A Trip to Remember Pt. 04 - Finale

*** Author's note. This is the conclusion to this story but there may be some follow ups down the line. It helps to read the first three parts first.

I slept through the night without waking with a cock in me. I realized as I began to stir that I kind of missed it. Regardless, it was an amazing night. Walking around dressed fully en femme and then being fucked in the middle of the pool deck amongst hundreds of people was the highlight of my sex life to that point. I got up and made my way to the bathroom. I realized we had really slept in. It was after 10:00. I guess there would be no yoga today. I took off all of my clothing until I was down to just the chastity cage. I had worn it over a weekend before, but this was the longest I had worn it. Despite the fact I was caged, I had several orgasms so far this trip. I guess there was no longer an excuse to remove it for that reason.

I showered and shaved. I even put on some lipstick that Jessica had left for me. I wasn't daring enough to try makeup beyond that yet, at least without some help. I went back into the room and Mark was stirring but not awake yet. I wanted to wake him up in a special way but figured I would put something on. I found some pink stockings and a pink garter belt. I also found my sissy collar and put it on, without the lock. I then located my pink ankle boots and put them on, without the locks. I figured this was good enough for some morning sex so I made my way to the bed and to wake up my man.

I crawled under the covers and Mark was, of course, sleeping naked. His cock was growing even before I touched it. Morning wood. His morning wood was considerably more impressive than anything I ever achieved as a man. I took his cock in my hand and began to lick up and down the shaft. I caressed his balls as I licked his member to life. It seemed he was at full mast pretty quickly and I took him into my mouth. I took my time and gradually got him further and further into my mouth and throat. He moaned and said, "Good morning baby." I moaned something of a reply with a mouthful of cock. He put his hands on the back of my head and began slight thrusts as I bobbed on the large cock in my mouth and throat. This went on for a while but eventually he picked up the pace of his thrusts and held my head tighter. He began fucking my throat, seemingly even deeper than I managed days ago. Finally, he held me tight and unloaded, right down my throat. I couldn't even taste it; it was practically right into my stomach.

He held me on his cock until he returned to normal size, at least normal for him. He then released me and I laid on the bed next to him. He inquired about what I wanted to do that day, our last aboard. I told him I was up for whatever he wanted. "Good answer, girl." He smiled and stood up pulling me so that I was laying at the edge of the bed, with my legs hanging off the side. He then went about the room gathering things like wrist and ankle cuffs and his rope. I was beginning to think that our day would be spent indoors, which was fine with me. He put the wrist and ankle cuffs on me. As he was doing that, he noticed the locks were not on my collar or boots, so he remedied that as well. He then proceeded to tie my arms up toward the head of the bed, spread out. He then did the same thing with my ankles, so I was effectively tied down, spread eagle, with my ass slightly raised off the edge of the bed. He looked at me and appeared to have a look like something wasn't right.

Mark set about the room looking in various suitcases until he found what he was looking for. He returned first with a ball gag and proceeded to strap it into place. It wasn't locked but with my arms tied up, there was no way I was removing it. He then had something else that I could not tell what it was. It looked like black latex. I soon found out it was a hood of some sort. He scooted beside me and lifted my head and began pulling it into place over my head. I was scared because I wasn't sure how I could breathe in it, but it turned out to have holes near the nose. What it did not have were holes for the eyes or mouth. I was effectively blindfolded and gagged. There was also some padding over the ears, so it was difficult to hear as well.

I was immobilized on my back, with no sight, no ability to talk, and very little ability to hear. I then felt something cool around my asshole. It seemed like he was pouring lube there. I felt him insert a finger, then two, then three. He kept applying more lube and working his fingers in me. I had been stretched many times that week, but this was still painful. I figured it was just a matter of time before his whole hand was inside me again, but it didn't get that far. He stopped and inserted the large vibrating plug into me. Its vibrations caused me to instantly start leaking pre-cum from my cage. I then heard Mark say, "I will be back." He was right next to my ear when he said it, but I could feel him get off the bed after. A few minutes later I thought I heard the cabin door close.

