tagTranssexuals & CrossdressersMy First Time, The Next Step

My First Time, The Next Step

byiser21©

In my first part I told you about Helen. I have been seeing her for about a year. And we have had great sex. She has taught me how to please her, and how to suck her. As I told you she is only about 4.5 inch's long. She has done me anally, but her size just does nothing for me. She could only get no more then 3" in me. I have thought of going out with some one new, but could never find one.

One night after a movie, a woman I work with walked by us. "Hi Amy, how's it going?" All Amy did was look at me and Helen. Never said a word. I have worked with Amy for four years. She is about 29 years old. When she has a dress on I can see her 36c tits, and great legs. All the guys ask her out but she never goes out with any of them. This was on Friday night.

Monday as Amy walked by me she stopped. "How was the movie?"

I looked up at her. In the four years at work she may have stopped 5 times and said something to me. "Great, I enjoyed it. And you, did you enjoy it?"

"No I never get to the show. No one ever asks. So I just stay at home."

"How about going to the show Friday night with me?" Just as I said it I thought.... No one has ever got a date with her.

"NO. That does not sound like a good idea." Fuck. Now she has told me no. This cunt needed a good one. Now all the guys will know she said no to me. Then I heard her say something. "I'm sorry. What did you say?"

"I said no to the movie, but how about dinner?" Her eyes never left me. Just looking right into me.

"Okay. Friday night then. How about steak? I'll need your phone number and address."

"Great. Be at my place at 6:00 pm. Do you know how to get to Old Brooklyn? I live off Pearl near State."

"Yes I do. I'll see you then. Or I should say later on in the office." Now I didn't know what to say. I took her address and looked at her. Thinking what do I say now. She smiled and walked away. "6:00 then Friday. BYE

For the rest of the week all I could do was think of Amy. Her long legs. Her eyes. Her mouth. And then I thought, what about sex? No she will never go for that. But she did have a thing about her. The way she sat. Her legs push together. Never letting anyone see her legs. Never bending over showing off. The week went slow.

At 6:00 Friday night I pulled in her drive. Nice house. Old but nice. I rang the bell. The door open and she stood in front of me. Not dressed up like I thought. But not underdressed.

"Come in Bob, I still have a few things to do." Great we might be all night. Not that that is a bad idea. But she did say 6:00. The house was old but the inside was newer looking. Large living room. I walked behind her to the dinning room. The table was set. It looked like she was going to eat dinner.

"I thought we would eat in. I have two steaks and all the things to go with it. I hope that is okay with you. Is it?"

"Sure, I think it is a great idea. Can I help?"

"No just sit and it will be out in a few minutes. You can sit at the head. Okay?"

She left and then came in with dinner. She put it down and walked out of the room. In one minute she walked back in. She had changed her clothes. Now she had on what looked like a silk rap around. Damn did she look great. All I could do was look and then said.

"Looks great on you. It........"

"It shows off my cleavage. Is that what you are thinking?" All I could do was look.

"Why yes... It does. And if I may say it is a nice cleavage at that. I'm sorry I should not have said that."

As we ate we talked. In one hour I felt I knew her. She asked if I was married, NO. Did I have any kids. NO Did I date. Yes only two woman, I could never tell her about Helen.

She looked at me and said. "How about that lady I saw you with last Friday? Just a friend?" I looked at her and said "Yes,.... A friend and." I stopped "How about you.

"No not married. No kids. No I do not have a guy friend. And no I'm not dating anyone. Would you care for a beer?"

"Yes. Let me help you."

"No just sit. I know what to do. And I'm a big girl." She took my dish and then walked back in with two glasses of beer. She stood on her side of the table and but her glass down then reached over to my side. As she bent over to set it down I could look down her top. Her cleavage was nice. And I could see the white meat. I just looked and she bent over more. As she set the glass down it hit a spoon and went all over me. Down my front and on my pants.

"OH SHIT. I sorry Bob. That was so......"

"No NO That's okay. I'm okay."

