Overcoming My Fear of Flying

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Uptight woman learns about masturbation from a rock groupie.
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Bluepen451
Bluepen451
1,402 Followers

Okay, I admit it. I was a prude. A 32-year-old accountant who always dressed in just about the most conservative business clothes possible (and Dockers and conservative blouses on my time off, what there was of it). Never married, and aside for a few brief and highly unsatisfactory dalliances, I had essentially no sex life. I was, on the other hand, a pretty successful accountant. Occasionally it occurred to me that the two were related, and not exactly an optimal life-work balance; but most of the time I didn't worry about it. At least I didn't worry about it until I met Florence. She turned me on (I wouldn't have used that phrase before I met Florence) to a whole new way of looking at life.

Florence was about as close to my complete opposite as a person could be. She worked in our accounting firm as an administrative assistant. She had long thick red hair that wanted, and was allowed, to go in every direction you could imagine. Her clothing consisted of long flowing dresses with wild colors and patterns and sandals, (even when it was snowing) and loose fitting peasant blouses that did little to hide the fact that her large bust was rarely restrained by any form of bra. Broad hips, big breasts and wild thick red hair—that was Flo. Generally we tried to keep her away from our more conservative clients, but we kept her around because she was really good at the work she did for us.

After April 15 of each year I take my annual post-tax season break. I have a cabin upstate where I usually go for my break. I walked into a little coffee house where I planned to spend some time reading the latest accounting bulletins from the Financial Accounting Standards Board (nice way to use time off, eh?). It was kind of a funky little place with recycled barn wood on the walls and a bunch of old rock concert posters for wall art. It smelled faintly of wood smoke from the wood stove near the back. The late morning sun shown weakly through the windows. There was hardly anyone in the place on a weekday in late April, but as I looked around I spotted Florence sipping on a cup of chi and reading an I-Pad.

"Florence, how are you?"

"Hi Sally. What are you doing here?" she responded as she set her I-Pad down.

"Its my annual post-tax season week off. Time to catch up on the latest releases from FASB."

Florence smiled and refrained from saying anything about how absurd that sounded.

"Get your coffee and join me."

When I returned with my three shot, 16 ounce latte, I noticed what she was reading (I am good at reading things on people's desks that are upside down. Bad habit, but occasionally useful). I did a double take as I read:

She dropped to her knees and slurped his rigid cock into her mouth. As she sucked on him he reached down and began massaging her tits. He grabbed a nipple with the fingers of one hand while the other hand massaged her other tit. His fingers twisted the nipple and pulled hard on it creating a shot of fire that went straight to her pussy.

I was so shocked that I had to read it again. As I confirmed what I thought had read, I realized that Florence had said something that I didn't hear.

"Oh yes, it is a nice day," I responded in what was almost certainly a complete non-sequitur.

A small smile crossed Florence's lips as she realized what had just happened, but she made no effort to cover up her reading material.

"Are you up here by yourself?" Florence asked.

I wondered if that was the question she had asked me that I had ignored, but I was still so shocked by what I had seen on her e-reader that I just ignored my prior lapse and responded, "Oh yes. I own a little cabin up here that I try to get away to on the weekends. I have it fixed up with high speed Internet service so it is almost like being in the office."

Another wry smile from Florence. "Sally you work too hard."

Probably so I thought, but that is what it takes to get ahead in life. "Well, that seems to be what it takes to get ahead," I said.

"Hmm. What are you trying to get ahead of?"

Her question stopped me cold. Between my prudish shock at the lurid material she was reading and the question, I was stuck for a response. That doesn't happen to me very often.

As I paused searching for a response, I read another piece of the text on her e-reader:

As she squatted before him he put his hands in her hair and begin to pull her head back and forth as he fucked her face. She balanced herself with one hand on his thigh, while she shoved two fingers of her other hand into her sloppy wet cunt.

I had never seen language like that before. Since I had completely lost the thread of the conversation, I just gave up and blurted out the only thing I really wanted to know, "What are you reading Florence?"

She couldn't manage a wry smile this time. It was full blown laugh.

