How Cara Learned to Stop Worrying

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Bored 30-something meets a seductive stranger.
4.2k words
4.35
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Part 1 of the 6 part series

Updated 09/22/2022
Created 10/10/2012
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phlight
phlight
23 Followers

(The following story is a work of fiction and as is the nature of fiction it's not realistic or responsible or any other R-words that keep the real world rolling round and round. I guess that's why they call them sexual fantasies. I hope you can keep it real and also enjoy the story. Inspired by a particularly detailed dream ...)

How Cara Learned to Stop Worrying – Pt. 1 – A bored 30-something meets a seductive stranger.

I could call this story the great romance of my life or the history of an unexpected connection that changed everything. Perhaps I could sub-title the tale, "How Cara learned to stop worrying and love..." Or I could be frank and say it like it is -- let me tell you about the hottest fuck I've ever had.

For starters, you should know that I have a tendency to be really boring. I spent my entire life up to the night of October 9, 2009 avoiding conflict and making other people happy. My childhood was unmarred by any great strife – I had two parents who tolerated each other, one amiable little brother, and a small circle of friends. I never broke a bone and endured only mild bullying because I never took physical or social risks. I was a straight A student not so much because I was thrilled by the subjects but because the thought of not getting As was unpleasant. This pattern of thought and behavior continued into university when I elected to major in accounting, because it was sensible and I'd be guaranteed a job straight out of school. My parents were pleased. I was bored.

My single act of "rebellion" – drunken, careless sex with my boyfriend on graduation night -- resulted in my son, Evan. I told myself to reap what I sowed, broke up with the boyfriend, and went back to the straight and narrow as soon as my baby was born. Desperate to make up for time lost during my pregnancy and maternity leave, and desperate to make up for what I perceived as a loss of my practical, dependable reputation, I plunked Evan into daycare and plunged headfirst into my career and adulthood. Not much changed for the next 14 years. I relied on my child to motivate me through life and relished seeing the world through his eyes. Yes, I had a small handful of boring boyfriends (all fellow accountants, all nice enough but distressingly one-dimensional in their quest to achieve the coveted title of PARTNER -- I was so bored at this point that the thought of labeling myself PARTNER'S WIFE reduced me to tears and always ended in a "It's not you, it's me conversation"). The concept of passion continued to elude me, so I decided to forget about myself as much as possible and focus on Evan. I did my best to keep him from inheriting my ennui by taking as many overseas excursions as I could cram into my work schedule.

I seemed to be doing well in that area, although I have to give Evan lots of credit for his natural talent. I was shocking myself this particular fall evening by attending my son's first lead role in a school play; shocked because this was certainly not something a young Cara would ever consider for an extracurricular activity – a spotlight on me? No way! After years of missing 75% of his class productions and performances as a tree, the letter U, or pilgrim #3 due to some "urgent" deadline at work, I settled into my auditorium seat to watch my son act with mixed feelings of pride and guilt. I had missed so much but I was able to be here for him tonight. True, I had to go back to the office after the show was over -- those deliverables wouldn't deliver themselves -- and Evan made it clear he was going out with a group of friends straight after the show and wouldn't need my embarrassing happy mother tears raining on his shoulders to crown his achievement. But still. I was here and I intended to be here a lot more. Evan's father, Reed, had moved to another state for a job opportunity and wouldn't be able to take up his usual role as Evan's cheering squad. I always tried to show Evan how much I loved him by providing for him behind the scenes, but in Reed's absence it was my turn to step it up and show my support for our sensitive, artistic son. I washere.

I flipped through the program forOur Town, noting the line "Evan Arkady as George Gibbs" with a small smile. As soon as I saw "Hana Nakamura as Emily Webb" I looked around for the one mom friend I had known since Evan was in kindergarten. I didn't know Sachi Nakamura very well -- we were friendly acquaintances that chatted at school open houses, and the most defining thing I knew about her was that she was a single mom, like me -- but I knew Evan was pretty good friends with Hana and that Sachi was probably bubbling over with pride at her daughter landing the lead female role. I didn't see her, but a minute or two before the lights dimmed the most exquisite male I've ever seen in the flesh walked through the open auditorium doors and headed straight for me! (I was seated near the door for a quick exit after the kids took their final bows and it was nearly a full house -- one of the last open seats was the one next to mine. Lucky me.)

