A Gay Cruise
(Please support Nifty at the donate link as I finally have and I answer all emails at mikedave01@yahoo.com.)
OK, I have finally lost it. I knew this day was coming, but it is here. I have officially lost my mind. I looked around the tight cabin on the ship. It wasn't uncomfortable, just tight. My roommate had his own bed and he promised me that there was no need for us to do anything sexual together while on the gay cruise. He just wanted to do a gay cruise again and needed a roommate. Yeah, right. Me rooming with someone in a naked or nearly naked situation with nothing like sex? Like that had worked so well for me in the past? Anyway. My hope was that Tim, the roomie, would find someone that floated his boat on this cruise (pun intended) and leave me out of his equation. I mean Tim is not unattractive. He has muscles still and has a nice face. But there is something fundamentally wrong with him healthwise, which he won't communicate. He's a medical doctor and seems to still practice parttime. He has a lovely condo looking down on downtown from one of the hills above it. And he can be persuasive. He and I have never done anything sexually, but I know he has wanted to. He started peppering me a few years ago about how much fun a gay cruise was and how you saw great places and could be yourself as a gay guy with gay guys. Well, I have never identified as gay, although men do turn me on, at least certain men. So, that argument wasn't too persuasive. But when he said I needed to get out of my rut, see new places, eat new foods, dance to new music, and meet new people, he started to break me down. He kept bringing over brochures with beautiful pics of places I hadn't been to before and food I hadn't tried. I did begin to feel that I was in a rut in my comfortable, but boring, life. Much against my better judgment I finally agreed to go on a cruise with Tim. I mean, being a widower after a super long marriage after which I buried my wife and now not dating anybody did mean I was in quite a rut. After exploring the cruises' web site and other sites, I did buy a new wardrobe for the trip. I was amused at the young guy at the men's store who helped me pick out clothes. It seemed he wanted to pick me out as well! I knew I was fantasizing about that though! Even though I'm in great shape and don't look my age, reality does intrude. I am officially a senior citizen, even if I don't feel like one. I wanted to look good on the cruise, but was not cruising (terrible pun once again intended). I really was interested in the new places, new food, and meeting new people (if not for sex). After acquiring my new wardrobe and thanking the young salesman, who seemed regretful that I didn't do more than thank him (!), I did go home to pack.
Tim and I flew to Miami to get on the Caribbean cruise. I have never liked Miami. For anyone who does, you can show me around there and change my mind. But, for me, it is conservative in the wrong kind of way, overreaching, and sprawling in the wrong kind of way as well. I would be glad to get on the ship/boat. Also glad Tim and I had separate rooms in the hotel. To be honest I have given up on sex, much less love, after a few tries since being single. But that's ok I guess. Fumbling with Tim in a hotel room was not on the docket.
The trip to the boat was fine as was embarking. A nice ship. My room with Tim was fine, I decided after checking it out. And then, alone in the room, is where this all begins. I thought I had truly lost it. What the hell was I doing on a gay cruise of the Caribbean? I thought back through all of my justifications for this trip. Yeah, I could afford it. Yeah, I wanted to see new places, eat new food, and meet new people. But I was lying to myself about not wanting to meet new people for sexual fun. I have always loved anything like sex and those with me seemed to have, too. And having had very little sex in years was not working for me anymore. I looked at myself in the room's mirror and realized that I was really vulnerable, not for the first time, sigh. Well, be careful and take things slowly I told myself. Remember you're on a gay cruise after all and all the guys on the cruise are on the make in one way or another! After that burst of honesty, I realized it was time to go on deck and wave bye bye to the USA.
I went on deck and enjoyed just being in the warm wind and smelling the salt water. I was enjoying being by myself, as I normally was. No big deal there. I enjoyed looking at the other passengers, who were all dressed to kill in various ways. Some were undressed to kill, too! That all amused me and I was glad I didn't need to dress that way. I guess I looked good in form-fitting clothes, thanks to the young salesman, but that was not that important to me, thank God. I looked around the deck big time eventually and saw only one guy alone looking out to sea. He looked like a nice guy. His expression was both intense and wistful. I watched him for a while. Much against my better judgment (and this trip was done in my better judgment?) I decided to approach him and just stand near him.
