Disclaimer: I know this isn’t particularly steamy, but perhaps it’ll pique your interest and give you enough background to want to read the second date, where it crosses a lot more lines.
I’m sure we all remember Yik Yak, that beautiful anonymous app that allowed us to speak our minds and be judged for our mistakes. Being in Boston, the community was vibrant. There were shenanigans, major league fuckups, desperate hookups, and most importantly, the establishment of alter ego characters. We’ve all been there, used our keyboards as masks and became someone we dare not be in real life. I became the sarcastic troll that is my constant inner monologue, whereas what everyone else sees is a driven student, well rounded, big dreams, some past struggles but the strength to overcome anything.
When Yik Yak left this world, it was replaced by Swiflie: flawed, not as much fun, not local, just, not Yik Yak. Still, the old home guard migrated over and life continued almost as normal. I befriended a much older user named FW after seeing his “Daily Wardrobe” selfie. I was smitten by his bold taste in colors and the way he handled the literal hundreds of thirsty girls who always commented. We struck up a conversation. I wooed him with my knowledge of menswear. He became intrigued at my line of study. Very quickly we started talking all day, every day. Not sexual, at first. Just very close friends. We started to let down our guards and let each other into our worlds; talked about our respective troubles at home, our anxieties, our future fears, our past mistakes. We talked about our sexual escapades, his from his days back at Harvard undergrad and then Harvard Law. He called his young self a “man whore,” and I didn’t disagree after hearing his sordid tales. He made me sick sometimes, on behalf of my fellow women, to the point where my dominant side slipped out. I told him in graphic detail what needed to be done to atone for his sins. I wanted him on all fours on a bed, bound, blindfolded, gagged, waiting. I wanted to drip hot wax down his torso and see him flinch, each drop a reminder of a woman he used and fucked like a toy. I wanted him at my feet, kneeling, learning and accepting his place as my submissive. He was shocked.
But it didn’t end. He wasn’t used to being told no. He wasn’t used to being told he was “less than.” He wasn’t used to, inexplicably, wanting to be used himself. And so it continued. The sexual desire was growing, from both sides, on even ground. Our chemistry was such that we could switch directions effortlessly – he could go from explicitly telling me how he needed to fuck my throat, hold me down and bruise me, to show the world that I was his, to being absolute putty in my hands. I called him my Thumb Ring, because he knew that he was just as under my control as I was under his spell.
I learned, weeks later, that he wasn’t single. In fact, so not single that he’d been married for eight years. Not an unhappy one; she was his intellectual and career equal. Emotionally and sexually, she failed miserably. I trusted that he wasn’t just telling me this to pacify me, to justify his bad behavior with me. He spoke about her objectively, even asked me for advice about how he should broach certain issues with her. I figured this flirtation would end in me giving him sufficient enough advice that it would help mend their marriage, and we would part ways. No harm, no foul. We hadn’t even met in person yet.
But it didn’t. We met up for drinks at a hotel in the city, with no expectations as to what would happen. After so long of just talking, it was time for us to actually meet. If it went poorly, that was most likely the end. If it went well … well, neither of us had thought that far ahead. His wife was out of town for a conference, and I trusted that he would remain a gentleman. We both obsessed and overthought everything, trying to come up with justifications, rationalizations, anything to make this seem less bad. But I couldn’t resist him. I wore an outfit somewhat reminiscent of Wonder Woman: cobalt blue shirt dress, red peep toe patent leather wedges with gold heels, and gold jewelry, most notably, a braided tricolor gold ring around my thumb. I needed to feel powerful; in his real life, he was a powerful man, from an affluent family, and I needed to feel like I could go to bat with the big boys. He wore jeans, a button down, and Ferragamo shoes, looking like the perfect after-work drinks companion.
It took a few drinks for us to settle down. There was obvious sexual tension. I had settled into the corner booth with my knee firmly touching his, to establish my place as the un-timid, unafraid girl who was not going to sit there and giggle politely at his jokes and let him walk all over me. We spent hours going back and forth with stories, each of us learning more and more about the other. He was a sharp, clever, quick witted man, even if he was shaking like a leaf. Our chemistry was undeniable, even the waitress could see it. Every time someone took a bathroom break, because we were drinking like there was no tomorrow, there was frantic texting of things we could not say out loud. I knew that he wanted me. I knew that I needed him like I needed air to breathe. We kissed breathlessly outside of the bathrooms as he pinned me against the wall and drank in the scent of my skin, the curve of my waist. He pulled me close and whispered filthy things into my ear and I was writhing, my lace panties soaking wet but untouched. And it couldn’t happen. He wasn’t ready to cross those lines with me.
By the time we left, it was almost 2 am. We were drunk. I had foolishly driven in, and we ambled towards my car to call him an uber home. We sat. We kissed. It was a blur of clothes and hands. He threw my mouth towards his crotch, revealing his cock outlined in his jeans. I asked to unzip him. He swatted my hands away, and told me to simply “Kiss it.” I obliged, but teased him hard. I kissed the outline, running my lips and tongue around the tip down to the base, all through his jeans. He moaned, pulling me back up for kiss after kiss. I had my hands tangled through his hair, down the buttons of his shirt, to reveal the thick fur on his chest. I gasped, out of pure happiness; I like my men furry. He moaned again, something about how this shouldn’t be happening, how he should stop me, how I should behave myself. We both got off on the illicit nature of all of this. Before I knew it, I had his throat in my hand. I asked him if he thought he could handle being choked, carefully, by me of all people. In a husky voice, he whispered, “Harder.” That’s all I needed to find his arteries and gently but firmly start to make him fade. He pinched me when it became too much. I let him sit, my hands around the back of his neck, holding his head steady as he breathed heavily and came back to me. “I want more,” he managed to choke out. I shook my head. Tonight was not the night.
We made out and petted each other for almost two hours in my car, the windows creating a picture perfect scene out of Titanic. Eventually, we realized the time. I had to be home. He had to be home. He called his uber. I sobered up and drove home. I was soaring for days, unable to come down from the feeling that I’d almost just fucked the very very married man of my dreams. The fact that I couldn’t have him made me want him even more. And we didn’t stop talking.
Next time on Teddy and Kitten: The Second Date.
Source: reddit.com/r/gonewildstories/comments/6oz8g7/teddy_and_kitten_the_first_date_mf_m36_f23_long
Superbly written. I’m looking forward to the next instalment with great interest.