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    Monday

    Beach Vacation

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    My wife, Jenn, and I have been married 15 years and together almost 20. We have 3 wonderful kids who are finally old enough to stay at our in laws for 10 days without needing constant supervision. We haven’t been away alone except for 2 overnight trips into the city in almost 12 years. We went to the Dominican for our honeymoon but we decided to go to a Sandals resort in Negril, Jamaica for our Winter vacation.

    In my eyes my wife is a Milf! She’s tall, long dirty blonde hair, great ass, small breasts and is still in pretty good shape despite pushing 40 and having 3 kids. Back in her 20’s she could rock a bikini and now at 38 she still looks really tasty to me at least. She felt differently and dressed quite modest and the only swimsuit she owned was a 2 piece that involved a tankini top and modest bottoms whenever she took the kids to the pool. I urged and more accurately begged her to buy a bikini or 2 for our trip. No one would know us and with no kids it was time to soak up the sun and drinks on the beach. She reluctantly bought a few bikinis and had begun heading to the gym a few months prior to our departure. I could tell she had lost a few pounds and toned up her tummy region before we left. I however had not seen the gym in forever as I work outdoors and I figure that’s enough of a workout. I’m 6 feet, 205 so it’s safe to say I could spare to lose 20 lbs or more.

    We had a very early departure from our snow covered province and arrived in the afternoon to our resort. Once we were off the plane the heat and humidity were very noticeable and I could not wait to make it to the hotel for a beer, a pair of shorts and sandals. Our room was quite nice and it had a balcony which I’d be using in the mornings as my wife is dying to sleep in while on vacation. Once we unpacked I grabbed my swim trunks, sandals and T-shirt and changed. My wife had changed as well into her bikini and although I had hoped for something more revealing I was quite happy to see her in something less mom like. She had a bright orange boy short bottom on with a dark floral print bikini top that showed off her small breasts as best as she could. The boy shorts bottoms are what caught my eye the most. The bottoms of her cheeks were damn near falling out. Of course she had to cover up with one of those wraps and brought a big beach towel to go with the towel I was carrying.

    We made our way to the beach and looked for some chairs but they were all taken so we just laid the towels on the ground. Being somewhat childish I dug a pit for myself to resemble a recliner chair and asked Jenn if she wanted one too? She replied “No, I’ll just take yours!” With that she took my spot and began reading a book while I made a new sand chair for myself. I was getting thirsty from the sun and headed to the bar to get us some drinks in our Contigo cups. When I returned my wife had shed her wrap and was applying sunscreen to her body. I snuck behind her and jokingly said “Would you like me to do your back Miss?” She laughed and handed me the bottle, leaned ahead and brushed her hair outta the way. I’m horny 24/7 and my wife knows it but she’s not into it like she used to be. We still have regular sex but it’s fairly routine and of course always in the bedroom. I have managed to bring toys into the bedroom and she never complains about having a vibrator inside her and one on her clit. When she cums, she almost always clamps her legs together and lets out a small moan. No wild thrashing or screaming.

    As I was applying the lotion I couldn’t help untie the knot on her top so I wouldn’t get lotion on her new bikini. I had hoped she would just let it fall and discard it but unfortunately she held her hands over her tits and then retied the knot. I told her “You can sunbath nude if you like? I won’t mind if people ogle my hot wife!” Jenn just laughed and said “You’d just love that wouldn’t you?” I of course would love to see her naked on a beach. After our drinks were gone we went for a walk down the beach to check out the other resorts. We often would walk into the resort to see the pool areas just to compare to ours. Soon it was 7 pm and I was getting hungry and tired from the long day so we headed back to our room, changed for supper and headed to eat. That night Jenn and I had sex and she slept naked for the first time in years.

    Day 2 was much the same except Jenn wore another new bikini. This one was a bandeau top with a typical bikini bottom which I absolutely loved. It concealed her breasts more but the lack of straps sure made me excited. Today we found some beach chairs under a makeshift umbrella hut which gave decent shade. We sat and read while sipping on our island drinks. I noticed the odd girl walk by topless along the beach much to my delight and I kept nudging my wife and mentioning she should do the same. Even though she has small breasts, they are very nice with big nipples that do get hard and are very obvious. For some reason whether it was the atmosphere or what I was dying to show her off. I was very lucky and proud of it.

