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Dear Diary: Day 1

We arrived at Hedo today and looking back, I have felt every emotion I have in my body throughout the day. Flying to Jamaica was an adventure due to the airport not wanting to accept my COVID letter but we made it through all of the checkpoints and were able to make the flight. I am proud to report that I had a yummy margarita at 9am with no regrets! I also put my phone on airplane mode for the flight but decided that I was not going to turn it back on the entire trip. Let’s see if I can last that long.


After we got to Montego Bay, I got very nervous. We still had a 1.5-hour bus ride but that turned into a 2-hour bus ride due to traffic. By the time we arrived, I was a ball of anxiety and exhaustion. The enthusiastic bellman named Batman helped me relax by welcoming me home and providing me a drink. That was very much needed and appreciated.


As we are sitting there, it was 7 minutes into my Hedo experience, a black car pulls up and a loud, bubbly blonde jumps out of the car. She was wearing bathing suit bottoms, or panties, I never really knew and a tank top that wasn't covering her large titties. I remember thinking to myself, I could never be that open and free. She was already heavily influenced by adult beverages, loud and vulgar. I just looked at Fox, my eyes were probably as big as small plates and I believe the color left my face. I told him; I can’t do this. Fox lovingly reassured me and we were taken to our room. As we walked to our room you could still hear her throughout the dining room. Her laugh was infectious yet terrifying. She was having the time of her life and I was more terrified than ever.


We went to our room and I was starving! I wanted to throw on a swimsuit and go eat but Fox wanted to unpack first. BTW, he is the slowest unpacker ever! Maybe I was just frustrated because I was hungry but come on! We finally ate some yummy food, got a drink and I began to feel better.


The theme for the evening was Rock Star and I feel like we were dressed sexy for the show. The food was great and the drinks were strong; however, the show was stunning. It was very energetic and a great introduction to what the week will hold for us. We met Carol and David from The Sexy Lifestyle for the first time as well.


I made a huge decision tonight to say yes to things I would normally say no to. It took me a minute but I finally shed my bathing suit bottoms and went to the pool naked for a quick swim but came back to the room to go bed early for Hedo but we were exhausted. I am excited to see what tomorrow brings.


Dear Diary: DAY 2

Day 2 at Hedo did not disappoint! One of the reasons I was having a hard time shedding my bathing suit bottoms yesterday was because I needed a wax. Thankfully the spa on the property helped me with that issue and I got a facial to help me relax. We met Carol and David for breakfast and had a great chat about who we are and what our goals were for this trip. They are so amazing! We also met a new couple at breakfast that we ended up hanging out with most of the day but I will talk about that more in a bit. Armed with my freshly waxed vagina and my newfound confidence we made our daytime debut at the nude pool.

The wife of our new friend couple and I relaxed in the ocean and looked for sea treasures. I did find a live sand dollar that became my pet. After a few hours of great conversation, flirting and adult beverages something happened that I still can’t believe I participated in. Our new friends that we were talking to and having fun with walked over to Fox and I while we were relaxing by the beach and the husband asked if he could kiss me. One thing led to another and we had a foursome on the beach. In front of EVERYONE on the beach and at the pool. It was invigorating. I just closed my eyes and let it happen. I was unable to have an orgasm, no matter how hard the couple tried but it was my first public sexual debut, cut me some slack.


Shortly after my sexual beach debut we got ready for dinner and the show. It was sports night and Fox and I dressed to the nines. I even won the costume contest! Later that night we danced, we flirted and then we had more play time with our new friends. This time I had multiple orgasms and just let go! It was beautiful watching Fox please her while I was being pleasured as well. FYI: the rooms have mirrors on the ceiling and that was sexy as hell. The couple was so sexy and so yummy!


To carry on with the first experiences while Hedonism ll, after the show but before our play time with our friends, we visited the courtyard where they have a DJ and dancing and this is where I gave our friend and Fox a blowjob… in the courtyard… in front of everyone. Who am I?


After our playtime with our friends, Fox and I went to the nude pool café and ordered delicious pizzas and unpacked everything that had happened throughout the entire day. Fox and I are absolutely blown away at the amount of fun we have had so far, and it is only day 2! I can’t imagine what tomorrow might bring.


