I am 58 years old. I have been pretty much single since I was dating age when I got my drivers license when I was 15. Over the years I have gotten many different women to do many different things. From swinging, going out in public in a dress with no panties, to flashing my friends in a bar, to wearing cum on her face in public and more.
But one thing that seems to stand out among all is, there have been a few women that said Anal was off limits and refused to even talk about it. But eventually got them not just do it but love it.
One example was, when I was 21 I was dating this 18 year old catholic girl that was adamant about not doing anal and that she wouldn’t even talk about it. Once I was fucking her real hard missionary style and as doing so, I reached around and started rubbing my finger on her asshole. She tried to move out of the way but I continued to fuck her real hard and she just didn’t have it in her to make me quit.
Just as she was cuming I shoved my finger into her asshole. Afterward she halfheartedly acted as if I done something bad. I just joked with her telling her she came so she liked it. The next day I was fucking her doggy style and I was hitting it pretty hard. As I was doing so I put my thumb on her asshole and was just rubbing it. She said stop but I didn’t and she kept moaning and groaning and was getting close to climax. Just as she was cuming I shoved my thumb into her ass and kept on fucking her. She screamed and came hard and fell on the bed breathing hard and shaking.
When she calmed down and was able to talk, she said I hate to admit it but I liked that. She said it made her orgasm more intense. I said it is time to talk about trying anal now. She said ok. After talking to her about it a few more times and teaching her that this was something that needed to be planned so we don’t make a mess. She should do an enema.
Back in the early 80s the only lube I knew of at the time was KY jelly. After her enema and came to the bed. We had a vibrator and I told her to put it on her clit. I lubed up her asshole as she masturbated with the vibrator I lubed up her asshole and finger fucked her asshole. She had a small orgasm. At that point I lubed up my dick real good. I put my dickhead at the entrance of her asshole and I told I will not push and for her to get into the vibrator and only push on my dick when she felt like it.
As she got excited and was bucking her hips, I kept the pressure in her asshole. I felt the head enter her asshole as she was bucking and having orgasms form the vibrator. Before long, my dick was half way in. At that point I said OK I am going to fuck you now.
She was so excited she couldn’t say anything. So I stated slowly and I could feel her relax. I started pumping in and out slowly and going more and more deep. Before long I was going in and out of her asshole all the way and she was cuming over and over and to the point I started to cuming inside her asshole.
After it was over, she said, I like that! She said it with enthusiasm. I said to her any time you want it just ask me. To which she said I will be asking a lot. And after that day she did. After that day it seemed she had an obsession with anything anal. She wanted me to go to the video rental store and rent a porn dedicated to anal. There was not much to choose from in those days but we did. Then she started to lick my asshole when she was going down on me without me asking or suggesting it. Almost every single time.
One day we were making a bet one time. I cannot even remember what the bet was but I do remember her saying the loser has to tongue fuck the winner’s asshole. I then said I don’t care if I win or lose. She said I know! With a smile in her face. One night we were drinking with some friends (another couple) and we all decided it was time to fuck.
My girlfriend and I was in the bedroom and our friends were in the adjoining room with the door wide open. She said out loud “FUCK ME IN MY ASS” I know they heard her but I didn’t care. I laid down on my back she got on top grabbed my dick and shoved it into her ass. No lube, no slow going, She just crammed herself down on me hard. She was screaming an orgasm in less than a minute. Afterword as we were all getting up and getting dressed and talking to out friends, as the friends were leaving the guy said, did y’all really do anal? I didn’t say anything and she said with enthusiasm YES! Her girlfriend said Ill never do that with a snarl in her voice to which my girlfriend said I used to be like you until he taught me how and now, I prefer it in my ass over my pussy.
I hated that the two of us split up because she would have been one of the few girls I would have wanted to stay with forever but that is for another conversation. But I can say I taught her and/or convinced her to do anal and she absolutely loved it.
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