Amanda Discovers Her New Side Ch. 01

I watched him as he jerked off. He used one hand to do so and I could see every muscle on his ripped body come to life. His balls bounced up and down with every stroke as we watched each other.

My attention turned back to Alex when I heard loud breathing coming from the laptop. He was really close now as evident by his pace, his hands almost a blur. "Baby, I can't wait for you to fuck me," I told Alex but my eyes were locked with Jack's. "I'm so desperate, I can't wait for your big cock to fill me up!" Shit! I slipped, but Alex must not have noticed because he didn't skip a beat. Alex was by no means big, he was average at best.

But my attention switched back to Jack. I slipped a finger into my wet folds as I penetrated myself, and rubbed my clit with the other hand. I sped up my pace quickly and there were now audible *squish* sounds as I finger-fucked myself. I imagined Jack taking me right here, stuffing his cock inside me and using my body for his pleasure. If he made any effort to do so, I don't think I would've had the willpower to resist him.

I roughly pinched one of my nipples as similar images went through my head. I thought about what it would feel like to have such a big muscled guy like Jack on top of me, fucking me, making me take his big cock. I was getting close to an orgasm now. My hips bucked up and down as I ground my wet pussy against my hand, trying to increase the pressure as much as I could.

But that all came to a close as Alex reached his climax. "Oh fuck, Ohhhhhh," Alex said as he moaned and grunted. I watched and slowed my pace as I watched him cum. It came out in slow dribbles and it got on his hands. I didn't stop touching myself and instead I left my fingers inside me, probing my insides. He grabbed some tissues and cleaned himself up. I felt guilty because Alex had just watched me masturbate while I thought about someone else when he thought I was fantasizing about him. What's worse is that someone else was naked in the room with me!

But Alex didn't sense anything was amiss. "Wow that was great Amanda," Alex said. "I can't wait to see you again. Love you, goodnight." And just like that Alex was gone. This angered me little since I didn't get to orgasm yet. I guess since he was done we were both finished? I couldn't blame him too much though I guess. Whenever we did things like that in person I never had an orgasm. So I guess it would be odd to expect him to let me finish.

But I was so horny! I was pretty close to finishing, I couldn't believe we just stopped like that. And that's when Jack got up and made his way over to me.

But I didn't stop playing with myself. One hand still pinched my nipple while the other rubbed my clit. Jack had that smirk on his face again as he walked over. His dick still looked rock hard. I felt my will giving in as he made his way over, his cock swinging back and forth. I'm sure he was loving this though. Here was some tipsy college freshman playing with herself, naked and spread eagle on her bed, while the ripped jock came over to take what was his.

Oh and I'm sure he could've taken me if he wanted to. In the state I was in, I don't think I could've refused. I know I should've felt horrible as I entertained thoughts of cheating on Alex, but the lust was overtaking me. I was so close to cumming just a few moments ago, and I wasn't far off now either. It wouldn't take much for him to just come over here and stick his dick in me. I was biting my lower lip in anticipation as he came over, a pleading and begging look on my face.

When he stopped, he was just inches away from me. This was the closest I had been to him while he was naked. Both of us naked for that matter! And wow, I knew his cock was huge, but it was something else seeing it up close like this. As he lazily stroked himself, I saw his beautiful cock in all its glory. I could see the veins bulging from it, his pubic hair was nice and trimmed, his loose hanging balls, and the big mushroom tip at the end of it all. I couldn't even contemplate trying to fit that thing in me, but in that moment all I wanted was to be filled up by him.

I was about to reach out and grab it, but before I did so Jack said "Wow, I can't believe he left you high and dry like that. You've gotta be pissed."

I tried to hide my disappointment, "Yeah it's not a big deal though. I had some fun." I didn't stop playing with myself as I said this.

"Still though, you didn't even get to cum. Whenever I'm with a girl, she always leaves satisfied," he said with a grin.

I moved myself so I was now lying down opposite the length of the bed, positioned directly in front of Jack, still spread eagle and playing with my wet pussy. "Well why don't you finish the job then? I'm really close. Just stick that thing in me, I can tell that you want it." I almost couldn't believe the words coming out of my mouth. A few weeks ago I never would've imagined myself saying something like this, especially to someone I wasn't dating! It must've been a mix of the alcohol and the desperate state I was in.

