Maine Friend: Winter Sailboat

Impulsively I posted the following listing on a popular website:

I am a professional married woman looking for a friend. I would like to get to know this person through email, chat, phone conversations and maybe meet someday. I have an active imagination and I'd like to share that part of me with someone. I want someone who is in a similar situation as I am, married but wanting to discreetly share fantasies.

My new friend would be in his 40's or 50's, good sense of humor, intelligent, honest and patient. How you look doesn't matter a whole lot if you can have a conversation and be genuine in what you want. I am looking for a potential long term friendship.

As for me, I am in my thirties and fit. I am not a beauty queen but I am attractive by most realistic standards. I run, a regular gym rat and take good care of myself. I am educated and when I'm not at the gym or running I am taking care of my house, family. I have a demanding career and I'm looking for an outlet to express another side of me that I can't seem to do in my current situation or perhaps don't want to do.

I'm not miserable and not in a miserable marriage. I'm a happy person but want to see what it's like to explore another person, his fantasies and my own as well.

That is how I met my friend from Maine.

Our first meeting after speaking on line was at a restaurant in a small town convenient to us both. Meeting him that day was almost as impulsive an act on my part as writing the listing. Some work commitments had been cancelled freeing up part of my day, he was on line so we agreed to meet.

I had not dated much in my life. I met my husband first year in college and I had worked through high school which did not leave much free time to socialize during my teen years. Perhaps the only way I could have met my friend this first time to do so impulsively or else the reasoning of why it all seemed wrong, the nervousness of facing someone new where potential for more had been discussed might have overwhelmed me and not allowed me to follow through. He seemed genuine, honest and the fantasies we had discussed were taking root deep in my imagination. I wanted to meet him.

Neither of us had seen other people since our marriages. I am in my 30's and he is in his 40's so for both of us, seeing someone new like this after meeting like we had filled us both with nervous anticipation. We had talked about our lives but in those discussions before we met we had also spoken about our fantasies, curiosities and desires to explore in ways that still scared us both. So, meeting a man for the first time knowing that he is the only person on the planet that knows the extent of my fantasy life was enough to make my knees weak, my hands sweaty and set me running in the opposite direction.

There is a full length mirror in my office building. Before leaving for this lunch I stopped and discretely checked myself out. I hadn't really looked at myself from the prospective of a 40 something man. I am 5'7" and fairly fit. My short skirt and dark hosiery showed my muscular legs that I earned from running 30 miles a week. The fitted black sweater over my 36D breasts also gave me some confidence that my friend might imagine what they might feel like to touch. My dark hair is somewhat long, but very curly. Yes, I was as confident enough not to run and decided my description in my listing was as accurate as I could be. Most men in their 40's might consider having at least lunch with me.

I did not go into the restaurant; he came outside to get me. I could barely look at him I was so nervous. In my fantasies I did not have a vision of what my friend would look like. How my friend would look had not played a role really in how I felt when during my erotic daydreams. However, my new friend was a pleasant surprise. I did not expect him to be cute, almost unbearably sexy.

The first thing I noticed was his mouth, how full and kissable it seemed. Given my nerves I was shocked that even a glint of sexual spark was able to ignite but it did when I saw his mouth smile at me the first time. Only a bit taller than me, dressed casually in jeans and fleece sweater, I could tell he was nervous as he turned various shades of red during our conversation. We had a nervous but comfortable conversation. We were even able to shift our conversation to what had brought me to write the listing and his response. This was a pleasant surprise to me that I was able to have this conversation with him given what we had spoken about on line and on the phone. It seemed I having little trouble imagining him naked and my mind was gloriously running through our previous discussions as I started to put a face to my newly developing daydreams.

No touching other than a departing hand shake, my shaky legs walked me to my vehicle and in a fog I drove back to work. We continued to talk on line and the phone until out of the blue the next Sunday morning we both realized that for a few hours that very afternoon would be alone. We decided to meet at a local bookstore and neither of knew exactly what we would do then. I saw him first and tapped him on the shoulder. Yes, he was still pretty darn cute. We wandered the store a bit then decided he would take me and show me his boat.

Of course this meant I had to get in his car. My mind raced with what my family and friends would think of me getting into the car of a man I met on the internet. I could see their faces flash through my mind as I imagined what they all would think if they knew. Always very responsible, never out of character, consistently predictable....this behavior was not expected of me. But, I happily and confidently jumped into his car with no ambivalence whatsoever.

It was a short drive to his boat. It was very cold and neither of us was exactly dressed for the 30 degree day. I was dressed in jeans, turtleneck and light jacket and he was dressed similarly. We climbed the ladder up to the deck and took me down and showed me the interior. Standing in the coldness of the bottom of this boat he suddenly and without warning kissed me. His lips felt like I had imagined they would, full and warm. We came together so closely and he wrapped me so thoroughly in his arms that the cold disappeared and all I could feel was his warmth.

His back to a wall, I faced him and we continued to embrace. Our hands were exploring, touching, wondering with fascination about the mystery of the other. My mouth kissed his and I could feel his response as I kissed his neck, his ears. His body was warm as my hands started to explore under his clothes. He raised my shirt, releasing my bra and took my nipple in his mouth. The cold air and his warm mouth shot made my nipple harden immediately. His hand held my breast as he kissed it, became familiar with it. My hand reached down and I could feel his erection through his jeans. My hand started to stroke him through his jeans and his hips moved to my hand. I could feel the outline of his cock as it pressed against his jeans. I could feel the head, the rim and long shaft.

Needing to feel him in my hand, I unbuttoned his jeans and slid my hand inside. He was almost hot in my hand and I could feel him respond as my fingers and thumb started to stroke. His size was new to me, as I stroked I wanted to feel him in my mouth. His cock was large, engorged and I could feel his pulse as my fingers stroked. Kissing my way down I took his cock in my mouth. Deep at first so he could feel the warmth of my entire mouth then letting my tongue explore by licking and lightly sucking his head and rim. My tongue could feel the bulging and pulsing of his shaft and head as my tongue flicked, licked and sucked. Keeping the head of his cock between my lips as my tongue swirled elicited a response from him that made me want to reach down into my own panties and touch myself.

His sounds, his movement into my mouth and the bulging veins soon told me he was going to cum. I wanted him to cum in my mouth, I wanted to taste him and feel his sheer pleasure of my tongue and lips. His hips moved, his moan low as he came filling my mouth with the warmness of his cum. Stroking him, kissing my way back up my mouth continued to enjoy his lips and his neck.

As we remained standing in that same spot, his thigh moved between my legs where I moved in rhythm to my own need to feel release. His fingers found their way into my panties and they found the wetness that wanted so badly. My hand wandered back down to stroke his cock and I could feel him come to life again as my fingers gently stroked.

Again, I leaned and took him in my mouth. My tongue tenderly stroked and prodded him to erection. The pulse was quick under my tongue, the fullness ready to erupt soon as I took him deep almost to his base. My mouth almost able to take him completely I could feel the throb of his cock as he readied to cum for the second time. His warm cum again filled my mouth. Draining him, stroking him to completion I stood and kissed him hello.