I was left to my thoughts. And the buzzing in my ass that felt so good but not good enough to get off. I began replaying the events of the last few days in my head and was so thankful that I had the opportunity to live out what otherwise would have remained fantasy. I usually believe fantasy is better than reality, but this week had been amazing. I don't know how long I laid there. It was probably an hour or two. I eventually heard what I thought may have been the cabin door. I could hear what sounded like voices, as in plural. I figured that maybe Mark had returned with James or Jessica, or both. I could then feel a hand and fingers begin tracing around my stuffed hole. Soon the plug was removed, and I was empty and likely significantly gaping. The hand began reaching into me and applying more lube. I could then feel a hand rubbing along my side and then I was lifted up, despite still being tied to the headboard. It stretched my arms and legs a bit due to the rope reaching its limit. I could feel someone, likely Mark, slid underneath me and lay on the bed where I had been laying. When I was lowered, I was lowered directly onto his cock. It filled me up, much better than the plug had. I was now laying on top of Mark, while I was still tied to the headboard. And his cock was fully inside me. He began to lift me while thrusting. He was essentially bouncing me up and down on his massive cock. I knew it was Mark. I could tell by the size of this cock. It had become so familiar that there was no doubt who was filling me.

After a few minutes of a good pounding, he slowed and lay still, albeit with his cock still fully inside me. I assumed he was resting before resuming the onslaught on my ass. Then the unexpected happened. I assumed we were putting on a good show for James and Jessica, but I then felt a hand begin rubbing around my asshole, which was still impaled on Mark. Then I felt a push at the entrance and realized someone was trying to push something else inside me. There was no way I could take even a pinky finger with the large cock that was already in me. But it persisted. It was slick so I assumed more lube had been added. I began to stretch beyond anything I had felt before and whatever it was began to slide in. It was large, maybe not as large as Mark, but it was big. And it was too big to be a finger. The object made its way further in. It had to be another cock. Was this James? He had never shown that type of interest in me before. Or was it someone else? If so, who? Who could be the second man fucking me at the same time. I had never had sex with a man before this week and now I was being fucked by two, simultaneously.

They began to work a rhythm. One would push in while the other retracted but they both stayed in me the whole time. I was being stretched so much but it was also feeling really good. I could feel my orgasm building. The pace quickened. I figured they couldn't last too long because I was so tight with two large cocks in me. My own orgasm began to wash over me, and I could feel tingling throughout my body. It was incredibly intense, and I didn't want it to end. I could feel cum leaking out of my cage and down between my legs, becoming additional lube for them to use on me. I was really being fucked now, and I think my own clit kept leaking throughout the ordeal. Had I not had a gag in my mouth I would have been yelling in ecstasy. I felt the man that was standing really start hammering and then he began shooting his load into me. Mark was still hammering away.

The standing man, who I assumed was James, slowly pulled out and Mark stayed in me but did slow considerably. He was still fully hard, so I assumed he had not cum yet. I assumed he was resting for another go but then I felt that feeling once again of something pushing at my asshole. Like before, it soon made its way in, and I was doubly stretched again. The two of them picked up the pace like before and I was in ecstasy again. I was also really confused. James is very capable as he fucks Jessica like a beast, but I doubted he could have gone again that quickly. So, there was a mystery man plowing my asshole along with Mark. I came again, and again. I don't think I was even leaking fluid anymore, but the orgasms came repeatedly. I had never been able to achieve anything close to this as a man, but as a sissy, I was quite the fuckslut. The men continued like the first time but this time, both of them climaxed at the same time. The standing man pulled out and I was leaking copious amounts of cum from my asshole. Mark lifted me off of him and he slid out from under me, laying me in a large pool of cum from multiple men. I was spent.

I heard some voices but wasn't able to make them out. I thought I heard the door again a couple minutes later. Then someone lay on the bed near me. I expected to be released but that didn't happen. I think Mark took a nap there next to me while cum continued to leak from my destroyed asshole. Eventually I heard more noise. There were definitely more people in the room. Then I felt someone removing my hood. I was able to see and hear again. Mark was sitting next to me on the bed and James and Jessica were standing near us.

