[ad_1]
This story follows on from My [M43] relationship with my wife [F36] [cuckold], which describes how my wife Jessica and I first got into the cuckold lifestyle.
Jessica and I went on a long vacation together almost a year after we had opened up our relationship. This was a very exciting time for us as by now we had grown comfortable and confident with our new lifestyle but still found it exciting and full of unexplored possibilities.
The preceding few months had been a busy time for both of us so, rather than booking a holiday that involved lots of travelling and sight-seeing as we usually did, we booked two weeks at a luxury all inclusive resort. We went with the sole intention of just being together and relaxing but we were excited about gonna a place far enough away that we could be almost certain that everyone would be a stranger and we maintained an open mind about what might happen. She had an IUD fitted and we had only been having unprotected sex since the begin of our relationship although I knew Jessica had a large stash of condoms in her wash bag for when she met her lovers and we decided to take this with us just in case.
The resort was almost like a little town, right by a stunning sandy beach and surrounded by hills. At the center was a enormous complex of about a dozen swimming pools of all different shapes and sizes with bars, restaurants and numerous other entertainment and leisure venues scattered around them, and with enormous gardens and apartment buildings around the outside. We had only booked a standard apartment but it was still absolutely stunning. The entrance led straight into a luxurious bedroom with a enormous double bed and an adjoining bathroom and dressing room and a pair of double doors from the bedroom led to a large living space with an massive private balcony overlooking the gardens.
This was the early part of the summer season so the weather was already hot but the resort had not become too crowded yet. We did lots of exploring and tried out a lot of the activities that were on offer over the first few days like having a couple’s massage and Jessica getting a French manicure (I have posted some pictures of Jessica from this holiday on u/mrsalvastar as “**Jessica – Holiday #1**”). Most of the people there were older couples or small groups of friends in their 30s or older and everyone mostly seemed to want to relax and keep to themselves, so we rarely had any opportunity to socialize
Our sex life had improved considerably since we had opened up our relationship and we had been having sex once or twice a week for a while, although at this time she also had two regular lovers and she would usually spend at lease one evening each week with one of them for a long and passionate sex session. I was concerned that I would not be able to give her what she was used to for the two weeks while we were away but when I told her this she found this genuinely funny. She told me that she was not an animal and that I was more than enough for her, although I still made an effort to have sex more than usual while we were there.
Jessica had been attending the gym at least a few times a week for almost six months and decided to take a break from exercising while we were away. At the same time I had been too caught up with work to do much exercise so I decided to take the opportunity to be more active while we were away. I took to hiking in the hills around the resort most afternoons, which left Jessica alone to read by the pool, walk up and down the beach and occasionally go for a swim. Her time at the gym had really paid off and her body looked absolutely fantastic although she still preferred to wear loose maxi dresses while we were out and a modest bikini underneath for when she went swimming.
On the sixth or seventh day at the resort, I headed down to the pool in the late afternoon after my hike to meet Jessica in her preferred sunbathing spot, but she was not there. After a few minutes of searching I found her nearby with a group of around twelve young men who looked to be in their mid 20s. She often managed to befriend groups of men as she was good looking and friendly so this was nothing unusual. I went over and she loudly introduced me to the few of them she was sitting with in a way that made it clear that she had been talking about me and that they were all expecting to meet me around now. I sat down and chatted with them for the rest of the evening. They all seemed like nice friendly people and it turned out that they were a group of friends who had all met at school and were staying at the resort for a couple of days to recover after a week-long cycling tour through the mountains.
We got on with two of the guys particularly well, Mike, who was average height with dark hair and who was very outgoing and funny, and Dave, who was tall and very well built with blond hair and who was fairly quiet and aloof but very good-natured and intelligent. The following evening was gonna be their last evening at the resort and the rest of their group were planning on getting an early night so after dinner we invited the two of them back to our room to play cards.
