Simple and Straightforward

I first saw her picture on the dating website I’d just joined. Her screen name was “simplesf” and she was older than me. Much older by my normal standards, whatever those standards might be. I hadn’t dated in two years, and hadn’t had a sustained relationship in even longer than that. So saying what was normal, and what wasn’t, was a guess at best.

But her picture caught my eye. And truth be told I’d always been attracted to older women. Her profile listed her as forty-two, and assuming that was the truth, that made her almost ten years older than me. I don’t think I’d ever dated anyone that was more than a few months older than me, and certainly no one a few years older, let alone ten. But something drew me to her picture. There was just something about her. I was hard to describe. To me she had this air about her, an air of sophistication, and confidence, and style. She just had something that most other women didn’t have, and it came through even though all I saw was her picture.

Her profile didn’t really say much about her. Paired with her picture, her profile made her seem mysterious, which I’m sure only added to my attraction. Her hair was dark, cut into a stylish bob that seemed to frame her face her perfectly. And her deep brown eyes set against high cheeks and fair skin seemed to glow. Other than that, her profile simply listed her as divorced with no children. Physically she was listed as tall and slender. Her location indicated she lived within twenty-five miles of me. She didn’t bother list any hobbies, or likes and dislikes, as most of the other profiles seemed to do. At the end of the profile she was characteristically brief as well, stating simply, “What you see is what you get.”

I wasn’t sure what I was doing. I had only recently decided to try the online dating scene as wasn’t sure what to expect. In the past week since I’d joined, I’d sent out about five feelers. I’m sure my profile seemed awkward, and my messages probably did too, and so far I hadn’t had any luck. Of the five messages I’d sent, I’d received only one reply, and she politely indicated she wasn’t interested. I didn’t expect much when I finally sent a message to “simplesf.” I felt awkward writing it, and even more awkward reading it back before I sent it. I briefly introduced myself, included a link to my profile, and mentioned how her picture and profile caught my eye, and that she seemed like she would be interesting to talk to.

My anticipation waned as two days had passed and she hadn’t replied. By then I had given up hope. I just assumed she wasn’t interested and that I would never hear from her again. I was disappointed to be sure, but I wasn’t surprised based on what had happened before. Still I found myself visiting her profile again, staring at her picture, and wondering what she was really like.

After work on the third day since I sent the message I logged into the website, and to my complete surprise, I had a message waiting for me from “simplesf.” As I stared at the message, my stomach sank and my hands began to twitch. I was a strange combination of fear and excitement. I paused before I clicked on the message, unsure what I really wanted to see, and even more unsure of what to expect. Finally after what seemed an abnormally long time I managed to click on the message. When it popped up my first reaction was one of disappointment. It was a very brief message and I thought surely would it say she was just not interested. But as my nerves calmed I realized that it simply stated “Tell me more about yourself.”

I agonized over my response, taking more than an hour to write two short paragraphs. In my response I did as she asked, and told her more about myself. I told her where I was from and where I grew up, where I went to college, and what I studied. I told her I was as an electrical engineer and worked in the semiconductor industry, and that in my spare time I liked to jog, and read, and drink coffee. I explained to her how my passion was black and white photography and that it took up a great deal of my free time. I tried to be simple and succinct. I wasn’t really sure how my message would come off. I had always been awkward and more than a bit shy, and I’m sure that somehow came across.

I must have read the message five times before I actually sent the message, making minor changes each time I read it. Finally I hit the send button and went to eat some dinner.

All through dinner I couldn’t keep my thoughts from wandering. I wondered what she would think and if she would even reply. After dinner I checked my e-mail again. Nothing. I must have checked it ten more times that night before I went to bed. I couldn’t stop thinking about her. All night I tossed and turned. Finally too restless to sleep I got up to check my mail again sometime in the middle of the night. I didn’t expect to see anything but I still had to check. When I saw a reply in my inbox my body immediately reacted. I swear I felt my stomach in my throat as I clicked on the message. Once again it was very short. It said nothing more than “Don’t you have any questions for me?”

