Surprise Date
We had some fun with the cuckolding thing. It happened twice now and we both loved it.
I really loved the excitement of wondering if my wife would be into this guy and what came next. The build up was just the best part, after the fucking of course.
We both agreed that it would be hot for the next time to arrange it upfront. We then both knew it was going to happen and we could enjoy the whole build-up towards the date together.
I did not want to put much effort into searching for a reliable new guy hoping for a match. We both are picky and very touchy when it comes to the vibe we get from someone.
My wife proposed we ask Tom for a second date. I liked Tom and agreed we should do this.
So I reached out to Tom again and asked him how he felt about this. Tom was enthusiastic from the start and loved to meet up again.
Because Tom lived an hour away, we thought it would be nice if my wife could stay for the night.
The thing I loved the most about the first hookup between Tom and my wife was the helpless feeling of watching the whole thing going down without me being able to do something about it. So we agreed that I could follow the whole act by video call. We planned the date two weeks later so the excitement could build up, but not for too long.
I took my wife shopping for some lingerie to wear on her date.
She fancied the classic stuff so it became stockings with a lace top. She would wear a sundress without a bra or panties. Just the stockings.
In the days before the date, we had sex multiple times. Every time one of us mentioned it we would get really hot and race to our bedroom.
And then the day finally came. I made sure I got the house to myself, so I brought the kids to our grandparents for the weekend.
When I came back my wife just finished showering and was putting on her make-up in front of the mirror. As I watched her from the door opening, she smiled at me and said: "Thank you, honey, I know we both enjoy this, but thank you for helping open up." As she put on her stockings my heart started racing. She looked incredibly hot.
She walked over to the wardrobe and I took a seat on the bed. She put on her high heels and saw the huge bulge I got in my pants. She took a few daring poses and asked: "Do you think Tom would like this?".
"Yes, dear," I stumbled.
She knew I was ready to jump her so she quickly covered herself up with a sundress.
"Good. I know you're about to explode, and if it wasn't for this date, I would jump you to. Just enjoy this, and I will make sure I take good care of you when I get back," she said.
She had to leave now or else she would be late. We gave each other a passionate kiss goodbye, and then she went in her car. I had an hour of free time before she arrived at Tom's, so I took a long shower and set up the equipment for the call in my home office, which has a couch to sit in comfort. I had a big screen in the middle of the room and made sure all the audio was connected so I could hear everything.
After just a little more than an hour, my phone rang. It was my wife. She said Tom had a professional camera set up with a better video quality than her phone. They were having a drink, and after that, Tom would set it up and send me a link. A few minutes later, I received a link in my email, and I clicked it.
Immediately, I saw Tom's bedroom with a good view of the bed. I could hear them talk in the other room. Sounded like they were having fun.
After seven excruciating minutes, I could hear the bedroom door opening and saw my wife walking in front of the camera. Tom arrived as well and waved at the camera.
"Now let me take a good look at you," he said to my wife.
She made a twirl in front of the camera. She did it fast enough so her dress went up and Tom could see she wasn't wearing anything underneath. She pointed at Tom's clothing and made a gesture that he should take them off. Tom quickly undressed till he was standing in nothing more than his boxer.
He took off her dress, and she took a seat on the side of the bed and slowly pulled down his boxer. She didn't waste any time and took his dick in her mouth. Immediately Tom moaned. As this was happening I removed my clothes and sat on the couch with my cock already hard.
Just one minute in I heard a knock on the door. It wasn't my door, it was over there.
The first thing that came to my mind was a package deliverer. Big spoiler to the fun but no worries. They can continue right after.
Tom stopped my wife from what she was doing and pulled her chin up.
" I invited a friend over for some more fun. If you want this, just say it. If you don't want this, I will go to the door and send him on his way. No harmed feelings". He said.
My jaw dropped to the floor. I was completely shocked and I could see my wife was as well.
The video and audio were one way. So we couldn't discuss this.
Would she do it or would this be the end of her date?
I could see she was thinking it over and looked quickly at the camera and back to Tom.
