Regrets. I've Had a Few...
Erotic Couplings Story

Regrets. I've Had a Few...

by Georgeburdell 18 min read 4.7 (2,200 views)
mf teen affair romance oral oral sex anal sex hotel
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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 like a minor change, but it shook up my routine both at home and on the road. I wasn't used to being at 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. Sports. Dreams for the future. Everything. And through it all, I slept every night dreaming that it was me cast as the man in her life.

Until her senior year that is. The day after my eighteenth birthday, I finally eked out enough courage to confess my feelings to her. It was a seminal moment. We were both adults now and the possibilities were endless. 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 favor. 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.

We met up on the Friday of Thanksgiving weekend at her parent's place that year. Her parents and sister were visiting her grandmother for the night, so we had the house to ourselves. A few drinks later, we were cuddled up on the couch watching TV when she started crying.

"Why do I always wind up with losers like that?" she asked between sobs.

"Hey, we all make bad decisions sometimes," I said, trying to be reassuring.

"You're not like that though, are you?" she asked, looking me dead in the eye.

"Never," I said with conviction. "I'm a lot of crappy things but a physical abuser isn't one of them."

She leaned in and kissed me. It surprised me, because I really wasn't expecting it.

"Oh God, I never should have let you go when I had the chance," she gasped as she broke the kiss.

My head and my heart (supported by other parts of the anatomy!) were in conflict. On one hand, there was the definite opportunity to move forward with the girl of my teenage wet dreams, but on the other hand I didn't just want to be the rebound guy scoring with the drunk.

"Jillian," I said in a halfhearted tone. "Are you sure you want to do this?"

She kissed me again in response, her tongue battling with my own as her hands began to unbutton the front of my shirt. She finally pulled back panting after a full minute.

"Tell me how I can thank you for saving me Georgie," she asked coyly.

This set off alarm bells in my head. It just felt wrong to try and take advantage of her in this situation when she was clearly still struggling with the scars of her last relationship, no doubt exacerbated by the alcohol.

"Jill, listen to me," I said firmly. "You don't need to thank me for anything. That's what friends are for. I couldn't live with myself if something had happened to you."

"Oh bullshit," she retorted in a harsher tone than I expected. "You spent all of high school trying to get into my pants and you're going to turn me down now?"

This was going downhill quickly. I pushed her away gently and stood up.

"Listen Jill, I think it's best if I head home now. I don't want to say or do anything both of us might regret later."

"Noooo," she wailed as the tears returned. "Don't leave. If you stay, I'll let you do anything you want."

I will admit I was tempted a little. "Anything you want" is such a vague and open-ended promise that any young male would be a fool to turn it down. So maybe I was a fool.

"No, it would be a bad idea," I said as I quickly buttoned my shirt back up and started heading for the door.

"Wait!" she wailed again from the couch. She pulled her shirt up over her head, baring her breasts to me for the first time. "Do you want to titty fuck me? I'll let you do that if you want."

I turned away.

"Enough Jillian, please. Let's just talk tomorrow when we're calmer and sober."

She stepped off the couch and pulled her shorts down next. She wasn't wearing any panties, so her bush of dark curly pubic hair came into view.

"Look at me Georgie. This is all yours. You can do anything you want, and I won't object. Just stay with me!"

I was at the front door now and turned the handle to open it. She came running up to me naked and tried to pull me back, tears streaming down her cheeks. I pulled her towards me and held her tight.

"Jillian, I can't do this right now, not with you in this state. Go get some rest. Let's talk tomorrow, ok?"

She sobbed into my shirt as I held her, my hands on her bare lower back just inches above where I would love for them to wander under different circumstances.

She eventually stopped sobbing and looked up at me.

"Oh God, I'm so sorry George. I uh, don't know what came over me," she spluttered.

"It's ok Jill," I said as I kissed her gently on her forehead. "Get some sleep and call me in the morning?"