I said nothing to the guy. I just stood near him in some kind of vague support, although I doubted he needed it, and didn't know how to give it anyway. After some time he noticed me. He appraised me (he did what?) and said nothing. As I started to move away, since he was obviously ok, he stopped me. He said, "I don't think I know you." I responded that I didn't know him either, but was just checking on him since he was alone looking out to sea. He looked at me big time then. He looked like he couldn't believe what I said. To be honest, I do get tired of being misunderstood, especially when I'm trying to do something nice. I started to leave again. I had done my duty. He was fine. He stopped me again and said, "Who are you and why would you care about me?" I sort of snorted. It took all of me not to go full (ex) New York on him. I said, "Dude, you were alone, thoughtful in the wrong kind of way, and looking out to sea. I have seen suicides in the past. Just wanted to make sure you weren't thinking about that." I looked him over much more carefully then. "And, dude, a guy as good-looking as you committing suicide would be quite a waste!" As expected, he burst out laughing. He sputtered, "Who the fuck are you?" I am who I am of course. I responded, "I am just a normal recently retired professor who worked with students for 45 years and saw a bit of some of them in you." I continued, "Look, I apologize for interrupting your reverie. It seems you are fine, but was just checking." He looked me over carefully again, assessing me again. He finally said, "I like you. Could we spend time together on this cruise getting to know each other?" I saw no reason why not and agreed to. It wasn't as if I had major sexual trysts planned on the cruise after all.
We wound up meeting for meals and for the trips to islands where we stopped. I started to like him a lot and finally had to ask his first name. When he said, "John" it was all I could do not to hoot, although he looked doubtful when I said I was "David". We started to have so much fun together that it disturbed me big time. He was smart, erudite, and knowledgeable. We both made each other laugh. We didn't go beyond long hugs to anything sexual even though we were on a gay cruise. The irony of that didn't amuse me alone in my cabin, although was glad that Tim was gone to some guy's bunk.
Look, this isn't working. I'm on a gay cruise with a guy I am seriously interested in and I'm not exploring possibilities with him? I am free and single finally. Guess I got to figure out if he is or not.
After a stop in Guadeloupe (and yes, I speak fluent French and was able to be a guide for John there and help him appreciate this part of France) I decided I had to broach John about "us" to find out if there were to be an "us". When I did he suddenly burst into tears! This was so not the guy I thought I knew that I didn't know what to do except hold him. He stopped from crying quickly and looked at me hard once again. He said, "You don't really know who I am, do you?" I growled in reply and said, "I know you're a smart and hot guy and I like you a lot. Not enough?" His sad expression said, no. He said, "David, I think I could love spending much more time with you now and when we return to the States. But you need to know who I am." My response was to say, "Can't we go to bed now and ignore the States for now?" His responsive smile was so amazing as to light up the day. "Yes David", he said. Let me find us a place and I'll give you a room number.
Well, that wasn't an expected response, but an ok one. Why not go to bed in a neutral place I guess. And if he could get access to a neutral place where neither one of us had anything invested that might not be the worst thing if we were going to take what was becoming a relationship to a new level. Ok, I'm back to the beginning of this "adventure". I was wondering about a lot of things, not least of which was whether John was some kind of criminal or even a serial murderer and had some kind of hold over the ship's management through threats from a gang of some kind so that he could find us a room on a crowded ship. I waved my head at my sudden silliness. I'm not a bad judge of character. If John were not a solid dude, I'd eat some kind of hat.
Sooner than expected my phone dinged with a room number from John. OK, I thought. Time to explore.
I guess I haven't described much about what John and I look like. I'm sort of the typical in shape 6'1 185 pound older guy with a nice face and decent hair, chest hair, and facial hair. I do stand up straight and am pretty athletic. I like to dance in a crazy way and am musical, too. John was more of a mystery. He is thinner than I am and almost as tall. His face is more craggier than pretty, but that suits me just fine. One of my old jokes is that if I want a woman I want a woman (and never any problem in getting one) but that if I want a man I want a man. And John was a man to be sure. Was he a man's man like I was? I suspected he could be and wanted to find out.
