Part 10
In 2005 the company I was working for sold and I received a big payday for my stock, I also started to receive job offers and decided to leave for a bigger opportunity with a company. It was also around the time I was turning 30 so I planned it out to have a month off between jobs since I have not had a break since high school since I went right into college and worked every summer. I planned 3 weeks of vacation 1st flying down to Florida and going on a cruise for a week, to be followed by flying to a resort for 2 weeks, then back home for a week before starting the new job. The 1st week on the cruise was fun, it was a singles cruise week and I did a lot of hooking up with just females getting laid the entire week, but no bi sex. I got off the cruise back in Florida and flew right to a resort for the next 2 weeks. The 1st couple days was similar to the cruise I hooked up with single girls and relaxed which is what I needed. A couple days into the trip while relaxing I met a couple Bob and Jill there for their 20th anniversary and were both 42 years old. Jill was about 5-6 120lbs long blond hair, and Bob was in shape about 5-11 salt and pepper hair. We had some good conversations over drinks and agreed to have late night cocktails together. That night we met for drinks and had a good time, and at what point Bob went to the restroom and Jill mentioned that Bob was going golfing the next day, she winked and said he would be gone in a couple hours as I was interested in getting together with her in their room. I was taken back at 1st and said wow nice offer and you are hot but not sure how smart that is with Bob here and I rejected her offer with her being upset by the rejection. Bob returned and they left to go back to their room. The next day I was having a late morning cocktail when Bob approached me, he had on his golf gear and grabbed a drink before the shuttle was taking him to the course. Before he left he said he and Jill agreed to have a fantasy week and what happens on the island stays on the island, he knew what she asked me last night because he is the one that approved it and said please reconsider her offer while he is gone.
I sat there drinking and was shocked by this but also very interested now, 30 minutes later as I was laying down Jill came and sat next to me. We talked, had drinks and flirted with each other, eventually making it into the pool where we messed around and finally kissing while she grabbed my cock through my trunks. We got out and had another drink letting the sun dry us as we continued to flirt and even kiss, finally she said are you going to fuck me or what. I wasted no time as we headed to her suite where we spent the afternoon giving each other oral and fucking each other multiple times. We made our way back outside grabbing drinks as she continued to flirt with me and kiss me and then Bob appeared after golfing all afternoon. This didn't stop Jill as she touched me kissed me in front of Bob and then they left saying they had to get dressed and have dinner and we agreed to have drinks late at night. I went back to my room and fell asleep for a couple hours after all the action. Once I got up I showed, dressed and made my way back to the bar area outside and had dinner and drinks. Later in the night I was approached by Jill who gave me a hug and invited me over to her table with Bob, she looked very hot in a nice tight dress. Once I sat down Jill sat very close to me with her hand on my leg and taking mine and putting on her leg. We had drinks and talked about Bob gold and some sports, after about 30 minutes Bob got up and said he was heading back to his room, as he left he said have fun as he winked. Jill and I had another drink and talked about our afternoon, my hand made it between her legs feeling her soaked pussy. Jill then went on to tell me that when her and Bob left earlier they went back to the room where she told him about what they did as he fucked her which was the best sex they ever had based on me warming her up for him. She then said he wants me to go back with you for a midnight session, but with one condition, I asked what that was. At this point I had a finger in her pussy and her hand was rubbing my cock, she leaned in and kissed me then whispered in my ear that he wants me to cum in her pussy so he can feel it later. We almost ran to my room where we had a fuck session for the next hour with both of us coming twice, and me both times in her pussy. After the 2nd time she got dressed, kissed me and said she will meet me tomorrow and left.
