From Fantasy to Bucket List to Reality - Our Hottest Experience (Long)

Have you had a fantasy that was on your sexual bucket list to actually do but haven't gotten around to it or your SO won't do it? Here is a story of one that both my wife and I shared that did become reality, and it was awesome!
A few years ago the wife and I would have occasional MFMs with a guy named Bob. Bob was our first time brining someone else in the bedroom and we definitely got lucky with him. He was a little older, eager to please, respected boundaries, was nice looking, well built, and had a thick 8” cock that he knew how to use. We got together with him seven times…most of the time both of us gave her pleasure, or in a few cases we took turns with her. Unfortunately, Bob’s job was going to be transferring him so we decided to get together with him one last time. We agreed on a date and then wifey dropped the bomb on me…she wanted to be Bob’s girlfriend for the night. We had discussed this as a possibility with someone, sometime, and Bob did seem like the perfect person to experiment with, so I agreed. However, wifey had more in mind. I would go along as a third wheel on the date, but she would be with him exclusively. I guess she had been listening to all those fantasies we had shared while fucking.
In the week leading up to her date, she cut me off from sex. She told me it wouldn’t be right to cheat on her boyfriend and wanted to save herself for him. She started sending him sexy texts and talked on the phone a few times, making sure I could hear her conversation. Each night we did something different in preparation for her date. One night we went out and she had me pick out condoms. She was giddy as I picked them out and asked if I would get hot at the thought of her rolling it down Bob’s hard cock. Another night we went to Victoria’s Secret to buy lingerie for her big night. At one point a cute salesgirl came over and asked wifey if she needed any help. Wifey held up a very sexy skimpy pair of panties and asked me if I thought her boyfriend would like taking them off her. The salesgirl just looked at me, then at our wedding rings, then back at me, and smiled while biting her lip. Another night we went buy some sexy heels, and then finally the last night was to buy a tight skirt and sexy blouse. She never degraded me, but she definitely was flaunting her night-to-be. Honestly, helping my wife prepare for someone is almost as hot as watching the actually sex itself. And for me, watching the foreplay/kissing is just as exciting as the fucking.
As the night approached the plan was for Bob to pick us up and take us to dinner. Although wifey had been talking sexy to him, she never actually told her of her entire plan. In the hours leading up to the date, wifey had me help her bathe. She knew the right things to say. She would ask what I thought about Bob making love to her, his tongue all over her body, and her having his cock deep in her throat. The buildup was incredible. She had me shave her little pussy, but leave a think “landing zone” above her clit. She said that Bob told her that it was his favorite look and she wanted to please him more than anything. I helped her dress, running the thigh highs up her legs, pulling her panties and skirt up in place, hooking her bra, and buttoning her blouse. And then she told me to go get ready while she finished up her makeup. But before I left she had one more surprise. She told me she was going to give her body over to Bob completely and she would do pretty much whatever he wanted. She asked if I was good with that I and told her yes, but she also said that if at any time I was uncomfortable I just had to tell her and she would stop at any time.
Bob arrived right on time. Wifey met him at the door and kissed him long and deep. She knows how much I love watching her kiss and make out with a guy. Bob reached around and grabbed her ass and pulled her tight against him. When they finally broke apart Bob told her how hot she looked and then shook my hand. Wife giggled and whispered into his ear. He seemed surprised and as I found out later her told her that she was all his that night and that I was only around for the ride and dinner. With that, we went out to Bob’s car. Wifey climbed in front with Bob and I sat in back. She snuggled as close as she could get to him and when we got to the restaurant after a short drive, Bob said that he had to sit there just a minute while he calmed down. Apparently, wifey had been playing with his cock through his pants on the way over and he had quite the hardon. After a few minutes, we exited the car and walked in, with them holding hands and snuggling the whole way.
The restaurant was nice and upscale, and had tablecloths. We had great conversations. Bob was not only a fuck buddy, but he had become a friend and was easy to talk to. But every once in a while I saw my wife squirm a little and give me a look that let me know that Bob was stealing a quick feel of her pussy. Frankly, I had never seen her so overtly horny. When we finally left the restaurant, the sexual tension was off the charts. Bob handed me the keys to his car and asked me to drive. He and wifey got in the back seat, and I had no more than left the parking lot when I looked in the rear view mirror and saw my wife head in Bob’s lap. I could hear her making noises as she sucked, and Bob close his eyes and leaned back his head. Wifey took a quick break leaned forward and asked if I like knowing she had Bob’s cock in her mouth. I replied that it turned me on very much, and then she told me to take the long way home by driving through the center of the city. She went back to driving through the city and at one point we were at a stop light and a guy pulled up beside us and looked over. He could obviously see my wife’s head bobbing up and down in Bob’s lap. He just smiled at me and waved and we drove on.
I finally got us back to the house and they quickly walked back into the house, disheveled and all. Once in the house, wifey asked me to pour us all some wine, and then started kissing Bob again. I handed them their glasses and the wifey took Bob by the hand and led him the bedroom. I started to follow, thinking I would get to watch, but she stopped me at the door, saying, “nope, Not tonight. It’s just me and my boyfriend. By the way, I don’t want to use a condom tonight. Is that okay?” She was on birth control, so I nodded yes, and with that she smiled, gave me a quick peck on the cheek, and shut the door.
As much as I wanted to watch her, I had asked for this very scenario many times in my fantasies, and now here it was. She was giving me my fantasy while living out her own as well. I wish I could tell you exactly what happened, but for the next nearly two hours I could only fantasize and wonder. They had turned on some music which masked all but the sounds of her loud cumming. Wifey cums very easily, and it was apparent that she was cumming a lot. I wanted to masturbate, but I was afraid that if I got invited into the bedroom I would not have wanted to waste my hardon.
Finally, the door opened and she peeked her head out and asked me to come in. When I approached the door she was snuggling back up against Bob. He put his arm around her, she laid back against him and spread her legs. “Come here” she said. I looked at her pussy. It was red and swollen, and in the low light I could see a bit of cum dripping put of her. “Come here and go down on me,” she said. Nervously, I approached her. I crawled up the bed towards her just fucked pussy. Again, I had spoke of this in fantasies, but had always thought there would be some planning and work up to it, it even happened at all. But here I was, just as I had fantasized about. As I approached them I could see Bob playing with her nipples and I could smell their sex. I put my mouth inches away from her open pussy and I could now clearly see Bob’s cum hanging on her labia and on the inside of her thigh. As I stuck my tongue out to touch her, I looked up and saw her turn her head to Bob and kiss him deep, her tongue sliding into his mouth. I closed my eyes and went for it. I could taste his cum first and surprisingly it didn’t bother me at all. I stuck my tongue deep into her and she gasped as I sucked up their combined cum. I had never even gone down on her after I had cum in her, much less another man, but here it was, and it was the most amazing, fucking sexy, taboo-thing ever, and I savored it. “I think he likes your cum,” I heard her say to Bob. “Yes, that’s it. Eat it. Eat my lovers cum out of me. If I had known you would have been this into it I would have done this a long time ago,” she said. I sucked her until she clenched up and came hard. Her leg squeezed hard against my head until she finally relaxed. She turned to Bob and kissed him again.
At that point, she asked me to leave again, and they spent the rest of the night together. She told me later about the details as best she could remember them. Bob fucked her in just about every position that night. At one point late in the night/early morning she back up against him and rubbed her ass against him until he got hard and woke up. She then got some lube, put it on her ass and his cock and asked him to fuck her ass. She wasn’t kidding when she said she was going to give herself completely to him.
The next morning she opened the door long enough to ask me to make them some coffee and told me that they were going to shower…and winked at me. The music wasn’t on this time and although the bathroom door was shut she did leave the bedroom door open. I could hear them fucking in the shower with wifey cumming several times. When they finally emerged, she came to me, kissed me deep and thanked me. She was reclaimed. Bob, ever the gentlemen, thanked me and said bye. That was the last we saw or heard form hi, but we used the experience for years and it was almost always the best sex ever. We tried similar experiences, but none every quite matched that goodbye girlfriend date with Bob. It definitely checked off nearly every box on the sex bucket list.
How about you?

