Vacation

** Next chapter in my life story. Please check out the other chapters to help make sense of this story. Also, feedback is greatly appreciated. Love hearing how these stories make people feel. **

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As I'm moving forward in my life, meeting with my known FWBs (see last chapters) and having fun, I run across a girl who will change the course of my next four months.

I found her accidentally while riding the train to work. Quite the random encounter. I had noticed her before on the train, but didn't think much of it. She wasn't strikingly beautiful and was dressed for work in a manner that didn't give much away. But on this day she sat next to me and we started up on conversation during a stoppage of the train due to mechanical issues.

A meaningless conversation about a broken train led to a quasi friendship, and the next day she sat by me again and we chatted it up some more. A few weeks go by and my new train friend, her name was Kim, and I know each other decently. Kim was 24 years old, had a boyfriend of two years and worked for a marketing firm in an entry level role. She was white, brown hair, slender body and about 5'6". Nothing too spectacular, just a cute girl.

I eventually had lunch, then drinks with her. It was a bit of a classic affair situation, I felt bad, but knew she was coming my way. When the night came where she came over to my place, I asked her if she was sure she wanted to do it and she responded by grabbing my package and giving it a good squeeze. The first time sex was nothing too special, other than that I finally got to see what she actually looked like. Her body was much better than I expected, her ass was smaller but tight and she had nice B boobs and a tight, slender body.

At the end of the night, we chatted and as I sent her out the door she said, "this is only the beginning" before walking out to her car. I wasn't quite sure what this meant, but took it as a good sign.

The next evening I got a knock on my door and I open it to find Kim. I figured something was up, she either got caught the night before, broke up with him or wanted to go again. She gave a sly smile and slid inside the door. Before I could shut the door and lock it she had slid off her shorts, and taken her top off. She was standing facing me in a red, one piece lingerie. It was lace and wrapped around her boobs and crossed over her stomach into a little g string on the bottom, barely covering her pussy and just a string of fabric down her ass.

My cock was immediately hard and I didn't care her situation at home. I walked up to her and started to kiss her neck and find her pussy before she stopped me.

She said, "Last night was just a warm up to see what type of guy you are. Make sure you were a naughty boy with a big dick. Now you are going to get the real me,"

She then reached down to her large purse and started pulling out a number of toys and what looked like a camera stand. She had a big black 10" dildo, classic rabbit 9" vibrator, anal plug, and a strap on with a ridiculously thick white 7" cock attached. She also had half a dozen garments.

She asked me where I wanted to begin and I was stumped as my mind turned. Fortunately I snapped to and picked up the anal plug, grabbed her hips and guided her to the bedroom as my hard cock bumped against her ass the entire way.

I bent her over the bed, her basically naked ass staring me in the face and I went to work kissing it and then guiding a hand under her to rub her pussy through the g string. I let me tongue guide itself along, tracking the thin string that split her ass, eventually finding her pussy opening. Slowly sliding what little fabric was in my way, I covered her pussy and ass in my saliva while entering her pussy with my tongue. My fingers were still working her clit, eventually sliding inside the fabric and working it up and down.

By this time my cock was breaking out of my pants and I took a short break to pull down my pants and boxers so that my big cock could fly free.

I went back to licking her up and down as she moaned her pleasure. I plunged my tongue back in and used a hand to start working on her little asshole. I got one finger in and started pounding away, my full intention to have her ass filled with the anal plug within minutes. As I licked her more she got wetter and wetter, her pussy juices dripping to her ass allowing me to add a finger and pound it hard. As she became more and more aroused she raised her ass higher and higher helping me finger bang it harder.

After a few minutes I stopped both and grabbed the anal plug. She didn't flinch a bit when the end of it first entered her well lubed ass. I stood right behind her, my cock sticking straight up as I worked it into her ass as the plug widened. She started to moan hard about halfway in and I used that to push it the rest of the way as she let out a scream as the plug found its home inside her.

