A Jamaican Vacation Ch. 01

The only silver lining of my fiancé calling off our wedding was that I still had a non-refundable trip to Jamaica already booked. The trip gave me something to look forward to after this nightmare of a month.

So a few days after my original wedding date, I hopped on a plane and went on my planned honeymoon by myself.

The resort was beautiful, and coming from New York in the winter, the weather was a welcome reprieve. The only bummer was they lost my checked bag, but I still had a few things in my carry-on that would get be through the first couple of days.

After dropping what I did have off in my room, I set out to find the resort convenient store, hoping they would have a swimsuit I could buy. All I wanted to do was grab a cocktail and hang out by the pool.

The good news is they did have swimsuits, the bad news was that they weren't my standard baggy board short style. They were much shorter and form fitting, made out of a stretchy material. The worker said that this was the style here, as they allow you to be more active on the beach, and that beach volleyball and soccer was so popular here.

I felt a little self conscious as I walked down to the pool wearing them. They felt a little tight on my ass, but no one else paid much attention. Even saw a couple of other guys in speedos, so it wasn't that bad. I guess these adult only resorts aren't what I was used to.

I found a poolside lounge chair, and was promptly greeted by a Jamaican guy who came and take my order. He was extremely friendly, but I couldn't help but notice how ripped he was. The guys working the pool didn't have to wear shirts, and this guy was fit.

I was laying down, but he must have been 6'5" and 230 pounds of muscle.

When he came back with my pina colada, he bent over to set my drink down, and introduced himself as Ty. I turned my head to introduce myself, but since I was in the lounge chair, I was pretty much eye level with his crotch. I quickly looked up to make eye contact with him, but couldn't help but notice a huge bulge in his swimsuit.

I introduced myself as Alex, and caught myself trying to glance another peek at his crotch. I'm not gay, or even bi, but I have always been mesmerized by big cocks in porn. Probably because I was 4 inches hard on a good day.

We made small talk for a minute, but then he gave me a wink and went back to work. The rest of the afternoon, I caught glimpses of a few of the other workers. They all had that tell tale bulge of a big black cock. I even noticed a few sets of women clearly ogling the bartenders and giggling while staring.

After a few drinks, I became self conscious of my appearance. I'm fit, but more of a cardio body. Also, I'm only about 5'7". I've gotten really into spin class lately, so I was down to 150 pounds. But the front of my already small bathing suit was pretty much flat. There weren't going to be any women sitting poolside looking my way after seeing these other men.

The rest of the day was pretty uneventful, just had a few too many cocktails and put myself to bed.

The next morning, I wanted to take a beach front spin class that they offered. I called the front desk to ask about my bags and to reserve a spot in the class. No luck with my bag, but they did have a spot for me in class.

I went back down to the store and purchased a tank top and a pair of spandex. They may have been women's spandex to be honest, but I'm used to biking in my spandex, so it was my preference. Only issue is that my spandex at home goes down to just above my knees, they only had two options, yoga pant style spandex, or short shorts.

Given the heat, and that people seemed to just wear less clothes here, I went for the shorts. I felt a bit silly putting them on, they were only a few inches below my ass, but whatever, no one seemed to pay me any attention.

When I got to the beach, Ty was running the class.

"Good morning Alex!" He greeted me.

The class was almost full, so he guided me towards one of the last available bikes. I couldn't help but notice how large his hand felt on my lower back as he ushered me towards the bike in the front row.

For the next hour Ty pretty much kicked out asses, but it was an awesome work out. I was pouring sweat and could really feel it in my ass and quads.

"Great job everyone!" Ty yelled. "Now the best part about spin on the beach is a post workout dip!"

On that note, he took off his shirt and ran to dive into the ocean. Like everyone else, I ripped off my shirt and went diving in too.

As I came up for air, I was right next to Ty.

"Great job out there today Alex! Hope to see you out here again, I think you have a lot of potential."

"Thanks Ty! You are a beast on that bike!" I complimented back.

"That's not the only place I'm a beast!" He laughed as he headed back to shore.

I wasn't 100% sure what he meant, but I had my assumptions based off of what I noticed yesterday, and today in class to be honest. I wonder how many white tourists he takes down with his big black cock working here.

