A Trans-Woman's Experience at Hedonism

Introduction to Hedonism

 

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, too 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:

1. Reward myself for meeting my fitness goal in running my 1st half-marathon, scheduled a week before bi-week

2. Seek validation that I actually am desirable

3. Enjoy a vacation on the beach

4. Start my international travel phase of my adult life

5. 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.

*********************************

 

Point of honesty: I have a lot of orgasms during my weeks at Hedonism, but not all of them are mind-blowing, leg shaking experiences. On an intensity scale of 1-10, a solid 2/3 are a 5 or below. Nice, but no eye rolling.

 

 

 

 

 

 

Day 01 – Saturday

 

 

Evening Vibes: 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 Vibes & 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. I love queer folk. 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 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, Frank.

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.

Frank 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. Frank 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 Frank’s tongue did as I opened his pants and took his full length into my mouth in one swift motion. Frank 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. Frank 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 Matt came by.

Matt was someone else that I had met earlier in the day on the bus. Matt was on their first trip to Hedo with their partner, Erica, but I already knew they played separately, so when he asked if he could join in, I was happy to scoot over. Matt joined me on our knees as Frank gave their consent too before we began to kiss each other with Frank’s shaft between our lips. We took turns catching our breath and catching Frank’s dick in our mouths. Eventually, Matt stood up to make out with Frank, and I took this opportunity to begin going down on Matt 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 Frank breathily say to Matt 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 Frank then knelt between my legs and Matt stood beside me. Frank’s tongue began to lap at my lips in slow but deliberate motions, seeking his prize. I couldn’t help myself from moaning onto Matt’s cock as Frank’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 Frank’s head between my legs and used Matt’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 Frank that he was successful and he pulled back. Both Frank and Matt 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.

*********************************

 

After a quick trip back to my room to clean myself up, I grabbed my empty drink cup and headed to the nude pool. I didn’t have any plans in mind aside from getting a refill and see what it’s like there at night as I was already absolutely exhausted. It was a travel day after-all and I haven’t slept yet.  Life had different plans though as I met a couple hanging out by themselves at one of the tables in the pool.

It was their last night at the resort & the conversation with them was easy, so I gave into my own desires to pursue them. The wife got distracted by somebody else who passed by; however, the husband was fixated on me. We began making out in the pool as hands once again began to explore my body. My already sensitive clit responded to his touch with a need for more. His cock was so close to my pussy that I could feel the water moving against me as I jerked his shaft. Before I knew what was happening, he lifted me out of the water & placed me sitting on the edge of the pool deck. His mouth immediately found my slit and I leaned back to give him full access. Putting my heels on the side of the pool opened me further as I once again noticed the eyes of the ever-growing crowd finding their way toward my body. I was so incredibly worked up that I came incredibly quickly, but he knew I wasn’t done. My orgasm faded as quickly as it came upon me and his efforts never slowed. His tongue was so consistent that I never fully came back down from my first orgasm as I felt yet another rise. My mewling growing louder as I couldn’t hold myself upright anymore, leaning back on my elbows so that I could still see the crowd around the dimly lit pool. I didn’t hold myself back this time as I let my passion escape my lips. This was the orgasm I’ve needed tonight. It came on like a wrecking ball tearing down a wall in a forceful slam & that intensity held in multiple waves, that tongue staying impressively consistent while swirling around my clit. Wave after wave washed over me as I fell fully back on the pool deck and my legs dropped into the water.

“He’s good at that, isn’t he?” I heard the wife chuckle, having come back at some point during our session.

“He definitely is and thank you for sharing,” was all I could muster as I was busy catching my breath while my core undulated in ongoing contractions.

As it turns out, they were pretty worn out from their week and were ready to head to bed, but I was happy to help them end their vacation on a high-note. We talked a bit more before they escorted me back to my room for the night.

It was time for me to go to bed too. Sadly, I haven’t gotten fucked yet, but I wasn’t searching for it tonight & the week is still young.

Today was a lot to take in, but I had my bestie to update. I promised her that I’d keep her updated on my travel & safety, but I absolutely didn’t expect to be sharing sex stories on day one!

I retreated to a table outside of my room with my weed & a bowl I purchased that day at “Hedo Weedo,” a legal shop to purchase marijuana in Jamaica that happened to be on-property, and started to recap my day. Short video after short video were recorded while I shared my recounted my tales of debauchery.

I found these short self-therapy sessions to be very cathartic as they helped me keep track of my slutty escapades & immediately committed to recounting every day to them… for now though, it was absolutely bedtime.

I barely stayed awake for a final shower to wash the nude pool off of me before my eyes were too heavy to keep open.

Gods I really liked all of those eyes on me…

 

 

 

 

 

 

*********************************

The thoughts that came after

 

I fear that was slutty of me.

Yes, there were naked people all around & lots of heavy petting to be seen, but I was literally the only person who was having any form of sex openly in either of those spaces. I don’t know either of those guys from Adam and yet there I was, doing all those things, with all those eyes…

But isn’t this why you’re here? Aren’t you seeking exactly this sort of sexual validation?

You’ve done your research and know that sex happens in the open here, so are you afraid you’re in trouble for some reason? Nobody said anything bad & in fact, you got a lot of praise for what you did!

Why does the fun feel hollow?

Oh boy was it fun ^__^ I want more!

More of those eyes… more of that desire… I want more.

Hold up… that was the first time anyone besides myself made me have an orgasm after my surgery!!!! I almost didn’t even realize that! Their tongues alone blinded me from my own story hahahahaha.

Oh… Nobody has fingered me either…

How do I broach that conversation about my anatomy being different? I definitely wouldn’t want to have that conversation on the dance floor.

Day 02 – Sunday

 

 

Evening Vibes: White Out Party

11:00AM Hedo Virgin Tour

1PM-2PM Educational sessions – Coming Out Q&A

1:30PM Orgy Day Play (KS)

6:00PM Cocktail Party (Courtyard)

10:00PM Hedo Playroom (Spa)

10:00PM Bi Orgy (KS) + Bi Dungeon (Dungeon)

10:30PM Lounge Party (Main Pool)

 

My Vibes & Trigger Warnings:

Masturbation

Orgy room

 

Today is when I did something stupid: I made firm plans to meet people at a specific place and time. Then I overhyped expectations & centered my day around it.

