A Trans-Woman's Experience at Hedonism

Year 01 – Night 02

Today is when I broke one of my cardinal rules of life-style events: don’t make hard plans.

Yes, this resort is incredibly supportive of those wanting to get naughty, it is still Jamaica & I came here for a vacation. Wanting to make sure that I got the most out of my vacation, I determined that day 2 would be all about rest and recovery. The only firm plan for the day was to get a massage + read some smut by the waterfront.

It is currently October, 2023, and I started a weight loss journey in October 2022. This was largely triggered by having had 3 knee surgeries and not being able to keep up with my 3 year old German Shepherd Dog due to knee pain + being generally out of shape. I set my goals on losing weight and running my first half-marathon, scheduled 1 week before my trip to Hedonism, with this vacation being my reward for accomplishing these goals. Because of my physical efforts, I came to Hedo in the best physical shape of my lift, albeit worn out.

The massage at the spa was exactly what my body needed. 80-minutes of tranquility as every muscle slowly released its tension. The staff was incredibly skilled in discovering the knots that have been building for months and breaking their hold on me. I could feel the stress wash away as I lost my sense of time. My mind went blank as the music softly filled my thoughts. Even 80-minutes went by far too quickly for how much my body seemed to need this form of release.

I eventually accepted that my massage was over & went right back to the beach to resume my book where I had left off. Chapters flew by as I enjoyed yet another Malibu Sunrise with the sounds of the waves crashing in front of me. This was the serenity I had been needing and my soul was feeling recharged as the sun began to set.

I returned to my room to prepare for dinner, but first I had a chore to accomplish: dilating. Part of having a neo-vagina is that it takes a little up-keep, so if I intend to be penetrated, I need to ensure that my vagina’s muscles are relaxed and prepared for what may come. This is a life-long thing for trans-women, and many cis-women too actually, so it’s more routine than pleasure focused… most times.

I had brought my favorite toys with me for the dual purpose of dilating + being used by myself or partners during play sessions & it was this that would help me next. Specifically, there’s a discontinued product by Lovense, called the Mission, that is a g-spot vibrator and is absolutely perfect for my body. The specialty of this toy is that the tighter you squeeze, the stronger it vibrates. The intent was to just dilate & get ready for dinner, but once my toy came to life I became distracted. My eyes were locked onto the image of myself reflected in the mirror on the ceiling over my bed. Naked, tattoos and piercings on display, legs splayed open, and my toy slowly entering myself as it rumbled against my tight opening.

Images from the story I had been reading all day flooded my mind as the body in the mirror took the place of the main character. My toy sliding in and out as the masturbation scene from my book drove my actions. As my passions rose, I would squeeze around the intruder, making it rumble more aggressively inside of me. Every thought, every sight, every feel, every sound fed each other until my body surged into my first orgasm of the day.

As my body recovered, I soon realized I spent more time dilating than planned & sprung out of bed to shower and do my makeup before meeting friends for dinner.

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An oral competition

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The thoughts that come after

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-Reserved for Publication-

Year 1 - Night 4