6 comments/ 79791 views/ 2 favorites Cabo Fun Ch. 01 By: cleenwheels Winters are brutal in the Midwest. So, when my friend called with an idea to get seven or eight guys together for a trip to Cabo in February I was immediately in. Now all I had to do was convince my wife that I needed to go! After a couple of weeks of being on my best behavior, I asked her and she surprised me by saying yes immediately. I sensed this would cost me later, but that was immaterial at the time. I called my friend and told him I had the green light. Fortunately, everyone else had gotten permission to go as well. My friend has a condo in Cabo and had made this trip a couple of years earlier. I had to miss that trip because my wife was pregnant and forbade my absence from her. The stories from that trip were legendary, and I know she always felt a little guilty for not letting me go. I'm sure that this helped my cause. Plans were quickly made for the trip and in no time we had tee times, fishing boats and dune buggies lined up. Six days and nights of fun awaited. Upon arrival in Cabo the debauchery began in earnest and Teutonic amounts of alcohol were consumed. We proceeded to golf, fish, and generally drink ourselves into oblivion. All of us are near 40 and this was a great chance to feel young and free again. And believe me we were feeling young and free. Every day after our selected activity we would end up at the condo pool for happy hour. Ninety minutes of two-for-one drinks and some poolside lounge time. We started playing a little water volleyball just so we wouldn't drink so damn much before dinner. Then we would head out, find a nice restaurant and end up at one of the local bars to watch the nightlife. The nightlife in Cabo is spectacular! If you've never been, you must go. Most of the time we just ogled the beautiful women and occasionally, we would find a willing dance partner to boogie with. But we were all married and just having a little harmless fun. On day four we started our now regular water volleyball game and were joined by three women who had just gotten to the condo for their annual girls trip. They were from California and were close to our age. All three were incredibly fun and friendly. They were all in great shape and looked great in their bikinis. Two of them were in sales and the other was a fitness instructor. After the first day, I ended up talking to them for about half an hour in the hot tub after our volleyball match. Just casual chit chat and nothing more. I said goodnight and headed up to shower and join the boys for another epic night of drinking and ogling. The next day we were done a little early with our activity and as I walked down to the beach I spied the three California girls. I walked over and said hello. Cara, the fitness instructor seemed especially friendly and pulled out some pictures of her kids. She asked if we were playing volleyball later and I replied that we were and she said they'd see us later. That night, the girls switched teams and Cara played on my team. A couple of times we got tangled up going for the same ball at the same time. I couldn't help but notice her taught body as we untangled. We finished up the game and I lingered in the hot tub for a while with them. This time all three of them seemed even more friendly but I decided that I needed to play it cool. I really had no intention of anything sexual at this point, but they were fun, attractive, and flirty. I was finding out that flirting was pretty fun. It is even more fun when both parties know that nothing is going to come of it! We pretty much stuck to our formula of eating well then finding a hot night spot to get tanked and marvel at the incredible plethora of good looking women. We were starting to wind down and only had one more day and night left before our plane left Cabo and took us back to reality. Probably a good thing as I was beginning to feel my liver swell. The last day we didn't have anything planned. Just a day to lounge at the pool and catch some rays at the beach. I grabbed my snorkeling gear and headed for the beach. On the way to the snorkeling spot I spied Cara running down the beach towards me. She looked fantastic as usual. She saw me and stopped close to me to chat. I noticed that the space between us was shrinking and she was definitely encroaching on my comfort zone. I could tell she was teasing me, and I did my best not to look uncomfortable as she leaned closer to talk to me. As our conversation ended she asked if we were on for volleyball again. I said I wasn't sure, but since it was our last night we probably wouldn't deviate from the formula. Her eyes immediately saddened when she heard me say "last night." She startled me by reaching out and stroking my arm as she said "See you later" and jogged off. I didn't notice any sparks during our volleyball session which actually relieved me quite a bit. After happy hour was over, Cara casually asked what our plans were for our last night. I told her that I wasn't sure, but I knew that we would end up at Cabo Wabo. She turned and left and said she'd see me later. Secretly, I hoped I wouldn't see her later. I had never seriously considered cheating on my wife, but I'd never really had the opportunity. In ten years of married life only once had anything remotely tempting happened, and I had deftly avoided indiscretion. The question that was beginning to form in my mind was; Could I avoid it again? Cabo Fun Ch. 02 So, after our last water volleyball game I lingered with the girls in the hot tub again. They asked where we were going that night and I told them we were