I was quick with the cock and didn't give her a chance to reset as I plunged my rock hard, pulsing thick cock into her snatch. That really made her moan and scream all at once as she dropped her ass and my cock came out of her pussy. She was now flat against the bed on her stomach and I followed her with my cock. My slipped my hands under her hips and drove my cock into her pussy, holding her in place as I sunk my cock as deep as it could go.

She moaned as I sunk my cock balls deep into her over and over again, my balls slapping against the bed. Her hands were grasping the bed holding on for the ride. After a few minutes of me stroking her deep she started to settle in and take it with less moaning. About this same time my cock couldn't take it any longer and I lost my load inside her, driving it deep inside. I slipped my cock out and smacked her ass as she let out a whimper.

I walked into the other room and retrieved the big black dildo and strap on. Kim has stood up and her eyes widened when she saw what was in my hand. I gently guided her back to the edge of the bed, this time on her back with her pussy at the edge. I pushed her legs back and started to slide the BBC into her. The BBC was a little less thick than mine but obviously longer at 10" compared to my 8".

I worked it in her, slowly filling her with the dildo. She had obviously taken it before as she skillfully took inch after inch until I was holding the base. She now had a black dildo base in her pussy and a purple anal plug in her ass. She was filled completely. I crawled up to the bed and dropped my still flaccid cock into her mouth and she sucked on me until it began to harden up. Once it was hard and sticking straight up I moved up the bed and dropped my balls in her mouth for her to suck on while I stroked my cock.

After a little bit of that I got back off the bed and started to fuck her with the BBC, from 10" deep to 1" deep and back again. I stroked my cock with the other hand as I worked her pussy over and over until she started cumming. And she came hard, squirting everywhere and screaming as her pussy and ass muscles tightened and contorted around their objects. Once she was finished I slipped out the BBC first and then the anal plug, relieving her.

Unfortunately for her now I was very hard, so I grabbed the strap on and put it on. I now had my hard cock with the strap on thick white cock right below mine. Going very slowly I guided my cock into her pussy and shortly after the strap on began to penetrate her anally, giving her a DP. It took a little work as her holes were now tightened back up, but I eventually sunk my cock balls deep and the strap on was all the way in also. From there I pounded as hard as the strap on would let me, her moaning growing louder and more distressed as she was stretched beyond her limits.

As I got close I pushed us both up the bed and rolled her on top of me so she could control. She rode me like a good slut, knowing that she needed to take it all the way in order for me to fill her with cum again. I blew my load as she had her eyes closed and teeth gritted taking the pleasure and pain of two large cocks inside her.

We finished the night in a more relaxed style, using her rabbit, trying on sexy clothes and fucking. She took the BBC again later as I gave her anal doggy style. But it was a much tamer experience.

We went on like this for weeks, her showing up, us fucking like animals. She said her boyfriend never opened to her and didn't like toys so they never used them. His loss.

Then one day I had the bright idea I was due for a vacation, and some people I knew in the swinging community were going on a swingers cruise to a swingers resort. I figured I might as well see if Kim could swing it. And she enough, she agreed. She traveled decently often with work and came up with a story that would last four days.

Before the cruise I told Kim she had better pack plenty of toys, outfits and swimsuits and don't be shy. By this point, I figured she wouldn't be.

We got to the cruise ship, boarded and headed to our room. When we got there Kim opened her bag and it looked like a sex shop. I was instantly hard just imagining what she brought. She had gone shopping and had a whole new set of toys and clothing items specifically for the trip. Perfect. Naturally we banged, me fucking her against the door to the room. Some people clapped as they walked by.

That evening after the ship set sail we hit the restaurant and then went back and changed for the night. There were some events planned but we just went to the bar to get our feel. Of course Kim wore a dress that would probably get indecent exposure on land. It was black, skin tight and went about four inches past her waist. When she bent in the slightest you could make out the tiny black thong she had on. She was obviously getting plenty of looks, especially this being a swingers cruise. We had some drinks, made some friends and hit the deck. We hadn't really discussed our intentions, but I figured things would get dirty sooner than later.

