I’m sure there’s a lot of us that have been on an all inclusive vacation or a cruise to some exotic destination and seen an attractive young man or woman the we thought about being with, even if it was only for a night. However, because we’re with some friends or maybe even that special someone that we’re also very attracted to, we never pursue it, but then later we wish we had.
I’m sure there’s a lot of us that have been on an all inclusive vacation or a cruise to some exotic destination and seen an attractive young man or woman the we thought about being with, even if it was only for a night. However, because we’re with some friends or maybe even that special someone that we’re also very attracted to, we never pursue it, but then later we wish we had.
A few years ago, I got to travel to Cancun with a few friends for a long deserved vacation. I was excited to get away for a week and being it was on the beach in Cancun, and it was an all inclusive resort, where we could eat at any of the hotel restaurant and drink at any of the bars, including the swim up ones, I could hardly wait.
Stepping off the plane and onto the tarmac, the heat hits you right away and as we hurried through the airport and boarded the hotel shuttle, our enthusiasm continued to grow. It was only a short ride to our hotel and once there, we all headed up to the front desk. Talking and laughing about what we wanted to do first, we decided we’d meet at the beach, and after we all got our room keys, we quickly went to our rooms to get settled in.
Our rooms were in the same wing of the hotel but of course they were scattered in different parts. My room didn’t face the ocean but I did have a pretty good view. It was great, very spacious, with a king sized bed, but wanting to see the ocean, I quickly changed and went down.
It was already midday when we met up at the beach and as I looked around, I couldn’t believe how beautiful it was. The beach had white sand, beautiful turquoise blue water, and it was dotted with little cabanas everywhere and plenty of lounge chairs too. We hung out there for a little while, going swimming and drinking, but as it started to get late, we decided to go back to our room and then meet up again to check out the restaurants.
It was fun to be footloose and after getting cleaned up a little, I met them down at one of the little restaurants that was down across from one of the hotel pools. There were quite a few restaurants and bars on the premises so it was hard to choose, and the one we decided to eat at, had a theme but they were all buffet style, at least the ones included in the all inclusive deal.
On one of our visits to this same hotel restaurant, we were lucky enough to have a waitress the was not only super friendly, and attentive, she was also very attractive. She was of course Latina or Mexican, but spoke very good English, and even though it was broken, interacting with her was a joy. She was very attractive, kind of short, had dark, shoulder length wavy hair, very tan, and even though she had a firm looking little body, she was thinly framed. On this particular occasion, she was wearing a tight little black skirt that showed off her legs, a red low cut top that accentuated her firm small little tits, and a bra that pushed them up, giving her cleavage.
Like, I said, she was very friendly and I found myself instantly attracted to her to the point where I went to that same restaurant for breakfast, lunch, and dinner, always hoping to see her.
Eventually, I found out that her name was Maria, and the next time I saw her I said, “You’re always here, aren’t you.”
This made her smile that I remembered her and as I smiled back I jokingly asked, “What do you do when you’re not having to work?”
I wasn’t sure she understood what I was asking, but she said, “I don’t know, I usually go home,” and smiling, she picked up our plates, and walked away.
As she left the table, my friends commented that I must really like her and then jokingly one of them told me I should ask her out. I was already seriously thinking the same thing but how could I possibly get her to meet up after she got off work? Continuing to contemplate how, I decided to try to time our leaving so I could stop her and nonchalantly ask her as we headed out.
Maria seemed a little nervous, as I stopped her and asked what she was doing after she got off. Hastily looking around, obviously nervous about something, she seemed worried as she nervously looked back at me and then in a concerned voice she told me, “I don’t know if it’s allowed.”
“You don’t know, if what’s allowed,” I thought, but then smiling I said, “Sorry, I didn’t know that was frowned upon.”
She obviously didn’t understand but I sensed she wanted to see me after work, and after looking around again she leaned toward me and said, “I’m done at two.”
Smiling, I quickly suggested, “How bout we meet down here at the pool?”
This made her cautiously smile and after nodding her head, she agreed. Shaking her hand as I left, I hurried to catch up with my friends. I was obviously grinning from ear to ear, beaming with excitement, but then thought, “God, I better have a plan.”
I explained to my friends what I had done, and one of the guys said, “Way to go,” which got the attention of his girlfriend that gave him a shoved saying, “Hey!”
Smiling as I headed up to my room, I hurriedly changed into my swimsuit and then quickly headed down to hang out by the pool we had decided on. It was kinda crowded but it was a huge pool and as I moved over by the swim up bar, and ordered something to drink, I impatiently looked around for her to show up. Continually looking at my watch, I started to feel a little anxious about the whole thing, and after a little while, I figured she was blowing me off or that maybe someone told her she shouldn’t. In either case, I felt she was rejecting my offer.
