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A True Cuckolding Story

 woman with bow around wrists, true cuckolding story

True Cuckolding Story Submitted By Anonymous Guest Author

This is a true sex story about cuckold sex where I watched my wife have sex with another man. It was a 30-year fantasy coming true. It happened when I was on holiday with my wife Debbie, and another couple (Liz & Mark) on a Greek Island called Kefalonia and is about the excellent service provided by a well-built 19-year-old waiter called Jim.

Debbie and I have been married for over 25 years, and I am the only sexual partner she has ever had. I have fantasized for many years about having a threesome, even before we were married, but Debbie was never keen.

We stayed in a beautiful boutique hotel on the eastern side of Kefalonia, Greece. It was staffed by a small number of amiable locals who wanted to provide everything to ensure we had a great holiday.

Jim is a 19-year-old poolside waiter, and as we spent most of the day by the pool, we became very friendly with him. Both girls had taken the latest best-seller "Fifty Shades of Grey" for a holiday read. I mention this purely as it may, in some way, influenced what was to develop during the week.

One afternoon after a couple of days lying by the pool, with both girls in reasonably conservative bikinis, Debbie asked if anyone fancied a drink and then wandered off to the bar to place the order. When she came back, she had a mischievous grin on her face. "Have you noticed how whenever you have a conversation with Jim, he always talks to your tits?" she asked Liz.

"Not with me," Liz replied, perhaps it's just your tits he likes." Nothing more was said until Jim arrived with a tray of drinks, and sure enough, his eyes went straight to Debbie's tits.

After Jim had left, Mark commented about Jim's focus of attention and said, "he's obviously got the hots for you, Debs, perhaps he fancies experiencing an older woman." After a few laughs, the conversation drifted off to other things, and nothing more was said.

Later that afternoon, when Debbie and I were alone, I brought the conversation back to Jim and his 'focus of attention', and in a joking way, I said, "perhaps we should give him something to really focus on." "What do you mean," Debs asked "something like a spot of topless bathing"? "Maybe," I replied, "let me think about it."

That evening, after a long day by the pool, the Ouzo was flowing, and Debs was in a great, if slightly tipsy mood. That was the point that I formulated my plan. I wandered over to the bar and casually asked Jim what time he finished work. "10:30," he replied.

I ordered the drinks and returned to the table. The time was now 10:15, so I started to make noises about being tired and turning in. "I hope you're not too tired" Debs piped up with a cheeky grin, she always gets horny when she's had too much to drink. "Never," I replied, and we both got up to say goodnight.

On the way to the room, I asked Debs if she fancied a nightcap and suggested she continue up to the room while I went to the bar to order some drinks from room service. When I got to the bar, Jim was there alone, and I ordered 2 Ouzos and asked him to deliver them to our room. "I'm just finishing," he replied, but I'll get someone else to deliver them. I looked him straight in the eye and said "Jim, both Debbie and I want you to deliver them personally and we will make sure it's worth your while" Jim obviously thought this meant a big tip, so agreed to say that he would deliver them on his way out of the hotel. PERFECT!

I then ran up to the room to make sure Debs did not fall asleep. As is often the case when she has had a bit too much to drink, she was lying spread-eagled on the bed fully clothed and in a husky voice said: "strip me." I looked at my watch, and it was 10:25, perfect timing. I gently began to remove Debbie's clothes, starting with her lightweight chiffon top, followed by her bra. I began to caress her tits gently while licking and nibbling her swollen nipples.

She began to moan softly, and while continuing to play with her tits with one hand, I slowly moved down the bed to remove her white skin tight leggings, revealing her streamlined red thong. As I removed her thong, exposing her clean, shaved fanny, there was a quiet knock at the door. I'm not even sure if Debbie heard it. I threw the bedsheet over her exposed body, slipped off the bed and went down the hall to the door.

I swung the door open to find Jim standing there, holding a tray containing 2 Ouzos. I told him to come in and immediately shut the door behind him. I told Jim to put the tray down, and as he did so, I glanced over at Debbie, she was staring at Jim with a horrified look on her face. Don't worry Hun, I said, Jim's just popped in for a chat. At this point, a look of realization came over her face, and a sparkling glint came into her eyes. "Come over here and talk to me then, Jim," she said in a husky voice.

It was now Jim's turn to look shocked, and he glanced at me for guidance. I simply winked at him and nodded my head. I sat down in the armchair, sipped my Ouzo, and began to watch my long time fantasy begin to be played out. As Jim got close to the bed, Debs removed the sheet from the top half of her body and asked Jim if her tits were as good in the flesh as they were in his imagination.

Again Jim looked at me for assurance, and again I nodded. At this point, the room's atmosphere was electric, and I don't think any of us knew what was going to happen next. Jim was still acting very coy, but Debbie reached up and began gently stroking the front of his knee-length shorts where his semi-hard bulge was starting to show.

