Anal Sex Experiences

This is a post partly inspired by the work of James Pennebaker, who has done a lot of research on writing as a means to express emotion, and to ultimately lower stress experienced from past events. I also wanted to explore my thoughts more on how anal play fits into my present and future sex life.

My first serious boyfriend in high school was sort of a jerk. He was one of those jerks that made you feel special if he was talking to you. My mom liked him; she thought he had an “open” face. He was generally respectful and considerate. His mom made us fried rice. He never had a curfew. He spent practically all of his time, money, and energy on his teal Chevrolet truck, which, incidentally, had its own tiny version of itself. The miniature teal Chevrolet truck sat on the dash, reminding me every time I got inside to go to a football game or to a movie, that perhaps this person I was dating was not the most mature person in the world. (But then again- I was in high school)

This was the person I first had sex with. It was very cliche. After prom. In his uncle’s Escalade. He bought condoms on our way home from prom. We parked in a public park’s parking lot and had sex in the back seat. I was 15. He was 16. 

I remember feeling so turned on, and so ready to do it. My mom and I had talked a couple of months before. She told me that if I needed birth control when I was in college, that she would be able to help me with that. I thought to myself, what a cool Mom! I felt supported, which also helped me feel ready with my decision. I felt like I was being safe, I was having very consensual and loving, respectful sex. I felt positively about my decision, and looking back, it still feels like a positive and healthy experience.

Anyways, after our first time, we couldn’t wait to do it again. (duh) But finding the right time was always so difficult. I had the strictest curfew of anyone I knew. I could hardly go over to a friend’s house without getting five phone calls from my parents. We had to design an elaborate plan: I would get permission to spend the day with him going on errands. We really did do those things, too. Visiting relatives, going to the bank, grocery store, etc. Except we stopped by his empty house in the middle of the day. 

We started in his bedroom, where we started with vaginal sex. Because he had a small bed, we moved to his parents’ room… I remember feeling guilty and ashamed for lying to my parents. I remember feeling uncomfortable with how sneaky I was being. So I probably was not turned on. I wanted to have sex, but I think that those negative feelings definitely impacted my experience.

In his parents’ room, I can’t exactly remember what happened, and what was said. I don’t particularly remember his asking me if he could try anal penetration, but he might have. What I do remember is him penetrating me anally, me feeling a deep sense of shame, and him pulling out after 10-30 seconds. I was shaky and guilty. I didn’t know what had just happened. We took a shower to rinse off. I know I didn’t orgasm at all from our second experience, and I remember really intense feelings of remorse.

I started reading Tristan Taormino’s The Ultimate Guide to Anal Sex for Women this past week. Since J and I have opened up and had so many explicit and honest conversations with one another about our desires, fears, boundaries, and fantasies, I have felt exponentially more comfortable with the idea of trying anal sex again. I honestly want to try it again, and reading Tristan’s book has been a liberating experience. For example, this paragraph spoke to me since it is pretty much what I experienced:

“Some people’s fears may be about anal sex being difficult, uncomfortable, painful, or impossible to enjoy. Women especially often veto anal sex because of a negative experience in the past. If a past partner tried to go from zero to sixty in five seconds by sticking his dick in your ass without warm-up, lube, or communication, then chances are it hurt a lot and you never want to do it again. Bad sexual experiences are difficult to overcome: who’d want to repeat something awful? Your partner needs to reassure you: this time, with him, it will be different. He’ll take his time, use plenty of lube, and work your ass up to his cock. You will be in control of the pace, and he’ll stop if you say so.” (p.21)

Since starting her book and having more conversation with J and our other partners about anal, I am so excited to work on warming up my mind and body to anal sex. J and I have tried a little anal fingering, and some slow full penetration. It feels good, and I also know that taking even longer to warm up, getting really turned on, and practicing to relax my muscles and mind will make it an even more enjoyable experience. I am so grateful that J and I have been having the conversations and experiences that make it possible for both of us to more fully process and move forward from our past experiences.

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