Judy's First Time Ch. 05

Judy’s First Time Ch. 5: Finger In The Ass

This is about Judy, my niece. If you can read the others 4 parts first. That way you will know how we got to this point. This part is how we started off with anal. This is just the first part of getting her ready for a good old ass fucking. Just the first finger. Then comes the enema, then my cock. Most likely in two parts.

It had been 5 days since Judy came to my bed. My back was better, if you remember I fell and hurt it. I could move around better now. Judy and I talked after the first night in bed. Since she was going to collage and needed to study we thought it better that we kept “our games” to just the weekends. Judy went to college, came home, fixed dinner, did her studies. Most of the nights we talked at dinner about her school and things that I did around the house. We never talked about what had happen that night with the hand job that lead to the first blow job. Then the shower. Or my first time fucking her. We both knew that it was going to happen the next weekend and I think we both felt that when the time came, we would talk.

Thursday night came and Judy dropped the bomb on me! “Uncle Bob. I know we told each other that we would only ‘play’ on the weekends! I was hoping that you could teach me, or help me with anal sex? I don’t want to get pregnant! And I know that most guys like anal. So could you help me with that? Or at least start to teach me about it?” I could not believe what she was asking me. My sweet indecent niece just came out and asked me to fuck her ass! She knew that I loved it. I had told her about the times I did that to my wife. Judy also had seen the video of me doing it. But to just come right out and ask! I was thinking of just taking her to my bed that night.

“Judy, have you ever tried anal?”

“I have tried it a few times. All of them hurt so bad. They never got in my ass! They just pushed and pushed. I had to stop them because of the pain. Watching you and Aunt Mary. You make it look so easy! You take time and do so many other things. Licking, then a finger! And watching Aunt Mary’s face as you push your cock in! I know that if anyone can teach me it is my Uncle Bob!”

Thank God I was sitting down. I had such a hard on. Thinking of her ass in my face. My finger pushing up into her ass. Then my cock. I put my hand in my lap and adjusted my cock. What I wanted to do was jack off or fuck her on the table. I got this shit eating grin on my face and Judy got a smile on her face.

“If your thinking of jacking off let me watch! Please?” I was just about to push back and do that but then I remembered what we promised each other. No sex on a school night.

“Judy this is a school night and we did make a deal. No sex on a school night. And I know if we start we’ll never stop! So I promise that I’ll keep it for tomorrow. Okay?” I placed my hand back on the table and started to eat once more. College was to important to her, and she always wanted to be a nurse. The look on her face told me that she felt the same. In a way I was glad. I would not want her to fail. And I knew that this was going to be a long process. Getting some ones ass ready to fuck was not a one night deal. After dinner Judy went to study. I watched some TV and then went to bed. I was just about asleep when I heard a knock.

“Uncle Bob? May I come in?”

“Sure honey, come on in.” I saw her standing in the door. I could see right through her nightgown. It was like she had nothing on at all. I think that she knew I could see through it. She stood at the door to long. She came to the side of my bed. Bent over and just gave me a short kiss. One quick soft loving kiss on my cheek.

“Good night Uncle Bob. I thought that you could use a kiss good night. Thanks.” She turned and walked to the door. She stopped at the door and let me see through her nightgown once more. All we could both hear was my breathing, and the beating of my heart. I could make out ever curve in her body. I could see that she had nothing under her gown. I could make out her pussy lips. I could also see her ass. She knew what she was doing. The door closed so slow I was almost ready to cry out her name. “Judy, Judy come back to me”, but I didn’t. Then I heard the click of it as it closed. Then darkness. I fell asleep.

When I woke up Judy was gone. I got out of bed dressed and drove to the drug story. I know I would have to buy a few things. Went home and had lunch. I knew Judy would be home around 3pm. I took a shower and got dressed. Judy walked in at 3:15pm and had a smile on her face from ear to ear. She walked up to me kissed me and said.

“Happy Friday! I have to take a bath. Should I put anything on, or just call you when I’m done?” Just thinking of what I was going to do got me hard.

