Date Night, Date 01

Date Night, Date 1

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This story is about a husband and wife that begin a cuckolding journey. Thus, if that theme is not for you, please move on and find stories with themes that you like.

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Sitting in the wine bar, on my stool at the small back bar, watching my wife on her date via the mirror behind the bar was an amazingly powerful experience. She started the date awkwardly as she just met the man, and now there is much less awkwardness as they laughed and talked, and drink wine together.

My wife was on this date because I encouraged her to do it. I encouraged her to pursue other men and cuckold me. It wasn't like I just told her this today and she went out on a date. We have been dealing with this strong desire of mine for almost a year. We have had other minor interactions. Mainly that weren't planned, but situations where she got flirted with at an event or at the bar and we let it play out a little bit, but this time the potential cuckolding was intentional.

We were in Northern Michigan, not too far from a great town called Traverse City and she wasn't on her date just with the man, instead, it was a double date with Chloe, a good friend's wife. It was these friends that we shared our cuckolding journey with. Chloe's husband, Dan, and I became friends because we both had the cuckolding fetish and we connected online. But then we became strong friends on many levels. The friendship started to involve our wives and we were lucky enough to convince both our wives to lock our dicks in chastity. That is a story all on its own, but now the four of us were together for a long weekend and we were hoping to move from chastity couples to cuckolding couples. And from my vantage point at the bar, I was betting it was going to be a successful weekend.

Chloe was with Mark, and my wife's date was Samuel, Mark's friend. Everyone was about the same age, in our 50s and no one was going to confuse the table for a group of supermodels out for some wine. Chloe and Katie were quite attractive, and Mark and Samuel were solidly handsome, but no modeling contracts were in the works. Chloe and Mark had been having a relationship for almost six months now, but they had yet to seal the deal. My wife and Samuel had been introduced remotely about two months ago and had engaged in a serious quantity of texting, but this was their first time meeting in person.

Katie was in what I would consider one of her more attractive outfits which was very casual, but still very sexy. She had a pair of Capri jeans on with some sexy sandals, and on the top, she wore a black sleeveless shirt that was just tight enough around her perfect breasts to certainly make her date notice. Chloe had on a V-neck white sweater and a pair of jeans that were full length and tight and showed off her sexy legs. Right now, what made both women even sexier were the big smiles they had on their face.

While the date started with that awkwardness I mentioned, at this point they were both well past that. Chloe and Mark had been an almost couple for quite a while and so they had a natural chemistry already but what was amazing to watch was how quickly Katie and Samuel clicked. What started with her being somewhat stiff was now completely the opposite. She was relaxed, and she was smiling.

About 20 minutes into the date the two men excuse themselves to use the restroom and up to that point, the two men had been on one side of the booth and the two women on the other but while the men were gone, the women moved, so that each one of them occupied one side of the booth. When the men came back, there were big smiles all around, and each man slid in next to their woman. I watched with fascination as another man slid into the booth and actually put his arm around my wife and leaned in and they kissed each other.

From that point forward they were a couple on a date. Their body language was clear. Samuel's advancement on my wife was not unnoticed by Chloe and Mark and soon they were sitting leaning against each other, and I noticed his hand was below the table assumingely on her leg and she made no attempt to change that position. They had wine and some food and just had a good time.

In real time I watched my wife pick up her phone and next thing you know my phone buzzed.

Samuel has suggested we go back to Mark's and continue our date. We will be ready to leave in about 20 minutes. Thank you again for driving us.

And that was my role for the this date. My friend Dan owns a car dealership, so I was driving one of the really nice and really big luxury SUVs that he sold. It was set up with two very comfortable rows of seats in the back and the two couples were occupying those seats for the day while I drove them around. Samuel did not know that I was Katie's husband, although he knew she was married. It was amazing to be in that role and it was something I had asked my wife to allow me to do both so they could drink without worry but also so that I could have the thrill.