    Once again we decided to head for a walk down the beach but headed the opposite way as yesterday. It wasn’t long and we were nearing the first resort. I noticed we had passed quite a few topless women and once we were up close I saw a buck naked man and woman walking towards us. My wife nudged back this time and said “why don’t you strip like that guy?” I replied with “You first, no one wants to see me over you sweetheart!” We walked into the resort to check it out and both of us were shocked to see lots of naked people lying around the pool and bar. We kept going and thankfully I had my sunglasses on so I could gawk at some of the women. Not all of them were attractive, some were easily 65, some in their 20’s and some anywhere in between. We headed towards another pool and when we got closer a worker stopped us and said no clothes allowed. Now he had my curiosity “No clothes at all in there?” He said “Hotel rules. This is the nude pool!” I had to know what this place was and why didn’t I book here. Hedonism he explained. I had never heard of it. I surely was going to google it tonight. The guy was super friendly and explained that we could purchase day or night passes to come on to the resort. We took in the scenery as he spoke and then I saw the biggest cock of my entire life walk just behind him. He was easily longer than I was fully hard and his cock was undoubtedly soft as he strolled by. He saw my wife beside me, stopped and admired her as he looked her up and down. He then opened his mouth and said to Jenn “Come on in, the pool is perfect!” I think my wife was speechless and in awe cause she was caught staring at his package. I was a little jealous to see her checking out this well hung guy but a little turned on at the same time. I offered my thanks to the worker to which he replied “No problem, come back anytime, guests are always welcome, mon!”

    We headed back towards the beach and went back to our room. We were both quiet it seemed as we changed for supper and headed to the bayside restaurant. It was my wife who first broke the ice and said “That resort was a bit eye opening eh? What was it called again?” “Hedonism” I replied. She then grabbed her iPhone and began typing which I assumed was a search of Hedonism. She began to explain the 2 different pools, prude and nude, and how anything goes at the nude side. Watching Jenn read and explain about Hedonism had my other brain at full attention as I got the feeling she was quite intrigued by the resort. I was dying to ask if she wanted to get passes and attend the party but wasn’t sure how to ask her. After supper we headed to the bar for a few drinks and chatted with a couple from England. We eventually retired to our room. I went into the bathroom to brush my teeth and because we never have sex 2 nights in a row I assumed I’d be soon asleep. I walked out into the bedroom and Jenn was butt naked spread eagle on the bed fingering herself. I was shocked to say the least, but needed no explanation or invitation. It was obvious Jenn was worked up and needed relief so I dove in head first and began licking her clit. It wasn’t a minute later and she was clamping her legs around my head and moaning hard. I couldn’t wait to fuck her. I adored her in every way and she looked more beautiful than ever at this very minute. I aimed my cock at her hole and fucked her hard and fast. I too wanted to cum and I wasn’t the least bit worried about lasting. I was soon cumming inside my wife and it was incredible. I rolled off of her and soon fell asleep.

    The next morning I woke up and headed to the balcony to google that resort for myself. What I read shocked me. There can be full on sex on the nude side in front of all to see. Special rooms for orgies and even toys. Also, a strict no means no and absolutely no cameras allowed. The thought of going there as a couple was intriguing. I have to admit getting a BJ from a few of those women I saw yesterday would be sweet but could I handle someone else with my wife. Jenn came to join me on the balcony around 10 am. We eventually got dressed for the beach and headed to find chairs around 1130. Jenn once again had a new bikini. This one looked great on her. Royal blue with white stripes. Once we were settled I headed for refills of our drinks at the pool bar. When I got back Jenn was applying sunscreen to her arms, stomach and her legs. I handed Jenn her drink and what happened next would change our lives forever. Jenn blurted out “You wanna get a pass for that resort? Thought while we were here we could check it out.” I nearly swallowed my own tongue but played it down. “Sure, sounds good” I couldn’t wait to enter the nude side, although I was nervous about being naked myself but quite excited to watch Jenn exposed. I wasn’t sure how far she would want to go but I was positive I wanted to try.

