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The Booty Blog: 4. Winston’s Story

Wicked Wanda's Anal anal sex Booty Blog Julia Winston sexpert Wicked Wanda's

Guest Writer:

Julia Winston

The short version of the story goes like this. Painfully virginal middle-class suburban girl grows up in painfully normal and comfortable 'proper' neighborhood. She learns about her body parts from books and school sex Ed. class. This girl will be a good girl, not sleep around in high school, meet her husband at 17, marry him at 21 and think that it will be perfectly fine to spend the rest of her life making herself climax after sex instead of during. At least I was capable of orgasm, I had an inkling that many women were not. Fast forward to age 22, when an unexpected man from my past reentered my life in the most serendipitous and wonderful of ways. Fast forward to the moment I realized that my marriage, although comfortable and loving and without any obvious flaws, was...how should I put this...boring. I started to get the feeling that perhaps I was missing something, that perhaps at the age of 21, I didn't know everything. I have always been a curious person, but at the time, I had trouble escaping the cultural paradigm on which I was raised. My husband was older than me and even less sexually experienced than I was.

It took a chance encounter with my high school sweetheart to get the curiosity flowing. It took his constant positivity and trustworthiness. It took months and months of excruciatingly chaste friendship until finally, my sexual-self emerged from the shadows, a surprise it seems, only to me. He knew I had it in me all along and he was determined to help my inner slut emerge and flourish. Our society loves sexy women but shuns women who love sex. I wasn't ready yet to be seen as a slut.

Our passion was palpable and rooted in pheromones and matching chemistry but our encounters were still reticent, cautious and controlled due to my inability to turn off my brain and surrender. I couldn't let go of mother culture. I was open though, and willing to try new things. We would watch porn together and talk about things that turned us on. I ALWAYS skipped the butt stuff. I thought it was the ultimate turn off. How could anal sex possibly be comfortable, clean or pleasurable for that matter. Surely only porn stars have anal sex and then surely only because they are being paid and men like it. My upbringing was germaphobic and private. Asses MUST be disgusting. So although I continued being 'adventurous' in my eyes, I was clearly not living up to the spirit of the word. During this period in my life, I tried anal sex once or twice and did not love it or hate it, just mostly felt indifferent and confused about it.

Fast forward again. Lovers have come and gone. None have insisted on anal and so I felt secure in the fact that this would not be a part of my sexual experience and was totally at peace with that. High school lover comes back into my life again and this time, our wild oats have been sowed with others and we are ready to move forward in exploration together. He has ALWAYS loved anal sex but I never knew how much. I wonder whether my reticence on this issue will cause our relationship to fall apart and so I open myself up to all possibilities. I let love and trust rule and throw all caution to the wayside. I decide to let him 'train' me. He knows what he is doing and I feel confident.

Those first couple months of my training were some of the most intense of my life. Not only was I expanding my sexual repertoire, but I felt my mind and spirit expanding as well. I gained a new appreciation for my body and what it is capable of. I felt pleasure I did not even know existed. My first ass plug was a beautiful metal weighted crystal jewel plug and it felt more like a piece of jewelry than a training tool. It made my ass feel pretty. It made me feel like the hole I had so overlooked was more special than I had given credit. As my sexual appetites changed and grew, I came to enjoy anal sex even more than conventional sex. I came to wish I could train longer and harder. I came to want to please my partner in ways I would have shunned 10 years before. And the pleasure and closeness was mutual. It was as if, through the magic of submission through anal sex, I had found a new calling.

I know this sounds dramatic and that a lot of people, even those who participate in the act, do not feel this way about anal sex, but I am a person who demands change and transformation. I am a person who is adventurous and open minded. My journey to better, closer and more intense sex with mind blowing double penetration anal orgasms and even squirting anal orgasms had now led me to want to share. My experience has led me to become a sex educator and to the creation of erotica and sexy content that suits my own tastes instead of relying on the creations of others. My constant need to improve myself and learn has led me to the extremes of anal sex, my original limits broken and smashed, I seek new and higher planes of existence. I seek to stretch and strengthen and use my body and be used. I seek to share my pleasure and my pain with others so they may get a glimpse of the revolution I have evoked in my own body. For if we do not even understand the pleasure potential of our own body, how can we be expected to understand another person?

 By: Julia Winston

Remember you can anonymously submit your stories and questions atbootyblog@wickedwandas.ca to get your questions answered and to share your experiences with our Wicked readers!



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