Is It Really That Simple?

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A single guy longs for a simple relationship.
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imhapless
imhapless
3,645 Followers

By the time that I, Brandon Miles, was 29 I had had a large number of failed relationships. I guess most of them were my fault since though I never analyzed it accurately at the time I seemed to be commitment averse. I'm not really sure why that is because I never said to myself "I'm not the type to marry," and my parents had been happily married for 35 years. Maybe I was that way because relationships really seemed complicated to me; I craved a simple one. Regardless of the reason for my inability at the time to determine why I was commitment averse, that's the situation that I found myself in.

While I lived near a big city, I also felt -- for whatever reason -- that my dating options were somewhat dwindling. My wide circle of friends had morphed from mostly single to mostly married, and many with kids. I considered the females of the married couples -- whether they were initially my friends or their husbands were -- off limits for moral and practical reasons, and I was rapidly running through my single acquaintances.

It sometimes was difficult being around my married female friends, especially the wives of husbands who initially were my friends. The wives seemed to take great delight in flirting with me. Some took it too far, and I do believe that if I had merely asked without hesitation some of them would have jumped in the sack with me. That made me nervous.

The flirty behavior seemed to be directly contrary to comportment of another type by some of my married female friends. They seemed to be upset that I, as the only single guy in our circle of friends, hadn't gotten married myself since -- as they not-too-subtly put it -- because they considered me a good catch. I guess they thought that because not only was I in good physical condition and at least somewhat good looking, but because even though I lived an understated life many of them knew that I was rich. I could never understand why many married women are unhappy unless male friends are also married.

While I never wanted to admit it to myself, looking in hindsight there was one straightforward reason that I was commitment averse; its simplicity was in stark contrast to the complicated relationships that unnerved me. I was enthralled, gobsmacked, bewitched, captivated, charmed -- whatever you want to call it -- by one of the married females who was a relatively recent addition to my circle of friends.

I'm not exactly sure how Eleanor Dawkins and her husband Josh first appeared in my group of friends -- I think that it was at a party hosted by my best friend Tim and his wife Sherry when I was 27 -- but they did. It was probably the third time that I met Eleanor before I became fully aware of the strange effect she had on me. It was strange not only because of my feelings, but also because she "wasn't my type."

Since I'm six feet four inches tall I had always dated tall women. I think that the shortest woman that I had ever gone out with since adulthood was five feet eight inches tall; Eleanor is five-five. I always dated extroverts; Eleanor is an ambivert. Most of my dates were brunettes with long hair; Eleanor is a strawberry blonde with medium length hair. I'm more a tit-man than anything else so most of my dates were with buxom women; Eleanor has average sized boobs. While I've always appreciated a nice ass, I've never been particularly hung up on that female feature; Eleanor has the best bubble butt I've ever seen, slightly "oversized" for her frame. At least there is one thing that Eleanor has in common with most of my dates -- she's intelligent.

What Eleanor had that no other woman I had ever met had was sultriness. "Sultry" seemed to exude from her pores. On a scale from "blah" to "Torrid" her sexuality was above "Torrid."

As earlier indicated, while all of the other wives in my circle of friends either playfully, or a few seriously, flirted with me, Eleanor never did. I would not call her "aloof" or "withdrawn," but she certainly wasn't "friendly" either. Perhaps the best word to describe her apparent attitude toward me was "casual."

While I was enamored with Eleanor, and what I knew about her I liked, I found her husband Josh to be haughty and unlikeable. I think that the only reason that Tim and Sherry introduced them to our group of friends is because Sherry was a long-time friend of Eleanor's and Tim had a remote business connection with Josh.

In any event, Eleanor was seriously fucking-up my life because I thought about her, on and off, at least about an hour a day. Fortunately I am good at multi-tasking, otherwise that could have caused loss of concentration, which in turn would have cost me scads of money in the business deals that I did weekly, either for myself or representing other people.

***********

At 29, after I had known Eleanor for about two years, I believed that I had been subtle in my appreciation of how sultry that she was. I did occasionally nonchalantly ask Sherry about her, but never expressed intense interest. I also believed that I had successfully avoided obviously ogling her, even during a pool party that Tim and Sherry hosted where I saw her in a bikini. Anticipating that possibility I had worn reflective sunglasses and loose swim trunks so my lust for what appeared to be her almost perfect female form was successfully hidden.

