a brief glance into another side of myself that needed to be explored.

Jack's face was one of pure bliss and ecstasy, and I felt some of that myself too. He was slowly thrusting himself in my hand, and I noticed there was still some cum dribbling out of his tip. I took my cue and put him back into my mouth. I went up and down his cock yet again, slowly and deliberately. My other hand still stroking him, milking him for every last drop. I needed to suck him dry.

We made eye contact again, his hand once again guiding my head up and down. We had this silent exchange where his face seemed to say "You belong down there, don't stop until you're done," and mine seemed to say "Yes I do, thank you for letting me please you." He let go of me and that's when I knew I could come up for air again. I still had his cum on my face and some on my hands, so I made a little show of greedily licking it up and swallowing it all, all the while staring at Jack directly in his eyes.

He was still pretty hard, after all that. I was sure that we could've kept going if we wanted to. But I had the self discipline to stop and not go any further. I could chalk that up as a small victory. I had the power to resist Jack, if I wanted to.

We didn't say anything else before we drifted off to sleep. Not that anything really needed to be said. It felt good to fall asleep in his strong arms, protected by him. But boy did I just make a mess of things. Alex would certainly not be happy with me. It was time to make it up to him and do some damage control. Starting tomorrow morning, I'd be a better girlfriend for him.

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The next morning I woke up around 8am. It was light out now. Surprisingly, I wasn't hungover. My mind was a little hazy from the night before, but I think I recalled everything that happened between me and Jack.

I was definitely a shitty girlfriend last night. What my boyfriend, Alex, thought was a private moment between us was actually shared with Jack. Alex didn't know but Jack watched me as Alex and I played with ourselves for each other to watch. Alex left the video chat before I was able to cum, and I had actually begged Jack to fuck me so I could. He didn't; he actually ate me out instead, but gave me a mind blowing orgasm.

And then, as if I couldn't get enough, I woke up in the middle of the night and gave him a blowjob! I gave him the best blowjob I had ever given anyone and probably enjoyed it as much as Jack did. Not only did he cum in my mouth, which I never let anyone do, but I hungrily licked up all of the leftovers. It felt so good to do all of that. I felt so sexy and slutty, it was something I never experienced before.

But it didn't matter how good I felt at the time because now I felt like the worst girlfriend ever. My sweet boyfriend would go nuts when he found out what I did and with who; I mean it was obvious how much he disliked Jack. I had to stop this before my relationship with Alex was unsalvageable. I had to let Jack know that this was over and we couldn't see each other anymore. It would hurt to do that, but I think I learned a lot about myself during this time. I felt like Alex and I would be able to recover and I could be a great girlfriend for him now. We still hadn't had sex yet, but that was going to change the first night I saw him next. I was going to blow his mind (among other things!).

In bed, Jack had an arm around me. I was able to get out of bed without waking him and slip into a new pair of underwear and bra, and put on a robe. I wanted to get refreshed a little before I talked to Jack, so I headed to the bathroom to wash my face and clear my head.

About 10 minutes later I got back to my room and by this time Jack was up. He was wearing that same pair of gray boxer briefs that he had on last night, and was sitting up on my bed with his back against the wall while going through his phone.

On my way over to him, I couldn't help but marvel at his body yet again. It was literally perfect, and of course I make out his package clearly through his underwear. He looked into my eyes as I made my way over. His look told me he knew what I was about to say.

I sat down on the bed and said "Hey, we really can't do that again. In fact I don't think I can see you anymore. I love my boyfriend and I want to be good for him."

"Its OK, I understand," Jack replied. "It really is too bad though. I had a really great night and it was fun being with you."

"I had a great time too but I have a boyfriend so I can't do things like that again. I'm trying to be a better person. I'm glad that you understand." It was a little awkward and tense after I said that, so to break the silence I tried to make some small talk.

"So you got any plans for today? Hardly anyone is on campus because of the holiday tomorrow," I asked as I turned my body more towards him to get more comfortable.

