The Cruise

My life was turned upside down last year. But now when I look back it was the best thing that could've happened to me in a selfish way because I was happier than I'd ever been now. Since I'd been a teen I'd always been into crossdressing and women's lingerie. That interest grew over time until I eventually had everything; wigs, make up, clothes, shoes, and everything else you'd need. Then I met my girlfriend, or should I say ex-girlfriend. We were together for nearly 8 years and had moved into an apartment together. For most of our relationship, I managed to supress my inner desire to dress, but eventually that became too much, and I started sneaking around and dressing when she wasn't in.

The problem with sneaking around is that you're always likely to get caught one day. And unfortunately for me, I did. One day when I thought she was at work and I had a day off, I waited until the afternoon before I started to change and get dressed. This normally meant I would usually have 3 or 4 hours before she would be home. On this one day though, she returned home a few hours early due to a power outage at her office. I had nowhere to go. I didn't hear her come in and didn't hear her walk into our bedroom until she started shouting and screaming at me.

I was lying on the bed in full crossdresser mode with my finger up my ass and the other around my cock whilst I had porn on my laptop. Let me tell you, I don't think there are many worse positions to be caught in. And that day was the end of our relationship, she threw me out of the apartment, and I had to move back home but that wasn't before she explained exactly why she was breaking up with me to everybody including my family. My Mom and Dad took some time to come around to what happened and when I moved back home, I wasn't allowed to dress, and I respected that. We had the difficult conversation when they asked me if I was gay or not, and the honest answer was 'I don't know.' I'd always found women attractive and wanted to have sex with them but there was always something in the back of mind that said I should try being with a man.

Six months later, I'd saved up enough money for an apartment of my own. This meant I could create my own space and I turned the spare bedroom which wasn't very big, into the wardrobe for my alter ego, Jessie. I was able to rebuild Jessies wardrobe and every month I got paid I would buy myself something. And once again I had everything I needed, including the breast forms which looked very realistic and cost me a hell of a lot. I hadn't slept with another woman since my ex which was now over a couple of years ago and I wasn't bothered. My curiosity got the better of me though and I tried sleeping with a man, and I chose a man who was older than me and experienced. He took my anal virginity, and it was on that night I realised two thing; one was that I was bisexual, and the other was that when I was with a man, my place was on my back with a cock inside me. I wasn't an overly tall guy, I was around 5"7 and quite slim with not a lot of muscle, I didn't work out. I wasn't blessed in the cock department either, when I was flaccid, I was normally 2 or 3 inches, and then when I was fully erect, I was no more than 5 or 6 inches.

And after I'd accepted what my sexuality really was, I found new friendship circles which were good for my mental health and helped me really work on the feminine side of my life which brought Jessie to life. And then over time, I started to spend more time as Jessie when I was out of work, and I started taking it a lot more seriously. I was now wearing panties more than I was wearing boxer briefs. I'd even started becoming bolder and wearing panties underneath my work outfits and whenever I went to the shops. I still wasn't brave enough to go out in my local area dressed as Jessie, but I'd made friends in the LGBT community and whenever we went away for a weekend of drinks, Jessie would always make an appearance. Once a month I was booked in with my local beautician who knew all about Jessie and she would do all my hair removal including the more intimate parts. Whenever I had an appointment, I always wore panties, and she never made a comment and seemed interested in my lifestyle.

I started sleeping with more men as well, enjoying the feeling of a cock thrusting in and out of my smooth ass. Some of them were even lucky enough to cum inside me if I let them. And I was enjoying this new side of me. Multiple times I'd let a man out of the front door of my apartment whilst the neighbours were either coming home or just going out and I just smiled and greeted them politely. They knew what I was up to but when the guys went home, I was back to being regular boring Jamie, so they just assumed they lived near a gay man who loved having sex with strangers.

