We met in college through my girlfriend at the time.  You were cute, and I was excited to see you around our dorm as you always had a smile on your face. For the first couple months, I saw you as a friend, until the late night conversations began.  To further fan the flames, we both occasionally worked the night shift where I would find myself staying up on nights that I didn’t have to work just to talk with you.  You had become a secret interest of mine. 

The conversations continued back and forth for weeks, hidden from those around us.  To that point, all we ever had was just that, conversations.  But that was about to change.  On a Friday night with mutual friends, I found myself in your presence. We were drinking some of the worst beer I’ve ever had; it tasted just like the aluminum can it was housed in.  Half-way through the case, everyone started to get hungry and I volunteered to go pick up some food.  When I arrived back, I knew I had missed something because the door was locked and “B” wouldn’t let me in right away. I casually asked what I had missed and was told “nothing”.  I didn’t find out until later that you decided to take off your top while I was away. 

The drinking continued to the point where the cardboard box used to store the beer turned into my outfit.  How I managed to squeeze into it is beyond me, but it served as a good laugh for those that were still awake that night.  In the late hours of the morning, things started to peter off.  People were falling asleep and returning to their own rooms. You had left and I was helping pick up the cans scattered about.  I noticed you had left your shot glass behind.  I saw this as my opportunity.  I walked down the hallway in only my boxers, and quietly knocked on your door. You opened it just a crack, asked what I wanted, and I told you I was returning your glass.  You had your body positioned in a way that only your face was showing, but smiled and invited me in.

I stepped in quickly as not to be spotted in the hallway.  It was only then I realized you were nearly naked.  I quickly sat in your roommate’s chair, and I could feel my cock begin to throb.  My heart was racing; I thought to myself “I can’t believe I’m doing this”.  The room was dark, with only the stray light from the street lights highlighting the walls.  You looked magnificent. Your breasts were perky, with puffy pink nipples. You had on lace panties that hugged your ass.  I still couldn’t believe I was in your room, with my girlfriend just down the hall.

We talked. You pried.  You asked me what we should do. I was paralyzed in thought, “can I really go through with this”? The look you gave me stunned, it was mesmerizing.  It practically begged for the response you wanted. My cock was now rock hard, but I just couldn’t do it.  I told you we should just talk, and that is what we did. For the next four hours, we lay half-naked on your bedroom floor bantering back and forth about who-knows-what. I remember falling asleep for about thirty minutes and then heading back to my room to shower.  While walking back I passed another guy on our floor, wearing only my boxers, and he acknowledged me with a head nod and a smirk.  He thought it was the walk of shame, but little did he know I couldn’t pull the trigger.

That night would haunt me for years to come.  I would always think back and say to myself “what if?”.  I was convinced that I would have at least done SOMETHING if presented the opportunity again.

Fast forward a couple of years and our online chatting would commence again.  It was riddled with sharing secrets and sexual chat.  You would tell me about your recent sexcapades and I would always push for more. I loved it, it made me hard, and also made me think back to the night that could have been.  By this time I was married, but you didn’t seem to mind.  You continued to entertain my need to occasionally catch up after months had gone by. 

I messaged you ever so often to see how you were doing, hear about your life’s adventures, and to live vicariously through your seemingly carefree lifestyle.  I especially loved it when you would send pictures.   I was reading you, trying to understand what I had missed out on years earlier.  I began to share more about myself, things only my wife knew about, and sometimes things she didn’t know.  It was great, and I always looked forward to seeing a notification that you had responded.

We half-heartedly joked that maybe we would run into each other sometime while I was traveling.  I wanted this to happen so badly, but it never worked out until recently.

I was set to visit the city you currently live in.  I told you that I would be in town and you responded with “I’d really like to meet up with you, if that’s something you’d be okay with”.  I know you were being polite, offering me an “out”.  It was more than okay with me, and it was the one thing I was looking forward to more than anything on that trip.

Once I was finally in town, we messaged back and forth deciding on a place and time to meet. I got a ride and waited patiently on a side street. Out of the corner of my eye, I spotted you, smiled, and we exchanged a hug.  We spent the night walking around town, you pointing out different landmarks while we caught up on our lives over that past couple of years.  We stopped at a bar for a beer and some chips, and the conversation continued.  I was so nervous I couldn’t eat, but I don’t think you noticed. I began to share secrets that I didn’t think I would ever tell anyone, the deepest of secrets that I held.  You countered with similar secrets; however, I wasn’t quite as surprised as you had always been so open.

