When I was going out with My Ex wife I really wanted to fuck her in the ass. She was not into it. So one day i was really pushing it. And she said she would let me have her ass if she can have mine first ... clearly thinking I would say no but when I said yes and she sort of was like er um ok ...we went to a local sex shop she picked out a dildo (Deal was it had to be close to the size of my dick) came home she said she had done anal once with a ex and hated it. She then said she gets to go first so I don't chicken out. I had never had anything in my ass accept a thermometer when little. She grabbed the lube told me to get on my hands and knees. Lubed up and finger fuck me for a bit. She had a old pair of underwear she ripped a hole in and when she started she was gentel but she had a mean streak in her personality after in she brutalized my ass. She tired out after really fucking me and she was like WOW guys really get a workout trusting like that. I looked down and there was shit on the dildo and i was a bit embarrassed. But i said my turn with a grin and knew she was gonna back out. Which she did saying i am not letting you fuck my ass the way I did yours. I told her throw the dildo in the tub i will wash it up but for now It is my turn and i promised I would be gentle... after a lil back and forth she finally said ok and I told her I would use a lot of lube she assume the position on all fours. I lubed her up and worked her asshole worked up to two fingers and the slowly slipped my head in. And sat still she immediately start beging me to move but go slow... which i did and then slowly got almost all the way in. I then proceeded to move in long slow strokes. I fucked her like that for about 20 minutes she came like 2 or 3 times and as i got close my cock swelled and she started yelling what are you doing how did you do that and a backed out as far as a could keeping my head in her and as i started to cum... I COMPLETELY began to brutalize her ass with about 20 deep hard strokes as I filled her asshole up. She never ask to peg me again. But she never said no to me again when I asked to fuck her ass.