I wasn’t sure what to think. Here I was trembling as I read her message, a thousand thoughts running through my mind. I’d spent an hour writing a message to her, and she spent all of ten seconds replying. I had no idea if she was interested, if she was just being polite, or if she was just teasing me. I spent the next hour thinking of questions to ask her. I had a million questions I wanted to ask. My list grew longer and longer and I tried to cut it down, but as I did I became acutely self-conscious. What kind of questions was I asking? As I read them over and over they seemed silly to me. I wanted to ask all the questions I had written down. I wanted to know the answers. But at the same time I felt embarrassed to ask. I felt like a little boy obsessively asking his teacher questions, trying to win her attention. In the end, I decided to just ask one question. My message was brief and to the point, just like hers had been. I asked “Where does ‘simplesf’ come from?”

The next day was torture. All day at work I couldn’t concentrate. All I thought about was her, and what she would say and do next. I wondered if she thought I was annoying and if she was already bored with me. I left work half an hour early just so I could check my e-mail at home, hoping there would be a response. As I logged in my whole body seemed to tremble, my breath was short, and my fingers twitched errantly as I typed. When I finally opened the inbox, I think my heart must have stopped. Another message awaited me. Like before, this message was brief. But unlike before, this one was two lines. The first line read “simplesf=simple & straightforward.” The second line read “Would you be interested in joining me for coffee this evening?”

By now my heart was pounding in my chest. My fingers trembled as I hit “reply.” I typed “yes” and asked where she would like to meet and at what time. After I sent the message I went to get something to eat. I made myself a quick sandwich but it was no use. I had no appetite, my mind was elsewhere along with my stomach. After half an hour I couldn’t wait any more. I logged in again to see if she had replied.

Her response was customarily brief. She said eight o’clock at Woodrow’s Coffee House. I immediately went to get ready.

By the time eight o’clock rolled around my nerves were shot. I was nothing but a frazzled mess. On the short drive over I panicked. I looked down and saw how poorly I was dressed. I felt like a little schoolboy in his schoolboy uniform. For some reason I wore khaki pants and a plain white button down shirt. As I dressed I thought to myself I didn’t want to stand out. I didn’t want to create any false impressions. I just wanted to be me. But as usual, I quickly began to doubt myself. What had I gotten myself into? Wha
t was I going to say? I already felt awkward and I hadn’t
even said hello yet. Part of me wanted to turn around and go home, and part of me wanted nothing more than to meet her.

I arrived at Woodrow’s five minutes early. I sat at a table inside, near the windows so I could watch the traffic flow by outside. I thought if nothing else, the traffic may give us something to talk about. As my eyes briefly moved to the cafĂ©’s front doors, she stepped through the doors at precisely eight o’clock.

Her profile on the web site was accurate. She was tall and slender just as described. Slender hips. Slender legs. Delicate arms. Small breasts. I immediately wondered if she was actually taller than me. She certainly was in the heels she had on, and I wondered if that would be the case flat footed as well. She was dressed in a navy blue pin stripe business suit. It was perfectly tailored and fit her slender frame extremely well. As she entered, she paused briefly to scan the room. Before I could stand up to greet her, she noticed me sitting at the table. I was glad she recognized me. Part of me worried that my picture on my profile wasn’t representative. Knowing that it was and that she recognized me helped calm my nerves ever so slightly.

As she approached me, I stood up to greet her and extended my hand.

“Hello,” I said. “I’m Josh.”

She took my hand replied. “Hello, I’m Melissa. It’s very nice to meet you.”

Instinctively I pulled out the chair for her at the table. She sat down immediately as if that was what she expected.

She definitely had a presence about her. The same feeling I felt looking at her picture carried over into real life. You could tell she had a quiet confidence and sophistication about her. And based on her outfit, her sense of style and taste seemed impeccable. I was immediately attracted to her, but at the same time I felt uncomfortable and a bit out of place. It was a bit odd, I didn’t feel like I was on a date at a coffee house, but rather her subordinate at a business meeting.