Yes, this resort is incredibly supportive of those wanting to get naughty, but it is still Jamaica & I came here for a vacation too. 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 life, albeit worn out.

The massage at the spa was exactly what my body needed. 80-minutes of tranquility as every muscle slowly relaxed. 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 care.

I eventually accepted that my massage was over, while I showered off the body scrub we finished with & went right back to the beach to resume my book. 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 specific curve of this device skates around my pelvic bone line none of my others toys can. 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 incredibly 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 what would be 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. 

*********************************

 

It may have just been social anxiety, or it may have been my innate attraction to people in official roles, or just the comfort of their friendliness, but I found myself often latched onto the hosts of this event this week. I joined a couple of them for dinner this evening at the Flame restaurant, sitting on the beachfront.

Flame had a robust menu ranging from ribs to Tilapia. Since I was sitting at the long communal table, I was surrounded by people with much more experience at this resort & deferred to their recommendations. Primary of which was to get multiple items from the menu since there were no restrictions.

The host group has regular meetings in their home area, so most attendees knew them and they helped introduce me to others and they also kept a safe eye on me being a single female attendee. I felt so incredibly safe in every regard this week. Regardless, they were amazing people whose company was yet another highlight of my week, so I kept coming back for more.

In particular was one host who I had been talking to ahead of our trip, Allie. We talked on the travel company’s app ahead of time. Allie and I just clicked easily and we both had vivid coloring in our hair so we were immediately drawn to each others peacocking and stuck around due to the personalities. I actually spent a LOT of time this trip with Allie when they weren’t working events.

Dinner passed, then we all went to the main dining room for another great performance by the resort’s entertainment crew. While I relaxed from the events of the day, I was also a bit horny, so I decided to head over to the Kama Sutra room that evening. During Bi-Week, the Kama Sutra room is converted into an orgy room. The orgy room is open multiple times a day and is composed of a lobby area where everyone disrobes + there are a couple of hosts for the sake of safety. Beyond the lobby existed a large main area with numerous beds spread around the room + more hosts to keep an eye on everyone and help change sheets, and a bathroom section in the back with shower stalls. There were also a few booths setup in the corner to serve as anonymous glory-hole options, only a curtain serving as privacy shields.

This was my first time in an orgy since my Domme’s birthday surprise, so the sights and sounds were overwhelming at first. There’s a general lack of inhibitions in this space and the sounds of grunts and orgasms proved it. Being bi-week, there was a unique element to this space: the boys were out to play with each other too and everyone was only here to cheerlead everyone else.

I came to the orgy room for one specific reason though: to find my first penis to fuck me. Remember, I am still a post-op virgin at this point. I haven’t actually been penetrated by anything aside from artificial penises since my surgery, so that’s years of longing for authenticity.

Through the travel group’s app, I had met someone that I actually wanted to be my first. They were another trans woman who enjoyed using their original equipment, and we were VERY into each other coming into this trip. Because I was so apprehensive about how my new equipment will work, I really wanted to be with someone who would take their time to treat me and it right… and other silly virginal thoughts. We had made plans for them to help me lose my virginity, but they weren’t arriving until this day, so we planned on making it happen tonight. When they messaged me during dinner that they were going to be in the orgy room that night, I set my sights on getting over this hurdle so that I could truly let loose for the rest of my trip. Losing my virginity so that I could hoe it up was my primary goal of this trip.

So we made firm plans & life evidently had different plans.

*********************************

 

I found her! She was sitting on the side of the room by herself, enjoying the show in front of them, so I went over to join them. We instantly hit it off and began making out and whispering to each other. Our hands were soon exploring each other as well, when suddenly she became distracted by something on the other side of the room by the door. She excused herself and left just as quickly as we clicked.

I was befuddled and felt aimless as my plans literally ran away.

I later found out that their partner was unhappy with our intensity and a boundary had been almost broken as they had agreed their first play session at Hedo would be together, even if others were involved too. I never did get the chance to connect deeper with this person as they both became sick during the week and when we did chance upon each other later, the vibes were ineffably off.

So there I was, horny and wanting more. I had tried to find them to find out what happened & eventually gave up to head back to the orgy room. When I returned, I set my sights on other goals – I was still holding out at this point for that one person to be my first, but I do love women and haven’t gotten that satisfaction yet today.

My luck changed now as I once again ran into Allie and they were not working at the moment. We teased each other only momentarily before a bed in front of us opened up and I asked them if they’d like to play, to which they almost squealed in agreement. It started innocently with laying next to each other, our lips meeting in sensual kisses as our hands explored our bodies. The sounds of the room helped to heighten our anticipation and I eventually rolled on top of them, pressing our bodies together, our legs between each others as we ground ourselves together for the extra pleasure awarded by strategic friction. Almost simultaneous to my kisses moving down her body, a couple laid down on the bed next to us. They were on a similar path as the husband began going down on his partner as I started enjoying Allie’s taste on my tongue. Both of the women in front of us began sharing their enjoyment with us as their sounds arose and we shared a sly smile between us. The competition began.

Before I could get fully into my meal, a fellow who Allie had been chasing had come by and asked if they could join before beginning to play with Allie’s tits, then moving to go down on me from behind. Alas he wasn’t too great at their actions, so eventually I had them stop as it proved more distracting than helpful, so they made their way back to Allie’s chest and lips.

So here we are – two beautiful women on their backs in the middle of an orgy room with a head between each of their legs, focusing on the people in front of us as dozens of people surround us doing their own things. I elicited a slightly louder moan from Allie, which was met in turn by the women next to us, then she got louder, to which I redoubled my efforts with my tongue. Long flat strokes up and down their entire length. Both of them growing louder as the rest of the room began to fade away from my attention with her thighs beginning to press against my head. It wasn’t a race between us, but rather a challenge of quality, or at least that’s how I was approaching this battle.