Suddenly, I saw her from across the pool, and trying to get her attention, I raised my hand waving at her. Finally when she saw me, she smiled and after a subtle wave, she again suspiciously looked around. She was in a white macrame style beach throw that kind of covered her, but not really. I thought she was pretty and the restaurant but seeing her like this, I couldn’t believe it.
Maria threw her towel on one of the pool lounge chairs as she got close and then taking off her throw, she tossed it on the chair too.
She had a great figure, tight tan little body and seeing her in that skimpy powder blue string bikini made me smile in anticipation. Staring in awe, dumbfounded by her beauty, I awkwardly moved toward her and as I greeted her in the shallow end as she went down the pool steps, I said, “Hi.”
Maria smiled as she continued into the pool and after shaking her hand as we got close, I said, “Wow, you look great.”
I felt really nervous to be with her, being she was so pretty, but as we moved over to the “swim up” bar and ordered a couple Pina coladas, I started to feel a little more at easels we started to drink. Maria was great, and yea she was probably a little nervous too. Moving away from the bar a little, to a more secluded part, we started joking with each other, splashing and innocently touching each other, even hugging.
It was fun, to be with her and after having more than just a couple foo foo drinks that went down way to easy, Maria happened to kiss me on the cheek. It surprised me and when I asked, “What was that for?”
She shyly smiled and said, “Thanks for asking me out.”
Smiling back at her, I grabbed her waist and after telling her, You’re really fun,” I leaned toward her giving her a kiss. She seemed a little embarrassed and after looking around again, she said, “Maybe we should go.”
I think she was trying to not be seen by her co-workers, in any case I said, How bout we meet up later and get something to eat.”
She smiled and hugging me she said, “Sure.”
As we got out of the pool and dried off I told her, “Okay, I’m going to go get cleaned up a little.”
Maria now wrapped her towel around her waist and after putting her throw back on she asked, “What room are you in, I’ll come up after I change.”
Immediately I told her, “You can change in my room and take a shower up there.”
As she searched for what to say she smiled and said, “I didn’t bring a change of clothes with me.”
Nodding, I shook her hand and as we walked into the hotel and went our separate ways, she was all I could think about. In my room, I quickly took a shower and threw on a shirt and some shorts. Thinking and hoping Maria and I might just end up doing it, I thought, “Maybe I shouldn’t wear any boxers.”
The shorts were almost like swim shorts and after throwing them on I sat there, waiting impatiently for her to show up. Suddenly there was a soft knock at the door and as I looked through the peephole and saw it was her, I took a deep breath and opened the door. Smiling as I took her hand, I asked her in, which made her smile too. Closing the door behind her, and turning to face her, I couldn’t help but give her a hug.
Looking at her and thinking how bad I wanted to be with her, I hugged her again and gave her a kiss. She really was pretty and the dress she was wearing accentuated her little body to the point where I looked at her and said, “Wow, you’re beautiful.”
Seeing her smile, as I continued to check her out, looking her up and down, she did the same to me. Her wavy hair and smile was great, and the short red and black skirt that she was wearing showed off her thighs, making me instantly look up. Maria was smiling too, and feeling a little anxious I said, “You look great.”
Maria shyly looked down and as I instinctively looked down too, I couldn’t help but look right down her top at her cleavage. She had on a tight black, low cut top that really made her boobs look great, and seeing her little nipples pushing against it, I constantly found myself looking down at her chest.
Hastily looking up, catching myself staring, and seeing her smiling, there was no doubt she had caught me. Looking up at her, she smiled nervously and then turning, she moved over to the bed. As she sat down and adjusted her skirt, al I could think about was wanting to get her in bed, and seeing that pretty smile and the red lipsticks she was wearing, really made me excited to think about being with her.
As I moved over to the bed and sat down next to her she said, “This is really nice.”
There was an awkward pause as I search for something to say, and as I looked at her, I think she was nervous too. I wanted to lay her back, I wanted to take advantage of her right there, but being nervous myself and not wanting to ruin it, I tried to contain myself.
Feeling we needed to get out of there before I made a fool of myself as we sat there, I asked about dinner. Maria shrugged and then as we discussed where to go, I asked, “What’s your favorite restaurant?”
She seemed a little taken back that I would be concerned with what she wanted but after settling on one of the restaurants on the other side of the complex, we stood up and left. As we headed that way, all I could think about was how nice it is to be with her, but also how can I get her in bed too .
Sitting down in the restaurant, we ordered some drinks and some appetizers, and ended up talking about our lives and families. It was nice but when she asked if I was married or if I had a girl friend, I had to lie. Yea, I had a girlfriend back in the states and when I asked her the same thing, Maria told me she lived at home with her parents and explained that she had to help support her parents and three siblings.
It was heart wrenching but I tried to put on an understanding face, and then wanting to change the subject I asked, “Do you have a boyfriend?”
