Catching up with an Old Friend

Roughly six weeks had passed since I broke up with my ex of several years. Since we had lived together, I ended up moving back home until I found a place for myself and got back on my feet. Now back in my home town, I took it upon myself to get back in touch with some old high school friends. One such friend, Drew, had contacted me a couple of weeks prior, but I had not spoken with him since. But tonight I had plans to meet with a group of friends I hadn't seen in a couple of years, including an old crush.

Upon arriving at the bar, I was surprised to see only half of the people I was expecting. Initially we had planned on a group of 8 to get together for drinks. I only saw three people sitting at a nearby table. As I approached I noticed that two of them were a long term couple, Hal and June. The third was my old crush, Ali, who currently had a boyfriend. After brief hugs and hellos, Hal explained the circumstances of several of the absent guests, while Ali explained how her boyfriend was feeling under the weather. Realizing it would just be the four of us, I thought now would be a great time to flirt with Ali.

We started with a round of beers and some nachos. June suggested a shot since it had been so long since we had all hung out. After a round of tequila shots, and another round of beers, everyone was feeling loose and the conversation was flowing smoothly. Though we hadn't seen each other in several years, it felt like hardly no time had passed.

Feeling rather comfortable, I would playfully touch Ali's leg or arm here and there as we talked and joked around. As I fell more and more under the influence, I began catching myself staring more and more at Ali. She was short, maybe only 5'2. She had very nice perky C sized boobs, and a very fit body from years of varsity soccer and cross country. Her skin was incredibly soft, and although I wouldn't say she was tan, she had a very nice complexion.

Just as we were really starting to get caught up in one another, something caught my eye from the corner of the bar. As I glanced over, I recognized the two guys who had just walked in. As I processed who they were, Hal stood up from his seat. "Nice, John and Drew are here. I texted them and said to come by since everyone else bailed out." Hal motioned to the two, signaling them over to our table.

My heart began to race in my chest as I watched Drew approach the table. It had been just about two weeks since our encounter and we had not spoken a word about it. How was I going to handle both Drew and Ali? Was Drew even going to say anything? I took a deep breath as Drew and John pulled up seats and plopped down at our table. Much to my relief, John immediately began by delivering a story of how they had just been kicked out of the last bar they were at. It took maybe five seconds to realize that both John and Drew were highly intoxicated, and suddenly I was much more at ease.

After a few more drinks, John decided to head home. The remaining five of us ordered one more round, and at this point it was very obvious that Drew was just about done. He hadn't said too much over the past hour, and much of his reactions were mere nods or mumbles. I took Hal aside, suggesting we bring Drew home and take the girls back to someones house. Hal obliged and we headed out.

We dropped Drew at his house and made sure he was able to make his way inside before we headed to our destination. By this point, June was also on the verge of passing out, and Hal said he was going to take her home. As I put the pieces together in my head, I realized that I couldn't bring Ali back home since I was living back with my mom, and I couldn't go to Ali's place because her boyfriend was there sick in bed. Hal, also realizing this, said he would separately drop us off. Knowing that it was now or never, I decided to make a move on Ali.

We were both in the back seat and were already sitting close to each other since Drew had been the third person in the back seat before getting dropped off. I looked over at Ali, admiring her delicate features and supple curves. As she glanced over at me, I looked into her eyes. She looked back into mine, smiling. As we held the gaze, the smile slowly faded, her tongue wetting her lips before she slowly nibbled her bottom lip. Upon seeing this I ran my right hand along her cheek and jaw line, running my hand through her hair to the back of her head. I heard a short gasp before I pressed my lips against hers. I could feel Ali's body going weak as she pressed her lips back against mine, simultaneously pushing her chest towards me.

As our tongues began to swirl around, my left hand slowly glided along Ali's leg, across her hip and up her waist before reaching the bottom of her breasts. Just as I began to cup her beautiful bosom, Hal interrupted from the front. "You crazy kids might want to cut that out pretty soon." I quickly looked up, noticing we were turning onto Ali's street and would be at her house shortly. While it was unlikely that her boyfriend would be outside waiting, it's possible he would be looking out the window. I looked back at Ali, into her eyes. She smiled again, scandalously rolling her eyes almost as if to say "woops". As I withdrew my hands from her gorgeous body, she adjusted her clothes, gave me a small kiss, and exited out of the car.