"Well it certainly isn't a FASB release," she said as she laughed. "It's a lot more interesting."

I was blushing crimson by this time.

"I guess it is," I mumbled.

"That is the beauty of these e-readers," she said. "You can sit in a café or on a plane and read anything you want and no one knows what you are reading. You would be amazed to find out how many of the folks who work for you read porn on their lunch hour."

"Really?"

"Yes, really."

"Why?"

Now I had asked Florence a question that stopped her cold. She just looked at me for several seconds while she tried to decide if I was serious.

"Because they're horny and the work they're doing is boring. Or maybe it is because the work they are doing is boring and that makes them horny. I have never quite been able to figure out the relationship between boredom and horniness."

"Oh."

"Don't tell me you don't read porn?" she asked.

"Uhh. No not really."

"Well you are really missing out. It is a lot more interesting than the FASB releases you are reading on that laptop you are carrying around."

"Where do you get it from?"

"Oh Sally, where have you been living? The Internet is awash with porn. If nothing else you can buy it for your e-reader or your tablet from Amazon. They have thousands of titles and they are cheap: ninety-nine cents to a couple of bucks. It isn't high quality literature, but it would be a nice change for you from FASB releases. And, she said with a teasing smile, "It's great to masturbate to."

That really stopped me. I just never spent time around people who talked about masturbating. I thought that the conversation had gone well beyond the limits of anything I had the courage to talk about so I deliberately and obviously changed the subject.

"So . . . do you come up here on a regular basis?"

Florence smiled again recognizing my obvious ploy to avoid an uncomfortable topic, but she was fundamentally a nice person, so she went along with it.

"Well my boyfriend and I like to come up here to spend weekends at the Plantation."

"Oh, what's that?" that I asked in innocence.

This time it Florence's turn to pause as she tried to figure out how to respond to me.

"Well, it's a kind of a club for people of like minds about social issues." She had decided I had suffered enough enlightenment for the day so she was trying to avoid telling me that she and her boy friend liked to spend their weekends at a nudist colony/swingers club.

We moved off the subject of sex and after about half an hour of idle chitchat, we both went our separate ways.

* * * * *

After Flo and I parted company, I tried to read the accounting literature, but I just couldn't focus on it. My mind kept going back to my conversation with Flo and the lurid material she was reading. Finally after dinner and a considerable quantity of wine, I fired up my laptop and began to cruise the Internet for porn. First, I just ran a Google search for "porn," but I quickly concluded I wasn't quite ready for what turned up there, so I narrowed the search to "dirty stories." I eventually found my way to a site called Literotica, which had an apparently unlimited number of stories in about a dozen or so categories. Like Flo said, not great literature, but they sure were more interesting than accounting literature. I read about a wide range of sexual activities until past midnight. I was so obsessed with it that I went back to it some part of everyday of my vacation.

Did I masturbate? Well, yes, but I was somewhat restrained about it as I had always been taught that it was somehow wrong or dirty. As a result, there was always a lot of guilt associated with it. Getting over my discomfort with sex—my fear of flying, if you will, was going to take some more effort. But I had no desire to stop.

* * * * *

For the next few days I stayed focused on work, but gradually I found myself pausing during the day and thinking about the nasty stories that I was reading in the evenings. Then one day about a month later I followed up on Flo's suggestion of an e-reader. I bought a Kindle and loaded it with a few pieces of erotic literature that I downloaded from Amazon (along with a couple of classic pieces of literature I could tell people I was reading if they asked). A few weeks after that I found myself with a day without a client lunch meeting, so I slipped my Kindle in my purse and went out to lunch by myself.

As I ate, I read a story that definitely wasn't accounting literature:

"As she got on the train Kindra realized that there was no place to sit, so she stood holding a pole. It was a hot muggy day, and she could feel the sweat dripping between her breasts. At the next stop, the train filled up even more, and she found herself face to chest with a tall, lean, dark haired man. He was enough taller than her and they were so close together that she couldn't really see his face. They didn't exchange a word, but Kindra realized that he was looking down the front of her blouse. Her cleavage was readily visible from his angle. She knew she should be offended, but the situation was just making her horny. She could feel the dampness increasing in her crotch and it wasn't from the same source as the drops of sweat trickling between her breasts. Fuck, this train ride is getting hot she thought—in more ways than one.

