This story is about a cheating girlfriend/wife with an underlying theme of cuckolding. You've been warned. Feel free to criticize (or praise) the story telling, language, structure, etc. If you're going offer an opinion on the morality of the girl, the manhood of the boyfriend, etc. I'm going to suggest you go pour yourself a glass of STFU. Enjoy.
I'd been dating my future husband Brian for about two years. I was relatively naïve about sex and coming from a conservative background did not have much experience. Brian made me feel safe and brought me along slowly. We had been dating for about a year before we had intercourse. Prior to that there had been a lot of dry humping to mutual satisfaction and a little bit of oral.
I won't say the first time we fucked was a disappointment but I didn't see stars either. It took Brian a few attempts to penetrate and he fell out a couple of times as well. He eventually found a rhythm and given our inexperience and concern about my getting pregnant he pulled out and came on my stomach. I remember it being reasonably pleasurable, but nothing special.
I guess I should give you a little more background. I was a year younger than Brian. I started dating him when he was senior and I was a junior in high school. I basically started dating him because my best friend was dating his friend. Brian is a good looking guy. He is about six feet tall, with a decent build and reasonably athletic.
In high school I was (still am) pretty hot. I'm about 5' 4" weigh 110 pounds with green eyes and dark hair. I was your classic cheerleading captain and prom queen. I had plenty of options for boyfriends. But my mother's old fashioned views on sex had an impact on me I was pretty inexperienced beyond kissing.
Brian took his time and I was also beginning to reject a lot of what my mother had told me was right and mostly wrong about sex. I had orgasmed with one other boyfriend before Brian while making out. I'm not sure the other boyfriend knew it had happened. With Brian the making out and heavy petting went to a new level for me. We would both consistently cum while dry humping. We also gave each other oral sex on occasion but I still was holding back on actually fucking. Brian seemed okay with it and that's pretty much how things went before he went away to college.
We had agreed to keep dating and stay faithful even though Brian would be living a couple of hours away and I would be starting my senior year in high school. I'm pretty sure Brian kept his promise. I didn't. I started seeing Matt. He was also very good looking. He also had a better build and a much bigger cock. I didn't fuck him either (yet) but I would get incredibly turned on both physically and psychologically while giving him a hand job or feeling him grind against my pussy while we dry humped. Brian had opened the door a crack to my sexuality and I was beginning to explore it.
As much fun as I had with Matt and as much as he turned me on.. he was the bad boy.. Brian was safer. I felt protected with Brian. Eventually, I stopped seeing Matt, more or less, once Brian got back from school and Brian and I began dating again that summer. Initially we had to get past all the jealousy and anger that Brian felt but we did. I also had to get over not having Matt's big cock to play with.
That summer Brian and I started to push the boundaries I had a little more too where we eventually did fuck. It was, like I alluded to before, okay. I didn't come from intercourse but Brian would make it happen for me with his hand or mouth. I just figured that's the way it was.
I ended up going to college in the same city as Brian. We were pretty much an item that whole year. I was at an all girls schools so there weren't a lot of alternatives for me. I met Brian's friends and roommates. He shared an apartment with four other guys and while I flirted plenty with several of his friends nothing happened (at least that year).
While we were away that year I also started to learn something about Brian. He liked hearing me tell him about the times I was with Matt. At first I would just playfully give him small details but Brian would press for more information to where I would be telling him how much bigger Matt's cock was than his, how hard it got, and good it felt. Brian would ask if I'd like to fuck him and the way he asked I knew he wanted an honest answer. Yes, I wanted to fuck Matt. Yes, I wanted to feel his cock inside me. By this time I think Brian knew he wasn't making me come when we fucked and I think both of us were wondering what would happen if I fucked somebody else.
There was only one problem with me fucking Matt. He had joined the Army and was stationed overseas.
That summer after my first year in college Brian and I both went home for the summer. We had the typical summer jobs and hung out with our friends. One of Brian's friends was Mike. They had been classmates in high school and worked together and even played softball. It was natural that I'd see a lot of him as well. I had actually dated Mike for a short period of time when I was much younger.
