My First Time Cheating

I had just turned 19 at the time that this happened, and even at that point I was already rather well experienced in all things sexual compared to many girls my age. I had been called the Two Week Wonder during high school because I'd date a guy for two weeks and usually put out, then dump him and move on. I thought it was the proper way to do things after all! Then when I went to college things changed a bit, and my horizons broadened, both in my sexual appetites and in my desire to have an actual relationship rather than a fling.

My first semester of college I spent time making friends, going out to party and studying. I had a few one night stands here and there but noting too memorable. I had become great friends with a girl that lived in the dorm over from me named Kerri, and she and I went out clubbing at least twice a week. She introduced me Liam, who I absolutely fell for. The sex was good, he was hot, and we got along great! He was a junior and stayed busy with a part time job and some school activities, so while I saw him often we weren't always joined at the hip, which meant I got a lot of time where it was just me and Kerri. We had been dating about 4 months at this point, a record for me!

It was a warm weekend in May, and one of Liam's friends, Judd, had invited Liam, me and Kerri down to a lake house for a party. We planned it out for at least three weeks and were excited to go. Liam got bad news though, and he was going to be forced to work out of area that Saturday. He worked part time for a construction company owned by his uncle, and sometimes they would need him to travel to different projects. I had met most of Liam's college friends by this point, but only one of them aside from Judd was going to be there. Most of the party would be people that Judd knew from work (he was 25, a bit older than us). To make a long story short it was decided that Kerri and I would go down Friday with Liam's friend Vance and his girlfriend Ashley and those two could "keep trouble away from us". Liam would come down Sunday morning.

Early Friday afternoon we got up with Vance and Ashley and had an hour long ride down to the Lake where we immediately got into our bikinis and took to the water. They had a nice dock with a lot of floats, and we were having a great time. The group there were mostly couples, though there were a few lone guys there. After quite a few drinks there were a lot of jokes about skinny dipping but nothing ever happened despite almost everyone agreeing to do it. Eventually at around 8pm the group decided they would leave and go eat then hit the local night club, but there was a problem. It was a 21 and over place, and me and Kerri were both 19, so we couldn't go. The problem was solved when three of the guys there offered to stay behind at the lake house with us. Two of them seemed like introverts and the other, a guy named Randall, was annoyed with one of the couples about something.

After the groups left me and Kerri kept drinking along with Randall, while the other two guys left without saying a word. By 10 that night Kerri was smashed and passed out in the house while me and Randall were still awake but very buzzed. Judd checked in with him and said they would be at the club for another couple of hours. We were bored and decided to go swimming again. This is when things got interesting, and I still remember it like it was yesterday.

As we walked on the dock I noticed Randall looking down at me. I wasn't the prettiest girl in the world, but I wasn't bad looking. I had been chubby as a kid and still had a little of that baby fat on my face, but mostly it was gone by then. The one thing I had going for me were by breasts -- they are rather large. 36DD to be exact, since I know people will be curious. Randall certainly couldn't help but stare at that point.

"So, your friend must be a lightweight," he said laughing. Just an excuse to chat because our conversation had died out I guess.

"Haha, yeah," I replied. "We drink in the dorms when we can, but she never really did it much back in high school," I told him, the situation becoming quite awkward.

As we walked to the water I took a better look at Randall, and wasn't overly impressed or disappointed. He was rather average, maybe a bit on the attractive side, and seemed to have a decently athletic body. He was wearing a black tanktop and red swim trunks. I realized I didn't know much about him other than he was around Judd's age and that he worked at a factory of some sort.

Once we got back down to the dock we sat around nursing our beers, not really having much to talk about, when I finally spoke up. It was probably the alcohol and boredom combined that made me say it, but I just made an innocent comment about earlier that day. "Too bad everyone chickened out with the skinny dipping earlier," I said.

Randall looked over to me and lifted his eyebrow. "Why, something you wanted to see," he said jokingly.

I shook my head. "No, not really, I was just bored and thought it would be funny. Don't think my boyfriend would like me doing it," I added in, remembering Liam for the first time in a while.

"Well, he's not here, so if nobody mentions it he wouldn't have anything to get mad about," Randall said in a joking, but not quite joking manner.

My heart was beating faster in my chest, I was getting nervous about it. I had never actually cheated before, but then again was skinny dipping actually cheating. I didn't think it was, though maybe it was close. Still, I wasn't sure, plus I didn't think we'd actually get past flirty conversation.

Then Randall looked over at me. "Well, I mean technically we could still go skinny dipping," he said, not joking at all. I tried to reply but I couldn't do anything but stare for a second. Then suddenly I blurted out, "YOU FIRST!".

To my surprise Randall stood up and took off this shirt, then slowly eased his swim trunks down. I could barely breathe since it was about the last situation I expected to be in that night, and what I saw made me forget I even needed air.

