The Vacation Ch. 01

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The story of my last vacation.
4k words
4.53
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Part 1 of the 2 part series

Updated 09/22/2022
Created 06/13/2008
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Last summer, my boyfriend and I finally broke things off after more than a year of living together. Breakups are never easy, and this one wasn't either. But it was inevitable. He just wasn't a good fit for me and I wasn't for him. After the break up, I decided I needed some space from people for a while. The last thing I needed in my life was more drama. So, for the months that followed, I threw myself into everything I could to avoid new relationships or conflict with people.

In many ways, this was a good thing. I got caught up at work, something I have never done before. I spent a lot of time with my family and friends. I even went to the movies with one of my uncles, something I hadn't done since I was little. I also started some hobbies that I had always wanted to. I did all these things and more and life became better because of it.

However, as good as it was, something was missing. It wasn't that I was missing my boyfriend. He became a distant memory within weeks of the break up. I was never one to dwell on break ups and I came to realize I liked not having him and all that drama around. However, there was one thing I missed, or needed. I missed having sex. I mean, I was never one that had to have sex every day to stay alive or anything, but it didn't take long till I was really missing it.

I would wake up in the middle of the night thinking about previous lovers. Flash backs of their chest, their arms, their butt and their penis would run through my head constantly. I would see men on the street and would look to see if I could see a bulge in their pants; see if I could catch them looking at me.

I started to watch porn on the Internet and chat with strangers about their sex lives in chat rooms. I found myself on multiple occasions watching men masturbating on cam in one of the yahoo chat rooms while I played with myself.

Over the winter, I decided I needed to get away for a while and take a vacation. Warmer weather was just what I needed. I called a number of my friends to see if any could join me. As my luck would have it, none of them could go. All were tied up with work, boyfriends, life, yada, yada, yada. So, instead of putting it off, I just decided to go for it and go alone.

Physically, I'm 27, with long brown hair and I'm a little thing. I weigh about 110 lbs. and I'm 5'4". I'm no model or anything, but I do OK.

It was a long drive and I did stop in Atlanta for the night on the way there, but I did finally make it to Miami around 3:00 in the afternoon. The rest of the day was pretty much uneventful. Mostly, I got settled into my room and took a walk on the beach. The weather was so nice. I had left Cincinnati at 30 degrees and slushy and here I was in paradise at 70 degrees and sunny. By nightfall, I was starting to wear out, but this was a vacation and I wasn't ready to let my days end early, so I went down by the pool where there was a little tiki-bar. I sat on one of the stools, and ordered a Pena Colada from the tanned blonde bartender.

As I sipped the cool drink, there were some nursing students laughing with one another at the bar. I wasn't sure they even knew I was there. I did listen in on their conversations, and they did seem nice enough, but they were into their stories with one another. I just sat off to the side quietly enjoying my drink listening in on whatever part of the conversation I could make out.

I hated to admit it, but I was already starting to feel lonely. I find sometimes that being single is a lonely life. I eat dinner alone most days. I do the same for lunch and here I was in paradise feeling that loneliness.

I wasn't paying much attention to things when a man stepped up to the bar next to me and ordered a beer. I guessed he was in his early forties, with dark brown hair, not really heavy, but he did carry a few extra pounds. He was wearing red and white swim shorts that still had sand on them and a tank top and like all the people around the beach, he looked as relaxed as he could be.

I was in relax mode also. All I had on was my bikini. At this point in the trip, I wasn't pushing the envelope of indecency too far. My bikini was white and a little skimpy, but it wasn't a thong and everything was amply covered.

After he made his order, he leaned on the bar, looked at me in the eyes and with a deep voice, said "hello" and flashed a great big shiny smile at me.

I was out with some friends a few months back and one of them was telling the story of how she got weirded out because this older man started gawking at her. This of course caused most of the other girls in the room to start telling their "gawk" stories. I'm not sure what I was thinking, but I had the audacity to ask "was he handsome?" which was followed by stares of amazement from the whole room. Anyway, I guess the point of this is that I've never been weirded out by older men looking me over a little and to be honest, I normally welcome a little of it.

