“Ten Men Waiting for Me at the Door? Send One of Them Home, I’m Tired.”
It’s a lovely feeling having acquaintances in different cities, states and/or countries. As you can probably tell, I enjoy meeting new faces and personalities whether I’m driving, walking or flying to different places of the world. There is so much outside of our small little world where we live and I plan on experiencing them all one day, eventually. The experience of new adventures, new foods, new cultures, new music, new dances and of course new people is fascinating to me. Of course, there is always a goal to get laid by at least one local man or traveler. Not getting laid on a trip makes me cranky and nobody wants me cranky on vacation! It doesn't necessarily have to be strangers all the time, I have traveled with men too (just imagine those stories)... You see, I travel 3-4 times a year (whether in the states or abroad somewhere), but the intention is always to learn something from all these locations. Of course, if I fall in love with a place, I do end up going there more than once (usually not to the same city though).
As you can tell, I’m not the type of person that is afraid of being alone. I have learned that this is an essential part of life. After my divorce, it was hard not to have someone around all the time which made me anxious and had me fucking people that I usually wouldn’t fuck out of boredom. I started to accept the reality that I could do anything with my time and once that happened, I actually started being happier alone. I became more comfortable with the quietness and being in my own skin which is a great accomplishment. If it worked for me, why can't it work for everyone else?
Let’s get back to traveling…I would say that traveling alone (not meeting anyone you know anywhere), is another essential part of life and I highly recommend it. Don’t get caught up with what the news portrays (it’s mostly wrong and over-exaggerated), just book a trip and live life! The solitude and freedom you will obtain from traveling alone is surreal.
Now you see, although I travel alone, that doesn’t necessarily mean I am alone. It’s fairly easy to meet people on vacation, for anyone actually. While we are all in the same resort, you will be seeing the same couples and groups of people at the same restaurants, pools, beaches, bars, you get the point… Also, people on vacation are usually looser and easier to talk to (especially if they start drinking at 10 AM when the bars open like me). If I hear anyone speaking English, then I’m starting a conversation with them and of course you see the staff there almost everyday. Just asking them where they came from is the best ice breaker for any conversation.
This story is going to encompass one of my many trips to the lovely island of Jamaica. Let me place a disclaimer here. Jamaica is my favorite island for many reasons, but the top three are: 1) humble people; 2) my obsession with the food and spices they use (real Jamaican food, not resort style); and 3) the fucking weed! On this memorable trip, I actually went with a girlfriend at the time. Although I went with a friend, I was actually alone starting from the second day of the trip. It was an amazing trip overall which was filled with new experiences...
Before I start, I have a question. Is having more than one sexual partner on the same day, something most people do? I honestly don’t know because this is a subject people don’t discuss very often. But here I am, telling you that it does happen. And I can’t be the only one among over 300 million in the United States alone? I would bet some money on this one that I am not the only person doing these promiscuous deeds!
Well this story goes like this...Me and a girlfriend at the time went to Jamaica one spring. Now this “girlfriend” was a single mom and was always desperate for attention. No seriously, it was exhausting at times. We went out to a local club the second night in Jamaica and met two locals that got pretty attached to us. We ended up bringing them back to our rooms (which is a huge no-no at an all-inclusive resorts), but who doesn’t like breaking the rules here and there? These two men weren’t meant to stay longer than one night. But that’s not what my “friend” had in mind. We both ended up fucking one of the guys but I must say I hit the gold mine (at least in size wise). This local younger man who I’m going to call “14DD” (probably 5 years younger than me, but he was definitely fuckable on looks along), had the biggest dick I have ever seen. Her and her boy-toy went to the bedroom and we stayed in the living room kissing and fondling each other. Now let me tell you, I first noticed that he had a huge dick when we were at the club grinding on each other, but seeing it in person was a whole different mind fuck. Picture this, skinny man, about 6 feet tall and his dick went all the way down to his knee. OMG! I seriously didn’t know where that was going but I made the best of it. Every position was painful. Every single one. I’m not even sure how the condom covered all of it (which is couldn’t). At one point, I tried sitting on top of him and got about a quarter way in until it couldn’t go anymore. I think the only reason I came was from the pain and the constant beating of my internal wall, because it honestly wasn’t pleasurable. We tried doing it doggy style (which was much better), but still his dick wasn’t getting even halfway in. What the fuck do you do with this thing. I kind of felt bad for him LOL. I’m betting I’m not the first woman to not know what to do with his dick. Seriously, it was out of control. At one point, my girl and her boy-toy walked by and just stopped to stare at the site of his dick in my pussy. I’m not exaggerating when I say this man had a 14 inch dick. Just so you know, I did some research on the depth of an average vagina which is anywhere between 3 up to 7 inches! Now go get a measuring tape and get an image of what I was dealing with. Holy fuck!
Although I did cum a few times too many, I didn’t actually enjoy the sex and was strangely a bit turned off by the whole experience. In my opinion, size isn’t the most important factor of a penis. To me, it’s more important that the person have a certain fucking rhythm and know what to do with his dick to provide pleasure to the woman. “14DD” did not know how to handle his own dick. He had to hold it at every angle. That shit was just too heavy to be anywhere alone.
The next morning, my girl (of course) has fallen in love with her boy-toy and ended up paying for him to stay at the resort. Ummm WTF, why are you paying for this man to spend OUR vacation together? Tremendous turnoff in my mind. Yes, I fuck people on vacation, but no one interferes with our vacation and no one gets invited to stay in our room. No one! The problem was, “14DD” wasn’t leaving his friend and I was in no way paying for him to stay in my room, so he paid his own way in. I was frustrated and voiced my concerns openly to the group. The understanding that this was only sex and having to spend time with this person for my entire trip wasn’t going to happen. I’m a happy single woman and I did not want a man next to me, not on this trip.