The woman next to us was seemingly getting close & I could tell that my own partner was closing in on their own home stretch as well, which is when I decided to make sure that I win. I began introducing fingers to my tongue’s efforts and it was over from this point. I found her g-spot as my tongue relentlessly continued to encircle her clit in the way her hips showed me. Once I curled my fingers to add increased pressure, she fell off the cliff. Both of the women began to cum, but Allie’s whole body spasmed as they clenched the bedsheet in a tight fist, stifling their sounds on the cock that made its way into her mouth. My fingers were unable to move against how tightly she squeezed me and bounced on my fingers. I could feel the waves of her orgasm flow from one right into a 2nd while seeing the male partner next to us sit up.

“That was fun” he winked toward me as he climbed on top of his partner, legs still holding my head firmly in place as Allie took their time enjoying the moment. Allie and I shared a kiss before I decided I needed a water break.

When I returned from getting a quick drink, no more than a few seconds later, the guy who had been joining us had Allie’s full attention as he mounted her. I wasn’t interested in them, so I gave her a kiss goodnight and decided to call it a night.

I wasn’t especially tired but wasn’t feeling in the mood for anyone else that was around tonight. I chose to go to the only known source of food at this hour, the nude pool’s grill.  The food wasn’t anything great here to be honest, but I had a great conversation with even more strangers I converted into friends before going to bed for the night.

*********************************

The thoughts that come after

 

            Yay for relaxation! That massage did wonders for helping my body recover. I actually think I’ll go back at the end of the week for another one before going home. Hell yeah, treat yourself!

            I’ve earned this… I’ve always told myself that “I’ll work really hard now so I can let myself enjoy life later,” but when am I going to let that “later” happen if not now??

            Mmmmmm, she’s pretty. OMG I’m going to get fucked tonight!!

            What the hell just happened?????? Did I upset them somehow? Did I do something wrong? Where’s they go?

            Oh well, not going to wallow in it, but what the hell do I do now?

            Oooooooo, she’s here and she’s NOT working ^__^

            HAHAHAHAHA, I win!!

            Ugh, that was rude of him…

            *********************************

 

 

Day 03 – Monday

 

 

Evening Vibes: Burning Desires

11:30AM Speed Dating (dining room)

12-5PM Nude pool party

12PM-1PM Educational sessions – BDSM Impact Q&A  (Disco)

12-1PM Educational Sessions: Anal 101 (Kama Sutra)

1-3PM BDSM Day Play (Disco)

6-7PM Wine Tasting (Piano Bar)

10PM Orgy Playroom (Kama Sutra)

10PM Dungeon Playroom (Disco)

 

My Vibes & Trigger Warnings:

3 different 3-somes

Pool-side cunnilingus

 

 

 

Speed dating is how I started my day today. We took over the main dining room and broke into two lines, with only one rotating. Mini-dates like these are wonderfully upbeat, all fun with no drama. We share our names, our desires, a joke or two, and incessantly flirt with everyone. I was finally able to put faces to names of those who chatted in the app without posting their own thirst traps in the social feeds.

I made a mental list of those who I hoped I’d run into again this week, including a beautiful throuple who were traveling together. Seemingly everyone was intrigued by their dynamics as they were usually swarmed too.

Not feeling especially sexual at the moment as the day was still early to me… being from the Pacific time-zone, I was multiple hours behind the majority of the attendees coming from the East Coast. I opted instead to explore more of what the resort had to offer for now & save my sexual batteries for the evening’s events.

“That’s a nice gym,” I thought to myself when I partook in the tour conducted by one of the host couples on day 2. I’ve never been the type to work out when away from home so I surprised myself when I ended up doing a full-body workout in Jamaica. The gym was incredibly nice though, and I was by myself so I had unfettered access to anything I wanted – which is apparently a theme for me here.

Despite working out regularly, I really don’t enjoy getting hot and sweaty, so I found the daytime activities to be a bit much for me. There was a regular party being held in the nude pool, but I preferred to find cooler environments to spend my time in when the sun was high. To be honest, I found it to be way too crowded for my socially anxious tastes too, so I often would walk by & instead choose to go talk to a friend I saw nearby in the shaded smoking sections because it was calmer there.  I found myself splitting my time fairly evenly between conversations with strangers at the clothing optional (aka “prude”) pool bar, sharing a joint in one of the smoking areas, the main dining room with complementary iced coffees with rum cream, or under the trees somewhere on the waterfront enjoying my book. I was doing whatever I wanted, whenever I wanted to.

Before I realized it, the day had passed & I hadn’t made any new connections to join for dinner, but I really wanted to try one of the three restaurants on property, outside of the main buffet or Flame again. I got very lucky as I ran into a couple from the night before as we simultaneously arrived outside of Harysan, which was being held on the main pool deck during construction of that restaurant’s space. Aaron and Stacey were 2 people who shared some fries with me while we were at the nude pool grill last night & I was happy to spend some more time getting to know these beautiful people.

I am unquestionably demi-sexual, so there has to be some form of connection for me to have a physical attraction to MOST people. Having dinner with friends is exactly what my neuro-spicy brain needed to get the most out of this trip if I wanted to play with them later… and it was apparent that we all wanted to play.

I joined Aaron and Stacey for dinner, and was also sat with 2 other couples, Zim + Natalie and Scott + Sabrina. Harysan is normally the hibachi and sushi restaurant, which currently had a limited seafood menu. The food was fantastic & the conversation jovial as the drinks were kept filled and our plates frequently replaced with more delectables. The dining experience was notable as I felt as though my time here was incredibly important to the staff keeping an eye on all of us.

The group broke apart after dinner, but I stuck with Stacey as Aaron tagged along, heading to the beach front for another show. This night was fire performers showing their well-practiced skills at the water line. Needless to say, it was hot. I left Aaron and Stacey after the show with plans to meet at the orgy room shortly.

I’m a bit impatient, so I ended up getting to the orgy room sooner than them; however, I conveniently ran into Scott + Sabrina as soon as I walked in from the lobby area. He was SO happy to see me and we soon found a bed opening up, grabbing it before anyone else could. Sabrina and I tore into each other as we laid next to each other as Scott reigned kisses upon both of our bodies. Sabrina pulled me on top of her and Scott began to lick both of us in long smooth strokes from one pussy to the other and back down. Scott eventually pulled back and Sabrina pushed me off her, onto my back, then climbed on top of me, straddling my face as they laid down into a 69 position. Feeling her weight hold me to the bed as I felt the hunger of her mouth drove me to return the pleasure she was delivering to me. My surroundings disappeared as her mouth did magical things to me. I felt her sit up and could tell that Scott had returned. Sabrina stayed right where she was as I held her hips firmly in place while her mouth now turned to Scott, standing beside her. They asked if I’d like to fuck and I gave my yes with a, hopefully cute, butt wiggle and squeal into the delicious pussy in front of me. They understood my meaning and I felt him kneel between my legs, positioning himself at my entrance.

