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Wife and I try a Cuckold Night Out
17/10/2021
My wife and I had been roleplaying about cuckolding and she was enjoying the idea of it.

One day she asked me if I’d actually wanted to be a cuckold for real, I was very surprised that she asked me that and even more surprised by my answer.

I said yes, but I would want to feel like I was part of the entire process. She just said okay that gives me something to think about

About a week later we were role playing again and while she had my dick in her hand teasing me about how small it is she asked me again if I wanted to be a cuckold, obviously at this moment I said yes.

She asked me several more times and I said yes each time. At this point she informed me that she had been chatting with a younger man at work that she was very sexually attracted to him…. I came immediately.

She said, I’ll take that as a sign of agreement and I just blushed she then said John had asked her out on a date in 2 weeks on a Saturday night and she had already told him yes but wanted me to help her look and feel her best for the date she then got out of bed and went to get my chastity device she said she knew she needed to have this on me for the next 2 weeks at least in order for this to go smoothly (my first though was 2 weeks?DAM) I completely missed the words “ At Least” but this is where the story gets fun for her and I.

Next day

1st thing I did was take her to get a tanning package so she could tan everyday for the next 2 weeks then I took her to a jewelry store and bought her the 1 KT diamond studded earrings she has always wanted she was shocked to say the least she told me she was really looking forward to wearing them for John my tiny dick tried to get hard immediately.

I then took her to Victoria Secret to get her matching bra and panties I found a white bra and panty set that I though would look great on her and she irritatingly said John had asked her to wear all black for the date because they were going to a theme type dinner party that was all black attire.

We then went to look for dresses she found short black dress that was very low cut in the front that she would never wear in the past, my wife had very large breast that she always tried to keep hidden, I asked her if she though the dress was a little revealing and she said why? You have asked me many times in the past to wear something like this why is it a problem now ? I said you are right and apologized.

Day 2
I went online and found a spa that offered Brazilian waxing, face scrubs and chemical face treatments and made her an appointment 5 days before her date Dawn insisted 5 days because she didn’t want her face to be red or have red bumps on her intimate areas.

Day 3

By day 3 of chastity I was so horny I could hardly stand it all of this thinking about her date was almost to much to handle but I still had a lot to do to help her prepare for her date so I went back online and found a very popular high end hair salon that did hair, nails, makeup for special occasions they didn’t have any appointments for the morning of her date so I was very worried but I did not give up I called the salon and spoke to the manager and told her this was and extremely important night for my wife and I would tip very big if someone could help.

She said she would call me back so I sat nervously for an hour (seemed like hours and hours) waiting for a call back. When my phone rang I answered very quickly, the manager (Nancy) told me that she was able to get one of the girls (Sabrina)to come in on her day off and help but reinforced that it was her day off so make sure Sabrina feels like we appreciate her. I was so relieved and told her I would make sure and thanked her several times.

Day 4
I woke up at 5AM to my little dick straining in my cage so I decided I would go ahead and get up I went in and showered, shaved I saw a new bottle of cologne on the sink so I opened it and sprayed some on I went to the kitchen and made the wife some coffee and took it to her in bed when I woke her up and handed her the coffee she started sniffing me and said WHY ARE YOU WEARING JOHNS COLOGNE? My eyes got big and I said I though you got that for me she yelled at me hell no go shower again wash that cologne off them go to the store and buy another bottle, I can’t give John an opened bottle of $500 cologne! I was thinking (holy shit) but my little dick was telling me to go to the store so that’s what I did.

Day 5
I woke up early again to my tiny dick straining in my cage so once again I got out of bed and showered went and got coffee for my wife she sat up in bed to drink her coffee and asked me to rub her feet. While I was rubbing her feet she asked me if the waxing I had scheduled was front and back, I told her I think it’s just the front she told me to call the spa and make sure I had scheduled a full Brazilian if I had not then inform them that she would be needed a full Brazilian when the spa opened I called the manager and he told me that I did not schedule a full Brazilian but it was not a problem he would change it on the schedule and let the specialist Jeremy know. When I heard the name Jeremy I was shocked and told him I thought I had scheduled with Stephanie, he informed me that Stephanie was no longer working for him and Jeremy took all of her clients I asked if he had any female specialist available for that day and he informed me that he did not my heart sunk to my stomach but I simply said okay and thanked him
When I got back to my wife I told her what the manager said and she just smiled and said that sounded like fun, I was so shocked but relieved she was not mad.