She nodded, more composed now. I opened the door and squeezed myself out. As I walked down the driveway, I remember seeing her standing there naked, only partially concealed by the half open door, her face streaked with tears. I couldn't help but think that I had made the wrong decision by leaving.

She called the next day to apologise, but it was another crack in the structure of our friendship that we couldnt just ignore. I won't say that we drifted apart because we still stayed in touch as much as before, but there was something different about it yet again.

And so, life progressed. I went to grad school abroad, had my heart broken by another girl and came back home. My job had me traveling to a wide range of places, and on one of these trips I met my future wife. We married in a tiny ceremony with only family present, and I made her hometown my new base.

Jillian started seeing a therapist who did her a world of good. She met a guy and married him. I couldn't attend the wedding as it was during my grad school days, and I was overseas. She had three kids, but the youngest sadly died in infancy and she retreated from the world again for a while. Her professional life moved forward as she won a few roles in commercials and TV shows. She also became involved with the local semi-professional touring theatre group. Which brings us back to the present day...

Jillian was bringing her show to town. I smiled at the thought. It had been nearly three years since we last met, spouses and kids in tow as we tried to catch up over the din of an Applebees while I visited my parents for Christmas. We also texted each other for birthdays and anniversaries and when a particularly funny meme took our fancy, but I hadn't actually had a chance to sit down and really talk to one of my oldest friends for probably the last 20 years.

"ive got a show there on sat maybe catch up?"

I texted her back.

"that would be awesome! just you or rick as well?"

"just me. hes watching the kids. will save ticket 4 u. just 1?"

"thanks yeah just the one"

"great ill call u when we get in on sat morn"

"its a date!"

No sooner had I sent the last message did I regret it. A date? Dude, this isn't high school anymore. And you are both married. Shit, I hope she doesn't take it the wrong way.

My phone beeped.

"xoxo"

I let out a sigh of relief. Why did I worry? This was Jillian, she knows what I meant.

I woke up later than usual on Saturday morning and decided to do a load of laundry. One silver lining of the new work schedule was that the company put me up in a studio apartment rather than a boring hotel room. Not that I really used my kitchenette for much other than to heat up leftovers, but the extra space and appliances were a welcome addition.

I was just finishing up the folding around 11am when my phone rang. The display showed Jillian's name.

"Jillian! Welcome to Tulsa!" I answered.

"Georgie! How are you?" I heard an excited voice respond.

"I'm good. Going a bit stir crazy in this town but surviving. Where are you now?"

"We just checked in at the hotel. Are you coming to the show tonight?"

"I wouldn't miss it for the world. What time does it start?"

"Curtains at 630pm but I need to be there by two to run through the sets and all the other stuff. You remember the drill, I'm sure."

"Haha yes. Good times."

"Hey, what are you doing for lunch? Wanna grab a quick bite?"

"Sure, are you up for Chipotle? There's one just down the street from your hotel and it has a nice outdoor patio."

"Oooh yes. It's been so long since I've had a chance to eat out again, what with the kids and the pandemic and everything."

"Great. See you in an hour!"

"Can't wait."

I arrived at the Chipotle a few minutes early and found a nice table outside on the patio. It was the early days of summer, so the weather was pleasantly warm but not overbearing. I busied myself checking sports scores on my phone as I waited.

I spotted her out of the corner of my eye from about 100 yards away. Jillian never really walked anywhere casually - she was always striding with purpose. That had not changed. I watched with amusement as this bundle of energy bounded up the steps wearing a blue and white striped blouse with a pair of mom jeans.

I held out my arms and she hugged me tight. It felt good to hold her again after so long. The pandemic had really helped me better appreciate the small pleasures that basic human contact brought to my life.

"Oh Georgie, it is so good to see you again. It's been too long!" she finally spoke after nearly a minute of crushing me with her embrace.