But Jack declined. "No. I don't think you're ready for this anyways." He started to turn away but I quickly sat up and grabbed his package with both of my hands, one hand holding his thick shaft and the other gently holding his balls. He was as rock hard as he looked. I couldn't even get my hand to close around his shaft all the way, that's how thick he was. There was precum dripping down his cock, I had never wanted to suck a dick more in my life.

"Please?" I asked with a puppy dog look on my face, "I'm so close, it really won't take long at all." I stroked his massive shaft and rubbed his balls as I begged him to finish me. I gently pulled him closer to the opening in between my legs, but just as I felt his dick touch my lips he pulled away again.

He didn't say anything as he went down on both knees. I was about to protest but I was cut off by his mouth making contact with my pussy. "Ohhhhhh fuck!" I moaned as he went down on me.

I had never been eaten out before, so this was all new to me. Jack started slow by kissing up and down my wet opening. He then reached both hands around my legs and gripped my thighs firmly as his kisses were replaced with just his tongue. I cried out in surprise and pleasure and he seemed to savor my taste as he took his time with me, his tongue tracing my folds.

I grinded my hips against him in response, too impatient to be content with his teasing. He knew how close I was before, so it wasn't long before he finally made his way to my clit. When he did, the pleasure I felt was more intense than I'd ever felt before. This time, I couldn't control it as my hips bucked up and down involuntarily against Jack's mouth. "Oohhh," I cried out as I glanced down to see Jack looking into my eyes as he ate me out, no doubt loving what he was doing to me. His grip on my legs tightened. I was so close. I reached down to grab the back of Jack's head and grinded my pussy against his face again, increasing the pressure.

A second later Jack let go of one of my legs and shifted. I was confused at first, but soon found out why as he inserted one of his fingers inside me. That's when I started having second thoughts about this; this was on a different level in my mind since he was actually penetrating me. Sure, letting him eat me out was cheating on my boyfriend. But at least I could've said I didn't let him inside me. But I was so close to finishing now that as quickly as those thoughts entered my mind I pushed them out.

It didn't take much after he first penetrated my soaking wet pussy. Slow at first, after a few moments he increased both his pace and the depth of his thrusts. He absolutely devoured my clit in his mouth as he finger fucked me. I felt the pressure explode as an orgasm rocked my body. I let go of Jack's head and grabbed my bedsheets like I was holding onto my life. I swear I went in and out of consciousness for the duration of it. I'm sure if I screamed out in pleasure, but in those moments I wasn't aware of much.

As I came to, I saw Jack putting on his underwear, awkwardly tucking away his big cock which was still hard. "Wait," I begged, "aren't you going to fuck me?"

"No, I don't think so. You're not ready for this anyways." I was very disappointed by this, but at the same time I was extremely satisfied. That was the last thing I remembered as I drifted off to sleep.

_____________

When I woke up, it was still dark outside. A quick glance at my alarm clock told me it was only 3 in the morning. I drank more than I intended, but I didn't feel sick. In fact, I was still pretty drunk.

I felt Jack shift behind me. From his breathing it sounded like he was still asleep. We were both on our sides, with him spooning me. Some time in between the time I fell asleep and now I had gained clothes. I wore a loose shirt and pajamas. Jack must've put them on me before he fell asleep. I felt safe encompassed by his body; his strong arms around me, his hands holding me. I could also feel something hard poking me near my butt. I wriggled my butt against him for fun, he was still asleep but I could've sworn I felt his shaft get even harder.

But that's when I realized what I was doing. I couldn't believe I had cheated on Alex! Just a few hours ago, I was completely naked in front of Jack, letting him eat me out. Not only letting him, I had actually begged him to fuck me, but I had to settle for what I got.

At the very least, I could still say that we didn't have full blown sex. Yes, we engaged in some sexual activities, but we didn't go all the way. I still had that much control over the situation. And if someone asked, I could still say that when I realized I had gone too far, we had stopped. I made a deal with myself that I would make it up to Alex when I saw him again. He would be in for the night of his life.