Back to my story, I know it was the wrong thing to do, but I gave him a beaming smile. The truth was, I didn't really care who he was or what he was. I needed someone to talk to and he seemed eager enough for the job. Of course it didn't hurt a bit that he had these beautiful brown eyes that seemed to twinkle when he looked at me. He seemed a little surprised at my reaction, and sat down next to me.

We exchanged pleasantries and all the normal stuff people talk about when they first meet and before long, the nursing girls went back toward the hotel laughing. So, I was left with the bar tender and my new friend Gary. The three of us chatted for a little while, and I found out that Gary was married and had two kids.

He was very engaging, I liked his smile and he flirted with me way too much. I know, most of you are saying to yourselves, what in the world are you doing, but this was something I just really needed. It had been so long since someone looked at me this way and it really felt good. Of course, I was on drink number 4 by then, so a little drunkenness can be blamed for some of my behavior.

The bartender was at the end of his evening and needed to close up the bar. He told us we were free to stay and chat, but that he had to close up and head home.

Gary looked like he was about to panic. He clearly didn't want the night to end, so he looked at me with those big brown eyes and said, "Let's stay for a while. Will you?"

I giggled and said "Sure. I've got nowhere else to be." So we ordered another round of drinks and continued talking and drinking alone while we finished our drinks.

I've been told more than once that I can be a little direct and pretty "no nonsense" and I was feeling pretty direct at the moment. I think it might have been the location. I mean, when you are a thousand miles from home and nobody knows anything about you or where you are from and you know you will never see these strangers again, I think it makes you do things you would never do at home.

All through the evening, I found myself sneaking little peaks at his shorts. I know it's perverted, but I just couldn't help what I was doing. Those bar stools are so awkward and as he sat there right across from me, legs all spread out, and I could almost see all the way up the leg of his shorts. Once, when he turned a certain way, I even think I saw his penis wobbling in there. Looking back, I can't even believe what I was doing, but I did.

There was a little pause in our chit-chat as I was avoiding his eyes and I just decided it was time to cut to the chase and find out why he was doing what he was doing and where this was going to lead.

"Why are you hitting on me so hard? I mean, I like it, but you have a family at home."

He was caught off guard. Up till that point, I hadn't really acknowledged his flirtations or really asked anything difficult, but, before we continued too much further, I wanted to know some more about what was in this guys head.

"Hmmmm....You caught me off guard with that, but, it's a fair question. I am obviously very attracted to you. I know what I'm doing is wrong, but I can't seem to stop. If you like, I will stop and head up stairs and quit bothering you."

"What is your home situation like?"

Again, I think I caught him off guard. He almost seemed that he expected me to ask him to quit and go up stairs. But he gathered his thoughts a little and answered my question.

"Well, I have a great wife and two great kids and a pretty good life."

"You seem to get along well enough."

"Yea, we do very well."

I had to pause for a second. He wasn't giving me anything to go on. I mean, if things are that good, why flirt so openly with someone else? Was the location doing things for him too? Or is he just a big cheater that does this wherever he goes? Am I just the next girl on the list?

Something was bothering me about this whole situation. Why would he say these things about his family if he just wanted to cheat on them?

I must have been looking away for a while, but I had to think this out a little and my head was a little fuzzy with alcohol. It took a few minutes, but it came to me what might be the problem. I wasn't sure how to approach the topic, but it didn't seem I was going to offend him. He had already shown that he was going to answer any question I asked him.

"How is your sex life?"

"Oh boy. You cut to the chase don't you?

I looked him straight in the eyes as I said, "I've been guilty of that before."

I wanted to watch his eyes and body language as he told me. This wasn't the time to tell lies and I wanted to make sure that wasn't happening.

"Well, we haven't had any form of sex in over a year."

"A whole year?"

"A whole year."

"Why? What's going on?"

"Our sex life was never what I would call shooting stars or anything. I was lucky if we did anything more than once a month. This part is a little embarrassing, but since you asked, I'll be honest with you about it. She caught me looking at porn on the Internet."

"And she quit having sex with you over that?"