"You look like you've had a rough day," Jessica said. I figured I did look a mess with my sweaty head and likely smeared lipstick. I wasn't able to say anything due to the ball gag still present in my mouth. "What have you all been up to?" she asked. I thought she would know since I figured one of those guys had to have been James, but it seemed like Jessica really didn't know.

"We have been having a little party here," Mark responded. "I invited a couple friends over that I met on deck when I was getting lunch."

Jessica looked shocked. "You little slut. No wonder you look so tore up. Your pussy is still open." She emphasized this by sliding a few fingers into me as I was still tied in place, spread eagle. She removed her fingers, and they were coated in cum which she proceeded to wipe off on my face.

James laughed at my predicament. "I think Cindy here has finally found her calling. We could probably make some money with her when we get home. She might give some of those Only Fans girls a run for their money."

Mark chimed in as well. "Yeah, I think we can continue to find some uses for her after the trip. I wouldn't mind tapping this sweet ass sometimes. She has become quite the little cumslut this week. She has potential."

It was weird to be discussed in this way. I was right there amongst them but was unable to talk. I was being referred to like a piece of meat. I guess that is what I have become this week. I was still expecting this all to come to an end tomorrow when we got off the ship but apparently it would continue in some way. I was excited at the thought of being filled by Mark again. The rest of the plan was scary. They then began to make dinner plans. It was then I realized I had not eaten all day. I was hungry and my stomach rumbled to let others know as well.

It was decided that we would meet in a little over an hour and go for a final dinner together. James and Jessica went next door leaving me with Mark. "I know you need to get ready, but I think I need another go first," he said. His cock was semi hard, but it easily slipped into my loose asshole. He didn't waste any time and began pounding me quickly once he reached a full erection. Despite all the fucking this week, and the many orgasms, it felt great once the pressure started on my prostate. He was an animal and was ramming into me with all the force he could muster. It was no time before my cum started leaking from me in another full body orgasm. This got him really excited, and he then shot yet another load into my ass. He then finally released me from the bondage. My jaw, wrists and ankles were all sore. So was my asshole for that matter.

I went and took another shower and by the time I was done, Jessica was there. She came into the bathroom with me. "Well babe, it's the last night. So, let's see what we can do for you this evening." I was given a pink bra and a pink garter belt. The garter belt was paired with some pink fishnet stockings. A very short pink dress covered this, but barely. The tops of my stockings were visible when I took a step. For shoes, it was the pink locking ankle boots. I was given the wig from the night before and Jessica helped with the makeup. I was still wearing the sissy collar. I don't think I was really passing anyway but the collar made it very clear what I actually was.

We set out to our dinner at one of the restaurants on board. Once again, Mark ordered for me. I didn't care what he ordered. I was just hungry. While we were having dinner, two black guys walked by our table and said hello to Mark. He replied," Hey guys, good to meet you today." They shook hands with Mark and were introduced quickly to James and Jessica. I thought I may have already met them. Regardless, Mark introduced me as Cindy. One of the guys winked at me. I smiled while turning bright red, but then they were off to wherever it was they were heading. It was embarrassing because I am nearly positive those were the two guys from double penetration earlier today.

After dinner we went for a walk around the promenade deck. The breeze was blowing, and I could feel it on my upper thighs and locked clit. The dress was not providing enough coverage to prevent that. James and Jessica held hands as they walked. Mark walked with his hand on my ass, under the dress. We stopped for ice cream. As I licked the ice cream Mark had chosen for me, he started staring at me. I think it was turning him on, so I tried to make a more seductive show for him. I slowly stuck my tongue further out and rolled it around the ice cream. "Ok, we are turning in for the night. I need to fuck this girl a few more times before we leave," he said. There were people walking by as he said it and they turned to look. Neither of us seemed to care at that point.

