Sister Golden Hair Delight

Copyright @ calibeachgirl

All rights reserved, 2010

There had been only thing I had not tried with Jimmy... anal and I wanted it, if I ever was going to do it, to be with him and soon. He was the amazing love of my life and our whirlwind romance just kept getting better and better.

To have said that I was nervous would have been an understatement. I had heard all kinds of things about it and had once thought it must be an 'acquired taste' for the woman since evidently it was every man's secret desire to get it up there, the final frontier.

This had been something my mother never told me about. In fact, for that matter she had never told me much of anything. I do believe now that in her mind ignorance guaranteed chastity. She was no help whatsoever in either teaching me or offering to answer questions.

Once I had been sleeping with Jimmy I had become so much more comfortable with the idea of having anal sex and I needed to know my own body.

I never had looked closely at it. I used a mirror and had a look. I wasn't sure whether I would or would not like what I saw. After all, when's the last time you did that?

I needed to explore myself by myself in the privacy of my bedroom or my bathroom. I needed to see how something entering me would feel and to either become comfortable with it or decide that it just wasn't for me.

I didn't want to try it with Jimmy first and then have to back out while he was trying to stick it in because I was either afraid or being hurt.

I knew enough that when I was tense my asshole was going to be closed tighter than I could ever imagine and nothing would be able to enter. It was amazing, I thought, how big a part of my mind played in the act of butt-fucking.

I wanted the decision to remain mine. No matter how much he respected me if I offered to do it without understanding what was required it would probably end in disaster and I couldn't afford that, I loved him too much.

I had to figure out how to be comfortable with getting it up the butt. I couldn't just ask my friend, Sue Anne, if she ever did it and how did that work out.

Visiting several adult websites, I got a lot of information. Most of what each one said was pretty much the same so I decided that was what I had to do.

I went into the bathroom and prepared an enema making sure it was a comfortable temperature. I wanted to be as clean as possible there. I didn't want him to get an infection and since we had not been using condoms it was unlikely we would if I decided to do it with him.

Trying to decide if I wanted to use the shower or the tub... I decided on the shower because if it didn't work out right I didn't want to be in a tub full of poop.

After the enema, though, I decided to move to the bedroom and do it there. It was a much friendlier place to be and if I fainted I was right there in bed. I didn't know...

I had lain there and took my fingers and moved them over the inside of my thighs and over my pussy. Eventually I was more comfortable with what I was planning to do and I drew my legs up and ran my fingers down the place between my pussy and my asshole.

Taking some fingers, I pushed against my asshole while my other hand was rubbing my clit. From what I had seen in the videos I watched, the women all rubbed their clit while having the man pound into their butts. Every one I looked at, though, seemed to be going too fast. I just couldn't believe that a woman could stand being slammed into so fast and so hard.

It must have been the 'naughtiness' of the act or just the excitement of doing something so different, so forbidden that I came hard after about ten minutes. I definitely felt relaxed after that and wasn't really afraid of doing it... at least as far as I had gone.

I wanted to take it nice and slow because it was late at night and he was gone on some military thing that I couldn't go to. I felt better about it because Major Paras had stayed behind.

Using the mirror again, I looked at my asshole. It didn't look all that big and I knew how big and long his dick was. I began to have misgivings about the whole thing but since he was gone and coming back two days later, this was my only chance to get something done in privacy.

I knew enough biology to know that the rectum could easily accommodate a large dick unless the man is a physical freak.

I had trimmed all my fingernails short. I knew that if this didn't work I had lost my beautiful inch-long nails for nothing so I had been determined to find out. I just didn't want to scratch the inside of my ass and really fuck myself up. How could I have explained it to the doctor?

I put on the vinyl gloves I got from the clinic downstairs for this great experiment but I knew we weren't going to be wearing gloves when we actually did it... that would a total turnoff and destroy whatever romance there was.

Smearing KY all over my asshole, I actually inserted my middle finger inside. It was actually uncomfortable for me... not the finger but just the position on the bed.

I decided that since I was most likely going to be in bed or on his couch I should try and position myself the same way we'd been having sex. Remembering back, we had more sex on that couch than we ever did in either his bedroom or mine... or that office floor.

Bending my legs up a bit, I brought my feet closer to me. I used my left hand to start rubbing my clit again and when I was feeling good I inserted the finger of my right. It was a little difficult so I squirted out and rubbed in some KY.

I decided right then that there was no such thing as too much KY. I could afford it. If this worked I was going to buy the stuff by the case.

