The Cruise

'That feels so good, fuck,' I started to squirm. 'Fuck, I'm gonna cum, fuck yes... yes... fuck... I'm cumming, you're making me cum.'

My cock started to erupt as cum splattered out all over me. She continued wanking me as I covered myself in cum, parts of the bed and even a little bit hit Jonny. I screamed all the way through the orgasm and was out of breath by the end of it. 'Fuck, you look so cute when you cum,' Nicola told me. 'Are you ready for Jonny's load?' She asked me as I nodded weakly to say I was.

Jonny moved off to the side of the bed nearest to him and grabbed me by the legs and pulled me towards him. He had me turn over again so he could fuck me doggy style. I got up onto my hands and knees like a good girl and waited for him to start fucking me again.

'Fuck she's tight,' he said as his cock entered me.

He started to pound my hole as I gripped onto the bed sheets in front of me. He was almost putting me through the bed with his power. I couldn't help but moan and look down towards my cock as cum continued to dribble out of me with every thrust. I couldn't hold my weight and I eventually collapsed face down onto the bed. But that didn't stop Jonny who continued to fuck me, he was just mounting me instead.

'Argh, fuck, I'm gonna cum.' Jonny started to really push himself deep inside of me before pulling out slightly and then slamming his way back in. 'I'm gonna cum, fuck, take it, take my fucking load,' he moaned.

He then let out a big grunt and I felt something warm inside me as he continued to fuck me as he pumped me full of his cum. Fuck it felt good. Once he'd finished, he moved off to the bathroom as I laid there recovering after an epic session. It was about ten minutes before I had any energy to move. I could feel Jonny's cum leaking out my ass, so I decided to get into the bathroom and get changed. I took my stuff with me and cleaned all my make-up off but left the wig on and removed my fake tits. I put on my VS slip and headed to the bed. Jonny was already under the duvet and Nicola was just putting her pyjama shorts on before we were all in bed. I was in between the two of them as we drifted off to sleep.

DAY 4 -- MADEIRA, PORTUGAL

I woke up the next morning to the sunlight beaming into the room because we'd forgotten to close the curtains and doors. You could hear the waves crashing against the ship which was relaxing but also the hustle and bustle of people as we'd docked at some point during the night. As I begun to stir, I'd turned onto my side in the night, so I was facing Nicola who was flat out on her back and Jonny who'd moved into spoon me with his arm across my chest.

I could feel his hard cock resting against my bare ass seen as though my slip had ridden up during the night. I started to move my ass back and forth gently until Jonny began to stir. He moved his arm that was across my chest and started to grab at my ass cheeks.

'I need to fuck that ass again,' he whispered into my ear.

'You can, just be gentle,' I told him. 'Some Daddy with a big cock fucked me hard last night so I'm a little sore.'

He moved his arm off me and reached to the bedside table where he'd left the lube. I heard him using the pump before he gently rubbed some on my ass and then he slowly slid his cock into my ass. He fucked me slowly and with care, this time it felt more like we were making love. He cuddled me into him with our heads next to each other as he started to kiss my neck. It was near impossible not to moan and disturb Nicola, but she still hadn't moved since we started fucking.

'Do you think she'd like it if I woke her up by playing with her pussy?' I asked him quietly.

'She'd fucking love it,' he told me.

I freed one of my arms and reached over to her. I slid my hand down her belly and into the top of her shorts before finding her pussy. I gently started to rub her pussy whilst Jonny fucked me. I could hear her softly moan as I played with her. She started to stir but wasn't completely awake, so I moved my hand down the lips of her pussy and started to feel her wetness, so I inserted a finger and started to fuck her.

She moaned again, but this time opened her eyes. 'Morning,' I smiled as she looked at me. But that smile soon turned to a giant O as Jonny fucked me a little quicker.

'Is he fucking you again?' She moved the hair from my wig away from my face. And I nodded to confirm her suspicions.

She turned to face me, but I kept my hand inside her shorts and still played with her pussy. She reached under my slip and started to play with my cock which reacted to her touch. I was hard as he slowly jerked my cock as Jonny fucked me slowly. She looked over the top of me so she could talk to Jonny.

'Should I let her fuck me babe?' She asked him.

'Only if I can fuck her at the same time.' He told her.