"My wife is very religious, and she felt betrayed. She was deeply hurt that I would seek out sexual pleasure somewhere else besides her."

I knew the problem. I had heard about it from some of my guy friends. These women get it into their head that a man is just going to go through life without any form of sex and the minute they try to find some form of relief, they treat them as the betrayer.

OK, I felt sorry for the guy. He was in a bad way, but does that have to be my problem? I've never been one that liked the phrase "Mercy Sex" or anything like it.

"C'mon. Let's go to your room. You probably don't know this, but I need this as bad as you do."

I know, you can't believe I just came out and said that. And I couldn't believe it either, but I did. However, this wasn't "Mercy Sex." Actually, it was the furthest thing from it. I was attracted to him. I loved the way he looked at me. I also didn't mind doing something against a woman that would do such a thing, even if she probably would never know I did it. And furthermore, I needed sex. I needed sex! I NEEDED SEX!

I could have knocked him over with a pin. His jaw dropped open and he seemed stunned.

I didn't really want to deal with the difficult questions or awkward silence or anything, so I just started walking toward the hotel, took a few steps, stopped, looked back, and said "are you coming?"

He looked away for a second, but looked back and said "Ahhh....Yea."

I used the time as we were walking to his room to set down some rules.

"Have you touched or been touched by another person over the last year?"

"No."

I stopped, looked him in the eye and very firmly said ..."Nobody?"

"Nope. Not a soul. The only person I've touched in the last 18 years is my wife and we haven't touched each other for more than a year."

I believed him. I believed every word of it, but, I turned away from him, continued walking and without looking at him said, "I'm not sure I want you inside me tonight, so we are going to need to use hands and such. Are you OK with that?"

He chuckled involuntarily. "Yea. I can live with that."

We got to his room and he fumbled a little to open the door, but finally, we were in.

The whole day, no, for months, this had been boiling inside of me. I knew what I wanted and he was just going to have to take it for a while (not that he wouldn't anyway).

I didn't even wait till I got to the bed. I was walking behind him down the hall toward the large king sided mattress in the back of the room and I stopped, took off my bikini bottoms and pulled the string on my top and let it drop. He didn't even see what hit him as I pushed him onto his back on the bed.

He looked up at me in complete amazement. He had just noticed that I was completely naked and he was trying to look at everything I had.

He was lying there with just his swim shorts and tank top and I wasn't wasting any time. Without hesitation, I reached out to the sides of his shorts, told him to pick up his bottom and proceeded to pull them down a little.

Right away I could see the dark brown hair of his pubic area peaking out through the top of his shorts. It was full and got fuller the more I pulled them down. As I tugged, I noticed they wouldn't come down any further. I mean the bottom seemed to slip off fine, but the front was apparently hooked on his penis. I found this quite amusing and giggled a little, but I also liked it. He was already hard and, as a woman, that really meant something to me.

I guess I hadn't really been surprised by it, but it, probably as much as anything else he said or did that evening, said that he wanted me, and not just a little.

I smiled at him a little and gave him a little giggle. "I think we need to unhook this a little" as I reached under the waist band, felt his stiffness, pushed it to the side a little and proceeded to pull the shorts down and expose it.

I didn't pull the shorts all the way down at this point. I just wanted to see it, to see what it looked like. I pulled his shorts down to just about mid-thigh, just enough to see it pulsing in front of me as it pointed toward his face. I could see the hairiness of it. I could see the balls, so hairy, and the veins that spider webbed around them just under the thin skin of his sack.

I've noticed that sometimes guys have shriveled up sacks and sometimes the balls within are larger, and loose or free flowing. Some day I'm going to ask someone to tell me why, but Gary's sack, at the moment, was loose, and the balls were swelled and I just needed to touch them.

I was staring at his penis and his balls, but only for a few seconds. I then looked up into his eyes, smiled, and said "I see you've been thinking naughty thoughts of me already. And thank you! I love it. It's beautiful." My eyes dropped back down and I reached out and grabbed his penis with one of my hands and started pulling his shorts off his legs with the other.

He gasped with air as soon as I touched it.

"Hmmmm...It has been a while hasn't it?"