Hold up, don’t get too hot and heavy, he had a problem performing… I feel like I hold a lot of responsibility for this as he couldn’t get lined up properly to enter me & I was a little too busy to help him find the target… damn neo-vag.

I’m honestly surprised it doesn’t happen to more people in that room because it’s seriously sensory overload from the moment you walk in. We tried, but life is life & unfortunately he went away instead of joining us. Sadly, Sabrina went with them as well, as a good partner should when we’re in need of support.

Thankfully though, Stacey and Aaron showed up while Sabrina was on my face & I didn’t even realize until after Scott had left. Even more conveniently, they had setup on the bed right next to us & invited me over when my last couple left me by myself. I was more than happy to slide over and join Stacey in blowing Aaron.

Aaron had evidently been waiting for me since the night before and quickly found himself asking if he could fuck me now too. I agreed, but under the condition that I could taste Stacey at the same time.

She repositioned themselves onto their back near one corner of the bed while I laid between her legs and lifted my ass in the air. This was it; I was about to be fucked and was so into this moment. I had lubed up before Scott had tried earlier, so Aaron had zero resistance as he slowly pushed into me from behind. Learning from my last encounter, I slid my fingers into myself first & they acted like a shoehorn, guiding him into me. One long slow stroke until his full length was buried inside of me. I focused only on relaxing my muscles to not squeeze him out of me as my body shivered in response to the alien intruder.

My tongue and mouth worked on autopilot as I couldn’t think of anything outside of him sliding in and out of me. Stretching me wider than my toys do but not as deep. I was in heaven as his pace slowly gained fervor. This felt right in a way that I was unaccustomed to. It was as though I’ve been intended to do a specific act my whole adult life & have been doing it completely backwards until this very moment when I found myself pushing back into Aaron’s thrusts. Faster and stronger by the stroke.

I suddenly heard Stacey’s moans as her orgasm approached and was brought back to the entire scene unfolding around me. Hearing his wife getting off under my tongue was seemingly all that he needed to finish his quest as his pace became hectic now. His compulsion to finish was palpable & I was the lucky recipient of his passions. His hands held my hips firm as he buried himself one last time, as deeply as he could, and let out a loud groan. I could feel him pulse and twitch inside of me through his condom as his body shook behind me. I squeezed my pelvic floor muscles to milk him dry before he fell back from me.  I guess I must’ve squeezed him too tightly though as I pulled the condom off of him as he withdrew.

I rolled over & Stacey was now beside me with some water ready for me since they finished a little before him and enjoyed the rest of our show from the sidelines. We all made out with each other for a minute before I excused myself to the bathroom in search of recovery for a minute. They thanked me as well & left the orgy room for the night. I’ll take pride in knowing I was enough for them tonight.

I just had a dick in my vagina!! 3+ years of waiting… building it up in my head… fantasizing about what it may be & the reality turned into something completely different.

Not yet. If I stop to think about it, that’s all I’ll do for the rest of the night. The ice is broken, so dive in!

*********************************

 

I was debating playing more with somebody else, but I wasn’t too into anyone that I currently saw hanging around the room, and didn’t want to interrupt any current play sessions, so I found myself ready to leave and get a fresh cocktail.

While gathering my belongings in the lobby, I saw someone sitting on the couch with an injured foot, and I began talking with them, foolishly assuming that I’d have a few moments of calmness. As it turns out, we found each other to be extremely attractive, so with us already being horny and tipsy, we were making out with little hesitation. Jamie seemingly had their eyes on me too and had been waiting for her chance with me too as she found her way to going down on me in quick order. I didn’t cum when Aaron was fucking me, so it took very little time for Jamie to get me there.

The oral skills I’m running into this week are notable by themselves!

Being even hornier now, I took my own turn with this beautiful woman to kneel in front of her as she now relaxed on the couch. The noises she made… they were so very playful and I wanted to draw out as many of them as I could. She had this purr, laughter, moan combination that hit my praise kink perfectly. They must be known by the hosts as one of the founders was staffing the lobby door at the time & jokingly told her not to squirt on the couch before somebody else dropped a towel on the couch next to her. We barely skipped a beat in sliding it under her and we continued, but now I was on a new mission based on what I just heard. I added my fingers to join my tongue and the noises only intensified. Her husband came back just in time to catch the finale. He had been running an errand for her due to her injured foot but was back now and kissing her while roughly playing with her chest. Eventually I came up for air and noticed another clean towel nearby, which I grabbed to dry off my own face, and the floor in-between us before rising up to begin kissing both of them.

He was cute, so I was into it when they sat me on the couch and began to go down on me together. I didn’t think that I had another orgasm in me at this point but when they started taking turns between kissing me or eating me out, I lost myself once more. They each approached my pussy differently each time they went back down. Sometimes they’d add a finger or only their mouth & then the other would take a turn and do something completely different. My brain couldn’t keep up with it all and I finally fell into orgasmic bliss once again.

    I need a break & I’m thirsty!

    They were just starting their night and went into the orgy room as I took a minute to recover before returning to my original hunt for another drink.

*********************************

 

Back to the nude pool I went…oh hey! Zim + Natalie are hanging out in the lounge chairs on the pool deck. Lucky me! I never got a good read on Zim, but I was certain that he liked to watch Natalie play.

They caught my attention as I walked past, not initially seeing them in the dimly lit area, but I stopped to chat before having Natalie join me while I refilled my drink. I began telling her all about my evening so far as she obsessively played with my tits. I adore having my breasts played with, so I was more than happy to let her tiny hands get their fill. She was a TINY girl, who could easily be picked up by literally anyone there, so my DD’s were more than she could grasp in each hand. She made a point to performatively play with them as such when we returned to sit next to her guy.

