Catching Up With an Old Friend Ch. 04

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.

Upon arriving home, I made a B-line for the shower, dropping my clothes on the floor and heading straight to the bathroom. After a quick shave and rinse off, I wrapped a towel around myself and headed out of the bathroom. Passing through the kitchen, I made myself a rum n coke before descending to my bedroom to get ready.

I entered my room, dropping my towel to the floor as I placed my drink down on my desk. I picked up my phone, seeing a few text messages pop up. Two were from Ali. "Hey! Can't wait for our fancy shmancy dinner tonight ;)", which was followed by another text reading "None of my bra's are comfortable under this dress, I dont think I'm going to wear one."

My dick immediately jumped, my head swirling as I imagined how Ali would look. A wave of excitement rushed over me. I knew I had to try and look good, although it would be hard matching up to her. I opened up an ironing board, setting my clothes atop it as I plugged in the iron. Once finished I threw my shirt on before picking up my phone to check my other text messages.

My eyes were quickly drawn to a message from Drew. After our few sexual encounters, I was still unsure of what our current stance was. The last time we had hung out, Drew had been beyond drunk and had fucked the daylights out of me. It was the first time I'd had another man take control of me. At the end of it, I blew a load on Drew's face. Though he didn't say anything, I could tell he was turned on by it. Since that night we had talked on occasion, but hadn't seen each other in person. After reading his text, I knew that would change.

"Yo man, I need to get drunk tonight, what you up to?" I hadn't heard from Drew in about a week, and couldn't think of a reason why he would want to drink so badly. Either way, my night was already full.

"Hey, I actually have plans with Ali tonight. What's goin on?" I replied, letting Drew know I was busy but not that I was blowing him off.

"Oh, cool cool. Well let me know when you get home, I won't need long." I reread over Drew's text message a couple of times before it's true meaning registered. Drew wanted to come over and use me to get a nut. Part of me was instantly exciting. For the first time Drew was openly acknowledging coming over to fuck, and he wasn't drunk yet either. At the same time, I was a little irritated by his phrasing, saying he was just going to come and use me and basically leave. Then it hit me. A light bulb went off in my head as I realized tonight was the night that I had been planning for. Tonight was the night when everything would reach its climax. I huge smirk crossed my face as I replied to Drew's last message.

"Absolutely. I won't be out too late, feel free to get started without me." I wanted to make sure Drew was as drunk as possible by the time I arrived, so I encouraged him to drink every chance I could. With the groundwork now laid, it was time to get the night's events rolling. I finished getting dressed and set out to meet Ali for dinner.

I arrived first, taking a seat at the bar and ordering a pair of drinks. It wasn't long before Ali caught my eye. As she walked through the door, my eyes slowly traced over her body, starting at her feet and slowly working their way up. She had on a pair of black stiletto heels which did an incredible job of adding length to her legs. As my eyes continued up her legs I admired her long gorgeous crimson red dress, tightly fit accentuating her curves. She was wearing a short little black coat, with her blonde her straightened and down one side. I almost couldn't believe this girl was here for me.

After realizing I was staring, I approached Ali and offered to take her coat. In just the dress she looked absolutely incredible. We took seats at the bar, finishing the drinks I had ordered before being seated at a table. We ate light, spending most of our money on wine as the sexual tension from lunch continued to grow. By the end of the dinner, we couldn't wait to tear into each other.

Upon leaving we found a cab. Ali had said Noah was staying at his parents' house for a couple of days due to the fight they had had. I was reluctant about going to their apartment, but wanted Ali so badly that I agreed anyways. Upon arriving, Ali entered the apartment first, making sure no one was home while I walked up and down the street for a couple of minutes. A text message from Ali let me know that the coast was clear, so I entered her building and ascended the stairs to her unit.

Upon opening the door, I was unable to take two steps into the apartment before noticing Ali standing a few feet from the door. Just as my eyes landed on her, her red dress dropped to her ankles. I froze as my eyes ran up and down Ali's gorgeous naked body. She stepped out of the dress, still wearing her long black heels. My eyes continued up her legs along her thighs. She stood sideways, slightly rotating her hips to give me a glimpse of her ass. She was wearing a black lace thong, most of being swallowed up by her beautiful round ass. Before I knew it I was running towards her.

