My ex-wife and I had a lot of problems, but none of them were in the bedroom.
First, the usual descriptions. My ex is a natural redhead, who, throughout our time together, weighed about 100-110 lbs, and has B to small C cup tits and a decent ass. I’m a little heavier than average, with an average sized cock. We usually had pretty intense sex, often lasting 1-1 1/2 hours with multiple orgasms for her. Since I am both a gentleman and a pervert, my bedroom rule is if it feels good, do it. She often got nervous trying new things, but once she got over her initial nervousness, there was very little she didn’t like. This is about the first time we tried anal sex, which became our favorite thing for a straight week.
Due to several reasons I won’t go into, my ex had to have surgery which forbade us from having any kind of vaginal intercourse for about a month. My ex, being extremely horny, did not take this well, and decided it was time she give into my desires of “more than just a tongue or finger (and she loved a tongue or a finger, but was nervous going further).” She was determined to be penetrated during the month, and I was only too happy to be the one to do it.
The first thing we did was get some anal beads and lube. We already had some lube, but we wanted to get the good stuff…yeah, I now know how dumb that sounds, but I was being offered virgin territory, so I was going to agree with anything. She also told me she was determined to get fucked, and, by the end of the night, for me to fill her ass with cum. She said that once she was used to me inside her, she wanted the filthiest dirty talk I could come up with. “No limits at all,” she said with a smile.
We started with making out like two horny teenagers, and I slowly stripped her clothes off and gave her a rubdown, to make her loose and relaxed. When she was ready, I picked up the beads and covered the first two or three with lube. I lubed up her ass next, and began to slowly insert them. Right away, I could tell she was enjoying herself. “Tell me if you want me to stop,” I said, enjoying the sight of her ass filled with about 3 beads out of the six. “Keep going, I want them all,” she said with a slight strain, and a smile. I slowly inserted the next three, larger beads. “This feels…pretty good,” she said. I took my incredibly hard cock out and and moved near her head. She started to suck my cock while I reached around and gently tugged the toy in her ass. “Let me know when you want the real thing,” I said. After a few minutes more of a really incredible blowjob, she popped my cock out of her mouth and said, “I’m ready.” I just smiled and moved down to kiss her deeply. As we were making out, I slowly pulled the beads out of her, one at a time. Feeling the moans as much as hearing them while we kissed was one of the best feelings ever.
Breaking the kiss, she got on her side in a spoon position, and wiggled her ass at me invitingly. “Go slow and be gentle, please.”
“Of course,” I replied, grabbing the lube. “I’ll be a perfect gentleman…until you don’t want me to be.” She lay on her side and stuck her ass slightly out towards me. Her ass was fairly well lubed already, but I added more. She motioned me to move in front of her, then took the lube from me and started stroking my cock with it. I moved around the bed and laid down behind her, in a spoon position. I began to rub my cock up and down her ass crack, and positioned the head at the extremely lubed hole. I made sure I was angled in such a way that that I was laying slightly lower and at an acute angle to her (didn’t know there’d be math involved, did you?). I pushed into her slowly, and damn was it tight, even after the toy. She let out a ragged moan and I stayed still, enjoying the sensation of my cock in the one place it had never been. “Tell me when you want more,” I said, struggling to keep my cock in her ass. It was so tight and kept trying to push me out. “N-now,” she said, breathing heavily and raggedly. I pushed in deeper, waiting to be told to stop. To my surprise, I wasn’t. “Do you like my dick where it is?” I asked her. She moaned out a yes, barely. Remembering what she had said earlier, I continued teasing her and talking dirty. “And where is my dick?” She didn’t answer, so I reached my hand around to squeeze her tits, slightly pinching and pulling her nipples one at a time. “I asked you a question, slut. Where is my hard cock buried?” At this I began slowly sliding my cock back, only to slide it further in. She gasped and moaned. I wish I had recorded the sounds she made, it was such a turn on. She finally whispered to me what I wanted to hear. “In my ass.” Smack! I gently smacked her ass. “Louder,” I said while beginning to slide my cock in and out of her tight hole. “In my ass!” she yelled. “Very good. I’ll fuck you slowly until you tell me you’re ready for me to go harder. The only catch,” I told her, “is that I want you to tell me in a really filthy way. Sound good?” With a smile, she said, “OK, just keep up the pace you’re going at.” I was only too happy to oblige. After a few more minutes of this slow, sensual fucking, she begin to moan more deeply. “OK,” she said. “OK what?” I replied with a smile, knowing full well what she wanted, but continuing to play our regular game. She hesitated so I thrust in a little more forcefully and repeated, “OK what?” She took a breath and said, “I want you to fuck my ass hard. Do whatever you want to me.”
I nearly came right there (I’ve said this before, but sometimes hearing the right words in bed just set me off).
Regaining my composure, I smiled a wicked smile at her and began to run my hands over her body. I stopped them first on her hips, next on her tits and lastly, on her neck. She practically purred when I wrapped my fingers slowly around her throat and squeezed slightly. As I did, I began to fuck her ass harder. She moaned more and deeper. I don’t think I’d ever heard her make those sounds. I started talking really dirty to her, about how her ass was mine now whenever I wanted it, for as long as I wanted it. How I was going to keep pounding her until I filled her tight ass with my cum. She only agreed and smiled and continued to moan. I told her it was time to have her asshole filled with my cum. She moaned out, “Please fill my ass with your cum.” That made me lose it and I did exactly that, as best I could. Her ass was squeezing my cock so hard that it was hard to actually get it all out.
After that night, we got a lot more daring (which is saying something…).
Source: reddit.com/r/gonewildstories/comments/8sy2m1/first_anal_with_my_ex_mf
This was fucking hot! Great writing.