First MILF
"Young man needs help learning about women. Please don't be creepy." was all I put in the ad. I knew I might get some pervs and creepers. But I was hoping for a nice girl that might want to give me advice or better yet take my virginity. It was the beginning of summer and I wanted to lose my virginity and I was starting to think that this might be the only way as I was not very good with girls at all..
Three weeks went by and nothing, not even a creeper or perv. I was pretty sure that maybe anyone looking at the ad might feel that I was a creeper. So I decided to forget about it. Then I got a reply. She said her name was Michelle and she was could help me with advice about girls. I told her my name was Jerry and we traded emails for some time. Then we decided to meet. I picked a location, the mall, to meet thinking if it was a dude or some kind of creeper I could run away being out in public and all. We had a location and time. So I got there a little early to set up a watch and if things did not seem right I would know straight away. We both knew what the other would be wearing so I sat nearby waiting some one called the name "Jerry, is that you?" It was a made up name, I turned to see a very pretty woman standing behind me, "Michelle? Wow I am so glad you are not a creepy pervy old guy." I said with a laugh. "I feel the same way" Michelle replied.
We sat at a table and started to talk. Michelle was an older woman, in her mid fifties. Fit and toned, he works out. Very pretty red hair and warm eyes. Her face does not look her age and she does not look like the type to be answering craigslist ads. She looked like a woman that would be getting sex from rich men. "My husband does not seem interested in me any more, you know for... um..sexually. Well I saw your ad and I was thinking, well, about, well I thought maybe we could help each other out. I have never done anything like this, I can't believe I am here. And my name is not Michelle, it is really Annie." She said looking very uneasy. "My real name is not Jerry, my name is Mike. I have never done this and I am glad that we got to know each other but I get it. I will go home and forget this happened." I said feeling let down. "No! No no Mike, I do think we are here for a reason and we should go forward, but slowly." Annie replied with a warm smile.
We met in person several more times and emailed even more, and text, over the next couple of weeks. And we started to become friends. Then Annie invited me to her house, she lived within bike riding distance from me. I got there and we got to talking. I told her the real reason I placed the ad. Annie said she was surprised by that as she enjoyed being around me and was sure others would be too. Then she told about her situation. I could not believe that this wonderful woman could not catch the eye of her husband. We moved form the kitchen to the couch and next thing I know we are kissing. I was unsure what to do or if I was kissing right. "You kiss really nice, you can move your hands over and feel me, if a woman does not want this she will push your hands away." Annie said. I started to explore her body with my hands, feeling her boobs. And she did the same, feeling my cock. I got her shirt off, then her bra. Her tits were cute, not huge, cute with hard nipples. "Can I suck them?" I asked feeling a little awkward. "I would love it if you did." Annie said. Off came my shirt and Annie pushed her tits against my chest. I thought I might nut my shorts right then and there.
Then off came her pants and then panties. She was now completely naked. Her natural red bush was was hot. Her body was not wrinkled at all like I expected, I was turned on by her. Off came my pants and she played with my cock as I fingered her sweet pussy. She laid back on the couch and pulled me on top of her guiding my cock into her cunt. She was wet and warm, tight. The feel was amazing, you all know how your first pussy felt. Once inside Annie I did not want to pull out. "What do you think? You feel so good inside me." Annie whispered. Well that was all I needed to hear and I came spraying my cum all over her insides. I could not have pulled out if I wanted but as soon as I was done I jumped up thinking she would be mad. "I am so sorry, I did not mean to I should have asked you.." I stammered. "No no worries, I wanted you to cum inside me, I wanted to feel you and to please you." Annie said with a warm smile. I felt good and looked down at her cum soaked bush and gaping sperm filled cunt. "Never worry about cumming inside me Mike, I want that. But other girls you should find out before hand so you do not knock someone up."
So after that we fucked almost every day. And Annie taught me alot about how to please a woman and how to please her. Our sex sessions got pretty intense and she would scream out when she orgasimed. "I have never felt so free during sex before." she would tell me. Her husband would fuck her once a month but I fucked her almost every day. We could not get enough of each other. This went on for the whole summer. When school started back it was harder to find time for us to get together. We did the best we could and I think this made our sex better. Annie told me to try out what I learned on other girls and report back to her. I think she liked knowing that I was fucking other girls while fucking her too. The next summer Annie and I started to hit hard again. She had a couple of friends that needed the attention of a young man like me. I started to bang them on regular basis also.