With that being decided, I wanted to go back to sleep. It seemed inconsiderate to wake up Jack and make him leave, so I let him stay in my bed. I slipped out of the bed so I could turn off the lights. I turned on the nightlight though, I didn't like to be in complete darkness.

I turned back to the bed and was almost caught off guard by the sight on my bed. Jack was still sleeping, but seeing him there stirred my urges once again. Even though it was dark, I could still see all of Jack and his ripped body, and the rise and fall of his muscular chest and abs as he breathed. The only piece of clothing he had on was a tight pair of gray boxer briefs. These clung tightly to his body, and his dick was easily visible through them as I could trace the outline of it with my fingers if I wanted to.

As I got closer to the bed, I could also make out a small wet spot on Jack's underwear right at the tip of his cock. Poor Jack! He must be having some type of wet dream. He had to endure watching me masturbate in front of him, while afterwards eating me out, and in return he didn't get anything! I kinda felt bad for him, but I had to remind myself that I was going to be faithful to Alex from now on.

But curiosity got the better of me. As I crawled back into bed, I just couldn't take my eyes off of him. Honestly his body was perfect. He was so well defined but he also wasn't one of those huge muscle-heads you see at the gyms sometimes; the ones who are so bulky it almost looks like they have a tough time moving around. His dick was still hidden in his underwear, but I could easily make out the shape and outline of it. I wondered if it was hard or not. Honestly it was hard to tell since it was so big and thick. It trailed pretty far down his leg and was almost poking out of the bottom of his underwear!

Before I reached for it, I made sure Jack was still asleep. It seemed like he was since he hadn't moved and his breathing hadn't changed since I woke up. When I made contact I teased it at first. I traced the outline of it with two fingers. After about a minute of that I started to slowly stroke it, with the underwear in between us.

I couldn't tell if I imagined it but it looked like the wet spot on his underwear was getting bigger. I was a little nervous now honestly. Since he kinda turned me down before, I wasn't sure how he'd react to this. But it was just some harmless teasing. He couldn't get too mad at me for that.

I was getting really turned on at this point. I started to think that I probably wouldn't have this chance again with Jack. This could be the last time we see each other, depending on how my next meeting with Alex goes. I had to see it one last time, just to see what I was missing. I mean, who knows when would be the chance I could see a huge cock like this again.

So without wasting any more time, I lifted up the waistband of his underwear and reached in to grab his cock. I took it out of his underwear but kept them on, it wasn't hard to do since it was so big. I still kept a hold of his waistband though so it wouldn't restrict anything.

I'd seen his cock up close before, but this was the closest I had gotten to it so far. Again I noticed his pubic hair was neatly trimmed. I held it by its base and could tell that he wasn't completely hard. Glistening at the tip of his dick was a small amount of precum. From its base I stroked him, slowly, a few times. After a few moments I could feel him swelling in my hand and a bit more precum oozed out of his mushroom-shaped tip. I noticed I was biting my lower lip pretty hard as the sight of all of this was really turning me on. I couldn't check with my hands to make sure but I knew my pussy was starting to get wet.

Stroking Jack's cock and seeing it ooze precum, in response to me, made it look just so delicious. At that point I couldn't remember ever wanting to suck a dick more in my life. In fact, it was probably the first time I really had the desire to want one in my mouth, the other times I did it just to please my partner.

Just a few hours ago Jack had given me the best orgasm of my life. I really wanted to make him feel just as good as he made me feel. No, I wouldn't fuck him, but I could let him inside my mouth and give him a memorable blowjob. In my opinion, this wasn't really escalating the situation with my boyfriend, Alex, any further. Jack had gone down on me and I would do the same to him. They were both events where we had oral sex. It wasn't really making things worse unless we had PIV sex. Plus, before I even let Jack finger me. Since technically he already penetrated me, a little blowjob couldn't possibly make things worse.

I looked up at Jack to see if he was awake yet. It appeared he wasn't, but I had a feeling that would change very soon. My hand still at the base of his dick, I increased the pace of my strokes. It looked so inviting, I couldn't wait any longer to get a taste of it. With his underwear still on, just the top half of his dick was in reach, so I started licking from the middle of his shaft up to the top of the head.

