I slowly worked it back in and deeper this time. Then I decided to try my thumb as it was my fattest finger and I also realized I could move it in a way that would stretch her out a bit. After about 5 minutes of this I slowly pulled it out of her ass. Again I noticed while her ass would return to a pucker after I had stretched it out it wouldn’t close back up completely.I lubed her asshole up with the KY again and then my cock. I put my cock against her asshole and slowly started to push. After a few minutes of unsuccessful entry I kept trying to push harder and harder until she finally said:OH, Fuck that hurts! This isn’t working. Maybe, I should just give you a blowjob instead. I’ll even let you cum on my face if you want.I retreated, kissed her and said “look if you want to stop we can, but I think what is wrong is you have to push out as I push in.”“You mean like I am taking a crap?”“Yes” I put some more lube on lined it back up and pushed. This time she pushed back and my dick. One day when my brother was out with some of his friends the urge was to strong and I had to try some of them on that is probably when I developed my love of long skirts and dresses. I just loved the way they moved when I walked and the way they felt against my legs. After that I was hooked anything feminine just had to try. The next thing that I tried was pantyhose and just let me tell you they are the most wonderful things in the world the way they make your legs feel and look is just amazing. They should make them for men that way it wouldn't be so wrong to wear them.When I was 10 we moved into a trailer in a trailer park in the country and that meant no more experimenting. Well one day I was outside running and tripped over a steel beam I don't remember what they where using it for but I broke 3 of my toes so that meant that I was stuck in the house watching TV that's when I found out that there where other people who had the same sick feelings that I had. They didn't seem to.
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