"Nah not really. I'll probably head to the gym soon and just chill later. Not many people are around so I'll take advantage of that and do my own thing," Jack said.

"Yeah I know what you mean. Alex and my roommate won't be back until tomorrow." Being so close to him on the bed I could feel his body heat. It made me a little tingly and I couldn't help but to keep stealing glances of his naked torso and arms.

He noticed me staring at him but before he could say anything about it I playfully threw my legs over his lap. This was my way of admitting he caught me looking but not getting called out for it.

"Ya know, you really have a fantastic body, It's almost like you go to the gym or something," I complimented him as I quickly ran my fingers across his abs. I wasn't sure why I was doing this but I just didn't want it to be awkward between us as I just let him down.

He chuckled and said "Yeah I guess you could say something like that." His stare was penetrating my eyes and I could feel his breath on me. I got that same tingly feeling again and went against my better judgement and kept up the compliments.

"I've never had the pleasure of being so close to a body like yours, let alone being able to touch it," I said as I traced circles on his muscular chest. "Your pecs are amazing."

I leaned in a little closer and softly said "You know, it really is too bad we can't see each other anymore. I was looking forward to having that big thing inside me, I don't think I'll ever have the opportunity again." I knew I shouldn't have said that but I was just saying what was on my mind.

"Yeah, unfortunately we won't get to experience that. But we'll have to get through it."

Before I could stop myself I started to kiss Jack's chest, making my way up to his neck. I was just enjoying his body one last time. I planted a few more sensuous kisses on his neck and looked up at him, our faces just inches from each other.

"Still, I don't think a goodbye kiss would hurt anything, do you?" And before he could respond I moved my lips to his and kissed him.

It was now that I realized we hadn't even kissed yet. Of course we had done just about everything else to each other, besides going all the way, but we didn't even kiss. So that's probably why I didn't see this as a big deal. We weren't going any further than before, so it didn't change anything. In the future, when I would come clean to Alex, this one kiss wouldn't make a difference at all.

It was immediately electrifying. A few pecks on the lips quickly turned into longer, more passionate kisses. I slipped my tongue into his mouth and it was met with no resistance. Our tongues danced as we explored each other's mouths. I put my hand on the side of Jack's face and pulled him even closer, if that were possible. Jack then pulled me up onto his lap, with one hand on my lower back and the other on my thigh. I could feel his hardness beneath me and shifted my butt just a little to tease him.

The lust and passion built at such a fast rate. At this point it registered in my brain that even though we had gotten to third base with each other, Jack never even got a chance to fully appreciate my body. To this point he hadn't touched my tits or my ass at all. It didn't seem fair that we had to end things without me giving him the pleasure of that. I had teased him so much on my webcam call with Alex. As long as I controlled the situation, I could give him these things without doing anything more serious. With me being on top anyways, this could easily work in my favor.

So I broke our kiss. Jack looked confused but didn't try to resume it. I got up and straddled him, with each of my knees on the outside of his legs. I slipped off my robe and threw it across the room. I was in just my panties and bra now, not that it was anything he hadn't seen before. I winked at him and smiled before resuming our kiss.

Jack put his hands on my hips as we explored each other's mouths once again. He then moved both of them to my ass and squeezed it roughly. It felt so good and I moaned into his mouth a little bit. He then gave my butt a little spank which caused me to yelp a little, it didn't hurt or anything but it was surprising. None of my other partners did anything like this but I could see myself liking it with the right person.

After a few more moments of Jack enjoying my butt, I decided to give him another piece of me. I grabbed one of his hands and placed it on my tits over my bra. He groped at my chest as he kissed me. It felt good but I wanted that skin to skin contact. I stopped our kiss so I could unhook my bra which also went flying across the room.

"Isn't that better?" I asked as Jack brought a hand up and felt up my chest, lightly tracing around it and squeezing.

"Yeah a lot better," he said.

