My wife and I have been together since we were 14 and 16. With that said, we are the only partners we have ever known. I was always the adventurous one, she was always the shy, embarrassed, and reluctant one. We have learned, and achieved an amazing sex life through our constant evolution and experimentation with sex. For the longest time, I could not figure out why she could not achieve what I thought of as an orgasm. She had no complaints, as she was happy with her sexual satisfaction, but I always wanted more for her. To me, getting her to achieve maximum pleasure was my duty, and goal as her lover and spouse.
When she was around 28 years old, I bought her a simple vibrator because we were going to be apart for about 3 weeks for work. She was VERY reluctant about masturbation. That was gross and undignified. Little did she know that I was a Jedi Master at this practice for a long time. We had a talk about how it was alright, and how I wanted her to try her new toy with me. She tried the vibrator in bed next to me, and I for the first time in her presence, pleasured myself next to her. I climaxed watching her have her first, in my opinion, orgasm. We were both enthralled at the new threshold we had met. This was a major stepping stone in our sex life. She learned that there was more out there than what she had known, and was intrigued. I was now more motivated than ever, and was not going to stop until I had her gasping for air and begging me to stop.
A few more years passed, we moved on to other toys, played with setting, atmosphere, adult toy shopping together, reading and what not. Our sex life was getting hotter and hotter. We could not be happier, but little did we know, there was always another mile stone. I had been anal erotic my entire life as I can remember. It was nothing I would ever bring up to her though. I was not gay, and she? Well she would never let me go there, would she?
We had become major fans to oral sex in our early thirties. It was just what we liked best, and we could really get into the control, seduction, passion, the show, and naughtiness of the act. I had read somewhere in my regular Jedi training online, that one could anally stimulate a women while orally pleasing her, and achieve amazing results. I think at this time, we also had just seen an episode of "Sex in the City" where one of the characters had just said that they had discovered the "holy grail" of sex, and it was that she had more than one hole that could be stimulated at once, or something like that. I was intrigued, because that was the grail I was looking for, and my wife didn't even know I was still seeking that grail. Boy would she be surprised, or should I say shocked.
So I made a plan to try a new experiment. That day, we had foreplay, heavy petting, passionate kissing, caressing, for almost an hour. I wanted the horniest, wettest women alive before I went down for the final moves. I did this on purpose because I wanted to make sure I had sufficient lubrication for a little surprise I had for her. I then went down and started my oral magic. I was pretty good at this, and she was always a willing partner. After slowly teasing her, and controlling her up and down with anticipation, she was wetter that I had ever seen her. I then started to massage her perineum with my finger, and achieved some even more promising results. Then I did the move I had been waiting for. The most taboo thing she could ever think of. During a deep passionate moment, I gently stroked her soaked outer anus with my finger. She reacted with an expected "HEY!" and it all stopped for a brief moment. I looked up and said, "you have trusted me all of our sex life, you need to trust me now, I promise, as always, I will not hurt you." She put her head back down on the pillow. I went back to my tongue lashing for a little bit and waited for her to relax to go back for my new move. I then started to caress her anus again gently as I orally pleased her. At first, she was as tight as a pinhole. She was clenching that pucker for all it was worth. then she started to relax a little and moan showing me that she was a little more accepting of the new stimuli. After a while, I noticed that I had to slow down with the oral pleasing to keep her from going over the edge, and that that tight little hole was warming up. I continued to encircle and put a little pressure on my new little spot until I knew she could no longer hold back. I no longer held back with my oral pleasure, but I had noticed something. The closer she was to having an orgasm, the more relaxed her anus was becoming. It was happening fast! Finally, her anus was so relaxed that I now had my finger deep inside her and was thrusting a very relaxed and open hole. So open in fact, two fingers could easily slip in, by I held back. Finally, she went into biggest orgasm I had ever seen, and as she did, her anus became more and more relaxed, much to my surprise. It was the exact opposite of what I had expected. She had the most convulsive orgasm I had ever seen. Her legs clenched around my head, her body writhed, and finally she begged me to stop. I looked up at her with a grin to see her face flushed, and gasping for more air. She said, I don't know what you just did, but my vision went dark for a moment.
I couldn't believe what I had just learned. A super orgasm was achieved! I had learned an amazing lesson about what made her tick. I am not saying this is true for all women by any means because this is the only one I have experience with. However that being said, what I have learned over these years is that she can have various kinds of orgasms. The kind she had in her teens, innocent passionate pleasures. The kind she had with toys in her 20's through today, hot intense, forced, and pleasurable moments. Or what we now see and the "holy grail" orgasm. She did not want anything to do with anal anything, however once she learned it was pleasurable and desirable, she relaxed to receive. It was counter intuitive to relax to orgasm, wasn't it? I mean an orgasm is supposed to be muscle intense tightening right? By allowing me to anally stimulate her, she learned in order for it to be most pleasurable, she must not clench down, and must relax. Just the opposite of what she thought. When she relaxed and received the pleasure, it amplified. It amplifies so much that your pleasure zones relax to an extreme, and the rest of your body convulses in waves. I.e. the major orgasm.
Now I can get her to orgasm many different ways by getting her to relax, more and more, even without anal stimulation. However when anal massage is applied, it forces her to relax to receive.
Needless to say, we found out this also works on me! We discovered this after a little more coaxing on my behalf, and a box of latex gloves and lube I bought her one day. =) My Jedi training had always been to tense up and clench my buttocks to orgasm. Sure it works like a charm. But when I was forced to relax during climax for the first time....lets just say, I too was blacking out, while what seemed like a gallon of fluid was launched somewhere into orbit. Needless to say, we have never looked back.