There was a large round table and six chairs on our private balcony where we spent the next few hours playing cards, drinking, laughing and joking. Jessica and I sat together on one side of the table and Mike and Dave sat opposite us. We ended up playing poker, using a few handfuls of coffee beans that we had taken from the bean-to-cup coffee machine in our room as poker chips. After a few drinks we had a laugh about playing strip poker instead and I joked that I bet they would love to see Jessica naked. We all laughed and Jessica blushed and hit me playfully on my arm, but we both noticed that the two guys awkwardly exchanged a look as well.
Not long after that Jessica complained about being too hot in her dress as it was still quite warm and humid even though it had gone dark over an hour before. She went into the bedroom to get changed as I continued to play poker and chat with the guys but was amused as they both seemed to attempt to take glances back over their shoulders into the bedroom to try to catch a glimpse of Jessica getting changed.
A few minutes later she returned in a bikini. It wasn’t anything particularly special compared to what other women had been wearing at the pool although it was noticeably more revealing than the bikinis that she had worn up to now and was by far the most revealing one that she had brought with her. She had also tied her shoulder-length hair into a short ponytail. She almost never wore her hair like this except when we had sex, so I saw this as a clear signal that this was what she wanted. I wondered it would be a long shot to get one, let alone both of these young men to have sex with her tonight but we were all a little drunk and getting on well so I decided to play along.
Instead of sitting next to me again, she took another chair and sat between Mike and Dave. We carried on playing cards and I worked hard to keep the conversation flowing naturally as I could tell the two of them and especially Dave weren’t sure what was happening and were feeling quite awkward in spite of them both having had at least two bottles of wine to drink over the past hour or so.
I enjoyed watching them discreetly glance at Jessica’s very petite and toned body and her take opportunities to flirt with them and touch them on the thigh or forearm whenever they won or lost a hand. After a while they started to relax and Jessica started to flirt even more obviously. She told them that she had been using a new body moisturizer and invited them to stroke her thighs to feel how soft and smooth her skin was. Mike and Dave hesitated at this point, apparently unsure about whether this would be crossing the line, but I smiled at them from across the table and said that whatever was fine with Jessica was fine with me.
Once they had started touching her thighs she began to stroke theirs, one with each hand, and gradually worked her way up to their crotches. After a few minutes they seemed to forget that I was there and Jessica started tentatively kissing them both on the neck. By this time the card game had been completely forgotten and I suggested that they head into the bedroom. Jessica looked up at me with a loving smile as she stood up and led both Dave and Mike by the hand through our suite and to the bed.
As soon as they were in the bedroom she let go of their hands, turned around and removed her bikini to reveal her naked body. Dave and Mike just stood their gawping as Jessica bent down to free the bikini bottoms from around her ankles and revealed her completely smooth and immaculate pussy. She stepped forward and kissed them both, first Mike and then Dave, encouraging them to put their arms on her and feel her body. She then jumped on the bed and invited them to get undressed and join her.
I had followed them from the balcony and was standing in the double doorway looking into the bedroom. They were both clearly nervous in spite of the amount of alcohol in their systems and I could sense how reluctant they both were to get undressed in front of each other but especially in front of me. Up to this point it had never even crossed my mind to join Jessica while she was making love to someone else and I had no intention of joining them now. It was also clear that my presence was risking ruining the atmosphere so I said that I would leave them alone to play together and went back into the living space, closing the double doors behind me. I had considered leaving our suite entirely and going down to one of the pool bars that were open into the early hours, but I did not feel that we knew these two men well enough for me to leave Jessica entirely alone with them. I poured myself a drink and headed back out onto the balcony to relax and enjoy the warm night breeze, satisfied in the knowledge that Jessica was being well looked after next door.