'We can make it work,' was her quick response as she started to shuffle around in bed.

She moved my hand out of her shorts and quickly removed them before turning over onto side and sliding in front of me. She reached behind and grabbed a hold of my cock and held it at the entrance to her pussy. I pushed forward as I felt the wetness and warmth of her pussy around my cock. It had been the first time in years that I'd felt a woman's pussy around my cock. I started to fuck her pussy which caused me to bounce back on Jonny's cock and before long we were all moaning.

The sensation of being fucked and fucking was too much for me and I embarrassingly came quickly inside Nicola. And then I held myself inside her whilst Jonny started to fuck me a little faster. He held my hips and fucked me until he dumped his second load inside me. Nicola then led me to the bathroom, and we showered together. Feeling bad for how quickly I came earlier, I went down on her and started to lick her pussy. I could taste myself as I licked her, but I made her cum twice before we exited the shower. I got dressed and said my goodbyes before heading back to my own room. On the way back to my room I noticed a sign advertising a party taking place tomorrow evening. It was a fetish party and the theme this time was lingerie, so that was something I'd be attending.

When I got back to my room, I showered and cleaned before dressing in my usual Jamie attire and headed off to explore Madeira. I spent a good few hours walking around the landmarks, shops, and beaches. I only stopped off for some lunch and then later dinner before arriving back at the ship about 7pm. I jumped straight into bed and treat myself to an early night after the exhausting two days I'd had.

DAY 5 -- DAY AT SEA

I awoke the next morning feeling completely refreshed. I'd slept for well over twelve hours, but I was feeling ready to go again. I drew back the curtains and completely forgot that we'd departed Portugal during the night and were now en route to our last stop before heading back to Tenerife. I was still feeling slightly sore after the last couple of days, so I took the morning and afternoon for some personal care. I spent the morning showering and looking after my poor ass that had taken some fucking over the last couple of days. But I'm sure I could manage a couple more days before heading back home to chill out and become celibate for the future to give my ass a rest.

The afternoon I booked myself into the spa for the full treatment. It wasn't cheap but it was exactly what I needed. I spent hours there getting massages, facials (not my favourite kind, but a close second), nails and hair done. They were even amazing when I asked them to work on my wig ready for the party this evening. After all the money I'd spent on treatments one of the ladies even offered me a free waxing when she noticed a bit of hair was starting to appear. By the end of the treatments, I felt like a new person. I was completely refreshed and ready for the party tonight and to see what adventures awaited me.

On my way back to my room, I headed to the information desk to find out more about the party which sounded amazing. The dress code was sexy underwear/lingerie for everyone. Anyone wearing anything else would be refused entry. I took some time when I got back to my room to get cleaned up. My ass was no longer sore which was a good thing. The day seemed to have disappeared before my eyes and I was quickly running out of time to get ready for this evening. I quickly put my make-up on, I was getting a lot better and quicker when it came to dressing as Jessie. I carefully placed my wig on after the hard work from the ladies in the salon.

Next up it was time to pick my outfit and luckily, I had brought just the thing. Out of my case I pulled out a pink lace bodysuit. To stop myself from popping out underneath it, I'd also brought a pink G-string that would hold my cock and balls in place underneath the bodysuit. I didn't bother with the tits as they looked weird without a bra. I teamed the bodysuit with a pair of black fishnet stockings and a full-length mesh robe which had a fluffy trim and sleeves. I looked in the mirror and even I thought I looked good without blowing my own trumpet. I grabbed a little purse that I could carry my essentials in and headed off downstairs to the party.

Upon entering the room, it was massively difficult not to get hard immediately. All around me were men and women dressed in all forms of lingerie and underwear. There were women walking around in crotchless panties, thongs, bodysuits & corsets. And then there was the men, walking round in mesh boxers, thongs & jockstraps. The waiters who were working the event were wearing nothing but an apron. And some of them were struggling to hide their excitement as guests flipped their aprons up to reveal hard cocks.

I found myself a table and settled down. I'd drank a couple of drinks before I decided to get up and started dancing. I bumped into Nicola and Jonny who were grinding on each other on the dancefloor. She pulled me in for a kiss before going back to her dancing. I found my own people to grind on and that was anybody that moved. Once I'd knackered myself out, I returned to my seat where I was sat with a couple of gay couples, and a new man and woman who I'd not seen before. They soon disappeared when a twink appeared and led them out of the room. He'd be on his back before long taking the seed of the older man who was watching his ass as he walked with his wife.