The whole vibe that I got from her was one of enjoying showing off, which makes sense as they were evidently a dancer, but I’m equally as bad. I love to tease and entice, so that she wanted to be silly and put on a show for everyone was absolutely something that I was into. The pool was pretty busy from what I’ve seen for the night-time crowd and we were on the lounge chairs right by the stairs to this area and the bar. Only a couple feet of distance separated the end of the lounge chairs and the pool’s edge. My eyes had adjusted to the lighting now and I could tell when heads were turned our way as conversations continued in the pool and all around us.

Her hands didn’t stay on only my chest for long. She had pushed me onto my back on the recliner next to her husband, pussy facing the pool, and was hovering over me at first, bent over at the waist. Biting, kissing, and suckling one nipple than the other as her fingers spread my pussy open for all to see when she wasn’t sliding a finger in and out of me. In turn, I spread my legs over the chair’s armrests to give everyone a better view and she took this opportunity to lower her mouth to my crotch, keeping her ass in the air and acrobatically doubling herself further in half. She already knew that I was a bit worn out for the day, so it was a light teasing touch she delivered upon my tender lips. Zim and I joked and laughed as she wiggled her butt in the air at those in the pool behind her, cheering her on until finally, it was my turn to put on a show.

I tend to be fairly subby, but I’m a switch at my core since sometimes I like to be in charge too. Only really with Femmes though. She had sat on my lap, so I put an arm around her and was able to stand up with ease, holding her light frame against my body. It felt no more difficult than when I was in the gym earlier that day. I held her there for a minute, kissing her deeply as my free hand played with her butt. I was pretty proud of myself when a cat-call came from the pool below us.

I spun around and lowered her onto the chair I was just laying down on, gently but with firmness indicating to stay put. She told me at the bar that she likes to be spanked sometimes, so I pulled both of her legs together and into the air, sat on the next chair over & told her to hold her legs. They were raised toward her head just enough to have her butt tilt off of the chair.

My fingers traced down the back of her leg as I took in the sight before me. Her hairless pussy and taught butt cheeks on direct display to those in the pool as most heads were now turned in our direction. A smack resonated across the pool-deck as my hand made contact with her ass. Again I let my fingers trace her body before another full handed smack to her other ass check. Left, then right, then left, with my fingers teasing her between each smack, feeling her wetness start to expose her excitement as my hand slid over her mound. They weren’t intended to hurt, so I took pity on her & used my one arm to hold her legs up when I could see her starting to tremble from the position. Allowing the weight to rest on my arm now, I began kissing the back of one leg, and then the other, from their heels all the way down to their curves of her ass cheeks.

When I was content, I moved to kneeling on her chair and lowered her legs on top of me. I kept my ass in the air for the sake of those in the pool and slowly fingered myself while tasting her. My fingers of my free hand again joined my mouth which drew a very communicative mewling from Natalie. I discovered what they liked and I was once again on a mission to do as instructed to earn my reward. Her hips soon began pushing against me more and more as she found herself getting louder. It was when someone in the pool called out “make her cum,” that her hands grasped the back of my head and her pussy squeezed my fingers tightly in place. She screamed out against the starry sky above us and was rewarded with cheers from our audience. I’m not sure which of them settled down first.

We had asked Zim if they’d like some attention too, but they weren’t out to have as much fun as we were this night, so that would be it for me today.

Now utterly exhausted, I made my way back to my room to get some rest.

 

*********************************

The thoughts that come after

 

It finally happened! I got fucked for real, with a penis in my vagina… MY pussy!

Is it bad to say it was anticlimactic? Seriously… 3+ years of waiting to experience the real thing & I’m not sure if it was worth all of the hype ¯\_(ツ)_/¯

I’m pretty sure I built it up in my head more than reality could match, but I don’t feel any guilt about wanting my “first time” to be special since it’s MY virginity after all.

It felt comfortingly “right” though. Like I’d been walking backwards instead of forward.

I’m not sure if it was disappointment or anger at myself I was feeling too… I was too tight and different and… “too trans” for my first potential partner to enter me.

It’s so unfair!! Why does my pussy have to be so much extra work.

That finger shoehorn trick is something I’ll have to remember for certain

Oh those eyes again. They do things to me…

*********************************

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Day 04 – Tuesday

 

 

Evening Vibes: Glow Rainbow Rave

12:00PM Bloody Mary Morning

12PM-1PM Educational sessions – Anal Sex 101 + 102 (Go a little deeper) (KS)

1PM Bi Orgy Day Play (KS)

10:00PM Bi Orgy (KS) + Bi Dungeon (Dungeon)

10:30PM Glow Party (Main Pool)

 

My Vibes & Trigger Warnings:

1-1 casual date

 

 

 

 

 

Running down the beach in a swimsuit = Bucket list item checked off.

There’s something performatively feminine about it & I know it’s driven from movie representations, but it’s another situation where I wanted to BE her, not be WITH her like the other boys did. Thankfully I’m feeling incredibly confident in my own body right now since I’m in the best shape I’ve been in for decades AND have been getting an overwhelming amount of sexual desire from those around me; therefore, I felt brave enough to make my dream a reality today.

I wanted to explore a little bit of the beach front today, so I put on the minimum of clothes needed and left through the beach gate leading to the Sandals resort next door. I didn’t go far, only 1.5 miles each way, but it proved to be a good exposure to what the other resorts looked like and how people were interacting with them.  I’d see a family getting ready to go out on a boat, or somebody fishing by themselves, and many people just lounging in chairs by the beach or pools. A small gift shop here or there too.

One very notable difference was in regards to the tree-coverage. Until I got past the last resort, there were no trees near the water front & it made me laugh when I realized why Hedo was different than all of the rest. Each day, there’d been boats coming close by our resort so that the tourists could get a look at us wild and crazy nudists. I get it, I love titties too! There were quite a few trees in the sand on Hedonism II, which made me incredibly happy as they gave me shade to take a nap or read my book, with less risk of burning in the sun. I really don’t think I would’ve enjoyed my beach time as much if I was at one of these other resorts.

I decided that today would be a rest day for me as I wasn’t too into the theme of the night, glow night (dance party). I’ve never really enjoyed dancing + I knew I’d be into tomorrow’s theme: Kink Day.