She then informed me that I need to to the store and get her an enema, I was really confused and asked her why she needed that. She told me that she was talking to John and he said he loved sex and hoped she was not one of those reserved good girls and she could not tell him no to anything because she was afraid if this night did not go well that he would not ask her out again.

The next 7 days went by like normal except I had to wake her up early every morning to give a massage and coffee and listen to her talk about John and how excited she was for Saturday night to happen but then my wife did something that shocked me more then anything so far, she told me that she needed me to go get a black suit with a black tie and a white shirt and I also need to rent a black SUV because I would be driving her on her date so John did not have to worry about parking and she would not have to walk a long distance to get into the party my tiny dick got hard immediately and I was very excited to do this for her she also informed me that John was booking them a hotel room and told him I’d call him for the number and book it myself so please call John and get the information she handed me her phone and said he listed as BBC daddy again I was shocked but didn’t say a word because my tiny dick was in complete control of me after 12 days in chastity and it was the first time I realized John was black.

I called John and and said hey this is Dawns husband, he said what’s up little guy that’s when I knew my wife had told him how small I am below the belt I was a little embarrassed but really just wanted to get the information and book the room before we hung up John said MAKE SURE ITS A SUITE I want my bitch to be happy I said yes sir and hung up the phone.

Date nite is finally here for my wife.

After 2 weeks of tanning my wife’s skin color looked great she had her hair colored a light blonde and she had been dieting and exercising like crazy and simply looked awesome. She has not let me see her naked since her waxing appointment her face looked 10 years younger from her appointment at the Spa for the face scrub and chemical treatment I spent the morning waiting setting at the beauty salon while she got her hair and make up done for her date I even heard her talking to the girl about what her plans were for the night.

Once home my wife went to get ready she told me to get my suit and leave the bedroom and do not come back we would leave at 7PM sharp so I need to pick John up at 6:30 make sure I open the door for him to get into the SUV then come back so John could pick her up. She told me make sure I always open the door for both of them every time without fail please do not embarrass her.

I was so nervous when I went to pick up John when I arrived I texted him that I had arrived (my wife put johns number in my phone as Dawns lover) when he walked out of his home I was amazed at how young he was, my wife is 50 and John looked to be 25 at least 6F5 dark black skin tone and looked to be very well built under his suit. As he got to the SUV I opened the door he handed me a dollar and told me to be a good boy tonight I just blushed and said yes sir.

We arrived to pick dawn up at 5 minutes til 7 and I asked John to please set still until,I opened his door because my wife might be watching, he smiled and said that sounded great I opened his door and he stepped out and said I bet this bitch is going to be a crazy good fuck tonight the older ones always want to prove they still have it then he smiled at me and said wait right here little guy.

When my wife walked out of the house she looked amazing her skin color was a dark bronze, her hair was a very light blond and the stylist made her hair look amazing. With the facial treatment she had received and the perfect make up she looked 35 she wore 4” high heels I assume to make her not feel so short next to John but made her about 2” taller thanI am the dress was way shorter then I though it was came to just a over her thighs she had on black thigh high hose and a Garder that the top of her hose just showed a little at the bottom of her dress. I was so jealous and horny looking at her John took her hand and walked her to the SUV as they got to the door John gave her the biggest and longest kiss and she accepted him immediately I then could tell how attracted my wife was to this man and I was jealous but again my tiny dick told me this is how it is suppose to be.

As I drove my wife and John to the party John had his hands all over my wife I was looking at them in the mirror and he winked at me and then asked her who she loved and she immediately said John and his man size cock she said she was tired of tiny dicks. John then asked her if he agreed to fuck her tonight she had to agree that she only fucked big dicks from now on, she immediately agreed I wanted to protest but my wife seemed to be really enjoying herself so I just sat quietly and drove we arrived at the party at 7:45PM as I opened the door and John and my wife stepped out my wife told me to go to the hotel and get the room ready make sure the wine was chilled and the lighting in the room was romantic she then said be back out front of the party at 11PM sharp. I then watch my wife walk hand in hand with John away from me my hart sunk but once again my little dick said GET TO THE HOTEL so off i went.