As he took his seat and nodded a quick "hello" my way without really seeing me, I nearly did a double take. Not only because he was strikingly attractive, but because I realized he was Sachi -- or what Sachi would look like if she was a man. He noticed me noticing him and offered his hand, eye contact, and a deep, warm voice.

"I can't believe the traffic out there! Hi, I'm Keiji Nakamura."

At first I couldn't speak. I think I was staring too hard. You guys, this guy. Was so hot. I know I'm supposed to show you and not just tell you, but take my word for it up front, okay? I took his hand and started as I felt an electric sensation go up my arm at the contact. I dropped his hand like a hot potato.

"Uh," I replied, trying to recover my senses. "Hi! Y-yes, you just made it in time. Are...are you Hana's dad?"

He smiled, revealing even, white teeth. "No, no. Just Uncle Keiji. My sister's got a bad cough but hopes she can make it to tomorrow's show. She was spitting nails about not being here for Hana, so I'm filling in. I don't know if I'll be able to clap as loud as she would, though."

"Oh," I said, gazing at his mouth. I was on my conversational A-game, that's for sure. Embarrassed at being so flustered by him, I looked down at my program and tried to appear engrossed.

"So, do you know Sachi?" he continued. "My sister?" I wished he would stop looking at me so I could think. I managed to speak again, somehow.

"Oh! Yes. I do. I'm sorry, brain fart. I'm, uh, Cara Brennan, my son is Evan Arkady. He and Hana, um, go way back to kindergarten; um, I've known Sachi since then. Nice to meet you." I tried to sound chipper, but my voice trembled and I was talking too fast between pauses to "um."Brain fart? What in the hell is wrong with me?

"Nice to meet you, too," he said, smiling again. Did I detect a hint of amusement in his voice? Oh god. Well, of course a person that looked like him was probably used to having this effect on dorks like me. "I've met Evan several times--" he began as the lights went down. Saved by the AV club kid. Phew! Keiji sat back in his chair and directed his eyes forward. I tried to do the same as the Stage Manager began to introduce us to the town of Grover's Corners.

Ugh. After my thirty second conversation with Keiji Nakamura, I was definitely too warm. I was wearing a black leather blazer over a form-fitting, grey stretch cotton dress with three-quarter sleeves and a hem just above the tops of my knees. Tall black leather boots completed the look (with a sensibly low heel, of course.) To avoid sweating on my work dress, I decided to take off the blazer. It was just the littlest bit too tight and I had to wiggle and turn a bit to get it off in my seat without elbowing the lady to my left. As I turned toward him I saw Keiji's attention go from the stage to my breasts. No way, I'm only a B cup! Nothing to write home about, and the neckline of the dress wasn't revealing at all. I guess they were straining a bit at the fabric of the dress as I struggled with the jacket, though.

Feeling warmer than ever, I finally got the stupid thing off, shoved it behind me, and crossed my arms over my chest as I tried to settle back and pay attention to the play. I managed to be a good audience member long enough to watch my son and Hana during the first act. They were fantastic, in my completely unbiased opinion.

As Act One wound down and the Stage Manager let the audience know we could have our smokes if we wanted (insert laughter here), I lost my mind. That's the only way I can explain my behavior, unless I want to blame pheromones or the alignment of the planets or hypnosis.

There wasn't much of an intermission between Acts One and Two, but I spent those few moments sneaking sidelong glances at Keiji while he browsed through his phone messages. He was just too good-looking for me to stop -- stylishly cut black hair with layers slightly longer at the front framed his symmetrical face. His features were perfectly formed with the best eyebrows I think I've ever seen on a guy, full lips, clean-shaven. His eyes were deep brown and could be described as "bedroom." They made his expression seem somehow bored and sensual at the same time. Like I said, he reminded me of Sachi at first glance so he was perhaps too "pretty" by those of you inclined to go after Manly MenTM, but he was most certainly in possession of XY chromosomes. His body was slight but not too thin; he was wearing a black button down shirt, open at the throat, with black jeans and -- this made me smile to myself -- black Converse Chuck Taylors.