I ended up taking a nap in a hammock on the beach later that morning before joining a friend for lunch.

We had found each other on the app & our mutual tattoos helped break the ice. The more we got to know each other, the more we both seemingly fell for each other. Sometimes people just click & I was easily clicking with her.

Lunch turned into more talking and drinks and more talking before we eventually went back to their room. This is the same girl that I had gotten a taste of in Kama Sutra earlier in the week before they got distracted by a dick… literally… and I had gone off on my own.

This time, there were no distractions for us.

We took our time going back and forth. She went down on me, then I went down on her, then she went down on me again, before I used her favorite toy on her.

I’m not going to go into the naughty details of this day since this was different than just hedonistic sex & I owe that the respect of what it was.

Despite my rules to not catch feeling throughout this trip, we had a full day together that felt like a date the entire time. What I will say is that I found someone incredible who I loved spending time with. 

I hadn’t yet been to Pastafari, the Italian restaurant, so we got pretty and finished our day together with a dinner date. The portions were larger here than the other restaurants & sat a bit heavier too. Lobster and steak and pasta though?? Really can’t go wrong with a combo like that. My body appreciated the carbs to help fuel all of the ongoing antics.

They aren’t a night-owl + I had promised myself to take it easy today, so we went our own ways after dinner. I think they had another shift to work at the orgy room too, but I needed some extra sleep today.

We still regularly connect outside of this event week, which is one of my favorite elements of this week in that the people are just GOOD people.

I have a couple rules though that kept me in check today:

1. I don’t do long distance relationships anymore.

2. Don’t catch feelings at these events. It’s too easy to perceive emotions when there’s a lot of sex, drugs, and alcohol involved, so my already high guard is on overdrive.

 

Despite my rules, I loved our whole date day: from lunch, to our room, to dinner. The whole day was a highlight of my trip.

But I’m tired now, and need to go to bed… I can send my bestie videos in the morning.

 

*********************************

The thoughts that come after

 

That was really cute. The whole day felt like a date.

They weren’t kidding when they said Hedonism is a marathon & we need to pace ourselves.

4 days down, 3 more to go.

*********************************

 

 

 

 

 

 

 

Day 05 – Wednesday

 

 

Evening Vibes: Kink in Paradise

12-5PM Nude pool party

12PM-1PM Educational sessions – The art of a scene (Disco)

12-1PM Educational Sessions: Anal 101 (Kama Sutra)

1-3PM BDSM Day Play (Disco)

2-4PM Beach Olympics (Prude Pool)

10PM Orgy Playroom (Kama Sutra)

10:30PM Dungeon Demonstration Showcase (Disco)

 

My Vibes & Trigger Warnings:

Rope Bondage

Orgasm Control

Marathon sexcapades

 

 

 

Gender, and sexualities, and kinks, oh my!

I got into kinky sex at a pretty young age when I kept finding myself in accidentally exhibitionistic acts. It starts with the simple “risk of getting caught if your parents come home early,” and maybe involves getting frisky with your partner when you’re out swimming with friends, then one day you don’t mind if somebody is watching because you DID get caught and the reaction wasn’t negative. Then the next thing you know, you’re cuffed and bent over a spanking bench with a ball gag in your mouth after your unknown numbered partner of the night because your Domme arranged a gang-bang for your birthday. Slippery slopes.

Needless to say, I was pretty excited for the theme of the day being “kink” and had an appropriate outfit chosen for the evening. Pasties were all that were set to hide my nipples as purple elastic straps of a harness encircled my torso, highlighting my tits & a very short schoolgirl style skirt completed the look I wanted to project. I wanted all of the attention tonight.

It was an interesting contrast to my other outfits this week. Each night’s theme awarded opportunity to get silly or slutty & I leaned into it a few nights. I had a new revealing strappy white dress for Monday’s white party, a rainbow tutu for the rainbow glow rave night, and my favorite festival appropriate dress for Friday’s Masquerade theme.

I didn’t obsess over these though as they were more useful as conversation fodder than anything else as I preferred to get naked again as soon as possible every night after dinner.

Being in no rush, I slept in once again today, dragging myself out of bed only just in time to catch the end of lunch service. My only goal until the evening was to observe the Beach Olympics, so I took my time to relax and chat with strangers over free refills of Malibu Sunrises at the main dining room’s bar.

Laugh if you want, but I stayed consistent with my drink of choice because I remained in a nice tipsy buzz and was well hydrated all week.

There are so very many people here that it’s hard to keep track of everyone or even make sure to meet everyone you hoped to. Sometimes it helped for me to stop for a few minutes in a busy walkway to let them come to me. I swear I was never alone for more than 2 minutes at this place! All I had to do was stop chasing my desires and they flocked me. I was always on the move to something, someone, somewhere, except for those rare moments like this when I was intentionally wasting time.

To feel desirable was essentially my primary goal of coming to this bi-week event. I’m not ashamed to admit it at all. Part of my trans experience is the unavoidable threat from society to be ostracized for living my life authentically. How can I truly believe that I’m wanted if society also thinks that I shouldn’t exist? Tricky mental gymnastics…

I was happy to have all of the attention… constantly… my ego grew 3 sizes this week.

Mid-afternoon rolled around and I walked downhill to the prude pool. The Beach Olympics were extremely entertaining as couples battled over silly games like you’d see on the Nickelodeon family game shows of the 90’s, if they were NC-17 rated. For one game, you had to hold a ball between your bodies, move to the other end of the pool, each do a 360 and go back, without dropping the ball. Every game was another less than discrete way to get two naked bodies together to do some activity better than anyone else & it was a fantastic time for all.

They happened to need a stop-watch for one game but forgot it; however, little miss runner had her fancy running watch on 24/7, so I got to have a mini-Vanna White moment and helped judge one competition from up on stage. Oh how I love those eyes on me.

Yes, I do indeed know what my heartrate is during sex & YES, it does correlate to the strength of an orgasm.

The games ended with multiple winners & I found myself looking forward to my next scheduled activity.