"Yes, bring him in," she said.
Tom turned around and walked to the door. I was baffled and couldn't move for a couple of seconds.
Then I felt my cock. It was harder than ever before.
Tom returned, followed by his friend, that already undressed himself. My wife stood up from the bedside. There was a short hug from Tom's friend. As he let go of my wife, I could see he already had a bulge in his boxer. He was ready for some fun. He quickly waved at the camera as my wife took place again on the bedside.
Tom and his friend took a stand in front of her so she would have a good view of now two bulges in their boxers.
With one hand, she pulled down Tom's boxer, and with the other one, his friend's boxer.
"Let's see what you brought me," she said.
She grabbed both cocks in her hands and started jerking on both. "You can pick up where we left," Tom said. My wife got the hint and took Tom's cock in her mouth while she was still jerking his friend. After a few seconds, she switched to the other cock and started sucking off his friend. She switched a few times until both guys were hard and all worked up.
Tom lifted my wife from the bedside and put her on all fours in the middle of the bed.
He crawled behind her and started licking her pussy from behind. His friend walked around and took place in front of her so she could continue sucking him.
She was moaning with his friend's cock in her mouth from the licking Tom did. Tom grabbed both of her ass cheeks and spread them wide open. He goes up with his tongue and starts licking her asshole. While he does that he is rubbing her clit with his fingers. My wife starts moaning harder and breathing heavier with a cock in her mouth. She tries to suck it, but Tom's licking brings her into ecstasy.
She lets his friend's cock slip out her mouth, and while she continues jerking it, she is telling them she's about to come.
"Oh yes baby, that's it. I'm cumming, I'm cumming!" She screamed now.
As Tom presses his tongue deep into her ass one more time she starts shivering and makes a loud moan before she drops on the bed.
She didn't have much time to catch her breath. Tom turned her around on her back and switched positions with his friend.
His friend lifts her legs and places his cock right in front of her pussy. With a soft push, he entered her pussy and starts pushing it in a bit further with every stroke. Tom is at the other end of the bed placing his cock in front of my wife's mouth. She starts sucking him all the way down to his balls.
His friend picked up the pace and is now pounding her pussy hard. You can by hear her muffled moans he was doing a good job on fucking her.
After some time Tom's friend wanted to change positions again. He lay down on his back and my wife climbed on top of him. With her hand, she holds his cock as she lowers herself on it. She starts riding him, and Tom is now standing next to her, enjoying some more of her blowjob skills.
Then she took out Tom's cock, looked up, and asked: "Would you fuck me in the ass, please?".
I was shocked again. She had never done this before. But the image of seeing my wife getting a double penetration almost made me blow my load.
Tom nodded and grabbed some lubricant from the nightstand. He massaged his cock with it, as well as my wife's ass.
She bended over a bit more without letting the cock slide out of her pussy. Tom takes position behind her and starts rubbing a finger over her asshole. Slowly he enters her ass with his finger. She moans as he pushes, and one finger is quickly followed by another.
He stretched her asshole and felt it loosen up.
My wife is an anal virgin, so this would be the first time someone fucked her in the ass.
Tom pulls out his fingers and places his cock against her tight hole. He pushes slowly, and the tip is going in smoothly.
He paused and waited for a sign of my wife so he could go further. My wife grabs her ass cheeks and spreads them, letting Tom know he can go in all the way.
Tom now applies some more pressure and his cock slowly disappears in her ass. When my wife felt his cock was all the way in, she started moving back and forth slowly.
I could not believe what I am seeing right now. My nose almost touched the screen, and my hand was moving faster around my cock.
They went faster and faster, and my wife was screaming with pleasure.
Soon I heard her screaming: "I am cumming again!".
Both of the guys were working on her hard, and I could see from their faces they were about to cum as well.
Tom said he was about to cum also and I could hear the same from his friend.
My wife started encouraging them: "Yes cum inside me. Fill me up with your cum".
Tom moaned loudly as he came inside her ass. And I could hear his friend unloading in her pussy. With a last stroke from both guys, my wife reached an intense orgasm.