Chloe's husband, Dan, would have been with us but Mark and Dan knew each other and the reason Mark and Chloe had not hooked up yet was because Mark felt uncomfortable sleeping with Dan's wife. Dan wanted it to happen, Chloe wanted it to happen, and if my view of how the date was currently going was accurate, it might finally actually happen.

Dan was home, but I was texting him constant updates, and my most recent one simply said that I would be surprised if the date didn't end up with both of us being an official cuck!. He asked why and I explained that both couples had really settled into an intimate comfort level and there seemed to be little holding them back from continuing. That was amazing to watch and while I watched, I pushed hard against my chastity cage, the cage my wife has kept me in for 5 1/2 weeks at this point. The intent was I would stay in chastity until after the date.

That's how we have been referring to it for the last month since it was set up; we call it the date. And it seemed like the date was going very well. I saw as the men paid the check and then I went out into the SUV and pulled it around to the front. I open the doors for them like a good driver would. Chloe and Mark came out first and then Katie and Samuel. I immediately noticed that Katie and Samuel were holding hands and I also noticed that my wife did not try to stop that behavior when she saw me. After they had climbed in, each man helping their woman, I closed the doors and got in the driver's seat and said, "where to?" Mark responded.

"We're going to continue the date at my house because I just got my hot tub fixed and someone needs to try it out, so just jump on the M22 north out of town and then I'll direct you from there."

I did as instructed, and as we drove the 30 minutes back to Mark's place, the couples chatted, and I noticed at one point my wife and Samuel were holding hands with their hands in his lap.

While my wife was new at this, Chloe and Mark had been playing with the possibility of cuckolding for a while and so she knew I was acutely aware of what was going on and she decided to have some fun with it. She said in a voice loud enough for everyone to hear including me, "should we have our driver stop somewhere so Katie and I can get bathing suits because we didn't bring any for the hot tub or should we just all plan to go au natural."

It was Samuel, who replied, "my vote is no stop!"

Katie replied, in a way that almost made me swerve off the road. "I agree with my man."

Then Chloe spoke and I could see the smile on her face as she both spoke the truth and teased the shit out of me, "Then let's just head straight to Mark's but if we are going to be without bathing suits, then the men need to do the same."

It was Mark who finally finished the conversation, "I think the four of us naked in my hot tub might be the most excitement my house has ever experienced, but I am definitely in."

As he said that, I saw Samuel reach his hand up and cup my wife's chin and turn her head towards him, and they immediately started to kiss. This behavior was not unnoticed by Chloe, and she turned and started to kiss Mark. Soon I was driving, and the only sound were the two couples making out in the backseats.

I watched Samuel's hand slide up my wife's torso and eventually cup her breast, and then I watched as he squeezed her breast as they kissed. His thumb was circling her obviously hard nipple, and they were still making out like teenagers. I finally had to interrupt because I didn't know where I was going.

"I'm sorry to interrupt your fun, but I do need directions here. I am pretty sure there is a turn I have to make soon."

Chloe and Mark stopped kissing, and Mark said "Next light, make a left, and then I'll direct you from there. The light is about 4 more miles." I noticed Katie and Samuel didn't stop kissing, I guess they figured they had four more miles to enjoy each other. As I made the left, they did stop kissing, and I also noticed that when he brought his hand down off my wife's breast, he held her hand and moved it over to his lap. I could only assume my wife was getting to the feel Samuel's cock through his pants. I later learned that his cock was quite a bit bigger than mine, and that, as soon as she felt it through his pants, she knew she was going to feel it in other ways, too.