"You too Jill, have you lost weight?" I asked. I couldn't actually tell if she had, but I know this is almost always a safe icebreaker.

She gave me a raised eyebrow as she giggled.

"You couldn't tell even if I had."

"Guilty!" I confessed. "But you do look good though."

"Enough flattery, I'm starving. The stuff on the plane was absolutely inedible. Can we go order?"

We went inside and placed our orders. Carnitas for her and Barbacoa for me, both in burritos. We collected the orders and sat back down on the patio to dig in.

"So how have you been keeping?" I asked between bites. "How are Rick and the kids?"

She hesitated for a second before answering, as if trying to decide how to respond.

"They are doing good. Well, physically at least."

I could sense something more.

"But?" I prompted.

She put her burrito down for a second and sighed.

"But Rick is really stressing me out. He's become one of those hardcore anti-vaxxers. I'm constantly worried about him getting sick, and now about him losing his job too. And it really stresses out Lauren too - she wants to get her shots when she turns 12 next month but she's worried about what her dad will say. So yeah...," she trailed off.

I shook my head gently.

"That sucks. I'm sorry."

"Ah well, it's what it is. What about you? How's Amanda?"

"Oh, she's fine. A bit stir crazy after having me underfoot at home for a full year, so I guess she's glad I'm back on the road now!"

"That's good. I'm happy for you guys," she said with a tinge of wistfulness.

We ate for a bit in silence, enjoying the gentle breeze and the company. I looked up and saw she had a smudge of sauce on her cheek.

"You've got something on you," I pointed out.

"Oops, where?" she asked as she pawed at the wrong side of her face.

"No, the other side!"

She moved her hand further up still on the wrong side.

I laughed and reached out to wipe the spot with my finger, holding it up in display.

"There we go, got it!"

She looked at me for a second and then gently pulled my finger towards her. She looked me straight in the eye, stuck out her tongue and then licked the sauce of my finger.

I laughed a bit awkwardly.

"Haha, that's one way of doing it I guess."

She blushed slightly but quickly grinned.

"Didn't want to waste a drop of the delicious sauce!"

"You know, I'm a real stick in the mud. I always get Barbacoa even though I've been tempted to order Carnitas a few times. Is it that good?"

"You've never had Carnitas? Here, try some...." She held out the burrito to me and gestured for me to take a bite. I hestitated for a brief instant, but then leaned forward and took a big bite. It was indeed pretty damn good.

We eased back into our old ways as we ate, as if the intervening years had just not happened. We chatted, we laughed, and we teased like only old friends who have no pretensions between them can.

A while later, Jillian looked at her phone.

"Shit, I need to go. The bus leaves for the theatre in 15 minutes. Can we continue this chat after the show?"

"Of course. I'll have the rental with me so maybe we can head out to dinner directly from there?"

"Perfect!" she exclaimed as she jumped up from her seat. She leaned over and kissed me on the cheek quickly and then turned to head out. I watched her stride away, her butt bouncing around at the back of her jeans, and for the first time in many years felt a pang for what might have been.

The show went well. It was a charity event of some sort, so there was a reasonable crowd, and I was pleasantly surprised by the production quality for this semi-professional production. It wound up around 8pm and I took a seat in the foyer to wait for Jillian to finish with everything backstage.

She emerged a few minutes later, having changed back into the same outfit she had been wearing at lunchtime.

"Did you enjoy it?" she asked excitedly as she approached me.

"It was excellent," I replied sincerely. "It's been so long since I've had a chance to watch you on stage."

"You flatterer," she laughed as she punched my arm gently. "I'm starving though, have you decided what we're doing for dinner?"

"How does Chinese sound? There's a place not too far away."

"Yes! Rick hates Chinese so we never order it at home. I'm definitely up for that."

We headed over to the restaurant and ordered our meals, deciding to share family style for convenience. We also ordered a bottle of wine between us, which arrived quickly. We clinked glasses and took our first sips.

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