She seemed hesitant and then smiling she said, “No.”
Looking at her, I smiling and couldn’t help but think she was holding back, probably for the same reason I was.
After paying the bill, we left and as we walked through the lobby Maria suggested we hit one of the clubs. Smiling I agreed and as we got some drinks and danced a little, I suddenly started to feel more than a little drunk. I’m sure she was feeling no pain too and when I suggested we should go, she nodded and smiling, she grabbed my arm.
Leaving and heading up to my room in the elevator, I took her hand and pulling her toward me, I leaned down to again kiss her. Closing her eyes and put her hands on my hips, she stretched up to kiss me. As Maria tilted her head and we kissed I thought, “Man, I hope this goes well.”
It was a quick ride up in the elevator but when it suddenly came to a jerking halt, we ended up pressing against each other. Smiling and giggling as the doors open, Maria grabbed my hand as we stepped off the elevator. Walking hand in hand down the hall to my room, I sensed some apprehension, not only on my part but her as well.
As we reached my room, I fumbled to take out my card key and as I held it against the lock, and opened the door, I led her in. As she continued into my room and again looked around she turned and smiling said, “This really is nice.”
Smiling back, as I sat on the edge of the bed, I casually prompted her to sit next to me. Slyly looking at me for a second,Maria moved to the other side, and as I watched, she climbed up on the bed. Turning to watch, I eventually stood up and as I faced her, she foxily crawled to the middle of the bed, seemingly suggesting for me to get on the bed too. Smiling, I cast the covers back a little and as I leaned onto the bed, Maria seductively smiled.
Climbing on the bed with her, we ended up kneeling and as we faced each other, I put my hands on her waist. She really was pretty and as I leaned into her, she closed her eyes and as we kissed, she put her hands on my waist too.
Maria then subtly moved her hands up my shirt, feeling on my chest and as we continued to kissed, I reached up to feel on her boobs. I knew she didn’t have on a bra, she really didn’t need one, and smiling as I felt on her firm little titties, I immediately started to get hard.
Moving around behind her as we knelt on the bed, I lifted her shirt slightly, and as I moved my hands up her blouse, continuing to feel on her boobs, she tilted her head back, so we could again kiss.
Sucking her neck now as I felt on her tits, I casually let my one hand slide down to her crotch. Maria now turned and as we faced each other, she smiled and then reaching down, she groped for my cock. When she eventually felt it, I could feel her smiling and as we stopped kissing, and we looked at each other I asked, “What?”
Maria shook her head smiling and then said, “I don’t usually do this kind of thing.”
“Oh no,” I thought but as we looked at each other Maria said, “I need you to know something,” I smiled and listened intently.
“What was she going to tell me,” I thought, but then when she said, “I do have a boyfriend,” I was kind of shocked.
I wasn’t sure why she was telling me this, but seeing her smiling, obviously looking for a reaction, I told myself, “I thought you said you didn’t,” as I continued to look at her.
I felt that maybe she was just saying it and as we looked at each other, I suspiciously asked, “Do you wanta stop?”
I didn’t want to stop, and seeing that it made her smile, I knew she didn’t want to stop either. Maria then seemed to back pedal and when she kissed me and said, “It’s okay, we really aren’t serious,” I pulled her close.
I didn’t know if I should keep going, but seeing her continuing to have a big smile, I said, “Maybe we should stop,” needing a definitive answer.
Maria leaned toward me and as she hugged me and we kissed she said, “No.”
Smiling excitably, I kissed her again and as we started to make out more passionately, feeling on each other as we kissed, and as I started to feel hot, I peeled my shirt off. This made Maria immediately start to feel on my chest again and when I tried to take her top off, she stopped me, but only briefly.
Pulling her top over her head and throwing it off the bed, I couldn’t help but smile as I looked at her tits. Looking up and giving her a kiss, I reached down and started to undo my shorts. I hoped she’d reach out and want to help and as they hung open, she looked down as I leaned away. Seeing her smile, I reached out and when I pulled her close, she tried to put her hand down my shorts. Grabbing for my cock, Maria looked up and smiled when she realized I didn’t have on underwear. Smiling myself, I inched my shorts down more, and as I laid back and kicked my feet out, Maria immediately pulled at my shorts. As we got them off, Maria looked up at me smiling as I leaned up on my elbows.
Maria’s gaze quickly went to my cock and as she started to rub it, I could see her smiling as she deliberately moved her hand up and down the length. Without hesitation, she suddenly went down, and as she took my cock in her mouth I though “Oh my god,” as I lay back.
It felt good, so good, I wanted to cum but, I wanted to fuck her, especially now that I knew she was open to it. Reaching down hold her head, letting her do it, I eventually leaned up and grabbed her. Stopping and looking up at me as I tried pulled her up, she smiled.