As Randall's trunks came down I saw the top of his cock, and it looked thick even soft. And the more his trunks went down, the longer and longer that cock seemed to grow. When he was done I was staring right at the biggest cock I had ever seen up to that point.

Liam was decent sized, probably just over 6.5 inches, and he was decently thick. He was my biggest, until Randall decided to skinny dip. His cock was somewhere between hard and soft, it was not only already thicker than Liam's but also longer! I wasn't an expert on cocks at that time, but I felt like one that big was not something I'd ever see again.

"Holy shit, that's huge," I said without really thinking about it. Just stating the truth. "That's like already bigger than my boyfriends and not even hard," I added, staring. My head was a mess, and I was in that strange mindset that you get when you're buzzed. You know what you're doing, but as long as it isn't dangerous you just don't care about the consequences. That was me. I knew I had a boyfriend. I knew I shouldn't cheat. But, at the same time this cock was something special and somewhere deep down I knew that this might be my only chance to experience something so unique.

I don't remember the exact words that were said next, but I do remember that I got so horny that I could barely think. I wasn't wearing the skimpiest bikni I owned (that would have been one of my thong bikinis) but it also wasn't very conservative. I remember being so turned on that I could feel the wetness of my juices running down my leg, and I probably could have started a campfire with how hot my pussy felt. I was almost in a trance, but I did remember that I was supposed to be naked too, so without much thought I pulled my top and bottoms off. Then we were naked.

I was breathing rather heavily, my eyes focused on his cock, and much to my delight it had started to grow even more. Liam's cock was one of those that starts really small and then grows a lot to full size, but Randall was a bit different. His started big and got bigger, but it didn't grow as much. If I had to guess he went from about 7 inches semi-hard to maybe 8.5 fully hard. But oh boy did it get thicker.

I walked up to Randall and reached out with my hand, grabbing the top of his huge cock. It was so heavy! It was very warm, and also uncircumsized. I had never seen an uncut cock before, so my first instinct was to play with it and examine the skin. I loved it! His cock also had a ton of veins, which was also a trait I learned that I preferred that night. I don't remember the details of our dirty talk, but I know he was very impressed with my breasts. We ended up kissing while he played with my tits and I stroked his cock. He was a better kisser than Liam, but I imagine he was quite experienced.

Our tongues explored each other's mouths for a while and our hands explored each others bodies. We were standing on the dock, secluded from view by the boathouse. He was a lot taller than me, so it made things a bit awkward when he finally had enough kissing and bent down to suck on my tits. He still made it work, and I never once let go of his lovely huge cock. I stroked it lightly, not wanting to make him cum, and also giving myself a change to feel it all over. My other hand moved around on his body, and I eventually began to fondle his balls. Once again something he had that was bigger than Liam, and while I never was all that excited by balls, the size of his did turn me on a bit more.

He was infatuated with my tits, and I didn't mind one bit. He was good and though my breasts aren't super sensitive, it still feels nice when someone plays with them. He had a skilled tongue and mouth which got me even more turned on. I took my hand off of his large balls and then guided his hand to my pussy.

He started playing with my clit, and then eventually slipped one finger inside. I was so turned on by that point, partially from our activities and partially from knowing I was cheating, that there was no resistance. While his cock was the biggest I had seen, I wasn't exactly a stranger to size thanks to one of my dildos. He started with just one finger, then two. But I was greedy. "You can put more in," I told him with a shaky voice. In the end he found that 4 fingers would fit in me, and he expertly used his thumb on my clit. I came for the first time from that.

After that I pushed him back a bit, then dropped to my knees. I wanted to get to know that dick better. I grabbed his dick with my right hand, bringing it to my mouth, then began to lick. It was a bit salty, but overall had a nice taste to it. My left hand began to cup and caress his huge balls. I licked my way from the bottom to the top, making sure to spend extra time circling my tongue on the head of his cock. I could feel his body reacting to me, which only spurred me on more.

I slapped myself in the face with his cock, and I could tell that was something that he didn't expect, but he clearly liked it. I continued to lick his cock, occasionally slapping it on my face. It was so heavy that it actually felt like it could hurt me if I slapped too hard. Finally I decided it was time for a proper blowjob and took him in my mouth.

I wasn't sure how I'd handle his girth, but surprisingly it went in without much effort. I guess I have a big mouth in the right way. I had given a lot of blowjobs by this point in my life, and I felt like I knew how to please a man. With Randall I found that his size made some of my tricks hard to do, but I still managed to suck him with some skill. He complimented my efforts every few seconds it felt like. He was so thick, but his cock, while hard, still had a bit of 'give' to it, so I found that I could force it down my throat. It wasn't super comfortable, but at the same time I was so turned on I didn't care.

My throat was getting a bit sore, and by this point I had drooled so much that his dick, my chin and my tits were covered with my saliva. As I sucked I used my tongue as best I could, making sure to focus on the head of his cock each time I could. His cock was so thick that I couldn't really do that as much as I would have liked, but he didn't seem to mind. I tried to see how far I could swallow it, but I found that about half way was as far as I could go, mainly because his cock was thickest in the middle and at that time I just wasn't quite skilled enough to go further. He was still amazed.

