Future Lovers

During a rather cold day in New York, I was sitting in my bedroom, getting ready for the most unlikely date I could think of. Jackson, my crush since High school, had asked me out. I was both nervous and excited, but also suspicious about it. I had heard rumors that he was dating another girl, and she did not really like me. Whether they were dating or not, I knew Jackson was making a mistake, seeing how that girl had a reputation of being fake, mean and manipulative. I am afraid she may be doing the same to Jackson.

Even if we are distant now, Jackson and I used to be like best friends. Our friends thought we would make a nice couple, and that kind of got clung onto me. After high school, Jackson became distant, and changed me for new friends, including that mean girl. Resentment soon grew from within me, but I could still see the same caring guy I had known for so many years, and I still liked him.

I painted my lips a chilled red wine, my long brown hair straightened to give edge to my face, and I put on a jacket over my pink shirt to be ready for the cold, finishing with casual jeans and my boots. I remember Jackson telling me how much he liked my relaxed fashion sense. I kept thinking about that while picking my clothes. We were going to a coffee shop, because his careful mind was smart enough to plan a date to go have a hot drink during this cold day.

Jackson had come back to town for only two weeks, before having to return to college. Having him away was both good and bad for me; I could get my mind off him for longer periods of time, but being apart for so long made me feel kind of uncomfortable around him, or just talking to him, whenever he was around. That, and the fact that he is seemingly dating a girl who hates me, and that I am not good with words yet have so much to say, make communication with him almost impossible. My mind is a wreck around him.

I tried to keep my cool. There must be a reason other than just catching up with me to ask me for a date; because if that is all what he wanted, then he could do so by text. I was feeling rather anxious already, overanalyzing the situation. All of sudden, I got a text from Jackson:

“I will be waiting for you at the café, I’m on my way there”

Then reality slapped me on the face. This was really happening, and Jackson was really looking forward to it. This seemed like something that would only happen in my fantasies. Without further hassle, I made my way out onto the cold streets of New York, to reach my destination and see Jackson for the first time in months.

I got there before I knew it. Maybe I tried to get there faster without realizing, for the thrill of seeing him. I spotted Jackson sitting on a table by the window, waving at me. With a smile, I approached his table then sat down.

“You look pretty today” He said as I sat down, putting his phone on his pocket. He was known for constantly using his phone, so the fact that he put it away made me feel a bit relaxed. “Thank you” I said softly. “You look good yourself” I added, looking into his eyes. It was harder than it sounds like.

We ordered some coffee and pastries, and talked for hours. Mostly about our childhood, college, and what we have been doing over the past few years. I was glad to find Jackson being a bit more mature about things; maybe college changed him? Regardless, it was as if I was talking to a better version of the same man. The upgrade. Then, bursting my naïve bubble, Jackson asked me:

“Have you been dating other guys?”

How dare he? How dare he break my comfort like that? Not only was I ashamed to say that I haven’t, I was feeling like I could not control myself from saying that he was the reason I did not want to see others.

“Not really, haven’t got time for that…” I said, looking away. “I heard you were dating that girl, Cynthia” I said, instantly getting his full attention.

“We did not really date. It was an on and off thing” he said confidently. “So she was like a fling? I thought you liked her” I said, then flinched. My words may reveal that I know more than he realizes, but he did not seem to care about my questions. “I did, but also we kind of were not meant to be, so we drifted apart” He seemed to be zoning out. “Do you want to go to my house, Dianne?”

I was in shock because of his question, but I agreed. We quickly got off the table, and then we took the train to his house. I was standing there, next to him. This was the oddest day of my life in recent times, because I totally thought Jackson hated me. While thinking about my entire life, we got to his house, which was suspiciously empty.

“I know we got distanced and I know I did not do the best to keep our friendship alive, but I regret it” He said, sitting down on the couch. “I understand you were busy, Jackson” I said in a broken voice, sitting beside him. “It’s not your fault” I said, lying to the months behind me where I spent nights telling myself that he was an ass. “It is my fault and I am sorry” He looked away from my face, and I looked down.

Before I could notice, in a swift motion, he held my face then kissed me. “Will you forgive me?” He asked, staring into my eyes. “I have been waiting for an apology, so, yes” I said, then kissed his shocked face. We continued to make out on his couch, then he took my jacket off. “It’s something I’ve wanted for a while…” He said, while caressing my hair.

“What is it?” I asked, and he stood up, proceeding to unzip his pants. As if I was psychic, I took his penis out of his pants, which was already hard, then began to suck on it. I was a newbie at this, so I did not really know if he would enjoy it, but his moans made me realize it was pleasuring. He bent down to kiss me, then proceed to undress me, and I just let him do it.

In the biggest twist of events, I had Jackson’s face on my pussy, eating it as if it was the last supper. I could feel his fingers slowly entering my wet pussy, as if he already knew the way inside my body. I held his head against my crotch as he went into it with his tongue, then he stood up to kiss me.

I spread my legs open on the sofa, then let him into me. He slid his penis into me, letting me feel something my fingers could never recreate. He thrusted into me swiftly and with passion, and he looked really hot while doing so. Added to this, his moans and groans turned me on like never before. This was my first time, but it was not awkward at all. It’s like we both were ready for it.

He pulled out, then I knelt in front of him instinctively to suck his dick once again. This time, I was more playful with my tongue, and grabbed his ass as I sucked. After a few minutes, he came a warm load into my mouth, which I swallowed completely. He held me up from the ground and kissed me, then we laid down on the sofa.

“I am glad we’re talking again” he said, panting. “I am glad you decided to show up” I said, then realized how blunt I sounded. We started to dress up, keeping in mind someone may come to the house at any minute now. After dressing up, we made out while standing up, and his phone began to ring. “Who is it?” I asked, and he did not let me see the screen. “It’s Cynthia…” He said, then muted the phone. “Aren’t you going to reply?” I was more concerned as to why she was calling than him ignoring her.

“I had told her I was going out with you. She may want to sabotage things a bit” he said, looking away. “I really don’t understand why she hates me. I don’t even know her and she just straight up wants to own you like property, then push me out of a cliff…” Before I continued my rambling, Jackson kissed me.

“The thing about Cynthia I told you about before, that we we’re not meant to be… I believe that is because she is not you” He said, then kissed me again.