After chatting for a few minutes at the rail, Kim let out a startled sound and I turned to see one of the friends we made had reached under her dress (not hard to do) and grabbed her ass. His name was Joe and his wife was laughing behind him, she was Brittany. They were mid 30s, attractive, looked like they worked out a lot. It was a very bold move but everyone got past it quickly. Kim got past it so quickly, that five minutes later she had his cock out stroking it as we all stood at the rail. She helped him shoot a load of cum into the ocean below, his above average cock going flaccid in her hand. Of course I took the opportunity to finger Brittany and get her off. She was bleach blonde, her pussy felt like she had probably been fucked by a few hundred guys over her life.

We all joked that we would see each other again (we would) and went on our way. At that point Kim decided she wanted to hit the hot tub. We headed back to the room and she started going through the endless swimsuits. Her first choice was a white bikini where the top was moderate coverage and the bottom was as scrunchy bottom that revealed a decent amount of ass. I immediately took it off her and asked her to try again. This time she grabbed a blue and green bikini and had the same top coverage and was also a scrunchy bottom but covered very little ass, much like a thong. I allowed that one.

We headed to the hot tub and found one with one other couple. They were late 40s/ early 50s Hispanic. In decent shape, she was curvy with big tits busting out of her top. He was Stephen and she was Jennifer. We settled in and began to chat with them, typical stuff. We found out that they had been on a few of these before and liked to swap in same room. Fun. I don't think either of us were really that interested, Altho they seemed nice and very easy going.

Another couple joined the hot tub, neither in great shape, mid 30s. The guy was decently overweight, although his giant balls were obvious in his bathing suit. She was less overweight, giant tits also. He was John and she was Lianne. This was their 2nd vacation like this and they were open full swap. Probably not for us, although I caught Kim looking at his seemingly giant balls as he entered the water.

Finally another couple entered, a little more our speed. Mid 30s, he was black and she was Hispanic. Both in reasonable shape, he was about 6'3", she was 5'1" so a giant discrepancy. They were very nice and had never been on a cruise but were familiar with swinging. He was Derek and she was Monica. She had a good set of boobs but not overwhelming.

Now eight of us and it was a bit more crowded. I had Jennifer next to me and Kim had Derek next to her. The conversation got livelier and a general consensus was formed that tops should come off, no complaints. Jennifer and Lianne's tits flopped out and nearly took up the entire hot tub. Jennifer's boob actually was up against my arm it was so big. The girls decided that if their tops came off, at least one guy had to lose their bottom so we played a game where the guys had to guess the exact size of boobs of each woman. The guy who was most incorrect had to lose their pants.

Unfortunately and fortunately John had no tit awareness and easily lost. He was by far the least attractive guy, but his seemingly huge balls were not a mistake. His balls looked like baseballs and his cock was surprisingly long as well. The girls smiled and complimented his large package, and Monica even cupped his balls a little as a joke. He obviously got rock hard at that and quickly got in the water. Unfortunately for him Lianne wouldn't let a hard cock go and started stroking him under the water.

That turned on Jennifer next to me and I noticed her start to stroke Stephen. I was ready for Kim to take care of me, but instead I felt her start to shake and look over to see her other arm going up and down on Derek's cock! Monica smiled as she noticed also. Unfortunately I was now sitting hard as the only guy whose cock wasn't being serviced.

I motioned to Monica and she swam around Derek and Kim and sat on my knee. I very carefully glided a hand to her bikini, and slid it inside to find her nice shaved pussy. It was a tight snatch, I wondered if Derek had a BBC and if he did, how much effort it took to fit inside. At this point a lot of moaning was going on as the hot tub had three hard dicks and one wet pussy (I was hard as well).

At this stage I wasn't as shy anymore, perhaps not shy at all, and so I discreetly moved Monica from my knee to placing her ass on my hard cock. I was still able to reach around and finger her, but got the benefit of her nice round booty grinding on my very hard cock. Fortunately for me, the group was very distracted and I was a pro. My bathing suit purposely had a way to open the fly and unleash the snake, which I did easily.