Mark and I retreated to the room where he literally tore the dress off of me. That would be one less thing to pack tomorrow, I guess. He was aggressively groping at me and forced me to my knees. He then whipped out his cock without removing his pants and forced it deep into my mouth. I was trying to lick it and give him a good sensual blowjob, but he was just fucking my mouth. He was able to get into my throat and continue the fucking. My throat was making all kinds of noises, but it didn't slow him down at all. The pounding continued for at least twenty minutes. I didn't think I would be able to talk tomorrow after this. Finally, he held my head tight and unloaded, once again deep into my throat. I sat back to catch my breath, and he removed his pants.

"Ok girl, I think we should try a little more musical practice. Why don't you get going on that trombone again." I didn't even hesitate. I just moved in behind him as he stood there and moved my tongue right between his cheeks, searching for home. Once I got up into his rosebud, I reached around and began stroking his cock back to life. It was taking a while, probably due to the number of orgasms he had already had. Eventually, he grew hard again, and I kept at it. Once again, I felt lucky that he tasted clean. He let me keep at it for a while but then turned around a picked me up, wrapping my legs around him. He sat me right down onto his massive cock and it slipped all the way in, without much resistance. Mark put my back up against the wall we shared with James and Jessica, and he began fucking me in earnest. It wasn't too long before we heard similar sounds coming from the other side of the wall. This fucking went on for at least fifteen minutes at an amazing pace, but Mark finally finished inside me again. I was trying to remember how many loads had been left in me this week. He sat me down on the bed. Fortunately, the room had been cleaned while we were at dinner. Mark lay next to me, and we both fell asleep.

Amazingly, I made it through the night without being used again. Jessica came by early in the morning to help me get ready and to pack. She unlocked my shoes so I could take a shower. She also helped me remove the locking sissy collar. I had become used to it but wasn't planning on wearing it home. The shower felt good, and I did feel cum running out of my hole. I got out of the shower to find my clothes laid out for me again. It consisted of a white T-shirt with the Virgin logo on it, red panties, very short red shorts and red slouch socks. I had my white converse shoes to wear as well. I was of course still wearing the chastity cage, and I didn't know when to bring this up. This was hardly a manly ensemble but considering what I had been wearing all week, this wasn't bad. I got dressed. Jessica had packed up our suitcases while I was getting ready.

The four of us went to breakfast before we left. Jessica told Mark, "Thanks for showing Cindy a good time this week. I am sure she appreciates it." I blushed. I really did appreciate it. I noticed Jessica hand something small over to Mark and he put it in his pocket. I didn't think much of it at the time. I figured it was some type of thank you gift. After breakfast we returned to our rooms and gathered our things for disembarkation. Thankfully the guys helped with our bags, and we made our way off the ship.

Once through customs, we had the opportunity to say our final goodbyes. I walked up to Mark with the intention of shaking his hand but instead I leaned in and hugged him. It just happened. He picked me up by my ass and spun me around before setting me back down. I turned to leave, and he smacked my ass one final time. James and Jessica made out passionately for a minute before we finally parted ways.

Jessica and I got into our Uber and made our way toward the airport. "Well that was quite the vacation," I said. "I wasn't expecting all that but thank you for making it all happen."

Jessica smiled and said, "I am glad you enjoyed it. You deserve it." She held my hand, and I looked into her eyes. Despite her obvious feelings for James, I felt we were in a good place. We were good for each other. We were a good team and we both enjoyed our life. My ass was still sore from the week's events. I am glad it all happened, but I was ready for a return to the normal world.

I asked Jessica what she had given Mark at breakfast. "I wanted to talk to you about that," she said. "Well, I don't know if you two ever discussed it, but Mark only lives about 45 minutes from us. He is interested in seeing Cindy some more. I didn't think you would mind. I gave him the key that Cindy needs." I knew what that meant. Mark now had the key to my chastity cage. "He will be deciding when, or if she ever gets it again. I thought he earned that right after this week. Also, James doesn't think it should be near me when unlocked so he felt it was better for Mark to have it too." I was speechless. While the sexy vacation had come to an end, apparently the foursome dynamic we had established was going to continue beyond the week. We made it to the airport and onto our flight. I looked out the window the whole flight, lost in thought. What did the future hold?