The Cruise

I worked my way back through the town and to the beach front. The sand looked like something out of a film in the Caribbean, golden and not an ounce of rubbish in site. I found another little café along the front and stopped for a lite bite to eat. While I was having my lunch, I was researching the beaches around the area and I found that if I walked along a little further and then over some rocks, I would find a gay beach where clothing was optional. So, once I paid my bill, off I went. Shoes in my hand as I walked along the beach feeling the sand between my toes. As I meandered along the beach, eventually a set of rocks came into site. When I reached them, there was a sign warning people that they were about to enter a nudist beach and no under 18s were allowed. I walked around the walks and the little cove opened in front of me. It was a private beach with sets of rocks all along and no views from the street.

There was a few people already on the beach, cocks swinging about in the water, some were casually chatting to each other, and some were sunbathing. I found myself a nice empty area and started laying down my things. I grabbed my towel from my bag and laid it out and then started taking my clothes off, starting with my shirt first, quickly followed by my shorts. Before I laid down and put some sun cream on, I wanted to feel the water on my body. I left my things and made my way down towards the waves, my booty swaying from side to side. It felt like all eyes were on me. I spent around 10 minutes in the water having a little paddle and cooling down before walking back to my towel.

I grabbed my sun cream from my bag and started rubbing it all over my body and legs after I dried myself off from being in the sea. It was then I noticed someone walking back over to their towel which was the next one along from mine. He was what I can only describe as a bronzed God. Beautifully tanned, a body sculpted from stone and a decent sized cock hanging between his legs. It was around 5 or 6 inches, and he was completely flaccid. He caught me staring at him and flashed me a smile as he laid down. I turned over onto my belly, pushing out my ass so he could get a good look. I was hoping that would entice him over... and it did.

'Necesitas ayuda con tu crema?' He said in a Spanish accent, and I had no idea what he was saying.

'lo siento no hablo español,' I replied to him. It was the only thing I'd learned from my Spanish language book on the plane journey here.

'Ah, you're English?' He said with another smile on his face. 'I was asking if you needed any help with your cream?'

'If you could,' I smiled at him. 'I would really appreciate it.'

He grabbed the cream from next to my towel and squirted some on my back and then began to massage it into my skin. His hands felt huge as he worked them all over my back, it was so good I let out an involuntary moan which made him laugh. He then had his hands over my ass and was kneading them like he was about to make some bread. I could feel his cock resting against the side of my leg.

'Do you mind if I join you?' He asked when he'd finished applying cream to my body. I agreed, obviously and he pulled his towel up next to mine and laid next to me.

We chatted for a while, and he spoke very good English. His name was Fernando and he worked in one of the bars on the strip. He said he'd picked up most of his English from talking to tourists in the bars during the summer. The bands on my wrist were noticed and he told me it was a common thing for them to be spotted about and about when the cruise ship was docked and waiting to depart. I flipped over onto my back again and 'accidentally' made contact with his cock which was resting against his leg.

'Gosh, it's so warm out today.' I wiped the sweat away from my forehead. 'Is there any shade around here to cool off?'

'I have a beachfront apartment we can go to if you like.' He checked his phone. 'How long have you got?'

I checked my own phone, and it was almost 1pm. 'I have a few hours to waste before getting back onboard.'

He started gathering his things together and I did the same. I put my t-shirt back on and grabbed my shorts, but he put his hand on my wrist. 'I think you should leave the shorts off,' he told me. 'You look sexy.'

It was a big step, but he had me feeling confident, so I did it. I shoved my shorts into my bag pack, threw it over my shoulders and put my sunglasses on. He slipped back into his swimming trunks, had his towel over his shoulder and off we went. He was much taller than I was and must've been well over 6ft. When we reached the end of the beach and were back onto the promenade, there were a lot more people around. But none of them seemed to stare at me, and the ones that did were undressing me with their eyes. The shirt I had on just to say reached my waist, so it was obvious what I was wearing on my bottom half, and I couldn't help but imagine that my booty was jiggling when I walked, putting on a show for those behind me. When we finally reached his apartment, he led me up the stairs to the third floor where his apartment was. He had his own private balcony overlooking the sea front with a parasol we could use to keep the suns off our body. The balcony wasn't overlooked from either side either so there was no chance of being watched by any nosey neighbours. He left me on the balcony and brought me out some nice cold drinks as we sat and continued chatting. I took my shirt off again as I was getting warm and asked him where his bathroom was so I could freshen up a little bit.

