Regrets, I've Had a Few...
Copyright© 2021 by GeorgeBurdell
Chapter 1
Romantic Sex Story: Chapter 1 - Jillian was the one that got away... or was it the one that I got away from? It's so hard to summarize nearly 25 years of knowing someone into a single label. So when I found out that she was coming to town and wanted to catch up, I knew that I had to meet up with her or I would regret it. And regrets were something that both Jillian and myself were familiar with from our past relationship.
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa mt/ft Romantic Anal Sex Oral Sex
The pandemic changed a lot of things.
I mean yeah sure, the big stuff changed. Masks, vaccines, testing ... all that kinda thing on a macro scale. But it also changed the smaller stuff. The routines and the relationships. For better or for worse, nothing was ever going to be the same as it was before.
One area that changed was the way my job handled our projects. It used to be the typical Monday to Thursday on the road lifestyle, home for the weekend, and then lather, rinse, repeat. Not anymore. Now it was three weeks on site, followed by a full week at home.
It seemed a minor change, but it shook up my routines both at home and on the road. I wasn’t used to being home when my wife was at work all day, and I wasn’t used to having to entertain myself on the road over the weekend. It wasn’t a bad thing to be out of my comfort zone, but it was just ... strange.
So it piqued my interest when I got a text from Jillian on a Tuesday afternoon.
“hey r u still working on that project in tulsa”
“yep still here”, I responded.
“oh kool u gona be around this wkd?”
“yeah its my onsite weekend”
“ive got a show there on sat maybe catch up?”
Ah Jillian. The one that got away ... or was it the one that I got away from? It’s so hard to summarize nearly 25 years of knowing someone into a single label. It is always more complicated than just that.
Jillian and I met in high school. She was a sophomore and crown princess of the drama club when we first crossed paths. While most of us in the club were amateur dilettantes at best, she had already made up her mind that acting was her calling in life and was determined to steamroll anything that got in her way. A few appearances in local TV commercials had cemented her place at the top of the drama club pyramid even as a sophomore.
So it was no surprise that the first time we met, it didn’t go well. Jillian didn’t have much time for freshmen to begin with, let alone upstart freshmen like me who were ready to challenge her authority. Suffice it to say that I didn’t have a clue how high school club politics worked and came away with egg on my face. Not literally, although if there were a role that involved standing still and being egged she probably would have cast me in it.
It got better from there. I guess we both matured from being confrontational teenagers into being more thoughtful young adults. I became her loyal lieutenant in the club. Whenever she needed something critical to be done, that task was delegated to me. I guess she was the first person to really appreciate my skills in project management - the ability to cut through the bullshit and get things done. My acting talents fell by the wayside, but I thrived on the administrative and technical side.
And through it all we became friends. Like really good friends. We’d talk on the phone at least every other evening and we kept to the same social circles so we crossed paths most weekends as well. I guess it was inevitable that I developed a huge crush. But the teenage me didn’t really know how to deal with that. I mean she was like the big sister I never had, so it would be wrong to admit having a crush wouldn’t it? So I played along as supporting cast, alternating between encouraging and consoling her as wannabe boyfriends came and went. We talked about everything. Boys. Girls. Sex. Sports. Dreams for the future. Everything. And through it all, I masturbated myself to sleep at night dreaming that it was me cast as the man in her life.
Until her senior year that is. I finally eked out enough courage to confess my feelings to her. It was a seminal moment. I actually recall feeling a physical weight being lifted off my shoulders. I think it confused her as well though. We kissed that afternoon, my first real kiss. I remember tentatively moving my tongue over her lips wondering if she would pull away in disgust, only to have her tongue reciprocate with an energy I never thought possible. But then again, Jillian never did things half heartedly.
The next few weeks had some of the highest highs and lowest lows of my teenage years. The day after we kissed, she told me that she wasn’t sure what her feelings were so we should take it slowly. I was crushed. But then a few days later, she called and asked me to a party as her date.
That was a fun evening. I don’t really remember the party much actually. We left early and decided to park somewhere. I put my hand on her leg as she drove and she gave me a strange look.
“Why don’t you be useful and put it a bit higher?”, I remember her asking.
So I did, and I remember running my fingertips over her jeans covered mound, marveling at how warm it felt even through the material. I kept going once we stopped the car, and watched in amazement as she eventually gripped the steering wheel tightly as she cried out with her orgasm, the first time that I had stimulated someone else to one.
She sorta returned the favour. We made out, fully clothed, as she rubbed her hands over the erection that was trapped in my own jeans. I came in my underwear pretty quickly and she giggled. I remember the feeling of euphoria at that moment. I was almost a man now. A woman had actually made me come.
That was a glorious few weeks. We sneaked out of drama club meetings early and made out after school. I got to feel up her tits under her shirt. She liked to rub me through my trousers as well and I got used to walking home with sticky underwear. But that’s all we did, fully clothed always, probably because neither of us had the courage to take the next step. Then suddenly one day the next month, she said that this was a bad idea since she was going off to college soon and we probably couldn’t make a long distance thing work. I didn’t know what to say, so I pretended to agree. We still remained close friends, but it wasn’t the same as it used to be.
Time moved on. We both went away to college in different places, her for drama and me for engineering. We emailed each other regularly, we called each other every couple of months, and we met up for coffee whenever we were home for vacations. She applied for some big theatre internships and scholarships, but they didn’t work out. She became more disillusioned as life began to carry her along with the current, rather than being able to steer her own course. Her existence devolved into a stream of questionable boyfriends as college became just another chore to get through. I tried to be as good a friend as possible, but I had my own life to live.
One October evening during my sophomore year, Jillian called me in hysterics. I could hear her boyfriend-of-the-month in the background screaming and I heard her say “put that down” before the call dropped. I called 911 and they sent a unit to her location. I’m glad I did that because it turns out the boyfriend was drunk and waving around a knife. That was the end of that relationship.
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