I briefly made eye contact with my wife, and she just smiled. I smiled back and then definitely for show, she leaned in and kissed Samuel. He smiled, and then they went back to just sitting there, but I knew that soon they were going to get even more intimate and then it was very likely I was going to end up cuckolded. I was actually impressed with myself that I was able to drive given how crazy my cuckold angst was. I was jealous, excited, humiliated, and aroused all at the same time. I had experienced these feelings when my wife and I had played with the cuckolding idea in the past, and I had felt it more acutely as it became obvious that they were hitting it off via text, but in that car, watching the prelude to my cuckolding, the power of my angst was all consuming. And it was one of the best feelings of my life. Hard to explain to others, but it was the feeling I greatly desired and in the moment, I was getting the super charged version.

A typical husband would be appalled at the thought of Samuel and Katie becoming an intimate couple, but that thought had me pushing against my cage so hard. It was what I wanted. I wanted my wife to give me the gift of cuckolding and I wanted her to have a lover that she could have great sex with and fun times with and not worry that I wouldn't still be there when she was done.

Mark directed me to the house, and I asked the group if I should wait or would this be an overnight thing, I said it in a way that was a clear invitation to the ladies to pick the second choice. Katie responded, "why don't you wait for a few hours, we're planning to have some fun, but we do need to get back home tonight. Will text you when it's time to go." Then she addressed the group, "In the meantime, let's go inside, get naked, jump in the hot tub, and see what happens."

Everybody laughed and I went around and opened the door for them, and then I watched my wife walk into the house while holding hands with the man who is going to cuckold me. For the next 3 1/2 hours I sat in the car and furiously texted with Dan, but neither of us heard a peep from our wives. It drove us nuts, both in a good and bad way. I got completely freaked out. I wanted so badly for my wife to cuckold me, but now that it was likely happening, I was in a partial panic. What if she didn't want me back? What if I her and Samuel became a real couple, and I was left out entirely. Dan kept me calm.

He was amazingly chill and kept reminding me that we wanted this and that it was actually better they were treating us to radio silence. I admired his confidence and calmness, and was very thankful I had him to talk me off many ledges as I waited in the driveway of the house where my wife was almost certainly cuckolding me. Finally, I got a text. Be out in about 20.

The timing was just about dead on and 20 minutes later the two ladies came out. Their hair was comb wet and they were back in their original clothes, and they both were walked out to the car by their respective men. There was serious kissing, and I watched as Samuel squeezed both of my wife's breasts as he kissed her passionately. They broke the kiss and Samuel said. "We look forward to tomorrow night. We are planning a wonderful dinner for the two of you here." He then looked at me, and at this point, I was not sure if he knew that I was Katie's husband, but he said, "and driver you're gonna have the night off because the ladies are going to drive themselves and stay the night." I simply said OK, and the two men helped the women into the car and they sat in the seats behind me. As I pulled away, everybody waved, and I started to drive back to Dan's.

"That was amazing!" It was Chloe speaking. Both of women let out the big sigh, and this whole time I was consumed with angst, jealousy, excitement, and every other emotion you can pack in to one body and mind. Finally, I felt my wife's hand reach up and touch my shoulder. She squeezed it and said, "You are now officially my cuckold. In fact, you are my cuckold a few times over." She squeezed my shoulder again and then pulled her hand back. I didn't know what to say. I was official! I was so excited. Finally, I just said, "did you have a good time."

It was such a dumb question because of course they had a good time. Chloe jumped into the conversation. "I think your poor husband is totally freaked out, so let me tell him that his wife and Samuel hit it off amazingly, and soon after we were in the hot tub there was no more conversation because we were all passionately intertwined, and it was the two of them that exited the hot tub for Samuel's bedroom, and it was the two of them having that energy that led to Mark taking me in his hot tub! I finally got my man and let me tell you he was amazing."

Now my wife jumped in and said, "and Samuel was spectacular. I suppose it's not teasing my poor husband if it's the truth, but you wanted me to be with a better man and Samuel is definitely a better man. He made me do something I haven't done with you in a decade which is come from Intercourse. In fact, I came twice just the first time he fucked me." My wife said all of this with excitement and confidence. That was almost as amazing as the fact that she had been fucked multiple times by another man. I loved this emerging version of my wife and was horny and jealous as fuck, but also genuinely happy for her. And happy for us. She was on a roll and kept going.

