tagTranssexuals & CrossdressersGreat Feeling Hands

Great Feeling Hands

byiser21©

It has been some time since I have sent in a story. So I'll tell you about me once more. My real age is 58, male, 5'11 " about 190. I bi so I enjoy both sides. Plus I have a thing for "TS's" and "CD's". It is the best of both worlds. Some off the things I write about are things I have done, some are of things I would like to try. More like what I fantasize about. I do hope you enjoy the reading.

The first time I met Wendy was the night I picked her up walking down Detroit road in Cleveland. I should not use the word walk. It was more like she was on parade. Showing off. Not just her walk, but her body. Legs to die for. She was about 5 foot 10 inches tall. What some would say , a tall glass of water. This one was a tall glass. Her legs must have been 36 inches long and went all the way up and made an ass out of themselves. She had on a short skirt that told you she was wearing a garter belt. You could see just a trace of it just above the hem of her skirt. She wore a blouse that was open at the top. And was a size or two to small. Three buttons were open and you could see her cleavage. You know that valley between her breasts. It had a soft smooth look. It looked more like they were made out of light chocolate. Yes she was a black woman. But I would not call her black. If I may use the term "Chocolate Woman". That would be more like it. More like the color of chocolate milk.

Her body made me pull my van over. At first I thought she was a "working girl". Then I thought I might be wrong. Someone that had a body like this could not be selling it. But I pulled over. It was cold that night so I had to open the window. As it went down , Wendy looked and walked over.

"Hi. Its cold out. Care for a ride"? I thought it was the best line to use. If this lady was a cop she might not bust me for asking this way. But then I thought if she is a cop she's going to bust me anyway.

" It is cold and yes I would like a ride". She opened the door, looked around and then got in. The door closed and the window went up.

"Would you like some heat? You look like you could use some". I could see that her nipples were sticking out. Nipples? Hell they looked like some one had put a large raisin in her top. Then again it may have been a grape. Her nipples stuck out so far you could dial an old phone with them. I was looking at them. And I knew she knew I was looking.

"Thanks, I could use some heat. In more ways then you think". That told me that she had to be a hooker, and not a cop. As I reached over to turn on the blower I looked down at her legs. Shit. They looked great. I could see she had stockings on and I could see her garter belt. Her stocking tops could be seen. I could tell my breathing started to speed up and I knew I was getting a hard on. I was thinking of something to say to let her know I was looking for more then just giving her a car ride.

"Tell me when you hot enough. And I'll stop it". I know that it was a dumb thing to say . It was the only thing I could think of other then just telling her that I would like a blow job.

A smile came to her face. "Honey turn up the heat all you like. That is why I'm out walking the streets. Are you a cop"? As Wendy said this I could see out of the corner of my eye she had pulled her top down just enough so her nipple was showing. She looked down at my cock. This is something I always ask for. I ask them if they are a cop and then I ask them to show me that they are not a cop. This is done by showing a part of the body. Nipple, cock or having her pull her panties down and seeing her pussy. But she beat me to it. Her nipple came into view. It looked like a grape. A small dark brown grape. Her skin around her nipple was like looking at a glass of chocolate milk. Smooth and so, so soft. I was just about to reach out and touch it. But I knew that I had to show her I was not a cop.

"How's this"? I reached down and pulled my cock out. I had my shirt over my open zipper and I could pull it out faster and better. I knew that most hookers asked to see something. My cock came into view. It started to get harder , my hand moved up and down. Jacking off is something I love to do. And love to watch. Since I'm bi I have been with both male and female. I started to jack off when I heard her say.

"That does look nice, so big can I touch it? Would you like if Wendy helps you do that? I love to jack-off guys". I felt her hand on my cock. It was rock hard by the time she put her cold hand on it. I watched as her hand started to move. Slow at first and then she started to move faster. Her hand would close on the down stroke and open on the up stroke. I could tell she knew how to jack a guy off.

"Lets get in the back so we have more room". I have no windows in the back and I have seats all the way in the back. That way I can stretch out. The carpet is soft. A person could kneel and not feel the hard floor. I know I have done it a few times. I was in the back with my pants down and started to pull them off.

"Hold on honey. First, what is it you want? Next I ask for money up front". Wendy was kneeling in front of me her hand still on my cock. She looked down at it and then started to bend as if she was going to suck it. Wendy only kissed the tip.

