A Defensive Side Trip

I'd been going out with several different ladies before hiring Tracy. Now they were getting ignored. Once I noticed, I decided that Tracy was to getting to me. The balance was shifting. I don't tend to go backwards, so I needed a new and powerful distraction. A few days later I sat down next to this very cute little thing on a flight back from Las Vegas.

She had long dark hair, big tits, and a great smile. I'm normally not crazy about big tits, so I wasn't that attracted. On the other hand, the guy traveling with me WAS into big tits. He was sitting across the isle and started hitting on her immediately. She began talking to me, I think as a defensive move.

This was the last flight of the night so I assumed she was local. I was right. Her name was Angela and she had broken up with some guy a week before. My friend drove her right into my arms. In under an hour, I was sliding her skirt up and rubbing the side of her ass underneath the arm rest while talking intensely and looking into her eyes. She was smiling at my audacity. Sometimes you get lucky. She was also telling me the different ways she liked to be kissed. This was going to be too easy. I'd found my distraction from Tracy.

But Angela seemed to have cooled by the time we got to the luggage carousel. She was being quiet. There were a lot of people around and I was standing right behind her. I decided to find out how adventuresome she was. She had on a very thin dress so I sort of moved forward until I could feel her ass against the front of my slacks. She started moving back against me gently.

She had taken the lead! I wasn't sure if I was ready to up the ante in such a public place. Fortunately, our bags came before we did. I offered her a ride home. She whispered in my ear, "You can take me anywhere you want," and then giggled.

Bingo! I rushed her to my house and even lead her into my bedroom, but by then she had cooled again. We were sitting on my bed drinking a beer and she said, "So why are we in your bedroom?"

Talk about hot and cold! She was totally chilled. I tried lots of things, but couldn't get pass this frontal defense. What a tease!

Then she put her beer down, jumped off the bed, and said, "Where's the phone book? I should call a cab." I told her I would take her home, but she said then I would just want to see HER bedroom. She got down in front of my night stand looking for the phone book.

I couldn't resist. I got down behind her and started humping her ass. She humped back! I gently raised her dress up over her back. She had a very nice ass. I grabbed her tits and really started digging in. She was breathing hard and pushing back. I kept it up.

Then I slid her panties to the side and put my hand over her pussy. She was already wet. Just as I was about to slide my finger in, she jumped up and said, "This is too soon," as she pulled her dress back down.

I looked down. The front of my pants were wet from where I had been dry (wet?) humping her. She seemed embarrassed. "Cool," I thought. It'll be more fun to wait. I can tease as long as she can, maybe longer. Little did I know.

I gave her a ride home, but she wouldn't invite me in. We talked in the car for a long time, which lead to some of that kissing she had described. This lead to more touching and she started breathing hard. All of a sudden she jumped out of the car and I had to roll the window down to make a date for later that week.

After a couple of days, we had a nice dinner with lots of verbal teasing on the side. Back at her place, we were watching a movie. I was sitting on her butt rubbing her back and she was moaning, but each time I tried to roll her over to undo her jeans, she would just roll back on her stomach. Her front was off limits.

Again with the weird hot and cold shifts. This lady seemed to be a paradox. She got hot quickly, then totally cold even faster. She seemed to freak out whenever I started getting close to penetration or even undressing her.

I figured it was the old problem of tease and commitment. There was some touching that night but that was about it. Every time I tried to take her clothes off, she would pull away. Then she would look at me as if I was supposed to know what was going on. I felt like an idiot. We even talked about it. She said I just needed to be in the right place with her. But she couldn't tell me where that place was. I didn't know it at the time but she was being literal.

This same MO went on for a couple of weeks. I began to take it as a personal challenge. In any case, it was a good break from Tracy who just teased me in an almost platonic way. At least Angela was teasing me in a SEXUAL way. But this wasn't the classic tease. There were times she was getting REALLY hot. I was sure she wasn't faking it. Or if she was, she was faking it really well. I could tell she wanted it. And she wanted it bad! So how would I get her comfortable? I had a feeling that once I managed that, it would be worth the effort. I was right.

After about the third or fourth date, we were at her house and I decided to take off early. This did the trick. As I opened the door to leave, she gave me this really hot kiss and wouldn't let go. She didn't want me to leave. I started playing with her ass as I was standing there. She started breathing hard again. This was good. I unzipped her pants in the front and popped the snap open. She didn't resist.

Next I moved both hands around her ass inside her panties. This was working. She was pushing her ass back against my fingers opening herself up to me. With one arm I held her tight so she couldn't wiggle away. With the other hand I moved down the crack of her ass. As my finger slid across the pucker, she went wild. Then I pushed my fingers farther down and slid all the way into her cunt from the back. She was soaked.