Amy stood up came around the table and kept saying she was sorry.

"Let me help you." She started to take my shirt off. "No. It's okay."

"No.... You can not sit in wet things. Let me wash them. You smell like beer." She had her hands on my shirt and belt. Opening them both at the same time. "Take them off and I'll wash them. Go into the bathroom and hand them to me. Do as I say."

I went into the bathroom took off my pants and shirt. I held them out the door. " Your shorts too." Thank God I didn't wear panties like I always do. I took off my boxers and gave them to her. "I'll drop them in the washer and you jump in the shower. Wash off that beer smell."

I was standing in the shower when I heard the door open. Then the shower door open. Amy stood looking at me. She still had on the silk rap around on. With out a word she stepped into the shower dressed. "Let me help you."

It was the sexiest thing I have ever seen. Her top started to get wet. And as it did I could see right thru it. As if she had nothing on at all. She picked up the soap and started to wash my arms. Then she went to me chest, then working down she came to my cock. Looking right in my eyes.

"We can not have this smelling like beer. Can we?" She slowly washed my cock. The more she washed the harder it got. Then harder it got the faster she washed it. She knelt down in front of me and put her nose right up to it.

"Now it smells like it should. I also like that you shave. I love a smooth cock." Looking up at me she put the tip in her mouth. Her tongue touched the tip. I could feel her mouth open and she took about an inch in. Her head came back and then bent forward. Now about two inch's. Then she pulled back. Then three, then four, then five, and then six. Fuck could this girl suck cock. Looking down was so the sexiest thing yet. I could see her sucking me and I could see her tits right thru her top. I have had girls strip for me and this was better. I could not take my eyes off her tits.

Her hands went under me and as she sucked my cock she started to wash my balls. Soon her fingers were on my ass. Washing me hole. Fuck if she keeps this up I'm going to cum. I pulled back some. She knew why.

She stood and I kissed her. I felt her tongue in my mouth and I sucked it like a small cock. I thought of Helen's small cock and thought of how I loved to suck her. My hand went to her top and I pulled it open. Her breast fell out. They felt so soft, but hard. I took a nipple in my mouth and sucked hard on it. I held it with my teeth and bite down on it. She never moved. I pull back with it still in my mouth and bite harder. Still not moving. Now I'll teach this cunt. I pulled back and bite down on it. She held my head with her hands.

"How did I know you like to give pain. I could tell that you would. But the question is, Can you take it too?" Her hand went to my nipple and she pulled on them. Pulling and turning. Then she let go. She bent over and said "Please, Please. Could you Please."

I let go and my hands went to her hips. I started to open the front and she turned so her back was to me. My cock went in her crack. I pushed forward and felt her ass push back. I went around with my hands and open the rap. It fell in the tub. I started to rub my hands up and down her sides. I worked in.

"You shave too?"

"Yes I do. Feel and tell me what you think."

I worked my hands between her legs. Then I felt it. I froze. I felt something that I was not thinking about. I pull back and she turned and looked at me.

"I thought you knew. I'm sorry Bob I thought you knew. You don't have to."

All I could do was look down at her. And see her cock. She had a cock. I never thought that she was a man. I looked at it and then knelt. I knelt down and looked up at her. " No I did not know." As I bent forward I open my mouth and took her in.

"I thought that Helen would have told you that I was........." That is all she could say. I started to suck her. Me The guy that a year ago never did it was sucking a cock about 6.5 inch's long. It looked like my cock. But not as round. I would say about two fingers wide. I could get in in my mouth and I was going to show her that I could suck cock like her. She held onto my head and I took it in and let it out. Took it in, let it out. Up and down. Up and down. Now I knew what it felt like to have a mouth full. I could feel it hitting the back of my mouth. Never have I felt that. I kept it up till I thought she would cum. I pulled back. Looking up at her once more.

"You said something about Helen. What did you say?"

"I thought Helen would have told you about me. I have known her for about a year now. She has told me all about you. How you have been looking for...... How can I say this."