 

Fantastic story, sounds like a great night.

 

Yes a great story and thank you for keeping it clean and within the rules framework

 

I have a few that became reality.
This one started later in life, I found a couple online looking for a man to do a strip show for her while he’s present.
And that she gets to play with the “stripper” A LOT. Well, I wanted to have some fun with a woman in front of her guy and I have always loved to be handled and stroked. She got handsy as soon as possible even though I tried the slow approach, as soon as my pants were low enough. Then I got to play with her breasts a lot, to the point I brought myself to orgasm between them. She had never had that done and she discovered she absolutely loved it.

I always wanted to have a woman who allows me to play with her breasts while she sleeps.
One evening I was with a younger woman and after some other fun things I asked if I could.
The only reason I stopped after a real good long time was that she had to go to work the next morning.
I was so tempted to give her more oral and have sex again but I chose to be considerate.

I had wanted to be with a woman who LOVES having a man in her mouth, not to stop after the finish. I met her online and she was disappointed when I asked her to start with her hands first, she was quick to tell me she wanted me to cum in her mouth.
Once I got played with enough she got what she wanted and she sucked greedily to completion and never stopped until I begged her to, she was doing it too hard. If I had not stopped her she would have kept going until I came again or went soft. I wanted that very much but she wanted to do it a little too hard to my liking.