I met John at the room very low down (pun intended) in the ship at the appointed time. He opened the door quickly on my knock and hustled me into the small, but quite adequate room. He searched my face deeply and then gave me the passionate kiss I had been waiting for, even if I didn't quite know I had. I responded with greater and pent-up passion. He felt it and couldn't help but gasp, "You want me that much?" "More than you can imagine" was the reply that startled me as much as him. But I realized it was the truth. We took our kiss to the bed/bunk then. Eventually I managed to start stripping him and let him strip me between kisses. I had seen him nearly naked when swimming in Speedos, but having a nearly naked John in my arms vs seeing him nearly naked was quite a different experience of course! And he seemed to enjoy the feel of me equally as much. Eventually it was time for the pièce de résistance, the unveiling of the cocks. His was first. His matched him perfectly, the hard, thick enough, 7 incher. Frankly it was beautiful and I wanted to go down on it immediately. John stopped me though. He then took my Speedos down to unveil my huge 8 incher with the big mushroom head. At this point I've had guys decide to walk away, after excuses of one kind or another. I had figured John wouldn't, but he had the chance to. At this point we could go our separate ways, although I would regret that big time. I had come to have feelings for John. All he said, was "Wow" and studied me naked. After a suitable time, I pulled him into me for a naked kiss. Test was passed. He didn't run away. After enough time I moved us both into a 69 position. I wanted to devour his gorgeous cock and wanted to see what he made of my huge cock. And, yes, this was a challenge. He responded well though. He didn't try to take all of me immediately but worked on me well. As for me, I soon had all of him in me and was slurping away quite happily. We enjoyed each other for quite a while that way. Eventually we came back to kissing front to front and nipples and chest together while rubbing our crotches and hard cocks together. We were both breathless at this point and sweaty. We broke off the kiss and looked at each other's masculine beauty. I found him beautiful and something wrenched in my heart, much against my better judgment once again. I looked into his dark blue eyes and saw something quite similar, or at least I thought I did. He started to say something and then relented. After more kissing and body frotting he asked if we could cum in each other's mouth and leave off fucking until our next time together since he needed to prepare for that! Well, I was astounded at his directness but also turned on by it. Here was a man who knew what he wanted and would get it, a man after my own heart. And that phrase made me give an existential shudder. He was a man after my own heart and I wanted him to have it, didn't I? He misunderstood my shudder and I had to explain that I wanted exactly what he wanted. His smile of relief was enough for me to go down on him immediately, wanting his cum! And damn, wasn't it a pleasure sucking him off and his beautiful cock? Sooner than I wanted I felt his balls tighten and his cock harden even further. In response, I allowed mine to follow suit. Soon we were flooding each other's mouth with hot cum! We saved enough to share cum in our snowball kiss afterwards. We then fell asleep briefly in each other's naked arms, naked bodies glued together. At this point if I had died I would have gone to heaven! Too soon we woke up and John looked at me deeply and seriously. "David", he said, "I have to go but I will be back with you as soon as I can. You can stay here if you would like. Here's your key to here" and he gave me a room key. I couldn't help but look quizzically then. He smiled sadly. "Later" was all he said. He then drew on his Speedo and clothes from God knows where. He was soon dressed and admired me still naked in bed. "David, next time can't come soon enough for me." He saw the affirmation in my eyes and gave me a real smile. He leaned over and gave me a quick, but very passionate, kiss before leaving me alone in the small room.
At this point I was so far afield that I didn't know if I'd heed the call from the cowherd to come back to the barn for the night. I eventually decided I didn't want to stay in the small and dark room any longer without John. I got dressed in what I could find and then went up to my room. Tim was still gone and I wondered a bit about his continued absence, but put the rest of my casual cruise clothes on. I decided fresh air on the deck and sun would be a good idea. I made my way to the upper deck and sort of reveled in the glory of creation then, even if I wondered about a lot of things. Eventually I realized that a few crew members were shadowing me and watching me. I finally said aloud in my best New York, "What?" That made them smile and they went away. Well, that confused me even further. I didn't hear from John the rest of the day except for a text to say, "Tomorrow". Frankly, nothing I wanted to read. I decided to do the cruise for real then. I went to the gym, swam in the big pool, did both wet and dry saunas and enjoyed the unusual food at meals and learned about the ingredients after quizzing the unexpectedly helpful waiters. I also went ashore by myself at Curaçao and enjoyed speaking the bit of Dutch I knew and had a blue drink. I did note I was being watched quite discreetly though and wondered about that. Well, no accounting for tastes I guessed!
I enjoyed the evening meal, even if no John. I was seated with a group of older couples who engaged me in very nice, if desultory, conversation. After all of the passion and questions about John, this was sort of a nice change of pace though. The service staff insisted we try wines that went with the meal and we had both an apéritif and a digestif. Frankly, I wasn't used to this much alcohol and was glad to go back to my room for a long night's rest. I was met by a staff person who opened my room for me and showed me a mini bottle of champagne in an ice bucket who told me that was to help me sleep and was a present from John. Well, I wasn't used to being wooed in the slightest and wasn't sure how I felt about it. Anyway, stripped naked and was soon asleep.
