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Wife Experiments on Holiday

"Linda agrees to extramarital sex, when far from home"

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After reading stories on here for years, I thought it was time I contributed. This is a true story, about something that happened when my wife Linda and I were on holiday in Crete a couple of years before covid.

First, a bit of background. I was in my mid-fifties and Linda was slightly younger at 50. We'd been happily married for 20 years, have no children and had what I guess you could call a vanilla sex life. It's good, we both enjoy it but we've never been tempted to swing or anything like that. It doesn't even come up much when we talked about fantasies. We're doing ok for ourselves, working together self-employed, and we look after ourselves. We don't go to the gym or anything, but we eat healthily and go walking and cycling. Linda is a 5ft 8" size 12 brunette, with beautiful 34DD boobs. She'd been complaining about being overweight and had a slight belly, but she looked absolutely gorgeous with those boobs and her full arse. I'm pretty average - 5ft 9", reasonable build for my age and with a quite thick dick of about 7".

We'd been having a good year with the business, but we'd been so busy and we really needed a break to unwind and relax. We decided to take a month off in the summer. We booked a hotel on the north coast of Crete, as we'd spent a fortnight there a few years before and it was a great place to relax. Linda had enjoyed the massages, and we'd both enjoyed the beach or lounging by the pool. It was quite a bit away from the resort type places on Crete that the younger folk go to, so it was nice and peaceful. Perfect place for us to chill for a few weeks. We arrived on the Saturday night and we had a pretty good room, with a nice balcony overlooking the med. We were tired after our journey, so we just had a quick nightcap on the balcony before going to bed.

When I woke up, Linda was already up. She was sitting at the table in our room with a cup of coffee, and looking at the facilities the hotel had to offer. I joined her at the table with some coffee of my own. We agreed that we'd just stay at the hotel most of the time on this trip, as the whole point of the holiday was to unwind and relax. She booked herself massages in the room for Monday, Wednesday and Friday mornings for the week ahead and we thought we'd just lounge about for most of the rest of the time. We were going to be there for a month so had plenty time to see the sights if we fancied that later. Sunday was spent mostly getting our bearings around the hotel, finding the many bars and restaurants, that sort of thing, as well as chilling by the pool.

Monday morning came around, and Linda's massage was booked for 10. Just as I was gathering up my towel, ipad and ipod for a morning reading by the pool there was a soft knock on the door. Linda opened it to admit her masseuse, who was an attractive looking short middle-aged Greek woman in a smart white tunic. She started to assemble the massage table as I gave Linda a peck on the cheek and told her I'd see her by the pool when she was done. It's a bit of a cliche, but when I got to the pool there were no loungers left. A group of four guys who sounded German beat me to the last of them, so I went to the smaller pool that was just around the corner. There, I set myself up to read and listen to music. Just over an hour later, Linda arrived and with a "hiya" she passed me a non-alcoholic cocktail and lay on the lounger I'd pulled next to mine. I asked her how the massage was and she said it was great, just what she needed and that she was feeling very relaxed. I asked if she'd got a "happy ending" and she laughed and said no and that anyway, she didn't think this was that sort of place. She asked why I'd chosen to sit at this pool and I explained about the lounger situation. We both preferred the other pool. It was larger and you were allowed to go topless there, no doubt why the German men had been so keen to go to that one. This smaller pool was family friendly, so it was a bit noiser with kids. Linda was keen to avoid white bits, so after lunch we checked the large pool again and found a spot. Linda removed her bikini top, freeing her boobs, and lay back on the lounger. I noticed her 34DDs were getting lots of looks from guys around the pool, especially the group of Germans. I didn't mind, I was very proud of Linda and how she looked and it was good to know I wasn't the only one who found her attractive. Anyway, I could hardly complain as I'd been ogling the other topless women who were around. When Linda sat up to put more sunscreen on her legs, her boobs fell forward and I noticed that the German guys were now talking quietly and looking over. I said to Linda "I think you've got some admirers" and she glanced at them and said "don't be so silly, I'm 10 years older than them". I'd read a lot stories of guys sharing their wives or being cuckolded, and I really liked them but with Linda being straight-laced and us having a good sex life I'd never thought it possible it would happen with us. We'd never even discussed it, apart from a drunken night years before when I'd asked her if she'd like to try it and she just said "no". Now, in the sun nearly 2,000 miles from home and after a few proper cocktails over the afternoon it did seem that she was sitting up more often, as if to give them a good view of her boobs, and sometimes when getting in or out of the pool she'd walk past them when she didn't really need to. We had great sex that night, she'd obviously liked the attention although I didn't push my luck by talking about it.