I don't know how long I sucked him off for, but my jaw eventually got tired (my knees hurt too) and I decided I wanted to feel that monster inside of me. My pussy was still dripping, my juices had even left a wet spot on the dock by my knees. The problem was that there wasn't anywhere that was very good to lay. Randall come up with a creative solution, however, and we were soon positioned doggy style with me supported on one of the rafts and him kneeling behind me on a towel.

"I want to feel it in me," I told him. We didn't have a condom, but I was on birth control and I was so turned on I didn't care about anything other than getting fucked. He slid up behind me and began to rub the tip of his cock over my pussy lips. I was so wet that it almost just slid in then. I don't think I had even been so wet before. Then he slipped the head in.

I moaned as I felt it go in. If anyone would have been awake and on the porch of the house we would have been busted right then. I had been LOUD. He had probably intended to go in slowly, but I was so wet that he ended up sliding about half way before his girth finally slowed him down. My pussy gripped him tightly and I looked over my shoulder to see his face. "Let me," I told him as I began to slide myself back onto the rest of his cock.

He was big, even bigger than the largest dildo I had, but not so much that it felt like I couldn't handle it. I rocked back and forth a few times, using my muscles to grip his large cock as I did. With each rock backwards I went a bit further, my pussy opening to accommodate his large member. I could feel myself stretching, and it even burned a bit, but the pleasure was so great it overwhelmed any other feeling. Finally I just leaned back slowly until I felt my ass bump against his body. It was fully inside of me!

At first I controlled the pace and he sat back simply responding to my movements. It only took me two or three minutes of slower, sensual fucking to get my first orgasm. His cock was so perfectly long and thick that it literally hit every single spot in my pussy with every thrust. I had been with one or two skilled partners before who knew how to fuck and could make their cocks hit all of the right places. But this was the first cock that hit them all at the same time. Fuck it was so good.

I kept looking back, locking eyes with him. I came another time, letting out another much too loud moan. Then I decided it was time to let him do the work. "Go wild big boy," I said to him, trying to give him my most sultry look but probably failing as I reacted to the pleasure I was feeling. Then he started to thrust into me how he wanted to, and I learned how it felt to actually properly get fucked.

"I've never had a girl that could actually handle me like this," he told me between heavy breaths as he began to ravish my pussy. He was fucking me like an animal, thrusting hard and fast. I could hear the loud clap of our bodies meeting and the wet noises my pussy made as his cock probed me over and over. I lost count of how many times I came after the fifth, but I would estimate at least ten times for the entire session. I couldn't even move anymore when he finally announced he was going to cum.

I wish I could tell you that I turned around and let him cover my tits, or that we both jumped up and he came on my face porn style. But I was spent and so was he, so he ended up pulling out and cumming all over my ass and back. His cum was warm, and it was a nice large load as far as I could tell.

"That was the best I've ever had," I told him when I finally was able to roll over to look at him. He had somehow managed to grab his phone and was sending a text. He looked down at me and smiled, reaching out to grab my tit. I didn't mind at all. "Yeah, you just ruined it for other women, I don't think I'm going to find anyone better," he responded. I reached out and pulled him over and we made out for a bit, my hand massaging his balls and playing with his semi-hard cock. I was still entranced by his foreskin, so I had a great time playing around with that, while he was still focused on my breasts.

His phone buzzed after we had been sitting there a few minutes. "Looks like they're heading back but need to stop for more booze," he told me. "We should clean up and hide the evidence."

I eventually decided to just jump into the lake and he followed suit. By the time everyone got back we had cleaned everything up as best we could. Randall had even splashed water on the dock to make the entire thing wet, thus covering up the sight of any strange wet spots. By the time everyone got back we were sitting at a picnic table sipping beers like nothing happened.

Saturday was a fun day overall, and we tried to find any way we could to repeat our Friday night performance. Luck wasn't on our side, so the best we got was some short makeout sessions and I was able to give him a bit of a handjob, but the rest of the group didn't go out again that night. Sunday came around and Liam showed up so we basically gave up on any further fun. We did exchange numbers and made plans to meet again if we ever could (we did twice more, but that was later in the year). From that point on, I almost always thought about Randall's dick any time I was masturbating, especially with my large dildo. I also thought of him a lot when I was having sex with Liam, wishing it was Randall instead. I felt a bit bad about that if I'm honest, but I couldn't help it.

The entire experience was by far the most exciting experience that I had up to that point in my sexual life. It was also the reason that I began to occasionally cheat on Liam, looking for that naughty, fun spark again. I did find it quite a few times and came to the conclusion that I really, really love cheating. I might be a bit of a bad person for that, but it's something I can't really help. I also realized that aside from the taboo cheating aspect of it, the size of his cock was another huge part of what made that night so hot. I still think about that night often.