*********************************

 

I had made plans for today to meet up with a couple that I endearingly refer to as Rope Boy and Rope Girl. They’re another couple that I ran into on the beach, while I was entering the nude side to read my book one morning, coffee in hand. They had a room near where I liked to read under the trees, and I’ve said hi in passing a couple times earlier in the trip. We started talking and realized the universe keeps putting us in the same place, so we decided to lean into it. I spent a good amount of time sitting in their hot tub already and was going back today to meet them there.

More enjoyable conversation ensued as we came to the shared mindset of wanting each other’s bodies & we agreed to take a few minutes to get ready then meet at one of the cabanas next to the prude pool on the beach. 

I foolishly went to the wrong one cabana, but Rope Girl found me. The cabanas are really just a bed on a raised platform with a bit of a ledge around the mattress + 4 wooden poles around the corners, and an open slats wooden roof above to provide shade. For our plans, this was a perfect venue.

We had already talked about our desires, boundaries, and backgrounds which made it very easy to trust them both to do what I had asked of them. 

Rope Boy was fortunate enough to have been properly taught how to perform bondage with rope. RB also spent a bit of time doing demonstrations, which Rope Girl has been known to help him with. They had an excellent chemistry that was charming and endearing in how clearly in love they are with each other & are so incredibly supportive. They’re also very in sync when they play together.

After we found each other at the right cabana, with a wonderful view of the ocean in front of us, we laid out all of our items needed for our scene. Lube, a couple toys like my favorite vibrator, and rope were the stars of today as they were neatly laid out on a towel at the edge of the mattress. RG and I decided to keep each other entertained while we waited for RB to get himself prepared. Knowing I’d lose the opportunity soon, I laid RG down on the bed and moved my lips down her body with hunger.  I’m a fan of all things “body modification” and I have personally had 27 piercings in total if you count re-piercings plus I have many tattoos. RG has numerous piercings in their labia which I had been waiting to play with. I let my tongue explore each as I began to learn about her. Seemingly just by the time that I had her figured out, Rope Boy was ready for us. It was my turn to lay on my back.

He began with my left leg, pulling my foot to my butt as loops were added a few inches apart, covering the length of my knee to ankle. He proceeded to attach this section of rope to one of the corner posts of the cabana so that my feet were pointed toward the ocean.

He progressed with a methodical care through each limb, securing it to either my own body or to the cabana. Rope Girl’s mouth met mine as Rope boy focused on my legs. Her tongue teased my nipple piercings as he secured my right leg to the other post, leaving me spread open for them.

He took extra care to check in with me at each step of his process to ensure that nothing was too tight or uncomfortable before progressing.

Once he was done with my lower half, they seamlessly swapped positions. Her kisses trailed down my stomach and teased my inner thighs as he tied my left arm to that post, leaving me feeling stretched as my right leg pulled me in the opposite direction.

Nothing was uncomfortable, but I was completely losing my ability to move. The rope biting into my skin only enhanced the moment.

Her mouth found my pussy as he began working on my final limb, securing my arm to itself in a similar fashion to my left leg, and then to the other post. Her fingers slipped into me when I surrendered my final bits of mobility.

He added one more length of rope to my torso & connected it to my limbs before adding a final strand, tossed over the roof slats above us. Rope Boy combined these, forcing my body to arch in display.

I was completely at their mercy now.

Content with his work, Rope Boy was now ready to join us a for a bit more interactive fun. My oral fixation squealed as he let me suck on his pierced cock. It was my first time playing with a Prince Albert. I could only barely move my head and was forced to prove my tongue’s worth as it traced his piercing. Pulsating my sucking to enhance my minimal movement, letting him grow inside of me.

Rope Girl left me with no room for thoughts outside of them as she had now swapped her fingers and tongue for my vibrator. She teased me mercilessly. I was on the edge of orgasm from the moment he put his dick in my mouth & she refused to let me cum.

My moaning was my only means of communication & I was begging for release. Repeatedly, she would completely remove my toy when she knew I was getting close, leaving my hips gyrating against the air with what little movement I had as my tongue mimicked the same circles around the head of his dick, never leaving my mouth.

Finally she graced me with what I yearned for, holding my vibrator against my clit, my pleasure muffled from above. I’ve never cum so hard in my life! I couldn’t think. I couldn’t move. All I could do was cum. My muscles tensed against my bounds as my pussy convulsed over and over again.

I felt my own juices pouring out of me in a way I’ve never felt before while my pussy clenched at nothing. My limbs tried in vain to let my muscles contract, to let me squeeze anything I could, but it was to no avail against my bounds… I’ve grown used to back-to-back orgasms, but never one that lasted this long, or this continuously.

I heard Rope Girl telling Rope Boy to look at something when he pulled out of my mouth mid-orgasm & later learned that it was to show off just how hard they made me cum.

I absolutely soaked that bed.

Because my prostate had become my g-spot during my surgery, I still released fluid during an orgasm; however, that’s the only natural wetness of my neo-vagina. Usually when I have an orgasm, it’s not even enough to escape my pussy, unless it’s a notably large orgasm & even then it’s not much more than a tiny wet-spot on the bed.

This bed was soaked.

Their aftercare was just as practiced as their setup as they took their time helping me settle. A bit more teasing and playful touching followed before they slowly began removing the ropes. The rope bites left a mesmerizing pattern on my skin, turning slightly red as the blood flow rushed back into each limb.

THAT was a perfect way to spend “Kink Day!” Easily top 3 sexual encounters of my life.

After we had all recovered, I made sure to profusely thank them for their efforts & we decided to do dinner together that night too.

We met at the agreed upon time at Flame this evening. This was my 2nd time at this restaurant, so I tried other items on the menu. There really wasn’t a reason to limit yourself at these restaurants, so I got 2 of each course’s options. The variety of options was indulgently fantastic.

Flame also happened to be right on the beach… right next to the cabana we played on earlier…that I could see from my seat, making me blush each time the memory flashed back.

*********************************

 

After dinner, I was left alone again to resume my hunt for play partners. I wasn’t kept waiting long.

I had returned to the main dining room to watch the resort’s stage performance for kink-day. It was a very sexual performance. Sitting at a table with friends I’ve made throughout the week, we gasped in unison when the scenes turned provocative and commiserated between scenes of how we want to have the same acts we watched performed on us. It was during a later break in the acts that Jason and Jamie came over to say hi.

