Our Vacation Cuckolding – I previously posted stories about my girlfriend (now wife) Jen and I’s experiences but never on this blog. It involved a holiday we had in Tenerife several years ago. On the holiday, we met an older man in his 50’s called Stu who ended up cucking us and making Jen his slut for the week. She was at the time 19 and seeing her with this much older man still ranks as one of the wildest and horniest experiences of my life.
I remember Jen arriving in the bar of our hotel wearing a black boob tube which in all honesty looked a dress size too small – her tits were barely kept in and as she walked she was constantly pulling it up. Her ass cheeks were almost visible and it was clear she was wearing neither panties or a bra. The heels were the sluttiest though – gold with a strap which curled up around her calves finishing just below the knee. She looked a complete slut and with her chunky necklace and bracelet her outfit was complete. I was in the bar with Stu’s friends – none of whom were aware I was her boyfriend and they all whistled and made crude comments when they saw her. “Fucking dirty bitch”, “Cockteaser, needs well fucked”, “looks like she could suck off every guy in the room” were a few of the nicer ones.
The two of them came over and Stu announced tonight was a karaoke night and that we should go to a local bar. To get in the spirit he ordered a round of drinks and some shots and over the course of the next hour we all got more and more drunk – including Jen who always seemed to have a shot put in front of her as soon as she downed one. We left to go to the next bar and it was obvious Jen was the drunkest there, she walked arm in arm with Stu and his mate, by this time not really bothered if her dress rode up or slipped down a bit more than it should. She looked a total slut – boobs almost out and her left ass cheek quite clearly on show. As we waited to enter the karaoke bar, I could see Stu’s mate Doug slide a hand onto Jen’s bare ass and start to rub it while Stu was talking to the bar man. We all went in and they continued to drink and drink – then Stu suggested Jen get up and sing. Now she is a great singer and one of her specialities in Black Velvet, so up she went and started to get really into it – swaying and dancing quite suggestively – much to the delight of the men in the audience, those at the front got a much better view than they expected!
After a few hours we decided to head back to our hotel and we left, again Jen in between Stu and Doug although now it was more like she was being helped along she was so drunk. As we walked the street was busy with drunk groups of guys, many passing by commented on Jen’s slutty look which Stu and Doug encouraged. We got back to the apartments and went back to Doug’s room – when Stu ran out of cigarettes and decided to go back to his room, leaving Jen alone with Doug and the rest of us. All of a sudden I realized how out of control the situation was and how vulnerable Jen was – but I couldn’t help but get hard at the possibilities. Doug had got out a bottle of tequila and we all began taking slammers, Jen however was by this stage about to pass out so Doug asked me to help him take her out to the balcony for some fresh air.
We got her out and he sat her on a chair, by this time her left boob had fallen out of her top and her dress was practically around her waist. “Fuck I cant reisist” he said “Stu will never know and she’s so fucked she’ll never remember” and with that he reached over and started groping Jens boobs, pulling them out of her top and mauling them hard, pulling her nipples then sucking on them. Jen moaned and Doug said to me “Come here and keep her quiet” with that I walked over and put my hand over her mouth. Doug then parted her legs and started finger fucking her furiously, to the point his palm was slapping against her mound. “You fucking love this you cock teasing little bitch don’t you” he whispered in my girlfriend’s ear as I covered her mouth to stop her moans.
Just then Doug stood up and took out his cock and told me to watch for Stu coming over from the other block. He unzipped his cock and stuffed it in Jen’s mouth, “That’s it you filthy slut – take it all the way down” he commanded as he roughly and frantically pumped into her mouth. He only lasted seconds until he grunted and his ass cheeks clenched and it was clear he was cumming in Jen’s mouth. “Fucking hot little cock tease – you got what you wanted didn’t you?” he asked holding Jen by cheeks “You love being the slut and you beter not tell Stu about this or else” Jen was so drunk it could have been Stu to her, but she nodded. Just then we heard Stu come back in the apartment – “How’s the party going” he asked, Doug and I smiled as did Jen – it was to be a long night of us watching Stu with Jen, pleasing her and making her moan endlessly until she said she was sore. Then he went at her one more time to ‘mark’ her so to speak…
The next morning Jen had no hangover which puzzled me? She told me how she faked being drunk so that she could show off her tits to everyone and have Doug fuck her too. I was taken aback and smiled. We then fucked the rest of the day until Stu took over at night. What a vacation!