Or at least I thought I was smiling to myself, but when I raised my eyes from his feet to catch another peek at his face he wasn't looking at his phone anymore -- he was looking straight at me. I couldn't stop my eyes from widening and I looked away, feeling like he caught me at something.Why does this guy make me feel like I'm Evan's age? I am such an asshole.

Despite my embarrassment I couldn't stop glancing over every ten seconds or so. The situation wasn't getting better. Now it seemed like nearly every time I looked, he was looking back. It would have been creepy or awkward if I wasn't so turned on. Yes, I had to admit it; it was the only explanation for why I was feeling so out of composure. The last time I'd slept with someone or even seriously flirted had been over a year ago, shortly before I broke up with Adam the Auditor. Keiji was about fifty times sexier than Adam the Auditor.

In the last seconds before the lights went down, I looked at Keiji and saw that he had directed his gaze to my bare legs, which were slightly parted.Jesus take the wheel.I shifted forward in my seat so that the skirt of my dress would pull up, taking my hemline from sensibly above the knee to approaching mid-thigh. I looked at him to gauge his reaction: success! It was his turn to get wide eyes, and he checked my face to see if my little wardrobe malfunction was deliberate. I kept my expression neutral and looked at the stage. The auditorium went dark.

My heart was racing at my daring. I was turned on but also mystified by his attention. I mean, I'm not bad-looking for 35, maybe a 7 out of 10? I've been told I resemble Parker Posey. I'm 5'8" with shoulder-length brunette hair, a smallish chest (they may be small but I've always liked my boobs; my nipples are pink andverysensitive), a flat tummy on a small waist that flares into my worst or best features, depending on your taste -- ample hips, thighs, and ass. I've always had some cushion for the pushin' back there no matter how little I eat or how much I exercise. Yep. I'm a pear. I expected guys like Keiji to go after 9+ women exclusively. Like maybe Natalie Portman or Jennifer Lawrence would look cute with him. I dunno. I was not used to attention from someone I was so attracted to on a basic physical level.

I tried to pay attention to the kids --You are here for Evan, Cara. EVAN.-- and despite my excitement I succeeded for a time, until I felt a slight pressure on the side of my thigh. Could it be...? It definitely was. He was pressing the side of his leg against mine, his eyes still on the stage. I was getting more and more aroused, but decided to pretend like I didn't feel anything. Keiji would not be ignored. A few minutes later, he rested his left hand on his leg. It was nearly too dark to see in the auditorium, but I watched him inch his hand over until it was onmythigh. Just the touch from his leg against mine had sent thrills running through me, but at this point his hand might as well have been directly on my clit. I could not believe my physical reaction to what was really a pretty nondescript sensation. He started to slide his hand, and my dress along with it, upward. In my utter surprise I looked directly at him -- but he had decided two could play at my game and was still watching the stage. I looked back at my lap and watched his hand and my dress continue their slow upward journey together, all the way up, up, up, until my crotch would've been revealed if not for the bunched fabric of the dress between my legs. The crotch in question was throbbing at this point, and I knew I was wet. I was frozen, stupefied that this was happening but loving every second of it. He began to slide his fingers, long and graceful, over the side of my thigh and onto my panties. I silently thanked whatever deity watched after dubious sexual activity that I had opted for a cute pair that day instead of old Aunt Flo warriors, and I further thanked said deity for making sure I had trimmed my womanly hedges the evening before.

As Emily and George -- Hana and Evan -- began to teach the audience about the origins of their relationship, Keiji moved his entire hand onto my mound and lightly pressed down. Whatever my rational brain was thinking (and it was thinking very little at this point) -- about what kind of creep was this guy, who does this at a school play, what if the woman on the other side of me sees what is going on, is this how you treat a lady, won't somebody think of the children, etc. -- the insane part of me suddenly made a decision. I was going to fuck this guy. As soon as possible. I took his hand in my own, removed it from my body, and put it back on his leg. Then I put my hand on his jeans and felt what I had been hoping to feel -- a rock hard bulge straining at the denim. Mimicking his moves, I lightly pressed down. After confirming that we were on the same page I yanked my dress down, grabbed my purse, stood up, and brushed past Keiji. I whooshed through the double doors of the auditorium into the fluorescent glare of the school's main hallway. It was at this point that the spell over me almost broke.