Tuesday passed pretty uneventfully. We took a bus from the hotel into the nearest town in the morning and had a look around the market, had a nice lunch in a restaurant there and returned to the hotel pool just as the afternoon was ending. Linda was topless again, but this time her German admirers were nowhere to be seen. We didn't stay long this time and returned to the room to change for dinner. We went to a different restaurant from the night before, and I noticed that the Germans were across the room dining there too. I nodded towards them and said "look, there's your friends" to Linda. She turned to see who I meant, and they noticed her turning to look at them. Throughout the rest of the dinner, I noticed they kept looking over at us. Their table was on the way to the toilet, and when I passed them on the way there a guy with light brown hair looked up at me, smiled and nodded in a sort of hello motion. When Linda passed their table returning from the toilet, the same guy looked up again and said "hi" to her. She muttered an embarrassed "hi" back to him and returned quickly to me. I told Linda that I thought he fancied her, to be told not to be so silly, that she was too old and was overweight. We had great sex again that night, and this time I did bring up her admirers, saying that they really fancied her, that she was really sexy, I bet they wanted to fuck her, that sort of thing and she seemed to really enjoy that.

On Wednesday morning, I got up to get down to the pool earlier so I could grab a couple of loungers. While Linda was having her massage, I was reading stories on my ipad about hotwives and the more I thought about it the more I became interested in trying it with her. She joined me next to the pool shortly after 11, saying that her massage had been from the same woman and was excellent, so relaxing, as she removed her top. We didn't see the Germans at all that day, but we did return to the topic of her being with another man and we discussed it on and off throughout the day and night. Wouldn't I be jealous, she asked. I told her I didn't think so, and that the thought of if turned me. She said it had been years since she'd been touched by another man, not since she met me, and that she'd be embarrassed. I asked her if she ever got bored with just me, and she said no and another man was a nice fantasy but she'd never go through with it.

On Thursday we were both by the pool early. Linda was just in her bikini bottoms and we were just relaxing. Again we started to talk about her having sex with another man, and I gave her my ipad already at some hotwife stories for her to read as I lay back listening to music. We lounged by the pool most of the morning, and returned there after lunch. Linda again took off her top to work on her tan. With the sun now up, we thought it was cocktails o'clock so I went off to the bar to get us a couple of drinks. It took longer than usual as there was just one bartender on, and I returned to Linda to find that she was sitting upright with her boobs still on display, talking to the German who'd said hi the other night. He was sitting on the side of my lounger. When I handed her the drink she nodded to her visitor and said "this is Karl" before taking a sip from her straw, he shook my hand and said hello as he stood up from the lounger. He stood at the foot of our loungers and we chatted for a while, him speaking very good English. He was over on holiday for two weeks with a a few of his friends. Linda was making no effort to cover herself, and I noticed as we talked that he seemed to be enjoying the view of her boobs and legs. There was a growing bulge in the front of his swimming shorts which Linda couldn't possibly not notice, but she didn't say anything about it. He seemed like a nice guy, and it wasn't long before he said goodbye and went over to join his friends about a third of the way around the pool from us. "I told you he fancied you" I told her, and she said that was nonsense so I pointed out that she'd given him a semi. She blushed a bit at that and said she'd thought it was just the way his shorts were arranged but I said "no, he wants to have sex with you". She said "well, he's not going to", but throughout the afternoon she did keep looking towards Karl and his friends, and they often saw her walking in just her tiny bikini bottoms as she went to and from the pool. We had another great night of sex that night, and this time the hotwife fantasies were first and foremost. Linda had been turned on by reading some stories and especially by showing herself to Karl, and the thought that she'd made him start to get hard really got her going.