They all held still for the next moments. Probably to recover from the intense moment. I was hypnotized by this spectacle, and when I pulled myself together, I noticed that my cum was all over the floor.
Tom was the first to move again and pulled out his cock from my wife's ass. Quickly followed by his friend. I could see the cum pouring out of both of her holes.
My wife turned her ass to the camera spreading her ass like she wanted to show me the proof that she has satisfied both guys.
She turned around, blew a kiss towards the camera and said: "we are going to take a shower and get some goodnight rest. See you tomorrow honey".
Tom walked up to the camera and soon after that the connection was gone.
I wanted to go to sleep as well but the images I just saw were going trough my mind stuck on the replay. I don't know how many times a jerked off that night but it was more than 3 times at least.
The next morning I woke up in the best mood since years. I started the preparations for when my wife got home. I got a text that she was getting in the car so I knew I had one hour before she would arrive.
I cleaned up the room and took a shower. When I was drying myself I could hear the front door. Quickly I headed to the bedroom in anticipation of the best sex we ever had.
She entered the bedroom wearing the same clothes that she left in. She saw me lying there naked on the bed and took of her sundress in the door opening.
"Are you ready dear"? She asked. She jumped on the bed next to me and started rubbing on my stomach slowly reaching down to my hard cock.
"Let me tell you about last night". She said.
"After the shower we all got in the same bed. We cuddled some and tried to fall asleep. After two hours I could still not fall asleep as the whole thing was going trough my mind over and over again. I was thinking maybe the guys couldn't sleep either. But they were lying still with their eyes closed. I was lying with my back to Tom and his hips were almost touching my ass. I felt his soft cock against my ass and started to stroke it a bit wondering if it would get hard again. I could feel it growing again and rubbing my pussy. Tom didn't say anything and kept his eyes closed. I could hear by his breathing he enjoyed it. When his cock felt fully hard again I let it slip inside and Tom slowly started fucking me again. In my enthusiasm I grabbed his friend's cock and softly jerked it. I felt his cock also growing again in my hands.
Tom started fucking me harder and I couldn't suppress my moans any longer. I went down with my head underneath the sheets and started sucking on his friend cock. They were both awake now.
I felt Tom's cock throbbing inside me and I let go of his friends cock. I arched my back so my face was next to Tom's and pulled his head closer with my arm so I could whisper in his ears. Cum for my baby, please fill me up again with your cum. Cum inside me baby, cum for me. And with my last words Tom came inside and I could feel his cum just flowing inside of me.
As Tom pulled out I turned around so his friend could also take another turn on me. His cock slipped inside and immediately started pounding away. I put my head down again so I could lick the last drops of cum out of Tom's cock. Then his friend was ready again. I pulled his head close to mine and whispered some encouragement in his ears. Give it to my baby, I want another load inside. Cum for me, cum for me! He pushed as hard as he could and I could feel his cock was inside up to his balls. I massaged his balls with one hand between my legs and felt he was cumming inside of me. I didn't stop massaging his balls until I felt his cock getting softer. This was just what I needed and we all fell asleep. In the morning we had some breakfast and took a shower together. They both took turns on me again. The even double penetrated me again while lifting me up in the air. After we washed up I kissed them goodbye and got in the car".
As she was telling me this she was slowly stroking my cock just soft enough not to make me cum during her report of what happened that night.
She climbed on top of me and let my cock slide inside her pussy. She started riding me passionately. She knew I could not hold it for long. "Yes baby, fuck me good. Show me why you are my number 1. Show me how much you liked what you saw. Cum for me baby, fill me up again. Give it to me!".
I felt my muscles tensing and almost lost my conscious when I started ejaculating inside her. I just didn't stop stop bursting inside her and it lasted a lot longer than normal. After I was done my wife smiled at me and gave me a passionate kiss.
"This was so hot baby. I just feel this is so much more cum than normally." She said.
She let herself slide of me and lied next to me.