I don’t know if it was her age, or the way she carried herself, or if it was simply my lack of confidence and inexperience, but I was definitely drawn to her. At the same time I felt unsure of my place. It was like her presence reached across the table and grabbed me.

The waitress soon came and took our order, and as she did I found myself looking across at her. Her picture did her justice as well, although up close and personal she did look slightly older than her picture. Crow’s feet had quietly begun to creep around both her eyes and mouth, but instead of detracting from her appearance, in a way they seemed to enhance it by adding depth and character to an already exquisite face. With the way she presented herself, she would have seemed awkward with the face of a twenty-five year old. But as she was, her face seemed to project her personality perfectly.

Our chat began slow. I found myself intimidated and it seemed like I was looking out the window and into the street more than I was looking at her. Once the coffee arrived and I had a few sips, I began to settle down. At the same time she began to grow a bit more talkative.

I asked her about her work, and she explained how she worked in advertising. She talked a bit about what she did exactly, what she liked about it, and what she didn’t. Overall, the feeling I felt from across the table was very cordial. I have to say, she dominated the conversation, leading it were she wanted to go and setting the tone. I simply followed her lead in what felt like a very natural way. As the time wore on, I found myself becoming more and more drawn to her. The way she smiled at me, the way she looked at me just seemed to suck my in effortlessly. Even though the conversation didn’t take on a sexual tone in any way, I nonetheless found myself wondering about her. Imagining what she would be like. Wondering how she would act. How she would look. The sounds she would make. But it was strange, as my thoughts turned sexual in nature, I felt more and more intimidated by her. The subordination I had felt when we first sat down never seemed to go away. If anything, it seemed to increase.

We sat and talked for nearly two hours when she said that she had to get going. Again, almost by instinct I stood and helped her with her chair. We walked together out of the coffee shop and into the parking lot. As we left I felt all eyes were on me. I’m sure we seemed like a strange pair to the other patrons. Out in the parking lot, I stopped at her car and shook her hand and thanked her for a good time. She smiled and said the same. To my complete surprise she asked if I would be interested in dinner the following evening.

For dinner, we met an Italian restaurant near Woodrow’s. It was more of the same. Once again, she seemed to come directly from work dressed in a black business suit, and once again the suit was perfectly tailored and looked stunning on her. I tried to dress a bit more stylish, donning a jacket and tie I had purchased earlier that day just for the occasion.

Even though I knew more of what to expect, the feelings from our experience at the coffee shop seemed to carry over. I couldn’t get over the way I felt in her presence. How I felt so intimidated and unsure of myself, and how she seemed to be so confident and in control.

As we started dinner, the conversation began much as before, about simple day to day activities and benign likes and dislikes. But as the evening wore on, the tone of the conversation changed. I don’t know if it was the wine, or something else entirely, but what had seemed banal and ordinary began to take on sexual overtones. She talked about her ex-husband, how they met, and how they broke up. She talked about other relationships she’d had since then, and she asked about me and the relationships I’d had. None of the conversation was overtly sexual in nature, although the sexual tension I felt building inside me was palpable. Once again my thoughts wandered to her, her relationship with her husband, and what the sex was like, and how it was in her other relationships as well. I wondered about her sexual personality and I envisioned how I would be with her myself. I imagined what it would be like. How she would act and how I would act as well.

I began to wonder if she was thinking some of the same thoughts about me as we talked. I wondered if she knew what I was thinking. Part of me felt embarrassed by it, but I couldn’t help myself. And part of me knew that she had me in this kind of sexual trance, unable to focus on anything but her. Part of me couldn’t help but think she encouraged it, and help feed it along. It was very subtle kind of tease, but she was so very good at it.

As we ordered desert, the sexual overtones, seemed to step up another notch. At first she simply touched me on the shoulder, and then further down my arm. When she did, my whole body tingled. I just wanted her to keep touching me. I didn’t want it to stop. As we ate our desert and talked, she continued to touch me playfully. Her contact was not overt, it seemed to flow with the conversation and be a natural part of it. Still, each time she touched me, it seemed to be a bit different. As we slowly finished desert, she brushed the back of her hand gently across my thigh.

