I don’t know why but I’ve always had an infatuation with older women. Back when I was just 18 I had a bad crush on a mature lady, a neighbor of ours named Evelyn. She was a widow in her late 50s, with long dark hair flecked with gray. She had a beautiful face for a woman that age, and I thought she might have been a model when she was younger. She had a medium build with a nice round butt. She used to walk around the countryside wearing a tweed skirt and followed by her dog. I guess she kept in shape by walking so much, and by working in her garden and her yard.
But all I knew for sure was she turned me on, and I wanted to fuck her in the worst way. She was always very friendly and cordial to me, but that was all. Then at one point she happened to mention that she liked chess. I quickly took up the game, and one day I suggested to her that we play sometime, and she agreed.
That got my foot in the door, and soon I was playing chess at her place every day. It was just chess, but I always left with a hard-on at the end of the evening, and I would jerk off repeatedly in my room once I got home. My lust for her was killing me, and I knew I had to do something, but I was very nervous and didn’t know how to go about it.
My chance came one night when I stopped by to take her a present from my parents and me, as we knew it was her birthday. She thanked me for the gift, but seemed a bit sad, since, as she said, she was now one year older. Stupidly, I said something about only being as old as you feel.
“In that case,” she said, “I must be a hundred.”
We both chuckled, and at that point I noticed a bottle of wine on her counter. She told me her sister had given it to her. I then suggested that we drink a toast to her birthday. She looked a little dubious and asked me if I was old enough to drink, and I said yes. She then asked me if I thought it would be all right with my parents. “They wouldn’t mind,” I told her. “They like you, and so do I–a lot.”
She blushed a little and poured us out two glasses of wine. I raised my glass and said, “To the beautiful Evelyn. Your beauty is only surpassed by your charm.”
“Oh, stop,” she laughed as we drank the wine. When it was gone I quickly poured another before she could stop me.
“To friendship and love,” I said, and we drank again.
Evelyn laughed again, but more sadly this time. “I don’t think much about love these days,” she told me. “What with my husband gone and all.”
I guess the wine made me bold. “You need to take a lover,” I said pointedly.
“Ha! A lover?” she replied. “Who on earth would want me?”
“I would,” I said quickly, and reached out to put my hand on hers. Then I leaned in to kiss her.
After only a second or two she pulled away. “Whoa!” she said. “You’re young enough to be my grandson.”
“So what?” I said, a little breathlessly. “You deserve to feel pleasure and to be wanted, and you’re such a beautiful woman.” Now I put my hand on her knee, just below the hem of her skirt, and began to caress it. She put her hand on mine as though to stop me, but as I continued she did nothing. We sat in silence, both looking down as I rubbed her smooth thigh, the hem of her dress rising as my hand moved higher. As I continued she mumbled something about how wrong this was, and when my fingertips brushed the edge of her panties, she gasped and grabbed for my wrist.
“No, we mustn’t!” she breathed. I looked into her eyes then, not saying a word, and finally she relaxed her grip, and my fingers slid under the panties to find her now wet crotch.
The warmth between her legs was phenomenal, and a series of thrills shot through me as I felt all over her crotch, then slid a finger inside her. This made her jump and gasp, and as I moved my searching fingers in and out of her she leaned her head back, her mouth hanging open as she moaned. “Oh my God, that’s lovely!” she panted. “It’s been so long!”
I kissed her again, then pushed her skirt all the way up to her waist, admiring her mature thighs, still smooth and nicely shaped. Then I began to ease her back on the couch, until she was lying there with me leaning over between her outstretched legs. When I grasped the waistband of her panties, she raised her round ass so I could more easily pull them down.
I was thrilled to realize now that she was actually giving herself to me. She was going to let me fuck her. I pushed my pants down, along with my undershorts, and my hard prick sprang out. I crawled up her body and got between her thighs. I teased her slightly by briefly rubbing the tip of my cock up and down her slit before slowly pushing into her.
Evelyn moaned and told me breathlessly how good it felt, and I have to say I definitely agreed with her. Her pussy was not the tightest I’d ever had—though up to that point I’d only had two other girls, both of them my age—but it was so smooth and warm and wet that it didn’t matter.
She still had her top on, and I kissed all over her cleavage as I thrust in and out of her, her moans filling the room. I tried to hold out as long as I could, and at one point I took hold of her ankles and held her legs high, going even deeper into her. But finally it was too much. I tried to fight it, but at last I exploded helplessly inside her, and when she felt it she came too, with a loud scream.
I had never come with such intensity before, and when it was over I collapsed on top of her, and we held each other as we panted for breath.
I was overjoyed to have had her, but I had no idea whether she would ever let me do it again, and Evelyn said nothing about it. But a couple of days later I went back there and found her nipping turnips in the garden. The sight of her bent over that way, with her firm round ass encased in that simple tweed skirt, had me hard in an instant. I slowly moved up behind her, and when I got close to her she looked over her shoulder and saw that it was me. Then she slowly turned back to what she was doing.
I closed the distance between us and pushed her skirt up over her hips rubbing her ass before I undid my pants and pushed them down. Then I tore away the crotch of her panties and slammed my cock into her from the rear. She cried out and hung her head as I began pounding away at her, and I kept it up until we both came.
Evelyn and I continued to play chess after that, but now every game ended with some form of sex. She soon showed me how good she was at pleasuring me orally, and I did the same for her. Even after I went off to college we continued our affair whenever I came home for summers or holidays, and no one but the two of us ever knew about it.
This went on until Evelyn’s death, which happened when I was in my junior year. After that I took a succession of mature lovers, none of whom were under 45. Now I am nearly 30, and the woman I’m seeing is 57. All I can say is thank God for older women.
—N.C., Little Rock, Arkansas