    It didn’t take long for us to get there and I quickly bought day passes as Jenn went to the ladies room. I didn’t know if she or I were up for the night passes as it sounded like at night things got pretty crazy. When she returned she wanted to head to the prude side first. We headed to the bar and I noticed a few women were topless but none without bottoms. All the guys still had trunks on. Jenn asked “You ok, if I take me top off? Are you kidding me? Of course I am, take the bottoms off too I thought. I said “I’m comfortable with it so long you are”. With that I watched in awe as my wonderful wife proceeded to take her bikini top off and let someone other than me see her tits in almost 2 decades. She put her top in our bag and walked over to a table. I wanted a drink badly so I went to the bar. There were 3 people ahead of me in line, one women in her 40’s who had big saggy tits and 2 guys. While I waited I couldn’t help watch Jenn sit at the table topless. I had a pretty good chubby as I waited my turn. As I ordered and watched the bartender mix the drinks I noticed a man and his wife, I assumed, were sitting at the table with Jenn. When I got back they introduced themselves as Ron and Sara. I sat down beside Jenn and thankfully still had my Oakley’s on so I could stare at Sara’s tits. They were pretty big and looked fake. She wasn’t a knockout in my opinion but pretty for her age. They were staying at the resort and had just got up for the day. My wife asked lots of questions. Almost too many but they weren’t shy to tell. Apparently there was quite a party last night and Sara mentioned she was a bit sore. Ron laughed and said “I’m not surprised!” My mind wanted to ask why but I’m pretty certain it was from sex. We talked for a while as Jenn asked more about their lifestyle, they were obviously swingers, but they were very respectful to us and very open. Ron and Sara got up and said they were headed to the other pool and hoped to see us again. Once they were out of hearing distance Jenn sheepishly asked “Do you wanna go to the other side?” I sarcastically said “When in Rome!” and stood to head out. Jenn sprung to her feet, still topless of course, and grabbed my hand as we headed toward the unknown of the “nude” pool. I just realized as we were walking that I’d have to disrobe if I wanted to enter. Could I keep my hard on down? Would Jenn be mad if I got hard around another woman. Oh boy, now I was worried.

    Once we entered my wife casually dropped her bikini bottoms and turned and motioned for me to do the same. I figured what the hell and stripped. I’m above average I’d say for dick size but no monster that’s for sure but I’ve always been able to shoot a big load, although Jenn never seemed too impressed when I’d toss a rope onto her face after I’d pull out. Jenn was a few steps ahead of me as she seemed headed to the pool. We got to the steps and she turned to head down them. In the bright sun she looked incredible in her birthday suit. It was when she was about to became waist deep in the water that I noticed something new. She had shaved her pubic hair completely off. She often trimmed or had a thick landing strip but never bald. That was the ignition that I didn’t need to a pretty obvious chubby that was coming on quickly. I sped up my steps and got into the pool before I was too embarrassed. There were only 6 people in the pool and about 10-12 hanging out by the bar and tables. Ron and Sara were in the pool and they made there way over to us. “Glad to see you guys again” said Ron. We chatted for a while and once my cock was finally deflated Jenn asked me to get another round of drinks. Ron offered to help so we both headed to the bar. Ron seemed nice and while at the bar he complimented Jenn and her good looks. I said thanks and of course said the same about Sara. I looked back towards the pool to see Sara was now pinching and fondling my wife’s breasts. I couldn’t believe it and like a young boy would, I nudged Ron with my arm and motioned to the action. All Ron said was “Sara really was intrigued by Jenn, surprised it took her this long to make a move”. A move? Was she bisexual? I watched in admiration as Sara continued mauling Jenn’s tits and I couldn’t help speculate that Jenn was totally into it. Even though her sunglasses concealed her eyes I could tell when she threw her head back slightly that she was overly excited. I was loving the show and once we had our drinks I headed straight back into the pool to get a front row seat. As I was getting close Sara stopped and whispered into Jenn’s ear. Whatever was said Jenn seemed to agree as she nodded and then followed Sara who was retreating out of the pool. As they got closer I questioned “Show’s over?” Sara replied “Just getting warmed up, let’s find a room though!” I followed like a new puppy as Sara led the way.

