*This is part of* [an ongoing series](https://www.reddit.com/user/aqualounger/comments/xrqbc3/my_infidelity_diaries_links_to_all_posts/)*. About me: Tall, dark hair, skinny in my youth but less so these days, with a cock on the small side of average. Oh, and for better or worse, I am a serial cheater. These are my stories — all of them real in every way, except for the names. I’m not sure what I hope to gain from writing all this down; maybe it will be cathartic for me, and hopefully it will be hot for you. Anyway, here’s what happened.*
Sheila and I met on a bitterly cold January night, during a particularly dark and snowy winter. I had been invited to my friend’s gig, and when I arrived she was standing near the stage. I don’t remember what she was wearing, but I remember her long, curly, dirty blond hair, and the casual tilt of her hip.
I was hooked immediately.
I saw she was nearly finished her beer, so I quickly bought a round and brought them over to her to introduce myself. We hit it off immediately. It was one of those kismet moments — we realized that we had many friends in common, and we both wondered aloud how it could be possible that we’d never met. I was finding this fact more and more tragic with each passing second, because by this point I had been married for just over three years.
Every time I looked at Shiela that night, I noticed something different about her. How big and blue her eyes were. How perfectly her neck met her shoulder. The gentle sway of her perfect breasts. Her massive smile. Her ass, her legs…fuck, I was falling head over heels.
We talked and drank all night, cheering as our friend’s band played their set. We stayed at the bar until it closed, and then just started walking and talking. In fact, we walked and talked all night, even though our faces were frozen. We made our way west (I didn’t tell her I lived east) along streets large and small, our boots crunching on the icy sidewalks. Eventually, we found ourselves at her place, and went inside to warm up.I knew she wanted me to kiss her, and holy fuck did I ever want to do it. But I didn’t; I was trying to avoid cheating at that point, and though our first night definitely went into the territory of emotional affair, I decided in that moment that it was somehow noble to avoid making it physical.
But I did get her number.
We started messaging every day. I loved talking to her. We chatted about everything under the sun. It was usually pretty light, but one day my hunger got the better of me:
Aqualounger: “Can I tell you something?”
Shiela: “Sure.”
“I wish I’d met you five years ago.”
She took a minute to reply. I held my breath. Finally her message appeared:
“I don’t know whether to blush or cry.”
Our messages got more intense from there. We talked about sex a lot — but for some reason never sexted with each other. But I do remember how hard I came in my bathroom after a chat session in which she told me “I cum so hard with a cock in my ass.”
By this point, winter had turned into spring, and we’d also seen each other several times — always at gigs. I’d joined my friend’s band (he never knew the real reason why), and my heart would skip a beat every time Shiela arrived at the bar where we were playing. We were careful not to focus exclusively on each other when we were in the same place, but I’d often catch her glancing over at me — or maybe she was catching me looking at her.
Finally, in late May, the dam burst.
I was asked to be a guest judge at a drunken spelling bee, and she came with a couple of our mutual friends (one of whom was my ex-girlfriend, Anne — [who I cheated on](https://www.reddit.com/r/gonewildstories/comments/m0yzg0/my_infidelity_diaries_robin_makes_an_offer/) when we were together, and with whom I had also cheated on my wife a couple of years prior…but that’s another story). The booze was flowing, and afterwards the four of us hung out on a patio after the event. Shiela and I were side by side, and before long we were touching each other’s legs under the table. I’m sure we were being obvious as hell, but at that point we were so drunk on lust for one another that we didn’t give a shit.
Finally we left the patio, and Shiela and I started walking again. We came to a schoolyard, and I couldn’t fucking take it any more. I pulled her in toward me, and kissed her. We clawed frantically at one another as our tongues intertwined, and all of the pent-up longing spilled forth from me in a flood. Within a minute, I had her tits in my hand for the first time. Another minute, and I felt her ass under her jeans, then slid my hand around to her clit.
It was not romantic. It was not even as hot as it could or should have been. But it was inevitable. If I were making this up, I would tell you that we had magical sex that night, or that she gave me the best blowjob of my life and then I made her cum over and over. But this is a REAL story, and none of that happened. (I mean, it did happen eventually, but not this first time. I’ll tell that story next, I swear.)We made out for 10 or 15 minutes, and then I realized how late it was. I had got in considerable shit from my wife for pulling an all-nighter with Shiela five months earlier, and though I certainly wasn’t going to be as forthcoming this time around, the time alone was enough to arouse significant suspicion. I walked Shiela to her bike, and we went our separate ways.
The next day, she told me that she regretted letting things get that far. I lied and said I did too. We still chatted often, but things cooled off as summer began. Then, at a midsummer music festival we attended with a huge group of friends (including my wife), I watched as Shiela and my best friend flirted mercilessly. They hooked up on the first night, fucked their way though the weekend, and stayed together for several months. If this year of my life were a movie, this stage would be that middle third where everything goes to shit.
Then, out of the blue, my friend dumped Shiela. I saw her a couple of days later at a party, and she was devastated. She asked me if I knew why my friend had ended things, and I told her honestly that I had no clue. What I didn’t tell her is that it made my heart soar. We talked a lot that night, and she cried on my shoulder. We left the party early, and I rode in a cab with her back to her place. Once again, outside her door, I was confronted with a choice. I knew she wanted me to come inside, and I knew what would happen if I did. Fuck, I wanted to — she looked so gorgeous with her big eyes full of tears. But of course, I couldn’t do that to her. I gave her a huge hug, kissed her on the forehead, and wished her good night.
It was a melodramatic end to my first year with Shiela, but it most certainly was not the end of our story. The next part has more sex in it, if that’s your thing, and I’ll post it as soon as I’m able. Stay tuned.
Source: reddit.com/r/gonewildstories/comments/1058a8z/my_infidelity_diaries_shiela_the_first_year