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. She kept sucking my cock while my wife tied my ankles and ran the rope under the couch and wrapped them around the legs on the front of the couch. It was all done too fast for me the realize what was happening. As soon as Heather pulled the rope tight I knew I was screwed. I was ass in the air, bent over the back of the couch and tied tight. It was then that they broke out the camera and told me it time for Heather's revenge. Jolene got a 6 inch strap-on out and proceeded to lube up my ass with her tongue. I was hardly wet when she started trying to push the rubber cock into my ass. It was so painful but I could do anything to stop her. Soon they realized they needed some lube. Once that was spread on it slid right in. That was when they started really tearing my ass up. They took turns fucking me with dildos, strap-ons and their tongues. The whole time keeping my cock on the verge of cumming with hand jobs and blow jobs. Then I saw Jolene put on a HUGE starp-on. It had to be 9 inches long and thick as hell. I kept telling them it wouldn't fit but they didn't want to hear it so they blind folded me and gagged me. The next thing I knew I felt this monster start to enter me. It hurt so much I thought my ass would rip out when she pulled it back out of me. It took about 5 minutes for her to get it all the way in and then she just sat there letting me get used to the size of this thing. Then she started to really fuck my ass. She was power fucking me while my wife video taped the whole thing. Then I felt my wife's mouth wrap around my cock and every time Jolene slammed into my ass my cock went all the way down her throat. I was actually enjoying this now. After about 5 minutes of this I felt my cock begin to twitch and so did Heather so she pulled away. Then I heard the 2 girls giggling and then my blind fold was taken off and the girls were both in front of me in a 69 position. How could that be I was still getting fucked????? I turned my head to see Jolene husband Dave fucking my virgin ass for all he was worth. It was right then that my cock let loose all over the back of the couch. I don't think I had ever cum so much in my whole life. It just kept pumping more and more cum out. Soon the girls came over and started licking it up right about the time Dave unloaded into my ass. It felt like a bigger load then I had just dumped on the couch and floor but this one was filling my ass. As soon as he pulled out it all came flowing down my ass and legs. The girls took turns licking Dave's 9 inch cock clean and giving my ass a good cleaning too. They finally untied me after I promised I wasn't mad but they held that tape over my head for years. Heather and I "team" up with Jolene and Dave all the time now. I'll fill you in on some of that later.
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