At the next stop people got on and people got off. Everyone rearranged themselves as they accommodated the change, but it was still very crowded. The tall stranger was behind her now. Kindra felt him pushing his hips against her. She wasn't sure whether it was because of the crowd or not, but it felt so good she didn't care. In response she moved her hips from left to right, rubbing against his thighs and crotch. As she moved, he pushed back. No question; they both knew what was going on and why. She was sure that she could feel an erection beneath the stranger's trousers. Her pussy was on fire.

One stop further there was another rush of people on and off the train. This time the stranger pulled her to the back of the car. He was still behind her pressing her firmly, but now she could feel his hands caressing her ass. Fuck, this feels good, she thought. Neither of them said a word.

Kindra looked about and determined that no one was paying the slightest bit of attention to her or the stranger fondling her ass. People were looking other directions, reading newspapers or e-readers, engaged in conversation or otherwise oblivious to what she and the stranger were up to. Encouraged by their lack of attention, Kindra took one hand off the pole and reached around behind herself. She slid her hand between herself and the stranger, being careful not to pry those oh so sexy hands off of her ass. Her hands found their way to his crotch where she began to massage a very large erection through his pants.

The stranger's response was to slide his right hand down Kindra's leg as his left hand continued to fondle her ass. When his right hand got to the bottom of her skirt, he slid it under the dress and around to the inside of her thigh. Then he began working his hand up the inside of her thigh. All the while Kindra continued to stroke his dick through his trousers. When his hand reached the top of her thigh Kindra deliberately widened her stance to give him better access to her pussy. The stranger quickly pulled her sopping panties aside and slipped two fingers into her cunt. Kindra jumped as she stifled a gasp, but then she settled back down on his fingers that were probing the inside of her pussy. Every so often his probing fingers would graze her G-spot and Kindra would jump again.

Without pausing his finger fucking, the stranger took the hand on Kindra's ass away for just long enough to pull down his zipper. Kindra slid a hand past the open zipper and wrapped it around his cock. It was hard as steel and hot as a poker just removed from a fire. She reached up to the tip and smeared the drops of pre-cum there over the head of his cock and then began to use it as a lubricant as she jerked him off. The stranger remained silent, but he was pumping his hips to force his cock through her slippery stroking hand.

Kindra could see the next train stop coming and that willed her cunt into a climax. Her pussy clamped down on the stranger's fingers as she gushed a small stream of liquid over his hand and down her leg. It was all she could do to remain on her feet as the climax ripped through her whole body.

Her climax set off the stranger. She felt his cock jump and then it began to pump streams of hot cum over her hand, just as the brakes began to squeal to bring the train to a halt at the next station.

Kindra quickly pulled her cum covered hand from the stranger's trousers as he did the same with his hand from her pussy. When the train came to a halt, the stranger stepped away from her towards the opening doors. As he left dropped his handkerchief on her shoulder for her to clean herself with. Then he was gone and Kindra realized she had never seen his face.

"Hello Sally."

I looked up to see Florence sliding into the seat across from me.

"I see you have some new reading material."

"Oh no, I was just reading the latest accounting literature," I lied.

Florence chuckled and gave me a look that said, "If you say so."

Florence's laugh was contagious and I couldn't restrain my self. "OK, you got me. This isn't accounting literature." I looked to see if anyone was listening to us, and said in a low voice, "It's a story about a woman and a stranger on a train. He presses against her and he fondles her to a climax while she does the same for him—all before they get to his stop, without being noticed by anyone. She never sees his face."

Florence responded, "Hmmm. Delicious. Sally I think you have seriously changed your style since the last time we had coffee."

"I know . . . well, I'm trying."

"What brought that about?"