    The room had a few beds and a shower. It was obvious this room was made for sex and most likely group sex. Sara had led Jenn to the edge of the bed where she sat down as Sara continued to massage her breasts. Jenn had put her sunglasses on her head and I could finally see the look in her eyes. She was definitely enjoying the touch of another woman. Only a few moments passed and Jenn was now raising her own arms to caress Sara for the first time since this all began. My wife reached up and grabbed the underside of Sara’s huge tits. Needless to say I was rock hard watching the show in front of me. Ron then spoke and suggested “Push her further up the bed honey!” With that Jenn needed no coaxing as she crawled backwards to the head of the bed as Sara crawled on all fours and right up on top of Jenn. Sara leaned down and began licking my wife’s breasts in a doggy style position. I couldn’t help but stare at Sara’s pussy which was practically winking at me in the position she was in. I had pretty much forgot Ron was naked beside me but when he started his way up onto the bed it soon jarred my memory. He crawled up behind his wife and in a swift motion inserted his penis inside her. Sara let out a moan and turned her head back to look at him and smile. When she turned back to my wife she went straight for Jenn’s crotch. I was still standing back a bit from the bed but from my vantage point it sure looked like she was licking Jenn’s vagina. I walked over to the side of the bed to check, sure enough, my wife was having her pussy licked by a woman. I figured it was time I join in on the fun so I crawled up onto the bed and pushed my groin towards Jenn’s face. I’m sure it looked like terrible amateur porn but I was so worked up I needed some satisfaction too. Jenn immediately grabbed my penis with her hand and began stroking and then soon was sucking me. I was surprised that I didn’t cum in her mouth immediately but I was so shocked by the whole situation in front of me that I was maybe to tense to release. It’s hard to describe to feeling of watching your normally somewhat prude wife and mother of your children having her vagina licked by a woman who is getting fucked doggy style while she gives you head. I’ll admit, I was enjoying it. She looked sexy as hell and satisfied as well. Sara stopped licking Jenn and told Ron to pull out. She then rolled over beside Jenn and spread her legs. Ron crawled over to his wife and continued to fuck her now in missionary position. I quickly got between Jenn’s legs and began to fuck her too. The whole time Jenn was focused on the actions of our neighbors as she couldn’t take her eyes off them. Watching Sara’s tits bounce as he fucked her was mesmerizing so I can’t say I blamed her.

    We had been in the room for maybe 10 minutes and when we entered I don’t remember closing a door or even if there was a door. The possible door wasn’t locked obviously as I noticed out of the corner of my eye a man standing there watching us. I stopped mid stroke as it startled me but I then continued as it was the same man from yesterday who we saw at the nude pool. The man with the huge penis. While Jenn was focused on Sara and Ron, I was focused on him and his cock. It was huge and he was stroking it with his one hand. I had only seen him flaccid yesterday and now he looked rock hard. I was no sandwich artist but it had to be a foot long.

    Mr foot long came close to the bed, smiled at me and gave a thumbs up as if to approve of our sex act. I pounded away at my wife as she unknowingly had an admirer to her side. Ron started to moan and grunt and as I looked over I seen him slam hard into his wife as she wrapped her legs right around his backside. He obviously had unloaded inside her and was finished. He pulled out of her and backed off the bed as I watched Sara’s vagina start to leak of his cum. He saw the newcomer and said “Hey Jeremy, want another turn with Sara?” They obviously knew each other and when Jeremy said “Of course!” My wife’s trance of Sara was broke and she whipped her head over to look at the new man apparently named Jeremy. She watched intently as he crawled up onto the bed, as did I, towards Sara.