I'm not sure how it started but eventually Brian, Mike and I would end up going out quite a bit together. Initially it was relatively innocent. We'd play miniature golf, maybe go to bar, just hang out really. Eventually though when we'd go out I'd end up dancing most of the night with Mike. We'd flirt a little bit and Brian would see us. Later Brian would ask about it and we would both get turned on by the thought of me doing something with Mike. I don't think we thought I'd fuck him but both of us enjoyed the idea of me giving him a hand job. Mike would tell me he had a big dick (locker room showers) and that intrigued me. As the summer went on we would go to the drive-in and I'd sit in the middle and flirt with Mike while Brian was sitting next to me. At some point Brian would always to leave to get popcorn (I know.. really) and while he was gone Mike and I would make out a little bit and I always made sure I'd rub his cock through his pants, getting him hard and turning me on. Eventually Brian would come back and other than sneaking in a few feels Mike and I would stop.
This went on for a few weeks. Brian, of course knew it was happening and encouraged me to keep it up. It was big turn on for both of us. I don't think Brian and Mike ever talked about it. But of course, Mike knew that Brian knew and finally one day after the three of us had been at the beach it was clear Mike wanted to finish what we were starting.
Mike had left his car at my house. Brian had to go to work so when Brian brought us back to my house it was time for Mike to come in. My mother and sisters were gone and when Brian left it was pretty clear that Mike and I were going get together. I was expecting Mike and I would make out and that I'd give him a hand job. I was not thinking we would fuck. I don't think Brian thought we would either. While we enjoyed all the flirting and play with Mike and stories about Matt I think both Brian and I thought we'd save the fucking for each other.
It didn't take long for Mike to make his move after Brian left. Up until then, probably because Brian was usually around I had been the aggressor with Mike. But this time, knowing he was gone Mike came right at me. We were passionately making out on my living room couch before Brian's car had left the driveway. I felt his hands move up my chest. We were already grinding away at each other when I moved my hand down to his pants and unbuckled his belt and grabbed his cock. He was already as hard as stone.
I was wearing a short jean skirt. One of Mike's hands had left my breast and was now rubbing my pussy. I wasn't planning on fucking him and when he tried to pull off my thong I told him no. He stopped. But his fingers still found his way into my cunt. I was very wet and I gripped his cock tighter and began to stroke. Soft moans were escaping from my lips. Mike positioned me under him and I assumed we were going to start dry humping. His cock was free but I still had my panties on though my skirt was now pushed up above my waist.
I felt Mike's weight on me and I spread my legs. I wanted badly to feel the hard pressure of his cock on my clit. Mike pushed himself up and down a couple of times, God, it felt good, and then I felt his fingers pull my thong aside. I felt Mike's cock bare cock press against my bare pussy. I started to say "no" but before I could get it out he slid deep into me on his first thrust. He slid deeper into me than I ever thought possible.
It usually took Brian two or three attempts to penetrate. But Mike was deep inside me in an instant and my body spasmed in pleasure. It was like nothing I had felt before. It felt like my pussy was on fire filled with a rod of hot steel. The no I had started to say turned into "oh goooodddd." After that I just remember pleasure as Mike fucked me hard until we both came in a way I never had. Mike filled my pussy with his cum and my cunt contracted around his cock again and again, milking all his seed deep into me. I wrapped my leg high around his back and we stayed like that for several minutes savoring the pleasure we had both just felt.
I didn't tell Brian right away. At first he thought we had just done the usual dry humping. When I did tell him about a year later he was pretty turned on. By then Brian knew something was very different about me. You know how they say marijuana is a gateway drug? Mike was my gateway fuck. We fucked a few more times that summer but when he left to go back to his school I knew I could never just fuck Brian anymore. I needed to fuck guys with big dicks and guys that knew how to use them.
Before that summer was over I had fucked Matt (home on leave) and my old high school history teach (mmhhmm). Eventually Brian heard about them, as well as a couple of his roommates. Brian knows about most of the guys I fucked. That first fuck with Mike opened our lives to a path I don't think either one of us ever expected.