Dear Diary: Day 3

Welcome to Day 3 at Hedo! My week of saying yes to things I wouldn’t normally say yes to continues to shock me! Today went better than I could have ever imagined. Since we had a late-night last night, we slept in and enjoyed a late breakfast, it was more of a brunch. Afterwards we dropped our clothes and headed straight to the nude pool. There were no hesitations, no embarrassment, I just went there without even thinking about it.

I started drinking a bit earlier than I normally would but it’s Hedo so there are no rules. The party was pumping, music was great and the party hosts were engaging. They included everyone, got everyone involved and did things to me that I never thought I would do. There was one host who was a tiny, gorgeous blonde who was using a toy on women. This toy was like no other toy I had ever seen before, it was a drilldo. Yes, it was a dildo attached to a Sawzall! What this hell is this contraption; I had Fox order one almost immediately.

When this sexy little snack asked for volunteers, my hand shot up. I am not sure what got into me, well I do, it was a drilldo! It was powerful and erotic all at the same time. She was rubbing my body and pleasuring me with this drilldo until I had an orgasm… in front of everyone at the pool. I have never felt so free! So proud of myself!


The theme for the evening was sexy school girl. I was tired from partying all day and didn’t want to really dress up but honestly it boils down to the fact that I wasn’t feeling comfortable with any of the costumes I had brought. I improvised and created something I felt comfortable in and we were on our way to dinner. I was wearing this tiny little plaid skirt that only covered half of my butt, my black bra and no panties!


During the show that evening they had another costume contest and I ran on stage to participate in this adventure. When it was my time to play to the crowd, I dropped it like and showed the entire crowd my bare ass and waxed vagina! I made it to the final 2 and it was declared a tie. I just continue to shock myself more and more on this trip.


We danced for a bit in the courtyard but Fox and I were so horny after the day so we went back to the room and had amazing sex! It was so intense and passionate. I think that Fox is seeing me trying new things and this is making him more attracted to me. Of course, we ended the evening by going to the nude pool café for our nightly pizza.

Remember that loud blonde I was scared of on day one? We had our late-night dinner with her and her husband. While they are loud and very outgoing, they are amazing!


Dear Diary: Day 4

Day 4 did not disappoint but I am convinced that there is no day at Hedo that isn’t mind blowing! We slept in again and had a late breakfast/early lunch at the grille. You might think that sleeping in would be a normal practice but Fox wakes up early every morning, every day so him sleeping in is rare.


During our lunch we met a fun couple that was from Texas. Immediately the men established that they were both in the Navy and even stationed at the same place. It was a fun moment seeing Fox get excited about meeting someone from his old life. After lunch I am sure you can guess where we ended up, the nude pool! That is where the party is at and I am not missing a great party! We started connecting more with the host group and we fit right in with their personalities. Fox was having ear issues during the afternoon and had to go rest in the room for about an hour. This was a very new experience for me. I am very outgoing but Fox is my comfort blanket and with him not being there I had some anxiety. I could have allowed this anxiety to stop me from having a good time and normally I would have just gone back to the room with him but I pushed through the uncomfortable.


In the middle of this anxiety, my being alone in a pool full of naked couples, I was voluntold to get ‘on stage’, the side of the pool where all of the action was taking place, to participate in a 8-way pussy train. First, I am very selective about going down on women to begin with and second, I have never done this for an audience before. I had so much anxiety going into this activity, I was looking for Fox to reassure me but he still wasn’t back, and I was afraid that I would make a fool of myself in front of everyone at the pool. But I did it! I went down on 2 different women during this activity. I even got great feedback from the ladies. I was so proud of myself! Fox was not there to witness this but he was told all about it when he returned. The look on his face, the admiration, the pride he was feeling for me doing something that was outside of my comfort zone made me fall in love with him all over again.