"Wendy my dear. I enjoy having someone watch me jack off and give me a helping hand. And I like to watch a lady do the same in front of me. I have $35. and that is it. How about it"?. I was placing my hands on her tits and I started to push her top down. She had a grin on her face. Not a smile but a grin. As if she was going to tell me something.

"Honey you got a deal. $35 and I'll give you the best hand job you have had in years. Better then you can give yourself. But as for me, I'm on the rag. So you doing me is out. But I do have a mouth an ass". Her look told me that seeing her pussy was out. But then I thought. No She had to be a female. Her hand was still moving up and down. I gave her the money and she went at it.

I sat back and watched her jack me off. I saw her reach into her bag and bring out some KY. I felt the cold jelly on my cock and I knew I was going to heaven. Her face got close and she watched my cock slide in and out of it. The car was not all that hot and I could feel her hot breath on my balls. From time to time Wendy would look up into my eyes and grin. That grin I would see more and more as time went on. I felt her tongue lick my balls. I could feel her hot breath on my ass. I was looking down between my open legs and watch this beauty jack me off.

"May I"? Wendy never waited for an answer. Her mouth open and I felt her suck in one of my balls. At the same time she never missed a beat. Her fist going up and down. The KY was doing it job. My cock felt like it was in a tight pussy. Soft and hot. Wendy pulled her head back and sucked harder on my ball sack. It hurt but felt great at the same time. With a pop sound my ball came out of her mouth. This time Wendy smiled. A smile that shown her white teeth. Her mouth was open and I could see she loved what she was doing. And so did I.

"Do you like doing that? Giving pain that is. You can do it some more if you like". Her tongue came out and she licked her upper lip. Then the corners of her mouth. Then she closed her mouth and I could see her stick out her tongue to make her lips wet all over. Her head bent to one side and she went under my cock and balls. I felt her blow hot air onto my anal hole and then I felt her suck in my left ball. This time she was not to gentle. I pulled up and back some but did not stop her. I felt her tongue licking my ball as she sucked it in deeper. It felt like a hot wet finger moving across it as she sucked and pull some. At the same time I could feel and see her hand jacking me off. This cunt knew how to jack a guy off. Not only that but she like sucking nuts too.

"May I"? I asked as I reached out with my right hand and started to pull her skirt up. I did not have to pull that much. It was almost all the way over her ass. I looked down and could see her panty covered ass. Red lace panties. I could see her red lace garter holding up her stockings. My hand moved over her ass. It felt cold. It felt soft and in the light from the street lights I could see a her brown skin. I rubbed across her cheek and then the other one. Damn was she hot. Her hand was no longer jacking me off but was making love to my cock. It felt like I was fucking her hand. I was pushing up with my hips to meet her hand as it came down. Her mouth still sucking my ball.

I pulled my hand back from her ass and then I just let go. I brought my hand down and slapped her cheek. Not to hard but enough that she felt a sting. Wendy did not move. Most of the time when you slap a lady on the ass she'll tell you to stop. Not this one. So I gave her one more. Then another one. Then another. I gave her about 20 when she pulled back and looked up at me. The look on her face told me she liked this game. I gave her 5 more.

With each slap the look on her face changed. It went from a sexy look to a kinky look. It was not from pain. I was not spanking her to give her pain. But to let her know that I enjoyed it as much as she did.

"I'm going to do something I don't do that much. I'm going to let you cum in my mouth. But it has to be the way I like to do it. Understand? Keep spanking me. And I'm going to jack you off into my mouth. I'm also going to do this". With that I felt her tongue lick my ass hole. It felt like a wet finger running across my hole. It had been years since someone had done that. At the same time Wendy's hand was making love to my cock. My own hand was spanking her ass. But this time I was doing it harder. Not to hard but harder then before. I could feel her breathing harder as I spanked her. I felt her push her tongue deeper into my ass. A sound came out of my mouth and I pushed my ass down. Wendy knew what this meant. And she pushed more. I felt her mouth come away from my ass and her hand from my cock.

"Don't move. I'm getting more KY". The KY was colder then before but felt great on my hot cock. Her fingers went around my cock and her face looked up at me. Her mouth open and I could feel her tongue on my balls once more. Licking and licking. Her top was pulled all the way down and I could see her breast. They must have been 36c.