Apparently, however, my feelings toward her were not as inconspicuous as I thought that they were.

Out of the blue on a Friday afternoon while I was still at my office I got a call on my cellphone from Eleanor. She must have gotten my number from Sherry, because I never gave it to her.

"Hello, Brandon Miles here," I answered my phone in my normal manner since it could be business or personal.

"Brandon, this is Eleanor Dawkins; I hope that you remember me from Sherry's parties," was the melodious voice on the other end.

I swear that my dick started to salute. "Uh, sure Eleanor; how...uh...are you?" I inarticulately replied.

"I'm doing fine Brandon, thanks for asking. The reason for my call is that I was wondering if there was a convenient time I could talk to you about a charity that I'm involved with."

I give five figures each to half a dozen charities every year before Christmas, don't accept phone solicitations or mailings from others during the year, but also give to charities that my friends specifically solicit -- and I'm sure that Sherry told Eleanor that.

"Uh...sure...uh...yeah," I stammered. "Actually I'm not doing anything tonight -- I've had a really hard week at work -- so you could come by when it's convenient tonight if that's possible."

"Great; would 6:00 p. m. be convenient -- unless you eat that early," she chuckled.

"No...that's fine," I replied trying not to sound anxious.

"I have your address from Sherry as 15 Chardonnay Ct.; is that correct?"

"Sure is."

"That's only about two miles from my condo. See you at six; bye," she concluded as she terminated the call.

I couldn't believe it but in the few minutes that I had talked to her I had pitted out my undershirt and my cock was more than half hard. "Down, boy," I mused. I needed to get my act together before she came over so that I didn't make a fool of myself.

I left work early -- I was planning to anyway in view of my taxing week -- but now instead of making a quick dinner and watching a baseball game on TV I needed to clean up my house and to shower. I got home about 4:30, worked for an hour tidying everything up -- because of my hard week I hadn't kept the house neat like I usually do -- and then showered and got into my nicest pair of slacks and short sleeve shirt. I was anxious because I had never, ever, been one-on-one with Eleanor before.

Eleanor arrived right on time in a rainbow colored knee-length sundress, a stylish hat, sunglasses, and three inch heels that obviously matched her dress. "Hi Brandon," she smiled.

"Uh...hi Eleanor," I sheepishly smiled back hoping that the dramatic effect that she had on me wasn't noticeable. "Won't you come in?"

"Thanks," she smiled as she brushed past me, causing me to gulp. "I really like your neighborhood -- it's so cheery," she smiled, "and your house is the nicest on the cul-de-sac."

"Thanks; I really like it here."

"Let me cut to the chase, Brandon," she only half-smiled, taking off her hat with a sweeping motion, placing it upside down on a hassock, and tossing her sunglasses in it and thereby displaying her intense cat-like green eyes. "Here's a brochure on the charity Strive For Success, which is dear to my heart. They provide tutoring for underprivileged kids," she continued, pulling a pamphlet from her purse and offering it to me while placing her purse near her hat.

"Uh...sounds interesting...nice," I mumbled.

"Having a chance to give you this brochure was only a pretext for me coming to see you, though," she half-sneered.

"Uh...what?" was my intelligent reply.

"The real reason I came here is to ask you why you're so enamored with me. Why does a smart, articulate guy like you get tongue-tied around me? Why do you always ogle my ass? Why do you ask Sherry about me? What is your fascination with me when many of the women you date are better-looking than I am? Aren't you embarrassed by how you act around me in public?" she rapid-fired questions at me, not waiting for an answer to any of them -- not that I would have been able to give halfway intelligent answers anyway.

"Uh...well...uh...geez...what makes...uh...you think...uh," I stammered in response trying to think of something -- anything -- to say that wasn't stupid.

When it was clear to her that she wasn't going to get any answers she pulled her sundress over her head and tossed it on top of her hat and purse -- she was naked underneath.