probably going to just play it by ear. There was a famous night spot in Cabo we hadn't been to yet, and I told them we would probably end up there eventually. I excused myself and went up to shower and get ready for dinner. The mood in the condo was a little more subdued than usual. I guess it was our last night and we had been partying all week so a little letdown was natural. We were all starting to think about going back to home, work, and families. It was a bit sad really, but the truth was that neither our livers nor our wallets could handle another week like this for a while. On top of that was the fact that we had been surrounded by top-notch women all week and the look but do not touch mantra was beginning to wear thin. The sexual tension was palpable. I too was looking forward to getting home for some much needed release with my wife. We found another great restaurant and dined on fresh seafood. Usually after dinner we were ready to hit the bars, but tonight everyone was tired. I could tell that we were going to have a quiet night, or so I thought! We lingered on the main street and did some window shopping. We walked by the fishing boats and lamented the fact that we didn't have another day to try and catch a marlin. We were just sort of wandering aimlessly when we came upon the famous nightspot. It was Thursday about 9 pm and by all accounts the crowd was a little bit light. Just as we were wondering if we should stay or go, we saw our three volleyball friends walk in. A thrill went through me as I saw them walk in. I really enjoyed their company. They were smart, funny, and safe. Safe in that they were married and platonic fun was still good fun. But what really got my attention was Kara. She was a vision. We had only seen them in the pool. We had only seen them in their semi-conservative bathing suits, but tonight they were dressed up, made up and definitely hotter than ever. Kara had make the biggest transformation. She was wearing a blue spaghetti strap dress that was just right. It was a silky dress that showed her feminine form without being so tight it was trashy. She was obviously one of those rare women who knew how to dress to impress. She was dressed sexily but in a conservative way. Her hair was down and she was wearing just a bit of makeup. She was divine. All of a sudden our evening had gotten the jump start it needed. The girls made it obvious that they wanted to have some fun and we weren't going to let them down. We found a table and promptly ordered a couple of buckets of beer and some tequila shots. After a couple of drinks, a band took the stage and started playing some great rock and roll. They played some new stuff and some old stuff. It was the perfect mix. In between sets the DJ would play newer dance stuff. I was dancing practically non-stop. I was having a great time trading off dancing with all three of them. At one point, Tina took my shirt off and threw it across the dance floor. There I was, dancing in only my shorts and flip flops. I felt someone's hands on my back and turned around surprised to see it was Kara. My shirt was returned to me by the bouncer who said if I didn't put it on I'd have to leave. I promptly re-robed. I headed back to our table and took a look around the bar. The whole place was crazy! People dancing on tables and chairs. Some girls in mini skirts were dancing on the bar, and they didn't care that you could look up and ogle their underwear choice. The whole place was crazy! It felt like the floor was rocking. I was at the table getting another beer when Kara came up behind me and clumsily put her hand around my waist into my front pocket. I knew my friends didn't see this as it was coming under the table. I tried to act cool as I gently removed her hand. She had gotten a pretty good feel of my package. As I turned towards her she just non-chalantly looked away, licked her lips and grabbed another beer herself. All I could think was; wow, did that really just happen? Just then the waitress arrived with a fresh tray of tequila shots. I licked my hand, added some salt and prepared to down my shot. Kara promptly grabbed my hand sucked off the salt and did her shot. I looked at her dumbfounded. Before I could say anything, she had offered her wrist and a salt shaker. I figured what the hell, you only live once. I gave her wrist a good lick, added some salt, sucked it off and did my shot as well. Smoothest shot of tequila I'd ever had. Kara grabbed my hand and led me back to the dance floor. This time our dancing was a little more intimate. She was close and had her hands under my shirt and was scratching my back. I didn't know how to react at first. I kept looking back at my friends, but they weren't paying us any attention at all-thank God. She grabbed my hands and placed them on her waist. I could feel her panties through her silky dress. She was obviously wearing one of those thongs that was so minimal it was really just held in place by small elastic rolls a little thicker than a rubber band. I found myself gently fingering them and at one point I gently snapped one just to get her reaction. She had no reaction at all except to continue stroking my back as we danced. Now I was worried. Next she reached into her purse and produced two pieces of gum. She popped one in her mouth and one in mine. I chewed as I danced and as I turned to face her, she put her arms around my neck and pulled herself up and planted a wet kiss on me. Impossible to refuse I kissed back. I heard some noise and looked up to see my friends giving me the penalty flag. Kara had her hands in my pants