I woke up early and put on shorts only to go on deck and feel the sun and breeze. Again staff were present, if not close. Again I wondered about that. I enjoyed a healthy fresh breakfast with a lot of fruits I didn't know after getting dressed. The wait staff was quite helpful in suggesting fruits I didn't know and naming them. Delicious of course. But again I wondered what was going on. I finally got a text from John asking if I could join him in the small room below in the afternoon around 2. Of course I could and said so! And noticed lots of guys looking at me once I put my phone away. But none of them approached me. OK, what is going on here? Guess I'd have to wait until 2 to find out though, after doing John though! I exercised later on in the morning and then had a very light lunch of oysters to inspire me for later, not that I needed much inspiration!
It took everything I had to wait until ten after two to knock on the door of the room down below. I had a key and could have just gone in, but, somehow, that seemed wrong, or at least impolite. Quite soon John opened the door. I walked in and we just looked at each other at first. I saw him with new eyes and I guess he did the same. My heart gave a quick tug then. I mean, who was this man I was falling in love with, if that's what was happening to me? I wasn't even sure what I was feeling. This was all so new to me. He must have seen the confusion on my face and suddenly he was in my arms! I pulled him as close to me as I could and then proceeded to kiss him as deeply and passionately as I knew how! He responded in kind! Soon, we were on the bed/bunk in the tightest embrace I had ever been in. I could feel every millimeter of his body against mine. Wow! I felt like cumming and we were still clothed! No, no, no, no, no! I managed to push him away, just barely, and started to strip. He got the idea and joined me. The mutual admiration society was now officially in session! Well, this wasn't going to take long, now was it? He pointed out the lube and all he said was that we were both clean, implying he had been tested recently, and that he knew much more about me than I knew about him! Well, shelve that thought for the moment. His truly fine thin mature body and small ass were mine! We resumed kissing, but this was a man with a mission it appeared. He soon lubed up my super hard huge cock and his small ass and then put his hole over my cock and gently eased it into him! Yessir! Soon, I was completely in him, balls deep. I looked at his face with concern, wanting to be sure he was ok with what probably was one of the biggest cocks he had ever had in him. To my relief all I saw was a smile of satisfaction and an expression of having done well. At that point I began to fuck him, or was it make love to him? My earlier confusion returned. What was it about him anyway? Shelve that thought as well, I chided myself, and focused on John and our fucking. Soon, I had enough of this position. I wanted to see his face and kiss him as I plowed him deep. I wanted to feel his chest against mine and our nipples to rub together as our faces did, too. I managed to move him onto his back without coming out of him and then resumed the best fuck I had ever had! I could feel him respond hugely to me and my pounding. I felt, rather than saw, his eyes roll back in his head. I'm not sure mine didn't as well. This couldn't last too long. It was just that intense. Too soon, I heard him gasp and he yelled out my name as his butt squeezed my cock as tightly as it ever had been. I felt his cum between us and knew I had made him cum hands-free by hitting his prostate too many times! That was way more than enough to push me over the edge and I yelled out my orgasm loud enough to be glad I was on a gay cruise!
We both started to come down from our orgasmic peaks finally and then just held each other naked. I think we both fell asleep for a few minutes after the rush of our sex/love. Eventually we realized we were sweaty and sticky and my cum was dripping out of John's oh-so-fine ass. He smiled a very sweet and bashful smile at me then. He said we should get cleaned up just enough in the shower here in this room and then put on robes and head up to his room for a more thorough cleaning up. Ok, I said, but wondered a bit. Good to his word we did a basic cleaning up and there were wonderful soft and thick robes waiting for us I hadn't noticed when I entered the room, so intent I was on John. Well, they did feel great on our still feverish skin, despite the shower. We put on our flips as well. John took me by the hand and led me to the elevator. We got in and he produced a key from the pocket of his robe (how had he known whose robe was whose?) and inserted it into a small keyhole I had never noticed and turned it a quarter turn. I noticed he was carefully not looking at me then. I have to admit I was puzzled, if not so stupid as to not start to guess at some of the answers I had been seeking.
We kept climbing and climbing and climbing. I noticed we went beyond the common decks and kept climbing. At the very top of the ship we stopped and the elevator opened. John led me out onto an extremely plush carpet and a very large room and a set of rooms it seemed. To say I was again nonplussed would be an understatement. He led me past a number of formal rooms and reception rooms and finally led me into a gym/exercise area that looked appointed for quite a team. He kept holding my hand and led me into a sauna and whirlpool area with showers as well. There he dropped his robe and took mine off me, too. There he and I got clean and scrubbed each other, enjoying our nakedness. Despite the weirdness of the setting I started to get hard again and felt he was, too. He smiled at me, an understanding smile, understanding what I didn't know, and got us new robes and slippers this time from the locker room equivalent. He then led us into a smaller, if not small, dining area, where quite a feast awaited us. I started to say something and John interrupted me and said, "Not yet". We ate and drank wonderful French food and wine. I was soon replete and a bit tipsy. We had said very little during the meal, except for remarking on the excellence of the food and wine. Several times I started to say something, but stopped before I did. This was John's scene and it was his time to talk. John looked hard at me and studied me one more time. He began slowly...