I stood and held her cock. Looking her right in the eye I said. "I have been looking for the right size cock to fuck me. Helen only has about 4.5 inch's and some of the other guys I know I could never take it..... To big. But I think that this is just the right size. Would you like to be....... the first?"

"Yes. Come with me and I'll teach you the right way to get fucked." We walked into her bedroom. She had me lie on my back. She knelt down and started to suck me once more. She worked her way down till I felt her tongue on my ass. She pulled my cheeks apart and I felt her tongue push on my hole. Soon she had about 1/2 inch in my ass. Then I felt her start to suck me once more. I felt her finger pushing on me. Then I felt something cool. K Y. Then I felt her finger go up into my ass. She sucked me and finger fucked me at the same time. Then I felt another finger. She had two fingers in me. I was breathing so fast I thought I was a train.

I heard a sound and I knew she was putting on a condom. " Always use them I hope you understand."

"Yes I do. And don't stop. I'll say the word "EGGS" if it hurts to much." She looked me in the face and said " Are you sure?"

"Yes. I have been thinking about this for a year." My breathing was going faster. I pull my legs up some and looking her right in the eyes. "Please fuck me. Be my first." I could feel her cock pushing in. I had an inch in me and it felt like 6. She pulled back and then pushed forward once more. One inch went in and then about 1/2 more. I took one deep breath and she pulled out some. I felt her put more K Y and then push harder. This time about 3 inch's went in. My eyes went back and I started to breath faster.

"Should I stop?" No, No, Please do it but go slow. She pulled out and then pushed. I took more of her sweet cock in. It felt like I had a foot in my ass. "That is about half of it. Should I do more?" Without me saying a word she pulled out and started to fuck my ass with short strokes. IN out. In out. In out. I felt her pushing and pulling. In and out. I have never felt anything like it. Now I know why woman like to get fucked. Now I know why they scream. FUCK ME FUCK ME. Now I know.

"Can you take more, my dear?" I was almost crying. It felt that great. I felt her push my legs up higher and then my knees hit my chest.

"Yes do it. Give me more. Go slow. But give it to me. I have never felt anything like this." Amy started to fuck me deeper. With each push I felt it more and more. Then I felt her balls hitting my ass. She was all the way in.

"My God Amy. I have never felt like this. I'm going to cum." Amy started to fuck me like I have fucked other woman. Hard. Fast. Deep. I felt her balls slap my ass cheeks and I could hear her tell me that I was tight. That she was going to fuck me till I scream.

And she did too. I was going up and over the top. Never have I thought getting fuck could ever feel like this. I should have done this years ago. I felt it coming on. I knew that I was close.

"Amy, soon very soon. I'm going to cum..... Cum with me." That is all I could say.

"When you feel like you are going to cum tell me. I'm going to teach you something that took me years to learn. You are going to learn the trick."

In and out. Push and pull. Faster and deeper. Long and short. Then I felt her fuck me hard. Harder then I have ever fuck a woman. I could hear her legs slap my ass and I could hear her balls hitting my ass.

"NOW. NOW. I'm going to cum." I felt her push in three more times. I felt her grab my cock and jack me off as she fucked me.

"Open your eyes. Now open your mouth. As I cum you are going to cum all over your face and mouth. Taste it. Think of me doing it in your mouth."

I had my eyes open and my cock was about 4 inch's from my mouth. I felt like I could suck myself. Amy fucked me and jack me off and I started to cum. She pump my cock as I came. I came in my own mouth. I have never done that. And at the same time she came in my ass. I could feel her come in the condom. I could see myself cum and see the look on her face.

This had to be the best time I have ever had. Now I know why woman like to get fucked. I also know why they like it in the ass. I know that I'm going to see a lot of this girl. And I'm not telling anyone at work.

Please e-mail me and tell me what you think of My first time. (Anal)

Report Story

byiser21© 0 comments/ 161864 views/ 12 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

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

heartDeathcakes, Jmack1965 and 10 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