Holiday 2 – Challenges

Introduction:
As I woke that morning I started to think about what had happened the night before. Had it really happened? Had Jen really entered that wet t-shirt competition, stripped naked and had her pussy and nipples licked and sucked by 3 complete strangers, all in a packed bar? Had she had an orgasm right there in front of them or was it all a dream? As I looked at Jen as she slept I knew it hadn’t been a dream. I remembered how turned on it made me as I watched Jen give herself so freely to the mouths of 3 complete strangers. I smiled as I thought about it.
Just then Jen woke up. She looked at me and said “I’m so sorry about last night, I don’t know what came over me”. I asked her “Did you enjoy it? Be honest”. Her eyes lowered and she meekly said “honestly? Yes, I did enjoy it” “What made you do it?” I asked. “Well” she said “It always turned you on when I stripped for you, I wanted to see how much it turned you on seeing me strip for a large group of strangers. As no one here knows us when I heard about the wet t-shirt contest I saw an opportunity and took it”. “But what about what happened with the 3 guys?” I asked. She replied “I saw the reactions that the other girls were getting and as each one went before me I was getting more and more turned on thinking about what I was about to do. When I started dancing and the men started cheering I got really turned on. I have never told you this but it has always been a fantasy of mine to be with a strange man and I was so turned on that I couldn’t resist. I didn’t expect to do what I did, but as soon as the 2 guys lips started sucking my nipples I wanted to come right there, that is why I got the third guy to lick my pussy. I hope I didn’t hurt you”.
“Why did you never tell me any of this?” I asked. “You never talk about your fantasies to me. What other fantasies do you have?”. “I was afraid if I told you that you would get mad and leave me” she said. “I will never leave you” I told her “especially not now I am getting to know the real you. I want you to experience as much as possible. Lets make a deal – we will act out each others fantasies but there has to be some ground rules. 1. Never with anyone we know. 2. Always use protection. 3. Always do things together. 4. Only on holidays. How does that sound?”. “I would love that” Jen said “and to think, I was afraid to talk to you about my fantasies. What do you want to do tonight?”. “Leave that to me, I’ll come up with something” I told her.
My mind started racing. I could not believe this. All my fantasies could become a reality, as could hers. I had never told Jen but the idea of her with other men had also been a fantasy of mine for a long time. A recurring fantasy popped into my head. It would be perfect for tonight. I began to plan for the evening. I would set Jen a number of challenges; she would have to pass each to get to the next challenge with the challenges getting sexier as they went on. I went to the shop and bought a deck of cards and a pen. I began writing challenges on the cards. By the time I was finished I had 10 challenges for her. I asked her if she was up for it and she said she was. As we got ready Jen must have drank nearly a full bottle of vodka – “to give me an extra bit of courage” she told me and smiled as I handed her her first challenge.
“Flash your tits at a stranger from the balcony” “That is easy” she said as she went to the balcony and called out to a group of men walking by. As they looked up she flashed her tits at them to cheers and whistles. She came back inside and said “I hope you have more difficult ones than that”. “Don’t worry” I told her, “They get a lot more interesting”. As we made our way to the bar I handed her 3 more easy tasks which she quickly completed. I handed her the 5th challenge. “Now we are getting places” she grinned. The card read “Find a group of at least 5 guys and kiss each passionately”. She looked around and spotted a group of 6 guys. She walked straight up to them and started kissing each one passionately as the others cheered her on. I immediately got a hard on as I watched them all kiss her and feel up her sexy body. She had a big smile on her face as she came back over and asked “What’s next?”. I handed her card number 6 as we walked into the bar.
I knew number 6 would be more difficult. It read “Find a male/female couple and kiss both” I already knew that she had no problem being with other men, would she hesitate about being with another woman? Jen looked at me and smiled “Naughty, naughty” she said. With that she started to work her way around the room chatting to people as she did so. Soon she seemed to be deep in conversation with one couple. She then looked over at me and pointed. The couple smiled so I waved back at them. As I did so Jen threw her arms around the woman and started kissing her, then moved over and started kissing him. She walked back over smiling “That was Jake and Lillian” she said “I like them, what’s next? This is getting interesting”
“Well, if you are enjoying this so much how about you share the enjoyment” I said as I handed her card number 7 – “Give a stranger a blowjob” “That will be easy” she said as she again looked around the room. She spotted 2 guys sitting at a table at the end of the bar. She went over and started chatting to them. Soon they were laughing and joking. She sat down between them and started stroking their cocks through their trousers, their smiles got bigger. Before long Jen had opened both of their trousers and was stroking their cocks under the table. Jen then slid down under the table and started sucking the cock of one of them while continuing to stroke the other’s cock. Before long I could see him jerking in the seat and when he stopped I knew that he was after blowing his load into Jen’s mouth. She then moved over and started sucking the other guys cock. As she did so she turned her ass towards the other guy, he wasted no time in dropping his hand and moving her thong to the side before sliding his finger into her wet pussy. I could see his hand getting faster and faster as he continued to finger fuck her. Before long the second guy also came in Jen’s mouth, this was enough to push Jen over the edge and with her pussy still being finger fucked she came to her first orgasm of the night. As she sat back up I saw her remove her thong completely and hand it to the guy who finger fucked her – a souvenir for the orgasm he had just given her. She whispered something in their ears and they nodded and she walked away.