By this point I was beyond aroused. I wondered if she knew how aroused I was and for some reason I wanted desperately to hide it from her. It felt like if she knew, she would know what kind of effect she had on me. And part of me didn’t want to give her that kind of control. As her had gently brushed my thigh, the waiter came and she asked for the check. As he walked she reached across my thigh and over to the rock hard cock between my legs. Gently she brushed her hand up and down along its length. My eyes involuntarily closed and my whole body shuddered as she did so. Slowly and deliberately she leaned closer and whispered in my ear as
her hand continued its motion, “You know this is mine don’t you?”
At that point I think my heart stopped. I was physically unable to mutter a response. By the time the waiter returned she had removed her hand and acted like nothing had just happened.

We paid the bill and got up to leave. I walked her to her car, not at all sure what to think or what would happen next. As she unlocked her car and I opened the door for her, she asked if I wanted to come back to her place for some coffee.

In fifteen minutes I found myself sitting on the couch in her living room wondering what I was doing there. My heart was pounding in my chest. I’m not sure I had ever been so nervous. I was totally under her spell. I felt like there was little I could do to resist anything. That alone scared me half to death.

She came back from the kitchen with two cups of coffee and unassumingly sat on the couch beside me. No mention was made of what had happened in the restaurant. Instead we just talked as before, much as we did at the beginning of the evening. The sexual innuendo was still there. The way she was sitting on the couch with her legs crossed, there was no way it couldn’t be.

After ten minutes of talking I finished my coffee and set my cup on the table in front of me. Melissa calmly continued to drink her coffee, but now instead of talking she just stared at me. It was almost a blank stare. Her look seemed like it was void of emotion, and as I looked at her I couldn’t help but wonder what she was thinking.

Suddenly, she lowered the cup from her lips and said “Why don’t you stand up?”

It was strange, part of me wondered why she would make such a request, enough so that I wanted to question it, but the other part of me, the part that was on auto-pilot did exactly as I was told. She continued staring at me as I stood directly in front of her. As I stood there, a thin smile crossed her lips.

She motioned for me to move around the table and to the center of the room. Once again, without question, I did as she directed me. The whole episode seemed very strange to me, yet I didn’t resist in any way.

“Take off your shirt,” Melissa said.

I took off my tie and as I began unbuttoning my shirt, I wondered what I was doing. I felt a strong urge to question what was going on, and as I moved my lips to ask, the other part of me thought better of it, and I just continued what I was doing.

“Now the pants.”

Before long I was standing in the middle of the living room in nothing but a pair of boxer shorts. Embarrassment overwhelmed me. I felt so awkward and intimidated. My rock hard cock was bulging out of my underwear and I was powerless to do anything about it.

“And the rest.”

As I slid my boxers over my hips, Melissa just stared at me expressionless. I had no idea what she was thinking or what she wanted me to do. But if I felt embarrassed standing in front of her in my underwear it was nothing compared to the way I felt now. Every insecurity I ever had seemed to come rushing though my body. I felt so naked and so alone. My rock hard cock seemed so tiny. All of me was on display for her to see. Part of me wanted to run out the door and never look back and part of me knew that wasn’t possible. I stood naked with my arms lamely at my sides for what seemed like ages as Melissa looked me up and down. She casually sipped her coffee as she sat and stared.

Finally she broke her silence and said, “Why don’t you stroke it for me?”

Almost as if by instinct now, I did what exactly as she said. I wrapped my right hand around my hard shaft and slowly moved it up and down. She watched in silence for a minute or two before she spoke again.

“Does that feel good?” she asked.

I couldn’t manage to muster an answer. Instead my eyes briefly rolled back in my head. As they opened, I saw that she had finished her coffee and had gotten up off the couch, and moved to take both of our empty cups back to the kitchen.

As she returned I continued to stroke my cock, and was inching ever closer to orgasm.

“You can stop now.”

