For many years, I used to answer ads and enjoy other men's wives. Husbands sought other men to join them and their wives for sexy fun, and I was more than happy to oblige. Occasionally, only the wife would advertise for a male, and I was always eager to fill the need, when invited.
These arranged meetings fulfilled my libido and were lots of fun, but over the years I wearied of the predictability of the sessions. They advertised, and when we met everyone knew the routine. Not that some weren't more zippy.
Over time, I realized that what I enjoyed most were situations where the wife wasn't sure and had to be coaxed. It occurred to me that I got more satisfaction from what I called "free range wife pussy" than from the more staged and predictable sessions.
I had been fortunate to have been invited by so many hubbys and wives for playtime, and I learned that a good sense of humor and kindly attitude was the key to success. And, of course, they were almost always looking for a bigger dick scenario, and although I don't have a monster cock like some of these stories brag about, my eight inches seemed to satisfy everyone.
Now, in my forties, I still respond to a few old friends who call or to their friends who want a to be fucked discretely by a trustworthy male. But I have ceased answering or placing ads. Now, I am experimenting with seeking out likely ladies who are "of a certain age" and underappreciated by their spouses. Believe me, there are plenty out there, and more than a few like to flirt.
It takes a different skill set to start from scratch, so to say. Answering ads was like shooting fish in a barrel, but free range pussy hunting requires patience and intuition. If successful, the rewards are correspondingly higher.
My target population are older women who are still lovely and in shape. Nowadays, more and more older women are working out and keeping their figures. I've been pleasantly surprised to find that the inventory of desirable older lovelies is fare more than I had thought. Ha, or maybe as I get older, my standards have shifted.
My first attempt was with a stately and lovely women about twenty years my senior. I met her through a civic organization where we were both members, and we've been acquaintances for several years. She caught my eye right away. I had been invited to her home, and I met her husband.
She confided in me one time, and that lit my fuse. Here's what happened.
We bumped into each other at a coffee shop, and sat together for a chat. She seemed sad, and I asked her what was bothering her. Alexandra was always dressed fashionably and wore colors that complemented her jet black hair. Her jewelry and hair were just right. She had high cheek bones and a cute sculpted nose. Her lips were thin but expressive. Very kissable, I thought.
I'd knows her long enough, and felt comfortable enough, to confide in me that although her marriage was fine and her husband was a good provider, she felt bad because her husband, Dale, kept a stash of Playboy Magazines in his dresser drawer. "Golly," she said, "Doesn't he know how that makes me feel? Like I'm not good enough?"
I sympathized, I let her talk and tried to convey my respect for her and my concern for what she'd told me. "Oh my," I said, "I suppose that's not unusual." I paused then added, "But how could anyone married to you ever be tempted by other women?"
She smiled and wiped away a little tear. "Thank you."
"Here," I said, "let me refill your coffee."
How strange, I thought, that Dale would collect magazines in this day of Internet porn. He must be an old fashioned guy.
We continued a conversation about her life and her marriage. I tried to conceal that fact that I wanted to fuck the daylights out of her then and there and that my cock was ready for the job. I played the sympathetic and understanding male friend. Several times, I reassured her of her beauty, a natural beauty and a soulful beauty that came from deep inside.
She thanked me repeatedly, and she apologized for bringing all this up.
"Oh, no," I said, "I'm glad you felt you could trust me. You needed to talk with someone."
She smiled. "I've always been a good girl," implying that she hadn't flirted or sought to have affairs during her marriage. I respected that, and told her so.
"Let me walk you to your car," I said. As she stepped across the floor I admired her shapely rear and the curve of her calves below the hem of her dress. In the parking lot, I walked her to her car and opened the driver's side door. I turned and offered her an embrace. We hugged briefly, nothing out of order, but she looked surprised when I kissed her on the cheek.
I held her car door open and stood in perfect position to see every bit of her legs she might reveal as she got into the driver's seat. I thought to myself, "Isn't it amazing that such a desirable woman should be slighted by her husband? Go figure."
Then I caught another break. She closed the car door, but she didn't notice that part of her skirt was hanging outside the bottom of the door.
I knocked on her side window, "Hey, watch out!"
She lowered her window, and I told her about the skirt.
"Oh! Thank you," she said as she opened the door. I grasped the door handle and opened it wide, and before she could adjust her clothing, I reached down and gathered up the material and took a chance.
As I adjusted her skirt, I took the liberty of lifting the hem of her skirt so that her entire legs were exposed, but I pretended it was a mistake, "Oh, pardon me," I told her. But then I saw her white panties. Alexandra squirmed in her seat trying to protect her modesty, but only succeeded in open and closing her legs in a way that let me get a nice view of what looked like a mass of puffy dark hair underneath her panties.
I held up her skirt and leaned into her car door. Gazing at her exposed legs and panties, I said, "I don't think any Playboy model could possibly be as lovely as this." Then I quickly dropped her clothing, politely closed her car door, and saw Alexandra's startled and blushing face. Then I added, "My apologies."
She quickly started the engine, backed up, then at the street corner signaled left but turned right. Clearly, the lady was rattled. And me? I had dared to step out of bounds, and I had a stiff and wet slick cock to deal with.
Once I got home, I texted Alexandra, "Wonderful to see you today. The more I see of you, the better, as far as I'm concerned." About an hour later, she texted back with just a little happy emoji. All that evening, I nursed my hard-on until it exploded while think of Alexandra.
The next week, I saw her at a committee meeting. Since our coffee and my boldness to steal a look up her dress, I had been eager to see Alexandra again. She saw me before the meeting started, and her face blushed. I greeted her and held her hand. If she was an old fashioned gal, I thought she might like that. I kept holding her hand as others come by and greeted us, then we sat next to each other.
Afterward, I walked her to her car. "Hope you don't have a wardrobe problem again," I said to her.
Alexandra sputtered a laugh and said, "If I do, I know you can solve it." My dick had started dripping from the moment I saw her that evening, and now I could feel a stream of sticky cum running down my leg. I laughed, too.
At her car, I started to say good night and not to push my luck this time, but then I turned back and took her in my arms. "What about a good night kiss?" I asked.
Alexandra was wide eyed, and I didn't wait for her to answer. I kissed her on one cheek, then the other, then looked into her eyes, "How about a kiss on the lips?" I leaned toward her, and she was almost limp in my arms. We kissed quickly, just a peck. Then I gave her a real kiss, a long moist kiss. As we kissed, I could feel her hard nipples against my chest.
When I drew back, she leaned in toward me. Not wanting to spoil the moment or to push ahead too fast, I released her and said good night as I walked away toward my car. I thought it was better to leave her in a high strung state rather than to ask for too much too quickly. I knew that she was thinking about straying from her husband. It was clear to me that Alexandra was on the brink.