“Your challenge was way to easy” she said “so I decided to double the difficulty” she said with a satisfied smile. “I may as well throw away challenge number 8” I laughed as I handed her the card that read “Have an orgasm without intercourse”. “Looks like I am one step ahead of you” she laughed. “Let’s have number 9”. She read it and looked at me with a concerned look on her face. “Are you sure you want me to do this?” she asked as she read “Fuck a stranger in the toilet of a bar”, “what we have been doing so far was just kissing and foreplay, but this is another man’s cock in my pussy, are you sure that you are ok with this?”. “Would you like to do it?” I asked. “Of course I would love to get fucked hard by a stranger, but only if you are ok with it.” “ Don’t worry” I said “ I will be in the next cubicle to you enjoying every moan you make, I may even peek over the top” I smiled. “Ok then, I will try to give you a good show” she said as we went off in search of the first cock other than mine to fuck her tight pussy in 7 years.
About 10 minutes later I saw her walking arm and arm with a hunky, muscular guy of about 25 with short blonde hair. I immediately went to the bathroom and went into the middle cubicle to ensure I would get to see the show. I heard the door of the next cubicle close and Jen giggle. I then heard kissing so I stood on the toilet and looked over the top. Jen wasted no time in getting his trousers off as they continued to kiss. As she pulled down his underwear a huge throbbing 10” cock sprung up. “Oh wow” said Jen “looks like I picked the right guy tonight, but you better put on a condom or no fun” I was relieved that Jen had remembered our rule about condoms. Before long they were back kissing and he moved Jen’s dress straps off her shoulders causing her dress to fall to the floor. As she stood in front of him completely naked he said “looks like I picked the right girl as well, a great body, and already ready for action under that dress”. “You have no idea” Jen said “now shut up and put that giant cock into my pussy and fuck me hard”. With that he put both hands on her ass and lowered her onto his cock as she leaned back against the wall for support. She had her head on his shoulder as he slowly lowered her onto his huge cock. She started moaning with pleasure as his cock spread her wet pussy lips and went deeper into her. It was a good job that the finger fucking she got earlier had prepared her pussy for such a huge cock.
She looked up at me and smiled. “I love you” she mouthed. It was too late to do anything now. Jen was now impaled on a 10” cock and all I could do is look on. When he was fully inside her he lowered her to the ground. He knew she could take his full length so turned her around and lined the tip of his cock against her pussy lips. In one swift thrust he buried his cock deep into Jen’s now soaking wet pussy “I am going to fuck harder that you have ever been fucked” he said as he started pounding his cock in and out of Jen’s pussy. Jen was moaning so loud that a crowd was starting to gather outside to hear what was going on. She did not care as she was getting fucked by a 10” cock and she was loving every minute of it. I watched as Jen came twice and they guy was still pounding away at her pussy. As he started to get faster I could tell that he was about to cum and with a last few thrusts he came causing Jen to leave out a scream of pleasure as she hit her fourth and biggest orgasm of the night. What a show she had given me. As she lay back on the toilet I looked at her naked body with sweat rolling down her tits from the fucking she had just received. They quickly dressed and as they left the toilet they got a round of applause from the waiting crowd.
I left shortly after and went to find Jen. She jumped into my arms and planted a huge kiss on my lips and said “Thank you so much for challenge number 9. Even though I had a huge cock fucking me it was the fact that I knew that you were watching me that turned me on so much. I hope you enjoyed it as much as I did”. With that I grabbed her hand, placed it on my cock which now was a raging hard-on and said “Does this answer your question?”. “Don’t worry” she said “I’ll take care of that too, now what is my final challenge?” “I don’t know if you will be able for it after the fucking you just got but here you go” I said as I handed her the last card – “Your fantasy come true – sex with multiple men”. She looked at me and said “I have a better idea, let’s go home instead. I reluctantly agreed, silently disappointed that I would not get to see the final challenge fulfilled.
When we got back to our hotel room I could not find the key. “Don’t worry, the door is open” said Jen. I looked at her puzzled as I could remember locking the door as we left. How could it be open now? She opened the door and we walked in. She turned on the light and to my surprise there were 3 naked men standing there in front of us. I immediately recognised them as Jake (the guy of the couple Jen had kissed) and the 2 guys whose cocks Jen had sucked under the table in the bar. Jen walked over to them and kissed each of them and stroked their cocks as she did so. Jen turned to me and smiled “I told you I was one step ahead of you, looks like the final challenge is possible after all. Oh, I also have another surprise for you, come on out” she called. With that the bathroom door opened and out walked a naked Lillian (Jakes girlfriend). She walked straight up to me and kissed me. “Lets finish the final challenge together” said Jen, but that is another story.

Read 10683 times |
Rated 87.8 % |
(41 votes)

Vote list (Close) :

Please rate this text: