tagTranssexuals & CrossdressersMeeting My Internet Friend

Meeting My Internet Friend


It had been 3 hours since I last e-mailed her. She told me that she would be at the park at noon. It was now 11:50 am. I was just getting out of my car. I looked around to see if her 95 red Ford van was in the parking lot. I was to meet her at the walking path. I looked around. No she was not here yet.

I started to think about how we met. I was in a chat room and I found her under panty lovers. We had been e-mailing for about 9 weeks. I had open up to her. I told her things about myself that I have never told anyone. Not even my wife. I have been married for 20 years. My wife never knew about my thing for panties, garters, stockings and cock. Yes I had a thing about CD’s and TS’s . I had been out with a few but never like this one.

Kathy was 22 to my 42. She was a part time cross dresser. She was bi like me, but love to play the part of the lady. Loved to play the part of the “first time”. And I also loved to play that game. Kathy had told me that she could pass as a woman. I told her that I would love to meet her and see if I could “once more let myself go”. So here I am looking for her car. It was now noon and I did not see it. I thought she might have lied and was not coming. I started walking back to my car when I heard.

“Bob, is that you. You look so...... young. You told me that you were in in your forties. But from what I can see you look more like 35. Is that you my love?

As she spoke I walked towards her. She looked more like she was in her late teens not mid 20’ts. And when she said she could pass. Hell I would have thought she was a women. When I got about 4 feet away she put her arms out and kissed me on the cheek. I held her and could feel every nerve in my body get tight. I could not speak.

Kathy was 5’ 5” tall. About 120 with blue eyes that you could walk into. She had on a dress that button up the front. The top three buttons were open. I was looking down at a pair of tits that looked real. Her dress came to about he knee. and her stocking legs looked great. She had on a pair of 4inch heels. I knew that I was getting hard.

“Kathy you look great. You said that you could pass but, you are great”. I took her hand and we started to walk down the path. Kathy held my hand. I felt like a school kid. But then I felt like a “dirty old man”. We had talked about this side of me. And Kathy told me that she loved to play this game. She had played it with more then one man my age.

As we walked we talked about the things we enjoyed and the things that we would like to try. We walked on for about 10 minutes. Then Kathy pulled me towards her and kissed me once more. I felt her hand move down between my legs and she took hold of my cock.

“Bob I have been thinking of this for 6 weeks. And now I’m going to have it. I know that you like to play so I’ll play the school girl and you and be my teacher. Now tell me Mr. Bob. What is it that you are going to teach me”?

I pulled her off the path and into the woods. I found a place that was open and I put a blanket down. I sat and looked up at Kathy. I still could not believe how she looked. I could see up her dress and she knew it.

“Mr. Bob. Are you looking up my dress? You do know that if the school found out you could lose your job”? Kathy took hold of her dress and started to pull it up. First her knees then the top of her stockings. I could now see the garter holding then up. Then I could see her lace panties. All in black. She knew that I loved the color black. With a smile on her face she held her dress high.

Mr. Bob, do you like what you see”? What could I do. My cock was hard. Harder then it had been for years.

“Kathy, yes I like what I see and yes I could get fired if they found out. But you are over 18. And we are on a field trip. Who will know. I’m not going to tell and I know that you, how shall I say. Need to pass. So if you let me see more, you might pass”. We had talked about this game. And we both knew what was going to happen.

Mr. Bob. Yes I’m over 18 and you are a dirty old man. You think that you can make me undress just by telling me that you will pass me. It is going to take more then that. And I do have a few things that you might not like. Mr. Bob. Pull your zipper down. Show me what you have for me. Then I might let you watch as I pull my panties down”.

I reached down and pull my zipper down. I had forgot that I had put on a pair of red lace panties. I undid my belt and unhooked my pants. I opened and Kathy could see my red lace panties. A smile came to her face. I reached down and pulled them down and my 7 inch cock came out. All I could do was look up at her. look at her panties and dream. I saw her hand come down to her panties and she rubbed herself. I reached down and started to jack off. That was what I loved to do.