Over the past year or so I had got used to leaving Jessica alone with other men to indulge her private slutty side. We had found a few young men on hook-up applications who were eager to meet up regularly and didn’t mind not being able to get to know her or get emotionally involved. It had become like a recreational activity for her. Some women like to go out drinking and dancing with friends, others like to play sport or run marathons, but Jessica liked to have sex. It didn’t make her any less my partner when she came back home to me and it gave me great pleasure to see how happy being able to freely indulge her sexual side made her. The fact that she could in theory be having all of this sex with me didn’t seem crucial, since women who like to go out drinking and playing sport with their friends cab also do those things with their partners, and over the first few years of our relationship we had learned that I was not able to give her as much sex as she wanted on my own. In fact, since she started meeting other men, we had been having more and better sex and our relationship with each other had improved drastically now that she felt sexually satisfied and I no longer felt pressure to give her more sex that I was capable of.
I did not eavesdrop on them although I could not help hearing some of what was happening in the next room and Jessica described what they did in great detail afterwards. At one point Jess slipped through the double doors on her own to get a drink from the refrigerator in the living area. Her hair and make up were a mess, her skin was flushed and her whole body was glistening with sweat. She didn’t say anything to me but waved at me as I was on the balcony and gave me a enormous beaming and excited smile.
As soon as they heard the doors close behind me the tension in the room dissipated and Mike and Dave’s inhibitions seemed to disappear. Mike was clearly more enthusiastic than Dave and quickly got undressed, joined Jessica on the bed and started kissing her. Dave also got undressed, but more slowly, and stood by the bed awkwardly until Jessica beckoned him down next to her. Now that they were all on the bed she lay on her back with her legs spread and Mike got down between her legs and started licking her pussy as Dave lay next to her and tentatively started kissing her and playing with her nipples.
When we started out we had a very strict rule that Jessica would use barrier protection even for oral sex but we had agreed to relax that rule because she loved to give blowjobs but hated the taste and feel of a condom in her mouth. In a break in their kissing she whispered to Dave that she wanted to take his cock in her mouth. He immediately got up and knelt next to her and she took the base of his cock in her hand and guided her mouth onto it she rested her other hand on the back of Mike’s head between her legs. Dave still seemed tentative but this quickly dissipated as Jessica massaged his glans with her mouth and he quickly started holding onto her head and thrusting his cock into her mouth, making her gag and gasp for air. This seemed to attract the attention of Mike and he got up from between her legs and moved over to Jessica’s head and held his cock out to her. Still with Dave’s cock in her mouth, she reached our and took Mike’s cock with her free hand and then turned her head and rammed her head down on Mike’s cock to take it as deep as she could.
Dave seemed to be uncomfortable being opposite Mike and went down to Jessica’s pussy and started fingering her and touching her clit. Jessica continued sucking Mike’s cock for a short while before looking down at Dave and saying, “aren’t you going to fuck me?”
We still had a hard rule about using condoms for vaginal sex and Jessica had taken her washbag filled with condoms out and left it on the nightstand when she had got changed earlier. In a short break from sucking Mike’s cock she leaned over to take a condom from the bag and handed it to Dave, who quickly opened it and rolled it down his erection. Jess repositioned herself so she was lying on her back with her head handing over the edge of the bed and invited Mike to get off the bed and fuck her throat while standing on the floor to make room for Dave to take her in the missionary position.
Once she was in position Dave climbed on top of her and she used her free hand to guide his cock to her pussy. She was so wet by this point that she could almost feel her wetness drip from her and he was able to push into her in almost a single smooth thrust. She gasped loudly from the sensation of being filled so suddenly and this was the first sound that I heard from the balcony that told me that they had started having sex.
Jessica had never been with two men at the same time before then and she told me that the feeling of being at the canter of attention and having two penises inside her at the same time, with Dave vigorously thrusting into her pussy and Mike enthusiastically fucking her throat, overwhelmed her senses. It wasn’t long before her throat couldn’t take anymore and she had to ask Mike to stop as she got her breath back. Without saying anything Dave flipped her over and picked her up by her hips and started taking her roughly from behind, spanking her ass and pulling her hair as he fucked her. This is the point that I started to clearly hear them from the next room – the bedframe banging against the wall, the slapping sound of their bodies impacting each other and the loud moaning sound that she made as she started really enjoying herself.