    Without a hello or hi he aimed his penis at her very wet vagina, inserted half of it and began thrusting. I had stopped to watch as it was an awesome sight to see Sara’s vagina expand and accept this half horse man. My wife finally spoke and it shocked me what she said “My god you have a huge cock!” I don’t think I’d ever in my entire life heard her use that word. He said proudly “Thanks, I’m quite happy with it!” In a somewhat failed attempt to save face in front of this man I began to thrust hard and fast into my wife, who by the way was once again locked into watching Sara get fucked by this man. Sadly I couldn’t last any longer, pulled out and came all over my wife’s pussy and stomach. She never even looked up at me as I did this and got off the bed. She did however lean over onto her side and laid her head onto Sara’s right breast and began to suck and lick it meanwhile taking her right hand and placing it onto her clit to begin rubbing. Once again I couldn’t help but stare in awe at my wife rubbing her cum covered pussy while licking the breast of a woman.

    Jeremy had obviously had his fair share of women and most likely very satisfied women. He pounded away at Sara like it was a hobby, changing speeds and different angles. She seemed to have no complaints as she moaned uncontrollably, something she was not doing when Ron fucked her. I was honestly ready to applaud his performance, and just then Sara started screaming that she was cumming! Jeremy just grinned and started pounding her as hard as he could and once she started to calm down he pulled out and started firing ropes of semen all over her breasts, stomach and then finally over her pussy. It was the biggest load I had ever seen. Jeremy slumped back and slowing stroked his cock and tried to milk every drop out of his organ. Even after this performance, albeit not overly long in duration, he was still hard. I turned my attention to my wife who was in a state of shock. Her mouth was wide open along with her eyes as she stared at him. Jeremy caught her staring at his cock and said “You wanna turn?” My wife smiled, turned to look at me and asked like a kid “Can I?” I didn’t know what to say. Sure I had dreamed of a threesome with my wife but had always envisioned it with me and another woman. Now she was asking for permission to have sex with a stranger with a huge penis. We had never discussed Sara playing with her which was technically cheating, but full on intercourse? Maybe it was the pressure of the situation, or me not wanting to look awkward in front of the 4 of them or maybe the vision of Jeremy fucking the shit out of my beautiful wife. I said firmly “Yes!” He nonchalantly moved in between her legs and used his tip to scoop up some of my cum that was still leaking from inside her and began to smear some on the head of his penis like it was KY lube. He then proceeded to push into my wife. With his size this was going to be a task for my wife’s vagina to handle. Like a pro he pushed in and backed out, each time he went slightly further until Jenn’s lips had engulfed the first inch of his shaft. Watching this was starting to add life back into my own penis although it wouldn’t need near the blood flow Jeremy’s did. I couldn’t help but grab my cock and stroke it in admiration of the act in front of me!

    With every thrust in and out Jeremy’s cock ventured further into my wife and when he was just over 2/3 of the way inside her I couldn’t help but wonder if she was feeling a new sensation cause I for sure hadn’t ever been that deep in her. He kept going further and further and when there was only about an inch left he pulled all the way out until just the tip was touching her pussy lips and held it there and paused. My wife was looking intently at his cock, waiting in anticipation of the next thrust, and when he didn’t proceed she spoke, “What’s wrong? Keep going! Jeremy replied with a smirk “You sure you want it all?” Jenn enthusiastically replied “Oh god yes!” With the encouragement from my wife Jeremy bottomed out on the next stroke and she let out a yelp. I loved watching her be pleasured by this man. I had no idea how exciting it would be to watch her get royally fucked by someone else and all along I had always hoped I would be the center of attention with multiple women. Despite my fondness of my wife’s pleasuring, I was rock hard and wanting to get in on the action as well. I once again went to the head of the bed in hopes to entice my wife into another blowjob. I had to say her name out loud in order to get her to notice me, her husband of 15 years, as she was locked in on the cock inside her. When she heard her name she did look up and saw me and my erection and she immediately grabbed it and began sucking. So for the first time ever my wife was taking on 2 men although that wouldn’t last long.