When I came back, he was sat on his chair and had removed his trunks again. I hadn't noticed before, but it seemed like he had a cock ring on. So, he'd either sneakily put it on when we got back, or I was seriously distracted on the beach. 'You know why we came here don't you?' He asked me. And I nodded to say I did. 'So, when are you going to get to it?' He was now lightly stroking his cock as he looked at me.

He pulled his chair away from the table and I put his towel on the floor so my knees wouldn't be uncomfortable. Then I dropped to my knees in front of him, his hard cock right in front of my face. I licked the head of his cock before taking it into my mouth hands free. I could feel him getting harder as I bobbed up and down. It just felt like it kept growing and growing and by the time it was fully hard, it must've been at least 8 inches and thick.

I continued to suck his cock and used my hands to jerk his shaft as there was no way I could fit the whole thing in my mouth, it was far too thick. He moaned quietly and moved his hand to the back of my head. He ran his fingers through my hair and kept telling me what a good job I was doing. I fondled his balls whilst I was working his cock. And then, he put his legs up, so they were on the table, presenting his ass to me. I took that as a hint and started licking his hole whilst jerking him off. He was really enjoying that as I licked around the entrance to his hole and in between his balls and ass.

Every time he moved; his ass kept sticking to his plastic chair, which was funny, but it can't have been comfortable. 'Should we take this inside where it's more comfortable?' I asked him. He agreed and he led me to his bedroom which was nice and air conditioned. The cold air had my nipples hard within seconds.

'Can I fuck you?' I was wondering how long it was going to take him to ask me that.

'Only if you fuck me hard enough that I'm screaming your name and cumming by the end of it.' I smiled and grabbed a hold of the ties on the side of my bikini bottom. I pulled them in one go and they fell off, leaving my cock standing there erect, looking even smaller compared to his monster. I walked over to his bed and climbed on, and positioned myself on all fours waiting.

He laughed, 'in that case, I better put on some music. I don't want to disturb the neighbours.' He flicked through his phone and then music started from the speaker he had beside his bed. I then felt Fernando behind me as he started to play with my ass. He squeezed my cheeks and gave them a little spanking.

'Fucking spank me Fernando?' I said looking back towards him.

He spanked me again, only this time a lot harder and I'm almost certain there would be a handprint on my ass. I then felt his fingers probing around my ass crack and then gently pressing when he reached my ass. The tip of his finger entered my ass and even that felt good. But his finger was soon removed and then I felt the cold sensation of lube dripping down my ass. And then his finger entered me again only this time it was with ease. He worked his finger in and out of my hole as I moaned. It was obvious he knew what he was doing as he soon had his finger pushing against my prostate.

'Oh, fuck yes,' I moaned. 'That feels so fucking good.'

The finger fucking continued for a few minutes, and he had me moaning all the way through. I reached between my legs and grabbed my cock. I stroked it gently as pre cum leaked from the tip and onto the bed beneath me. I needed his cock now; he was warming me up perfectly but now I was ready for the main event.

'Fernando.' I turned to face him; he stopped the movement of his fingers. 'Grab a condom and get that dick inside me now.'

And he did exactly that. He moved to the bedside cabinet and grabbed a condom from the drawer. It took him a few moments to get himself sorted but I soon felt him again. This time the pressure was far more intense as he tried to push his cock inside me. He was gentle as I felt the head of his cock push past my sphincter and into my ass. That was painful at first, but he held himself there to give me time to adjust. And then he started to slide himself inside me inch by inch until his balls were touching my ass.

'Oh, my fucking god.' I nearly screamed. 'You're so fucking big.'

He slowly started to withdraw himself before punching deep inside me once more. I was an experienced cock taker, but the thickness of his cock was something else. But the discomfort and slight pain that I had soon disappeared when he got himself into a rhythm. He had a hold of my hips and started to get faster and faster, soon you could hear our bodies slapping together over the top of the music.