"I know they're not much but I hope you like them." I still wasn't comfortable with the size of my breasts. I always saw girls with huge tits around campus and I couldn't help but to get jealous.

Jack wasn't having any of that and said "No, they're wonderful." He squeezed one hard, brought his face up to the nipple, and gave it a deep kiss followed by lightly sucking on it.

"Oooohh fuck," I moaned. Now he was squeezing both of them with his hands and he brought his lips to the other one. In response I grinded my crotch against his. I could feel he was as hard as ever now, the only barrier between my pussy and his cock was our underwear.

I rode him dry like that, with my boobs buried in his face as I grabbed his shoulders hard for support. I could feel my clit being stimulated as I threw my head back, staring straight up at the ceiling. "Uuunnhh," I moaned again. I felt like I needed him inside me, I needed him to fuck me. This was quickly becoming too much for me to handle. But I'm sure Jack loved the sight of me, grinding against him and enjoying the pleasure it created.

Abruptly I got off of him before we went any further. So much lust had built up in those few moments, I was glad I got off when I did in case I did something regrettable. Jack looked disappointed but didn't try to push me any further.

I did feel bad for teasing him so much. And even though I wasn't on him anymore, I was still just as horny as ever. But I was proud of myself for not going all the way. I was in the mood for a little reward.

"I'm sorry we can't go any further, but I can send you off with a little something. Maybe you can finish off later," I told him with a wink. He looked somewhat relieved by that. I couldn't just let him go like that. Maybe it was a little selfish, but I wanted to feel that huge dick in my mouth one last time, maybe get a little practice in.

So I peeled off his underwear, with Jack lifting his butt to help, and tossed them aside. He was completely nude now. Up close to his massive cock again, I admired how long and thick it was. It literally stuck straight up in the air, its veins were bulging and I could see it pulsing. It was so hot I'm not sure how I didn't just jump on it right then and there.

I waited no longer and leaned down to spit right on the head, wasting no time in getting it wet. I put the head in my mouth and sucked a little. I was impatient this time, and instead of teasing him, my mouth went up and down his cock. After a couple times I wrapped one of my hands around it, right at the end of my mouth, and spread the wetness further down his cock.

Again I tried to see how much I could get in. I got about halfway when I could feel the tip hit the back of my throat. Maybe I was imagining it but I think it fit just a little bit more in my mouth this time. While all the way down, I pressed my lips to his thick shaft and licked down as far as I could. I did this a few more times, going down as far as I could, sucking, and licking.

I could hear Jack grunting in pleasure. I quickened my pace now, going up and down his shaft faster than before. He pulled my hair out of the way and put that hand on the back of my head, pushing me down and thrusting his hips up in sync with my movements.

It was then that I realized I could probably get away with just a little bit more. This opportunity was once in a lifetime, I mean when would I encounter someone, and something, this big again? I just wanted to feel it inside me and fill me up, just for a second. I wouldn't even have to put much of it in me to feel it stretch me out! If I could just do that, I wouldn't really call it fucking. It would only be a few seconds. Afterwards, I could finish off Jack with my hands and let him cum on me and I'm sure he'd love that.

So again I abruptly stopped what I was doing and got up. Jack looked disappointed but that changed when he saw what I was doing.

I straddled him, with my knees on the outsides of his legs. He held onto my hips as I knelt down and his dick made contact with my panties. I leaned in closer so I could whisper to him "I just need to feel it inside me. Its so fucking big, I just want to feel it stretch me out for a few seconds."

With one hand I slid my panties to the side and with the other I grabbed his cock and lined it up to my entrance. He held onto one of my hips and held the base of his dick with his other hand. Needless to say at this point I was completely soaked. I rubbed his thick cock up my lips a few times, reaching up to my clit. It felt so good but I needed it in me. I was glad that I was still wearing my panties because I could just hop off and cover up after a little bit. It gave me an extra layer of security to be able to not let things get out of hand.