Straight Male / 33
About ten years ago my wife (Lisa) an I were moving from Phoenix to Baltimore. The moving company took most of our belongings, but we decided to drive our cars ourselves. For the drive, my wife had her friend Jane ride with her. Full disclosure...at this point in our marriage we had an understanding that my wife was free to have sexual experiences outside of our marriage. In fact, she had several such experiences with Jane and (sometimes) her husband.
On the first day we made it just east of Amarillo and got two hotel rooms next to a Dairy Queen. While I decided to go to sleep, Lisa and Jane walked over to Dairy Queen to grab a bite to eat. I fell asleep immediately and did not wake up until Lisa came into our room around 7am the next morning. She apologized and said something came up.
As we were leaving the next morning, Jane surprisingly jumped in the car for me for the first part of the trip that day. During the drive, Jane told me what happened. They met a college kid working at Dairy Queen and invited him back to Jane's hotel room for a drink. The two girls started making out in from of the guy, eventually taking their clothes off so that my wife could go down on Jane. After a few minutes, my wife felt a tongue in her pussy and the threesome was on. Jane came quickly and then begged to be fucked. Unfortunately the guy only lasted a couple of minutes. Lisa was happy to clean up both of them with her mouth and he quickly got hard again. This time Lisa laid the guy on his back and mounted his young cock. Meanwhile, Jane mounted his face, forcing him to lick her pussy. This time the guy lasted few minutes, but eventually shot his load into my wife. At that point, they all collapsed and eventually fell asleep. When the ladies woke up the nest morning, he was gone.
I was not shocked by the story, but I was confused why Jane was telling me. Of course, I was hard as a rock and could not do anything about it with Jane in the car. For the next hour and a half, Jane would mentioned how big the guys cock was and how much he came. She would also mention how hot it was to see Lisa ride his cock. Then the conversation turned to me.
For the first time ever, I heard the word "cuckold." Jane explained that I was a "sissy" cuckold who stayed at home while my wife was free to fuck whomever and whenever she wanted. I did not argue, because she was right. Jane then proceeded to tell me that they were taking things to the "next level" the following night. At the next stop, Jane switched vehicles and I was alone trying to figure what she meant. About 8 hours later we pulled into our hotel in Nashville. To surprise, Lisa had only booked one room foe the three of us. Of course, I thought this would be my change for a threesome - and I was right, kind of.
After dinner, where we all had too much to drink, we went back to the hotel room. I was told to take a quick shower. During the shower, Jane came in and surprised me with a small enema bag and proceeded to tell me how to use it. Confused, I asked why, but she then raised her voice and commanded me to do it. Luckily there were instructions, so I cleaned out my ass.
When I was done, I walked into the room to find Jane fucking my wife with a large strapon. I had seen videos of two women doing this, but never imagined I would see it in person, let along one of them being my wife. And Jane was hot...I has always had a secret crush on her and now I was seeing her naked fucking my wife. After my wife came, Jane said it was my turn. As it turns out, she meant something different and now I understood. That night they would take the sissy cuckold to a whole other level.
Jane had me bend over the side of the bed and proceeded to lube up my ass. Initially, she penetrated me with her fingers, but eventually she entered me with a smaller strapon that she used on my wife. Initially, I felt only pain. After a couple of minutes, there was some pleasure. The longer it went, the better it felt. My wife started laughing I pointed out that Jane was no longer moving and I was now actually pushing myself back into the strapon. At that point I was on the verge of cumming and my wife placed a plastic near my cock to catch the cum and feed it to me.
That was not the last time Jane fucked my ass. She visits us a couple of times a year and always brings a strapon. The one time she forgot, she made me go to the store with her to purchase a new one. I am a sissy cuckold.
On the first day we made it just east of Amarillo and got two hotel rooms next to a Dairy Queen. While I decided to go to sleep, Lisa and Jane walked over to Dairy Queen to grab a bite to eat. I fell asleep immediately and did not wake up until Lisa came into our room around 7am the next morning. She apologized and said something came up.
As we were leaving the next morning, Jane surprisingly jumped in the car for me for the first part of the trip that day. During the drive, Jane told me what happened. They met a college kid working at Dairy Queen and invited him back to Jane's hotel room for a drink. The two girls started making out in from of the guy, eventually taking their clothes off so that my wife could go down on Jane. After a few minutes, my wife felt a tongue in her pussy and the threesome was on. Jane came quickly and then begged to be fucked. Unfortunately the guy only lasted a couple of minutes. Lisa was happy to clean up both of them with her mouth and he quickly got hard again. This time Lisa laid the guy on his back and mounted his young cock. Meanwhile, Jane mounted his face, forcing him to lick her pussy. This time the guy lasted few minutes, but eventually shot his load into my wife. At that point, they all collapsed and eventually fell asleep. When the ladies woke up the nest morning, he was gone.
I was not shocked by the story, but I was confused why Jane was telling me. Of course, I was hard as a rock and could not do anything about it with Jane in the car. For the next hour and a half, Jane would mentioned how big the guys cock was and how much he came. She would also mention how hot it was to see Lisa ride his cock. Then the conversation turned to me.
For the first time ever, I heard the word "cuckold." Jane explained that I was a "sissy" cuckold who stayed at home while my wife was free to fuck whomever and whenever she wanted. I did not argue, because she was right. Jane then proceeded to tell me that they were taking things to the "next level" the following night. At the next stop, Jane switched vehicles and I was alone trying to figure what she meant. About 8 hours later we pulled into our hotel in Nashville. To surprise, Lisa had only booked one room foe the three of us. Of course, I thought this would be my change for a threesome - and I was right, kind of.
After dinner, where we all had too much to drink, we went back to the hotel room. I was told to take a quick shower. During the shower, Jane came in and surprised me with a small enema bag and proceeded to tell me how to use it. Confused, I asked why, but she then raised her voice and commanded me to do it. Luckily there were instructions, so I cleaned out my ass.
When I was done, I walked into the room to find Jane fucking my wife with a large strapon. I had seen videos of two women doing this, but never imagined I would see it in person, let along one of them being my wife. And Jane was hot...I has always had a secret crush on her and now I was seeing her naked fucking my wife. After my wife came, Jane said it was my turn. As it turns out, she meant something different and now I understood. That night they would take the sissy cuckold to a whole other level.
Jane had me bend over the side of the bed and proceeded to lube up my ass. Initially, she penetrated me with her fingers, but eventually she entered me with a smaller strapon that she used on my wife. Initially, I felt only pain. After a couple of minutes, there was some pleasure. The longer it went, the better it felt. My wife started laughing I pointed out that Jane was no longer moving and I was now actually pushing myself back into the strapon. At that point I was on the verge of cumming and my wife placed a plastic near my cock to catch the cum and feed it to me.
That was not the last time Jane fucked my ass. She visits us a couple of times a year and always brings a strapon. The one time she forgot, she made me go to the store with her to purchase a new one. I am a sissy cuckold.
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