'Oh baby, your ass is so fucking tight.' I loved the sound of his accent, it really made me weak at the knees.

I had my arms stretched out in front of me, gripping onto the other side of the bed to try and stop myself from being thrust over the other side. 'Fuck... can I... fuck... ride you please?'

He gave my ass another stinging slap and pulled out before laying down on the bed next to me. I struggled to my knees as they were already turning to jelly, but somehow, I managed to mount him with my feet planted either side of his hips. I held his dick straight and lowered myself down gently. Once his cock was back inside me again, I leaned back, resting my hands in between his ankles whilst he held onto my feet. Then I began to rock backwards and forwards, grinding myself into his cock. After doing that for a little while, I then started to bounce up and down slowly. Watching his face, and then watching his cock slowly disappear into my ass. My own cock was flopping around as I fucked him, leaving trails of pre cum from wherever my cock made contact with my body. Fernando then started meeting my thrusts. I then just held myself in position as he rifled his cock in and out of my ass, making me scream. My whole body started to feel warm, and I felt like I could cum at any minute.

'I'm starting to get close,' Fernando then pushed me off his cock, 'Lie down on your back,' I liked this dominant side to him. He moved to the side of the bed and then pulled me to the edge by my legs so that my ass was hanging off the end.

He lined up his cock with my ass and was soon fucking me again. I held my legs wide for him and he started to play with my cock and balls. He twirled his fingers around the head of my cock, and soon my cock was reacting to the touch and starting to get hard. As he was fucking me, Fernando then started to play with my hard cock, slowly jerking me off. With the combination of his hand on my cock and his dick in my ass, I could feel my orgasm coming.

'Oh, fuck me Fernando, keep fucking me.' I moaned at him. 'Yes. You're going to make me cum Fernando, fuck, I'm going to cum with your dick in my ass.' He let go of my dick, but I was already past the point of no return. Cum shot out of my cock as it writhed about, jerking all over the place. Cum was now all over me, the bed and some even managed to land on Fernando. He continued to fuck me whilst I was still reeling from my orgasm, but I could sense he too was getting close.

'I want to cum on your face baby, is that okay?' He asked me, slightly breathless from all the fucking. I looked up at him in between my legs as he fucked me and gave him my best 'yes please' face. The intensity of the fucking then increased as he pushed himself towards his own orgasm.

In an instant, he pulled his cock out of my ass and ripped the condom off. I scrambled to get off the bed and down onto my knees like all good sluts. Sitting underneath this monster of a man who was now furiously jerking his cock as I had my mouth open awaiting my prize. He then let out an alpha male scream and started to paint my face in his cum. It seemed like it was never going to stop, by the time he was finished, I swallowed a couple of mouthfuls and still had some all around my face but fuck I enjoyed it.

Fernando then allowed me to shower so I could clean up before walking back to the ship. Once out the shower I walked back into the bedroom where he was still laid on the bed.

'Have you seen my bag?' I asked him.

'It's still on the balcony.' He told me.

I wandered onto the balcony and back into the heat. I dropped the towel seen as though no-one could see and let the heat hit my naked body. I reached around to feel my well fucked hole before finding my bag and retrieving the panties I'd brought with me. I slipped into the cheeky panties and stood for a little while. Fernando eventually joined me, carrying my clothes.

'You're so fucking sexy,' he told me as he handed me my things. I got dressed and kissed him goodbye as I made my way back to the ship.

I made it back onboard with around 30 minutes to spare. It was a little bit too close for comfort, but I wouldn't have missed Fernando's cock for the world. It would have been worth missing the ship just so he could fuck me for another week. When I was back on the ship, I went straight for some food before retiring to my suite for the night. I didn't have the energy to socialise but tomorrow would be spent on the ship so it would give me plenty of time to get to know people.

DAY 3 -- DAY AT SEA

Another good night's sleep was what was needed after the day before. And that's what I got, waking around 10.30am. I dragged myself out of bed and pulled the curtains back and was greeted by views of the sea. The ship set sail during the night and we now heading for a little Portuguese island called Madeira. For me though, today was a Jessie day. I hadn't had enough chance to spend time as Jessie, so I wasn't going to miss out today. We weren't due to arrive in Madeira until late into the night, so I had no distractions, and just plenty of time to explore.