We did it again a couple of times that day knowing we both found something we absolutely loved.
I really loved the excitement of wondering if my wife would be into this guy and what came next. The build up was just the best part, after the fucking of course.
We both agreed that it would be hot for the next time to arrange it upfront. We then both knew it was going to happen and we could enjoy the whole build-up towards the date together.
I did not want to put much effort into searching for a reliable new guy hoping for a match. We both are picky and very touchy when it comes to the vibe we get from someone.
My wife proposed we ask Tom for a second date. I liked Tom and agreed we should do this.
So I reached out to Tom again and asked him how he felt about this. Tom was enthusiastic from the start and loved to meet up again.
Because Tom lived an hour away, we thought it would be nice if my wife could stay for the night.
The thing I loved the most about the first hookup between Tom and my wife was the helpless feeling of watching the whole thing going down without me being able to do something about it. So we agreed that I could follow the whole act by video call. We planned the date two weeks later so the excitement could build up, but not for too long.
I took my wife shopping for some lingerie to wear on her date.
She fancied the classic stuff so it became stockings with a lace top. She would wear a sundress without a bra or panties. Just the stockings.
In the days before the date, we had sex multiple times. Every time one of us mentioned it we would get really hot and race to our bedroom.
And then the day finally came. I made sure I got the house to myself, so I brought the kids to our grandparents for the weekend.
When I came back my wife just finished showering and was putting on her make-up in front of the mirror. As I watched her from the door opening, she smiled at me and said: "Thank you, honey, I know we both enjoy this, but thank you for helping open up." As she put on her stockings my heart started racing. She looked incredibly hot.
She walked over to the wardrobe and I took a seat on the bed. She put on her high heels and saw the huge bulge I got in my pants. She took a few daring poses and asked: "Do you think Tom would like this?".
"Yes, dear," I stumbled.
She knew I was ready to jump her so she quickly covered herself up with a sundress.
"Good. I know you're about to explode, and if it wasn't for this date, I would jump you to. Just enjoy this, and I will make sure I take good care of you when I get back," she said.
She had to leave now or else she would be late. We gave each other a passionate kiss goodbye, and then she went in her car. I had an hour of free time before she arrived at Tom's, so I took a long shower and set up the equipment for the call in my home office, which has a couch to sit in comfort. I had a big screen in the middle of the room and made sure all the audio was connected so I could hear everything.
After just a little more than an hour, my phone rang. It was my wife. She said Tom had a professional camera set up with a better video quality than her phone. They were having a drink, and after that, Tom would set it up and send me a link. A few minutes later, I received a link in my email, and I clicked it.
Immediately, I saw Tom's bedroom with a good view of the bed. I could hear them talk in the other room. Sounded like they were having fun.
After seven excruciating minutes, I could hear the bedroom door opening and saw my wife walking in front of the camera. Tom arrived as well and waved at the camera.
"Now let me take a good look at you," he said to my wife.
She made a twirl in front of the camera. She did it fast enough so her dress went up and Tom could see she wasn't wearing anything underneath. She pointed at Tom's clothing and made a gesture that he should take them off. Tom quickly undressed till he was standing in nothing more than his boxer.
He took off her dress, and she took a seat on the side of the bed and slowly pulled down his boxer. She didn't waste any time and took his dick in her mouth. Immediately Tom moaned. As this was happening I removed my clothes and sat on the couch with my cock already hard.
Just one minute in I heard a knock on the door. It wasn't my door, it was over there.
The first thing that came to my mind was a package deliverer. Big spoiler to the fun but no worries. They can continue right after.
Tom stopped my wife from what she was doing and pulled her chin up.
" I invited a friend over for some more fun. If you want this, just say it. If you don't want this, I will go to the door and send him on his way. No harmed feelings". He said.
My jaw dropped to the floor. I was completely shocked and I could see my wife was as well.
The video and audio were one way. So we couldn't discuss this.
Would she do it or would this be the end of her date?
I could see she was thinking it over and looked quickly at the camera and back to Tom.
"Yes, bring him in," she said.
