I met Heather in High School and we hit it off right away. We were both perverts in our own way and open to just about anything. We did a lot of video taping and I kept all of the tapes after we split up. The best tape was the one in which we tried anal for the first time. It was great for me but she didn't enjoy it as much as she did later on in life. We always took turns tying each other up and this was one of those times. I had her lying on the bed face down tied to all 4 bed posts. It was then that I told her we were going to try anal for the first time. She was not too pleased by this but knew there was no way she was talking me out of it. I loved her perfect ass and wanted to fuck since the day we met. This was finally my chance. I started by licking her asshole and getting it nice and wet. Then I slowly started putting fingers in one at a time until I had 3 fingers buried into her knuckle deep. She was enjoying this since I was teasing her clit with my other hand the whole time. After about 10 minutes of this I sat up and smeared my 7 inch cock with a ton of anal lube. Then i started to push my had dick into her ass.
This was my 1st time trying anal too so I had no idea what I was doing. I just started slamming my cock in and out of her going deeper each time. She was screaming but I thought it was pleasure not pain. Her ass was so tight I only lasted a few minutes before dropping a huge load into her ass. It was spilling out all around my dick as I finished pumping into her. When I pulled out I came around to have her lick me clean and that's when I realized those screams weren't pleasure. She was crying and mad as hell at me. She want to kill me. We got passed it but still broke up about 4 months later. I showed that tape to all of my buddies and we laughed our asses off about it. Word got back to her however and she was not too please with me. We went our separate ways to different colleges but after graduation we both came home and wound up getting married. She still looked great with her long brown hair, 36c tits and the best ass I've ever scene.
Heather was still crazy as ever in bed and we had tons of fun. One year for my birthday she told me she had a BIG surprise for me and that I would love it. It would be just like old times. So I was thrilled when she told me that she had finally talked her friend Jolene into a 3sum. I always wanted to fuck Jolene. She was athletic with monster 38DD tits and rockin body to go with it. Jolene was married but they were swingers so I figured he was cool with it. That night Jolene came over and we got pretty drunk before the girls informed me that they want to tie me up. Jolene got on her knees in front of me and took my pants down. She then proceeded to give me the best blowjob I had ever gotten. While she was doing this my wife tied my hands to ropes and then ran them over the back of the couch so that I was now bent over the back of the couch with Jolene trapped between me and the couch.