Clothing Optional:
A Trans Woman's Erotic Memoir
Day 01 – Saturday
Host Events: Cowboys and Cowgirls
2PM Nude Pool Party
7:45PM Opening Ceremony (Dining Room)
10:00PM Bi Orgy (KS)
10:00PM Hedo Playroom (Spa)
10:30PM Meet & Greet (Courtyard)
My Events/Trigger Warnings:
Exhibitionism
I’m finally here! It took 14+ hours to get to Jamaica from Oregon, but I’m finally here!
Exactly as I’d hoped for, I immediately found amazingly accepting people who already see me as just another person, not merely an object for their sexual desires. The 90-minute bus ride from the airport was nothing but laughs as every seat was taken by others on their own adventures toward hedonistic fulfillment, which helped the ride pass very quickly while we all joked about wearing too many clothes on our way to a nude resort in the hot Jamaican sun. Once we made it to the resort, the levels of kinship only accelerated as we found friends from the travel company’s app waiting for us to arrive with open arms & swag bags.
Around every turn were more friendly folks and easy conversation, setting anxieties about being a solo traveler at ease. With zero hesitation after having my bags brought to my room, I decided it was time to disrobe & explore this wonderland further. I grabbed my drink cup & made a direct line to the “prude pool’s” bar to get my first of many Malibu Sunrises that would fuel my own adventures throughout the week.
Honestly, it was shocking how quickly I became comfortable with my own nudity.
Being a post-op trans woman, I couldn’t help but have those apprehensive thoughts run through my head while I explored in spite of them. Overcoming those negative self-perceptions was one of my two primary goals of this trip – I needed the validation that I am desirable. Yes, my friends tell me I’m pretty, but I’ve been hiding at home throughout most of my decade long transition, including those worst years of covid, so I haven’t been comfortable stepping out and dating. The sex-clubs were validating in their own ways, but I haven’t been to them since before I had my gender affirming vaginoplasty in September 2020, so I had the extra apprehensions now about being a virgin of 3+ years again too. I came here to grow out of my cocoon.
I was happily surprised at how many conversations I easily fell into with absolute strangers – some of them risqué, but most very vanilla in talking about being on vacation in the same way that I’ve encountered at other resorts where everyone remains clothed. It was just like anywhere else… merely doing it nude.
There was however an underlying sexual charge to the air everywhere on the resort that was undeniable & unavoidable. It wasn’t pushy in any way, but it was persistent. You could feel the inhibitions of everyone fall away as we dropped our masks along with our clothes, and the authenticity of those around you was intoxicating by itself.
Alas, after a couple of hours, it was time to throw on a swimsuit cover-up that consisted of only 2 straps for my shoulders & a piece of cloth that wrapped around my body, only so that I was appropriate for the eating areas. I had no need to wear anything else as I expected to be naked again as soon as dinner time was over.
The first day passed quickly as I explored then joined some new friends for dinner and a show in the main dining room. The resort did an excellent job of ensuring excellent food options were available while the entertainment staff kept us smiling. Dinner passed just as swiftly as the rest of my first few hours on property before it was time for a meet-and-greet in the main courtyard.
Couples and groups filtered in and out as music played just loudly enough to get guests bouncing along without interfering with conversations. The mood lighting of the area was a wonderful contrast to the stars shining above us in the open-air setting. I found myself easily joining conversations with random strangers again, quickly making friends until I chanced upon a slightly older gentleman that I had met on the bus earlier that day, FM.
While I’m only in my late 30’s, the age range of attendees was a mix of late 20’s to 70+, with the majority appearing to be in their 40’s and 50’s. Age wasn’t a factor at any point in this adventure though. Same as our genitals, age is just another part of our life. To me, my attraction is based on Hearts, Not Parts.
FM and I had started innocently talking about our travel day, quickly turning flirty, then raunchy before we started making out in the center of the dance floor of the courtyard. Our hands explored each other’s bodies as I felt my desires grow and his own excitement begin to press against me.
Starting to feel the heat of the moment combined with the humidity envelop us, I quickly removed my cover, leaving me nude in the center of dozens of strangers. FM found my pieced tits and began to kiss one while pinching my other nipple. Just as swiftly as his lips found my body, his hand found my crotch and he placed his open palm directly on top of me with a firm pressure. I couldn’t help but lower myself onto his hand and grind against him as he continued to suckle my breasts.
Feeling a desire to satisfy my oral fixations, I leaned down to his ear and asked if I could go down on him, to which he only responded with “please,” while standing straight in front of me. It was apparent that he needed no further encouragement as I dropped do my knees in front of him. I could see the crowd turn toward us in anticipation as they continued their conversations like this was an every-day occurrence. The attention of the crowd made my nipples even harder than FM’s tongue did as I opened his pants and took his full length into my mouth in one swift motion. FM let out a small whimper of approval as I swirled my tongue around him before beginning to bob on his full length. I couldn’t help but keep my eyes searching the reactions of the crowd – I was the center of attention and I loved every second of it. I was now determined to put on a show as I changed my pace and depth, never letting him fully out of my mouth. FM told me that he’s not likely to reach climax, but to please continue as long as I’d like to – and this is when DM came by.
DM was someone else that I had met earlier in the day on the bus. DM was on their first trip to Hedo with their partner, EW, but I already knew they played separately, so when he asked if he could join in, I was happy to scoot over. DM joined me on our knees as FM gave their consent too before we began to kiss each other with FM’s shaft between our lips. We took turns catching our breath and catching FM’s dick in our mouths. Eventually, DM stood up to make out with FM, and I took this opportunity to begin going down on DM as well. I kneeled between these two men making out as I switched from one dick in my mouth to the other.
I could hear the audience talking about our show & I only felt the heat in me grow further. I was able to pick up on FM breathily say to DM that he wanted to go down on me too, to which I enthusiastically encouraged him to follow his desires.
We moved to a nearby chair as FM then knelt between my legs and DM stood beside me. FM’s tongue began to lap at my lips in slow but deliberate motions, seeking his prize. I couldn’t help myself from moaning onto DM’s cock as FM’s tongue found my clit and he circled it quickly. I was already so turned on that time passed quickly. I was lost in the sensations of a hard cock sliding in and out of my throat while a tongue explored me with enthusiasm. I came quickly from all of the attention as I squeezed FM’s head between my legs and used DM’s cock to stifle my cries of bliss. It wasn’t a necessarily large orgasm, until I heard the cheering. Opening my eyes as the orgasm was mid-swing, I saw 2 couples a few feet away who were giving my show an ovation & that alone amplified my orgasm and made it continue longer than originally assumed it was going to last.
Eventually my shaking legs were enough to tell FM that he was successful and he pulled back. Both FM and DM kissed me and stroked my ego telling me how hot that was to watch while being a part of it before taking a step back to compose themselves as well.
That was enough for now as we all had other plans for the night, so we talked for another minute and then went our separate ways for the evening.
I wasn’t done though, as I had my eyes on heading to the nude pool.
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Reserved for Publication