The rest of the car ride was spent trying to contain to bulging erection in my pants. Hal knew I had a long term crush on Ali so he didn't say anything about what had happened. Upon dropping me off, we said our goodbyes. Once inside, I kicked back on the couch, unbuttoning my jeans and relieving some of the strain on my aching cock. I took out my phone, realizing I hadn't looked at it the whole time I had been fixated on Ali. There were two messages, both from Drew.

"Hey man, you guys still out drinking? I just sobered up a little, let's meet up." This message had come in nearly an hour ago. The next one had come in within the past ten minutes. "Drinks at your place?" While there were several aspects to take into account, I responded immediately.

"Yea, come by. My mom's in bed so come in the back door." My mother was a light sleeper and I didn't want to wake her, it was nearly 2am. By coming in the back door, we could easily go down to the basement where I had temporarily set up a room. Once Drew arrived, it was evident that he was still very drunk. I led him to the basement stairs, pointing to my room down on the left, as I returned to the kitchen to get us some drinks.

When I got down to the room, Drew was sitting on the bed, looking through my collection of DVDs and video games on the bottom of my book shelf. I handed him a rum n coke. "Looks like someone had a fun night tonight, huh?" Drew inquired, shooting a quick glance down at my crotch and raising an eyebrow. I looked down, forgetting that my pants were still unbuttoned and slightly unzipped.

"Oh, haha, woops." I laughed, slightly embarrassed. I sat down at my computer chair as I began to explain what happened with Ali. Drew, at one time or another, had also had a crush on Ali, so he was quickly able to understand my dilemma. After finally getting that far, then having to stop short, it can be quite a strain on the old cock n balls. As we talked about Ali, I could feel the bulge in my pants beginning to grow again. I took a deep swig of my drink, my other hand slowly sliding inside my pants and over my now throbbing cock. "Throw a movie on while I get us another drink" I said, standing up and reaching over to Drew for his glass. He had maybe a third of the drink left, but down it with one gulp. I took the glass from him as he grabbed a DVD from the bookcase.

I filled up the next two drinks, making them slightly stronger than the last ones. I was starting to feel pretty intoxicated at this point, and was wondering how Drew was even still up after the condition he was in earlier. Upon returning downstairs, I saw a movie up on the tv screen with the start menu playing over and over. I glanced over at the bed to see Drew laying down, seemingly passed out, with the remote still in his hand. I chuckled to myself. "Drew. Hey Drew you alive buddy?" A very faint mumble was all I heard, but no real response. I set Drew's drink down on the stand next to the bed before placing mine at the computer. I turned off the light and hit play on the movie.

With Drew asleep, I decided to drop my pants and plop down in my computer chair. As I sipped on my drink, I found my hand slowly returning to the bulge in my boxers. I slowly began rubbing my cock, stroking the full length of it. As I continued, my eyes would quickly glance over at Drew to see if he was awake. After a few more minutes, and no movement from Drew, I unbuttoned my boxers, allowing my hard cock to spring free. I leaned back in my chair, now stroking my cock freely. I looked back over at Drew, thinking about the encounter we had a couple of weeks ago. Drew had seemed to enjoy it, but had mentioned nothing about it since. Yet tonight he asked to come over for drinks. He must have been getting at something, right?

I picked up my rum n coke, taking another heavy gulp. As I stroked my cock I couldn't help but remember what Drew's cock looked like. It had been magnificent. Without further hesitation I stood up out of my chair and approached the bed. I didn't bother to say anything, instead electing to poke Drew's leg and see if he reacted. Nothing. With that, I reached up and undid his fly. I slowly pulled apart the flaps of the zipper, sliding my thumb and pointer finger into his pants. Then there it was, the soft yet thick base of his cock. I wrapped my fingers around it, lightly moving it until I was able to free the head from his pants.

