Original photo by Lucky
We did it. We finally did it. After years of admiring him from afar, after months of pretending we were just friends, after weeks of playing with our growing sexual tension, Kris and I finally had sex. But, before I get into the details of our long-awaited sexual encounter, let me catch you up on our relationship so far…
I met Kris about three years ago when I started attending a weekly trivia night at a local pub. He was the bartender with all the tattoos and witty retorts, and I immediately developed a crush on him. As I continued attending trivia night on a somewhat regular basis, and even occasionally hung out at the bar on other nights, Kris became more and more friendly. He learned my name, he knew my drink of choice (a PBR with a lime), and we even became Facebook friends.
I never truly thought anything would come of this flirtation. I had no idea if he was in a relationship. I didn’t know if he was open to non-monogamy. I didn’t even know if he was actually attracted to me or if his flirtation was just that of a friendly bartender, and it didn’t really matter. It was nice to go somewhere with a (handsome) friendly face and just hang out.
Eventually, we began to hang out outside of the bar. We’d go bar hopping and end up completely tanked, and finish off the night passing out on his couch together watching TV. Everyone around us assumed we were sleeping together, but it didn’t start out that way. He teased me a lot about my “alternative lifestyle,” claiming his Catholic upbringing would never allow him to get involved with a girl like me. I didn’t take it as an insult – at least, not most of the time. He wasn’t judging me. I’m aware that my lifestyle doesn’t work for everyone. I know it’s scary to some people, and goes against certain lifelong convictions. And, as much as I’d like for more people to give it a try, I am generally not interested in being a part of someone’s experiment as they try out a new way of being in relationships. I’ve had my heart broken too many times (and have unintentionally broken a few of my own).
Between his fears and mine, there were a hundred reasons for us not to date, despite our growing attraction to each other. And the friendship we were forming was so…I don’t know…it just made me so happy that I didn’t want to risk ruining it on a romance that was sure to crash and burn. Unfortunately, hearts and hormones are rarely rational. We were falling for each other, and it was only a matter of time before we would give in. And honestly, we were dating long before we admitted it to ourselves or anyone else.
I barely remember the first time we kissed. We’d been drinking, as usual, so the night is a bit fuzzy. I was feeling close to him because he’d finally admitted to me that he had herpes. Honestly, I’d suspected it for some time. I’m not sure if it was his semi-celibate lifestyle or just the bitterness in his voice when the topic came up, but I just had this feeling about it and I was glad that he finally felt close enough and comfortable enough with me to tell me. Maybe I wanted to show him that it didn’t matter to me, or maybe I was just feeling especially bold and randy from the mixture of alcohol and whippets, but it wasn’t long before I ended up straddling him as he sat on his couch, shoving my tongue into his mouth.
The next morning I half-jokingly apologized for attacking him with my tongue. Admittedly, I was mostly saying it to gauge his reaction and get some idea of how he felt about it. I was just too afraid to ask. His response was somewhat encouraging: “Well, it’s not like I was pulling away.”
Surprisingly, though, that wasn’t actually the first time we’d blurred the line between friends and lovers. Several weeks before our first kiss, as we laid in his bed on the verge of passing out after a night of drinking, his hands began to wander. It wasn’t uncommon for us to snuggle up in bed together at the end of the night. Even on the first night I ever passed out at his house he wrapped his arms around me as we watched TV and drifted off to sleep. I always thought it was sweet. But on this night, for whatever reason, Kris wanted more. As he slipped his fingers under the waistband of my panties I became both excited and nervous. I wanted him so badly, but this wasn’t supposed to happen. We were just supposed to be friends. What if this changed things? Was a drunken night of pleasure – pleasure I’d been fantasizing about for some time – worth risking this amazing new friendship we were building? My head was spinning. My panties were soaking. I squirmed away and giggled.
“Wait, wait,” I said, playfully. “We’re just friends. We’re not supposed to do things like that.” I don’t remember his response. I only remember him pulling me back toward him and sliding his hand back into my panties and between my legs. I squeezed my thighs together and placed my hand over his, but I didn’t pull it away. I wasn’t sure we should continue, but I didn’t want him to stop. My breathing became heavy as I sat there, trying to decide what to do. He gently wedged his leg between mind and spread my thighs apart. “No fair!” I said, laughing. But I didn’t resist. I wanted him so badly.
He gently worked his fingers inside of my soaking wet pussy. I whimpered slightly, but shyness kept me mostly quiet except for my deep, heaving breaths. I can’t remember the last time I felt quite so shy in bed. Usually, by the time I reach this stage with someone, I am fairly comfortable and confident. Perhaps that’s because most of my partners – especially the men – are easy to read and I’m more certain of their attraction to me. But here, with Kris, everything was different. I had no idea how he felt about me or what he wanted. Should I touch him, too? Was this all there would be or would we go even further tonight (or ever)? Even as he worked more fingers into me – 3…4…oh god, yes – my mind was reeling. It felt so good. It was so exciting. And I had no idea how to feel about it. I’m sure I would have come very quickly if I hadn’t been so wrapped up in my own head, but I never actually did.
I did eventually reach over and begin stroking him. His breathing became heavier and eventually he pulled his hand away so that we were both focused completely on him. It was incredibly hot to listen to his occasional whimper and moan as I ran my palm up and down his hard cock. He didn’t come, either, though. After a little while, he pulled my hand out of his underwear and placed it on his chest, and we drifted off to sleep.
The next day we joked that we’d graduated from being just friends to friends who occasionally get drunk and “make out.” I teased him that “making out” usually involved tongues, and we hadn’t even kissed. I was glad that we were able to talk about it so casually, though, and that there didn’t seem to be any awkwardness about what had happened. I wondered if it would happen again. Would we start doing this all the time? Would it always just be drunken fun between friends, or would it eventually turn into something more? I wasn’t sure what I wanted the answers to be. At least, not yet.
Stay tuned for the rest of the story…