Friday morning came, and the last of the massages Linda had booked for herself. Again, I went down to the pool early to book us a spot and Linda would join me after her massage. When she found me by the pool at about 11:15, she seemed a bit flustered. I asked how her massage was, and she said it was great but this time it had been a man. When he arrived he apologised that her usual masseuse Maria was off today and he was the only one available. He offered a refund if Linda would feel uncomfortable being massaged by a male, but she'd said that no it was fine. I asked if he'd given her a happy ending, and she said "it's still not that kind of place" and that he was very professional. He'd given her the exact massage Maria would have done, and there was nothing inappropriate. She said it felt more sexual though, not because of what he was doing so much but what was going on in her head. She was really enjoying being touched by this strange man, and even though she didn't find him remotely attractive she was getting pretty aroused through the massage. I asked her if she wished it had been Karl massaging her instead, and she just looked at me and said "oh yes". We went straight back to our room and as soon as we were in the door our clothes were off and we were at it like rabbits on the bed. I asked Linda if she wished it was Karl here fucking her and she again said "oh yes". We got lunch delivered to the room and spent the afternoon having sex and talking about what was going on. Linda said that yes, since we were so far from home and nobody knew us here, she'd be willing to have sex with somebody. Karl definitely seemed the best candidate, as she liked him and it had been obvious that he fancied her. Linda agreed to spend some time with him, go out to dinner alone with him and if she felt comfortable enough then, well, she'd see what happened. Later that night after dinner we spotted Karl and his friends at a table at the bar as we entered it. Karl gave us a big smile and a wave and we went over to them. He introduced his friends, they were Christoph, Jens and Matthias. We stood chatting to them for a short time, they all had excellent English, before we went to find our own table. After a couple of drinks, on top of the wine with dinner, Linda said she needed a pee and set off to find the toilets. I caught Karl's eye and waved him over. He sat opposite me and as we were pushed for time I just asked him outright if he fancied Linda. Yes, he said, she's a very attractive woman. Would he like to have sex with her, I asked. A little surprised look and then yes, of course I would if she wanted to. Linda returned as I was explaining the circumstances to Karl and telling him what she'd said about maybe dinner, and he asked her if she was sure. He then said "what about tomorrow night? I'll take you out for dinner in town and see if we click". I held her hand to reassure her I was fine with her going on a date and after thinking for a few seconds she said to Karl "ok, dinner tomorrow night". We agreed for him to collect her from our room at six o'clock. With that, he rejoined his friends. I assume he must have told them what was happening, as they kept looking over at our table while they were talking. This was making Linda feel a bit self-conscious, so we left the bar and returned to our room.