After my last birthday I was now just one more year away from being the big 3-0. And it didn't feel like I'd done much, and I wanted to celebrate my last year by doing something special. At the beginning of the year, I booked myself onto a one-week cruise around the Canary Islands. I'd always wanted to go on a cruise but always felt like I needed somebody to go with. But after being in the LGBT forums for a while, I came across a cruise that was aimed at LGBT people who were single or in a couple and were just looking for some fun, and by fun, I mean sex. But anybody could go on the cruise, you just had to be aware you were going to be around all sorts of different activities. Once I'd seen it, I couldn't wait to get booked on. I had a bit of extra money from a COVID bonus the company I work for had given employees for reaching targets and keeping the company earning profits. Using this money, I booked myself a bigger room than just the standard cabin, it was classed as a suite, but I'd have a living space, bed, en-suite, and a large wardrobe. The ship would be departing from Tenerife so all I had to do was catch my flight there and make my way to the ship. And I suppose now I suppose I can tell you about my first cruise experience.

DAY 1 -- BOARDING AT TENERIFE

The only flight I could get was from Manchester airport, so I decided to drive down from Leeds and leave my car parked at the airport. With me I had two suitcases, a smaller one with my male clothes in for flying and getting on the ship and then an extremely large suitcase with all my clothes and other bits and pieces in for Jessie. I had to pay extra for the smaller suitcase, but I didn't mind. The flight passed quickly and before long we were landing in Tenerife and with it being early May, the temperatures were warm. Upon arrival at the airport, anybody who was attending the cruise were ushered onto a coach and driven to the dock where we would be able to board the ship.

As the coach pulled into the dock, the ship was bigger than could have ever imagined. We walked up the ramp and into the check in area where there were already some queues of people. And I could see that the people who were being checked in were all being handed wristbands. When I reached the desk, it was all explained to me, you could be given up to three wristbands. Firstly, they asked whether you were attending in a couple, single male, single female, or CD/TV. When I told them I was a crossdresser I was handed a pink wristband. If I chose the second wristband it's because I was signifying that I was interested in men and if so, what my preferred position was (top, bottom or versatile). I took the orange band which said I was a bottom, and I was really looking for anyone wearing a blue band which was the people who were only looking to top. The last band was to prove if I'd had a full sexual health check before I'd arrived which I had. So, I handed over the paperwork and I was given a yellow wristband which would tell other people that sex without condoms was a possibility if we both had the yellow wristband.

After all the formalities were completed, I was given a map of the ship, an itinerary and then a bell boy guided me too my suite and they even took care of the suitcases for me. My room was more than suitable for my needs, it was large enough and I wasted no time whatsoever in unpacking Jessie's things and getting them hung up. I stripped out of my jeans and boxers (I'd only worn them to avoid any embarrassing moments with airport security) and I slipped into a pair of shorts and panties and headed back out to explore the ship. The place I was looking for was the nail salon. Once I'd found it, I paid to have both my fingers and toes painted a lovely shade of red and they'd hopefully last me the duration of the cruise.

After that, I returned to my cabin and transformed myself into Jessie ahead of the introductory dinner that would be taking place in the ships main restaurant. The full transformation usually took me an hour. By the time I was done, I had a shoulder length blonde wig on, and I'd curled the hair. I was wearing a full-length red ball gown which had a thigh high split on one side and wasn't completely skin-tight so you couldn't see the slight bulge underneath although that wasn't massive. Underneath the gown I had a matching black lace lingerie set on, the panties were just briefs and the bra covered my realistic fake tits. I finished the outfit with a pair of small black heels.

I headed down to the dinner party which was being hosted by the captain of the ship. I was seated on a table with a mixture of different people. I was sat with an older male and female couple, a couple of individual older guys, another transgender person, and a gay male couple where one of them was a lot older than the other. There was no shortage of male and female couples on the ship and I was interested in getting to know them to find out why they were here and what they were looking for. A long-time fantasy of mine involved pegging and a married couple so who knows, that could happen on this trip. I couldn't see many wristbands around the table as they were covered up by their suits but mine were on show for everyone to see.