But wait there’s more! The fun only continued pool side. Remember that tiny snack of a woman who used the drilldo on me? Well, she got me again! She called me up to play with me with this toy that sucked and licked my clit while vibrating. Ummm, I squirted almost immediately. When she pulled the toy away from me, my juices flew all over the crowd that had gathered around to watch. Can I just tell you how embarrassed I was! I was mortified! This is another toy that Fox purchased. The toys are going to arrive before we even get home.


The theme for the evening was Jamaica Day and dinner was held outside and the show was great. We danced and enjoyed the company of many new friends that we made today. Fox was called up to the stage for a sexy man contest. He worked the crowd, flirted with the ladies and then dropped into the splits! The crowd loved his show! After the show the group we were hanging out with at the pool held a large ball volleyball game, men vs. women. Of course, the women won!


After our victorious win Fox and I took a walk by the ocean and unpacked the events of the day. It was a day that I needed to unpack with him after being so anxious throughout the day. Oh, and of course we got our midnight pizza fix, LOL. What can I say, the pizza is amazing!


Dear Diary: Day 5

Wait, it is only day 5? I feel like we have been here for much longer. We woke up early today and went on a Catamaran trip with about 80 other people. Our first stop was the reef and I pushed past a slight fear and went snorkeling. Fox was so sweet and didn’t leave my side. It was beautiful but there weren’t many fish so I got bored pretty quickly. We returned to the boat and found a comfortable spot to relax on the nets.


There were so many sexual happenings taking place around the boat. It was sexy, exciting and quite arousing. Somehow, I ended up in the lap of one woman who was playing with my breasts while another beautiful lady pleasured my clit with a vibrator and another one whispered naughty things in my ear. Oh, did I mention that Fox was using the drilldo on me. This was extremely over stimulating! Again, everyone was watching, I just closed my eyes and tried to relax as much as I could.


Our next stop was the caves. These specific caves were the filming location for one of the James Bond movies. The cave bar was still there for us to see. We even had locals where were cliff jumping for our enjoyment. It was a great experience! While we were traveling back to the resort, we had a sweet dolphin play with our catamaran and follow us for a bit. We had a full day already and it was only 2:00 pm.


Upon our return we had our first interview while at the resort. We got to talk with Randy, a great man who sees the world in the most positive way. It was such a great interview! Of course, after we wrapped, we all met back at the nude pool to continue the party!

One thing we quickly learned; with Topless Travel the party never stops! Per usual, I was adventurous and gave Fox a blowjob on the side of the pool for all to see. I already had a full day of fun but there was much more to come.


We got a group together of new friends and had dinner at Harrysan, the hibachi grill before the evening show. That was fun to bring a group of people together that probably wouldn’t had connected. After dinner we all went to change into our evening wear. The theme for the evening was the glow party. I was so excited to wear my costume and I felt amazing! The party was fun, we danced, we partied and laughed until my side hurt! I can’t express how free I felt today!


We went to the playroom to have some fun with a couple for a bit. It started off OK but they were new and got a bit overstimulated so we ended the evening with them and Fox and I went to the hot tub for some fun time for us! Also, we needed our midnight pizza fix.


Dear Diary: Day 6

Day 6 from paradise! Yesterday was exhausting! After all of the midnight pizza and alcohol, I needed to work out for a bit to work on my self-image. The workout felt great and very much needed. Afterwards, I scheduled Fox and I a couples massage by the beach. That was my first couples massage, as well as my first massage on the beach. We spent much of the afternoon relaxing and spending time together but of course we ended up at the pool for the party. We were pretty low-key for this party due to being tired.


During the pool party Carol and David came up to us and asked me if I knew how to salsa dance. I am absolutely not the best dancer but I can shake my ass, LOL. They had a motive and once they found out that we were extending our trip, they implemented their plan. Harry, the owner, was looking for a salsa dancing partner for the next night to perform on stage during the even show. To say I was a willing participant would be a lie but I knew that this was an honor so I agreed. What was I thinking? Have I lost my mind?


I am thankful that we had a restful day because the theme of the evening was leather/fetish night and the show was SEXY! Fox was in a leather vest with his hair pulled back, he had his paddles around his waist… He was fucking hot! I felt sexy and submissive by his side.