“Would you like to eat first?” I felt funny asking her that. We both knew what we were going to do that night. But it still felt funny asking her.

Looking at me she gave me that smile, or grin I have started to love. Then spoke in a sexy voice.

“No! Can we eat later? Between it?” Now it hit me. She wanted to start right now. I took a step towards her and took her hand. If I was going to teach her I would have to take her by the hand and walk her thru it step by step.

“Come with me my dear. I’ll show you, and teach you! I’ll take you step by step! First off we have to make sure your clean! Inside and out!” The look on her face. I knew then that she had no idea of what I meant. We walked to the bathroom and I started to undress her. First came her blouse. I unbuttoned it very slowly. She was going to help but I pushed her hands away.

“This is part of the fun! Taking your clothes off is half the fun. So just let me do the work. You relax and enjoy.” I pulled her blouse off her and looked at her bra. Judy loved to wear sexy lingerie. A nice lace bra. It shows off her tits. I knelt and took off her shoes. I looked up and could see her breasts pushing at her bra. Trying to pop out. I unhooked her pants and pulled them down. I purposely left her panties on. Something about Judy in panties and a bra. Now standing only in a black lace bra and black lace panties. So sexy. I stood and reached around her. I found the clasp and unhooked it. I took her bra off her shoulders and watched as her nipples came into sight. They started to get hard as soon as the air hit them. Or maybe it was something else that made them hard. I bent down as if to kiss them. I could see them rise and fall as she was breathing. Tonight was my night. I got closer and closer to her right nipple. I could feel her hot breath on the back of my neck. I felt her hands on my head pushing it closer and closer. I pull back.

“Not so fast my dear! I told you this is half the fun. I’ll do the work. You just relax and enjoy. Now, what was I doing?” The look in her eyes. Judy looked like she was going to cry. She had her mouth closed and she was breathing through her nose. Making a sound that told me she was dieing to have me kiss them, bite them, lick them or suck them. It sounded like she had just ran a 4 minute mile. Her moth closed as if she was in pain. She was now breathing through her teeth. I bent back down towards her nipples. I got about one inch away from her left nipple. Her breathing was so deep and fast that her nipples came up and down with each breath. Then I looked up at her. Her eyes locking onto my eyes. I knew what to do. I open my mouth and licked my lips. Looking at her nipples and then back into her eyes. I was just about a quarter inch from her nipple. I could feel it hitting my lips as she sucked in one last deep breath. Holding it for that touch she wanted. I bent down and then knelt on the floor.

“I almost forgot to take your panties off! They have to come off before we can...” I was now pulling her panties down. I could see the top of her pussy come into view. I could hear her breathing once more.

“Damn you! You know I want you to lick them. To kiss them. You bastard! You wait. I’ll get you for that, my little pretty!” I knew that this was all part of the game. I pull her panties all the way down and she stepped out of them. I looked back up and was face to face with her pussy. I bent forward and just kissed it. Right out of the blue, no warning. Placing a kiss right on her cunt. Something I knew she would not expect me to do. As I kissed it I felt her open her legs. I pushed my tongue out and licked her lips. I turned my head some. That way I could get a little deeper in. My hands went to her ass and I pulled her closer. I felt her bend back, which made her cunt open more. My tongue went deeper in. I could hear her moan. I felt her hips start to move some, as if she was fucking my tongue. My tongue became my second cock. Much smaller then my real cock. (thank God). Judy now had her mouth opened. I could hear her breathing faster and faster. She was saying something but I could not make out what she was saying. I felt her lips open more. I then felt her cum! I could taste it more then feel it. Judy had the sweetest tasting cum. A flavor all by itself. I sucked and licked at her cunt. Then I felt her ready to cum once more. I licked deeper and then pulled back. Once more I could hear her.

“You are a real mother fucker do you know that! I was so close! I could just slap you!” The look on her face told me all I wanted to know.

“I know my dear! This is all part of getting you ready.” I took her hand and helped her into the tub. The look on her face was priceless. I knew she thought I was going to give her a bath but I never turn on the water. I had placed a towel in the tub. It was folded. Looking at her I pointed to the towel and said.

