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I Paid a Stranger $9 to Teach Me How to Orgasm

Up until just a couple of days ago, I had never experienced an orgasm from masturbating, only from Melbourne escort girl. I guess that’s fine and all since orgasms should not be the be-all and end-all of pleasure, but it had gotten to the point where I had zero desire to touch myself at all because of it.

I tried so many different positions, techniques, and vibrators—and nothing. I just couldn’t get there and was honestly over it. (Like, you try lying down, sitting up, looking in a mirror, and attempting external clitoris pleasure, internal pleasure, internal and external pleasure and tell me you wouldn’t be fed up too.)

Of course, the sensations from a new vibrator or my fingers would feel nice, but nice is what you call someone who holds the door for you. The words “nice” and “masturbating” shouldn’t live in the same sentence. So, yeah, I pretty much gave up on the whole thing for a lil bit.

That said, FOMO is a real thing, and because my friends were, and still are, always flexing their orgasms, I decided I’d continue to persist because I am very clearly missing something here. And thankfully, I was recently put on to this $9/month app called Dipsea by a friend.

Dipsea is like porn without the visuals Melbourne escort services. It’s Melbourne sex audio porn. You have your selection of super-erotic stories to listen to whenever you damn well please, typically ranging anywhere from 5 to 20ish minutes. (Some are even narrated by Sarunas J. Jackson, aka Dro from Insecure. Yum.) The app is also created by women for women, so you know they know what’s up.

But here’s what really sold me: In addition to the library of erotic stories it offers, it also has a wellness section that includes guided audio teachings for people learning to masturbate for the first time. Clearly, this is what I needed.

 

My Mission to Orgasm, Part I: Guided Masturbation
Starting with the basics was a must. I had a lot of shame associated with masturbating (most likely because it has really never been openly discussed for most of my life, so I attached a taboo stigma sticker to it), which is probably why I had trouble in the first place.

Because of that, I began my journey with Dipsea’s guided self-touch tool first. It’s basically 45 minutes of exercises that go step by step in explaining techniques on how to touch yourself properly.

When I pressed play, I heard a sexy, smooth male voice. He started by talking me through the visualization of what I wanted to fantasize and then moved into instructing me on how and where to touch myself, starting with my boobs. Later, he instructed I start to work my way down and use my fingers to caress my vulva and clitoris. It was super, super hot.

After about 10 minutes, we moved into a section called “sensation play,” which was all about waking up my senses. The only prop required: an ice cube.

The sexy man suggested I place the ice cube along my wrist, on my lips, down my belly, and then to my vulva, all while visualizing someone actually touching me that way. Trust me, when doing this, you will feel the anticipation build.

Around midway through, we started moving into an edging section. This was really just a huge tease of running a vibrator along my body, my nipples, etc. before just placing it right on my clitoris. I had never thought about doing that with my sex toy before just placing it right on my clitoris, but it seriously made all the difference.

Lastly, the session closed out with guidance on how to change up your masturbating habits if whatever you’re doing isn’t working for you. The narrator made sure to emphasize that masturbating as a whole is not about orgasming but instead learning what feels good.

He instructed I use my fingers to touch the parts of my body that I’d normally neglect when masturbating, like my neck, my forearms, my thighs, etc. Then he set a rhythm and tempo to rub your skin in sync with—but TBH, this one did not get me going like the others because it felt a little too unfamiliar to me.

Once the audio ended, though, believe me when I say that I was well prepared and ready to dive into one of Dipsea’s erotic stories.

 

My Mission to Orgasm, Part II: Masturbating to a Sexy College Professor
After browsing, the one story that piqued my interest the most: “Lecture Me I, Melbourne masturbation.” It was an erotic fantasy about fucking your professor—basically my only fantasy all throughout college. I grabbed my vibrator and pressed play.

The story was narrated by a woman. She started by setting up the plot at first, describing how she would go into her professor’s room during office hours, and then it slowly began to escalate to something more. As I was listening, it reminded me of my college days, thinking about one professor in particular I always had my eye on.

After around seven-ish minutes in, the sex started to pick up and the woman was no longer narrating. Instead, I was listening to her exchange words with the professor himself. It was as if I were a voyeur listening and watching.

As the story ramped up and I listened to them both moan through my headphones as he bent her over his desk, it was time to go from using my fingers directly to my vibrator. I started to focus on the story and stimulation, which inadvertently helped me get outside of my own head and thoughts for the first time. I could picture myself being fucked on the hard wood desk by my college professor, moaning with pleasure every time he went in and out of me.

Just as the professor in the audio started going faster and harder, I started to feel myself getting closer and closer to orgasm, until I didn’t even know what was happening. By the time he finished in the story, I had orgasmed too. Finally.

 

Final Thoughts
I’m fortunately one of the rare women who can orgasm from partnered, penetrative sex, so I do know what an orgasm feels like. But let me tell you, my first-ever masturbation orgasm? Totally different. It was exactly as cheesy as people describe it: It’s earth-shattering, as if your body just fell off a cliff, and maybe even a huge explosion that just took off too. It was…wow. Just wow.

So my mission was accomplished. An orgasm was had, all thanks to Dipsea. But after taking myself through all the preparation, I’m realizing now that the pressure to orgasm from masturbating could’ve been the exact thing holding me back. (Oh, the irony.)

Had I just relaxed, let myself feel all the feels, and focused in on a fantasy or let my mind wander where it wanted to, maybe it wouldn’t have taken so long. Who knows.

But what I do know: Dipsea is amazing if you are like me and want to reteach yourself how to masturbate. (Believe me, it’s necessary.) And although not all the stories I listened to fully did it for me, it’s a great app to get lost in while looking to achieve your deepest fantasy—and that, my friends, will be listening to one of these stories with my boyfriend during partnered sex. Stay tuned.

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