The following morning, we stayed in bed later than usual talking about Linda's date night. She was extremely nervous, and kept asking herself what she's done, what's she playing at, a married woman, an old woman, that sort of thing. This carried on for most of the day, despite my reassurances that she was a beautiful and sexy woman, that it was all fine, it could just be a nice dinner she didn't have to go further but I was perfectly happy for it to if she wanted. We weren't at the pool long that day, just a couple of hours after lunch, and there was no sign of Karl or his friends. At about half four, Linda said "I suppose I'd better go and get ready" so we went back to our room. She spent about half an hour relaxing in the bath, before I heard it being drained and the shower running. At about quarter past five she came back into the room, wrapped in a towel with another small towel around her hair. She said that she'd decided, this was just going to be dinner and she wasn't going to have sex with him. I said ok, and that was totally up to her but that she should enjoy her night whatever happened. It was strange watching her get ready for her date. I'd seen it so many times before, but this time it was to go out with somebody else, a guy we'd barely met. Because she'd decided this was just going to be a friendly dinner, she didn't put on any of her sexy panties or stockings, just a small pair of black knickers. Likewise with her bra, not one of her sexy ones just a nice, functional black one. She wore a long black dress and black heels, and sat doing her hair and make-up. She then stood, faced me and said "well, how do I look?". She looked stunning, and I told her so. It was about ten to six now, so Karl might arrive at any momment. She was extremely nervous, trembling slightly with her voice breaking as she spoke. I handed her a glass of wine and sat on the bed next to her with my arm around her shoulders telling her how gorgeous she looked, just to enjoy herself and that everything is fine. She said she'd keep in touch on Facebook messenger, to let me know she was ok and how things were going. A couple of minutes after six, there was a knock at the door. I opened the door to find Karl there, dressed neatly in a shirt, suit jacket and trousers. I let him in and there was a few minutes of awkward small-talk. He'd booked a table at a restaurant he'd been at before, so he knew it was good. I poured him a glass of wine, and he drank that while Linda finished hers. He then said that they needed to go, and told me not to worry and that she was safe and would enjoy herself. Linda stood, put her phone in her bag and gave me a kiss, saying "I'll not be late". With that, they left the room and the door closed, leaving me on my own.

I was too nervous about what was going on to head anywhere to eat, so I ordered room service. At about seven o'clock, my phone pinged with a message from Linda. It just said "arrived at restaurant, seems nice". I couldn't think about anything else all night, was just wondering how it was going, what were they talking about, etc. I tried watching the TV, but it was a waste of time. I sent her a message at about eight, just asking how it was going. Her reply was just "fine". An hour after that, my phone pinged again and she said "going to a bar to get a drink". This was interesting, as it meant she wasn't wanting to come straight back after dinner. They must have only been in the bar for about an hour or so, because at about half ten I got a message that said "in taxi back to hotel". It was about a half hour trip to the hotel from town, so I expected she'd get back at about eleven but elven came and went, as did midnight. I sent her a message asking if everything was ok and got no reply. Just after one in the morning, I heard her opening the door and she came into the room. She was a bit drunk, and was looking a bit dishevelled. "Hello," she said, "sorry I'm a bit late". I gave her a big hug and told her it was fine. So, I asked, how was dinner? Nice, she said, as she sat on the edge of the bed to take her shoes off. Is Karl nice, I asked - "yes" she said. She stood to remove her dress and bra as I asked if she'd enjoyed the bar - "yes" she said. I then said it was a while since she'd said they were going back to the hotel and she looked at me and said "I went to his room and I fucked him". My cock immediately jumped to attention at that. I'd suspected, or rather hoped, that was what was happening but I really didn't think she'd go through with it. She pulled her knickers off and told me to fuck her, and I didn't need much persuasion. She lay back on the bed and opened her legs, her pussy looked amazing. Definitely looked used, it was redder in colour than usual and slightly swollen looking. In between her open lips she looked soaked. I was desperate to tongue her as it looked so good, but she pushed my head away. I tried again and she pushed me away again and said "no". I asked why not and she said "I'm full of cum". Linda had an IUD fitted so we never used condoms, but the thought that another man had cum into her was extremely exciting. "He came inside you?" I asked almost in disbelief, and she said "twice". My cock easily slipped into her, well lubed with Karl's cum as she was, and I was soon pumping away at her like a man possessed. She came a few seconds before I gave her her third load of cum of the night. She was almost immediately half asleep, and was fighting off my questions with "we'll talk in the morning". The only question I got an answer to was when I asked if she'd enjoyed it, and would she do it again - "definitely" she said, before turning over to sleep.

In part two, I'll write about what happened over the following week before Karl and his friends returned home.

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Written by Holiday Cuck

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