We had a different experience after the show. I had met a couple earlier by the pool who had been wanting to meet me but hadn’t had the chance yet. The same couple ended up sitting close to us for the show. 


Afterward, I introduced Fox to them and decided that we were going to give them a tutorial on how to spank. I allowed the husband to spank me, Fox spanked his wife and things were going great. It was an educational experience to be had by all. We moved the experience down to the outdoor beds by the pool so we could continue the tutorial. This went on for an hour. Watching Fox work with a couple so intensely made my sapiosexual heart almost burst. He was so gentle with the couple, explaining why things were done a specific way, teaching them safety as they advanced in their skills. We ended up having side-by-side play which was a huge step for the couple. Fox took me in the playroom where the swing was and I had an incredible orgasm. Him in his costume, between my legs, grabbing the chains on the sex swing… it was all so erotic!


Dear Diary: Day 7

Day 7 and show day! This was supposed to be our original departure date but when in Hedo, you never want to leave. We once again slept in and enjoyed a very slow start to the day which was very nice. I woke up tangled in nerves. I still can’t believe I agreed to dance with the owner of the resort.


During the early afternoon we had the privilege of interviewing Marc and Chelsea from Topless Travel. They are such a fun couple and excellent party hosts… and might I add that I am attracted to both of them!


Of course, we ended up at the pool party for a bit where it rained but the party didn’t stop! I had dance rehearsal at 4:00pm with Harry and Winston so I left Fox to fend for himself and I went to face another fear. The rehearsal went well, I got a beautiful costume and I felt ready to do my best and have fun. My favorite part of the afternoon was being able to sit down with Harry for about 2 hours and learn about him and his journey to becoming the owner of Hedo. He was so inviting and easy to talk to.


After practice I went back to the pool and found Fox. I was so energized and ready for the evening. I wanted to impress Fox as well as every other guest at the resort. Let’s face it, I wanted to be the center of attention for a short amount of time.


I limited my alcohol intake throughout the day so my nerves were very high going into the process of getting ready for the evening. I made sure my make up was perfect, my hair was somewhat cute and my costume was perfect! Winston didn’t want me to wear my costume to dinner so I had to hide it until our dance. I didn’t eat dinner before the dance because I was afraid I would throw up. To say I was nervous would have been an understatement. When the time came, I kissed Fox and went backstage to get ready. I did guzzle a glass of wine backstage to help calm my nerves.


Winston cued us and we were shuffled on the stage. The music began, I tuned out the entire world and focused on Harry. The song was very long, 6 minutes, and I followed him as best as I could. It wasn’t the best dance but I gave it one hell of a try. We got a standing ovation afterwards and many people came up to me afterwards to tell him how good I did. I have to admit, I was a sweaty mess afterwards, extremely thirsty and exhausted from being on the adrenaline high for several hours. I was so proud of myself but I was prouder of the way Fox looked at me after the dance!


Fox and I went back to our room so I can clean up a bit and then we returned to the party to hang out with Carol and David. To continue with the theme of being hedonistic, I deep throated David in the courtyard in front of anyone who wanted to watch! This is not something I would do publicly due to my fear of gagging and throwing up but I just went with it.


We did end the night fairly early with our friends but not with each other. I was starving due to not having dinner so Fox and I went to the midnight pizza bar and had our pizza down by the beach. We discussed and processed the events from the day and then went to bed.


Dear Diary: Day 8

I am exhausted! Day 8 in… wait, where are we again? I had to wake up super early for my class and I feel as if I was a zombie for the first part of class. It wasn’t until our lunch break that I was able to pull myself together enough to get proper clothes on and begin to wake up. Note for future Stephanie: Don’t try to go to class while on vacation!


After class we got to interview the very sexy couple from My Frisky Business and learn all about them and their journey into the lifestyle. This couple is the type of couple that are almost too sexy. They resemble Greek gods and goddesses! Fox told me that the wife mentioned several times that she wanted to play with me but I am just too intimidated by her to even pursue that option. I know, I need to work on that insecurity but not today.

