Older Women Make Beautiful Lovers

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This story takes place in the summer of my 19th year. I had returned to my hometown after an accident which had left me hospitalized for two months. Upon returning I needed to determine a direction for my life. I had enlisted in the army and was awaiting my active duty date in late 1969 when the accident happened. The damage to my body was sufficient to cancel my enlistment and give me a get home free pass from Uncle Sam’s party in Viet Nam. While many of my friends had suffered as a result of that war, I was not sorry that I did not have to go.

So here I was, back in town and not sure of what to do with myself, the band that I had been in before I left for the Army was still together and upon contacting them I was welcomed back with open arms. We were all around the same age and single so we decided to rent a house together so that we could devote much time to practice and recording. Earlier that year before my enlistment, one of the members of the band arranged for his mother who was a tailor to make some show jackets for us. I had never met the lady before and so I was amazed to see this petite woman of 37 (at the time) and pleased at the same time. We had to go to his parent’s house to be measured and then fitted for the jackets. Each time I went for a fitting, his mother would be very pleasant to me and offer me a soft drink, the last fitting took the longest as she kept fussing with seams and re-sewing things as I watched and waited for the “try this on now” that came after every adjustment.

Alice (not her real name) was petite as I said, 115 lbs. Slender, with about 32C breasts and a tiny waist. Each time she bent over to tug on my coat and make sure it hung right, I tried to see down her blouse but to no avail. Now, months later, the experience of a lifetime was just ahead for me. The band had moved in together, and her husband had moved out to live with a much younger woman. So, it was not unusual for her to stop by the house and play house mother to all the boys in the band, making sure the refrigerator contained some healthy items in addition to beer, and that we were all in good health. It was on one of these such visits that she was sitting in the kitchen and her demeanor was anything but the usual chipper smile we were all used to. It seems that she had just found out that in addition to moving out with this young lady, her husband had been carrying on for sometime with some others along his travel route on the road. He was an outside salesman for a line of goods that were sold primarily to women so he had a number of places he could play along the way.

The dark clouds over her head did not seem to be showing any promise of lifting as I pulled up at the table. Her son Tom was across the table from her shaking his head and she was saying.

“I just wish I had someone that I could go out and have a couple of drinks with, but I just don’t know anyone, I have spent way too much time at home for the last few years.”

Tom said, “Maybe that would be good if you could just go let your hair down some, and have more than just a couple of drinks.”

“Well,” she said, “I am not going to go anywhere and have anything alone, that would just make me feel worse.” “Talk about pitiful,” she continued, “out drinking by yourself after your husband has run off.”

I had the feeling that I needed to add something positive to the conversation so I interjected. “Hell, you might start out the evening alone, but I doubt with your looks that you would stay that way for long.”

Tom looked at me in a bit of surprise after what I had said, and Alice replied, “That’s sweet of you to say Stan, but I don’t want to end up with anyone I don’t know at the end of the evening, and that is probably what would happen given my present state of mind.”

Now it was my turn to look surprised, but not as surprised as I was about to become. Tom really gave me a start when he turned to me and said. “Stan, why don’t you take Mom out, you look old enough to get into a bar, you do it all the time, and she would be safe with you.?”

I didn’t really know what to say, she was looking at me and waiting for an answer just like Tom was, although there was a hint of a smile on her face for the first time since I had seated myself at the table with them.

“Well, I suppose, if Alice would like that, we could go to Santa Cruz this evening .” “I have no plans and we are not booked anywhere for two more weeks.” I smiled at her and said, “It would be an honor to escort the prettiest lady I know out for some drinks.”

“And dancing?” Alice smiled a bit more.

“I think I can find us a place to do a bit of both, if you like.” My mind was running away with itself, her attitude seemed to improve greatly, and the fantasies I had often entertained with her as the featured player while masturbating were colliding behind my eyes so vividly, it was hard to conceal my growing erection.

There was a time agreed upon and in preparation for the evening, I had to remind myself that this was Tom’s mother, and not some date that I had an opportunity of scoring with, over and over I said it to myself, but that did not stop me from continuing to prepare with the shadow of hope in the back of my mind. As the appointed time approached, I was positively aching with the hope that I might have another shot at an older woman.

The doorbell sounded distant, it was a cool, but not cold, California summer night, the sun had just set, and the smell of freshly cut grass permeated the air after the Saturday afternoon gardening and watering that took place in most of the neighborhoods like this one. I was not prepared for what I saw as she opened the door, and the look on my face must have spoken volumes. “Is everything alright?” she asked. “You look incredible!” was all I could manage. Her laughter was delightful and she said something about that being a good reaction and handed me the keys to her Cadillac. I had learned early on that, not only do ladies like to have their door opened, but when you did, you got the opportunity to enjoy viewing legs at their finest….and hers were fine. Encased in sheer nylons under a shorter than normal black skirt with a white peasant blouse worn off of her shoulders, she looked good enough to eat.

Closing her door, I moved around to the driver seat and after getting things adjusted to accommodate my 6’3” frame, inserted the key in the ignition, started the car and backed out of the driveway. We were just a driveway away from her house when she said. “Let me see if I still remember how to do this.” And slid across the seat next to me. “After all,” she said “if this is to be a proper date, the girl does sit next to the boy doesn’t she?”

If this is to be a proper date I would be hoping for much more, is what I thought. What I said was, “I don’t think you have lost your touch at all.” Looking down at her dainty feet held together on hump and the skirt that had ridden up her thighs enough to give me a real desire to see more.

“I am happy to hear that,” she said “I was really concerned that I might not be what you wanted.” And after saying that she placed her hand on my thigh and then slid it down to a position that allowed her to place her elbow on the bulge in my pants and sigh contentedly.

During the half hour ride to the coast, we made small talk about the band, and about new outfits that we might have her make for us. She giggled as she talked about the various fittings she had done, about how every one of the guys were nervous and fidgeting except for me….she laughed and said that when I first walked into her living room to be measured that she had thought to herself how much she would love to measure me for a pair of pants too, and that she had scolded herself for her thoughts. I was looking down at her legs now and her delicately crossed ankles as she looked up at me. “I feel safe with you, but I don’t want to, I have wanted to be alone with you from the first time I touched your body.” She looked down at her hand, and squeezed my thigh as she said this.

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