As I got to her, Ali jumped up, wrapping her arms and legs around me. My hands immediately went around her and under her ass, firmly squeezing her cheeks while holding her up against me. Her bare naked breasts pushed into my chest. They had to have been 36C's, which are quite large on a girl as small as she is. We feverishly made out, swirling our tongues around in each other's mouths. As we were still standing in her hallway, I wanted to take her somewhere but didn't know the apartment layout. I opened my right, glancing around as Ali still swirling her tongue around mine, licking at my lips. I saw a bedroom, but felt it wouldn't be right having sex in her and her boyfriend's bed. I then opened my left eye, seeing what looked like a living room around the corner.

As I walked into the living room, Ali still in my arms, I could feel that she was trying desperately to unbutton my shirt but was drunkenly fumbling with the buttons. She was giggling about it, so I decided to take matters into my own hands. I set her down momentarily, reaching inside my shirt with both hands and ripping the front open, sending buttons flying across the room. I felt like Hulk Hogan, which for a guy is a pretty damn good feeling. Ali let out a loud gasp, staring at my now defined chest and what I like to consider manly chest hair. She ran forward at me, tackling me onto the couch behind me.

As I fell down, Ali straddled me. We continued kissing as my hands made their way all over her body, firmly pressing against her thighs, squeezing her ass, and pinching at her nipples. She slid her arms over my shoulders and down my back, sliding my shirt off of me. She was slowly rocking her hips back and forth, grinding against my now rock hard cock. After a few moments, she slid down off of me onto her knees. She slowly undid my belt and zipper with one hand as she stroked my cock through my pants with her other hand. She had barely begun to pull off my pants before my cock sprung out. I pushed my hips up, helping to slide my pants down to my ankles. Ali turned her attention towards my pleading cock.

Ali took my throbbing cock in her hand and began lightly stroking the shaft. I'm uncircumcised, and Ali immediately took advantage of that. She slowly licked the underside of my cock, bringing her tongue up to the tip, and flicking at the foreskin. As she continued pumping my cock, she opened her mouth wide, placing it over the tip of my cock before pressing her lips down against it. I then felt an incredible sensation. Ali was pushing her tongue inside my foreskin, swirling around against mushroom tip of my dick. My eyes rolled into the back of my head as I tilted my head back. Not long after, with my cock still in her mouth, Ali pulled down on my shaft, pulling my foreskin back, but keeping her mouth and swirling tongue on my cock head. She then began bobbing up and down while stroking at a different pace. The combination of sensations was unlike any I'd ever felt. I couldn't take it any longer. I reached down and took hold and Ali's wrists, ushering her to come up.

Ali looked up at me, smiling with her eyes. She gave a few more sensuous swirls of her tongue around my cock before slowly grinding her body up against me. She slowly slid up, dragging her tits up against my cock as she did so. Eventually she was straddling me again, her gorgeous natural tits now in my face. Ali reached down between her legs, sliding the fabric of her lace underwear to one side, as she gripped my cock and placed it at the entrance of her pussy.

I could feel the heat coming off of her. I could tell before I was even inside her how wet she was. My hands again had a mind of their own as they caressed her body. Ali would slowly lower herself down, allowed her lips to press down over my cock, before lifting herself back up. I wanted so badly to thrust myself inside her, but at the same time the teasing was incredible. It was incredibly arousing, and the more she kept it from me, the more I wanted it.

On the fourth or fifth effort, I felt Ali's pussy slide further down my cock. At first I thought it might just be another inch or so, that she would continue teasing me, but she pushed her pussy down further. Then, almost out of instinct, my hips shot forward. My cock thrust up into Ali's pussy as I drove almost my entire length inside of her. She let out a gasp, quickly pulling herself up, before quickly slamming back down. Her ass cheeks slapped against my thighs, the sound of her wet pussy now evident. And with that, we were off.

My hands firmly gripped Ali's hips as I pushed my own forward, leaning back as far as I could on the couch. She would bounce up and down on my cock, slamming her pussy down on my throbbing member, stopping every few moments to gyrate her hips and grind back and forth. I would pull her towards me, pulling her tits to my face, sucking on her nipples, playfully biting at them. With her tits in my mouth, I reached behind her, grabbing and spanking her ass, trying to make each smack louder than the last. "Ahh fuck! Yes! Yes, harder!" Ali would shout, digging her nails into my back, clawing at me as I continued to thrust my cock into her.