"And just so you know, we ended up back in the hot tub and we switched, and Samuel took me in the hot tub or really I took him, and Mark and Chloe headed for Mark's bedroom for some more traditional sex. As soon as they left, I climbed on top of Samuel and straddled him, and we kissed while I bounced on his perfect cock. He played with my tits, and it was amazing, eventually I just threw my head back and screamed fuck, as another orgasm ripped through my body. He eventually finished and I looked at him and said that he could have me anytime he wants."

Chloe jumped in and said, "And in case you were wondering, Mark and I fucked long and slow while you two kids were getting wild in the hot tub! Damn he made me cum just about as hard as I ever had. I can't wait to tell Dan all about it!"

My wife laughed and said, "And Dan will love that!" And she was right. Both Dan and I not only wanted our wives to have another man, but we wanted to hear all about it. In fact, we liked it better when our wives teased and taunted us about our chastity and now they were going to be able to take that to the next level because we were now officially cuckolds. My wife seemed to sense this and dove right in.

"While we waited for you two lovebirds, we made out like horny teenagers and then he started to tell me about the date he planned for us tomorrow night. He said we we're going to have dinner and drinks, more hot tub time, great bedroom sex, and he told me the kitchen countertops could be fun too. I agreed and tomorrow my man is going to boost me up onto the marble countertops and fuck me silly!" She then addressed me more directly, "have we ever had countertop sex?"

I croaked out a "no" and she laughed. "Yeah, I didn't think so!" She then leaned up and spoke into my ear, "and you know what, I think that will be something I am going to really enjoy!"

Chloe laughed and said, "don't tease him too hard, Dan will have to kill him if he crashes this car!"

My wife took the tease to the next level, "Oh, I am not teasing him, just stating the obvious truth!"

Both ladies laughed and then my wife continued with the story of their time at Mark's. I absolutely loved it, with my only disappointment being that Dan wasn't with us to hear all of this. Then again, I knew Chloe would retell it for him because according to Dan, Chloe loved unlocking him and teasing him both verbally and physically until his dick exploded. I was pretty certain that was on the docket for when I delivered Chloe to him in about 15 more minutes. It made me wonder what my wife would do. The truth was, I didn't care, I was already in heaven so whatever she wanted was ok with me.

"When Mark and Chloe returned, Samuel told them the plan. Mark was sitting on the edge of the hot tub, completely naked and Chloe ran her hand down Mark's stomach and grabbed his cock and squeezed it and said we are definitely having date two. Chloe then started to stroke his cock and soon Mark was fully back to life and it was amazing because then Chloe stood in the hot tun and bent over and gave her man a blow job. Samuel and I just watched until the scene got him hard again and then he positioned me on the edge of the hot and he stood in the hot tub and he fucked me. It was perfect."

My wife moaned as she recalled this. She truly had great sex and just describing it was making her horny. But after a deep sigh, she continued.

"All four of us were enjoying the shit of the moment and then in what was the most amazing point of the evening I came. Samuel came, and Mark came all at the same time, it was a cacophony of moaning and grunting and amazing sexual pleasure. Oh, and by the way that happened only about 30 minutes before we came out."

We were now only 5 minutes from Dan and Chloe's house, and I wasn't sure my dick had ever pushed that hard against my cage. Hearing my wife describe the amazing evening she had was truly incredible and outrageously arousing.

They told me a few other intimate details of their date and when we got back to the house, Chloe went immediately to Dan, grabbed his hand and pulled him to their bedroom. In my case, Katie and I went into our room and then she kissed me passionately. When we broke the kiss, she looked at me and said, "thank you for this. It is amazing but you are still going to stay in chastity because as we agreed originally this weekend is about me and Samuel. Tonight made me feel unbelievable and I'm not going to ruin it. I'm going to save myself for him again tomorrow."