My wife, Laura is no stranger to women as she is bi. However, she has never been in a relationship with a trans female, something that I always wanted to change.
Let me start from the beginning...
I am retired but work part time as a driving instructor. Most of my students are teenagers but every now and then I get an adult student, which is a nice change for me.
One weekend I was assigned an adult woman to give lessons to. From her chart she was scheduled for 10 lessons as she was a beginner. Her name was Diane.
So, this one Saturday morning I went to her house to pick her up for her first lesson. When she came out I was pleasantly surprised at how pretty she was. She was wearing a tank top and white shorts for her lesson. After she got in the car we went over some paperwork and I advised he of how I taught and what to expect. I gave her some literature to take with her for her future reference.
I then told her to move over to the driver side so we could start the lesson. I got out and headed to the passenger side as she went around to the driver side of the car. Just as she was going to get into the car she slipped and fell down. I quickly went over to her and picked her up. She complained that her ankle hurt so I helped her back into her house and had her sit down and told her to raise her foot up. I asked her if she had ice and she said she did so I went and got some and wrapped it around her ankle. As she was resting I called my office and explained the situation. They told me to stay and make sure she was ok.
After about a half hour or so, she said the pain was less and I could see the swelling went down a little.
She thanked me for helping her and staying with her. Then she said she wanted to change her clothes. So I helped her to her bedroom and then left her. A short time later she called me to help her. I went into the bedroom and there she was trying to get her tight shorts off so she could put on something else. She then asked me to help her get her shorts off. I told her that I didn't think I should do that but she insisted. So, I moved over to her and grabbed the sides of the shorts which were really tight on her. They were tough to pull down when I suddenly gave them a hard yank and off they came along with her panties. That's when I got the surprise of my life. As her shorts and panties came down, her cock popped out.
I was shocked and apologized and quickly left the room. A few minutes later she hobbled out and sat down besides me.
"Diane, I am so sorry that happened."
"It's all right. It wasn't your fault. I hope you forgive me."
"Look, I am really sorry that happened. I think I should go now. I won't tell anyone. I promise."
"John, it's ok, really. Is this the first time you have seen a trans female?"
"In person, yes. But I have seen many in porn movies."
"Do you like seeing them?"
"Being honest, yes. I think they are special."
"John, are you married?"
"Yes. I would love to see my with with a trans female though."
"Really. You want her to have sex with a tranny?"
"I sure would."
"Would you like me to have sex with her,?"
"Sure, but that will never happen."
"Want me to try?"
"Are you serious?"
"Of course I am. Hell, I would love to have sex with you. Would you like that?"
"Yes, I would."
"Call your office and tell them I am still a bit shaken and that I would like you to stay until a friend of mine comes over."
I called the office and told them.out of the story and they said stay until her friend relieves me.
As soon as I hung up Diane took me into her bedroom. She was already partly naked and told me to undress which I did as she finished undressing. We got on the bed. Her cock was as hard as mine and I wasted no time in sucking it. We then started kissing and making out. Our cocks and balls touching.
Then she told me to get on all fours. I did and she started lubing my ass and her cock and then I felt her cock head pressing against my asshole. She gently washed her cock into my ass. Surprisingly, her cock easily slid into my ass and soon it was completely inside me. She started fucking my ass and it wasn't long before she came in ass. God, it felt amazing.
Then we reversed positions and it was now my turn to slip my cock in her ass. As she was on all fours, I pressed my cock into her ass, filling it with my hard cock. When I was all the way in, I started fucking her. It wasn't long before I shot my cum into her ass.
We both fell to the side, cum still oozing from my cock.
After awhile I said, "So how are you going to fuck my wife?"
"I need all her info. Then I will figure out a plan to seduce her. Just remember, this is what you asked for. I will be in touch with you. See you at our next lesson. You will.owe me big time afterwards though."
"Ok."
A week went by when the next lesson with Diane was here.
This time there was no accidents and the lesson went well. As we finished the lesson Diane said, "Tonight starts my plan. I hope you are ready for this."
"I am excited and am wondering how you will pull this off."
"Never mind. Just remember you will owe me big time."
"I know."
That night when Laura and I were home she got a text message. Then after a few minutes Laura came to me and said, "I got the strangest texts. They were from some woman named Diane. The first one read 'Nice to meet you. Will stay in touch Diane' Then that followed by 'Sorry wrong person but I bet you're a nice person'...then the last one read 'Sorry for the texts...my mistake....I owe you a lunch...let me know when and where' Diane....
I laughed and said, "A new girlfriend?"
"I texted her back and said 'No need for a lunch but you do seem very nice...another time, Laura'.
We both laughed and called it a night.
