I wished we had gone into the other room that night. I know I was drunk, but I meant it when I said it. “If you wanted to, we could go into the other room. I’d bend you over and put my tongue in your ass right now.”
It didn’t matter that our respective fiancees were in the other room. Part of the thrill was whispering that in your ear, hoping you’d say yes, and knowing they’d be drunk enough that, maybe, they didn’t know what they’d seen. Or maybe they would? That was just as thrilling to me.
I always wondered if you had similar regrets. If there were unfulfilled moments for you, moments you wish had been filled – pun intended. I wondered that about when we moved you across the state for your new job.
I drove to your city, two hours from my house, to help you pack. I knew I was in trouble when I saw you wearing those rolled up sportshorts. They weren’t so far up that I could see your ass hanging out, but I caught a glimpse or two when you bent over.
When we had to stop back at my place on the way to your new one to feed my dog, all I wanted to do was take a break from driving that moving truck. I wanted to steer the conversation to the bedroom, to slip us out of our sweaty clothes, and work up a sweat with your legs in the air.
I wondered about it when I moved into your apartment after I broke up with that one girlfriend – the one you hated.
“I knew she couldn’t do anything good!” you’d shouted as we whined about her over wine. “I bet she’s not even good at sucking cock.”
I should have known that was a come-on, and I probably shouldn’t have said, “That might be the one thing she can do right: she is a great fuck.” I might have been too drunk to see that it made you jealous. We should have been sloppily making out and fucking on that old, puffy couch you’d gotten from a friend. I remember walking in through the side door to see you riding your Tinder date one night. I never saw him again, but I think you made sure I’d see you walk out of the shower every so often.
I wondered about that night when you and the fiancee came up for the weekend, when all of us got drunk, when I told you that I wanted to taste your ass. I wanted much more than that, but you already knew it. At least, I assumed, or hoped, you did.
Then the day came when you told me that you and the now-husband had been having issues. My wife fell asleep on the couch when it became obvious that her team wasn’t going to advance further in March Madness, and I kept talking to you. Like my ex you hated, we talked about how he was bad with money and how he was kinda aloof most nights after work. I was surprised when you told me the two of you were less sexually compatible than you’d hoped.
I was more surprised with how forthcoming you were in that department. You wanted him to be more manly, more assertive. You’d tell him what you wanted, and he’d do the opposite. “I say left, and he goes right,” you said. I joked saying that I hoped you didn’t mean literally. You quipped back with, “No. Up and down better?” I don’t know why that immediately turned me on, and I don’t know why I told you that it made for a much better mental image. I don’t regret that.
Just like I hope you don’t regret sending me that surprise nude later that night. I had gone to bed, and woke up hard. When I checked my phone and saw what you sent, I leaned over to make sure my wife was still asleep. That thrill was back. I don’t know if she woke up while I masturbated to that image and my imagination, but the thrill ended up spurting all over my stomach and chest.
I opened our texts multiple times that morning. I looked at it after breakfast. I looked again after I got in my car and kissed my wife goodbye. I looked at it every hour, at least, until my lunch break. I was shaking when I typed that next text to you, when I typed that confession to you. I told you that I had also been unhappy with my marriage, that I needed more out of my sex life, and that I regretted us not having the fun we should have.
I almost didn’t send that text. I stared at it for what felt like hours. I hit send. No more regrets.
Now, I’m standing here just inside the hotel room we booked. The door closed behind me. The last of its light glinted off the diamonds in your wedding and engagment rings. You layed back on the bed and propped yourself up on your elbows. The black leather straps you’re wearing around your breasts press into and slightly redden your pale skin. The leather garter straps do the same to your thighs and waistline.
The door closes, and the light from the hallway disappears behind me. The evening sun shines through the open window, shimmering off the gold fasteners affixed to the leather at the joints. I scan from your face, down to your exposed breasts and pierced nipples. I can feel my cock growing in my boxers and slacks. I gaze down to your pussy, revealed by your legs wide-open, your heels up on the bed and knees in the air.
“Is this what you’d wished for, daddy?” you ask.
“Many times over,” I say.
I’m sure there are people outside of this room who would say that what we are doing is wrong. But, I think we both agree, that there is nothing wrong with not having any more regrets.
Source: reddit.com/r/eroticliterature/comments/twm58t/regrets_friendshipsinfidelity