I started to gently push my fingertip into my asshole. I pushed like I was going to have a poop and I could feel it opening up much more easily because of the KY and it went in a ways and then it popped out. It seems that I had to keep pushing otherwise the muscles there would push it out. I tried to relax like the website said to and got it in.

It felt strange but not hurting. All the while I was still rubbing my clit and had been nearing a climax and then I came. Damn, that had felt so good that first time.

Feeling like a little girl with my hand in the cookie jar, I wiggled my finger around trying to see what it felt like. It was soft and seemed very friendly.

After all this time, I still feel it's a wonderfully different sensation than anything I've ever felt before doing it.

It is funny to think that I thought I had a pretty nice ass back that first day we met when I got all dressed up to meet him and then I was working to prepare to shove his dick up it.

I moved my finger around in different directions to see what each one felt like. I even took the fingers of my left hand that were now buried in my pussy and pressed back against the finger in my ass.

Cumming again, I decided to lie there for a while getting my breath back.

I got up to get a drink of orange juice.

I had known that one finger was not his dick and did and did not look forward to the next finger going in.

Putting a whole fucking tube of KY around and inside my asshole, I got my courage up and slid my index finger in alongside my middle one and carefully, so slowly began to spread them apart a little. I stopped for a few minutes waiting for everything to catch up including my beating heart and breathing.

When I felt ready enough to continue I decided to practice trying to relax my asshole. That actually came pretty easy and I was surprised.

Maybe this was something I could really get into and when he wasn't available going on some military thing I could take care of myself.

I couldn't believe how much time had gone by. I had been in bed for over an hour and still only had two fingers in my ass. If it had gotten any later it would have been early the next morning.

I carefully slid in another finger from my left hand and really started massaging my clit with my right hand thumb while the rest of those fingers were now moving quickly into and out my pussy. I felt like I had been so sure I was going to cum but I didn't.

Lying there in bed, I stared at the ceiling wondering just how I had gotten to the point where I had my fingers up my ass. It wasn't what I was expecting when I met him that day for lunch.

It was dim in the room with only the nightstand light on. I had thought about lighting some candles but I didn't want to burn my apartment up in case something went wrong.

I opened the plastic bad I had put my mail-order dildo and butt-plugs in. Earlier I had thoroughly cleaned them and now I was actually going to do it. I remembering looking at it and mentally comparing that dildo with Jimmy's dick. His was just a bit larger and this dildo looked plenty big already.

I took both hands away and wiped them on the towel from the bathroom I had put on the sheet. Putting an entire KY tube's worth on it I slowly pushed it in just a bit and tried to get used to the feeling.

It was a strange different feeling, not good, not bad. At least it didn't hurt. I found that I did like the feeling just after it was pushed in and pulled back. I liked the way my asshole tightened up and tried to grab it.

I moved it some more and pushed it farther in. I found that it didn't matter to me how far it went in and I had actually preferred it staying just within the first couple of inches or so.

I was realistic, though, and realized that since it didn't hurt much at all I was going to let Jimmy do it all the way. I was going to ask him to first do it in and out near the hole so that I could also feel good.

I now understand why the women in the videos were frantically fingering their clits.

For Jimmy and all men I guessed, the tightness of any woman's asshole clutching the length of the man's dick was what was going to set them off. I also realized that any pussy, not matter how tight, was not going to approach the tightness of an ass. I just had to make sure that I had put plenty of KY in there and on his dick.

I left the dildo in there for a while getting used to the fullness and finally pulled it out and left it on my stomach. It's pale color contrasted with my darker skin and it was funny to think that's how Jimmy's dick would look.

I decided that for the first time it was going to be his dick only and maybe every time after we had oral. The combination of my hand and something big in my ass seemed just the thing to bring me off quick and hard. I only planned on doing it in my pussy if we wanted to have a child.

I eventually went back into the bathroom to clean up and I looked at my ass. My hole was still open a bit but as I watched it slowly closed back up.

It was still a good looking ass and I was exercising twice a day to keep it that way. If only I wasn't feeling so nauseous once in a while each morning.

I was his lover, his soon-to-be wife and companion for life and I didn't want to be afraid and spoil the experience with him. I had been sincere about anal sex with him and wanted it to be a pleasant time for both of us.

If it worked out that we both liked it I was determined to satisfy him but I was going to tell him when I was comfortable doing it. As many times as we've had sex it seemed like it was eventually going to be a choice of morning, noon or night... or a combination of the three.