Sometimes memories can be a good thing. Other times, they can be torture. Nostalgia is defined as a yearning for the past, often in an idealized form. The word's root is of Greek origin meaning "pain, ache" and it was actually treated as a form of melancholy in medieval Europe.

I point this out because I have been battling with an intense feeling of nostalgia lately regarding a past "lover". I wrote about her in a previous post entitled "My Best Friend's Girl" about a hand job she gave me in a hotel stairwell. This girl's sexuality and passion rivals that of the most motivated porn star - at least in my memories...

Currently she's engaged to a man much older than her, and while he is "nice" and "friendly", that's about all he has going for him. She used to be vibrant, spontaneous, fun loving and very enigmatic. He turned her into a couch potato who's idea of fun on a Friday night is staying in watching "Survivor" on the DVR. It's a shame actually, because this guy she's engaged to is technically her "rebound". If you read my previous post, she used to date my best friend for a number of years, and during their "breaks" was when we had our little romps. We never had sex, unfortunately, mostly due to my hesitancy to cross an imaginary line I had drawn for myself. That line still exists, and connects my regret with my nostalgia.

Despite never having had sex, she is easily hands down the sole occupant of my top 5 most intense sexual experiences. Ironic, right?

The one previously described in detail is up there in terms of ranking. This story is right there with it...

Rewind a few years. We used to hang out late nights - usually just watching movies, smoking cigarettes and pot, and complaining about our relationships. I was generally complaining about being the victim of unrequited love, while she bitched and moaned about her inattentive, unmotivated, unloving douche of a on again/off again boyfriend, aka my best friend. It was wrong being there, I knew that. But they were on a "break" and as long as nothing happened, it was all good, right? Wrong..

We ended up kissing late one night. Out of the blue, completely unplanned and unexpected. We both admitted later on that it was what we wanted all along. But we were fighting it. To this day, I think we still are.

But this one night, not too long after that first kiss, we were in her living room, sitting on the floor by her fireplace smoking cigarettes. This was because her mom, who smoked, would complain if we did in the house, so the chimney provided just the right draft to pull our smoke up and out without her mother ever knowing. I'll never forget - she was wearing all black. Tight, long sleeved, V-cut, sheer black shirt. And tight, form fitting, black "yoga" pants. As she bent over to put the cigarette out, I stared at her ass, and imagined it bare naked bent over in front of me as I pounded her pussy with my rock hard cock.

After she put it out, she took mine from my hand mid drag, sucked a final puff from it, then stubbed it out with the other one. She looked into my eyes with an intense gaze, exhaled, then leaned in to kiss me. I fought my instincts, and pulled away quickly. She looked hurt and upset, but I quickly starting explaining as to point out why I had done that.

I pointed out that we had both agreed to not "hook up" anymore. It was wrong on so many levels. We were both betraying my best friend in our own way, and being dishonest. But that sneaking around feeling is what made it so intense at the time, and we couldn't help it.

She announced her plans to leave for Florida in a month and to live with her grandma. All so she could "figure things out with my life" as she put it.

Well that did it. Her admission that she was leaving coupled with her ample cleavage staring me in the face eliminated any sense of impending guilt I'd feel or anticipate. I grabbed her and pulled her to me. I whispered "God, you're sexy" and we started aggressively making out. I ran my hands through her hair as her hands roamed my back and neck. I pulled her down on top of me - or maybe she pushed me down on my back - either way, I ended up laying down flat with her mounting me in the cowgirl position. We were both fully clothed, but I could still feel the wetness of her mound through her pants. I gently rubbed her clit as she used her hands flat on the ground to position herself directly on my hard cock. This girl has an amazing talent with her hip motions that I can only hope to experience further before it’s too late. In this instance, it was the standard example of “dry fucking”, but I’ll be damned if I don’t still jerk off to memories of it today. She ground her clit into my cock so expertly that I thought I’d cum right there in my pants.

She started picking up the pace, and I left it completely up to her to see where it went. Nowadays I’m prone to take charge in a sexual situation, but back then, and especially with her, I left it to her discretion where it would go. She started moaning and bucking even harder and for a quick moment, I thought for sure we’d start fucking for real right there on her living room floor with the chance of her mom, dad, brother or sisters coming into the room at any moment. That thought was hot, but it wasn’t to be…

After about 5-10 minutes of intense dry humping, she removed herself from off on top of me. We both caught our breath for the moment, but then her hands started traveling south. She started on my chest and ran her hands all over my torso and stomach, slowly making her way to my belt line. My mind was racing with what was the come. As she started unbuckling my belt, my cock did somersaults in my pants. When she undid the button and pulled down the zipper, I swear a stiff breeze would’ve made me blow my load all over right then and there. Next, she gently opened my pants up, and started rubbing lightly along my belt line which always turns me on. Then she took both hands, gripped the elastic, and eased it up and over my throbbing penis. At first, only the tip popped out, and I swear I could see disappointment on her face. We laughed years later when we relived the moment that she first saw/grabbed my cock because she thought “oh my God, it’s so small.” Luckily, she continued with the elastic movement, and eventually unleashed all 7” of my member, and I swear this time I saw her eyes light up.

We started kissing passionately again, and as she closed her grip slowly around my cock, I couldn’t help arching my hips up to meet her. She started stroking slow at first, but picked up the pace with an expert hand before I knew what was happening. No one, besides myself, has ever given such an amazing and complete hand job. She knows her way around a cock. Back then (and probably still today), I was susceptible to cumming quick whenever I was fooling around with a new girl, so I tried to slow things down a bit. I sat up as much as I could with her on top of me and her hand on my cock to kiss her neck and suck on her earlobe. I ran my hands up her stomach, under her shirt and bra to grip both titties in a firm and loving embrace. I squeezed them slowly, gently but with a lot of strength and vigor and her whole body tensed under my grip. I could tell she wanted it. But then she did what would become her MO. She picked up the pace with her hand, pushed me back, and started cranking away. I’ll never understand why she was so quick to want to make me cum, but at this point I wasn’t complaining.

I lay down again as she positioned herself to get maximum leverage while stroking my cock. She cooed in my ear and continued to kiss me deeply with her tongue circling mine as I let loose a massive explosive of cum into the air and all over her hands. She slowed down and squeezed tighter, still stroking and milking every last drop of cum out of my cock and onto her fingers. Then she did something I can still see in my head today – she took off her shirt, wiped my cock and her hand clean, then rolled it up into a ball and threw it towards the couch – all in one fluid motion! Then she whispered, “At least you won’t have to go home frustrated tonight” because we had joked about the blue balls I’d gone home with from all the hard core make out sessions we had shared prior.

This is just one of many experiences I’ve had with her. Too many if you ask me when you take into account that we never got to fuck and get it over with. There were close calls, and excuses. Begging and pleading. Missed opportunities that will always haunt me. My only wish is that she comes to her senses and either A) leaves this schlub she’s with now, or B) at least decides to finish what we started before she gets married. We always said it was something we would do before we die. I’m hoping it’s sooner rather than later.

I have a current gf who I love. I’ve been with her for almost 2 years, and marriage talks are starting up. But I don’t know if I can knowing I’ll harbor this regret and yearning in me every time I see this girl. Hopefully nostalgia haunts her too. Then maybe, just maybe, we can finally put it to rest.