Older/Younger Adventure Pt. 02 - The Cruise

My adventures with my older mentor continued and I was learning more and more and becoming more proficient at the sexual adventures. During my winter break from school, he suggested we take a cruise, I was interested but had never been on one. He said a bunch of his friends 4 other couples had asked him to come and he said sure and wanted to know whether I was interested, I finally said OK.

We went to where the cruise ships leave and joined up with the other four couples, mostly men except one female. They all seemed like a group of fun people ranging in age from 25 to 65, and a mixture of body sizes and races.

I didn't know what to expect so I just sort of went with the flow. We had a group of nice cabins side by side, We checked in did what I guess is normal for cruising and then started off on our cruise to the Caribbean. We were in our cabin when my friend came out naked from the bathroom and strolled out on our balcony. I was sort of taken aback, but realized you could only see it from the right and left of our balcony.

l went out to find him stroking his fine cock, he invited me over and I stroked him also, then he pushed my head down and I was soon enjoying some tasty cock, as I was sucking him I heard someone commenting, I popped up and heard one our adjoining couples looking over and saying he liked what he saw and wanted to know if he could join in, my friend looked at me and said sure.

I think that is when I realized this was going to be quite the adventure. The man came around dropped his pants and I saw this stout thick cock, not very long but thick. he stroked as i continued to suck, then he came over and my friend started to suck him, I could hear him moaning so I knew he wasn't going to last long so I stopped sucking my friend and started on the other man, he lasted at 1 minute and came, a lot, it was very tasty and I savored it all. Then he quickly went down on my friend and I got my first real voyeuristic watch as he took his load. When we were finished I saw a couple more heads in cabins next to us and realized it was about to be a very fun 7 days.

That night as we were sitting in our cabin chatting, he asked how I felt about people watching and participating in our sex, I told him I had never thought about it before but it was very exciting, he said very good because you might get to know all of my friends that way before this trip is over, he smiled and I did also.

That night we had some intense sex as he fucked me and told me he wanted to watch me with other people, I told him the way he was fucking and talking made me want that also as I started to cum while he fucked me. He said we were going to try some other things also if I didn't object. He never made me do anything I didn't want too.

The next morning at breakfast I met all his friends who were about to become mine also, the first full day we just were going to mingle together and get to know each other, our likes dislikes and such. We met in one couples cabin and everybody threw their keycards to the cabins in a container, we then each grabbed one and whoever matched up were partners for the evening. Think it was a swinger thing. Of all things I got matched up with the female, just went with the flow we chatted and she told me what she wanted to do to me. I was a little confused but went along with it.

When we got to her cabin, she was not wasting time, she quickly grabbed my cock and said, yummy, she unzipped my pants and stroked me, quickly she dropped to her knees and licked and sucked me, she was very good. She stopped stood up and said it was my turn, she quickly took off her top and had some really well shaped breasts, i sucked them and moved my way down to remove her skirt, surprise, she was a very well endowed man, I now knew what she meant when she said she was going to fuck me in the ass, not a strap on but the real deal.

I was soon sucking and licking her cock and balls, it had a mushroom head and was fairly long and thick, much to my surprise she told me to lick her ass, I obliged as I was getting much enjoyment out of doing it, she then turned me around and said, this is going to be a little painful but will be worth it. She lubed me and next thing I felt her pressing her mushroom head at my ass, it popped in, a little pain but fortunately my partner is a good size and I handled it, she then said here it come and she rammed forward, this took me by surprise but I relaxed and started to enjoy it. She was slamming away telling me how tight I was, I was really enjoying the dirty talk. Before too long I heard her start to moan and she was fucking me faster, soon I felt as she came in my ass, she kept going and I thought she was going to continue but she soon pulled out and pushed my head down and told me to clean her up, i was a little unsure but soon had her cock in my mouth and found myself enjoying it. She then told me to stop and asked how I enjoyed my first shemale experience. I think the smile on my face and my hard cock was enough of an answer.

When I got back to my cabin, I could hear some laughing and walked in as my friend and two others were sitting naked chatting, they asked how I enjoyed my experience, I told them it was quite the surprise but a very very pleasant one. One of the other gentlemen stood up and said how about we get together tomorrow, I looked and was surprised to see a HUGE cock, I think my eyes bugged out because he said your partner told me you wouldn't have a problem handling me, I said it would be a pleasure trying. It would be an adventure with the largest cock I had ever seen plus my first with an black man.

That night I slept good and dreamt about taking his huge cock, in the morning I asked my partner if he had ever been with him and he said no, but he knew him and his partner and they were not aggressive and he would be patient, that put me at ease.

The next day we met in his cabin and he didn't waste time, he quickly undressed me and started stroking our cocks together, mine although not real small was quite small compared to his, he slowly pushed my head down and I licked the tip of his beautiful cock, the head was very large so I put it in my mouth and licked and sucked on it, he moaned and started to push more into my mouth, not a lot but more than I was used to handling and I gagged, he pulled out and apologized but I went right back on it and tried to get more in my mouth, it was a tough feat so I just took what I could comfortably and licked up and down the shaft, suck his balls and he pushed my head towards his ass and I knew what he liked.

I licked and tongued his ass and he then grabbed me turned me around and proceeded to rim me, very expertly as I was really relaxing and enjoying it, he eventually took his tongue out and put a finger in and stretched my ass a little, then a second finger and more stretching he had long fingers so he went pretty deep in my ass. Eventually he pulled his fingers out and gradually move his large cock to my asshole, rubbing it up and down and eventually pushing at the entrance, he didn't force it so I relaxed a little more and eventually the head popped inside, I felt very full for only having the head in but he took his time and eventually pushed a little more in, now I really felt full but also very excited.

He pulled me up on my knees and started a slow stroking motion, gradually inserting a little more each time, eventually I felt him against my ass and knew he was all the way in, I squeezed my ass muscles and he moaned, I also began moving back and forth, he whispered that felt nice but he wanted to fuck me, so he started a very fluid motion and was pulling most of his cock out and putting it back in, it was really hot, he asked if he could be a little more aggressive and I said yes, he began fucking me with vigor and I was really enjoying it, a tiny bit of pain but much pleasure. He then turned me over and put my legs over his shoulders and went to town, I thought he was going to be coming out my mouth as deep as it felt.

When I grabbed his ass and pulled him he went faster and a little rougher, a new experience but one I really enjoyed, soon I could hear him moaning and knew he was close, he asked if I wanted it in my ass or on my chest or whatever, I told him to stay where he was and he unloaded a monster load. This would not be the last time we hooked up, it was very erotic and intense.

As our trip progressed there was lot of sex with different men, I got fucked a lot, fucked a lot and lots of oral, rimming, cum, even got used by 4 men at the same time, it was very intense, but very erotic, haven't been on any cruises since but have checked into a couple all gay cruises, maybe one of these days, but still see a few of the men I met on the cruise for some hot get togethers.