Up and down his shaft my tongue went, getting his dick nice and wet. Mixed in with my saliva was his precum, adding to the wetness. It tasted so good, unlike with other partners where I simply put up with the taste of it. I looked back up at Jack, I still couldn't tell if he was awake yet but his breathing was a little louder. Oh well, soon enough he'd awake to this college freshman sucking his big dick, pleasuring him.

And that's what I liked about this situation, that I was in complete control. I had most of my clothes on and I really doubted he would stop me once he finally woke up. There was no chance of this going any further. He had made me cum so it was only fair that I'd get him to cum as well.

I switched my gaze back to his cock. I kissed his shaft slowly from the middle, just as I licked earlier, up to the head. I kissed the head too, I french kissed it at first, swirling my tongue around his now bulging head. Still holding his cock, I realized it was still growing in my hands, if that was even possible.

Next I engulfed the whole tip of his cock in my mouth. A moan escaped from my lips when it was all in my mouth. I didn't mean to so loudly but it just happened. I continued swirling my tongue around the tip, and made my way down just a little further. Up and down I continued on Jack's cock, going down just past the tip only about an inch. Even though I barely had that much of his dick in me, my mouth still felt like it couldn't take too much more. It was probably because he was so thick. Like I mentioned before, his big cock dwarfed Alex's, and was definitely much bigger than the two guys I had sex with in high school.

While going down on him, I once again looked up at Jack and made eye contact, since he was finally awake. His face was contorted in pleasure from what I was doing to him. He didn't take his eyes off of me though. I got up to take a breath and licked his shaft once more for good measure. I smiled and looked at him in the eyes and said "Let's get these off of you," with a wink. I took my hand off of his dick and used both hands to get his underwear off of him. He silently responded by lifting his butt up I could take them off quickly.

At last, there was no more clothing in the way. I tossed his underwear on the ground. I slid my hand into my panties briefly, just to see how wet I was. Aware that Jack was watching me, I brought my wet fingers to my mouth and sucked off my own fluids. I had never done that before, but in the moment it seemed right, and honestly it wasn't that bad. Jack seemed to like it, he was now stroking his dick with one hand. As he did so, his balls went up and down with his strokes, and it definitely seemed like his was at full mast now. I playfully batted away his hand and leaned closer down to his crotch.

"That's what I'm for now," I said with another wink. He smiled and I was about to go down on him but got a better idea. "Why don't you slide this way? That would make it easier for me." I motioned to the side of the bed and he sat up and moved where I requested. This way, I could suck him off and not have to bend over awkwardly. Plus, I could watch his reactions from this angle.

I grabbed a pillow from the bed and placed it under me as I bent down on both of my knees. Now, his legs were hanging off the bed with his feet touching the floor, and I was knelt down in front of him with the perfect angle to give him head.

I wrapped one hand around his thick cock and noticed that my fingers didn't even go around all the way! This thing was probably just as thick as my forearm (and I had learned later that Jack was about 8.5 inches long!). I stroked it a few times before adding my other hand to the mix, pumping him with both hands now. "Holy shit!" I said, "I've got both hands on this thing and there's still some left over! I can't wait to have it inside me." Of course I was talking about blowing him, but a little teasing wouldn't hurt.

Now being so close to them, I took note that he completely shaved his balls, while the rest of his pubic hair he kept trimmed instead. I had never had or wanted anyone's balls in my mouth before, but they just looked so inviting. Such a nice complement to the huge hunk of meat that I was jerking off. I took one hand off his dick, while the other still slowly stroked his shaft, and fondled his balls. I did it gently and he seemed to like it.

But I soon let go of them. I leaned in closer and licked his sack instead. After a little teasing I got ambitious and put one in my mouth, swirling my tongue around it like I did with the tip of his cock. I let that one out of my mouth and switched to the other one. I felt Jack put a hand on the back of my head and I looked up at him in response, my eyes wide and staring at him directly. "You want me to suck your cock some more?" I asked him.

"Fuck yeah, suck that dick."