We also did a round table discussion with David and Carol from The Sexy Lifestyle. This couple… words can’t express who much confidence they instilled in me over this past week! They have helped me realize that I am enough, I have a message that people want to hear, and they have cheered on my growth wholeheartedly throughout this trip. I am walking away from our round table with a deeper understanding of myself and my sexual journey due to them believing in me!


During the pool party Fox and I played a game and competed against 5 other couples where we put a water bottle between our legs and “peed” in a shot glass that was in the man’s mouth. We won! Good to know that if I ever grow a penis, I can aim that sucker well! We won a new toy that we will play with later!


We had dinner and enjoyed the evening show with Carol and David then Fox and I went to the courtyard to dance the night away with a sexy couple that we had been flirting with all day. Can I just tell you how sexy Fox was dressed tonight!! He is my favorite human and I can’t get enough of him sometimes. We were hot and sweaty from dancing and decided to head to the pool with our friends to cool off and flirt a bit more. It was during this midnight pool adventure where we learned about bacon grilled cheese from the nude pool grille…. Where has this been all of my life! WOW!!!


We didn’t play with our friends but we did go back to our room and played together with our new toy. Honestly, Fox was so sexy throughout the night, I was very excited to have him all to myself!


Dear Diary: Day 9

Day 9 in Heaven! I had class most of the day and it was absolutely mentally draining! I love my school, I love learning about all things sex, but the class weekends are packed with information, speakers and thought-provoking cases. Not to mention that we are at Hedo and we are partying late into the night. When will I learn that I am not young any longer and can’t pull all-nighters like I used to?


After class we went to the pool party. Fox had been there without me for a bit so when I arrived, he had his sights locked in on a very attractive couple that had arrived the day before. I met them and was just as interested in learning more about them as well. The husband was a bit forward and quickly started kissing me. I have had many firsts on this trip and I was wearing down from the week of excitement, not to mention being in class all day. I was flattered but I feel it was a bit much for my current frame of mind. Fox was having the time of his life with two beautiful ladies wrapped around his waist, boobs in his face and his hands on each of their asses.


During our afternoon pool time with the new couple, they told us that they only play separately and up until this moment, Fox and I had not played separately at the resort. Fox and I had a private conversation about me being comfortable with us playing separately and we established our boundaries for the evening.


The theme for dinner was sports night and we dressed in the same costumes from the week before and looks just as good, LOL. After dinner and the show, we met the couple back at the pool where we finalized our plans to play. While we were kissing and fondling in the pool, I decided to ask if the husband wanted to go to the hut and play. I was so nervous and it was out of my element but since this was the trip of firsts for me, I used my voice and asked. The play was fun and about 15 minutes into us being in the hut Fox came in and told me that they were going to play on another outside bed. This caused me some anxiety but I just closed my eyes and took a deep breath. Fox and I met back at the room around 3:45 am.

I feel I have many feelings that I need to process through after this experience and I hope that tomorrow I am able to verbalize my feelings and thoughts about this experience more clearly to Fox. Good night!


Dear Diary: Our Final Day

This is our final day in Hedo and honestly, I am ready to go home. I had class for the first part of the day and all I wanted to do today was relax by the beach. As soon as we got to the beach Fox found a sexy couple and he immediately plopped down beside them and began talking. He picks on me for talking to everyone but this man can talk just as much as I can, LOL. 


The couple was fun and we invited them to Lobster Island to have lunch with us. We all kayaked over to the island, selected our juicy lobsters and visited over lunch.

We went to the pool for a bit but the crowd had changed and with me being so tired, I was ready to relax by the ocean for a while. But for the sake of the party, we kept going! Thankfully Fox and David had scheduled a sunset photo shoot for me and Carol so that was my way to exit the pool so I could go get ready. The photo shoot was great, the sunset was stunning and this was the perfect last night at the resort!


We had dinner with Carol and David at Harrysan. Unfortunately, Fox and I were extremely exhausted and I don’t feel that we were great dinner guests. We ended the evening early and packed up for our early departure in the morning. While we were laying in bed, Fox and I reflected on the entire trip and negotiated with each other when we would be back again. Good night! THE END

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