My cock saluted so fast that it hurt banging into my zipper. I had thought that her body was an almost perfect female form when I saw her in a bikini; now I knew that it was perfect from her perky breasts with elongated nipples to her tiny slit with protruding clitoris, to her phenomenal thighs parted slightly at her crotch.

As I stood there dumbfounded she continued. "I think that if I fuck you once and you see that I'm ordinary that will snap you out of your stupor." With that she approached me, put her arms around my neck and pulled my face towards her, and laid a zealous kiss to end all zealous kisses on my lips. When she finally broke it off she snarled "You're a big strong boy -- why don't you carry me back to your bed, and we'll get down to business." With that she pulled on my neck, jumped her ass up. I caught her and started walking toward the bedroom. As I walked, stumbling into walls on occasion when she would kiss my neck and cheeks, I felt my cock turn into a piece of steel.

After I laid Eleanor down on the bed like an automaton I started undressing; fortunately I didn't have many clothes on, with few easily destroyed fasteners, so I wouldn't have to go to a tailor to save some wardrobe items. When I moved into bed she flipped around, got on top, started sucking my cock, and put her pussy over my face.

As she enthusiastically sucked I fingered her pussy and tongued her clit. She had me blowing a load in her mouth in about a minute flat, and while swallowing apparently had a min-orgasm of her own as a result of my abuse of her clitoris. Even after I was done discharging she continued to stroke my cock, and then started fondling and sucking my testicles. I continued to manipulate her pussy. Her pussy tasted like cucumbers, and her crotch looked delicious and her ass felt firm and shapely.

My dick never really got soft, but it did wilt slightly. However, as a result of her oral abilities it was back to being a piece of iron in no time. Once it was clearly hard she rotated 180 degrees, aligned her tiny slit with my cock, and impaled herself. She screamed as my cock penetrated her extremely snug pussy, then regained her composure, and started riding me like I was a rented mule. It seemed that her pussy moved back-and-forth, in circles, and forward and to the rear, all at the same time and simultaneously with squeezing and releasing her pc muscles like she was a milking machine.

Her tits were a little larger than they looked when she was dressed, and her nipples stood proud and hard like long pencil erasers. I latched onto them and squeezed and released them as she let out a long string of invectives like "Don't waste your chance to fuck me you pencil-dicked prick," "fuck my pussy off, bastard," "fill my pussy with a gallon of cum you wimp," and many other dirty, outrageous, diatribes. When she said "fill my pussy" I suddenly realized that I wasn't wearing a condom -- but there was no way in hell I was going to interrupt the ride of my life.

It wasn't long before she made what appeared to be a concerted effort to clamp her pussy on my cock, which in turn was quickly followed by me injecting her with what seemed like a quart of seminal fluid, causing me to grunt like a pen full of hogs, and her to scream like a banshee.

Exactly what followed I'm not really sure of. I do remember that my orgasm was so intense that I blacked out for a while -- more intense by a factor of three than any other in my life. I temporarily came to life when I felt the void formed when she moved her pussy off of my dick, but soon after that I went into a twilight zone, probably occasioned by more endorphins flowing through my brain than at any other time in my life, essentially drugging me. I only snapped out of my personal twilight zone when a dressed Eleanor kissed me and smiled as she said "That was fun," and then followed that quip with "You can send a check for $5,000 to Strive For Success in the envelope with the pamphlet that I gave you. Be sure to mention that I solicited it from you." With another kiss, she was gone.

I eventually dragged my ass out of bed, although it felt like someone had surgically removed my spine. I aimlessly stumbled around naked until hunger pangs hit. A coldish shower woke me up somewhat -- at least enough so that I had the energy to put on my clothes and make and eat a turkey sandwich and open up a prepared salad clamshell.

I don't think that Eleanor really believed that by fucking me she'd allow me to purge my attraction to her from my mind. I chuckled when I recalled her saying that she was an ordinary fuck; in reality she was a fantastic to the 10th power fuck! Now my mind was more messed up than ever as I stared into space, with the TV on but not paying any attention to it, trying to figure out where I went from there. I did write a check for $5,000 to Strive For Success for mailing the next day. As I was writing the check for the first time the fact that she was married popped into my head; for some reason this didn't disturb me probably because I never even had time to think once she presented her naked body to me, and maybe because I also didn't like Josh. I remember thinking that maybe I'd feel guilty in the future, but I never did.