"Spank my harder. As hard as you like I enjoy it. I enjoy a red ass. I also love to spank others. But that will be next time. I'm going to do something I have not done in a few years". With that I felt her take both of my balls into her mouth. My hand came down on her ass. Not as hard as I could , but enough so it made her move. Then I felt her suck my balls harder. And I spanked her harder. This went on for about 2 minutes. I felt her pull away from my balls and lick my ass once more. I felt her push her tongue in and then I knew it was something else.

All I could do was take a deep breath. I held it and then I felt something going up inside my ass. I knew it was not her tongue. It was her finger. Wendy had but KY on her finger and was now fucking my ass. I looked down and all I could see was her eyes looking at me. My head moved up and down telling her that it was okay. Her hand going up and down and her finger going in and out.

Wendy pulled back and I could watch her tits bounce up and down as she jacked my off. How sexy is that. To have a lady like this jack you off and finger your ass, at the same time. Fuck Yes. It was great. Her finger moved in deep and her hand moved. Her finger bent and she found what she was looking for. My prostate gland. This lady knew her way around an asshole. I bit down on my lower lip and her finger moved left and right. I looked down at her and she was loving ever minute of this. She had a shit eating grin on her face.

"You like"? That is all she said.

"Yes I do like. You know your way around an ass and a cock. What else can you do"? I felt her finger come out of my ass and the look on my face told it all.

"Don't move. I'm getting more KY. I need it. You have such a tight hole. Has anyone ever done this to you"? Then I felt her finger back at my ass. But this time when it went in it was bigger. It slide in and came out and went back in. Wendy was now fucking my ass with two fingers. A low cry came out of my mouth. I could not move. It was like I was tied down and was helpless. My leg spread open and this hand was doing what ever it wanted to do. I could not speak. My eyes half closed and my mouth open. I had stopped spanking her a long time back. All I could do was open my eyes and watch as she did what she wanted . She had control over me. She moved around and was now sitting more then kneeling in front of me. Her legs crossed and her skirt all the way up. Her top was down and I could see her tits bouncing and her right hand jacking me off and her left hand moving in and out with her fingers pushing into my ass.

"I'm getting close my dear. I'm almost ready to shoot". I was looking down at her and hoping that she was going to take me in her mouth. I guess my face said it all.

"Yes my dear. I'm going to let you cum in my mouth. I want you to shoot your cum into my mouth. All over my lips. On my face. Shoot it till it drips on my tits. Let me lick your cock clean. Then I'm going to let you lick my lips and suck your cum off my nipples". Wendy was looking into my eyes as she told me this. She also moved some. Now I could see the front of her panties. Her red lace panties. One thing I love about lace is that you can see thru it. I felt my cum starting to move. Soon I was going to cum in her mouth. Then I saw it. Wendy had a cock not a pussy.

With that I started to shoot. I open my mouth and eyes and looked down at her cock. It was about 6" long and sticking out the top of her panties. I reached out with my hand to hold her face.

"Now". That is all I said. I started to cum. Wendy jacked me off into her mouth and onto her face. I was looking down at her cock and she knew I could see it. This sent her over the edge.

"Cum for me. Cum all over my face. Let me fuck your ass with my fingers. Let me lick the cum from your balls. Force me to lick your cock clean.". With that she pulled her fingers from my ass and I started to cum. I came on her face and in her mouth. all over he lips. I watched as she jack my cock off and pulled all the cum from it. At the same time I watched her grab her cock and pull it three times. Wendy started to cum.. She placed her hand on the tip and started to cry. Her hand filled with her cum.

I watched as she licked my cock clean and then my balls. She then looked at me and brought her other hand up to her mouth.

"Does this turn you on"? With that Wendy licked her own cum from her fingers. Sucking them like a cat cleaning it's paws.

"Yes it does". That is all I could say. I was watching her lick her fingers and I was also looking at her cock.

"Next time I'll let you jack me off as I do the same to you. Okay"?

I gave her $20 more that night and got her phone number. And yes I did go and see her. And yes I'm going to write about it.

Please drop me an e-mail and let me know what you think of Wendy. This part of the story is true.

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