The next morning, like the previous day I made my way to the bar for late morning drinks, I had lunch and relaxed but no sign of Jill or Bob. A couple hours later I saw them getting off a shuttle where they must have gone on a trip. Jill came over to me and said will I be here for a bit and I said yes, and she said good she will be back in 30 and gave me a kiss and left. She returned as she said and had a drink with me then said will I take her back to her room for a nice afternoon snack, and off we went. We got back to her room and I was taken back. There was Bob wearing only panties with his arms and legs tied to a chair, and also gagged. The chair was in front of the bed in the room where Jill sat me down there and we kissed and made out like two teenagers. After a couple minutes of this Jill pulled me off the couch so we were both standing right in front of Bob, she pulled off her bikini and she grabbed me to suck her nipples, she then looked at Bob and said you want me on my knees, and he just shook his head yes, as she fell to her knees and lowed my trunks releasing my cock ad Bob moaned into his gag. She took my cock and looked at Bob again and said honey this is the cock that's been fucking your wife, and with that she took my cock in her mouth while her husband watched. With this scene I didn't last long and after a couple minutes I exploded in her mouth while she took it all in her mouth while Bob watched on. She kept sucking me, and rubbing my balls, getting me hard again and then led me to the bed where she positioned us so Bob could see us perfectly as I fucked his wife. Since I came already I was able to last a while as we fucked in many different positions, also Jill was very verbal making comments about how my cock was bigger and I fucked her better than Bob. I finally came in her as we laid next to each other catching our breath, she made a comment saying that was the best fuck I ever had. She then asked me would I please untie Bob if he has to do something. I went over and untied him, he got up, took the gag out and went right into the bed as Jill spread her legs and he ate my own cum out of her pussy. I stood there watching Bob eat cum out of his wife's pussy, my own cum, she verbally called him names, saying this is what he always wanted to do. As I watched I somehow got hard again and Jill noticed this, so she motioned me over to lay on the bed. She changed positions, getting up on all fours as she instructed Bob to eat her out from behind and sucked my cock. After about 5 minutes Jill let my cock slip out, and looked at me and asked me can my husband suck your cock. I was so horny I nodded my head and Jill rolled to the side and said pussy boy suck his cock until he comes. Bob took my cock in his mouth and gave me a good blow job, I could tell this wasn't his 1st time but probably hid from Jill, based on her talk saying this is something he always wanted to try. I lasted about 5 minutes before I exploded in his mouth with him taking it all since it wasn't that much since this was my 3rd time. I got dressed as they laid on the bed and I left.
That night I didn't see them so I just hung out alone at the bar having drinks and relaxed listening to music. The next day I didn't see them as they probably went on a trip. I relaxed all day catching up on rest and enjoying the drinks and weather. I went back to my room around dinner time, to take a shower and as I got out there was a knock on the door and it was Jill dressed very sexy, I let her in and she gave me a kiss and asked me if I wanted a date for the night, to which I agreed. We had a romantic dinner on the beach which she setup followed by a show we went to back for drinks and then back to my room where we had a couple hours of amazing sex and then fell asleep. We woke in the morning, which led to a fuck session which the led to the shower where we fucked in there and back to the bed where we talked about our amazing night. It led to us talking about the other day with Bob sucking me and asking was I into that which I told her I was Bi and enjoyed it. She liked hearing that and asked if I was up for it again, and I said I think I could be convinced. She said she was going for a spa day all afternoon, can I please take care of her husband's fantasies, I said maybe she kissed me and said she had to go and leave. I went to the bar around my normal time and shortly after noon Bob came up to me and we had drinks. After a couple drinks I said to Bob that wasn't the 1st time you sucked a cock the other day was it. He said no it wasn't but Jill didn't know, he went on to tell me he was BI and had his 1st experience with a coworker a couple years ago, I told him about myself also, and then we headed to his room. Once in his room we hopped into the bed into a 69, and then he begged me to fuck him, he had lube but no rubbers and my thought process was I have been fucking his wife bareback wo oh well. He was a good fuck, nice and tight, and after some time I was ready to come and asked him where he wanted it and he yelled in me so I unloaded in his ass. We then headed to the shower to clean up which then led to kissing and oral in there until we were back in the bed with me fucking him again, until Jill walked in. All she said was this is hot as she removed her clothes and got on the bed so Bob can eat her out while I fucked him. After a couple minutes of this she said don't come to me, and to pull out. I pulled out as I was standing there and Jill told Bob to clean my cock off and give it to her, Bob obeyed and sucked my cock, then led me to the bed where Jill was laying there with her legs spread, Bob took my cock and guided it to her pussy pushing m cock into his wife and then kissed me and said please fuck my wife. I fucked Jill hard for the next couple minutes until she came and I came in her pussy. As I pulled out Bob jumped right in to clean her pussy out. As I was leaving they said they both wanted to have dinner with me tonight, I agreed and met them for dinner, and afterwards drinks and music. It was getting late and Jill said she was tired from fucking me all night and her spa day so she was calling it a night, she gave us both a kiss and said try not to have too much fun. Bob asked was I up for some more action, and I said I was but I need help now, he asked with what and I said I have been taking care of you too but I am in need of some fucking to me, and grabbed his sock thru his shorts and said how about this in my ass tonight. He didn't need to be told twice and we headed back to my room, where we 69 and he fucked me bareback twice coming at me both times.
The three of us played for the next couple days until they left a day before I left, we lived back in the states I on the east coast and them in the middle of the county. We exchanged information promising to keep in touch and me thinking we never would but we did. As I write this story this encounter took place 16 years ago, and we get together to this day a couple times a year and vacation together which has led to many amazing encounters which I will share later on. What a Great vacation.
Part 11 to Cum