I immediately did as I was told and found myself more embarrassed than ever, realizing now that I was completely subject to her every whim.

I watched as she made her way toward the back of the house, wondering where she had gone. By now, I knew I was completely out of control. I couldn’t help myself. She had me wrapped around her finger and she knew it. I continued to stand naked in the center of the living room until several minutes later she called for me to join her. I felt like a little puppy dog.

In the back of the house was her bedroom, she had the lights turned down low and several candles were burning. It was dark, but not dark enough where you couldn’t see. She directed me to sit on a small ottoman at the end of her bed as she disappeared into the bathroom.

When she came out of the bathroom, my eyes blinked unsure of what I was seeing. The blink was just a natural reaction. I knew what I saw, and I knew what I had to do. As she approached, I got up from the ottoman and found myself moving to my knees. She didn’t have to ask. She didn’t have to say anything. I knew exactly what she wanted and I was powerless to do anything about it.

I took the cock in slowly at first. It looked and seemed so real, but yet I knew it wasn’t. As my lips tasted it’s rubbery tip my body became overloaded with emotion.

What was I doing? What had I gotten myself into? Why was I on my knees with a cock sliding in and out of my mouth? I felt so vulnerable. I felt so weak.

Melissa stroked my hair as I took the cock deeper and deeper into my mouth, until if finally disappeared, leaving only the black harness strapped around Melissa’s hips to remain.

She encouraged me to suck it, clearly reveling in it. Her hand moved to the back of my head forcing me onto it. The cock fit perfectly. My mouth had never felt so full. It seemed like every nerve inside my mouth was overloaded. I found myself looking up at her as the six inches disappeared into my mouth. As I looked up, she looked down at me and smiled, her hand on the back of my head continuing to guide me.

“You like that don’t you?”

“Uh…yeesssss….hmmmm,” I mumbled.

I felt like half a man as I said it. But at the same time I found it so erotic. I felt so open, so lost, so vulnerable, so powerless. Part of me wanted to do nothing more that to suck her cock. Part of me wanted to take it as deep into my mouth as I could. Being on my knees, with her hand on the back of my head, I felt so dominated and humbled, and so alive at the same time.

After about five minutes on my knees she finally pulled away. I knew what was next. It was obvious. And I knew there was nothing I could do about it.

Without being told I assumed the position. My body leaned over the ottoman with my arms and legs on the floor straddling it and my ass high up in the air. As I lay so prone and so vulnerable, I looked up to see my reflection in the mirror directly in front of me. I immediately closed my eyes, too embarrassed to see myself in such a state.

The next thing I know I felt the warm, slick, gel sliding between my cheeks. So slowly and so ever so gently her fingers slid along my crack. I yelped when the first finger went in, unaccustomed to the unusual sensation. I yelped again when one finger turned to two, and then two to three.

By the time she placed her hands on my hips to mount me, I was begging her, just as she so clearly wanted.

“Please fuck me. Please.”

As she slid in the first time, I watched myself in the mirror as I squealed. She only went part way in, but as she pulled the cock out of me, I watched in the mirror as she smiled.

“Please, please.” I begged.

I groaned as she ent
ered me again.

“Deeper…please…deeper.”

The sensations and feeling that ran through my body as she fucked me were nothing like I had ever felt before. All I could do was watch in the mirror as she fucked me
silly, so powerful, so in-control. I was reduced to a little boy, squealing, begging, wanting. I’d never felt so overwhelmed and so completely overtaken. With her every grunt, I felt more powerless out of control. With her every stroke, I felt more like her toy.

When it was over, I was hers. Totally. Completely. Utterly. There was nothing else that I could be.

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No Responses to “Simple and Straightforward”

  1. Tamuck

    Nice…

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  2. this is a dissapointment. i wanted to hear about a milf being nailed, not some boy being fucked in the ass

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  3. chiquita

    this is incredibly well-written. even tho it’s not my thing, i really appreciate the artful story telling.

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  4. creameater

    love it, nice to hear a story where the milf pounds the boy with a strap on.

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