"I'm not sure. I just started thinking after we met in the coffee house up north. It occurred to me that perhaps I didn't have quite the right degree of balance in my life."

"You mean it has occurred to you that it is better to die thinking you spent too much time getting laid than too much time reading FASB releases?" Flo responded.

God this woman had a penchant for getting right to the heart of a matter. "Yeah, something like that," I responded after a moment's hesitation.

"Well you can carry it too far the other way too," she said. "Believe me I know."

"Really?" I asked.

"Oh yeah, but that is a story for another time."

"Okay, but I would like to hear it."

"So now what are we going to do?" Flo asked, changing the subject away from her past.

I looked at my watch. "Time to go back to work."

"Really? How much work do you think you will get done after spending your lunch hour reading that?"

I laughed. "You're right, but I have client meetings this afternoon and the first one starts in half an hour, so I don't have much of a choice. What about you, Flo?"

"Well of course I am going back to work," She responded with a smirk. "I was reading accounting materials over lunch. No problem for me."

"Really?" I asked.

"Not!" she responded with a laugh.

"So we won't be getting a hundred percent out of you this afternoon, eh, Flo?"

We both broke up laughing.

"Can I read your story?" she asked. "It sounded pretty hot."

"Absolutely. Let's get together after work."

"OK. Come to my place. Six o'clock," Flo responded.

"Right," I said as I gathered my things to return to work.

* * * * *

Toward the end of the day I dropped by Florence's cubicle to get instructions to her house.

"It's on the river south of town," she said. "It isn't far but it is a little hard to find. Why don't you just ride out with me?"

"Okay . . . but can you give me a ride back to town later?"

"Sure thing. Like I said, its not that far—just hard to find."

"Well, I am done for the day so as soon as you get through, just come by my office and we can leave together."

"Okay, I need just a few minutes to finish up my work for today on this spread sheet."

Half an hour later we were in Florence's VW microbus headed south along the river. Imagine that; me in a VW microbus. I had read about them and seen them in movies and on the street, but I had never actually been in one. The engine sounded like a sewing machine in pain and the old body rattled on every bump in the road. The seats were worn and there were several strings of beads hanging from the rear view mirror, which had about half of its glass in it. I was thinking, I know we pay you more than this Flo, but of course I didn't say it. Besides, even if I had, I am not sure I could have been heard over the noise the van was making. Oh well, one of the things I had decided while I was upstate was that I needed to change my lifestyle a bit, and although riding around in an ancient microbus hadn't been something that occurred to me, what the hell, it was different than my late model Lexus.

As we wandered down the two-lane road that followed the river, the trees and brush closed in on the road so that we were almost in a green tunnel.

"Florence, I said loudly enough to be heard over the car, "How did you get a home down here? This is all protected wetlands and it floods every ten years or so."

"I inherited it from my mother," she responded. "It was an old hippy commune in the sixties, and she wound up being the last member of the commune, so she owned it."

"Really, how does that work?"

"Well it works best when you have a partner who is a lawyer that files a quiet title action for you, and no one shows up to object."

"Ah. I see."

"How big is the property?"

"I have about 20 acres. The house sits on a little hill above the flood level, but the orchard, the pasture, my vegetable garden, and the rest of the property, which is just woods and brush, do get flooded from time to time. There are lots of deer and other animals, and no one ever comes down here and bothers me."

"Isn't it a little lonely?"

"Nah. I have two dogs, a bunch of cats, three goats, chickens and a live-in boy friend, when he is town."

"Oh. What does he do?"

"He runs a sound board for rock bands at concerts. I guess he is good at it because he is away on a gig a lot of the time."

We try to make up for it when he is home," she said as she looked over at me with a wink and a smile.

Flo yanked hard on the steering wheel, and the bus dived into narrow slot between the trees on a one-lane dirt track headed towards the river. It twisted through the trees for a hundred yards or so until it opened up in a graveled parking area in front of a rambling old two story house. Maintenance on the house looked like it pretty much matched the maintenance the bus had received—only what was minimally necessary to keep it functioning.

Bluepen451
Bluepen451
1,402 Followers