I was a breast person ever before I reached legal age so I am keeping things in my adult days. Besides, nothing happened before anyway.
I always had the fantasy of being with a woman who absolutely loves her breasts played with a lot. Very very much played with.
That happened many years ago and it repeated itself a few cherished times but let’s pick one adventure that happened almost 3 years ago.
Fast forward to the rented room halfway between where we both live and after some kissing and touching I was on top doing nothing but fondling her breasts. She already told me she loved it before we got together and I promised her we would find out if she could reach orgasm that way.
She was happily squirming and moaning as I groped, squeezed, caressed them like it was going to be the last time of my life I was going to have breasts. She was loving it!!
Then I started using my mouth. That took things to the next level and soon she put the pillow over her face to scream and swear while having her first ever breast orgasm.
She was excited and giggling like a little girl for a while about it. I wanted to keep going, she did too but her body had to have a break.
I gave her two more before we had sex.
Skipping a few things, I was ready to give her oral later and I already knew she loved it.
She turned me down! Because she WANTED me to use my hands instead so I could use my mouth on her breasts again.
My only “regret” was that I could have stopped a few times A) to play with her longer,
B) to let it build up longer for her and give her longer pleasures
But when she orgasmed, I don’t know if that could be called fireworks or earthquake but definitely strong tremors that lasted a couple of minutes where I could not touch her body at all or it became way too sensitive.
And it was her birthday, and the first time she had sex for her birthday.

Teach a woman how to give oral, blowjobs.
Don’t get me wrong, I so love pleasuring a woman and having sex together.
It was her who asked me to show her how to.
(I did it with my first gf but not the same)
She was self conscious about being watched, I said the right thing because after that she was pleased to see me watching her.
And I ended up making her want to make me cum in her mouth, turned out she became a cock sucking addict who often asked me to take it out so she could do it, wanting me to grab her head.
We also discovered she could orgasm with her breasts too.

Last fantasy here, still with the same woman.
I always wanted to try very slow penetration.
I mean very slow. We tried it one evening and from that day she only wanted it slow.
I absolutely loved it too, especially that she loved it made it even better.

 

In a not too distant past I started wanting to film someone taking care of me, my pleasure.
It took me some courage to finally ask, and I asked the right one who was open to it.
I filmed a couple of beautiful HJ and BJ to completion, things I will always keep for personal private use.
I was able to shift the filming to capture swaying breasts during the action, and also me fondling her breasts.
I was able to capture her taking me deep a few times, the pulsations and contractions during the final orgasm as she edged me a few times.

 

And probably the last one, I had most of my fantasies become reality.
It doesn’t matter if it’s very basic but it was still something I have always wanted.
Are you already wrote about this woman in a different thread.
I used to tell dirty stories for this woman and she wanted to try everything I wrote.
The day we were getting together, she told me to wear thin PJ pants with a fly, nothing else under. The idea was to go for an evening drive and she would give me a blowjob while I drove.

I sure enjoyed having her mouth giving me pleasure, and my pleasure was more than physical because I knew she was loving it.
I took my time driving safely with the car on cruise control and having me in her mouth was all that mattered to her at that moment.

however, the actual fantasy for myself was something else after she had hers.
I wanted my penis to be played with and touched during the drive back while I played with her breasts the entire ride.
She was very into the idea, she took her bra off and we had more fun on the return drive.
I loved feeling her nipples become erect under my touch, and the way she loved being touched. I would still love to find someone to do that thing all over again

 

All very hot stories . Sitting here with a hardon and nowhere to go with it . I'll figure something out !

 

True story again, something I had wanted to try for a couple of years or more.

I contacted this woman online and after discussing a few things we agreed to meet somewhere. I was on the road unable to be somewhere completely comfortable and private, and she was not able to bring me to her place. So we agreed to have her hop in my car and she give me directions to a quiet spot she knows.

We moved to the backseat do you have more space and it was not long before she took me in her mouth because I mentioned that I had not had a nice blowjob in quite a while.
It didn’t take long to feel extra hard and I tried to move myself to watch her do better.
Then I got brave and asked if she would allow me to use my phone camera to be able to watch, and then I went one step beyond and asked if I could film it.
She agreed!! So there I was aiming the camera to be able to capture her blow job, my hard veiny cock in her mouth, and able to watch it from a nice perspective while looking at her pleasing my cock on the screen.
I am quite certain she liked it, because she gave me a lot of licking and she looked at herself sucking my cock many times.

I had her stroke my cock and I filmed it also, and I played with her jiggling breasts while she stroked me. After a few minutes the inevitable happened and she placed her lips over my cock too allow me to experience an orgasm during a blowjob.
I got to watch the movie a few times while masturbating by myself days later.