I had the hotel room all set, wine was on ice and I had red scarfs over the Lights (red lighting is my wife’s favorite) I headed back to the party and waited until exactly 11PM I pulled up to the entrance and my wife and John were walking out, I could tell my wife had been drinking and John was holding her around her waist to steady her I opened the door for them to get in my wife looked at me and said you will never fuck me again then John put his hand on her ass and helped her into the car then he looked at me and said take us to the hotel so we can consummate our new relationship I was completely shocked by what was just said but again my tiny dick told me to keep Dawn happy.

On the drive to the hotel they could not keep their hands off each other they were kissing passionately and John was rubbing her breast and had his hand between her legs rubbing her Pussy she kept moaning and saying she could not wait to feel him inside her. John then put his hand on the back of her head and said he wanted her to suck his dick until they got to the hotel Dawn smiled reached down and unzipped his pants and pulled out the biggest cock I have ever seen we both gasped at the same time his cock was already what I though was completely hard and looked to be about 13” long and she had trouble getting it into her mouth John told her to hold still and open wide as she can then put his hand on the back of her head and shoved it down my wife gagged at first but John held her in place and said just relax before long my wife was taking about 8” and John was moaning as we pulled into the hotel parking lot I heard John tell my wife he was coming and to make sure she swallowed it as I pulled up to the entrance and parked my wife told me to wait a minute she was not finished cleaning the cum off this beautiful cock.

My wife started helping John put his massive beast away I asked if they still needed the room John replied “real men cum multiple times, of course we need the room” I could see my wife’s face light up with excitement as my wife and John left the SUV my wife told me to park then come in and pour them some wine I once again was shocked and wondered if my wife was going to make me watch.

I parked and went into the hotel room my wife informed me that the bag I had brought for her to the room was actually for me so please take the bag into the bathroom and change into what she had brought for me then come pour them some wine.

When I pulled the items out of the bag it was a pair of white crotchless panties so my pink chastity was showing a short school girl skirt white thigh high socks a white silk shirt that said Johns #2 whore and a pair of black flats I was so embarrassed but once again my tiny dick was having fun so I got dressed and walked out of the bathroom with my hands in front of my chastity. Dawn looked at me and said you look great but you can’t pour the wine with your hands there I’m thirst so hurry up.

For the rest of the night I sat beside of the bed and listen to another man give my wife multiple orgasms and cumming in her pussy at least 6 times. By morning my wife was so worn out she told me to drive John home then come back and get her I went to get dressed and she asked me what I was doing? I replied I’m getting dressed she responded you are already dressed and John is in a hurry so wear what you have on.

John put his arm around me and said come on girl you will be fine as we got to the suv John took the keys and said he would drive since I would be a little busy during the drive I was very confused, John opened the door for me and slapped me on the ass as I got in the passenger side, I let out a little Yelp and John just laughed. As John got in the drivers side of the car he unzipped his pants and looked at me and said he still had one more in the chamber and I had about 30 minutes to get it out or I’d be walking back to the hotel I just sat there not sure what to do. John then picked up his phone and called Dawn and said yes, I told him but he is just setting there John then put his phone on speaker and I heard my wife yell DO WHAT YOU ARE TOLD IF YOU WANT TO STAY MARRIED TO ME I put my head down and said yes ma’am.

As John drove I gave him the best blow job I could as we pulled up to his place he held my head to the side and came all over my face and hair. He told me not to wipe it off because my wife wanted to see it. As John got out of the SUV he removed the keys from the ignition and threw them into his yard and told me to go find them I was so embarrassed with what I was wearing fresh cum all over my face and in my hair but I found the keys quickly and headed back to pick up my wife.

As I entered the hotel my wife was wearing a large black strapon she told me it was an exact duplicate of johns cock and I need to get use to it because he would be fucking both of us in the future.

Hope you enjoyed this story but this is only the beginning a lot more has happened.


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