    Ron musta had the same idea as me as he crawled onto Jenn’s right side and grabbed her hand and placed it on his cock. She looked over at Ron, smiled and began stroking him while blowing me and getting fucked by Jeremy. Now there was only one hole left and I was definitely thinking I’d love to see her do anal. I knew I couldn’t last much longer given the situation and I told my wife I was about to cum, she never missed a beat and pulled me from her mouth and aimed it at her tits. I unloaded a pretty good sized load onto her breasts and sat on the bed beside her. She quit stroking Ron and began blowing him as well and soon she had another load on her chest as he too unloaded for the 2nd time. Now only Jeremy was left to orgasm but not before my wife began moaning and thrashing as she obviously was having her own orgasm. She was massaging her breasts while she came and rubbing our semen all over her torso. Jeremy kept pounding away but then stopped and suggested they switch positions. He pulled out and laid beside Jenn who took the hint and went to straddle him cowgirl style. He stopped her and said “Go reverse !”

    Jenn straddled him, grabbed his cock, aimed it at her now gaping pussy and slide down onto the shaft and began bouncing. Jeremy placed his hands on her ass and helped support her bouncing. At that moment I had desperately wanted a camera to capture this picture. It may seem weird but seeing her ride him like a porn Star was stunning in my eyes. This went on for about a minute and then Jeremy shouted he was gonna cum. My wife shouted “Oh god” and started ride him as fast as she could. Jeremy obviously took the hint that she wanted him to cum inside and he began to grunt. I still had a birds eye view from my spot on the bed and after about 5 strokes I could see his cum running out of Jenn while it coated the shaft of his cock. He had unloaded another huge amount inside her and it was beginning to pool at the base of his shaft. Eventually Jenn stopped riding him and just sat on his midsection with his cock still inside her. She was breathing heavily but slowly and then Sara spoke “Well done Newbie! He has been refused by more than one woman because of his size!” Jenn smiled and finally dismounted Jeremy, cum was dripping out and onto the bed as she went to sit on the edge of it.

    She was gently rubbing her swollen pussy and massaging the cum around her opening and we all began discussing the experience. It felt a bit awkward cause normally I put my clothes on after sex but my clothes were still in a bag that we left at the pool. I sure hoped they were still there. Jenn had nothing but positives to say about the “experience” and Sara was more than happy to hear she was enjoying the lifestyle. Did this mean we were swingers now? After quite awhile we all headed back to the pool for some drinks and eventually we headed back down the beach to our resort.

    When we got into our room Jenn was almost panicking, “Do you hate me? My god what have I done?” I grabbed and hugged her and said “Calm down Honey, I was there with you. It’s ok, I wanted it to happen!” “You’re not mad? I just had sex with another man?” I continued to reassure her that I was totally ok with it and was excited to watch her take on Jeremy’s size. I was more worried she’d only want his big penis and not mine anymore. We talked about the day and decided that we both wanted to go back tomorrow. That night Jenn gave me a blowjob as she said she needed a break “down there”.

    The next day we went back and today we met more couples and a few single women. We ended up in someone’s room where there were 3 girls and 2 guys, myself included. Jenn went down on one of the girls while getting fucked Doggy style by a guy named Daniel. I got a blow job from both the girls, Pam and Tammy and fucked my wife again in front of them. This trend continued every day until we left. Although I never made a list, my wife slept with 18-20 different men including a few black guys and of course Jeremy a few more times. I only had sex with 2 other women, Sara once and a girl named Angie. Angie was only 23 but she had been swinging for years. I mostly watched, got BJ’s or fucked my wife. The most adventurous she got was having anal sex with Daniel while I was in her pussy. It was exciting feeling him penetrating her anus while I was in her vagina.

    The week ended, we flew home to the kids and our normal life. There is no doubt in my mind we are closer than ever and we laugh more than I can ever remember. We plan to go back next winter and maybe stay right on the resort. We have no plans of swinging in our area but our sex life is so good I’m not sure why we would. Still puts a smile on my face when I think how my once prudish wife went from boring swimsuits to group sex with multiple men in one week. I still think seeing Jeremy’s big cock that first day at Hedonism is what set her on her way.

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