Tom turned around and walked to the door. I was baffled and couldn't move for a couple of seconds.
Then I felt my cock. It was harder than ever before.
Tom returned, followed by his friend, that already undressed himself. My wife stood up from the bedside. There was a short hug from Tom's friend. As he let go of my wife, I could see he already had a bulge in his boxer. He was ready for some fun. He quickly waved at the camera as my wife took place again on the bedside.
Tom and his friend took a stand in front of her so she would have a good view of now two bulges in their boxers.
With one hand, she pulled down Tom's boxer, and with the other one, his friend's boxer.
"Let's see what you brought me," she said.
She grabbed both cocks in her hands and started jerking on both. "You can pick up where we left," Tom said. My wife got the hint and took Tom's cock in her mouth while she was still jerking his friend. After a few seconds, she switched to the other cock and started sucking off his friend. She switched a few times until both guys were hard and all worked up.
Tom lifted my wife from the bedside and put her on all fours in the middle of the bed.
He crawled behind her and started licking her pussy from behind. His friend walked around and took place in front of her so she could continue sucking him.
She was moaning with his friend's cock in her mouth from the licking Tom did. Tom grabbed both of her ass cheeks and spread them wide open. He goes up with his tongue and starts licking her asshole. While he does that he is rubbing her clit with his fingers. My wife starts moaning harder and breathing heavier with a cock in her mouth. She tries to suck it, but Tom's licking brings her into ecstasy.
She lets his friend's cock slip out her mouth, and while she continues jerking it, she is telling them she's about to come.
"Oh yes baby, that's it. I'm cumming, I'm cumming!" She screamed now.
As Tom presses his tongue deep into her ass one more time she starts shivering and makes a loud moan before she drops on the bed.
She didn't have much time to catch her breath. Tom turned her around on her back and switched positions with his friend.
His friend lifts her legs and places his cock right in front of her pussy. With a soft push, he entered her pussy and starts pushing it in a bit further with every stroke. Tom is at the other end of the bed placing his cock in front of my wife's mouth. She starts sucking him all the way down to his balls.
His friend picked up the pace and is now pounding her pussy hard. You can by hear her muffled moans he was doing a good job on fucking her.
After some time Tom's friend wanted to change positions again. He lay down on his back and my wife climbed on top of him. With her hand, she holds his cock as she lowers herself on it. She starts riding him, and Tom is now standing next to her, enjoying some more of her blowjob skills.
Then she took out Tom's cock, looked up, and asked: "Would you fuck me in the ass, please?".
I was shocked again. She had never done this before. But the image of seeing my wife getting a double penetration almost made me blow my load.
Tom nodded and grabbed some lubricant from the nightstand. He massaged his cock with it, as well as my wife's ass.
She bended over a bit more without letting the cock slide out of her pussy. Tom takes position behind her and starts rubbing a finger over her asshole. Slowly he enters her ass with his finger. She moans as he pushes, and one finger is quickly followed by another.
He stretched her asshole and felt it loosen up.
My wife is an anal virgin, so this would be the first time someone fucked her in the ass.
Tom pulls out his fingers and places his cock against her tight hole. He pushes slowly, and the tip is going in smoothly.
He paused and waited for a sign of my wife so he could go further. My wife grabs her ass cheeks and spreads them, letting Tom know he can go in all the way.
Tom now applies some more pressure and his cock slowly disappears in her ass. When my wife felt his cock was all the way in, she started moving back and forth slowly.
I could not believe what I am seeing right now. My nose almost touched the screen, and my hand was moving faster around my cock.
They went faster and faster, and my wife was screaming with pleasure.
Soon I heard her screaming: "I am cumming again!".
Both of the guys were working on her hard, and I could see from their faces they were about to cum as well.
Tom said he was about to cum also and I could hear the same from his friend.
My wife started encouraging them: "Yes cum inside me. Fill me up with your cum".
Tom moaned loudly as he came inside her ass. And I could hear his friend unloading in her pussy. With a last stroke from both guys, my wife reached an intense orgasm.