I started my day no different to any other. I jumped in the shower, removed any unsightly body hair that might have appeared and made sure I was nice and clean, ready for the day. I spent the next 30 minutes to an hour getting my make-up right before putting my blonde wig on and tying it up into a high ponytail. My outfit of choice for breakfast was an orange VS thong with matching bra, a white top and a black mini skirt that just stopped below the thigh. A simple pair of flip flops were my comfy choice of footwear. Once I was ready, I left my room and headed down to the breakfast room. And on my way down, for the first time since getting on the ship I could hear other people having sex. It was a relief to know I wasn't the only one overindulging in cock on this holiday.

At breakfast, I grabbed my usual bowl of cereal and headed to a table where I'd normally sit on my own and enjoy a quiet breakfast. Only coming down this late in the morning was that people were already starting to filter through for their lunch, so the place was packed out and there wasn't many seats left. Shortly after I'd sat down, a married couple approached where I was sat. There wasn't a lot of male/female couples on this cruise but there was still more than I expected.

'Do you mind if we sit here?' The lady asked.

'Of course, please do.' I told them.

They sat down opposite me and at first, we ate in complete silence whilst I flicked through my phone before going back for a second plate of food to get me by until I needed something to eat this evening. When I got back to the table, I could hear them whispering something to each other, so I just flashed a smile at them when I took my seat.

'I'm so sorry if this is rude,' the lady spoke up. 'But are you trans?'

I laughed. 'I'm a crossdresser.'

'No way, I'd have never been able to tell really. There's a couple of obvious signs that you can't do much about, but the way you present yourself is perfectly feminine.' The lady was very complimentary.

'Good looking too.' Her husband muttered. It was then for the first time that I noticed what wristbands he had on. I noticed he was wearing the magical combination of blue and yellow. Then I remembered I hadn't put mine back on when I got out the shower this morning. The couple both had strong Scottish accents which I didn't mind.

'I'm Nicola,' she offered her hand across the table.

'Jessie,' I replied accepting her handshake.

'This is Jonny,' she pointed towards her husband.

I offered my hand to Jonny, and he took it and kissed me on the top of my hand. They were both friendly which was lovely. Nicola was a MILF. She had big tits, lovely long brown hair, and a figure I'd kill for. Jonny was wearing a vest now which showed off his big arms that were covered in tattoos. He was bald, but had a beard to compensate for the lack of hair on his head. It was clear that they both enjoyed working out. They continued chatting to me for a while even after we'd both finished eating. I couldn't work out if they were genuinely interested in me or whether they were just being nice.

'Me and Jonny have a tennis game later with one of the staff, we'd love it if you'd join us? That's if you play tennis?' Nicola asked.

'It's been a long time since I've held a racquet but I'm more than ready to play with some new balls.' Jonny's ears seemed to perk up after that statement.

'Perfect,' we all stood up and started walking towards the exit 'We'll see you in there in about 30 minutes. Bring your swimsuit as well because we're going to the top deck when we're done.'

We went our separate ways and I quickly headed to the sports shop seen as though I hadn't brought anything sporty with me. I settled on a white tennis skirt with the built-in shorts, a pink sports bra, and a white cap. I went back to my suite and quickly got changed. I slipped into my most sporty looking underwear which was a regular thong that was comfortable enough to move around in. Only problem was that the thong was pink, and it showed clearly through the shorts underneath the skirt. I remembered to put my wristbands back on, packed my swimming stuff into a bag with some spare panties and headed on up to the sports deck. It was still on the top deck but was at the other end of the ship.

When I got to the court, Nicola and Jonny were already warming up with the member of staff that was there. He was introduced to me as Juan. He was a lot older than Nicola and Jonny who had told me they were 41 and 48, respectively. But Juan gave off strong coach vibes and I don't think he was here to fuck about. I was put on Jonny's team and the game began. An hour later, we'd lost heavily but I didn't care because we'd had fun. I teased Jonny all the way through the game, bending over in front of him whenever I got chance and with the sea breeze, my skirt was often blown up giving a perfect view of my thong underneath.