It wasn’t long before Mike started to feel left out and he got onto the bed, pulled her around so there was space for him to kneel in front of her, and put his cock in her mouth so she was being spit roasted by the two of them. Dave was fucking her so hard that with each thrust he was pushing her onto Mike’s cock and forcing him hard down her throat. After a few minutes of this Dave’s pace started to go faster and he took hold of her ponytail and pulled it hard so her head jerked back and Mike’s cock slipped from her mouth. He thrust into her hard and fast as she moaned uncontrollably until finally he came with a few long deep thrusts.
Dave quickly withdrew from her and was replaced by Mike as he quickly moved around behind her and pushed his cock into her pussy. He started fucking her just as hard as Dave but was more vocal and told her how he had wanted to fuck her since he had first seen her and how much of a naughty slut she was. It was only after he had cum as well and they lay down on the bed next to each other to get their breaths back that they realized Dave had gone into the bathroom and still hadn’t come out.
Jessica took Mike’s used condom and went into the bathroom to put it in the trash and check on Dave. She found him sitting in the toiled with his head in his hands. He looked up and smiled reassuringly at her when she came in. She asked him whether he was alright and he explained that this was a very overwhelming experience for him and that he wasn’t comfortable being in the room while she and Mike were having sex and was probably gonna get dressed and go now.
She did not like the sound of this as she was still far from satisfied and was looking forward to continuing to have sex for the next couple of hours. She put her arm around him and whispered to him that he was one of the best fucks she had ever had and that she wanted more, and that she didn’t think his friend Mike would be enough to satisfy her on his own. This made him laugh and relax and after a few minutes came out of the bathroom.
By this time Dave was ready to go again so after some more oral she had sex with him for about fifteen minutes in numerous different positions until he came and then she had sex with Mike again. She continued to let them take it in turns fucking her one or two more times over the next couple of hours until neither of them had the energy to have sex again, at which point she suggested that they call it a night. She put on her robe as they got dressed and then she saw them out. She then brushed her teeth and took a shower and she at all times did after before seeing me after meeting one of her lovers.
Around three hours after I had left the three of them alone Jessica opened the double doors and told me that I should come back to the bedroom. When I entered the room it was warm and smelled faintly of sweat and sex. I went into the bathroom to take a leak and saw that the bin was filled with used condoms, maybe six or eight of them.
As I came out of the bathroom she was lying on the bed, freshly showered and dressed in a thin night dress. She was awake but clearly exhausted. We kissed and caressed each others bodies and fell asleep in each other’s arms.
The next morning I woke up very early, almost at first light. It had only been a few hours since we had gone to sleep but my mind would not let me rest with the memories of what she had done last night. I had to have her now.
She was sleeping in her side next to me still wearing just her thin night dress and I climbed on top of her, rolled her onto her back and pushed her legs aside with my knees. This quickly woke her up and she smiled at me, knowing exactly how I was feeling and what I wanted to do to her. My cock was already hard and, although she barely had time to get wet, she guided it to her pussy and I pushed inside her hard. She winced from the pain of taking me inside her when she had hardly started to get wet but this quickly transitioned into an expression of exhilaration – she liked this sensation.
I took hold of both of her wrists and held her arms over her head, pushed her legs further aside and looked deep into her eyes as I held my cock inside her. I whispered to her how naughty she had been last night and how much of a slut she was and this made her moan and her body spasm slightly. I continued to just hold my throbbing cock all the way in her pussy, making her feel me deep inside her, and to whisper to her how good her pussy felt and how horny it made me for my cock to be where two other cocks had been only a few hours earlier. This pushed her over the edge and she almost screamed as her body spasmed under me with a enormous and intense orgasm.
After her orgasm had subsided I let go of her arms, got up on my knees and started to fuck her hard and fast with all my weight behind each thrust. I gently slapped her face and stuck my fingers down her throat to make her gag as I fucked her until I came very had and filled her with my semen, reclaiming her as I had done so many times over the past year.
NSFW: yes
[ad_2]
