The oldest women I ever had sex with
This is a true story. It has not been exaggerated or embellished in any way and is told in the sequence that it happened.
When I was a young man in my early 30's, I wanted sex as often as possible. I soon discovered that I preferred slightly older women who were widowed or divorced. Back then, there was no Internet, so we corresponded through newspaper ads in the "Personals" section. We wrote letters (not e-mails) and talked on the telephone (not texting). One ad intrigued me. It read: "Very old widow seeks companionship."
I contacted her and she told me that her name was Mildred and that she had been widowed for 35 years. We agreed to meet, and I would take her out to dinner. When I arrived at her house, she greeted me at the door. I guessed that she was about 85 years old and was dressed in a red dress, wearing makeup and nylons and heels. Even though Mildred was very old, she was still attractive, and we went off to dinner.
During dinner, I asked her why she had placed the ad, and she said it was at the insistence of her much younger niece. I asked her how many responses she had received, and she told me that, because of the way that she had worded it, I was the only person who had responded.
We had a great time and when we went back to her place, she invited me in and we sat on her couch. She then said to me "Now that we've met and you see how old I am, I'll probably never see you again." "On the contrary" I replied, "I intend to see much, much more of you. I then leaned over and gave her a kiss on her lips.
She didn't resist the kiss, and I held it for a long time. I opened my lips and slipped my tongue into her mouth. Still, she didn't resist but it took her a long while before she responded with her own tongue. After the kiss ended, Mildred said "Wow, I've never been kissed like that before."
"Didn't your husband kiss you like that?" I asked. "Him" she snorted "He never did anything. All that he did was shove it in, do his business, and then roll over and go to sleep. No wonder we never had any kids."
"Well, I'm not going to treat you like that." Then I leaned over and gave her another deep kiss. This time she eagerly responded with her own tongue. Having gone this far, I reached up and gently took her left breast in my hand. There was a sudden shock on her part, but she didn't push my hand away.
I continued to gently fondle her breast and began searching for the nipple. I soon found it through the fabric of her dress and the bra and began to massage it. I could feel it getting hard and Mildred let out a gentle sigh. She was obviously enjoying the attention and made no effort to stop me.
I reached down and put my hand on her nyloned knee. I love women in nylons and began to massage her leg. Slowly I worked my hand up under the dress and fondled and stroked her thigh. Mildred never stopped me and kept muttering how nice it was to have a man paying attention to her.
Eventually I reached her crotch and discovered that she was wearing pantyhose. Not to be deterred and having been so successful this far, I moved my hand up to the top of the pantyhose and slid my hand down into her panties. For an instant, Mildred froze, and I thought that she was going to stop me. But then she relaxed, and I began to fondle her vulva. My middle finger slid down and then entered her surprisingly wet vagina.
At this point, Mildred was totally relaxed as I continued to play with her pussy. I slid my now very wet finger up and found her clitoris. I began to rub gentle circles on it as I masturbated her. It took a long time but, eventually Mildred shuddered and had, what must have been her first orgasm in her whole life.
When it was over, Mildred asked "What was that? I've never felt like that in my whole life." "You just had an orgasm. Didn't you ever masturbate and do that?" Mildred blushed and said "I was taught that good girls don't touch themselves down there." I replied "Well, you're a very good girl and, from now on, you can touch yourself like that whenever you want" And so began many years of sex with Mildred.
The next time we met, Mildred insisted on making dinner for me. After a wonderful dinner, we retired to the couch and began playing. Over the phone, I had told her that I didn't care for pantyhose and, this time, when I slid my hand up under her dress, I discovered that she was wearing seamed nylons and a garter belt ... and no panties! From then on, Mildred always wore nylons when we were together.
We went into the bedroom and, after many, many years, Mildred had a man making love to her. After we were undressed and I saw her totally naked, she said "Now that you see me in the altogether, do you still want to play with me?" "What do you think?" I replied as I showed her my very erect penis sticking straight out. "May I touch it?" she asked. "You can do whatever you want to it, it's all yours." I replied. So, for the first time, Mildred handled a man's erection.
We climbed into bed and began to play. Having read that older women can be dry, I had brought along a tube of KY and applied it to my erection. I spread her legs apart and gently, for the first time in over 35 years, my erection entered her vagina. I moved slowly in and out and I soon came in Mildred as we made love for the first of many wonderful lovemaking sessions.
Over time, I ate Mildred's pussy and gave her orgasms that way. She also learned how to give me blowjobs and became an expert as making me cum with her mouth.
For many years, our sex was wonderful and very satisfying. But eventually age caught up with her and she went into the hospital for the last time. I visited her there and she was very happy to see me. As our visit was ending, she whispered to me "Please, play with me one last time."
She was in a private room, so I closed the door and put a chair against it. Then, sliding my hand under her hospital gown, I masturbated her to a climax. Mildred then rolled to the edge of the bed and whispered to me "My turn." I opened my pants, and she took my penis in her mouth. Sure enough, her skillful mouth soon brought me to an intense climax and she swallowed all of my seed.
"Now I can die in peace." Mildred whispered. "Nonsense" I replied. "You'll soon be home, and we can continue to make love." She just smiled as she drifted off to sleep.
The next day, I called the hospital, and they told me that Mildred had peacefully died in her sleep during the night. Then the nurse asked me a question. "What did you say to her when you visited yesterday? Mildred had such a happy smile on her face when she died."
I lied and said that I had told Mildred how much she was loved and how much everyone thought so much about her. But I didn't tell them the real reason for Mildred's last enjoyment.
