Confession of a Lifetime

Where to begin...

It's quite intimidating getting started on this writing project! Even though I stopped feeling guilty a long time ago, I suppose I'm overwhelmed by the amount of information I will need to cover, in order to tell you everything.

Starting at the very beginning seems to make the most sense, but first I'll introduce myself, then we will get right into it. My name is Kristen (alias), and I have been happily married to my husband Rob (alias) for fifteen years. This series will be the only place that I ever confess publicly, that I've been cheating on Rob for around 20 years, for the entire duration of our relationship. I strongly believe that nobody who knows us IRL is ever going to find out about this, and I'd like to keep it that way, I'm good at keeping a secret. All names I provide will be aliases and I will also be keeping our location information vague, but I will provide you as much information as I can.

Rob and I are currently both 39 years old, and he is the only long-term relationship that I've ever had. I've always thought that it's nice to be with someone the same age as me, he understands all of my jokes and references, we are great together. Rob was my highschool sweetheart, he was the first man I ever dated seriously, besides the usual innocent early experimenting like kissing someone on a dare lol.

We were dating before this, but, things took a bit of a turn the year after we graduated high school. Rob had just turned 19 and I was 18 at the time (sounds cliche but it's true), my birthday was later in the year. Rob and I had been having sex less frequently in the months leading up to our graduation, I remember that during the summer of that year, the most recent time I had sex with Rob was on our two year anniversary which was in March, so it would have been at least three months that had passed since then. In those three months there had been a lot of opportunities for us to be intimate that had been missed, in my opinion, and I was feeling disappointed.

The first of these missed opportunities was at Rob's birthday (late April), it had already been a month since we fucked on our anniversary and I was hoping that having some fun with friends was going to rekindle the spark. We spent a long weekend evening at a friend's house party which he had organized for Rob as a surprise (I had been tasked with making sure he didn't make other plans that evening). Everyone was having a lot of fun but at the end of the night Rob was asleep early, he claimed he was stressed and overworked preparing for our exams, which made sense.

I love Rob, and at this point in our history I still viewed cheating as a bad thing to do, which I think was naive. I didn't want to risk hurting his feelings by having my needs met elsewhere, but a month felt like a long time. I have always been a little bit hypersexual, in hindsight. I could tolerate a week or two without that level of physical affection, but a month without sex was weighing on me a lot! Nothing especially bad happened that night, the party took place on the actual date of Rob's 19th birthday so I figured it would be extra wrong if I cheated on his birthday. Looking back on it now, I think this was when my mind started wandering to the possibility of cheating though, and when I started to feel excited thinking about the possibility of going through with it.

Anyway, I'm starting to get a bit rambly now. All that had happened on the night of his birthday party is there was a late night game of strip poker that took place after most people had fallen asleep or gone home. I won the game, so I didn't even need to get completely naked, which I felt proud of! This felt mostly innocent and pretty normal in terms of just being a common party game, even though it was definitely sexually charged, nobody was touching each other or anything so I thought it seemed fine. We played with four people including myself, the other three players were a girl I had been best friends with for years (Maya), one of Rob's friends from his hockey team (Jeremy), and Maya's older sister Taylor.

As an aside here, I just feel the need to insert that while I can understand it may seem a bit inappropriate, the relationship between Taylor and Maya was in no way sexual or incestuous. Apologies to any readers who are into that but, they were nothing but sisterly to each other. Jeremy made a few pervy comments about this during the game, but we all just told him to shut up and be respectful lol.

I've always been excellent at card games so I felt very confident about my abilities going in. Jeremy had always been a bit of a perv and had made comments about me several times in the past which I had just brushed off. Oddly enough strip poker wasn't even Jeremy's suggestion although of course he happily went along with it. Taylor had been the one to suggest we play the game, according to gossip I heard through Maya, apparently Taylor had been secretly hooking up with Jeremy for the past several months. Taylor was two years older than us and in university, but Jeremy was one year older than Rob so, there was only a one year age gap between Jeremy and Taylor, it didn't seem all that weird or unusual. Anyway, according to what Maya told me that Taylor had told her, Jeremy allegedly had an enormous dick. I'm pretty certain that Taylor wanted to use the game as an opportunity to show us that she wasn't exaggerating.

Besides, like I mentioned, Maya was my best friend. We had been to the pool together along with Taylor, and had all changed in the same changing room, so it seemed like completely harmless fun between the three of us, and I can't lie that I was excited about the possibility of seeing Jeremy naked with my own eyes as well (Taylor's descriptions were intriguing).

So we start playing, and Maya plays terribly lol. She was completely naked so quickly, which was extra unfortunate because she wasn't supposed to get dressed again until we finished the game. I was doing very well so I took off my shirt and socks and lent them to her so she could buy herself back into the game with two clothing items. So we are sitting there, I'm wearing a bra and a skirt and panties, Maya is wearing my shirt and socks, Taylor is wearing only shorts and panties so her tits are out, and Jeremy is down to only his boxers. At this point we can clearly see Jeremy's shape through his boxers so it was already very obvious that Taylor was NOT exaggerating about his size, but Maya and I both whispered in each other's ear that we wanted to see it come all the way out, so we kept playing.

Maya again didn't last long at all (I think she's not really the strategy games type), and had lost both of the clothing items I lent her over the course of the next few rounds, so she had left the table and was just sitting on the couch. Jeremy kept staring at her and was even ballsy enough to ask if she would spread her legs and give him a look at her but she just rolled her eyes at him, and Taylor and I told him to just pay attention to the damn game. At this point, I am down to bra and panties, Taylor is wearing only panties, and Jeremy is somehow hanging onto his boxers for dear life with a few strong hands in a row.

The next round, Taylor loses her panties and is out of the game, she makes her way over to the couch with Maya. Jeremy makes a few more pervy comments but the game continues.

Anyway, I won the game on the next round with a huge bluff. I went "all in" immediately, meaning that I would be required to get completely naked if my bluff was called... but I saw Jeremy looking visibly nervous and I knew he had nothing, it worked! Jeremy folds his last hand and makes some petty jab at me about how it's uncool that I take these games so seriously, I think he was just disappointed he wouldn't be seeing me naked, it was clear he wanted to see all of us.

So... he stands up, his boxers come off, and... OMG. Forget not exaggerating, Taylor was underselling it even. Jeremy was absolutely hung, I was astonished, I'd never seen anything like that. He was easily 8 inches long and probably slightly more, but the girth... lord almighty, the girth was unbelievable. It helped a lot that both Taylor and Maya were nude so he was quite hard already.

Jeremy made some dumb pass at Taylor suggesting that she should give him a blowjob, but she shut him down and got a little pissed saying "that's my sister so take it easy save it for another time" or something along those lines. Then we all went to bed, he was visibly disappointed nothing was going to happen, but we all made him promise that he wouldn't tell Rob we had played the game. I didn't feel like I necessarily did anything wrong, but I also knew he'd be uncomfortable if he found out I saw his friend's dick, so everyone decided it'd be best to keep it secret.

Maya and I snickered with Taylor a little before bed about how we were blown away by his size, we asked her some questions about what it felt like and she admitted that it had taken some getting used to lol. But, then we all just carried on like nothing happened!

Rob woke up the following morning with me in bed next to him, and never found out about the game we played (not even 21 years later).

The problem is that little bit of fun definitely awakened something in me that became difficult to keep under control in the years to come... but this is getting a little long, I will save that for part two.