As my mind wandered, I felt my penis twitch to life and decided I should just let myself cool down in the ocean. I bet it would be hot to see him hook up with one of those giggly women by the pool yesterday.

I wonder what it's like for someone to take their first big cock, especially a big black cock. The women in porn seem to love it, but what it is like for the average woman who may have never had anything larger than average. It has to be an adjustment. Both in terms of actually having sex in the moment, but also mentally. How you see men, and smaller men like me, as sexual beings has to change too.

I digress.

Later that afternoon, I went back to the pool for happy hour. No sign of my bag yet. So I washed my spin outfit in the sink and put my swimsuit back on and headed to the pool.

Luckily for me, Ty was working again. He saw me coming and greeted me with a big pina colada. He knew exactly what I wanted.

After laying out poolside for a bit, I decided to get some shade so I went to sit at the bar and order my drink. Since Ty was working the bar, I ended up just chatting with him. Next thing I knew, a couple of hours passed. He was really quite charming.

Between the sun earlier and the drinks, I was really tipsy. Ty said he was about to be on his break and was going to smoke some weed if I wanted to join. I had forgotten it was legal here.

"Absolutely! I haven't smoked weed in a while, but I used to love it growing up. Want to go up to my room? I have a killer balcony off of my suite."

"Eager boy!" Ty responded. "There's plenty of time for that later. Let's go to a sunset party instead. I have to get the weed there anyways."

Oh my god, I just invited him up to my room. I didn't even realize how that sounded. He was probably reading into that, I didn't mean anything like that.

I played it cool.

"Yea absolutely, that sounds great. Are there going to be any chicks there?"

"Probably, but we can have fun without them too!"

After a few minute walk down the beach, we got to this great little spot with about 20 other people.

"Pretty much anyone here that is black works at the resort or one close by." Ty laughed.

"So who are the 4 other white women?" I asked.

"Like you. Just friends who are here for a good time."

These women were definitely looking to try big black cock with no strings attached. You could tell just by how they were throwing themselves at the various guys.

Ty passed me a joint, I took a hit. Then another. And another. After a few minutes, I was flying. It's been a while since I've smoked, and I was starting to almost be uncomfortably high.

I was feeling and focusing on everything. The sand in between my toes, the setting sunlight on my skin, the feel of my swimsuit hugging my ass.

I forgot how horny weed made me. All I wanted to do was get off, but there's no way I could compete with Ty and his friends. I don't stand a chance with these girls.

Also, why was I the only guy in a tiny little swimsuit. I looked like a girl in short gym shorts. I tugged at the ends, trying to make them longer.

"What are you doing?" Asked Ty, "you're legs and ass look great in those short shorts. They fit you perfectly."

"Thanks Ty, they just seem so short. I feel like I'm wearing girls shorts."

"Well aren't you?"

"Aren't I what?"

"Aren't you wearing girls shorts?"

"No, I got them at the hotel store. The airline lost my bag."

Ty nearly spit out his drink from laughing, "which store?" he prodded.

"Isn't there just the one by the breakfast buffet?"

"No sweetie, that's the girls store. The guys store is over by the tennis courts. The shorts you are wearing isn't even a swimsuit, it's just short gym shorts."

I blushed. I couldn't believe it, I was wearing girls clothes. And that means my spin outfit was for girls too. I've essentially been cross dressing since getting to Jamaica. I wanted to put my head in the sand.

Ty, sensing my embarrassment, put his arm around my shoulder and handed me the join again.

"Who cares Alex, or should I say Alexis, you look hot. All of these other women are trashy. You have an amazing body and I bet you know how to use it."

I didn't even know what to say, I just laughed.

Then, without hesitation, he pulled me into him and kissed me deep. I was completely caught off guard. I put my hands on his chest and pushed him back. He was so much bigger than me though I barely moved him more than a few inches.

"What are you doing, I'm not gay."

"Are you sure? Looks like part of you might feel differently about it," Ty responded, still holding my hips.

I looked down, but didn't need to. My little penis got hard when pressed up to his warm, hard body. The weed also didn't help my case, it always made me horny.

"It's just the weed, it always makes me horny. And then your body is so warm, it would have happened with anyone."