Rest in Peace Mildred. I'll never forget you.
When I was a young man in my early 30's, I wanted sex as often as possible. I soon discovered that I preferred slightly older women who were widowed or divorced. Back then, there was no Internet, so we corresponded through newspaper ads in the "Personals" section. We wrote letters (not e-mails) and talked on the telephone (not texting). One ad intrigued me. It read: "Very old widow seeks companionship."
I contacted her and she told me that her name was Mildred and that she had been widowed for 35 years. We agreed to meet, and I would take her out to dinner. When I arrived at her house, she greeted me at the door. I guessed that she was about 85 years old and was dressed in a red dress, wearing makeup and nylons and heels. Even though Mildred was very old, she was still attractive, and we went off to dinner.
During dinner, I asked her why she had placed the ad, and she said it was at the insistence of her much younger niece. I asked her how many responses she had received, and she told me that, because of the way that she had worded it, I was the only person who had responded.
We had a great time and when we went back to her place, she invited me in and we sat on her couch. She then said to me "Now that we've met and you see how old I am, I'll probably never see you again." "On the contrary" I replied, "I intend to see much, much more of you. I then leaned over and gave her a kiss on her lips.
She didn't resist the kiss, and I held it for a long time. I opened my lips and slipped my tongue into her mouth. Still, she didn't resist but it took her a long while before she responded with her own tongue. After the kiss ended, Mildred said "Wow, I've never been kissed like that before."
"Didn't your husband kiss you like that?" I asked. "Him" she snorted "He never did anything. All that he did was shove it in, do his business, and then roll over and go to sleep. No wonder we never had any kids."
"Well, I'm not going to treat you like that." Then I leaned over and gave her another deep kiss. This time she eagerly responded with her own tongue. Having gone this far, I reached up and gently took her left breast in my hand. There was a sudden shock on her part, but she didn't push my hand away.
I continued to gently fondle her breast and began searching for the nipple. I soon found it through the fabric of her dress and the bra and began to massage it. I could feel it getting hard and Mildred let out a gentle sigh. She was obviously enjoying the attention and made no effort to stop me.
I reached down and put my hand on her nyloned knee. I love women in nylons and began to massage her leg. Slowly I worked my hand up under the dress and fondled and stroked her thigh. Mildred never stopped me and kept muttering how nice it was to have a man paying attention to her.
Eventually I reached her crotch and discovered that she was wearing pantyhose. Not to be deterred and having been so successful this far, I moved my hand up to the top of the pantyhose and slid my hand down into her panties. For an instant, Mildred froze, and I thought that she was going to stop me. But then she relaxed, and I began to fondle her vulva. My middle finger slid down and then entered her surprisingly wet vagina.
At this point, Mildred was totally relaxed as I continued to play with her pussy. I slid my now very wet finger up and found her clitoris. I began to rub gentle circles on it as I masturbated her. It took a long time but, eventually Mildred shuddered and had, what must have been her first orgasm in her whole life.
When it was over, Mildred asked "What was that? I've never felt like that in my whole life." "You just had an orgasm. Didn't you ever masturbate and do that?" Mildred blushed and said "I was taught that good girls don't touch themselves down there." I replied "Well, you're a very good girl and, from now on, you can touch yourself like that whenever you want" And so began many years of sex with Mildred.
The next time we met, Mildred insisted on making dinner for me. After a wonderful dinner, we retired to the couch and began playing. Over the phone, I had told her that I didn't care for pantyhose and, this time, when I slid my hand up under her dress, I discovered that she was wearing seamed nylons and a garter belt ... and no panties! From then on, Mildred always wore nylons when we were together.
We went into the bedroom and, after many, many years, Mildred had a man making love to her. After we were undressed and I saw her totally naked, she said "Now that you see me in the altogether, do you still want to play with me?" "What do you think?" I replied as I showed her my very erect penis sticking straight out. "May I touch it?" she asked. "You can do whatever you want to it, it's all yours." I replied. So, for the first time, Mildred handled a man's erection.
We climbed into bed and began to play. Having read that older women can be dry, I had brought along a tube of KY and applied it to my erection. I spread her legs apart and gently, for the first time in over 35 years, my erection entered her vagina. I moved slowly in and out and I soon came in Mildred as we made love for the first of many wonderful lovemaking sessions.
Over time, I ate Mildred's pussy and gave her orgasms that way. She also learned how to give me blowjobs and became an expert as making me cum with her mouth.
For many years, our sex was wonderful and very satisfying. But eventually age caught up with her and she went into the hospital for the last time. I visited her there and she was very happy to see me. As our visit was ending, she whispered to me "Please, play with me one last time."
She was in a private room, so I closed the door and put a chair against it. Then, sliding my hand under her hospital gown, I masturbated her to a climax. Mildred then rolled to the edge of the bed and whispered to me "My turn." I opened my pants, and she took my penis in her mouth. Sure enough, her skillful mouth soon brought me to an intense climax and she swallowed all of my seed.
"Now I can die in peace." Mildred whispered. "Nonsense" I replied. "You'll soon be home, and we can continue to make love." She just smiled as she drifted off to sleep.
The next day, I called the hospital, and they told me that Mildred had peacefully died in her sleep during the night. Then the nurse asked me a question. "What did you say to her when you visited yesterday? Mildred had such a happy smile on her face when she died."
I lied and said that I had told Mildred how much she was loved and how much everyone thought so much about her. But I didn't tell them the real reason for Mildred's last enjoyment.
Rest in Peace Mildred. I'll never forget you.
7ヶ月前
