The summer was winding down. After breaking up with my ex-girlfriend in the spring, I had looked forward to a long summer of random hookups and one night stands until I was ready to get back into the dating scene. While things didn't necessarily go as initially planned, I couldn't complain with how the summer had gone thus far. Since becoming single, I'd had a chance to get back in touch with a few old high school friends.
Having lived together with my ex, our separation forced me to move back in with my mother until I found a place of my own. I took up residency in the finished basement, thinking it would only a take a few months of saving before I was on my feet again. Not wanting to sit and dwell on my past relationship, I had tried to get myself back out there as quick as possible. Upon hanging out with old friends, I quickly found myself caught up in two intriguing situations.
On one hand, I had started a fling with an old crush, a short blonde with a sensational body and a fun personality. At the same time, I had gotten myself into a very unexpected situation with an old buddy, most of our rendezvouses ending with some form of oral or anal penetration, although neither of us "were gay".
Initially I had been very unsure of how to approach my predicament, unsure of how to proceed with each individual. As certain events unraveled, I found myself seeing more clearly how things needed to go. Knowing that the two relationships couldn't continue much longer, I planned for a night when everything would reach its climax.
It had been almost three weeks since I had first hooked up with Ali. Our first encounter, a drunken make-out in a cab, was followed by a little fling in a movie theater bathroom. Although Ali had a boyfriend, it wasn't enough to prevent her from acting on prior emotions from our high school days. I had always had a crush on Ali when we were younger, and only recently found out she had felt the same. I had been too nervous to approach her, her always having other boyfriends or being hit on by bigger, taller guys.
Now that we had finally hooked up, I couldn't get enough of her. Most of our hookups took place in movie theaters, bathrooms, or parking lots. Within seconds of arrival we would ravage each other, passionately kissing and groping. Ali's body was incredible. Petite and slim, with nice round tits and a round ass. She took care of herself and it showed. Each of our encounters so far had ended with Ali giving me a blowjob, or me fingering her or eating her out. I had wanted so badly to fuck her, but Ali wasn't going to make it easy, and knew how to really tease a guy.
The fact that Ali was still in relationship made it easier for me to accept the fact that she didn't want to have sex just yet. She was already cheating on her boyfriend with me, but having sex with two people simultaneously can take a toll on someone mentally. I didn't want to be too aggressive about the topic, so our oral hookups were more than enough for me.
As I sat on my lunch break at work one day, I received a text from Ali. "Ugh Noah and I just got into a huge fight, I really just cant stand him sometimes." I had only met her boyfriend Noah a handful of times, and I personally thought he was a douche. Since Ali was still dating him, I didn't want to blatantly bash him, so instead chose an alternative route.
"How are you doing?" I replied in a text. "Do you want to get a drink to maybe take your mind off things?"
"That sounds like a great idea!" Ali quickly replied. With that, we agreed to grab a bite for lunch.
We arrived at a nearby UNO's for lunch. I gave Ali a big hug, squeezing her tightly as we walked into the restaurant. After ordering a round of drinks and some nachos, we exchanged small talk. As we finished our first drink, the sexual tension between us had risen drastically.
"So what are we going to do now?" Ali inquired, taking a serious tone as she placed her drink down. I looked up at her, realizing she was clearly implying something. I considered the idea of going to a nearby bathroom, as we had at the movies, but also knew that several of my coworkers frequented this restaurant for lunch. It wasn't worth the risk. Knowing I had to be back at work in roughly fifteen minutes, I tried to think of a way we could prolong the festivities until later that night.
"The first thing we're going to do is order another drink." I smirked, signaling to our waiter. A smile crossed Ali's face as she nodded. "And then tonight I'm going to take you out for a nice fancy dinner. We'll get dressed up, get a bottle of wine, order some fancy food, really make a night out of it." Ali giggled to herself at the suggestion, noticeably buzzed from her second drink.
"Ahh that sounds amazing. I haven't gotten dressed up in so long. Let's do it." Ali had a big smile on her face, daydreaming about the idea. I could only smile as I looked back at her. After paying the tab, we said our goodbyes, heading back to our respective workplaces, each with daydreams floating in our heads.
As I sat at work, still slightly buzzed from lunch, I couldn't stop thinking about my date. I was eager to get home, get ready and get out the door. Knowing we were dressing up, I planned on ironing my nicest suit and really playing up the "fancy" aspect of dinner.
