Sister and Brother Ch. 03
My sister and I rested for a while after the incredible orgasms we had just had. Unlike the first time we had been together, my cock was getting softer. I wasn't going to be able to do her ass.
My sister looked at my softening cock and said, "Looks like that awesome dick is taking a rest."
"Yeah, I'm sorry we cant keep going." I replied.
"Oh, who says we can't?" she said.
She leaned over and gently began to stroke my soft dick. She gently ran her fingers over the underside of it and around the purple head. There was no response. She then began to massage my balls with her other hand and still there was no rise. But my sister wasn't deterred, she just kept up her efforts and leaned over and started to lick my now soft dick. Her efforts with her mouth had little effect. My penis became a little more firm, but it seemed to be out of action for a while.
I looked at my sister, "I'm sorry." I said. "I wish we could keep going, but something seems not to be co-operating."
"It's not your fault." She said. "But who said we can't keep going?"
"What do you mean?" I asked.
My sister poured some more wine and said, "Well, we can do other things. A soft dick doesn't mean an end to fun."
She handed me one glass of wine and took a sip from the other.
"I had an awesome time last time and have so far tonight, but I think we have only scratched the surface; there are many other things we can explore." She said.
My sister had my interest. I had some ideas of what she might mean but wanted to hear her say it. So I asked, "Do you have something in particular in mind?"
"Please, don't act dumb. The way you fucked me in my ass would prove to anyone that you know how to do anal, probably form first hand experience." She replied.
I just grinned trying to look innocent. She could see right through me.
"Don't give me that innocent look. I bet you have tried fucking your ass before, lots of times I bet." She said.
She was partly right. There had been many times when I was dressed up that I would rub my fingers around my asshole. I would gently press against the opening and slightly push my finger in a little. Sometimes I would get more adventurous and glide my finger in further and move it around in my ass, rubbing against my prostate and making myself cum in a way I had never experienced before. But I had never gone farther than just my fingers. The technique I had used in fucking my sisters ass I had picked up from reading the stories others had written.
"I have never really had my ass fucked. I have played around with it but never had more than a finger up there." I told her.
"Well you don't know what you are missing then. I will have to take care of you." She said.
My heart began beating harder and I was getting turned on again. My cock was still quite soft though but it didn't matter to me. I was going to be ass fucked.
My sister went to her dresser and took out a dildo. It wasn't too big, but not too small either.
"We'll start with this. It seems about right for a virgin ass." She said.
I picked it up and looked at it. It was a good size, it didn't seem like it would rip me open all at once. It looked a lot like my own cock, pink and smooth with the veins and ridges in the right places. I was excited and nervous all at once.
"I don't want you to worry at all I will make this awesome for you. I am going to do you missionary stile like a virgin should be fucked the first time" she told me.
She smiled at me and lay me on my back. Then she took a pillow and put it under my ass to raise it up a little. Next she spread my legs apart and had me hold on to them with my arms. This was basically the position I had fucked her cunt in a little while ago.
I was a little nervous and asked, "Are you sure this is the best way for a first time."
She replied, "I know what you are thinking. You are probably thinking that fucking from behind 'doggie style' is better. But it isn't always so. This way we can see each other and let each other know what is going on. Also things are a little better lined up this way and it's also a more relaxed position for you so I can penetrate you easier."
Since she had been the one with a dick in her ass before I wasn't going to argue. Besides I just wanted to feel that dildo pushed into my ass.
"Just try to relax your ass." She said as she began. She started by squeezing a little lubricant on her fingers and gently massaging my ass hole. My cock was still soft but was leaking pre-cum all over my lingerie. My dick wasn't getting any harder but my excitement was obvious.
Next she slid one finger then another into my ass. It felt so good. She massaged around in my sphincter loosening the muscles and spreading the lubricant around. After a few moments of this she pulled he fingers out and squirted a little more of the lubricant on my ass hole and spread some on the dildo in a motion like she was giving it a hand job. My cock was still soft but the pre-cum was leaking out everywhere.