'I was hoping I'd bump into you this evening.' I heard the familiar voice as Geoff, who was wearing just a mesh pair of briefs that showed off his cock, took a seat next to me around the table.

'Geoff,' I said. 'So lovely to see you again.'

'Jessie, you look incredible.' He said as he leaned across to me and planted a kiss on both of my cheeks.

'Have you been enjoying the cruise?' I asked him. 'I haven't seen you around since the first night.'

'I became a tourist in Tenerife. And then I've spent a day locked away with a twink who just needed fucking constantly. And then I was out and about on the beach yesterday. How about you?'

'Well after I sucked your cock, I was fucked by a hot Spanish guy in Tenerife, and I met a lovely couple who both fucked me last night and this morning.' I looked across and seen them leaving with another crossdresser. 'That's them there, sneaking out.'

'If they're not going to take you back to their room this evening, does that mean you might be looking for someone else?' I could sense the hope in his voice.

'I would be, but I'm super tired. I might just head off to bed.' I couldn't resist teasing him.

'Oh,' I watched his face drop as he thought he might not get to spend the night with me.

'I'm kidding,' I placed my hand on his thigh and leaned over and kissed him. 'Would you like to come back to my room this evening? It's a warm night and my balcony is very private.'

'That sounds perfect,' Geoff stood before me. I grabbed a hold of his cock before standing with him and walking towards the exit. He had his hand on my ass, showing everyone, he was taking me to fuck me. On the way out, there was multiple people mounting each other in public. If we stayed around long enough, this would turn into a full-blown orgy.

On the way back to my room, the noises coming from the rooms around us were more than I'd ever heard before. There were cries of pleasure and moans of satisfaction coming from every room as we walked along the corridor to my room at the very end. I had the nice long balcony at the end of the ship so wasn't overlooked by any neighbours. When we were back in the room, I poured us a couple of drinks and sat on the balcony taking in the views across the ocean and the lights of the other ships in the distance.

Our glasses were soon empty, so I got up and got us another drink, when I came back this time, I handed him his drink and then sat on his lap. He had his free hand around my back and then he placed his drink on the table so he could rub his hand across my legs.

'You look so sexy tonight, Jessie,' he told me as he looked into my eyes. 'I've been thinking about fucking you ever since the first night, I've done nothing but dream about you.'

I leaned in and kissed him again, 'well after tonight you won't have to dream anymore.'

I continued to kiss him as my hands started to roam all over his body before finding the bulge in his briefs. I rubbed his cock through the mesh, and I could feel him stiffen with every movement of my hand. I stopped kissing hm and started to kiss my way down his body. I was quickly off his lap and down onto my knees in front of him. I took my robe off and folded it underneath my knees, so it was a little more comfortable. I hooked my fingers into the sides of his briefs and started to pull them down. Geoff lifted his ass off the seat, so it was easier for me to get them off.

His hard cock bounced free from the briefs. I took it in my hands whilst I slowly jerked him off, staring straight at him whilst I was biting my lip. He wasn't the biggest guy I'd been with, but he was perfect for me after the last couple of fucks I had. I started to lean forward and took his cock into my mouth, swallowing the whole thing with ease. Whilst he was deep in my mouth, I started to use my tongue to work his shaft which had him going crazy. He was moaning loudly but I didn't care. The people above and below might be able to hear but they were probably fucking themselves.

'Oh god,' he continued to moan. 'Your mouth is fucking incredible.'

I started to bob up and down on his dick, paying particular attention to the head of his cock. I used my hands to twist them around his shaft. My aim was to bring him to the edge of orgasm every time before letting him calm down. I wanted him to fuck me, but didn't want him to fuck me for long. I had a good feeling about tomorrow and wanted to give my ass as much chance to recover.

'Fuck you need to slow down otherwise I'm not gonna make it in your ass.' I let his cock fall out of my mouth and smiled at him.

