tagTranssexuals & CrossdressersTotally Sexy Massage

Totally Sexy Massage

byiser21©

A few years ago I was looking in the paper. I read an ad that said, "Totally and Sexy Massage." Come get your "T. S. Massage." The T and S was bigger then the rest. Totally and sexy.... Now that sounded nice to me. I had not had a massage in years. And a sexy one at that. So I called. Told her what time to be at my hotel and then sat back.

When I open the door I saw a young woman standing in front of me. She must have been all of 25 years old. She had on a black blouse. Open about 3 buttons. Her cleavage was showing. I would say about a 36 b with a tight bra, that made them come up and out. She stood about 5'7" with 3" heels. She had a mini skirt on that made her legs look longer. Stockings and a red bow in her hair. She looked like she just came home from school.

"Hi, I'm Judy. You called for a massage. Have you ever had a 'Totally Sexy Massage"? Her tongue came out and licked her upper lip. She took a deep breath and held it. Her breast almost popped out of her top.

"Sad to say, no I have not had one. But it looks like I'm going to." My eyes went from her face to her legs. They stopped at her breast and then down to her hips. Then down to her legs. Back up and I just looked in her eyes. "Care to come in"?

"You do know what a "Totally Sexy Massage is. It is a T. S. Massage. Totally Sexy Massage." Her eyes never moved. She was looking me right in the eyes. "Yes I would love to come in."

We talked and she told me that it would be $175. for her "Totally Sexy T. S. Massage."

"Lets go for it. It has been a long time. So How would you like me? On my back or front"? I thought I would act cool. I stood in front of her with a towel around me. I then got on her table and got on my stomach. She placed her oil on the side.

She started on my back. First with my legs. Her hands went up and down my legs. Stopping just before hitting my cock. I was feeling better then I had felt in weeks. Her hands went to my back. This woman could give a massage. She worked my back. Then down they went. Down to my ass. She pulled the towel down and started to massage my ass cheeks. I was breathing deeper by now. And her hands felt great kneading and rubbing my cheeks. I almost forgot the real reason I called her. Now her hands went lower. Right to the base of my ass. right to the spot that my balls started. Then down my legs. Believe it or not, I did not have a hard on yet. It felt that great.

"Turn over and I'll start on the front." I rolled over as she held the towel in place. Now I could look up and down and she her. She was standing on my right. Her blouse was open more then it was when she started. Her bra made her breast stand out. She looked into my eyes and said.

"Top or bottom"? I thought that she meant me so I said. "Top."

Her hands went to her blouse and unbutton the rest of them. Off it came. All I could do was stare at her breast. Damn.... they looked like they came right out of a book. Her black lace bra made them come up and together. I just looked at them. A smile on my face. I felt the starting of a hard on. I closed my eyes and I felt her hands once more on me.

"You like"? I felt her hands on my chest and felt them move around. Her hands went lower and soon they were right above my cock. I'm not that big. I would say about 6.5." Her hands stopped just before she touched me. They went to the side and down to my legs. I now had my eyes open and she looked me right in the eyes and said. "Now the bottom"? It was more of a question then anything else.

I could see her unzip her skirt. She pulled it down and she stood back up. I was looking at her face as she did it. But now I looked down. Her black lace bra was still on. Her breast rising and falling. My eyes went down more. I could see black lace panties. No hair. Just the way I like it. I thought to my self Shaved Pussy. The best pussy out. She also had on a black lace garter belt. Hooked to it was silk stockings. They went all the way down to her 3" heels. She turned to the right so I could see her side. Back up with my eyes and her legs went all the way up to her ass. Her garter belt made her ass stick out. And with her lace panties on ,I had to touch it. I ran my hand across her leg. Up and up till I reached her soft white ass. Smooth and cool. I ran my fingers across her lace panties. I reached her crack. I pulled her panties down. She turned and looked at my cock. It was now full, hard from looking at her.

"Now I'm going to suck your cock. I'm going to take it into my mouth and suck you till you scream.... or cream." With that she took hold of my cock. Looked at it and then kissed the tip. Her mouth open and with one downward motion took the whole cock in. I'm not that big. About 6.5." But that bitch took it all in one try. No woman has ever done that. Her mouth started to make love to my cock. Not like the others that let you fuck her mouth. But she made love to it. Judy loved to suck cock. Her mouth came off my cock and then back down. Up and down. Her tongue was moving to the right and left. Her mouth going up and down. All at the same time. This girl could give a dead man a hard on. I knew I was going to cum. And she knew it too.

I ran my hand up between her legs and was hell bent on sticking my finger up her cunt as I came. I felt her stockings, the top of them and then I felt her cold leg. Her smooth thigh and then her lace panties. Her shaved legs. I felt both legs and I knew I soon would feel her shaved pussy. I felt the heat from her and then I felt.

A cock. I felt a cock. How could she have a cock. It was to be a shaved pussy. But it was a small shaved cock. All this time she had a cock and not a pussy. Judy kept on sucking me. Her hand was jacking me off and she was going to make me cum. Then I felt her pussy.... no cock.

I pulled her panties to the side and I saw her small but hard cock. It must have been only 4" long. A hard cock, but so small. I have thought of sucking one, one day. And this was going to be that day. As her mouth sucked me and her hand jacked me I felt her cock. I started to jack her off. This was all new to me. Jacking off a woman's cock. And I knew I was going to ask her if I could suck it.

"The way you are holding my clit, you act like you didn't know? Did you"? Her sweet eyes looking at me.

"No. I thought you........ ." You thought I was a woman, is that what you are trying to tell me. You thought I had a pussy. You thought I was going to let you finger my cunt. Lick my cunt. Is that what you thought?"

"Yes it is. But now I think I might like to. You know try to.... I think I might like to. Then if you ." What could I say. My eyes never left her cock.

"So, you would like to suck my 4" clit? Is that it? Would you like to try a 69? Let me show you how it feels to have a cock in your mouth. Lie back and let me get on top."

Now I was on my back, looking up at a small cock. Her shaved legs around my head. I felt her take me back in her mouth. Her hot wet mouth. Her tongue licking my cock as it goes in and out. "Take me in your mouth and just let it happen. Just do what you think you might like."

"It is so small. I think I can get it all in my mouth. Let me try." I felt the tip of her cock, or clit on my tongue. Then I felt it slid into my mouth. Then I felt her small balls resting on my chin. I had it all in my mouth. Her whole cock was in my mouth. I felt her head going up and down. Then I felt her finger go into my ass. This was new to me. I licked my finger and did the same. Soon I was sucking her and finger fucking her. Faster and faster we went.

"I'm going to cum. Take my cum in your mouth. Taste my cum. Let me be your first." I was now letting her fuck my face. As I finger fucked her ass, she fucked my face.

"I'm going to cum. Take it." I felt her push herself into my mouth and I felt her cock explode. Then I felt it on my tongue. Then in my mouth. It was salty. But I like the taste. Her finger was deep in my ass. I felt myself ready. I sucked and pulled harder on her cock and then I shot. I came in her mouth and she sucked me.

When I was done Judy looked at me and asked me. "Was that you first time? Tell me the truth."

I could never lie to a sweet sexy thing like her. The one thing I love is to make them think it was my first time. So I told her the truth.

'Yes it was. I have never done that before." And I'll keep telling them all the same..

Write me and let me know how it was your first time...

Report Story

byiser21© 0 comments/ 141285 views/ 6 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartOtherJP, 21anna and 4 other people favorited this story! 

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel