Clothing Optional:
A Trans Woman's Erotic Memoir
It’s time to stop hiding. It’s time to stop putting up walls to protect myself. It’s time to get out of my head. It’s time to stop hating my body. It’s time to lose my virginity!
My life has taken many surprise twists and turns, leading me to choosing celibacy for the last 3 years. After having my Gender Affirming Vaginoplasty in September 2020, I was too afraid of covid to date, then too afraid of my neo-vagina not being desirable to future partners, too afraid of my new pussy being too tight for my partners or squeezing them out of me, too afraid that I wouldn’t get sexual pleasure from being penetrated & make me regret having the surgery, too afraid of settling into relationships with the wrong people again, to afraid of wasting my newfound virginity, too afraid of far too much. I’ve tried dating post-op; however, I kept getting disappointed in failed connections, leading to a lack of 2nd dates & I was too intimidated to go back to the sex clubs.
It was all I my head, but I couldn’t overcome these thoughts.
I was trying though. I was on the dating apps and attempting to make connections. I was making myself vulnerable. I wasn’t willing to lower my standards again, so I was being very picky; however, I was giving anyone a chance if they made a modicum of effort to complete their profiles or engage me in conversations.
Alas, nobody seemed worthy to my standards & I remained single. Every few months, I’d drop my standards further as the horniness rose.
I wasn’t willing to go back to the clubs for anonymous sex with straight cis folks for my first time experiencing intercourse with my new custom made vagina, since I did want it to be special.
I wanted it to be with someone who wouldn’t balk at the idea of me being surgically created. I wanted someone who wanted me for me, not just as a fetish. I wanted to be special to someone.
Maybe that’s the problem: straight cis folks were what I kept encountering…. Maybe if I search for bisexual friendly events.
That’s when I found it: Hedonism II in Jamaica had a planned resort takeover by a group called “Bi-Events” out of Florida. I dove into researching everything I could about this resort + the hosting group.
Like many others, I heard about Hedonism II many years ago, when I was still a teenager, thanks to the prolific stories of debauchery and nudity. I never thought I’d actually go though. My life evolved many times over since I was that silly horny teenager and I have since found myself gaining a comfort with visiting nudist resorts and Life-style (swinger) clubs. There was still apprehension since being a trans-woman isn’t always fully welcomed in these circles, so when I heard about a hotel takeover week of bi-sexual attendees, I saw my opportunity to experience this land of revelry.
My logic was simple and formed my goals for my trip:
-
Reward myself for meeting my fitness goal in running my 1st half-marathon, scheduled a week before bi-week
-
Seek validation that I actually am desirable
-
Enjoy a vacation on the beach
-
Start my international travel phase of my adult life
-
Lose my virginity in a memorable way/location
There was no hesitation in reaching out to the travel company, Tom’s Trips, to reserve a single occupancy room with an ocean view. I immediately paid my balance when requested & then got access to their private app for their guests, and that’s when it all began.
I posted thirst traps and introduction posts to the app’s social feed, making friends and sexual goals alike.
The months dragged as I worked on a base tan while simultaneously increasing my weekly running miles. I was on a mission!
Before I knew it, October came and it was time for a new chapter of my life to begin.