Eleanor screwed up my date Saturday night; it was a disaster. She also screwed up my Sunday afternoon date, a near-disaster. I was so preoccupied both times that I was present in body but not mind. Fortunately I realized how miserable I had been during each outing so at the end of each I apologized for being distracted and begged each date to give me another chance. I promised to take them to the restaurant of their choice, no matter how expensive, if they agreed. Fortunately that temporarily saved both relationships -- although between the two outings it would probably cost me $800-$900.

Things got a little better for me when I went back to work the next week and had a number of challenging projects that I had to deal with, although if I had any downtime images of Eleanor fucking my brains out would reappear. I had her cellphone number from when she called me the past Friday to arrange to meet. Whenever I had some downtime I tried to call her -- she never answered the phone and I didn't leave a message. I really don't know what I would have said if she did answer; "Want to fuck again?" was what I would have wanted to say, but I doubt that I would have been able to be that direct.

Two weeks after my best sexual experience in history with a date I went to a party at Tim and Sherry's house; of course Eleanor was there. She never sought me out and when we interacted she treated me no differently than before -- casually. She gave me no signals, positive or negative, and even though she talked to me in a group for 15-20 minutes she never said anything in any way flirty or provocative. I wanted to jump her bones, but was somehow able to restrain myself and act almost normally. I don't think that my date saw me staring at Eleanor's ass the dozen or so times that I caught myself.

Things moved slowly along for about the next month. I only tried to call Eleanor three or four times during that period, and saw her two times, one time with a group at a restaurant, another time during a group picnic. She treated me the same as always during these interactions -- neither aloof nor friendly.

On a Saturday morning six weeks and one day after my supreme sexual experience I was getting ready to go to the gym and work out for a few hours when there was a knock at my door. Standing there in a raincoat and high heels with makeup on and her hair pulled back was Eleanor Dawkins.

"We need to talk," she said timidly; "can I please come in?" I was almost too stunned to speak. "Uh.. OK" I stuttered, fortunately with at least the presence of mind to close the front door.

The demure, submissive woman standing in front of me bore no resemblance -- in attitude -- to the aggressive, confident, woman who appeared six weeks earlier. Physically, she may have been even more spectacular than I remembered as she shed her coat -- her only article of clothing aside from her high heels. Only looking me in the eye periodically, the rest of the time staring at the floor, she mumbled "I guess that my first visit didn't cure you of staring at me. Do you think that if we had sex again it might help?"

After that astonishing statement she slowly approached me, put her hands around my neck, buried her fact in my chest, and simply hugged me.

My mind was in turmoil. I didn't know how to react. When she got on her tip-toes and whispered in my ear "You can do with me what you want to," I picked her up and carried her to my bed

When I placed her on my bed she scooted up toward the headboard and with an innocent look on her face spread her legs. I went after her honeypot with my mouth and all ten digits. Instead of swearing at me like she did the last time, this time she simply groaned and occasionally said "Oh yes; Oh yes!"

After she had a rip-roaring orgasm she actually thanked me, and then through glassy eyes she stared at me, and moved her arms apart, inviting me into her grasp. I moved up the bed, kissed her as she hugged me, and then penetrated her in two strokes, the first about halfway in, the second burying my male member in her tight chasm. After a minute or two of reciprocating in her, with only meek sounds of pleasure coming from her, it was like I was making love instead of fucking. She urged me on only with contented whimpers. By the time that we reached an in-sync crescendo I felt like I had never felt before in my life.

When we both came down from our climaxes and my cock popped out of her pussy, she cuddled up to me and thanked me again. I didn't know what to say in response to that except the truth. "That was the most loving experience of my life," I replied. Soon thereafter she pushed herself away from me -- I could swear that there was a tear in her eye -- and said "I'm sorry Brandon, but I have to go." Then she gave me another of her zealous over-the-top kisses, and literally ran out of my bedroom. Moments later I heard the front door open and close.

imhapless
imhapless
3,645 Followers
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