"Are you sure about that Alexis?" He grabbed my hand, before I could protest he put it on the bulge of his bathing suit. "It had nothing to do with feeling my big black cock press against your stomach when I kissed you?"

He held my hand there, making me rub my hand up and down on his big black cock. He was so much stronger than me. I felt his big black cock start to come to life. He was truly massive. He was so much larger than me that I didn't even have a frame of reference with my own penis.

This whole time we were still only standing a couple inches apart. I never retreated further. Why didn't I?

"I don't know Ty," I argued meekly.

"I do, let's just relax for a minute. I think we both need to cool down a bit, or else we are going to fuck right here on the beach in front of all these people."

He grabbed me by the hand and walked me over to a cooler, grabbing us a couple of Coronas. I noticed people staring at us.

"Don't worry about them," Ty said, "everyone of those white girls will be taking big black cock tonight too. You are just the first one to pair up."

What did he think was going to happen? I'm high, I'm horny, I'm going with the flow. But nothing more was going to happen tonight, or ever.

We walked about 20 feet away and he plopped down on the sand, pulling me down with him. He was sitting with his legs open, and I was sitting in the sand right in front of him.

He pulled me back so my ass was pressed up against his crotch. I sat up straight, but after a few minutes of watching the sunset, I found myself leaning back against his chest.

I heard the sound of the lighter behind me. He was lighting the joint back up. After what sounded like a big hit, he turned my head towards him and gave me another deep kiss, blowing the smoke into my mouth.

Turning like that caused me to lose my balance a bit though. I put my hand on his thigh to steady myself. He took this opportunity to spin me around all the way. I was now on my knees in between his legs with one hand on his thigh and the other on his chest while he kissed me deep.

I felt his hands on my ass. His hands were so large. They covered my entire ass. I was helpless as he lifted me onto him. I couldn't keep kneeling in this positing. So I was now straddling him. I moved me hands behind his neck and grasped him tight. He was in complete control.

With both of his hands on my ass, and me getting into position, my women's shorts were pulled even tighter. I could feel the elastic stretch on my upper thigh.

All of a sudden, I stopped.

"What's wrong sweetie?" He asked, still keeping a firm grip on my ass.

"Nothing, don't worry about it. It's nothing."

"Tell me sweetie."

"Well, it's just. I've never been with a guy before. Haven't even kissed one. And, well, I can feel your big black cock against my little penis and it's kind of shocking. Just having a lot of emotions right now."

"That's ok Alexis, that's perfectly natural. I can imagine how challenging this is for you. But you are doing great. I think you are about to learn who you really are. On that note, why don't we go up to your room. I can't lose my job due to public nudity on the beach."

"I don't know Ty," I responded, "maybe we should just call it a night."

"If that's what you want, but at least let me walk you to your room."

"Ok that would be great, I'm pretty high anyways."

Like a gentleman, Ty walked me to my room. When we got there, he pushed me against the door and gave me a deep good night kiss.

God, he was a good kisser. I've always been on the man's side of kissing, but being on the receiving end just seemed to come more natural to me. I felt like I was a better kisser in this role. I hope he thought so too.

"How about one last joint on the balcony, then I'll head off and we can go back to normal tomorrow?" Ty asked.

"Sure why not, it's a beautiful night anyways."

We sat down in the chairs on the balcony. After a couple of hits I got up to get my phone to put some music on. As o walked back down, Ty grabbed my hand and pulled me onto his lap.

As my booty shorts covered ass hit his big black cock again, I felt that familiar twitch in my crotch. I was getting hard again. I felt really good about diffusing the situation earlier as I cooled down from walking to my room. But I was getting really worked up again. Hopefully he won't realize.

As I was smoking the joint, I felt him nuzzle into me and kiss me on my neck. With his one hand he grabbed my left breast as you would a woman, with his right hand he put his hand down the front of my shorts.

"Just as I expected," he said and he found my small but hard penis. He held my penis with his thumb and index finger, stroking me up and down within the confines of my booty shorts.

He was going so slow, it was keeping me horny and felt so good, but I wasn't going to get any relief from it. I started to move my hips back and forth and up and down to force the issue and go faster. But when I did that, he stopped moving his hand. I was essentially just fucking his two fingers.