The door was still open, so I kicked it closed. I didn't want to break the moment. She started to roll away but I held on. I got my fingers back into her from behind. Then I felt her relax in my arms. She started humping my fingers. I had my thumb against her asshole and massaged it for added effect. She was making little grunting sounds. All of a sudden, she screamed and came, convulsing in my arms. We fell down on the carpet with my fingers still in her.

I didn't want her to cool off. I grabbed her pants and pulled them off but just dropped mine to my ankles. I wasn't taking any chances. I fell between her legs and reached down to slide it in. She was very wet everywhere. I just barely got the head in and was ready to drive home when I felt her hands around my cock. She was holding me from getting any farther in! Bizarre!

She moaned, "Wait..."

So what the hell? We had already talked about disease and rubbers. No problems, she was on the pill and this was before AIDS was popular. What was this about? She held on to my cock and kept rubbing it up and down her slit from her asshole to her clit and back again. I would wait until she got it at the right angle and then try to push through her hand. Once it almost went in because her hand was slippery, but she scooted back and said, "You're dangerous."

I laughed and rolled off her.

"I'm dangerous?" I yelled, "What about YOU?"

She had such a forlorn look. And then she whispered, "Don't give up on me."

I moved to kiss her, but she just turned her back to me and we were in the spoon position with her wet and naked ass against my cock. I held her a few minutes thinking she just needed to relax, but of course my cock naturally slid into the crack of her ass. I thought we were relaxing but she started pushing her ass up and down my cock very slowly. This was crazy! I was getting close to raping her! At some point logic leaves you. I grab my dick and pushed it down so that it would go in as she moved her butt back on the next up-stroke.

Flashes of pain! Finger nails! She had her hand over the opening of her cunt! I pulled my cock back with my hand and she said she was sorry. I wasn't injured badly. Or maybe I was just in shock. Then I got pissed. I started humping her with just a couple inches of my cock sticking out of my fist. Everything was soaked. If I got close, it would slip right in. We were wrestling, but she wasn't really trying to get away. With my other hand I tried to pull her arm away to gain access to her cunt. If this was rape, it was weirdly cooperatively.

As I pulled at her arm, she rolled with it keeping her hand between her legs, pop! It went in! No. My cock was in her ass! I didn't give a shit. I took my hand away and drove hard. Everything was so slippery, there was no resistance. I went in her ass all the way up to my balls. I was tired of being nice. I just started fucking her in the ass real hard. She screamed. I froze, finally realizing how rough I had been. Then she yelled, "DON'T STOP!"

Immediately, I was back up to speed. Again she started screaming, "Yes, Yes, Yes, Yes, Yes, Yes," in rhythm to the pounding I was giving her. I wasn't trying to be nice either. She seemed to like it rough.

Well, you get the idea. I rolled her on to her stomach and thrust into her deep and fast. We both started coming hard. The tension had been so high for so long. It was a great fuck even if it was in her ass. I stayed in her for a long time as my dick got soft, then rolled off.

As I was lying there afterwards, it hit me. This is what she wanted all along. She WANTED to be fucked in the ASS. And I was supposed to figure it out on my own. I started laughing. She looked at me. She knew I'd figured it out. We talked about it later.

It was something about her not wanting to be the one responsible for suggesting such a dirty deed. After all, this WAS the eighties. She didn't want me to think she was THAT kind of girl unless I was THAT kind of guy.

And if I wasn't THAT kind of guy, she said it probably wouldn't work out anyway. She said if she let guys into her pussy first, it was a lot harder to get her way later on.

She turned out to be a very hot little lady and this affair lasted for the next several months, actually right up until I finally captured Tracy's heart. And yes, I did manage to get into Angela's cunt -- lots, even later that night. It was just that she wanted someone who was comfortable doing her in the ass first. Her little dance was how she qualified her dates. I was glad I'd finally passed the test.

She didn't know it at the time, but I'm not really into ass fucking. I did give it to her in the ass on a regular basis, but that's because she dug it so much. I got more ass fucking with her in that few months than in the rest of my life combined. And she did have a beautiful ass.

About the only other way we had sex was with her lying flat on her stomach and me fucking her pussy from behind. She said it felt almost as good as doing her in the ass if I put all my weight on her.

I did manage to try a couple more conventional positions, but if I started playing, she would roll on to her stomach and stick her ass in the air. She just liked getting it from behind. I could choose the hole. If I picked her ass, she pushed back. If I choose her cunt, she laid down flat. It was fun either way.

So what's the point? The moral of this story is, if something seems to be a paradox, you just don't have enough information. Keep trying. And what does this have to do with Tracy? A lot. You'll see. I don't know about you, but I need a break.