"Now remember, just relax and if it doesn't feel right just let me know." She said and I nodded OK.
She put the head of the dildo at the opening of my ass and moved it around in circles. The feeling was incredible and I loved it. My ass relaxed as the pleasure coursed through out my body and she slowly pushed the head of the dildo into me.
She took her time gently easing the dildo into me. Each fraction of an inch got me more and more excited. I wanted to feel the whole thing pushed into me. I wanted my ass fucked and I wanted it now.
"Please put it all the way in me." I asked.
My sister said nothing but just started pushing the dildo into me harder. Suddenly there was resistance and I felt pain. But almost instantly the pain was replaced with a pleasure I had never known before.
My sister saw the look on my face change from pleasure to pain and then to ecstasy and said, "I think I just hit your prostate. That is like the "G-spot" for a man, you should really enjoy this now."
She pushed the dildo into me a little further and the pleasure increased. I couldn't believe how good it felt. I was in heaven. The fullness I felt along with the stimulation of my "g-spot" combined to give me pleasure I had never known could exist.
My heart was beating fast and I was breathing heavily. I looked at my sister and said, "Please fuck my ass for real. I am ready."
She slid the dildo out almost all of the way. When the head got to my sphincter I felt a wave of pleasure and tightened my muscles around the dildo. My sister pushed it back in and again stimulated my prostate. I couldn't believe the feelings.
When I had fucked my sister wearing her lingerie and high heels I thought that nothing could exceed that experience. I had been wrong. Again I was dressed in a hot sexy outfit, complete with thigh-high stockings and high heel boots, enjoying taboo sexual pleasure with my sister. But now to heighten the experience she was fucking my ass with a dildo. The excitement was incredible and the pleasure I was getting from my ass were pushing me to a level of ecstasy I never would have imagined possible.
My sister began to slide the dildo back and forth in my ass, just as I had done with my cock when I was fucking her pussy a little while ago. With each stroke the dildo rubbed my prostate and made my dick leak a little more. She began to pick up the pace and I started to move my hips to meet her thrusts. The dildo was getting deeper and deeper and felt better with each thrust.
I began to feel a wave of pleasure build within me that I had never felt before. I felt an orgasm coming but it was different. It started deeper within my groin and wasn't centered so much in my cock and balls. It spread through out my groin, down my legs and up my back. My body began to contract and my thighs squeezed together, pulling the dildo into my ass. My ass began to pulsate and the muscles in my groin were squeezing and pulsing too. I arched my back up and began to moan loudly. I couldn't contain myself. My head was spinning. I could feel my cock pulsing and leaking cum on my belly, even though it still wasn't hard. This was like nothing I had ever experienced.
My sister kept thrusting the dildo in my ass. It was becoming more difficult for her to do it since my muscles were contracting, my hips were bucking and I was squirming all over. The thrusting of the dildo just kept this awesome orgasm going until I felt like it wouldn't ever end.
Finally, my body began to return to normal and I started to catch my breath. I couldn't believe what I had just experienced. There was cum all over my lingerie, dripping down from my belly along my sides onto the bed. My cock was still soft but was twitching along with my ass hole. I was exhausted but couldn't remember feeling so wonderful before.
M sister slowly slid the dildo out of my ass. As it came out I felt little waves of pleasure pulse up through my body.
"I can't believe how awesome that was." I said to my sister. "It was like nothing I have ever experienced before."
My sister came and lay on top of me and gently kissed me. There was still plenty of cum on me but she didn't seem to care.
"I'm glad you liked it so much, brother. But things don't have to stop here you know. There is still a lot more we can do. We have all weekend." She said. "But I think we both need a rest now. Why don't we sleep together and enjoy each other in a less sexual way."
I agreed. The amazing orgasms and the wine had made me sleepy. As I lay in bed with my sister I tried to imagine what might come next, but I soon fell asleep.