A pair of students handing out tickets to stragglers looked my way as I stood there blinking like a deer in headlights. Rationality started to return --where are you, in a school, what are you doing in this school, you should be watching the play --and I started toward the direction of the parking lot and the sanctuary of my Toyota to pull myself together. That's when I heard the doors open behind me. I looked back and there he was, eyes locked onto mine. I felt a spike of arousal mixed with alarm. He smiled and held up my blazer, forgotten on the seat behind me. He was about to speak when I turned back toward the students and demanded, "Where are the bathrooms?!"

"Uhh...down that hall until you hit the guidance office. Then turn left. Halfway down is the teacher's lounge and then the girl's bathroom will be on your right."

I didn't pause to thank the kid, but turned on my heel and marched in the opposite direction of the parking lot, deeper into the school. As the insane autopilot took over my body again and thoughts emptied, I heard Keiji's footsteps following me. He didn't say anything to the students; they didn't say anything to him. Maybe they assumed we were together. Well. We were going to be together, soon.

I saw the guidance office and turned left. The deserted hallway echoed the falls of my boot heels and the softer steps of Keiji's sneakers. I walked faster; he matched my pace but didn't attempt to catch up to me. I realized I was panting as I approached the teacher's lounge, which as far as I could tell was a just a solid gray door set in a white wall. My autopilot allowed one thought to interject --There!-- so I grasped the doorknob and turned. It was unlocked and the door swung open into pitch blackness. I stepped through the doorway and took a few steps inside, stopping when I was out of the patch of light shining in from the hallway. Before I had time to turn around the light disappeared and I heard thesnick!of the door latching. Again I felt the stirrings of panic, anxious thoughts beginning, but then the lights came on with their familiar buzz. I turned and he was standing still, unsmiling, his hand on the light switch. I took a step toward him, part of my mind thinking,The door, you idiot!and the autopilot held silent...I took another step and was within reaching distance.

My blazer hit the floor with a soft slap and we were all over each other and I was laughing, exhilarated. He pushed me up against the cold cinder block wall of the teacher's lounge and kissed me, softly at first but growing in intensity until I felt my lips must be bruising. The movements of his tongue in my mouth described what he was planning for us elsewhere. He held me to the wall with the kiss while his hands slid down my body to their target -- again, the bottom of my dress. This time he was quick, and yanked the fabric up and over my hips in one smooth movement. I couldn't help him fast enough and my own hands scrabbled at the waistline of his jeans, finally gaining purchase on the stupid button and the stupid zipper. As I fumbled with him he had my panties down as far as his arms would reach. I shimmied my legs to get them all the way off. He pushed down on his jeans and underwear; as they bunched around his calves he moved in between my spread legs. I was bracing myself for impact when he pulled his face back from mine. I looked into his eyes again and saw not a hint of boredom.

"Yes?" he asked.

"Yes," I answered.

He slipped an arm around my waist and pressed his body into mine. We were a similar height so all he needed to do was raise up on his toes slightly. I moaned at the sensation of him sliding into me. I was so wet, so soaking fucking wet. Every other time I'd had sex for the first time with someone I remembered being so self-conscious of every movement, judging myself the whole time. All I could think with Keiji wasmore,andfaster, andharder. I don't know if I said as much but that's what he did and the next time I paid attention to myself it was because I was nearly sobbing into his shoulder.

"Yes, yes, yes, ugggghhhh fuck yeeeeesssss," I groaned. I was going to come, and come hard. I had never had an orgasm from penetrative sex before but something new was happening to me. It was as if my whole world was in my pussy and my clit. To make things even better, he seemed to be fucking me harder with each passing moment. Another first -- I'd never slept with a guy who could fuck me so hard with such stamina. He must have a personal trainer or something. The knowledge of where we were, that we could be discovered at any moment, made everything that much more darkly exciting.

"Don't stop," I pleaded, still talking into his shoulder. I felt him shake his head --Nope. Not planning on it.

I started to come. I somehow had the presence of mind not to scream as the orgasm overtook me and my pussy clamped around his cock, over and over and over. He pounded me mercilessly through it as I hung onto his neck and shoulders and tried to keep standing through the overwhelming pleasure. I felt the moisture from my pussy increase between our legs.

phlight
phlight
23 Followers
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