[1rustywood]

I starting dating a smoking hot girl after a 2 year college relationship ended with someone my new gf knew from work. She knew we had sex for a long while. When she would question me about it, I felt uncomfortable as I was afraid of upsetting her. She assured me not to hold back the details but most certainly did. Soon after one of her digging for details attempt we were fooling around. Low and behold she for the first time went down on me with a motivation I had never seen. She stopped briefly only to mention if it was better than my ex's Debbie's bj's. I never even told her she gave me bj's. Was she assuming, digging for more details, I didn't know or care for that matter. Shit! I was getting blown! She was motivated like I had never seen before. It was great! Obviously, it got me thinking how could I get her to swallow or do anal when she has already told me her disgust with them.

I figured if I could only get her to believe Debbie liked both I thought she would try them with me! But how to I do this? she already thought I was too decent and respectful to discuss such things. So here's what I did, the next time she brought up my previous sex, Which she did often, I would change the discussion from my past to others and indirectly hint about anal or swallowing that I heard other girls did and enjoyed. Just to put the acts in her mind but not related to me or my old gf. Sure enough the next time she was prying me for details she wanted to know if Debbie did anal with me. Here's where I deserve an Oscar! I acted nervous and like I was lying as I said nooooo with a bit of a quiver. She thought I was lying! But I was not, Debbie never swallowed or took it up the ass for me!

These insecurities she had would just eat at her. She wanted me forget my past and she was bound and determined to make new memories. Sure enough, not long after this talk, she appeared unannounced in my bedroom. I still lived at home. She took our clothes off and said she wanted me put it in her ass! I acted cool and caring again, saying are you sure, I don't think you'll like it, I've heard its very painful. All the while excitement was raging and I wanted to pound her tiny firm little ass! She insisted! So I laid her on my waterbed face down and massaged her sweet hole for preparation. I climbed on top, trying not to be to forceful, and eventually penetrated her. Oh my God! The sensation was so great I just froze to feel all the sensations. So tight! So Soft with two ass cheeks as bumpers. It felt better than anything I ever felt before! When I started to gently trust, I propped myself up with my arms while her head was biting my pillow. Then I noticed my headboard had a mirror and I could look down and see a bit of her face. While she was withering to what I thought was delight, she also glanced up and saw the mirror. She was not enjoying this at all. She stared at me with tears and mascara running down her face. I had to stop trusting. Talk about a major throb, for the only time in my life I felt the floodgates of my already hard cock open and throb with pressure. It actually hurt my cock so much I was afraid it was going to burst! No Shit!! As I said are you sure about this, I slowly started pumping again. I was not stopping for anything but I wanted her to think I cared. So as I sweet talked her I returned to pounding away and blew like never before or since.

Unfortunately, we never did anal again, but let me tell you it was worth it!