By the time I finished high school I had many women, older and younger, that I serviced on a regular basis. Placing that ad and meeting Annie was the best thing to ever happen to me. I can not say that if you guys place an ad in craigslist you will find the greatest fuck buddy, but you never know.
Three weeks went by and nothing, not even a creeper or perv. I was pretty sure that maybe anyone looking at the ad might feel that I was a creeper. So I decided to forget about it. Then I got a reply. She said her name was Michelle and she was could help me with advice about girls. I told her my name was Jerry and we traded emails for some time. Then we decided to meet. I picked a location, the mall, to meet thinking if it was a dude or some kind of creeper I could run away being out in public and all. We had a location and time. So I got there a little early to set up a watch and if things did not seem right I would know straight away. We both knew what the other would be wearing so I sat nearby waiting some one called the name "Jerry, is that you?" It was a made up name, I turned to see a very pretty woman standing behind me, "Michelle? Wow I am so glad you are not a creepy pervy old guy." I said with a laugh. "I feel the same way" Michelle replied.
We sat at a table and started to talk. Michelle was an older woman, in her mid fifties. Fit and toned, he works out. Very pretty red hair and warm eyes. Her face does not look her age and she does not look like the type to be answering craigslist ads. She looked like a woman that would be getting sex from rich men. "My husband does not seem interested in me any more, you know for... um..sexually. Well I saw your ad and I was thinking, well, about, well I thought maybe we could help each other out. I have never done anything like this, I can't believe I am here. And my name is not Michelle, it is really Annie." She said looking very uneasy. "My real name is not Jerry, my name is Mike. I have never done this and I am glad that we got to know each other but I get it. I will go home and forget this happened." I said feeling let down. "No! No no Mike, I do think we are here for a reason and we should go forward, but slowly." Annie replied with a warm smile.
We met in person several more times and emailed even more, and text, over the next couple of weeks. And we started to become friends. Then Annie invited me to her house, she lived within bike riding distance from me. I got there and we got to talking. I told her the real reason I placed the ad. Annie said she was surprised by that as she enjoyed being around me and was sure others would be too. Then she told about her situation. I could not believe that this wonderful woman could not catch the eye of her husband. We moved form the kitchen to the couch and next thing I know we are kissing. I was unsure what to do or if I was kissing right. "You kiss really nice, you can move your hands over and feel me, if a woman does not want this she will push your hands away." Annie said. I started to explore her body with my hands, feeling her boobs. And she did the same, feeling my cock. I got her shirt off, then her bra. Her tits were cute, not huge, cute with hard nipples. "Can I suck them?" I asked feeling a little awkward. "I would love it if you did." Annie said. Off came my shirt and Annie pushed her tits against my chest. I thought I might nut my shorts right then and there.
Then off came her pants and then panties. She was now completely naked. Her natural red bush was was hot. Her body was not wrinkled at all like I expected, I was turned on by her. Off came my pants and she played with my cock as I fingered her sweet pussy. She laid back on the couch and pulled me on top of her guiding my cock into her cunt. She was wet and warm, tight. The feel was amazing, you all know how your first pussy felt. Once inside Annie I did not want to pull out. "What do you think? You feel so good inside me." Annie whispered. Well that was all I needed to hear and I came spraying my cum all over her insides. I could not have pulled out if I wanted but as soon as I was done I jumped up thinking she would be mad. "I am so sorry, I did not mean to I should have asked you.." I stammered. "No no worries, I wanted you to cum inside me, I wanted to feel you and to please you." Annie said with a warm smile. I felt good and looked down at her cum soaked bush and gaping sperm filled cunt. "Never worry about cumming inside me Mike, I want that. But other girls you should find out before hand so you do not knock someone up."
So after that we fucked almost every day. And Annie taught me alot about how to please a woman and how to please her. Our sex sessions got pretty intense and she would scream out when she orgasimed. "I have never felt so free during sex before." she would tell me. Her husband would fuck her once a month but I fucked her almost every day. We could not get enough of each other. This went on for the whole summer. When school started back it was harder to find time for us to get together. We did the best we could and I think this made our sex better. Annie told me to try out what I learned on other girls and report back to her. I think she liked knowing that I was fucking other girls while fucking her too. The next summer Annie and I started to hit hard again. She had a couple of friends that needed the attention of a young man like me. I started to bang them on regular basis also.
By the time I finished high school I had many women, older and younger, that I serviced on a regular basis. Placing that ad and meeting Annie was the best thing to ever happen to me. I can not say that if you guys place an ad in craigslist you will find the greatest fuck buddy, but you never know.
6 years ago