Monica turned and gave me a little grin as she could tell her thong bikini ass was now grinding on my cock without anything in the way. She rotated her hips a little ways, and reached her hand down to slide away what little fabric her bikini had. Next thing I knew my cock was fully engulfed in pussy. It wasn't as tight as I expected, and I suspected Derek must be packing plenty of heat.

It took two or three minutes,but eventually Derek looked over and asked, "Are you riding his cock?"

Monica slyly smiled, "Maybe..."

Derek just smiled and leaned back, enjoying a vigorous effort by Kim.

It was about that moment that John's large balls and cock erupted, his hips shooting up and his cock making surface as some of his cum shot out. Now the unfortunate part (and something that you have to live with on a swingers cruise) is that Johns giant load of cum was in the hot tub floating around everyone. It was pretty much silently decided that we didn't want to continue to play in John's cum, and so everybody got out of the hot tub. Stephen was our first, his hard average cock nearing orgasm, followed by Jennifer, her tits swinging.

Then Derek stood up and his BBC was no joke, a long 9" pipe that was perfectly even and straight. Kim got up after him, reaching around to continue tugging on his cock. Then Derek did something I didn't aanticipate, he turned, picked up Kim underneath her ass and carried her about 15 feet to a recliner chair, moved aside her bikini and began pounding her. In the matter of seconds he went from a handjob to destroying Kim's pussy. I could only imagine if her boyfriend knew she was on a vacation where she had already fucked her lover, given a handjob to a stranger and was now having her pussy bottomed out by a stranger BBC.

Made me so horny that my cock hurt it was so hard. Fortunately Monica was right there and she wasn't done with me as she guided me to the ground, inches from the edge. She hopped on top and began riding my cock like a good girl, bouncing her sizable ass up and down, accepting my cock all the way. I could hear Kim moaning as she was being railed, his balls making audible slapping noises as he drove into her. I had no clue where Stephen and Jennifer were, assumed they watched. John was still in the hot tub, watching the action outside.

I heard Derek moan as he blew his load into Kim and that helped me explode into Monica as I grabbed her ass and thrust my dick as deep as it went and rolled us around so that I could thrust my loads into her. For whatever reason I had a very large load and shot around ten streams of cum into her, filling her up.

Derek and I both pulled out, our limp cocks swaying in the room. We kind of laughed and exchanged places, going to check on our respective girls.

From there we all gathered our things and made our way, saying we hope to see each other again.

We made land the next day, and stopped at a specific resort for the day/night. There was a big party and events scheduled for the night by the staff. We spent most of the day hanging at the beach, Kim showing off her ass in a micro black thong bikini (two strings of fabric, with one string going between her pussy lips). She wasn't playing around. We chatted with two couples, both in their early 30s and very attractive.

Couple one was Mark and Steph. Both were white, he was about 6'1", obviously lifted weights frequently and was an attractive guy. She was about 5'3", but toned with obvious fake C tits (she went topless), blonde hair that was dyed.

Couple two were Eric (not exactly) and Amber. He was Croatian and she was from American but of Thai heritage. He was about 6'5", good looking guy, in shape but not overly muscular. She was 5'5", slim body with surprisingly nice tits (B/C) and a very tight booty.

We hit it off with both couples, had some fun chatter but nothing else. I think all the guys were having trouble keeping from staying hard; as mentioned Kim had on the smallest bikini possible, Steph was topless with a thong bikini bottom and Amber had on a little more clothing, although the bottom was also in a thong style. Based on what we had seen on the cruise, these were some of the more attractive people.

That night we fucked once we got back to the hotel room at the resort, I was horned up from seeing tits and ass all day and needed to bang my good slut. We both got ready, it was Caribbean themed and so I put on a dumb flower shirt with swimsuit shorts and Kim put on a little Hawaiian type skirt with a thong bikini underneath and a top that was basically just a bra, showing her entire stomach.

We headed to the event which was around one of the pools and general area around it. Very quickly it became clear that the "staff" who were putting on the show consisted of a bunch of very attractive men and women wearing little. The night progressed, drinks were served, food was available and the staff held games and contests meant to be on the risqué side. The male staff members flirted with all the women, most of them wearing some type of Speedo/male thong.