I watched the show’s finale while sitting on Jason’s lap, adding to the teasing of the evening. I asked them with a wink if we’d all like to go to our rooms to start our evening. The response was gleefully receptive as we locked arms and began heading to their room on the nude side of the resort.

It was mere seconds after entering the room that I was spun around, back to a wall, as their lips explored by body. My schoolgirl outfit’s skirt’s Velcro waistband was opened and dropped to the floor, leaving me standing in only a few straps of cloth encircling my chest and torso, the purple harness drawing attention to my curves. Jamie left me with Jason as they turned on some mood lighting and music & I took this opportunity to move him to sit on the bed.

Straddling Jason’s waist, I ground against him as our lips battled aggressively for control. Having a desire to be in charge for the moment, I stood up from Jason’s lap and lowered myself to my knees in front of him. There was no need for teasing tonight, so I began to bob on his shaft with earnest desire. I wanted him inside of me and was determined to help him be prepared to fuck me. I used my free hand to prepare my still wet pussy for them too. Sensing their readiness, I climbed onto the bed and crawled toward the leg-spread Jamie, who had been watching me suck off their partner. Only a quick kiss stopped me before lowering my face to their mound as I raised my ass in the air for Jason.

Jamie’s noises were music to my ears while my tongue explored her depths. I adored them at Kama Sutra’s lobby and was hungry for more of them. My tongue was the star of our show only for a moment before Jason was kneeling on the bed behind me, lining themselves up to enter me in doggy-style. They chose to fuck my ass first for a few minutes before they wanted to change. I was annoyed because we hadn’t talked about it, but I still enjoy anal. It just wasn’t what I truly wanted. I was overjoyed when they were interested in my pussy next. They found their mark with ease thanks to my fingers guiding the way and were buried completely in one forceful stroke. My pussy welcomed the intruder, muscles relaxed and wanting. His pace at first was slow as he slid his full length in and out. I squeezed his cock each time that I felt his balls bounce into my clit. My moans filling the delicious treat in front of me. It wasn’t until I started to push back in time with his thrusts that his speed increased.

Gods this felt incredible.

This was the first time that I have been properly fucked in my own pussy. The new sensations were distracting as I tried to understand what I was feeling from where. The stretching of my opening was a consistent source of pleasure from his member never leaving my vagina. My clit springing into my mind each time his balls made contact. The sting from deep inside when he bottomed out my depth & most wonderful of all was the pressure on my g-spot as the head of his cock rubbed against it on each stroke. The most intense sensations were from feeling my g-spot being pressed against my pelvic bone each time he pulled backwards.

I’m so incredibly happy that I fought for the right to see a surgeon who was known to have high success rates in their patients being orgasmic. This was everything that I hoped it would be.

His pace was impressively consistent as it drove me over the edge to my first orgasm of the night. I was having trouble multi-tasking at the moment & they knew it.

With impressively smooth movements, they rolled me onto my back so that Jamie could sit on my face as Jason continued to fuck me. Her hips were grinding against me as I gave up caring about oxygen. I only wanted to consume her. They used me for their pleasure, kissing each other while their hands roamed my body. Her hand found my clit and she played with it as her other hand pinched my pierced nipples. She was intentional in her actions, keeping me worked up but not climaxing, as her own orgasm was approaching. She pinched my nipples hard as she came, encouraging Jason to fuck me with renewed pace, sending me over my own orgasmic cliff once again, to one much larger one than the first time.

Jamie crawled off of me and excused themselves to the bathroom while he repositioned me once again, now standing at the side of the bed with me on my back and legs in the air. His endurance was truly impressive as he continued to plow into me. I was cock-drunk at this point. My pussy soaking wet thanks to my own orgasms. I had no sense of time as he continued to take me, that is until Jamie crawled back onto the bed and began suckling my tits as they hovered over me. I tried my best to do the same to her between ragged breathes in time with Jason’s persistent thrusts.

We made one final position change as I crawled further under Jamie so that we were now in a 69-position, near the other edge of the bed. Our lips were perfectly aligned as Jason entered her from behind now. I was mesmerized to be this close to their coupling directly above me. Watching his shaft disappear inside of her and reappear, only for me to lick at his entire length before disappearing once again. He gave me tastes of her pussy off of his cock from time to time, but my tongue was everywhere I could get it between these two. I’d focus on her clit when he fucked her, licked his shaft when he made slow long strokes, sucked his balls when he held himself at full depth, all the while, her tongue and fingers never slowed their attention upon me, making me cum one final time.

Jason’s pace quickened soon after and his groans grew louder, signaling the end of his marathon fucking. He pulled himself out of her before implanting himself fully in my throat and releasing his load. My own hands grasped his butt and held him fully in my throat as his spasms slowly subsided before he collapsed beside us.

I was exhausted once again & we all needed a bit to recover from our shaking limbs.

I was asked if I’d like to use a strap-on and fuck Jamie, but I had to tap out as my pussy was too sensitive for anything else at this point. What I didn’t tell them was how the concept of returning to a thrusting motion, using a phallus to penetrate someone else didn’t sit well with my mind’s journey this week. I was here to explore being fucked, not return to being a fucker, so I couldn’t wrap my head around it in the moment. Trans BS mental gymnastics strikes again. They fully understood and praised themselves for a job well done.

They walked me back to my room and we said our goodbyes before I headed to the shower, with the intent to get some much-needed sleep.

 

 

*********************************

The thoughts that come after

 

            I really missed being tied up. Giving up control, letting my brain turn off completely, just existing in the moment, trusting someone to treat me properly… and they ABSOLUTELY treated me properly.

            I’m sooooo glad I asked him to take pictures before untying me ^__^

            It’s interesting how I only have this thought with women: what do they think of how I taste? I’ve gone down on post-op trans women & frankly, it tasted more like dick than pussy. Jamie kept coming back for more though… and so did Allie!

            This is what keeps me from dating women right now. I’m afraid that when it comes to women who like women, they’ll be disappointed in how my pussy tastes, how it feels, how it stretches or doesn’t, how lube is such a requirement… I’m afraid that this is something that would turn them off and not want a long-term relationship because that one aspect of our sex-lives.

            BUT HEY! I got fucked REALLY well tonight!!!

*********************************