The captain delivered his speech and we had eaten our meal and were now onto drinks. They'd cleared an area for a dance floor and many couples were already hitting it off the dance floor and I'd seen multiple people leaving the room holding hands and I was already wondering whether they were together or not and what it was they were going to do. I was still seated at my table, still not confident on my feet in heels when an older gentlemen came and sat next to me.

'I've brought champagne for the lady,' he said as he placed the glass in front of me. He was handsome in his bow tie and suit. He was bald but had a strong grey beard which I liked. I would've said he was in his early 50s and from the accent was clearly English. 'I hope that's okay, may I take a seat?'

'Of course.' I took a sip of the drink. 'The champagne is very much appreciated.'

We spent the next 30 minutes or so getting to know each other, and he asked me questions about my life. It was lovely to talk to somebody who seemed so genuinely interested in my journey in life and he was so supportive of the choices I'd made. He told me about himself, how he'd always known he was gay but as he got older, he'd started to appreciate the ladies who had a little extra. I'd only known this man less than an hour, but he already made me feel special. After a while, our chairs had moved so close that I was sat on his lap. He had his arm around the back of my chair and his other one he gently moved onto my thigh. He then leaned over and kissed me. And I couldn't help myself but kiss him back.

'We could get out of here if you like?' He asked cheekily before flashing his yellow wristband.

I rested my hand on his thigh and slowly worked it towards his groin. 'I'm really tired after all the travelling today.' I could see the look of disappointment across his face. 'But if you'd like to show me your cabin, maybe there's something else I could do for you.'

He stood and helped me to my feet and then we walked hand in hand out of the room to the elevator. When we reached the elevator, he let go of my hand and moved it around my back and to my ass. He gave it a little squeeze as the doors opened and we entered. We quickly closed the doors so no-one else could join us and we kissed all the way to the floor he was on. He then led me by the hand again to his room, used his key card to open the door and once it was closed behind me, he threw me against the wall and started kissing me.

His tongue explored my mouth, and I did the same to him. He put his arms above my head against the wall and I started rubbing my hand against his crotch. I could already feel his hard cock, it didn't feel massive, but it was more than good enough for my first night on the cruise. I then started undressing him. I started with the jacket, he moved his hands so I could remove it and drop it on the floor. We continued kissing as I started fumbling with the buttons on his shirt, he helped me by removing the bow tie. Once I had his shirt undone, I untucked it from his trousers and then started undoing his belt before unbuttoning his trousers and pulling down the zip.

I then reached my hand into his trousers and pulled his cock from his briefs and gently started stroking him. I broke off the kiss and started kissing his neck, before I gently nibbled on his ear and then whispered to him, 'wouldn't you rather be comfy on the bed for this?'

He then moved towards the bed, stepping out of his clothes as he walked and then he was in front of me completely naked with his hard cock standing straight out in front of him. He also had a hairy chest which really added to his manliness. I followed him over to the bed, and stopped him before he laid down. 'Could you help me out of my dress?' I asked him. 'I don't want to get saliva and cum all over it.' I held my hair up above the neckline where the zip was and felt him the lower the zip which went halfway down my back. He then helped me slip my arms out of the dress before I seductively bent over in front of him as I pulled it over my ass and picked it up off the floor.

I folded my dress over the chair in front of the vanity table and returned to the bed. He was already laid down, stroking his cock and his eyes never left me as I approached the bed. I purposely climbed over him to get to the other side and as I did, he spanked my ass causing me to yelp. I then took his cock in my hand and licked him from the bottom of his shaft all the way to the top of the head and then swirled my tongue all around. He was already moaning, which was a good sign. I genuinely was exhausted, but I needed my fix of cock before bed.

Next, I took the head of his cock into my mouth and swallowed the whole of his cock with ease. He had his hand on the back of my head, pushing me down every time I came up from deep throating his cock. I was finally able to let his cock fall from my mouth, a long string of saliva still connecting my mouth to his cock. I then jerked off his extremely wet cock whilst I licked and sucked on his balls. The way he was moaning, he sounded like he was in heaven. My own cock was rock hard in my panties and was straining to get free.