He stood up and moved me over towards the railing on the balcony. Before he could spin me around, I squatted down and took his cock into my mouth again. Putting my hands on his ass, I pulled him towards me, telling him I wanted him to face fuck me. Which he did. By the time I'd finished my saliva was all over his cock as he pulled me up to my feet and turned me around.

'Lube?' He asked.

'In the bathroom by the sink.' Geoff quickly disappeared but was soon back and squirting lube all over my ass.

I spread my legs wide as I leaned over the balcony. He appeared behind me and pulled the bodysuit to the side and pulled the G-string from my ass. He then placed his hand on my lower back as I felt the pressure of his cock at the entrance to my ass. With a little push, he was inside me and he let out the biggest moan I'd heard since I got on the cruise.

'Does it feel good?' I moaned back to him.

'So, fucking good,' he said as he started to thrust himself inside me. 'Your ass is fucking amazing.'

'Is it better than you dreamed?' I kept teasing him.

'Fuck yes, I'm never taking my cock out of your ass again.'

He continued to fuck me while my head was over the balcony. I started to moan as he picked up the pace and started to really pound me. I could see the room below had the lights on their balcony turned on, no doubt they could hear me. Then a head appeared over the balcony below, directly looking up at me. All they could see was my chest and head moving backwards and forwards over the balcony as Geoff fucked me.

'I'm so sorry,' I moaned, talking down to them. 'He's just fucking my ass too good.'

The person below smiled, then disappeared back to whatever they were doing, and I told Geoff it was best we moved inside to reduce the noise levels. Geoff reluctantly pulled out of my ass, he almost seemed annoyed that he had to remove himself for me for roughly thirty seconds. Once inside I closed the balcony door, and I didn't even get chance to move. Geoff had me pressed against the glass as he put his cock straight back inside me.

'Fuck,' I moaned. 'You really are enjoying yourself aren't you.'

He just grunted and continued to fuck me. My moans started to steam up the glass in front of me and my face was practically pressed against the glass. I loved a good dominant fuck, and this was no different. And to be honest, I didn't think he'd be this good. He had me well and truly cock drunk and I could feel my body submitting to him as my legs started to wobble and give way beneath me.

'Oh fuck, oh fuck,' I kept moaning. 'You're fucking me so good Daddy, but I feel like I'm gonna collapse.'

'You better get on the floor then.' He said as he pulled out of me, spun me around and started pushing me onto my hands and knees.

I was now on the floor, on my hands and knees, ass pointing straight up into the air and my face flat against the floor. I could feel the cool air blowing around my fucked ass. But that soon stopped when he put his cock back into my ass. I looked up and could see into the mirror in front of me as Geoff mounted me again, positioning himself above my ass before starting to fuck me again. I watched in the reflection as he bounced up and down, pummelling his cock inside me repeatedly, my mouth was wide open as he milked my prostate.

'Fuck,' he started to grunt. 'Fuck. I'm gonna cum soon. Fuck.'

'I want to look into your eyes as you breed me Daddy,' I managed to mumble out as the fucking continued.

He granted my request, removing his cock so I had chance to turn over and lay on my back. He grabbed my legs and pulled them apart, as he pushed his cock back inside me. The fucking resumed and I reached for my cock and pulled it free from my panties and bodysuit and started jerking myself off. The pleasure I was feeling at the minute was immense, nothing like I'd ever felt before. Very quickly, I could feel my own orgasm approaching. I reached out with my spare hand and rested it on his chest, feeling the hair which made him look so manly to me.

'I'm gonna cum. I'm gonna fucking fill your ass.' He started to fuck me faster and I could feel his heart beating faster through his chest. Then he started grunting and each grunt seemed to get longer and then I felt his orgasm hit him. The warmth of his cum started to fill me up, I could feel it inside me. And it just seemed to keep going and going, it was like he was never going to stop.

I continued to jerk my own cock and I hit my own orgasm shortly after Geoff did. My moan was more of a high-pitched squeal as I covered myself in cum with Geoff breathing heavily above me. We both just stayed in that position as we recovered from our orgasms. I could feel Geoff getting softer in my ass until his cock slipped out of my hole followed by a big drop of his cum.

'I'm not just saying this, but that was one of the best fucks I've ever had,' I told him as I was still regaining my breath. 'If you'd have done that to me on the first day, we'd have never seen the outside of your room.'