I didn't give him a chance to answer and just started stroking him with one hand then I took my other and cupped and tugged a little on his pouch.

He was in a daze at this point and didn't really know what hit him. He almost seemed as though he was going to quit breathing, as he would suck in air and exhaled in large bursts. I had him where I wanted. I was really enjoying what I did to him.

After I had been stroking him for a few minutes, I thought I would really do something to blow his mind. An old boyfriend of mine showed me how if you stick a finger in his bum while you are doing things to his penis, it drives the guy nuts.

I proceeded to take my hand from his balls and slowly trace a line with my middle finger down to his anus. Without hesitation, I pushed the first knuckle of my middle finger in.

Without warning, he said "Oh my God!" and started to buck his hips. It wasn't 5 seconds till cum squirted all over his shirt and belly as he tried to groan and buck against my hand.

"That sure didn't take much." I giggled as I continued to slow down my strokes.

"Oh, my Fucking God!" was all he could say as his body continued to spasm.

Normally, I don't really like that word and I don't often use it, but in this case, I knew he didn't use it often either and I took it as a real compliment.

Now it was my turn, but I needed to clean him up a little before I took care of that. I got up quickly and went into the bathroom to get a towel. As I started to come back, I had a grin from ear to ear. I wasn't sure why, but I think I was turning red from embarrassment. He could here me walking back into the room and immediately looked my way as he took off the shirt and he just drank me in. He looked at everything I had and he told me "you are unbelievable."

I loved the complement, but now wasn't the time. I'm sure it made me blush even more, but I had an ache that needed attention. When I got to the bed, I just crawled up on my hands and knees, pushed him back a little and proceeded to clean up the mess that was all over his belly and penis.

When all was cleaned up, he stopped me, gently pushed me back on my back and said "now it's your turn" as he moved down to the bottom of the bed and started moving my ankles apart.

"Can I lick you?"

"If you don't soon, I WILL SCREAM!"

He laughed as he leaned forward and without warning, I could feel his tongue on my clit as he used his fingers to pull my labia apart. That's exactly what I needed. Oh, the stars were coming quick and I sucked in a large gulp of air as his tongue darted under my hood.

He was good at this, or maybe he wasn't. I didn't care. All I knew was that he was hitting the right spots and I was moving quickly toward orgasmic bliss. He continued his tongue assault on my clit and I could feel he was starting to put his fingers inside. Again, to my surprise, he seemed to do just the right thing and I felt that little tingle inside as he gently rubbed two fingers along the top inside of my vagina. That was good. Oh, that was good.

I have never been one that likes to shave my pubic hair. I never really had much to shave anyway, but for now, my little brown patch of hair was au natural and I could feel my pubic hair, especially along the edges of my labia, getting all matted and sticky from his assaults and from my own flow of moisture. Maybe this was mostly my own because I could feel the trickle of something wet rolling down over my anus. I was soaked and I could feel that build up in my belly coming in waves.

I guess he was right. It was my turn. He continued licking my clit as he separated my labia with the fingers of his one hand. With his other hand, he gently caressed the inside right under my clit. I grabbed his hair with both of my hands, and pushed my pelvis hard against his face as all my muscles started to tighten. I dug in my heels pushed my head back, curled my toes and closed my eyes as that feeling pulsed in me.

As it came in waves, I could hear myself, almost as if it was someone else in the room, saying "Yes, Yes, Yes" as I bucked against him and had the most wonderful orgasm I could have imagined, but my body and vagina couldn't take any more. I get real sensitive down there after I have a strong orgasm and I involuntarily moved my head forward and my legs clamped to stop his assault. He seemed to understand and giggled a little as he pulled away and let my body convulse there on the bed as I breathed hard as if I had just ran miles and could do nothing but try to catch my breath.

"Emmmm....That was good Gary!"

"You're telling me. But, I have to apologize for being so quick and all." He really seemed embarrassed by it.

"Don't apologize. You could have paid me no better complement."

I could tell he appreciated that. He got up on his knees and moved toward me and sort of plopped down on me and gave me a huge hug as he whispered in my ear softly "you're something else Jennifer, you really are something else."

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