That morning, after they handled the payment of the room, they all went to the pool and I honestly couldn’t deal with the clinginess of “14DD”. He had hearts in his eyes when he talked to me and I didn’t feel the same way especially now that they were staying in the room with us. Hell no! I’m still going to be me... I told them I’m going to explore the island and just left them. Meanwhile, I had been flirting with this taxi driver that had been trying to get us to do an excursion since we checked in. He was always around and we had been flirting for the past 3 days. I negotiated a price with him to take me to Negril and to make a few stops for real Jamaican food and souvenirs. Let’s just say I got my money’s worth on that excursion. It got a bit hot and heavy in the car to Negril. The drive was an hour and half long and during that time, we stopped a few times to fuck, to eat, to shop and to fuck again. He literally pulled off to the side of the highway and had no cares in the world. I clearly didn’t give a fuck either. We finally arrive in Negril, Rick’s café to be exact. This was a touristy spot where people jump off cliffs, hang out, drink and party. I was already completely fucked up at this point and thought it would be a great idea to jump off one of these cliffs. Choice of 3 different heights and of course, I choose the highest one. This might have been the dumbest thing I have done. Bypass all the danger signs and get myself to the edge of the cliff. I was supposed to jump straight with my arms at my side. Well let’s just say fear and gravity took over and I didn’t go straight at all. I slapped the water with my ass hitting the water first (in the sitting position). I had a very hard time swimming to the side because my ass was on fire. I tell you, I played it off pretty cool, but the amount of pain I experienced hitting that water was unforgettable. He drove me back to the hotel (stopped once more for some more fucking) and I went to my room to assess the damage of my poor ass. My entire lower ass (right above the thigh line) was BLUE. All I can think about is how the fuck am I going to fuck someone with a blue ass. That blue turned black and purple in a week. Well I have to say I wouldn’t do it again, but I’m glad I have this story to tell.
Now I’m back at the resort and still avoiding “14DD” and trying to get some me time. I go to the beach and lay down to get some some and relax. This handsome older man comes and sits next to me and we spark up a conversation. This man was from Chicago and had a great personality which just means that we got along very well. We ate on the beach together, drinks were flowing, smoked a few blunts and I’m still on the high from cliff jumping and my prior sexual sessions. We end up in the ocean and start fooling around. He starts fingering me under water and all I can do is try to keep a straight face around the other travelers in the ocean. I get extremely turned on which makes me want to find a nice secluded area for some more fucking. We took a walk to the far end of the island to find a secluded beach chair under a nice tree (I’m not the only person who has used this area for sex)! I end up fucking this man in broad daylight (blue ass and all). A few people might have seen or heard something, but no one interrupted. He was very sensual and had a lot of experience… He felt really good inside of me, unlike the huge dick I had the night before or the one I had just a few hours ago. I cum a few times, he cums a few more and we go our separate ways.
I end up in the room to shower and get dressed for whatever the night brings. I eat dinner and of course still drinking and smoking. I end up at the sports bar to play some pool and bar games with a few interesting couples and tourists. I connect with another Jamaican that was doing security at the resort. Nice, tall, fit man that apparently has been watching my every move since check in a few days ago. It was interesting to hear what he had seen since I checked into the resort. This security man ends up following me everywhere in the resort that night (claims he was worried I was alone). Complete bullshit, but I can obviously tell he wanted a taste. I explained my room situation (two uninvited men) and he ends up getting me a key to another room (I didn’t ask, but I’m guessing he has a connect at the front desk). As I’m walking on the beach in the middle of the night, I feel him watching me and worried about me. I started teasing him which turns him on to the fullest. We get in the room (I think this was his intention of giving me a key from the beginning) and start fooling around. Smallish penis (not that impressive) but I could work with it. We fucked for a few and I sucked him off so good that he ended up cumming in my mouth (great accomplishment in my eyes)! What happens next is something most women don’t expect on a first fuck. He asked me to marry him. Ummm, you are kidding right?
This shit doesn’t flatter me, it’s actually another turn off. See, I have had my share of Jamaican men (even in the states) and they are all very similar in expectations. They get attached to women very quickly. So knowing when to say no and not get strung along is a life skill that I learned. Most of these men want something from you. You can’t imagine how many men have asked me for visas and other ridiculous requests like money, meals, drug trafficking, marriage, I can keep going… Yes, I have heard it all and I love being strong enough to be able to say, "No thank you!, dude!" This is a sexapade, not a lifelong commitment. It’s sad to know that some women do say yes to these things and end up in very bad places...
The rest of the trip was amusing to say the least. I had 4 men that I fucked all in the same resort (I told you it was easy to find people). They all saw me flirting with at least one or the other in their presence. The texts and looks I got were laughable. Of course, when vacation ended, everyone went back to their normal lives (which is exactly what’s supposed to happen). My girl and I ended up not staying friends because of this vacation and of course, her and her boy-toy grew apart once she went back home. What did she really expect?
So the bottom line is, how many sexual experiences in one day is actually too many? No one is judging (maybe you are, but oh well, what happened on this vacation is not the norm), but why not have 4 different experiences in a foreign country with people you probably will not see again? I didn’t plan on fucking all 4 in the span of 22 hours, but it happened. It might have been the weed, the alcohol, the men; I honestly don’t know, but all I can say is that each man gave me a new experience to remember and another unforgettable story. Blue bruised ass and all...