“Mr. Bob is this what you want to see? Is this why you took me into the woods? Would you like me to watch you do that nasty thing as I pull my panties down? Is it Mr. Bob”?

My hand never stopped moving. I was jacking off in front of her. And this was the first time we ever met. I looked up into her eyes but she was looking at my hand. Kathy was watching me jack-off and licking her lips as she did. I looked back down at her panties and she was now pulling them down. Kathy turned to one side then the other. She must have been looking to see if anyone was around. Then with her legs together she pulled her panties down to her knees.

I thought ...... Now I was going to get to see her for the first time. My hand never stopped moving. Up and down. Fast and the slow. Back up and then back down. As her panties came down I looked at her. I could see a “Y”. Her legs made a big “Y”. Now hair. Kathy had never told me that she shaved. I liked that little girl look. It looked like she would have a “Bottom Pussy”. That is what I call them. A pussy that is on the bottom. Now Kathy stood. Her dress pulled up. Her panties down to her knees and her garter and stockings looking back at me.

“Mr. Bob. Pull your pants down and off. But leave on your panties. I like them”. This was the first time I remembered that I had panties on. I took my shoes off and then my pants. Now I am lying on my back. Red lace panties pulled down under my balls and jacking off for this great looking lady. She is taking off her dress and now is standing in front of me only in bra, garter, stockings and panties pulled down to her knees. Kathy turns sideways and steeps out of her panties. She gives them to me and turns back towards me.

“Mr. Bob put them in your mouth and suck them”. I can see that “Y” once more. When am I going to get a look at her........ You know. I place her panties in my mouth and suck them I smell her and I like what I smell. I watch her as she now starts to bend. She kneels and then bend towards me. I feel her hand on my thighs and the I feel her hand on my cock. She opens her mouth and I feel her lips on my cock. Kathy pulls back.

“Mr. Bob. If I do this for you will I get a good grade? If I stick your cock in my mouth will you pass me? If I take you all the way into my mouth, will you give me, say an A?

Or do I have to stick my tongue here”?

With that she took her finger and started to stick it in my ass. Her head bent and I felt her mouth take my cock back into it. Her head going up and down. Faster and faster she went. More and more of me went into her mouth. I felt her finger going deeper into my ass. This lady knew how to suck a cock. I was going to cum and I told her to please stop.

Kathy pulled off and stood up. She took one step over me and I could now see what I have been waiting for. Her boy clit. What we call her “long clit”. It to was shaved. Kathy stood over me for about one minute. Letting me see her. It was long about 7 inches. Hard and smooth as a baby’s ass. Kathy reached down and took it in her hand. She was now jacking off with me. But then she took one more step and knelt down. Once in that 69. She went back at me. I opened my mouth and felt her go in.

I have not had a cock in my mouth in 5 years. But as they say. “Once a cock sucker, always a cock sucked”. I went right back to it. I felt her finger going back in my ass and I felt her mouth take me all the way down. I was getting one of the best blow jobs I have had in years. And I was hoping that I was doing the same to Kathy. I felt my cock getting harder and I knew I was going to cum.

“Kathy, I’m going to cum. Do you want it in you.......”? That is all I got out. I felt her stick one more finger in my ass and I started to shoot. Kathy sucked my cum like now one has ever done. I felt her pull every drop out. Then I felt her push hard into my mouth. Kathy never asked. But just shoot off in my mouth. I sucked and pulled what I could but I know that my mouth was full. I do not like to swallow but I had to. Most of it was dripping out and down my chin. Kathy pulled off my cock and licked the tip. She took it into her hands and milked it dry. Then I did something I never do. I kissed her. I got to taste my cum. We must have kissed for 2 minutes.

Kathy was on her back and was trying to pull her panties up when we saw someone watching us. We both knew it was a cop. I pulled my pants up and was trying to get them zipped when the cop came out of the woods. Kathy was just putting her cock back into her panties.

But i’ll have to tell you about that later

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