We finished up and went for a walk on the pier.  The waves crashed and we watched airplanes land and take-off in the distance.  We continued to wander around the coolest of places late into the morning.  Staring into houses we could never afford, lit up but with no life inside.

We were back to the same scenario presented many years ago.  You had the same look about you, it was piercing. It was impossible to ignore.  I was at the proverbial fork in the road. Take one path and I cheat, potentially regretting it. Take the other path and do nothing, and likely regret it.  I was getting cold, needed to piss, and was starting to shake from the adrenaline as I had made up my mind.  I asked where we should go next and was delighted when you said your apartment.

We arranged for a ride to pick us up and head back to your place. It was agonizing. Stop after stop, it seemed like it was taking forever.  When we finally arrived, you made me wait downstairs. I was anxious, ready to commit to my decision.  And finally, there we were. You started to take off your bra and I removed my shirt. You had a wardrobe malfunction and asked for help. I was more than happy to oblige and assisted in removing your shirt. I was greeted by a perky set of twins. We began to kiss, caressing each other’s body. After a few moments, we each stripped down until we were completely naked. 

You laid there on the bed, and I made my way on top of you. We continued to kiss. I slowly worked my way down to your breasts and flicked your nipples with the tip of my tongue.  They were fully erect.  My mouth continued down your body until I arrived at your well manicured pussy. I began to lick your clit while pinching your nipples. You began to moan and ran your fingers through my hair.  I continued, licking circles around your clit until you couldn’t take it anymore and pushed me away. I had made you cum.

There was a break in the action for a few minutes while we both caught our breath.  I went back for round two, this time adding my fingers to the mix.  You were wet, and I had no issue sliding two fingers into your pussy. I could feel your g-spot becoming swollen and pressed it firmly as I lapped at your clit. Following another set of pleasurable moans, you pushed my head away while you came again.

I turned over on my back anxiously waiting for what would happen next.  You climbed on top of me straddling my legs. My cock was fully erect; there was no hiding my excitement.  You grabbed it without hesitation and began licking from the base of the shaft all the way to the tip. You commented on the size, which was flattering.  You placed the tip in your mouth and slowly began to slide it to the back of your throat. In and out. You would occasionally spit on the shaft and stroke me with your hand, which felt amazing. You neglected nothing.

You continued this for quite some time, and I began to feel something that is difficult to describe.  The sensation that you were creating was phenomenal, and my breathing began to labor.  I could feel my hands and feet beginning to tingle.  You continued to stroke my cock with your mouth. The tingling was spreading over my entire body and I was beginning to lose control.  I felt all of the muscles in my body begin to tighten until a reached a point where I felt paralyzed.  I couldn’t open my hands or hardly bend my arms.  During all of this, you never came off my cock.  You persisted until I absolutely could not take it anymore. The feeling was pure ecstasy.

You allowed me a few moments to recover, and began playing with my cock again.  We opted for a change in position, with you on your back and your head hanging over the edge of the bed.  I inserted my cock into your mouth and thrust until it stopped in your throat.  We continued this for a little while, and I think I even heard you exclaim “this is a good view”.  I then got back on the bed, lying on my back, and you began to straddle me again. I admired your body; the curves and tan lines. Your skin was smooth and I couldn’t keep my hands off of you.

You continued to stroke me. I could feel you grinding on my leg and felt a warm sensation. We both realized that you were incredibly wet, practically dripping from your pussy. You quickly fingered yourself and displayed the sticky juices between your fingers.  I had never seen a woman this wet before.  I grabbed my cock and began to stroke until I was about to cum.  You were gracious enough to wrap your lips around the tip while I unloaded into your mouth.  Without skipping a beat, you swallowed the entire mouthful.

We both lie there on our backs, staring at each other with smirks on our faces. You likely could have continued until later in the morning, but I was satisfied. This is where I was willing to draw the line, and you were okay with that.  We both lay casually for a while until your roommate’s cat interrupted.  By this time it was late, and I needed to get back and try to catch some sleep. We got dressed, walked downstairs, and exchanged a hug and a goodbye before I left. I was exhausted, but you couldn’t wipe the smile off my face if you tried.

Thinking back on that night, it fills a void that I didn’t really know existed.  Yes, I had thought about our previous encounter, years ago, many times. Fittingly, this seemed like closure.