and was finding that her kiss was having the desired effect on my member. I decided that I needed to get off the dance floor and back to the table. It had been fun so far, but we were getting close to a line that I didn't intend to cross. We got back to the table and before I could catch my breath, she had licked my neck and showered it with salt. I did the same and we did a simultaneous body shot. Now it had gone too far and I knew it. In a desperate attempt to pull myself from the inevitable, I made my way to the bathroom. I did my business, looked in the mirror and tried to form a game plan. I decided that there would be no more dancing and it was time to gather in the safety of numbers at the table with my friends. When I exited the bathroom Kara was standing outside with a bottle of water. Finally, some sense had taken over her. She said she was done dancing and wanted to go back to the condo but her friends weren't ready to go yet. She asked if I would walk her home. I knew a couple of things at this point; I was drunk, She was drunk, A little fresh air wouldn't hurt, and I didn't need any more alcohol. We left together. Cabo Fun Ch. 03 The walk back to the condo was relaxing. Without the music and the dirty dancing we had a civil conversation and I was feeling more at ease. Besides, once we got back to the condo there was really nowhere to go and be alone. We went down to the beach and she and I talked for about thirty minutes. Then she leaned over and kissed me. When she withdrew, she said "Lets find somewhere to go fuck." That was it, I was all in. My room was out because I didn't need my six friends walking in on us. Even though it was a two bedroom suite, there was nowhere to hide. I work pretty closely with all six of them, and all of their wives are friends with my wife. This made my room a poor choice. It turned out that she was in a one bedroom condo with her two friends so we were a bit S.O.L. Just then I spied the cabana on the beach. It was about 1:30 am and the place was dead. I led her into the cabana and found a couple of massage tables in the corner. I closed the curtains and put them together. We hopped up on them and I offered her a massage. She slipped the straps off her shoulders and her dress fell to the floor. She hopped onto the table wearing only her bra and a g string. I quickly got naked and slid beside her on the table. I undid her bra and placed her face down on the table. I climbed on top of her and straddled her legs. I confess I am an ass man, and I admired the most perfect ass I have ever seen. I slid the g-string off and she moaned softly. Just as I started my erotic back massage that turns women into putty, I heard a voice from outside, "Sir it is security, that cabana is closed." No way this was happening! Everything was perfect until this point. Well, maybe it was divine intervention, karma, whatever. At this point we got dressed and left the cabana. Fortunately security wasn't upset and they just let us go. We wandered for about 20 minutes and were about to say goodnight when her roommates walked by. They didn't see us, but Kara said they slept in the bedroom and she had the pullout, and in about 20 minutes we would have privacy. I could see my roommates had returned and no privacy was available in our suite. Somehow, the next 20 minutes passed and we slowly entered her room. All was quiet and there was a hat on the doorknob. We weren't sure what that meant, but we weren't going to ask. She quickly led me to the pullout which had already been turned down. In our hasty retreat from the cabana, she hadn't bothered putting on her underwear, so she slid out of her dress again. There was soft light in the room which gave me a great view. She was incredibly gorgeous. Her long brown hair flowed around her glowing face and her eyes sparkled with excitement. Her perfect C-cup breasts stood at pert attention. Beneath her breasts lay an incredibly toned flat abdomen which led to a silky smooth shaved mound. Her labia were full and round. I was in heaven. She laid down and patted the bed. There was no turning back now. I quickly disrobed again, and I saw the pleasure grow in her eyes when she saw my penis. I admittedly have a very fit body and engage in multiple sports. I've never thought of my member as large, but it is average length and has much more girth than average. Like all men, I wish for that extra inch, but you have to use what you were given. Anyway, I sensed her approval which went a long way in getting me excited. I laid down next to her and we explored each others bodies with our hands. It was obvious we were both pleased. It was like discovering a new world. Every crease, bulge and valley was mapped with our hands. We chatted nervously, both of us saying that we had never done this before. Which was true for me and, I believe, true for her as well. She turned to me and said "I really want to do this, do you?" I replied that I did. It was a once in a lifetime experience that I did not intend to pass up. Unfortunately, I had no protection with me, but she assured me that she was covered. Once our consent was mutual our hands found their way to their respective targets. She was more than wet and as I placed my finger at her vaginal opening and kissed her, I could smell her desire. I was about to start my usual pussy caressing, when whe abruptly pulled my hand away and buried her head in my crotch. She licked my testicles and slid her tongue up my shaft. I looked down in ecstasy as this beautiful woman expertly brought my penis to full attention. She stopped and smiled at me then hopped on top