I got my start being an anal bottom when I was trying to get my GF to try anal. She said, "If it feels so good, how about if I use my new strap-on on you?" What could I say but, "Of course, Honey." I did and she did. First I used a enema bulb and warm water to clean myself out, three times. Then I took a hot shower. I came back into the bedroom where she already had her new strap-on on. It was large, 9 X 6 inches, with a big, mushroom head and heavy, bumpy veins on the shaft. I do not know what I was thinking when we bought it, because she had never had anything larger than 7 X 5 inches then. But, we kissed a lot and then she had me lay on the bed on my stomach with my legs open. She started rimming me, something she had never done until then. Her tongue is very long, probably twice a long as mine, and it felt so good as she pushed it in my ass as deep as she could, again and again. Then she used a finger to gently lube my ass, and begin to open it up. This was followed by two lubed fingers, as she got me to relax my ass more and more.
She had me slide off the bed until my knees were on the floor. She brought the strap-on and a magnum size Trojan condom around to my head, She unwrapped the condom and rolled it onto the strap-on. Then she had me suck on the strap-on. It was so big I thought I was going to choke on it. I tried to deep throat it but could only get about half of it in. However, as she took it out of my mouth there was a lot of thick, slimy throat juices on it.
She then went in back of me, squirted some lube on the strap-on, and started rubbing it up and down in my butt crack, back and forth over my anus. Soon, she began concentrating on my anus with the head of the strap-on, pushing it into the opening and letting it come out, each time getting a little deeper and deeper. She apparently used a lot of lube, and I could feel it gradually opening my anus. Suddenly, as she pushed it in, it "popped" past my sphincter. I exclaimed, "Oh!" She kept it there and asked if I was OK. I told her with a groan, "Yes." She then started moving the dildo in and out of my ass, not withdrawing the head beyond my sphincter, but each time getting it deeper and deeper in my ass. By this time it was feeling very good, especially as the big veins on the dildo moved in and out of my sphincter and the rim of my anus.
I realized that she had it all the way into me as I felt the balls of the dildo rest against my balls. She bumped it there several times and asked me how it felt. I told her that it felt great. She started moving it in and out, using the whole length in each stroke. Oh, it felt unbelievably great! My ass felt so full, and so good! I realized that my cock was hard against the bed under me. She got faster and faster and soon she was really pounding my ass with the full 9 inches each stroke. I was groaning as she hit bottom each time. Soon, I could feel an orgasm begin to happen, groaned, and told her that I was about cum. She said, "Cum, cum, I want to pump the cum out of you!" And cum I did, over and over, grunting each time, until I could pump no more. She kept the strap-on deep in me and lay forward onto my back, her hard nipples pressing against my back. I was exhausted, and so was she. We lay like that for probably 10 minutes, until she got up, and pulled the strap-on out of my ass. She slide out of the harness and dropped it on the floor. Then she lay down beside me, pulled me over to her and we French kissed for a long time. After we rested for a while, she had me roll over so she could look at the big wet cum spot on the bed. She laughed and said, "I don't think you have ever cum that much in me!" I agreed.
Since then we moved on to me giving her anal with my cock, and during our swing sessions with others, both of us having sex with guys that had cocks as large as 9 X 6 inches, and her using her strap-on on guys. It is just a guess, but we estimate that in the four years since then, she has used her strap-on on over 60 guys (many of them multiple times), and every one has loved it. She usually starts them of on their stomach, and then when they are used to it, she has them flip over onto their back so we can alternate with me sucking, and then her stroking, their cocks until they cum. All the guys agree that they had the biggest orgasms ever when she was drilling them with her strap-on.