Loving Myself: Exactly What You Think It Is

I’ve been working with a sex coach and erotica writing mentor, Strawberry Smutcakes. I’ve talked with her about my internal sex life, the mental gymnastics I go through when I’m having sex, and the guilt I feel about the porn I watch, which usually involves elements of lesbian coercion, as well as some compulsion on my part.

She recommended that I masturbate without porn, focusing on the sensations in my body, what feel good and right to me.


My wife, Concetta, is on her period this week, and I’m also on nights, so our sex is interrupted from two different directions. I found myself with time on my hands, and decided to try out the exercise.

It was actually really difficult. Have I ever masturbated without thinking about something sexy to get off? I don’t think I have. I’ve masturbated without porn, though not since the advent of smart phones.

So, I turned the lights out, got out my favorite Vaseline (friction is the enemy!), and began to stroke myself. The lights were off, the room was dark, and I was lying down with my feet crossed, my shorts down to mid thighs. I stroked, and stroked, pushed on my perineum, nothing much happening.

I sighed. I considered how my stroke sessions usually went. I focused on finding the videos, then cueing them to the most key moments where the seduced is acquiescing to the seducer. If she presents insufficient resistance, I move on to another one. If she isn’t a great actress, I move on. If it’s too rough, and she seems legitimately distressed, rather than turned on and just a little anxious, I move on. Meanwhile, I’m squeezing my penis, stroking it, moving it through its paces. I’m trying to get myself to come when I’ve seen enough of the movie to be satisfied with the experience, and it’s become less and less satisfactory.

I often try to make this happen quickly, because my time is limited. So, I’m putting pressure on myself. I try stroking harder, different, I try changing the source material. Often the videos end up rougher than what I’d like, closer to rape than a forceful seduction, and then I feel guilty about that.

Back to stroking. I went to google. Could I do the prostate massage? Would that help? I found an Ask Men article, describing prostate massage. I wasn’t about to put my own finger in my anus. I was willing to explore my perineum to try and find a spot to put pressure on it.

Then I looked up other masturbation tips. It’s really counter-intuitive. Men are so classically associated with being chronic masturbators, that you think we’d be really good at it. I’ve spent a lot of time and practice working to turn Concetta on. But I’ve never done foreplay on myself, and I’ve never done anything with a guy.

The article said to try using my other hand, moving my hips, touching my neck and squeezing my nipple, relaxing as much as possible. I followed orders. I went back to my perineum, spreading my legs after bringing my shorts all the way down. This time I actually found my prostate, much closer to my rectum than I thought. I pushed, and found that mild bladder tingle, and that my strokes were feeling better.

I tried thrusting my hips, feeling my nipples, my neck and hair. It was OK. The hips did the most for me. I was warming up, starting to feel good. But I still wasn’t fully erect, and I was tired. I logged in to Porn Hub, found a boss spanking and dominating her secretary, and tried my new prostate massage. It felt really good.

I’m going to need a few more sessions before I can pull this off without any visual aids. I think I’ve learned not only practical technique lessons, but also I broader lesson for myself. I’m not a horse being mechanically masturbated for artificial insemination. I’m a romantic, kinky, sexy guy, and I’m as sensitive to stimuli and foreplay as Concetta is, even if I’m the one doing it to myself.

This whole process of working with Strawberry Smutcakes is fascinating. I’m taking all this semi-conscious material and moving it into the realm of consciousness, and finding really deep understanding about myself within.

Update: wife and kids are out of town, and I got home and decided to make myself the girl.

I went to my bedroom, closed the drapes, and lit a candle. I put a towel on the bed, and found the small vibrator and bottle of lube we keep. I was really relaxed at this point, which helped.

Now, I had a much better orientation to where my prostate was. I slathered myself in lube, and started working. I pushed on the prostate, and decided I was going to go for broke. I started massaging my anus.

It felt good, really good. My major anus kneading experience has been Concetta’s, and mine’s bigger. I found I could work it from a few different angles, and it felt really good, like I was inflating my dick. I could push with one hand and pull my cock with the other. I pinched my nipple, hard, and it felt really good. Now I was the girl, and my hands were the guy.

I’ve never ventured into my own rectum. It always had an association with filth, and with feminizing myself. I ask myself, OK, were you going to die never knowing you had a g-spot buried in your tail? That’s like leaving money on the table.

I did still have to put porn on to orgasm, but I wasn’t so focused on the action, dragging my tortured prick to try and keep it engaged. I was watching the porn, and enjoying the sensations much more.

This feels like a colossal discovery. When I came, I smiled, and I pumped out easily twice as much ejaculate as normal. I joke with Concetta that it’s Diet Sperm now that I’ve had my vasectomy, and my swimmers are trapped in the vas. It’s all just prostaglandins and mucus and water, these days.


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