Maria eventually let go of my cock and as she moved up, and I had her slide on top of me, we kissed.
It was so hot and wanting to be in her, I rolled her to her back and got on top of her. Kneeling in front of her, I looked up at her and started pulling down her skirt.
Immediately, I felt on her pussy through her panties. I wanted to fuck and as I went down and mouthed her pussy, she gasped. Pulling her panties down and moving between her, I leaned on top of her and as we kissed Maria asking, “Do you have any protection, you know a condom?”
I did and as I leaned back up and went to get it out of my short she said, “I’ve got one in my bag.”
Looking at her inquisitively and seeing her smile, I smile too. Quickly sliding off the bed, I rummaged through my short pockets and after finding it, I smiled and got back on the bed. Holding out her hand, wanting me to give it to her, I smiled and after opening the package, she took it from me.
Laying on my back now, Maria smiled and then immediately tried to roll it down over the head of my cock. She was obviously nervous and so I reached down and helped her roll it down the length. She was visibly excited as she looked at me, and as I coaxed her to climb on top of me, she did. Straddling my waist, I pushed her back, and as I tried to guide my cock into her wet little pussy, she reached back to help.
Maria took charge, and when she slid the head of my cock between the lips of her pussy, and she leaned back, my cock seemed to easily slip in. It was tight and definitely warm inside her, and after looking down at me, almost in a trance, she slowly started moving up and down.
Wanting to be deeper inside her, I put my hands on her waist and scooting her back, she put her hands on my chest. Arching her back slightly, I reached up and as I felt on her tits, she looked down at me smiling. Maria leaned down now and after a kiss, she again moved up and down on my cock, but a little faster now. It felt so good, and as I bucked my hips up, I knew it wasn’t going to take long. Yea, her pussy was wet, but it was still really tight and before I knew it, I was going to cum.
Maria had her eyes closed, obviously concentrating, and I sensed she wanted to get off too. Continuing to buck my hips as she bobbed up and down, I really wanted her to cum too. Smiling, as she leaned forward, and after a kiss, I felt I wanted to be on top.
Pulling her down and kissing her, I tried to roll us to the side, which of course made my cock slip out. Looking at me she asked, “What’s wrong?”
Nothing was wrong and after getting her rolled to her back, I quickly climbed on top of her. Smiling, I asked her, “Are you okay,” which made her smile and adjust herself under me.
Giving her another kiss, I reached down and pushing my cock back in her, she spread her legs a little more. Immediately, I trying to fuck her, I put my hands under her shoulders, and resting on my elbows, I put my head next to hers. Maria put her arms around my neck as I continued to thrust into her, and when I started to breathe a little hard, I wanted to cum.
Suddenly I felt it, and stopping I said, “I’m going to cum.”
Holding me tight as my cock started to pulsate and cum spewed out, filling the condom inside her, I tried to hold her still. It felt so good and when I tried to move my cock in and out of her again, I again asked if she was okay. My cock continued to buck, but only faintly and when I looked at her, Maria smiled and then hugging me she asked, “Did you cum?”
I’m sure she could feel the warmth, but I think she felt the need to ask and after kissing her again I said, “Oh yea.”
My cock had started to go limp now and as I started to pull out, I made sure to reach down and grab the condom before it slipped off. Lifting off her as I pulled out, we both ended up looking down. Seeing the condom hanging off the end of my cock, heavy with cum, I smiled, and after grabbing it and carefully sliding it off, I held it out. Looking at her and seeing her smile, I twisted it so it wouldn’t leak, and after dropping it off the edge of the bed, I deliberately flopped next to her.
Maria continued to smile and then as she leaned toward me, she held me, we kissed. Pulling the covers back over us I smiled and said, “That felt good.”
Maria smiled too and hugging me again, she turned to face me and said, “This was nice.”
Giving her a big hug, I kissed her on the head and as we lay together, we ended up falling asleep.
It really did feel good, but as I woke up in the morning, she was gone. Laying there wondering what happened, I worried that I might have done something. Looking around, to see if anything was missing, I noticed that the condom was gone. “Where was it,” I thought, but as I went into the bathroom to take a shower there it was in the trash.
Smiling I thought, “Had she cleaned up?”
I didn’t know what to think but then later that morning, I went looking for her in the restaurant downstairs, it was immediately obvious that she wasn’t working. I wanted to see her and talk to her but I was scheduled to leave the next morning. “Would I ever see her again, I thought?”
The next day when I got ready to leave, and I went down to the lobby to check, I saw her across the lobby. I wanted to go over and talk to her, but it was obvious she working. Maria did look over and smiling, I felt she was down there to see me before I left.
I have wanted to go back to Cancun to see her again, but it has been a long time now since we spent the day together. I think about her now and then, and still want to visit in hopes of seeing her again.