Just as his cock came into sight, Drew lightly shifted in his sleep. Taken aback by his sudden movement, I quickly jumped back, returning to my seat. My eyes stayed glued on his face, but he remained asleep. After about a minute, I approached him again, his cock still freely out in the night air. Looking down at it, I was surprised to see that limp, his cock was almost the same size as mine. When I had seen it before, he was already hard when he took it out. I was surprised to think that his cock could even grow to be so big, and the more I thought about it, the more I wanted to see it.

I looked up at Drew's face again, and he was still in a deep sleep. With my left hand still gripping my own cock, I leaned over the bed, placing my right hand around the base of Drew's cock and guiding my mouth right over his dickhead. I took his whole cock in my mouth, lightly sucking and pulling on it, stretching out the shaft. Within seconds I could feel Drew's cock beginning to harden. My head began to bob up and down on his still hardening cock. Each time I went up and down, I applied more saliva, making the motion easier each and every time. And with each and every motion, Drew's cock grew harder, thicker and taller.

Drew's cock soon reached the 9+ inches I had remembered, and with my right hand firmly gripping the base of his shaft, I was surprised at how much of his cock I was able to take in my mouth. I was also surprised by how much I was enjoying this overall. I had considered myself straight my whole life, yet here I was going down on this magnificently beautiful cock. I wanted nothing more than to make him cum again.

In inhaled as much of his cock as I could, gagging and spitting on it before going back down and licking it all up. Suddenly I wanted nothing more than this cock, and I don't know whether it was the alcohol or not, but I wanted it inside me. I slid my boxers down and stood up on the bed over Drew. With my back facing him, I bent my knees and slowly lowered myself down on his throbbing cock. I felt his thick head pressing against my tight asshole. As I went lower, I began to feel a sharp pain shooting up through me. I quickly lifted myself up, took a breath and slowly lowered myself back down. I felt the pain again, but this time it was less severe, and as I slowly pushed down more, I felt the pop of his cock entering my asshole.

"Oh fuck" I gasped, letting out a soft moan as well. I began slowly raising and lowering myself on Drew's cock. Once the pain had mostly subsided, I found myself going down further and further on his cock. Eventually I felt my ass cheeks land at the base of his shaft, and the head of his cock felt like it was in my stomach. Still firmly stroking my own cock, I began to increase the pace, bouncing my ass up and down on this rock hard cock. I could hear Drew's breathing becoming more rapid, but I was so turned on I didn't care to stop or slow down.

It was just as I heard my ass slap against Drew's thighs and balls that I heard him. "Whoa, what the fuck!" Drew exclaimed in a shocked voice. Before I had time to decide whether to stop or keep going, I felt hands grab each of my hips and suddenly Drew thrust his cock upwards. "Oh shit, oh fuck yea!" Drew shouted. He then began quickly pumping up and down, each time pulling my hips down to slam onto his cock. My own cock was harder than I had ever felt it, and I was jerking off like crazy. Suddenly Drew gave one last thrust, pulling me down hard and letting out a long "Aaaaaahh". I felt two ropes of cum suddenly shoot into my ass, as my insides began to fill with warmth.

Knowing that Drew had cum, I quickly hopped off of his cock and turned around the face him. With my own cock ready to erupt, I began shooting load after load of cum onto Drew's still erect dick. It was like no orgasm I had ever had. As I finished, I looked down at Drew's cock, now covered in both his cum and my own, and without a second thought I dropped down and licked up every drop. Once the mess had been cleaned up, we proceeded to get dressed. It was in the wee hours of the morning now, so I threw on a pair of pajama pants. Drew got up, adjusting his jeans and putting himself away. As he walked over to the door, he looked back over at me. "If anybody asks, you dropped me off earlier and we didn't see each other again tonight." And with that, he left.

As I laid down in bed, I couldn't stop thinking about not only the situation I had gotten myself into with Drew, but also what had happened earlier in the night with Ali. Both completely different scenarios, yet I was so incredibly turned on by both. In one situation I was the dominant one, controlling the short beautiful blonde and having my hands all over her delicate body. In the other situation, I was a passive whore, worshiping another man's cock and pleasuring him every way I could. If only there was some way to get the best of both situations. As the thoughts raced around in my head, I felt my cock coming back to life yet again.