They all held still for the next moments. Probably to recover from the intense moment. I was hypnotized by this spectacle, and when I pulled myself together, I noticed that my cum was all over the floor.
Tom was the first to move again and pulled out his cock from my wife's ass. Quickly followed by his friend. I could see the cum pouring out of both of her holes.
My wife turned her ass to the camera spreading her ass like she wanted to show me the proof that she has satisfied both guys.
She turned around, blew a kiss towards the camera and said: "we are going to take a shower and get some goodnight rest. See you tomorrow honey".
Tom walked up to the camera and soon after that the connection was gone.
I wanted to go to sleep as well but the images I just saw were going trough my mind stuck on the replay. I don't know how many times a jerked off that night but it was more than 3 times at least.
The next morning I woke up in the best mood since years. I started the preparations for when my wife got home. I got a text that she was getting in the car so I knew I had one hour before she would arrive.
I cleaned up the room and took a shower. When I was drying myself I could hear the front door. Quickly I headed to the bedroom in anticipation of the best sex we ever had.
She entered the bedroom wearing the same clothes that she left in. She saw me lying there naked on the bed and took of her sundress in the door opening.
"Are you ready dear"? She asked. She jumped on the bed next to me and started rubbing on my stomach slowly reaching down to my hard cock.
"Let me tell you about last night". She said.
"After the shower we all got in the same bed. We cuddled some and tried to fall asleep. After two hours I could still not fall asleep as the whole thing was going trough my mind over and over again. I was thinking maybe the guys couldn't sleep either. But they were lying still with their eyes closed. I was lying with my back to Tom and his hips were almost touching my ass. I felt his soft cock against my ass and started to stroke it a bit wondering if it would get hard again. I could feel it growing again and rubbing my pussy. Tom didn't say anything and kept his eyes closed. I could hear by his breathing he enjoyed it. When his cock felt fully hard again I let it slip inside and Tom slowly started fucking me again. In my enthusiasm I grabbed his friend's cock and softly jerked it. I felt his cock also growing again in my hands.
Tom started fucking me harder and I couldn't suppress my moans any longer. I went down with my head underneath the sheets and started sucking on his friend cock. They were both awake now.
I felt Tom's cock throbbing inside me and I let go of his friends cock. I arched my back so my face was next to Tom's and pulled his head closer with my arm so I could whisper in his ears. Cum for my baby, please fill me up again with your cum. Cum inside me baby, cum for me. And with my last words Tom came inside and I could feel his cum just flowing inside of me.
As Tom pulled out I turned around so his friend could also take another turn on me. His cock slipped inside and immediately started pounding away. I put my head down again so I could lick the last drops of cum out of Tom's cock. Then his friend was ready again. I pulled his head close to mine and whispered some encouragement in his ears. Give it to my baby, I want another load inside. Cum for me, cum for me! He pushed as hard as he could and I could feel his cock was inside up to his balls. I massaged his balls with one hand between my legs and felt he was cumming inside of me. I didn't stop massaging his balls until I felt his cock getting softer. This was just what I needed and we all fell asleep. In the morning we had some breakfast and took a shower together. They both took turns on me again. The even double penetrated me again while lifting me up in the air. After we washed up I kissed them goodbye and got in the car".
As she was telling me this she was slowly stroking my cock just soft enough not to make me cum during her report of what happened that night.
She climbed on top of me and let my cock slide inside her pussy. She started riding me passionately. She knew I could not hold it for long. "Yes baby, fuck me good. Show me why you are my number 1. Show me how much you liked what you saw. Cum for me baby, fill me up again. Give it to me!".
I felt my muscles tensing and almost lost my conscious when I started ejaculating inside her. I just didn't stop stop bursting inside her and it lasted a lot longer than normal. After I was done my wife smiled at me and gave me a passionate kiss.
"This was so hot baby. I just feel this is so much more cum than normally." She said.
She let herself slide of me and lied next to me.
We did it again a couple of times that day knowing we both found something we absolutely loved.
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