'Oh fuck,' he moaned. 'I've never been so close to cumming this quick before.' He moaned again. 'Fuck, you're too good at this.'

I continued to work his balls and shaft at the same time. I was rubbing my thumb over the head of his cock which had him squirming. 'Let me know when you're close Daddy,' I told him.

'I'm already fucking close,' he replied. 'If you put it back in your mouth, you're about to get a taste of Daddy's seed.'

I followed his instruction and took his cock back in my mouth. I used my tongue to circle the head of his cock whilst my hand jerked him off. I could feel him fidgeting beneath me and could sense that he was getting closer with every pump of his cock. He was trying to hold back, he kept trying to move my hand out the way and then tried to stop me sucking him, but he couldn't stop the inevitable.

'I'm gonna cum,' he warned me. 'Fuck, it's cumming, it's cumming.'

I held my mouth in position over his cock as I felt him pump his cum inside me. I swallowed everything I could but some of it leaked out the side of my mouth. I quickly scooped that up when I'd let his cock go. He laid, breathing heavily as I scooted off to the bathroom to clean myself up. I reached inside my own panties and felt how wet they were. Fuck it felt good to leak pre cum like that. When I got back into the room, he was on the end of the bed waiting for me.

'Is there anything I could do for you?' He asked me. I took a hold of his hand and brushed it against the front of my wet panties.

'You already did what you needed to,' I told him.

'That's so fucking hot.' He smiled at me.

I couldn't be bothered getting my dress back on, so he kindly offered me one of his robes from the bathroom which I accepted before heading for the door. He kissed me as he opened it and I went to walk off before he stopped me.

'Should we not at least exchange names?' He laughed.

'Jessie,' I held out my hand for him to shake.

'Geoff,' he replied, shaking my hand before bringing me in for one last kiss.

I then headed back to my room carrying my dress and heels in one hand, wearing just a robe with lingerie underneath. I passed a few people en route back to my suite, but no one seemed to care or give me funny looks. I imagine they were doing their own walk of shame. All in all, I would say day one was successful, and I was looking forward to the rest of the trip.

DAY 2 -- EXPLORING TENERIFE

I awoke the next day feeling refreshed and ready for another fun filled day. The ship was yet to depart Tenerife so we would have the opportunity to explore the area of Puerto de la Cruz. The plan was for the ship to depart in the evening, so we were all expected to be back on board by 5pm. I stepped out onto the balcony of my room and welt the warm breeze brush across my face. It was already getting warm so I decided it would be too much hassle to be out and about dressed as Jessie all day and I'd pass out from the heat.

I jumped in the shower, freshened myself up, and cleaned myself out in case I encountered any sexy time later. My outfit of choice was a simple t-shirt and denim shorts, but underneath the denim shorts I slipped into a tie side thong bikini bottom that contained my cock but really showed off my ass. I packed together a little backpack with a beach towel at the bottom and some essentials and made my way off the boat. On my way out, I was given a little pass card with my identifier on so I could get back on board before we left.

On my travels I found a nice little café to enjoy a light breakfast before wandering around the shops. I couldn't resist buying some jewellery that would really suit Jessie as well as some more swimsuits for around the pool on the ship. I continued my wandering, making my way down all the windy streets and eventually found myself on the main strip where all the bars were. Obviously, many of them were closed but they offered a good time if I ever decided to come back. A lot of them seemed LGBT friendly as well which was a nice thing as it wasn't always common in some holiday destinations.

A lot of people were very friendly when I walked past them as well, receiving a lot of 'hello's' and 'hola's' as I passed workers setting up outside the bars ready for another day. A lot of people were checking me out as well which was knew to me. I wasn't sure if I was giving off some sort of vibe, but a lot of men seemed interested in me. Maybe it was the way I was walking, but I really wasn't sure. As I continued to walk, I remembered I was wearing the wristbands from the cruise ship, maybe the locals were used to seeing people wearing these and they knew what they meant?