I saw a change come over Jim's face, and a look of anticipation appeared in his eyes. Jim began pressing himself into her hand with his eyes closed. I had never imagined she would take the lead like this; the very best I had ever imagined was that she would cooperate after some gentle persuasion. I got up from my viewing point, went over to the bed, and removed the remaining sheet from the bed to expose all of her body.

Jim could now see everything she had to offer, and I could tell from the now large bulge in the front of his shorts that he was keen to try all she was prepared to give. Debs slowly undid the fly on Jim's shorts. He was not wearing any underpants, so his cock was immediately exposed. She eased it gently out of his shorts and slid his balls up and out of his open fly. I think this was the first time Debbie had seen an uncut cock, and it seemed to fascinate her. As the shiny bright red tip of his knob began to protrude from under its protective foreskin, she got to her knees and began to suck and lick his balls while she wanked his cock.

Jim began to moan like fuck; he loved it! His cock was now full, erect and throbbing, and now it was my turn to be shocked, as I watched my previously un-adventurous wife take Jim's cock between her puckered lips and I watched in fascination as it disappeared into her wet, pink mouth. Now I'm not small by any means, but Jim's cock put mine to shame, and she was struggling to get it all in. She persevered through, and I watched in sheer ecstasy as Debs gorged herself on Jim's swollen cock.

At one point, I swear she took it right in up to the hilt and buried her face in his mass of thick black pubic hair. Jim was by this time going wild, and I was sure that he was going to cum. I wanted this fantastic experience to last forever, so I leaned over and whispered into Debbie's ear, "don't rush it, babe, take him gently and make it last." She sighed, but reluctantly released Jims cock very slowly, nibbling on the bell end as it exited her mouth. It was now shiny and wet from the juices of her mouth, and she told me to give Jim some direction.

I spread her legs wide and said to Jim, "come on, mate, let's have some real fun with her." Jim obliged by sliding across the bed and guided his cock to the entrance of Debbie's swollen pussy. Unfortunately, what happened next was all too predictable. We later discovered Jim, who was still a virgin, moaned and shot his load of white creamy cum all over Debbie's fanny and stomach. And what a load it was, it went everywhere. Her stomach looked like someone had sprayed it with double cream. She groaned in frustration, while Jim's face took on a look of major embarrassment.

I took control and told Jim to sit in the chair, take a few sips of Ouzo, and get his stamina back. I then got between Debbie's legs and began to kiss, lick and nibble her swollen mound and her erect clit. The taste of Jim's cum, mixed with Debbie's love juices, was fantastically erotic, and I can still taste the cocktail of flavors to this day. My work on Deb's clit quickly brought her back to a frenzied state, and as I raised myself up in preparation to give her the fucking of her life, I noticed Jim playing with his once more swollen cock.

I beckoned him over and told him, "it's your party, mate; go for it." He didn't need telling twice and immediately lunged towards her open fanny lips with his cock. Due to his inexperience, he missed the target, and Debbie squealed in pain. I reached down to guide him into her and could barely get my hand around its girth; it was so swollen. I gently moved his cock to the entrance of her sopping wet pussy, and as it entered her, he gave out a long low groan. As Jim's enormous cock gradually disappeared inside Debbie, she let out an ecstatic squeal and began to shout, "fuck me, fuck me."

This coarse language from my previously naive wife, coupled with all this action, was becoming too much for me, so I positioned myself just in front of Debbie's mouth. Without even asking, she instantly began to gobble my cock. I couldn't believe it, my wife being spit-roasted; Heaven. After 3 or 4 minutes, I could tell that Jim was again ready to shoot his load, me too.

I took Debbie's head in my hands and began to fuck her mouth as if there was no tomorrow. Jim let out some loud groans, and I knew it was time. I relaxed and let my cock do the rest. Within seconds, I was spurting into my beloved wife's mouth, and Jim was spunking inside her fanny. Debs let out a silent scream and then gulp down my cum while she came to a shuddering climax. We were all exhausted and collapsed in a heap on the bed, and I drifted off into an exhausted sleep.

I am not sure exactly what it was that woke me, but as I came to, I could hear whispers and muffled giggles. I looked across the room, and Jim sat in the chair with Debbie straddling him, her body grinding into his crotch, with her head flung back like a wanton slut. She had Jim's head held in both hands and was pushing his face into her tits. Initially, I felt a bit jealous as this was supposed to be a threesome. However, it was one of the sexiest sights I had ever seen.

My once innocent wife now fully converted into a raging nympho, being shagged by a 19-year-old hunk. After watching for a few seconds, my cock was once again standing to attention, and I just laid back, watched the show, and did what any red-blooded male would do and wanked myself into oblivion.

Jim left us shortly after, and Debbie and I collapsed onto the bed in exhaustion. As we were drifting off, Debs leaned over to me and whispered: "that was fantastic, BUT remember, what happens in Kefalonia stays in Kefalonia, it's our secret and can't ever happen again." Reluctantly, I had to agree, but I am keeping my fingers crossed.

This is a true cuckolding story. The hotel exists in a town on the East of Kefalonia, and Jim is a real waiter at the hotel. Only the names have been changed to protect the 'innocent.'

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