Ali leaned turned to the side, hopping off of me and positioning herself on the couch facing the back, her ass sticking out facing the remember. I knew exactly what she wanted, jumping to my feet without hesitation. I stood behind her, admiring her gorgeous ass, still accentuated by the lace thong she was wearing. I reached down, again sliding the fabric slightly to the side before reaching under and lightly rubbing Ali's pussy. She was soaking wet, and that got me incredibly worked up. I rubbed around her pussy, gathering her juices on my finger before slowly sliding up to her clit. I began slowly rubbing her clit with her natural juices as I could hear her whimper. I removed my hand, instead gripping my cock, and placed it at her opening.

I placed both hands on each of Ali's asscheeks, lightly spreading her open, allowing my cock to easily glide into her pussy. As she had done to me, I ever so gently inserted just the head, barely breaching her lips, before withdrawing, and then again lightly pushing back in. I could sense her arousal with every "ooh" and "aah" she let out, until finally, as she had done to me, I slammed into her.

Because of how wet she was, my dick easily slid all the way into her busy. My thighs slammed into her ass, my balls slapping loudly against her pussy. "Oh fuck!" Ali screamed, her face being pushed forward into the couch, muffling her screams. I firmly gripped Ali's ass as I continued driving my cock into her. Her head slowly sank down the cushions, her ass pressing higher into the air. I began to loudly spank Ali's ass as I pounded her pussy. I looked down at Ali's face, which was now turned to the side. "Oh fuck, oh my god yes, fuck, fuck me, yes." I could hear Ali saying as she squeezed her own tits, firmly squeezing her nipples.

Upon seeing this, I was ready to blow. "Oh fuck baby I'm gonna cum." My thrusts began to become longer and slower. "Ohh fuck yes, where do you want it?"

"Oh yea baby? You're gonna cum for me? Yea, I want you to cum deep inside that pussy, I want you to make this pussy yours. Yea, fuck me."

I had never heard Ali talk so dirty, but those words were all I needed. I firmly slapped Ali's ass with both hands, squeezing her ass cheeks and thrusting my full length inside of her. "FUCK!" Ali screamed.

"Ali?! Ali, are you okay?!" My head darted to the side. As I looked out towards the hallway, I saw Noah walking forward, picking up the red dress Ali had removed moments earlier. "Ali, I heard screams, are you.." Noah's voice trailed off as his eyes turned towards the living room. It was in this moment that I realized I had forgotten to close the door behind me when I first entered Ali's apartment. It was also in this moment that I realized I was about to full out blow my load inside Ali. With Noah staring at us, my knees went weak as I pushed my cock as deep inside Ali's pussy as I could. I felt load after load shoot out of my cock, each one further weakening my legs.

"What the fuck?!?" Noah shouted across the room. With my orgasm almost done, I pumped my cock into Ali two more times, fully relieving myself. "What the fuck is this!!" Noah again exclaimed. This time Ali turned and jumped up from the couch. She must have been so caught up in the moment that she hadn't heard him at first, especially with her head buried in the couch.

"Oh my god, Noah!! What the fuck are you doing here?! Get out!" Ali screamed, covering herself with a pillow from the couch as she stood up. "You can't just fucking show up here unannounced!" As Ali stepped away from the couch, a glob of cum fell from her pussy, splattering on the floor. I could see that Noah noticed it, but didn't want to acknowledge it.

"Unannounced?! I fucking live here! We've been arguing for one day, I come over and this is what's going on?!" Noah gestured over to me. Realizing my pants were still around my ankles, my shoes still on, and Noah and Ali being more caught up yelling at each other, I took the first out I could get. I quickly pulled my pants up to my waist and made a B-line for the back door. "Hey where the fuck do you think you're going?!" I heard Noah's voice trailing off as I ran as quickly as I could down the back staircase, practically jumping down each entire flight of stairs. As I exited the building, I made my way to the nearest main street in hopes of flagging down a cab. Though I didn't have a shirt, I had my pants, which meant I still have my phone, my keys and my wallet.