“Kneel on the towel. Face the back of the tub and just kneel down and get on all fours.” Judy looked at me in a crazy way. She had no idea of what was going to happen. She must have thought I was going to fuck her here in the tube. Since the tub is big enough for two people to be in it at once I had her more towards the back. She was on all fours with the cute and dainty little ass sticking up. I put my finger in the KY I had placed earlier by the tub and started to rub her ass with it. I felt her tighten up some.

“Just relax. This is what the others didn’t do. First you have to get your muscles to relax. You see you have a muscle that goes all around your asshole. Then right inside, about one or two inches in you have another one.” As I was talking I was moving my finger around her hole. Just around her little brown rose. Her ass was much higher then before. She was now bent down in front. Her ass more in a 45degreeto the rest of her body. Her head bent down resting on her arms. I once more dipped my finger into the KY and placed it back on her “brown rose.” I was now pushing in as I moved it around. It took about five minutes but soon I was sliding my finger about one inch in and out. Then once again some more KY. Back to her ass and in about two inches. Back and forth. In and out. I could feel her muscles relaxing. With each push in I felt a little more of my finger go in. Then back all the way out and more KY. Once again I placed my finger on her hole and pushed. This time it went in all the way. I felt her open and just take my finger. I pushed all the way in and when I hit bottom I just stopped. Not moving. I felt her ass muscles tighten and then relax. Then tighten once more. Her breathing was getting deeper and deeper. I knew she had her fingers in her pussy. I felt them when I pushed all the way in. And I knew she felt my finger deep in her ass. All I could hear was her moaning and breathing.

“Judy! Just keep your finger in your pussy! Don’t take it out! And do not move them. Let me do the work. But remember do not remove your finger. I’m going to give you an ass cum! What I need you to do is to push down like you are trying to poop, but not to hard. Yes just like your doing!” With that I started to finger fuck her ass. In and out, in and out. I could hear her breathing faster and faster. Her moans came louder, and faster. I could hear her saying things. Calling me names. Telling me that she was going to die. I felt her finger moving just a little and I knew she was near the top. Then a scream that filled the bathroom.

All I heard was “AH!” But it was so long and loud. I felt her ass tighten around my finger and I knew I had to stop moving it. Judy was screaming out so loud I though she was in pain. But I know that she was in a world of her own. I guess you would have to have had an ass orgasm to know what I’m talking about. When I have one, it feels ten times better then the other ones. My wife told me that it is like you are coming out your ass, pussy and head. All at the same time. She told me every nerve in her body is working to make her cum. And I guess it is like that with me. But the first one is always the best I guess. You have no idea what to expect. Like your first fuck, or your first blow job.

Then I heard Judy crying. I knew that she was not in pain. I also knew the reason. Mary cried the first time she had on. And almost every time I gave her an ass orgasm she would cry. She told me that it felt that good she just had to cry. More like a cry of joy. I just kept my finger in her ass. Then I started to pull it out. Judy’s ass tighten up so tight that I had to pull my finger out. Her ass muscles tighten so that I could not just let it slid out. She has holding my finger in.

“Oh my God! What the fuck happen! That was unbelievable. Just un-fucking-believable! I thought it was going to hurt like hell! My God Uncle Bob!” She was turning towards me. Then her eyes open wide.

“You still have your clothes on! How did you do that? How could you have fucked me with your clothes on?” Judy thought I had used my cock. She had no idea that it was just my finger. I pulled my hand up from behind her and she saw my finger.

“That was just your finger! It felt so big. So long! If that felt that way with just your finger. Then how in the hell am I going to take your cock? It won’t fit! It will split me in half.”

“Judy my dear slow down. First came my tongue. Then my finger. Next I’m going to give you a nice warm enema. That will clean you out. Then I’ll use my tongue. Then my finger. Then two fingers. By then you my dear will be ready for the real thing. If not, we have all weekend. But judging from how you took to my finger. I think that by midnight you’ll have most of my cock in this tight ass!” And with that I started to push my finger once more into her ass. And this time it went in a little easier.