"David, you are you, are you not?" I nodded affirmation. "You are as honest as the day is long. You are blunt, you pull no punches, and you have gotten into trouble for that as an academic, have you not?" Guilty as charged and no secret. "And how do you feel about me, honest man?" John suddenly looked embarrassed and said, "Don't answer that. You can't, until you know who I am and decide if I have tricked you or not." I nodded my head in agreement. This was John's show, not mine. He had to be as honest as I am if we were going to move on. John looked as if he would rather be anywhere but here, but my fixed expression let him know he had to level with me. He understood immediately. He was not a stupid man by any stretch of the imagination. "Well David", he said, "I am quite wealthy." I looked around where we were and gave him a very exaggerated nod. To his credit he blushed and said, "Extremely wealthy". Point taken, I thought, but so what? He followed my expressions. "It took a long time for my advisors to allow me to take this cruise. I had to promise to let them vet every person who signed up for the cruise in detail before they would let anyone on the ship. Eventually they vetted the full thousand guys on this cruise in detail." He stopped for a minute to let me absorb everything. "And they gave me a summary about everyone. But there was one guy who stood out in the summary and that was you." He looked on the verge of crying, but I wanted and needed him to continue. He realized he had to after looking at my expression one more time. "Yes, David, I wanted to meet you. I hope you don't think this is sick, but I sort of fell in love with you before meeting you, based upon everything I could find out about you. You are an amazing man. You are so true and loyal. You were so great to your late wife as she abused you. Your children are amazing people already, too. And you are yourself and true to yourself, are you not?" This time I let him let the tears fall. He looked at me hard again. "Yes, the time alone at the rail looking out to sea as we left the USA was a set up for you." It was all I could do not to glare at him then. "But you passed with flying colors as always. You saw me for who I am and made sure I was not going to commit suicide. You were ready to leave forever when you saw I was ok enough.' I nodded. "But that wasn't an act. If you hadn't checked on me I might have tried to jump. I am that alone and have been most of my life. Splendid isolation is one of the worst fates I wouldn't wish on anyone." Well, there was a lot of privilege talking here, but being the gilded queen was certainly not fun I'm sure. And it was all I could do not to ask him if he had felt like Richie Rich growing up, but one look at him was enough to make me realize he had worked hard at being as normal as he was allowed to be. "And when you turned out to be the man I have always been looking for, smart, funny, learned, as well as handsome as heck, I lost the rest of my heart to you. And when you seemed to feel the same way about me, I was determined to give myself to you, even if you spurned me after finding out the truth about me." With that he stopped and waited. I held up a finger for him to wait while I processed everything. To be honest, I hated him being rich. I didn't mind anything else. The fact that he wanted me so much to do everything possible to have me was amazingly flattering, especially since I found him every bit as attractive as he found me. I mean, I had already given him at least half my heart and now wanted to give him the rest. He had been honest in his account, including his initial seduction of me. Ok, all is ok except for his money I finally decided. I finally asked, "How wealthy are you?" He grimaced and said, "I'm one of the wealthiest people in the world." Well, that was so not ok! He knew it wasn't. OK, too much to process once again. I looked at John and where we were. This was not going to work. I motioned to him to get out of the sauna and whirlpool area and back into our robes and flips. He looked puzzled but did what I motioned him to do. Eventually I found our way out of the penthouse suite or whatever this place was and got us back to the elevator. I pushed the buttons to get us back to my room. I figured that there would be no Tim there and that the room would be for just us. Figured that was part of what John's advisors would have set up to be sure I was safe on the ship, since I was certainly "a person of interest" to John. I knew there had to be a 24/7 team watching John and now, me, too. At this point none of that mattered. The fact that there had to be cameras everywhere didn't matter. Even so I wanted to be in familiar territory. I took John into my room on the ship and had us drop the robes and flips. With both of us naked again, I took him into my arms and said, "John, I'm willing to try to be yours if you're willing to try to be mine. I do love you and have lost my heart to you. If you have found me an amazing person, I have found you the same. We'll figure out the money you have and the need for your security, I promise." (I could just about hear the sighs of relief from John's security detail). But now, you're mine and I'm yours." And that was that for the rest of our lives.
Fin