and placed my cock at her vaginal opening. She slowly worked her way down until her cunt had swallowed every inch of my cock. She grinned at me and said "Mmm that feels better than I ever thought it would." I really had no reply. She leaned in closely and said "I've wanted to fuck you since day the first day I saw you." I was a little surprised because I really couldn't tell, but that didn't really matter now. I let her ride me for what seemed like forever and she came at least once. I was trying my damndest not to cum quickly and was holding out well. My penis never left her as we switched positions a half dozen times. We ended up in missionary and we were pounding away at each other. Our thrusting was animal intense. Our pelves would meet and grind with equal force in perfect rhythm. Without a doubt I was having my best sexual performance ever. After about twenty minutes of intense pounding, I felt that familiar pressure in my balls. I told her I was going to come and she pulled me tighter towards her and wrapped her legs around me. She squeezed every last bit of air out of me as my ejaculate flowed into her pussy. It was like a fountain of cum was overflowing out her cunt. Finally, I dismounted and we laid there silent catching our breath. She got up to get some water and I went to the bathroom. I looked in the mirror disbelieving what had just happened. I didn't really know how to feel. I had just cheated on my wife with a woman who had just cheated on her husband. I felt a little guilty, but it had been the best sex I had ever had. I walked out to the room and found her on the bed beckoning me back over. I looked at the clock and couldn't believe it was 3 a.m. already. My plane left at 9:30 and I needed some sleep. But I wasn't going anywhere yet. I laid back down and we shared our thoughts about the sex and the cheating. It seemed we were both in agreement; best sex ever, worth every moment, and something that probably wouldn't or couldn't happen again-especially as perfect as it was. She told me she came multiple times which I believed. Plus she told me she "liked my size." Apparently I was much larger than her husband and she had never really had experience with a penis as big as mine. I didn't really let this go to my head since I knew I was just a little above average. Of course, I didn't need to tell her that. If she thought I was King Kong, OK by me! It became fairly obvious we weren't done with each other yet, and she began pulling at my cock again. I was bit knackered from our first go around and needed a bit more refractory time, but with time rapidly fading I steeled myself for another round. Quite honestly, my penis was barely up to the challenge. I couldn't get it as hard as it needed to be as indeed she was very tight. I told her I needed some water and got a drink. When I came back I was completely flaccid and wasn't sure round 2 was going to happen. I had to try. So I suggested we 69, as this is something that always turns me on. I had forgotten that she hadn't cleaned up and I buried my face into her pussy to find I was eating my own cream pie-something I had never done before. The taste was interesting. I could definitely taste and smell my cum, but mixed with her sweet pussy juice it was so yummy. The smell and taste had my mind reeling and my cock hardening. Hard as ever now, I stopped and reversed myself and entered her. We started engaging in an epic fuck. With every thrust we were in perfect sync. Doggy style, reverse cowgirl, one leg up. She scratched my back and dug her nails into my flesh. It was all good. Her skin was like butter and her flesh was firm as I massaged and pulled her buttocks to me. She was cumming again and again, and I felt like I could last an hour. Time stood still. Finally back in missionary I started pounding her pussy as she screamed in ecstasy. Her head was off the bead and she was cumming wildly and loudly! I buried my cock deep in her as she squeezed me with her legs and left another load deep inside her. I rolled off wet with sweat and cum. We caught our breath and chatted some more. Neither one of us had any regrets. We lamented the fact that she lived in California and that I lived in the Midwest. I told her that she was the greatest and that this was the best sex I had ever had and she related the same to me. She asked if sex always lasted that long for me. Although I had been able to extend a bit longer than usual it wasn't much longer than my regular time. I told her that usually it was a little shorter, but not by much. I sensed that maybe she wasn't getting the best sex at home. About this time I looked at the clock and about shit my pants. It was 5:30 a.m. I had to go. We said our goodbyes and I dressed. A part of me didn't want to leave, but a part of me did. Fortunately, I didn't have any way of changing my plans. I headed back to the condo and found everyone passed out. I laid down on the couch and caught 30 minutes of sleep. I was awoken by our leader and told I had twenty minutes to get packed and down to the airport van. I made it but just barely. Of course everyone wondered where I had been. Since no one witnessed anything I had plausible deniability. I used this to my advantage although I'm sure they have their doubts that we just went for a walk and talked. Still, they all passed out about 3 a.m. so they didn't really know when I got back. My little secret. As I went to the airport bathroom I remembered I hadn't showered yet. My cock was damp and crusty, and I couldn't resist smelling our sweet intermingled juices one last time as I put my fingers to my nose.