However that has consequences that I wasn't thinking of. I had essentially been grinding my ass onto his big black cock. I felt him start to harden up, he was huge. It honestly felt like I was grinding in someone's forearm. What was I doing? I stopped.

"Why'd you stop Alexis?"

Ugh why was he calling me Alexis? Was it because of my booty shorts and tank top? Why was I calling them booty shorts!

"Well I was trying to get off but you stopped and then I realized I was just grinding on your big black cock."

"And that's so bad why? I'm going to get you off tonight Alexis, but it's not going to be like this. I don't give hand jobs, I was just playing with your clit."

"It's not a clit, it's my penis."

"Well let's compare then, because from my position you are wearing girls shorts grinding on my big black cock."

He stood up, and since I was on his lap I stood up with him. In one quick move he spun me around so I was facing him and then he tugged my shorts down so they dropped to the floor.

I stood there completely exposed. I still had a tank top on, but since that too was a girls tank top, I stopped right at my waistline. My little penis was hard and sticking straight out.

"This is not a man's cock," Ty said sternly, looking me in my eyes. "But that doesn't mean you are not an extremely sexual being."

He pulled down his shorts slowly. Out sprung the biggest black cock I could have ever imagined. And I say sprung because as he pulled his shorts down, it was like a slow unveiling. The further he pulled his shorts down, more and more of his big black cock became exposed. After about 10 inches of this, he gave his shorts one final tug and his big black cock shot up like a mast.

I was standing less than a foot away from

Him and his big black cock rubbed against my little penis and balls before resting against my stomach. I instinctively reached for it. But with both hands. I couldn't believe that I could fit two hands on it, and there was room for more.

And then there was the thickness. I had one hand face down on the top and the other face up on the underside, and I couldn't even touch my hands.

And then there was the head. It was huge. Like an apricot. This was a big black cock.

He just stood there, I was entranced. I'm not sure how long we stood like that, but eventually I felt him place two fingers under my chin and tilt my head up.

"My eyes are up here Alexis," he laughed.

I didn't even realize it, but I was biting my lower lip in angst as I was exploring his magnificent big black cock.

He took one last hit of weed, and kissed me one more time, blowing the smoke into my mouth.

It was a big hit and I felt my knees get weak. He took this opportunity of wobbly knees to put his hands on my shoulders and guide me down to the ground in front of him. Not rough, but intentional and firm.

"Why don't you get a closer look at what's going to make you a woman."

I kept stroking his big black cock, but was now kneeling in front of him. He was so big that I had to arch my back away from him to get spacing.

"Why don't you give it a kiss, tell it how excited you are to have met him."

I kept stroking and eventually gained up the courage. I lifted his cock in and leaned into his big black cock, kissing the underside.

His big black cock was so massive that it felt like I was holding an old phone next to my face as I kissed him again and again.

I worked my way around his cock and eventually decided to go in for the real thing. I was going to give him head. I opened wide and got his entire head in my mouth. My jaw couldn't open any wider.

As I adjusted to the size, I reached out with both hands. Not just to steady myself on his cock, but also to stroke him. I knew from watching porn that with even smaller cocks than this, a lot of times you can only get the head in and need to keep him stimulated with your hands.

However, after a minute or two of this I tried to take more, and more, and more. I never knew it, but I didn't really have much of a gag reflex at all. I never got the whole thing in, but I got about 6 inches in, halfway there.

I looked up at him. His big black cock still lodged down my throat.

"This is impressive Alexis! You are going to love what comes next. But I need to make a quick call. Care if I sit?"

"Hmm hmmm" was all I could get out. Why did I try to talk with his big black cock in my mouth? I knew it was a rhetorical question. I'm such a dumb slut.

He said down on the chair and grabbed his phone off of the table. I crawled toward him a bit to improve me angle, going back to kissing and licking his underside. Every now and then I would just stop and set his cock next to my head so I could be fully entranced in its size.

I don't know who he was calling. But heard him ask someone for a few favors, said extra small a couple times. Then I also heard the words black, long blonde hair with blue eyes, lube, tomorrow too and then said my room number.